Stilbenoid

Stilbenoids are secondary products of heartwood formation in trees that can act as phytoalexins. In chemical terms, they are hydroxylated derivatives of stilbene. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones.[1] An alternative bacterial stilbenoid ketosynthase-directed pathway exists in bacterial symbionts of 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]

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
Oligomeric forms
Glycosides
Oligomeric forms glycosides

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. 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. 
  4. ^ a b c d e Oligostilbenoids from Shorea gibbosa and their cytotoxic properties against P-388 cells. Haryoto Saroyobudiono, Lia D. Juliawaty, Yana M. Syah, Sjamsul A. Achmad, Euis H. Hakim, Jalifah Latip and Ikram M. Said, Journal of Natural Medicines, Volume 62, Number 2 / avril 2008
  5. ^ a b c A modified oligostilbenoid, diptoindonesin C, from Shorea pinanga Scheff. Yana M. Syah; Euis H. Hakim; Emilio L. Ghisalberti; Afghani Jayuska; Didin Mujahidin; Sjamsul A. Achmad, Natural Product Research, Volume 23, Issue 7 October 2009
  6. ^ Flexuosol A, a New Tetrastilbene from Vitis flexuosa. Wen-wu Li, Bo-gang Li and Yao-zu Chen, J. Nat. Prod., 1998, 61 (5), pp 646–647, doi:10.1021/np970457v
Stilbenoids and their glycosides
Stilbenoids
Glycosides
of resveratrol
Oligomeric forms
Ampelopsin A | Amurensin A, B, G and H | Carasinol B | Diptoindonesin C | Diptoindonesin F | Flexuosol A | Gnetin H | Hemsleyanol D | Kobophenol A | Laetevirenol A, B, C, D and E | Vaticanol B | Viniferal | Tetramers : Laetevirenol F and G
of resveratrol
Ampelopsin E | Dimers : ε-viniferin, Parthenocissin A, Quadrangularin A, Pallidol and Amurensin A | Trimers : α-viniferin, Laevifonol (an ε-viniferin-ascorbic acid hybrid compound), Malaysianol A, trans-diptoindonesin B | Tetramers : Hopeaphenol | Vitisins A, B and C
Oligomeric forms glycosides
Diptoindonesin A | Laevifoside (O-glucoside of ampelopsin A)
Misc
Synthetic
Stilbenoid drugs
Phenylpropanoids