Marine-Natural-Products

REVIEW www.rsc.org/npr | Natural Product Reports

Marine natural products

John W. Blunt,*a Brent R. Copp,b Wan-Ping Hu,a Murray H. G. Munro,a Peter T. Northcotec andMichele R. Prinsepd

Received (in Cambridge, UK) 7th November 2006First published as an Advance Article on the web 11th January 2007DOI: 10.1039/b603047p

Covering: 2005. Previous review: Nat. Prod. Rep., 2006, 23, 26

This review covers the literature published in 2005 for marine natural products, with 704 citations (493for the period January to December 2005) referring to compounds isolated from marine microorganismsand phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs,tunicates and echinoderms. The emphasis is on new compounds (812 for 2005), together with theirrelevant biological activities, source organisms and country of origin. Biosynthetic studies, firstsyntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

1 Introduction2 Reviews3 Marine microorganisms and phytoplankton4 Green algae5 Brown algae6 Red algae7 Sponges8 Coelenterates9 Bryozoans10 Molluscs11 Tunicates (ascidians)12 Echinoderms13 Miscellaneous14 Conclusions15 References

1 Introduction

This review is of the literature for 2005 and describes 812 newcompounds from 283 articles, an increase of ∼13% from thenumber of compounds reported for 2004. As in previous reviews,we show structures only for new compounds, or for previouslyreported compounds where there has been a structural revisionor a newly established stereochemistry. Previously reported com-pounds for which first syntheses or new bioactivities are described,are referenced, but separate structures are generally not shown. Ina departure from past practice, no reference is made in the textto the establishment of absolute stereochemistry when standardmethods (e.g. Mosher, Marfey, X-ray crystallography) have beenused, unless there are some unusual features associated with theuse of these techniques. However, where such determinationshave been made for a compound, that compound’s identifyingnumber in the diagrams is distinguished by addition of a †.

aDepartment of Chemistry, University of Canterbury, Christchurch, NewZealand. E-mail: [email protected] of Chemistry, University of Auckland, Auckland, New ZealandcSchool of Chemical and Physical Sciences, Victoria University of Welling-ton, Wellington, New ZealanddDepartment of Chemistry, University of Waikato, Hamilton, New Zealand

Stereochemistries shown for compounds not labelled with † shouldbe assumed to be relative.

It is with great sadness that for a third year we note the passing ofa chemist eminent in the field. On 3 February 2006 our colleaguePierre Potier, Professor of Chemistry at the Museum Nationald’Histoire Naturelle in Paris, Member of the French Academyof Sciences and former Director of the Institut de Chemie desSubstances Naturelles, passed away. Professor Potier was notedfor his inspirational work on anticancer drugs and in the marinearea for his pioneering marine natural product work in the NewCaledonia area including the advancement of girolline towardsclinical trials.

2 Reviews

There continues to be a steady stream of reviews on specific topicswithin marine natural products, but with only one review1 givingoverall coverage of the 2003 literature. Several reviews explore thedevelopment of marine compounds as drugs.2–6 There have beenreviews on aspects of the chemistry and bioactivity of compoundsfrom soft corals,7 cyanobacteria and microalgae,8 cyanobac-teria and macroalgae,9 sponges,10,11 cnidaria,12 hoplonomertea,platyhelminthes, polychaetes, bryozoans and hemichordata,13

echinoderms,14–16 ascidians and fish,17 the gorgonian Pseudoptero-gorgia elisabethae,18 ascidians of the genus Aplidium,19 the spongegenus Halichondria,20 and terpenes from the soft coral genusSinularia.21 Specific types of bioactivity associated with marinenatural products have been reviewed in articles on anticancerdrugs,22 agents for treating tuberculosis, malaria, osteoporosis andAlzheimer’s disease,23 antifoulants,24 treatments for neurologicaldisorders,25 anti-inflammatory agents,26,27 anti-HIV compounds,28

and topoisomerase inhibitors.29 Growing interest in marine mi-croorganisms is reflected in several reviews.30–35 Reviews on severalaspects of the chemistry,36–38 toxicology,39–41 assay,42 and riskfactors43,44 of marine toxins have appeared. Particular classesof compounds from marine organisms continue to be wellreviewed, with offerings on pyrroloiminoquinone alkaloids,45,46

polymethyleneamine alkaloids,47 fatty acids from lipids,48 indolealkaloids,49,50 guanidine derivatives,51 bromopyrrole alkaloids,52

This journal is © The Royal Society of Chemistry 2007 Nat. Prod. Rep., 2007, 24, 31–86 | 31

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http://dx.doi.org/10.1039/B603047P

John Blunt obtained his BSc (Hons) and PhD degrees from the University of Canterbury, followed by postdoctoral appointments inBiochemistry at the University of Wisconsin-Madison, and with Sir Ewart Jones at Oxford University. He took up a lectureship at theUniversity of Canterbury in 1970, where he is now a Professor. His research interests are with natural products, and the application of NMRtechniques to structural problems.

Brent Copp received his BSc (Hons) and PhD degrees from the University of Canterbury, where he studied the isolation, structure elucidationand structure–activity relationships of biologically active marine natural products under the guidance of Professors Blunt and Munro. Heundertook postdoctoral research with Jon Clardy at Cornell and Chris Ireland at the University of Utah. 1992–93 was spent working inindustry as an isolation chemist with Xenova Plc, before returning to New Zealand to take a lectureship at the University of Auckland, wherehe is currently a Senior Lecturer.

Wan-Ping Hu received her BSc (Hons) and PhD degrees from the University of Canterbury, where she studied molecular beams withProfessor Peter Harland. She carried out postdoctoral research with Professor Stephen Price at University College London before returningto New Zealand where she is currently a research associate at the University of Canterbury working on breath testing projects using SIFT-MSfor clinical studies, in addition to maintenance of the MarinLit database.

Murray Munro, University of Canterbury, Christchurch New Zealand, has worked on natural products, mainly of New Zealand origin,right through his career. Following a sabbatical with Ken Rinehart at the University of Illinois in 1973, interest in marine natural productsdeveloped with a particular focus on bioactive compounds. In recent years his research interests have widened to include terrestrial and marinefungi and actinomycetes as well as marine invertebrates.

Peter Northcote received his BSc and PhD degrees from the University of British Columbia, Canada where he was a member of R. J. Andersen’smarine natural products research group. He carried out postdoctoral research with Professors Blunt and Munro at the University of Canterburybefore taking a position as a senior research scientist at Lederle Laboratories, American Cyanamid Co. He joined the faculty of the VictoriaUniversity of Wellington in 1994 where he is currently an Associate Professor in organic chemistry.

Michele Prinsep received her BSc (Hons) and PhD degrees from the University of Canterbury, where she studied the isolation and structuralelucidation of biologically active secondary metabolites from sponges and bryozoans under the supervision of Professors Blunt and Munro.She undertook postdoctoral research on cyanobacteria with Richard Moore at the University of Hawaii before returning to New Zealand totake up a lectureship at the University of Waikato, where she is currently a Senior Lecturer.

John W. Blunt Brent R. Copp Wan-Ping Hu Murray H. G. Munro Peter T. Northcote Michele R. Prinsep

phenylpyruvic acid oxime derivatives,53 triterpenoids,54 imidazole,oxazole and thiazole alkaloids,55 sponge alkaloids,56 iminiumalkaloids,57 diterpene-containing adenine alkaloids,58 unusualsterols from sponges,59 and briarane-related diterpenoids.60 Therehave been several reviews for different classes of compounds fromall natural sources, but where the contributions from marinesources are relatively minor, such reviews have not been noted here.Biosynthesis of marine natural products in microorganisms61 andmolluscs62 has been reviewed, and the use of microbial genetics toensure adequate supplies of marine compounds for developmentas drugs is surveyed.63 The role of symbiotic bacteria in metaboliteproduction and the analysis of the appropriate biosynthesis geneclusters has been reviewed.64,65 In the first of what is expectedto be a continuing series, a broad review on synthetic aspectsof marine natural products covering publications in 2003 hasappeared.66 More specific reviews that appeared in 2005 relating tothe synthesis of marine natural products will be referenced in thethird of that series. There has been a useful review of the methods

used for the isolation of marine natural products.67 The MarinLitdatabase68 continues to be updated and has again been used as thebasis for the preparation of this present review.

3 Marine microorganisms and phytoplankton

Microorganisms continue to be a productive and successful focusfor much marine natural products research. The actinomyceteSalinispora tropica, that had previously yielded salinosporamideA,69 also contained several related metabolites, salinosporamidesB 1 and C 270 and the unprecedented chlorinated macrolidessporolides A 3 and B 4.71 The structures of the sporolides areremarkable in that 23 of the 24 carbons of the skeletons areeither oxygenated or sp2 hybridised.71 Salinosporamides A and B 1inhibited human colon carcinoma HCT-116 cells with salinospo-ramide A being the most potent. Salinosporamide A also exhibitedextreme potency against several non-small cell lung, CNS andbreast cancer cell lines at the NCI.70 A new genus of actinomycete

32 | Nat. Prod. Rep., 2007, 24, 31–86 This journal is © The Royal Society of Chemistry 2007

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from deep water sediment (La Jolla, California) has yielded threechlorinated dihydroquinones 5–7. Two known analogues werealso isolated,72,73 with the absolute configuration of one of theseanalogues established recently74 and that of the other, 8, reportedin 2005. Compounds 5–8 displayed significant activity against

methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecium (VREF), and were cytotoxic tohuman colon carcinoma HCT-116 cells.75 Thallusin 9, isolatedfrom an epiphytic marine bacterium obtained from the surface ofthe green alga Monostroma oxyspermum (Japan),76 is a potent dif-ferentiation inducer of M. oxyspermum and induced germinationin other green macroalgae.77 A Thermoactinomyces species isolatedfrom mud (Mecherchar, Republic of Palau) was the source of thecyclic peptide mechercharmycin A 10 as well as the linear congenermechercharmycin B 11.78 Mechercharmycin A 10 was activeagainst A-549 lung and Jurkat human leukaemia cell lines, and wasalso reported as a cytotoxic compound in a patent also publishedin 2005.79 A yellow pigment 12, an analogue of the tambjaminealkaloids,80–82 has been isolated from the marine bacterium Pseu-doalteromonas tunicata83 (source not given).84 Cell-free culture

supernatant of the psychrophilic aerobic bacterium P. haloplanktisobtained from seawater (Dumont d’Urville station, Antarctica)contained a diketopiperazine 13. Two further diketopiperazines,known synthetic compounds,85,86 were reported for the first timefrom a natural source. Two linear peptides 14 and 15, stableto bacterial proteolytic enzymes, were also isolated. Peptide 15

displayed antioxidant activity in the 1,1-diphenyl-2-picrylhydrazyl(DPPH) free radical scavenging assay.87 Streptomyces nodosus, iso-lated from marine sediment (Scripps Canyon, California), yieldedthe antibiotic lajollamycin 16 active against both drug-sensitiveand drug-resistant Gram positive microorganisms and inhibitedgrowth of the murine melanoma cell line B16-F10.88 The chlorine-containing manumycin derivatives, chinikomycins A 17 and B 18were isolated from a Streptomyces species obtained from sediment(Jiaozhou Bay, China). Both 17 and 18 displayed antitumouractivity against a number of human cancer cell lines.89


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A Streptomyces species isolated from an unidentified sponge (JaejuIsland, Korea) was the source of the cyclic peptides dehydroxyno-cardamine 19 and desmethylenylnocardamine 20, weak inhibitorsof the recombinant enzyme sortase B.90 The pyrrolosesquiterpenes,glaciapyrroles A–C 21–23 were obtained from a Streptomycesspecies isolated from marine sediment (Alaska). GlaciapyrroleA 21 exhibited activity against HT-29 and B16-F10 cell lines.91

A resistomycin derivative, 1-hydroxy-1-norresistomycin 24, hasbeen independently isolated from different cultures of sediment-derived Streptomyces species, one from Laguna de Terminos, Gulfof Mexico92 and the other from Streptomyces chibaensis (Bay ofBengal, India).93 Compound 24 was active against E. coli, S. aureusand Streptomyces viridochromogenes92 and cytotoxic to HMO2(gastric adenocarcinoma) and HePG2 (hepatic carcinoma) celllines.93 Feigrisolide C 25, isolated originally from Streptomycesgriseus,94 was also isolated from a marine Streptomyces species.95

Structures proposed in each instance have been corrected bychemical reactions of natural feigrisolide C and confirmed bytotal synthesis.96 From a North Sea strain of Streptomyces,new methyl branched c- and d-lactones 26–31 were obtainedalong with two previously reported lactones97,98 isolated for thefirst time from a natural source.99 A Streptomyces species frommarine driftwood (West Coast, New Zealand) gave four new cyto-toxic anthracycline derivatives (7S*,9R*,10R*)-pyrromycin 32,(7R*,9R*,10R*)-pyrromycin 33, 1-hydroxyauramycin T 34 and

1-hydroxysulfurmycin T 35.100 An Actinomadura species from seasediment (Jiaozhou Bay, China) contained the staurosporine ana-logue ZHD-0501 36, an inhibitor of the proliferation of a varietyof murine and human cancer cell lines.101 The phenolic bisabolanesesquiterpenoids (+)-curcutetraol 37 and (−)-curcutriolamide 38were isolated from a co-culture of unidentified bacterium and fun-gus separated from marine sediment (Bahamas). Total synthesisof (±)-curcutetraol was achieved in seven steps from o-hydroxy-p-methylacetophenone.102 2,5-Dimethyl-3-(methylsulfanyl) pyrazine39, one of several 2,5-dialkylpyrazines identified in extracts ofthe Alphaproteobacteria Loktanella sp. (North Sea), has beenpreviously reported as a flavouring agent103 but this was thefirst isolation from a natural source.104 Himeic acids A–C 40–42 were isolated from an Aspergillus species separated from themussel Mytilus edulis (Toyama Bay, Sea of Japan). Himeic acidA 40 inhibited the ubiquitin-activating enzyme E1.105 Aspergillusvarians (Sakhalin Island, Russia) yielded the known compoundpatulin106 and 43, the 4-epi-isomer of a known compound.107 Thisis the first report of patulin from the marine environment. Bothcompounds were active against the sea urchin Strongylocentrusintermedius, cytotoxic to embryos and spermatoxic to sperm.108

The cerebroside asperiamide A 44 has been reported from a


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fungus described as Asperillus sp. (presumably Aspergillus sp.)isolated from seawater (Mei-Zhou Gulf, China).109 ScalusamidesA–C 45–47, pyrrolidine alkaloids, originated from Penicilliumcitrinum separated from the gastrointestine of the parrot fishScalus ovifrons (Hedo Cape, Okinawa). The absolute configurationof C-2 was established as (R), but all three compounds wereshown to be epimeric mixtures at C-7. Scalusamide A 45 showedweak antifungal activity against Cryptococcus neoformans and

antibacterial activity against Micrococcus luteus.110 The samefungus also yielded the tetracyclic alkaloid, perinadine A 48,weakly active against L1210 cells and was antibacterial againstM. luteus and B. subtilis.111 P. citrinum, separated from the redalga Actinotrichia fragilis (Hedo Cape, Okinawa), was the sourceof citrinadin B 49 and the previously isolated citrinadin A 50.112

Citrinadin B 49 was modestly cytotoxic against L1210 cells.113

Two sorbicillin-derived alkaloids, the sorbicillactones A 51 andB 52, were isolated from a saltwater culture of P. chrysogenum,separated from the interior of the sponge Ircinia fasciculata (Bightof Fetovaia, Sicily). The biosynthesis of sorbicillactone A 51 wasexamined with 13C-labelled precursors and found to arise viaan unprecedented pathway from acetate, S-adenosyl methionine,alanine and a biosynthetic equivalent of fumaric acid. Sorbicillac-tone A 51 was active against HIV, had neuroprotective potentialand was selectively active against L5178y cells.114 Penicilliumterrestre from marine sediment (Jiaozhou Bay, China) generated anumber of new metabolites; the polyketides penicillones A 53 andB 54,115 two benzoquinone derivatives 55 and 56, two bisorbicilli-noids 57 and 58116 and the bisorbicillinoids dihydrotrichodimerol59 and tetrahydrotrichodimerol 60.117 Trichodimerol118–120 was

isolated from a marine source for the first time.117 Againstthe P388 and A-549 cell lines, dihydrotrichodimerol 59 andtetrahydrotrichodimerol 60 were cytotoxic,117 bisorbicillinoids 57and 58 were antiproliferative,116 penicillone A 53 displayed weak


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cytotoxicity while penicillone B 54 was weakly cytotoxic to A-549cells only.115 The diastereoisomeric quinolinones 61 and 62 wereisolated from P. janczewskii derived from surface water (GermanBight, Helgoland Island). Both compounds were cytotoxic to arange of human tumour cell lines, with 62 strongly cytotoxic toSKOV-3 cells (human ovarian carcinoma).121 P. auratiogriseum,derived from the sponge Mycale plumose (Qingdao, China),was the source organism for the benzoate 63, a cytotoxicagent against tsFT210 cells.122 A new xanthocillin 64 and threeknown xanthocillins,123 all thrombopoietin mimics, were isolatedfrom a marine Basipetospora species (source not given).124 On

fermentation, the fungus Clonostachys rogersoniana from thesponge Halichondria japonica (Numazu, Japan), gave the cyclicnonapeptides, clonostachysins A 65 and B 66, motility inhibitorsof the dinoflagellate Prorocentrum micans.125 The mitosporic

fungus Geniculosporum sp. associated with a red algal Polysiphoniaspecies (Ahrenshoop, Baltic Sea) was cultured to yield eleven newbotryane compounds 67–77, some of which displayed modestgrowth inhibition of alga, bacteria and fungi.126 Myrothenones A78 and B 79, new amino-5-ethenylcyclopentenones, were obtainedfrom the fungus Myrothecium sp. isolated from the surface of thegreen alga Enteromorpha compressa (Busan, Korea). MyrothenoneA 78 inhibited tyrosinase.127 The polyketide glycoside, cladionolA 80, isolated from the fungus Gliocladium sp., separated fromthe sea grass Syringodium isoetifolium (Maeda Cape, Okinawa),was moderately cytotoxic to L1210 and KB cells.128 Emericella

variecolor, isolated from marine sediment (Gokasyo Gulf, Japan),yielded the polyketide shimalactone A 81, a compound whichinduced neuritogenesis in neuroblastoma neuro-2a cells at lowconcentration, but was cytotoxic at higher concentration.129

Peribysins E–G 82–84, from Periconia byssoides, separated fromthe sea hare Aplysia kurodai (Osaka, Bay of Japan), were inhibitorsof adhesion of human leukaemia HL-60 cells to human umbilicalvein endothelial cells (HUVEC).130 The absolute configurationof the known peribysin A 85131 was established. Four novelditerpenoids, libertellenones A–D 86–89, were isolated from a co-culture of a marine a-proteobacterium and an established cultureof the fungus Libertella sp. separated from an ascidian collectedin the Bahamas. The metabolites were not found in pure culturesand are proposed to be of fungal origin. The bacterium used wasisolated originally as a contaminant of a fungal culture and was thesame strain which induced pestalone production in another marinefungus.132 The libertellenones exhibited cytotoxicity against HCT-116 cells with 89 being the most potent.133 A Cladosporium speciesassociated with the Red Sea sponge Niphates rowi (Gulf of Aqaba)was the source of a hexaketide pandangolide 1a 90, and the knowndiastereomer pandangalide 1 91,134 along with iso-cladospolideB 92.134 Absolute configurations of 90–92 were determined byRiguera’s method135 and circular dichroism, and confirmed theabsolute configuration of 92 suggested previously.136,137 Phomopsisasparagi, from the sponge Rhadphidophlus juniperina (U.S. VirginIslands), produced chaetoglobosin-510, 93, chaetoglobosin-54094 and chaetoglobosin-542 95 when challenged with the knownF-actin inhibitor138 jasplakinolide139/jaspamide140 obtained fromJaspis sponges. Chaetoglobosin-542 95 had antimicrofilamentactivity and was cytotoxic towards L1210 and C38 cell lines.141

Xyloketal G 96 was isolated from the marine-derived mangrovefungus Xylaria sp. separated from seeds of an angiosperm (MaiPo, Hong Kong),142 while a Xylaria species isolated from seedsof the mangrove Avicenna marina (Hong Kong) produced thedimeric xyloketal F 97. Xyloketal F was a potent L-calciumchannel blocker while xyloketals A and B143 were also blockers,but less potent.144 Diaporthelactone 98, and the known


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compounds 7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one145

and mycoepoxydiene,146 were isolated from a Diaporthe species, amarine fungus growing in submerged rotten leaves of the mangrove

Kandelia candel (Fugong, China), and were cytotoxic against theKB and Raji cell lines.147 Lyngbya majuscula (Alotau Bay, PapuaNew Guinea) yielded five lyngbyabellin analogues, lyngbyabellinsE–I 99–103, which were cytotoxic to NCI-H460 and neuro-2a

cell lines.148 Lyngbya semiplena (Wewak Bay, Papua New Guinea)was the source of four new depsipeptides, wewakpeptins A–D


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104–107, cytotoxic to brine shrimp and to the NCI-H460 andneuro-2a cell lines.149 Ankaraholides A 108 and B 109, glycosylatedswinholides, were isolated from the cyanobacterium Geitlerinemasp. (Nosy Mitso-ankaraha Island, Madagascar) while swinholideA (previously isolated from the sponge Theonella swinhoei150) wasisolated from a cyanobacterium collected in the Fiji Islands. Thesetwo findings represent the first direct isolations of swinholides fromcyanobacteria, establishing unequivocally that cyanobacteria canproduce these metabolites (previously isolated from sponges butlocalised to heterotrophic bacteria). Ankaraholide A possessedcomparable activity to swinholide A, inhibiting proliferation inNCI-H460, neuro-2a and MDA-MB-435 cell lines and inhibitingcytokinesis.151 From the filamentous mat-forming cyanobacteriumPhormidium sp. (Bise, Okinawa) the 2-alkylpyridine alkaloidsphormidinines A 110 and B 111 were isolated.152 Majusculoicacid 112, a brominated cyclopropyl fatty acid with modestantifungal activity, was isolated from a cyanobacterial matassemblage (Sweetings Cay, Bahamas).153 When the coastalcyanobacterium Synechococcus sp. (Woods Hole OceanographicInstitution) was cultured under iron-limiting growth conditions,the synechobactins A–C 113–115 were produced.154 The newamphidinol AM7 116, from the dinoflagellate Amphidinium klebsiiobtained from a surface wash of a seaweed (Aburatsubo Bay,Japan), is sulfated, has a truncated polyhydroxyl chain, and hasthe shortest carbon backbone of any of the known amphidinols.AM7 116 was active towards Aspergillus niger and also possessedhaemolytic activity.155 Five amphidinol analogues, amphidinols 9–13 117–121 were isolated from Amphidinium carterae (Kauauroa,New Zealand). All were haemolytic against mouse erythrocytes,cytotoxic against P388 cells and antifungal towards Aspergillusniger to varying degrees. Those containing a sulfate ester atC-1, namely amphidinols 11–13 119–121, had much reducedhaemolytic and antifungal activities.156 Luteophanol D 122, aweakly antibacterial polyhydroxy compound, was obtained froman Amphidinium species, isolated from the marine acoel flatworm

Pseudaphanostoma luteocoloris (Okinawa).157 The 26-memberedmacrolides, amphidinolides B4 123 and B5 124, obtained froman Amphidinium species, isolated from a marine acoel flatwormAmphiscolops sp. (Ma’eda Cape, Okinawa), were potently cy-totoxic against L1210 and KB cell lines.158 From A. carterae(Hainan Island, China), an unsaturated glycoglycerolipid 125 wasisolated,159 while a glycosylated yessotoxin analogue, glycoyesso-toxin A 126 originated from Protoceratium reticulatum from aculture collection at the Centro Oceanografico de Vigo.160 Twofurther yessotoxin analogues, 127 and 128, trihydroxylated amidesof 41a-homoyessotoxin and 9-methyl-41a-homoyessotoxin respec-tively, have been isolated from P. reticulatum, isolate CAWD40161

(Cawthron Institute Culture Collection).162 20-Methyl spirolide G129 was isolated concurrently from the microalga Alexandriumostenfeldii and from the mussel Mytilus edulis (Skjer, Norway).163

The polyether gymnocin-B 130, isolated from the red tide dinoflag-ellate Karenia mikimotoi (Kushimoto Bay, Japan),164 possessesthe greatest number (15) of contiguous ether rings known todate. The absolute configuration was not initially determined,as preparation of MTPA esters was unsuccessful, probably dueto steric hindrance,164 but the full absolute configuration wassubsequently determined using a variety of approaches includingconformational analysis of derivatives and chirality determinationbased on porphyrin–porphyrin circular dichroism exciton-coupledinteractions over distance.165 Gymnocin-B was cytotoxic to P388cells, but only weakly ichthyotoxic.164 K. brevis (Wilson’s 58clone) contained a polyether compound, brevenal 131, whichcompetitively displaces brevetoxin from the binding site in ratbrain synaptosomes and can antagonise toxic effects of brevetoxinsin fish, but is itself non-toxic to fish.166 Artificial cultures ofProrocentrum lima and P. belizeanum from strains obtained fromthe IEO (Vigo) produced new ester derivatives of okadaic acid: P.lima was the source of 132–134 and P. belizeanum 135.167 Thepolyketide prorocentrin 136, an inhibitor of DLD-1 and RP-MI7951 cell lines, was isolated from P. lima (northern coast of


