Aqabamycins A-G: novel nitro maleimides from a marine Vibrio species: II. Structure elucidation.

Clarisse Blandine Fotso Fondja Yao, Wael Al Zereini, Serge Fotso, Heidrun Anke, Hartmut Laatsch

Institute for Organic and Biomolecular Chemistry, Georg-August University Göttingen, Göttingen, Germany.

The Journal of antibiotics 2010 Jun

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The structures of secondary metabolites with antibacterial and cytotoxic activities produced by a marine Vibrio strain from the Red Sea were elucidated. Aqabamycin A (1a) and seven further nitro-substituted maleimide derivates named aqabamycins B-G (1b-f and 2) were obtained together with 12 known metabolites, 3-nitro-1H-indazole (3), indazole-3-carbaldehyde (4), 3-nitro-4-hydroxycinnamic acid, 4-hydroxycinnamic acid, 3-nitro-4-hydroxybenzaldehyde, phenyl-2-bis-indolylmethane (5a), turbomycin B (5b), vibrindole A (6), phenylacetic acid, 3-hydroxybenzoic acid, benzoic acid and 1,4-dithiane (7). Some of the known metabolites (for example, 3, 4 and 7) are described in this study for the first time as natural products. Their structures were elucidated based on 1D and 2D NMR, MS spectra and by comparison with synthetic material.

Citation

Clarisse Blandine Fotso Fondja Yao, Wael Al Zereini, Serge Fotso, Heidrun Anke, Hartmut Laatsch. Aqabamycins A-G: novel nitro maleimides from a marine Vibrio species: II. Structure elucidation. The Journal of antibiotics. 2010 Jun;63(6):303-8