Skip to main content
SpringerLink
Log in
Book cover

Natural Products Isolation pp 353–390Cite as

Isolation of Marine Natural Products

  • Protocol

Part of the book series: Methods in Biotechnology ((MIBT,volume 20))

Summary

Marine organisms offer a wealth of chemically diverse compounds that have been evolutionarily preselected to modulate biochemical pathways. Many industrial and academic groups are accessing this source using advanced technology platforms. The purpose of this chapter is to offer some practical guidance in the process of extraction and isolation of marine natural products. Special attention is given to the isolation procedures adapted to the physical and chemical characteristics of the compounds isolated. Recent advances in isolation technology, including automation and direct integration into high-throughput screening systems, are also discussed.

This sheet is adapted from one obtained from Phil Crews’ research group, University of California, Santa Cruz, USA. It must be adapted for each different phylum under investigation.

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

Protocol
USD   49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   159.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Springer Nature is developing a new tool to find and evaluate Protocols. Learn more

References

  1. Faulkner, D. J. (1995) Marine natural products. Nat. Prod. Rep. 12, 223–269.

    Article  CAS  Google Scholar 

  2. Faulkner, D. J. (1996) Marine natural products. Nat. Prod. Rep. 13, 75–125.

    Article  CAS  Google Scholar 

  3. Faulkner, D. J. (1997) Marine natural products. Nat. Prod. Rep. 14, 259–302.

    Article  CAS  Google Scholar 

  4. Faulkner, D. J. (1998) Marine natural products. Nat. Prod. Rep. 15, 113–158.

    Article  CAS  Google Scholar 

  5. Faulkner, D. J. (1999) Marine natural products. Nat. Prod. Rep. 16, 155–198.

    Article  Google Scholar 

  6. Faulkner, D. J. (2000) Marine natural products. Nat. Prod. Rep. 17, 7–55.

    Article  CAS  Google Scholar 

  7. Faulkner, D. J. (2001) Marine natural products. Nat. Prod. Rep. 18, 1–49.

    Article  CAS  Google Scholar 

  8. Faulkner, D. J. (2002) Marine natural products. Nat. Prod. Rep. 19, 1–48.

    CAS  Google Scholar 

  9. Blunt, J. W., Copp, B. R., Munro, M. H. G., Northcote, P. T., and Prinsep, M. R. (2003) Marine natural products. Nat. Prod. Rep. 20, 1–48.

    Article  CAS  Google Scholar 

  10. Blunt, J. W., Copp, B. R., Munro, M. H. G., Northcote, P. T., and Prinsep, M. R. (2004) Marine natural products. Nat. Prod. Rep. 21, 1–49.

    Article  CAS  Google Scholar 

  11. Shimizu, Y. (1985) Bioactive marine natural products, with emphasis on handling of water-soluble compounds. J. Nat. Prod. 48, 223–235.

    Article  CAS  Google Scholar 

  12. Quinn, R. J. (1988) Chemistry of aqueous marine extracts: isolation techniques, in Bioorganic Marine Chemistry, vol. 2 (Scheuer, p., Coll J. C., Elyalov, G. B., and Quinn, R. J., eds.), Springer-Verlag, Berlin, Heidelberg, pp. 1–41.

    Google Scholar 

  13. Riguera, R. (1997) Isolating bioactive compounds from marine organisms. J. Marine Biotech. 5, 187–193.

    CAS  Google Scholar 

  14. Wright, A. E. (1998) Isolation of marine natural products, in Methods in Biotechnology, vol. 4: Natural Products Isolation (Cannell, R. J. P., ed.), Humana, Totowa, NJ, pp. 365–408.

    Chapter  Google Scholar 

  15. Pettit, G. R., Cichacz, Z., Gao, F., et al. (1994) Antineoplastic agents 300. Isolation and structure of the rare human cancer inhibitory macrocyclic lactones spongistatins 8 and 9. J. Chem. Soc. Chem. Commun. 58:1605–1606.

    Article  Google Scholar 

  16. Pettit, G. R. (1996) Progress in the discovery of biosynthetic anticancer drugs. J. Nat. Prod. 59, 812–821.

    Article  CAS  Google Scholar 

  17. Pettit, G. R., Kamano, Y., Herald, C. L., et al. (1987) The isolation and structure of a remarkable marine animal antineoplastic constituent: dolastatin 10. J. Am. Chem. Soc. 109, 6883–6885.

