Induced production of methyl bromodihydroxyphenyl acetates by the marine-derived fungus Aspergillus sp

Chem Pharm Bull (Tokyo). 2013;61(4):483-5. doi: 10.1248/cpb.c12-01048.

Abstract

The addition of metal bromides (NaBr and CaBr2) during fermentation of a marine isolate of the fungus Aspergillus sp. induced production of two new brominated dihydroxyphenylacetic acid derivatives, methyl 2-(6-bromo-3,4-dihydroxyphenyl)acetate (1) and methyl 2-(2,5-dibromo-3,4-dihydroxyphenyl)acetate (2), and a known compound, 2-(3,4-dihydroxyphenyl)acetic acid (3). The structures of the two new compounds (1, 2) were assigned through the combination of spectroscopic data analyses and comparison with the spectral data of compound 3. Compounds 1-3 exhibited potent radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 values (14.2, 12.1, 11.0 µm, respectively) demonstrating greater activity than the positive control (l-ascorbic acid; IC50, 20.0 µm).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Acetates / isolation & purification
  • Aspergillus / chemistry*
  • Bioreactors
  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / isolation & purification
  • Hydrocarbons, Brominated / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Phenylacetates / chemistry*
  • Phenylacetates / isolation & purification

Substances

  • 2-(6-bromo-3,4-dihydroxyphenyl)acetate
  • Acetates
  • Free Radical Scavengers
  • Hydrocarbons, Brominated
  • Phenylacetates
  • methyl 2-(2,5-dibromo-3,4-dihydroxyphenyl)acetate