Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata

Journal of Natural Products

Volumn 59, Issue 2, 1996, Pages 100-108

  Rieser, Matthew J ^a   Gu, Zhe Ming ^b   Fang, Xin Ping ^b   Zeng, Lu ^b   Wood, Karl V ^b   McLaughlin, Jerry L ^b  

^a AgrEvo Research Center   (United States)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; ANNONACIN; ANNONACIN 10 ONE; ARIANACIN; CYTOTOXIC AGENT; DOXORUBICIN; GONIOTHALAMICIN; JAVORICIN; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOASSAY; CANCER CELL CULTURE; CANCER INHIBITION; COLON ADENOCARCINOMA; CYTOTOXICITY TEST; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG ISOLATION; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; MEDICINAL PLANT; NONHUMAN; PLANT SEED; STEREOCHEMISTRY;

4-BUTYROLACTONE; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BREAST NEOPLASMS; DRUG SCREENING ASSAYS, ANTITUMOR; HT29 CELLS; HUMANS; LUNG NEOPLASMS; PLANT TUMORS; PLANTS, MEDICINAL; SEEDS; TUMOR CELLS, CULTURED;

EID: 0030484785     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np960037q     Document Type: Article

References (31)

1. Morton, J. Fruits of Warm Climates; Media, Inc.: Miami, FL, 1973; pp 75-80.
2. Awan, J. A.; Kar, A.; Udoudoh, P. J. Plant Foods Human Nut. 1980, 30, 163-168.
3. Kooiman, P. Carbohydr. Res. 1971, 20, 329-337.
4. Koesriharti, In Plant Resources of South-East Asia, No. 2, Edible Fruits and Nuts; Verheij, E. W., Coronel, R. E., Eds.; Pudoc Wageningen, Prosea Foundation: Bogor, Indonesia; and Pudoc-DLO: S Wageningen, Netherlands, 1991; pp 75-78.
5. Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobson, L. B.; Nichols, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31-34.
6. McLaughlin, J. L. Methods in Plant Biochemistry; Hostettman, K., Ed.; Academic Press: London, 1991; Vol. 6, pp 1-30.
7. McCloud, T. G.; Smith, D. L.; Chang, C.-J.; Cassady, J. M. Experientia 1987, 43, 947-949.
8. Cassady, J. M.; Chang, C.-J.; Cooks, R. G. Natural Products Chemistry; Atta-ur-Rahman and LeQuesne, P. W., Eds.; Springer Verlag: Vienna, 1988; Vol. 3, pp 291-305.
9. Xu, L.-Z.; Chang, C.-J.; Yu, J.-G.; Cassady, J. M. J. Org Chem. 1989, 4, 5418-5421.
10. Rieser, M. J.; Fang, X.-P.; Anderson, J. E.; Miesbauer, L., Smith, D. L.; McLaughlin, J. L. Helv. Chim. Acta 1993, 76, 2433-2444. Erratum: 1994, 77, 882.
11. Rieser, M. J.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L. Tetrahedron Lett. 1991, 32, 1137-1140.
12. Boris, C.; Loiseau, P.; Cortes, D.; Myint, S. H.; Hocquemiller, R.; Gayral, P.; Cavé, A.; Laurens, A. Planta Med. 1991, 57, 434-436.
13. Myint, S. H.; Laurens, A.; Hocquemiller, R.; Cavé, A. Heterocycles 1990, 31, 861-867.
14. Cortes, D.; Myint, S. H.; Laurens, A.; Hocquemiller, R.; Leboeuf, M.; M. Cavé, M. Can. J. Chem. 1991, 69, 8-11.
15. Myint, S. H.; Cortes, D.; Laurens, A.; Hocquemiller, R.; Leboeuf, M.; Cavé, A.; Cotte, J.; Queros, A. M. Phytochemistry 1991, 30, 3335-3338.
16. Alkofahi, A.; Rupprecht, J. K.; Liu, Y.-M., Chang, C.-J.; Smith, McLaughlin, J. L. Experientia 1990, 46, 539-541.
17. Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
18. Fang, X.-P.; Rieser, M. J.; Gu, Z.-M ; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-48 and 50-67.
19. Rupprecht, J. K.; Chang, C.-J.; Cassady, J. M.; McLaughlin, J. L.; Mikolajczak, K. L.; Weislander, D. Heterocycles 1986, 24, 1197-1201.
20. Hanson, P. Studies on Stereochemistry of the Annonaceous Acetogenins: The Total Synthesis of Hexepi-Uvaricin and Ent-Bullatacin, Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 1993, p 134.
21. Gu, Z.-M.; Zeng, L.; Fang, X.-P.; Colman-Saizarbitoria, T.; Huo, M.; McLaughlin, J. L. J. Org. Chem. 1994, 59, 5162-5172.
22. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
23. Ohtani, I.; Kusumi, T., Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
24. Rieser, M. J.; Hui, Y.-H.; Rupprecht, J. K; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hanson, P. R.; Zhuang, Z.; Hoye, T. R. J. Am. Chem. Soc. 1992, 114, 10 203-10 213
25. Woo, M.-H.; Zeng, L.; Ye, Q.; Gu, Z.-M., Zhao, G.-X.; McLaughlin, J. L. Bioorg. Med. Chem. Lett. 1995, 5, 1131-1140
26. Ahammadsahib, K. I.; Hollingworth, R. M.; McGovren, J. P.; Hui, Y.-H., McLaughlin, J. L Life Sci. 1993, 53, 1113-1120.
27. Morre, D. J.; Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-348.
28. Ferrigni, N. R.; Putnam, J. E.; Jacobson, L. B.; Nichols, D. E.; Moore, D. L.; McLaughlin, J. L.; Powell, R. G.; Smith, C. R. J. Nat. Prod. 1982, 45, 679-686.
29. Giard, D. J.; Aaronson, S. A.; Todaro, G. J.; Arnstein, P.; Kersey, J. H.; Dosik, H ; Parks, W. P. J. Natl. Cancer Inst. 1973, 55, 1417-1423.
30. Soule, H. D.; Vazquez, J.; Long, A.; Albert, S.; Brennan, M. J. Natl. Cancer Inst. 1973, 51, 1409-1416.
31. Fogh J.; Trempe, G. In Human Tumor Cells, In Vitro; Fogh, J., Ed.; Plenum Press: New York, 1975; p 115