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Taiwan).168 Neosymbioimine 137, in addition to the previouslyreported symbioimine 138,169 originated from a dinoflagellateSymbiodinium species separated from the acoel flatworm Am-phiscolops sp. (Sesoko Island, Okinawa). Symbioimine 138 hadanti-resorptive activity,57 and inhibited cyclooxygenase-2 (COX-2) activity.170 An inseparable mixture of polyhydroxylated 61–66-membered macrolides, termed the zooxanthellamide Cs (ZAD-C1 to ZAD-C5) 139–143 was obtained from a Symbiodiniumspecies (a sand beach in Hawaii).171 Detailed NMR spectroscopicanalyses determined that the mixture consisted of five macrolac-tonised analogues of zooxanthellamide A, previously isolated fromthe same microalgae.172 The mixture displayed vasoconstrictiveactivity on rat blood vessels.173 From the diatom Thalassiosirarotula (source not given) a series of C16 oxylipins 144–151 wereisolated. These are formally derived by the unprecedented enzymicoxidation of C16 fatty acids. In support of this, a network ofoxygenase-mediated transformations that require C16 fatty acids

as substrates was demonstrated.174 A dihydroxysterol 152 wasobtained from a phytoplankton Diacronema species (Sampayo,Portugal).175 Aspernigrins A and B were originally isolated froma sponge-derived culture of Aspergillus niger.176 The structureof aspernigrin B 153 has now been revised177 based on X-rayanalysis of aspernigrin A reisolated from another source.178 Thefirst total synthesis of dragonamide 154, a lipopeptide fromLyngbya majuscula,179 was reported, and led to a reassignmentof the configuration at the stereogenic centre in the alkyne-bearing fragment.180 Total synthesis of a thiomarinol derivativeisolated from Alteromonas rava originally separated from Dar-winella rosacea181 has been reported.182 A short stereocontrolledsequence starting from p-methoxyphenol was employed in thetotal synthesis of yanuthones A–C and 22-deacylyanuthone A,183

originally isolated from Aspergillus niger separated from anAplidium sp. ascidian.184 An asymmetric synthesis of abyssomicinC, a polyketide from the actinomycete Verrucosispora sp.,185 has


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been reported,186 as has the total synthesis of the heptapeptidecyclomarin C187 from a Streptomyces species.188 Syntheses ofsemiplenamide C,189 a fatty acid amide isolated from Lyngbyasemiplena190 and pitipeptolide A,191 a cyclodepsipeptide originallyisolated from L. majuscula have appeared.192 Tryptoquivaline J,193

from Aspergillus fumigatus, has been isolated from a marinestrain of the fungus for the first time.194 The known microbialpigment metacycloprodigiosin195 was isolated from the actino-mycete Saccharopolyspora sp. associated with the sponge Mycaleplumose (Qingdao coast, China) and displayed significant cyto-toxicity against five human cancer cell lines.196 Bacillomycin D,first isolated from a terrestrial strain of Bacillus subtilis,197 hasbeen isolated from a strain separated from the sponge Stellettavalidissima (Kuril Islands, Russia) and showed pH-dependentcytotoxic activity against Ehrlich carcinoma cells198 and wasalso cytotoxic towards murine erythrocytes.199 A marine-derivedAspergillus species yielded the polyketides (+)-epoxydon,200

(+)-epoxydon monoacetate,201 gentisyl alcohol,202 3-chlorogentisylalcohol202 and methylhydroquinone203 as potent antibacterialagents against MRSA and multi-drug-resistant Staphylococcusaureus (MDRSA). The first four metabolites also exhibited signif-icant radical scavenging activity against DPPH.204 Gymnodimine,originally isolated from a Gymnodinium species,205 sensitised the

neuro-2a cell line to the apoptotic effects of another algal toxin,okadaic acid, raising the possibility that algal blooms involvingthe production of both of these classes of metabolites maygenerate greater cytotoxicity and pose more severe public healthproblems.206 Biosynthesis of pentabromopseudilin,207,208 originallyisolated from Pseudomonas bromoutilis but also produced byother marine bacteria such as Alteromonas, has been studied.Feeding studies with A. luteoviolaceus demonstrated that thepyrrole ring is derived from proline.209 Biosynthetic studies onSymbiodinium sp., the dinoflagellate symbiont of the Caribbeangorgonian Pseudopterogorgia bipinnata, using 3H-labelled ger-anylgeranyl diphosphate indicated that this alga was capable ofbiosynthesising diterpenes previously ascribed210 solely to the hostcoral.211 A fluorescent system has been described that profilesthe connection between biosynthetic production and autotoxicityusing complementary okadaic acid producing and nonproducingstrains of the dinoflagellate genus Prorocentrum.212

4 Green algae

Relatively few new secondary metabolites have been reportedfrom green algae but the number still represents an increasefrom the 2004 review.213 Caulerpa brownii (Tasmania, Australia)occurs in branched and unbranched forms, each of which hasyielded a number of novel diterpenoids. Unbranched materialwas the source of 155–159 and another diterpenoid reportedpreviously as a synthetic compound.214 The branched form yieldedthe terpenoid ester 160.215 Avrainvillea nigricans (Portsmouth,


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Dominica), yielded the glycoglycerolipid avrainvilloside 161 whichcontains the very rare 6-deoxy-6-aminoglucose moiety.216 Ahalogenated biindole 162 and an apo-carotenone 163 were iso-lated from Chaetomorpha basiretorsa (Naozhou Island, China),217

while clerosterol palmityl ester 164 was obtained from Codiumfragile (Qingdao coast, China).218 A solid-phase total synthesisof kahalalide A 165, isolated from a Bryopsis species and itspredator Elysia rufrescens,219,220 established the stereochemistry ofthe methylbutyrate sidechain as (S).221 The mild antimycobacterialactivity of 165 and related analogues was also reported. Thelong-chain aldehyde (8Z,11Z,14Z)-8,11,14-heptadecatrienal, acomponent of the essential oil of Ulva pertusa,222 has beensynthesised.223

5 Brown algae

Terpenes and polyphenols continue to be the predominant classesof compounds reported from brown algae. The sargachromanolsA–P 166–181, meroterpenoids of the chromene class, were iso-lated from Sargassum siliquastrum (Jaeju Island, Korea). Thecompounds all exhibited significant activity in the DPPH assaywhile compounds 172 and 180 were also inhibitors of butyl-choline esterase.224 The known plastoquinones 182 and 183225

were isolated from S. micracanthum. Compound 182 displayedsignificant antioxidant activity while in contrast, 183 was potentlyactive against human cytomegalovirus (HCMV) in vitro.226 S.micracanthum (Toyama Bay, Japan) was the source of the stronglyantioxidant plastoquinones 184–187, while compounds 185–187 also showed antiproliferative effects against 26-L5 cells.227

Taonia atomaria (Serifos Island, Central Aegean Sea), was thesource of the meroditerpenes atomarianones A 188 and B 189,cytotoxic agents against the NSCLC-N6 and A-549 cell lines.228


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(Z)-Sargaquinone 190, the more saturated analogue 191, andthe known sargaquinone229 were also isolated from T. atomaria,and were anti-inflammatory agents by inhibition of leukotrienebiosynthesis.230 Five meroditerpenoids, 2b,3a-epitaondiol 192,flabellinol 193, flabellinone 194, stypotriolaldehyde 195 stypo-hydroperoxide 196 and the previously reported stypoldione231

were isolated from Stypopodium flabelliforme (Long Island, PapuaNew Guinea) and were variously active in a range of bioassaysincluding cytotoxicity, sodium channels as well as modulationof intracellular calcium concentrations.232 Dictyopteris divaricata(Qingdao, China) was the source of the bisnorsesquiterpenes197–199 and the norsesquiterpene 200.233 The linear diterpenoids

201–205 were isolated from Bifurcaria bifurcata (Southern Brit-tany, France),234 and the absolute configuration of C-13 deter-mined for 204 and 205, requiring revision of the stereochem-istry of eleganediol 206.235 Sargochromenol, originally isolated


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from Sargassum serratifolium,236 was shown to promote neuriteoutgrowth and survival in PC12D cells via distinct signallingpathways.237 Phloroglucinol238 and the phloroglucinol derivativeseckstolonol,239 eckol,240 phlorofucofuroeckol A241 and dieckol242

were isolated from the brown alga Ecklonia stolonifera as hepato-protective agents.243 (±)-Yahazunol244 and cyclozonarone245 werecytostatic and cytotoxic agents against several human tumour celllines, while zonarol, zonarone and isozonarol246 also displayedcytotoxicity against various human tumour cell lines.247

6 Red algae

Reports of red algal metabolites have increased from the pre-vious review but the field is still dominated by terpene andhalogenated polyphenol chemistry. Five sulfur-containing poly-bromoindoles 207–211 were isolated from Laurencia brongniartii(Ken-Ting National Park, South Taiwan), of which 210 and211 were active against P388 cells and 210 against HT-29cells.248 From L. brongniartii (Kikai Island, Japan), five sulfur-containing polybrominated bisindoles 212–216 were isolated.249 A

number of sesquiterpenes were isolated from L. tristicha (NaozhouIsland, China). These included seven new compounds 217–223250 along with 10-hydroxyepiaplysin 224, 10-hydroxyaplysin225 and 10-hydroxybromoepiaplysin 226, all previously reportedas synthetic intermediates251,252 but now isolated as naturalproducts.253 Compound 222 has a novel rearranged skeleton whilecompound 220 was previously reported as a synthetic racemate.254

Laurebiphenyl, a dimeric sesquiterpene reported previously fromL. nidifica,255 was also isolated and exhibited moderate cytotoxicityagainst several human cancer cell lines.250 The cuparene sesquiter-penes 227–229, isolated from L. microcladia (Chios Island, NorthAegean Sea), were cytotoxic against the NSCLC-N6 and A-549 cancer cell lines.256 Laureperoxide 230, 10-bromoisoaplysin231, isodebromolaurinterol 232 and 10-hydroxyisolaurene 233 arecuparene-derived sesquiterpenes isolated from L. okamurai (NanjiIsland, China).257 Six diterpene compounds representing a new

skeletal type, the dactylomelanes, were isolated from a Laurenciaspecies (Paraıso Floral, Canary Islands). The compounds werethe relatively unstable E-dactylohydroperoxide A 234 and Z-dactylohydroperoxide A 235, dactylohydroperoxide B 236, thealcohol 237, dactylohydroperoxide C 238 and puctatene 239.258

L. luzonensis (Kudaka Island, Okinawa) was the source of thediterpene luzodiol 240 and five snyderane sesquiterpenes 241–245.259 A brominated C15 polyketide allene chinzallene 246, and


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a brominated diterpene 247 originated from another Laurenciaspecies (Hatomisaki, Chinzei, Japan). The diterpene was alsoisolated from a collection made at Hachijo-jina Island, Tokyo.260

From Carpopeltis crispata (Johgashima Island, Japan) the ochto-dene derivatives 248–252 were isolated. All are regioisomers

or stereoisomers of known compounds261,262 from an Ochtodesspecies.263 Three new bromophenols 253–255 and two bromophe-nols known previously only as synthetic compounds,264–267 camefrom Symphyocladia latiuscula (Dalian, China). All of the bro-mophenols were significant aldose reductase inhibitors.268 Threebromophenols coupled to pyroglutamic acid derivatives 256–258and a bromophenol coupled with deoxyguanosine 259 were iso-lated from Rhodomela confervoides (Qingdao, China). Compound257 is a possible artifact since in aqueous methanol 256 con-verts to 257 on standing.269 The polyhalogenated monoterpenes,plocoralides A–C 260–262 have been isolated from the red algaPlocamium corallorhiza (Kalk Bay, South Africa). Plocaralides B261 and C 262, in addition to three other compounds previouslyisolated from a Plocamium species270,271 and Aplysia californica,272

displayed moderate activity against the human oesophageal cancercell line WHCO1.273 From a Galaura species (Xisha Island,

South China Sea), the cycloartane triterpenes galaxaurols A–E 263–267 were isolated,274 while from Ptilonia magellanica(Straits of Magellan, Chile), three pyranosyl-like polyhalogenatedmetabolites, the pyranosylmagellanicus A–C 268–270, and theputative biogenetic precursor 271 were discovered.275 Corallina-furan 272 and corallinaether 273, a brominated dibenzofuran anddiphenyl ether respectively, were isolated from crustose corallinered algae (Yomitan, Okinawa). Both were toxic to larvae ofthe scleractinian coral Pseudosiderastrea tayamai.276 Callophycusserratus collected from several Fijian sites was the source ofthree antibacterial and antifungal diterpene-benzoate compounds,bromophycolides A 274 and B 275, and a non-halogenatedcompound 276. Bromophycolide A 274 was also anti-HIV activeand cytotoxic to several human tumour cell lines by specificinduction of apoptosis.277 Synthesis of agardhilactone 277, aneicosanoid isolated from the red alga Agardhiella subulata,278 hasbeen reported and resulted in a revised structure.279 The iso-meric conjugated trienes (5E,7E,9E,14Z,17Z)-eicosapentaenoicacid and (5Z,7E,9E,14Z,17Z)-eicosapentaneoic acid, originallyisolated from Ptilota filicina,280 have been synthesised from methyl5-oxopentanoate and found to be cytotoxic to DLD-1 cells byinduction of apoptosis.281 A stereoselective and concise totalsynthesis of (−)-isoprelaurefucin from Laurencia nipponica282

has been completed283 and the total synthesis of (−)-isodomoicacid C, originally isolated from Chondria armata,284 has been


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reported.285 Free-radical chemistry was utilised in the totalsyntheses of several terpenoids with 7-membered heterocyclesincluding laukarlaol286 from Laurencia karlae.287 2,3,6-Tribromo-4,5-dihydroxybenzyl methyl ether,288 isolated from Symphyocladialatiuscula (Pusan, Korea), was active against wild type HSV-1, aswell as APr HSV-1 and TK-HSV-1 and significantly delayed theappearance of lesions in infected mice without toxicity.289

7 Sponges

Sponges continue to attract considerable attention from bothsynthetic and natural product chemists. New ceramides andsphingolipids continue to be isolated from sponges, and theuse of tandem MS to detect and determine the structure ofthese ceramides has been described.290 Ircinia fasciculata (China)contained ircisulfamide 278 and ircicerebroside 279.291 Hali-clonacerebroside 280 was isolated from a Haliclona species andreported in 2004.292 Vesparioside 281 was obtained from Sphe-ciospongia vesparia (Bahamas),293 while an Amphimedon species(Japan) yielded the amphimelibiosides A–F 282–287.294 The

immunostimulatory glycosphingolipid damicoside 288 was iso-lated from Axinella damicornis (SW coast of Italy).295 Rhizochalinaincrustata (Seychelles Islands) contained rhizochalin A 289.296

The glycolipid discoside 290, isolated as the peracetate derivative291, was obtained from Discodermia dissoluta (Bahamas).297

A hybrid glycolipid–tetrahydroisoquinoline, oceanalin A 292,obtained from an Australian Oceanapia species, was anti-fungal against Candida glabrata.298 A series of iminosugar-like


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N-cyclised sphingolipids, batzellasides A–C 293–295, obtainedfrom a Batzella species (Madagascar), were inhibitors of Rafkinase.299 A remarkably complex polysulfated glycolipid, ax-inelloside A 296 with telomerase inhibitory activity, was iso-lated from Axinella infundibula (Japan).300 Two monoglycerides,homaxinolins A 297 and B 298, a phosphatidyl choline,homaxicholine A 299 and a cytotoxic fatty acid 300 were

obtained from a Korean Homaxinella species.301 Untenone A302

and plakevulin A,303 originally isolated from Plakortis species,have been synthesised.304 Syntheses of hachijodine A and B,305

originally isolated from Xestospongia and Amphimedon speciesrespectively,306 and three irciniasulfonic acids,307 originally isolatedfrom an Ircinia species,308 have been reported. Two groups haveindependently reported the synthesis309,310 of pachastrissamine(jaspine B), originally isolated from a Pachastrissa species311

and subsequently from a Jaspis species.312 Caminoside A, fromCaminus sphaeroconia,313 has been synthesised.314 A series ofacetylenic fatty acid derivatives, strongylodiols D–J 301–307,were obtained as non-racemic mixtures of enantiomers froman Okinawan Petrosia (Strongylophora).315 Diplynes C and E,isolated from a Diplastrella species316 have been synthesised


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asymmetrically allowing tentative assignment of the relativestereochemistries of the series.317 The syntheses of (−)-siphonodioland (−)-tetrahydrosiphonodiol, isolated from Siphonochalinatruncata,318,319 have been reported.320 Methyl peroxyacarnoates Aand D, isolated from Acarnus cf. bergquistae321 and bicladoty-lota322 respectively, have been synthesised.323 Four branched chainpolyketide-derived metabolites, lehualides A–D 308–311, wereisolated from a Plakortis species (Hawaii). Compounds 309and 311 were cytotoxic to cancer cell lines.324 Plakortis simplex(Norway), collected from 280 m by manned submersible, yieldedtwo cycloperoxy-methyl esters 312 and 313 of which 313 was

moderately cytotoxic.325 Two furanylidenic methyl esters, 314 and315, from P. angulospiculatus (Brazil), were cytotoxic to brineshrimp.326 Spongosoritin A 316 was isolated from a Spongosoritesspecies (Fiji).327 The reported structure of 316 is identical to thatof 315 without relative stereochemistry specified. Although theoptical rotations were similar, the reported NMR data show somesignificant differences; these compounds may be diastereomeric.Plakortis zyggompha (Martinique, Caribbean Sea) containeddinor-spiculoic acid 317, and the weakly cytotoxic iso-318 andnor-spiculoic acids A 319.328 From what appears to be the samecollection of P. zyggompha, a series of cytotoxic cycloperoxides320–326 were also isolated. Plakortide Q 320 was isolated asan acid while 321–326 were isolated as methyl esters preparedwith TMSCHN2.329 Interestingly, a sample of the crude extractof the sponge left standing in methanol for one year yielded themethyl esters directly; this finding may go some way to accountingfor the prevalence of methyl esters as reported metabolitesof Plakortis species. P. simplex (Bahamas) yielded two enone-containing branched chain metabolites, 327 and 328, and two anti-malarial cycloperoxides, 329 and 330.330 Unaware of the previousreport, 329 was named plakortide Q, while 330 has previouslybeen isolated from P. halichondroides without complete rela-tive stereochemistry.331 Methyl (2Z,6R,8R,9E)-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate, originally isolated from P. halichon-drioides,123 has been synthesised as a racemic mixture.332 Threenew aurantosides G–I 331–333 have been isolated from Theonellaswinhoei (Papua New Guinea).333 Ircinia felix (Brazil) was thesource of 4H-pyran-20-ol acetate 334.334 An inhibitor of the


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protein-tyrosine phosphatase CDC25A, 335, was isolated froma Xestospongia species (Sulawesi, Indonesia), along with anotherpolycyclic quinone 336.335 A Hyrtios species (Hawaii) yielded atrichloro metabolite poipuol 337.336 Psymberin 338 (irciniastatinA), independently isolated from a Psammocinia species337 andIrcinia ramosa,338 has been synthesised establishing the identityand absolute stereochemistry, the relative stereochemistry at C-3 and confirming the originally proposed stereochemistry forpsymberin.339 The relative and absolute stereochemistry of theC-1 to C-6 side chain was independently established by synthesis

of a degradation product.340 Cylindramide, isolated from Hali-chondria cylindrata,341 has been synthesised enantiomerically.342

13-Deoxytedanolide, isolated from Mycale adhaerans,343 bindsto the 60S large ribosome subunit, thereby inhibiting proteinsynthesis.344 Two independent groups have shown that pateamine,originally isolated from Mycale hentscheli,345 inhibits eukaryoticprotein synthesis initiation.346,347 Potently bioactive peptides ofnon-ribosomal origin are a feature of sponge chemistry andcontinue to attract the attention of natural product and syntheticresearchers alike. The moderately cytotoxic koshikamide A2 339was isolated from the same Japanese Theonella species that yieldedkoshikamide A1.348 A Haliclona species contained kendarimide A340. By synthesising a series of diastereoisomeric tetrapeptidescorresponding to the region in 340 containing the 8-membereddisulfide ring system it was concluded that the two contributingcysteine residues had an L configuration.349 The picomolar activecytotoxins polytheonamides A 341 and B 342, originally isolatedfrom Theonella swinhoei,350,351 have been re-isolated from thesame sponge, and from spectroscopic and chemical analyses thestructures have been revised to those of the sulfoxide epimers.352

Halipeptin D 343 has been isolated from Leiosella cf. arenifibrosa(Philippines),353 while halipeptins A354 344 and D 343 have beensynthesised, confirming the presence of the thiazoline ring andestablishing the relative stereochemistry of the side chain and ab-solute configuration. Intriguingly, the reported potent biologicalactivity of halipeptins A and D was not confirmed by the synthesis,as the synthetic samples both showed weak cytotoxicity only.355

A Phakellia species (Chuuk, Micronesia) yielded the cytotoxicpeptide phakellistatin 14 345.356 Dominicin 346 was isolated fromEurypon laughlini (Dominica).357 Syntheses of phakellistatin 7 andthe proline-rich phakellistatins 8 and 9, all isolated from Phakelliacostata,358 have been reported.359 The synthetic phakellistatin 7was spectroscopically identical to the natural compound whiledata for the phakellistatins 8 and 9 differed, again highlighting thedifficulties associated with proline cis–trans isomerism. Also, allcompounds were only weakly bioactive, in contrast to the potentactivities originally reported.358 The determination of the stere-ochemistry of b-methoxytyrosine (b-MeOTyr) found in severalsponge-derived cyclic peptides has received considerable attention.Callipeltin A 347, originally isolated from a Callipelta species(New Caledonia), was reported without stereochemistry at the b-MeOTyr residue due to degradation during acid hydrolysis.360 Allfour possible stereoisomers of b-MeOTyr were synthesised andsubjected to oxidative ozonolysis to yield the corresponding b-methoxyaspartates. Callipeltin A was then subjected to ozonolysisand acid hydrolysis. Marfey’s analysis of the synthetic andcallipeltin derived residues established the b-MeOTyr residueas (2R,3R).361 The same general technique of hydrolysis andoxidation was used to determine a (2R,3R) configuration forthe b-MeOTyr of papuamide B 348,362 isolated from a Theonellaspecies.363 In a similar study, the stereochemistry of b-MeOTyrin papuamide A 349, originally isolated from two species ofTheonella,363 was determined. In this case all four stereoisomers ofb-MeOTyr were synthesised and incorporated into a tripeptidecorresponding to the b-MeOTyr tripeptide sequence originallyrecovered from partial hydrolysis of 349. Comparison of theNMR spectra led to the assignment of this residue as (2R,3R)as above.364 Rather surprisingly, the b-MeOTyr of neamphamideA 350, isolated from Neamphius huxleyi,365 was (2S,3R) in


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contrast to the above examples. In the same study, theremaining stereochemical uncertainties were determined: 4-amino-7-guanidino-2,3-dihydroxyheptanoic acid was assignedas (2R,3R,4S), and 3-hydroxy-2,4,6-trimethylheptanoic acidas (2R,3R,4R), establishing the full stereochemistry of themolecule.362 Two epi-sulfoxides, neopetrosiamides A 351 and B352, found to inhibit amoeboid invasion by human tumour cells,were isolated from a Neopetrosia species (Papua New Guinea).366

Macrolides and related uncyclised PKS-derived molecules featurestrongly in sponge metabolite chemistry. A series of potentlycytotoxic 1,3-polyols, the mycapolyols A–F 353–358, have beenobtained from Mycale izuensis (South Japan).367 Another JapaneseMycale species yielded secomycalolide A 359, an inhibitor of

proteasome activity.368 Spongistatin 1, isolated from a Spongiaspecies,369 was found to be an effective antifungal agent in vitro aswell as in vivo in mice against Candida albicans and Cryptococcusneotormans.370 The structure of swinholide A, isolated fromTheonella swinhoei,150 bound to actin has been determined, reveal-ing a similar binding site to the trioxazole sponge metabolites.371 Asynthesis of haterumalide NA, isolated from an Ircinia species,372

has been reported.373 The original structure of clavosolide A, fromMyriastra clavosa (Philippines),374 has been synthesised and onthe basis of the very similar, but not identical spectroscopic data,it was proposed that the natural compound was a diastereomerof the synthetic compound with inversion of the stereogeniccentres at the cyclopropyl rings.375 A pentabrominated diphenyl


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ether 360 has been isolated from Dysidea herbacea (GreatBarrier Reef, Australia),376 and two other diphenyl ethers, 3,5-dibromo-2-(2′,4′-dibromophenoxy)phenol and 4,6-dibromo-2-(2′,4′-dibromophenoxy)phenol, previously isolated from Dysideaherbacea,377 are inhibitors of the Tie2 kinase involved inangiogenesis.378 A general synthetic strategy for the bastadins,macrocyclic brominated phenyl ethers typical of Ianthellabasta,379–382 has been reported with syntheses of bastadins 5, 10,12, 16, 20 and 21 achieved.383 The importance of marine spongesas a source of novel alkaloids, in particular those with antitu-mour activity, has been recognized and reviewed.56 A series ofpyrrolidinones, dysidamides D–G 361–364, epi-G 365 and H 366,and the related seco compounds 367 and 368 were isolated fromLamellodysidea herbacea (formerly Dysidea) (Red Sea).384 Therelative stereochemistry of dysithiazolamide 369, from a Dysideaspecies (Sulawesi, Indonesia), was determined by an extension ofthe J-based Murata method to include nitrogen substituents.385

