Antifungal Activities of Equisetin, Zearalenone, and 8'-Hydroxyaearalenone Isolated from Fusarium Species against Plant Pathogenic Fungi.

Fusarium속 균주로부터 분리한 Equisetin, Zearalenone 및 8'-Hydroxyzearalenone의 식물병원곰팡이에 대한 항균활성

  • 김진철 (한국화학연구원 농약스크리닝연구팀) ;
  • 박중협 (한국화학연구원 농약스크리닝연구팀) ;
  • 최경자 (한국화학연구원 농약스크리닝연구팀) ;
  • 김흥태 (한국화학연구원 농약스크리닝연구팀) ;
  • 최용호 (한국화학연구원 농약스크리닝연구팀) ;
  • 조광연 (한국화학연구원 농약스크리닝연구팀)
  • Published : 2002.12.01

Abstract

Antifungal substances were isolated from solid cultures of Fusarium equiseti FO-68 obtained from arrowhead and Fusarium sp. FO-510 obtained from egg plant, and then their antifungal activities were investigated against plant pathogenic fungi in vitro and in vivo. An antifungal substance was purifed from rice solid cultures of F. equiseti FO-68 and identified as equisetin. In addition, two antibiotic substances were isolated from solid cultures of Fusarium sp. FO-510 and their chemical structures were determined to be zearalenone and 8'-hydroxyzearalenone. in vitro, equisetin and zearalenone inhibited mycelial growth of most of the plant pathogenic fungi tested, whereas 8'-hydroxyzearalenone hardly inhibited fungal growth. In vitro, equisetin effectively controlled the development of tomato gray mold and tomato late blight. Zearalenone exhibited in vivo antifungal activity against rice blast, rice sheath blight, tomato gray mold, and tomato late blight. However, 8'-hydroxyzearale-none did not control the development of plant diseases except tomato gray mold. This is the first report on the antifungal activities of equisetin, zearalenone, and 8'-hydroxyzearalenone.

