Biosurfactants from Marine Cyanobacteria Collected in Sabah, Malaysia

J Nat Prod. 2020 Jun 26;83(6):1925-1930. doi: 10.1021/acs.jnatprod.0c00164. Epub 2020 May 20.

Abstract

Chemical investigation of the organic extract from Moorea bouillonii, collected in Sabah, Malaysia, led to the isolation of three new chlorinated fatty acid amides, columbamides F (1), G (2), and H (3). The planar structures of 1-3 were established by a combination of mass spectrometric and NMR spectroscopic analyses. The absolute configuration of 1 was determined by Marfey's analysis of its hydrolysate and chiral-phase HPLC analysis after conversion and esterification with Ohrui's acid, (1S,2S)-2-(anthracene-2,3-dicarboximido)cyclohexanecarboxylic acid. Compound 1 showed biosurfactant activity by an oil displacement assay. Related known fatty acid amides columbamide D and serinolamide C exhibited biosurfactant activity with critical micelle concentrations of about 0.34 and 0.78 mM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Cyanobacteria / chemistry*
  • Drug Screening Assays, Antitumor
  • Fatty Acids / chemistry
  • Magnetic Resonance Spectroscopy
  • Malaysia
  • Micelles
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oils / chemistry
  • Surface Tension
  • Surface-Active Agents / chemistry*

Substances

  • Fatty Acids
  • Micelles
  • Oils
  • Surface-Active Agents

Supplementary concepts

  • Moorea bouillonii