Asitrilobins A and B: Cytotoxic mono-THF annonaceous acetogenins from the seeds of Asimina triloba

Phytochemistry

Volumn 50, Issue 6, 1999, Pages 1033-1040

  Woo, Mi Hee ^a   Kim, Dal Hwan ^a   McLaughlin, Jerry L ^b  

^a Catholic University of Daegu   (South Korea)

^b PURDUE UNIVERSITY   (United States)

Author keywords

Annonaceae; Asitrilobins A and B; Cytotoxicities; Index Asimina triloba; Mono tetrahydrofuran Acetogenins; Seed

Indexed keywords

ACETOGENIN; ANNONACIN; ANTINEOPLASTIC AGENT; ASITRILOBIN A; ASITRILOBIN B; FURAN DERIVATIVE; LACTONE;

ANIMAL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL CULTURE; CHEMICAL ANALYSIS; CHEMISTRY; CONFORMATIONAL TRANSITION; CYTOTOXICITY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG EFFECT; DRUG INDICATION; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; HUMAN; ISOLATION AND PURIFICATION; PLANT SEED; SHRIMP; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; TOXICITY TESTING; TREE;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; DECAPODA (CRUSTACEA); DRUG SCREENING ASSAYS, ANTITUMOR; FURANS; HUMANS; LACTONES; SEEDS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; STEREOISOMERISM; TOXICITY TESTS; TREES; TUMOR CELLS, CULTURED;

AGOUTI PACA; ANIMALIA; ANNONACEAE; ANOSTRACA; ASIMINA TRILOBA; DECAPODA (CRUSTACEA);

EID: 0033103520     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(98)00632-3     Document Type: Article

References (32)

