scholarly journals Conversion of Linoleic Acid into 10-Hydroxy-12(Z)-octadecenoic Acid by Whole Cells of Stenotrophomonas nitritireducens

2008 ◽  
Vol 24 (1) ◽  
pp. 182-186 ◽  
Author(s):  
I.-S. Yu ◽  
H.-J. Kim ◽  
D.-K. Oh
Keyword(s):  
Linoleic Acid ◽  
Octadecenoic Acid ◽  
Whole Cells ◽  
Stenotrophomonas Nitritireducens

scholarly journals Differences in the metabolism of esterified and unesterified linoleic acid by rumen micro-organisms

1969 ◽  
Vol 23 (4) ◽  
pp. 869-878 ◽  
Author(s):  
J. H. Moore ◽  
R. C. Noble ◽  
W. Steele ◽  
J. W. Czerkawski
Keyword(s):  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Stearic Acid ◽  
Octadecenoic Acid ◽  
Time Intervals ◽  
Micro Organisms ◽  
Hydrolysis Of ◽  
Maize Oil

1. Sheep were given intraruminal infusions of maize oil or linoleic acid and samples of contents were taken from the rumen and abomasum at different times after the infusions. Hydrolysis of the maize oil occurred in the rumen with the production of mono- and di-glycerides as intermediates. Linoleic acid derived from the maize oil was hydrogenated to stearic acid. When linoleic acid was infused into the rumen, little or no stearic acid was produced and octadecenoic acid accumulated.2. When linoleic acid or maize oil was incubated with rumen contents in an artificial rumen and samples of the reaction mixtures were taken from the apparatus after various time intervals, the results were similar to those obtained in vivo, except that the hydrolysis of maize oil did not give rise to mono- and di-glycerides.3. These results are discussed in relation to previous findings on the effects of intraruminal infusions of maize oil or linoleic acid on the fatty acid composition of the blood triglycerides of sheep.

scholarly journals In silico characterization of linoleic acid biotransformation to rumenic acid in food derived Lactobacillus plantarum YW11

2020 ◽  
Author(s):  
Tariq Aziz ◽  
Abid Sarwar ◽  
Muhammad Fahim ◽  
Sam Al Dalali ◽  
Zia Ud Din ◽  
...  
Keyword(s):  
Linoleic Acid ◽  
Conjugated Linoleic Acid ◽  
Lactobacillus Plantarum ◽  
In Silico ◽  
Octadecadienoic Acid ◽  
Scale Up ◽  
Octadecenoic Acid ◽  
Acid Ethyl Ester ◽  
Dependent Manner ◽  
In Silico Characterization

Lactobacillus plantarum YW11 capability to convert linoleic acid into conjugated linoleic acid and other metabolites was studied in a dose-dependent manner by supplementing LA at different concentrations. L. plantarum YW11 displayed a uniform distinctive growth curve of CLA and other metabolites at concentrations of LA ranging from 1% (w/v) to 10% (w/v), with slightly increased growth at higher LA concentrations. The biotransformation capability of L. plantarum YW11 evaluated by GC-MS revealed a total of one CLA isomer, i.e. 9-cis,11-trans-octadecadienoic acid, also known as the rumenic acid (RA), one linoleic acid isomer (linoelaidic acid), and LA metabolites: (E)-9-octadecenoic acid ethyl ester, trans, trans-9,12-octadecadienoic acid, propyl ester and stearic acid. All the metabolites of linoleic acid were produced from 1 to 10% LA supplemented MRS media, while surprisingly the only conjugated linoleic acid compound was produced at 10% LA. To assess the presence of putative enzymes, responsible for conversion of LA into CLA, in silico characterization was carried out. The in silico characterization revealed presence of four enzymes (10-linoleic acid hydratase, linoleate isomerase, acetoacetate decarboxylase and dehydrogenase) that may be involved in the production of CLA (rumenic acid) and LA isomers. The biotransformation ability of L. plantarum YW11 to convert LA into RA has great prospects for biotechnological and industrial implications that could be exploited in the future scale-up experiments.

scholarly journals Brown Fat–Activating Lipokine 12,13-diHOME in Human Milk Is Associated With Infant Adiposity

2020 ◽  
Author(s):  
Danielle Wolfs ◽  
Matthew D Lynes ◽  
Yu-Hua Tseng ◽  
Stephanie Pierce ◽  
Valerie Bussberg ◽  
...  
Keyword(s):  
Linoleic Acid ◽  
Human Milk ◽  
Octadecenoic Acid ◽  
Brown Fat ◽  
Protective Effects ◽  
Z Score ◽  
Anthropometric Measures ◽  
Medical Centers ◽  
Academic Medical ◽  
Infant Weight Gain

