Preparation of Chiral Triacylglycerols, &lt;i&gt;sn&lt;/i&gt;-POO and &lt;i&gt;sn&lt;/i&gt;-OOP, via Lipase-mediated Acidolysis Reaction

Yamamoto, Yukihiro; Yoshida, Hajime; Nagai, Toshiharu; Hara, Setsuko

doi:10.5650/jos.ess17149

Cited by 7 publications

(2 citation statements)

References 18 publications

(8 reference statements)

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“…1d–f), indicating complete separation of the two enantiomers. By modifying the ratio of sn‐ OOP to sn‐ POO according to the method reported by Yamamoto et al (2018), we were able to identify the R‐form and L‐form peaks (data not shown). The peak with the shorter retention time (RT) (34.4 min) originated from sn‐ OOP, while that with the longer RT (35.5 min) was attributed to sn‐ POO.…”

Section: Resultsmentioning

confidence: 94%

A Practical Method for Analysis of Triacylglycerol Isomers Using Supercritical Fluid Chromatography

Masuda

Abe²,

Murano

2020

J Americ Oil Chem Soc

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Triacylglycerol (TAG) isomers have been reported to have differing physical and nutritional properties. The analysis of TAG isomers is therefore important for understanding the physical properties of lipids as well as their digestion and absorption. However, methods for the quantitative analysis of TAG regioisomers and enantiomers in vegetable oils and biological samples are still under development. Recently, methods using recycle high‐performance liquid chromatography (HPLC) and silver ion column‐HPLC have been reported. However the recycle HPLC method requires more than 1 hour, in general, for each sample that is analyzed. Furthermore, existing methods are unable to quantify regioisomers and enantiomers simultaneously. Thus, we aimed to develop a practical method to simultaneously quantify regioisomers and enantiomers of TAG. Three isomers of sn‐POO, OPO, and OOP were separated by supercritical fluid chromatography coupled with triple quadrupole mass spectrometer (SFC/MS/MS) using a CHIRALPAK® IG‐U column with acetonitrile and methanol as mobile phase. The separation was completed in 40 min, which is a shorter run time than the conventional techniques published to date. Linear calibration curves with standards were obtained and used to quantify sn‐OPO, sn‐POO, and sn‐OOP in extra virgin olive oil, refined olive oil, palm oil, palm olein, and interesterified palm olein.

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Section: Resultsmentioning

confidence: 94%

A Practical Method for Analysis of Triacylglycerol Isomers Using Supercritical Fluid Chromatography

Masuda

Abe²,

Murano

2020

J Americ Oil Chem Soc

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“…The mixture was incubated in the dark at 60℃, and agitated at 600 rpm for 48 h. To terminate the reaction, the enzyme was filtered off and the filtrate was removed by evaporation. This reaction mixture was applied to a Florisil ® column for chromatographic separation to obtain the target CLA-TAG fraction, as previously reported 13) .…”

Section: Preparation Of Cla-tagmentioning

confidence: 99%

Effect of Molecular Form of Conjugated Linoleic Acid on Oxidative Stability : Comparison of Triacylglycerol and Phosphatidylcholine Form

et al. 2020

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acid 4) .It is known that the oxidative stability of lipids is affected not only by their fatty acid compositions, but also by their molecular species and lipid form 7) . For example, in the TAG form, polyunsaturated fatty acids (PUFAs) , such as DHA and eicosapentaenoic acid (EPA) , substituted at the sn-2 position, are more stable than those substituted at the sn-1 (3) position 8,9) . A similar conclusion was reached for TAG containing conjugated linolenic acid based on conductometric determination under oxidative conditions (90℃ and air flow of 20 L/h) 10) . However, few studies have compared the oxidative stability of the TAG form and phospholipid form of unsaturated fatty acids. Of the few reports, Grandois et al. reported that the phosphatidylcholine (PC) form of oleic acid and linoleic acid is more resistant to oxidative degradation than the TAG form when oxidized under heating conditions (50-175℃) 11) .To date, no comparative analysis of the oxidative stability of CLA in the TAG and PC form, with CLA substituted at the sn-2 position (CLA-TAG and CLA-PC) , has been documented. The objective of this study is to reveal the effects of the molecular form of CLA, with different lipid forms Abstract: The health benefits of conjugated linoleic acid (CLA), a functional lipid with anti-cancer, antiobesity, and hypotensive activity, have garnered increasing attention. The current study was conducted to determine the oxidative stability of CLA in the form of triacylglycerol (CLA-TAG) and phosphatidylcholine (CLA-PC) at the sn-2 position. Oxidation was performed at 30℃ or 40℃ in the dark. Hydroperoxides, as the primary oxidation products, were analyzed using diphenyl-1-pyrenylphosphine. Thiobarbituric acid reactive substances (TBARS) and volatile compounds were monitored as secondary oxidation products. The results suggest that CLA-PC was more stable against oxidation than CLA-TAG from the perspective of suppression of the generation of hydroperoxides and TBARS. However, CLA-PC produced more volatile compounds than CLA-TAG. We suggest that choline was released during the oxidation of CLA-PC, and acted as an antioxidant. The ensuing reaction between choline and hydroperoxide induced the generation of volatile compounds such as pentanal, hexanal, and heptanal.

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Immobilization of lipases on hydrophobic supports: immobilization mechanism, advantages, problems, and solutions

Rodrigues

Virgen-Ortíz

Santos

et al. 2019

Biotechnology Advances

453

291

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Lipases are the most widely used enzymes in biocatalysis, and the most utilized method for enzyme immobilization is using hydrophobic supports at low ionic strength. This method allows the one step immobilization, purification, stabilization, and hyperactivation of lipases, and that is the main cause of their popularity. This review focuses on these lipase immobilization supports. First, the advantages of these supports for lipase immobilization will be presented and the likeliest immobilization mechanism (interfacial activation on the support surface) will be revised. Then, its main shortcoming will be discussed: enzyme desorption under certain conditions (such as high temperature, presence of cosolvents or detergent molecules). Methods to overcome this problem include physical or chemical crosslinking of the immobilized enzyme molecules or using heterofunctional supports. Thus, supports containing hydrophobic acyl chain plus epoxy, glutaraldehyde, ionic, vinylsulfone or glyoxyl groups have been designed. This prevents enzyme desorption and improved enzyme stability, but it may have some limitations, that will be discussed and some additional solutions will be proposed (e.g., chemical amination of the enzyme to have a full covalent enzyme-support reaction). These immobilized lipases may be subject to unfolding and refolding strategies to reactivate inactivated enzymes. Finally, these biocatalysts have been used in new strategies for enzyme coimmobilization, where the most stable enzyme could be reutilized after desorption of the least stable one after its inactivation.

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Preparation of Chiral Triacylglycerols, <i>sn</i>-POO and <i>sn</i>-OOP, via Lipase-mediated Acidolysis Reaction

Cited by 7 publications

References 18 publications

A Practical Method for Analysis of Triacylglycerol Isomers Using Supercritical Fluid Chromatography

A Practical Method for Analysis of Triacylglycerol Isomers Using Supercritical Fluid Chromatography

Effect of Molecular Form of Conjugated Linoleic Acid on Oxidative Stability : Comparison of Triacylglycerol and Phosphatidylcholine Form

Immobilization of lipases on hydrophobic supports: immobilization mechanism, advantages, problems, and solutions

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