Welcome to Journal of Tea Science,Today is

Review on Enzymatic Biosynthesis of Theanine

  • CHEN Lin ,
  • ZHANG Zheng-zhu ,
  • CHEN Jian ,
  • ZHANG Ying-gen ,
  • WAN Xiao-chun
Expand
  • 1. Tea Research Institute, Fujian Academy of Agricultural Sciences, Fu’an 355015, China;
    2. Anhui Agricultural University, Key Laboratory of Tea Biochemistry & Biotechnology, Ministry of Education, Hefei 230036, China;

Received date: 2010-06-29

  Revised date: 2010-09-02

  Online published: 2019-09-06

Abstract

As a characteristic component in tea plant (Camellia sinensis), theanine has many favorable physiological effects, such as promoting relaxation, enhancing memory, neuroprotection, modulation of chemotherapy, etc. So far, seven kinds of enzyme have been discovered by which theanine can be synthesized. They are respectively named as theanine synthetase, glutamine synthetase, γ-glutamylmethylamide synthetase, glutamate synthetase, γ-glutamylcysteine synthetase, glutaminase and γ-glutamyltranspeptidase. The two representative reaction types for theanine biosynthesis are linking reaction between glutamic acid and ethylamine in the presence of ATP and γ-glutamyl transfer reaction in which γ-glutamyl group from hydrolysis of glutamine is transferred to ethylamine. In order to apply and develop the exiting methods for microbial production of theanine, the ways involved in enzymatic synthesis of theanine are systematically summarized in this paper.

Cite this article

CHEN Lin , ZHANG Zheng-zhu , CHEN Jian , ZHANG Ying-gen , WAN Xiao-chun . Review on Enzymatic Biosynthesis of Theanine[J]. Journal of Tea Science, 2011 , 31(1) : 1 -10 . DOI: 10.13305/j.cnki.jts.2011.01.001