Abstract Context Little is known about the specific breastmilk components responsible for protective effects on infant obesity. Whether 12,13-dihydroxy-9Z-octadecenoic acid (12,13-diHOME), an oxidized linoleic acid metabolite and activator of brown fat metabolism, is present in human milk, or linked to infant adiposity, is unknown. Objective To examine associations between concentrations of 12,13-diHOME in human milk and infant adiposity. Design Prospective cohort study from 2015 to 2019, following participants from birth to 6 months of age. Setting Academic medical centers. Participants Volunteer sample of 58 exclusively breastfeeding mother-infant pairs; exclusion criteria included smoking, gestational diabetes, and health conditions with the potential to influence maternal or infant weight gain. Main Outcome Measures Infant anthropometric measures including weight, length, body mass index (BMI), and body composition at birth and at 1, 3, and 6 months postpartum. Results We report for the first time that 12,13-diHOME is present in human milk. Higher milk 12,13-diHOME level was associated with increased weight-for-length Z-score at birth (β = 0.5742, P = 0.0008), lower infant fat mass at 1 month (P = 0.021), and reduced gain in BMI Z-score from 0 to 6 months (β = −0.3997, P = 0.025). We observed similar associations between infant adiposity and milk abundance of related oxidized linoleic acid metabolites 12,13-Epoxy-9(Z)-octadecenoic acid (12,13-epOME) and 9,10-Dihydroxy-12-octadecenoic acid (9,10-diHOME), and metabolites linked to thermogenesis including succinate and lyso-phosphatidylglycerol 18:0. Milk abundance of 12,13-diHOME was not associated with maternal BMI, but was positively associated with maternal height, milk glucose concentration, and was significantly increased after a bout of moderate exercise. Conclusions We report novel associations between milk abundance of 12,13-diHOME and adiposity during infancy.

scholarly journals Observations on the pattern on biohydrogenation of esterified and unesterified linoleic acid in the rumen

1974 ◽  
Vol 31 (1) ◽  
pp. 99-108 ◽  
Author(s):  
R. C. Noble ◽  
J. H. Moore ◽  
C. G. Harfoot
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Free Fatty Acids ◽  
Free Acid ◽  
Octadecenoic Acid ◽  
Conjugated Diene ◽  
Plasma Triglycerides ◽  
Fatty Acid Compositions

1. Studies have been made of the effects of different concentrations of either free or esterified linoleic acid on the biohydrogenation of linoleic acid by rumen micro-organisms in vitro. A comparison has been made with the changes which occurred in the fatty acid compositions of rumen free fatty acids and plasma triglycerides of sheep given intraruminal infusions of linoleic acid or maize oil.2. In the in vitro experiments, with increasing concentrations of 18:2 added as the free fatty acid, a decreasing proportion of this 18:2 was hydrogenated to 18:0 andtrans-11-octadecenoic acid accumulated. The accumulation of large amounts oftrans-11-octadecenoic acid was accompanied in all instances by the accumulation of a conjugated diene identified ascis-9,trans-11-octadecadienoic acid. There appeared to be a product–precursor relationship between the conjugated diene and thetrans-11 monoene.3. When linoleic acid was presented in vitro as the triglyceride, the extent to which hydrogenation occurred was, in all instances, greater than when equivalent amounts of 18:2 were presented as the free acid. Only small amounts of thecis-9,trans-11 diene were detected, and there was no apparent product–precursor relationship between this conjugated diene and the C18monoenoic acids. The C18monoenoic acids that accumulated consisted of bothcisandtransisomers; thecisisomers consisted largely ofcis-9- andcis-11-octadecenoic acids, which together comprised about 30% of the C18monoenoic acids present.4. The infusion of free linoleic acid into the rumen of sheep resulted in an increase in the proportion of total 18:1 and a decrease in the proportions of 16:0 and 18:0 in the total rumen free fatty acids. This increase which occurred in the concentration of 18:1 consisted predominantly of thetrans-11 isomer. A concomitant increase in the concentration of the C18trans-11 acid was observed to occur in the fatty acids of the plasma triglycerides. Infusion of maize oil into the rumen of sheep resulted in little change in the fatty acid compositions of either the free fatty acids in the rumen or the triglycerides of the plasma.5. The findings in vitro and in vivo are discussed with reference to each other and with reference to the possibility that biohydrogenation of 18:2 derived from the triglyceride proceeds by a different pathway from that of 18:2 presented as the free acid.

scholarly journals Inhibitory effect of the gut microbial linoleic acid metabolites, 10-oxo-trans-11-octadecenoic acid and 10-hydroxy-cis-12-octadecenoic acid, on BV-2 microglial cell activation

