scholarly journals Lipase Catalyzed Acidolysis for Efficient Synthesis of Phospholipids Enriched with Isomerically Pure cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid

Catalysts ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 1012 ◽  
Author(s):  
Natalia Niezgoda ◽  
Anna Gliszczyńska
Keyword(s):  
Linoleic Acid ◽  
Conjugated Linoleic Acid ◽  
Biological Effects ◽  
Reaction System ◽  
Rhizomucor Miehei ◽  
Egg Yolk ◽  
Biologically Active ◽  
Molar Ratio ◽  
Active Compounds ◽  
Cla Isomers

The production of phospholipid (PL) conjugates with biologically active compounds is nowadays an extensively employed approach. This type of phospholipids conjugates could improve bioavailability of many poorly absorbed active compounds such as isomers of conjugated linoleic acid (CLA), which exhibit versatile biological effects. The studies were carried out to elaborate an efficient enzymatic method for the synthesis of phospholipids with pure (>90%) cis-9,trans-11 and trans-10,cis-12 CLA isomers. For this purpose, three commercially available immobilized lipases were examined in respect to specificity towards CLA isomers in acidolysis of egg-yolk phosphatidylcholine (PC). Different incorporation rates were observed for the individual CLA isomers. Under optimal conditions: PC/CLA molar ratio 1:6; Rhizomucor miehei lipase loading 24% wt. based on substrates; heptane; DMF, 5% (v/v); water activity (aw), 0.11; 45 °C; magnetic stirring, 300 rpm; 48 h., effective incorporation (EINC) of CLA isomers into PC reached ca. 50%. The EINC of CLA isomers was elevated for 25–30% only by adding a water mimic (DMF) and reducing aw to 0.11 comparing to the reaction system performed at aw = 0.23. The developed method of phosphatidylcholine acidolysis is the first described in the literature dealing with isometrically pure CLA and allow to obtain very high effective incorporation.

scholarly journals Mechanisms of Anticancer Activity of a Fatty Acid Mixture Extracted from Hen Egg Yolks Enriched in Conjugated Linoleic Acid Diene (CLA) against WM793 Melanoma Cells

Nutrients ◽  
2021 ◽  
Vol 13 (7) ◽  
pp. 2348
Author(s):  
Dominik Domagała ◽  
Teresa Leszczyńska ◽  
Aneta Koronowicz ◽  
Barbara Domagała ◽  
Mariola Drozdowska ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Cancer Cells ◽  
Conjugated Linoleic Acid ◽  
Egg Yolk ◽  
Mitochondrial Pathway ◽  
Fatty Acid Mixture ◽  
Biologically Active ◽  
Acid Mixture

The conjugated linoleic acid (CLA) diene is a biologically active compound with proven health-promoting effects. In terms of anticancer properties, it has been shown that CLA reduces the proliferation of cancer cells. In this study, it has been demonstrated that a mixture of fatty acids, isolated from chicken egg yolk enriched in CLA isomers by biofortification, reduces (by 30.5%) the proliferation of human melanoma cancer cells line WM793 to a greater extent than a mixture of fatty acids not containing these isomers. At the same time, the tested fatty acid mixtures show no effect on human normal BJ fibroblast cells. For the first time, the genes with increased expression have been identified and the proteins have been activated by the fatty acid mixture of CLA-enriched egg yolk, mainly responsible for mitochondrial pathway-dependent apoptosis.

Conjugated linoleic acid (CLA) isomers in human adipose tissue

1997 ◽  
Vol 205 (6) ◽  
pp. 415-418 ◽  
Author(s):  
J. Fritsche ◽  
Magdi M. Mossoba ◽  
Martin P. Yurawecz ◽  
John A. G. Roach ◽  
Najibullah Sehat ◽  
...  
Keyword(s):  
Adipose Tissue ◽  
Linoleic Acid ◽  
Conjugated Linoleic Acid ◽  
Human Adipose Tissue ◽  
Cla Isomers

scholarly journals Production of Structured Phosphatidylcholine with High Content of Myristic Acid by Lipase-Catalyzed Acidolysis and Interesterification

Catalysts ◽  
2018 ◽  
Vol 8 (7) ◽  
pp. 281 ◽  
Author(s):  
Anna Chojnacka ◽  
Witold Gładkowski
Keyword(s):  
Myristic Acid ◽  
Rhizomucor Miehei ◽  
Egg Yolk ◽  
Thermomyces Lanuginosus ◽  
Molar Ratio ◽  
Acyl Donor ◽  
Thermomyces Lanuginosus Lipase ◽  
Screening Experiments ◽  
Miehei Lipase ◽  
Acyl Donors

