Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures.

Abstract

Moderate consumption of wine is associated with a reduced risk of cancer. Grape plant cell cultures were used to purify 12 phenols: the stilbenoids trans-astringin, trans-piceid (2), trans-resveratroloside, trans-resveratrol, trans-piceatannol, cis-resveratroloside, cis-piceid, and cis-resveratrol; the flavans (+)-catechin, (-)-epicatechin, and epicatechin 3-O-gallate; and the flavan dimer procyanidin B2 3'-O-gallate. These compounds were evaluated for potential to inhibit cyclooxygenases and preneoplastic lesion formation in carcinogen-treated mouse mammary glands in organ culture. At 10 micrograms/ml, trans-astringin and trans-piceatannol inhibited development of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in mouse mammary glands with 68.8% and 76.9% inhibition, respectively, compared with untreated glands. The latter compound was the most potent of the 12 compounds tested in this assay, with the exception of trans-resveratrol (87.5% inhibition). In the cyclooxygenase (COX)-1 assay, trans isomers of the stilbenoids appear to be more active than cis isomers: trans-resveratrol [50% inhibitory concentration (IC50) = 14.9 microM, 96%] vs. cis-resveratrol (IC50 = 55.4 microM). In the COX-2 assay, among the compounds tested, only trans- and cis-resveratrol exhibited significant inhibitory activity (IC50 = 32.2 and 50.2 microM, respectively). This is the first report showing the potential cancer-chemopreventive activity of trans-astringin, a plant stilbenoid recently found in wine. trans-Astringin and its aglycone trans-piceatannol were active in the mouse mammary gland organ culture assay but did not exhibit activity in COX-1 and COX-2 assays. trans-Resveratrol was active in all three of the bioassays used in this investigation. These findings suggest that trans-astringin and trans-piceatannol may function as potential cancer-chemopreventive agents by a mechanism different from that of trans-resveratrol.

• Authors: P Waffo-Téguo, M E Hawthorne, M Cuendet, J M Mérillon, A D Kinghorn, J M Pezzuto, R G Mehta
• Journal: Nutrition and cancer (Nutr Cancer) Vol. 40 Issue 2 Pg. 173-9 ( 2001) ISSN: 0163-5581 [Print] United States
• PMID: 11962253 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Anticarcinogenic Agents
• Biflavonoids
• Cyclooxygenase 2 Inhibitors
• Cyclooxygenase Inhibitors
• Isoenzymes
• Membrane Proteins
• Phenols
• Plant Extracts
• Proanthocyanidins
• Stilbenes
• procyanidin B2
• 9,10-Dimethyl-1,2-benzanthracene
• Catechin
• epicatechin gallate
• Cyclooxygenase 1
• Cyclooxygenase 2
• Prostaglandin-Endoperoxide Synthases
• Ptgs1 protein, mouse
• Resveratrol

Topics

• 9,10-Dimethyl-1,2-benzanthracene
• Animals
• Anticarcinogenic Agents (pharmacology, therapeutic use)
• Biflavonoids
• Catechin (analogs & derivatives, pharmacology, therapeutic use)
• Cells, Cultured
• Chromatography, High Pressure Liquid
• Cyclooxygenase 1
• Cyclooxygenase 2
• Cyclooxygenase 2 Inhibitors
• Cyclooxygenase Inhibitors (pharmacology)
• Female
• Isoenzymes (antagonists & inhibitors, metabolism)
• Mammary Neoplasms, Experimental (chemically induced, prevention & control)
• Membrane Proteins
• Mice
• Mice, Inbred BALB C
• Organ Culture Techniques
• Oxygen Consumption
• Phenols (isolation & purification)
• Plant Extracts (chemistry)
• Proanthocyanidins
• Prostaglandin-Endoperoxide Synthases (metabolism)
• Resveratrol
• Stilbenes (pharmacology, therapeutic use)
• Vitis (chemistry)
• Wine (analysis)