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Research Progress in Enzymatic Synthesis of Vitamin E Ester Derivatives

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Research Progress in Enzymatic Synthesis of Vitamin E Ester Derivatives catalysts Review Research Progress in Enzymatic Synthesis of Vitamin E Ester Derivatives Zhiqiang Zou 1, Lingmei Dai 1, Dehua Liu 1,2 and Wei Du 1,2,* 1 Key Laboratory for Industrial Biocatalysis, Department of Chemical Engineering, Tsinghua University, Ministry of Education, Beijing 100084, China; [email protected] (Z.Z.); [email protected] (L.D.); [email protected] (D.L.) 2 Tsinghua Innovation Center in Dongguan, Dongguan 523808, China * Correspondence: [email protected] Abstract: Vitamin E is easily oxidized by light, air, oxidizing agents and heat, limiting its application in many ways. Compared to vitamin E, vitamin E ester derivatives exhibit improved stability and a stronger antioxidant capacity, and even gain new biological functions. In recent years, enzymatic synthesis of vitamin E ester derivatives has received increasing attention due to its environmental friendliness, high catalytic efficiency, and inherent selectivity. This paper reviews the related progress of lipase-mediated preparation of vitamin E ester derivatives. The function of different vitamin E ester derivatives, and the main factors influencing the enzymatic acylation process, including enzyme species, acyl donor and acceptor, reaction media and water activity, are summarized in this paper. Finally, the perspective of lipase-catalyzed synthesis of vitamin E ester derivatives is also discussed. Keywords: antioxidants; derivatives; lipase; vitamin E; vitamin E ester Citation: Zou, Z.; Dai, L.; Liu, D.; Du, W. Research Progress in Enzymatic Synthesis of Vitamin E Ester Derivatives. Catalysts 2021, 11, 739. 1. Introduction https://doi.org/10.3390/ Vitamin E (VE) is a group of eight liposoluble compounds, including four tocopherols catal11060739 and four tocotrienols. They are all composed of benzodihydropyran rings and 2-position phytogroups (Table1). Tocopherol has three chiral carbon atoms, and there are three Academic Editors: isolated double bonds on the phytogroups of tocotrienol [1]. Vegetable oil extracted from Rodica-Mihaela Dinică and oil-bearing seeds and nuts is the most abundant source of natural vitamin E. The total Lidia Favier vitamin E content in different oils varies from thousands ppm to tens ppm, and contains a variety of tocopherols and tocotrienols [2]. Chemically synthesized vitamin E is mainly a Received: 22 April 2021 racemic alpha-tocopherol by using trimethylhydroquinone and racemic isophytol [3]. Accepted: 15 June 2021 Natural antioxidant vitamin E is more suitable for food additives, health care, cosmet- Published: 16 June 2021 ics and other industries compared to synthetic antioxidants such as terbutyl hydroquinone (TBHQ), butyl hydroxytoluene (BHT), butyl hydroxyanisole (BHA), and propyl gallate, Publisher’s Note: MDPI stays neutral which may form toxic or carcinogenic compounds after degradation [4,5]. with regard to jurisdictional claims in Vitamin E is easily oxidized and is unstable to light and singlet oxygen. The antioxi- published maps and institutional affil- dant property of VE is reflected either in its termination of the free radical chain reaction iations. (Figure1a), or in the way that itself can be oxidized and lose its antioxidant property (Figure1b). Herein, when vitamin E is extracted from natural sources or is synthesized by chemical methods, it easily loses its original antioxidant function when added to products due to its own oxidation during the process of production, transportation, and storage. Copyright: © 2021 by the authors. Therefore, the modification on vitamin E to improve its stability is significant in promoting Licensee MDPI, Basel, Switzerland. its wider application [5]. This article is an open access article It is well recognized that vitamin E ester derivatives have a wide range of applica- distributed under the terms and tions in pharmaceuticals, cosmetics, daily chemicals, and other fields. At present, the conditions of the Creative Commons Attribution (CC BY) license (https:// most popular vitamin E ester products in the market are vitamin E acetate, vitamin E creativecommons.org/licenses/by/ succinate, vitamin E linoleic acid ester, and vitamin E niacin ester. Vitamin E acetate has 4.0/). been demonstrated to be effective in dealing with inflammation elimination, periodontal Catalysts 2021, 11, 739. https://doi.org/10.3390/catal11060739 https://www.mdpi.com/journal/catalysts ReviewReview ResearchResearch Progress Progress in in Enzymatic Enzymatic Synthesis Synthesis of of Vitamin Vitamin E EEster Ester Derivatives Review Derivatives Research ProgressZhiqiangZhiqiang Zou in Zou 1, LingmeiEnzymatic 1, Lingmei Dai Dai 1, Dehua 1, DehuaSynthesis Liu Liu 1,2 and 1,2 and Wei of Wei Du Vitamin Du 1,2,* 1,2,* E Ester Derivatives 1 Key1 KeyLaboratory Laboratory for Industrial for Industrial Biocatalysis, Biocatalysis, Department Department of Chemical of Chemical Engineering, Engineering, Tsinghua Tsinghua University, University, MinistryMinistry of Education, of Education, Beijing Beijing 100084, 100084, China China; [email protected]; [email protected] (Z.Z.); (Z.Z.); Zhiqiang Zou 1, Lingmei Dai 1, Dehua Liu 1,2 and Wei Du 1,2,* [email protected]@tsinghua.edu.cn (L.D.); (L.D.); [email protected] [email protected] (D.L (D.L.) .) 