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

• Published in: Journal of antibiotics Vol. 63; no. 6; pp. 297 - 301
• Main Authors: Al-Zereini, Wael, Fotso Fondja Yao, Clarisse Blanchine, Laatsch, Hartmut, Anke, Heidrun
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 01.06.2010; Springer Nature; Nature Publishing Group
• Subjects: 631/154/349; 631/154/436/2388; 631/1647/2230; 631/326/41/2535; Animals; Anthozoa - microbiology; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Antifungal Agents - pharmacology; Bacteria - drug effects; Bacteriology; Biomedical and Life Sciences; Bioorganic Chemistry; Biotechnology & Applied Microbiology; Fermentation; Fungi - drug effects; Immunology; Life Sciences; Life Sciences & Biomedicine; Maleimides - isolation & purification; Maleimides - pharmacology; Medicinal Chemistry; Metabolites; Microbial Sensitivity Tests; Microbiology; Organic Chemistry; original-article; Pharmacology & Pharmacy; Science & Technology; Secondary metabolites; Vibrio - metabolism; antibacterial activity; marine bacteria; cytotoxic activity; aromatic nitro compounds; species; aqabamycins; ICE BACTERIUM; Vibrio species; PARAHAEMOLYTICUS; TETRODOTOXIN
• ISSN: 0021-8820; 1881-1469
• DOI: 10.1038/ja.2010.34

In a screening of marine bacteria, a Vibrio species isolated from the surface of the soft coral Sinularia polydactyla collected in the Red Sea was found to be a prolific producer of secondary metabolites with antibacterial and cytotoxic activities. Seven novel maleimide derivatives named aqabamycin A ( 1a ), aqabamycin B (1b ), aqabamycin C ( 1c ), aqabamycin D ( 1d ), aqabamycin E ( 1e and 1e′ ), aqabamycin F ( 1f ) and aqabamycin G ( 2 ) were isolated together with several known metabolites such as 3-nitro-1 H -indazole ( 3 ), indazole-3-carbaldehyde ( 4 ), phenyl-2-bis-indolylmethane ( 5a ), turbomycin B ( 5b ), vibrindole A ( 6 ), 1,4-dithiane ( 7 ), 3-(3-nitro-4-hydroxyphenyl)-2-propenoic acid ( 8 ), 3-nitro-4-hydroxybenzaldehyde ( 9 ), phenylacetic acid, benzoic acid, 3-hydroxybenzoic acid and 4-hydroxycinnamic acid. The aqabamycins, except aqabamycin A, bear a nitro group. Compounds 3 , 4 , 7 are described here for the first time from a natural source and vibrindole A was found to have cytotoxic activity.