The activity of acis‐9‐fatty acid hydratase produced by aPseudomonas sp. (NRRL B‐3266) isolated from soil was compared with that of another isolate previously reported (NRRL B‐2994). The presence of appropriate fatty acids for at least 4 hr during aerobic growth in yeast extract medium increased subsequent enzyme activity. Such cells anaerobically hydrated severalcis‐9‐alkenoic acids to 10‐hydroxy fatty acids and aerobically formed 10‐keto acids, which were partially degraded to shorter chain keto acids. Melting point, gas chromatography, infrared, mass spectrometry and optical rotatory dispersion data are given. Six fatty acids havingcis‐9‐unsaturation produced hydrated products, but several enoic acids havingtrans‐9‐unsaturation or double bonds in other than the 9 position were inactive as substrates. The (−)‐10‐hydroxypalmitic acid produced from palmitoleic acid is considered to have the D configuration. Yields of 71% crude crystalline product from 15 g of oleic acid and 53% from 11 g of palmitoleic acid were obtained in 5‐liter anaerobic fermentations with NRRL B‐3266. Methyl esters, triolein and oleyl alcohol were not hydrated.
The trypsin-inhibitory activity observed in cooked soybeans fermented by Rhizopus oligosporus (fungus used in tempeh fermentation) has been examined. The active compounds have now been isolated by ethanol extraction and thin-layer chromatography and have been identified as free fatty acids by infrared spectroscopy and gas-liquid chromatography. Oleic, lineoleic, and linolenic acids are primarily responsible for the increased trypsin-inhibiting activity of cooked soybeans after fermentation. The free fatty acids are liberated from oil in the soybeans by fungal lipase, and they differ from other reported soybean trypsin inhibitors that are protein in nature. Free fatty acids have been previously reported to inhibit various enzymes, such as glycolytic, glyconeogenic, lipogenic, and also proteolytic. Their effect appears to be a nonspecific type of inhibition. Further studies are required to determine their physiological relevance, if any.
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