Skip to main content

Isolation, Structural, and Mode-of Action Studies on Bioactive Marine Natural Products

  • Chapter

Abstract

Despite the current interest in bioactive marine compounds, our knowledge is limited because of the short history of this area of research. Moreover, the difficulties associated with the collection and isolation of marine samples in comparison to terrestrial samples have hampered progress. However, there are great possibilities for exciting discoveries, both academic and practical.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Barrow, C. J., Nakaniski, K., and Tachibana, K., 1992, Structural considerations for the pore forming properties of pardaxin, Biochim. Biophys. Acta (Submitted).

    Google Scholar 

  • Borst, D. W, Laufer, H., Landau, M., Chang, E. S., Hertz, W. A., Baker, E. C., and Schooley, D. A., 1987, Methyl farnesoate and its role in crustacean reproduction and development, Insect Biochem. 37: 1123–1127.

    Google Scholar 

  • Brown, F A., Jr., and Cunningham, O., 1939, Influence of the sinus gland of crustaceans on normal viability and ecdysis, Biol. Bull. 77: 104–114.

    Article  Google Scholar 

  • Brown, L. R., Lauterwein, J., and Wüthrich, K., 1980, High resolution 1H-NMR studies of self-aggregation of melittin in aqueous solution, Biochim. Biophys. Acta 622: 231–244.

    Article  PubMed  CAS  Google Scholar 

  • Bruening, R. C., Oltz, E. M., Furukawa, J., Nakanishi, K., and Kustin, K., 1985, Isolation and structure of tunichrome B-1, a reducing blood pigment from the tunicate Ascidia nigra, J. Am. Chem. Soc. 107: 5298.

    Article  CAS  Google Scholar 

  • Bruening, R. C., Oltz, E. M., Furukawa, J., Nakanishi, K., and Kustin, K., 1986, Isolation of tunichrome B-1, a reducing blood pigment of the sea squirt, Ascidia nigra, J. Nat. Prod. 49: 193–204.

    Article  PubMed  CAS  Google Scholar 

  • Bulls, A. R., Pippin, C. G., Hahn, F E., and Raymond, K. N., 1990, J. Am. Chem. Soc. 112:2627. Carlson, R. M. K., 1975, Proc. Natl. Acad. Sci. USA 72: 2217.

    Google Scholar 

  • Chang, E. S., and O’Connor, J. D., 1977, Secretion of a-ecdysone by crab Y-organs in vitro, Proc. Natl. Acad. Sci. USA 74: 615–618.

    Article  PubMed  CAS  Google Scholar 

  • Chang, E. S., Sage, B. A., and O’Connor, J. D., 1976, The qualitative and quantitative determinations of ecdysones in tissues of the crab, Pachygrapsus crassipes, following molt induction, Gen. Comp. Endocrinol. 30: 21–33.

    Article  PubMed  CAS  Google Scholar 

  • Chang, E. S., Prestwich, G. D., and Bruce, M. J., 1990, Amino acid sequence of a peptide with both molt-inhibiting and hyperglycemic activities in the lobster, Homarus americanus, Biochem. Biophys. Res. Commun. 171: 818–826.

    Google Scholar 

  • Chou, P Y., and Fasman, G. D., 1978, Empirical predictions of protein conformation, Annu. Rev. Biochem. 47: 251–276.

    Article  PubMed  CAS  Google Scholar 

  • Clark, E., 1974, The Red Sea’s shark proof fish, Natl. Geogr. Mag. 146: 719–727.

    Google Scholar 

  • Clark, E., and George, A., 1979, Toxic soles, Pardachirus marmoratus from the Red Sea and P. pavoninus from Japan, with notes on other species, Environ. Biol. Fishes 4: 103–123.

    Article  Google Scholar 

  • Dingley, A. L., Kustin, K., Macara, I. G., and McLeod, G. C., 1981, Accumulation of vandium by tunicate blood cells occurs via a specific anion transport system, Biochim. Biophys. Acta 649: 493–502.

    Article  CAS  Google Scholar 

  • Frank, P, Carlson, R. M. K., and Hodgson, K. O., 1986, Vandyl ion EPR as a noninvasive probe of pH in intact vanadocytes from Ascidia ceratodes, Inorg. Chem. 25: 470–478.

    CAS  Google Scholar 

  • Frank, P, Hedman, B., Carlson, R. M. K., Tyson, T. A., Roe, A. L., and Hodgson, K. 0., 1987, A large reservoir of sulfate and sulfonate resides within plasma cells from Ascidia ceratodes, revealed by absorption near-edge structure spectroscopy, Biochemistry 26: 4975–4979.

