Structural and conformational analysis of proanthocyanidins from parapiptadenia rigida and their wound-healing properties

Journal of Natural Products

Volumn 74, Issue 6, 2011, Pages 1427-1436

  Schmidt, Cleber A ^a   Murillo, Renato ^b   Heinzmann, Berta ^c   Laufer, Stefan ^d   Wray, Victor ^e   Merfort, Irmgard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b UNIVERSIDAD DE COSTA RICA   (Costa Rica)

^c FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^d UNIVERSITY OF TÜBINGEN   (Germany)

^e HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

(4ALPHA-8) BIS 4' O METHYLGALLOCATECHIN; 4' O METHYLGALLOCATECHIN (4ALPHA-8) 4' O METHYLEPIGALLOCATECHIN; EPICATECHIN (4BETA-8) 4' O METHYLGALLOCATECHIN; EPIGALLOCATECHIN (4BETA-8) 4' O METHYLGALLOCATECHIN; EPIGALLOCATECHIN (4BETA-8) EPIGALLOCATECHIN 3 O GALLATE; PARAPIPTADENIA RIGIDA EXTRACT; PLANT EXTRACT; PROANTHOCYANIDIN DERIVATIVE; PRODELPHINIDIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DRUG CONFORMATION; DRUG ISOLATION; DRUG STRUCTURE; MEDICINAL PLANT; MOUSE; NONHUMAN; PARAPIPTADENIA RIGIDA; STRUCTURE ACTIVITY RELATION; WOUND HEALING;

BRAZIL; CRYSTALLOGRAPHY, X-RAY; FABACEAE; HUMANS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT BARK; PROANTHOCYANIDINS; WOUND HEALING;

PARAPIPTADENIA RIGIDA;

EID: 79959707671     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200158g     Document Type: Article

References (57)

