Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures.
Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-beta-D-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11'-O-beta-D-glucopyranoside (2), were isolated together with the known resveratrol (E)-dehydrodimer (3) and pallidol (4) from Vitis vinifera cell cultures. The structures and stereochemistry of the new compounds were determined on the basis of spectroscopic data analysis. Compounds 1 and 2 are dimers that belong to a new type of oligostilbene formed from a resveratrol unit and a resveratrol glucoside unit. Compounds 1 and 3 exhibited nonspecific inhibitory activity against cyclooxygenase-1 and -2, with IC(50) values in the range of 5 microM, whereas compound 4 was approximately 10-fold less active.
Waffo-Teguo
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P
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
Lee
D
D
Cuendet
M
M
Mérillon
J
J
Pezzuto
J M
JM
Kinghorn
A D
AD
D002478:Cells, Cultured; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D007527:Isoenzymes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011451:Prostaglandin-Endoperoxide Synthases / Q000737:chemistry; D019685:Rosales / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013267:Stilbenes
D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D005960:Glucosides; D007527:Isoenzymes; D013267:Stilbenes; C428196:resveratrol dehydrodimer 11-O-glucopyranoside; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases