磷脂酰丝氨酸的酶法制备与分离研究进展
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摘要
磷脂酰丝氨酸(PS)的制备有溶剂提取法、化学合成法和酶转化法。采用溶剂提取法从动物组织提取PS由于"疯牛病"原因而受质疑;化学合成法成本较高,工艺复杂,且纯度和收率有待提高;酶转化法具有反应条件温和、反应易控、高效简单的优势,越来越受到关注。主要对磷脂酰丝氨酸的酶法制备以及分离纯化方法进行了综述,对其生产制备过程提出了合理的建议和策略。
Phosphatidylserine( PS) can be prepared by solvent extraction,chemical synthesis and enzymatic synthesis.PS extracted from animal tissues by solvent extraction is questioned because of bovine spongiform encephalopathy.Chemical synthesis has the weakness of high cost and complex process,also the purity and yield need to be improved.Enzymatic synthesis has the advantages of mild conditions,easy to control and high efficiency,and it attracts a lot of attention.The preparation of PS by enzymatic synthesis and the separation and purification methods were reviewed,and some reasonable suggestions and strategies were put forward.
Phosphatidylserine( PS) can be prepared by solvent extraction,chemical synthesis and enzymatic synthesis.PS extracted from animal tissues by solvent extraction is questioned because of bovine spongiform encephalopathy.Chemical synthesis has the weakness of high cost and complex process,also the purity and yield need to be improved.Enzymatic synthesis has the advantages of mild conditions,easy to control and high efficiency,and it attracts a lot of attention.The preparation of PS by enzymatic synthesis and the separation and purification methods were reviewed,and some reasonable suggestions and strategies were put forward.
引文
[1] MOZZI R,BURATTA S,GORACCI G. Metabolism and functions of phosphatidylserine in mammalian brain[J].Neurochem Res,2003,28(2):195-214.
[2]HOSOKAWA M,SHIMATANI T,KANADA T,et al.Conversion to docosahexaenoic acid-containing phosphatidylserine from squid skin lecithin by phospholipase D-mediated transphosphatidylation[J]. J Agric Food Chem,2000,48(10):4550-4554.
[3]张忆雪.酶法制磷脂酰丝氨酸[D].北京:北京化工大学,2013.
[4]韩海霞.磷脂酶D的制备及其在磷脂酰丝氨酸合成中的应用[D].江苏无锡:江南大学,2014.
[5]杨学利.高产磷脂酶D菌株的筛选、鉴定及活性研究[D].成都:四川师范大学,2016.
[6]张芹.酶法合成富含n-3 PUFA的磷脂酰丝氨酸的研究[D].山东青岛:中国海洋大学,2015.
[7]朱南南.磷脂酶D催化磷脂酰基转移合成磷脂酰丝氨酸反应的研究[D].西安:西北大学,2015.
[8]钱娟,庞洋,王昕.磷脂酶D的制备及催化磷脂酰胆碱合成磷脂酰丝氨酸[J].中国油脂,2017,42(9):66-71.
[9]路福平,张业尼,李玉.双液相体系中磷脂酶D转酯合成磷脂酰丝氨酸的研究[C].济南:全国发酵行业高峰论坛暨中国发酵工业协会2007年行业大会,2007.
[10]LIM S K,CHOI J W,CHUNG M H,et al. Production and characterization of extracellular phospholipase D from Streptomyces sp. YU100[J]. J Microbiol Biotechnol,2002,12(2):189-195.
[11]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 Technol,2016,118(5):803-813.
[12]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.
[13]周炳华.葡萄糖酸水溶液作为一种绿色可持续介质促进有机反应的研究[D].武汉:华中科技大学,2013.
[14] DUAN Z Q,HU F. Efficient synthesis of phosphatidylserine in 2-methyltetrahydrofuran[J]. J Biotechnol,2013,163(1):45-49.
[15]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(1):115-119.
[16]BI Y H,DUAN Z Q,LI X Q,et al. Introducing biobased ionic liquids as the non-aqueous media for enzymatic synthesis of phosphatidylserine[J]. J Agric Food Chem,2015,63(5):1558-1561.
[17]YANG S L,DUAN Z Q. Insight into enzymatic synthesis of phosphatidylserine in deep eutectic solvents[J]. Catal Commun,2016,82:16-19.
