Stilbenes

Stilbenes are a class of organic compounds with the general formula (C6H5CH=CHC6H5). They are characterized by a 1,2-diphenylethylene nucleus. Stilbenes are derived from the biosynthesis of phenylpropanoids and tyrosine. They can be produced in plants and microorganisms through different pathways. Stilbenes are found in the skins of grapes and in wine, particularly red wine.

Structure and Classification

Stilbenes are hydrocarbons that consist of a ethylene (ethene) group flanked by two phenyl groups. They can exist as either cis or trans isomers, with the trans form being more stable due to the greater separation of the phenyl groups.

Stilbenes can be classified into three main types: monomeric, oligomeric, and polymeric. Monomeric stilbenes include resveratrol, piceatannol, and pterostilbene. Oligomeric stilbenes, also known as viniferins, are dimers or trimers of resveratrol. Polymeric stilbenes, such as ε-viniferin, are larger molecules composed of multiple resveratrol units.

Biosynthesis

Stilbenes are synthesized from the amino acid phenylalanine in a process that involves several enzymes, including phenylalanine ammonia lyase (PAL), cinnamate 4-hydroxylase (C4H), and stilbene synthase (STS). The biosynthesis of stilbenes is part of the larger phenylpropanoid pathway, which also leads to the production of flavonoids and lignin.

Biological Activity and Uses

Stilbenes have been found to have a variety of biological activities, including antioxidant, anti-inflammatory, anticancer, and antimicrobial effects. They are also known to have cardioprotective and neuroprotective properties.

Resveratrol, a type of stilbene, has been extensively studied for its potential health benefits. It has been found to extend the lifespan of several organisms, and it has been suggested as a potential treatment for a variety of diseases, including cancer, cardiovascular disease, and neurodegenerative diseases.

See Also

• Phenylpropanoid
• Resveratrol
• Phenylalanine ammonia lyase
• ε-viniferin

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