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キラル高速液体クロマトグラフィー/大気圧化学イオン化質量分析法によるグリシドール脂肪酸エステルの光学異性体分析

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Title: キラル高速液体クロマトグラフィー/大気圧化学イオン化質量分析法によるグリシドール脂肪酸エステルの光学異性体分析
Other Titles: Analysis of enantiomeric glycidyl fatty acid esters by chiral-phase HPLC/MS with atmospheric pressure chemical ionization
Authors: 吉岡, 智史1 Browse this author
西村, 一彦2 Browse this author
高村, 岳樹3 Browse this author
酒々井, 眞澄4 Browse this author
津田, 洋幸5 Browse this author
板橋, 豊6 Browse this author →KAKEN DB
Authors(alt): Yoshioka, Satoshi1
Nishimura, Kazuhiko2
Takamura, Takeji3
Suzui, Masumi4
Tsuda, Hiroyuki5
Itabashi, Yutaka6
Keywords: Glycidyl fatty acid ester
Enantiomer
Diacylglycerol-rich oil
Chiral-phase HPLC
Atmospheric pressure chemical ionization mass spectrometry
Issue Date: 5-Sep-2012
Publisher: 日本分析化学会
Journal Title: 分析化学
Volume: 61
Issue: 9
Start Page: 783
End Page: 790
Publisher DOI: 10.2116/bunsekikagaku.61.783
Abstract: キラル高速液体クロマトグラフィー/質量分析法(HPLC/MS)を用いて,食用油に微量存在し,安全性が危惧されているグリシドール脂肪酸エステル(GE)の光学異性体を分離,定量する方法を検討した.HPLC分析には,アミロース誘導体を固定相とするカラムとアセトニトリルに少量のメタノールを添加した移動相を使用した.MSには四重極型質量分析計を用いて,大気圧化学イオン化法で正イオンスペクトルを測定した.その結果,炭素数と不飽和度の異なるGEの光学異性体が明瞭に分離され,それぞれから顕著なプロトン化分子 [M+H]+ が検出された.このイオンを用いる選択イオン検出法によって,ジアシルグリセロールを約80%含有する食用油(DAG油)を直接分析した結果,アシル基の異なる5種のGE(16:0-GE,18:0-GE,18:1-GE,18:2-GE,18:3-GE)が検出され,これらはいずれも(R)-異性体と(S)-異性体のほぼ等量混合物であることが明らかになった.得られた結果から,DAG油に含まれるGEの光学異性体は,ほぼラセミ体の1-モノアシルグリセロールから生成するものと考えられた.
A simple and selective method was developed for the determination of enantiomeric glycidyl fatty acid esters (GE) in refined edible oils, which are undesirable trace contaminants formed during refining processes. For this purpose, chiral-phase high-performance liquid chromatography (HPLC) was performed with a column containing amylose tris(3,5-dimethylphenylcarbamate) as a chiral selector, using an acetonitrile/methanol mixture as the mobile phase, which gave clear enantiomer resolution of synthetic saturated and unsaturated GE racemates. This was followed by on-line atmospheric pressure chemical ionization mass spectrometry (APCI/MS) to obtain prominent protonated [M+H]+ molecules, by which individual GE molecules could be identified and quantified. The quantification of GE enantiomers was performed in the selected ion monitoring (SIM) of [M+H]+ . This chiralphase HPLC/APCI-MS-SIM method was standardized with synthetic GE racemates, and applied to the separation, identification and quantification of individual GE enantiomers in a commercial diacylglycerol (DAG)-rich oil produced originally from soybean oil and rapeseed oil. The results clearly showed that the DAG-rich oil contained almost equal amounts of Rand S-enantiomers of glycidyl palmitate (16 : 0-GE), stearate (18 : 0-GE), oleate (18 : 1-GE), linoleate (18 : 2-GE), and linolenate (18 : 3-GE), suggesting that both enantiomers would be formed from the corresponding almost racemic 1-monoacylglycerols. The most predominant GE was 18 : 2-GE, followed by 18 : 1-GE, which accounted for 107 and 25 μg g-1, respectively, reflecting the fatty acid composition of the DAG oil.
Type: article
URI: http://hdl.handle.net/2115/50328
Appears in Collections:水産科学院・水産科学研究院 (Graduate School of Fisheries Sciences / Faculty of Fisheries Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 板橋 豊

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