The nematocidal agents, echinobetaines A 370 and B 371, wereisolated from a species of Echinodictyum (S. Australia), and syn-theses reported.386,387 In the same study, norzooanemonin 372 wasreported from a variety of Australian sponges.387 An adrenalineanalogue, S1319 originally isolated from a Dysidea species,388


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has been synthesised.389 An alkyl pyridinium dimer 373 withagonist activity against chemokine receptor CXCR3 was iso-lated from an unidentified sponge (Bahamas).390 The battle overdetermining the true structure of pyrinodemin A rages on.12,13

Alkene positional isomers have been synthesised and the NMRand MS data compared with data from the natural product,originally isolated from an Amphimedon species.391 The closestmatch was found to be 374, but the authors concede that untilmore natural material is available for a complete spectral analysis,some doubt remains.392 In a separate study the same alkene isomerswere synthesised asymmetrically and compared by chiral HPLCanalysis to a sample of the natural substance and were foundto co-elute with a racemic mixture of 375.393 Makaluvic acid C376 and the cytotoxic N-1-b-D-ribofuranosylmakaluvic acid C 377were both isolated from Strongylodesma aliwaliensis (E. coast ofSouth Africa).394 A Latrunculia species (New Zealand) containedthe cytotoxic dimeric discorhabdin W 378.395 Zyzzya fuliginosa

(E. Australia) yielded the moderately cytotoxic zyzzyanones B–D379–381.396 A series of bromoindole metabolites 382–385 wereisolated from a Thorectandra species (Papua New Guinea).397

In the same study, two further related metabolites 386 and387 were described from a Smenospongia species (Papua NewGuinea). A range of metabolites from both sponges displayed

activity against Staphylococcus epidermis. A Psammoclemmaspecies (New Caledonia) yielded the cytotoxic echinosulfonicacid D 388.398 Dendridine A 389, a bis-indole alkaloid withantimicrobial activity, was obtained from a Dictyodendrillaspecies (Okinawa).399 (6R)-6′′-Debromohamacanthin A 390, (6R)-6′-debromohamacanthin A 391, (+)-(S)-6′′-debromohamacanthinB 392 and dibromodeoxytopsentin 393 were isolated from aSpongosorites species (Korea).400 In an independent study, (−)-(R)-6′-debromohamacanthin B 394 was obtained from what appears tobe the same Korean Spongosorites species. Although the structureillustrated is the 6′-debromo derivative, it is referred to in the textof this study as the 6′′-debromo derivative. Since the NMR solventsused in the two studies were different, a direct comparison of data


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cannot be made. In this second report, a series of related knownmetabolites were also isolated, several of which (deoxytopsentin,bromodeoxytopsentin and bromotopsentin) were inhibitors ofbacterial sortase A.401 Three moderately cytotoxic indole alka-loids, hyrtioerectines A–C 395–397, were isolated from Hyrtioserectus (Red Sea, Egypt).402 An Okinawan unidentified memberof the Thorectidae family contained the antibacterial imidazole-b-carboline alkaloid gesashidine A 398.403 Three new manzamine-

type alkaloids 399–401 were isolated from an Acanthostrongy-lophora species (Indonesia) and reported in 2004. Compound 401had antimalarial and antituberculosis activity.404 The synthesisof the (−) antipode of cis-dihydrohamacanthin B, originallyisolated from Rhaphisia lacazei,405 was reported.406 From Axinella

damicornis (Corsica), the alkylpyridinium-pyrrole alkaloiddaminin 402 was isolated and synthesised. While lacking cyto-toxicity, the compound was found to inhibit Ca2+ uptake byneurons.407 Petrosamine B 403, an inhibitor of the Helicobacterpylori enzyme aspartyl semialdehyde dehydrogenase, was isolatedfrom an Oceanapia species (Gulf of Carpentaria, Australia).408

Variolin B, originally isolated from Kirkpatrickia variolosa,409 andknown to be a potent antitumour agent, inhibits cyclin dependentkinase (CDK) activity causing p53-independent apoptosis.410

An enantiospecific synthesis of cribrostatin IV, isolated fromCribrochalina vasculum,411 has been achieved.412 Renieramycin G,originally isolated from Xestospongia caycedoi,413 has been inde-pendently synthesised in both racemic414 and enantiospecific415

forms. The polyphenolic alkaloid dictyodendrin B, isolated fromDictyodendrilla verongiformis,416 has been synthesised.417 Laughine404, a guanidine-bromopyrrole alkaloid, was isolated from thesame Dominican sponge, Eurypon laughlini, as dominicin 346described earlier in this review.357 Didiscus oxeata (Jamaica) wasfound to contain mukanadin D 405.418 Cyclooroidin, originallyisolated from Agelas oroides,419 has been synthesised.420 Enan-tiospecific syntheses of (S)-(−)-longamide B, (S)-(−)-hanishinand (S)-(−)-longamide B methyl ester have been reported es-tablishing the configuration of the laevorotary enantiomers ofthese compounds.421 Two ptilomycalin/crambescidin-type guani-dine alkaloids, batzelladine J 406 and crambescidic acid 407were obtained from Monanchora unguifera (Caribbean coast ofPanama).422 A total synthesis of crambescidin 431, originallyisolated from a Monanchora species,423 has been achieved.424


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(−)-Crambidine 408, originally isolated as the tetraacetate fromCrambe crambe,425 has been synthesised establishing the relativestereochemistry.426 A bromotyrosine derived carbamic acid methylester 409 was isolated from Psammaplysilla purpurea (South-ern India).427 11-N-Methylmoloka’iamine 410, 11-N-cyano-11-methylmoloka’iamine 411 and kuchinoenamine 412, all withantibacterial activity against the fish pathogen Aeromonas hy-drophila, were obtained from a Hexadella species (Japan).428 AFOXO1a inhibition assay was used to isolate psammaplysenes A413 and B 414 from a Psammaplysilla species (Indian Ocean),429

while in a separate paper, the syntheses are reported.430 Pseu-doceratina purpurea (Gulf of Thailand) contained purpurocer-atic acids A 415 and B 416.431 The C-11 stereochemistries offistularin-3 417 (from Aplysina fistularis,432) and 11-epi-fistularin-3 418 (from Agelas oroides433) were determined as (11S) and(11R) respectively. The variability of the C-11 stereochemistryof these, and related compounds from different organisms, wasexamined.434 Synthesis of the proposed structure of calafianin,originally isolated from Aplysina gerardogreeni,435 and the 6,6′

diastereomer 419 confirmed that 419 was the correct structure of

the natural compound.436 A species of Erylus (S. Australia) was thesource of N3,5′-cycloxanthosine 420, the first naturally occurringcyclonucleoside, but already known as a synthetic product.437

Agelasine E, originally isolated from an Agelas species,438 hasbeen synthesised.439 A synthesis of the proposed structure ofepi-agelasine C, originally isolated from Agelas mauritiana,440

led to a structural revision of epi-agelasine C to 421 and ofagelasine C, also isolated from an Agelas species,441 to 422.442

Four merosesquiterpenes, 20-O-acetyl-21-hydroxy-ent-isozonarol423, 20-O-acetylneoaverol 424, ent-yahazunol 425 and dysienone426 were obtained from two Dysidea species (Gulf of California).Compounds 423 and 426 were cytotoxic.443 Dysidea cf. cristagalli(New Zealand) yielded the previously described 20-O-acetyl-21-hydroxy-ent-isozonarol 423, as well as 20-O-acetylneoaverol424 and the deacetylquinone analogue 427. Both new com-pounds inhibited superoxide production by human neutrophils.444

Hatarumadienone 428, a nor-puupehenone type meroterpenoidisolated from a Dysidea species (Okinawa), inhibited the divisionof fertilised sea urchin eggs.445 A racemic synthesis establishedthat smenochromene D (Smenospongia species446) and likonide B(Hyatella species447) were enantiomers.448 Strongylophorines 13–19 429–435, isolated from Strongylophora strongylata (Okinawa),inhibited the maturation of starfish oocytes.449 Two polypreny-lated hydroquinones 436 and 437, inhibitors of leucotrieneproduction in porcine leukocytes, were isolated from Irciniaspinosula (Greece).450 Pelorol, originally isolated from Dacty-lospongia elegans451 and Petrospongia metachromia,451 was foundto be a Src homology inositol-5-phosphatase (SHIP) activator,and was synthesised from (+)-sclareolide confirming the previ-ous assignment of absolute stereochemistry.452 Similarly, (−)-15-oxopuupehenol, originally isolated from a Hyrtios species,453

was synthesised from (−)-sclareol.454 A microwave-mediated


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Claisen rearrangement was used to synthesise panicein, originallyisolated from Halichondria panicea.455,456 Three bisabolene-typesesquiterpenoids 438–440 were reported from a Myrmekiodermaspecies (Vanuatu).457 Two halogenated derivatives of helianane 441and 442 were obtained from Spirastrella hartmani (Martinique).458


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An ethanolic extract of Dysidea arenaria (New Caledonia) yieldedan ethyl ether, 9-hydroxyfurodysinin-O-ethyl lactone 443, whichthe authors suggest was an artifact of the ethanolic extractionprocess.459 A Halichondria species (Okinawa) yielded a series ofantimicrobial nitrogen-containing eudesmane sesquiterpenoids,halichonadins A–D 444–447.460 A new curcuphenol analogue 448,several dimeric dicurcuphenols A–E 449–453 and dicurcuphenolether F 454 were obtained from Didiscus aceratus (Papua New

Guinea). The dimers were synthesised from curcuphenol using theenzyme laccase, and the absolute stereochemistries of the biphenylaxes of 450 and 451 were determined using vibrational (IR)CD spectra.461 Both (+)-(8S)-12-nordrimane-8,11-diacetate and(+)-11-hydroxy-12-nordrim-9-en-8-one, originally isolated froma Dysidea species,462 have been synthesised.247 The isocopalanediterpenoid mycgranol 455 was isolated from Mycale aff. graveleyi(Kenya).463 Axinyssa tethyoides (Okinawa) contained two 13-epi-neoverrucosanyl sulfates 456 and 457.464 Two rearrangedspongane diterpenoids, omriolides A 458 and B 459 were obtainedfrom Dictyodendrilla aff. retiara (Kenya).465 A re-isolation ofamphilectene diterpenoids, originally isolated from a CaribbeanCribrochalina species,466 has led to a reassignment of the absolutestereochemistry of 460 and the relative stereochemistries of 461–463. A new compound 464 was also described in the same study.467

A re-isolation of microcionin-1 465 from Fasciospongia cavernosa,but originally isolated from Microciona toxystila,468 establishedthe relative stereochemistry with the unusual cis-fused ring A/Bsystem.469 (−)-Marginatone, from Aplysilla glacialis,470 has beensynthesised confirming the absolute stereochemical assignment.471

Three partially cyclised sesterterpenoids 16-oxoluffariellolide 466,16-hydroxyluffariellolide 467, and 468, all with phosphataseCdc25B inhibitory activity, were isolated from a Thorectandraspecies (Papua New Guinea).472 19-Methoxyscalarin 469, fromHyrtios erectus (China), was reported in 2004.473 The hyrtiosins

A–E 470–474, scalarane type sesterterpenoids, were isolatedfrom two separate collections of Hyrtios erecta (Hainan Island,China).474 Hyrtios erecta (Maldives) yielded the cytotoxic ses-terstatin 6 475,475 while a collection of the same sponge fromthe Egyptian Red Sea yielded sesterstatin 7 476.476 Ircinin-1,originally isolated from Ircinia oros,477 has been found to inducecell cycle arrest and apoptosis.478 Enantiospecific syntheses ofluffolide, isolated from a Luffariella species,479 16,25-dihydroxy-cheilantha-13(24),17-dien-19,25-olide and 25-hydroxycheilantha-13(24),15,17-trien-19,25-olide, isolated from an Ircinia species,480

have been reported.481 A series of cytotoxic, highly degradedsteroids, demethylincisterols A1–A4 477–480 were isolated froma Homaxinella species (Korea). In the same study, four butoxy-derivatised sterols, homaxisterols A1–A4 481–484, were also


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isolated from the same sponge.482 Iotrochoto birotulata (HainanIsland, China) contained three 4-en-3-one sterols 485–487.483

Several polyhydroxylated sterols 488–491 were isolated from

Lamellodysidea (Dysidea) herbacea (Red Sea), and 490 and491 were active against Candida albicans.484 Another series ofpolyhydroxylated sterols, dysideasterols A–E 492–496, were iso-lated from a Dysidea species (Hainan Island, China).485 Twomoderately cytotoxic steroids 497 and 498 were obtained froma new species of Euryspongia (Vanuatu).486 Stylisterols A–C499–501 and the unusual ring-fused cyclopropane-containing


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hatomasterol 502 were obtained from a Stylissa species(Okinawa).487 The cytotoxic steroidal alkaloid plakinamine I503 was isolated from a Corticium species (Vanuatu).488 An

unusual oxime containing steroid, (3E)-cholest-4-en-3,6-dione-3-oxime 504 was isolated from Cinachyrella australiensis (China).489

Two steroidal glycosides, erylosides K 505 and L 506 fromErylus lendenfeldi (Red Sea), were selectively active against ayeast strain defective in double stranded DNA repair. Theabsolute stereochemistry of eryloside A 507, originally isolatedfrom the same sponge, has also been established.490 A Jaspisspecies (Hainan Island, China) yielded 22,23-dihydrostellettin D508.491 The cytotoxic triterpenoid sodwanone S 509 was obtained

from Axinella weltneri (Comoros Island, Indian Ocean).492 Thesarasinosides J–M 510–513, triterpene glycosides isolated fromMelophlus sarassinorum (Sulawesi, Indonesia), were antimicrobialto B. subtilis and S. cerevisae.493 Prianos osiros (Pohnpei, Microne-sia) contained the unusual cytotoxic carotenoid 514.494

8 Coelenterates

There has been a noticeable increase in the number of newmetabolites reported from coelenterates over the 2002–2005period. The fatty acid ethyl ester 515 was isolated from thesoft coral Nephthea hainansis (China), along with a sesquiter-pene metabolite (see later).495 The polyacetylene carboxylic acidsmontiporic acids A and C, previously reported from Montiporadigitata,496,497 are potent feeding attractants of the coral predatormollusc Drupella cornus.498 (±)-1-Nonadecyloxy-2,3-propanediol,previously reported from the sponge Desmapsamma anchorata,499

was identified as a weakly cytotoxic constituent of Dendronephthyagigantea (Korea).500 Three sphingolipids 516–518 and a sterol (seelater) were isolated from Lobophytum sp. (Indian Ocean).501 Ahomologue of 518, 519, was obtained from a Lobophytum species(South China Sea).502 The dominant sphingolipid of Subergorgiasuberosa (Indian Ocean) was 520,503 while confertamides A 521and B 522 were identified in extracts of Sinularia conferta(China).504 A structurally-related sphingosine derivative,505 re-isolated from Sinularia crassa (Indian Ocean), exhibited anti-inflammatory activity.506 Caucanolides A–F 523–528 were isolatedfrom Pseudopterogorgia bipinnata (Colombia),507 and while 523and 526 exhibited mild activity towards Plasmodium falciparum,523 also exhibited cytotoxicity towards a panel of tumourcell lines. Meroditerpenoids chabrolonaphthoquinone B 529,


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chabrolobenzoquinones E–H 530–533 and chabrolohydroxyben-zoquinones E–G 534–536 were isolated as mildly cytotoxicconstituents of Nephthea chabrolii (Taiwan).508 Oxygenated


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sesquiterpenes gibberodione 537, peroxygibberol 538 and sinugib-berodiol 539 were isolated from Sinularia gibberosa (Taiwan).509

Mild cytotoxicity was ascribed to 538. Bicyclic sesquiterpene 540was reported from Nephthea hainansis (China).495 Chlorinatednorsesquiterpene paralemnolin A 541 and co-metabolites B 542and C 543 were isolated from the soft coral Paralemnalia thyrsoides(Taiwan).510 Seven sesquiterpenoid metabolites 544–550, com-

prising elemane, eudesmane and germacrane skeletal types, werereported as mildly antiplasmodial constituents of a Eunicea species(Caribbean).511 Laevinols A–H 551–558, laevinone A 559 and theknown decalin 560 were isolated from Lemnalia laevis (Taiwan).512

The sesquiterpene alkaloid 561 was reported as a mildly cytotoxicmetabolite of the gorgonian Subergorgia suberosa (China).513

Linderazulene 562 and two new congeners 563 and 564 wereisolated as mildly cytotoxic constituents of a deep-sea collectionof the gorgonian Paramuricea sp. (Curacao).514 As noted in the2004 review in this series,213 three publications presenting newpterosin diterpene glycosides from Pseudopterogorgia elisabethae


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unwittingly led to duplication in structures and trivial names.515–517

Communication with the authors of these studies has now ledto the following clarification of trivial names associated withstructures: pseudopterosin P 565, Q 566, R 567, S 568, 3′-O-acetyl-pseudopterosin Q 569, 2′-O-acetyl-pseudopterosin Q 570,pseudopterosin T 571, U 572, V 573, 3′-O-acetyl-pseudopterosinU 574, 2′-O-acetyl-pseudopterosin U 575, pseudopterosin W576, X 577 and Y 578.518 No structural revisions are proposed.7-Hydroxyerogorgiaene and 7,8-dihydroxyerogorgiaene havebeen shown to be intermediates in the biosynthesis of thepseudopterosins.519 Of ten diterpenes, the pacificins A–J 579–588,isolated from Nephthea pacifica (Taiwan), only 581 and 586 were

cytotoxic (mild).520 Microclavatin 589 and the previously reportedcembranolide capillolide,521 were isolated as cytotoxic componentsof the soft coral Sinularia microclavata (China).522 Sarcophyton sp.(China) was the source of sarcophytonolides A–D 590–593.523 Therelative configuration of leptolide 594, isolated from Leptogorgiaalba (Panama), was determined by X-ray analysis.524 A numberof known diterpenes were also isolated in the same study from L.alba or L. rigida; combinations of CD spectra and X-ray analysesled to the determination of absolute configuration of pukalidealdehyde 595, lophotoxin 596, pukalide 597, lopholide 598and 13a-acetoxypukalide 599. Sinularolides A–E 600–604 wereisolated from Sinularia gibberosa (China).525 Of these, 601–604were mildly cytotoxic. 2-Hydroperoxysarcophine 605 was reportedas a natural product from the soft coral Lobophytum crassum(China).526 In addition to the known metabolites sinuleptolide 606and 5-epi-sinuleptolide 607,527 isocembranoid sinulochmodin B608, dimeric norcembranoid sinulochmodin A 609, and yonaranediterpene sinulochmodin C 610 were also reported from Sinularialochmodes (Taiwan).528 The absolute configurations of 606 and607 were determined and by comparison of [a]D values, theabsolute configurations of 608 and 609 were implied. The knowncembranoid sinulariol D, previously obtained from a Sinulariaspecies,529 was reported as mildly cytotoxic.530 Two separate reportshave described the bioassay-directed fractionation of an extractfrom Xenia umbellata (Taiwan) leading to the mildly cytotoxicditerpenoids xenibellols A 611 and B 612531 and umbellactal 613.532

The architecturally-impressive pentacyclic diterpene intricarene614 was reported from Pseudopterogorgia kallos (Colombia), withstructural confirmation by X-ray analysis.533 A number of newexamples of briarane diterpenoids were presented in separate


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reports from Briareum sp. (Japan). Violides Q–V 615–620 andrelated metabolites 621–625 were reported from a Briareum species(Bonotsu, Kagoshima Prefecture),534 while a Briareum species(Amami Oshima, Kagoshima Prefecture) yielded briarlides I–R 626–635.535,536 Mild cytotoxicity was observed for 615, 616,618 and 622. In a separate report, further investigation ofBriareum sp. (Bonotsu) led to the isolation of briviolides A–D636–639, 12-O-acetylbriviolide D 640, 9-deacetoxybriviolide D641, 4-acetoxybriviolide D 642 and briviolides E–I 643–648.537,538

Mild cytotoxicity was observed for 637, 639–641 and 644. 8,17-

Epoxybriarane diterpenes briarenol A 649539 and briaranolidesA–J 650–659540 were isolated respectively from Taiwanese andOkinawan collections of Briareum sp. Renillins A–D 660–663were identified as feeding deterrent components of an extractof the sea pansy Renilla reniformis (North Carolina).541 Chlo-rinated briaranes juncenolides F 664 and G 665 were isolatedfrom Junceella juncea (Taiwan),542 while Junceella fragilis(South China Sea) yielded junceellonoids C–E 666–668.543 The


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absolute configuration of the eunicellin-class diterpenoid 11-acetoxy-4-deoxyasbestinin 669, originally isolated from Bri-areum asbestinum,544 has been determined by stereoselective totalsynthesis.545 New eunicellins klyxumines A 670 and B 671 andepoxycladines A–D 672–675 were reported from specimens ofKlyxum flaccidum and Cladiella kashmani (Kenya).546 Vigulariol676, previously known as a reaction intermediate in the stereos-elective synthesis of the sclerophytins,547 was isolated from thesea pen Vigularia juncea (Taiwan).548 Australins A–D 677–680were isolated from Cladiella australis (Taiwan), but only 678 wasmildly cytotoxic.549 Xenicane diterpenes 681–688 were reportedfrom Xenia blumi (Taiwan)550 while Xenia florida (Taiwan) wasthe source of xeniolactones A–C 689–691.551 Mild cytotoxicitywas observed for 681–684, 686, 687 and 689. The nor-xenicanemetabolite xenibellal 692 was reported as a mildly cytotoxiccomponent of Xenia umbellata (Taiwan).552 Confertdiate 693 is atetracyclic diterpenoid isolated from Sinularia conferta (China),504

while sterol 694 was reported from a Lobophytum species (India).501


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3-Oxo-sterols 695–701 were reported as mildly cytotoxic metabo-lites of Anthomastus bathyproctus (Antarctica)553 and 702 and703 were isolated from Nephthea bayeri (China),554 while the19-acetoxy-sterols 704 and 705 were reported from a soft coralSinularia species (China).555 The polyoxygenated sterols hippuris-terones J–L 706–708, the hippuristerols E 709 and F 710 and thecyclopropyl-containing sterol 711 were isolated from Isis hippuris(Taiwan),556 while Sinularia dissecta (China) was the source of 712–717.557 Rare examples of cholesterol-3-formate esters 718 and 719and A-nor sterols 720–722 were reported from Dendronephthyasp. (China).558 The hemiketal steroid cladiellin A 723, isolatedfrom Cladiella sp. (China), along with two dehydration productswere found to have radical scavenging properties.559 The 24-ketal steroids suberoretisteroids A–E 724–728 were reported fromSubergorgia reticulata (China).560 Structure elucidation, whichincluded X-ray analysis of 724,561 necessitated a structural revisionof 729 previously reported from Gorgonella umbraculum.562 Similarconclusions were made by another group working on the samespecies of gorgonian from the same locale.563 Their studies led tothe determination of absolute configuration of 724 (which theynamed reticulatin) and 729. In addition, this study also reported

the structure of reticulatic acid 730. In addition to a number ofknown congeners, eleven new examples of hippuristanol sterols,731–741, were reported from Isis hippuris (Taiwan).564 The abso-lute configuration of the known sterol 742565 was determined onbiogenetic grounds and imputed to all but 741 of the compounds


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reported. Steroidal glycosides 743 and 744 were obtained fromCladiella sp. (China),566 while 745–748 were isolated from Junceellajuncea (China).567 Gorgosterol derivatives previously isolated fromEunicea laciniata568 and Plexaurella grisea,569 were reported to


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be agonists of Liver X receptors.570 A sea anemone of theorder Actinaria was the source of diterpenoids actiniarins A–C 749–751, moderate inhibitors of recombinant human cdc25Bphosphatase.571 The usual class of natural products isolated fromanemones, peptides and protein toxins, have been reviewed,572

and new examples reported. Antheopsis maculata (Japan) was thesource of crab toxic peptides Am I–III,573 while acrorhagins I andII are 50 and 44 residue peptides respectively isolated from Actiniaequina (Japan).574 Cytolytic toxins Or–A and Or–G were isolated

from Oulactis orientalis (Japan) and found to form ion channels inbilayer lipid membranes.575 Cangitoxin, a 4958 Da peptide isolatedfrom Bunodosoma cangicum (Brazil), acts on sodium channels.576

9 Bryozoans

Remarkably, there have been no reports of new bryozoan chem-istry. Some analogues of amathamide A (originally obtained fromAmathia wilsoni577) have been prepared and their antimicrobialactivities studied.578

10 Molluscs

The number of new metabolites reported annually from molluscshas been somewhat cyclical over the 2002–2005 period, with amodest increase reported in 2005. A range of minor nonmethylene-interrupted di-, tri- and tetraenoic fatty acids were identified inextracts of the gonads of limpets Cellana grata and Collisella dor-suosa (Japan).579 Turbostatins 1–4 752–755 were isolated as cyto-

toxic components of the Asian topshell snail Turbo stenogyrus(Taiwan).580 20-Methyl spirolide G 129 was identified by MS/MSanalysis of extracts of Mytilus edulis (Norway).163 Further biolog-ical testing of the hexacyclic alkaloid lamellarin D, first reportedfrom Lamellaria sp. in 1985581 has identified lamellarin D to be apro-apoptotic agent which remains cytotoxic in multidrug resis-tant cell lines.582 Molluscs of the order Sacoglossa are a renownedsource of polypropionate-derived metabolites.583 Pyrone 756, andthe possibly artefactual peroxy derivative 757, were isolated fromPlacobranchus ocellatus (India).584 The bicyclo[4.2.0]octane coreof 756 is analogous to that contained in the related metaboliteselysiapyrones A 758 and B 759 reported from Elysia diomedea.585

