title: Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures.
abstract: 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.
authors.affiliation: 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.
authors.forename: P
authors.initials: P
authors.lastname: Waffo-Teguo
authors.forename: D
authors.initials: D
authors.lastname: Lee
authors.forename: M
authors.initials: M
authors.lastname: Cuendet
authors.forename: J
authors.initials: J
authors.lastname: Mérillon
authors.forename: J M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: A D
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: 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
chemical_list: 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