Chemical constituents from the fruits of Withania coagulans (Stocks) Dunal

Document Type: Original Article

Authors

1 Phytopharmaceuticals Research Laboratory, School of Pharmaceutical Education and Research, Jamia Hamdard, P.O. Hamdard Nagar, New Delhi-110062, India

2 College of Pharmacy, Jazan University, Jazan, Saudi Arabia

Abstract

Withania coagulans (Stocks) Dunal (family: Solanaceae) is a rigid undershrub found in Iran, Afghani­stan, Pakistan, northern India and Nepal. Its fruits are used to treat asthma, biliousness, flatulent colic, cough, diabetes, dyspepsia, liver complaints, intestinal infections, skin rashes, stomachache, strangury and wounds. The air-dried fruits of W. coagulans were exhaustively extracted with methanol in a Soxhlet apparatus. The concentrated methanol extract was adsorbed on silica gel to be chromatographed on a silica gel column. The column was eluted with dichloromethane, ethyl acetate and methanol suc­cessively to isolate ten new phytoconstituents characterized as (3R,4R)-dihydroxyadipic-γ,γ’-dilactone (n-hexa-1(3),4(5)-diolide, 2), (20S,22R)-1-oxo-witha-2,24-dienolide (withacoagulanide A, 3), (20S,22R)- 1-oxo-witha-24-enolide (withacoagulanide B, 4), (20S,22R)-1-oxo-witha-6β-ol-2,24-dienolide (witha­coagulanide C, 5), (20S,22R)-1-oxo-witha-3β,5β-diol-24-enolide (withacoagulanide D, 6), (20S,22R)-1- oxo-witha-6β-ol-2,24-dienolide-6β-D-arabinopyranosyl-2′-(2′′-methoxy)-benzoate (withacoagunalide C 6-arabinosyl 2′-O-anisate, 7), (20S,22R)-1-oxo-witha-3β-ol-24-enolide-3β-O-D-galactoyranosyl- (2′→1′′)-β-O-D-galactopyranoside (3-O-digalactosyl withacoagulanide B, 8), 1-oxo-3-seco-witha-21, 27, 28-trioic acid-24-ene-6β-ol-19(8), 18(11)-diolide-6β-O-D-galacuronopyranoside (3-secowithacoag­ulanolide 6β-olyl galactourinoside, 10), (20S,22R)-1-oxo-witha-6β-ol-2,24-enolide-6β-O-D-(4′-acetoxy arabinopyranosyl-(2′→1′′)-(3′′,4′′-diacetoxy arabinopyranosyl)-2′′-(2′′′-methoxy)-benzoate (withacoag­ulanide C 6β-olyl diarabinosyl 2′′-(O)-anisate, 11) and n-hexanoyl-β-O-D-xylopyranosyl-(2′→1′′)-β-O-D-xylopyranosyl-(2′′→1′′′)-β-O-D-xylopyrano- side (caproyl trixyloside, 12) along with the known rare chemical compounds identified as cetyl palmitate (hexadecyl hexadecanoate, 1) and glyceryl-1,2-di­hexadecanoate-3-phosphate (glyceryl-1,2-dipalmityl 3-phosphate, 9). The structures of isolated phyto­constituents were established on the basis of analysis of spectral data and chemical means.

Graphical Abstract

Chemical constituents from the fruits of Withania coagulans (Stocks) Dunal

Keywords


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