The proposed biogenesis of the bicyclic core is via an 8p–6p elec-trocyclic cascade. A biomimetic synthesis of elysiapyrones A and B


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utilised such a pathway586 and a biomimetic synthesis of (±)-9,10-deoxytridachione based upon an electrocyclisation step has alsobeen reported.587 9,10-Deoxytridachione also reacts under tripletexcited state sensitisation to afford photodeoxytridachione583

which has the ecological implications of polypropionates actingas natural sunscreening agents.588 Related pyrone, cyercene A,589

also undergoes photoisomerisation to yield alkene isomers andhydroperoxides which have been reported previously as naturalproducts.590 The structure proposed for tridachiahydropyrone 760,isolated from Tridachia crispata,591 has been synthesised but thespectroscopic data observed did not match that reported for thenatural product. A revision of the structure of the natural productis required.592 The absolute configuration of the trans-decalin 761isolated from the limpet Trimusculus reticulatus593 has been deter-mined by stereoselective synthesis.594 Carotenoids 762–764 werereported from the oyster Crassostrea gigas (Japan)595 while a 4265Da defensin antimicrobial peptide was isolated from the Americanoyster Crassostrea virginica.596 Two conotoxins, l-conotoxinsSIIIA and KIIIA, were characterised by cDNA analysis of Conusstriatus and C. kinoshitai (Pacific) and subsequent solid-phase

synthesis.597 A more classical approach led to the isolation ofpeptide de7a from the venom of C. delessertii (Mexico),598 andrg11a from C. regius (Brazil).599 The biological activities of bothpeptides have yet to be characterised. The solution structureof d-Am2766, a highly hydrophobic conotoxin isolated from C.

amadis600 has been studied by 3D NMR spectroscopy.601 Tworeviews cover the chemical ecology of New Zealand opistho-branch molluscs,602 and the role played in ink secretions fromthe sea hare Aplysia californica.603 Sesquiterpenes 765–767, inaddition to a number of known derivatives, were isolated fromA. dactylomela (Canary Islands).604 in vitro antitumour evaluationsupported the hypothesis that acetylation leads to a decreasein metabolite toxicity. Three C15-halogenated compounds 768–770 were isolated from A. dactylomela (China).605 The structureand absolute configuration of 768 was established and it wasconcluded that 769 and 770 were enantiomers of previouslyreported natural products606 of defined absolute configuration.607

This study also necessitated the stereochemical revision of (3E)-epi-pinnatifidenyne, previously reported from Laurencia obtusa,608

to ent-768. The related metabolite (3Z)-bromofucin 771 was iso-lated from extracts of Aplysia parvula (South Africa).609 Acetatesof laurinterol 772 and debromolaurinterol 773, previously knownas semi-synthetic compounds, were reported as mildly bioactivenatural products from Aplysia kurodai (Japan).610 Bursatella leachii(Thailand) was the source of the known metabolite hectochlorin774, the deacetyl analogue 775 and the structurally-unrelated776.611 Both 774 and 775 were potently cytotoxic. Degraded sterolsaplykurodinone-1 777 and -2 778 were isolated from skin extractsof the sea hare Syphonota geographica (Greece).612 The stereo-chemical assignment of (+)-aurilol 779, isolated from the sea hareDolabella auricularia,613 has been achieved via stereoselective totalsynthesis.614 Analogues of dolastatin 11, also originally isolated


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from D. auricularia,615 have been synthesised and evaluated forantitumour activity and stimulatory effects on the polymerisationof actin.616 Two groups have reported the stereoselective synthesisof the nor-sesquiterpene (+)-austrodoral 780, originally isolatedfrom the Antarctic nudibranch Austrodoris kerguelenensis,617

starting from either (−)-sclareol618 or (+)-sclareolide.619 Fura-nosesquiterpenes alcohols pelseneeriols-1 781 and -2 782 wereisolated from the mantle of the nudibranch Doriopsilla pelseneeri(Portugal).469 Syntheses of 5-methyl-2-((2E,6E)-3,7,11-trimethyl-2,6-dodecadien-9-onyl)benzo-1,4-quinone and the hydroquinone,isolated from the South African nudibranch Leminda millecra,620

have been reported.621 The absolute configurations of nudibranch-derived diterpenes norrisolide 783,622 isolated from Chromodorisnorrisi,623 and dorisenone C 784624 from C. obsoleta,625 have

been determined by stereoselective syntheses. The stereoselectivesynthesis of (−)-jorumycin, isolated from the Pacific nudibranchJorunna funebris,626 has confirmed the absolute configuration ofthe cytotoxic tetrahydroisoquinoline alkaloid and also providedrelated structures for preliminary examination of structure–activity relationships.415

11 Tunicates (ascidians)

The number of new metabolites reported annually from ascidianshas been steadily declining over the 2002–2005 period. A didemnidascidian (Okinawa) was the source of biselides A–E 785–789,627 of

which 785 and 787 were modestly cytotoxic towards a panel oftumour cell lines. The absolute configuration of bistramide C 790,isolated from Lissoclinum bistratum,628 has been determined bycomputational analysis629 and total synthesis.630 Two long chainpolyacetoxy acyl amino acids, sagittamides A 791 and B 792 wereisolated from an unidentified ascidian (Pohnpei).631 Aplidium aff.densum (Oman) was the source of the meroterpenes methoxy-conidiol 793 and didehydroconicol 794,632 while the ubiquinonederivatives glabruquinones A 795 and B 796 were reportedfrom Aplidium glabrum (Far East).633 The structures of 795 and796 were confirmed by synthesis and 795 was found to exhibitin vitro cancer preventive activity in a tumour cell transformationassay. The structures of the demethoxy diprenylquinone analoguesverapliquinones A and B, isolated from Brittany specimens of Ap-lidium sp.,634 have also been confirmed by synthesis.456 Extracts ofAplidium conicum (Mediterranean) yielded 1,1-dioxo-1,4-thiazinecontaining aplidinones A–C 797–799635 and thiaplidiaquinones A800 and B 801.636 Bioassay evaluation of 800 and 801 demonstratedthat the compounds had entered the cells, and induced theintracellular production of reactive oxygen species leading to


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disruption of mitochondrial potential and cell death by apoptosis.Perspicamides A 802 and B 803 are quinolinecarboxylic acidderivatives isolated from Botrylloides perspicum (Australia).637

Synoicum macroglossum (India) was the source of a modestly

a-glucosidase inhibitory alkaloid, tiruchanduramine 804. Thestructure was confirmed by synthesis.638 A full account of thestructure elucidation of lissoclibadin 1639 from Lissoclinum cf.badium (Indonesia) has been reported, along with two new con-geners, lissoclibadins 2 805 and 3 806.640 All three metabolitesexhibited varying degrees of cytotoxicity and antibiotic properties.Investigations of the chemistry of colour morphs of a Cystodytesspecies (Mediterranean) led to the isolation of deacetylshermil-amine B 807.561 In addition to a number of known congeners, newlamellarin alkaloids 808–811 were isolated from Didemnum obscu-rum (India).641 Potent cytotoxicity towards colorectal tumour cellswas observed. An unidentified ascidian of the family Polycitoridae(Flores, Indonesia) contained two tricyclic alkaloids, polycitorolsA 812 and B 813, closely related to the known cylindricines,642

together with the known compound lepadiformine.643,644 Two


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studies have reported that the biosynthetic genes for productionof the patellamide cyclic peptides reside within Prochloron sp.,the cyanobacterial symbiont of Lissoclinum patella.645,646 Thestructures of cyclic peptides bistratamides F–I, isolated from Lis-soclinum bistratum,647 have been confirmed by total synthesis,648,649

as were the structures of the Didemnum molle metabolites650 did-molamides A and B.651 The antimalarial activity of cyclic peptidesulithiacyclamide and patellamides A–C has been reported.652 Theabsolute stereochemistry of (+)-pseudodistomin D 814, reportedin 1997 from Pseudodistoma megalarva,653 has been establishedby total synthesis.654 Stereoselective synthesis of the Nephteis

fasicularis metabolite655 (−)-fasicularin has been reported.656 Theoriginal isolation report of fasicularin noted differential activitytowards DNA repair-deficient yeast mutants. The DNA damagingability of a racemic preparation of the alkaloid has now beenstudied in depth.657 The structurally related quinolizidine anddecahydroquinoline alkaloids (−)-pictamine658 and (−)-lepadinB659 block neuronal nicotinic receptors.660 Ningalin D, an MDRreversing cytotoxic alkaloid originally reported from Didemnumsp. (Australia),661 has been synthesised and structure–activityrelationships studied.662 The cyclodepsipeptide aplidine continuesthrough clinical trials663 with a recent report detailing structuresof human liver microsome induced metabolism.664 The in vivoactivity profile of ET-743 has been summarised665 and the anti-inflammatory properties reported.666 The solution structure ofvanabin2, a vanadium binding protein from Ascidia sydneiensissamea, has been studied by NMR spectroscopy.667

12 Echinoderms

The number of new metabolites reported annually from echino-derms has remained relatively constant over the 2002–2005 period.While echinoderms are a well documented source of biologicallyactive saponins and glycolipids,16,668 they also represent an impor-tant food source.15 The naphthoquinone metabolites echinaminesA 815 and B 816 were isolated from the sea urchin Scaphechinusmirabilis (Japan Sea), and the structures confirmed by semi-synthesis from known urchin quinones.668 Radical scavengingproperties were observed for both compounds. Ceramide lipids817–819 were isolated from the starfish Distolasterias nipon (EastSea, Korea).669 The sea cucumber Stichopus japonicus was thesource of five glycolipid molecular species SJC-1 820, SJC-2 821,SJC-3 822, SJC-4 823 and SJC-5 824.670 Linckiacerebroside A825 was identified as a new glycolipid from the starfish Linckialaevigata (Japan).671 Further attempts at purification of the compo-nents of the glucocerebroside molecular species HLC-2, previouslyreported from the sea cucumber Holothuria leucospilota,672 ledto the characterisation of 826.673 The ante-iso type side chainconfiguration of 826 was determined by synthesis.674 A gangliosidemolecular species LLG-5 827, containing an unusual trisialosylmoiety, was isolated from the Japanese starfish Linckia laevigata.675

In addition to a number of known compounds, the isopropy-

lidenedioxy sterol 828 was reported from the starfish Asterinapectinifera (China).676 Further investigation of the constituents ofthe Far-Eastern starfish Ctenodiscus crispatus led to the isolationof 829 as a mixture of C-24 and C-25 stereoisomers, togetherwith 830 and 831. The side chain stereochemistry of the knownstructurally-related sterol 832677 was defined as (24R,25R).678

The cyclopropane-containing hydroxysteroid phrygiasterol 833and steroid glycoside phrygioside B 834 were isolated from theFar-Eastern starfish Hippasteria phrygiana.679 Mild cytotoxicitytowards, and apoptotic induction of, Ehrlich carcinoma cellswas observed. Two b-D-xylosides, minutosides A 835 and B 836,were reported from the starfish Anasterias minuta (Patagonia).680

Minutoside B 836 bears an unusual amidohypotaurine sidechain.Both 835 and 836 were modestly antifungal. Studies of twospecies of Far-Eastern starfishes, Henricia aspera and H. tu-mida led to identification of a number of new polyhydroxylsteroids and glycosides.681 Henricia aspera was the source ofasperosides A 837 and B 838, H. tumida the source of 839 and840, while tumidosides A 841 and B 842 were isolated fromboth species. All six metabolites exhibited moderate cytostaticactivity towards sea urchin eggs. Bioassay-directed fractionationof extracts from the starfish Certonardoa semiregularis (Korea)led to the characterisation of the moderately cytotoxic saponincertonardoside P2 843, and inactive certonardoside I3 844.682

The isolation of the bioactive asterosaponins 845–850 from thecushion star Culcita novaeguineae (China) has been detailedin three separate reports.683–685 The triterpene nobilisidenols A851 and 852 were isolated from Holothuria nobilis (China).686

Triterpene glycosides, holothurins B2 853, B3 854 and B4 855, werereported from a collection of Holothuria polii (Bay of Naples).687

Six triterpene tetraosides, intercedensides D–I 856–861, wereisolated as cytotoxic constituents of the sea cucumber Mensamariaintercedens (China).688 This study also concluded that the sidechainstereochemistry of intercedenside A 862689 should be corrected to(22Z). Bioassay-directed fractionation of an extract of the seacucumber Pentacta quadrangularis (China) yielded the dual anti-angiogenic and anti-proliferative saponin, philinopside A 863.690

However, no spectroscopic data were reported to support thestructure shown. The sea cucumber Australostichopus mollis (NewZealand) was the source of the monosulfated triterpene glycosidesmollisosides A 864, B1 865 and B2 866,691 while Stichopus parvi-mensis (Baja California), yielded the oligoglycosides parvimosidesA 867 and B 868.692 A smooth muscle-relaxing hexadecapeptidewas characterised from the starfish Asterina pectinifera.693


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13 Miscellaneous

Methoxylated polybrominated biphenyls, including the new ana-logue 869, have been identified as bioaccumulated natural productsin a number of marine mammals.694,695 A further range of toxicpeptides have been identified in skin secretions of the soapfishGrammistes sexlineatus.696 The hydroid Campanularia sp. (NewZealand) was the source of the guanidine 870,697 while a Chinesecollection of the annelid Arenicola cristata led to the isolation ofthe cytotoxic sulfated sterol arenicolsterol A 871.698 The modestlycytotoxic cymodienol 872 and cymodiene 873 were isolatedfrom the sea grass Cymodocea nodosa (coastal areas of centralGreece).699 In two separate studies, the mangrove plant Bruguieragymnorrhiza (China) yielded phenols 874–878700 and diterpenes879–881.701 The phenol 876 was moderately active towards arange of microorganisms, while the diterpene 881 was mildly

cytotoxic towards mouse fibroblast cells. A second species ofChinese mangrove plant, Bruguiera sexangula var. rhynchopetala,was the source of the diterpenes 882–884 and the disulfide quinone

885.702 Bruguiera gymnorrhiza (China) yielded related diterpenes886–889.703 Mild cytotoxicity was observed for 888 and 889.

14 Conclusions

In reviewing the literature for 2001, the observation was made thatthe rate of increase in publications of new compounds comparedwith 1965–2000 might have been easing.704 The publication rate foreach of the years 2001–2005 has varied somewhat, but at the end ofthis period, using numbers extracted from MarinLit,68 the steadyarithmetic increase observable since 1965 continues (see Fig. 1).

Fig. 1 Numbers of marine natural products for the period 1965–2005.

The geographic origins and the phyla sampled for 2001–2005were examined to establish the differences, if any, compared with


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the sampling over the previous 36 years. These 2001–2005 data areshown in Fig. 2 and 3 as percentages of the totals for 1965–2005.

Fig. 2 Citations for source regions for the period 2001–2005 as apercentage of the totals for 1965–2005.

Fig. 3 Citations for source phyla for the period 2001–2005 as a percentageof the totals for 1965–2005.

Although the geographical descriptors used in MarinLit are notprecise, the large increase from the China Sea as a source area isunmistakable. While the absolute numbers of samples are less,there has also been a notable increase in sampling from the NorthSea, the Baltic and Russian territories.

Few people would be surprised by the observation that 45% ofthe accumulated literature on marine microorganisms has beenpublished since 2000. Other phyla show (relatively) increasedinterest also. These “traditional” phyla, such as Porifera, Chordataand Coelenterata, are significant as the absolute numbers for1965–2000 reported for these phyla are much larger than thosefor microorganisms. It is pertinent to note that some 40% of thework for 2001–2005 on coelenterates has been sourced from theChina Sea.

Analysis of the data for 2001–2005 period against the accumu-lated records from 1965 onwards suggests that the study of marine

natural products is thriving, attracting new research groupings andmaking rapid progress in exploring alternative source phyla andgeographical areas.

15 References

1 J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote and M. R.Prinsep, Nat. Prod. Rep., 2005, 22, 15.

2 C.-Y. Wang, M.-Y. Geng and H.-S. Guan, Chin. J. New Drugs, 2005,14, 278.

3 A. M. S. Mayer and M. T. Hamann, Comp. Biochem. Physiol., Part C:Toxicol. Pharmacol., 2005, 140, 265.

4 M. S. Butler, Nat. Prod. Rep., 2005, 22, 162.5 G. M. Cragg and D. J. Newman, Pure Appl. Chem., 2005, 77, 1923.6 G. M. Cragg and D. J. Newman, Pure Appl. Chem., 2005, 77, 7.7 X.-H. Yan and Y.-W. Guo, Chin. J. Nat. Med., 2005, 3, 65.8 S. Singh, B. N. Kate and U. C. Banerjee, Crit. Rev. Biotechnol., 2005,

25, 73.9 T. Okino, Kaiyo Seibutsu Seibun no Riyo, 2005, 47.

10 S. Tsukamoto, Kaiyo Seibutsu Seibun no Riyo, 2005, 60.11 D. Sipkema, M. C. R. Franssen, R. Osinga, J. Tramper and R. H.

Wijffels, Mar. Biotechnol., 2005, 7, 142.12 K. Iguchi, Kaiyo Seibutsu Seibun no Riyo, 2005, 97.13 S. Fukuzawa, Kaiyo Seibutsu Seibun no Riyo, 2005, 132.14 T. Miyamoto, Kaiyo Seibutsu Seibun no Riyo, 2005, 145.15 M. S. Kelly, Prog. Mol. Subcell. Biol., 2005, 39, 139.16 Y. Yokota, Prog. Mol. Subcell. Biol., 2005, 39, 251.17 M. Ishibashi, Kaiyo Seibutsu Seibun no Riyo, 2005, 159.18 T. J. Heckrodt and J. Mulzer, Top. Curr. Chem., 2005, 244, 1.19 E. Zubia, M. J. Ortega and J. Salva, Mini–Rev. Org. Chem., 2005, 2,

389.20 J. Sun, H. Lin, S. Li, G. Liu, C. Zhang and H. Zhang, Zhongcaoyao,

2005, 36, 609.21 H. N. Kamel and M. Slattery, Pharm. Biol., 2005, 43, 253.22 T. L. Simmons, E. Andrianasolo, K. McPhail, P. Flatt and W. H.

Gerwick, Mol. Cancer Ther., 2005, 4, 333.23 M.-L. Bourguet-Kondracki and J. M. Kornprobst, Adv. Biochem. Eng.

Biotechnol., 2005, 97, 105.24 Y. Nogata, Kaiyo Seibutsu Seibun no Riyo, 2005, 290.25 D. Alonso, A. Castro and A. Martinez, Expert Opin. Ther. Pat., 2005,

15, 1377.26 L. Gomez-Paloma, M. C. Monti, S. Terracciano, A. Casapullo and

R. Riccio, Curr. Org. Chem., 2005, 9, 1419.27 R. A. Keyzers and M. T. Davies-Coleman, Chem. Soc. Rev., 2005, 34,

355.28 I. P. Singh, S. B. Bharate and K. K. Bhutani, Curr. Sci., 2005, 89, 269.29 N. Dias, H. Vezin, A. Lansiaux and C. Bailly, Top. Curr. Chem., 2005,

253, 89.30 L. Zhang, R. An, J. Wang, N. Sun, S. Zhang, J. Hu and J. Kuai, Curr.

Opin. Microbiol., 2005, 8, 276.31 A. T. Bull, J. E. M. Stach, A. C. Ward and M. Goodfellow, Antonie

van Leeuwenhoek, 2005, 87, 65.32 C. Imada, Antonie van Leeuwenhoek, 2005, 87, 59.33 B. S. Moore, J. A. Kalaitzis and L. Xiang, Antonie van Leeuwenhoek,

2005, 87, 49.34 P. R. Jensen, T. J. Mincer, P. G. Williams and W. Fenical, Antonie van

Leeuwenhoek, 2005, 87, 43.35 H. P. Fiedler, C. Bruntner, A. T. Bull, A. C. Ward, M. Goodfellow, O.

Potterat, C. Puder and G. Mihm, Antonie van Leeuwenhoek, 2005, 87,37.

36 J. Clayden, B. Read and K. R. Hebditch, Tetrahedron, 2005, 61, 5713.37 T. Yasumoto, Proc. Jpn. Acad., Ser. B, 2005, 81, 43.38 K. Yasumoto, Kagaku to Seibutsu, 2005, 43, 153.39 C. Wiegand and S. Pflugmacher, Toxicol. Appl. Pharmacol., 2005, 203,

201.40 M. A. Friedman and B. E. Levin, J. Int. Neuropsychol. Soc., 2005, 11,

331.41 L. E. Fleming, L. C. Backer and D. G. Baden, Environ. Health

Perspect., 2005, 113, 618.42 G. P. Rossini, Toxicology, 2005, 207, 451.43 M. C. C. Batoreu, E. Dias, P. Pereira and S. Franca, Environ. Toxicol.

Pharmacol., 2005, 19, 401.


Dow

nloa

ded

on 2

3 Ja

nuar

y 20

11Pu

blis

hed

on h

ttp://

pubs

.rsc

.org

| do

i:10.

1039

/B60

3047

PView Online


44 G. A. Codd, L. F. Morrison and J. S. Metcalf, Toxicol. Appl.Pharmacol., 2005, 203, 264.

45 Y. Harayama and Y. Kita, Curr. Org. Chem., 2005, 9, 1567.46 E. M. Antunes, B. R. Copp, M. T. Davies-Coleman and T. Samaai,

Nat. Prod. Rep., 2005, 22, 62.47 L. N. Rogosa, N. F. Salakhutdinov and G. A. Tolstikov, Russ. J. Bioorg.

Chem., 2005, 31, 507.48 J. P. Berge and G. Barnathan, Adv. Biochem. Eng. Biotechnol., 2005,

96, 49.49 W. Gul and M. T. Hamann, Life Sci., 2005, 78, 442.50 M. Somei and F. Yamada, Nat. Prod. Rep., 2005, 22, 73.51 R. G. S. Berlinck and M. H. Kossuga, Nat. Prod. Rep., 2005, 22,

516.52 J.-F. Liu, S.-P. Guo and B. Jiang, Chin. J. Org. Chem., 2005, 25,

788.53 T. Ogamino and S. Nishiyama, J. Synth. Org. Chem., Jpn., 2005, 63,

583.54 J. D. Connolly and R. A. Hill, Nat. Prod. Rep., 2005, 22, 230.55 Z. Jin, Nat. Prod. Rep., 2005, 22, 196.56 V. M. Dembitsky, T. A. Gloriozova and V. V. Poroikov, Mini–Rev.

Med. Chem., 2005, 5, 319.57 M. Kita and D. Uemura, Chem. Lett., 2005, 34, 454.58 M. Ohba, Recent Res. Dev. Org. Chem., 2005, 9, 71.59 N. S. Sarma, M. S. R. Krishna and S. R. Rao, Mar. Drugs, 2005, 3,

84.60 P.-J. Sung, P.-C. Chang, L.-S. Fang, J.-H. Sheu, W.-C. Chen, Y.-P. Chen

and M.-R. Lin, Heterocycles, 2005, 65, 195.61 B. S. Moore, Nat. Prod. Rep., 2005, 22, 580.62 A. Fontana, A. Cutignano and G. d’Ippolito, in Biocatalysis: Chem-

istry and Biology, ed. A. Trincone, Research Signpost, Trivandrum,India, 2005, p. 167.

63 J. L. Fortman and D. H. Sherman, ChemBioChem, 2005, 6, 960.64 J. Piel, D. Butzke, N. Fusetani, D. Hui, M. Platzer, G. Wen and S.

Matsunaga, J. Nat. Prod., 2005, 68, 472.65 J. Piel, Naturwiss. Rundsch., 2005, 58, 5.66 G. M. Nicholas and A. J. Phillips, Nat. Prod. Rep., 2005, 22, 144.67 W. E. Houssen and M. Jaspars, Methods Biotechnol., 2005, 20, 353.68 MarinLit database, Department of Chemistry, University of Canter-

bury: http://www.chem.canterbury.ac.nz/marinlit/marinlit.shtml.69 R. H. Feling, G. O. Buchanan, T. J. Mincer, C. A. Kauffman, P. R.

Jensen and W. Fenical, Angew. Chem., Int. Ed., 2003, 42, 355.70 P. G. Williams, G. O. Buchanan, R. H. Feling, C. A. Kauffman, P. R.

Jensen and W. Fenical, J. Org. Chem., 2005, 70, 6196.71 G. O. Buchanan, P. G. Williams, R. H. Feling, C. A. Kauffman, P. R.