1. Schmidt, C. A.; Murillo, R.; Bruhn, T.; Bringmann, G.; Goettert, M.; Heinzmann, B.; Brecht, V.; Laufer, S. A.; Merfort, I. J. Nat. Prod. 2010, 73, 2035-2041
2. Avancini, C.; Wiest, J. M.; Dall'Agnol, R.; Haas, J. S.; von Poser, G. L. Lat. Am. J. Pharm. 2008, 27, 894-899
3. de Souza, G. C.; Haas, A. P. S.; von Poser, G. L.; Schapoval, E. E. S.; Elisabetsky, E. J. Ethnopharmacol. 2004, 90, 135-143
4. Souza, G. C.; Hass, A. P. S.; Poser, G. L. V.; Elisabetsky, E. Rev. Bras. Plant. Med. 2004, 6, 83-91
5. Ferreira, D.; Slade, D. Nat. Prod. Rep. 2002, 19, 517-541
6. Hemingway, R. W.; Karchesy, J. J. Chemistry and Significance of Condensed Tannins; Plenum Press: New York, 1989.
7. Aron, P. M.; Kennedy, J. A. Mol. Nutr. Food Res. 2008, 52, 79-104
8. de la Iglesia, R.; Milagro, F. I.; Campion, J.; Boque, N.; Martinez, J. A. Biofactors 2010, 36, 159-168
9. Sen, C. K.; Khanna, S.; Gordillo, G.; Bagchi, D.; Bagchi, M.; Roy, S. Ann. N.Y. Acad. Sci. 2002, 957, 239-249
10. Nonaka, G. I.; Muta, M.; Nishioka, I. Phytochemistry 1983, 22, 237-241
11. de Mello, J. P.; Petereit, F.; Nahrstedt, A. Phytochemistry 1996, 41, 807-813
12. Sun, D. W.; Zhao, Z. C.; Wong, H.; Foo, L. Y. Phytochemistry 1988, 27, 579-583
13. Saijo, R.; Nonaka, G.; Nishioka, I. Phytochemistry 1989 28, 2443-2446
14. Nonaka, G.; Aiko, Y.; Aritake, K.; Nishioka, I. Chem. Pharm. Bull. 1992, 40, 2671-2673
15. Hashimoto, F.; Nonaka, G.; Nishioka, I. Chem. Pharm. Bull. 1989, 37, 3255-3263
16. Danne, A.; Petereit, F.; Nahrstedt, A. Phytochemistry 1994, 37, 533-538
17. Lakenbrink, C.; Engelhardt, U. H.; Wray, V. J. Agric. Food Chem. 1999, 47, 4621-4624
18. Hatano, T.; Hemingway, R. W. J. Chem. Soc., Perkin Trans. II 1997, 1035-1043
19. Shoji, T.; Mutsuga, M.; Nakamura, T.; Kanda, T.; Akiyama, H.; Goda, Y. J. Agric. Food Chem. 2003, 51, 3806-3813
20. Fletcher, A. C.; Porter, L. J.; Haslam, E.; Gupta, R. K. J. Chem. Soc., Perkin Trans. I 1977, 1628-1637
21. Hemingway, R. W.; Tobiason, F. L.; Mcgraw, G. W.; Steynberg, J. P. Magn. Reson. Chem. 1996, 34, 424-433
22. Davis, A. L.; Cai, Y.; Davies, A. P.; Lewis, J. R. Magn. Reson. Chem. 1996, 34, 887-890
23. Shen, C. C.; Chang, Y. S.; Ho, L. K. Phytochemistry 1993, 34, 843-845
24. Tarascou, I.; Barathieu, K.; Simon, C.; Ducasse, M. A.; Andre, Y.; Fouquet, E.; Dufourc, E. J.; de Freitas, V.; Laguerre, M.; Pianet, I. Magn. Reson. Chem. 2006, 44, 868-880
25. Botha, J. J.; Ferreira, D.; Roux, D. G. J. Chem. Soc., Perkin Trans. I 1981, 1235-1245
26. Slade, D.; Ferreira, D.; Marais, J. P. J. Phytochemistry 2005, 66, 2177-2215
27. Ding, Y. Q.; Li, X. C.; Ferreira, D. J. Nat. Prod. 2010, 73, 435-440
28. Danne, A.; Petereit, F.; Nahrstedt, A. Phytochemistry 1993, 34, 1129-1133
29. Tanaka, T.; Ishida, N.; Ishimatsu, M.; Nonaka, G.; Nishioka, I. Chem. Pharm. Bull. 1992, 40, 2092-2098
30. Foo, L. Y.; Lu, Y.; Mcnabb, W. C.; Waghorn, G.; Ulyatt, M. J. Phytochemistry 1997, 45, 1689-1696
31. Lee, M. W.; Morimoto S.; Nonaka, G. I.; Nishioka, I. Phytochemistry 1992, 31, 2117-2120
32. Malik, A.; Kuliev, Z. A.; Akhmedov, U. A.; Vdovin, A. D.; Abdullaev, N. D. Khim. Prir. Soedin. 1997, 232-237
33. Zhang, Y. J.; Tanaka, T.; Iwamoto, Y.; Yang, C. R.; Kouno, I. J. Nat. Prod. 2000, 63, 1507-1510
34. Yokozawa, T.; Kashiwada, Y.; Hattori, M.; Chung, H. Y. Biol. Pharm. Bull. 2002, 25, 748-752
35. Yokozawa, T.; Nakagawa, T. Food Chem. Toxicol. 2004, 42, 975-981
36. de Mello, J. C. P.; Petereit, F.; Nahrstedt, A. Phytochemistry 1999, 51, 1105-1107
37. Sun, D. W.; Wong, H.; Foo, L. Y. Phytochemistry 1987, 26, 1825-1829
38. Balas, L.; Vercauteren, J.; Laguerre, M. Magn. Reson. Chem. 1995, 33, 85-94
39. Steynberg, J. P.; Brandt, E. V.; Ferreira, D.; Helfer, C. A.; Mattice, W. L.; Gornik, D.; Hemingway, R. W. Magn. Reson. Chem. 1995, 33, 611-620
40. Porter, L. J.; Wong, R. Y.; Benson, M.; Chan, B. G.; Vishwanadhan, V. N.; Gandour, R. D.; Mattice, W. L. J. Chem. Res. Synop. 1986, 86-87
41. Ferreira, D.; Bekker, R. Nat. Prod. Rep 1996, 13, 411-433
42. Haslam, E. Phytochemistry 1977, 16, 1625-1640
43. Ferreira, D.; Steynberg, J. P.; Roux, D. G.; Brandt, E. V. Tetrahedron 1992, 48, 1743-1803
44. Ferreira, D.; Marais, J. P. J.; Coleman, C. M.; Slade, D. Comprehensive Natural Products II; Elsevier: Amsterdam, 2010; Chapter 6.18, pp 605-659.
45. Fronza, M.; Heinzmann, B.; Hamburger, M.; Laufer, S.; Merfort, I. J. Ethnopharmacol. 2009, 126, 463-467
46. Zhang, Y. J.; Nagao, T.; Tanaka, T.; Yang, C. R.; Okabe, H.; Kouno, I. Biol. Pharm. Bull. 2004, 27, 251-255
47. Tourino, S.; Lizarraga, D.; Carreras, A.; Lorenzo, S.; Ugartondo, V.; Mitjans, M.; Vinardell, M. P.; Julia, L.; Cascante, M.; Torres, J. L. Chem. Res. Toxicol. 2008, 21, 696-704
48. Khanna, S.; Venojarvi, M.; Roy, S.; Sharma, N.; Trikha, P.; Bagchi, D.; Bagchi, M.; Sen, C. K. Free Radical Biol. Med. 2002, 33, 1089-1096
49. Khanna, S.; Roy, S.; Bagchi, D.; Bagchi, M.; Sen, C. K. Free Radical Biol. Med. 2001, 31, 38-42
50. Appleton, I. Idrugs 2003, 6, 1067-1072
51. Mackenzie, G. G.; Carrasquedo, F.; Delfino, J. M.; Keen, C. L.; Fraga, C. G.; Oteiza, P. I. FASEB J. 2003, 17, 167-192
52. Mackenzie, G. G.; Delfino, J. M.; Keen, C. L.; Fraga, C. G.; Oteiza, P. I. Biochem. Pharmacol. 2009, 78, 1252-1262
53. Schmidt, C.; Fronza, M.; Goettert, M.; Geller, F.; Luik, S.; Flores, E. M. M.; Bittencourt, C. F.; Zanetti, G. D.; Heinzmann, B. M.; Laufer, S.; Merfort, I. J. Ethnopharmacol. 2009, 122, 523-532
54. Selinummi, J.; Seppala, J.; Yli-Harja, O.; Puhakka, J. A. Biotechniques 2005, 39, 859-863
55. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63
56. Karplus, M. J. Am. Chem. Soc. 1963, 85, 2870-2871
57. Aydin, R.; Gunther, H. Magn. Reson. Chem. 1990, 28, 448-457