Journal of Lipid Research, Vol 31, 1711-1717, Copyright © 1990 by Lipid Research, Inc.
HPLC resolution of diacylglycerol moieties of natural triacylglycerols on a chiral phase consisting of bonded (R)-(+)-1-(1-naphthyl)ethylamine
Y Itabashi, A Kukis, L Marai and T Takagi
Banting and Best Department of Medical Research, University of Toronto, Canada.
Chiral phase high performance liquid chromatographic resolution of sn-
1,2(2,3)- and X-1,3-diacylglycerols generated by partial Grignard
degradation from natural triacylglycerols was carried out using a chiral
column (25 cm x 4.6 mm i.d.) containing (R)-(+)-1-(1- napthyl)ethylamine
polymer chemically bonded to 300A wide pore spherical silica (5 microns
particles). The diacylglycerols were chromatographed as
3,5-dinitrophenyl-urethanes and detected at 226 or 254 nm UV. By an
isocratic elution with n-hexane- 1,2-dichloroethane- ethanol 40:10:1
(v/v/v) as the mobile phase, the sn-1,2(2,3)- diacylglycerols from corn,
linseed, and menhaden oils were resolved into two clearly distinguishable
enantiomer groups, although some peak overlappings between the enantiomers
were observed in the linseed and menhaden oil diacylglycerols. In addition
to the excellent enantiomer resolution, each enantiomer and the
X-1,3-isomers were partially resolved into several peaks, which could be
tentatively identified on the basis of equivalent carbon number. It is
concluded that chiral phase high performance liquid chromatography can be
utilized for effective resolution, identification, and quantitation of
enantiomeric diacylglycerols from complex natural mixtures.
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