Spectroscopic analyses and chemical transformation for structure elucidation of two novel indole alkaloids from Gelsemium elegans

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3341-3344

  Yamada, Yousuke ^a   Kitajima, Mariko ^a   Kogure, Noriyuki ^a   Wongseripipatana, Sumphan ^b   Takayama, Hiromitsu ^a  

^a CHIBA UNIVERSITY   (Japan)

^b CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Alkaloid; Chemical transformation; Gelsedine; Gelsemium; Indole; Spectroscopy

Indexed keywords

GELSEOXAZOLIDININE; GELSEVANILLIDINE; INDOLE ALKALOID; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG; VANILLIN;

ARTICLE; CHEMICAL ANALYSIS; DRUG ISOLATION; DRUG STRUCTURE; GELSEMIUM; GELSEMIUM ELEGANS; NONHUMAN; SPECTROSCOPY; STRUCTURE ANALYSIS;

GELSEMIUM; GELSEMIUM ELEGANS;

EID: 65549132986     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.092     Document Type: Article

References (28)

1. Kitajima M. J. Nat. Med. 61 (2007) 14-23
2. Takayama H., and Sakai S. In: Cordell G.A. (Ed). The Alkaloids Vol. 49 (1997), Academic, San Diego, CA Chapter 1, and references cited therein
3. Yin S., He X., Wu Y., and Yue J. Chem. Asian J. 3 (2008) 1824-1829
4. Xu Y., Yang S., Liao S., Zhang H., Lin L., Ding J., and Yue J. J. Nat. Prod. 69 (2006) 1347-1350
5. Kitajima M., Arai Y., Takayama H., and Aimi N. Proc. Jpn. Acad. Ser. B 74 (1998) 159-163
6. Rujjanawate C., Kanjanapothi D., and Panthong A. J. Ethnopharmacol. 89 (2003) 91-95
7. Kitajima M., Nakamura T., Kogure N., Ogawa M., Mitsuno Y., Ono K., Yano S., Aimi N., and Takayama H. J. Nat. Prod. 69 (2006) 715-718
8. J. Nat. Prod. 70 (2007) 142
9. Lai K.D., Trinh T.T., Tran V.S., and Pham G.D. Tap. Chi. Hoa. Hoc. 42 (2004) 199-204
10. Zhamg L., Lin J., and Wu Z. J. Chin. Med. Mater. 26 (2003) 451-453
11. Chi D.-B., Lei L.-S., Jin H., Pang J.-X., and Jiang Y.-P. Acad. J. First Med. Coll. PLA 23 (2003) 911-913
12. Yamada Y., Kitajima M., Kogure N., and Takayama H. Tetrahedron 64 (2008) 7690-7694
13. Kogure N., Kobayashi H., Ishii N., Kitajima M., Wongseripipatana S., and Takayama H. Tetrahedron Lett. 49 (2008) 3638-3642
14. Kogure N., Ishii N., Kobayashi H., Kitajima M., Wongseripipatana S., and Takayama H. Chem. Pharm. Bull. 56 (2008) 870-872
15. Kogure N., Someya A., Urano A., Kitajima M., and Takayama H. J. Nat. Med. 61 (2007) 208-212
16. Kogure N., Ishii N., Kitajima M., Wongseripipatana S., and Takayama H. Org. Lett. 8 (2006) 3085-3088
17. Kogure N., Nishiya C., Kitajima M., and Takayama H. Tetrahedron Lett. 46 (2005) 5857-5861
18. Kitajima M., Kogure N., Yamaguchi K., Takayama H., and Aimi N. Org. Lett. 5 (2003) 2075-2078
19. Kitajima M., Urano A., Kogure N., Takayama H., and Aimi N. Chem. Pharm. Bull. 51 (2003) 1211-1214
20. 3/MeOH gradient) and then by MPLC (5% MeOH/AcOEt) to give gelseoxazolidinine.
21. 5, 461.2076); CD (c 0.219 mmol/L, MeOH, 24 °C) Δε (λ nm) 0 (352), +2.81 (306), 0 (278), -8.15 (258), 0 (243), +3.64 (236), 0 (227), -23.34 (211).
22. Rankinidine used in this study was isolated from G. rankinii:. Schun Y., and Cordell G.A. J. Nat. Prod. 49 (1986) 806-808
23. Takayama H., Tominaga Y., Kitajima M., Aimi N., and Sakai S. J. Org. Chem. 54 (1994) 4381-4385
24. The possible mechanism for the oxidative cleavage of the enamine double bond with excess m-CPBA is shown below. {A figure is presented}
25. Du X., Dai Y., Zhang C., Lu S., and Liu Z. Acta Chim. Sin. 40 (1982) 1137-1141
26. 6, 428.1947); CD (c 0.369 mmol/L, MeOH, 24 °C) Δε (λ nm) 0 (305), -4.46 (260), 0 (249), +7.81(236), 0 (222), -9.30 (212).
27. Lin L., Cordell G.A., Ni C., and Clardy J. Phytochemistry 29 (1990) 3013-3017
28. 4, 370.1892); CD (c 0.351 mmol/L, MeOH, 24 °C) Δε (λ nm) 0 (300), -1.46 (278), -5.73 (262), 0 (250), +11.08 (234), 0 (223), -19.82 (212).