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Applied and Environmental Microbiology, January 2004, p. 114-120, Vol. 70, No. 1
0099-2240/04/$08.00+0     DOI: 10.1128/AEM.70.1.114-120.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.

Structure and Characterization of Flavolipids, a Novel Class of Biosurfactants Produced by Flavobacterium sp. Strain MTN11

Adria A. Bodour,1 Claudia Guerrero-Barajas,2 Beth V. Jiorle,3 Mark E. Malcomson,3 Amanda K. Paull,3 Arpad Somogyi,3 Long N. Trinh,3 Robert B. Bates,3 and Raina M. Maier4*

Department of Earth and Environmental Science, The University of Texas—San Antonio, San Antonio, Texas 78249,1 Department of Chemical and Environmental Engineering,2 Department of Chemistry,3 Department of Soil, Water and Environmental Science, The University of Arizona, Tucson, Arizona 857214

Received 20 June 2003/ Accepted 2 October 2003

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.

* Corresponding author. Mailing address: Department of Soil, Water and Environmental Science, University of Arizona, 429 Shantz Building #38, Tucson, AZ 85721. Phone: (520) 621-7231. Fax: (520) 626-6782. E-mail: rmaier{at}ag.arizona.edu.

Applied and Environmental Microbiology, January 2004, p. 114-120, Vol. 70, No. 1
0099-2240/04/$08.00+0     DOI: 10.1128/AEM.70.1.114-120.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.



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