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Journal of Applied Phycology

, Volume 2, Issue 4, pp 305–308 | Cite as

Antimicrobial activities of polyether compounds of dinoflagellate origins

  • Hiroshi Nagai
  • Masayuki Satake
  • Takeshi Yasumoto
Article

Abstract

Twelve polyether compounds originating from dinoflagellates were tested for growth-inhibiting activities againstAspergillus niger, Penicillium funiculosum, Candida rugosa, Escherichia coli, Bacillus megaterium andStaphylococcus aureus by a paper disc method. These polyethers represent six groups of different skeletons and originate from three species;Prorocentrum lima, Dinophysis fortii andGambierdiscus toxicus. Potent antifungal activities were observed with okadaic acid and its two congeners, desulfated yessotoxin, and ciguatoxin but not with okadaic acid esters, prorocentrolide, pectenotoxin-1, yessotoxin, maitotoxin, and desulphated maitotoxin. The antifungal activities and mouse lethalities of the polyethers were markedly affected by slight modification of their structures. Antibacterial potency of the tested compounds was not significant.

Key words

polyether antimicrobial activity dinoflagellate antifungals chemical modification 

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References

  1. Fujiki H, Suganuma M, Suguri H, Yoshizawa S, Ojika M, Wakamatsu K, Yamada K, Sugimura T (1987) Induction of ornithine decarboxylase activity in mouse skin by a possible tumor promoter, okadaic acid. Proc. Jpn. Acad. Ser. B. 63: 51–53.Google Scholar
  2. Gusovsky F, Daly JW (1990) Maitotoxin: A unique pharmacological tool for research on calcium-dependent mechanisms. Biochem. Pharmacol. 39: 1633–1639.PubMedGoogle Scholar
  3. Kao CY (1966) Tetrodotoxin, saxitoxin and their significance in the study of excitation phenomenon. Pharm. Rev. 18: 997–1049.PubMedGoogle Scholar
  4. Haystead TAJ, Sim ATR, Carling D, Honnor RC, Tsukitani Y, Cohen P, Hardie DG (1989) Effects of the tumor promoter okadaic acid on intracellular protein phosphorylation and metabolism. Nature 337: 78–81.PubMedGoogle Scholar
  5. Legrand AM, Litaudon M, Genthon JN, Bagnis R, Yasumoto T (1989) Isolation and some properties of ciguatoxin. J. Appl. Phycol. 1: 183–188.Google Scholar
  6. Murakami M, Makabe K, Yamaguchi K, Konosu S (1988) Goniodomin A, a novel polyether macrolide from the dinoflagellateGoniodoma pseudogonyaulax. Tetrahedron Lett. 29: 1149–1152.Google Scholar
  7. Murakami Y, Oshima Y, Yasumoto T (1982) Identification of okadaic acid as a toxic component of a marine dinoflagellateProrocentrum lima. Bull. Jpn. Soc. Sci. Fish. 48: 69–72.Google Scholar
  8. Murata M, Kumagai M, Lee JS, Yasumoto T (1987) Isolation and structure of yessotoxin, a novel polyether compound implicated in diarrhetic shellfish poisoning. Tetrahedron Lett. 28: 5869–5872.Google Scholar
  9. Murata M, Legrand AM, Ishibashi Y, Fukui M, Yasumoto T (1990) Structures and configuration of ciguatoxin from the moray eelGymnothorax javanicus and its likely precursor from the dinoflagellateGambierdiscus toxicus. J. Am. Chem. Soc. 112: 4380–4386.Google Scholar
  10. Torigoe K, Murata M, Yasumoto T, Iwashita T (1988) Prorocentrolide, a toxic nitrogenous macrocycle from a marine dinoflagellate,Prorocentrum lima. J. Am. Chem. Soc. 110: 7876–7877.Google Scholar
  11. Nakazawa S (1980) Basic knowledge of antibiotics. Nanzando, Tokyo, 204 pp. (in Japanese).Google Scholar
  12. Yanagi T, Murata M, Torigoe K, Yasumoto T (1989) Biological activities of Semisynthetic analogs of dinophysistoxin-3, the major diarrhetic shellfish toxin. Agric. Biol. Chem. 53: 525–529.Google Scholar
  13. Yasumoto T, Murata M, Oshima Y, Sano M, Matsumoto GK, Clardy J (1985) Diarrhetic shellfish toxins. Tetrahedron 41: 1019–1025.Google Scholar
  14. Yasumoto Y, Seino N, Murakami Y, Murata M (1987) Toxins produced by benthic dinoflagellates. Biol. Bull. 172: 128–131.Google Scholar
  15. Yasumoto T (1988) Bioactive substances of synbiotic microalgae. J. Synth. Org. Chem. Jpn. 46: 478–489.Google Scholar
  16. Yokoyama A, Murata M, Oshima Y, Iwashita T, Yasumoto T (1988) Some chemical properties of maitotoxin, a putative calcium channel agonist from a marine dinoflagellate. J. Biochem. 104: 184–187.PubMedGoogle Scholar

Copyright information

© Kluwer Academic Publishers 1990

Authors and Affiliations

  • Hiroshi Nagai
    • 1
  • Masayuki Satake
    • 2
  • Takeshi Yasumoto
    • 2
  1. 1.Taiyo Central R&D Institute, Taiyo Fishery Co. LTD.TokyoJapan
  2. 2.Faculty of AgricultureTohoku UniversitySendaiJapan

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