Jensen and W. Fenical, Org. Lett., 2005, 7, 2731.72 D. S. Fukuda, J. S. Mynderse, P. J. Baker, D. M. Berry, L. D. Boeck,

R. C. Yao, F. P. Mertz, W. M. Nakatsukasa, J. Mabe and J. Ott,J. Antibiot., 1990, 43, 623.

73 D. S. Fukuda, J. S. Mynderse and R. C. Yao, U.S. Patent 4904590,1990.

74 I. E. Soria-Mercado, P. R. Jensen, W. Fenical, S. Kassel and J. Golen,Acta Crystallogr., Sect. E, 2004, 60, 1627.

75 I. E. Soria-Mercado, A. Prieto-Davo, P. R. Jensen and W. Fenical,J. Nat. Prod., 2005, 68, 904.

76 Y. Matsuo, M. Suzuki, H. Kasai, Y. Shizuri and S. Harayama, Environ.Microbiol., 2003, 5, 25.

77 Y. Matsuo, H. Imagawa, M. Nishizawa and Y. Shizuri, Science, 2005,307, 1598.

78 K. Kanoh, Y. Matsuo, K. Adachi, H. Imagawa, M. Nishizawa and Y.Shizuri, J. Antibiot., 2005, 58, 289.

79 P. Romero, L. Malet, L. M. Canedo, C. Cuevas and J. Fernando Reyes,PCT Int. Appl., WO 2005000880 A2 20050106, 2005.

80 A. J. Blackman and C. Li, Aust. J. Chem., 1994, 47, 1625.81 N. Lindquist and W. Fenical, Experientia, 1991, 47, 504.82 B. Carte and D. J. Faulkner, J. Org. Chem., 1983, 48, 2314.83 C. Holmstrom, S. James, B. A. Neilan, D. C. White and S. Kjelleberg,

Int. J. Syst. Bacteriol., 1998, 48, 1205.84 A. Franks, P. Haywood, C. Holmstrom, S. Egan, S. Kjelleberg and N.

Kumar, Molecules, 2005, 10, 1286.85 J. Vicar, M. Budesinsky and K. Blaha, Collect. Czech. Chem.

Commun., 1973, 38, 1940.86 J. Vicar, J. Smolikova and K. Blaha, Collect. Czech. Chem. Commun.,

1973, 38, 1957.87 M. Mitova, M. L. Tutino, G. Infusini, G. Marino and S. De Rosa,

Mar. Biotechnol., 2005, 7, 523.

88 R. R. Manam, S. Teisan, D. J. White, B. Nicholson, J. Grodberg,S. T. C. Neuteboom, K. S. Lam, D. A. Mosca, G. K. Lloyd andB. C. M. Potts, J. Nat. Prod., 2005, 68, 240.

89 F. Li, R. P. Maskey, S. Qin, I. Sattler, H. H. Fiebig, A. Maier, A. Zeeckand H. Laatsch, J. Nat. Prod., 2005, 68, 349.

90 H.-S. Lee, H. J. Shin, K. H. Jang, T. S. Kim, K.-B. Oh and J. Shin,J. Nat. Prod., 2005, 68, 623.

91 V. R. Macherla, J. Liu, C. Bellows, S. Teisan, B. Nicholson, K. S. Lamand B. C. M. Potts, J. Nat. Prod., 2005, 68, 780.

92 I. Kock, R. P. Maskey, M. A. F. Biabani, E. Helmke and H. Laatsch,J. Antibiot., 2005, 58, 530.

93 A. Gorajana, B. V. V. S. N. Kurada, S. Peela, P. Jangam, S. Vinjamuri,E. Poluri and A. Zeeck, J. Antibiot., 2005, 58, 526.

94 Y.-Q. Tang, I. Sattler, R. Thiericke, S. Grabley and X.-Z. Feng,J. Antibiot., 2000, 53, 934.

95 M. P. Sobolevskaya, S. Fotso, U. Havash, V. A. Denisenko, E. Helmke,N. G. Prokofeva, T. A. Kuznetsova, H. Laatsch and G. B. Elyakov,Chem. Nat. Compd., 2004, 40, 282.

96 W. H. Kim, J. H. Jung and E. Lee, J. Org. Chem., 2005, 70, 8190.97 H. Mertens, O. Schmidt and K. Adam, Patents DE 1083011, 1960,

and GB 875720.98 J. F. McGhie, W. A. Ross, D. Evans and J. E. Tomlin, J. Chem. Soc.,

1962, 350.99 J. S. Dickschat, T. Martens, T. Brinkhoff, M. Simon and S. Schulz,

Chem. Biodiversity, 2005, 2, 837.100 R. K. Phipps, J. W. Blunt, A. L. J. Cole and M. H. G. Munro,

ARKIVOC, 2004, 94.101 X.-X. Han, C.-B. Cui, Q.-Q. Gu, W.-M. Zhu, H.-B. Liu, J.-Y. Gu and

H. Osada, Tetrahedron Lett., 2005, 46, 6137.102 T. Mulhaupt, H. Kaspar, S. Otto, M. Reichert, G. Bringmann and T.

Lindel, Eur. J. Org. Chem., 2005, 2, 334.103 M. Winter, F. Gautschi, I. Flament, M. Stoll and I. M. Goldman,

U.S. Patent, 3924015, 1975.104 J. S. Dickschat, H. Reichenbach, I. Wagner-Dobler and S. Schulz,

Eur. J. Org. Chem., 2005, 4141.105 S. Tsukamoto, H. Hirota, M. Imachi, M. Fujimuro, H. Onuki, T. Ohta

and H. Yokosawa, Bioorg. Med. Chem. Lett., 2005, 15, 191.106 S. A. Waksman, E. S. Horning and E. L. Spencer, Science, 1942, 96,

202.107 K. Tatsuta, T. Tsuchiya, N. Mikami, S. Umezawa, H. Umezawa and

H. Naganawa, J. Antibiot., 1974, 27, 579.108 O. F. Smetanina, A. I. Kalinovskii, Y. V. Khudyakov, O. P. Moiseenko,

M. V. Pivkin, N. I. Menzorova, Y. T. Sibirtsev and T. A. Kuznetsova,Chem. Nat. Compd., 2005, 41, 243.

109 M.-A. Ouyang, R. Liu and Y.-H. Kuo, J. Asian Nat. Prod. Res., 2005,7, 761.

110 M. Tsuda, M. Sasaki, T. Mugishima, K. Komatsu, T. Sone, M.Tanaka, Y. Mikami and J. Kobayashi, J. Nat. Prod., 2005, 68, 273.

111 M. Sasaki, M. Tsuda, M. Sekiguchi, Y. Mikami and J. Kobayashi,Org. Lett., 2005, 7, 4261.

112 M. Tsuda, Y. Kasai, K. Komatsu, T. Sone, M. Tanaka, Y. Mikami andJ. Kobayashi, Org. Lett., 2004, 6, 3087.

113 T. Mugishima, M. Tsuda, Y. Kasai, H. Ishiyama, E. Fukushi, J.Kawabata, M. Watanabe, K. Akao and J. Kobayashi, J. Org. Chem.,2005, 70, 9430.

114 G. Bringmann, G. Lang, T. A. M. Gulder, H. Tsuruta, J. Muhlbacher,K. Maksimenka, S. Steffens, K. Schaumann, R. Stohr, J. Wiese,J. F. Imhoff, S. Perovic-Ottstadt, O. Boreiko and W. E. G. Muller,Tetrahedron, 2005, 61, 7252.

115 W. Liu, Q. Gu, W. Zhu, C. Cui, G. Fan, T. Zhu, H. Liu and Y. Fang,Tetrahedron Lett., 2005, 46, 4993.

116 W. Liu, Q. Gu, W. Zhu, C. Cui and G. Fan, J. Antibiot., 2005, 58, 441.117 W. Liu, Q. Gu, W. Zhu, C. Cui and G. Fan, J. Antibiot., 2005, 58, 621.118 R. Andrarde, W. A. Ayer and P. P. Mebe, Can. J. Chem., 1992, 70,

2526.119 N. Abe, T. Murata and A. Hirota, Biosci., Biotechnol., Biochem., 1998,

62, 661.120 G. A. Warr, J. A. Veitch, A. W. Walsh, G. A. Hesler, D. M. Pirnit, J. E.

Leet, P.-F. M. Lin, I. A. Medina, K. D. McBrien, S. Forenza, J. M.Clark and K. S. Lam, J. Antibiot., 1996, 49, 234.

121 J. He, U. Lion, I. Sattler, F. A. Gollmick, S. Grabley, J. Cai, M. Meiners,H. Schunke, K. Schaumann, U. Dechert and M. Krohn, J. Nat. Prod.,2005, 68, 1397.

122 Z. H. Xin, W. M. Zhu, Q. Q. Gu, Y. C. Fang, L. Duan and C. B. Cui,Chin. Chem. Lett., 2005, 16, 1227.


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i:10.

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123 A. Takatsuki, S. Suzuki, K. Ando, G. Tamura and K. Arima,J. Antibiot., 1968, 21, 671.

124 R. Sakai, T. Nakamura, T. Nishino, M. Yamamoto, A. Miyamura, H.Miyamoto, N. Ishiwata, N. Komatsu, H. Kamiya and N. Tsuruzoe,Bioorg. Med. Chem., 2005, 13, 6388.

125 K. Adachi, K. Kanoh, P. Wisespongp, M. Nishijima and Y. Shizuri,J. Antibiot., 2005, 58, 145.

126 K. Krohn, J. Dai, U. Florke, H.-J. Aust, S. Drager and B. Schulz,J. Nat. Prod., 2005, 68, 400.

127 X. Li, M. K. Kim, U. Lee, S.-K. Kim, J. S. Kang, H. D. Choi andB. W. Son, Chem. Pharm. Bull., 2005, 53, 453.

128 Y. Kasai, K. Komatsu, H. Shigemori, M. Tsuda, Y. Mikami and J.Kobayashi, J. Nat. Prod., 2005, 68, 777.

129 H. Wei, T. Itoh, M. Kinoshita, N. Kotoku, S. Aoki and M. Kobayashi,Tetrahedron, 2005, 61, 8054.

130 T. Yamada, M. Iritani, K. Minoura, K. Kawai and A. Numata, Org.Biomol. Chem., 2004, 2, 2131.

131 T. Yamada, M. Doi, A. Miura, W. Harada, M. Hiramura, K. Minoura,R. Tanaka and A. Numata, J. Antibiot., 2005, 58, 185.

132 M. Cueto, P. R. Jensen, C. Kauffman, W. Fenical, E. Lobkovsky andJ. Clardy, J. Nat. Prod., 2001, 64, 1444.

133 D.-C. Oh, P. R. Jensen, C. A. Kauffman and W. Fenical, Bioorg. Med.Chem., 2005, 13, 5267.

134 C. J. Smith, D. Abbanat, V. S. Bernan, W. M. Maiese, M. Greenstein,J. Jompa, A. Tahir and C. M. Ireland, J. Nat. Prod., 2000, 63, 142.

135 R. Garcia, J. M. Seco, S. A. Vazquez, E. Quinoa and R. Riguera,J. Org. Chem., 2002, 67, 4579.

136 X. Franck, M. E. Vaz Araujo, J.-C. Jullian, R. Hocquemiller and B.Figadere, Tetrahedron Lett., 2001, 42, 2801.

137 S. Gesner, N. Cohen, M. Ilan, O. Yarden and S. Carmeli, J. Nat. Prod.,2005, 68, 1350.

138 A. M. J. Senderowicz, G. Kaur, E. Sainz, C. Laing, W. D. Inman, J.Rodriguez, P. Crews, L. Malspeis, M. R. Grever, E. A. Sausville andK. L. K. Duncan, J. Natl. Cancer Inst., 1995, 87, 46.

139 P. Crews, L. V. Manes and M. Boehler, Tetrahedron Lett., 1986, 27,2797.

140 T. M. Zabriskie, J. A. Klocke, C. M. Ireland, A. H. Marcus, T. F.Molinski, D. J. Faulkner, C. Xu and J. Clardy, J. Am. Chem. Soc.,1986, 108, 3123.

141 O. E. Christian, J. Compton, K. R. Christian, S. L. Mooberry, F. A.Valeriote and P. Crews, J. Nat. Prod., 2005, 68, 1592.

142 X. Wu, X. Liu, G. Jiang, Y. Lin, W. Chan and L. L. P. Vrijmoed, Chem.Nat. Compd., 2005, 41, 27.

143 Y. Lin, X. Wu, S. Feng, G. Jiang, J. Luo, S. Zhou, L. L. Vrijmoed,E. B. Jones, K. Krohn, K. Steingrover and F. Zsila, J. Org. Chem.,2001, 66, 6252.

144 X. Y. Wu, X. H. Liu, Y. C. Lin, J. H. Luo, Z. G. She, L. Houjin, W. L.Chan, S. Antus, T. Kurtan, B. Elsasser and K. Krohn, Eur. J. Org.Chem., 2005, 4061.

145 H. Raistrick and D. J. Ross, Biochem. J., 1952, 50, 635.146 P. Cai, A. T. McPhail, E. Krainer, B. Katz, C. Pearce, C. Boros, B.

Caceres, D. Smith and D. R. Houck, Tetrahedron Lett., 1999, 40,1479.

147 X. Lin, Y. Huang, M. Fang, J. Wang, Z. Zheng and W. Su, FEMSMicrobiol. Lett., 2005, 251, 53.

148 B. Han, K. L. McPhail, H. Gross, D. E. Goeger, S. L. Mooberry andW. H. Gerwick, Tetrahedron, 2005, 61, 11723.

149 B. Han, D. Goeger, C. S. Maier and W. H. Gerwick, J. Org. Chem.,2005, 70, 3133.

150 S. Carmely and Y. Kashman, Tetrahedron Lett., 1985, 26, 511.151 E. H. Andrianasolo, H. Gross, D. Goeger, M. Musafija-Girt, K.

McPhail, R. M. Leal, S. L. Mooberry and W. H. Gerwick, Org. Lett.,2005, 7, 1375.

152 T. Teruya, K. Kobayashi, K. Suenaga and H. Kigoshi, TetrahedronLett., 2005, 46, 4001.

153 J. B. MacMillan and T. F. Molinski, J. Nat. Prod., 2005, 68, 604.154 Y. Ito and A. Butler, Limnol. Oceanogr., 2005, 50, 1918.155 N. Morsy, S. Matsuoka, T. Houdai, N. Matsumori, S. Adachi, M.

Murata, T. Iwashita and T. Fujita, Tetrahedron, 2005, 61, 8606.156 R. Echigoya, L. Rhodes, Y. Oshima and M. Satake, Harmful Algae,

2005, 4, 383.157 T. Kubota, A. Takahashi, M. Tsuda and J. Kobayashi, Mar. Drugs,

2005, 3, 113.158 M. Tsuda, Y. Kariya, R. Iwamoto, E. Fukushi, J. Kawabata and J.

Kobayashi, Mar. Drugs, 2005, 3, 1.

159 J. Wu, L. J. Long, Y. Song, S. Zhang, Q. X. Li, H. S. Huang and Z. H.Xiao, Chem. Pharm. Bull., 2005, 53, 330.

160 M. L. Souto, J. J. Fernandez, J. M. Franco, B. Paz, L. V. Gil and M.Norte, J. Nat. Prod., 2005, 68, 420.

161 C. O. Miles, A. L. Wilkins, A. D. Hawkes, A. Selwood, D. J. Jensen,J. Aasen, R. Munday, I. A. Samdal, L. R. Briggs, V. Beuzenberg andA. L. MacKenzie, Toxicon, 2004, 44, 325.

162 C. O. Miles, A. L. Wilkins, A. D. Hawkes, A. I. Selwood, D. J. Jensen,R. Munday, J. M. Cooney and V. Beuzenberg, Toxicon, 2005, 45, 61.

163 J. Aasen, S. L. MacKinnon, P. LeBlanc, J. A. Walter, P. Hovgaard, T.Aune and M. A. Quilliam, Chem. Res. Toxicol., 2005, 18, 509.

164 M. Satake, Y. Tanaka, Y. Ishikura, Y. Oshima, H. Naoki and T.Yasumoto, Tetrahedron Lett., 2005, 46, 3537.

165 K. Tanaka, Y. Itagaki, M. Satake, H. Naoki, T. Yasumoto, K.Nakanishi and N. Berova, J. Am. Chem. Soc., 2005, 127, 9561.

166 A. J. Bourdelais, H. M. Jacocks, J. L. C. Wright, P. M. Bigwarfe, Jr.and D. G. Baden, J. Nat. Prod., 2005, 68, 2.

167 B. Suarez-Gomez, M. L. Souto, P. G. Cruz, J. J. Fernandez and M.Norte, J. Nat. Prod., 2005, 68, 596.

168 C.-K. Lu, H.-N. Chou, C.-K. Lee and T.-H. Lee, Org. Lett., 2005, 7,3893.

169 M. Kita, M. Kondo, T. Koyama, K. Yamada, T. Matsumoto, K.-H.Lee, J.-T. Woo and D. Uemura, J. Am. Chem. Soc., 2004, 126, 4794.

170 M. Kita, N. Ohishi, K. Washida, M. Kondo, T. Koyama, K. Yamadaand D. Uemura, Bioorg. Med. Chem., 2005, 13, 5253.

171 A. A. Carlos, B. K. Baillie, M. Kawachi and T. Maruyama, J. Phycol.,1999, 35, 1054.

172 K. Onodera, H. Nakamura, Y. Oba and M. Ojika, Tetrahedron, 2003,59, 1067.

173 K. Onodera, H. Nakamura, Y. Oba, Y. Ohizumi and M. Ojika, J. Am.Chem. Soc., 2005, 127, 10406.

174 G. d’Ippolito, A. Cutignano, R. Briante, F. Febbraio, G. Cimino andA. Fontana, Org. Biomol. Chem., 2005, 3, 4065.

175 A. P. Rauter, M. M. Filipe, C. Prata, J. P. Noronha, M. A. M. Sampayo,J. Justino and J. Bermejo, Fitoterapia, 2005, 76, 433.

176 J. Hiort, K. Maksimenka, M. Reichert, S. Perovic-Ottstadt, W. H.Lin, V. Wray, K. Steube, K. Schaumann, H. Weber, P. Proksch, R.Ebel, W. E. G. Mueller and G. Bringmann, J. Nat. Prod., 2004, 67,1532.

177 J. Hiort, K. Maksimenka, M. Reichert, S. Perovic-Ottstadt, W. H. Lin,V. Wray, K. Steube, K. Schaumann, A. Weber, P. Proksch, R. Ebel,W. E. G. Muller and G. Bringmann, J. Nat. Prod., 2005, 68, 1821.

178 Y. H. Ye, H. L. Zhu, Y. C. Song, J. Y. Liu and R. X. Tan, J. Nat. Prod.,2005, 68, 1106.

179 J. I. Jimenez and P. J. Scheuer, J. Nat. Prod., 2001, 64, 200.180 H. Chen, Y. Feng, Z. Xu and T. Ye, Tetrahedron, 2005, 61, 11132.181 D. B. Stierle and A. A. Stierle, Experientia, 1992, 48, 1165.182 X. Gao and D. G. Hall, J. Am. Chem. Soc., 2005, 127, 1628.183 T. S. Bugni, D. Abbanat, V. S. Bernan, W. M. Maiese, M. Greenstein,

R. M. Van Wagoner and C. M. Ireland, J. Org. Chem., 2000, 65, 7195.184 G. Mehta and S. C. Pan, Tetrahedron Lett., 2005, 46, 5219.185 B. Bister, D. Bischoff, M. Strobele, J. Riedlinger, A. Reicke, F. Wolter,

A. T. Bull, H. Zahner, H.-P. Fiedler and R. D. Sussmuth, Angew.Chem., Int. Ed., 2004, 43, 2574.

186 C. W. Zapf, B. A. Harrison, C. Drahl and E. J. Sorensen, Angew.Chem., Int. Ed., 2005, 44, 6533.

187 M. K. Renner, Y. C. Shen, X. C. Cheng, P. R. Jensen, W. Frankmolle,C. A. Kauffman, W. Fenical, E. Lobkovsky and J. Clardy, J. Am.Chem. Soc., 1999, 121, 11273.

188 S. J. Wen, T. S. Hu and Z. J. Yao, Tetrahedron, 2005, 61, 4931.189 B. Han, K. L. McPhail, A. Ligresti, V. Di Marzo and W. H. Gerwick,

J. Nat. Prod., 2003, 66, 1364.190 I. R. Davies, M. Cheeseman, D. Gangani Niyadurupola and S. D.

Bull, Tetrahedron Lett., 2005, 46, 5547.191 H. Luesch, R. Pangilinan, W. Y. Yoshida, R. E. Moore and V. J. Paul,

J. Nat. Prod., 2001, 64, 304.192 Y. Peng, H. Pang, Z. Xu and T. Ye, Lett. Org. Chem., 2005, 2, 703.193 M. Yamazaki, H. Fujimoto and E. Okuyama, Chem. Pharm. Bull.,

1978, 26, 111.194 S. S. Afiyatullov, A. I. Kalinovskii, M. V. Pivkin, P. S. Dmitrenok and

T. A. Kuznetsova, Chem. Nat. Compd., 2005, 41, 236.195 H. H. Wasserman, G. C. Rodgers and D. D. Keith, J. Am. Chem. Soc.,

1969, 91, 1263.196 R. Liu, C.-B. Cui, L. Duan, Q.-Q. Gu and W.-M. Zhu, Arch. Pharm.

Res., 2005, 28, 1341.


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11Pu

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on h

ttp://

pubs

.rsc

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| do

i:10.

1039

/B60

3047

PView Online


197 F. Peypoux, F. Besson, G. Michel, C. Lenzen, L. Dierickx and L.Delcambe, J. Antibiot., 1980, 33, 1146.

198 G. K. Oleinikova, A. S. Dmitrenok, V. G. Voinov, E. L. Chaikina,L. S. Shevchenko and T. A. Kuznetsova, Chem. Nat. Compd., 2005,41, 461.

199 G. K. Oleinikova, A. S. Dmitrenok, V. G. Voinov, E. L. Chaikina,L. S. Shevchenko and T. A. Kuznetsova, Chem. Nat. Compd., 2005,41, 240.

200 A. Closse, R. Mauli, H. P. Sigg and A. G. Sandoz, Helv. Chim. Acta,1965, 49, 204.

201 G. Assante, L. Camarda, G. Nasini and L. Merlini, Phytopathol.Mediterr., 1980, 19, 163.

202 M. Sequin-Frey and C. Tamm, Helv. Chim. Acta, 1971, 54,851.

203 A. R. Burnett and R. H. Thomson, J. Chem. Soc. C, 1968, 857.204 Y. Li, X. Li and B. W. Son, Nat. Prod. Sci., 2005, 11, 136.205 T. Seki, M. Satake, L. Mackenzie, H. F. Kaspar and T. Yasumoto,

Tetrahedron Lett., 1995, 36, 7093.206 M. Dragunow, M. Trzoss, M. A. Brimble, R. Cameron, V. Beuzenberg,

P. Holland and D. Mountfort, Environ. Toxicol. Pharmacol., 2005, 20,305.

207 F. M. Lovel, J. Am. Chem. Soc., 1966, 88, 4510.208 P. R. Burkholder, R. M. Pfister and F. H. Leitz, Appl. Microbiol., 1966,

14, 649.209 J. D. Peschke, U. Hanefeld and H. Laatsch, Biosci., Biotechnol.,

Biochem., 2005, 69, 628.210 A. D. Rodriguez, J.-G. Shi and S. D. Huang, J. Nat. Prod., 1999, 62,

1228.211 J. M. Boehnlein, L. Z. Santiago-Vazquez and R. G. Kerr, Mar. Ecol.:

Prog. Ser., 2005, 303, 105.212 J. S. Sandler, W. Fenical, B. M. Gulledge, A. R. Chamberlin and J. J.

La Clair, J. Am. Chem. Soc., 2005, 127, 9320.213 J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote and M. R.

Prinsep, Nat. Prod. Rep., 2006, 23, 26.214 H. Kogen, K. Tago, S. Kaneko, K. Hamano, K. Onodera, H.

Haruyama, K. Minagawa, T. Kinoshita, T. Ishikawa, T. Tanimotoand Y. Tsujita, J. Antibiot., 1996, 49, 624.

215 J. T. Handley and A. J. Blackman, Aust. J. Chem., 2005, 58, 39.216 R. J. Andersen and O. Taglialatela-Scafati, J. Nat. Prod., 2005, 68,

1428.217 D. Y. Shi, L. J. Han, J. Sun, S. Li, S. J. Wang, Y. C. Yang, X. Fan and

J. G. Shi, Chin. Chem. Lett., 2005, 16, 777.218 S.-W. Yin, C.-Y. Wang, X.-M. Li and B.-G. Wang, Biochem. Syst.

Ecol., 2005, 33, 1288.219 M. T. Hamann, C. S. Otto, P. J. Scheuer and D. C. Dunbar, J. Org.

Chem., 1996, 61, 6594.220 M. T. Hamann, C. S. Otto, P. J. Scheuer and D. C. Dunbar, J. Org.

Chem., 1998, 63, 4856.221 L. Bourel-Bonnet, K. V. Rao, M. T. Hamann and A. Ganesan, J. Med.

Chem., 2005, 48, 1330.222 T. Kajiwara, A. Hatanaka, T. Kawai, M. Ishihara and T. Tuneya,

Nippon Suisan Gakkaishi, 1987, 53, 1901.223 Y. Akakabe, K. Washizu, K. Matsui and T. Kajiwara, Biosci.,

Biotechnol., Biochem., 2005, 69, 1348.224 K. H. Jang, B. H. Lee, B. W. Choi, H.-S. Lee and J. Shin, J. Nat. Prod.,

2005, 68, 716.225 K. Inaoka, Y. Nishizawa, H. Tone and T. Kamiya, Jpn. Kokai Tokkyo

Koho, JP H04-49259, 1992.226 M. Iwashima, J. Mori, X. Ting, T. Matsunaga, K. Hayashi, D.

Shinoda, H. Saito, U. Sankawa and T. Hayashi, Biol. Pharm. Bull.,2005, 28, 374.

227 J. Mori, M. Iwashima, H. Wakasugi, H. Saito, T. Matsunaga, M.Ogasawara, S. Takahashi, H. Suzuki and T. Hayashi, Chem. Pharm.Bull., 2005, 53, 1159.

