Biomimetic one-pot preparation of a black tea polyphenol theasinensin A from epigallocatechin gallate by treatment with copper(II) chloride and ascorbic acid

Chemical and Pharmaceutical Bulletin

Volumn 59, Issue 9, 2011, Pages 1183-1185

  Shii, Takuya ^a   Miyamoto, Makoto ^a   Matsuo, Yosuke ^a   Tanaka, Takashi ^a   Kouno, Isao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Black tea; Copper(II) chloride; Dehydrotheasinensin A; Epigallocatechin gallate; Theasinensin A

Indexed keywords

ASCORBIC ACID; COPPER CHLORIDE; EPIGALLOCATECHIN GALLATE; POLYPHENOL DERIVATIVE; THEASINENSIN A; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; ONE POT SYNTHESIS; STEREOCHEMISTRY; TEA; THEA NIGRA;

ASCORBIC ACID; BENZOPYRANS; BIOMIMETIC MATERIALS; CATECHIN; COPPER; DIMERIZATION; OXIDATION-REDUCTION; PHENOLS; POLYPHENOLS; STEREOISOMERISM; TEA;

EID: 80052292128     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.59.1183     Document Type: Article

References (30)

1. Ho C.-T., Lin J.-K., Shahidi F., "Tea and Tea Products, Chemistry and Health-Promoting Properties," CRC Press, Boca Raton, 2009.
2. Ferretti A., Flanagan V. P., Bondarovich H. A., Gianturco M. A., J. Agric. Food Chem., 16, 756-761 (1968).
3. Nonaka G., Kawahara O., Nishioka I., Chem. Pharm. Bull., 31, 3906-3914 (1983).
4. Hashimoto F., Nonaka G., Nishioka I., Chem. Pharm. Bull., 36, 1676-1684 (1988).
5. Hou D.-X., Masuzaki S., Tanigawa S., Hashimoto F., Chen J., Sogo T., Fujii M., J. Agric. Food Chem., 58, 12735-12743 (2010).
6. Neilson A. P., Song B. J., Sapper T. N., Bomser J. A., Ferruzzi M. G., Nutr. Res., 30, 327-340 (2010).
7. Toshima A., Matsui T., Noguchi M., Qiu J., Tamaya K., Miyata Y., Tanaka T., Tanaka K., J. Sci. Food Agric., 90, 1545-1550 (2010).
8. Tanaka T., Mine C., Watarumi S., Fujioka T., Mihashi K., Zhang Y.-J., Kouno I., J. Nat. Prod., 65, 1582-1587 (2002).
9. Tanaka T., Watarumi S., Matsuo Y., Kamei M., Kouno I., Tetrahedron, 59, 7939-7947 (2003).
10. Matsuo Y., Yamada Y., Tanaka T., Kouno I., Phytochemistry, 69, 3054-3061 (2008).
11. Li Y., Tanaka T., Kouno I., Phytochemistry, 68, 1081-1088 (2007).
12. Gardner E. J., Ruxton C. H. S., Leeds A. R., Eur. J. Clin. Nutr., 61, 3-18 (2007).
13. Ruxton C. H. S., Nutr. Bull., 33, 91-101 (2008).
14. Kusano R., Andou H., Fujieda M., Tanaka T., Matsuo Y., Kouno I., Chem. Pharm. Bull., 56, 266-272 (2008).
15. Takino Y., Imagawa H., Horikawa H., Tanaka A., Agric. Biol. Chem., 28, 64-71 (1964).
16. Takino Y., Ferretti A., Flanagan V., Gianturco M., Vogel M., Tetrahedron Lett., 6, 4019-4025 (1965).
17. Collier P. D., Bryce T., Mallows R., Thomas P. E., Frost D. J., Korver O., Wilkins C. K., Tetrahedron, 29, 125-142 (1973).
18. Tanaka T., Mine C., Inoue K., Matsuda M., Kouno I., J. Agric. Food Chem., 50, 2142-2148 (2002).
19. Tanaka T., Matsuo Y., Kouno I., J. Agric. Food Chem., 53, 7571-7578 (2005).
20. Krebs B., Merkel M., Rompel A., J. Argent. Chem. Soc., 92, 1-15 (2004).
21. Decker H., Tuczek F., Trends Biochem. Sci., 25, 392-397 (2000).
22. Tanaka T., Matsuo Y., Kouno I., Int. J. Mol. Sci., 11, 14-40 (2010).
23. Haslam E., Phytochemistry, 64, 61-73 (2003).
24. Roberts E. A. H., Chem. Ind., 1957, 1354-1355 (1957).
25. Wardman P., J. Phys. Chem. Ref. Data, 18, 1637-1755 (1989).
26. Hashimoto F., Nonaka G., Nishioka I., Chem. Pharm. Bull., 40, 1383-1389 (1992).
27. Tanaka T., Miyata Y., Tamaya K., Kusano R., Matsuo Y., Tamaru S., Tanaka K., Matsui T., Maeda M., Kouno I., J. Agric. Food Chem., 57, 5816-5822 (2009).
28. Matsuo Y., Tanaka T., Kouno I., Tetrahedron Lett., 50, 1348-1351 (2009).
29. Tanaka T., Inoue K., Betsumiya Y., Mine C., Kouno I., J. Agric. Food Chem., 49, 5785-5789 (2001).
30. Tanaka T., Mine C., Kouno I., Tetrahedron, 58, 8851-8856 (2002).