Skip to main content
Log in

Symbiotic and dietary marine microalgae as a source of bioactive molecules–experience from natural products research

  • Published:
Journal of Applied Phycology Aims and scope Submit manuscript

Abstract

Cyanobacterial metabolites have proven to be invaluable as tools in thedissection of signal transduction pathways in mammalian cells and some arecurrently under clinical evaluation as drug candidates. It is now also realizedthat cyanobacteria are the true biosynthetic origin of many bioactive moleculesisolated from marine invertebrates; marine invertebrates may sequestercyanobacteria through diet or by symbiosis. This review discusses thedietary-derived cyanobacterial origin of the dolastatins, potent cytotoxiccompounds, originally isolated from the Indian Ocean sea hare,Dolabella auricularia. A discussion on the dietarydissemination of cyanobacterial metabolites through the marine food chain isalso presented. Reference to the metabolites isolated fromDysidea sponges is given to illustrate their origin fromsymbiotic cyanobacteria associated with this organism.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Biskupiak J.E. and Ireland C.M. 1984. Revised absolute configuration of dysidenin and isodysidenin. Tetrahedron Letts. 25: 2935-2936.

    Google Scholar 

  • Carmeli S., Moore R.E. and Patterson G.M.L. 1990. Tolytoxin and new scytophycins from three species of Scytonema. J. Nat. Prod. 53: 1533-1542.

    Google Scholar 

  • Carter D.C., Moore R.E., Mynderse J.S., Niemczura W.P. and Todd J.S. 1984. Structure of majusculamide C a cyclic depsipeptide from Lyngbya majuscula. J. Org. Chem. 49: 236-241.

    Google Scholar 

  • Faulkner D.J. 2000. Marine natural products. Nat. Prod. Rep. 17: 7-55.

    Google Scholar 

  • Harrigan G.G., Yoshida W.Y., Moore R.E., Nagle D.G., Park P.U., Biggs J. et al. 1998a. Isolation, structure determination, and biological activity of dolastatin 12 and lyngbyastatin 1 from Lyngbya majuscula/Schizothrix calcicola cyanobacterial assemblages. J. Nat. Prod. 61: 1221-1225.

    Google Scholar 

  • Harrigan G.G., Luesch H., Yoshida W.Y., Moore R.E., Nagle D.G., Paul V.J. et al. 1998b. Symplostatin 1: A dolastatin 10 analogue from the marine cyanobacterium Symploca hydnoides. J. Nat. Prod. 61: 1075-1077.

    Google Scholar 

  • Harrigan G.G., Luesch H., Yoshida W.Y., Moore R.E., Nagle D.G. and Paul V.J. 1999. Symplostatin 2 a dolastatin 13 analogue from the marine cyanobacterium Symploca hydnoides. J. Nat. Prod. 62: 655-658.

    Google Scholar 

  • Harrigan G.G., Luesch H., Moore R.E. and Paul V.J. 2000. The anticancer dolastatins as cyanobacterial metabolites. Spec. publ. R. Soc. Chem. 257: 126-139.

    Google Scholar 

  • Harrigan G.G., Goetz G.H., Luesch H., Yang S. and Likos J. 2001. Dysideaprolines A-F and barbaleucamides A-B novel polychlorinated compounds from a Dysidea sp. J. Nat. Prod. in-press.

  • Jaspars M. and Lawton L.A. 1998. Cyanobacteria - a novel source of pharmaceuticals. Curr. Opin. Drug Discovery and Development: 77-84.

  • Jiménez J. and Scheuer P.J. 2001. New lipopeptides from the Caribbean cyanobacterium Lyngbya majuscula. J. Nat. Prod. 64: 200-203.

    Google Scholar 

  • Kimura J., Takada Y., Goetz G., Nakao Y. and Scheuer P.J. 2000. The absolute stereochemistry of a new cyclic depsipeptide. In: 2000 Conference. Pacifichem, Honolulu, Hawaii, USA.