References

[1] Casimir J, Jadot J, Renard M.Separation and characterization of N-ethyl-γ-glutamine in Xerocomus badius (Boletus ladius)[J]. Biochim Biophys Acta, 1960(39): 462-468.
[2] Li J, Li P, Liu F.Production of theanine by Xerocomus badius (mushroom) using submerged fermentation[J]. LWT-Food Sci Technol, 2008, 41(5): 883-889.
[3] Tsushida T, Takeo T.Occurrence of theanine in Camellia japonica and Camellia sasanqua seedlings[J]. Agric Biol Chem, 1984, 48(11): 2861-2862.
[4] Deng W W, Ogita S, Ashihara H.Distribution and biosynthesis of theanine in Theaceae plants[J]. Plant Physiol Bioch, 2010, 48(1): 70-72.
[5] 陈林. 茶树体内茶氨酸代谢及其相关酶的基础方法研究[D]. 合肥: 安徽农业大学, 2008.
[6] 宛晓春. 茶叶生物化学: 第三版[M]. 北京: 中国农业出版社, 2003: 32-34.
[7] 钟俊辉, 陶文沂. 茶愈伤组织培养及其茶氨酸的累积[J]. 无锡轻工大学学报: 食品与生物技术, 1997, 16(3): 1-7.
[8] Matsuura, T, Kakuda T, Kinoshita T, et al. Theanine formation by tea suspension cells[J]. Biosci Biotechnol Biochem, 1992, 56(8): 1179-1181.
[9] 陈瑛, 钟俊辉. 茶细胞悬浮培养生产茶氨酸的工艺条件研究[J]. 绍兴文理学院学报, 1998, 18(5): 71-75.
[10] Sasaoka K, Inagaki H, Kito M.Studies on the biosynthesis of theanine in tea seedlings. Synthesis of theanine by the homogenate of tea seedlings[J]. Agric Biol Chem, 1963, 27(6): 467-468.
[11] Sasaoka K, Kito M, Onishi Y.Some properties of the theanine synthesizing enzyme in tea seedlings[J]. Agric Biol Chem, 1965, 29(11): 984-988.
[12] 李平, 宛晓春, 李健, 等. 茶氨酸的衍生化及毛细管电泳定量技术[J]. 茶叶科学, 2004, 24(2): 119-123.
[13] 李平, 李健, 李娟, 等. 茶籽培育及茶氨酸合成酶活力测定条件的研究[J]. 安徽农业大学学报, 2005, 32(2): 158-161.
[14] Li P, Wan X C, Zhang Z Z, et al. A novel assay method for theanine synthetase activity by capillary electrophoresis[J]. J Chromatogr, B: Anal Technol Biomed Life Sci, 2005, 819(1): 81-84.
[15] Okada Y, Koseki M, Chu M,et al. Protein and cDNA sequences of two theanine synthetases from Camellia sinensis: JP, 2006254780[P].2006-09-28.
[16] Deng W W, Ogita S, Ashihara H.Biosynthesis of theanine (γ-ethylamino-L-glutamic acid) in seedlings of Camellia sinensis[J]. Phytochem Lett, 2008, 1(2): 115-119.
[17] Sasaoka K, Onishi Y, Kito M.Synthesis of theanine by pea seed acetone powder extract[J]. Agric Biol Chem, 1964, 28(5): 318-324.
[18] Sasaoka K, Onishi Y, Kito M.Synthesis of theanine by pigeon liver acetone powder extract[J]. Agric Biol Chem, 1964, 28(5): 325-330.
[19] 立木隆. 細菌におけるグルタミン―グルタミン酸生合成系の機能解析と応用[J]. 日本農芸化學会誌, 1983, 57(11): 1155-1164.
[20] Tachiki T, Suzuki H, Wakisaka S, et al. Production of γ-glutamylmethylamide and γ-glutamylethylamide by coupling of bakers' yeast preparations and bacterial glutamine synthetase[J]. J Gen Appl Microbiol, 1986, 32(6): 545-548.
[21] Yamamoto S, Uchimura K, Wakayama M. et al. Purification and characterization of glutamine synthetase of Pseudomonas taetrolens Y-30: An enzyme usable for production of theanine by coupling with the alcoholic fermentation system of baker's yeast[J]. Biosci Biotechnol Biochem, 2004, 68(9): 1888-1897.
[22] Yamamoto S, Wakayama M, Tachiki T.Theanine production by coupled fermentation with energy transfer employing Pseudomonas taetrolens Y-30 glutamine synthetase and Baker's yeast cells[J]. Biosci Biotechnol Biochem, 2005, 69(4): 784-789.
[23] Yamamoto S, Wakayama M, Tachiki T.Cloning and expression of Pseudomonas taetrolens Y-30 gene encoding glutamine synthetase: an enzyme available for theanine production by coupled fermentation with energy transfer[J]. Biosci Biotechnol Biochem, 2006, 70(2): 500-507.
[24] 朱文娴, 黎星辉, 王丽鸳, 等. 利用GS基因构建茶氨酸生物合成工程菌的研究[J]. 茶叶科学, 2008, 28(4): 242-248.
[25] 朱文娴, 房婉萍, 成浩, 等. 谷氨酰胺合成酶催化合成茶氨酸条件的优化[J]. 南京农业大学学报, 2009, 32(3): 135-138.
