食品与发酵工业 >

2024 , Vol. 50 >Issue 11: 195 - 200

DOI: https://doi.org/10.13995/j.cnki.11-1802/ts.035372

研究报告

鱼粉压榨液中二十碳五烯酸和二十二碳六烯酸的富集及其甘油酯化

  • 王竞 ,
  • 毕云华 ,
  • 黄佳婷 ,
  • 孟柯 ,
  • 曹少谦 ,
  • 戚向阳
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  • (浙江万里学院 生物与环境学院,浙江 宁波,315100)
第一作者:硕士研究生(曹少谦副教授和戚向阳教授为共同通信作者,E-mail:shaoqiancao@sina.com;qixiangyang85@sina.com)

收稿日期: 2023-03-07

  修回日期: 2023-04-19

  网络出版日期: 2024-07-12

基金资助

宁波市公益性研究计划项目(202002N3073)

收起

Enrichment and glyceride synthesis of eicosapentaenoic acid and docosahexaenoic from pressed liquor of fish meal processing

  • WANG Jing ,
  • BI Yunhua ,
  • HUANG Jiating ,
  • MENG Ke ,
  • CAO Shaoqian ,
  • QI Xiangyang
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  • (College of Biological and Environmental Sciences, Zhejiang Wanli University, Ningbo 315100, China)

Received date: 2023-03-07

  Revised date: 2023-04-19

  Online published: 2024-07-12

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摘要

该文从鱼粉压榨液中富集二十碳五烯酸(eicosapentaenoic acid,EPA)和二十二碳六烯酸(docosahexaenoic acid,DHA),进而采用固定化酶CALB-A两步法催化合成甘油酯型鱼油。结果表明,经一级分子蒸馏富集的乙酯型鱼油中EPA+DHA含量为43.2%,回收率为87.04%;以固定化酶CALB-A催化该乙酯型鱼油和甘油反应合成甘油酯型鱼油,优化后的条件为,以甘油/乙酯物质的量比1∶4、2%加酶量(以底物总质量计)、底物浓度20%(质量分数)、反应温度50 ℃的条件在叔丁醇溶剂中反应6 h,回收的油相以3%加酶量(以底物总质量计)、反应温度50 ℃、真空条件下反应24 h,乙酯的转化率可以达到68.27%,甘油三酯(triacylglycerol,TAG)产率为62.51%;脂肪酸分析表明得到TAG中脂肪酸组成与原料一致。

关键词： 鱼粉压榨液; 分子蒸馏; 固定化酶; 甘油三酯

本文引用格式

王竞 , 毕云华 , 黄佳婷 , 孟柯 , 曹少谦 , 戚向阳 . 鱼粉压榨液中二十碳五烯酸和二十二碳六烯酸的富集及其甘油酯化[J]. 食品与发酵工业, 2024 , 50(11) : 195 -200 . DOI: 10.13995/j.cnki.11-1802/ts.035372

Abstract

Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) were enriched from pressed liquor of fish meal processing, and then glyceride was synthesized by immobilized enzyme CALB-A in two steps.Results showed that the total content of EPA and DHA in ethyl ester fish oil enriched by first-order molecular distillation was 43.2%, and the recovery rate was 87.04%.The esterification of ethyl ester fish oil with glycerol was catalyzed by the immobilized enzyme CALB-A to synthesize the glyceride of fish oil.The optimum conditions were that the molar ratio of glycerol to ethyl ester was 1∶4, the reaction was carried out in tert-butanol solvent at 50 ℃ for 6 h with a substrate concentration of 20% and enzyme addition of 2%, and then the recovered oil phase was reacted subsequently at 50 ℃ for 24 h under vacuum with enzyme addition of 3%.The conversion rate of ethyl ester and the yield of triglyceride (TAG) were 68.27% and 62.51%, respectively.The analysis of fatty acids showed that the fatty acid composition in TAG was consistent with that of raw materials.

