Selective synthesis of human milk fat-style structured triglycerides from microalgal oil in a microfluidic reactor packed with immobilized lipase

Wang, Jun; Liu, Xi; Wang, Xu -Dong; Dong, Tao; Zhao, Xing -Yu; Zhu, Dan; Mei, Yi -Yuan; Wu, Guo -Hua

doi:10.1016/j.biortech.2016.08.023

Title: Selective synthesis of human milk fat-style structured triglycerides from microalgal oil in a microfluidic reactor packed with immobilized lipase

Journal Article · Thu Aug 18 00:00:00 EDT 2016 · Bioresource Technology

DOI: https://doi.org/10.1016/j.biortech.2016.08.023 · OSTI ID:1326324

Wang, Jun ^[1]; Liu, Xi ^[2]; Wang, Xu -Dong ^[2]; Dong, Tao ^[3]; Zhao, Xing -Yu ^[2]; Zhu, Dan ^[2]; Mei, Yi -Yuan ^[2]; Wu, Guo -Hua ^[1]

Jiangsu Univ. of Science and Technology, Zhenjiang (People's Republic of China); Chinese Academy of Agricultural Sciences, Zhenjiang (People's Republic of China)
Jiangsu Univ. of Science and Technology, Zhenjiang (People's Republic of China)
National Renewable Energy Lab. (NREL), Golden, CO (United States)

Human milk fat-style structured triacylglycerols were produced from microalgal oil in a continuous microfluidic reactor packed with immobilized lipase for the first time. A remarkably high conversion efficiency was demonstrated in the microreactor with reaction time being reduced by 8 times, Michaelis constant decreased 10 times, the lipase reuse times increased 2.25-fold compared to those in a batch reactor. In addition, the content of palmitic acid at sn-2 position (89.0%) and polyunsaturated fatty acids at sn-1, 3 positions (81.3%) are slightly improved compared to the product in a batch reactor. The increase of melting points (1.7 °C) and decrease of crystallizing point (3 °C) implied higher quality product was produced using the microfluidic technology. The main cost can be reduced from 212.3 to 14.6 per batch with the microreactor. Altogether, the microfluidic bioconversion technology is promising for modified functional lipids production allowing for cost-effective approach to produce high-value microalgal coproducts.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: NREL (National Renewable Energy Laboratory (NREL), Golden, CO (United States))

Sponsoring Organization:: Jiangsu Province; Jiangsu University of Science and Technology; Modern Agro-industry Technology Research System of China; USDOE

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1326324

Report Number(s):: NREL/JA-5100--67110

Journal Information:: Bioresource Technology, Journal Name: Bioresource Technology Journal Issue: C Vol. 220; ISSN 0960-8524

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (33)

