Isolation and cytotoxic evaluation of marine sponge-derived norterpene peroxides

Journal of Natural Products

Volumn 61, Issue 2, 1998, Pages 241-247

  Sperry, Sam ^a   Valeriote, Frederick A ^b   Corbett, Thomas H ^b   Crews, Phillip ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TERPENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DRUG ISOLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PORIFERA; TERPENES; TUMOR CELLS, CULTURED;

EID: 0031881662     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np970467w     Document Type: Article

References (35)

1. Kashman, Y.; Rotem, M. Tetrahedron Lett. 1979, 1707-1708.
2. (a) Albericci, M.; Collart-Lempereur, M.; Braekman, J. C.; Daloze, D.; Tursch, B. Tetrahedron Lett. 1979, 2687-2690.
3. (b) Albericci, M.; Braekman, J. C.; Daloze, D.; Tursch, B. Tetrahedron 1982, 38, 1881-1890.
4. Sokoloff, S.; Halevy, S.; Usieli, V.; Colorni, A.; Sarel, S. Experientia 1982, 38, 337-338.
5. Nuapapuin A was formerly referred to as methyl nuapapuanoate; Manes, L. V.; Bakus, G. J.; Crews, P. Tetrahedron Lett. 1984, 25, 931-934.
6. Reexammation of our voucher by Dr. M. C. Diaz (UCSC, Institute of Marine Sciences) indicates it to be Diacarnus cf. spinopoculum (family Latrunculiidae, order Poecilosclerida). The family Latrunculiidae can arguably be placed in orders Hadromerida or Poecilosclerida: Kelly-Borges, M.; Vacelet, J. Mem. Queensl. Mus. 1995, 38, 477-503.
7. (a) Capon, R. J.; MacLeod, J. K. Tetrahedron 1985, 41, 3391-3404.
8. (b) Capon, R. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: Amsterdam, 1991, Vol. 9; pp 15-33.
9. (c) Faulkner, D. J.; He, H.; Lu, H. S. M.; Clardy, J. J. Org. Chem. 1991, 56, 2112-2115.
10. (d) Capon, R. J. J. Nat. Prod. 1991, 54, 190-195.
11. Tanaka, J.; Higa, T.; Suwanborirux, K.; Kokpol, U.; Bernardinelli, G.; Jefford, C. W. J. Org. Chem. 1993, 58, 2999-3002.
12. Capon, R. J.; MacLeod, J. K.; Willis, A. C. J. Org. Chem. 1987, 52, 339-342.
13. Polyketide peroxides: (a) Quiñoà, E.; Kho, E.; Manes, L. V.; Crews, P.; Bakus, G. J. J. Org. Chem. 1986, 51, 4260-4264.
14. (b) Varoglu, M.; Peters, B. M.; Crews, P. J. Nat. Prod. 1995, 58, 27-36.
15. (c) Ichiba, T.; Scheuer, P. J.; Kelly-Borges, M. Tetrahedron 1995, 51, 12195-12202; U.S. patent 5514705 A.
16. (d) Horton, P. A.; Longley, R. E.; Kelly-Borges, M.; McConnell, O. J.; Ballas, L. M. J. Nat. Prod. 1994, 57, 1374-1381.
17. (e) Rudi, A.; Kashman, Y. J. Nat. Prod. 1993, 56, 1827-1830.
18. (f) Davidson, B. S. Tetrahedron Lett. 1991, 32, 7167-7170.
19. (g) Gunasekera, S. P.; Gunasekera, M.; Gunawardana, G. P.; McCarthy, P.; Burres, N. J. Nat. Prod. 1990, 53, 669-674.
20. (h) Toth, S. I.; Schmitz, F. J. J. Nat. Prod. 1994, 57, 123-127. Norterpene Peroxides:
21. 7; patent appl., EP 610076 A1.
22. (a) Valeriote, F.; Corbett, T.; LoRusso, P.; Moore, R. E.; Scheuer, P.; Patterson, G.; Paul, V.; Grindey, G.; Bonjouklian, R.; Pearce, H.; Suffness, M. Intl. J. Pharmacog. 1995, 33 (Suppl), 59-66.
23. (b) Valeriote, F.; Corbett, T.; Edelstein, M.; Baker, L. Cancer Invest. 1996, 14, 124-141.
24. (c) Corbett, T. H.; Valeriote, F. A.; Polin, L.; Panchapor, C.; Pugh, S.; White, K.; Lowichik, N.; Knight, J.; Bissery, M.-C.; Wozniak, A.; LoRusso, P.; Biernat, L.; Polin, D.; Knight, L.; Biggar, S.; Looney, D.; Demchik, L.; Jones, J.; Jones, L.; Scott, B.; Palmer, K.; Essenmacher, S.; Lisow, L.; Mattes, K. C.; Cavanaugh, P. R.; Rake, J. B.; Baker, L. In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development; Valeriote, F. A., Corbett, T. H., Baker, L. H., Eds.; Kluwer Academic: Norwell, MA, 1992; pp 35-87.
25. For our standard extraction procedure see: Rodríguez, J.; Nieto, R. M.; Crews, P. J. Nat. Prod. 1993, 56, 2034-2040.
26. Structure 11 was previously described as a synthetic product: Semenovski, A. V.; Smit, V. A.; Kucherov, V. F. Dokl. Akad. SSSR. 1965, 160, 1097-1101.
27. A partial listing of these models includes the following: (a) zaatirin: Rudi, A.; Kashman, Y. J. Nat. Prod. 1992, 55, 1408-1414.
28. (b) oceanapamine: Boyd, K. G.; Harper, M. K.; Faulkner, D. J. J. Nat. Prod. 1993, 58, 302-305.
29. (c) agellesine E: Wu, H.; Nakamura, H.; Kobayashi, J.; Ohizumi, Y.; Hirata, Y. Tetrahedron Lett. 1984, 25, 3719-3722.
30. (d) pallescensone: Cambie, R. C.; Craw, P. A.; Bergquist, P. R.; Karuso, P. J. Nat. Prod. 1987, 50, 948-949.
31. Cytotoxicity measurements for (+)-1b may be unreliable because of its instability.
32. Hollingshead, M. G.; Alley, M. C.; Camalier, R. F.; Abbot, B. J.; Mayo, J. G.; Malspeis, L.; Grever, M. R. Life Sci. 1995, 57, 131-141.
33. Munro, M. H. G.; Blunt, J. W.; Lake, R. J.; Litaudon, M.; Battershill, C. N.; Page, M. J. In Sponges in Time and Space; van Soest, R. W. M., van Kempen, Th.M. G., Braekman, J. C., Eds.; A. A. Balkema: Rotterdam, 1994; pp 473-484.
34. Behr, D.; Wahlberg, I.; Nishida, T.; Enzell, C. R. Acta Chem. Scand. B 1977, 31, 609-613.
35. Hefner, J.; Rubenstein, S. M.; Ketchum, R. E. B.; Gibson, D. M.; Williams, R. M.; Croteau, R. Chem. Biol. 1996, 3, 479-489.