triglycerides and 1-3-distearoyl-2-oleoylglycerol

In the present study, we investigated the effect of long-acyl chain SFA, namely palmitic acid (16:0) and stearic acid (18:0), at sn-1, 3 positions of TAG on obesity. Throughout the 15 weeks of the experimental period, C57BL/6 mice were fed diets fortified with cocoa butter, sal stearin (SAL), palm mid fraction (PMF) and high-oleic sunflower oil (HOS). The sn-1, 3 positions were varied by 16:0, 18:0 and 18:1, whilst the sn-2 position was preserved with 18:1. The HOS-enriched diet was found to lead to the highest fat deposition. This was in accordance with our previous postulation. Upon normalisation of total fat deposited with food intake to obtain the fat:feed ratio, interestingly, mice fed the SAL-enriched diet exhibited significantly lower visceral fat/feed and total fat/feed compared with those fed the PMF-enriched diet, despite their similarity in SFA-unsaturated fatty acid-SFA profile. That long-chain SFA at sn-1, 3 positions concomitantly with an unsaturated FA at the sn-2 position exert an obesity-reducing effect was further validated. The present study is the first of its kind to demonstrate that SFA of different chain lengths at sn-1, 3 positions exert profound effects on fat accretion.

Topics: Adiposity; Animals; Diet, High-Fat; Dietary Fats; Feces; Intestinal Absorption; Intra-Abdominal Fat; Male; Mice; Mice, Inbred C57BL; Obesity; Oleic Acid; Palm Oil; Palmitic Acid; Plant Oils; Random Allocation; Stearic Acids; Subcutaneous Fat; Sunflower Oil; Triglycerides; Triolein; Weight Gain

An improved crystal structure model has been established for the beta2 polymorph of the symmetric mono-unsaturated triacylglycerol 1,3-distearoyl-2-oleoylglycerol (SOS) and the equivalent beta-V polymorph of Ivory Coast cocoa butter. In addition, the crystal structures of the beta2 polymorphs are reported for the triacylglycerols 1,3-dipalmitoyl-2-oleoylglycerol (POP) and 1-palmitoyl-2-oleoyl-3-stearoylglycerol (POS), which are, together with SOS, the major components of cocoa butter, and that of 1-stearoyl-2-oleoyl-3-arachidoylglycerol (SOA). The existence of beta2-POS and beta2-SOA has not been previously reported in the literature. All structures have been solved from high-resolution laboratory or synchrotron powder diffraction data with the direct-space parallel-tempering program FOX and refined with the Rietveld module of GSAS. All compounds crystallize in similar monoclinic unit cells (Cc) with very long b axes (>127 A). The oleic chains are packed together and sandwiched between saturated chain layers, forming acyl-chain three-packs. An analysis of the beta2 polymorphs and beta1 polymorphs [van Mechelen et al. (2006). Acta Cryst. B62, 1121-1130] shows that they contain the same three-packs and differ only in the symmetry relation between the three-packs. The three-pack build-up provides an explanation of the mechanism of the phase transition that causes the formation of fat bloom on dark chocolate.

Topics: Crystallization; Glycerol; Models, Molecular; Phase Transition; Powder Diffraction; Triglycerides