Stilbenoids are hydroxylated derivatives of

stilbene Stilbene may refer to one of the two stereoisomers of 1,2-diphenylethene: * (''E'')-Stilbene (''trans'' isomer) * (''Z'')-Stilbene (''cis'' isomer) See also * Stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C ...

. They have a C₆–C₂–C₆ structure. In biochemical terms, they belong to the family of

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...

s and share most of their

biosynthesis Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme-Catalysis, catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthe ...

pathway with chalcones. Most stilbenoids are produced by plants, and the only known exception is the antimicrobial stilbenoid drug tapinarof which is biosynthesized by the Gram-negative bacterium '' Photorhabdus luminescens.''

Chemistry

Stilbenoids are hydroxylated derivatives of

and have a C₆–C₂–C₆ structure. They belong to the family of

s and share most of their

pathway with chalcones. Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization, called stilbene photocyclization to form dihydrophenanthrenes. Oligomeric forms are known as oligostilbenoids.

Types

;Aglycones *

Piceatannol Piceatannol is the organic compound with the formula . Classified as a stilbenoid and a phenol, it is a white solid, although samples often are yellow owing to impurities. Natural occurrences Piceatannol and its glucoside, astringin, are foun ...

in the roots of Norway spruces * Pinosylvin is a fungal toxin protecting wood from fungal infection, found in trees of the pine family *

Pterostilbene Pterostilbene () (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role. Natural occurrence Pterostilbene is found in almonds, various ''Vaccinium'' berries ( ...

in almonds, pine and

vaccinium ''Vaccinium'' is a common and widespread genus of shrubs or dwarf shrubs in the heath family (Ericaceae). The fruits of many species are eaten by humans and some are of commercial importance, including the cranberry, blueberry, bilberry (wh ...

berries *

Resveratrol Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacterium, ba ...

in grapes ;Glycosides *

Astringin Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of ''Picea sitchensis'' and ''Picea abies'' (Norway spruce). It is also present in ''Vitis vinifera'' cells cultures and in wine Wine is an alcoholic ...

in the bark of Norway spruce * Piceid is a resveratrol derivative in grape juices

Production

Stilbenoids are produced in various plants, for example they are secondary products of

heartwood Wood is a structural tissue/material found as xylem in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulosic fibers that are strong in tension and embedded in a matrix of lignin t ...

formation in trees that can act as phytoalexins. Another example is

resveratrol Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacterium, ba ...

, an antifungal which is found in

grape A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began approximately 8,0 ...

s and which has been suggested to have health benefits. Ampelopsin A and Ampelopsin B are resveratrol dimers produced in porcelain berry. A bacterial stilbenoid, (''E'')-3,5-dihydroxy-4-isopropyl-''trans''-stilbene, is produced by '' Photorhabdus'' which is a bacterial symbiont of insect nematodes called '' Heterorhabditis''. Stilbenoids are

secondary metabolite Secondary metabolites, also called ''specialised metabolites'', ''secondary products'', or ''natural products'', are organic compounds produced by any lifeform, e.g. bacteria, archaea, fungi, animals, or plants, which are not directly involved ...

s present in

Cannabis sativa ''Cannabis sativa'' is an annual Herbaceous plant, herbaceous flowering plant. The species was first classified by Carl Linnaeus in 1753. The specific epithet ''Sativum, sativa'' means 'cultivated'. Indigenous to East Asia, Eastern Asia, the pla ...

Properties

Phytoalexins have been suggested by some studies to be responsible for resistance to some tree diseases, such as pine wilt.

References

Books

* * {{Phenylpropanoids Wood extracts