Simultaneous Quantification of Mixed-Acid Triacylglycerol Positional Isomers and Enantiomers in Palm Oil and Lard by Chiral High-Performance Liquid Chromatography Coupled with Mass Spectrometry

Toshiharu Nagai,Kazuaki Yoshinaga,Naohiro Gotoh,Yutaka Itabashi,Hoyo Mizobe,Erika Kasamatsu,Akihiko Yoshida,Tetsuaki Kinoshita

doi:10.3390/sym12091385

Toshiharu Nagai, Kazuaki Yoshinaga + Show 6 more

Open Access

https://doi.org/10.3390/sym12091385

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Abstract

Palm oil and lard are edible fats which are rich in palmitic (P) and oleic acids (O). In this study, triacylglycerol (TAG) positional isomers (symmetric and asymmetric isomers) and enantiomers (asymmetric isomers) in palm oil and lard were quantified simultaneously by using liquid chromatography/mass spectrometry. The CHIRALPAK IF-3 column used in our previous study recognized the difference of TAG isomers consisting of P and O in palm oil and lard, separated sn-OPP/sn-PPO/sn-POP and sn-OPO/sn-OOP/sn-POO into each isomer peak, and enabled the quantification of these TAG isomers with good recovery (95–120%). Although sn-POP and sn-OPO were the major TAGs in palm oil and lard, a comparison of the abundance ratios of TAG enantiomers such as sn-PPO/sn-OPP and sn-OOP/sn-POO revealed that there were slightly more TAG enantiomers with O at the sn-1 position and P at the sn-3 position in palm oil and P at the sn-1 position and O at the sn-3 position in lard. These results were consistent with previous reports for the positional distribution of fatty acids of palm oil and lard. This is the first study that has enabled all TAG isomers consisting of P and O in natural oils and fats to be individually quantified by mass spectrometry.

Highlights

Oils and fats originated from plants and animals are widely used in a variety of industries.Triacylglycerol (TAG) is a main component of edible oils and fats, and their physical and nutritional properties depend on TAG compositions
In 2011, we developed a reversed phase (RP) high performance liquid chromatography (HPLC) method using Sunrise C28 column
Althoughfats fatsand andoils oilsare areaggregates aggregatesofofmany manyTAGs, TAGs,ititisisexpected expectedthat that different the physical properties of semi-solid fats such as palm oil and lard can be evaluated by examining the physical properties of semi-solid fats such as palm oil and lard can be evaluated by examining theisomers isomersofofthe themajor majorTAGs

Summary

Introduction

Oils and fats originated from plants and animals are widely used in a variety of industries. Sunrise C28 column separated TAG positional isomers saturated and one unsaturated fatty acids such as sn-POP/sn-PPO (or sn-OPP). For developed a new chiral HPLC method using CHIRALPAK IF-3 column (Daicel Corporation) which can this reason, we have developed a new chiral HPLC method using CHIRALPAK IF-3 column (Daicel simultaneously separate TAG positional isomers and enantiomers such as sn-OPP/sn-PPO/sn-POP and Corporation) which can simultaneously separate TAG positional isomers and enantiomers such as sn-OPO/sn-OOP/sn-POO [17]. We applied this chiral HPLC to the simultaneous quantification of naturally occurring TAG isomers, sn-OPP/sn-PPO/sn-POP and with mass spectrometry (MS) to the simultaneous quantification of naturally occurring TAG isomers, sn-OPO/sn-OOP/sn-POO in palm oil and lard. No study has ever separated all these TAG positional sn-OPP/sn-PPO/sn-POP and sn-OPO/sn-OOP/sn-POO in palm oil and lard.

Materials and Reagents

Preparation of Standard Solutions

Preparation of Sample Solution

Discussion

Findings

Conclusions