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J Antibiot (Tokyo). 2002 Jul;55(7):635-42.

Structure and biosynthesis of cetoniacytone A, a cytotoxic aminocarba sugar produced by an endosymbiontic Actinomyces.

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Institut für Organische Chemie, Universität Göttingen, Germany.


Cetoniacytone A (1) and some related minor components (2, 6, 7) were produced by Actinomyces sp. (strain Lu 9419), which was isolated from the intestines of a rose chafer (Cetonia aureata). The structures of the novel metabolites were established by detailed spectroscopic analysis. The absolute configuration of 1 was determined by X-ray analysis and derivatisation with chiral acids. 1 exhibits a significant cytotoxicity against selected tumor cell lines. The biosynthesis of 1 was studied by feeding 13C labelled precursors. The results suggest that the characteristic p-C7N skeleton of the aminocarba sugar is formed via the pentose phosphate pathway by cyclisation of a heptulose phosphate intermediate.

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