Applying Mosher's method to acetogenins bearing vicinal diols. The absolute configurations of muricatetrocin C and rollidecins A and B, new bioactive acetogenins from Rollinia mucosa

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 8, 1996, Pages 1281-1286

  Shi, Guoen ^a   Gu, Zhe Ming ^a   He, Kan ^a   Wood, Karl V ^a   Zeng, Lu ^a   Ye, Qing ^a   MacDougal, John M ^b   McLaughlin, Jerry L ^a  

^a PURDUE UNIVERSITY   (United States)

^b MISSOURI BOTANICAL GARDEN   (United States)

Author keywords

Acetogenins; Muricatetrocin C; Rollidecin A; Rollidecin B; Rollinia mucosa

Indexed keywords

ACETOGENIN; ANTINEOPLASTIC AGENT; DOXORUBICIN; MURICATETROCIN; ROLLIDECIN A; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTEMIA; ARTICLE; CANCER CELL CULTURE; CHIRALITY; CONTROLLED STUDY; CYTOTOXICITY; DERIVATIZATION; DRUG ISOLATION; DRUG STRUCTURE; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; PLANT; STEREOCHEMISTRY; TECHNIQUE;

ANIMALIA; ANNONACEAE; ARTEMIA; ROLLINIA MUCOSA;

EID: 0030220269     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00114-9     Document Type: Article

References (24)

1. 1. Shi, G.; Zeng, L.; Gu, Z.-M; MacDougal, J. M.; McLaughlin, J. L. Heterocycles 1995, 41, 1785.
2. 2. Shi, G.; Alfonso, D.; Fatope, M. O.; Zeng, L.; Gu, Z.-M.; Zhao, G.-X.; He, K.; MacDougal, J. M.; McLaughlin, J. L. J. Am. Chem. Soc. 1995, 117, 10409.
3. 3. Shi, G.; Ye, Q.; He, K.; McLaughlin, J. L. J. Nat. Prod. 1996, (in press).
4. 4. Rieser, M. J.; Fang, X.-P.; Anderson, J. E.; Miesbauer, L. R.; Smith, D. L.; McLaughlin, J. L. Helv. Chim. Acta 1993, 76, 2433; erratum 1994, 77, 882.
5. 5. Gu, Z.-M.; Fang, X.-P.; Zeng, L.; Kozlowski, J. F.; McLaughlin, J. L. Bioorg. Med. Chem. Lett. 1994, 4, 473.
6. 6. (a) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237;
7. (b) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal., 1993, 4, 27;
8. (c) Gu, Z.-M; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T.; Mata, R.; Romeo, J. T., Eds.; Plenum: New York, 1995; Vol. 29, pp 249.
9. 7. Fujimoto, Y.; Murasaki, C.; Shimada, H.; Nishioka, S.; Kakinuma, K.; Singh, S.; Singh, M.; Gupta, Y. K.; Sahai, M. Chem. Pharm. Bull. 1994, 42, 1175.
10. 8. Born, L.; Lieb, F. J.; Lorentzen, P.; Moeschler, H.; Nonfon, M.; Söllner, R.; Wendisch, D. Planta Med. 1990, 56, 312.
11. 9. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512;
12. (b) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143.
13. 10. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
14. 11. Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801.
15. 12. Shimada, H.; Nishioka, S.; Singh, S.; Sahai, M.; Fujimoto, Y. Tetrahedron Lett. 1994, 35, 3961.
16. 13. Gu, Z.-M.; Fang, X.-P.; Zeng, L.; Song, R.; Ng, J. H.; Wood, K. V.; Smith, D. L.; McLaughlin, J. L. J. Org. Chem. 1994, 59, 3472.
17. 14. Zhao, G.-X.; Gu, Z.-M.; Zeng, L.; Chao, J.-F.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L. Tetrahedron 1995, 51, 7149.
18. 15. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8529.
19. 16. McLaughlin, J. L. In Methods in Plant Biochemistry; Hostettmann, K., Ed.; Academic: London, 1991; Vol. 6, pp 1-35; Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichols, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31.
20. 16. McLaughlin, J. L. In Methods in Plant Biochemistry; Hostettmann, K., Ed.; Academic: London, 1991; Vol. 6, pp 1-35; Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichols, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31.
21. 1
22. 18. Ahammadsahib, K. I.; Hollingworth, R. M.; McGovren, J. P.; Hui, Y.-H.; McLaughlin, J. L. Life Sci. 1993, 53, 1113.
23. 19. Morré, D. J.; Cabo, R. D.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343.
24. 20. Landolt, J. L.; Ahammadsdahib, K. I.; Hollingworth, R. M.; Barr, R.; Crane, F. L.; Buerck, N. L.; McCabe, G. P.; McLaughlin, J. L. Chem.-Biol. Interact. 1995, 98, 1.