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Resveratrol (3,5,4′-Trihydroxystilbene) is a natural polyphenol with a stilbene structure. Its chemical structure was characterized in 1940 by Takaoka, who isolated it from the root of Veratrum grandiflorum. However, it has been present in medicinal preparations, such as darakchasava or manakka , for more than 2000 years. Its basic structure consists of two phenolic rings bonded together by a double styrene bond, which forms the 3,5,4′-Trihydroxystilbene (molecular weight 228.25 g/mol). This double bond is responsible for the isometric cis- and trans-forms of resveratrol. It is worth mentioning that the trans-isomer is the most stable from the steric point of view. There are many synthetic and natural analogues of resveratrol, as well as adducts, derivatives, and conjugates, including glucosides. The synthesis of resveratrol decreases regularly during the grape ripening process, which explains the increasing susceptibility of mature fruits to infection by Botrytis cinerea.
Resveratrol is a phytoalexin. These chemicals are characterized by their low molecular weight and their ability to inhibit the progress of certain infections. The accumulation of these substances in plants is produced by a mechanism of resistance to parasites and other adverse conditions, like fungal infection, UV radiation, chemical substances and, in general, stressful factors for the plant. In fact, resveratrol is produced by more than 70 species of plants in response to such stressful situations. The concentration of resveratrol in plants depends on various factors. For example, in vines, the two most important factors are the weather and presence of fungus. Resveratrol can be found in some fruits, which are part of the human diet, such as blueberries (Vaccinium spp.), blackberries (Morus spp.), and peanuts (Arachis hypogaea). However, red wine is the main source of resveratrol in the Mediterranean diet.
Resveratrol content in red wine comes from grapes (Vitaceae). In particular, the richest sources are the skin, seeds, petioles, and woody parts. For that reason, red wine is richer in resveratrol than white wine, because during the production of red wine, parts of the grape where resveratrol is concentrated are macerated. This does not happen in white wine]. Alcohol formation during grape fermentation facilitates its solubility and thus its extraction. Cis- and trans-isomers coexist in plants and in wine. However, cis-resveratrol has never been found in grape extract. The trans-isomer appears to be the more predominant and stable natural form. Cis-isomerisation can occur when the trans-isoform is exposed to solar or artificial light or ultraviolet radiation at a wavelength of 254 or 366 nm..
Although less important in our culture, the richest source of resveratrol is the Polygonum cuspidatum herb, whose root extract has played a very important role in Japanese and Chinese traditional medicine. In fact, it is the main active ingredient in ko-jo-kon, which is used in the treatment of several cardiovascular diseases. Veratrum grandiflorum has a high content of resveratrol in leaves, when the plant is damaged by any chemical treatment. Furthermore, the roots and rhizomes of Veratrum formosanum are also rich in resveratrol and, in fact, a preparation of this plant has been traditionally used in east Asia to treat hypertension.
Article Produced By
Neelam Khaper
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