Daphmanidins E and F, alkaloids from Daphniphyllum teijsmannii

Journal of Natural Products

Volumn 69, Issue 3, 2006, Pages 418-420

  Morita, Hiroshi ^a   Ishioka, Nozomi ^b   Takatsu, Hiroshi ^a,b   Iizuka, Toru ^a   Kobayashi, Jun'ichi ^b  

^a HOSHI UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; DAPHMANIDIN E; DAPHMANIDIN F; DAPHNIPHYLLUM TEIJSMANNII EXTRACT; NORADRENALIN; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANIMAL TISSUE; AORTA; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG INHIBITION; DRUG ISOLATION; DRUG STRUCTURE; MALE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF; RAT; VASODILATATION;

ALKALOIDS; ANIMALS; AORTA; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; JAPAN; MOLECULAR STRUCTURE; PLANT LEAVES; PLANTS, MEDICINAL; RATS; VASODILATOR AGENTS;

ANIMALIA; DAPHNIPHYLLUM;

EID: 33645979312     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0503799     Document Type: Article

References (20)

1. Kobayashi, J.; Morita, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, The Daphniphyllum Alkaloids; 2003; Vol. 60, p 165.
2. Heathcock, C. H. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14323-14327, and references therein.
3. Morita, H.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 1999, 64, 7208-7212.
4. Morita, H.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2000, 65, 3558-3562.
5. (a) Morita, H.; Yoshida, N.; Kobayashi, J. Tetrahedron 1999, 55, 12549-12556.
6. (b) Morita, H.; Yoshida, N.; Kobayashi, J. Tetrahedron 2000, 56, 2641-2646.
7. (c) Morita, H.; Kobayashi, J. Tetrahedron 2002, 58, 6637-6641.
8. Kobayashi, J.; Inaba, Y.; Shiro, M.; Yoshida, N.; Morita, H. J. Am. Chem. Soc. 2001, 123, 11402-11408.
9. Morita, H.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2002, 67, 2278-2282.
10. Kobayashi, J.; Ueno, S.; Morita, H. J. Org. Chem. 2002, 67, 6546-6549.
11. Morita, H.; Kobayashi, J. Org. Lett. 2003, 5, 2895-2898.
12. (a) Takatsu, H.; Morita, H., Ya-Ching, S.; Kobayashi, J. Tetrahedron 2004, 60, 6279-6284.
13. (b) Morita, H.; Takatsu, H.; Ya-Ching, S.; Kobayashi, J. Tetrahedron Lett. 2004, 45, 901-904.
14. (c) Kobayashi, J.; Takatsu, H.; Ya-Ching S.; Morita, H. Org. Lett. 2003, 5, 1733-1736.
15. (d) Morita, H.; Takatsu, H.; Kobayashi, J. Tetrahedron 2003, 59, 3575-3579.
16. Morita, H.; Ishioka, N.; Takatsu, H.; Shinzato, T.; Hoshino, T.; Obara, Y.; Nakahata, N.; Kobayashi, J. Org. Lett. 2005, 7, 459-462.
17. The iminium carbon (C-1) observed at δ 202.93 for the TFA salt of 1 was shifted to δ 188.45 for free base. Some examples: Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.-z.; Chem, H.-s. J. Am. Chem. Soc. 1995, 117, 1155-1156.
18. Chou, T.; Haino, T.; Kuramoto, M.; Uemura, D. Tetrahedron Lett. 1996, 37, 4027-4030.
19. Conformational search and molecular mechanics calculations were conducted with the Macromodel program: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
20. Nagai, M.; Noguchi, M.; Iizuka, T.; Otani, K.; Kamata, K. Biol. Pharm. Bull. 1996, 19, 228-232.