Stilbenoid

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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 are secondary products of heartwood formation in trees that can act as phytoalexins.

A bacterial stilbenoid, produced in an alternative ketosynthase-directed pathway, (E)-;3,5-Dihydroxy-4-isopropyl-trans-stilbene, exists in Photorhabdus bacterial symbionts of Heterorhabditis nematodes.[2]

An example of a stilbenoid is resveratrol, which is found in grapes and which has been suggested to have many health benefits.[3]

Oligomeric forms are known as oligostilbenoids.

Chemistry[edit]

Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization to form dihydrophenanthrenes.

Phytoalexin properties[edit]

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

Known stilbenoids[edit]

Aglycones
Glycosides

See also[edit]

References[edit]

  1. ^ 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): 3505–11. doi:10.1021/jf0602673. PMID 19127717. 
  2. ^ 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): 1942–5. doi:10.1002/anie.200705148. PMID 18236486. 
  3. ^ Jang MS, Cai EN, Udeani GO (1997). "Cancer chemopreventive activity of resveratrol, a natural product derived from grapes". Science 275 (5297): 218–20. doi:10.1126/science.275.5297.218. PMID 8985016. 
  • Hillis WE (1987) Heartwood and tree exudates. Springer, Berlin Heidelberg New York.
  • Yamada T, Ito S (1993) Chemical defense responses of wilt-resistant pine species, Pinus strobus and P. taeda, against Bursaphelenchus xylophilus infection. Ann Phytopathol Soc Jpn 59:666–672.