Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana

Tetrahedron Letters

Volumn 51, Issue 2, 2010, Pages 269-272

  Low, Yun Yee ^a   Lim, Kuan Hon ^a   Choo, Yeun Mun ^a   Pang, Huey Shen ^a   Etoh, Tadahiro ^b   Hayashi, Masahiko ^b   Komiyama, Kanki ^c   Kam, Toh Seok ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b IWAKI MEISEI UNIVERSITY   (Japan)

^c KITASATO UNIVERSITY   (Japan)

Author keywords

Alkaloids; Biological activity; NMR; Partial synthesis; Tabernaemontana

Indexed keywords

IBOGAINE; INDOLE ALKALOID; LIROFOLINE A; LIROFOLINE B; PLANT EXTRACT; TABERNAEMONTANA CORYMBOSA EXTRACT; TABERNAEMONTANA DIVARICATA EXTRACT; UNCLASSIFIED DRUG; VINCRISTINE;

ARTICLE; BARK; CARBON NUCLEAR MAGNETIC RESONANCE; CARCINOMA CELL; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; IC 50; MEDICINAL PLANT; MULTIDRUG RESISTANCE; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PLANT STEM; PROTON NUCLEAR MAGNETIC RESONANCE; TABERNAEMONTANA CORYMBOSA; TABERNAEMONTANA DIVARICATA; UTERINE CERVIX CARCINOMA;

TABERNAEMONTANA; TABERNAEMONTANA CORYMBOSA; TABERNAEMONTANA DIVARICATA;

EID: 71049175371     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.122     Document Type: Article

References (40)

1. Van Beek T.A., Verpoorte R., Baerheim Svendsen A., Leeuwenberg A.J.M., and Bisset N.G. J. Ethnopharmacol. 10 (1984) 1
2. Danieli B., and Palmisano G. In: Brossi A. (Ed). The Alkaloids Vol. 27 (1986), Academic Press, Orlando 1-130
3. Kam T.S., and Choo Y.M. In: Cordell G.A. (Ed). The Alkaloids Vol. 63 (2006), Academic Press, Amsterdam 181-337
4. Kam T.S. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 14 (1999), Pergamon, Amsterdam 285-435
5. Lim K.H., Etoh T., Hayashi M., Komiyama K., and Kam T.S. Tetrahedron Lett. 50 (2009) 752
6. Lim K.H., and Kam T.S. Tetrahedron Lett. 50 (2009) 3756
7. Kam T.S., Sim K.M., and Lim T.M. Tetrahedron Lett. 40 (1999) 5409
8. Kam T.S., Sim K.M., and Lim T.M. Tetrahedron Lett. 41 (2000) 2733
9. Kam T.S., Sim K.M., and Lim T.M. Tetrahedron Lett. 42 (2001) 4721
10. Kam T.S., Loh K.Y., Lim L.H., Loong W.L., Chuah C.H., and Chen W. Tetrahedron Lett. 33 (1992) 969
11. Lim K.H., Hiraku O., Komiyama K., and Kam T.S. J. Nat. Prod. 71 (2008) 1591
12. Kam T.S., Sim K.M., Pang H.S., Koyano T., Hayashi M., and Komiyama K. Bioorg. Med. Chem. Lett. 14 (2004) 4487
13. Kam T.S., Sim K.M., and Pang H.S. J. Nat. Prod. 66 (2003) 11
14. Kam T.S., and Sim K.M. Phytochemistry 63 (2003) 625
15. Kam T.S., and Sim K.M. Helv. Chim. Acta 86 (2003) 122
16. Kam T.S., and Sim K.M. J. Nat. Prod. 65 (2002) 669
17. Kam T.S., and Sim K.M. Helv. Chim. Acta 85 (2002) 1027
18. Kam T.S., and Sim K.M. Heterocycles 57 (2002) 2137
19. Kam T.S., and Sim K.M. Heterocycles 55 (2001) 2405
20. Kam T.S., Sim K.M., Koyano T., Toyoshima M., Hayashi M., and Komiyama K. Bioorg. Med. Chem. Lett. 8 (1998) 1693
21. Kam T.S., Pang H.S., Choo Y.M., and Komiyama K. Chem. Biodiv. 1 (2004) 646
22. Kam T.S., and Pang H.S. Heterocycles 63 (2004) 845
23. Kam T.S., Pang H.S., and Lim T.M. Org. Biomol. Chem. 1 (2003) 1292
24. Kam T.S., Anuradha S., and Loh K.Y. Nat. Prod. Lett. 8 (1996) 49
25. Kam T.S., and Anuradha S. Nat. Prod. Lett. 7 (1995) 191
26. Kam T.S., Loh K.Y., and Chen W. J. Nat. Prod. 56 (1993) 1865
27. Extraction was carried out on ca. 13 kg of bark of T. corymbosa and ca. 2.5 kg of bark of T. divaricata.
28. 2, 324.1838).
29. 3+H, 355.2022).
30. Buchi G., and Manning R.E. J. Am. Chem. Soc. 88 (1966) 2532
31. Langlois N., Gueritte F., Langlois Y., and Potier P. J. Am. Chem. Soc. 98 (1976) 7017
32. Langlois N., Gueritte F., Langlois Y., and Potier P. Tetrahedron Lett. (1976) 1487
33. Kutney J.P., Joshua A.V., and Liao P.H. Heterocycles 6 (1977) 297
34. Honma Y., and Ban Y. Heterocycles 6 (1977) 291
35. Kutney J.P., Joshua A.V., Liao P.H., and Worth B.R. Can. J. Chem. 55 (1977) 3235
36. Honma Y., and Ban Y. Tetrahedron Lett. (1978) 155
37. Andriamialisoa R.Z., Langlois N., Langlois Y., and Potier P. Can. J. Chem. 57 (1979) 2572
38. Mangeney P., Langlois N., Leroy C., Riche C., and Langlois Y. J. Org. Chem. 47 (1982) 4261
39. 2, 327.2073).
40. 2, 327.2067).