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Production of 14-Oxo-cis-11-eicosenoic Acid from Lesquerolic Acid by Sphingobacterium multivorum NRRL B-23212

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Journal of the American Oil Chemists' Society

Abstract

The objective of this study was to explore the extent of microbial conversion of lesquerolic acid (14-hydroxy-cis-11-eicosenoic acid; LQA) by whole cell catalysis and to identify the newly converted products. Among compost isolates including NRRL strains B-23212 (Sphingobacterium multivorum), B-23213 (Acinetobacter sp.), B-23257 (Enterobacter cloacae B), B-23259 (Escherichia sp.) and B-23260 (Pseudomonas aeruginosa) the S. multivorum strain was the only microorganism that converted LQA to produce a new product identified as 14-oxo-cis-11-eicosenoic acid by GC-MS and NMR analyses. The conversion yield was 47.4% in 48 h at 200 rpm and 28°C in small shake flask experiments. In comparison, both Acinetobacter and Pseudomonas strains failed to convert LQA to major new products but used LQA apparently as an energy source during fermentation. For structural analysis, 6.88 g of 14-oxo-cis-11-eicosenoic acid was produced from converting 11 g LQA (a 62% yield) in 72 h at 200 rpm and 28 °C in Fernbach flasks using 18-h-old NRRL B-23212 cultures and an improved medium that also contained EDTA and glycerol in lieu of glucose as carbon source. NRRL B-23212 was further identified by 16S rRNA gene sequence analysis as a unique strain of S. multivorum. Therefore, S. multivorum NRRL B-23212 possesses an enzymatic activity presumably a secondary alcohol dehydrogenase for converting LQA to produce 14-oxo-cis-11-eicosenoic acid, a first report that demonstrates the functional modification of LQA by whole cell catalysis.

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Acknowledgments

We thank Karen Ray for excellent technical support, Linda Manthey for GC analysis, Trina Hartman and Dr. Neil Price for mass spectral analysis and Dr. David Weisleder for NMR analysis. Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the product, and the use of the name by USDA implies no approval of the product to the exclusion of others that may also be suitable.

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Authors and Affiliations

  1. Microbial Genomics and Bioprocessing Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, US Department of Agriculture, 1815 North University Street, Peoria, IL, 61604, USA

    Tsung Min Kuo, Alejandro Rooney & William E. Levinson

  2. New Crops Processing and Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, US Department of Agriculture, 1815 North University Street, Peoria, IL, 61604, USA

    Terry A. Isbell & Hans Frykman

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  1. Tsung Min Kuo
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  2. Terry A. Isbell
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  4. William E. Levinson
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Correspondence to Tsung Min Kuo.

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Kuo, T.M., Isbell, T.A., Rooney, A. et al. Production of 14-Oxo-cis-11-eicosenoic Acid from Lesquerolic Acid by Sphingobacterium multivorum NRRL B-23212. J Amer Oil Chem Soc 84, 639–643 (2007). https://doi.org/10.1007/s11746-007-1085-x

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  • DOI: https://doi.org/10.1007/s11746-007-1085-x

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