Key words： pressed liquor of fish meal processing; molecular distillation; immobilized enzyme; triglyceride

参考文献

[1] 李强, 肖井坤, 孙家峰.电解法处理鱼粉废水[J].大连海事大学学报, 2007, 33(1):146-149.
LI Q, XIAO J K, SUN J F.Study on treatment of fish meal wastewater by electrolysis[J].Journal of Dalian Maritime University, 2007, 33(1):146-149.
[2] GARCIA-SIFUENTES C, PACHECO-AGUILAR R, LUGO-SÁNCHEZ M, et al.Properties of recovered solids from stick-water treated by centrifugation and pH shift[J].Food Chemistry, 2009, 114(1):197-203.
[3] 王亚男, 徐茂琴, 季晓敏, 等.分子蒸馏富集金枪鱼鱼油ω-3脂肪酸的研究[J].中国食品学报, 2014, 14(7):52-58.
WANG Y N, XU M Q, JI X M, et al.Study on ω-3 fatty acids enrichment of tuna oil with molecular distillation[J].Journal of Chinese Institute of Food Science and Technology, 2014, 14(7):52-58.
[4] HAO L P, CAO X J, HUR B K.Separation of single component of EPA and DHA from fish oil using silver ion modified molecular sieve 13X under supercritical condition[J].Journal of Industrial and Engineering Chemistry, 2008, 14(5):639-643.
[5] 刘书成, 李德涛, 欧冠强, 等.尿素包合法富集蛇鲻鱼油中EPA和DHA的研究[J].广东海洋大学学报, 2008, 28(3):61-65.
LIU S C, LI D T, OU G Q, et al.Concentration of DHA and EPA from fish oil of Saurida elongate by urea complexation[J].Journal of Guangdong Ocean University, 2008, 28(3):61-65.
[6] MEDINA A R, GIMÉNEZ A G, CAMACHO F G, et al.Concentration and purification of stearidonic, eicosapentaenoic, and docosahexaenoic acids from cod liver oil and the marine microalga Isochrysis galbana[J].Journal of the American Oil Chemists’ Society, 1995, 72(5):575-583.
[7] 刘汝萃, 王彩华, 肖晶, 等.鱼油的提取、富集与应用研究进展[J].粮食与食品工业, 2017, 24(5):5-8.
LIU R C, WANG C H, XIAO J, et al.Study on the extraction, enrichment and application of fish oil[J].Cereal & Food Industry, 2017, 24(5):5-8.
[8] LAWSON L D, HUGHES B G.Human absorption of fish oil fatty acids as triacylglycerols, free acids, or ethyl esters[J].Biochemical and Biophysical Research Communications, 1988, 152(1):328-335.
[9] 邵佩霞. 富含多不饱和脂肪酸甘油酯的酶法制备[D].广州:华南理工大学, 2010.
SHAO P X.Enzymatic preparation of glycerides rich in polyunsaturated fatty acids[D].Guangzhou:South China University of Technology, 2010.
[10] IKEDA I, SASAKI E, YASUNAMI H, et al.Digestion and lymphatic transport of eicosapentaenoic and docosahexaenoic acids given in the form of triacylglycerol, free acid and ethyl ester in rats[J].Biochimica et Biophysica Acta, 1995, 1259(3):297-304.
[11] 王琳琳, 高兴明, 韦海涛, 等.固定化酶在食品工业中的应用研究进展[J].轻工学报, 2021, 36(2):25-33.
WANG L L, GAO X M, WEI H T, et al.Research progress in the application of immobilized enzymes in food industry[J].Journal of Light Industry, 2021, 36(2):25-33.
[12] 李彦锋, 李军荣, 伏莲娣.固定化酶的制备及应用[J].高分子通报, 2001(2):13-17;23.
LI Y F, LI J R, FU L D.Preparation and application of immobilized enzymes[J].Polymer Bulletin, 2001(2):13-17;23.
[13] ZHAO X B, QI F, YUAN C L, et al.Lipase-catalyzed process for biodiesel production:Enzyme immobilization, process simulation and optimization[J].Renewable and Sustainable Energy Reviews, 2015, 44:182-197.
