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The HPLC resolution of the enantiomeric sn-1, 2- and sn-2, 3-diacylglycerol (DG) moieties of fish-oil triacylglycerols (TGs) having different fatty acid compositions was carried out on a chiral stationary phase, (R)-1-(1-naphthyl)ethylamine. The DGs were generated from TGs of tuna orbital, pomfret flesh and pacific saury flesh by partial Grignard degradation ; they were chromatographed as 3, 5-dinitrophenylurethanes. By an isocratic elution with n-hexane-1, 2-dichloroethane-ethanol 40 : 30 : 1 (v/v/v) as the mobile phase, the sn-1, 2 (2, 3)-DGs from tuna orbital and pomfret flesh were resolved into two clearly distinguishable enantiomer groups, although some peak overlappings between the enantiomers were observed in the latter sample. On the other hand, no clear enatiomer resolution was obtained for the saury flesh DGs. The poorer resolution was mainly caused by the existence of large amounts of long-chain monounsaturated fatty acids (20 : 1 and 22 : 1) in the molecules.

Separation, Detection, and Functional Materials. Chiral-phase HPLC resolution of enantiomeric diacylglycerol moieties of fish-oil triacylglycerols.