Practical isolation of polygodial from Tasmannia lanceolata: a viable scaffold for synthesis.

نویسندگان

  • Jeremy Just
  • Timothy B Jordan
  • Brett Paull
  • Alex C Bissember
  • Jason A Smith
چکیده

Polygodial, a valuable sesquiterpene dialdehyde featuring an epimerizable stereocenter was efficiently extracted and isolated in gram-scale quantities (3.3% w/w) from Tasmannia lanceolata (Tasmanian native pepper) via a recently developed rapid pressurised hot water extraction (PHWE) technique that utilises an unmodified household espresso machine. This method was compared to the maceration of T. lanceolata under a range of conditions. Polygodial was used to achieve semi-syntheses of closely related sesquiterpene natural products drimendiol, (-)-drimenol, (+)-euryfuran, and some non-natural derivatives.

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The methanolic extract from the leaves of Tasmannia lanceolata and its principal constituent, polygodial, were found to show potent protective effects on ethanol-induced gastric lesions in rats, and the structure–activity relation of polygodial in gastromucosal protection

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 13 46  شماره 

صفحات  -

تاریخ انتشار 2015