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Query: UMLS:C0393754 (HSA)
 2,996 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

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.
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PMID:Production of 10-ketostearic acid and 10-hydroxystearic acid by strains of Sphingobacterium thalpophilum isolated from composted manure. 1059 23

A microbial isolate, Flavobacterium sp. strain DS5, produces 10-ketostearic acid (10-KSA) from oleic acid in 85% yield. This is the first report on this type of reaction catalyzed by a Flavobacterium strain. The product was purified to give white, plate-like crystals melting at 79.2 degrees C. The optimum time, pH, and temperature for the production of 10-KSA are 36 h, 7.5, and 30 degrees C, respectively. A small amount of 10-hydroxystearic acid (10-HSA) (about 10% of the amount of the main product, 10-KSA) is also produced during the bioconversion. 10-KSA is not further metabolized by strain DS5 and accumulates in the medium. In contrast to growing cells, a resting-cell suspension of strain DS5 produces 10-HSA and 10-KSA in a ratio of 1:3. The crude cell extract obtained from ultrasonic disruption of the cells converts oleic acid mainly to 10-HSA (10-HSA/10-KSA ratio, 97:3). This result strongly suggested that oleic acid is converted to 10-KSA via 10-HSA. Enzymes catalyzing the hydration and secondary alcohol dehydrogenation are cell associated. Product 10-HSA from strain DS5 is 66% enantiomeric excess in the 10(R) form. The oleic acid conversion enzyme(s) reacts with unsaturated fatty acids in the order oleic acid > palmitoleic acid > linoleic acid > linolenic acid > gamma-linolenic acid > myristoleic acid.
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PMID:Production of 10-Ketostearic Acid from Oleic Acid by Flavobacterium sp. Strain DS5 (NRRL B-14859). 1634 14

Flavobacterium sp. strain DS5 (NRRL B-14859) was used to convert two vegetable oils, olive oil and soybean oil, directly to oxygenated fatty acids such as 10-ketostearic acid (10-KSA) and 10-hydroxystearic acid (10-HSA). Lipase addition to the culture was required because strain DS5 did not induce lipase activity to release free fatty acids from vegetable oils. 10-KSA production was higher from olive oil than from soybean oil because olive oil contains more oleic acid, the precursor of 10-KSA. The optimum amounts of olive oil and lipase addition for 10-KSA production were determined as 0.3ml and 1mg (specific activity=700units/mg) per 50ml culture medium, respectively. At these conditions, 2.8g/L of 10-KSA and 0.40g/L of 10-HSA were obtained from olive oil as a substrate.
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PMID:Production of oxygenated fatty acids from vegetable oils by Flavobacterium sp. strain DS5. 1981 19

A systematic study of the importance of functional group position and type on the gelator efficiencies of structurally simple, low molecular-mass gelators is reported. Thus, the gelation abilities of a series of positional isomers of ketooctadecanoic acid (n-KSA) are compared in a wide range of liquids. The gelation abilities of the n-KSA as a function of n, the keto group position along the chain, are characterized by several structural, thermal, and rheological techniques and are compared with those of the corresponding hydroxyoctadecanoic acid isomers (n-HSA) and the parent molecule, octadecanoic acid (SA). Analyses of the gels according to the strengths of functional group interactions along the alkyl chain in terms of group position and type are made. The conclusions derived from the study indicate that gel stability is enhanced when the functional group is located relatively far from the carboxylic headgroup and when group-group interactions are stronger (i.e., hydrogen-bonding interactions are stronger in the n-HSA than dipole interactions in the n-KSA, which are stronger than the London dispersion interactions in SA). Co-crystals of the keto- and hydroxy-substituted octadecanoic acids are found to be less efficient gelators than even the ketooctadecanoic acids, due to molecular packing and limited group interactions within the gelator networks.
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PMID:Comparison of dipolar, H-bonding, and dispersive interactions on gelation efficiency of positional isomers of keto and hydroxy substituted octadecanoic acids. 2367 43