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
Shimizu, Y. (1985) Bioactive marine natural products, with emphasis on handling of water-soluble compounds. J. Nat. Prod. 48, 223–235.
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.
Lepane, V. (1999) Comparison of XAD resins for the isolation of humic substances from seawater. J. Chromatogr. A 845, 329–335.
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.
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.
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.
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.
Fu, T. and Pocklington, R. (1983) Quantitative adsorption of organic matter from seawater on solid matrices. Marine Chem. 13, 255–264.
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.
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.
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.
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.
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.
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.
Gastaldo, L., Marinelli, D., Restelli, E., and Quarta, C. (1996) Improvement of the kirromycin fermentation by resin addition. J. Ind. Microbiol. 16, 305–308.
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.
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.
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.
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.
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.
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.
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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
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