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Bioorganic chemistry of host-specific toxins from microbes and self-defense substances from plants involved in host-parasite interactions

Research Project

Project/Area Number 03455025
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 広領域
Research InstitutionThe Institute of Physical and Chemical Reserch, Lab.of Plant Growth Regulation

Principal Investigator

KONO Yoshiki  RIKEN, Lab.of Plant Growth Regulation senior scientist, 植物生活環制御研究室, 副主任研究員 (90087578)

Co-Investigator(Kenkyū-buntansha) SUZUKI Yoshikatsu  RIKEN, Lab.of Plant Growth Regulation scientist, 植物生活環制御研究室, 先任研究員 (00087579)
Project Period (FY) 1991 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥5,600,000 (Direct Cost: ¥5,600,000)
Fiscal Year 1993: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1992: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1991: ¥3,400,000 (Direct Cost: ¥3,400,000)
Keywordshost-specific toxin / HMT-toxin / PM-toxin / structure-activity relationship / pyriculol related compounds / oryzalide / Xanthomonas campestris / Oryza officinalis / Xanthomonus campestris / 抗細菌物質 / イネ白葉枯れ病 / 抗いもち菌物質 / oryza officinalis / jasmonic acid related / Oryzalide / Xanthomonas oryzae / Pyricularia oryzae / Oryza-Officicnalis / HMT-toxin / PM-toxin / トウモロコシごま葉枯病 / 植物毒素 / 病原毒素 / Pyriculol / Helminthosporium maydis
Research Abstract

Objective : In interactions between a host-plant and pathogen, a host-plant produces self-defense substances against microbes and a pathogen sometimes produces a host-selective substances. Objectives in our experiments were : a) Clarification of structure-activity relationships of HMT- and PM-toxins. Isolation of phytotoxins from Pyricularia oryzae and Helminthosporium sorghicola. b) Studies on resistant mechanism of rice plant against a bacterial leaf blight caused by Xanthomonas campestris pv. oryzae. c) Isolation of antifungal substances from leaves of wild rice, Oryza officinalis, W0002 which shows resistant against rice blast disease. Isolation and identification of antifungal substances from other plant extracts.
Results : a) i) Above 30 compounds related to HMT- and PM-toxins were synthesized and compared their activity using a susceptible corn leaf. At least four beta-ketol groups are required to express high activity and also spacing methylene functions between each beta-ketol group required above seven for high activity. ii) Two novel pyriculol related compounds were isolated and identified as phytotoxins from the solid culture of Pyricularia oryzae. b) Ten novel antibacterial diterpenes were isolated from a flag leaf of abacterial leaf blight-resistant cultivar of rice plant and determined their structures. Quantitative analysis of oryzalides using GC-MS-SIM suggested that a role of oryzalides might be an inhibitin. c) (-)-jasmonic acid and two novel fatty acids, 12-hydroxy-9(Z)-dodecenoic acid and 11-hydroxy-9(Z)-undecenoic acid, were isolated and identified from healthy leaves of wild rice, Oryza officinalis W0002 as a antifungal substance.

Report

(4 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • 1991 Annual Research Report
  • Research Products

    (29 results)

All Other

All Publications (29 results)

