New angucyclines and antimicrobial diketopiperazines from the marine mollusk-derived actinomycete Saccharothrix espanaensis An 113

Nat Prod Commun. 2010 Apr;5(4):597-602.

Abstract

Two new angucyclines, saccharothrixmicines A (2) and B (3), together with three known diketopiperazines 4-6 were isolated from the actinomycete Saccharothrix espanaensis An 113 associated with the marine mollusk Anadara broughtoni. Their structures were determined by HRESI-MS and 1D and 2D NMR. Compounds 2 and 3 differ in aglycone and glycosidic bond type. 2 is an alpha-L-6-deoxyaltrose-phenylglycoside of a benz[a]anthraquinone aglycone, while 3 is an O-glycoside of the same sugar linked to C-7 of the known angucyclinone (1). A saccharothrixmicine-containing fraction exhibited activity towards Candida albicans and Xanthomonas sp. pv. badrii whereas the diketopiperazines showed antibiotic activities against Vibrio alginolyticus and Vibrio parahaemolyticus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinobacteria / chemistry*
  • Animals
  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Diketopiperazines / chemistry
  • Diketopiperazines / isolation & purification*
  • Diketopiperazines / pharmacology
  • Microbial Sensitivity Tests
  • Mollusca / microbiology*
  • Nuclear Magnetic Resonance, Biomolecular
  • Optical Rotation
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • Anthraquinones
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Diketopiperazines