Trinorlupeol: A Major Nonsterol Triterpenoid in Arabidopsis

Trinorlupeol: A Major Nonsterol Triterpenoid in Arabidopsis

We report the structure determination of 20,29,30-trinorlup-18-en-3β-ol (trinorlupeol) and establish this novel C27 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...

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Veröffentlicht in:Organic letters 2008-05, Vol.10 (10), p.1897-1900
Hauptverfasser: Shan, Hui, Wilson, William K, Phillips, Dereth R, Bartel, Bonnie, Matsuda, Seiichi P. T
Format: Artikel
Sprache:eng
Schlagworte:
Arabidopsis - chemistry
Molecular Conformation
Stereoisomerism
Triterpenes - blood
Triterpenes - chemistry
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Zusammenfassung:We report the structure determination of 20,29,30-trinorlup-18-en-3β-ol (trinorlupeol) and establish this novel C27 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800389q