triglycerides and 1-3-dioleoyl-2-palmitoylglycerol

Owing to the increasing reports of the harmful effects of trans and saturated fatty acids, the demand for trans- and saturated-fatty-acid-free oil and fat products is increasing among consumers. However, it is difficult to maintain the product stability and shape retention of such oil and fat products. As a result, there is a high demand in the processed oil and fat industry to develop solutions to such problems. Herein, we used molecular compound (MC) crystals in an attempt to find alternatives to trans and saturated fatty acids. The MCs used were 1,3-dioleoyl-2-palmitoyl-

Topics: Calibration; Calorimetry, Differential Scanning; Cold Temperature; Crystallization; Drug Design; Fatty Acids; Glycerol; Oleic Acid; Palm Oil; Phase Transition; Plant Oils; Synchrotrons; Triglycerides; X-Ray Diffraction

Fat randomization and interesterification change triacylglycerol (TAG) structure and its solid fat content profile. It has not been thoroughly investigated whether these changes affect lipid metabolism.. Two experiments were conducted to investigate the effects of TAG structure and solid fat content on feed intake, body weight change, and serum metabolite concentrations in mice. An experiment used two fats rich in 1,2-dipalmitoyl-3-oleoylglycerol (PPO) and 1,3-dipalmitoyl-2-oleoylglycerol (POP) as comparative pair of fats to assess the effect of TAG structure since PPO and POP have the same fatty acid composition and solid fat content at 37 °C. Another experiment used a fat rich in 1-palmitoyl-2,3-dioleoylglycerol (POO) with solid fat content of zero at 37 °C and a mixture of fats that had the same general fatty acid composition and palmitic acid positional distribution, but with solid fat content of 22 % at 37 °C. This pair of fats was used to examine the effect of solid fat content on blood lipid profile.. After 6-week feeding, the pair of fats with different solid fat contents did not significantly affect the concentrations of total serum cholesterol, HDL cholesterol, TAG, non-esterified fatty acid (NEFA), or blood glucose. However, the PPO fat significantly reduced feed intake, body weight, and serum glucose concentration as compared to POP.. These results suggest that the presence of solid fat at the level examined does not affect lipid metabolism and lipemia, but PPO diet significantly affects NEFA and glucose concentrations. Palmitic acid at the sn-2 position of the TAG may have significant effect on appetite, which may be mediated via the gut receptors.

Topics: Animals; Blood Glucose; Body Weight; Cholesterol, HDL; Cholesterol, LDL; Dietary Fats; Fasting; Fatty Acids; Fatty Acids, Nonesterified; Lipid Metabolism; Male; Mice; Mice, Inbred C57BL; Palmitic Acid; Triglycerides

We systematically examined the phase behavior of binary mixtures of mixed-acid triacylglycerols (TAGs) containing palmitic and oleic acid moieties 1,3-dioleoyl-2-palmitoyl-glycerol (OPO), 1,2-dipalmitoyl-3-oleoyl-rac-glycerol (PPO), and 1,2-dioleoyl-3-palmitoyl-rac-glycerol (OOP), which are widely present in natural fats and are employed in the food, pharmaceutical, and cosmetic industries. Differential scanning calorimetry and X-ray diffraction methods were applied to observe the mixing behavior of PPO/OPO, OOP/OPO, and PPO/OOP under metastable and stable conditions. The results led to three conclusions: (1) Eutectic behavior was observed in PPO/OPO. (2) Molecular compound (MC) crystals were formed in the mixtures of OOP/OPO and PPO/OOP. (3) However, the MC crystals occurred only under metastable conditions and tended to separate into component TAGs to form eutectic mixture systems after 17 months of incubation. These results were contrary to those of previous studies on 1,3-dipalmitoyl-2-oleoyl glycerol (POP)/OPO and POP/PPO in which the MC crystals were thermodynamically stable. We determined that specific molecular interactions may cause this different phase behavior (stability of POP/OPO and POP/PPO MC crystals and metastability of OOP/OPO and PPO/OOP MC crystals). All results confirm the significant effects of molecular structures of glycerol groups, interactions of fatty acid chains, and polymorphism of the component TAGs on the mixing behavior of mixed-acid TAGs.

