Stilbenoid

Class of chemical compounds related to stilbene

Chemical structure of resveratrol, a well-known stilbenoid.

Stilbenoids are a class of phenolic compounds that are derived from the stilbene structure. These compounds are characterized by the presence of a 1,2-diphenylethylene backbone, which is a type of diarylethene. Stilbenoids are naturally occurring and are found in a variety of plant species, where they often serve as phytoalexins, compounds that are produced by plants in response to pathogen attack.

Chemical Structure

Stilbenoids are based on the stilbene structure, which consists of two phenyl rings connected by an ethylene bridge. This structure allows for the possibility of cis-trans isomerism, although the trans form is more stable and more common in nature. The basic structure can be modified by the addition of various functional groups, leading to a wide variety of stilbenoid compounds.

Biosynthesis

Stilbenoids are synthesized in plants through the phenylpropanoid pathway, which is a major metabolic pathway responsible for the production of many secondary metabolites. The key enzyme involved in the biosynthesis of stilbenoids is stilbene synthase, which catalyzes the formation of the stilbene backbone from p-coumaroyl-CoA and three molecules of malonyl-CoA.

Biological Activity

Stilbenoids are known for their diverse biological activities. They have been studied for their antioxidant, anti-inflammatory, anticancer, and antimicrobial properties. One of the most studied stilbenoids is resveratrol, which is found in the skin of grapes, blueberries, and other fruits. Resveratrol has gained attention for its potential health benefits, including cardioprotective effects and its role in longevity.

Occurrence

Stilbenoids are found in a variety of plant species, including grapes, peanuts, and certain types of berries. They are also present in red wine, which is a significant dietary source of resveratrol. The concentration of stilbenoids in plants can vary depending on environmental factors and the presence of pathogens.

Applications

Due to their biological activities, stilbenoids have potential applications in medicine, cosmetics, and agriculture. In medicine, they are being investigated for their potential to prevent or treat various diseases. In cosmetics, stilbenoids are used for their antioxidant properties, which can help protect the skin from damage. In agriculture, they are studied for their role in plant defense and their potential use as natural pesticides.

Related pages

• Phenolic compounds
• Phytoalexins
• Resveratrol
• Phenylpropanoid pathway