Antioxidants resveratrol

Becker, J. V., Armstrong, G. O., van der Merwe, M. J., Lambrechts, M. G., Vivier, M. A., Pretoiius, 1. S. (2003) Metabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrol. FFMS Yeast Research, 4, 79-85. 

Ray, P.S. Maulik, G. Cordis, G.A. Bertelli, A.A.E. Bertelli, A. Das, D.K. The red wine antioxidant resveratrol protects isolated rat hearts from ischemia reper-fusion injury. Free Radical Biol. Med. 1999, 27, 160-169. 

DSM produces the antioxidant Resveratrol, the component in red wine that is responsible for a number of positive health effects also known as The French paradox . They have published a total synthesis of Resveratrol that is based on a Heck approach using acetylated intermediates (Scheme 13) [48, 49]. The best yield (94%) and highest substrate/catalyst ratio (2,000) were achieved using the palladacycle catalyst developed by Najera and co-workers [49, 50]. Hydrolysis of the tris-acetate provided Resveratrol in good yield. 

Documented effects The alkaloid spherophysine, which was isolated from the aboveground plant parts, has hypotensive activity and effects uterine action. In the form of a benzoic-acid salt, it is used for essential hypertension of the first and second degrees. Spherophysine is used for arterial hypertension, weak birthing activity (labor difficulties), and post natal bleeding (Sokolov and Zamotaev 1989). A stilbene isolated from the plant was synthesized and tested for antioxidant activity and showed superior antioxidative activity when compared to the well-known antioxidants resveratrol, vitamin C and butylated hydroxyanisole (BHA) (Venkateswarlu et al. 2003). Additionally, synthesized stilbenes based on naturally occurring compounds were active against leukemia and lymphoma cell lines (Tolomeo et al. 2005). 

It is well known that drinking wine and grape juices will reduce cardiovascular, cerebrovascular, and peripheral vascular risks due to the presence of resveratrol. As a natural antioxidant, resveratrol is able to prevent LDL oxidation, scavenge intracellular reactive oxygen species, lower the oxidative stress, and induce NO synthesis. Resveratrol modulates various aspects of cardiovascular diseases and is effective against atherosclerosis, hypertension, ischemia reperfusion injury and heart failure, and many other cardiac dysfunctions [111]. 

Gurusamy, N., Ray, D., Lekli, 1., and Das, D.K. 2010. Red wine antioxidant resveratrol-modified cardiac stem cells regenerate infarcted myocardium. J CellMolMed. 74 2235-9. 

Olas B and Wachowicz B. 2002. Resveratrol and vitamin C as antioxidants in blood platelets. Thromb Res 106(2) 143-148. 

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. 

Classic antioxidants, vitamin E, vitamin C, and others can suppress the activation of apoptosis. For example, ascorbic acid prevented cytochrome c release and caspase activation in human leukemia cells exposed to hydrogen peroxide [128], Pretreatment with A -acctylcystcinc, ascorbate, and vitamin E decreased homocysteine thiolactone-induced apoptosis in human promyelocytic leukemia HL-60 cells [129]. Resveratrol protected rat brain mitochondria from anoxia-reoxygenation damage by the inhibition of cytochrome c release and the reduction of superoxide production [130]. However, it should be mentioned that the proapoptotic effect of ascorbate, gallic acid, or epigallocatechin gallate has been shown in the same human promyelocytic leukemia cells [131]. 

There are numerous other polyphenolic compounds possessing in vitro and in vivo antioxidative activity. Several examples of these compounds are cited below. One of nonflavonoid polyphenols of particular interest is resveratrol (3,5,4 -trihydroxy-Znmv-stilbcne, Figure 29.8), which has been identified as a potential cancer chemopreventive agent and an antimutagen [182]. It has been found that resveratrol is the efficient inhibitor of cyclooxygenase and the inhibitor of free radical-mediated cellular processes. For example, resveratrol is a better free radical scavenger than a-tocopherol or ascorbic acid but has nearly the same activity as... 

A comparison with its different derivatives shows that 4 -OH is not a sole reactive group responsible for the antioxidant activity of resveratrol, while the trans-conformation is absolutely necessary for the inhibition of cell proliferation [187], However, similar to flavonoids resveratrol may exhibit prooxidant properties, for example to promote DNA fragmentation, although its prooxidant activity seems to be unimportant under physiological conditions [188],... 

In addition to their possible prooxidant activity (see above) polyphenols and flavonoids may influence cancer cells via their antioxidant properties. Recently, Jang et al. [219] studied cancer chemopreventive activity of resveratrol, a natural polyphenolic compound derived from grapes (Chapter 29). These authors showed that resveratrol inhibited the development of preneoplastic lesions in carcinogen-treated mouse mammary glands in culture and inhibited tumorigenesis in a mouse skin cancer model. Flavonoids silymarin and silibinin also exhibited antitumor-promoting effects at the stage I tumor promotion in mouse skin [220] and manifested antiproliferative effects in rat prostate cancer cells [221]. 

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 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. 

Giilgin, I. (2010). Antioxidant properties of resveratrol A structure-insight. Innov. Food Sci. Emerg. Technol. 11,210-218. 

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). 

Resveratrol has also been reported to offer protection against cardiovascular disease, such as coronary heart disease. The effects of resveratrol on factors implicated in the development of coronary heart disease - human platelet aggregation and the synthesis of eicosanoids (lipids) from arachidonate by platelets - were investigated and compared with the actions of other wine phenolics - catechin (1.39), epicatechin (7.18a), and quercetin (1.43) - and the antioxidants a-tocopherol (7.10a), hydroquinone and butylated hydroxytoluene. Resveratrol and quercetin demonstrated a dose-dependent inhibition of platelet aggregation, whereas the other compounds tested were inactive. Resveratrol also inhibited the synthesis of the eicosanoids in a dose-dependent manner, whereas the other phenolics were less effective of not effective at all. Removal of the alcohol from the wine did not diminish the effect on platelet aggregation (Pace-Asciak et al., 1995 Goldberg et al., 1995). 

The pharmacokinetic dispositions of other stilbenes that are structurally similar to resveratrol and have pharmacological activity across many anticancer, anti-inflammatory, and antioxidant assays have been studied. The pharmacokinetics was characterized in male Sprague-Dawley rats after single intravenous... 

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