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

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

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

Black Mustard• Interactions

– Acetaminophen and other drugs metabolized by CYP 2E1

– Anticoagulants, NSAID, prostacylin– Antidiabetics

Herb to Herb– Anticoagulants – feverfew, ginkgo– Antihyperglycemic - glucomannan

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

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

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