Reinvestigation of the Stereochemistry of the C-Glycosidic Ellagitannins, Vescalagin and Castalagin

Organic Letters

Volumn 17, Issue 1, 2015, Pages 46-49

  Matsuo, Yosuke ^a   Wakamatsu, Hatsumi ^a   Omar, Mohamed ^a   Tanaka, Takashi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TANNIN; VESCALAGIN;

CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; OAK;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROLYZABLE TANNINS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; QUERCUS;

EID: 84925285404     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503212v     Document Type: Article

References (44)

1. Nonaka, G.; Nakayama, S.; Nishioka, I. Chem. Pharm. Bull. 1989, 37, 2030-2036
2. Viriot, C.; Scalbert, A.; Lapierre, C.; Moutounet, M. J. Agric. Food Chem. 1993, 41, 1872-1879
3. König, M.; Scholz, E.; Hartmann, R.; Lehmann, W.; Rimpler, H. J. Nat. Prod. 1994, 57, 1411-1415
4. Zhentian, L.; Jervis, J.; Helm, R. F. Phytochemistry 1999, 51, 751-756
5. Ito, H.; Yamaguchi, K.; Kim, T.-H.; Khennouf, S.; Gharzouli, K.; Yoshida, T. J. Nat. Prod. 2002, 65, 339-345
6. Jordão, A. M.; Ricardo-da-Silva, J. M.; Laureano, O. Holzforschung 2007, 61, 155-160
7. Fernandes, A.; Fernandes, I.; Cruz, L.; Mateus, N.; Cabral, M.; de Freitas, V. J. Agric. Food Chem. 2009, 57, 11154-11160
8. Omar, M.; Matsuo, Y.; Maeda, H.; Saito, Y.; Tanaka, T. Phytochem. Lett. 2013, 6, 486-490
9. Alañón, M. E.; Castro-Vázquez, L.; Díaz-Maroto, M. C.; Gordon, M. H.; Perez-Coello, M. S. Food Chem. 2011, 128, 997-1002
10. Vilhelmova, N.; Jacquet, R.; Quideau, S.; Stoyanova, A.; Galabov, A. S. Antiviral Res. 2011, 89, 174-181
11. Auzanneau, C.; Montaudon, D.; Jacquet, R.; Puyo, S.; Pouységu, L.; Deffieux, D.; Elkaoukabi-Chaibi, A.; De Giorgi, F.; Ichas, F.; Quideau, S.; Pourquier, P. Mol. Pharmacol. 2012, 82, 134-141
12. Glabasnia, A.; Hofmann, T. J. Agric. Food Chem. 2006, 54, 3380-3390
13. Mayer, W.; Gabler, W.; Riester, A.; Korger, H. Justus Liebigs Ann. Chem. 1967, 707, 177-181
14. Mayer, W.; Jochims, J. C. Justus Liebigs Ann. Chem. 1969, 721, 186-193
15. Mayer, W.; Seitz, H.; Jochims, J. C.; Schauerte, K.; Schilling, G. Justus Liebigs Ann. Chem. 1971, 751, 60-68
16. Nonaka, G.; Ishimaru, K.; Watanabe, M.; Nishioka, I.; Yamauchi, T.; Wan, A. S. C. Chem. Pharm. Bull. 1987, 35, 217-220
17. Nonaka, G.; Sakai, T.; Tanaka, T.; Mihashi, K.; Nishioka, I. Chem. Pharm. Bull. 1990, 38, 2151-2156
18. Vivas, N.; Laguerre, M.; Pianet de Boissel, I.; Vivas de Gaulejac, N.; Nonier, M.-F. J. Agric. Food Chem. 2004, 52, 2073-2078
19. Vivas, N.; Laguerre, M.; Glories, Y.; Bourgeois, G.; Vitry, C. Phytochemistry 1995, 39, 1193-1199
20. Haasnoot, C. A. G.; De Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783-2792
21. Quideau, S.; Deffieux, D.; Douat-Casassus, C.; Pouységu, L. Angew. Chem., Int. Ed. 2011, 50, 586-621
22. Pouységu, L.; Deffieux, D.; Malik, G.; Natangelo, A.; Quideau, S. Nat. Prod. Rep. 2011, 28, 853-874
23. Chemistry and Biology of Ellagitannins: An Underestimated Class of Bioactive Plant Polyphenols; Quideau, S., Ed.; World Scientific Publishing: Singapore, 2009.
24. Salminen, J.-P. In Recent Advances in Polyphenol Research; Romani, A.; Lattanzio, V.; Quideau, S., Eds.; Wiley: Chichester, U.K., 2014; Vol. 4, pp 83-113.
25. Salminen, J.-P.; Karonen, M.; Sinkkonen, J. Chem.-Eur. J. 2011, 17, 2806-2816
26. Barbehenn, R. V.; Constabel, C. P. Phytochemistry 2011, 72, 1551-1565
27. Yoshida, T.; Amakura, Y.; Yoshimura, M. Int. J. Mol. Sci. 2010, 11, 79-106
28. Tantillo, D. J. Nat. Prod. Rep. 2013, 30, 1079-1086
29. Nugroho, A. E.; Morita, H. J. Nat. Med. 2014, 68, 1-10
30. Zhao, S.-D.; Shen, L.; Luo, D.-Q.; Zhu, H.-J. Curr. Org. Chem. 2011, 15, 1843-1862
31. Li, X.-C.; Ferreira, D.; Ding, Y. Curr. Org. Chem. 2010, 14, 1678-1697
32. Berova, N.; Bari, L. D.; Pescitelli, G. Chem. Soc. Rev. 2007, 36, 914-931
33. Lodewyk, M. W.; Siebert, M. R.; Tantillo, D. J. Chem. Rev. 2012, 112, 1839-1862
34. Micco, S. D.; Chini, M. G.; Riccio, R.; Bifulco, G. Eur. J. Org. Chem. 2010, 1411-1434
35. Okuda, T.; Yoshida, T.; Hatano, T.; Koga, T.; Toh, N.; Kuriyama, K. Tetrahedron Lett. 1982, 23, 3937-3940
36. Mayer, W.; Einwiller, A.; Jochims, J. C. Justus Liebigs Ann. Chem. 1967, 707, 182-189
37. Mayer, W.; Kuhlmann, F.; Schilling, G. Justus Liebigs Ann. Chem. 1971, 747, 51-59
38. Bally, T.; Rablen, P. R. J. Org. Chem. 2011, 76, 4818-4830
39. Hervé du Penhoat, C. L. M.; Michon, V. M. F.; Peng, S.; Viriot, C.; Scalbert, A.; Gage, D. J. Chem. Soc., Perkin Trans. 1 1991, 1653-1660
40. Tanaka, T.; Ueda, N.; Shinohara, H.; Nonaka, G.; Fujioka, T.; Mihashi, K.; Kouno, I. Chem. Pharm. Bull. 1996, 44, 2236-2242
41. Ishimaru, K.; Nonaka, G.; Nishioka, I. Chem. Pharm. Bull. 1987, 35, 602-610
42. Lin, T.-C.; Tanaka, T.; Nonaka, G.; Nishioka, I.; Young, T.-J. Chem. Pharm. Bull. 1991, 39, 1144-1147
43. Nonaka, G.; Ishimaru, K.; Mihashi, K.; Iwase, Y.; Ageta, M.; Nishioka, I. Chem. Pharm. Bull. 1988, 36, 857-869
44. Petit, E.; Lefeuvre, D.; Jacquet, R.; Pouységu, L.; Deffieux, D.; Quideau, S. Angew. Chem., Int. Ed. 2013, 52, 11530-11533