228 D. Abatis, C. Vagias, D. Galanakis, J. N. Norris, D. Moreau, C.Roussakis and V. Roussis, Tetrahedron Lett., 2005, 46, 8525.

229 M. Ishitsuka, T. Kusumi, Y. Nomura, T. Konno and H. Kakisawa,Chem. Lett., 1979, 1269.

230 L.-A. Tziveleka, D. Abatis, K. Paulus, R. Bauer, C. Vagias and V.Roussis, Chem. Biodiversity, 2005, 2, 901.

231 W. H. Gerwick, W. Fenical, N. Fritsch and J. Clardy, TetrahedronLett., 1979, 145.

232 O. M. M. Sabry, S. Andrews, K. L. McPhail, D. E. Goeger, A. Yokochi,K. T. LePage, T. F. Murray and W. H. Gerwick, J. Nat. Prod., 2005,68, 1022.

233 F. Song, X. Xu, S. Li, S. Wang, J. Zhao, P. Cao, Y. Yang, X. Fan, J.Shi, L. He and Y. Lu, J. Nat. Prod., 2005, 68, 1309.

234 A. Ortalo-Magne, G. Culioli, R. Valls, B. Pucci and L. Piovetti,Phytochemistry, 2005, 66, 2316.

235 J. F. Biard, J. F. Verbist, R. Floch and Y. Letourneux, TetrahedronLett., 1980, 21, 1849.

236 T. Kusumi, Y. Shibata, M. Ishizuka, T. Kinoshita and H. Kakizawa,Chem. Lett., 1979, 277.

237 C. K. Tsang, A. Ina, T. Goto and Y. Kamei, Neuroscience, 2005, 132,633.

238 C. F. Cross, E. J. Bevan and J. F. Briggs, Chem.–Ztg., 1907, 31, 725.239 H. S. Kang, H. Y. Chung, J. H. Jung, B. W. Son and J. S. Choi, Chem.

Pharm. Bull., 2003, 51, 1012.240 Y. Fukuyama, M. Kodama, I. Miura, Z. Kinzyo, M. Kido, H. Mori,

Y. Nakayama and M. Takahashi, Chem. Pharm. Bull., 1989, 37, 349.241 Y. Fukuyama, M. Kodama, I. Miura, Z. Kinzyo, H. Mori, Y.

Nakayama and M. Takahashi, Chem. Pharm. Bull., 1990, 38, 133.242 Y. Fukuyama, I. Miura, Z. Kinzyo, Y. Nakayama, M. Takahashi and

M. Kido, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 1983, 26,126.

243 Y. C. Kim, R. B. An, N. Y. Yoon, T. J. Nam and J. S. Choi, Arch.Pharm. Res., 2005, 28, 1376.

244 M. Ochi, H. Kotsuki, K. Muraoka and T. Tokoroyama, Bull. Chem.Soc. Jpn., 1979, 52, 629.

245 K. Kurata, K. Taniguchi and M. Suzuki, Phytochemistry, 1996, 41,749.

246 W. Fenical, J. J. Sims, D. Squatrito, R. M. Wing and P. Radlick, J. Org.Chem., 1973, 38, 2383.

247 T. Laube, W. Beil and K. Seifert, Tetrahedron, 2005, 61, 1141.248 A. A. El-Gamal, W.-L. Wang and C.-Y. Duh, J. Nat. Prod., 2005, 68,

815.249 N. K. Kubota, H. Iwamoto, Y. Fukazawa and Y. Uchio, Heterocycles,

2005, 65, 2675.250 J. Sun, D. Shi, M. Ma, S. Li, S. Wang, L. Han, Y. Yang, X. Fan, J. Shi

and L. He, J. Nat. Prod., 2005, 68, 915.251 K. Yamada, H. Yazawa, D. Uemura, M. Toda and Y. Hirata,

Tetrahedron, 1969, 25, 3509.252 H. Nemoto, M. Nagamochi, H. Ishibashi and K. Fukumoto, J. Org.

Chem., 1994, 59, 74.253 J. Sun, L. J. Han, D. Y. Shi, X. Fan, S. J. Wang, S. Li, Y. C. Yang and

J. G. Shi, Chin. Chem. Lett., 2005, 16, 1611.254 D. J. Goldsmith, T. K. John, C. D. Kwong and G. R. Painter, III,

J. Org. Chem., 1980, 45, 3989.255 Y. Shizuri and K. Yamada, Phytochemistry, 1985, 24, 1385.256 M. Kladi, C. Vagias, G. Furnari, D. Moreau, C. Roussakis and V.

Roussis, Tetrahedron Lett., 2005, 46, 5723.257 S. Mao and Y. Guo, Helv. Chim. Acta, 2005, 88, 1034.258 J. J. Fernandez, M. L. Souto, L. V. Gil and M. Norte, Tetrahedron,

2005, 61, 8910.259 M. Kuniyoshi, P. G. Wahome, T. Miono, T. Hashimoto, M. Yokoyama,

K. L. Shrestha and T. Higa, J. Nat. Prod., 2005, 68, 1314.260 M. Suzuki, T. Kawamoto, C. S. Vairappan, T. Ishii, T. Abe and M.

Masuda, Phytochemistry, 2005, 66, 2787.261 O. J. McConnell and W. Fenical, J. Org. Chem., 1978, 43, 4238.262 V. J. Paul, O. J. McConnell and W. Fenical, J. Org. Chem., 1980, 45,

3401.263 J. Kimura, Y. Tobita, T. Motoyama, Y. Ataka and Y. Takada, J. Nat.

Prod., 2005, 68, 585.264 S. Mataka, H. Eguchi, K. Takahashi, T. Hatta and M. Tashiro, Bull.

Chem. Soc. Jpn., 1989, 62, 3127.265 K. Nishizawa and J. Y. Satoh, Chem. Soc. Jpn., 1975, 48, 1875.266 J. E. Lightowler and H. J. Rylance, Br. J. Pharmacol., 1964, 22, 221.267 V. L. Afanas’eva, A. V. Lyubeshkin, S. S. Kovaleva, M. R. Bagreeva,

O. S. Anisimova and R. G. Glushkov, Khim.-Farm. Zh., 1987, 21,1367.

268 W. Wang, Y. Okada, H. Shi, Y. Wang and T. Okuyama, J. Nat. Prod.,2005, 68, 620.

269 J. Zhao, M. Ma, S. Wang, S. Li, P. Cao, Y. Yang, Y. Lu, J. Shi, N. Xu,X. Fan and L. He, J. Nat. Prod., 2005, 68, 691.

270 D. B. Stierle, R. M. Wing and J. J. Sims, Tetrahedron, 1979, 35,2855.

271 M. D. Higgs, D. J. Vanderah and D. J. Faulkner, Tetrahedron, 1977,33, 2775.

272 C. Ireland, M. O. Stallard, D. J. Faulkner, J. Finer and J. Clardy, J. Org.Chem., 1976, 41, 2461.


Dow

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PView Online


273 M. G. Knott, H. Mkwananzi, C. E. Arendse, D. T. Hendricks, J. J.Bolton and D. R. Beukes, Phytochemistry, 2005, 66, 1108.

274 W.-H. Zhang, H.-M. Zhong and C.-T. Che, J. Asian Nat. Prod. Res.,2005, 7, 59.

275 M. Lorenzo, M. Cueto, A. San-Martın, V. Fajardo and J. Darias,Tetrahedron, 2005, 61, 9550.

276 M. Kitamura, T. Koyama, Y. Nakano and D. Uemura, Chem. Lett.,2005, 34, 1272.

277 J. Kubanek, A. C. Prusak, T. W. Snell, R. A. Giese, K. I. Hardcastle,C. R. Fairchild, W. Aalbersberg, C. Raventos-Suarez and M. E. Hay,Org. Lett., 2005, 7, 5261.

278 M. A. Graber, W. H. Gerwick and D. P. Cheney, Tetrahedron Lett.,1996, 37, 4635.

279 H. Miyaoka, Y. Hara, I. Shinohara, T. Kurokawa and Y. Yamada,Tetrahedron Lett., 2005, 46, 7945.

280 A. Lopez and W. H. Gerwick, Lipids, 1987, 22, 190.281 T. Tsuzuki, K. Tanaka, S. Kuwahara and T. Miyazawa, Lipids, 2005,

40, 147.282 E. Kurosawa, A. Fukuzawa and T. Irie, Tetrahedron Lett., 1973, 42,

4135.283 H. Lee, H. Kim, T. Yoon, B. Kim, S. Kim, H.-D. Kim and D. Kim,

J. Org. Chem., 2005, 70, 8723.284 M. Maeda, T. Kodama, T. Tanaka, H. Yoshizumi, T. Takemoto, K.

Nomoto and T. Fujita, Chem. Pharm. Bull., 1986, 34, 4892.285 J. Clayden, F. E. Knowles and I. R. Baldwin, J. Am. Chem. Soc., 2005,

127, 2412.286 J. Y. Su, Y. L. Zhong, L. M. Zeng, H. M. Wu and K. Ma,

Phytochemistry, 1995, 40, 195.287 J. Justicia, J. L. Oller-Lopez, A. G. Campana, J. E. Oltra, J. M. Cuerva,

E. Bunuel and D. J. Cardenas, J. Am. Chem. Soc., 2005, 127, 14911.288 H. J. Park, Park, H. Y. Chung, J. Kim and J. S. Choi, J. Fish. Sci.

Technol., 1999, 2, 1.289 H. Park, M. Kurokawa, K. Shiraki, N. Nakamura, J. Choi and M.

Hattori, Biol. Pharm. Bull., 2005, 28, 2258.290 S. Tilvi, M. Majik and C. G. Naik, Eur. J. Mass Spectrom., 2005, 11,

345.291 G. W. Zhang, X. Q. Ma, C. X. Zhang, J. Y. Su, W. C. Ye, X. Q. Zhang,

X. S. Yao and L. M. Zeng, Helv. Chim. Acta, 2005, 88, 885.292 S. N. Ayyad, Mansoura Sci. Bull., A: Chem., 2004, 31, 115.293 V. Costantino, E. Fattorusso, C. Imperatore and A. Mangoni,

Eur. J. Org. Chem., 2005, 2, 368.294 C. Emura, R. Higuchi, T. Miyamoto and R. W. M. Van Soest, J. Org.

Chem., 2005, 70, 3031.295 V. Costantino, M. D’Esposito, E. Fattorusso, A. Mangoni, N. Basilico,

S. Parapini and D. Taramelli, J. Med. Chem., 2005, 48, 7411.296 T. N. Makarieva, A. G. Guzii, V. A. Denisenko, P. S. Dmitrenok, E. A.

Santalova, E. V. Pokanevich, T. F. Molinski and V. A. Stonik, J. Nat.Prod., 2005, 68, 255.

297 L. Barbieri, V. Costantino, E. Fattorusso and A. Mangoni, J. Nat.Prod., 2005, 68, 1527.

298 T. N. Makarieva, V. A. Denisenko, P. S. Dmitrenok, A. G. Guzii,E. A. Santalova, V. A. Stonik, J. B. MacMillan and T. F. Molinski,Org. Lett., 2005, 7, 2897.

299 N. L. Segraves and P. Crews, J. Nat. Prod., 2005, 68, 118.300 K. Warabi, T. Hamada, Y. Nakao, S. Matsunaga, H. Hirota, R. W. M.

van Soest and N. Fusetani, J. Am. Chem. Soc., 2005, 127, 13262.301 T. A. Mansoor, B. H. Bae, J. Hong, C. O. Lee, K. S. Im and J. H. Jung,

Lipids, 2005, 40, 981.302 M. Ishibashi, S. Takeuchi and J. Kobayashi, Tetrahedron Lett., 1993,

34, 3749.303 M. Tsuda, T. Endo, M. Perpelescu, S. Yoshida, K. Watanabe, J.

Fromont, Y. Mikami and J. Kobayashi, Tetrahedron, 2003, 59, 1137.304 H. Mizutani, M. Watanabe and T. Honda, Synlett, 2005, 793.305 S. C. Jain, R. Kumar, R. Goswami, M. K. Pandey, S. Khurana, L.

Rohatgi and K. Gyanda, Pure Appl. Chem., 2005, 77, 185.306 S. Tsukamoto, M. Takahashi, S. Matsunaga, N. Fusetani and R. W. M.

van Soest, J. Nat. Prod., 2000, 63, 682.307 A. P. Dobbs, A. Venturelli, L. A. Butler and R. J. Parker, Synlett,

2005, 4, 652.308 A. Kawakami, T. Miyamoto, R. Higuchi, M. Kuwano and R. W. M.

van Soest, Tetrahedron Lett., 2001, 42, 3335.309 N. Sudhakar, A. Ravi Kumar, A. Prabhakar, B. Jagadeesh and B.

Venkateswara Rao, Tetrahedron Lett., 2005, 46, 325.310 P. Bhaket, K. Morris, C. S. Stauffer and A. Datta, Org. Lett., 2005, 7,

875.

311 I. Kuroda, M. Musman, I. I. Ohtani, T. Ichiba, J. Tanaka, D. G.Gravalos and T. Higa, J. Nat. Prod., 2002, 65, 1505.

312 V. Ledroit, C. Debitus, C. Lavaud and G. Massiot, Tetrahedron Lett.,2003, 44, 225.

313 R. G. Linington, M. Robertson, A. Gauthier, B. B. Findlay, R. vanSoest and R. J. Andersen, Org. Lett., 2002, 4, 4089.

314 J. Sun, X. Han and B. Yu, Synlett, 2005, 437.315 K. Watanabe, Y. Tsuda, M. Hamada, M. Omori, G. Mori, K. Iguchi,

H. Naoki, T. Fujita and R. W. M. Van Soest, J. Nat. Prod., 2005, 68,1001.

316 M. L. Lerch, M. K. Harper and D. J. Faulkner, J. Nat. Prod., 2003,66, 667.

317 B. W. Gung, C. Gibeau and A. Jones, Tetrahedron: Asymmetry, 2005,16, 3107.

318 H. Tada and F. Yasuda, Chem. Lett., 1984, 779.319 N. Fusetani, M. Sugano, S. Matsunaga and K. Hashimoto, Tetrahe-

dron Lett., 1987, 28, 4311.320 S. Lopez, F. Fernandez-Trillo, P. Midon, L. Castedo and C. Saa, J. Org.

Chem., 2005, 70, 6346.321 T. Yosief, A. Rudi, Y. Wolde-ab and Y. Kashman, J. Nat. Prod., 1998,

61, 491.322 A. Fontana, G. d’Ippolito, L. D’Souza, E. Mollo, P. S. Parameswaram

and G. Cimino, J. Nat. Prod., 2001, 64, 131.323 C. Xu, J. M. Raible and P. H. Dussault, Org. Lett., 2005, 7, 2509.324 N. Sata, H. Abinsay, W. Y. Yoshida, F. D. Horgen, N. Sitachitta, M.

Kelly and P. J. Scheuer, J. Nat. Prod., 2005, 68, 1400.325 M. Holzwarth, J. M. Trendel, P. Albrecht, A. Maier and W. Michaelis,

J. Nat. Prod., 2005, 68, 759.326 R. A. Epifanio, L. S. Pinheiro and N. C. Alves, J. Braz. Chem. Soc.,

2005, 16, 1367.327 R. J. Capon, S. Singh, S. Ali and S. Sotheeswaran, Aust. J. Chem.,

2005, 58, 18.328 F. Berrue, O. P. Thomas, R. Fernandez and P. Amade, J. Nat. Prod.,

2005, 68, 547.329 F. Berrue, O. P. Thomas, C. F. L. Bon, F. Reyes and P. Amade,

Tetrahedron, 2005, 61, 11843.330 C. Campagnuolo, E. Fattorusso, A. Romano, O. Taglialatela-Scafati,

N. Basilico, S. Parapini and D. Taramelli, Eur. J. Org. Chem., 2005,23, 5077.

331 D. B. Stierle and D. J. Faulkner, J. Org. Chem., 1980, 45, 3396.332 M. Akiyama, Y. Isoda, M. Nishimoto, A. Kobayashi, D. Togawa, N.

Hirao, A. Kuboki and S. Ohira, Tetrahedron Lett., 2005, 46, 7483.333 A. S. Ratnayake, R. A. Davis, M. K. Harper, C. A. Veltri, C. D.

Andjelic, L. R. Barrows and C. M. Ireland, J. Nat. Prod., 2005, 68,104.

334 A. C. Granato, J. H. H. L. de Oliveira, M. H. R. Seleghim, R. G. S.Berlinck, M. L. Macedo, A. G. Ferreira, R. M. da Rocha, E. Hajdu,S. Peixinho, C. O. Pessoa, M. O. Moraes and B. C. Cavalcanti, Quim.Nova, 2005, 28, 192.

335 S. Cao, C. Foster, M. Brisson, J. S. Lazo and D. G. I. Kingston, Bioorg.Med. Chem., 2005, 13, 999.

336 N. Sata, M. A. Galario, N. Sitachitta, P. J. Scheuer and M. Kelly,J. Nat. Prod., 2005, 68, 262.

337 R. H. Cichewicz, F. A. Valeriote and P. Crews, Org. Lett., 2004, 6,1951.

338 G. R. Pettit, J. Xu, J. Chapuis, R. K. Pettit, L. P. Tackett, D. L. Doubek,J. N. A. Hooper and J. M. Shmidt, J. Med. Chem., 2004, 47, 1149.

339 X. Jiang, J. Garcıa-Fortanet and J. K. De Brabander, J. Am. Chem.Soc., 2005, 127, 11254.

340 M. E. Green, J. C. Rech and P. E. Floreancig, Org. Lett., 2005, 7, 4117.341 S. Kanazawa, N. Fusetani and S. Matsunaga, Tetrahedron Lett., 1993,

34, 1065.342 N. Cramer, S. Laschat, A. Baro, H. Schwalbe and C. Richter, Angew.

Chem., Int. Ed., 2005, 44, 820.343 N. Fusetani, T. Sugawara, S. Matsunaga and H. Hirota, J. Org. Chem.,

1991, 56, 4971.344 S. Nishimura, S. Matsunaga, M. Yoshida, H. Hirota, S. Yokoyama

and N. Fusetani, Bioorg. Med. Chem., 2005, 13, 449.345 P. T. Northcote, J. W. Blunt and M. H. G. Munro, Tetrahedron Lett.,

1991, 32, 6411.346 M. E. Bordeleau, J. Mathews, J. Wojnar, L. Linquist, O. Novac, E.

Janowsky, N. Sonenburg, P. Northcote, P. Teesdale-Spittle and J.Pelletier, Proc. Natl. Acad. Sci. U. S. A., 2005, 102, 10460.

347 W. K. Low, Y. J. Dang, T. Schneider-Poetsch, Z. G. Shi, N. S. Choi,W. C. Merrick, D. Romo and J. O. Liu, Mol. Cell, 2005, 20, 709.


Dow

nloa

ded

on 2

3 Ja

nuar

y 20

11Pu

blis

hed

on h

ttp://

pubs

.rsc

.org

| do

i:10.

1039

/B60

3047

PView Online


348 T. Araki, S. Matsunaga and N. Fusetani, Biosci., Biotechnol.,Biochem., 2005, 69, 1318.

349 N. Kotoku, L. Cao, S. Aoki and M. Kobayashi, Heterocycles, 2005,65, 563.

350 T. Hamada, T. Sugawara, S. Matsunaga and N. Fusetani, TetrahedronLett., 1994, 35, 719.

351 T. Hamada, T. Sugawara, S. Matsunaga and N. Fusetani, TetrahedronLett., 1994, 35, 609.

352 T. Hamada, S. Matsunaga, G. Yano and N. Fusetani, J. Am. Chem.Soc., 2005, 127, 110.

353 K. C. Nicolaou, D. Schlawe, D. W. Kim, D. A. Longbottom, R. G.de Noronha, D. E. Lizos, R. R. Manam and D. J. Faulkner, Chem.–Eur. J., 2005, 11, 6197.

354 A. Randazzo, G. Bifulco, C. Giannini, M. Bucci, C. Debitus, G. Cirinoand L. Gomez-Paloma, J. Am. Chem. Soc., 2001, 123, 10870.

355 K. C. Nicolaou, D. W. Kim, D. Schlawe, D. E. Lizos, R. G. de Noronhaand D. A. Longbottom, Angew. Chem., Int. Ed., 2005, 44, 4925.

356 G. R. Pettit and R. Tan, J. Nat. Prod., 2005, 68, 60.357 D. E. Williams, B. O. Patrick, H. W. Behrisch, R. Van Soest, M.

Roberge and R. J. Andersen, J. Nat. Prod., 2005, 68, 327.358 G. R. Pettit, J. Xu, A. Dorsaz and M. D. Williams, Bioorg. Med. Chem.

Lett., 1995, 5, 1339.359 A. Napolitano, I. Bruno, R. Riccio and L. Gomez-Paloma, Tetrahe-

dron, 2005, 61, 6808.360 A. Zampella, M. V. D’Auria, L. Gomez-Paloma, A. Casapullo, L.

Minale, C. Debitus and Y. Henin, J. Am. Chem. Soc., 1996, 118,6202.

361 A. Zampella, R. D’Orsi, V. Sepe, A. Casapullo, M. C. Monti and M. V.D’Auria, Org. Lett., 2005, 7, 3585.

362 N. Oku, A. G. Benson Krishnamoorthy, R. L. Ferguson, M. Z. Lipton,L. R. Phillips, K. R. Gustafson and J. B. McMahon, J. Org. Chem.,2005, 70, 6842.

363 P. W. Ford, K. R. Gustafson, T. C. McKee, N. Shigematsu, L. K.Maurizi, L. K. Pannell, D. E. Williams, E. D. de Silva and P. Lassota,J. Am. Chem. Soc., 1999, 121, 5899.

364 K. Makino, E. Nagata and Y. Hamada, Tetrahedron Lett., 2005, 46,6827.

365 N. Oku, K. R. Gustafson, L. K. Cartner, J. A. Wilson, N. Shigamatsu,S. Hess, L. K. Pannell, M. R. Boyd and J. B. McMahon, J. Nat. Prod.,2004, 67, 1407.

366 D. E. Williams, P. Austin, A. R. Diaz-Marrero, R. Van Soest, T.Matainaho, C. D. Roskelley, M. Roberge and R. J. Andersen, Org.Lett., 2005, 7, 4173.

367 P. Phuwapraisirisan, S. Matsunaga and N. Fusetani, Org. Lett., 2005,7, 2233.

368 S. Tsukamoto, K. Koimaru and K. Ohta, Mar. Drugs, 2005, 3, 29.369 G. R. Pettit, Z. A. Chicaz, F. Gao, C. L. Herald, M. R. Boyd, J. M.

Schmidt and J. N. A. Hooper, J. Org. Chem., 1993, 58, 1302.370 R. K. Pettit, T. Woyke, S. Pon, Z. A. Cichacz, G. R. Pettit and C. L.

Herald, Med. Mycol., 2005, 43, 453.371 V. A. Klenchin, R. King, J. Tanaka, G. Marriott and I. Rayment,

Chem. Biol., 2005, 12, 287.372 N. Takada, H. Sato, K. Suenaga, H. Arimoto, K. Yamada, K. Ueda

and D. Uemura, Tetrahedron Lett., 1999, 40, 6309.373 T. R. Hoye and J. Wang, J. Am. Chem. Soc., 2005, 127, 6950.374 M. R. Rao and D. J. Faulkner, J. Nat. Prod., 2002, 65, 386.375 C. S. Barry, N. Bushby, J. P. H. Charmant, J. D. Elsworth, J. R. Harding

and C. L. Willis, Chem. Commun., 2005, 5097.376 M. S. Agrawal and B. F. Bowden, Mar. Drugs, 2005, 3, 9.377 B. Carte and D. J. Faulkner, Tetrahedron, 1981, 37, 2335.378 Y. M. Xu, R. K. Johnson and S. M. Hecht, Bioorg. Med. Chem., 2005,

13, 657.379 R. Kazlauskas, R. O. Lidgard, P. T. Murphy and R. J. Wells,

Tetrahedron Lett., 1980, 21, 2277.380 R. Kazlauskas, R. O. Lidgard, P. T. Murphy, R. J. Wells and J. F.

Blount, Aust. J. Chem., 1981, 34, 765.381 E. O. Pordesimo and F. J. Schmitz, J. Org. Chem., 1990, 55, 4704.382 M. S. Butler, T. K. Lim, R. J. Capon and L. S. Hammond,

Aust. J. Chem., 1991, 44, 287.383 E. A. Couladouros, E. N. Pitsinos, V. I. Moutsos and G. Sarakinos,

Chem.–Eur. J., 2005, 11, 406.384 P. Sauleau, P. Retailleau, J. Vacelet and M.-L. Bourguet-Kondracki,

Tetrahedron, 2005, 61, 955.385 A. Arda, J. Rodrıguez, R. M. Nieto, C. Bassarello, L. Gomez-Paloma,

G. Bifulco and C. Jimenez, Tetrahedron, 2005, 61, 10093.

386 R. J. Capon, D. Vuong, E. Lacey and J. H. Gill, J. Nat. Prod., 2005,68, 179.

387 R. J. Capon, D. Vuong, M. McNally, T. Peterle, N. Trotter, E. Laceyand J. H. Gill, Org. Biomol. Chem., 2005, 3, 118.

388 H. Suzuki, K. Shindo, A. Ueno, T. Miura, M. Takei, M. Sakakibara,H. Fukamachi, J. Tanaka and T. Higa, Bioorg. Med. Chem. Lett.,1999, 9, 1361.

