Aqabamycins A-G: novel nitro maleimides from a marine Vibrio species. I. Taxonomy, fermentation, isolation and biological activities

Al-Zereini, Wael A.; Yao, Clarisse Blanchine Fotso Fondja; Laatsch, Hartmut; Anke, Heidrun

doi:10.1038/ja.2010.34

Cited by 52 publications

(37 citation statements)

References 17 publications

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“…7 HPLC separation of the extract, as described in the previous paper, 4 delivered a series of six further diphenylmaleimides, which were, however, all nitrated: aqabamycin B (1b) had a mass of m/z 326 (EI-MS) and presented similar chemical properties as 1a. The H,H COSY spectrum confirmed the two fragments derived from the proton NMR spectrum.…”

Section: Resultsmentioning

confidence: 99%

“…4 Extracts of this strain yielded 19 compounds, among them eight new pyrrole-2,5-diones. Most of these metabolites are diphenyl-maleimides containing 16 carbon atoms; aqabamycin G (2) is an exception with 18 carbon atoms due to an indole residue.…”

Section: Resultsmentioning

confidence: 99%

“…4 After various separation steps on normal-phase and reversed-phase silica gel, the bis-indole derivatives vibrindole A (6), phenyl-2-bis-indolylmethane (5a) and its cationic form, the red turbomycin B (5b), were isolated.…”

Section: Bis-indolylmethanesmentioning

confidence: 99%

“…Compound 5a was obtained as reddish oil (containing some 5b) from fraction B, 4 which gave a red color with anisaldehyde/sulfuric acid. The proton NMR spectrum indicated a broad 2H singlet at d 10.90 and a further 1H singlet at d 5.82.…”

Section: Bis-indolylmethanesmentioning

confidence: 99%

“…The taxonomy of strain WMBA, its fermentation, the isolation and purification of the compounds as well as their biological activities were reported in a previous paper. 4 …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2010

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Bis-indolylmethanesmentioning

confidence: 99%

Section: Bis-indolylmethanesmentioning

confidence: 99%

“…The taxonomy of strain WMBA, its fermentation, the isolation and purification of the compounds as well as their biological activities were reported in a previous paper. 4 …”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations