Biosynthesis of furan fatty acids (F-acids) by a marine bacterium, Shewanella putrefaciens.
A mutant derived from Shewanella putrefaciens 8CS7-4 treated with N-methyl-N'-nitro-N-nitrosoguanidine was found to produce 15-20 mg of a furan fatty acid (F-acid), 10,13-epoxy-11-methyloctadeca-10,12-dienoic acid (F18), per liter of growth medium (10-15% of total fatty acids). Capillary gas chromatography-mass spectrometry and proton nuclear magnetic resonance analysis of the fatty acid methyl esters of the mutant revealed the presence of other F-acids, 8,11-epoxy-9-methylhexadeca-8,10-dienoic acid (F16), 6,9-epoxy-7-methyltetradeca-6,8-dienoic acid (F14), and methyl branched unsaturated fatty acids, 11-methyl-12E-octadecenoic acid (11-me-18:1) and 11-methyl-10E,12E-octadecadienoic acid (1-me-18:2). About 90% of F-acids were present in phospholipids, in which the F-acids were found to be exclusively linked at the sn-1 position. 11-me-18:1 and 11-me-18:2 were also detected in the sn-1 position. Firstly, 11-me-18:1 increased and reached a maximum at 12 h, and then decreased rapidly. Secondly, the 11-me-18:2 content reached a maximum at 24 h, when 11-me-18:1 was little detected, and then decreased. Finally, the amount of F18 began to increase after 20 h and reached a plateau at 36 h. These results suggest that 11-me-18:1 and 11-me-18:2 are precursors of F18.
Shirasaka
N
N
Department of Agricultural Chemistry, Kyoto University, Sakyo-ku, Japan.
Nishi
K
K
Shimizu
S
S
D000818:Animals; D005227:Fatty Acids / Q000096:biosynthesis* / Q000737:chemistry / Q000378:metabolism; D005399:Fishes / Q000382:microbiology; D005663:Furans / Q000737:chemistry / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D006092:Gram-Negative Facultatively Anaerobic Rods / Q000235:genetics / Q000254:growth & development / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D016296:Mutagenesis; D010714:Phosphatidylethanolamines / Q000737:chemistry; D010715:Phosphatidylglycerols / Q000737:chemistry
D005227:Fatty Acids; D005663:Furans; D010714:Phosphatidylethanolamines; D010715:Phosphatidylglycerols