磷脂酶D特性及其在功能性磷脂生产中的应用

doi:10.19640/j.cnki.jtau.2021.02.016

天津农学院学报 ›› 2021, Vol. 28 ›› Issue (2): 79-84.doi: 10.19640/j.cnki.jtau.2021.02.016

磷脂酶D特性及其在功能性磷脂生产中的应用

陈景^1,2, 陈建华^1,2, 刘凯^1,2, 吴海清^1,2,*

1.天津农学院食品科学与生物工程学院,天津 300392;
2.天津市农副产品深加工技术工程中心,天津 300392

收稿日期:2020-06-15 发布日期:2021-07-26
通讯作者: 吴海清（1982—）,女,实验师,硕士,研究方向：农产品加工、发酵微生物。E-mail：haiqing_w@yeah.net。
作者简介:陈景（1996—）,女,本科在读,研究方向：生物工程。E-mail：2417336926@qq.com。
基金资助:
天津农学院大学生创新创业训练计划项目（201810061215）

Characteristics of phospholipase D and its application in the production of functional phospholipids

Chen Jing^1,2, Zhen Jianhua^1,2, Liu Kai, Wu Haiqing^1,2,*

1. College of Food Science and Bioengineering, Tianjin Agricultural University, Tianjin 300392, China;
2. Tianjin Engineering and Technology Research Center of Agricultural Products Processing, Tianjin 300392, China

Received:2020-06-15 Published:2021-07-26

摘要/Abstract

摘要： 磷脂酶D（Phospholipase D,PLD）是催化磷酸二脂键水解和碱基交换反应的一类酶的总称。生产中利用PLD的转酯作用来制备功能性磷脂。本文介绍了磷脂酶的分子结构、催化机理及功能,以及磷脂酰丝氨酸（PS）、磷脂酰甘油（PG）、磷脂酰乙醇胺（PE）和磷脂酰肌醇（PI）的生产方法,包括物理萃取法、化学合成法和酶促合成法,酶促合成法是目前制备功能性磷脂最主要的方法。此外,对今后功能性磷脂的研究做了展望,期望可以通过改进技术条件、工艺体系来提高PLD的催化性能,为稀有磷脂的工业化生产提供理论及相关技术支持。

关键词: 磷脂酶D, 特性, 功能性磷脂, 制备方法, 应用

Abstract: Phospholipase D (PLD) is a kind of enzyme which catalyzes the hydrolysis and base exchange of phosphodiesters. Functional phospholipids are prepared by transesterification of PLD. This paper introduced the molecular structure, catalytic mechanism and function of phospholipase. The production methods of phosphatidylserine (PS), phosphatidylglycerol (PG), phosphatidylethanolamine (PE) and phosphatidylinositol (PI) were mainly introduced, including physical extraction, chemical synthesis and enzymatic synthesis. Enzymatic synthesis is the most important method to prepare functional phospholipids. In addition, this paper prospected the future research on functional phospholipids. It is expected that the catalytic performance of PLD can be improved by improving the technical conditions and process system, which will provide theoretical and technical support for the industrial production of rare phospholipids.

Key words: phospholipase D, characteristic, functional phospholipid, preparation method, application

中图分类号:

TQ426.97

陈景, 陈建华, 刘凯, 吴海清. 磷脂酶D特性及其在功能性磷脂生产中的应用[J]. 天津农学院学报, 2021, 28(2): 79-84.

Chen Jing, Zhen Jianhua, Liu Kai, Wu Haiqing. Characteristics of phospholipase D and its application in the production of functional phospholipids[J]. Journal of Tianjin Agricultural University, 2021, 28(2): 79-84.

