高纯度茶氨酸的合成与特性

doi:10.13305/j.cnki.jts.2003.02.003

Abstract

Abstract: An improved synthesis method of L-Theanine, γ - glutamylethylamide was reported as the dehydratation of L-glutamic acid to pyrrolidone carboxylic acid (PCA), then PCA reaction with absolute ethylamine (99%, gas-liquid) with the yield of 92.6%. After re-crystallization in 84% ethanol solution the highest pure theanine (A type) is obtained with a yield of 37.4%. The crystals appear as tetra-rectangular prisms with a silk luster under transmission and scanning electron microscopy (TEM and SEM). The melting point of A theanine is 224°C. The B theanine synthesized from L-PCA shapes as cabbage leaves with curved borders under SEM and with a m. p. of 217 - 218°C as reference data. By using HPLC, it is confirmed that A and B theanine are mix-isomers. The A theanine consists of 47.9% L-theanine and the B theanine consists of 90.9% L-theanine. The rotation (α) of 100% L- theanine was + 8.57°.

Key words: Theanine, Synthesis of theanine, Characterization of theanine

CLC Number:

Q946

YAN Shou He, Jean-Pierre DUFOUR, Marc MEURENS. Synthesis and Characterization of Highly Pure Theanine[J]. Journal of Tea Science, 2003, 23(2): 99-104.

References

[1] Sakato Y.The chemical constituents of tea: III, A new amide, theanine[J]. J. Agric. Chem. Soc. Jap., 1950, 23: 262-267.
[2] Kito M, KoKura H, Izaki J, Sasaoka K. Theanine, a precusor of the phloroglucinol nucleus of catechins in tea plants[J]. Phytochem., 1968, 7:599-603.
[3] Takeo T.Biosynthesis of ethylamine in tea plant[A]. The Proceedings of the IV Int. Cong. of Food Sci. and Techn[C]. Ia, 1974, 55-57.
[4] Anan T, Amano I., Nakagawa M.Relation between changes of chemical. compositions and taste of green tea: I. Changes in contents of some ingredients during heating of green tea[J]. J. Jap. Soc. Food Sci. Technol., 1981, 28: 74-78.
[5] Hara T.Volatile compounds formed on roasting L-theanine with D-glucose[J]. J. Agric. Chem. Soc. Jap., 1981, 55: 1069-1072.
[6] Nakagawa M, Anan T, Ishima M.Relationship of green tea taste to chemical Composition[J]. Bull. Nat. Res. Inst. Tea, 1981, 17: 69-123.
[7] Yan S H, Meurens M, Dufour J P.Taste quality control of china tea by NIRS method[A]. The Proceeding of 2d Int. Cong, Edited by Iwamoto, M. & Kawano, S., Japan Korin Pub Co ed (Japan), 1990, 1: 66-173.
[8] Sadzuka Y, Sugiyama T, Miyagishima A, Nozawa Y, Hirota S.The effects of theanine, as a novel biochemical modulator on the antitumor activity of adeiamycin[J]. Cancer-letters, 1996, 105(2): 203-209.
[9] Sadzuka Y, Sugiyama T, Sonobe T.Improvement of idarubicin induced antitumor activity and bone marrow suppression by theanine, a component of tea[J]. Cancer-letters, 2000, 158(2), 119-124.
[10] Sugiyama T, Sadzuka Y, Tanaka K, Sonobe T.Inhibition of glutamate transporter by theanine enhances the therapeutic efficacy of doxorubicin[J]. Toxicology-letters, 2001, 121(2), 89-96.
[11] Menozzi A Appiani G, 1892 Sopra un nuovo acido derivato dal glutammico. Gazz. Chim. Ital., 22, 105-108.
[12] Menozzi A, Appiani G, 1892 Sopra alcuni derivati dell’acido glutammico: acidi piroglutammici e piroglutammidi.Gazz. Chim. Ital., 24, 370-391.
[13] Abderhalden E, Kautzsch K, 1910 Zur kenntnis der glutaminsäure und der Pyrrolidoncarbonsäure.Physiol. Chem., 68, 447-459.
[14] Beecham A F, 1954 The action of ammonia and other bases on γ-methyl and γ- ethyl L-glutamate.J. Am. Chem. Soc., 76, 4615.
[15] Lichtenstein N, 1942 Preparation of γ-alkylamides of glutamic acid.J. Am. Chem. Soc., 64, 1021-1022.
[16] Sakato Y, Hashizume T, Kishimoto Y, 1950 The chemical constituents of tea: V, Synthesis of theanine,J. Agric. Chem. Soc. Jap., 23, 269-271.
[17] Kawagishi H, Sugiyama K, 1992 Facile and large-scale synthesis of L- theanine. Biosci. Biotech. Biochem., 56,(4) 689.
[18] Marfey P, 1984 Determination of D-amino acids: II, Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene.Carlsberg Res. Commun., 49, 591-596.

