From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Resveratrol is a biologically important stilbenoid.

Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones.[1] Stilbenoids can be produced by plants and bacteria.


Stilbenoids are hydroxylated derivatives of stilbene and have a C6–C2–C6 structure. They belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones.[1] Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization, called Stilbene photocyclization to form dihydrophenanthrenes. Oligomeric forms are known as oligostilbenoids.


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


Stilbenoids are produced in various plants, for example they are secondary products of heartwood formation in trees that can act as phytoalexins. Another example is resveratrol, an antifungal which is found in grapes and which has been suggested to have health benefits.[2] 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.[3]

Stilbenoids are secondary metabolites present in Cannabis sativa.[4]


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

See also[edit]


  1. ^ a b V. S. Sobolev; B. W. Horn; T. L. Potter; S. T. Deyrup; J. B. Gloer (2006). "Production of Stilbenoids and Phenolic Acids by the Peanut Plant at Early Stages of Growth". J. Agric. Food Chem. 54 (10): 3505–3511. doi:10.1021/jf0602673. PMID 19127717.
  2. ^ Jang MS, Cai EN, Udeani GO (1997). "Cancer chemopreventive activity of resveratrol, a natural product derived from grapes". Science. 275 (5297): 218–220. doi:10.1126/science.275.5297.218. PMID 8985016.
  3. ^ Joyce SA, Brachmann AO, Glazer I, Lango L, Schwär G, Clarke DJ, Bode HB (2008). "Bacterial biosynthesis of a multipotent stilbene". Angew Chem Int Ed Engl. 47 (10): 1942–1945. CiteSeerX doi:10.1002/anie.200705148. PMID 18236486.
  4. ^ Flores-Sanchez, Isvett Josefina; Verpoorte, Robert (2008-10-01). "Secondary metabolism in cannabis". Phytochemistry Reviews. 7 (3): 615–639. doi:10.1007/s11101-008-9094-4.