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

J Antibiot (Tokyo). 2010 Jun;63(6):297-301. doi: 10.1038/ja.2010.34. Epub 2010 Apr 30.

Abstract

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-1H-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.

MeSH terms

  • Animals
  • Anthozoa / microbiology
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / pharmacology
  • Bacteria / drug effects
  • Fermentation
  • Fungi / drug effects
  • Maleimides / isolation & purification*
  • Maleimides / pharmacology
  • Microbial Sensitivity Tests
  • Vibrio / metabolism*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Maleimides
  • aqabamycin A
  • aqabamycin B
  • aqabamycin C
  • aqabamycin D
  • aqabamycin E
  • aqabamycin F
  • aqabamycin G