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Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures
P Waffo-Teguo1, D Lee, M Cuendet
1Program 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.
Journal of Natural Products
|February 15, 2001
Summary
Researchers discovered two new resveratrol dimer glucosides from Vitis vinifera cell cultures. These compounds, along with known stilbenes, show cyclooxygenase-1 and -2 inhibitory activity, suggesting potential anti-inflammatory properties.
Area of Science:
- Phytochemistry
- Natural Products Chemistry
- Pharmacology
Background:
- Vitis vinifera (grapevine) is a rich source of stilbenoids, known for their diverse biological activities.
- Oligostilbenes, formed by the oligomerization of stilbene units, represent a less explored class of natural products.
- Understanding the chemical diversity and bioactivity of Vitis vinifera secondary metabolites is crucial for discovering new therapeutic agents.
Purpose of the Study:
- To isolate and characterize novel stilbene dimer glucosides from Vitis vinifera cell cultures.
- To elucidate the structures and stereochemistry of the newly identified compounds.
- To evaluate the cyclooxygenase (COX) inhibitory activity of the isolated stilbenes.
Main Methods:
- Extraction and isolation of compounds from Vitis vinifera cell cultures.
- Structure elucidation using comprehensive spectroscopic data analysis (e.g., NMR, MS).
- In vitro enzymatic assays to determine cyclooxygenase-1 and -2 inhibitory activity (IC50 values).
Main Results:
- 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 successfully isolated.
- Compounds 1 and 2 represent a novel class of oligostilbenes, derived from resveratrol and its glucoside.
- Compounds 1 and the known resveratrol (E)-dehydrodimer (3) demonstrated non-specific inhibition of cyclooxygenase-1 and -2, with IC50 values around 5 microM.
Conclusions:
- The isolation of novel oligostilbenes from Vitis vinifera cell cultures expands the known chemical diversity of plant stilbenoids.
- The identified compounds possess cyclooxygenase inhibitory activity, indicating potential anti-inflammatory effects.
- Further research into these novel compounds could lead to the development of new therapeutic strategies targeting inflammatory pathways.