Four novel gelsenicine-related oxindole alkaloids from the leaves of Gelsemium elegans Benth.

Organic Letters

Volumn 8, Issue 14, 2006, Pages 3085-3088

  Kogure, Noriyuki ^a   Ishii, Naoko ^a   Kitajima, Mariko ^a   Wongseripipatana, Sumphan ^b   Takayama, Hiromitsu ^a  

^a CHIBA UNIVERSITY   (Japan)

^b CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

RAUWOLFIA ALKALOID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GELSEMIUM; ISOLATION AND PURIFICATION; MEDICINAL PLANT; PLANT LEAF; THAILAND;

GELSEMIUM; MOLECULAR STRUCTURE; PLANT LEAVES; PLANTS, MEDICINAL; SECOLOGANIN TRYPTAMINE ALKALOIDS; THAILAND;

EID: 33746644152     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061062i     Document Type: Article

References (21)

1. Kitajima, M.; Arai, Y.; Takayama, H.; Aimi, N. Proc. Jpn. Acad., Ser. B 1998, 74, 159-163.
2. Takayama, H.; Sakai, S. Gelsemium Alkaloids. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1997; Vol. 49, Chapter 1, and references therein.
3. Kitajima, M.; Nakamura, T.; Kogure, N.; Ogawa, M.; Mitsuno, Y.; Ono, K.; Yano, S.; Aimi, N.; Takayama, H. J. Nat. Prod. 2006, 69, 715-718.
4. (a) Mardin, A.; O'Donnell, C. J.; Oh, T.; Old, D. W.; Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 2005, 127, 18054-18065.
5. (b) Yokoshima, S.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2000, 39, 4073-4075.
6. (c) Atarashi, S.; Choi, J.-K.; Ha, D. C.; Hart, D. J.; Kuzmich, D.; Lee, C. S.; Ramesh, S.; Wu, S. C. J. Am. Chem. Soc. 1997, 119, 6226-6241.
7. (d) Ng, F. W.; Lin, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 9812-9824.
8. (e) Beyersbergen van Henegouhen, W. G.; Fieseler, R. M.; Rutjes, F. P. J. T.; Hiemstra, H. Angew. Chem., Int. Ed. 1999, 38, 2214-2217.
9. (a) Kitajima, M.; Kogure, N.; Yamaguchi, K.; Takayama, H.; Aimi, N. Org. Lett. 2003, 5, 2075-2078.
10. (b) Kogure, N.; Nishiya, C.; Kitajima, M.; Takayama, H. Tetrahedron Lett. 2005, 46, 5857-5861.
11. (c) Kitajima, M.; Urano, A.; Kogure, N.; Takayama, H.; Aimi, N. Chem. Pharm. Bull. 2003, 51, 1211-1214.
12. 4, 315.1345); CD (c = 0.229 mmol/L, MeOH, 24 °C) Δ∈ (nm) 0 (300), -5.86 (261), 0 (248), +8.91 (235), 0 (224), -26.98 (211).
13. a) Du, X. B.; Dai, Y. H.; Zhang, C. L.; Lu, S. L.; Liu, Z. G. Huaxue Xuebao 1982, 40, 1137-1141.
14. (b) Yan, J. S.; Chen, Y. W. Yaoxue Xuebao 1983, 18, 104-112.
15. (c) Takayama, H.; Tominaga, Y.; Kitajima, M.; Aimi, N.; Sakai, S. J. Org. Chem. 1994, 59, 4381-4385.
16. 6, 373.1400); CD (c = 0.232 mmol/L, MeOH, 24 °C) Δ∈ (nm) 0 (300), -5.07 (262), 0 (248), +7.72 (235), 0 (223), +15.10 (211).
17. 5, 421.1763); CD (c = 0.305 mmol/L, MeOH, 24 °C) Δ∈ (nm) 0 (338), +0.85 (308), 0 (296), -4.90 (260), 0 (244), +2.15 (236), 0 (227), -11.91 (212).
18. 8, 539.2393); CD (c = 0.195 mmol/L, MeOH, 24 °C) Δ∈ (nm) 0 (327), -12.0 (282), -1.0 (256), -14.3 (226), 0 (217), +17.0 (210).
19. a) Ponglux, D.; Wongseripipatana, S.; Takayama, H.; Ogata, K.; Aimi, N.; Sakai, S. Tetrahedron Lett. 1988, 29, 5395-5396.
20. (b) Lin, L. Z.; Cordell, G. A.; Ni, C. Z.; Clardy, J. J. Org. Chem. 1989, 54, 3199-3202.
21. Takayama, H.; Morohoshi, Y.; Kitajima, M.; Aimi, N.; Wongseripipatana, S.; Ponglux, D.; Sakai, S. Nat. Prod. Lett. 1994, 5, 15-20.