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At least 199 records · Page 11Linked to original sources
PubMed1996

Production of hydroxy fatty acid (10-hydroxy-12(Z)-octadecenoic acid) by Lactobacillus plantarum from linoleic acid and its cardiac effects to guinea pig papillary muscles.

Lactobacillus plantarum produced 10-hydroxy-12(Z)-octadecenoic acid (10-OHODA) from linoleic acid. It was suspected that 10-OHODA might be closely related to leukotoxin (9,10-epoxy-12-octa-decenoic acid (LTx)) which was regarded as a toxic and/or defensive substance in living beings. The cardiac effect of 10-OHODA, which was biosynthesized by Lactobacillus plantarum, on an isolated guinea-pig papillary muscle was determined. Its effect on the contractile force of the tissue preparations was examined both in terms of its concentration and the time of exposure. A decrease in muscular tension was observed immediately after administration of 10-OHODA at concentrations of 30, 100, and 300 microM. We also compared the effect of 10-OHODA on muscle tension with that of LTx and its isomer 12,13-epoxy-9-octadecenoic acid (LTx'). Each inhibitory effect on the contractile force of the papillary muscle was statistically significant in the concentration of 300 microM 5 min after administration compared to the control in the absence of each fatty acid, suggesting that 10-OHODA is likely to exert some influence on the circulatory system together with LTx and LTx'.

Animals↗
PubMed1982

Oxidation of the 17-aldol (20 beta hydroxy-21-aldehyde) intermediate of corticosteroid metabolism to hydroxy acids by homogeneous human liver aldehyde dehydrogenases.

In human liver, the oxidation of corticosteroids to 20-hydroxy-21-oic acids proceeds via the formation and oxidation of aldol (20-hydroxy-21-aldehyde) intermediates. Human liver aldehyde dehydrogenases E1 and E2, which we have previously purified to homogeneity, catalyzed the oxidation of the aldol isomer of cortisol (isocortisol) or of 11-deoxycorticosterone (isoDOC) by E1 and E2 respectively, were identified by the criteria of chromatographic mobility, derivatization, and reverse isotope dilution of 4-14C labeled acid end products. Both enzymes showed broad substrate specificity and oxidized both 17-hydroxy and 17-deoxy steroids, though at widely varying rates. Kinetic analysis of the course of oxidation of isocortisol and isoDOC by NAD+ gave intersecting initial velocity plots that conform with a sequential mechanism. The inhibition patterns for both enzymes with thionicotinamide adenine dinucleotide or chloral hydrate were consistent with random sequential behavior.

Adrenal Cortex Hormones↗
PubMed2005

Remarkable diastereomeric rearrangement of an alpha-acyloxy beta-ketosulfide to an alpha-acyloxy thioester: a novel approach to the synthesis of optically active (2S,3S) beta-amino alpha-hydroxy acids.

[reaction: see text] A novel and efficient synthetic method is described for (2S,3S)-3-amino-2-hydroxy-4-phenyl butyric acid derivatives, which are useful intermediates of enzyme inhibitors. This involves a Pummerer rearrangement of a beta-ketosulfoxide derived from l-phenylalanine followed by highly stereoselective acyl migration. From these studies, it appears that nitrogen-protecting groups exert a substantial influence over stereoselectivity. The mechanism of the rearrangement is discussed. beta-Amino alpha-hydroxy carboxylic acids are important pharmaceutical intermediates, and this method may provide a versatile synthesis from various amino acids in a few steps.

HIV Protease Inhibitors↗