Lipase‐Catalyzed Synthesis of Medium‐Long‐Medium Type Structured Lipids Using Tricaprylin and Trilinolenin as Substrate Models

Abstract

The synthesis of medium‐long‐medium type structured lipids (SL) by the interesterification of tricaprylin (TC) and trilinolenin (TLN), using selected commercial lipases from Rhizomucor miehei (Lipozyme RM IM) and Candida antarctica (Novozym 435) was investigated. Although the bioconversion yield (BY) for Lipozyme RM IM (24.7 %) was close to that for Novozym 435 (24.0 %), the initial enzyme activity was 6.3 μmol CLnC/g enzyme/min and 1.6 μmol CLnC/g enzyme/min, respectively. Lipozyme RM IM was subsequently selected for further investigation. The structural analyses of SL indicated that the major products were 1,3‐dicapryl‐2‐linolenyl glycerol (CLnC) and 1(3)‐capryl‐2,3(1)‐dilinolenyl glycerol (CLnLn). In order to optimize the BY, selected parameters were investigated. The experimental results showed that using hexane as the reaction medium, at an initial water activity (aw) of 0.06, 10 mg solid enzyme/mL, substrate molar ratio of TC to TLN of 6:1 and a reaction time of 9 h, resulted in the highest BY (73.2 %). Using the optimized conditions, the effects of TLN concentration and other selective parameters, including the denaturation of the enzyme, controlling the aw and the addition of silica gel, on the mass productivity (PM), enzymatic productivity (PE) and volumetric productivity (PV) of the interesterification reaction, were also investigated.

Lipase-Catalyzed Interesterification for the Synthesis of Medium-Long-Medium (MLM) Structured Lipids

“…Caprylic acid-linoleic acid-caprylic acid, and caprylic acid-oleic acid-caprylic acid were also produced at amount ratios of 4.09–4.19 and 8.44–8.53%, respectively. As an example of esterification type three, Bai et al ( 59 ) reported the utilization of tricaprylin and trilinolenin as substrates, and either Lipozyme RM IM or Novozyme 435 as a catalyst. Caprylic acid-linolenic acid-caprylic acid and caprylic acid-linolenic acid-linolenic acid were reported to be the dominant products.…”

“…Moreover, palm kernel oil and coconut oil are reported as sources of MCFAs, containing higher amounts of lauric acid predominantly at sn -1,3 positions ( 40 ). Other potential substrates in MLM synthesis can be seen in Table 2 ( 39 , 43 , 56 - 59 ).…”

“…and free fatty acids are MCFA sources. Several combinations of substrates for MLM lipid synthesis have been reported such as tricaprylin and trilinolenin ( 59 ), triolein and caprylic acid ( 60 ), olive oil and caprylic acid ( 61 , 62 ), modified pine nut oil and capric acid ( 63 ), canola oil and caprylic acid ( 64 , 65 ), soybean oil and caprylic acid ( 7 , 66 - 68 ), and corn oil and caprylic acid ( 69 ).…”

Biotechnology in Future Food Lipids: Opportunities and Challenges

“…However, the usage of two single TAG molecules and an sn-1,3-specific lipase might be a good choice to solve this problem. Bai et al (2013) adopted tricaprylin and trilinolenin as substrates and Lipozyme RM IM or Novozym 435 as a catalyst. CyLnCy and CyLnLn (Ln, linolenic acid) were found to be the most dominant TAGs.…”

Recent Research Trends on the Enzymatic Synthesis of Structured Lipids

“…The reason is because they are generally produced through lipase‐catalyzed interesterification of plant oils (usually soybean, rapeseed, and cottonseed oils) with MCTs (such as coconut and palm kernel oil). In similar manners to the industrial production of MLCTs, several recent studies have attempted to produce non‐MLM‐type MLCTs via interesterification of LCTs with MCTs using sn ‐1,3‐specific or nonspecific lipases as the biocatalyst (Bai and others ; Khodadadi and others ; Perignon and others ; Yang and others ; Khodadadi and Kermasha ,b). Non‐MLM‐type MLCTs were also obtained through acidolysis of LCTs with MCFAs (Casas‐Godoy and others ) or direct esterification of glycerol with a mixture of LCFAs and MCFAs in the presence of a nonspecific lipase (Yang and others ) or acidolysis of LCTs with a mixture of LCFAs and MCFAs using an sn ‐1,3‐specific lipase as the biocatalyst (Kocak and others ).…”