Wines resveratrol

Bertelli, A. (2009). Grapes, wines, resveratrol, and heart health. J. Cardiovasc. Pharm. 54, 468-476. 

The presence of and relationship between trans- and cis-resveratrol monomers in the varietal wines from Dalmatia (Croatia), produced according to the Croatian appellation of origin system, were reported [19]. Standard methods of analysis for general wine components were used for a preliminary control of the selected wines. Resveratrol monomers in wine were measured by HPLC. Significant differences... 

Phenolic compounds, primarily flavonoids, have antioxidant properties which may contribute to health benefits of wine consumption (Kanner et ai, 1994 Frankel, 1994). Wine consumption has a possible cardioprotective effect and may prevent thrombosis (Frankel, 1994). Epicatechin and quercetin are more effective in preventing LDL (low density lipoprotein) oxidation than a-tocopherol (vitamin E) (Frankel, 1994). Quercetin is found at an average concentration of 25 mg/L in red wine. Catechin and epicatechins are among the most abundant phenolics in wine and are present at about 150 mg/ L in red wine and about 15 mg/ L in white wine. Resveratrol is thought to be of major importance as a dietary antioxidant in red wines, but levels are much lower than catechin/epicatechin (Frankel, 1994). 

Polyphenolics are important constituents of grapes in determining the color, taste, and body of wines. Unlike other alcoholic beverages, red wine, which is obtained after about 10 days of maceration, contains phenolic compounds in substantial concentrations of up to 4 g L . Due to the lower maceration time, white and rose wines contain about a tenth of the polyphenol levels of red wines [1]. Among these compounds, stilbenoids constitute an important subclass, whose overall levels can reach over 100 mg in red wine. Resveratrol is one of the major stilbenoids of red wine with numerous promising biological activities. 

Other phenolic compounds included proanthocyanins (02-10-mers and >10 polymers), lignins, and stilbenes. The other phenolic compounds (mg 100 ml ) with high maximum values in alcoholic beverages were tyrosol (0.6. 5), syringaldehyde (0. 5), resveratrol 3-0-glucoside (0. 4), >10 polymers (11.0), 04-06-mers (6.7), 07-10-mers (5.0), and 02-mers (4.0) in red grape wine, resveratrol (1.4-4.4) in red muscadine grape wine, and tyrosol (5.7) in sherry. 

Patil BS, Jayaprakasha GK, Chidambara Murthy KN, Vikiam A (2009) Bioactive compounds historical perspectives, opportunities and challenges. J Agric Food Chem 57 8142-8160 Bertelli AAA, Das DK (2009) Grapes, wines, resveratrol, and heart health. J Cardiovasc Pharmacol 54 468-476... 

Guerrero RF, Garcia-Parrilla MC, Puertas B, Cantos-Villar E (2009) Wine, resveratrol and health a review. Nat Prod Commun 4 635-658... 

Levite D, Adrian M and Tamm L (2000), Preliminary results of resveratrol in wine of organic and conventional vineyards , in Wilier H and Meier U, Proceedings 6th International Congress on Organic Viticulture, 25-26 August 2000, Ackerstrasse, Germany, 256-257. 

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. 

People in France eat a lot of fatty foods but suffer less from fatal heart strokes than people in the northern regions of Europe or in North America, where wine is not consumed on a regular basis ( French paradox ). There is an increased favorable effect from red wine. The unique cardioprotective properties of red wine are due to the action of flavonoids, which are minimal in white wine. The best-researched flavonoids are resveratrol and quercetin, which confer antioxidant properties more potent than a-tocopherol. 

Wine Phenolics (mg/1) Gallic acid (qg/ml) Rutin (jUg/ml) Trans- resveratrol (qg/ml) Quercetin (Ug/ml)... 

Fig. 2.77. Chromatogram of a reverse-phase HPLC of Azorean (Basalto) red wine monitored at 306 nm. Peaks 1 = frans-pieceid 2 = cw-pieceid 3 = /nms-resvcralrol 4 = cis-resveratrol 5 = quercetin. Reprinted with permission from J. A. B. Baptista et al. [194].

Another study employed a similar RP-HPLC method for the determination of trails- and d.v-rcsvcratrol, catechin, epicatechin, quercetin and rutin in wines and musts. Wine samples were filtered and diluted when necessary and used for analysis without any other pretreatment. Separation was performed in an ODS column (150 X 4 mm i.d. paricle size 5 71m) at ambient temperature. The gradient began with ACN-5 per cent aqueous acetic acid (9 91, v/v) for 0-10 min to 25 75 in 1 min hold for 11 min to 70 30 in 1 min, hold for 5 min. The flow rate was 1 ml/min. Analytes were detected by DAD. Fluorescence detection used 280/315 nm (excitation/emission) for catechin and epicatechin 314/370 nm for fims-resveratrol and 260/370 nm for d.v-rcsvcratrol. Chromatograms of a red wine sample obtained at different... 

Fig. 2.79. Chromatograms of a white (I) and red wine sample (II). (LC-DAD signals at three different wavelenghts 256, 324, 365 nm). Peak identification 1 = gallic acid 2 = protocatechuic acid 3 = p-hydroxybenzoic acid 4 = vanillic acid 5 = caffeic acid 6 = (+)-catechin 7 = syringic acid 8 = p-coumaric acid 9 = ( — )-epicatechin 10 = ferulic acid 11 = fraras-resveratrol 12 = rutin 13 = myricetin 14 = cw-resveratrol 15 = quercetin A = caftaric acid B = coutaric acid. Reprinted with permission from M. Castellari et al. [196],...

Fig. 2.82. Chromatograms for a red wine sample using gradient elution and photodiode array detection. Flow rate, lml/min. Peak identification 1 = catechin 2 = epicatechin 4 = irans-resveratrol 6 = quercetin. Reprinted with permission from P. Vinas et al. [198].

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 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. 

There are a lot of stories of the resveratrol type small, naturally occurring molecules for which there is evidence of important physiological properties. Resveratrol, or one of its chemical relatives, may prove to be a valuable compound for human health. It may also prove to be a curiosity. Time will tell stay tuned. In the meantime, the resveratrol story is a boon for the makers and marketers of red wine. I do not know if we really need an excuse to drink a glass of red wine but it is convenient to have one. 

Curcumin, a polyphenolic constituent isolated from Curcuma longa L. Zingiberaceae (Fig. 6), and a methanol extract of the dried powdered turmeric rhizome were both active against 19 strains of HP, including five CagA- - strains. The MIC range was 6.25-50 /tg/mL. In addition, a red wine Vitis vinifera) and resveratrol, inhibited the growth of HP... 

Fig. 6. Phenolic constituents curcumin and the gingerols isolated from Zingiber officinale L. and Curcuma longa L., and resveratrol from a red wine extract. All have significant inhibitory activities on Cag- - strains of HP.

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. (2000) Red wine and resveratrol inhibit the growth of Helicobacter pylori in vitro. Am J Gastroenterol 95 1849. 

Resveratrol is another type of polyphenol, a stilbene derivative, that has assumed greater relevance in recent years as a constituent of grapes and wine, as well as other food products, with antioxidant, anti-inflammatory, anti-platelet, and cancer preventative properties. Coupled with the cardiovascular benefits of moderate amounts of alcohol, and the beneficial antioxidant effects of flavonoids, red wine has now emerged as an unlikely but most acceptable medicinal agent. 

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. 

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