L-Theanine: Properties, synthesis and isolation from tea

Journal of the Science of Food and Agriculture

Volumn 91, Issue 11, 2011, Pages 1931-1939

  Vuong, Quan V ^a   Bowyer, Michael C ^a   Roach, Paul D ^a  

^a UNIVERSITY OF NEWCASTLE   (Australia)

Author keywords

Health benefits; Isolation; Properties; Synthesis; Tea; Theanine

Indexed keywords

ANTIHYPERTENSIVE AGENT; ANTINEOPLASTIC AGENT; ANXIOLYTIC AGENT; GLUTAMIC ACID DERIVATIVE; THEANINE;

ANIMAL; CHEMISTRY; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; PLANT LEAF; PLANT ROOT; REVIEW; TEA;

ANIMALS; ANTI-ANXIETY AGENTS; ANTIHYPERTENSIVE AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMELLIA SINENSIS; GLUTAMATES; HUMANS; PLANT LEAVES; PLANT ROOTS; TEA;

CAMELLIA SINENSIS;

EID: 79960106680     PISSN: 00225142     EISSN: 10970010     Source Type: Journal    
DOI: 10.1002/jsfa.4373     Document Type: Review

References (80)

1. Sakato Y, The chemical constituents of tea: III. A new amide theanine. Nippon Nogei Kagakukaishi 23: 262-267 (1949).
2. Wan X, Zhang Z and Li D, Chemistry and biological properties of theanine, in Tea and Tea Products, ed. by Ho CT, Lin JK and Shahidi F. CRC Press, Boca Raton, pp. 255-274 (2009).
3. Deng WW, Ogita S and Ashihara H, Distribution and biosynthesis of theanine in Theaceae plants. Plant Physiol Biochem 48: 70-72 (2010).
4. Deng WW, Ogita S and Ashihara H, Biosynthesis of theanine (γ-ethylamino-l-glutamic acid) in seedlings of Camellia sinensis. Phytochem Lett 1: 115-119 (2008).
5. Suzuki H, Yamada C and Kato K, γ-Glutamyl compounds and their enzymatic production using bacterial γ-glutamyltranspeptidase. Amino Acids 32: 333-340 (2007).
6. Juneja LR, Chu DC, Okubo T, Nagato Y and Yokogoshi H, L-Theanine-a unique amino acid of green tea and its relaxation effect in humans. Trends Food Sci Technol 10: 199-204 (1999).
7. Balentine DA, Harbowy ME and Graham HN, Tea: The plant and its manufacture; chemistry and consumption of the beverage, in Caffeine, ed. by Spiller GA. CRC Press, Boca Raton, pp. 35-72 (1998).
8. Chu DC, Green tea-its cultivation, processing of the leaves for drinking materials, and kinds of green tea, in Chemistry and Applications of Green Tea, ed. by Yamamoto T, Juneja LR, Chu DC and Kim M. CRC Press, Boca Raton, pp. 1-11 (1997).
9. Chu DC, Kobayashi K, Juneja LR and Yamamoto T, Theanine-its synthesis, isolation, and physiological activity, in Chemistry and Applications of Green Tea, ed. by Yamamoto T, Juneja LR, Chu DC and Kim M. CRC Press, Boca Raton, pp. 129-135 (1997).
10. Hara Y, Green Tea: Health Benefits and Applications. Marcel Dekker, Inc, New York (2001).
11. Ekborg-Ott KH, Taylor A and Armstrong DW, Varietal differences in the total and enantiomeric composition of theanine in tea. J Agric Food Chem 45: 353-363 (1997).
12. Bryan J, Psychological effects of dietary components of tea: caffeine and L-theanine. Nutr Rev 66: 82-90 (2007).
13. Huber LG, Green Tea catechins and L-theanine in integrative cancer care: A review of the research. Altern Complement Ther 9: 294-298 (2003).
14. Chu DC and Juneja LR, General chemical composition of green tea and its infusion, in Chemistry and Applications of Green Tea, ed. by Yamamoto T, Juneja LR, Chu DC and Kim M, CRC Press, Boca Raton, pp. 13-22 (1997).
15. Nobre AC, Rao A and Owen GN, L-theanine, a natural constituent in tea, and its effect on mental state. Asia Pac J Clin Nutr 17: 167-168 (2008).
16. Kobayashi K, Nagato Y, Aoi N, Juneja LR, Kim M, Yamamoto T, et al, Effects of L-theanine on the release of α-brain waves in human volunteers. Nippon Nogei Kagakukaishi 72: 153-157 (1998).
17. Lu K, Gray MA, Oliver C, Liley DT, Harrison BJ, Bartholomeusz CF, et al, The acute effects of L-theanine in comparison with alprazolam on anticipatory anxiety in humans. Hum Psychopharmacol Clin 19: 457-465 (2004).
