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pinosylvin : ウィキペディア英語版
pinosylvin

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Pinosylvin is a pre-infectious stilbenoid toxin (i.e. synthesized prior to infection), contrary to phytoalexins which are synthesized during infection. It is present in the heartwood of ''Pinaceae''.〔Screening Analyses of Pinosylvin Stilbenes, Resin Acids and Lignans in Norwegian Conifers. Hanne Hovelstad, Ingebjorg Leirset, Karin Oyaas and Anne Fiksdahl, Molecules, 2006, 11(1), pages 103-114, 〕 It is a fungitoxin protecting the wood from fungal infection.〔Antibacterial and antifungal activity of pinosylvin, a constituent of pine. S.K. Lee, H.J. Lee, H.Y. Min, E.J. Park, K.M. Lee, Y.H. Ahn, Y.J. Cho and J.H. Pyee, Fitoterapia, Volume 76, Issue 2, March 2005, Pages 258–260, 〕 It is also found in ''Gnetum cleistostachyum''.〔Stilbenes from Gnetum cleistostachyum. Yao Chun-Suo, Lin Mao, LIiu Xin and Wang Ying-Hong, Huaxue xuebao, 2003, volume 61, no 8, pages 1331-1334, 〕
Injected in rats, pinosylvin shows a rapid glucuronidation and a poor bioavailability.〔Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. Kathryn A. Roupe, Jaime A. Yáñez, Xiao Wei Teng and Neal M. Davies, Journal of Pharmacy and Pharmacology, November 2006, Volume 58, Issue 11, pages 1443–1450, 〕
== Biosynthesis ==
Pinosylvin synthase is an enzyme that catalyzes the chemical reaction 3 malonyl-CoA + cinnamoyl-CoA → 4 CoA + pinosylvin + 4 CO2
This biosynthesis is noteworthy because plant biosyntheses employing cinnamic acid as a starting point are rare compared to the more common use of p-coumaric acid. Only a few identified compounds, such as anigorufone and curcumin, use cinnamic acid as their start molecule.

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