    CAS  Google Scholar 

  • Freeman, J. A., 1980, Hormonal control of chitinolytic activity in the integument of Balanusamphitrite, in vitro, Comp. Biochem. Physiol. 65A: 13–17.

    Article  Google Scholar 

  • Gabe, M., 1953, Sur l’existence, chez quelques crustacés malacostracés, d’un organe comparable à la glande de la mue des insectes, C. R. Acad. Sci. Paris 237: 1111–1113.

    PubMed  CAS  Google Scholar 

  • Gruber, S. H., 1977, The visual system of sharks, Am. Zool. 17: 453–469.

    Google Scholar 

  • Gruber, S. H., 1981, Shark repellents: Perspectives for the future, Oceanus 24 (4): 72–76.

    Google Scholar 

  • Hochachka, P W, and Guppy, M., 1987, Metabolic Arrest and the Control of Biological Time, Harvard University Press, Cambridge, Massachusetts.

    Google Scholar 

  • Horenstein, B. A., and Nakanishi, K.,1989, Synthesis of unprotected (±)-tunichrome An-1, a tunicate blood pigment, J. Am. Chem. Soc. 111: 6242–6246.

    Google Scholar 

  • Huberman, A., and Aguilar, M. B., 1989, A neuropeptide with molt-inhibiting hormone activity from the sinus gland of the Mexican crayfish Procambarus bouvieri (Ortmann), Comp. Biochem. Physiol. 93B: 299–305.

    Google Scholar 

  • Jegla, T. C., Ruland, C., Kegel, G., and Keller, R., 1983, The role of the Y-organ and cephalic gland in ecdysteroid production and the control of molting in the crayfish Orconectes limosus, J. Comp. Physiol. 152B: 91–95.

    CAS  Google Scholar 

  • Kalmijin, A. J., 1966, Electro-perception in sharks and rays, Nature 212: 1232–1233.

    Article  Google Scholar 

  • Kappler, C., Kabbouh, M., Hetru, C., Durst, F., and Hoffmann, J. A., 1988, Characterization of three hydroxylases involved in the final steps of biosynthesis of the steroid hormone ecdysone in Locusta migratoria insecta orthoptera, J. Steroid Biochem. 31: 891–898.

    Article  PubMed  CAS  Google Scholar 

  • Kim, D., Li, Y., and Nakanishi, K., 1991, Isolation of unstable tunichromes from tunicate blood via protection—deprotection, J. Chem. Soc. Chem. Commun. 1991: 9–10.

    Article  Google Scholar 

  • Kim, D., Li, Y., Horenstein, B. A., and Nakanishi, K., 1990, Synthesis of tunichromes Mm-1 and Mm-2, blood pigments of the iron-assimilating tunicate, Molgula manhattensis, Tetrahedron Lett. 31: 7119–7122.

    Article  CAS  Google Scholar 

  • Kime-Hunt, E., Spartalian, K.,and Carrano, C. J., 1988, Models for vanadium-tunichrome interactions, J. Chem. Soc. Chem. Commun. 1988: 1217–1218.

    Google Scholar 

  • Kleinholz, L. H., 1985, Biochemistry of crustacean hormones, in: The Biology of Crustacea, Vol. 9 ( D. E. Bliss and L. H. Mantel, eds.), Academic Press, New York, pp. 463–522.

    Google Scholar 

  • Kotake, M., Sakan, T., and Senoh, S., 1951, Studies on amino acids IV. The synthesis of 3-hydroxykynurenie, J. Am. Chem. Soc. 73: 1832–1834.

    Article  CAS  Google Scholar 

  • Lachaise, F., 1989, Diversity of molting hormones in Crustacea, in: Ecdysone, From Chemistry to Mode of Action ( J. Koolman, ed.), Thieme Medical, New York, pp. 313–318.

    Google Scholar 

  • Lachaise, E, and Feyereisen, R., 1976, Métabolisme de l’ecdysone par divers organes de Carcinus maenas L. incubés in vitro, C. R. Acad. Sci. Paris 283: 1445–1448.

    Google Scholar 

  • Laufer, H., Landau, M., Homola, E., and Borst, D. W, 1987, Methyl farnesoate: Its site of synthesis and regulation of secretion in a juvenile crustacean, Insect Biochem. 17: 1129–1131.

