Structure and relative potency of several karlotoxins from Karlodinium veneficum

Journal of Natural Products

Volumn 73, Issue 8, 2010, Pages 1360-1365

  Van Wagoner, Ryan M ^a   Deeds, Jonathan R ^b   Tatters, Avery O ^a   Place, Allen R ^c   Tomas, Carmelo R ^a   Wright, Jeffrey L C ^a  

^a UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

^b CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^c UNIVERSITY OF MARYLAND CENTER FOR ENVIRONMENTAL SCIENCE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KARLOTOXIN 1; KARLOTOXIN 3; KARLOTOXIN 4; KARLOTOXIN 5; KARLOTOXIN 6; KARLOTOXIN 7; TOXIN; UNCLASSIFIED DRUG; HEMOLYTIC AGENT; MACROLIDE; MARINE TOXIN; POLYENE; PYRAN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DINOFLAGELLATE; DRUG ACTIVITY; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; HEMOLYSIS; KARLODINIUM WENEFICUM; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SULFONATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ERYTHROCYTE; HUMAN; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE;

DINOFLAGELLIDA; ERYTHROCYTES; HEMOLYTIC AGENTS; HUMANS; MACROLIDES; MARINE TOXINS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; POLYENES; PYRANS;

EID: 77956224854     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np100158r     Document Type: Article

References (36)

1. Deeds, J. R., Terlizzi, D. E., Adolf, J. E., Stoecker, D. K., and Place, A. R. Harmful Algae 2002, 1, 169-189
2. Adolf, J. E., Bachvaroff, T. R., Krupatkina, D. N., Nonogaki, H., Brown, P. J. P., Lewitus, A. J., Harvey, H. R., and Place, A. R. Afr. J. Mar. Sci. 2006, 28, 415-419
3. Kempton, J. W., Lewitus, A. J., Deeds, J. R., Law, J. M., and Place, A. R. Harmful Algae 2002, 1, 233-241
4. Van Wagoner, R. M., Deeds, J. R., Satake, M., Ribeiro, A. A., Place, A. R., and Wright, J. L. C. Tetrahedron Lett. 2008, 49, 6457-6461
5. Bachvaroff, T. R., Adolf, J. E., and Place, A. R. J. Phycol. 2009, 45, 137-153
6. Mooney, B. D., de Salas, M., Hallegraeff, G. M., and Place, A. R. J. Phycol. 2009, 45, 164-175
7. Abbott, B. C. and Ballantine, D. J. Mar. Biol. Assoc. U.K. 1957, 36, 169-189
8. Nielsen, M. V. Mar. Ecol.: Prog. Ser. 1993, 95, 273-277
9. Deeds, J. R., Reimschuessel, R., and Place, A. R. J. Aq. Anim. Health 2006, 18, 136-148
10. Sheng, J., Malkiel, E., Katz, J., Adolf, J. E., and Place, A. R. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 2082-2087
11. Adolf, J. E., Krupatkina, D., Bachvaroff, T., and Place, A. R. Harmful Algae 2007, 6, 400-412
12. Adolf, J. E., Bachvaroff, T., and Place, A. R. Harmful Algae 2008, 8, 119-128
13. Deeds, J. R. and Place, A. R. Afr. J. Mar. Sci. 2006, 28, 421-425
14. Place, A. R., Harvey, H. R., Bai, X., and Coats, D. W. Afr. J. Mar. Sci. 2006, 28, 347-351
15. Place, A. R., Bai, X., Kim, S., Sengco, M. R., and Coats, D. W. J. Phycol. 2009, 45, 375-385
16. Hall, N. S., Litaker, R. W., Fensin, E., Adolf, J. E., Bowers, H. A., Place, A. R., and Paerl, H. W. Estuaries Coasts 2008, 31, 402-418
17. Place, A. R., Saito, K., Deeds, J. R., Robledo, J. A. F., and Vasta, G. R. In Seafood and Freshwater Toxins: Pharmacology, Physiology, and Detection, 2nd ed.; Botana, L. M., Ed.; Taylor and Francis: Boca Raton, FL, 2008; pp 717 - 752.
18. Deeds, J. R., Kibler, S. R., Tester, P. A., and Place, A. R. In Harmful Algae 2002. Proceedings of the Xth International Conference on Harmful Algae; Steidinger, K. A., Landsberg, J. H., Tomas, C. R., and Vargo, G. A., Eds.; Florida Fish and Wildlife Conservation Commission, Florida Institute of Oceanography, and Intergovernmental Oceanographic Commission of UNESCO: St. Petersburg, FL, 2004.
19. Peng, J., Place, A. R., Yoshida, W., Anklin, C., and Hamann, M. T. J. Am. Chem. Soc. 2010, 132, 3277-3279
20. Satake, M., Murata, M., Yasumoto, T., Fujita, T., and Naoki, H. J. Am. Chem. Soc. 1991, 113, 9859-9861
21. Bachvaroff, T. R., Adolf, J. E., Squier, A. H., Harvey, H. R., and Place, A. R. Harmful Algae 2008, 7, 473-484
22. Doi, Y., Ishibashi, M., Nakamichi, H., Kosaka, T., Ishikawa, T., and Kobayashi, J. I. J. Org. Chem. 1997, 62, 3820-3823
23. Morsy, N., Matsuoka, S., Houdai, T., Matsumori, N., Adachi, S., Murata, M., Iwashita, T., and Fujita, T. Tetrahedron 2005, 61, 8606-8610
24. Morsy, N., Houdai, T., Matsuoka, S., Matsumori, N., Adachi, S., Oishi, T., Murata, M., Iwashita, T., and Fujita, T. Bioorg. Med. Chem. 2006, 14, 6548-6554
25. Meng, Y., Van Wagoner, R. M., Misner, I., Tomas, C., and Wright, J. L. C. J. Nat. Prod. 2010, 73, 409-415
26. Silverstein, R. M., Bassler, G. C., and Morrill, T. C. In Spectrometric Identification of Organic Compounds, 5th ed.; John Wiley & Sons, Inc.: New York, 1991; p 298.
27. Houdai, T., Matsuoka, S., Matsumori, N., and Murata, M. Biochim. Biophys. Acta Biomembr. 2004, 1667, 91-100
28. Houdai, T., Matsuoka, S., Morsy, N., Matsumori, N., Satake, M., and Murata, M. Tetrahedron 2005, 61, 2795-2802
29. Morsy, N., Houdai, T., Konoki, K., Matsumori, N., Oishi, T., and Murata, M. Bioorg. Med. Chem. 2008, 16, 3084-3090
30. Echigoya, R., Rhodes, L., Oshima, Y., and Satake, M. Harmful Algae 2005, 4, 383-389
31. Houdai, T., Matsuoka, S., Murata, M., Satake, M., Ota, S., Oshima, Y., and Rhodes, L. L. Tetrahedron 2001, 57, 5551-5555
32. Wright, J. L. C., Hu, T., McLachlan, J. L., Needham, J., and Walter, J. A. J. Am. Chem. Soc. 1996, 118, 8757-8758
33. Igarashi, T., Satake, M., and Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480
34. Igarashi, T., Satake, M., and Yasumoto, T. J. Am. Chem. Soc. 1999, 121, 8499-8511
35. Eschbach, E., Scharsack, J. P., John, U., and Medlin, L. K. J. Appl. Toxicol. 2001, 21, 513-519
36. Guillard, R. R. L. In Culture of Marine Invertebrate Animals; Smith, W. L. and Chanley, M. H., Eds.; Plenum Press: New York, 1975; pp 26 - 60.