Preparation and Characterization of 1,3-Dioleoyl-2-palmitoylglycerol

Abstract

1,3-Dioleoyl-2-palmitoylglycerol, an important triacylglycerol in infant formulas, was effectively enriched by a two-step process: (a) dry fractionation of leaf lard and (b) enzymatic acidolysis of the fractionated leaf lard. In step a, the 1,3-dioleoyl-2-palmitoylglycerol content was increased from 16.77 to 30.73% after programmed temperature treatment of the leaf lard at 60 °C for 20 min followed by 34 °C for 10 h. In step b, 43.72% of the 1,3-dioleoyl-2-palmitoylglycerol content was obtained at the optimal conditions of enzymatic acidolysis: a substrate molar ratio of 1:4 (the fractionated leaf lard/camellia oil fatty acids), 6% (w/w) of enzyme loading, and 6 h of reaction time at 45 °C. On the basis of gas chromatography determination and "deducting score" principle, a model was properly established for characterizing the quality of triacylglycerols enriched with 1,3-dioleoyl-2-palmitoylglycerol. This approach would be a valuable contribution in structured lipids industries because only gas chromatography determination was involved.

Production of Human Milk Fat Substitutes by Interesterification of Tripalmitin with Ethyl Oleate Catalyzed by Candida parapsilosis Lipase/Acyltransferase

“…Acidolysis reaction of tripalmitin or butterfat or lard (rich in palmitic acid at sn-2 position) with oleic acid or polyunsaturated fatty acids or interesterification of tripalmitin (or other oils containing palmitic acid at sn-2 position) with blends of oils, are the most used reactions, as presented in several reviews , 2019Ferreira-Dias and Tecelão, 2014;Şahín-Yeşilçubuk and Akoh, 2017). The synthesis of OPO, by multistep reactions, has also been reported (Chen et al, 2004;Qin et al, 2011;Schmid et al, 1999). However, due to the toxicity of methanol (Lotti et al, 2015), ethyl esters should be preferred over methyl esters as acyl donors for the production of food products.…”

“…In addition, ethyl esters, being more volatile than free fatty acids (FFA), are more easily recovered from the reaction media by distillation, which leads to more cost-effective downstream processing. The synthesis of OPO, by multistep reactions, has also been reported (Chen et al, 2004;Qin et al, 2011;Schmid et al, 1999). In most of these studies, expensive commercial immobilized sn-1,3 regioselective lipases have been used as catalysts.…”

Fatty acid specificity ofT1lipase and its potential in acylglycerol synthesis

“…. T1 lipase had a funnel‐like catalytic pocket (18 × 25 Å) with an area of 901.6 Å and a volume of 1110.4 Å (as calculated by CASTp) . The acyl binding pocket was lined by Thr‐168, Leu‐170, Met‐173, Val‐174, Thr‐177, Phe‐181, Leu‐183, Phe‐290, Val‐294, Ile‐319 and Val‐320.…”

“…Research in recent years has received much attention for using microbial lipases to produce n ‐3 polyunsaturated fatty acid concentrates, reduced‐calorie structured lipids, human milk fat substitutes, monoacylglycerols (MAGs) and diacylglycerols (DAGs) . Lipases have been increasingly used as biocatalysts for the production of those value‐added products by virtue of their high degree of specificity, mild reaction conditions and renewable nature.…”

Recent Research Trends on the Enzymatic Synthesis of Structured Lipids

“…Table lists 22 different examples of recently published studies to prepare HMFSs. Similar to the industrial manufacturing procedure of HMFSs, 10 studies have produced HMFSs through acidolysis of palmitic acid‐rich fats, such as tripalmitin, palm stearin, lard, and milk fats with oleic acid or free FAs obtained from oleic acid‐rich plant oils, such as olive, rapeseed, sunflower, hazelnut, and camellia oils, although most of the studies employed a batch‐type reaction system (Sorensen and others ; Tecelao and others ; Ilyasoglu and others ; Qin and others , ; Zou and others , ; Yuksel and Yesilcubuk ; Pande and others ; Zhang and others ). Intake of polyunsaturated FAs (PUFAs), including arachidonic acid (20:4 n ‐6), EPA (20:5 n ‐3), and DHA (22:6 n ‐3), plays a crucial role in proper growth and development of infants.…”