    Article  CAS  Google Scholar 

  • Lazarovici, P, Primor, N., and Loew, L. M., 1986, Purification and pore-forming activity of two hydrophobic polypeptides from the secretion of the Red Sea Moses sole (Pardachirus marmoratus), J. Biol. Chem. 261: 16704–16713.

    PubMed  CAS  Google Scholar 

  • Lazarovici, P, Primor, N., Gennaro, J., Fox, J., Shai, Y., Lelkes, P. I., Caratsch, C. G., Raghunathan, G., Guy, H. R., Shih, Y. L., and Edwards, C., 1990, Origin, chemistry, and mechanisms of action of a repellent, presynaptic excitatory, ionophore polypeptide, in: Marine Toxins: Origin, Structure, and Molecular Pharmacology ( S. Hall and G. Strichartz, eds.), American Chemical Society, Washington, D.C., pp. 347–364.

    Google Scholar 

  • Lee, S., Kustin, K., Robinson, W. E., Frankel, R. B., and Spartalian, K., 1988, Magnetic properties of tunicate blood cells. I. Ascidia nigra, J. Inorg. Biochem. 33: 183–192.

    Article  PubMed  CAS  Google Scholar 

  • Lee, S., Nakanishi, K., and Kustin, K., 1990, The intracellular pH of tunicate blood cells: Ascidia ceratodes whole blood, morula cells, vacuoles and cytoplasm. Biochem. Biophys. Acta 1033: 311–317.

    Article  PubMed  CAS  Google Scholar 

  • Lowe, M. E., Horn, D. H. S., and Galbraith, M. N., 1968, The role of crustecdysone in the molting crayfish, Experientia 24: 518–519.

    Article  PubMed  CAS  Google Scholar 

  • Macara, I. G., McLeod, G. C., and Kustin, K., 1979, Isolation, properties and structural studies on a compound from tunicate blood cells that may be involved in vanadium accumulation, Biochem. J. 181: 457–465.

    PubMed  CAS  Google Scholar 

  • Mattson, M. P, and Spaziani, E., 1986, Regulation of the stress-responsive X-organ—Y-organ axis by 5-hydroxy-tryptamine in the crab. Cancer antennarius, Gen. Comp. Endocrinol. 62: 419–427.

    Article  PubMed  CAS  Google Scholar 

  • Mattson, M. P., and Spaziani, E., 1987, Demonstration of protein kinase C activity in crustacean Y-organs and partial definition of its role in regulation of ecdysteroidogenesis, Mol. Cell. Endocrinol. 49: 159–172.

    Article  PubMed  CAS  Google Scholar 

  • Megusar, F., 1912, Experimente über den Farbwechsel der Crustaceen, Arch. Entwickl.-Mech. 33: 462.

    Article  Google Scholar 

  • Moran, A., Korchak, Z., Moran, N., and Primor, N., 1984, Surfactant and channel-forming activities of the Moses sole toxin, in: Toxins, Drugs, and Pollutants in Marine Animals ( L. Bolis, J. Zadunaisky, and R. Gilles, eds.), Springer-Verlag, Berlin, pp. 13–25.

    Google Scholar 

  • Naya, Y., and Sonobe, H., 1990, Molt-regulating factors: Comparative study in crustaceans and insects, Heredity 44: 62–67 [in Japanese].

    Google Scholar 

  • Naya, Y., Kishida, K., Sugiyama, M., Murata, M., Mild, W, Ohnishi, M., and Nakanishi, K., 1988, Endogenous inhibitor of ecdysone synthesis in crabs, Experientia 44: 50–52.

    Article  PubMed  CAS  Google Scholar 

  • Naya, Y., Ohnishi, M., Ikeda, M., Miki, W, and Nakanishi, K., 1989, What is molt-inhibiting hormone? The role of an ecdysteroidogenesis inhibitor in the crustacean molting cycle, Proc. Natl. Acad. Sci. USA 86: 6826–6829.

    Article  PubMed  CAS  Google Scholar 

  • Neilands, J. B., 1984, Siderophores of bacteria and fungi, Microbiol. Sci. 1: 9–14.

    PubMed  CAS  Google Scholar 

  • Newcom, R. W, Stuenkel, E. L., and Cooke, I. M., 1985, Characterization, biosynthesis and release of neuropeptides from the X-organ-sinus gland system of the crab Cardisoma carnifex, Am. Zool. 25: 157–171.

