Configurational studies of complexes of tea catechins with caffeine and various cyclodextrins

Planta Medica

Volumn 77, Issue 11, 2011, Pages 1099-1109

  Ishizu, Takashi ^a   Kajitani, Shinya ^a   Tsutsumi, Hiroyuki ^a   Sato, Takashi ^a   Yamamoto, Hideji ^a   Hirata, Chikako ^a  

^a FUKUYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CAFFEINE; CATECHIN; CYCLODEXTRIN DERIVATIVE; ENT GALLOCATECHIN 3 O GALLATE; EPIGALLOCATECHIN GALLATE; GAMMA CYCLODEXTRIN; HYDROXYL GROUP; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; STEREOCHEMISTRY; TEA; X RAY CRYSTALLOGRAPHY;

CAFFEINE; CATECHIN; CRYSTALLOGRAPHY, X-RAY; CYCLODEXTRINS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; STEREOISOMERISM; TEA; WATER;

EID: 79960730155     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0030-1270982     Document Type: Review

References (31)

1. Hemingway R W., Foo L Y., Porter L J. Linkage isomerism in trimeric and polymeric 2,3-cis procyanidins. J Chem Soc [Perkin I] 1982 1209-1216
2. Porter L J. Flavans and proanthocyanidins. Harborne JB The flavonoids: advances in research since 1980. London Chapmann and Hall 1988 21-62
3. Kuroda Y, Hara Y. Health effects of tea and its catechins. New York, Boston, Dordrecht, London, Moscow Kluwer Academic/Plenum Publishers 2004 11-60
4. Lambert J D., Yang C S. Cancer chemopreventive activity and bioavailability of tea and tea polyphenols. Mutat Res 2003 523524 201-208 (Pubitemid 36293247)
5. Ahmad N, Cheng P, Mukhtar H. Cell cycle dysregulation by green tea polyphenol epigallocatechin-3-gallate. Biochem Biophys Res Commun 2000 275 328-334
6. Maeda-Yamamoto M, Kawahara H, Tahara N, Tsuji K, Hara Y, Isemura M. Effects of tea polyphenols on the invasion and matrix metalloproteinases activities of human fibrosarcoma HT1080 cells. J Agric Food Chem 1999 47 2350-2354 (Pubitemid 29325123)
7. Sazuka M, Imazawa H, Shoji Y, Mita T, Hara Y, Isemura M. Inhibition of collagenases from mouse lung carcinoma cells by green tea catechins and black tea theaflavins. Biosci Biotechnol Biochem 1997 61 1504-1506 (Pubitemid 127472971)
8. Hashimoto F, Ono M, Masuoka C, Ito Y, Sakata Y, Shimizu K, Nonaka G, Nishioka I, Nohara T. Evaluation of the anti-oxidative effect (in vitro) of tea polyphenols. Biosci Biotechnol Biochem 2003 67 396-401 (Pubitemid 39251999)
9. Kimura M, Umegaki K, Kasuya Y, Sugisawa A, Higuchi M. The relation between single/double or repeated tea catechin ingestions and plasma antioxidant activity in humans. Eur J Clin Nutr 2002 56 1186-1193 (Pubitemid 36124407)
10. Hayashi N, Ujihara T. Biting effect' stabilizing gallate-type catechin/quaternary ammonium ion complexes. Tetrahedron 2007 63 9802-9809 (Pubitemid 47238960)
11. Tezuka M, Suzuki H, Suzuki Y, Hara Y, Okada S. Inactivation effect of tea leaf catechins on human type-A influenza virus. Jpn J Toxicol Environ Health 1997 43 311-315 (Pubitemid 28011364)
12. Okabe S, Suganuma M, Hayashi M, Sueoka E, Komori A, Fujiki H. Mechanisms of growth inhibition of human lung cancer cell line, PC-9, by tea polyphenols. Jpn J Cancer Res 1997 88 639-643 (Pubitemid 27394047)
13. 2+ mediated oxidative modification of low density lipoprotein. Biol Pharm Bull 1994 17 1567-1572
14. Hara Y, Watanabe M. Antibacterial activity of tea polyphenols against clostridium botulinum. Nippon Shokuhin Kogyo Gakkaishi 1989 36 951-955
15. Martin R, Lilley T H., Falshaw C P., Haslam E, Begley M J., Magnolato D. The caffeine-potassium chlorogenate molecular complex. Phytochemistry 1986 26 273-279
16. Gaffney S H., Martin R, Lilley T H., Haslam E, Magnolato D. The association of polyphenols with caffeine and - and -cyclodextrin in aqueous media. J Chem Soc Chem Commun 1986 2 107-109 (Pubitemid 17010313)
17. Horman I, Viani R. The nature and conformation of the caffeine-chlorogenate complex of coffee. J Food Sci 1972 37 925-927
18. Maruyama N, Suzuki Y, Sakata K, Yagi A, Ina K. NMR spectroscopic and computer graphics studies on the creaming down of tea. Proceedings of the International Symposium on Tea Science, Shizuoka-shi, Japan 1991 145-149
19. Cai Y, Gaffney S H., Lilley T H., Magnolato D, Martin R, Spencer C M., Haslam E. Polyphenol interactions. Part 4. Model studies with caffeine and cyclodextrins. J Chem Soc [Perkin II] 1990 2197-2209
20. 1H-NMR. Biosci Biotechnol Biochem 2004 68 2512-2518 (Pubitemid 40218181)
21. Tsutsumi H, Sato T, Ishizu T. Offset - interaction in crystal structure of ()-gallocatechin-3- O -gallate. Chem Pharm Bull 2010 58 572-574
22. Ishizu T, Tsutsumi H, Sato T, Yamamoto H, Shiro M. Crystal structure of complex of gallocatechin gallate and caffeine. Chem Lett 2009 38 230-231
23. Ishizu T, Tsutsumi H, Sato T. Interaction between gallocatechin gallate and caffeine in crystal structure of 1:2 and 2:2 complexes. Tetrahedron Lett 2009 50 4121-4124
24. Wong J W., Yuen K H. Inclusion complexation of artemisinin with -, -, and -cyclodextrins. Drug Dev Indian Pharm 2003 29 1035-1044
25. Ishizu T, Kajitani S, Tsutsumi H, Yamamoto H, Harano K. Diastereomeric difference of inclusion modes between ()-epicatechin gallate, ()-epigallocatechin gallate and (+)-gallocatechin gallate, with -cyclodextrin in aqueous solvent. Magn Reson Chem 2007 46 448-456
26. Ishizu T, Hirata C, Yamamoto H, Harano K. Structure and intramolecular flexibility of -cyclodextrin complex with ()-epigallocatechin gallate in aqueous solvent. Magn Reson Chem 2006 44 776-783 (Pubitemid 44113938)
27. Ishizu T, Tsutsumi H, Yamamoto H, Harano K. NMR spectroscopic characterization of inclusion complexes comprising cyclodextrins and gallated catechins in aqueous solution: cavity size dependency. Magn Reson Chem 2008 47 283-287
28. Giacovazzo C. Fundamentals of crystallography, 2nd edition. IUCr texts on crystallography 7. Oxford IUCr/Oxford University Press 2002 237-243
29. Job P. Formation and stability of inorganic complexes in solution. Ann Chem 1928 9 113-203
30. Karplus M, Anderson DH. Valence-bond interpretation of electron-coupled nuclear spin interactions; application to methane. J Chem Phys 1959 30 6-10
31. WinMOPAC V3.9. Tokyo Fujitsu Ltd 2004