Biosynthesis, characterization and biological evalutation of Fe(III) and Cu(II) complexes of neoaspergillic acid, a hydroxamate siderophore produced by co-cultures of two marine-derived mangrove epiphytic fungi

Nat Prod Commun. 2011 Aug;6(8):1137-40.

Abstract

A hydroxamate siderophore, neoaspergillic acid (1), and a red pigment, ferrineoaspergillin (2) which is an Fe(III) complex of 1, were produced by co-cultures of two epiphytic fungi from a rotten fruit of the mangrove Avicennia marina from the South China Sea, and a new Cu(II) complex of 1, designated as cuprineoaspergillin (3), was also prepared by treatment of 1 with cupric acetate. All the compounds (1-3) were characterized by physical and chemical techniques, including 1H NMR, ESIMS, and photoelectron energy spectra. In the bioassays, compounds 1-3 showed significant inhibitory activities against selected Gram-positive and Gram-negative bacteria, and compound 1 also exhibited moderate inhibitory activities against human cancer cell lines SPC-A-1, BEL-7402, SGC-7901 and K562.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology
  • Avicennia / microbiology*
  • Cell Line, Tumor
  • Coculture Techniques
  • Copper / chemistry*
  • Copper / metabolism
  • Copper / pharmacology
  • Ferric Compounds / chemistry*
  • Ferric Compounds / metabolism
  • Ferric Compounds / pharmacology
  • Fruit / microbiology
  • Fusarium / metabolism
  • Humans
  • Iron / chemistry*
  • Iron / metabolism
  • Iron / pharmacology
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / metabolism
  • Organometallic Compounds / pharmacology
  • Pyrazines / chemistry*
  • Pyrazines / metabolism
  • Pyrazines / pharmacology

Substances

  • Antineoplastic Agents
  • Ferric Compounds
  • Organometallic Compounds
  • Pyrazines
  • cuprineoaspergillin
  • ferrineoaspergillin
  • aspergillic acid
  • Copper
  • Iron