Topics: Calorimetry, Differential Scanning; Complex Mixtures; Models, Molecular; Oleic Acid; Thermodynamics; Transition Temperature; Triglycerides; X-Ray Diffraction

The phase behavior of a binary mixture of triacylglycerol (TAG), POP (1,3-dipalmitoyl-2-oleoyl-sn-glycerol), and OPO (1,3-dioleoyl-2-palmitoyl-sn-glycerol) in an organic solvent, n-dodecane, was examined by DSC and synchrotron radiation X-ray diffraction (SR-XRD). In our previous study on POP-OPO mixtures in neat liquid, the formation of molecular compound (MC) crystals of POP/OPO = 50/50 was observed (Minato et al. J. Am. Oil Chem. Soc. 1997, 74, 1213-1220). The purpose of the present study was to determine whether MC is formed in the POP-OPO mixture system in diluted solution when n-dodecane (C(12)) is added to the mixture as a solvent. Two solution systems having weight concentration ratios of POP and OPO to n-dodecane ((POP+OPO):C(12)) of 50:50 (50% solution) and 20:80 (20% solution) were prepared. We found that MC formed at a ratio of POP/OPO = 50/50 in both 50% solution and 20% solution in the stable and metastable states. Differences between the neat liquid and solution systems appeared in two results. In the first, the melting temperatures of MC crystals were lowered from 32.0 degrees C (neat liquid) to 20.4 degrees C (50% solution) and 18.0 degrees C (20% solution). In the second, the beta polymorph of the MC was always observed in the two solutions under the conditions examined in the present study, whereas alpha and beta polymorphs were observed in the neat liquid. These differences were caused by thermodynamic solvent effects. However, we conclude that aliphatic chain-chain interactions through palmitic and oleic acid moieties forming the MC of POP-OPO having a double chain length structure are not disturbed by solute-solvent interactions.

Topics: Alkanes; Calorimetry, Differential Scanning; Glycerol; Thermodynamics; Triglycerides; X-Ray Diffraction

The effects of 1,3-dioleoyl-2-palmitoyl glycerol (OPO) on lymph chylomicron transport, composition and size in rats were investigated in comparison with 1,2-dioleoyl-3-palmitoyl glycerol (OOP). The OPO and OOP were prepared by enzymatic transesterification reactions. The concentrations of OPO and OOP in the preparations were 65.7 g/100 g, and the composition of fatty acids was similar for each. The OPO preparation contained triacylglycerols with 76.6% of the palmitic acid in the sn-2 position, whereas 100% of the oleic acid was esterified to the sn-2 position in the OOP preparation. Rats were infused with lipid emulsion containing 150 g/L of OPO or OOP via a stomach catheter. Lymph was collected through the mesenteric lymphatic trunk at 1-h intervals for 12 h. Collected lymph chylomicrons were analyzed for triacylglycerol, fatty acids, apolipoprotein A-I and particle size. The maximum transport rates of triacylglycerols in the OPO group were higher than those in the OOP group. The overall absorption of triacylglycerols, palmitic acid and oleic acid in the OPO group was also higher than that in the OOP group. In the chylomicrons, 60-70% of the fatty acids at the sn-2 position of the infused triacylglycerol was transported at the original position. The transport rates of dioleoyl-palmitoyl glycerol in the OPO group were higher than those in the OOP group. The transport rates of apolipoprotein A-I did not differ between groups, whereas the mean diameter of the chylomicrons in the OPO group was larger than that in the OOP group. These results indicate that OPO is absorbed and transported more effectively than OOP.

Topics: Animals; Apolipoprotein A-I; Biological Transport; Chylomicrons; Fatty Acids; Lymph; Male; Oleic Acids; Palmitic Acids; Particle Size; Rats; Rats, Sprague-Dawley; Triglycerides