    Article  CAS  Google Scholar 

  18. VanMiddlesworth, F., Cannell, R. J. P. (1998) Dereplication and partial identification of natural products, in Methods in Biotechnology, vol. 4: Natural Products Isolation (Cannell, R. J. P., ed.), Humana, Totowa, NJ, pp. 279–327.

    Chapter  Google Scholar 

  19. Shimizu, Y. (1998) Purification of water-soluble natural products, in Methods in Biotechnology, vol. 4: Natural Products Isolation (Cannell, R. J. P., ed.), Humana, Totowa, NJ, pp. 329–341.

    Chapter  Google Scholar 

  20. Stead, P. (1998) Isolation by preparative HPLC, in Methods in Biotechnology, vol. 4: Natural Products Isolation (Cannell, R. J. P., ed.), Humana, Totowa, NJ, pp. 165–208.

    Chapter  Google Scholar 

  21. Cannell, R. J. P. (1998) How to approach the isolation of a natural product, in Methods in Biotechnology, vol. 4: Natural Products Isolation (Cannell, R. J. P., ed.), Humana, Totowa, NJ, pp. 1–51.

    Chapter  Google Scholar 

  22. Bradshaw, T. P. (2000) A User’s Guide: Introduction to Peptide and Protein HPLC. Phenomenex, USA.

    Google Scholar 

  23. Dufresne, C. (1998) Isolation by ion-exchange chromatography, in Methods in Biotechnology, vol. 4: Natural Products Isolation (Cannell, R. J. P., ed.), Humana, Totowa, NJ, pp. 141–164.

    Chapter  Google Scholar 

  24. Solid Phase Extraction Reference Manual and User Guide. Phenomenex, USA.

    Google Scholar 

  25. Houghton, P. J. and Raman, A. (1998) Laboratory Handbook for the Fractionation of Natural Extracts, Chapman & Hall, London, UK.

    Google Scholar 

  26. Thurman, E. M. and Mills, M. S. (1998) Solid Phase Extraction: Principles and Practice, John Wiley & Sons, New York.

    Google Scholar 

  27. Rodriguez, J., Nieto, R. M., and Crews, P. (1993) New structures and bioac-tivity patterns of bengazole alkaloids from a Choristid marine sponge. J. Nat. Prod. 56, 2034–2040.

    Article  CAS  Google Scholar 

  28. Rashid, M. A., Gustafson, K. R., Cartner, L. K., Pannell, L. K., and Boyd, M. R. (2001) New nitrogenous constituents from the South African marine ascidian Pseudodistoma sp. Tetrahedron 57, 5751–5755.

    Article  CAS  Google Scholar 

  29. Chang, L. C., Otero-Quintero, S., Nicholas, G. M., and Bewley, C. A. (2001) Phyllolactones A-E: new bishomoscalarane sesterterpenes from the marine sponge Phyllospongia lamellose. Tetrahedron 57, 5731–5738.

    Article  CAS  Google Scholar 

  30. Venkat, E. and Kothadarama, S. (1998) Supercritical fluid methods, in Methods in Biotechnology, vol. 4: Natural Products Isolation (Cannell, R. J. P., ed.), Humana, Totowa, NJ, pp. 91–109.

    Chapter  Google Scholar 

  31. Gao, D., Okuda, R., and Lopez-Avila, V. (2001) Supercritical fluid extraction of halogenated monoterpenes from the red alga Plocamium cartilagineum. J. AOACInt. 84, 1313–1331.

    CAS  Google Scholar 

  32. Subra, P. and Boissinot, P. (1991) Supercritical fluid extraction from a brown alga by stage wise pressure increase. J. Chromatogr. 543, 413–424.

    Article  CAS  Google Scholar 

  33. Stahl, E. (1965) Thin Layer Chromatography—A Laboratory Handbook, Springer-Verlag, Berlin.

    Google Scholar 

  34. Wagner, H. and Bladt, S. (1995). Plant Drug Analysis—A Thin Layer Chromatography Atlas, Springer-Verlag, Berlin.

    Google Scholar 

  35. Hamburger, M. O. and Cordell, G. A. (1987) A direct bioautographic TLC assay for compounds possessing antibacterial activity. J. Nat. Prod. 50, 19–22.

    Article  CAS  Google Scholar 

  36. Burres, N. S., Hunter, J. E., and Wright, A. E. (1989) A mammalian cell agar-diffusion assay for the detection of toxic compounds. J. Nat. Prod. 52, 522–527.

    Article  CAS  Google Scholar 

  37. Zhou, S. and Hamburger, M. (1996) Application of liquid chromatography-atmospheric pressure ionisation mass spectrometry in natural products analysis: evaluation and optimisation of electrospray and heated nebulizer interfaces J. Chromatogr. A 755, 189–204.

