Reaxys webinar jan2015_naturalproducts

Christine Flemming

Elsevier Product Training Manager

[email protected]

SEARCHING FOR NATURAL PRODUCTS IN REAXYS

Reaxys webinar

January 27, 2015

AGENDA

Natural Product content in Reaxys

Natural Product Search Form

Other ways to search for Natural Product information in Reaxys

NATURAL PRODUCT CONTENT SOURCES

3

Here’s just a few…..

4

NATURAL PRODUCT CONTENT SOURCES

What kind of NP information is extracted?

Isolation from animals, plants, marine life, bacteria, etc.

Frog

Stems, leaves, etc.

Location

Genus and species

WAYS TO FIND NATURAL PRODUCT INFORMATION

5

• Ask Reaxys• INP field• Literature search• Substance name search• Bioactivity search• Structure search• Substance Basic Index

DEMO

• FIND NATURALLY OCCURRING XANTHONES

• FIND SUBSTANCES ISOLATED FROM GARCINIABRECTEATA

• VIEW ACTIVITY PROFILES FOR SUBSTANCES SIMILAR TO A UNIQUE SUBSTANCE FROM GARCINIA BRACTEATA

• VIEW AN ACTIVITY PROFILE AND LIST OF CITATIONS FOR HYDROXYCITRIC ACID

• CREATE A LIST OF THE MOST ACTIVE COMPOUNDS DERIVED FROM STARFISH

6

PRESENTER | DATE | NAME OF PRESENTATION

7

INTRO

8

NATURAL PRODUCT FORM

9

Find naturally occurring Xanthones

Using the “exists” check box


10

1638 hits

56 instances of isolation from NP

View the NP data


11

Bioactivity data for mangostanin

View the bioactivity data

Targets

Effect


13

Isolation from Natural Product Field

>1000 hits

46 hits (some could be false positives)

14

Isolation from Natural Product FieldNATURAL PRODUCT FORM

39 hits

The semicolon is interpreted as “OR”.

Add “NEXT” and bracteata to the query. Important! You must add the parentheses or the search will not work!

If uncertain of the spelling for

“bracteata”, just truncate

using an asterisk as a wildcard.

ASK REAXYS

18

98 hits

Find a list of substances

ASK REAXYS

19


View the Effects profile using the Analysis View

ASK REAXYS

20

View the Effects profile using the Heatmap


ASK REAXYS

21

Switch from “Substances to “Citations” context

ASK REAXYS

22

23

Quick search for literature

Search fields for

bibliographic information

Search fields for terms

LITERATURE

Click the Literature button

24

BIBLIOGRAPHIC FIELDS

25

Search fields for

bibliographic information

Search fields for terms

LITERATURE

Anti*nflammatory marine NEXT natural products

WHEN YOU SEARCH LITERATURE IN REAXYS YOU ARE SEARCHING ….

26

>48 MILLION RECORDS

• Bibliography

• Terms in titles and abstracts

• Keywords from:

• Authors

• Reaxys

• COMPENDEX

• EMBASE

• GEObase

• MEDLINE

• Indexes of:

• Species

• Geographical Terms

Many of these records additionally contain

• Substances

• Reactions

• Bioactivities

• Properties

LITERATURE

STARFISH

27

Year/Articles

Pisaster ochraceus Stichaster australis

Asterias amurensisAcanthaster planci

29

Steroids from the cold water starfish ctenodiscus crispatus with cytotoxic and apoptotic effects on human hepatocellular

carcinoma and glioblastoma cells

Chemical investigation on the methanol extract of the starfish Ctenodiscus crispatus resulted in the isolation of five steroids,

(22E,24?)-26,27-bisnor-24- methyl-5α-cholest-22-en-3β,5,6β,15α,25-pentol 25-O-sulfate (1), (22E,24R,25R)-24-methyl-5α-

cholest-22-en-3β,5,6β, 15α,25,26-hexol 26-O-sulfate (2), (28R)-24-ethyl-5α- cholesta-3β,5,6β,8,15α,28,29-heptaol-24-sulfate

(3), (25S)-5α-cholestane-3β,5,6β,15α,16β,26-hexaol (4), and ?7-sitosterol (5). Their structures were identified by extensive

spectroscopic analyses, including 1D, 2D NMR and MS and chemical methods. Compound 4 showed cytotoxicity against human

hepatoma HepG2 and glioblastoma U87MG cells via inhibition of cell growth and induction of apoptosis. Induction of apoptosis

by 4 was demonstrated by cell death, DNA fragmentation, increased Bax/Bcl-2 protein ratio and the activation of caspase-3,

caspase-9 and poly (ADP-ribose) polymerase (PARP).

Quang, Tran Hong; Lee, Dong-Sung; Han, Se Jong; Kim, I. Chan; Yim, Joung

Han; Kim, Youn-Chul; Oh, Hyuncheol

Bulletin of the Korean Chemical Society, 2014 , vol. 35, # 8 p. 2335 - 2341

Shin, Hee Jae; Lee, Hwa-Sun; Lee, Jong Seok; Shin, Junho; Lee,

Min Ah; Lee, Hyi-Seung; Lee, Yeon-Ju; Yun, Jieun; Kang, Jong

Soon Marine Drugs, 2014 , vol. 12, # 6 p. 3283 - 3291

Violapyrones H and I, new cytotoxic compounds isolated from Streptomyces sp. associated with the marine starfish

Acanthaster planci

Two new α-pyrone derivatives, violapyrones H (1) and I (2), along with known violapyrones B (3) and C ( 4) were isolated from

the fermentation broth of a marine actinomycete Streptomyces sp. The strain was derived from a crown-of-thorns starfish,

Acanthaster planci, collected from Chuuk, Federated States of Micronesia. The structures of violapyrones were elucidated by

the analysis of 1D and 2D NMR and HR-ESIMS data. Violapyrones (1-4) exhibited cytotoxicity against 10 human cancer cell lines

with GI50 values of 1.10-26.12 μg/mL when tested using sulforhodamine B (SRB) assay. This is the first report on the

cytotoxicity of violapyrones against cancer cell lines and the absolute configuration of violapyrone C.

violapyrone I

30

Biologically active glycosides from asteroida, XXXIV: Isolation

and structure of cerebrosides from the starfish Stellaster

equestris

1-O-(β-D-Glucopyranosyl)-(2S,3R,4E,8E,10E)-2-<(2R)-2-

hydroxytetracosanoylamino>-9-methyl-4,8,10-octadecatriene-1,3-diol

Eight cerebrosides, S-1-3 (1), S-1-4 (2), S-1-5 (3), S-2a-3 (4), S-2a-11 (5), S-2b-2 (6), S-2b-4 (7) and S-2b-16 (8), were

isolated from the three cerebroside molecular species S-1, S-2a and S-2b obtained from the less polar fraction of the

chloroform/methanol extract of the starfish Stellaster equestris. The structures of these cerebrosides were determined on

the basis of chemical and spectroscopic evidence. Compounds 4-8 are, to the authors' knowledge, new cerebrosides. ©

VCH Verlagsgesellschaft mbH, 1996.

31stellaster equestris

STARFISH

32

Pisaster ochraceus Stichaster australis

Asterias amurensisAcanthaster planci

THANK YOU

38

Reaxys webinar jan2015_naturalproducts

Science

Transcript of Reaxys webinar jan2015_naturalproducts