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Synthetic studies on bioactive natural products related to the chemical control of agricultural ecosystem

Research Project

Project/Area Number 13660103
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

KUWAHARA Shigefumi  Graduate School of Agricultural Science Division of Life Science, Professor, 大学院・農学研究科, 教授 (30170145)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥4,200,000 (Direct Cost: ¥4,200,000)
Fiscal Year 2002: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 2001: ¥2,500,000 (Direct Cost: ¥2,500,000)
Keywordsazadirachtin / Eysarcoris parvus / Pseudococcus cryptus / isorobinal / pyricuol / volicitin / phytoalexin / pteridic acid / azadirachtin / antifeedant / Eysarcoris aeneua / isorobinal / volicitin / Pseudococcus cryptus / Hyoscyamus albus / oryzalexin S / pheromone / oryzalexin / Spodoptera exigua / elicitor / phytoalexin
Research Abstract

Synthetic Studies were conducted on azadirachtin (1, insect antifeedant), (Z)-exo-α-bergamotenal (2, sex pheromone of Eysarcoris parvus), isorobinal (3, novel cyclic monoterpene from the astigmatid mite), volicitin (4, elicitor from the Spodoptera exigua), the sex pheromone of the citriculus mealybug (5), a phytoalexin isolated from Hyoscyamus albus (6), oryzalexin S (7, phytozlexin from the rice plant), tabtoxinine-β-lactam (8, phytotoxin from Pseudomonas tabaci), pyricuol (9, phytotoxin from Magnaporthe grisea), and ptericids A and B (10 and 11, auxin-like plant growth promoter from Streptomyces hygroscopicus). A model compound of 1 containg the bicyclo[2.2.1]heptane ring connected to the B ring was synthesized by using the Beckmann rearrangement of a petacyclic precursor. Synthesis of 2, 3, 4, 5, 9 was accomplished from farnesic acid, perilaldehyde, lactic acid, a-pinene, and 2,3-dimethylpheno1, respectively. Synthetic efforts toward 6, 7, 8, 10, and 11 were now in progress.

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] Babak Heidary Alizadeh: "Synthesis of the racemate of (Z)-exo-α-bergamotenal, a sex pheromone component of the whitespotted spined bug, Eysarcoris parvus Uhler"Biosci.ence, Biotechnology, and Biochemistry. 66. 1415-1418 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Seiji Itoh: "Synthesis of the (17R)-and (17S)-isomers of volicitin, an elicitor of plant volatiles contained in the oral secretion of the beet armyworm"Biosci.ence, Biotechnology, and Biochemistry. 66. 1591-1596 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Ting Liang: "Synthesis of both enantiomers of isorobinal, a novel cyclic monoterpene isolated form the astigmatid mite, Rhizoglyphus sp"Biosci.ence, Biotechnology, and Biochemistry. 66. 2501-2503 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiromasa Kiyota: "First synthesis of (±)-pyricuol, a plant pathogen isolated from rice blast disease fungus Magnaporthe grisea"Synlett. 219-220 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] B.H.Alizadeh, S.Kuwahara, W.S.Leal, and H-C.Men: "Synthesis of the racemat of (Z)-exo-α-bergamotenal, a sex pheromone component of the whitespotted spined bug, Eysarcoris parvus Uhler"Biosci. Biotechnol. Biochem. 66. 1415-1418 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S.Itoh, S.Kuwahara, M.Hasegawa, and O.Kodama: "Synthesis of (17R)- and (17S)- isomers of volicitin, and elicitor of plant volatiles contained in the oral secretion of the beet armyworm"Biosci. Biotech. Biochem. 66. 1591-1596 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Liang and S.Kuwahara: "Synthesis of both enantiomers of isorobinal, a novel cyclic monoterpene isolated from the astigmatid mite, Rhyzoglyphus sp"Biosci. Biotech. Biochem. 66. 2501-2503 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Kiyota, R.Ueda, T.Oritani, and S.Kuwahara: "First synthesis of (±)-pyricuol, a plant pathogen isolated from rice blast disease fungus Magnaporthe grisea"Synlett. 21-220 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] B.H.Alizadeh, S.Kuwahara, W.S.Leal, H.-C.Men: "Synthesis of the racemate of (Z)-exo-α-bergamotenal, a sex pheromone component of the whitespotted spined bug, Eysarcoris parvus Uhier"Biosci. Biotechnol. Biochem.. 66. 1415-1418 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] S.Itoh, S.Kuwahara.M.Hasegawa, O.Kodama: "Synthesis of (17R)-and (17S)-isomers of volicitin, an elicitor of plant volatiles contained in the oral secretion of the beet armyworm"Biosci. Biotechnol. Biochem.. 66. 2501-2503 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Liang, S.Kuwahara: "Synthesis of both enantiomers of isorobinal, a novel cyclic monoterpene isolated from the astigmatid mite, Rhyzoglyphus sp."Biosci. Biotechnol. Biochem.. 66. 2501-2503 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Arai, H.Sugie, S.Hiradate, S.Kuwahara, N.Itagaki: "Identification of the sex pheromone of Pseudococcus cryptus Hempel (Homoptera : Pseudococcidae)"J. Chem. Ecol.. 29(in press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] B.H.Alizadeh, S.Kuwahara W.S.Leal, H.-C.Men: "Synthesis of the racemate of (Z)-exo-α-bergamotenal, a sex pheromone component of the whitespotted spined bug, Eysarcoris parvus Uhler"Biosci. Biotechnol. Biochem.. 66(印刷中). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] S.Itoh, S.Kuwahara M.Hasegawa, O.Kodama: "Synthesis of (17R)- and (17S)-isomers of volicitin, an elicitor of plant volatiles contained in the oral secretion of the beet armyworm"Biosci. Biotechnol. Biochem.. 66(印刷中). (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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