A Three-Minute Synthesis and Purification of Ibuprofen: Pushing the Limits of Continuous-Flow Processing Snead, David R.; Jamison, Timothy F. Angewandte Chemie International Edition, Vol. 54, Issue 3 https://doi.org/10.1002/anie.201409093	journal	December 2014
Structured lipids enriched with unsaturated fatty acids produced by enzymatic acidolysis of silkworm pupae oil using oleic acid: Enzymatic synthesis of structured lipid Zhao, Xing-Yu; Wang, Xu-Dong; Liu, Xi European Journal of Lipid Science and Technology, Vol. 117, Issue 6 https://doi.org/10.1002/ejlt.201400438	journal	January 2015
Determination of Adsorption and Kinetic Parameters for Methyl tert-Butyl Ether Synthesis from tert-Butyl Alcohol and Methanol Ziyang, Zhang; Hidajat, K.; Ray, Ajay K. Journal of Catalysis, Vol. 200, Issue 2 https://doi.org/10.1006/jcat.2001.3180	journal	June 2001
Effect of Processing and Storage Parameters on the Oxidative Deterioration of Oil-in-Water Emulsions Dimakou, Charikleia P.; Kiokias, Sotirios N.; Tsaprouni, Ioanna V. Food Biophysics, Vol. 2, Issue 1 https://doi.org/10.1007/s11483-007-9027-6	journal	February 2007
Bioreactors with immobilized lipases: State of the art Balcão, Victor M.; Paiva, Ana L.; Xavier Malcata, F. Enzyme and Microbial Technology, Vol. 18, Issue 6 https://doi.org/10.1016/0141-0229(95)00125-5	journal	May 1996
Effect of low frequency ultrasound on microalgae solvent extraction: Analysis of products, energy consumption and emissions Ferreira, Ana F.; Dias, Ana Paula Soares; Silva, Carla M. Algal Research, Vol. 14 https://doi.org/10.1016/j.algal.2015.12.015	journal	March 2016
Synthesis of biodiesel from a model waste oil feedstock using a carbon-based solid acid catalyst: Reaction and separation Shu, Qing; Nawaz, Zeeshan; Gao, Jixian Bioresource Technology, Vol. 101, Issue 14 https://doi.org/10.1016/j.biortech.2010.02.050	journal	July 2010
Two-step in situ biodiesel production from microalgae with high free fatty acid content Dong, Tao; Wang, Jun; Miao, Chao Bioresource Technology, Vol. 136 https://doi.org/10.1016/j.biortech.2013.02.105	journal	May 2013
A novel continuous flow biosynthesis of caffeic acid phenethyl ester from alkyl caffeate and phenethanol in a packed bed microreactor Wang, Jun; Gu, Shuang-Shuang; Cui, Hong-Sheng Bioresource Technology, Vol. 158 https://doi.org/10.1016/j.biortech.2014.01.145	journal	April 2014
From microalgae oil to produce novel structured triacylglycerols enriched with unsaturated fatty acids Wang, Jun; Wang, Xu-Dong; Zhao, Xing-Yu Bioresource Technology, Vol. 184 https://doi.org/10.1016/j.biortech.2014.09.133	journal	May 2015
Microalgal lipids biochemistry and biotechnological perspectives Bellou, Stamatia; Baeshen, Mohammed N.; Elazzazy, Ahmed M. Biotechnology Advances, Vol. 32, Issue 8 https://doi.org/10.1016/j.biotechadv.2014.10.003	journal	December 2014
Kinetic study of catalytic esterification of butyric acid and n-butanol over Dowex 50Wx8-400 Ju, In Bum; Lim, Hye-Won; Jeon, Wonjin Chemical Engineering Journal, Vol. 168, Issue 1 https://doi.org/10.1016/j.cej.2010.12.086	journal	March 2011
Study of the microwave lipid extraction from microalgae for biodiesel production Dai, Yong-Ming; Chen, Kung-Tung; Chen, Chiing-Chang Chemical Engineering Journal, Vol. 250 https://doi.org/10.1016/j.cej.2014.04.031	journal	August 2014
Kinetic study of catalytic esterification of acrylic acid with butanol catalyzed by different ion exchange resins Sert, Emine; Buluklu, Aslı Deniz; Karakuş, Simge Chemical Engineering and Processing: Process Intensification, Vol. 73 https://doi.org/10.1016/j.cep.2013.06.004	journal	November 2013
Synthesis of 2-monoacylglycerols and structured triacylglycerols rich in polyunsaturated fatty acids by enzyme catalyzed reactions Rodríguez, Alicia; Esteban, Luis; Martín, Lorena Enzyme and Microbial Technology, Vol. 51, Issue 3 https://doi.org/10.1016/j.enzmictec.2012.05.006	journal	August 2012
Immobilised enzyme microreactor for screening of multi-step bioconversions: Characterisation of a de novo transketolase-ω-transaminase pathway to synthesise chiral amino alcohols Matosevic, S.; Lye, G. J.; Baganz, F. Journal of Biotechnology, Vol. 155, Issue 3 https://doi.org/10.1016/j.jbiotec.2011.07.017	journal	September 2011
CO oxidation over CuO/Ce1−xCuxO2−δ and Ce1−xCuxO2−δ catalysts: Synergetic effects and kinetic study Jia, Ai-Ping; Hu, Geng-Shen; Meng, Lian Journal of Catalysis, Vol. 289 https://doi.org/10.1016/j.jcat.2012.02.010	journal	May 2012
