Isolation of montecristin, a key metabolite in biogenesis of acetogenins from Annona muricata and its structure elucidation by using tandem mass spectrometry

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 510-513

  Gleye, C ^a   Laurens, A ^a   Hocquemiller, R ^a   Cave A ^a   Laprevote O ^b   Serani, L ^b  

^a UNIVERSITÉ PARIS SUD   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; MONTECRISTIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PHYTOCHEMISTRY;

EID: 0031029395     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960901j     Document Type: Article

References (24)

1. Kerharo, J. La pharmacopée sénégalaise traditionelle, Vigot frères: Paris, 1974; pp 144-146.
2. Fang, X. P.; Rieser, M. J.; Gu, Z. H.; Zhao, G. X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-48.
3. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Hertz, W., Ed.; Springer Verlag: New York, 1996; Vol. 70, pp 81-288.
4. Leboeuf, M.; Legueut, C.; Cavé, A.; Desconclois, J. F.; Forgacs, P.; Jacquemin H. Planta Med. 1981, 42, 37-44.
5. Rieser, M. J.; Fang, X. P.; Rupprecht, J. K.; Hui, Y. H.; Smith, D. L.; McLaughlin, J. L. Planta Med. 1993, 59, 91-92.
6. Roblot, F.; Laugel, T.; Leboeuf, M.; Cavé, A.; Laprévote, O. Phytochemistry 1993, 34, 281-285.
7. Kirchner, J. G. In Technique of organic chemistry; Perry, E. S., Weissberger, A., Eds.; Interscience: New York, 1967; Vol. 12, pp 147-186.
8. Schmitz, F. J.; Kraus, K. W.; Ciereszko, L. S.; Sifford, D. H.; Weinheimer, A. J. Tetrahedron Lett. 1966, 1, 97-103.
9. Gaudemer, A. In Stereochemistry; Kagan, H. B., Ed.; Thieme: Stuggart, 1977; Vol. 1, pp 44-136.
10. Gu, Z. H.; Zhao, G. X.; Oberlies, N. H.; Zeng, L.; McLaughlin J. L. In Phytochemistry of Medicinal Plants; Amason, J. T., Ed.; Plenum Press: New York, 1995; Vol. 29, pp 249-310.
11. Adams, J.; Gross, M. L. Anal. Chem. 1987, 59, 1576-1582.
12. Tomer K. B.; Jensen, N. J.; Gross, M. L. Anal. Chem. 1986, 58, 2429-2433.
13. Jensen, N. J.; Tomer, K. B.; Gross, M. L. J. Am. Chem. Soc. 1985, 107, 1863-1868.
14. Laprévote, O.; Girard, C.; Das, B. C.; Laugel, T.; Roblot, F.; Leboeuf, M.; Cavé A. Rapid Commun. Mass Spectrom. 1992, 6, 352-355.
15. Sahpaz, S.; Laurens, A.; Hocquemiller, R.; Cavé, A.; Cortes, D. Can. J. Chem. 1994, 72, 1533-1536.
16. Tam, V. T.; Pham, Q. C. H.; Chappe, B.; Roblot, F.; Laprévote, O.; Figadère, B.; Cavé, A. Nat. Prod. Lett. 1994, 4, 255-262.
17. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Leboeuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, J. E., Eds.; Plenum Press: New York, 1993; Vol. 27, pp 167-202.
18. Laprévote, O.; Das, B. C. Tetrahedron 1994, 50, 8479-8490.
19. Zheng, X. C.; Yang, R. Z.; Quin, G. W.; Xu, R. S.; Fan, D. J. Acta Bot. Sin. 1995, 37, 238-243.
20. Meneses Da Silva, E. L.; Roblot, F.; Mahuteau, J.; Cavé, A. J. Nat. Prod. 1996, 59, 528-530.
21. Gromek, D.; Figadère, B.; Hocquemiller, R.; Cavé, A.; Cortes, D. Tetrahedron 1993, 49, 5247-5252.
22. Ballard, K. D.; Gaskell, S. J.; Jennings, R. K. C.; Scrivens, J. H.; Vickers, R. G. Rapid Commun. Mass Spectrom. 1992, 6, 553-559.
23. Scrivens, J. H.; Rollins, K.; Jennings, R. K. C.; Bordoli, R. S.; Bateman, R. H. Rapid Commun. Mass Spectrom. 1992, 6, 272-277.
24. Bordoli, R. S.; Bateman, R. H. Int. J. Mass. Spectrom. Ion Proc. 1992, 122, 243-254.