    Google Scholar 

  • Ohnishi, M., Nakanishi, K., and Naya, Y., 1991, Down-regulation of ecdysteroidogenesis: Physiological dynamics of prothoracic and Y-glands, CHIMICAoggi 9: 53–56.

    CAS  Google Scholar 

  • Oltz, E. M., Bruening, R. C., Smith, M. J., Kustin, K., and Nakanishi, K., 1988, The tunichromes. A class of reducing blood pigments from sea squirts: Isolation, structures, and vanadium chemistry, J. Am. Chem. Soc. 110: 6162–6172.

    Article  PubMed  CAS  Google Scholar 

  • Oltz, E. M., Pollack, S., Delohery, T., Smith, M. J., Ojika, M., Lee, S., Kustin, K., and Nakanishi, K., 1989, Distribution of tunichrome and vanadium in sea squirt blood cells sorted by flow cytometry, Experientia 45: 186–190.

    Article  PubMed  CAS  Google Scholar 

  • Passano, L. M., 1960, Molting and its control, in: The Physiology of Crustacea, Vol. 1 ( T. H. Waterman, ed.), Academic Press, New York, pp. 473–536.

    Google Scholar 

  • Primor, N., 1985, Pharyngeal cavity and the gills are the target organ for the repellent action of pardaxin in shark, Experientia 41: 693–695.

    Article  PubMed  CAS  Google Scholar 

  • Primor, N., Parness, J., and Zlotkin, E., 1978, Pardaxin, the toxic factor from the skin secretion of the flatfish Pardachirus marmoratus (Soleidae), in: Toxins: Animal, Plant and Microbial ( P. Rosenberg, ed.), Pergamon Press, Oxford, pp. 539–547.

    Google Scholar 

  • Schaffer, J., Kramer, K. J., Garbow, J. R., Jacob, G. S., Stejskal, E. O., Hopkins, T. L., and Speirs, R. D., 1987, Aromatic cross-links in insect cuticle: Detection by solid-state 13C and 15N NMR, Science 235: 1200–1204.

    Article  Google Scholar 

  • Schmidt, U., Lieberknect, A., and Wild, J., 1988, Didehydroamino acid (DDAA) and didehydropeptides (DDP), Synthesis 1988: 159–172.

    Article  Google Scholar 

  • Skinner, D. M., 1985, Molting and regulation, in: The Biology of Crustacea, Vol. 9 ( D. E. Bliss and L. H. Mantel, eds.), Academic Press, New York, pp. 43–146.

    Google Scholar 

  • Smith, M. J., 1989, Vanadium biochemistry: The unknown role of vanadium-containing cells in ascidians (sea squirts), Experientia 45: 452–457.

    Article  PubMed  CAS  Google Scholar 

  • Smith, S. L., 1985, Regulation of ecdysteroid titer: Synthesis, in: Comprehensive Insect Physiology, Biochemistry and Pharmacology (G. A. Kerkut and L. I. Gilbert, eds.), Pergamon Press, Oxford, Vol. 7, pp. 295–341.

    Google Scholar 

  • Sonobe, H., Kanba, M., Ohta, K., Ikeda, M., and Naya, Y., 1991, In vitro secretion of ecdysteroids by Y-organs of the crayfish, Procambarus clarkii, Experientia 47: 948–952.

    CAS  Google Scholar 

  • Soyez, D., and Kleinholz, L. H., 1977, Molt-inhibiting factor from the crustacean eyestalk, Gen. Comp. Endocrinol. 31: 233–242.

    Article  PubMed  CAS  Google Scholar 

  • Spaziani, E., 1988, Serum high-density lipoprotein in the crab, Cancer antennarius Stimpson: II. Annual Cycles, J. Exp. Zool. 246: 315–318.

    Article  CAS  Google Scholar 

  • Sugumaran, M., 1987, Quinone methide sclerotization: A revised mechanism for b-sclerotization of insect cuticle, Bioorg. Chem. 15: 194–211.

    Article  CAS  Google Scholar 

  • Tachibana, K., and Gruber, S. H., 1988, Shark repellent lipophilic constituents in the defense secretion of the Moses sole (Pardachirus marmoratus), Toxicon 26: 839–853.

    Article  PubMed  CAS  Google Scholar 

  • Tachibana, K., Sakaitani, M., and Nakanishi, K., 1985, Pavoninins, shark-repelling and ichthyotoxic steroid N-acetylglucosaminides from the sole Pardachirus pavoninus (Soleidae), Tetrahedron 41: 1027–1037.

