Abstract
This study reports the properties of immobilized MAS1-H108A lipase from marine Streptomyces sp. strain W007 on XAD1180 resin and its application in the synthesis of n-3 polyunsaturated fatty acids (PUFA)-rich triacylglycerols (TAG) for the first time. It was found that the optimal temperature and pH for both immobilized MAS1-H108A lipase and free lipase MAS1-H108A were 70 °C and 7.0, respectively. However, immobilized MAS1-H108A lipase exhibited higher thermostability when compared with free lipase MAS1-H108A. It was also interesting that both immobilized MAS1-H108A lipase and free lipase MAS1-H108A showed no regiospecificity in the hydrolysis of triolein. Subsequently, immobilized MAS1-H108A lipase and free lipase MAS1-H108A were employed to catalyze glycerolysis of n-3 PUFA-rich ethyl esters (EE) and esterification of n-3 PUFA with glycerol under vacuum in the solvent-free system. The results showed that n-3 PUFA-rich TAG were synthesized efficiently by non-regiospecific immobilized MAS1-H108A lipase and TAG contents separately reached 92.07% and 76.13% during the esterification and glycerolysis reactions, which were significantly higher than those (71.82% and 39.62%, respectively) obtained by free lipase MAS1-H108A. Besides, TAG exhibited similar n-3 PUFA composition to the substrate. These findings indicated that non-regiospecific immobilized MAS1-H108A lipase is a promising and efficient biocatalyst for the industrial synthesis of n-3 PUFA-rich TAG.
Similar content being viewed by others
References
Cleland LG, Caughey GE, James MJ, Proudman SM (2006) Reduction of cardiovascular risk factors with long term fish oil treatment in early rheumatoid arthritis. J Rheumatol 33:1973–1979
Corsetto PA, Montorfano G, Zava S, Jovenitti IE, Cremona A, Berra B, Rizzo AM (2011) Effects of n-3 PUFAs on breast cancer cells through their incorporation in plasma membranes. Lipids Health Dis 12:10–73
Giudetti AM, Cagnazzo R (2012) Beneficial effects of n-3 PUFA on Chronic airway inflammatory diseases. Prostag Oth Lipid M 99:57–67
Lawson LD, Hughes BG (1988) Human absorption of fish oil fatty acids as triacylglycerols, free acids, or ethyl esters. Biochem Bioph Res Co 152:328–335
Valenzuela A, Valenzuela V, Sanhueza J, Nieto S (2005) Effect of supplementation with docosahexaenoic acid ethyl ester and sn-2 docosahexaenyl monoacylglyceride on plasma and erythrocyte fatty acids in rats. Ann Nutr Metab 49:49–53
Nestel PJ (2000) Fish oil and cardiovascular disease: lipids and arterial function. Am J Clin Nutr 71:228S-231S
Ghasemi Fard S, Wang F, Sinclair AJ, Elliott G, Turchini GM (2019) How does high DHA fish oil affect health? A systematic review of evidence. Crit Rev Food Sci 59:1684–1727
Ellulu MS, Khaza’aiAbedRahmatIsmailRanneh HYAPY (2015) Role of fish oil in human health and possible mechanism to reduce the inflammation. Inflammopharmacology 23:79–89
Saraswathi V, Gao L, Morrow JD, Chait A, Niswender KD, Hasty AH (2007) Fish oil increases cholesterol storage in white adipose tissue with concomitant decreases in inflammation, hepatic steatosis, and atherosclerosis in mice. J Nutr 137:1776–1782
Kosugi Y, Azuma N (1994) Synthesis of triacylglycerol from polyunsaturated fatty acid by immobilized lipase. J Am Oil Chem Soc 71:1397–1403
Picq M, Bernoud-Hubac N, Lagarde M (2013) Synthesis and biological interest of structured docosahexaenoic acid-containing triacylglycerols and phospholipids. Curr Org Chem 17:841–847
Moreno-Pérez S, Luna P, Señorans FJ, Guisán JM, Fernandez-Lorente G (2015) Enzymatic synthesis of triacylglycerols of docosahexaenoic acid: transesterification of its ethyl esters with glycerol. Food Chem 187:225–229
Li DM, Wang WF, Li XH, Durrani R, Yang B, Wang YH (2017) Preparation of highly pure n-3 PUFA-enriched triacylglycerols by two-step enzymatic reactions combined with molecular Distillation. J Am Oil Chem Soc 94:225–233
Wang WF, Li T, Ning ZX, Wang YH, Yang B, Ma YJ, Yang XQ (2012) A process for the synthesis of PUFA-enriched triglycerides from high-acid crude fish oil. J Food Eng 109:366–371
Lin TJ, Chen SW, Chang AC (2006) Enrichment of n-3 PUFA contents on triglycerides of fish oil by lipase-catalyzed trans-esterification under supercritical conditions. Biochem Eng J 29:27–34
Liu SC, Zhang CH, Hong PZ, Ji HW (2007) Lipase-catalysed acylglycerol synthesis of glycerol and n-3 PUFA from tuna oil: optimisation of process parameters. Food Chem 103:1009–1015
Sun ZM, Xue CH, Guo ZX, Cong HH, Wang YM, Xue Y, Wang JF (2015) Preparation of triacylglycerols enriched in DHA from single cell glycerides via molecular distillation and enzymatic glycerolysis. J Aquat Food Prod T 24:796–806
Li DM, Wang WF, Liu PZ, Xu L, Faiza M, Yang B, Wang YH (2017) Immobilization of candida antarctica lipase B onto ECR1030 resin and its application in the synthesis of n-3 PUFA-rich triacylglycerols. Eur J Lipid Sci Tech 119:1700266
