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Open Access Articles- Top Results for Stilbenoid

Stilbenoid

File:Resveratrol.svg
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

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

Phytoalexin properties

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

Known stilbenoids

Aglycones
Glycosides

See also

References

  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. PMID 19127717. doi:10.1021/jf0602673. 
  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. PMID 18236486. doi:10.1002/anie.200705148. 
  3. Jang MS, Cai EN, Udeani GO (1997). "Cancer chemopreventive activity of resveratrol, a natural product derived from grapes". Science 275 (5297): 218–20. PMID 8985016. doi:10.1126/science.275.5297.218. 
  • 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.