Trinorlupeol: a major nonsterol triterpenoid in Arabidopsis

Organic Letters
Hui ShanSeiichi P T Matsuda

Abstract

We report the structure determination of 20,29,30-trinorlup-18-en-3beta-ol (trinorlupeol) and establish this novel C 27 metabolite as a major nonsterol triterpenoid in Arabidopsis thaliana. Trinorlupeol was concentrated in cuticular waxes, notably in the plant stem, floral buds, and seedpods, but not in leaves. Based on expression data and functional characterization of A. thaliana oxidosqualene cyclases, we propose that LUP1 is the cyclase responsible for trinorlupeol biosynthesis. Also described are two oxidized trinorlupeols and additional biosynthetic insights.

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Citations

Feb 22, 2011·Phytochemistry·Jörg M AugustinSøren Bak
Nov 4, 2008·Plant Physiology and Biochemistry : PPB·Masaaki ShibuyaYutaka Ebizuka
Apr 24, 2012·Journal of Lipids·Naïm Stiti, Marie-Andrée Hartmann
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Dec 22, 2009·Natural Product Reports·Joseph D Connolly, Robert A Hill
May 19, 2009·Organic Letters·Pietro MorlacchiSeiichi P T Matsuda
Apr 11, 2013·Journal of the American Chemical Society·Dorianne A CastilloSeiichi P T Matsuda

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