Pharmacokinetics of theanine enantiomers in rats

Chirality

Volumn 17, Issue 3, 2005, Pages 154-162

  Desai, Meera J ^a   Gill, Manmeet S ^a   Hsu, Walter H ^a   Armstrong, Daniel W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Absorption; Chiral; Excretion; LC MS; Metabolism; Pharmacokinetics; Theanine

Indexed keywords

AMINO ACID; DRUG ADDITIVE; SUNTHEANINE; THEANINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BIOEQUIVALENCE; CHIRALITY; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG ELIMINATION; DRUG URINE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOMER; INTESTINE ABSORPTION; ISOMER; KIDNEY METABOLISM; LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; TEA;

ANIMALS; CHROMATOGRAPHY, LIQUID; GLUTAMATES; MALE; MASS SPECTROMETRY; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM;

EID: 14844333252     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20144     Document Type: Article

References (29)

1. Sakato Y. The chemical constituents of tea; III. A new amide theanine. Nippon Nogei Kagaku Kaishi 1949;23:262-267.
2. Ekborg-Ott KH, Taylor A, Armstrong DW. Varietal differences in the total and enantiomeric composition of theanine in tea. J Agric Food Chem 1997;45:353-363.
3. Goto T, Horie H, Ozeki Y, Masuda H, Warashina J. Chemical composition of Japanese green tea on market. Tea Res J 1994;80:23-28.
4. Casimir J, Jadot J, Renard M. Separation and characterization of N-ethyl-γ-glutamine in Xerocomus badius (Boletus ladius). Biochim Biophys Acta 1960;39:462-468.
5. Nagasawa K, Aoki H, Yasuda E, Nagai K, Shimohama S, Fujimoto S. Possible involvement of group I mGluRs in neuroprotective effect of theanine. Biochem Biophys Res Commun 2004;320:116-122.
6. Zhang G, Miura Y, Yagasaki K. Effects of dietary powdered green tea and theanine on tumor growth and endogenous hyperlipidemia in hepatoma-bearing rats. Biosci Biotechnol Biochem 2002;66: 711-716.
7. Sugiyama T, Sadzuka Y. Theanine and glutamate transporter inhibitors enhance the antitumor efficacy of chemotherapeutic agents. Biochim Biophys Acta 2003;1653:47-59.
8. Yokozawa T, Dong E. Influence of green tea and its three major components upon low-density lipoprotein oxidation. Exp Toxicol Pathol 1997;49:329-335.
9. Yokogoshi H, Kobayashi M. Hypotensive effect of γ- glutamylethylamide in spontaneously hypertensive rats. Life Sci 1998;62:1065-1068.
10. Yokogoshi H, Terashima T. Effect of theanine, γ-glutamylethylamide, on brain monoamines, striatal dopamine release and some kinds of behavior in rats. Nutrition 2000;16:776-777.
11. Kamath AB, Wang L, Das H, Li L, Reinhold VN, Bukowski JF. Antigens in tea-beverage prime human Vγ2Vδ2 T cells in vitro and in vivo for memory and nonmemory antibacterial cytokine responses. Proc Natl Acad Sci U S A 2003;100:6009-6014.
12. Ding Y, Yu H, 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 2002;982: 237-244.
13. Terashima T, Takido J, Yokogoshi H. Time-dependent changes of amino acids in the serum, liver, brain and urine of rats administered with theanine. Biosci Biotechnol Biochem 1999;63:615-618.
14. Unno T, Suzuki Y, Kakuda T, Hayakawa T, Tsuge H. Metabolism of theanine, γ-glutamylethylamide, in rats. J Agric Food Chem 1999;47: 1593-1596.
15. Petritis K, Valleix A, Elfakir C, Dreux M. Simultaneous analysis of underivatized chiral amino acids by liquid-chromatography-ionspray tandem mass spectrometry using a teicoplanin chiral stationary phase. J Chromatogr A 2001;913:331-340.
16. Desai MJ, Armstrong DW. Analysis of native amino acid and peptide enantiomers by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. J Mass Spectrom 2004;39:177-187.
17. Desai MJ, Armstrong DW. Transforming chiral liquid chromatography methodologies into more sensitive liquid chromatography - electrospray ionization mass spectrometry without losing enantioselectivity. J Chromatogr A 2004;1035:203-210.
18. Desai MJ, Armstrong DW. Analysis of derivatized and underivatized theanine enantiomers by high-performance liquid chromatography/atmospheric pressure ionization-mass spectrometry. Rapid Commun Mass Spectrom 2004;18:251-256.
19. Hem A, Smith AJ, Solberg P. Saphenous vein puncture for blood sampling of the mouse, rat, hamster, gerbil, guinea pig, ferret and mink. Lab Anim 1998;32:364-368.
20. Poison C, Sarkar P, Incledon B, Ragucaran V, Grant R. Optimization of protein precipitation based upon effectiveness of protein removal and ionization effect in liquiD-chromatography-tandem mass spectrometry. J Chromatogr B 2003;785:263-275.
21. Carducci C, Birarelli M, Leuzzi V, Santagata G, Serafini P, Antonozzi I. Automated method for the measurement of amino acids in urine by high-performance liquid chromatography. J Chromatogr A 1996;729: 173-180.
22. Carpino LA, Cohen BJ, Stephens KE, Sadat-Aalaee SY, Tien JH, Langridge DC. ((9-Flurorenylmethyl)oxy)carbonyl (Fmoc) amino acid chlorides. Synthesis, characterization, and applications to the rapid synthesis of short peptide segments. J Org Chem 1986;51:3732-3734.
23. Tsuge H, Sano S, Hayakawa T, Kakuda T, Unno T. Theanine, γ-glutamylethylamide, is metabolized by renal phosphate-independent glutaminase. Biochim Biophys Acta 2003;1620:47-53.
24. Kitaoka S, Hayashi H, Yokogoshi H, Suzuki Y. Transmural potential changes associated with the in vitro absorption of theanine in the guinea pig intestine. Biosci Biotech Biochem 1996;60:1768-1771.
25. Oguri S, Kumazaki M, Kitou R, Nonoyama H, Tooda N. Elucidation of intestinal absorption of D,L-amino acid enantiomers and aging in rats. Biochim Biophys Acta 1999;1472:107-114.
26. Silbernagl S, Volkl H. Amino acid reabsorption in the proximal tubule of rat kidney: stereospecificity and passive diffusion studied by continuous microperfusion. Pflugers Arch 1977;367:221-227.
27. Lehmann WD, Theobald N, Fischer R, Heinrich HC. Stereospecificity of phenylalanine plasma kinetics and hydroxylation in man following oral application of a stable isotope-labeled pseudo-racemic mixture of L- and D-phenylalanine. Clin Chim Acta 1983;128:181-198.
28. Armstrong DW, Gasper MP, Lee SH, Ercal N, Zukowski J. Factors controlling the level and determination of D-amino acids in the urine and plasma of laboratory rodents. Amino Acids 1993;5:299-315.
29. Bruckner H, Schieber A. Ascertainment of D-amino acids in germ-free, gnotobiotic and normal laboratory rats. Biomed Chromatogr 2001;15: 257-262.