Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures

Pierre Waffo-Teguo; Dongho Lee; Muriel Cuendet; Jean Michel Mërillon; John M. Pezzuto; A. Douglas Kinghorn

doi:10.1021/np000426r

Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures

Pierre Waffo-Teguo, Dongho Lee, Muriel Cuendet, Jean Michel Mërillon, John M. Pezzuto, A. Douglas Kinghorn

Research output: Contribution to journal › Article

86 Citations (Scopus)

Abstract

Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11′-O-β-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 IC₅₀ values in the range of 5 μM, whereas compound 4 was approximately 10-fold less active.

Original language	English
Pages (from-to)	136-138
Number of pages	3
Journal	Journal of Natural Products
Volume	64
Issue number	1
DOIs	https://doi.org/10.1021/np000426r
Publication status	Published - 2001 Feb 10
Externally published	Yes

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ASJC Scopus subject areas

Plant Science
Chemistry (miscellaneous)
Drug Discovery
Organic Chemistry
Pharmacology

Cite this

Waffo-Teguo, P., Lee, D., Cuendet, M., Mërillon, J. M., Pezzuto, J. M., & Douglas Kinghorn, A. (2001). Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures. Journal of Natural Products, 64(1), 136-138. https://doi.org/10.1021/np000426r

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abstract = "Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11′-O-β-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 IC50 values in the range of 5 μM, whereas compound 4 was approximately 10-fold less active.",

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AU - Waffo-Teguo, Pierre

AU - Lee, Dongho

AU - Cuendet, Muriel

AU - Mërillon, Jean Michel

AU - Pezzuto, John M.

AU - Douglas Kinghorn, A.

PY - 2001/2/10

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N2 - Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11′-O-β-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 IC50 values in the range of 5 μM, whereas compound 4 was approximately 10-fold less active.

AB - Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11′-O-β-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 IC50 values in the range of 5 μM, whereas compound 4 was approximately 10-fold less active.

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10.1021/np000426r