What is Resveratrol?

CHEMICAL AND PHYSICAL PROPERTIES

 

Resveratrol’s formal chemical name is (E)-5-(4-hydroxystyryl)benzene-1,3-diol. Its other names are Trans-3,5,4′-trihydroxystilbene; 3,4′,5-stilbenetriol; trans-resveratrol and (E)-5-(p-hydroxystyryl)resorcinol. It is a stilbenoid, naturally produced in some plants with the help of the enzyme stilbene synthase. When produced, it helps defend the plant against environmental stresses and ultraviolet radiation that cause disease. Resveratrol is a polyphenolic phytoalexin which has antibiotic capabilities for the plants.

 

At room temperature resveratrol is a solid off-white powder. Its melting point is 253 to 255˚C. Its molecular formula is C14H12O3 and molecular weight is 228.25 g/mol. Resveratrol is a fat-soluble compound and soluble in ethanol at ~50 mg/ml, in DMSO at 16 mg/ml at least, and is only very slightly soluble in water at ~3 mg/100 ml. Resveratrol exists as two structural isomers: cis- (Z) and trans- (E). Both cis- and trans-resveratrol are glucosides, which mean they bound to a glucose molecule. When exposed to heat or ultraviolet radiation, the trans- form can undergo isomerisation to the cis- form. Resveratrol occurs predominantly in the trans- form, which is the more stable form of resveratrol. It was found to be stable at 75% humidity and 40˚C in the presence of air, all of which are conditions of “accelerated stability.” Trans-resveratrol is more biologically active and more commonly studied compared to the cis- form.

 

Resveratrol is a polyphenol, a type of antioxidant. Antioxidants are substances that slow down the damaging effects of oxidative stress. When our body cells use oxygen, they produce unstable molecules known as free radicals that have potential to cause damage by attacking healthy cells. Antioxidants reduce their effect by binding together with the free radicals, thus decreasing their destructive power. Besides the commonly known sources of antioxidants, such as Vitamins A and C in vegetables and fruits, antioxidants are also found in polyphenols. Polyphenols can be classified into two main forms: flavonoids and nonflavonoids. Flavonoids are found in foods such as oranges, apples, grape juice, tea, and cocoa. Resveratrol is one of the nonflavonoids that is currently an intriguing topic of research. Scientific studies carried out on mice have found that nonflavonoids seem to help prevent arteries from becoming clogged with fatty substances.

 

Resveratrol therefore has antibiotic capabilities for the plants which produce it, and has antioxidant properties which may prevent and repair damage done by free radical cells in the body. In addition to these, some studies have shown that resveratrol is an anti-mutagen and an anti-inflammatory. As an anti-mutagen, it inhibits the mutation of healthy normal cells into cancerous growths and tumors. As an anti-inflammatory, resveratrol reduces inflammation, treating pain.