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.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Cells, Cultured
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Cyclooxygenase 1
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Cyclooxygenase 2
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors / chemistry*
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Cyclooxygenase Inhibitors / isolation & purification
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Glucosides / chemistry*
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Glucosides / isolation & purification
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Isoenzymes / chemistry
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Prostaglandin-Endoperoxide Synthases / chemistry
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Rosales / chemistry*
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Spectrophotometry, Infrared
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Spectrophotometry, Ultraviolet
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Stilbenes*
Substances
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors
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Glucosides
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Isoenzymes
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Stilbenes
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resveratrol dehydrodimer 11-O-glucopyranoside
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Cyclooxygenase 1
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Cyclooxygenase 2
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Prostaglandin-Endoperoxide Synthases