New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense

Journal of Natural Products

Volumn 67, Issue 7, 2004, Pages 1119-1124

  Abdel Halim, Osama Bashir ^a,b   Morikawa, Toshio ^b   Ando, Shin ^b   Matsuda, Hisashi ^b   Yoshikawa, Masayuki ^b  

^a MANSOURA UNIVERSITY   (Egypt)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 HYDROXYCRINAMINE; ALKALOID; BULBISPERMINE; CRINAMINE; CRINUM YEMENSE EXTRACT; INDUCIBLE NITRIC OXIDE SYNTHASE; LIPOPOLYSACCHARIDE; LYCORINE; METHANOL; NITRIC OXIDE; PLANT EXTRACT; UNCLASSIFIED DRUG; YEMENINE A; YEMENINE B; YEMENINE C;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRINUM; CRINUM YEMENSE; DRUG ISOLATION; ENZYME INDUCTION; MACROPHAGE ACTIVATION; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; AMARYLLIDACEAE ALKALOIDS; CRINUM; ENZYME INHIBITORS; INDOLIZINES; LIPOPOLYSACCHARIDES; MACROPHAGES, PERITONEAL; MOLECULAR STRUCTURE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE TYPE II; PHENANTHRIDINES; PLANTS, MEDICINAL; YEMEN;

ANIMALIA; CRINUM; CRINUM YEMENSE;

EID: 3242758865     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np030529k     Document Type: Article

References (46)

