Lecture 27 - Isothiocyanate Glycosides [Compatibility Mode]
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Transcript of Lecture 27 - Isothiocyanate Glycosides [Compatibility Mode]
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PHARM. DChemical Pharmacognosy- I
Lecture 27 May 9th, 2011
IsothiocyanateGlycosides
M. M. AhsanAhsan KhalidKhalid, , B.PharmB.Pharm, Pharm. D, Pharm. DM.PhilM.Phil Scholar (RIPS/RIU)Scholar (RIPS/RIU)
HIPSHIPS--HUKICHUKIC
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Isothiocyanate Glycosides• Also known as glucosinolates• R represents: CH2 = CHCH2 (sinigrin)
p-HOC6H4CH2 (sinalbin)• abundant in dicot families: Brassicaceae,
Capparidaceae, Resedaceae• many glucosinolates have anti-thyroid and
goiter - inducing effect in man• in mustard vegetables
indolmethylglucosinolate (mammary cancer) -H+ -- indole 3 - carbinol
4 - methylsulfinyl isothiocyanate (broccoli) - induces anti-cancer enzymes
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Isothiocyanate Glycosides
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Black Mustard NF XI (1960)Synonym: brown or chinese mustard, Sinapis
nigraOrigin: dried ripe seed of Brassica nigra or B.
juncea (Brassicaceae)Constituent:
sinigrin ---H+---- allyl isothiocyanate + KHSO4 + glucose
- sinigrin (potassium myronate)- allyl isothiocyanate (mustard oil - volatile)
Use: local irritant, emetic,externally: rubefacient, vesicant, pulmonary congestion, rheumatic arthritiscommercial: condiment
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Black Mustard• Interactions
– Acetaminophen and other drugs metabolized by CYP 2E1
– Anticoagulants, NSAID, prostacylin– Antidiabetics
Herb to Herb– Anticoagulants – feverfew, ginkgo– Antihyperglycemic - glucomannan
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White MustardSynonym: yellow or English mustardOrigin: dried seeds of Brassica alba
(Brassicaceae)Constituent:
sinalbin --H+--- p - hydroxybenzylisothiocyanateUse: same use as black mustard
Note:p-hydroxybenzylisothiocyanate (acrinyl
isothiocyanate) is pungent tasting, almost odorless oil
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Organosulfur drug (Garlic)Synonym: bawang, garlicOrigin: bulb of Allium sativum(Liliaceae)Constituent:
alliin --H+-- allicin (diallyl thiosulfinate)-air and water ----- diallyl disulfide + dillyl trisulfide
Use: - anti-hyperlipidemic activity- enhances blood fibrinolytic activity - inhibits platelet aggregation (antithrombotic
agent)Note:alliin - sulfur containing amino acid derivative of S - allyl -
cysteine sulfoxide
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Garlic• Aroma, flavor and medicinal properties –
sulfur containing cpds (aliin, ajoen, allicin)• Inhibits lipid synthesis - cholesterol• Anticoagulant – inhibit platelet aggregation
– Allicin, ajoen• blood glucose - insulin, glycogen storage