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Purification of Water-Soluble Natural Products

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Natural Products Isolation

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

Summary

Despite the remarkable advancement in purification methods, the isolation of small water-soluble molecules still remains a mystery for natural-product researchers. A general approach to extract and fractionate water-soluble compounds from biological materials and fluids including seawater is presented in this chapter. Some important techniques and special caution needed to deal with water-soluble compounds are also included. The chapter also presents information and discussions about various matrices, such as C18 silica gel, resins, and size-exclusion materials with respect to extraction and desalting of water-soluble compounds. In particular, applications and limitations of the increasingly popular nonionic resins are added in this edition. Four typical examples of isolation of water-soluble compounds, which were carried out in the authors’ laboratory, are presented in detail. They are: (1) the isolation of amesic shellfish poison, domoic acid, from cultured diatom cells, (2) the isolation of tetrodotoxin derivatives from a newt, (3) the isolation of an aminotetrasaccharide from cultured cyanobacterium cells, and (4) isolation of glycosidic polyether antitumor compounds from the culture broth of a marine dinoflagellate.

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References

  1. 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 

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

    Chapter  Google Scholar 

  3. Lepane, V. (1999) Comparison of XAD resins for the isolation of humic substances from seawater. J. Chromatogr. A 845, 329–335.

    Article  CAS  Google Scholar 

  4. Weigel, S., Bester, K., and Hühnerfuss, H. (2001) New method for rapid solid-phase extraction of large-volume water samples and its application to non-target screening of North Sea water for organic contaminants by gas chromatography-mass spectrometry. J. Chromatogr. A 912, 151–161.

    Article  CAS  Google Scholar 

  5. Hubberten, U., Lara, R. J., and Kattner, C. (1994) Amino acid composition of seawater and dissolved humic substances in the Greenland Sea. Marine Chem. 45, 121–128.

    Article  CAS  Google Scholar 

  6. Leonard, J. D. and Crewe, R. N. (1983) Study on the extraction of organic compounds from seawater with XAD-2 resin. Marine Chem. 12, 222.

    Article  Google Scholar 

  7. Slauenwhite, D. E. and Wangersky, P. J. (1996) Extraction of marine organic matter on XAD-2: effect of sample acidification and development of an in situ pre-acidification technique. Marine Chem. 54, 107–117.

    Article  CAS  Google Scholar 

  8. Fu, T. and Pocklington, R. (1983) Quantitative adsorption of organic matter from seawater on solid matrices. Marine Chem. 13, 255–264.

    Article  CAS  Google Scholar 

  9. Font, G., Mañes, J., Moltó, J. C., and Picó, Y. (1993) Solid-phase extraction in multi-residue pesticide analysis of water. J. Chromatogr. A 642, 135–161.

    Article  CAS  Google Scholar 

  10. Tolosa, I., Readman, J. W., and Mee, L. D. (1996) Comparison of the performance of solid-phase extraction techniques in recovering organo-phosphorus and organochlorine compounds from water. J. Chromatogr. A 725, 93–106.

    Article  CAS  Google Scholar 

  11. Davankov, V., Tsyurupa, M., Ilyin, M. D., and Pavalova, L. (2002) Hypercross-linked polystyrene and its potentials for liquid chromatography: a mini-review. J. Chromatogr. A 965, 65–73.

    Article  CAS  Google Scholar 

  12. Adachi, T., Ando, S., and Watanabe, J. (2002) Characterization of synthetic adsorbents with fine particle sizes for preparative-scale chromatographic separation J. Chromatogr. A 944, 41–59.

    Article  CAS  Google Scholar 

  13. Lee, J C., Park, H. R., Park, D. J., Lee, H. B., Kim, Y. B., and Kim, C. J. (2003) Improved production of teicoplanin using adsorbent resin in fermentations. Lett. Appl. Microbiol. 37, 196–200.

    Article  CAS  Google Scholar 

  14. Marshall, V. P., McWethy, S. J., Sirotti, J. M., and Cialdella, J. I. (1990) The effect of neutral resins on the fermentation production of rubradirin. J. Ind. Microbiol. 5, 283–288.

    Article  CAS  Google Scholar 

  15. Gastaldo, L., Marinelli, D., Restelli, E., and Quarta, C. (1996) Improvement of the kirromycin fermentation by resin addition. J. Ind. Microbiol. 16, 305–308.

    Article  CAS  Google Scholar 

  16. Hori, A. and Shimizu, Y. (1983) Biosynthetic N-enrichment and N-NMR spectra of neosaxitoxin and gonyautoxin-ll: application to the structure determination. J. Chem. Soc. Chem. Commun. 790–792.

    Google Scholar 

  17. Kotaki, Y. and Shimizu, Y. (1993) 1-Hydroxy-5, 11-dideoxytetroddotoxin, the first N-hydroxyl and ring-deoxy derivative of tetrodotoxin found in the newt Tricha granulosa. J. Am. Chem. Soc. 115, 827–830.

    Article  CAS  Google Scholar 

  18. Maranda, L., Wang, R., Masuda, K., and Shimizu, Y. (1990) Investigation of the source of domoic acid in mussels; in Toxic Marine Phytoplankton (Granèli, E., Sundström, B., Edler, L., and Anderson, D. M., eds.), Elsevier, Amsterdam, pp. 300–304.

    Google Scholar 

  19. Wright, J. L. C., Boyd, R. K., de Freitas, A. S. W., et al. (1989) Identification of domoic acid, a neuroexcitatory amino acid in toxic mussels from eastern Prince Edward Island. Can. J. Chem. 67, 481–490.

    Article  CAS  Google Scholar 

  20. Thammana, S., Suzuki, J., Shimizu, Y., Lobkovsky, E., and Clardy, J. (2002) An aminotetrasaccharide derivative from a filamentous cyanobacterium Anabena sp. 43rd Annual Meeting of the American Society of Pharmacognosy Abstracts, p. 107.

    Google Scholar 

  21. Konishi, M., Yang, X., Li, B., and Shimizu, Y. (2004) Highly cytotoxic metabolites from the culture supernatant of the temperate dinoflagellate Protoceratium cf. reticulatum. J. Nat. Prod., 67, 1309–1313.

    Article  CAS  Google Scholar 

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© 2006 Humana Press Inc., Totowa,NJ

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Shimizu, Y., Li, B. (2006). Purification of Water-Soluble 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/10.1385/1-59259-955-9:415

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  • DOI: https://doi.org/10.1385/1-59259-955-9:415

  • Publisher Name: Humana Press

  • Print ISBN: 978-1-58829-447-0

  • Online ISBN: 978-1-59259-955-4

  • eBook Packages: Springer Protocols

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