[18]胡飞,段章群,王淮,等.生物酶法制备磷脂酰丝氨酸的研究进展[J].中国油脂,2012,37(6):54-58.
[19]宋晚平,任静,王磊,等.一种粉末磷脂酰丝氨酸的制备方法:CN101230365[P]. 2008-07-30.
[20] BIRICHEVSKAYA L L,KISEL M A. Use of phospholipase D from Streptomyces netropsis for the biocatalytic synthesis of phosphatidylserine[J]. Vestsi Natsyyanalnaj Akadehmii Navuk Belarusi Seryya Biyalagichnykh Navuk,2008(4):86-90.
[21]PINSOLLE A,ROY P,CANSELL M. Modulation of enzymatic PS synthesis by liposome membrane composition[J]. Colloids Surfaces B Biointerf,2014,115(3):157-163.
[22]于刚,徐伟,栾东磊,等.亚临界R134a流体中酶法制备富含多不饱和脂肪酸的磷脂酰丝氨酸[J].高技术通讯,2008,18(10):1075-1080.
[23]严明,高璐,魏淼,等.一种固定化磷脂酶D催化制备磷脂酰丝氨酸的方法:CN103966277A[P]. 2014-08-06.
[24] LIU Y,ZHANG T,QIAO J,et al. High-yield phosphatidylserine production via yeast surface display of phospholipase D from Streptomyces chromofuscus on Pichia pastoris[J]. J Agric Food Chem,2014,62(23):5354-5360.
[25]ROUSER G,SIMON G,KRITCHEVSKY G. Species variations in phospholipid class distribution of organs:I.Kidney,liver and spleen[J]. Lipids,1969,4(6):599.
[26]XU G,WAKI H,KON K,et al. Thin-layer chromatography of phospholipids and their lyso forms:application to determination of extracts from rat hippocampal CA1 region[J]. Microchem J,1996,53(1):29-33.
[27]贺杠.磷脂酶D催化合成磷脂酰丝氨酸的色谱分离研究[D].西安:西北大学,2011.
[28]PIETSCH A,LORENZ R L. Rapid separation of the major phospholipid classes on a single aminopropyl cartridge[J]. Lipids,1993,28(10):945-947.
[29]韩山山,张康逸,黄健花,等.树脂柱色谱纯化甘油磷脂酰胆碱[J].中国油脂,2012,37(3):47-51.
[30]卢学清,王智华,洪筱坤.等度反相高效液相色谱法测定熊胆中磷脂类化合物[J].色谱,2000,18(1):57-60.
[31]苏永恒,张伟,马青青.高效液相色谱-蒸发光散射检测法测定保健食品中的磷脂酰丝氨酸[J].中国卫生检验杂志,2017(6):792-794.
[32]柳仁民,王海兵,周建民.制备色谱技术及装备研究进展[J].现代制造,2011(2):10-15.
[33]曹栋,裘爱泳,王兴国.超临界流体分离大豆磷脂酰胆碱[J].中国油脂,2002,27(3):72-73.
[2]HOSOKAWA M,SHIMATANI T,KANADA T,et al.Conversion to docosahexaenoic acid-containing phosphatidylserine from squid skin lecithin by phospholipase D-mediated transphosphatidylation[J]. J Agric Food Chem,2000,48(10):4550-4554.
[3]张忆雪.酶法制磷脂酰丝氨酸[D].北京:北京化工大学,2013.
[4]韩海霞.磷脂酶D的制备及其在磷脂酰丝氨酸合成中的应用[D].江苏无锡:江南大学,2014.
[5]杨学利.高产磷脂酶D菌株的筛选、鉴定及活性研究[D].成都:四川师范大学,2016.
[6]张芹.酶法合成富含n-3 PUFA的磷脂酰丝氨酸的研究[D].山东青岛:中国海洋大学,2015.
[7]朱南南.磷脂酶D催化磷脂酰基转移合成磷脂酰丝氨酸反应的研究[D].西安:西北大学,2015.
[8]钱娟,庞洋,王昕.磷脂酶D的制备及催化磷脂酰胆碱合成磷脂酰丝氨酸[J].中国油脂,2017,42(9):66-71.
