10-ketostearic-acid and 10-hydroxystearic-acid

Fatty acids (FA) bearing oxygenated functions and present in esterified form in triacylglycerols are widespread in nature but very little is known about their occurrence in dairy products. A method based on gas chromatography (with flame ionization detector and mass spectrometry detectors), including the previous isolation of polar FA methyl esters by solid-phase extraction, was applied to quantify oxygenated FA in milk fat. Samples obtained from ewes and goats fed with a variety of oil sources were studied. Fatty acids identified were 8-ketopalmitic, 8-hydroxypalmitic, 10-ketostearic, and mainly 10-hydroxystearic acids. The highest levels of 10-ketostearic acid were obtained in milk from animals fed olive oil (up to 1.5%) and from those fed long-chain n-3 FA-enriched diets (0.5-1.0%). In all samples, 10-hydroxystearic acid, not reported so far in milk, was the second most abundant oxygenated FA (up to 0.8%). The high correlation obtained between contents of 10-ketostearic and 10-hydroxystearic acids would confirm the existence of a common pathway of formation in the rumen, whereas the presence of 8-ketopalmitate and 8-hydroxypalmitate could be putatively attributed to mechanisms of β-oxidation in the tissues. The influence of cis-9 C18:1 and trans-10 C18:1 as precursors of these compounds in milk and the metabolic pathways involved in their formation are discussed.

Topics: Animal Nutritional Physiological Phenomena; Animals; Diet; Dietary Fats; Fatty Acids; Female; Gas Chromatography-Mass Spectrometry; Goats; Milk; Sheep; Stearic Acids

The formation of hydroxystearic acid (HSA) and ketostearic acid (KSA) from oleic acid transformation has been documented in a variety of microbial species, including several isolated from the rumen of domesticated ruminant species. However, their ruminal production rates have not been established as influenced by fatty acid source. Dosing continuous cultures of mixed ruminal microorganisms with 1-(13C)-oleic acid increased the 13C enrichment of both HSA and KSA at 24 h postdosing, and showed that the majority (96 and 85%, respectively) of the HSA and KSA present in the 24-h samples originated from oleic acid. Several experiments using batch cultures of ruminal microorganisms showed that production of HSA and KSA was directly related to oleic acid input but was not affected by elaidic acid input, and that HSA was further metabolized to KSA but not to other fatty acids. When continuous cultures of ruminal microorganisms were supplemented with soybean oil or canola oil, production of 10-HSA + 10-KSA was related to oleic acid input but not to linoleic acid input. Daily production of 10-HSA + 10-KSA across treatments was 14.4 micromol/100 micromol oleic acid input into the cultures or 31.1 micromol/100 micromol oleic acid net loss. The results of this study quantify the formation of 10-HSA and 10-KSA from oleic acid transformation by ruminal microorganisms, and show that their accumulation in ruminal contents is directly related to the extent of oleic acid input and biotransformation by the rumen microbiota.

Topics: Animals; Carbon Isotopes; Cattle; Fatty Acids; Fermentation; Linoleic Acid; Oleic Acid; Rumen; Stearic Acids

Six strains of Sphingobacterium thalpophilum were isolated from a compost mixture enriched with oleic acid. These strains converted oleic acid to 10-ketostearic acid (10-KSA; 87-94% of the total conversion product) and to 10-hydroxystearic acid (10-HSA; 6-13%) exhibiting three levels of total product yields. The predominant production of 10-KSA by these new S. thalpophilum isolates is in contrast to strain 142b (NRRL B-14797) previously isolated from a commercial compost, which produces exclusively 10-HSA. The production yield of greater than 75% 10-KSA was achieved in 36 h, acting on 0.26 g of oleic acid in 30-ml fermentation broth incubated with agitation at 28 degrees C. For easy maintenance, fast-growth, and high bioreactivity, these S. thalpophilum strains are suited for developing a large-scale production of 10-KSA and 10-HSA.

Topics: Bacteriological Techniques; Chlorobi; Manure; Mass Spectrometry; Oleic Acid; Spectroscopy, Fourier Transform Infrared; Stearic Acids