389 R. A. Fairhurst, D. Janus and A. Lawrence, Org. Lett., 2005, 7,4697.

390 J. G. Ondeyka, K. B. Herath, H. Jayasuriya, J. D. Polishook, G. F. Bills,A. W. Dombrowski, M. Mojena, G. Koch, J. DiSalvo, J. DeMartino,Z. Guan, W. Nanakorn and C. Morenberg, Mol. Diversity, 2005, 9,123.

391 M. Tsuda, K. Hirano and J. Kobayashi, Tetrahedron Lett., 1999, 40,4819.

392 S. P. Romeril, V. Lee, J. E. Baldwin and T. D. W. Claridge, Tetrahedron,2005, 61, 1127.

393 H. Ishiyama, M. Tsuda, T. Endo and J. Kobayashi, Molecules, 2005,10, 312.

394 R. A. Keyzers, C. E. Arendse, D. T. Hendricks, T. Samaai and M. T.Davies-Coleman, J. Nat. Prod., 2005, 68, 506.

395 G. Lang, A. Pinkert, J. W. Blunt and M. H. G. Munro, J. Nat. Prod.,2005, 68, 1796.

396 N. K. Utkina, A. E. Makarchenko and V. A. Denisenko, J. Nat. Prod.,2005, 68, 1424.

397 N. L. Segraves and P. Crews, J. Nat. Prod., 2005, 68, 1484.398 S. Rubnov, C. Chevallier, O. Thoison, C. Debitus, O. Laprevote, D.

Grenard and T. Sevenet, Nat. Prod. Res., 2005, 19, 75.399 M. Tsuda, Y. Takahashi, J. Fromont, Y. Mikami and J. Kobayashi,

J. Nat. Prod., 2005, 68, 1277.400 B. Q. Bao, Q. S. Sun, X. S. Yao, J. K. Hong, C. O. Lee, C. J. Sim, K. S.

Im and J. H. Jung, J. Nat. Prod., 2005, 68, 711.401 K. B. Oh, W. Mar, S. Kim, J. Y. Kim, M. N. Oh, J. G. Kim, D. Shin,

C. J. Sim and J. Shin, Bioorg. Med. Chem. Lett., 2005, 15, 4927.402 D. T. A. Youssef, J. Nat. Prod., 2005, 68, 1416.403 Y. Iinuma, S. Kozawa, H. Ishiyama, M. Tsuda, E. Fukushi, J.

Kawabata, J. Fromont and J. Kobayashi, J. Nat. Prod., 2005, 68, 1109.404 V. K. Rao, N. Kasanah, S. Wahyuono, B. L. Tekwani, R. F. Schinazi

and M. T. Hamann, J. Nat. Prod., 2004, 67, 1314.405 A. Casapullo, G. Bifulco, I. Bruno and R. Riccio, J. Nat. Prod., 2000,

63, 447.406 T. Kouko, K. Matsumura and T. Kawasaki, Tetrahedron, 2005, 61,

2309.407 A. Aiello, M. D’Esposito, E. Fattorusso, M. Menna, W. E. G. Muller,

S. Perovic-Ottstadt, H. Tsuruta, T. A. M. Gulder and G. Bringmann,Tetrahedron, 2005, 61, 7266.

408 A. R. Carroll, A. Ngo, R. J. Quinn, J. Redburn and J. N. A. Hooper,J. Nat. Prod., 2005, 68, 804.

409 N. B. Perry, L. Ettouati, M. Litaudon, J. W. Blunt and M. H. G.Munro, Tetrahedron, 1994, 50, 3987.

410 M. Simone, E. Erba, G. Damia, F. Vikhanskaya, A. M. Di Francesco,R. Riccardi, C. Bailly, C. Cuevas, J. M. F. Sousa-Faro and M.D’Incalci, Eur. J. Cancer, 2005, 41, 2366.

411 G. R. Pettit, J. C. Knight, J. C. Collins, D. L. Herald, R. K. Pettit,M. R. Boyd and V. G. Young, J. Nat. Prod., 2000, 63, 793.

412 C. Chan, R. Heid, S. Zheng, J. Guo, B. Zhou, T. Furuuchi and S. J.Danishefsky, J. Am. Chem. Soc., 2005, 127, 4596.

413 B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721.414 P. Magnus and K. S. Matthews, J. Am. Chem. Soc., 2005, 127, 12476.415 J. W. Lane, Y. Chen and R. M. Williams, J. Am. Chem. Soc., 2005,

127, 12684.416 K. Warabi, S. Matsunaga, R. W. M. van Soest and N. Fusetani, J. Org.

Chem., 2003, 68, 2765.417 A. Furstner, M. M. Domostoj and B. Scheiper, J. Am. Chem. Soc.,

2005, 127, 11620.418 J. F. Hu, J. Peng, A. B. Kazi, M. Kelly and M. T. Hamann, J. Chem.

Res., 2005, 7, 427.419 E. Fattorusso and O. Taglialatela-Scafati, Tetrahedron Lett., 2000, 41,

9917.420 G. Papeo, M. A. G. Z. Frau, D. Borghi and M. Varasi, Tetrahedron

Lett., 2005, 46, 8635.421 J. Patel, N. Pelloux-Leon, F. Minassian and Y. Vallee, J. Org. Chem.,

2005, 70, 9081.422 W. A. Gallimore, M. Kelly and P. J. Scheuer, J. Nat. Prod., 2005, 68,

1420.


Dow

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ttp://

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.rsc

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i:10.

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PView Online


423 J. C. Braekman, D. Daloze, H. Tavares, E. Hajdu and R. W. M. vanSoest, J. Nat. Prod., 2000, 63, 193.

424 Z. D. Aron and L. E. Overman, J. Am. Chem. Soc., 2005, 127, 3380.425 R. G. S. Berlinck, J. C. Braekman, D. Daloze, I. Bruno, R. Riccio, S.

Ferri, S. Spampinato and E. Speroni, J. Nat. Prod., 1993, 56, 1007.426 L. E. Overman and Y. H. Rhee, J. Am. Chem. Soc., 2005, 127, 15652.427 K. Ravinder, A. V. Reddy, T. V. Raju and Y. Venkateswarlu,

ARKIVOC, 2005, 51.428 S. Matsunaga, H. Kobayashi, R. W. M. van Soest and N. Fusetani,

J. Org. Chem., 2005, 70, 1893.429 F. C. Schroeder, T. R. Kau, P. A. Silver and J. Clardy, J. Nat. Prod.,

2005, 68, 574.430 S. N. Georgiades and J. Clardy, Org. Lett., 2005, 7, 4091.431 A. Kijjoa, J. Bessa, R. Wattanadilok, P. Sawangwong, M. S. J.

Nascimento, M. Pedro, A. M. S. Silva, G. Eaton, R. van Soest and W.Herz, Z. Naturforsch., B: Chem. Sci., 2005, 60, 904.

432 Y. Gopichand and F. J. Schmitz, Tetrahedron Lett., 1979, 3921.433 G. M. Konig and A. D. Wright, Heterocycles, 1993, 36, 1351.434 E. W. Rogers, M. F. de Oliveira, R. G. S. Berlinck, G. M. Konig and

T. F. Molinski, J. Nat. Prod., 2005, 68, 891.435 R. D. Encarnacion, E. Sandoval, J. Malmstrom and C. Christo-

phersen, J. Nat. Prod., 2000, 63, 874.436 T. Ogamino and S. Nishiyama, Tetrahedron Lett., 2005, 46, 1083.437 R. J. Capon and N. S. Trotter, J. Nat. Prod., 2005, 68, 1689.438 H. Wu, H. Nakamura, J. Kobayashi, Y. Ohizumi and Y. Hirata,

Tetrahedron Lett., 1984, 25, 3719.439 A. K. Bakkestuen, L. L. Gundersen, D. Petersen, B. T. Utenova and

A. Vik, Org. Biomol. Chem., 2005, 3, 1025.440 T. Hattori, K. Adachi and Y. Shizuri, J. Nat. Prod., 1997, 60, 411.441 H. Nakamura, H. Wu, Y. Ohizumi and Y. Hirata, Tetrahedron Lett.,

1984, 25, 2989.442 I. S. Marcos, N. Garcıa, A. J. Sexmero, P. Basabe, D. Dıez and J. G.

Urones, Tetrahedron, 2005, 61, 11672.443 E. Perez-Garcıa, E. Zubıa, M. J. Ortega and J. L. Carballo, J. Nat.

Prod., 2005, 68, 653.444 C. E. McNamara, L. Larsen, N. B. Perry, J. L. Harper, M. V. Berridge,

E. W. Chia, M. Kelly and V. L. Webb, J. Nat. Prod., 2005, 68, 1431.445 K. Ueda, T. Ueta, E. R. O. Siwu, M. Kita and D. Uemura, Chem.

Lett., 2005, 34, 1530.446 Y. Venkateswarlu, D. J. Faulkner, J. L. R. Steiner, E. Corcoran and J.

Clardy, J. Org. Chem., 1991, 56, 6271.447 A. Rudi, Y. Benayahu and Y. Kashman, Org. Lett., 2004, 6, 4013.448 B. S. Olson and D. Trauner, Synlett, 2005, 4, 700.449 H. Liu, M. Namikoshi, K. Akano, H. Kobayashi, H. Nagai and X.

Yao, J. Asian Nat. Prod. Res., 2005, 7, 661.450 E. Goclik, G. M. Konig, A. D. Wright and R. Kaminsky, J. Nat.

Prod., 2000, 63, 1150.451 J. H. Kwak, F. J. Schmitz and M. Kelly, J. Nat. Prod., 2000, 63, 1153.452 L. Yang, D. E. Williams, A. Mui, C. Ong, G. Krystal, R. van Soest

and R. J. Andersen, Org. Lett., 2005, 7, 1073.453 S. S. Nasu, B. K. S. Yeung, M. T. Hamann, P. J. Scheuer, M. Kelly-

Borges and K. Goin, J. Org. Chem., 1995, 60, 7290.454 E. J. Alvarez-Manzaneda, R. Chahboun, I. B. Perez, E. Cabrera, E.

Alvarez and R. Alvarez-Manzaneda, Org. Lett., 2005, 7, 1477.455 G. Cimino, S. De Stefano and L. Minale, Tetrahedron, 1973, 29, 2565.456 C. J. Davis, T. E. Hurst, A. M. Jacob and C. J. Moody, J. Org. Chem.,

2005, 70, 4414.457 Y. Letourneux, J. M. Brunel, R. Fernandez, M. Dherbomez and C.

Debitus, Heterocycl. Commun., 2005, 11, 291.458 M. J. Martın, F. Berrue, P. Amade, R. Fernandez, A. Francesch, F.

Reyes and C. Cuevas, J. Nat. Prod., 2005, 68, 1554.459 A. M. Piggott and P. Karuso, Molecules, 2005, 10, 1292.460 H. Ishiyama, A. Hashimoto, J. Fromont, Y. Hoshino, Y. Mikami and

J. Kobayashi, Tetrahedron, 2005, 61, 1101.461 R. H. Cichewicz, L. J. Clifford, P. R. Lassen, X. L. Cao, T. B.

Freedman, L. A. Nafie, J. D. Deschamps, V. A. Kenyon, J. R.Flanary, T. R. Holman and P. Crews, Bioorg. Med. Chem., 2005, 13,5600.

462 V. J. Paul, Y. Seo, K. W. Cho, J. R. Rho, J. Shin and P. R. Bergquist,J. Nat. Prod., 1997, 60, 1115.

463 A. Rudi, Y. Benayahu and Y. Kashman, J. Nat. Prod., 2005, 68, 280.464 H. Shimogawa, T. Teruya, K. Suenaga and H. Kigoshi, Bull. Chem.

Soc. Jpn., 2005, 78, 1345.465 A. Rudi, Y. Erez, Y. Benayahu and Y. Kashman, Tetrahedron Lett.,

2005, 46, 8613.

466 M. L. Ciavatta, A. Fontana, S. Puliti, G. Scognamiglio and G. Cimino,Tetrahedron, 1999, 55, 12629.

467 M. L. Ciavatta, M. Gavagnin, E. Manzo, R. Puliti, C. A. Mattia, L.Mazzarella, G. Cimino, J. S. Simpson and M. J. Garson, Tetrahedron,2005, 61, 8049.

468 G. Cimino, S. De Stefano, A. Guerriero and L. Minale, TetrahedronLett., 1975, 3723.

469 H. Gaspar, M. Gavagnin, G. Calado, F. Castelluccio, E. Mollo andG. Cimino, Tetrahedron, 2005, 61, 11032.

470 M. Tischler, R. J. Andersen, M. I. Choudhary and J. Clardy, J. Org.Chem., 1991, 56, 42.

471 M. Kolympadi, M. Liapis and V. Ragoussis, Tetrahedron, 2005, 61,2003.

472 S. Cao, C. Foster, J. S. Lazo and D. G. I. Kingston, Bioorg. Med.Chem., 2005, 13, 5094.

473 M. Li, L. Li, Z. Deng, Y. Qiu and W. Lin, Bopuxue Zazhi, 2004, 21,323.

474 Z. G. Yu, K. S. Bi and Y. W. Guo, Helv. Chim. Acta, 2005, 88, 1004.475 G. R. Pettit, R. Tan and Z. A. Cichacz, J. Nat. Prod., 2005, 68,

1253.476 D. T. A. Youssef, L. A. Shaala and S. Emara, J. Nat. Prod., 2005, 68,

1782.477 G. Cimino, S. De Stefano, L. Minale and E. Fattorusso, Tetrahedron,

1972, 28, 333.478 H. J. Choi, Y. H. Choi, S. B. Yee, E. Im, J. H. Jung and N. D. Kim,

Mol. Carcinog., 2005, 44, 162.479 M. R. Kernan, D. J. Faulkner, L. Parkanyi, J. Clardy, M. S. de Carvalho

and R. S. Jacobs, Experientia, 1989, 45, 388.480 M. S. Buchanan, A. Edser, G. King, J. Whitmore and R. J. Quinn,

J. Nat. Prod., 2001, 64, 300.481 P. Basabe, S. Delgado, I. S. Marcos, D. Diez, A. Diego, M. De Roman

and J. G. Urones, J. Org. Chem., 2005, 70, 9480.482 T. A. Mansoor, J. Hong, C. O. Lee, S. J. Bae, K. S. Im and J. H. Jung,

J. Nat. Prod., 2005, 68, 331.483 L. Li, Z. Deng, H. Fu, J. Li, W. Lin and P. Proksch, J. Asian Nat. Prod.

Res., 2005, 7, 115.484 P. Sauleau and M.-L. Bourguet-Kondracki, Steroids, 2005, 70, 954.485 X. C. Huang, Y. W. Guo, E. Mollo and G. Cimino, Helv. Chim. Acta,

2005, 88, 281.486 A. Mandeau, C. Debitus, M. F. Aries and B. David, Steroids, 2005,

70, 873.487 H. Mitome, N. Shirato, A. Hoshino, H. Miyaoka, Y. Yamada and

R. W. M. Van Soest, Steroids, 2005, 70, 63.488 A. Zampella, R. D’Orsi, V. Sepe, S. De Marino, N. Borbone, A.

Valentin, C. Debitus, F. Zollo and M. V. D’Auria, Eur. J. Org. Chem.,2005, 20, 4359.

489 D. Xiao, X. Peng, S. Deng, W. Ma and H. Wu, Chin. J. Org. Chem.,2005, 25, 1606.

490 J. S. Sandler, S. L. Forsburg and D. J. Faulkner, Tetrahedron, 2005, 61,1199.

491 S. A. Tang, Z. W. Deng, J. Li, H. Z. Fu, Y. H. Pei, S. Zhang and W. H.Lin, Chin. Chem. Lett., 2005, 16, 353.

492 C. F.-L. Bon, F. Berrue, O. P. Thomas, F. Reyes and P. Amade, J. Nat.Prod., 2005, 68, 1284.

493 H. F. Dai, R. A. Edrada, R. Ebel, M. Nimtz, V. Wray and P. Proksch,J. Nat. Prod., 2005, 68, 1231.

494 E. W. Rogers and T. F. Molinski, J. Nat. Prod., 2005, 68, 450.495 G. Q. Li, X. Li, Z. W. Deng, H. S. Guan and W. H. Lin, Chin. Chem.

Lett., 2005, 16, 494.496 N. Fusetani, T. Toyoda, N. Asai, S. Matsunaga and T. Maruyama,

J. Nat. Prod., 1996, 59, 796.497 N. Alam, B. H. Bae, J. Hong, C. O. Lee, K. S. Im and J. H. Jung,

J. Nat. Prod., 2001, 64, 1059.498 M. Kita, M. Kitamura, T. Koyama, T. Teruya, H. Matsumoto, Y.

Nakano and D. Uemura, Tetrahedron Lett., 2005, 46, 8583.499 L. Quijano, F. Cruz, I. Navarrete, P. Gomez and T. Rios, Lipids, 1994,

29, 731.500 A. Han, J. Song, D. S. Jang, H. Min, S. K. Lee and E. Seo, Arch.

Pharm. Res., 2005, 28, 290.501 P. Muralidhar, M. M. Kumar, N. Krishna, C. B. Rao and D. V. Rao,

Chem. Pharm. Bull., 2005, 53, 168.502 X. He, S. Yan, L. Zeng and J. Su, Zhongshan Daxue Xuebao, Ziran

Kexueban, 2005, 44, 113.503 C. Subrahmanyam, S. Ratnar Kumar and G. Damodar Reddy,

Indian J. Chem., Sect. B, 2005, 44, 2186.


Dow

nloa

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on 2

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on h

ttp://

pubs

.rsc

.org

| do

i:10.

1039

/B60

3047

PView Online


504 J.-Y. Su, Y.-Y. Kuang, L.-M. Zeng and H. Li, J. Asian Nat. Prod. Res.,2005, 7, 107.

505 V. Anjaneyulu and P. Radhika, Indian J. Chem., Sect. B, 1999, 38, 457.506 P. Radhika, P. R. Rao, J. Archana and N. K. Rao, Biol. Pharm. Bull.,

2005, 28, 1311.507 C. A. Ospina, A. D. Rodrıguez, J. A. Sanchez, E. Ortega-Barria, T. L.

Capson and A. M. S. Mayer, J. Nat. Prod., 2005, 68, 1519.508 J.-H. Su, A. F. Ahmed, P.-J. Sung, Y.-C. Wu and J.-H. Sheu, J. Nat.

Prod., 2005, 68, 1651.509 A. F. Ahmed, Y.-H. Kuo, C.-F. Dai and J.-H. Sheu, J. Nat. Prod.,

2005, 68, 1208.510 H.-C. Huang, C.-H. Chao, J.-H. Liao, M. Y. Chiang, C.-F. Dai, Y.-C.

Wu and J.-H. Sheu, Tetrahedron Lett., 2005, 46, 7711.511 S. P. Garzon, A. D. Rodrıguez, J. A. Sanchez and E. Ortega-Barria,

J. Nat. Prod., 2005, 68, 1354.512 A. A. H. El-Gamal, E.-P. Chiu, C.-H. Li, S.-Y. Cheng, C.-F. Dai and

C.-Y. Duh, J. Nat. Prod., 2005, 68, 1749.513 S.-H. Qi, S. Zhang, X. Li and Q.-X. Li, J. Nat. Prod., 2005, 68, 1288.514 N. S. Reddy, J. K. Reed, R. E. Longley and A. E. Wright, J. Nat. Prod.,

2005, 68, 248.515 A. Ata, H. Y. Win, D. Holt, P. Holloway, E. P. Segstro and G. S.

Jayatilake, Helv. Chim. Acta, 2004, 87, 1090.516 C. Duque, M. Puyana, G. Narvaez, O. Osorno, N. Hara and Y.

Fujimoto, Tetrahedron, 2004, 60, 10627.517 I. I. Rodrıguez, Y.-P. Shi, O. J. Garcia, A. D. Rodrıguez, A. M. S.

Mayer, J. A. Sanchez, E. Ortega-Barria and J. Gonzalez, J. Nat. Prod.,2004, 67, 1672.

518 A. D. Rodrıguez, personal communication, 2006.519 T. Ferns and R. G. Kerr, Tetrahedron, 2005, 61, 12358.520 A. A. H. El-Gamal, S.-K. Wang, C.-F. Dai, I.-G. Chen and C.-Y. Duh,

J. Nat. Prod., 2005, 68, 74.521 J. Y. Su, R. L. Yang, Y. Y. Kuang and L. M. Zeng, J. Nat. Prod., 2000,

63, 1543.522 C.-X. Zhang, S.-J. Yan, G.-W. Zhang, W.-G. Lu, J.-Y. Su, L.-M. Zeng,

L.-Q. Gu, X.-P. Yang and Y.-J. Lian, J. Nat. Prod., 2005, 68, 1087.523 R. Jia, Y.-W. Guo, E. Mollo and G. Cimino, Helv. Chim. Acta, 2005,

88, 1028.524 M. Gutierrez, T. L. Capson, H. M. Guzman, J. Gonzalez, E. Ortega-

Barria, E. Quinoa and R. Riguera, J. Nat. Prod., 2005, 68, 614.525 G. Li, Y. Zhang, Z. Deng, L. van Ofwegen, P. Proksch and W. Lin,

J. Nat. Prod., 2005, 68, 649.526 S. W. Yin, Y. P. Shi, X. M. Li and B. G. Wang, Chin. Chem. Lett.,

2005, 16, 1489.527 A. F. Ahmed, R.-T. Shiue, G.-H. Wang, C.-F. Dai, Y.-H. Kuo and

J.-H. Sheu, Tetrahedron, 2003, 59, 7337.528 Y.-J. Tseng, A. F. Ahmed, C.-F. Dai, M. Y. Chiang and J.-H. Sheu,

Org. Lett., 2005, 7, 3813.529 M. Kobayashi and T. Hamaguchi, Chem. Pharm. Bull., 1988, 36, 3780.530 Y.-L. Zhang, X.-L. Tang, G.-Q. Li and W.-H. Lin, Qingdao Keji Daxue

Xuebao, Ziran Kexueban, 2005, 26, 215.531 A. A. H. El-Gamal, S.-K. Wang and C.-Y. Duh, Org. Lett., 2005, 7,

2023.532 A. A. H. El-Gamal, S.-K. Wang and C.-Y. Duh, Tetrahedron Lett.,

2005, 46, 6095.533 J. Marrero, A. D. Rodrıguez and C. L. Barnes, Org. Lett., 2005, 7,

1877.534 T. Iwagawa, K. Babazono, M. Nakatani, M. Doe, Y. Morimoto and

K. Takemura, Heterocycles, 2005, 65, 607.535 T. Iwagawa, N. Nishitani, M. Nakatani, M. Doe, Y. Morimoto and

K. Takemura, J. Nat. Prod., 2005, 68, 31.536 T. Iwagawa, N. Nishitani, M. Nakatani, M. Doe, Y. Morimoto and

K. Takemura, J. Nat. Prod., 2005, 68, 818.537 T. Iwagawa, K. Babazono, H. Okamura, M. Nakatani, M. Doe, Y.

Morimoto, M. Shiro and K. Takemura, Heterocycles, 2005, 65, 2083.538 T. Iwagawa, K. Babazono, H. Okamura, M. Nakatani, M. Doe, Y.

Morimoto, M. Shiro and K. Takemura, Heterocycles, 2005, 65, 3093.539 P.-J. Sung, W.-P. Hu, L.-S. Fang, T.-Y. Fan and J.-J. Wang, Nat. Prod.

Res., 2005, 19, 689.540 A. Hoshino, H. Mitome, S. Tamai, H. Takiyama and H. Miyaoka,

J. Nat. Prod., 2005, 68, 1328.541 T. Barsby and J. Kubanek, J. Nat. Prod., 2005, 68, 511.542 Y.-C. Lin, Y.-L. Huang, A. T. Khalil, M.-H. Chen and Y.-C. Shen,

Chem. Pharm. Bull., 2005, 53, 128.543 S.-H. Qi, S. Zhang, Y.-M. Wen, Z.-H. Xiao and Q.-X. Li, Helv. Chim.

Acta, 2005, 88, 2349.

544 J. J. Morales, D. Lorenzo and A. D. Rodrıguez, J. Nat. Prod., 1991,54, 1368.

545 M. T. Crimmins and J. M. Ellis, J. Am. Chem. Soc., 2005, 127, 17200.546 L. Chill, N. Berrer, Y. Benayahu and Y. Kashman, J. Nat. Prod., 2005,

68, 19.547 P. Bernardelli, O. M. Moradei, D. Friedrich, J. Yang, F. Gallou, B. P.

Dyck, R. W. Doskotch, T. Lange and L. A. Paquette, J. Am. Chem.Soc., 2001, 123, 9021.

548 J.-H. Su, H.-C. Huang, C.-H. Chao, L.-Y. Yan, Y.-C. Wu, C.-C. Wuand J.-H. Shen, Bull. Chem. Soc. Jpn., 2005, 78, 877.

