Structure and characterization of flavolipids, a novel class of biosurfactants produced by Flavobacterium sp. strain MTN11

Appl Environ Microbiol. 2004 Jan;70(1):114-20. doi: 10.1128/AEM.70.1.114-120.2004.

Abstract

Herein we report the structure and selected properties of a new class of biosurfactants that we have named the flavolipids. The flavolipids exhibit a unique polar moiety that features citric acid and two cadaverine molecules. Flavolipids were produced by a soil isolate, Flavobacterium sp. strain MTN11 (accession number AY162137), during growth in mineral salts medium, with 2% glucose as the sole carbon and energy source. MTN11 produced a mixture of at least 37 flavolipids ranging from 584 to 686 in molecular weight (MW). The structure of the major component (23%; MW = 668) was determined to be 4-[[5-(7-methyl-(E)-2-octenoylhydroxyamino)pentyl]amino]-2-[2-[[5-(7-methyl-(E)-2-octenoylhydroxyamino)pentyl]amino]-2-oxoethyl]-2-hydroxy-4-oxobutanoic acid. The partially purified flavolipid mixture isolated from strain MTN11 exhibited a critical micelle concentration of 300 mg/liter and reduced surface tension to 26.0 mN/m, indicating strong surfactant activity. The flavolipid mixture was a strong and stable emulsifier even at concentrations as low as 19 mg/liter. It was also an effective solubilizing agent, and in a biodegradation study, it enhanced hexadecane mineralization by two isolates, MTN11 (100-fold) and Pseudomonas aeruginosa ATCC 9027 (2.5-fold), over an 8-day period. The flavolipid-cadmium stability constant was measured to be 3.61, which is comparable to that for organic ligands such as oxalic acid and acetic acid. In summary, the flavolipids represent a new class of biosurfactants that have potential for use in a variety of biotechnological and industrial applications.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkanes
  • Biodegradation, Environmental
  • Emulsifying Agents
  • Flavobacterium / growth & development
  • Flavobacterium / metabolism*
  • Lipoproteins / chemistry
  • Lipoproteins / metabolism
  • Magnetic Resonance Spectroscopy
  • Micelles
  • Solubility
  • Surface Tension
  • Surface-Active Agents / chemistry*
  • Surface-Active Agents / classification
  • Surface-Active Agents / metabolism*

Substances

  • Alkanes
  • Emulsifying Agents
  • Lipoproteins
  • Micelles
  • Surface-Active Agents
  • n-hexadecane