1. Wood, J. R. I. A Handbook of the Yemen Flora; White Stable Litho Printers Ltd.: London, 1997; p 405.
2. Boit, H. G.; Dopke, W.; Stender, W. Chem. Ber. 1957, 90, 2203-2205.
3. Tram, N. T. N.; Titorenkova, T. V.; Bankova, V. S.; Handjieva, N. V.; Popov, S. S. Fitoterapia 2002, 73, 183-208.
4. Suffness, M.; Cordell, G. A. The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 25, pp 1-355.
5. Ghosal, S.; Saini, K. S.; Razdan, S. Phytochemistry 1985, 24, 2141-2156.
6. Martin, S. F. The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, pp 251-376.
7. Yoshikawa, M.; Murakami, T.; Wakao, S.; Ishikado, A.; Murakami, N.; Yamahara, J.; Matsuda, H. Heterocycles 1997, 45, 1815-1824.
8. Yoshikawa, M.; Murakami, T.; Ishikado, A.; Wakao, S.; Murakami, N.; Matsuda, H. Heterocycles 1997, 46, 301-308.
9. Yoshikawa, M.; Murakami, T.; Kishi, A.; Sakurama, T.; Matsuda, H.; Nomura, M.; Matsuda, H.; Kubo, M. Chem. Pharm. Bull. 1998, 46, 886-888.
10. Murakami, T.; Kishi, A.; Sakurama, T.; Matsuda, H.; Yoshikawa, M. Heterocycles 2001, 54, 957-966.
11. Matsuda, H.; Shimoda, H.; Yoshikawa, M. Bioorg. Med. Chem. 2001, 9, 1031-1035.
12. Shimoda, H.; Nishida, N.; Ninomiya, K.; Matsuda, H.; Yoshikawa, M. Heterocycles 2001, 55, 2043-2050.
13. Likhitwitayawuid, K.; Angerhofer, C. K.; Chai, H.; Pezzuto, J. M.; Cordell, G. A. J. Nat. Prod. 1993, 56, 1331-1338.
14. Ali, A. A.; El Sayed, H. M.; Abdallah, O. M.; Steglich, W. Phytochemistry 1986, 25, 2399-2401.
15. Viladomat, F.; Sellés, M.; Codina, C.; Bastida, J. Planta Med. 1997, 63, 583.
16. Tato, M. P. V.; Castedo, L.; Riguera, R. Heterocycles 1988, 27, 2833-2838.
17. Ali, A. A.; Ramadan, M. A.; Frahm, A. W. Planta Med. 1984, 424-427.
18. Kobayashi, S.; Tokumoto, T.; Kihara, M.; Imakura, Y.; Shingu, T.; Taira, Z. Chem. Pharm. Bull. 1984, 32, 3015-3022.
19. Tsuda, Y.; Kashiwaba, N.; Kumar, V. Chem. Pharm. Bull. 1984, 32, 3023-3027.
20. 1H COSY, DEPT, and HMBC experiments.
21. De Angelis, G. G.; Wildman, W. C. Tetrahedron 1969, 25, 5099-5112.
22. Pham, L. H.; Döpke, W.; Wagner, J.; Mügge, C. Phytochemistry 1998, 48, 371-376.
23. Yoshikawa, M.; Murakami, T.; Shimada, H.; Yoshizumi, S.; Saka, M.; Yamahara, J.; Matsuda, H. Chem. Pharm. Bull. 1998, 46, 1008-1014.
24. Matsuda, H.; Murakami, T.; Kageura, T.; Ninomiya, K.; Toguchida, I.; Nishida, N.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 1998, 8, 2191-2196.
25. Yoshikawa, M.; Morikawa, T.; Toguchida, I.; Harima, S.; Matsuda, H. Chem. Pharm. Bull. 2000, 48, 651-656.
26. Matsuda, H.; Morikawa, T.; Ando, S.; Toguchida, I.; Yoshikawa, M. Bioorg. Med. Chem. 2003, 11, 1995-2000.
27. Matsuda, H.; Kageura, T.; Morikawa, T.; Toguchida, I.; Harima, S.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 2000, 10, 323-327.
28. Kageura, T.; Matsuda, H.; Morikawa, T.; Toguchida, I.; Harima, S.; Oda, M.; Yoshikawa, M. Bioorg. Med. Chem. 2001, 9, 1887-1893.
29. Matsuda, H.; Kageura, T.; Oda, M.; Morikawa, T.; Sakamoto, Y.; Yoshikawa, M. Chem. Pharm. Bull. 2001, 49, 716-720.
30. Yoshikawa, M.; Morikawa, T.; Xu, F.; Ando, S.; Matsuda, H. Heterocycles 2003, 60, 1787-1792.
31. Matsuda, H.; Ninomiya, K.; Morikawa, T.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 1998, 8, 339-344.
32. Matsuda, H.; Morikawa, T.; Toguchida, I.; Ninomiya, K.; Yoshikawa, M. Heterocycles 2001, 55, 841-846.
33. Matsuda, H.; Morikawa, T.; Toguchida, I.; Ninomiya, K.; Yoshikawa, M. Chem. Pharm. Bull. 2001, 49, 1558-1566.
34. Matsuda, H.; Kageura, T.; Toguchida, I.; Ueda, H.; Morikawa, T.; Yoshikawa, M. Life Sci. 2000, 66, 2151-2157.
35. Muraoka, O.; Fujimoto, M.; Tanabe, G.; Kubo, M.; Minematsu, T.; Matsuda, H.; Morikawa, T.; Toguchida, I.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 2001, 11, 2217-2220.
36. Morikawa, T.; Matsuda, H.; Toguchida, I.; Ueda, K.; Yoshikawa, M. J. Nat. Prod. 2002, 65, 1468-1474.
37. Matsuda, H.; Toguchida, I.; Ninomiya, K.; Kageura, T.; Morikawa, T.; Yoshikawa, M. Bioorg. Med. Chem. 2003, 11, 709-715.
38. Matsuda, H.; Morikawa, T.; Sakamoto, Y.; Toguchida, I.; Yoshikawa, M. Heterocycles 2002, 56, 45-50.
39. Matsuda, H.; Morikawa, T.; Sakamoto, Y.; Toguchida, I.; Yoshikawa, M. Bioorg. Med. Chem. 2002, 10, 2527-2534.
40. Matsuda, H.; Kageura, T.; Toguchida, I.; Murakami, T.; Kishi, A.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 1999, 9, 3081-3086.
41. Morikawa, T.; Tao, J.; Ando, S.; Matsuda, H.; Yoshikawa, M. J. Nat. Prod. 2003, 66, 638-645.
42. Tao, J.; Morikawa, T.; Ando, S.; Matsuda, H.; Yoshikawa, M. Chem. Pharm. Bull. 2003, 51, 654-662.
43. Tao, J.; Morikawa, T.; Toguchida, I.; Ando, S.; Matsuda, H.; Yoshikawa, M. Bioorg. Med. Chem. 2002, 10, 4005-4012.
44. Morikawa, T.; Tao, J.; Toguchida, I.; Matsuda, H.; Yoshikawa, M. J. Nat. Prod. 2003, 66, 86-91.
45. Abdel-Halim, O. B.; Sekine, T.; Saito, K.; Halim, A. F.; Abdel-Fattah, H.; Murakoshi, I. Phytochemistry 1992, 31, 3251-3253.
46. Abdel-Halim, O. B. Phytochemistry 1995, 40, 1323-1325.