Studies on the lipase induced degradation of lipid based drug delivery systems Schwab, Martin; Sax, Gerhard; Schulze, Sandra Journal of Controlled Release, Vol. 140, Issue 1 https://doi.org/10.1016/j.jconrel.2009.07.008	journal	November 2009
Lipase-catalysed incorporation of EPA into emu oil: Formation and characterisation of new structured lipids Akanbi, Taiwo O.; Barrow, Colin J. Journal of Functional Foods, Vol. 19 https://doi.org/10.1016/j.jff.2014.11.010	journal	December 2015
Optimized synthesis of 1,3-dioleoyl-2-palmitoylglycerol-rich triacylglycerol via interesterification catalyzed by a lipase from Thermomyces lanuginosus Lee, Jeung Hee; Son, Jeoung Mae; Akoh, Casimir C. New Biotechnology, Vol. 27, Issue 1 https://doi.org/10.1016/j.nbt.2009.10.006	journal	February 2010
Continuous steroid biotransformations in microchannel reactors Marques, Marco P. C.; Fernandes, Pedro; Cabral, Joaquim M. S. New Biotechnology, Vol. 29, Issue 2 https://doi.org/10.1016/j.nbt.2011.10.001	journal	January 2012
Production of structured triacylglycerols (STAG) rich in docosahexaenoic acid (DHA) in position 2 by acidolysis of tuna oil catalyzed by lipases Hita, Estrella; Robles, Alfonso; Camacho, Belén Process Biochemistry, Vol. 42, Issue 3 https://doi.org/10.1016/j.procbio.2006.09.023	journal	March 2007
Isoamyl acetate synthesis in imidazolium-based ionic liquids using packed bed enzyme microreactor Cvjetko, Marina; Vorkapić-Furač, Jasna; Žnidaršič-Plazl, Polona Process Biochemistry, Vol. 47, Issue 9 https://doi.org/10.1016/j.procbio.2012.04.028	journal	September 2012
A specific and potent inhibitor of glucosylceramide synthase for substrate inhibition therapy of Gaucher disease McEachern, Kerry Anne; Fung, John; Komarnitsky, Svetlana Molecular Genetics and Metabolism, Vol. 91, Issue 3 https://doi.org/10.1016/j.ymgme.2007.04.001	journal	July 2007
Stearidonic Acid Soybean Oil Enriched with Palmitic Acid at the sn -2 Position by Enzymatic Interesterification for Use as Human Milk Fat Analogues Teichert, Sarah A.; Akoh, Casimir C. Journal of Agricultural and Food Chemistry, Vol. 59, Issue 10 https://doi.org/10.1021/jf200336t	journal	May 2011
Modifications of Stearidonic Acid Soybean Oil by Enzymatic Acidolysis for the Production of Human Milk Fat Analogues Teichert, Sarah A.; Akoh, Casimir C. Journal of Agricultural and Food Chemistry, Vol. 59, Issue 24 https://doi.org/10.1021/jf203718w	journal	December 2011
Preparation of Human Milk Fat Substitutes from Palm Stearin with Arachidonic and Docosahexaenoic Acid: Combination of Enzymatic and Physical Methods Zou, Xiao-Qiang; Huang, Jian-Hua; Jin, Qing-Zhe Journal of Agricultural and Food Chemistry, Vol. 60, Issue 37 https://doi.org/10.1021/jf3017354	journal	September 2012
Lipozyme RM IM-Catalyzed Acidolysis of Cinnamomum camphora Seed Oil with Oleic Acid To Produce Human Milk Fat Substitutes Enriched in Medium-Chain Fatty Acids Zou, Xian-Guo; Hu, Jiang-Ning; Zhao, Man-Li Journal of Agricultural and Food Chemistry, Vol. 62, Issue 43 https://doi.org/10.1021/jf503691p	journal	October 2014
Continuous Fabrication of Biocatalyst Immobilized Microparticles Using Photopolymerization and Immiscible Liquids in Microfluidic Systems Jeong, Won Je; Kim, Jeong Yun; Choo, Jaebum Langmuir, Vol. 21, Issue 9 https://doi.org/10.1021/la050105l	journal	April 2005
APA-style human milk fat analogue from silkworm pupae oil: Enzymatic production and improving storage stability using alkyl caffeates Liu, Xi; Wang, Xudong; Pang, Na Scientific Reports, Vol. 5, Issue 1 https://doi.org/10.1038/srep17909	journal	December 2015
Selective esterification to produce microalgal biodiesel and enrich polyunsaturated fatty acid using zeolite as a catalyst Dong, Tao; Yu, Xiaochen; Miao, Chao RSC Advances, Vol. 5, Issue 103 https://doi.org/10.1039/C5RA17512G	journal	January 2015
The kinetics of carboxymethylcellulose–ficin in packed beds Lilly, Md; Hornby, We; Crook, Em Biochemical Journal, Vol. 100, Issue 3 https://doi.org/10.1042/bj1000718	journal	September 1966
Preliminary Study on Acyl Incorporation and Migration in the Production of 1,3-diacylglycerol by Immobilized Lipozyme RM IM-catalyzed Esterification Meng, Zong; Lu, Shan; Geng, Wenxin Food Science and Technology Research, Vol. 20, Issue 2 https://doi.org/10.3136/fstr.20.175	journal	January 2014