[9]路福平,张业尼,李玉.双液相体系中磷脂酶D转酯合成磷脂酰丝氨酸的研究[C].济南:全国发酵行业高峰论坛暨中国发酵工业协会2007年行业大会,2007.
[10]LIM S K,CHOI J W,CHUNG M H,et al. Production and characterization of extracellular phospholipase D from Streptomyces sp. YU100[J]. J Microbiol Biotechnol,2002,12(2):189-195.
[11]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 Technol,2016,118(5):803-813.
[12]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.
[13]周炳华.葡萄糖酸水溶液作为一种绿色可持续介质促进有机反应的研究[D].武汉:华中科技大学,2013.
[14] DUAN Z Q,HU F. Efficient synthesis of phosphatidylserine in 2-methyltetrahydrofuran[J]. J Biotechnol,2013,163(1):45-49.
[15]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(1):115-119.
[16]BI Y H,DUAN Z Q,LI X Q,et al. Introducing biobased ionic liquids as the non-aqueous media for enzymatic synthesis of phosphatidylserine[J]. J Agric Food Chem,2015,63(5):1558-1561.
[17]YANG S L,DUAN Z Q. Insight into enzymatic synthesis of phosphatidylserine in deep eutectic solvents[J]. Catal Commun,2016,82:16-19.
[18]胡飞,段章群,王淮,等.生物酶法制备磷脂酰丝氨酸的研究进展[J].中国油脂,2012,37(6):54-58.
[19]宋晚平,任静,王磊,等.一种粉末磷脂酰丝氨酸的制备方法:CN101230365[P]. 2008-07-30.
[20] BIRICHEVSKAYA L L,KISEL M A. Use of phospholipase D from Streptomyces netropsis for the biocatalytic synthesis of phosphatidylserine[J]. Vestsi Natsyyanalnaj Akadehmii Navuk Belarusi Seryya Biyalagichnykh Navuk,2008(4):86-90.
[21]PINSOLLE A,ROY P,CANSELL M. Modulation of enzymatic PS synthesis by liposome membrane composition[J]. Colloids Surfaces B Biointerf,2014,115(3):157-163.
[22]于刚,徐伟,栾东磊,等.亚临界R134a流体中酶法制备富含多不饱和脂肪酸的磷脂酰丝氨酸[J].高技术通讯,2008,18(10):1075-1080.
[23]严明,高璐,魏淼,等.一种固定化磷脂酶D催化制备磷脂酰丝氨酸的方法:CN103966277A[P]. 2014-08-06.
[24] LIU Y,ZHANG T,QIAO J,et al. High-yield phosphatidylserine production via yeast surface display of phospholipase D from Streptomyces chromofuscus on Pichia pastoris[J]. J Agric Food Chem,2014,62(23):5354-5360.
[25]ROUSER G,SIMON G,KRITCHEVSKY G. Species variations in phospholipid class distribution of organs:I.Kidney,liver and spleen[J]. Lipids,1969,4(6):599.
[26]XU G,WAKI H,KON K,et al. Thin-layer chromatography of phospholipids and their lyso forms:application to determination of extracts from rat hippocampal CA1 region[J]. Microchem J,1996,53(1):29-33.
[27]贺杠.磷脂酶D催化合成磷脂酰丝氨酸的色谱分离研究[D].西安:西北大学,2011.
[28]PIETSCH A,LORENZ R L. Rapid separation of the major phospholipid classes on a single aminopropyl cartridge[J]. Lipids,1993,28(10):945-947.
[29]韩山山,张康逸,黄健花,等.树脂柱色谱纯化甘油磷脂酰胆碱[J].中国油脂,2012,37(3):47-51.
[30]卢学清,王智华,洪筱坤.等度反相高效液相色谱法测定熊胆中磷脂类化合物[J].色谱,2000,18(1):57-60.
[31]苏永恒,张伟,马青青.高效液相色谱-蒸发光散射检测法测定保健食品中的磷脂酰丝氨酸[J].中国卫生检验杂志,2017(6):792-794.
[32]柳仁民,王海兵,周建民.制备色谱技术及装备研究进展[J].现代制造,2011(2):10-15.
[33]曹栋,裘爱泳,王兴国.超临界流体分离大豆磷脂酰胆碱[J].中国油脂,2002,27(3):72-73.