Synthesis and Characterization of Highly Pure Theanine

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Comments

Recommended 10

[1]	HUANG Qiuping, XIE Chenyang, LI Xinyu, JIN Bin, ZENG Zhen, QIAN Bo, DAI Ling, SONG Jiale. L-Theanine Ameliorated Clinical Symptoms in Letrozole-Induced Polycystic Ovary Syndrome Rats [J]. Journal of Tea Science, 2021, 41(6): 831-842.
[2]	CHEN Meiyan, LIU Fen, LIN Yong, ZUO Gaolong, ZUO Yingpeng, LIU Zhonghua. Intervention Effects of L-Theanine on the Damage of Hippocampus and Gut in CUMS Depressed Rats [J]. Journal of Tea Science, 2021, 41(4): 511-524.
[3]	MAO Peng, WANG Liyuan, BAI Peixian, WEI Kang, RUAN Li, ZHNAG Yazhen, CHENG Hao. Identification and Analysis of Analogue Theanine Synthase Gene Family in Tomato [J]. Journal of Tea Science, 2021, 41(2): 173-183.
[4]	JIN Ke, HUANG Jian'an, XIONG Ligui, LIU Shuoqian, QIN Xiaohong, PENG Jing, LI Yinhua, LI Juan. Research of Theanine-related Genes Expressed in Etiolated Tea Plant (Camellia Sinensis) [J]. Journal of Tea Science, 2021, 41(1): 40-47.
[5]	ZENG Li, XIAO Wenjun. Advances in Brain Diseases Prevention and Treatment of L- theanine [J]. Journal of Tea Science, 2019, 39(2): 193-202.
[6]	PENG Yingqi, XIAO Wenjun, ZHANG Sheng, YUAN Dongyin, LIN Ling, ZHOU Yang, GONG Zhihua. Effects of L-theanine on Intestinal Morphology and Free Amino Acids in Mice [J]. Journal of Tea Science, 2019, 39(1): 43-54.
[7]	ZHU Chengbo, WU Xiaomei, FENG Lixia, HUANG Xiangpeng, PANG Linjiang, YANG Huqing, FANG Zhengwei, WANG Ying, LAI Shuyu, ZHANG Yiming. Rapid Detection of Theanine in Green Tea Based on Direct-reading Colorimetric Strips [J]. Journal of Tea Science, 2018, 38(3): 244-252.
[8]	LI Xiaojie, MA Jianqiang, YAO Mingzhe, CHEN Liang. SNP Detection and Mapping of Theanine Synthetase Gene in Tea Plant [J]. Journal of Tea Science, 2017, 37(3): 251-257.
[9]	GUO Chen, LIU Linfeng, XIANG Yi, LUO Li, LIN Ling, XIAO Wenjun. L-theanine Attenuates Tissue and Oxidative Damages in Heat Stressed Mice [J]. Journal of Tea Science, 2017, 37(1): 17-24.
[10]	LIU Zunying, LIU Qiuling, DENG Yanli, CHEN Ling, XIAO Wenjun. Study on the Protective Effect of L-Theanine on the Intestinal in Mice with Immune Stress Induced by ETEC [J]. Journal of Tea Science, 2016, 36(5): 469-476.
[11]	LIU Qiuling, GONG Zhihua, CHENG Ling, LIU Zunying, DENG Yanli, CHEN Dong, XIAO Wenjun. Study on the Protective Effect of L-Theanine on the Liver of Mice with Immune Stress Induced by ETEC [J]. Journal of Tea Science, 2016, 36(5): 484-490.
[12]	PENG Bin, LIU Zhonghua, LIN Yong, LIN Haiyan, HUANG Jian'an. The Ameliorative Effect of L-theanine on Chronic Unpredictable Mild Stress-induced Depression in Rats [J]. Journal of Tea Science, 2014, 34(4): 355-363.
[13]	LIU Xiaohui, JIE Guoliang, LIN Kang, WU Yuanyuan, WANG Yuefei, TU Youying. Research on Synergistic Protection and Repairing Effects of EGCG and Theanine in Oxidative Damaged Cells [J]. Journal of Tea Science, 2014, 34(3): 239-247.
[14]	YU Xi-chong, YANG Wei, WU Bo-la. Theanine Depressed the Food Intake and Gastric Emptying in Female Mice via Lateral Hypothalamic AMPA and NMDA Receptor [J]. Journal of Tea Science, 2013, 33(5): 429-435.
[15]	TAN Jun-feng, LIN Zhi, PENG Qun-hua, GUO Li, LV Hai-peng. Evaluation on the Alleviating Physical Fatigue Function of Theanine Compound Preparation [J]. Journal of Tea Science, 2012, 32(6): 530-534.