Marine Natural Products

Diversity in Molecular Structure and Bioactivity
  • Paul J. Scheuer
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 391)


The difference between a harmful toxin and a beneficial drug is largely a matter of dose. Historically, toxins provided important leads towards drug discovery, as their purification could be followed by a readily available and unambiguous bioassay — death of a small rodent. Modern sensitive enzyme-based assays have made all natural products — organic compounds isolated from living organisms — a potential source for drug discovery. The oceans of the earth which cover 70% of its surface and are the habitat of a rich and diverse fauna and flora, much of it still to be discovered and described, offer a prime resource for new molecular structures with a broad spectrum of bioactivities.


Human Immunodeficiency Virus Type Okadaic Acid Elenic Acid Marine Natural Product Ciguatera Fish Poisoning 
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  1. 1.
    Juagdan, E. G., Kalidindi, R. S., Scheuer, P. J., and Kelly-Borges, M. 1995. Elenic acid, an inhibitor of topoisomerase II, from a sponge, Plakinastrella sp., Tetrahedron Lett., 36:3977–3980.CrossRefGoogle Scholar
  2. 2.
    Kasahara, K., Fujiwara, Y., Sugimoto, Y., Nishio, K., Tamura, T., Matsuda, T., Saijo, N. 1992. Determinants of response to the DNA topoisomerase II inhibitors doxorubicin and etoposide in human lung cancer cell lines,. J. Natl. Cancer Inst. 84:113–118.PubMedCrossRefGoogle Scholar
  3. 3.
    Carney, J. R. and Scheuer, P. J. 1993. Popolohuanone E, a topoisomerase-II inhibitor with selective lung tumor cytotoxicity from the Pohnpei sponge, Dysidea sp., Tetrahedron Lett. 34:3727–3730.CrossRefGoogle Scholar
  4. 4.
    Luibrand, R. T., Erdman, T. R., Vollmer, J. J., Scheuer, P. J., Finer, J. and Clardy, J. 1979. Ilimaquinone, a sesquiterpenoid quinone from a marine sponge, Tetrahedron 35:609–612.CrossRefGoogle Scholar
  5. 5.
    Loya, S., Tal, R., Kashman, Y. and Hizi, A. 1990. Ilimaquinone, a selective inhibitor of the RNase H activity of human immunodeficiency virus type I reverse transcriptase, Antimicrob. Agents Chemother. 34:2009–2012.PubMedGoogle Scholar
  6. 6.
    Takizawa, P. A., Yucel, J. K., Veit, B., Faulkner, D. J.; Deerinck, T., Soto, G., Ellisman, M. and Malhotra, V. 1993. Complete vesiculation of Golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone. Cell 73:1079–1090.PubMedCrossRefGoogle Scholar
  7. 7.
    Woodward, R. B. 1964. Structure of Tetrodotoxin, Pure Appl. Chem. 9:49–74CrossRefGoogle Scholar
  8. 8.
    Mosher, H. S., Fuhrman, F. A., Buchwald, H. D. and Fischer, H. G. 1964. Tarichatoxin-tetrodotoxin: A potent neurotoxin, Science 144:1100–1110.PubMedCrossRefGoogle Scholar
  9. 9.
    Yasumoto, T., Yasumura, D., Yotsu, M., Michishita, T., Endo, A. and Kotaki, Y. 1986. Bacterial production of tetrodotoxin and anhydrotetrodotoxin by Pseudomonas sp., Agrie. Biol. Chem. 50: 793–795.CrossRefGoogle Scholar
  10. 10.
    Noguchi, T., Jeon, J.-K., Arakawa, O., Sugita, H., Deguchi, Y, Shida, Y. and Hashimoto, K. 1986. Occurrence of tetrodotoxin and anhydrotetrodotoxin in Vibrios sp. isolated from the intestines of a xanthid crab, Atergatis floridus, J. Biochem. 99: 311–314.PubMedGoogle Scholar
  11. 11.
    Tachibana, K. 1980. Structural studies on marine toxins. Ph.D. Dissertation, University of Hawaii, Honolulu, HI.Google Scholar
  12. 12.
