Stereochemistry of the Black Tea Pigments Theacitrins A and C

Journal of Natural Products

Volumn 79, Issue 1, 2016, Pages 189-195

  Matsuo, Yosuke ^a   Okuda, Keita ^a   Morikawa, Hitomi ^a   Oowatashi, Ryosuke ^a   Saito, Yoshinori ^a   Tanaka, Takashi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPIGALLOCATECHIN; EPIGALLOCATECHIN GALLATE; POLYPHENOL DERIVATIVE; THEACITRIN A; THEACITRIN C; UNCLASSIFIED DRUG; CATECHIN; GALLOCATECHIN; PIGMENT; POLYPHENOL; TEA;

ABSORPTION; AQUEOUS SOLUTION; AROMATIZATION; ARTICLE; CIRCULAR DICHROISM; COVALENT BOND; DEGRADATION; DIASTEREOISOMER; DIMERIZATION; HEAT TREATMENT; HYDROLYSIS; NONHUMAN; OXIDATION; OXIDATIVE COUPLING; STEREOCHEMISTRY; STEREOISOMERISM; TEA; ANALOGS AND DERIVATIVES; CAMELLIA SINENSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION REACTION;

CAMELLIA SINENSIS; CATECHIN; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; PIGMENTS, BIOLOGICAL; POLYPHENOLS; TEA;

EID: 84956786738     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00832     Document Type: Article

References (26)

1. Crozier, A.; Jaganath, I. B.; Clifford, M. N. Nat. Prod. Rep. 2009, 26, 1001-1043 10.1039/b802662a
2. Quideau, S.; Deffieux, D.; Douat-Casassus, C.; Pouységu, L. Angew. Chem., Int. Ed. 2011, 50, 586-621 10.1002/anie.201000044
3. Cheynier, V. Phytochem. Rev. 2012, 11, 153-177 10.1007/s11101-012-9242-8
4. Haslam, E. Phytochemistry 2003, 64, 61-73 10.1016/S0031-9422(03)00355-8
5. Drynan, J. W.; Clifford, M. N.; Obuchowicz, J.; Kuhnert, N. Nat. Prod. Rep. 2010, 27, 417-462 10.1039/b912523j
6. Tanaka, T.; Matsuo, Y.; Kouno, I. Int. J. Mol. Sci. 2010, 11, 14-40 10.3390/ijms11010014
7. Li, S.; Lo, C.-Y.; Pan, M.-H.; Lai, C.-S.; Ho, C.-T. Food Funct. 2013, 4, 10-18 10.1039/C2FO30093A
8. Davis, A. L.; Lewis, J. R.; Cai, Y.; Powell, C.; Davis, A. P.; Wilkins, J. P. G.; Pudney, P.; Clifford, M. N. Phytochemistry 1997, 46, 1397-1402 10.1016/S0031-9422(97)00508-6
9. Matsuo, Y.; Li, Y.; Watarumi, S.; Tanaka, T.; Kouno, I. Tetrahedron 2011, 67, 2051-2059 10.1016/j.tet.2011.01.058
10. Qi, X. Fitoterapia 2010, 81, 205-209 10.1016/j.fitote.2009.09.004
11. Nugroho, A. E.; Morita, H. J. Nat. Med. 2014, 68, 1-10 10.1007/s11418-013-0768-x
12. Li, X.-C.; Ferreira, D.; Ding, Y. Curr. Org. Chem. 2010, 14, 1678-1697 10.2174/138527210792927717
13. Lodewyk, M. W.; Siebert, M. R.; Tantillo, D. J. Chem. Rev. 2012, 112, 1839-1862 10.1021/cr200106v
14. Di Micco, S.; Chini, M. G.; Riccio, R.; Bifulco, G. Eur. J. Org. Chem. 2010, 2010, 1411-1434 10.1002/ejoc.200901255
15. Willoughby, P. H.; Jansma, M. J.; Hoye, T. R. Nat. Protoc. 2014, 9, 643-660 10.1038/nprot.2014.042
16. Smith, S. G.; Goodman, J. M. J. Am. Chem. Soc. 2010, 132, 12946-12959. Web applet for DP4: http://www-jmg.ch.cam.ac.uk/tools/nmr/DP4/.
17. Matsuo, Y.; Tanaka, T.; Kouno, I. Tetrahedron 2006, 62, 4774-4783 10.1016/j.tet.2006.03.021
18. Matsuo, Y.; Tanaka, T.; Kouno, I. Tetrahedron Lett. 2009, 50, 1348-1351 10.1016/j.tetlet.2009.01.030
19. Yanase, E.; Sawaki, K.; Nakatsuka, S. Synlett 2005, 2661-2663 10.1055/s-2005-917094
20. Nonaka, G.; Kawahara, O.; Nishioka, I. Chem. Pharm. Bull. 1983, 31, 3906-3914 10.1248/cpb.31.3906
21. Tanaka, T.; Mine, C.; Inoue, K.; Matsuda, M.; Kouno, I. J. Agric. Food Chem. 2002, 50, 2142-2148 10.1021/jf011301a
22. Nishimura, M.; Fukuda, C.; Murata, M.; Homma, S. J. Sci. Food Agric. 2003, 83, 1156-1162 10.1002/jsfa.1518
23. Tanaka, T.; Watarumi, S.; Matsuo, Y.; Kamei, M.; Kouno, I. Tetrahedron 2003, 59, 7939-7947 10.1016/j.tet.2003.08.025
24. Stewart, J. J. P. MOPAC2012; Stewart Computational Chemistry: Colorado Springs, CO, 2012.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, M. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01; Gaussian, Inc.: Wallingford, CT, 2010.
26. Dennington, R.; Keith, T.; Millam, J. GaussView, Version 5.0.9; Semichem Inc.: Shawnee Mission, KS, 2009.