18. Kimura K, Ozeki M, Juneja LR and Ohira H, L-Theanine reduces psychological and physiological stress responses. Biol Psychol 74: 39-45 (2007).
19. Haskell CF, Kennedy DO, Milne AL, Wesnes KA and Scholey AB, The effects of L-theanine, caffeine and their combination on cognition and mood. Biol Psychol 77: 113-122 (2008).
20. Owen GN, Parnell H, Bruin EAD and Rycroft JA, The combined effects of L-theanine and caffeine on cognitive performance and mood. Nutr Neurosci 11: 193-198 (2008).
21. Gomez-Ramirez M, Higgins BA, Rycroft JA, Owen GN, Mahoney J, Shapener M, et al, The deployment of intersensory selective attention: A high-density electrical mapping study of the effects of theanine. Clin Neuropharmacol 30: 25-38 (2007).
22. Liu Q, Duan H, Luan J, Yagasaki K and Zhang G, Effects of theanine on growth of human lung cancer and leukemia cells as well as migration and invasion of human lung cancer cells. Cytotechnology 59: 211-217 (2009).
23. Friedman M, Mackey BE, Kim HJ, Lee IS, Lee KR, Lee SU, et al, Structure-activity relationships of tea compounds against human cancer cells. J Agric Food Chem 55: 243-253 (2007).
24. Zhang G, Miura Y and Yagasaki K, Inhibitory effects of theanine and sera from theanine-fed rats on receptor-mediated cancer cell invasion beneath mesothelial-cell monolayers. Cytotechnology 36: 195-200 (2001).
25. Yokogoshi H and Kobayashi M, Hypotensive effect of γ-glutamylmethylamide in spontaneously hypertensive rats. Life Sci 62: 1065-1068 (1998).
26. Rogers PJ, Smith JE, Heatherley SV and Pleydell-Pearce CW, Time for tea: Mood, blood pressure and cognitive performance effects of caffeine and theanine administered alone and together. Psychopharmacology 195: 569-577 (2007).
27. Kurihara S, Shibahara S, Arisaka H and Akiyama Y, Enhancement of antigen-specific immunoglobulin G production in mice by co-administration of L-cystine and L-theanine. J Vet Med Sci 69: 1263-1270 (2007).
28. Miyagawa K, Hayashi Y, Kurihara S and Maeda A, Co-administration of L-cystine and L-theanine enhances efficacy of influenza vaccination in elderly persons: Nutritional status-dependent immunogenicity. Geriatr Gerontol Int 8: 243-250 (2008).
29. Takagi Y, Kurihara S, Higashi N, Morikawa S, Kase T, Maeda A, et al, Combined administration of L-cystine and L-theanine enhances immune functions and protects against influenza virus infection in aged mice. J Vet Med Sci 72: 157-165 (2010).
30. Zheng G, Sayama K, Okubo T, Juneja LR and Oguni L, Anti-obesity effects of three major components of green tea, catechins, caffeine and theanine, in mice. In Vivo 18: 55-62 (2004).
31. Terashima T, Takido J and Yokogoshi H, Time-dependent changes of amino acids in the serum, liver, brain and urine of rats administered with theanine. Biosci Biotechnol Biochem 63: 615-618 (1999).
32. Cooper R, Morré DJ and Morré DM, Medicinal benefits of green tea: Part I. Review of noncancer health benefits. J Altern Complement Med 11: 521-528 (2005).
33. Mason R, 200 mg of Zen: L-theanine boosts alpha waves, promotes alert relaxation. Altern Complement Ther 7: 91-95 (2001).
34. Di X, Yan J, Zhao Y, Zhang J, Shi Z, Chang Y, et al, L-Theanine protects the APP (Swedish mutation) transgenic SH-SY5Y cell against glutamate-induced excitotoxicity via inhibition of the NMDA receptor pathway. Neuroscience 18: 778-786 (2010).
35. Sugiyama T and Sadzuka Y, Theanine, a specific glutamate derivative in green tea, reduces the adverse reactions of doxorubicin by changing the glutathione level. Cancer Lett 212: 177-184 (2004).
36. Sadzuka Y, Sugiyama T, Suzuki T and Sonobe T, Enhancement of the activity of doxorubicin by inhibition of glutamate transporter. Toxicol Lett 123: 159-167 (2001).