导出引用管理器 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

链接本文: http://xuebao.tjau.edu.cn/CN/10.19640/j.cnki.jtau.2021.02.016

http://xuebao.tjau.edu.cn/CN/Y2021/V28/I2/79

参考文献

[1] LIU Y H,HUANG L,FU Y,et al.A novel process for phosphatidylserine production using a Pichia pastoris whole cell biocatalyst with overexpression of phospholipase D from Streptomyces halstedii in a purely aqueous system[J]. Food Chem,2019,274(39):535-542.
[2] CHOOJIT S,BORNSCHEUER U T,UPAICHIT A,et al.Efficient phosphatidylserine synthesis by a phospholipase D from Streptomyces sp. SC734 isolated from soil-contaminated palm oil[J]. Eur J Lipid Sci Tech,2015,118(5):803-813.
[3] HUANG T T,LÜ X Q,LI J H,et al.Combinatorial fine-tuning of phospholipase D expression by Bacillus subtilis WB600 for the production of phosphatidylserine[J]. J Microbiol Biotechnol,2018,28(12):2046-2056.
[4] MAO X Z,LIU Q Q,QIU Y Q,et al.Identification of a novel phospholipase D with high transphosphatidylation activity and its application in synthesis of phosphatidylserine and DHA phosphatidylserine[J]. J Biotechnol,2017,249:51-58.
[5] KIDD P M.Phosphatidylserine:membrane nutrient for memory. A clinical and mechanistic assessment[J]. Alternative Medicine Review,1996,1(2):70-84.
[6] HIRAYAMA S,TERASAWA K,RABELER R,et al.The effect of phosphatidylserine administration on memory and symptoms of attention-deficit hyperactivity disorder: a randomised,double-blind,placebo-controlled clinical trial[J]. J Hum Nutr Diet,2014,27(Suppl2):284-291.
[7] BIRGE R B,BOELTZ S,KUMAR S,et al.Phosphatidylserine is a global immunosuppressive signal in efferocytosis,infectious disease,and cancer[J]. Cell Death and Differen,2016,23(6):962-978.
[8] VAN DER VEEN J N,LINGRELL S,MC CLDSKEY,et al. A role for phosphatidylcholine and phosphatidylethanolamine in hepatic insulin signaling[J]. The FASEB Journal,2019,33(4):5045-5057.
[9] DAMNJANOVIĆ J,IWASAKI Y.Phospholipase D as a catalyst:Application in phospholipid synthesis, molecular structure and protein engineering[J]. J Biosci Bioeng,2013,116(3):271-280.
[10] YANG S F,FREER S,BENSON A A.Transphosphatidylation by phospholipase D[J]. J Biol Chem,1967,242(3):477-484.
[11] MC DERMOTT M, WAKELAM M J O,MORRIS A J. Phospholipase D[J]. Biochem Cell Biol,2004,82(1):225-253.
[12] DE MARIA L,VIND J,OXENBOLL K M.et al.Phospholipases and their industrial applications[J]. App Microbiol Biotechnol,2007,74:290-300.
[13] OGINO C,KURODA S,TOKUYAMA S,et al.Phospholipase D from Streptoverticillium cinnamoneum:Protein engineering and application for phospholipid production[J]. Mol Catal B:Enzym,2003,23:107-115.
[14] LEIROS I,HOUGH E,D’ARRIGO P,et al. Crystallization and preliminary X-ray diffraction studies of phospholipase D from Streptomyces sp.[J]. Acta Crystallogr D Biol Crystallogr,2000,56:466-468.
[15] OGINO C,DAIDO H,OHMURA Y,et al.Remarkable enhancement in PLD activity from Streptoverticillium cinnamoneum by substituting serine residue into the GG/GS motif[J]. Biochim Biophys Acta,2007,1774(6):671-678.
[16] 李冰麟. 磷酯酶D催化磷酯酰基转移反应生产稀有及非天然磷酯的研究[D]. 西安:西北大学,2019.
[17] 饶雪娥,林伟玲. 磷酯酰丝氨酸的应用研究进展[J]. 海峡药学,2015,27(11):9-11.
[18] TARFAROSH S F A,TROMBOO U,BHAT M F. Search for a perfect nootropic supplement combination-Can we increase human intelligence by nutritional supplements?[J]. Journal of Pharmacognosy and Phytochemistry,2017,6:1020-1024.
[19] NAKASHIMA R,KADO K,KUME T,et al.Synthesis of didocosahexaenoylphosphatidylserine[J]. Biosci Biotechnol Biochem,1997,61(12):1991-1994.
[20] 周彦峰,张涛,江波,等. 磷酯酰丝氨酸的酶法制备与分离研究进能[J]. 中国油酯,2018,43(10):53-57.
[21] LAMPKINS A J,O’ NEIL E J,SMITH B D. Bio-orthogonal phosphatidylserine conjugates for delivery and imaging applications[J]. J Org Chem,2008,73:6053-6058.
[22] GUANTI G,BANFI L,BASSO A,et al.Optimized synthesis of phosphatidylserine[J]. Amino Acids,2010,39:367-373.
[23] PRICE N,FEI T,CLARK S,et al.Extraction of phospholipids from a dairyby-product(whey protein phospholipid concentrate)using ethanol[J]. J Dairy Sci,2018,101:8778-8787.