Li DM, Wang WF, Qin XL, Li XX, Yang B, Wang YH (2016) A novel process for the synthesis of highly pure n-3 polyunsaturated fatty acid (PUFA)-enriched triglycerides by combined transesterification and ethanolysis. J Agri Food Chem 64:6533–6538
Bispo P, Batista I, Bernardino RJ, Bandarra NM (2014) Preparation of triacylglycerols rich in omega-3 fatty acids from sardine oil using a Rhizomucor miehei lipase: focus in the EPA/DHA ratio. Appl Biochem Biotech 172:1866–1881
Yuan DJ, Lan DM, Xin RP, Yang B, Wang YH (2015) Screening and characterization of a thermostable lipase from marine Streptomyces sp. Strain W007. Biotechnol Appl Bioc 63:41–50
Zhao ZX, Hou SL, Lan DM, Wang XM, Liu JS, Khan FI, Wang YH (2017) Crystal structure of a lipase from Streptomyces sp. strain W007–implications for thermostability and regiospecificity. FEBS J 284:3506–3519
Zhao G, Wang JR, Tang QY, Lan DM, Wang YH (2018) Improving the catalytic activity and thermostability of MAS1 lipase by alanine substitution. Mol Biotechnol 60:319–328
Li DM, Wang WF, Zhang L, Liu N, Faiza M, Tan CP, Yang B, Lan DM, Wang YH (2018) Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process. Eur J Lipid Sci Tech 120:1700529
Lian WS, Li DM, Zhang L, Wang WF, Faiza M, Tan CP, Yang B, Lan DM, Wang YH (2018) Synthesis of conjugated linoleic acid-rich triacylglycerols by immobilized mutant lipase with excellent capability and recyclability. Enzyme Microb Tech 117:56–63
Dong Z, Jiang MY, Shi J, Zheng MM, Huang FH (2019) Preparation of immobilized lipase based on hollow mesoporous silica spheres and its application in ester synthesis. Molecules 24:395
Xing X, Jia JQ, Zhang JF, Zhou ZW, Li J, Wang N, Yu XQ (2019) CALB immobilized onto magnetic nanoparticles for efficient kinetic resolution of racemic secondary alcohols: long-term stability and reusability. Molecules 24:490
Yang B, Wang YH, Yang JG (2006) Optimization of enzymatic degumming process for rapeseed oil. J Am Oil Chem Soc 83:653–658
Basso A, Froment L, Hesseler M, Serban S (2013) New highly robust divinyl benzene/acrylate polymer for immobilization of lipase CALB. Eur J Lipid Sci Technol 115:468–472
Wang WF, Xu Y, Qin XL, Lan DM, Yang B, Wang YH (2014) Immobilization of lipase SMG1 and its application in synthesis partical glycerides. Eur J Lipid Sci Technol 116:1063–1069
Wang XM, Li DM, Qu M, Durrani R, Yang B, Wang YH (2017) Immobilized MAS1 lipase showed high esterification activity in the production of triacylglycerols with n-3 polyunsaturated fatty acids. Food Chem 216:260–267
Senanayake SPJ, Shahidi F (1999) Enzymatic incorporation of docosahexaenoic acid into borage oil. J Am Oil Chem Soc 76:1009–1015
Qin XL, Huang HH, Lan DM, Wang YH, Yang B (2014) Typoselectivity of crude Geobacillus sp. T1 lipase fused with a cellulose-binding domain and its use in the synthesis of structured lipids. J Am Oil Chem Soc 91:55–62
Wang YH, Mai QY, Qin XL, Yang B, Wang ZL, Chen HT (2010) Establishment of an evaluation model for human milk fat substitutes. J Agric Food Chem 58:642–649
Qin XL, Wang YM, Wang YH, Huang HH, Yang B (2011) Preparation and characterization of 1,3-dioleoyl-2-palmitoylglycerol. J Agric Food Chem 59:5714–5719
Li DM, Qin XL, Wang JR, Yang B, Wang WF, Huang WL, Wang YH (2015) Hydrolysis of soybean oil to produce diacylglycerol by a lipase from Rhizopus oryzae. J Mol Catal B-Enzym 115:43–50
Liu N, Li DM, Wang WF, Hollmann F, Xu L, Ma YJ, Yang B, Bai WD, Sun XT, Wang YH (2018) Production and immobilization of lipase PCL and its application in synthesis of α-linolenic acid-rich diacylglycerol. J Food Biochem 42:e12574
Li XX, Li DM, Wang WF, Durrani R, Yang B, Wang YH (2016) Immobilization of SMG1-F278N lipase onto a novel epoxy resin: Characterization and its application in synthesis of partial glycerides. J Mol Catal B Enzym 133:154–160
Acknowledgements
This work was supported by the National Key R & D Program of China (2018YFC0311104), National Natural Science Foundation of China (31801462), National Science Fund for Distinguished Young Scholars (31725022), Guangdong MEPP Fund (NO.GDOE[2019]A20), Education and Research Project of Young and Middle-aged Teachers of Fujian Province (JT180467), the Cultivation Program for the Outstanding Young Scientific Research Talents of Fujian Province University (2018), Science and Technology Department of Putian (2018NP2003), Natural Science Foundation of Fujian Province (2020J05211, 2018J05063), Science and Technology Planning project of Putian University (2018055).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Wang, X., Zhao, X., Qin, X. et al. Properties of immobilized MAS1-H108A lipase and its application in the efficient synthesis of n-3 PUFA-rich triacylglycerols. Bioprocess Biosyst Eng 44, 575–584 (2021). https://doi.org/10.1007/s00449-020-02470-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00449-020-02470-x