ARS | Publication request: Production of 14-oxo-cis-11-eicosenoic acid from lesquerolic acid by genetically variable Sphingobacterium multivorum strains

Submitted to: Meeting Abstract
Publication Type: Abstract
Publication Acceptance Date: August 23, 2007
Publication Date: August 23, 2007
Citation: Kuo, T., Rooney, A.P., Isbell, T. 2007. Production of 14-oxo-cis-11-eicosenoic acid from lesquerolic acid by genetically variable Sphingobacterium multivorum strains [abstract]. American Chemical Society. p. 78.

Technical Abstract: The objective of this study was to explore the extent of microbial conversion of lesquerolic acid (LQA; 14-hydroxy-cis-11-eicosenoic acid) by whole cell catalysis and to identify the newly converted product. Among 17 environmental isolates selected from compost amended with soybean oil and unsaturated fatty acids including such species as Sphingobacterium, Acinetobacter, Enterobacter, Escherichia, Pseudomonas, and Serratia; Sphingobacterium multivorum identified by 16S rRNA gene sequence analysis was the only microbial species that exhibited the ability of LQA conversion. In small shake flask experiments, strains of S. multivorum displayed the activity for converting LQA to a major new product with yields ranging from about 45% for NRRL B-23213 to none for NRRL B-14797. For structural analysis, 6.88 g of the new compound representing a yield of more than 62% in 72 h was produced by strain NRRL B-23213 in Fernbach flasks using a culture medium that also contained EDTA and used glycerol in lieu of glucose as carbon source. Displaying a similar retention time as LQA on GC, the new compound was determined as 14-oxo-cis-11-eicosenoic acid by GC-MS and NMR analyses. Therefore, strains of S. multivorum have possessed specific 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.