[14] 路雪纯, 辛嘉英, 张帅, 等.脂肪酶固定化及其在食品领域中应用的研究进展[J].食品工业科技, 2021, 42(17):423-431.
LU X C, XIN J Y, ZHANG S, et al.Research progress of lipase immobilization and its application in food field[J].Science and Technology of Food Industry, 2021, 42(17):423-431.
[15] WANG J, ZHU L L, WANG J Z, et al.Enzymatic Synthesis of Functional Structured Lipids from Glycerol and Naturally Phenolic Antioxidants[M]//Glycerine Production and Transformation - An Innovative Platform for Sustainable Biorefinery and Energy.IntechOpen, 2019.
[16] ISHIKAWA T, MINEGISHI H, SHIMANE Y.Production and characterization of halophilic esterase and lipase from halophilic microorganisms[J].Studia Universitatis Babes-Bolyai, Biologia, 2019, 64(1):124.
[17] 朱东奇, 李道明, 王卫飞, 等.酶法全酯化合成富含EPA/DHA甘油酯工艺研究[J].中国粮油学报, 2017, 32(8):63-70.
ZHU D Q, LI D M, WANG W F, et al.Technical study of EPA/DHA-enriched glycerides by enzymatic holoesterification process[J].Journal of the Chinese Cereals and Oils Association, 2017, 32(8):63-70.
[18] SOLAESA Á G, SANZ M T, MELGOSA R, et al.Substrates emulsification process to improve lipase-catalyzed sardine oil glycerolysis in different systems.Evaluation of lipid oxidation of the reaction products[J].Food Research International, 2017, 100(Pt 1):572-578.
[19] 王升帆, 王庭, 郗锋剑, 等.固定化脂肪酶催化制备甘油三酯型鱼油[J].中国油脂, 2021, 46(8):97-100;109.
WANG S F, WANG T, XI F J, et al.Preparation of triglyceride fish oil catalyzed by immobilized lipase[J].China Oils and Fats, 2021, 46(8):97-100;109.
[20] 马良, 张延秀, 范书琴, 等.酶法制备高含量多不饱和脂肪酸甘油三酯的工艺[J].食品工业, 2022, 43(6):43-45.
MA L, ZHANG Y X, FAN S Q, et al.The preparation of high-content polyunsaturated fatty acid triglyceride by enzymatic method[J].The Food Industry, 2022, 43(6):43-45.
[21] 李冲冲, 李子豪, 柳余莉, 等.鱼粉加工副产物中鱼油的精炼及其脂肪酸组成分析[J].食品科学, 2015, 36(20):190-193.
LI C C, LI Z H, LIU Y L, et al.Refinement of fish oil from byproducts of fish meal processing and its fatty acid composition analysis[J].Food Science, 2015, 36(20):190-193.
[22] 张蒙娜, 宋恭帅, 彭茜, 等.响应面法优化精制沙丁鱼油乙酯化工艺[J].食品工业科技, 2018, 39(20):122-127.
ZHANG M N, SONG G S, PENG X, et al.Optimization of ethyl esterification process of refined sardine oil by response surface methodology[J].Science and Technology of Food Industry, 2018, 39(20):122-127.
[23] XU Y, GUO S H, WANG W F, et al.Enzymatic hydrolysis of palm stearin to produce diacylglycerol with a highly thermostable lipase[J].European Journal of Lipid Science and Technology, 2013, 115(5):564-570.
[24] 刘向前, 李道明, 王卫飞, 等.Lipozyme CALB L固定化及催化合成EPA/DHA甘油酯的研究[J].中国油脂, 2016, 41(11):21-26.
LIU X Q, LI D M, WANG W F, et al.Immobilization of Lipozyme CALB L and its application in synthesis of EPA/DHA-enriched glycerides[J].China Oils and Fats, 2016, 41(11):21-26.
[25] 王卫飞, 马永钧, 范海星, 等.酶法合成富含DHA、EPA甘油三酯的研究[J].中国油脂, 2011, 36(2):5-8.
WANG W F, MA Y J, FAN H X, et al.Enzymatic production of DHA and EPA-enriched triacylglycerols[J].China Oils and Fats, 2011, 36(2):5-8.
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