[24] 崔益玮,俞喜娜,李诗言,等. 虾头中磷酯提取与组学分析[J]. 食品科学,2018,39(20):218-225.
[25] MAO X,LIU Q,QIU Y,et al.Identification of a novel phospholipase D with high transphosphatidylation activity and its application in synthesis of phosphatidylserine and DHA-phosphatidylserine[J]. J Biotechnol,2017,249:51-58.
[26] CHOOJIT S,BORNSCHEUER U T,UPAICHIT A,et al.Efficient phosphatidylserine synthesis by a phospholipase D from Streptomyces sp. SC734 isolated from soil contaminated palm oil[J]. Eur J Lipid Sci Tech,2016,118:803-813.
[27] IWASAKI Y,MIZUMOTO Y,OKADA T,et al.An aqueous suspension system for phospholipase D-mediated synthesis of PS without toxic organic solvent[J]. J Am Oil Chem Soc,2003,80(7):653-657.
[28] LI B,WANG J,ZHANG X,et al.An enzyme net coating the surface of nanoparticles:A simple and efficient method for the immobilization of phospholipase D[J]. Ind Eng Chem Res,2016,55:10555-10565.
[29] ZHANG X L,LI B L,WANG J,et al.High-yield and sustainable production of phosphatidylserine in purely aqueous solutions via adsorption of phosphatidylcholine on Triton-X-100-Modified Silica[J]. J Agric Food Chem,2017,65:10767-10774.
[30] 张忆雪. 梅法制磷酯酰丝氨酸[D]. 北京:北京化工大学,2013.
[31] QIN W,WU C J,SONG W,et al.A novel high-yield process of phospholipase D-mediated phosphatidylserine production with cyclopentyl methyl ether[J]. Process Biochem,2018,66:146-149.
[32] BI Y H,DUAN Z Q,DU W Y,et al.Improved synthesis of phosphatidylserine using bio-based solvents,limonene and p-cymene[J]. Biotechnol Lett,2015,37:115-119.
[33] D’ARRIGO P,CERIOLI L,CHIAPPE C,et al. Improvements in the enzymatic synthesis of phosphatidylserine employing ionic liquids[J]. J Mol Catal B:Enzym,2012,84:132-135.
[34] SHIROUCHI B,NAGAO K,INOUE N,et al.Dietary phosphatidylinositol prevents the development of nonalcoholic fatty liver disease in Zucker(fa/fa)rats[J]. J Agri Food Chem,2008,56:2375-2379.
[35] INAFUKU M,NAGAO K,INAFUKU A,et al.Dietary phosphatidylinositol protects C57BL/6 mice from concanavalin A-induced liver injury by modulating immune cell functions[J]. Mol Nutr Food Res,2013,57:1671-1679.
[36] POLI A,BILLI A M,MONGIORGI S,et al.Nuclear phosphatidylinositol signaling: Focus on phosphatidylinositol phosphate kinases and phospholipases C[J]. J Cell Physiol,2016,231:1645-1655.
[37] LI B L, DUAN D D, WANG J, et al.Improving phospholipase D activity and selectivity by bio-imprinting-immobilization to produce phosphatidylglycerol[J]. Journal of Biotechnology,2018,281:67-73.
[38] DAMNJANOVIC J,KUROIWA C,TANAKA H,et al.Directing positional specificity in enzymatic synthesis of bioactive 1-phosphatidylinositol by protein engineering of a phospholipase D[J]. Biotechnol Bioeng,2016,113:62-71.
[39] SERRANO A G,PEREZ-GIL J.Protein-lipid interactions and surface activity in the pulmonary surfactant system[J]. Chem Phys Lipids,2006,141:105-118.
[40] SUZURI K,YAMAMOTO Y,HOSOKAWA M,et al.Effect of alpha-tocopherol on the synthesis of phosphatidylglycerol catalyzed by phospholipase D in an aqueous system[J]. Biotechnol Lett,2009,31:719-723.
[41] FOLCH J.Brain cephalin, a mixture of phosphatides. Sepration from it of phosphatidyl serine, phosphatidyl ethanolamine,and a fraction containing an inositol phosphatide[J]. Journal of Biological Chemistry,1942,146(1):35-44.
[42] VAN DER VEEN J N,LINGRELL S,MC CLOSKEY N,et al. A role for phosphatidylcholine and phosphatidylethanolamine in hepatic insulin signaling[J]. The FASEB Journal,2019,33:5045-5057.
[43] 邓杨敏,李冰麟,董文博,等. 磷脂酰乙醇胺的酶促合成及底物抑制力学[J]. 化工进展,2017,36(7):2601-2606.
[44] SONG S,CHEONG L Z,FALKEBORG M,et al.Facile synthesis of phosphatidyl saccharides for preparation of anionic nanoliposomes with enhanced stability[J]. PLOSONE,2013,8(9):e73891.
[45] YAMAMOTO Y,KURIHARA H,MIYASHITA K,et al.Synthesis of novel phospholipids that bind phenylalkanols and hydroquinone via phospholipase D-catalyzed transphosphatidylation[J]. New Biotechnology,2011,28(1):1-6.