2 Tsinghua2 Tsinghua Innovation Innovation Center Center in Dongguan, in Dongguan, Guangdong Guangdong 523808, 523808, China China 1 Key Laboratory for Industrial* CorrespondenceBiocatalysis,* Correspondence Department: duwei@tsinghua: duwei@tsinghua of Chemical .edu.cnEngineering,.edu.cn Tsinghua University, Ministry of Education, Beijing 100084, China; [email protected] (Z.Z.); [email protected] (L.D.); [email protected] (D.L.) Abstract: Vitamin E is easily oxidized by light, air, oxidizing agents and heat, limiting its application 2 Tsinghua Innovation Center in Dongguan,Abstract: GuangdongVitamin E 523808, is easily China oxidized by light, air, oxidizing agents and heat, limiting its application * Correspondence: duwei@tsinghuain manyin .edu.cnmany ways. ways. Compared Compared to vitamin to vitamin E, vitamin E, vitamin E ester E ester derivatives derivatives exhibit exhibit improved improved stability stability and and a a strongerstronger antioxidant antioxidant capacity capacity, and, and even even gain gain new new biological biological functions. functions. In recent In recent years, years, enzymatic enzymatic Abstract: Vitamin E is easilysynthesis oxidizedsynthesis ofby vitaminlight, of vitamin air, Eoxidizing ester E ester derivatives agents derivatives and heat,has hasreceived limiting received its increasin application increasing attention g attention due due to its to environmentalits environmental in many ways. Compared to vitamin E, vitamin E ester derivatives exhibit improved stability and a friendliness,friendliness, high high catalytic catalytic efficiency efficiency, and, and inherent inherent selectivity. selectivity. This This paper paper reviews reviews the therelated related pro- pro- stronger antioxidant capacity, and even gain new biological functions. In recent years, enzymatic gressgress of lipase of lipase-mediated-mediated preparation preparation of vitamin of vitamin E ester E ester derivatives. derivatives. The The function function of different of different vita- vita- synthesis of vitamin E ester derivatives has received increasing attention due to its environmental min E ester derivatives, and the main factors influencing the enzymatic acylation process, including friendliness, high catalytic efficiencymin E, esterand inherent derivat ives,selectivity. and the This main paper factors reviews influencing the related the pro- enzymatic acylation process, including gress of lipase-mediated preparationenzymeenzyme species, of species,vitamin acyl acylE donor ester donor derivatives. and and acceptor, acceptor, The reactionfunction reaction mediaof different media and and vita-water water activity activity, are, aresummarized summarized in this in this min E ester derivatives, andpaper. thepaper. main Finally, factors Finally, the influencing theperspective perspective the enzymatic of lipase of lipase acylation-catalyzed-catalyzed process, synthesis synthesis including of vitamin of vitamin E ester E ester derivatives derivatives is also is also enzyme species, acyl donordiscussed. anddiscussed. acceptor, reaction media and water activity, are summarized in this Citation:Citation: Zou,paper. Zou, Z.; Dai,Finally, Z.; Dai,L.; Liu, L.;the D.;Liu, perspective D.; of lipase-catalyzed synthesis of vitamin E ester derivatives is also Du, W. Research Progress in Du, W.discussed. Research Progress in Keywords:Keywords: antioxidants antioxidants; derivatives; derivatives; lipase; lipase; vitamin; vitamin E; vitamin E; vitamin E ester E ester Citation: Zou, Z.; Dai, L.; Liu,Enzymatic D.; Enzymatic Synthesis Synthesis of Vitamin of Vitamin Du, W. Research Progress in E EsterE Ester Derivatives.Keywords: Derivatives. Catalysts antioxidants Catalysts ; derivatives; lipase; vitamin E; vitamin E ester Enzymatic Synthesis of Vitamin 2021,2021 11, x., 11 https://doi.org/, x. https://doi.org/ E Ester Derivatives. Catalysts 10.3390/xxxxx10.3390/xxxxx 2021, 11, x. https://doi.org/ 1. Introduction1. Introduction 10.3390/xxxxx AcademicAcademicCatalysts1. Editor: Introduction Editor:2021 , 11 , 739 VitaminVitamin E (VE) E (VE) is a is group a group of eight of eight liposoluble liposoluble compounds, compounds, including including four four tocopher- tocopher-2 of 11 Rodica-Mihaela
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