[26] Zhou X, Zhang Z P, Jia X H. et al. Mn2+ enhances theanine-forming activity of recombinant glutamine synthetase from Bacillus subtilis in Escherichia coli[J]. World J Microbiol Biotechnol, 2008, 24(8): 1267-1272.
[27] Kimura T, Sugahara I, Hanai K, et al. Purification and characterization of γ-glutamylmethylamide synthetase from Methylophaga sp. AA-30[J]. Biosci Biotechnol Biochem, 1992, 56(5): 708-711.
[28] Leisinger T, van der Ploeg J, Kiener A M,et al. Pseudomonas ipu operon and recombinant microorganisms for production of L-alaninol and γ-glutamyl amides: WO, 2001073038[P], 2001-10-04.
[29] Yamamoto S, Wakayama M, Tachiki T.Characterization of theanine-forming enzyme from Methylovorus mays No. 9 in respect to utilization of theanine production[J]. Biosci Biotechnol Biochem, 2007, 71(2): 545-552.
[30] Yamamoto S, Wakayama M, Tachiki T.Cloning and expression of Methylovorus mays No. 9 gene encoding γ-glutamylmethylamide synthetase: an enzyme usable in theanine formation by coupling with the alcoholic fermentation system of baker's yeast[J]. Biosci Biotechnol Biochem, 2008, 72(1): 101-109.
[31] Yamamoto S, Morihara Y, Wakayama M. et al. Theanine production by coupled fermentation with energy transfer using γ-glutamylmethylamide synthetase of Methylovorus mays No. 9[J]. Biosci Biotechnol Biochem, 2008, 72(5): 1206-1211.
[32] Yamamoto Y, Ishiguro K, Kawaguchi N. Dentifrice compositions containing sodium lauroyl sarcosine, menthol,theanine and method for suppressing unpleasant tastes of dentifrice compositions: JP, 2009143811[P], 2009-07-02.
[33] Tachiki T, Doi T, Koseki M. Microbial manufacture of theanine[P]. JP2009225705, 2009-10-08.
[34] Lam H M, Coschigano K T, Oliveira I C, et al. The molecular-genetics of nitrogen assimilation into amino acids in higher plants[J]. Annu Rev Plant Physiol Plant Mol Biol, 1996, 47: 569-593.
[35] Tochikura T, Tachiki T. Microbial production of theanine-related compounds: JP, 58040094[P], 1983-03-08.
[36] Miyake K, Kakita S.A novel catalytic ability of γ-glutamylcysteine synthetase of Escherichia coli and its application in theanine production[J]. Biosci Biotechnol Biochem, 2009, 73(12): 2677-2683.
[37] Miyake K, Hashimoto S I. Manufacture of γ-glutaramide compounds using γ-glutamylcysteine synthetase or recombinant microorganism: WO, 2006121055[P], 2006-11-16.
[38] Soda K, Ohshima M, Yamamoto T.Purification and properties of isoenzymes of glutaminase from Pseudomonas aeruginosa[J]. Biochem Biophys Res Commun, 1972, 46(3): 1278-1284.
[39] Soda K, Ohshima M, Yamamoto T.Purification, crystallization, and characterization of glutaminases A and B from Pseudomonas aeruginosa[C]. Ferment Technol Today, Proc Int Ferment Symp, 4th, 1972: 339-345.
[40] Abelian V H, Okubo T, Shamtsian M M, et al. A novel method of production of theanine by immobilized Pseudomonas nitroreducens cells[J]. Biosci Biotechnol Biochem, 1993, 57(3): 481-483.
[41] Abelian V H, Okubo T, Mutoh K, et al. A continuous production method for theanine by immobilized Pseudomonas nitroreducens cells[J]. J Ferment Bioeng, 1993, 76(3): 195-198.
[42] Ookubo T, Bui E A, Muto K,et al. Theanine manufacture with immobilized bacteria: JP, 05328986[P],1993-12-14.
[43] Yamada T, Naemura Y, Shiode T,et al. Manufacture of theanine with glutaminase: JP, 05068578[P], 1993-03-23.
[44] Tachiki T, Yamada T, Ueda M, et al. Purification and some properties of glutaminase from Pseudomonas nitroreducens IFO 12694[J]. Biosci Biotechnol Biochem, 1996, 60(7): 1160-1164.
