title: Enantiomeric separation of asymmetric triacylglycerol by recycle high-performance liquid chromatography with chiral column.
abstract: In our previous studies, we employed recycle HPLC for the separation of triacylglycerol (TAG)-positional isomers (PIs). In this study, a recycle HPLC system equipped with a polysaccharide-based chiral column was applied to the enantiomeric separation of some asymmetric TAGs having straight-chain C16-C18 acyl residues. As a result, 1,2-dipalmitoyl-3-oleoyl-rac-glycerol (rac-PPO), 1,2-dioleoyl-3-palmitoyl-rac-glycerol (rac-OOP), and 1,2-dipalmitoyl-3-linoleoyl-rac-glycerol (rac-PPL) were resolved into their respective enantiomers. However, neither 1,2-dioleoyl-3-linoleoyl-rac-glycerol (rac-OOL), consisting of only unsaturated fatty acids, nor 1,2-dipalmitoyl-3-stearoyl-rac-glycerol (rac-PPS), consisting of only saturated fatty acids, was resolved. These results suggest that the asymmetric TAGs, used in this study, having both a palmitic acid moiety and an oleic acid (or a linoleic acid) moiety at the sn-1 or sn-3 positions are resolved by the chiral column. This new chiral separation method can be used in combination with atmospheric pressure chemical ionization mass spectrometry to determine the sn-OOP/sn-POO ratio in palm oil. This method is applicable for the chiral separation of asymmetric TAGs in palm oil.
authors.affiliation: Tsukishima Foods Industry Co., Ltd., Tokyo, Japan. t-nagai@tsukishima.co.jp
authors.forename: Toshiharu
authors.initials: T
authors.lastname: Nagai
authors.forename: Hoyo
authors.initials: H
authors.lastname: Mizobe
authors.forename: Ikuko
authors.initials: I
authors.lastname: Otake
authors.forename: Kenji
authors.initials: K
authors.lastname: Ichioka
authors.forename: Koichi
authors.initials: K
authors.lastname: Kojima
authors.forename: Yumiko
authors.initials: Y
authors.lastname: Matsumoto
authors.forename: Naohiro
authors.initials: N
authors.lastname: Gotoh
authors.forename: Ikuma
authors.initials: I
authors.lastname: Kuroda
authors.forename: Shun
authors.initials: S
authors.lastname: Wada
mesh_terms: D002482:Cellulose / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D017743:Equipment Reuse; D048448:Phenylcarbamates / Q000737:chemistry; D013237:Stereoisomerism; D014280:Triglycerides / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D048448:Phenylcarbamates; D014280:Triglycerides; C065943:cellulose tris-3,5-dimethylphenyl-carbamate; D002482:Cellulose