Triterpene saponin hemi-biosynthesis of a leaf beetle's (Platyphora kollari) defensive secretion
2007
Ghostin, Jean | Habib-Jiwan, Jean-Louis | Rozenberg, Raoul | Daloze, Désiré | Pasteels, Jacques M | Braekman, Jean-Claude
The adults of the leaf beetle Platyphora kollari (Chrysomelidae) are able to metabolise the oleanane triterpene β-amyrin (1) into the glycoside 3-O-β-d-glucopyranosyl-(1[rightward arrow]4)-β-d-glucuronopyranosyl-hederagenin (2) that is stored in their defensive glands. The aim of this study was to test the hypothesis that oleanolic acid (3) is an intermediate in the conversion of 1 into 2 and to check whether the sequestration of pentacyclic triterpenes is selective in favour of β-amyrin (1). To this end, adults of P. kollari were fed with Ipomoea batatas leaf disks painted with a solution of [2,2,3-²H₃]oleanolic acid or [2,2,3-²H₃]α-amyrin and the secretion of their defensive glands analysed by HPLC-ESIMS. The data presented in this work indicated that the first step of the transformation of β-amyrin (1) into the sequestered glycoside 2 is its oxidation into oleanolic acid (3) and that this conversion is selective but not specific in favour of β-amyrin (1).
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