磷脂酶D特性及其在功能性磷脂生产中的应用

Characteristics of phospholipase D and its application in the production of functional phospholipids

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	张冉冉, 张桂霞, 王丹, 刘彤, 张涛, 韩世峰. 两个枣品种幼树在天津地区生长及光合特性研究[J]. 天津农学院学报, 2023, 30(5): 1-5.
[2]	侯佳聪, 邱安然, 常琳, 于玮玮, 王丽娟, 龙鸿. 遮阴对森林草莓分株生理特性的影响[J]. 天津农学院学报, 2023, 30(4): 1-7.
[3]	王威, 卢树昌. 新建温室土壤培肥技术及应用研究进展[J]. 天津农学院学报, 2023, 30(4): 78-83.
[4]	豆静静, 郑志伟, 高卓卓. 变化初始含水率条件下土壤入渗特性试验及模拟研究[J]. 天津农学院学报, 2023, 30(2): 11-17.
[5]	崔宇翔, 刘毅, 吴彦飞, 张清靖, 张树林. 我国渔稻共生种养发展概况[J]. 天津农学院学报, 2023, 30(2): 69-74.
[6]	雷海波, 王胜杰, 王浩迪, 杨奕曼, 郑润东, 刘文. 尿素缓释肥在我国农作物生产中的应用研究状况与前景[J]. 天津农学院学报, 2023, 30(2): 80-85.
[7]	于小涵, 孙金辉, 徐海龙. 层次分析法在我国海洋生态系统中的应用进展[J]. 天津农学院学报, 2023, 30(1): 80-83.
[8]	杜锦, 高星, 陈瀚, 杨吉林, 刘建, 向春阳. 天津地区10个水稻品种顶土能力比较研究[J]. 天津农学院学报, 2022, 29(4): 21-25.
[9]	王丹, 王璐瑶, 董家僖, 田秀平. 盐胁迫下水杨酸对苜蓿幼苗生理特性的影响[J]. 天津农学院学报, 2022, 29(3): 19-22.
[10]	潘镭文, 向春阳, 丁建文, 刘江波, 杜锦, 曹高燚. 外源水杨酸处理油菜幼苗对盐胁迫的生理响应[J]. 天津农学院学报, 2022, 29(2): 22-26.
[11]	李天杰, 李蕊, 蒋鑫, 杨静慧, 刘艳军, 王芝学. 天津市蓟州区观赏木本植物新品种生长特性比较[J]. 天津农学院学报, 2022, 29(1): 15-18.
[12]	张伟龙, 张般般, 杨静慧, 刘艳军, 张超, 冯国华. 不同时期蓝莓黄化规律及生长与黄化的关系[J]. 天津农学院学报, 2022, 29(1): 24-27.
[13]	丁建文, 张晓辰, 杨兴, 杜锦, 曹高燚, 向春阳. 盐胁迫下外源赤霉素对糯玉米幼苗生理特性的影响[J]. 天津农学院学报, 2022, 29(1): 37-41.
[14]	李夏雯, 卢树昌. 旱直播稻与常规移栽稻栽培技术研究进展比较探讨[J]. 天津农学院学报, 2021, 28(4): 63-70.
[15]	张倩颖, 祁杰, 毕起源, 韩蓄, 曾倩, 彭锦星. 地沟油检测技术研究进展[J]. 天津农学院学报, 2021, 28(3): 86-89.