    Article  CAS  Google Scholar 

  38. Silva, G. L., Lee, I., and Kinghorn, A. D. (1998) Special problems with the extraction of plants, in Methods in Biotechnology, vol. 4: Natural Products Isolation (Cannell, R. J. P., ed.), Humana, Totowa, NJ, pp. 343–364.

    Chapter  Google Scholar 

  39. Kupchan, S. M., Britton, R. W., Ziegler, M. F., and Siegel, C. W. (1973) Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica. J. Org. Chem. 38, 178–179.

    Article  CAS  Google Scholar 

  40. West, L. M. and Northcote, P. T. (2000) Peloruside A: a potent cytotoxic macrolide isolated from the New Zealand marine sponge Mycale sp. J. Org. Chem. 65, 445–449.

    Article  CAS  Google Scholar 

  41. West, L. M., Northcote, P. T., Hood, K. A., Miller, J. H., and Page, M. J. (2000) Mycalamide D, a new cytotoxic amide from the New Zealand marine sponge Mycale species. J. Nat. Prod. 63, 707–709.

    Article  CAS  Google Scholar 

  42. Allgeier, M. C., Nussbaum, M. A., and Risley, D. S. (2003) Comparison of an evaporative light-scattering detector and a chemiluminescent nitrogen detector for analysing compounds lacking a sufficient UV chromophore. LCGCN. Am. 21,376–381.

    CAS  Google Scholar 

  43. Shigematsu, N. (1997) Dereplication of natural products using LC/MS. J. Mass Spectrom Soc. Jpn. 45, 295–300.

    CAS  Google Scholar 

  44. Pannell, L. K. and Shigematsu, N. (1998) Increased speed and accuracy of structural determination of biologically active natural products using LC-MS. Am. Lab. 30, 28–30.

    CAS  Google Scholar 

  45. Bobzin, S. C., Yang, S., and Kasten, T. P. (2000) LC-NMR: a new tool to expedite the dereplication and identification of natural products. J. Indust. Microbiol. Biotech. 25, 342–345.

    Article  CAS  Google Scholar 

  46. Pullen, F. S., Swanson, A. G., Newman, M. J., and Richards, D. S. (1995) Online liquid chromatography/nuclear magnetic resonance/mass spectrometry—a powerful spectrometric tool for the analysis of mixtures of pharmaceutical interest. Rapid Commun. Mass Spectrom. 9, 1003–1006.

    Article  CAS  Google Scholar 

  47. Adel, U., Kock, C., Speitling, M., and Hansske, F. G. (2002) Modern methods to produce natural-product libraries. Curr. Opin. Chem. Biol. 6,453–458.

    Article  Google Scholar 

  48. God, R., Gumm, H., Heuer, C., and Juschka, M. (1999) Online coupling of HPLC and solid-phase extraction for preparative chromatography. GIT Lab J. 3, 188–191.

    CAS  Google Scholar 

  49. Middleditch, B. S. (1989) Analytical artifacts: GC, MS, HPLC, TLC and PC. J. Chromatogr. Library 44.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Marine Natural Products Laboratory, Chemistry Department, Aberdeen University, Aberdeen, Scotland, UK

    Wael E. Houssen & Marcel Jaspars

Authors
  1. Wael E. Houssen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marcel Jaspars
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Pharmaceutical Biotechnology Research Group school of Biomedical Sciences, University of Ulster at Coleraine, Coleraine, Northern Ireland, UK

    Satyajit D. Sarker

  2. Molecular Nature Limited Plas Gogerddan, Aberystwyth, Wales, UK

    Zahid Latif

  3. Phytochemistry Research Lab Department of Pharmaceutical Sciences, University of Strathclyde, Glasgow, Scotland, UK

    Alexander I. Gray

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Humana Press Inc., Totowa,NJ

About this protocol

Cite this protocol

Houssen, W.E., Jaspars, M. (2006). Isolation of Marine Natural Products. In: Sarker, S.D., Latif, Z., Gray, A.I. (eds) Natural Products Isolation. Methods in Biotechnology, vol 20. Humana Press. https://doi.org/10.1385/1-59259-955-9:353

Download citation

  • DOI: https://doi.org/10.1385/1-59259-955-9:353

  • Publisher Name: Humana Press

  • Print ISBN: 978-1-58829-447-0

  • Online ISBN: 978-1-59259-955-4

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics

Search

Navigation