Cited By (6)

One hour enzymatic synthesis of structure lipids enriched unsaturated fatty acids from silkworm pupae oil under microwave irradiation Wang, Jin‐Zheng; Liu, Xi; Li, Wen‐Jing Journal of Chemical Technology & Biotechnology, Vol. 95, Issue 2 https://doi.org/10.1002/jctb.5924	journal	February 2019
Use of sulfated cellulose nanocrystals towards stability enhancement of gelatin-encapsulated tea polyphenols Sun, Bo; Zhang, Min; Ni, Yonghao Cellulose, Vol. 25, Issue 9 https://doi.org/10.1007/s10570-018-1918-9	journal	July 2018
Microfluidic tools for lipid production and modification: a review Wang, Jin-Zheng; Zhu, Lin-Lin; Zhang, Fan Environmental Science and Pollution Research, Vol. 26, Issue 35 https://doi.org/10.1007/s11356-019-05833-4	journal	July 2019
Advances in plant materials, food by-products, and algae conversion into biofuels: use of environmentally friendly technologies Kamani, Mohammad Hassan; Eş, Ismail; Lorenzo, Jose M. Green Chemistry, Vol. 21, Issue 12 https://doi.org/10.1039/c8gc03860k	journal	January 2019
Microfluidic immobilized enzyme reactors for continuous biocatalysis Zhu, Yujiao; Chen, Qingming; Shao, Liyang Reaction Chemistry & Engineering, Vol. 5, Issue 1 https://doi.org/10.1039/c9re00217k	journal	January 2020
Synthesis, physicochemical properties, and health aspects of structured lipids: A review Guo, Yalong; Cai, Zhixiang; Xie, Yanping Comprehensive Reviews in Food Science and Food Safety, Vol. 19, Issue 2 https://doi.org/10.1111/1541-4337.12537	journal	January 2020

Similar Records

Use of a fluorescent radiolabeled triacylglycerol as a substrate for lipoprotein lipase and hepatic triglyceride lipase

Journal Article · Wed Jun 01 00:00:00 EDT 1988 · Lipids; (United States) · OSTI ID:6544794

Dousset, N; Negre, A; Salvayre, R; +3 more

Biomass and Neutral Lipid Production in Geothermal Microalgal Consortia

Journal Article · Sun Feb 15 23:00:00 EST 2015 · Frontiers in Bioengineering and Biotechnology · OSTI ID:1630050

Bywaters, Kathryn F.; Fritsen, Christian H.

Crystal Structure of Proteus mirabilis Lipase, a Novel Lipase from the Proteus/Psychrophilic Subfamily of Lipase Family I.1

Journal Article · Tue Dec 25 23:00:00 EST 2012 · PLoS ONE · OSTI ID:1904726

Korman, Tyler P.; Bowie, James U.

Related Subjects

09 BIOMASS FUELS
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
coproduct
microalgae oil
microfluidic bioconversion
polyunsaturated fatty acid
structured triacylglycerols

Title: Selective synthesis of human milk fat-style structured triglycerides from microalgal oil in a microfluidic reactor packed with immobilized lipase

Citation Formats

References (33)

Cited By (6)

Similar Records

Related Subjects