  • Kobayashi M., Kurosu M., Ohyabu N., Wang W., Fujii S. and Kitagawa I. 1994. The absolute stereostructure of arenastatin A, a potent cytotoxic depsipeptide from the Okinawan marine sponge Dysidea arenaria. Chem. Pharm. Bull. 42: 2196-2198.

    Google Scholar 

  • Marner F.J., Moore R.E., Hirotsu K. and Clardy J. 1977. Majusculamides A and B; two epimeric lipopetides from Lyngbya majuscula Gomont. J. Org. Chem. 42: 2815-2819.

    Google Scholar 

  • Moore R.E. 1996. Cyclic peptides and depsipeptides from cyanobacteria - a review. J. Industr. Microbiol. 16: 134-143.

    Google Scholar 

  • Nakao Y., Yoshida W.Y. and Scheuer P.J. 1996. Pupukeamide a linear tetrapeptide from a cephalaspidean mollusk Philinopsis speciosa. Tetrahedron Letts. 37: 8993-8996.

    Google Scholar 

  • Orjala J. and Gerwick W.H. 1996. Barbamide, a chlorinated metabolite with molluscicidal activity from the Caribbean cyanobacterium Lyngbya majuscula. J. Nat. Prod. 59: 427-430.

    Google Scholar 

  • Pettit G.R. 1996. Progress in the discovery of biosynthetic anticancer drugs. J. Nat. Prod. 59: 812-821.

    Google Scholar 

  • Pettit G.R., Xu J., Hogan F., Williams M.D., Doubek D.L., Schmidt J.M. et al. 1997. Isolation and structure elucidation of the human cancer cell growth inhibitory cyclodepsipeptide dolastatin 16. J. Nat. Prod. 60: 752-754.

    Google Scholar 

  • Reese M.T., Gulavita N.K., Nakao Y., Hamman M.T., Yoshida W.Y., Coval S.J. et al. 1996. Kululolide-a cytotoxic depsipeptide from cepahalaspidean mollusk Philinopsis speciosa. J. Am. Chem. Soc. 118: 11081-11084.

    Google Scholar 

  • Skulberg O.M. 2000. Microalgae as a source of bioactive molecules-experience from cyanophyte research. J. Appl. Phycol. 12: 341-348.

    Google Scholar 

  • Suenaga K., Nagoya T., Shibata T., Kigoshi H. and Yamada K. 1997. Dolabelides C and D cytotoxic metabolites isolated from the sea hare Dolabella auricularia. J. Nat. Prod. 60: 155-157.

    Google Scholar 

  • Trimurtulu G., Ohtani I., Patterson G.M.L., Moore R.E., Corbett T.H., Valeriote F.A. et al. 1994. Total structures of cryptophycins, potent antitumor depsipeptides from the blue-green alga Nostoc sp. strain GSV 224. J. Am. Chem. Soc. 116: 4729-4737.

    Google Scholar 

  • Unson M.D. and Faulkner D.J. 1993. Cyanobacterial symbiont biosynthesis of chlorinated metabolites from Dysidea herbacea (Porifera). Experientia 49: 349-353.

    Google Scholar 

  • van Sande J., Deneubourg F., Beauwens R., Braekman J.C., Daloze D. and Dumont J.E. 1990. Inhibition of iodide transport in thyroid cells by dysidenin a marine toxin and some of its analogs. Mol. Pharmacol. 37: 583-589.

    Google Scholar 

  • Yamada K., Ojika M., Ishigaki T., Yoshida Y., Ekimoto E. and Arakawa M. 1993. Apylronine A a potent antitumor substance and the congeners apylronines B and C isolated from the sea hare Apylsia kurodai. J. Am. Chem. Soc. 115: 11020-11021.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Harrigan, G.G., Goetz, G. Symbiotic and dietary marine microalgae as a source of bioactive molecules–experience from natural products research. Journal of Applied Phycology 14, 103–108 (2002). https://doi.org/10.1023/A:1019570122349

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1019570122349

Navigation