    Article  CAS  Google Scholar 

  • Tachibana, K., Xu, W-H., Barrow, C. J., and Imoto, S., 1989, Action of pardaxins and their des analogues on artificial liposomes, in: Peptide Chemistry 1988 ( M. Ueki, ed.), Protein Research Foundation, Osaka, pp. 279–282.

    Google Scholar 

  • Terwillinger, T. C., and Eisenberg, D., 1982, The structure of melittin: Interpretation of the structure, J. Biol. Chem. 257: 6016–6022.

    Google Scholar 

  • Testa, B., and Jenner, P., 1981, Inhibitors of cytochrome P-450s and their mechanism of action, in: Drug Metabolism Reviews (F. J. Di Carlo, ed.), Marcel Dekker, New York, Vol. 12 (1), pp. 1–117.

    Google Scholar 

  • Thompson, S. A., Tachibana, K., Nakanishi, K., and Kubota, I., 1986, Melittin-like peptides from the shark-repelling defense secretion of the sole Pardachirus pavoninus, Science 233: 341–343.

    Article  PubMed  CAS  Google Scholar 

  • Thompson, S. A., Minakata, H., Xu, W.-H., Tachibana, K., Nakanishi, K., and Kubota, I., 1987, Melittin-like amphiphilic peptides in the defense secretion of the sole Pardachirus pavoninus: Isolation, structures, and bioactivity, in: Peptide Chemistry 1986 ( T. Miyazawa, ed.), Protein Research Foundation, Osaka, pp. 181–184.

    Google Scholar 

  • Thompson, S. A., Tachibana, K., Kubota, I., and Zlotkin, E., 1988, Amino acid sequence of pardaxin in the defense secretion of the Red Sea Moses sole, in: Peptide Chemistry 1987 ( T. Shiba and S. Sakakibara, eds.), Protein Research Foundation, Osaka, pp. 127–130.

    Google Scholar 

  • Watson, R. D., and Spaziani, E., 1985, Effects of eyestalk removal on cholesterol uptake and ecdysone secretion by crab Cancer antennarius Y-organs in vitro, Gen. Comp. Endocrinol. 57: 360–370.

    Article  PubMed  CAS  Google Scholar 

  • Webster, S. G., and Keller, R., 1986, Purification, characterization and amino acid composition of the putative moult-inhibiting hormone (MIH) of Carcinus maenas (Crustacea, Decapoda), J. Comp. Physiol. 1568: 617–624.

    Google Scholar 

  • Webster, S. G., and Keller, R., 1989, Molt inhibiting hormone, in: Ecdysone, From Chemistry to Mode of Action (J. Koolman, ed.), Thieme Medical, New York, pp. 211–216.

    Google Scholar 

  • Zagorsky, M. G., Norman, D. G., Barrow, C. J., Iwashita, T., Tachibana, K., and Patel, D. J., 1991, Solution structure of pardaxin P-2, Biochemistry 30: 8009–8017.

    Article  Google Scholar 

  • Zahuranec, B. J. (ed.), 1983, Shark Repellents from the Sea: New Perspectives, Westview Press, Boulder, Colorado.

    Google Scholar 

  • Zahuranec, B. J., and Baldridge, Jr., H. D., 1983, Shark research and the United States Navy, in: Shark Repellents from the Sea: New Perspectives (B. J. Zahuranec, ed.), Westview Press, Boulder, Colorado, pp. 1–10.

    Google Scholar 

  • Zeleny, C., 1905, Compensatory regulation, J. Exp. Zool. 2: 1–102.

    Article  Google Scholar 

  • Zlotkin, E., and Barenholz, Y., 1983, On the membranal action of pardaxin, in: Shark Repellents from the Sea: New Perspectives ( B. J. Zahuranec, ed.), Westview Press, Boulder, Colorado, pp. 157–171.

    Google Scholar 

  • Zlotkin, E., and Gruber, S. H., 1984, Synthetic surfactants: A new approach to the development of shark repellents, Arch. Toxicol. 56: 55–58.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1993 Springer Science+Business Media New York

About this chapter

Cite this chapter

Naya, Y., Tachibana, K., Nakanishi, K. (1993). Isolation, Structural, and Mode-of Action Studies on Bioactive Marine Natural Products. In: Attaway, D.H., Zaborsky, O.R. (eds) Pharmaceutical and Bioactive Natural Products. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-2391-2_2

Download citation

  • DOI: https://doi.org/10.1007/978-1-4899-2391-2_2

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-2393-6

  • Online ISBN: 978-1-4899-2391-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics