Abstract
Tripalmitin-(PPP, 81.2%), 1,3-dipalmitoyl-2-oleoylglycerol-(POP, 64.4%), 1,2-dipalmitoyl-3-oleoylglycerol-(PPO, 86.5%), and 1,3-dioleoyl-2-palmitoylglycerol-(OPO, 50.2%)-rich lipids with different regiospecific positions of palmitic acid (P) were synthesized via acetone fractionation and lipase-catalyzed acidolysis, and their physicochemical and hydrolytic characteristics were compared. Triacylglycerols (TAGs) with higher content of P, wherein P was at the sn-1 (or 3) position, had higher melting points, crystallization temperatures, and packing densities of fat crystals compared to those with a lower content of P, and with P at the sn-2 position. The in vitro digestion degree calculated as released fatty acid (FA) (%) at 30, 60, and 120 min was in the following order: OPO-rich > PPO-rich > POP-rich lipids. At 120 min, in vitro digestion of the OPO-rich lipid released 92.6% of fatty acids, resulting in the highest digestibility, while 89.7% and 87.2% of fatty acids were released from the OPO-rich and PPO-rich lipids, respectively. Over the digestion period, the TAG and monoacylglycerol (MAG) contents decreased, while the diacylglycerol (DAG) content initially increased and then decreased, and the 1,2-DAG content exceeded the 1,3-DAG content. Therefore, the content and stereospecific position of P attached to a specific TAG affected the physicochemical and in vitro digestion characteristics of the lipids.
Highlights
Triacylglycerol (TAG) is a lipid class consisting of one glycerol molecule linked to three fatty acids (FAs) via ester bonds
The type and regiospecific position of FAs incorporated into glycerol molecules affect the physicochemical and digestion characteristics of TAGs, such as the TAG profile, solid fat content, polymorphism, crystal morphology, melting point, and melting and crystallization temperatures [1]
Acetone fractionation of palm stearin consisting of TAG (96.9 mmol%) and DAG (3.1 mmol%) at 28 ◦C produced PPP-rich lipid, which was in the solid phase and consisted entirely of TAG (100 mmol%), and POPrich lipid, which was in the liquid phase and consisted of 93.4 mmol% TAG, 6.3 mmol% DAG, and 0.3 mmol% MAG
Summary
Triacylglycerol (TAG) is a lipid class consisting of one glycerol molecule linked to three fatty acids (FAs) via ester bonds. Studies comparing the digestion characteristics of lipids containing TAGs with different types of FAs (such as P, O, or S) and the incorporated positions of the FAs are still limited. Four lipids were synthesized to assess the physicochemical and digestion characteristics of TAGs varying in the regiospecific position of palmitic acid. The physicochemical properties of the PPP-rich, POP-rich, PPO-rich, and OPO-rich lipids were compared by analyzing the compositions of acylglycerol, TAGs, and FAs; melting and crystallization properties; and crystal morphologies. The digestion characteristics of the POP-rich, PPO-rich, and OPO-rich lipids were assessed by measuring their FA hydrolysis rates using an in vitro multi-step digestion model and by analyzing the changes in the acylglycerol and TAG compositions of the hydrolyzed lipids over digestion time
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