549 A. F. Ahmed, M.-H. Wu, G.-H. Wang, Y.-C. Wu and J.-H. Sheu,J. Nat. Prod., 2005, 68, 1051.

550 A. A. H. El-Gamal, C.-Y. Chiang, S.-H. Huang, S.-K. Wang and C.-Y.Duh, J. Nat. Prod., 2005, 68, 1336.

551 Y.-C. Shen, Y.-C. Lin, A. F. Ahmed and Y.-H. Kuo, Tetrahedron Lett.,2005, 46, 4793.

552 A. A. H. El-Gamal, S.-K. Wang and C.-Y. Duh, Tetrahedron Lett.,2005, 46, 4499.

553 G. G. Mellado, E. Zubıa, M. J. Ortega and P. J. Lopez-Gonzalez,J. Nat. Prod., 2005, 68, 1111.

554 X. H. Yan and Y. W. Guo, Chin. Chem. Lett., 2005, 16, 356.555 R. Jia, Y.-W. Guo, E. Mollo and G. Cimino, Nat. Prod. Res., 2005,

19, 789.556 C.-H. Chao, L.-F. Huang, S.-L. Wu, J.-H. Su, H.-C. Huang and J.-H.

Sheu, J. Nat. Prod., 2005, 68, 1366.557 P. Jin, Z. Deng, Y. Pei, H. Fu, J. Li, L. van Ofwegen, P. Proksch and

W. Lin, Steroids, 2005, 70, 487.558 G. Li, Z. Deng, H. Guan, L. van Ofwegen, P. Proksch and W. Lin,

Steroids, 2005, 70, 13.559 G.-W. Zhang, X.-Q. Ma, H. Kurihara, C.-X. Zhang, X.-S. Yao, J.-Y.

Su and L.-M. Zeng, Org. Lett., 2005, 7, 991.560 W. Zhang, Y.-W. Guo, M. Gavagnin, E. Mollo and G. Cimino, Helv.

Chim. Acta, 2005, 88, 87.561 W. Zhang, G.-M. Yao and Y.-W. Guo, Acta Crystallogr., Sect. E, 2005,

61, o2884.562 C. Subrahmanyam and S. R. Kumar, J. Chem. Res., Synop., 2000, 182.563 J. Yang, S.-H. Qi, S. Zhang, J. Wu and Z.-H. Xiao, Chin. J. Chem.,

2005, 23, 1218.564 C.-H. Chao, L.-F. Huang, Y.-L. Yang, J.-H. Su, G.-H. Wang, M. Y.

Chiang, Y.-C. Wu, C.-F. Dai and J.-H. Sheu, J. Nat. Prod., 2005, 68,880.

565 C. B. Rao, K. V. Ramana, D. V. Rao, E. Fahy and D. J. Faulkner,J. Nat. Prod., 1988, 51, 954.

566 G.-W. Zhang, X.-Q. Ma, S.-J. Yan, L.-M. Zeng and J.-Y. Su, GaodengXuexiao Huaxue Xuebao, 2005, 26, 81.

567 S. Qi, S. Zhang, J. Huang, Z. Xiao, J. Wu and Q. Li, Magn. Reson.Chem., 2005, 43, 266.

568 H. T. D’Armas, B. S. Mootoo and W. F. Reynolds, J. Nat. Prod., 2000,63, 1669.

569 A. Rueda, E. Zubia, M. J. Ortega and J. Salva, Steroids, 2001, 66, 897.570 H. Jayasuriya, K. B. Herath, J. G. Ondeyka, Z. Guan, R. P. Borris,

S. Tiwari, W. de Jong, F. Chavez, J. Moss, D. W. Stevenson, H. T.Beck, M. Slattery, N. Zamora, M. Schulman, A. Ali, N. Sharma, K.MacNaul, N. Hayes, J. G. Menke and S. B. Singh, J. Nat. Prod., 2005,68, 1247.

571 S. Cao, C. Foster, J. S. Lazo and D. G. I. Kingston, Bioorg. Med.Chem., 2005, 13, 5830.

572 H. Nagai, Kaiyo Seibutsu Seibun no Riyo, 2005, 106.573 T. Honma, Y. Hasegawa, M. Ishida, H. Nagai, Y. Nagashima and K.

Shiomi, Toxicon, 2005, 45, 33.574 T. Honma, S. Minagawa, H. Nagai, M. Ishida, Y. Nagashima and K.

Shiomi, Toxicon, 2005, 46, 768.575 A. P. Il’ina, M. M. Monastyrnaya, I. N. Sokotun, T. A. Egorov, Y. A.

Nazarenko, G. N. Likhatskaya and E. P. Kozlovskaya, Russ. J. Bioorg.Chem., 2005, 31, 34.

576 R. B. Cunha, A. N. C. Santana, P. C. Amaral, M. D. F. Carvalho,D. M. F. Carvalho, E. A. Cavalheiro, B. Maigret, C. A. O. Ricart,B. A. Cardi, M. V. Sousa and K. M. Carvalho, Toxicon, 2005, 45, 207.

577 A. J. Blackman and D. J. Matthews, Heterocycles, 1985, 23, 2829.578 M. Ramirez-Osuna, D. Chavez, L. Hernandez, E. Molins, R. So-

manathan and G. Aguirre, Molecules, 2005, 10, 295.579 H. Kawashima, Lipids, 2005, 40, 627.580 G. R. Pettit, Y. Tang and J. C. Knight, J. Nat. Prod., 2005, 68, 974.581 R. J. Andersen, D. J. Faulkner, H. Cun-heng, G. D. Van Duyne and J.

Clardy, J. Am. Chem. Soc., 1985, 107, 5492.


Dow

nloa

ded

on 2

3 Ja

nuar

y 20

11Pu

blis

hed

on h

ttp://

pubs

.rsc

.org

| do

i:10.

1039

/B60

3047

PView Online


582 M. Vanhuyse, J. Kluza, C. Tardy, G. Otero, C. Cuevas, C. Bailly andA. Lansiaux, Cancer Lett., 2005, 221, 165.

583 C. M. Ireland and P. J. Scheuer, Science, 1979, 205, 922.584 E. Manzo, M. L. Ciavatta, M. Gavagnin, E. Mollo, S. Wahidulla and

G. Cimino, Tetrahedron Lett., 2005, 46, 465.585 M. Cueto, L. D’Croz, J. L. Mate, A. San-Martın and J. Darias, Org.

Lett., 2005, 7, 415.586 J. E. Barbarow, A. K. Miller and D. Trauner, Org. Lett., 2005, 7, 2901.587 J. E. Moses, R. M. Adlington, R. Rodriguez, S. J. Eade and J. E.

Baldwin, Chem. Commun., 2005, 1687.588 D. R. Zuidema, A. K. Miller, D. Trauner and P. B. Jones, Org. Lett.,

2005, 7, 4959.589 V. Di Marzo, R. R. Vardaro, L. De Petrocellis, G. Villani, R. Minei

and G. Cimino, Experientia, 1991, 47, 1221.590 D. R. Zuidema and P. B. Jones, J. Nat. Prod., 2005, 68, 481.591 M. Gavagnin, E. Mollo, G. Cimino and J. Ortea, Tetrahedron Lett.,

1996, 37, 4259.592 D. W. Jeffery, M. V. Perkins and J. M. White, Org. Lett., 2005, 7,

1581.593 D. C. Manker and D. J. Faulkner, Tetrahedron, 1987, 43, 3677.594 A. Pathak, J. Aslaoui and C. Morin, J. Org. Chem., 2005, 70, 4184.595 T. Maoka, Y. Fujiwara, K. Hashimoto and N. Akimoto, Chem.

Pharm. Bull., 2005, 53, 1207.596 J.-K. Seo, J. M. Crawford, K. L. Stone and E. J. Noga, Biochem.

Biophys. Res. Commun., 2005, 338, 1998.597 G. Bulaj, P. J. West, J. E. Garrett, M. Marsh, M.-M. Zhang, R. S.

Norton, B. J. Smith, D. Yoshikami and B. M. Olivera, Biochemistry,2005, 44, 7259.

598 M. B. Aguilar, E. Lopez-Vera, J. S. Imperial, A. Falcon, B. M. Oliveraand E. P. Heimer dela Cotera, Peptides, 2005, 26, 23.

599 M. C. V. Braga, K. Konno, F. C. V. Portaro, J. C. de Freitas, T. Yamane,B. M. Olivera and D. C. Pimenta, Toxicon, 2005, 45, 113.

600 S. Sudarslal, S. Majumdar, P. Ramasamy, R. Dhawan, P. P. Pal, M.Ramaswami, A. K. Lala, S. K. Sikdar, S. P. Sarma, K. S. Krishnanand P. Balaram, FEBS Lett., 2003, 553, 209.

601 S. P. Sarma, G. S. Kumar, S. Sudarslal, P. Iengar, P. Ramasamy, S. K.Sikdar, K. S. Krishnan and P. Balaram, Chem. Biodiversity, 2005, 2,535.

602 T. Grkovic, D. R. Appleton and B. R. Copp, Chem. N. Z., 2005, 69,12.

603 C. E. Kicklighter, S. Shabani, P. M. Johnson and C. D. Derby, Curr.Biol., 2005, 15, 549.

604 T. Dias, I. Brito, L. Moujir, N. Paiz, J. Darias and M. Cueto, J. Nat.Prod., 2005, 68, 1677.

605 E. Manzo, M. L. Ciavatta, M. Gavagnin, R. Puliti, E. Mollo, Y.-W.Guo, C. A. Mattia, L. Mazzarella and G. Cimino, Tetrahedron, 2005,61, 7456.

606 M. Norte, A. G. Gonzalez, F. Cataldo, M. L. Rodrıguez and I. Brito,Tetrahedron, 1991, 47, 9411.

607 D. Awakura, K. Fujiwara and A. Murai, Chem. Lett., 1999, 461.608 D. Iliopoulou, C. Vagias, C. Harvala and V. Roussis, Phytochemistry,

2002, 59, 111.609 K. L. McPhail and M. T. Davies-Coleman, Nat. Prod. Res., 2005, 19,

449.610 S. Tsukamoto, Y. Yamashita and T. Ohta, Mar. Drugs, 2005, 3, 22.611 S. Suntornchashwej, N. Chaichit, M. Isobe and K. Suwanborirux,

J. Nat. Prod., 2005, 68, 951.612 M. Gavagnin, M. Carbone, M. Nappo, E. Mollo, V. Roussis and G.

Cimino, Tetrahedron, 2005, 61, 617.613 K. Suenaga, T. Shibata, N. Takada, H. Kigoshi and K. Yamada,

J. Nat. Prod., 1998, 61, 515.614 Y. Morimoto, Y. Nishikawa and M. Takaishi, J. Am. Chem. Soc., 2005,

127, 5806.615 G. R. Pettit, Y. Kamano, H. Kizu, C. Dufresne, C. L. Herald,

R. J. Bontems, J. M. Schmidt, F. E. Boettner and R. A. Nieman,Heterocycles, 1989, 28, 553.

616 M. A. Ali, R. B. Bates, Z. D. Crane, C. W. Dicus, M. R. Gramme,E. Hamel, J. Marcischak, D. S. Martinez, K. J. McClure, P. Nakkiew,G. R. Pettit, C. C. Stessman, B. A. Sufi and G. V. Yarick, Bioorg. Med.Chem., 2005, 13, 4138.

617 M. Gavagnin, M. Carbone, E. Mollo and G. Cimino, TetrahedronLett., 2003, 44, 1495.

618 E. J. Alvarez-Manzaneda, R. Chahboun, I. Barranco, E. C. Torres,E. Alvarez and R. Alvarez-Manzaneda, Tetrahedron Lett., 2005, 46,5321.

619 V. Kulcitki, N. Ungur, M. Gavagnin, M. Carbone and G. Cimino,Eur. J. Org. Chem., 2005, 1816.

620 K. L. McPhail, M. T. Davies-Coleman and J. Starmer, J. Nat. Prod.,2001, 64, 1183.

621 C.-H. Li, S.-J. Da, X.-S. Chen, G.-L. Zhou, Z.-X. Xie and Y. Li,Huaxue Xuebao, 2005, 63, 2158.

622 T. P. Brady, S. H. Kim, K. Wen, C. Kim and E. A. Theodorakis,Chem.–Eur. J., 2005, 11, 7175.

623 J. E. Hochlowski, D. J. Faulkner, G. K. Matsumoto and J. Clardy,J. Org. Chem., 1983, 48, 1142.

624 A. Abad, C. Agullo, A. C. Cunat and A. B. Garcıa, Tetrahedron, 2005,61, 1961.

625 T. Miyamoto, K. Sakamoto, K. Arao, T. Komori, R. Higuchi and T.Sasaki, Tetrahedron, 1996, 52, 8187.

626 A. Fontana, P. Cavaliere, S. Wahidulla, C. G. Naik and G. Cimino,Tetrahedron, 2000, 56, 7305.

627 T. Teruya, K. Suenaga, S. Maruyama, M. Kurotaki and H. Kigoshi,Tetrahedron, 2005, 61, 6561.

628 J.-F. Biard, C. Roussakis, J.-M. Kornprobst, D. Gouiffes-Barbin, J.-F.Verbist, P. Cotelle, M. P. Foster, C. M. Ireland and C. Debitus, J. Nat.Prod., 1994, 57, 1336.

629 G. Zuber, M.-R. Goldsmith, T. D. Hopkins, D. N. Beratan and P.Wipf, Org. Lett., 2005, 7, 5269.

630 P. Wipf and T. D. Hopkins, Chem. Commun., 2005, 3421.631 S. C. Lievens and T. F. Molinski, Org. Lett., 2005, 7, 2281.632 A. Simon-Levert, A. Arrault, N. Bontemps-Subielos, C. Canal and B.

Banaigs, J. Nat. Prod., 2005, 68, 1412.633 L. K. Shubina, S. N. Fedorov, O. S. Radchenko, N. N. Balaneva, S. A.

Kolesnikova, P. S. Dmitrenok, A. Bode, Z. Dong and V. A. Stonik,Tetrahedron Lett., 2005, 46, 559.

634 G. Guella, I. Mancini and F. Pietra, Helv. Chim. Acta, 1987, 70, 621.635 A. Aiello, E. Fattorusso, P. Luciano, A. Mangoni and M. Menna,

Eur. J. Org. Chem., 2005, 5024.636 A. Aiello, E. Fattorusso, P. Luciano, A. Macho, M. Menna and E.

Munoz, J. Med. Chem., 2005, 48, 3410.637 M. J. McKay, A. R. Carroll and R. J. Quinn, J. Nat. Prod., 2005, 68,

1776.638 K. Ravinder, A. V. Reddy, P. Krishnaiah, P. Ramesh, S. Ramakrishna,

H. Laatsch and Y. Venkateswarlu, Tetrahedron Lett., 2005, 46, 5475.639 H. Liu, S. B. Pratasik, T. Nishikawa, T. Shida, K. Tachibana, T.

Fujiwara, H. Nagai, H. Kobayashi and M. Namikoshi, TetrahedronLett., 2004, 45, 7015.

640 H. Liu, T. Fujiwara, T. Nishikawa, Y. Mishima, H. Nagai, T. Shida, K.Tachibana, H. Kobayashi, R. E. P. Mangindaan and M. Namikoshi,Tetrahedron, 2005, 61, 8611.

641 S. Malla Reddy, M. Srinivasulu, N. Satyanarayana, A. K. Kondapiand Y. Venkateswarlu, Tetrahedron, 2005, 61, 9242.

642 A. J. Blackman, C. P. Li, D. C. R. Hockless, B. W. Skelton and A. H.White, Tetrahedron, 1993, 49, 8645.

643 J. F. Baird, S. Guyot, C. Roussakis, J. F. Verbist, J. Vercauteren, J. F.Weber and K. Boukef, Tetrahedron Lett., 1994, 35, 2691.

644 H. H. Issa, J. Tanaka, R. Rachmat, A. Setiawan, A. Trianto and T.Higa, Mar. Drugs, 2005, 3, 78.

645 E. W. Schmidt, J. T. Nelson, D. A. Rasko, S. Sudek, J. A. Eisen, M. G.Haygood and J. Ravel, Proc. Natl. Acad. Sci. U. S. A., 2005, 102, 7315.

646 P. F. Long, W. C. Dunlap, C. N. Battershill and M. Jaspars,ChemBioChem, 2005, 6, 1760.

647 L. J. Perez and D. J. Faulkner, J. Nat. Prod., 2003, 66, 247.648 S.-L. You and J. W. Kelly, Tetrahedron, 2005, 61, 241.649 Y. Yonezawa, N. Tani and C.-G. Shin, Bull. Chem. Soc. Jpn., 2005, 78,

1492.650 A. Rudi, L. Chill, M. Aknin and Y. Kashman, J. Nat. Prod., 2003, 66,

575.651 S.-L. You and J. W. Kelly, Tetrahedron Lett., 2005, 46, 2567.652 S. Kumar-Roine, M. Frostin, A. Al-Mourabit, A.-G. Duigou, J.

Pusset, S. Ali, M. Sauvain, S. Sotheeswaran and D. Laurent, ACGCChem. Res. Commun., 2005, 18, 25.

653 A. J. Freyer, A. D. Patil, L. Killmer, N. Troupe, M. Mentzer, B. Carte,L. Faucette and R. K. Johnson, J. Nat. Prod., 1997, 60, 986.

654 B. M. Trost and D. R. Fandrick, Org. Lett., 2005, 7, 823.655 A. D. Patil, A. J. Freyer, R. Reichwein, B. Carte, L. B. Killmer, L.

Faucette, R. K. Johnson and D. J. Faulkner, Tetrahedron Lett., 1997,38, 363.

656 H. Abe, S. Aoyagi and C. Kibayashi, J. Am. Chem. Soc., 2005, 127,1473.


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657 S. Dutta, H. Abe, S. Aoyagi, C. Kibayashi and K. S. Gates, J. Am.Chem. Soc., 2005, 127, 15004.

658 F. Kong and D. J. Faulkner, Tetrahedron Lett., 1991, 32, 3667.659 J. Kubanek, D. E. Williams, E. D. de Silva, T. Allen and R. J. Andersen,

Tetrahedron Lett., 1995, 36, 6189.660 H. Tsuneki, Y. You, N. Toyooka, T. Sasaoka, H. Nemoto, J. A. Dani

and I. Kimura, Biol. Pharm. Bull., 2005, 28, 611.661 H. Kang and W. Fenical, J. Org. Chem., 1997, 62, 3254.662 A. Hamasaki, J. M. Zimpleman, I. Hwang and D. L. Boger, J. Am.

Chem. Soc., 2005, 127, 10767.663 S. Faivre, S. Chieze, C. Delbaldo, N. Ady-Vago, C. Guzman, L. Lopez-

Lazaro, S. Lozahic, J. Jimeno, F. Pico, J. P. Armand, J. A. L. Martinand E. Raymond, J. Clin. Oncol., 2005, 23, 7871.

664 E. F. A. Brandon, R. D. van Ooijen, R. W. Sparidans, L. L. Lazaro,A. J. R. Heck, J. H. Beijnen and J. H. M. Schellens, J. Mass Spectrom.,2005, 40, 821.

665 J. Fayette, I. R. Coquard, L. Alberti, D. Ranchere, H. Boyle and J.-Y.Blay, Oncologist, 2005, 10, 827.

666 P. Allavena, M. Signorelli, M. Chieppa, E. Erba, G. Bianchi, F.Marchesi, C. O. Olimpio, C. Bonardi, A. Garbi, A. Lissoni, F. deBraud, J. Jimeno and M. D’Incalci, Cancer Res., 2005, 65, 2964.

667 T. Hamada, M. Asanuma, T. Ueki, F. Hayashi, N. Kobayashi, S.Yokoyama, H. Michibata and H. Hirota, J. Am. Chem. Soc., 2005,127, 4216.

668 N. P. Mischenko, S. A. Fedoreyev, N. D. Pokhilo, V. P. Anufriev, V. A.Denisenko and V. P. Glazunov, J. Nat. Prod., 2005, 68, 1390.

669 J. R. Rho and Y. H. Kim, Bull. Korean Chem. Soc., 2005, 26, 1457.670 F. Kisa, K. Yamada, M. Kaneko, M. Inagaki and R. Higuchi, Chem.

Pharm. Bull., 2005, 53, 382.671 T. Maruta, T. Saito, M. Inagaki, O. Shibata and R. Higuchi, Chem.

Pharm. Bull., 2005, 53, 1255.672 K. Yamada, R. Matsubara, M. Kaneko, T. Miyamoto and R. Higuchi,

Chem. Pharm. Bull., 2001, 49, 447.673 K. Yamada, N. Wada, H. Onaka, R. Matsubara, R. Isobe, M. Inagaki

and R. Higuchi, Chem. Pharm. Bull., 2005, 53, 788.674 K. Yamada, H. Onaka, M. Tanaka, M. Inagaki and R. Higuchi,

Chem. Pharm. Bull., 2005, 53, 1333.675 M. Inagaki, T. Miyamoto, R. Isobe and R. Higuchi, Chem. Pharm.

Bull., 2005, 53, 1551.676 L.-X. Zhang, X. Fan and J.-G. Shi, J. Asian Nat. Prod. Res., 2005, 7,

25.677 A. A. Kicha, A. I. Kalinovsky, N. V. Ivanchina, Y. N. El’kin and V. A.

Stonik, Russ. Chem. Bull., 1994, 43, 1726.678 A. A. Kicha, N. V. Ivanchina, A. I. Kalinovsky, P. S. Dmitrenok and

V. A. Stonik, Russ. Chem. Bull., 2005, 54, 1266.679 E. V. Levina, A. I. Kalinovsky, P. V. Andriyashenko, P. S. Dmitrenok,

D. L. Aminin and V. A. Stonik, J. Nat. Prod., 2005, 68, 1541.680 H. D. Chludil and M. S. Maier, J. Nat. Prod., 2005, 68, 1279.

681 E. V. Levina, A. I. Kalinovsky, V. A. Stonik, P. S. Dmitrenok and P. V.Andriyashchenko, Russ. J. Bioorg. Chem., 2005, 31, 467.

682 W. Wang, H. Jang, J. Hong, C.-O. Lee, S.-J. Bae, S. Shin and J. H.Jung, Arch. Pharm. Res., 2005, 28, 285.

683 H. F. Tang, Y. H. Yi, L. Li, P. Sun, D. Z. Zhou and B. S. Liu, Chin.Chem. Lett., 2005, 16, 619.

684 H.-F. Tang, Y.-H. Yi, L. Li, P. Sun, S.-Q. Zhang and Y.-P. Zhao, PlantaMed., 2005, 71, 458.

685 H.-F. Tang, Y.-H. Yi, L. Li, P. Sun, S.-Q. Zhang and Y.-P. Zhao, J. Nat.Prod., 2005, 68, 337.

686 J. Wu, Y. Yi, H. Wu, Q. He, Z. Zou and S. Zhang, Zhongguo TianranYaowu, 2005, 3, 276.

687 A. S. Silchenko, V. A. Stonik, S. A. Avilov, V. I. Kalinin, A. I.Kalinovsky, A. M. Zaharenko, A. V. Smirnov, E. Mollo and G.Cimino, J. Nat. Prod., 2005, 68, 564.

688 Z. Zou, Y. Yi, H. Wu, X. Yao, L. Du, W. Jiuhong, C.-C. Liaw andK.-H. Lee, J. Nat. Prod., 2005, 68, 540.

689 Z.-R. Zou, Y.-H. Yi, H.-M. Wu, J.-H. Wu, C.-C. Liaw and K.-H. Lee,J. Nat. Prod., 2003, 66, 1055.

690 Y. Tong, X. Zhang, F. Tian, Y. Yi, Q. Xu, L. Li, L. Tong, L. Lin andJ. Ding, Int. J. Cancer, 2005, 114, 843.

691 G. Moraes, P. T. Northcote, A. S. Silchenko, A. S. Antonov, A. I.Kalinovsky, P. S. Dmitrenok, S. A. Avilov, V. I. Kalinin and V. A.Stonik, J. Nat. Prod., 2005, 68, 842.

692 A. M. de Moncerrat Iniguez-Martinez, G. Guerra-Rivas, T. Rios andL. Quijano, J. Nat. Prod., 2005, 68, 1669.

693 E. J. Kim, C.-H. Kim, H.-J. Go, I. H. Kim, S. H. An, H.-Y. Sohn,H. Y. Park, H. D. Yoon, Y.-C. Chang, Y.-K. Hong and N. G. Park,J. Korean Fish. Soc., 2005, 38, 148.

694 E. L. Teuten, L. Xu and C. M. Reddy, Science, 2005, 307, 917.695 G. Marsh, M. Athanasiadou, I. Athanassiadis, A. Bergman, T. Endo

and K. Haraguchi, Environ. Sci. Technol., 2005, 39, 8684.696 N. Sugiyama, M. Araki, M. Ishida, Y. Nagashima and K. Shiomi,

Toxicon, 2005, 45, 595.697 W. E. Houssen and M. Jaspars, J. Nat. Prod., 2005, 68, 453.698 B. Chen, X. R. Shen and J. L. Kong, Chin. J. Chem., 2005, 23, 599.699 I. Kontiza, C. Vagias, J. Jakupovic, D. Moreau, C. Roussakis and V.

Roussis, Tetrahedron Lett., 2005, 46, 2845.700 L. Han, X. Huang, I. Sattler, U. Moellmann, H. Fu, W. Lin and S.

Grabley, Planta Med., 2005, 71, 160.701 L. Han, X. Huang, I. Sattler, H.-M. Dahse, H. Fu, S. Grabley and W.

Lin, Pharmazie, 2005, 60, 705.702 S. Bao, Z. Deng, H. Fu, P. Proksch and W. Lin, Helv. Chim. Acta,

2005, 88, 2757.703 L. Han, X. Huang, I. Sattler, H.-M. Dahse, H. Fu, W. Lin and S.

Grabley, J. Nat. Prod., 2004, 67, 1620.704 J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote and M. R.

Prinsep, Nat. Prod. Rep., 2003, 20, 1.


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