1. Ahammadahib, K. I., Hollingworth, R. M., McGovren, J. P., Hui, Y. -H., and McLaughlin, J. L. (1993). Life Sci., 53, 1113.
2. Callaway, M. B. (1990). In The PawPaw (Asimina triloba) (pp. 1). Kentucky State University Press, Frankfort.
3. Cave, A., Figadere, B., Laurens, A. and Zechmeister, D. C. (1997). In W. Herz, G. W., Kirby, R. E. Moore, W. Steglich, Ch. Tamm (Eds.), Progress in the Chemistry of Organic Natural Products (pp. 81). Spring Verlag, New York.
4. Fang, X. P., Rieser, R. J., Gu, Z. M., Zhao, G. X., and McLaughlin, J. L. (1993). Phytochem. Anal., 4, 49.
5. Fogh, J., and Trempe, G. (1975). In J. Fogh (Ed.), Human tumor cells in vitro (pp. 115). Plenum Press, New York.
6. Giard, D. L., Aaronson, G. J., Arnstein, P., Kersey, J. H., Dosik, H., and Parks, W. P. (1973). J. Nat. Prod., 51, 1417.
7. Gu, Z. -M., Fang, Z. -P., Zeng, L., Song, R., Ng, J. H., Wood, K. V., Smith, D. L., and McLaughlin, J. L. (1994). J. Org. Chem., 59, 3472.
8. Gu, Z.-M., Zhao, G.-X., Oberlies, N. H., Zeng, L., and McLaughlin, J. L. (1995). In J. T. Arnason, R. Mata, J. T. Romeo (Eds.), Recent Advances in Phytochemistry (Vol. 29, pp. 249). Plenum Press, New York.
9. He, K., Shi, G., Zhao, G. -X., Zeng, L., Ye, Q., Schwedler, J. L., Wood, K. V., and McLaughlin, J. L. (1996). J. Nat. Prod., 59, 1029.
10. He, K., Zhao, G. -X., Shi, G., Zeng, L., Chao, J. -F., and McLaughlin, J. L. (1997). Bioorg. Med. Chem., 5, 501.
11. Hoye, T. R., Hanson, P. R., Hasenwinkel, L. E., Raminez, E. A., and Zhuang, Z. (1994). Tetrahedron Lett., 35, 8525.
12. Hoye, T. R., Hanson, P. R., Hasenwinkel, L. E., Raminez, E. A., and Zhuang, Z. (1994). Tetrahedron Lett., 35, 8529.
13. Hui, Y. -H., Rupprecht, J. K., Kozlowski, J. F., Wood, K. V., McLaughlin, J. L., Hanson, P. R., Zhuang, Z. -P., and Hoye, T. R. (1992). J. Am. Chem. Soc., 114, 10203.
14. Kaighn, M. E., Narayan, K. S., Ohnuki, Y., Lechner, J. F., and Jones, L. W. (1979). Invest. Urol., 17, 16.
15. McLaughlin, J. L. (1991). In K. Hostettmann (Ed.), Methods in Plant Biochemistry (Vol. 6, pp. 1). Academic Press, London.
16. Meyer, B. N., Ferrigni, N. R., Putnam, J. E., Jacobsen, L. B., Nichols, D. E., and McLaughlin, J. L. (1982). Planta Med., 45, 31.
17. Moore, D. J., de Caro, R., Farley, C., Oberlies, N. H., and McLaughlin, J. L. (1995). Life Sci., 56, 343.
18. Rieser, M. J., Fang, X. -P., Anderson, J. E., Miesbauer, L. R., Smith, D. L., and McLaughlin, J. L. (1993). Helv. Chim. Acta, 76, 2433.
19. Rieser, M. J., Fang, X. -P., Anderson, J. E., Miesbauer, L. R., Smith, D. L., and McLaughlin, J. L. (1994). Helv. Chim. Acta, 77, 882.
20. Soule, H. D., Vazquez, J., Long, A., Albert, S., and Brennam, M. J. (1973). Natl. Cancer Inst., 51, 1409.
21. Woo, M. H., Cho, K. Y., Zhang, Y., Zeng, L., Gu, Z. -M., and McLaughlin, J. L. (1995). J. Nat. Prod., 58, 1533.
22. Woo, M. H., Zeng, L., and McLaughlin, J. L. (1995). Heterocycles, 41, 1731.
23. Woo, M. H., Zeng, L., Ye, Q., Gu, Z. -M., Zhao, G. -X., and McLaughlin, J. L. (1995). Bioorg. Med. Chem. Lett., 5, 1135.
24. Yunis, A. A., Arimura, G. K., and Russin, D. (1977). Int. J. Cancer, 19, 128.
25. Zeng, L., Ye, Q., Oberlies, N. H., Shi, G., Gu, Z. -M., He, K., and McLaughlin, J. L. (1996). Nat. Prod. Rep., 13, 275.
26. Zhao, G. -X., Chao, J. -F., Zeng, L., and McLaughlin, J. L. (1996). Natural Toxins, 4, 128.
27. Zhao, G. -X., Chao, J. -F., Zeng, L., Rieser, M. J., and McLaughlin, J. L. (1996). Bioorg. Med. Chem., 4, 25.
28. Zhao, G. -X., Gu, Z. -M., Zeng, L., Chao, J. -F., Kozlowski, J. F., Wood, K. V., and McLaughlin, J. L. (1995). Tetrahedron, 26, 7149.
29. Zhao, G. -X., Hui, Y. -H., and McLaughlin, J. L. (1992). J. Nat. Prod., 55, 347.
30. Zhao, G. -X., Miesbauer, L. R., Smith, D. L., and McLaughlin, J. L. (1994). J. Med. Chem., 37, 1971.
31. Zhao, G. -X., Ng, J. H., Kozlowski, J. F., Smith, D. L., and McLaughlin, J. L. (1994). Heterocycles, 38, 1897.
32. Zhao, G. -X., Rieser, M. J., Hui, Y. -H., Miesbauer, L. R., Smith, D. L., and McLaughlin, J. L. (1993). Phytochemitry, 33, 1065.