alpha-Viniferin

Catalog No.	CFN97068
CAS No.	62218-13-7
Molecular Weight:	678.7
Molecular Formula	C42H30O9
DBs	[PubChem]:274953313 [ChEMBL]:66359 [PCIDB]:15693

Standard InChI:

InChI=1S/C42H30O9/c43-22-7-1-19(2-8-22)40-37-28-13-25(46)17-32-35(28)39(42(50-32)21-5-11-24(45)12-6-21)30-15-27(48)18-33-36(30)38(29-14-26(47)16-31(49-40)34(29)37)41(51-33)20-3-9-23(44)10-4-20/h1-18,37-48H/t37-,38-,39+,40+,41+,42-/m0/s1

Biological Activity

Alpha-viniferin isolated from Caragana chamlagu is a trimer of resveratrol, has anti-inflammatory, anti-oxidant, anti-arthritis, and anti-tumor activities;alpha-viniferin strongly inhibits 7 of the 9 CYP isoforms (except CYP2A6 and CYP2E1); alpha-viniferin strongly inhibits CYP2C19-mediated omeprazole 5-hydroxylation and CYP3A4-catalyzed midazolam 1-hydroxylation with IC 50 values of 0.93 and 1.2μM, respectively.^[1]

(+)-Alpha-viniferin, a stilbene trimer from Caragana chamlague, inhibits acetylcholine

-sterase (AChE) activity in a dose-dependent manner, the IC50 value is 2.0 microM.^[2]

Alpha-viniferin at doses> 30 mg/kg(p. o.) or > 3 mg/kg (i. v.)shows significant anti-inflammatory activity through inhibition of cyclooxygenase-2 and inducible nitric oxide synthase on carrageenin-induced paw edema in mice; alpha-Viniferin showed an inhibitory effect with an IC(50) value of 4.9 microM on COX-2 activity, but a very weak inhibitory effect at 100 microM on COX-1 activity; alpha-Viniferin inhibited synthesis of iNOS transcript with an IC50 value of 4.7 microM.^[3]

Alpha-viniferin is a prostaglandin H2 synthase inhibitor, the inhibitory potency of (+)-alpha-viniferin is about 3- to 4-fold stronger than that of resveratrol on cyclooxygenase activity of prostaglandin H2 synthase partially purified from sheep seminal vesicles.^[4]