References

  1. J. Antibiot. v.30 The strobilurins-new antifungal antibiotics from the Basidiomycete Strobilurus tenacellus Anke,T.;F.Oberwinkler;W.Steglich;G.Schramm https://doi.org/10.7164/antibiotics.30.806
  2. Antimicrob. Ag. Chemother v.5 Antibiotic produced by Fusarium equiseti NRRL 5537 Burmeister,H.R.;G.A.Bennett;R.F.Vesonder;W.Hesseltine https://doi.org/10.1128/AAC.5.6.634
  3. Med. Res. Rev. v.20 Current lead natural products for the chemotherapy of human immunodeficiency virus (HIV) infection De Clercq, E. https://doi.org/10.1002/1098-1128(200009)20:5<323::AID-MED1>3.0.CO;2-A
  4. Basic Plant Pathology Methods Chemical control Dhiangra,O.D.;J.B.Sinclair
  5. Proceedings of the Brighton Crop Protection Conference-Pests and Diseases v.1 ICIA5504: a novel, broadspectrum, systemic β-methoxyacrylate fungicide Godwin,J.R.;V.M.Anthony;J.M.Clough;C.R.A.Godfrey
  6. Pestic. Sci. v.43 Fungicidal effects BASF490F on the development and fine structures of plant pathognic fungi Gold,R.E.;G.M.Leinhos https://doi.org/10.1002/ps.2780430316
  7. Abstracts of Papers, 222nd ACS National Meeting HIV integrase inhibition: dihydroxynaphthalene analogs of equisetin Handy,S.T.;D.Omune;G.Menon
  8. Abstracts of Papers, 219th ACS National Meeting Simplified analogs of equisetin: Potential new HIV integrase inhibitors Handy,S.T.;K.Chang
  9. Antiviral Chem. and Chemother v.10 Isolation and characterization of novel human immunodeficiency virus integrase inhibitors from fungal metabolites Hazuda,D.;C.U.Blau;P.Felock;J.Hastings;B.Pramanik;A.Wolfe;F.Bushman;C.Farnet;M.Goetz;M.Williams;K.Silverman;R.Lingham;S.Shingh https://doi.org/10.1177/095632029901000202
  10. J. Agr. Food. Chem. v.22 Characterization of two isomers of 8'-hydroxyzearalenone and other derivatives of zearalenone Jackson,R.A.;S.W.Fenton;C.J.Mirocha;G.Davis https://doi.org/10.1021/jf60196a039
  11. Plant Pathol. J. v.15 Antibiotic and phytotoxic activities of ophiobolins from Helminthosporium species Kim,H.J.;J.C.Kim;B.S.Kim;H.G.Kim;K.Y.Cho
  12. Pest Manag. Sci. v.57 Activity against plant pathogenic fungi of phomalactone isolated from Nigrospora sphaerica Kim,J.C.;G.J.Choi;J.H.Park;H.T.Kim;K.Y.Cho https://doi.org/10.1002/ps.318
  13. Appl. Environ. Microbiol. v.59 Natural occurrence of Fusarium mycotoxins(Trichothecenes and zearalenone) in barley and corn in Korea Kim,J.C.;H.J.Kang;D.H.Lee;Y.W.Lee;T.Yoshizawa
  14. Appl. Environ. Microbiol. v.60 Sambutoxin, a new mycotoxin produced by toxic Fusarium isolates obtained from rotted potato tubers Kim,J.C.;Y.W.Lee
  15. J. Bioenerg. Biomembr. v.25 Effects of equisetin on rat liver mitochondria: evidence for substrate anion carriers of the inner membrane Koenig,T.;A.Kapus;B.Sarkadi https://doi.org/10.1007/BF01108410
  16. Mycotoxins in human and animal health Zearalenone Mirocha,C.J.;S.V.Pathre;C.M.Christensen;J.V.Rodricks(ed.);H.W.Hesseltine(ed.);M.A.Mehlman(ed.)
  17. Phytopathology v.85 Respiratory characteristics in Pyricularia oryzae exposed to a novel alkoxyiminoacetamide fungicide Mizutani,A.;H.Yukioka;H.Tamura;N.Mik;M.Masuko;R.Takeda https://doi.org/10.1094/Phyto-85-306
  18. Folia Microbiol.(Praque) v.14 Antifungal antibiotic of the Basidiomycete Oudemansiella mucida Musilek,V;J.Cerna;V.Sasek;M.Semerdzieva;M.Vondracek https://doi.org/10.1007/BF02872707
  19. Kor. J. Pestic. Sci. v.4 Biological activities of Fusarium isolates from soil and plants Park,J.H.;J.C.Kim;G.J.Choi;H.T.Kim;K.S.Hong;C.Song;J.S.Kim;J.G.Kim;K.Y.Cho
  20. J. Am. Chem. Soc. v.111 Characterization of the Fusarium toxin equisetin: the use of phenylboronates in structure assignment Phillips,N.J.;J.T.Goodwin;A.Fraiman;R.J.Cole;D.G.Lynn https://doi.org/10.1021/ja00203a025
  21. J. Antibiot. v.55 CJ-21,058, a new SecA inhibitor isolated from a fungus Sugie,Y.;S.Inaki;Y.Kato;H.Nishida;C.H.Pang;T.Saito;S.Sakemi;F.Dib-Haji;J.P.Mueller;J.Sutcliffe;Y.Kojima https://doi.org/10.7164/antibiotics.55.25
  22. Fusarium mycotoxins, taxonomy, and pathogenicity Metabolites of Fusarium Vesonder,R.F.;P.Golinski;Chelkowski,J.(ed.)
  23. Mycological Research v.103 Phytotoxicity of equisetin and epi-equisetin isolated from Fusarium equiseti and F. pallidoroseum Wheeler,M.H.;R.D.Stipanovic;L.S.Puckhaber https://doi.org/10.1017/S0953756298008119
  24. Tennen Yoki Kagobutsu Toronkai Koen Yoshishu v.41 Synthetic studies on fungal metabolites with HIV-I integrase inhibitory activity Yuki,K.;N.Satoyoshi;M.Shindo;K.Shishido