    Tachibana, K., Scheuer, P. J., Tsukitani, Y, Kikuchi, H., vanEngen, D., Clardy, J., Gopichand, Y. and Schmitz, F. J. 1981. Okadaic acid, a cytotoxic polyether from sponges of the genus Halichondria, J. Am. Chem. Soc. 103: 2469–2471.CrossRefGoogle Scholar
  13. 13.
    Murakami, Y, Oshima, Y. and Yasumoto, T. 1982. The identification of okadaic acid as a toxic component of a marine dinoflagellate Prorocentrum lima, Bull. Jap. Soc. Sei. Fish., 48: 69–72.Google Scholar
  14. 14.
    Scheuer, P. J. 1994. Ciguatera and its offshoots: Encounters en route to a molecular structure. Tetrahedron, 50: 3–18.CrossRefGoogle Scholar
  15. 15.
    Suganuma, M, Fujiki, H., Suguri, H., Yoshizawa, S., Hirota, M., Nakayasu, M., Ojika, M., Wakamatsu, K., Yamada, K. and Sugimura, T. 1988. Okadaic acid: An additional non-phorbol-12-tetradecanoate-13-acetate-type tumor promoter, Proc. Natl. Acad. Sci., U.S.A. 85: 1768–1771.PubMedCrossRefGoogle Scholar
  16. 16.
    Haystead, T. A. J., Sim, A. T. R., Carling, D., Honnor, R. C, Tsukitani, Y, Cohen P. and Hardie, D. G. 1989. Effects of the rumor promoter okadaic acid on intracellular protein phosphorylation and metabolism. Nature, 337: 78–81.PubMedCrossRefGoogle Scholar
  17. 17.
    Cohen, P., Holmes, C. F. B. and Tsukitani, Y. 1990. Okadaic acid: a new probe for the study of cellular regulation, Trends Biochem. Sci. 15: 98–102.Google Scholar
  18. 18.
    Scheuer, P. J. 1990. Some marine ecological phenomena: Chemical basis and biomedical potential, Science 248: 173–177.PubMedCrossRefGoogle Scholar
  19. 19.
    Yamamura, S. and Hirata, Y. 1963. Structure of aplysin and aplysinol, naturally occurring bromo-com-pounds, Tetrahedron 19: 1485–1496.CrossRefGoogle Scholar
  20. 20.
    Irie, T., Yasunari, Y., Suzuki, T., Imei, N., Kurosawa, E. and Masamune, T. 1965. A new sesquiterpene hydrocarbon from Laurencia glandulifera.Google Scholar
  21. 21.
    Ireland, C. and Scheuer, P.J. 1979. Photosynthetic marine mollusks. In vivo 14C incorporation into metabolites of the Sacoglossan Placobranchus ocellatus, Science 203:922–923.Google Scholar
  22. 22.
    Kay, A. E. 1979. Hawaiian Marine Shells. Bishop Museum Press, Honolulu, HI, p. 454.Google Scholar
  23. 23.
    Hamann, M. T. 1992. Biologically active constituents of some marine invertebrates. Ph.D. Dissertation, University of Hawaii, Honolulu, HI.Google Scholar
  24. 24.
    Hamann, M. T. and Scheuer, P. J. 1993. Kahalalide F, a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the green alga Bryopsis sp. J. Am. Chem. Soc., 115:5825–5826.CrossRefGoogle Scholar
  25. 25.
    Burreson, B. J., Scheuer, P. J., Finer, J. and Clardy, J. 1975. 9-Isocyanopupukeanane, a marine invertebrate allomone, J. Am. Chem. Soc. 97:4763–4764.Google Scholar
  26. 26.
    Johannes, R. E. 1963. A poison-secreting nudibranch (Mollusca: Opisthobranchia), Veliger 5:104–105.Google Scholar
  27. 27.
    Pham, A. T., Ichiba, T., Yoshida, W. Y., Scheuer, P. J., Uchida, T., Tanaka, J. and Higa, T. 1991. Two marine sesquiterpene thiocyanates, Tetrahedron Lett., 32:4843–4846.CrossRefGoogle Scholar
  28. 28.
    DiBlasio, B., Fattorusso, E., Magno, S., Mayol, L., Pedone, C, Santocroce, C and Sica, D. 1976. Axisonitrile-3, axisothiocyanate-3, and axamide-3. Sesquiterpenes with a novel spiro[4,5] decane skeleton from the sponge Axinella cannabina, Tetrahedron 32:473–478.CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1996

Authors and Affiliations

  • Paul J. Scheuer
    • 1
  1. 1.University of Hawaii at ManoaHonoluluUSAUSA

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