  • [Publications] Minoru Watanabe: "A novel C_<19>-Kaurane type diterpene(Oryzalide A),a new antimicrobial compound isolated from healthy..." Agric.Biol.Chem.54. 1103-1105 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshiki Kono: "Structures of oryzalides A and B,and oryzalic acid A,a group of novel antimicrobial diterpenes..." Agric.Biol.Chem.55. 803-811 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshikatsu Suzuki: "Toxic activity of mimics of the host-specific pathotoxin PM-toxin on corn carmying Texas---." Agric.Biol.Chem.55. 1061-1070 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshiki Kono: "Structures of two novel pyriculol-related compounds and identification of naturally produced epipyriculol..." Agric.Biol.Chem.55. 2785-2791 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Germano Cord Neto: "Isolation and identification of(-1-jasmonic acid from wild rice,Oryza officinalis,as an antifungal substance" Agric.Biol.Chem.55. 3097-3098 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Manabu Watanabe: "Structures of oryzalic acid B and three related compounds,a group of novel antibacterial diterpenes,.." Biosci.Biotech.Biochem.56. 113-117 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Watanabe, Y.Sakai, T.Teraoko, H.Abe, Y.Kono, J.Uzawa, K.Kobayashi, Y.Suzuki and A.Sakurai: ""A novel C19-kaurane type diterpene (Oryzalide A), a new antimicrobial compound islated from healthy leaves of a bacterial leaf blight-resistant cultivar of rice plant"" Agric.Biol.Chem. 54. 1103-1105 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] J.Zhang, K.Takahashi, Y.Kono, Y.Suzuki, S.Takeuchi, T.Shimazu, I.Yamaguchi, M.Chijimatsu, A.Sakurai, Y.Sato and H.Kitamura: ""Bioactive condensed tannins from bark : chemical properties, enzyme inhibition and anti-plant-viral activities"" J.Pesticide Sci.15. 585-591 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Sassa, M.Nukina and Y.Suzuki: ""Deoxyfunicone, a new gamma-pyrone metabolite from a resorcylide-producing fungus (Penicillium sp.)"" Agric.Biol.Chem. 55. 2415-2416 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Kono, S.Sekido, I.Yamaguchi, H.Kondo, Y.Suzuki, G.C.Neto, A.Sakurai and H.Yaegashi: ""Structures of two novel pyriculol-related compounds and identification of naturally produced epipyriculol from Pyricularia oryzae"" Agric.Biol.Chem. 55. 2785-2791 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] G.C.Neto, Y.Kono, H.Hyakutake, M.Watanabe, Y.Suzuki and A.Sakurai: ""Isolation and identification of (-)-jasmonic acid from wild rice, Oryzae officinalis, as an antifungal substance" Agric.Biol.Chem. 55. 3097-3098 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Kono, J.Uzawa, K.Kobayashi, Y.Suzuki, M.Uramoto, A.Sakurai, M.Watanabe, T.Teraoka, D.Hosokawa, M.Watanabe and H.Kondo: ""Structures of oryzalides A and B, and oryzalic acid A, a group of novel antimicrobial diterpenes, isolated from healthy leaves of a bacterial leaf blight-resistant cultivar of rice plant"" Agric.Biol.Chem. 55. 803-811 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Y.Suzuki Y.Kono, Y.Takahashi, K.Suenaga, J.M.Daly, H.W.Knoche and A.Sakurai: ""Toxic activity of mimics of the host-specific pathotoxin PM-toxin on Corn carrying Texas male-sterile cytoplasm"" Agric.Biol.Chem. 55. 1061-1070 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Watanabe, Y.Kono, M.Watanabe, J.Uzawa, T.Teraoka, D.Hosokawa, Y.Suzuki, A.Sakurai and M.Teraguchi: ""Structures of oryzalic acid B and three related compounds, a group of novel antibacterial diterpenes, isolated from leaves of bacterial leaf blight-resistant cultivar of rice"" Biosci.Biotech.Biochem. 56. 113-117 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yoshiki kono: "structures of oryzalides A and B,and oryzalic acid A,a group of novel antimicrobial diterpenes,isolated from nealthyleaves・・・" Agric.Biol.Chem.55. 803-811 (1991)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoshikatsu Suzuki: "Toxic activity of mimics of the host-specific pathotoxin PM-toxin on corn carrying texas male-sterile cytoplasm" Agric.Biol.Chem.55. 1061-1070 (1991)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoshiki Kono: "Structures of two nivel pyriculol-related compounds and identification of naturally produced epi pyriculol from Pyricularia oryzae" Agric.Biol.Chem.55. 2785-2791 (1991)

    • Related Report
      1993 Annual Research Report
  • [Publications] Germano Cord Neto: "Isolation and identification of (-)-jasmonic acid from wildrice,oryza officinalis,as an antifungal substance" Agric.Biol.Chem.55. 3097-3098 (1991)

    • Related Report
      1993 Annual Research Report
  • [Publications] Manabu Watanabe: "Structures of oryzalic acid B and three related compounds,a group of novel antibacterial diterpenes,isolated from leaves・・・" Biosci.Biotech.Biochem.56. 113-117 (1992)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoshiki Kono: "Structures of oryzalides A and B,and oryzalic acidA,a group of novel antimicro bial diterpens,isolated from nealty leaves of a bacterial leaf blight-resistant cultiuar of nice plant" Agric Biol.Chem.55. 803-811 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] Yoshikatsu Suzuki: "Toxic activity of mimics of the host-specific pathotoxin PM-toxin on corn carrying Texas male-sterile cytoplasm" Agric.Biol,Chem.55. 1061-1070 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] Yoshiki Kono: "Structures of two novel pyriculol-related compounds and identification of naturally produced epipyriculol from pyricularia oryzae" Agric.Biol,Chem.55. 2785-2791 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] Germano Cord Neto: "Isolation and identification of(-)-jasmonic acid from wild rice.oryza officinalis as an antifungal substarxe" Agric.Biol.Chem.55. 3097-3098 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] MaNabu Watanabe: "Structures of oryzalic acid B and three related compounds,a group of novel antibacterial diterpens,isolated from leaves of a bacterial leaf blight-resistant cldtivar offitce" Biosci,Biotech,Biochem.56. 113-117 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Yoshiki Kono: "Structures of oryzalides A and B,and oryzalic acid A,a group of novel antimicronial diterpenes,isolated from healthy leaves of a bacterial leaf blight-resistant cultivar of rice plat" Agric.Biol.Chem. 55. 803-811 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yoshikatsu Suzuki: "Toxic activity of mimics of the host-specific pathotoxin PM-toxin on corn carrying Texas male-sterile cytoplasm" Agric.Biol.Chem. 55. 1061-1070 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yoshiki Kono: "Structures of two novel pyriculol-related compounds and identification of naturally produced epipyriculol from Pyricularia oryzae" Agric.Biol.Chem. 55. 2785-2791 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Germano Cord Neto: "Isolation and identification of (-)-jasmonic acid from wildrice,Oryza officinalis.as an antifungal substance" Agric.Biol.Chem. 55. 3097-3098 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Manabu Watanabe: "Structures of oryzalic acid B and three related compounds,a group of novel antibacterial diterpenes,isolated from leaves of a bacterial leat blight-resistant cultivar of rice" Biosci.Biotech.Biochem.56. 113-117 (1992)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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