2018 ◽  
Vol 138 (1) ◽  
pp. 9-15 ◽  
Author(s):  
Shiori Ikeguchi ◽  
Yasuhiko Izumi ◽  
Nahoko Kitamura ◽  
Shigenobu Kishino ◽  
Jun Ogawa ◽  
...  
Keyword(s):  
Linoleic Acid ◽  
Cell Activation ◽  
Microglial Cell ◽  
Octadecenoic Acid ◽  
Inhibitory Effect ◽  
Acid Metabolites

scholarly journals Kinetics and function of two mutants of CLA hydrase from Lactobacillus plantarum p-8

2020 ◽  
Vol 367 (12) ◽  
Author(s):  
Wei Zhao ◽  
Lili Zhao ◽  
Tongtong Zhao ◽  
Chao Zhi ◽  
Meiqi Liu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Escherichia Coli ◽  
Gas Chromatography ◽  
Linoleic Acid ◽  
Flavin Adenine Dinucleotide ◽  
Octadecenoic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
Directed Mutation ◽  
And Function ◽  
Optimal Ph

ABSTRACT In this work, the gene of conjugated linoleic acid hydrase (CLA-HY) was cloned from L. plantarum p-8, and the protein of CLA-HY was expressed in Escherichia coli BL21. Gas chromatography-mass spectrometry was employed to verify that the purified CLA-HY can convert linoleic acid (LA) into 10-hydroxy-cis-12-octadecenoic acid (10-HOE) in the presence of flavin adenine dinucleotide (FAD). The optimal pH and temperature for maximizing CLA-HY catalytic activity were found to be 6.0 and 35°C, respectively. In addition, the catalytic ability of CLA-HY can be inhibited by a number of cations such as Mg2+, Mn2+, Zn2+, Cu2+, Fe2+, Fe3+, Ni2+ and Ca2+. Finally, the Km,Vmax, Kcat and Kcat/Km of CLA-HY were determined as 7.62 mM, 2.59 mM h−1, 8.33 × 103 h−1 and 1.09 × 103 mM−1 h−1, respectively. Moreover, it was demonstrated that both M76 and G74 residues played significant roles in catalysing the conversion of LA into 10-HOE using site-directed mutation technology and molecular simulations.

scholarly journals The hydrogenation of the series of methylene-interruptedcis,cis-octadecadienoic acids by pure cultures of six rumen bacteria

1984 ◽  
Vol 52 (1) ◽  
pp. 171-177 ◽  
Author(s):  
Patrick Kemp ◽  
David J. Lander ◽  
R. T. Holman
Keyword(s):  
Linoleic Acid ◽  
Stearic Acid ◽  
Octadecadienoic Acid ◽  
Octadecenoic Acid ◽  
Rumen Bacteria ◽  
Pure Cultures ◽  
Octadecenoic Acids ◽  
Octadecadienoic Acids ◽  
Cis Isomer ◽  
Stimulation Of

1. The hydrogenation of all the methylene-interrupted cis, cis-octadecadienoic acids was examined using pure cultures of six rumen bacteria able to hydrogenate linoleic acid to stearic acid or its immediate precursor, trans-1 1-octadecenoic acid, after first conjugating the linoleic acid to cis,truns-9, 1 1-octadecadienoic acid.2. Only the Δ 14-cis, 17-cis-isomer was not hydrogenated by at least one of the bacteria and no evidence was found that conjugation was necessary before hydrogenation except for the Δ 2-cis,5-cis- and Δ 9-cis, 12-cis-isomers. Several isomers were hydrogenated to an extent close to that achieved with linoleic acid (Δ 9-cis, 124s).3. Those bacteria only able to hydrogenate linoleic to trans-1 1-octadecenoic acid gave only octadecenoic acid products and those bacteria able to hydrogenate linoleic acid to stearic gave variable yields of octadecenoic acids and stearic acid except with the isomers Δ 12-cis, 15-cis and Δ 13-cis, Idcis when only octadecenoic acids were detected.4. At the substrate levels used (20 μg/ml), both inhibition and stimulation of growth were found but no common pattern emerged, nor was the growth consistently related to the extent of hydrogenation.

scholarly journals Duodenal and Milk Trans Octadecenoic Acid and Conjugated Linoleic Acid (CLA) Isomers Indicate that Postabsorptive Synthesis Is the Predominant Source of cis-9-Containing CLA in Lactating Dairy Cows

2002 ◽  
Vol 132 (6) ◽  
pp. 1235-1241 ◽  
Author(s):  
Liliana S. Piperova ◽  
Joseph Sampugna ◽  
Beverly B. Teter ◽  
Kenneth F. Kalscheur ◽  
Martin P. Yurawecz ◽  
...  
Keyword(s):  
Linoleic Acid ◽  
Dairy Cows ◽  
Conjugated Linoleic Acid ◽  
Octadecenoic Acid ◽  
Lactating Dairy Cows ◽  
Cla Isomers ◽  
Trans Octadecenoic Acid
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