37. Yamano H and Miyagawa K, Buffer capacity curves of green tea extracts using a personal computer with numerically treated online software. Food Sci Technol Int Tokyo 3: 69-73 (2009).
38. Vuong VQ, Golding JB, Nguyen M and Roach PD, Extraction and isolation of catechins from tea. J Sep Sci 33: 3415-3428 (2010).
39. Ishizu T, Tsutsumi H and Sato T, Interaction between gallocatechin gallate and caffeine in crystal structure of 1:2 and 2:2 complexes. Tetrahedron Lett 50: 4121-4124 (2009).
40. Liang H, Liang Y, Dong J, Lu J, Xu H and Wang H, Decaffeination of fresh green tea leaf (Camellia sinensis) by hot water treatment. Food Chem 101: 1451-1456 (2007).
41. Narukawa M, Morita K and Hayshi Y, L-Theanine elicits an umami taste with inosine 5'-monophosphate. Biosci Biotechnol Biochem 72: 3015-3017 (2008).
42. de Araujo IET, Kringelbach ML, Rolls ET and Hobden P, Representation of umami taste in the human brain. J Neurophysiol 90: 313-319 (2003).
43. Yamaguchi S, The umami taste, in Food Taste Chemistry, ed. by Boudreau JC. ACS, Houston, pp. 33-51 (1979).
44. Chen CN, Liang CM, Lai JR, Tsai YJ, Tsay JS and Lin JK, Capillary electrophoretic determination of theanine, caffeine, and catechins in fresh tea leaves and oolong tea and their effects on rat neurosphere adhesion and migration. J Agric Food Chem 51: 7495-7503 (2003).
45. Hsiao HY, Chen RLC and Cheng TJ, Determination of tea fermentation degree by a rapid micellar electrokinetic chromatography. Food Chem 120: 632-636 (2010).
46. Peng L, Song X, Shi X, Li J and Ye C, An improved HPLC method for simultaneous determination of phenolic compounds, purine alkaloids and theanine in Camellia species. J Food Compos Anal 21: 559-563 (2008).
47. Syu KY, Lin CL, Huang HC and Lin JK, Determination of theanine, GABA, and other amino acids in green, oolong, black, and pu-erh teas with dabsylation and high performance liquid chromatography. J Agric Food Chem 56: 7637-7643 (2008).
48. Li P, Wan XC, Zhang ZZ, Li J and Shen ZJ, A novel assay method for theanine synthetase activity by capillary electrophoresis. J Chromatogr B 819: 81-84 (2005).
49. Kvasnič ka F and Krátká J, Isotachophoretic determination of theanine. Cent Eur J Chem 4: 216-222 (2006).
50. Ding Y, Yu H and Mou S, Direct determination of free amino acids and sugars in green tea by anion-exchange chromatography with integrated pulsed amperometric detection. J Chromatogr A 982: 237-244 (2002).
51. Horie H, Determination of tea components by enzymatic flow injection analysis. Jpn Agric Res Quart 34: 191-194 (2000).
52. Lichtenstein N, Preparation of c-alkylamides of glutamic acid. J Am Chem Soc 64: 1021-1022 (1942).
53. Kawagishi H and Sugiyama K, Facile and large-scale synthesis of L-theanine. Biosci Biotechnol Biochem 56: 689 (1992).
54. Yan SH, Dufour JP and Meurens M, Synthesis and characterization of highly pure theanine. J Tea Sci 23: 99-104 (2003).
55. Gu H, Jiang Y and Wang J, A practical synthesis of ethyl L-glutamine (L-theanine). Org Prep Proced Int 36: 182-185 (2004).
56. Zhang F, Zheng QZ, Jiao QC, Liu JZ and Zhao GH, Enzymatic synthesis of theanine from glutamic acid γ-methyl ester and ethylamine by immobilized Escherichia coli cells with γ-glutamyltranspeptidase activity. Amino Acids 39: 1177-1182 (2010).
57. Nandakumar R, Yoshimune K, Wakayama M and Moriguchi M, Microbial glutaminase: biochemistry, molecular approaches and applications in the food industry. J Mol Catalysis B-Enzymes 23: 87-100 (2003).
58. Tachiki T, Yamada T, Mizuno K, Ueda M, Shiode JI and Fukami H, γ-Glutamyl transfer reactions by glutaminase from Pseudomonas nitroreducens IFO 12 694 and their application for the syntheses of theanine and γ-glutamylmethylamide. Biosci Biotechnol Biochem 62: 1279-1283 (1998).
