Structure and biosynthesis of cetoniacytone A, a cytotoxic aminocarba sugar produced by an endosymbiontic Actinomyces.
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.
Schlörke
Oliver
O
Institut für Organische Chemie, Universität Göttingen, Germany.
Krastel
Philipp
P
Müller
Ilka
I
Usón
Isabel
I
Dettner
Konrad
K
Zeeck
Axel
A
D000190:Actinomyces / Q000737:chemistry* / Q000378:metabolism; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D018360:Crystallography, X-Ray; D003470:Culture Media; D003512:Cyclohexanones / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005285:Fermentation; D005947:Glucose / Q000378:metabolism; D005990:Glycerol / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013559:Symbiosis; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D003470:Culture Media; D003512:Cyclohexanones; C466782:cetoniacytone A; C466783:cetoniacytone B; D005947:Glucose; D005990:Glycerol