PHARM.

D Chemical Pharmacognosy- I Lecture 27 May 9th, 2011

Isothiocyanate Glycosides
M. Ahsan Khalid, B.Pharm, Pharm. D B.Pharm,
M.Phil Scholar (RIPS/RIU) HIPSHIPS-HUKIC

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

Isothiocyanate Glycosides

Black Mustard NF XI (1960)

Synonym: brown or chinese mustard, Sinapis nigra Origin: 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 arthritis commercial: condiment

Black Mustard
Interactions
Acetaminophen and other drugs metabolized by CYP 2E1 Anticoagulants, NSAID, prostacylin Antidiabetics Herb to Herb Anticoagulants feverfew, ginkgo Antihyperglycemic - glucomannan

White Mustard
Synonym: yellow or English mustard Origin: dried seeds of Brassica alba (Brassicaceae) Constituent: sinalbin --H+--- p - hydroxybenzylisothiocyanate Use: same use as black mustard Note: p-hydroxybenzylisothiocyanate (acrinyl isothiocyanate) is pungent tasting, almost odorless oil

Organosulfur drug (Garlic)

Synonym: bawang, garlic Origin: 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

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