Absorption of synthetic, stereochemically defined acylglycerols in the rat.

The stereochemistry of fat digestion and absorption was investigated in rats with thoracic duct fistulas, after feeding synthetic triacylglycerol or alkyldiacylglycerol. After feeding 1,2-dilauroyl-3-oleoyl-sn-glycerol, dilauroyloleoylglycerol and lauroyldioleoylglycerol were the most abundant chyle triacylglycerols. Positional analysis of the fatty acid distribution and the absence of optical activity indicated that the following structures dominated: rac-1,2-dilauroyl-3-oleoylglycerol and rac-1,3-dioleoyl-2-lauroylglycerol. Therefore, the triacylglycerol resynthesized from 2-lauroylglycerol (pre-cursor to 60% of chyle triacylglycerol) and other precursors was essentially racemic. Chyle phospholipids contained largely endogenous fatty acids, and the proportion of lauric acid was very low. A racemic mixture of 1,2-di[3H] oleoyl-3-tetradecyl-sn-glycerol and 1-tetradecyl-2,3-di[12C] oleoyl-sn-glycerol was absorbed to a lower degree than triacylglycerol. The appearace of oleic acid with different labels in chyle and intestinal lipids did not differ, indicating the absence of stereospecificity in fat digestion. Possible explanations for the low absorption are discussed.