[45] Tachiki T, Yamada T, Mizuno K, et al. γ-Glutamyl transfer reactions by glutaminase from Pseudomonas nitroreducens IFO 12694 and their application for the syntheses of theanine and γ-glutamylmethylamide[J]. Biosci Biotechnol Biochem, 1998, 62(7): 1279-1283.
[46] 王春晖. 茶氨酸生物合成研究[D]. 杭州: 中国农业科学院茶叶研究所, 2005.
[47] Aoi N, Tanaka Y, Kobayashi K. Production method for L-theanine: JP, 11225789[P], 1999-08-24.
[48] Senba H, Nishi K. Enzymic manufacture of α-amino acid ω-amides from α-amino acid ω-esters: JP, 2007185132[P], 2007-07-26.
[49] Tachiki T, Okada Y, Ozeki M,et al. Theanine manufacture with Pseudomonas citronellolis: WO, 2004016798[P], 2004-02-26.
[50] Tachiki T, Okada Y, Ozeki M,et al. Process for producing theanine: US, 007335497[P], 2004-02-26.
[51] Okada Y, Ozeki M, Aoi N. Enzymic manufacture of theanine: WO, 2006001296[P], 2006-01-05.
[52] Shimizu Y. Manufacture of L-γ-glutamyl lower alkylamides with γ-glutamyltranspeptidase: JP, 05284983[P], 1993-02-11.
[53] Suzuki H, Izuka S, Miyakawa N, et al. Enzymatic production of theanine, an "umami" component of tea, from glutamine and ethylamine with bacterial γ-glutamyltranspeptidase[J]. Enzyme Microb Technol, 2002, 31(6): 884-889.
[54] 郭亮, 沈微, 王正祥, 等. 生物转化法生产茶氨酸的重组大肠杆菌的构建[J]. 食品与生物技术学报, 2005, 24(2): 41-45.
[55] 王贤波, 王丽鸳, 成浩, 等. 茶氨酸生物合成工程菌构建[J]. 茶叶科学, 2007, 27(1): 61-66.
[56] 王丽鸳, 王贤波, 成浩, 等. 基因工程菌生物合成茶氨酸条件研究[J]. 茶叶科学, 2007, 27(2): 111-116.
[57] 陆文渊. 茶氨酸生物合成基因工程菌发酵工艺的研究[D]. 杭州: 中国农业科学院茶叶研究所, 2008.
[58] 朱文娴, 王丽鸳, 成浩, 等. 催化合成茶氨酸的基因工程菌的构建及重组基因的表达[J]. 江苏农业学报, 2008, 24(3): 257-262.
[59] 贾晓鹤, 陈莉, 赵宁伟, 等. 生物转化法应用重组谷氨酰转肽酶合成L-茶氨酸[J]. 食品工业科技, 2008, 29(2): 166-169.
[60] Yao Y F, Weng Y M, Hu H Y, et al. Expression optimization and biochemical characterization of a recombinant γ-glutamyltranspeptidase from Escherichia coli Novablue[J]. Protein J, 2006, 25(6): 431-441.
[61] Hung C P, Lo H F, Hsu W H, et al. Immobilization of Escherichia coli novablue γ-glutamyltranspeptidase in Ca-alginate-k-carrageenan beads[J]. Appl Biochem Biotechnol 2008, 150(2): 157-170.
[62] 江波, 张涛, 帅玉英. 天然茶氨酸的制备方法: 中国, 101343618[P], 2009-01-14.
[63] 刘冬英. 茶氨酸产生菌的选育[D]. 广州: 广东药学院, 2009.
[64] 傅锦坚. 微生物酶法生产茶氨酸的研究[D]. 广州: 广东药学院, 2009.
[65] Suzuki H, Izuka S, Minami H, et al. Use of bacterial γ-glutamyltranspeptidase for enzymatic synthesis of γ-D-glutamyl compounds[J]. Appl Environ Microbiol, 2003, 69(11): 6399-6404.
[66] Kumagaya H, Suzuki H. γ-D-glutamyl compounds manufacture with γ-glutamyl transpeptidase: JP, 2005080503[P], 2005-03-31.
[67] 姚忠, 邓海霞, 周治, 等. 一种酶法合成L-茶氨酸的方法: 中国, 101270376[P], 2008-09-24.
[68] 邓海霞, 姚忠, 周治, 等. 以L-谷氨酰胺-铜(Ⅱ)配合物为供体酶法制备茶氨酸[J]. 化工学报, 2008, 59(12): 3115-3119.
[69] 焦庆才, 张飞, 刘均忠等. L-茶氨酸酶法转化制备方法: 中国, 101560532[P], 2009-10-21.
[70] 张飞, 熊吉滨, 刘均忠, 等. L-谷氨酰肼为底物酶法制备茶氨酸[J]. 精细化工, 2010, 27(2): 130-132,141.
[71] Tsushida T, Takeo T.Purification and some properties of tea leaf amine oxidase[J]. Agric Biol Chem, 1985, 49(2): 319-326.
[72] Kito M, Kokura H, Izaki J, et al. Theanine, a precursor of the phloroglucinol nucleus of catechins in tea plants[J]. Phytochemistry, 1968, 7(4): 599-603.
[73] 小西茂毅, 高橋英一. 茶幼苗におけるテアニンの代謝と代謝産物の再移動: 茶樹におけるテアニンおよびその関連物質の代謝と制御: 第6報[J]. 日本土壌肥料学雑誌, 1969, 40(11): 479-484.
[74] Deng W W, Ogita S, Ashihara H.Ethylamine content and theanine biosynthesis in different organs of Camellia sinensis seedlings[J]. Z Naturforsch C, 2009, 64(5/6): 387-390.
[75] 陈林, 张应根, 陈键, 等. 茶树体内茶氨酸代谢及其酶学研究进展[J]. 茶叶科学技术, 2009 (3): 1-7.
[76] 李靓. 茶氨酸保健功效研究及其保健食品开发[D]. 杭州: 中国农业科学院茶叶研究所, 2009.
[77] Liu B, Li P, Zhang C L, et al. Theanine synthesized by immobilizing Pseudomonas nitroreducens LY in nanofibrous membranes[J]. Process Biochemistry, 2010, 45(8): 1330-1333.
Outlines

/