Synthesis of structured phosphatidylcholine (PC) enriched with myristic acid (MA) was conducted by acidolysis and interesterification reactions using immobilized lipases as catalysts and two acyl donors: trimyristin (TMA) isolated from ground nutmeg, and myristic acid obtained by saponification of TMA. Screening experiments indicated that the most effective biocatalyst for interesterification was Rhizomucor miehei lipase (RML), whereas for acidolysis, the most active were Thermomyces lanuginosus lipase (TLL) and RML. The effect of the molar ratio of substrates (egg-yolk PC/acyl donor), enzyme loading, and different solvent on the incorporation of MA into PC and on PC recovery was studied. The maximal incorporation of MA (44 wt%) was achieved after 48 h of RML-catalyzed interesterification in hexane using substrates molar ratio (PC/trimyristin) 1/5 and 30% enzyme load. Comparable results were obtained in toluene with 1/3 substrates molar ratio. Interesterification of PC with trimyristin resulted in significantly higher MA incorporation than acidolysis with myristic acid, particularly in the reactions catalyzed by RML.

scholarly journals  A new internal standard for HPLC assay of conjugated linoleic acid in animal tissues and milk

2011 ◽  
Vol 56 (No. 1) ◽  
pp. 23-29 ◽  
Author(s):  
M. Czauderna ◽  
J. Kowalczyk ◽  
M. Marounek ◽  
J.P. Michalski ◽  
A.J. Rozbicka-Wieczorek
Keyword(s):  
Fatty Acids ◽  
Linoleic Acid ◽  
Conjugated Linoleic Acid ◽  
Biological Samples ◽  
Mobile Phase ◽  
Sorbic Acid ◽  
Internal Standard ◽  
Silver Ion ◽  
Animal Origin ◽  
Cla Isomers

A new method for the quantification of underivatized conjugated linoleic acid (CLA) isomers and CLA-metabolites by silver ion liquid chromatography (Ag<sup>+</sup>-HPLC) with photodiode array detection (DAD) is described. Conjugated fatty acids (CFA) and sorbic acid as the internal standard (IS) were separated on two 5 &mu;m Chrompac ChromSpher Lipids columns (250 &times; 4.6 mm). Biological samples were hydrolyzed with 1M KOH in methanol and 2M KOH in water at room temperature for 12 h. Hydrolyzates were acidified and the free fatty acids were extracted with dichloromethane. The organic solvent was removed and then the residue was re-dissolved in hexane and centrifuged. The supernatant was injected onto the columns. The mobile phase of 1.6% acetic acid and 0.0125% acetonitrile in hexane was chosen as the optimum mobile phase for fractionation of IS, CLA isomers and CLA-metabolites in all assayed biological samples. The use of two silver ion-exchange columns with direct UV detection (Ag<sup>+</sup>-HPLC-DAD) offers satisfactory precision of the IS quantification and low limits of detection of IS and CLA isomers (0.60 and 0.21&ndash;0.35 ng, respectively). The presented simple Ag<sup>+</sup>-HPLC-DAD method with sorbic acid as the IS can be used for direct determination of underivatized CLA isomers in specimens of animal origin. &nbsp;

Comparison of Methylation Methods for the Quantitation of Conjugated Linoleic Acid Isomers

1993 ◽  
Vol 76 (3) ◽  
pp. 644-649 ◽  
Author(s):  
Nalur Chandrasekaran Shantha ◽  
Eric Andrew Decker ◽  
Bernhard Hennig
Keyword(s):  
Linoleic Acid ◽  
Conjugated Linoleic Acid ◽  
Sodium Methoxide ◽  
Boron Trifluoride ◽  
Acetyl Chloride ◽  
Octadecadienoic Acid ◽  
Methyl Esters ◽  
Low Concentrations ◽  
Cla Isomers ◽  
In Cis

Abstract Four methylation methods were evaluated for use in the gas chromatographic (GC) quantitation of conjugated linoleic acid (CLA) isomers, which are potential anticarcinogen. The methods were (1) sodium methoxide in methanol (NaOMe-MeOH), (2) American Oil Chemists' Society (AOCS) procedure Ce 2-66, which involves methanolic sodium hydroxide followed by boron trifluoride in methanol, (3) tetramethylguanidine in methanol (TMG-MeOH), and (4) direct transesterification with methanolbenzene- acetyl chloride (DAC). Purified methyl esters of isomerized linoleic acid containing 86% CLA isomers were methylated and analyzed by GC. The AOCS and DAC methods resulted in 3 and 50% losses in cis-9,trans-11-octadecadienoic acid (9c, 111 CLA isomer) and trans-10,cis-12 octadecadienoic acid (10t, 12c CLA isomers), respectively. Compared with the control, the AOCS and DAC methods increased the yield of the trans,trans CLA isomers (trans-9,trans-11- and trans-10, trans-12-octadecadienoic acid) by 1.07-fold and a 10-fold, respectively. A non-CLA artifact that eluted close to CLA peaks was formed during methylation by the AOCS and DAC methods. Thus, the DAC and AOCS methods are not suitable for quantitation of CLA isomers. The NaOMe-MeOH and TMG-MeOH methods, however, are suitable for quantitation of CLA isomers in fats containing low concentrations of free fatty acids.

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