[Production of hydroxy and oxo fatty acids by microorganisms as a model of adipocere formation].
Microbial synthesis of hydroxy and oxo fatty acids was studied as one of the model of experimental adipocere formation. Conversion of various fatty acids into 10-hydroxy and 10-oxo fatty acids by Micrococcus luteus was also studied. Fatty acids possessing cis-9-unsaturated forms were converted into 10-hydroxy and 10-oxo fatty acids. On the other hand, enoic acids possessing trans-9-unsaturated form or the ones which do not have double bond at the 9 -carbon position were inactive as substrates. 10-Hydroxypalmitic and 10-hydroxystearic acids were converted into the corresponding 10-oxo fatty acids but the 10-oxo fatty acids were inactive as substrates. To study the mechanism of the formation of 10-hydroxy and 10-oxo fatty acids, the crude enzyme preparation from Flavobacterium meningosepticum solubilized by sonication was used. The mechanism of hydration and dehydrogenation was proved by gas chromatography-mass spectrometry of 10-hydroxy and 10-oxo fatty acids produced from oleic acid in the presence of D2O or H218O. These results indicate that oleic acid is hydrated to 10-hydroxystearic acid at first and then, the latter compound is dehydrogenated to 10-oxostearic acid.
Gotouda
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Department of Legal Medicine, Hokkaido University School of Medicine, Sapporo, Japan.
D005227:Fatty Acids / Q000096:biosynthesis*; D005417:Flavobacterium / Q000201:enzymology / Q000378:metabolism*; D007651:Keto Acids / Q000138:chemical synthesis*; D008837:Micrococcus / Q000378:metabolism*; D019301:Oleic Acid; D009829:Oleic Acids / Q000378:metabolism; D011180:Postmortem Changes
D005227:Fatty Acids; D007651:Keto Acids; D009829:Oleic Acids; D019301:Oleic Acid