Biosynthetic origins of the isoprene units of gaudichaudianic acid in Piper gaudichaudianum (Piperaceae) |
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Authors: | Lopes Adriana A Baldoqui Debora C López Silvia N Kato Massuo J Bolzani Vanderlan da S Furlan Maysa |
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Affiliation: | Instituto de Química, Universidade Estadual Paulista, C.P. 355, CEP 14801-970 Araraquara, SP, Brazil. |
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Abstract: | The biosynthesis of (2S)-2-methyl-2-(4'-methyl-3'-pentenyl)-8-(3'-methyl-2-butenyl)-2H-1-benzopyran-6-carboxylic acid (gaudichaudianic acid), the major metabolite in leaves and roots of Piper gaudichaudianum Kunth (Piperaceae), has been investigated employing [1-(13)C]-D-glucose as precursor. The labelling pattern in the isolated gaudichaudianic acid was determined by quantitative (13)C NMR spectroscopy analysis and was consistent with involvement of both mevalonic acid and 2-C-methyl-D-erythritol-4-phosphate pathways in the formation of the dimethylallyl- and geranyl-derived moieties. The results confirmed that both plastidic and cytoplasmic pathways are able to provide isopentenyl diphosphate units for prenylation of p-hydroxybenzoic acid. |
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