Production of MLM Type Structured Lipids From Grapeseed Oil Catalyzed by Non‐Commercial Lipases

Abstract

Low calorie triacylglycerols (TAG) presenting medium-chain fatty acids (M) at positions sn-1,3 and long-chain fatty acids (L) at position sn-2 are known as MLM. This study aims at the production of MLM by acidolysis of grapeseed oil with medium-chain caprylic (C8:0) or capric (C10:0) acids. Grapeseed oil is used as source of long-chain polyunsaturated fatty acids (FAs), especially linoleic acid, at sn-2 position in TAG. Reactions are performed in batch, in solvent-free systems, during 48 h. Novel non-commercial sn-1,3 regioselective lipases are used as alternative to high-cost commercial biocatalysts, namely, the heterologous lipase from Rhizopus oryzae (rROL) immobilized in Amberlite TM IRA 96 and Carica papaya lipase (CPL)self-immobilized in papaya latex. The highest productions of new TAG are achieved at 40 C, molar ratio TAG:M of 1:2, after 48 h, with both biocatalysts, with yields varying between 38 and 69%. rROL immobilized in Amberlite IRA 96 shows a preference toward caprylic acid while CPL shows no preference toward caprylic or capric acid. First-order deactivation kinetics is observed for both biocatalysts. Halflives at 40 C are 166 and 118 h for rROL and 96 and 81 h for CPL, in the acidolysis of grapeseed oil with C8:0 or C10:0, respectively. Practical Applications: Grapeseeds of Vitis vinifera L. are a by-product of the wine industry. Using grapeseed oil to produce added-value functional oils rich in linoleic acid (essential fatty acid) may be a way of improving the revenues of the enological and oil sectors. Both lipases, and mainly Carica papaya lipase self-immobilized in papaya latex, due to its low-cost production and easy preparation, are promising non-commercial biocatalysts for the synthesis of MLM in solvent-free media. The use of a solvent-free system, in addition of being a green option, is also preferred for economic reasons, avoiding the costs with solvent and solvent recovery.

Enzymatic modification of grapeseed (Vitis vinifera L.) oil aiming to obtain dietary triacylglycerols in a batch reactor

“…With Lipozyme TL IM ® and Novozym 435 ® , the results of the present study are close to those described by Nunes et al (2011): 28.8 mol% and 30.4 mol% of incorporation, respectively. The acidolysis of grapeseed oil with caprylic or capric acid was also performed in solvent-free media, using non-commercial sn-1,3 regioselective lipases namely: the recombinant lipase from Rhizopus oryzae immobilized in Amberlite™ IRA 96 and Carica papaya lipase self-immobilized in papaya latex (Costa et al, 2018). Yields of new TAGs were between 38 and 69 mol%, after 48 h acidolysis at 40°C, molar ratio fatty acid:oil of 2:1.…”

“…The specificity of this lipase is directly related to the size of the fatty acid chain, and the enzyme has a preference for fatty acids with longer carbon chain (Rodrigues & Fernandez-Lafuente, 2010a;Rodrigues & Fernandez-Lafuente, 2010b;Caballero et al, 2014). On the contrary, the recombinant lipase of Rhizopus oryzae immobilized in Amberlite IRA 96 showed a preference towards caprylic acid while Carica papaya lipase self-immobilized in papaya latex showed no preference towards caprylic or capric acid (Costa et al, 2018).…”

“…In addition, it has a high amount of antioxidant compounds, such as tocopherols (vitamin E) and tocotrienols (Raeisi, Tajik, Aliakbarlu, Mirhosseini, & Hosseini, 2015). The use of grapeseed oil for producing MLM-type TAGs by acidolysis with caprylic or capric acids, in solvent-free media, catalyzed by non-commercial sn-1,3 regioselective recombinant Rhizopus oryzae lipase and Carica papaya lipase self-immobilized in papaya latex was recently reported (Costa et al, 2018).…”

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

“…Khodadadi et al ( 43 ) also reported that Lipozyme TL IM and Novozyme 435 were more effective in transesterification reaction between flaxseed oil and tricaprylin than Lipozyme RM IM and Amano DF. Table 1 ( 44 , 48 - 53 ) summarizes the utilization of immobilized lipase for MLM lipase synthesis.…”

Extraction and Characterization of Coffee Silverskin Oil and Its Valorization by Enzymatic Hydrolysis

“…Coffee is one of the most consumed beverages in the world and global consumption of 161 million of 60 kg coffee bags per year. So, there is a production of coffee byproducts such as coffee silverskin (CS) [1][2][3]. The CS is the thin tegument that covers the two coffee seeds and it is the only byproduct generated during green bean roasting and represents about 4.2 % (w/w) of coffee beans.…”