59. Abelian VH, Okubo T, Mutoh K, Chu DC, Kim M and Yamamoto T, A continuous production method for theanine by immobilized Pseudomonas nitroreducens cells. J Ferment Bioeng 76: 195-198 (1993).
60. Miyake K and Kakita S, A novel catalytic ability of γ-glutamylcysteine synthetase of Escherichia coli and its application in theanine production. Biosci Biotechnol Biochem 73: 2677-2683 (2009).
61. Yamamoto S, Wakayama M and Tachiki T, Theanine production by coupled fermentation with energy transfer employing Pseudomonas taetrolens Y-30 glutamine synthetase and baker's yeast cells. Biosci Biotechnol Biochem 69: 784-789 (2005).
62. Yamamoto S, Wakayama M and 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. Biosci Biotechnol Biochem 72: 101-109 (2008).
63. 2+ enhances theanine-forming activity of recombinant glutamine synthetase from Bacillus subtilis in Escherichia coli. World J Microb Biotechnol 24: 1267-1272 (2008).
64. Suzuki H, Izuka S, Miyakawa N and Kumagai H, Enzymatic production of theanine, an 'umami' component of tea, from glutamine and ethylamine with bacterial γ-glutamyltranspeptidase. Enzyme Microb Technol 31: 884-889 (2002).
65. Zhang F, Zheng QZ, Jiao QC, Liu JZ and Zhao GH, Synthesis of theanine from glutamic acid γ-methyl ester and ethylamine catalyzed by Escherichia coli having γ-glutamyltranspeptidase activity. Biotechnol Lett 32: 1147-1150 (2010).
66. Zhang Y, Chen B, Huang Z and Shi Z, Preparative isolation and purification of L-theanine by HPLC. J Liq Chromatogr Relat Technol 27: 875-884 (2004).
67. Lachová M, Lehotay J, Karasová G, Skačáni I and Armstrong DW, Isolation of L-theanine from plant material using a molecularly imprinted polymer. J Liq Chromatogr Relat Technol 30: 2045-2058 (2007).
68. Ekamayake A and Li JJ, Process for enriching extracts of natural theanine. US Patent 689910 (2007).
69. Baudouin SX, Process for purifying theanine. European Patent EP2144868 (A1) (2010).
70. Food and Agriculture Organization. Current situation and medium-term outlook, in Committee on Commodity Problems, Intergovernmental Group on Tea (2008). Hangzhou, China. Available: .
71. Astill C, Birch MR, Dacombe C, Humphrey PG and Martin PT, Factors affecting the caffeine and polyphenol contents of black and green tea infusions. J Agric Food Chem 49: 5340-5347 (2001).
72. Wang L and Weller CL, Recent advances in extraction of nutraceuticals from plants. Trends Food Sci Technol 17: 300-312 (2006).
73. Mandal V, Mohan Y and Hemalatha S, Microwave assisted extraction-An innovative and promising extraction tool for medicinal plant research. Pharmacog Rev 1: 7-18 (2007).
74. Amarowicz R, Shahidi F and Wiczkowski W, Separation of individual catechins from green tea using silica gel column chromatography and HPLC. J Food Lipids 10: 165-177 (2003).
75. Kang JH, Chung T, Go JH and Row KH, Separation of epigallocatechin gallate from Korean green tea by RP-HPLC. J Liq Chromatogr Relat Technol 23: 2739-2749 (2000).
76. Gailliot FP, Initial extraction and product capture, in Natural Products Isolation, ed. by Cannell RJP. Humana Press, Totowa, pp. 53-89 (1998).
77. Zhao R, Yan Y, Li M and Yan H, Selective adsorption of tea polyphenols from aqueous solution of the mixture with caffeine on macroporous crosslinked poly(N-vinyl-2-pyrrolidinone). React Funct Polym 68: 768-774 (2008).
78. Bailey AT, Yuhasz D and Zeng WB, Method for isolation of caffeine-free catechins from green tea. US Patent 6210679 (2001).
79. LišKa I, Fifty years of solid-phase extraction in water analysis-Historical development and overview. J Chromatogr A 885: 3-16 (2000).
80. Sablani SS and Rahman MS, Fundamental of food dehydration, in Food Drying Science and Technology, ed. by Hui YH, Clary C, Farid MM, Fasina OO, Noomhorm A and Welti-Chanes J. DES Technical Publications, Pennsylvania, pp. 1-42 (2008).