Resveratrol in red wine

Resveratrol has a long history. It was initially isolated from the roots of white hellebore in 1940. No one paid much attention. In 1963, it was isolated from a plant used for centuries in traditional Japanese and Chinese medicine. Again, this did not attract much attention. The story got a lot hotter in 1992 when the presence of resveratrol in red wine was suggested to be associated with the cardioprotective effects of red wine. 

Subsequent studies in experimental animals have yielded provocative results. Resveratrol is known to extend the lifespan of a number of organisms from yeast to vertebrates. Resveratrol is also known to prevent or slow the progression of cancer, cardiovascular diseases, diabetes, inflammation, and ischemic injuries in experimental animals. In short, the suggestion that resveratrol in red wine may be responsible for favorable outcomes in human health is supported by a number of studies in experimental animals. However, the support is suggestive but certainly not definitive. Carefully controlled clinical trials in people will be required to establish the role, if any, of resveratrol or related small molecules in human health. Such clinical trials are currently underway. 

Bertelli AA, Giovannini L, Giannessi D, Migliori M, Bernini W, Fregoni M, Bertelli A. 1995. Antiplatelet activity of synthetic and natural resveratrol in red wine. Int J Tissue React 17 1-3. 

Stervbo U, Vang O, Bonnesen C. 2007. A review of the content of the putative chemopreventive phytoalexin resveratrol in red wine. Food Chem 101 449-457. 

The primary dietary source of trans-resveratrol is red wine. Although the concentration of resveratrol in red wine is variable, it has been found to be much higher than in white wines. Using chromatographic analysis, several studies have investigated... 

Careri, M., C. Corradini, L. Elviri, 1. Nicoletti, and 1. Zagnoni. (2003). Direct HPLC Analysis of Quercetin and trans-Resveratrol in Red Wine, Grape, and Winemaking Byproducts, /, Agric, Food Chem. 51, (18), 5226-5231. 

Airado, D., Galeano, T. and Durin, I. (2010) Determination of trans-resveratrol in red wine by adsorptive stripping square-wave voltammetry with medium exchange. Food Chem., 122,1320-1326. 

Mattivi F, Reniero F and Korhammer S. 1995. Isolation, characterization, and evolution in red wine vinification of resveratrol monomers. J Agric Food Chem 43(7)1820-1823. 

Condensation of coumaric acid with malonic acid yields the basic chalcone and stilbane skeletons (see Fig. 3.6). Stilbenes are found in most vascular plants, where they exhibit fungicidal and to a lesser extent antibiotic properties. They function as both constitutive and inducible defense substances. Some stilbenes inhibit fungal spore germination and hyphal growth, whereas others are toxic to insects and parasitic nematodes (round-worms). They also possess antifeeding and nematicide properties in mammals. For example, resveratrol (a stilbene in red wine) suppresses tumor formation in mammals. 

There is a more interesting, and possibly more important, explanation. A principal difference between American and French diets is the consumption of wine, specifically red wine. Could there be something in wine that accounts for the French Paradox Attention has been focused on a class of compounds found in red wine called polyphenols (they are found in white wine as well but in much smaller amounts). These have potent antioxidant properties. Most of the attention has been focused on resveratrol ... 

Resveratrol, (Fig. 6) a stilbene present in red wine had an MIC of 25 jUg/mL for the HP strains tested, while the red wine extract had an MIC range of 25-50 /ng/mL. Interestingly, resveratrol was also more active against CagA-v strains of HP than CagA- strains. ... 

Mahady GB, Pendland SL, Chadwick LR. (2003) Resveratrol and red wine extracts inhibit the growth of CagA+ strains of Helicobacter pylori in vitro. Am J Gastroenterol 9 1440-1441. 

Kasdallah-Grissa, A. et al. (2007) Resveratrol, a red wine polyphenol, attenuates ethanol-induced oxidative stress in rat liver. Life Sciences, 80 (11), 1033-1039. 

Wallerath, T., Deckert, G., Temes, T., Anderson, H., Li, H., Witte, K., and Forstermann, U., Resveratrol, a polyphenolic ph54oalexin present in red wine, enhances expression and activity of endothelial nitric oxide synthase. Circulation, 106, 1652, 2002. 

Many naturally occurring antioxidants are found in common foods. These include the green tea catechins,5 6 resveratrol from red wine,7 curcumin from curry powder,8 sul-foraphane from cruciferous vegetables,9 etc. Some synthetic materials are also added to foods to prevent rancidity of lipids. Examples include butylated hydroxy toluene (BHT) and butylated hydroxy anisole (BHA). 

The anti-carcinogenic effects of resveratrol were also tested in vivo, by examination of mammary glands of mice treated with DMBA and TPA. A dose-dependent reduction in the formation of tumors was observed when the mice were treated with resveratrol. Resveratrol is present in high concentrations in the skins of grapes (50-100 pg/g) and, consequently, in red wine (1.5-3 mg/1). Based on these experiments, the consumption of grapes and grape products appears to have beneficial effects. 

Vitaglione P, Sforza S, Galaverna G, Ghidini C, Caporaso N, Yescovi PP, Fogliano Y, Marchelli R. 2005. Bioavailability of traw-resveratrol from red wine in humans. Mol Nutr Food Res 49 495-504. 

Koop P, 1998. Resveratrol, a phytoestrogen found in red wine. A possible explanation for the conundrum of the French paradox Eur J Endocrinol 138 619-620. 

Su HC, Hung LM, Chen JK. 2006. Resveratrol, a red wine antioxidant, possesses an insulin-like effect in streptozotocin-induced diabetic rats. Am J Physiol Endocrinol Metab 290 E1339-E1346. 

Different hypotheses have been raised to explain these purported beneficial effects. Ono et al. have shown that the neuroprotective effects of various polyphenols (e.g., myricetin, morin, and, to a lesser extent, quercetin) may be due to their ability to inhibit amyloid fibrils and to destabilize fibrilized forms of Ap,20 suggesting that they could be considered as new therapeutic agents for the treatment of AP-associated diseases.21 Resveratrol, a red-wine polyphenol, has been proposed to promote the intracellular degradation of Ap by a proteasome-dependent and secretase-independent activity.22 Based on these findings, we compared the effects of polyphenols found in teas and red wine, using the model of AP-induced toxicity in rat hippocampal primary cell cultures. 

Resveratrol, a plant polyphenol found in red wine and grapes, enhanced the ability of butyrate to induce differentiation. 

The most common sequence uses three malonyl CoA acylations followed by cyclization to a new aromatic ring. The simplest type is exemplified by resveratrole, the compound in red wine that helps to prevent heart disease. Each step in this sequence is a simple reaction that you have met before. 

Perrone, G., Nicoletti, 1., Pascale, M., De Rossi, A., De Girolamo, A., Visconti, A. (2007). Positive correlation between high levels of ochratoxin A and resveratrol-related compounds in red wines. J. Agric. Food Chem., 55, 6807-6812. 

Vitaglione, R, Sforza, S., Galavema, G., Ghidini, C., Caporaso, N., Vescovi, P. R, Fogliano, V, Marchelli, R. (2005). Bioavailability of trans-resveratrol from red wine in humans. Mol. Nutr. Food Res., 49, 495-504. 

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