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Synthesis of New Indolic Plant Hormones and Their Application to Plant Tissue Cultures

Research Project

Project/Area Number 63860017
Research Category

Grant-in-Aid for Developmental Scientific Research (B).

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionNagoya University

Principal Investigator

MARUMO Shingo  Nagoya Univ., Dept. Agriculture, Professor, 農学部, 教授 (30023394)

Co-Investigator(Kenkyū-buntansha) SASSA Takeshi  Yamagata Univ., Dept. Agriculture, Professor, 農学部, 教授 (80023456)
NATSUME Masahiro  Nagoya Univ., Dept. Agriculture, Research Associate, 農学部, 助手 (10201683)
SAKAGAMI Youji  Nagoya Univ., Dept. Agriculture, Associate Professor, 農学部, 助教授 (80107408)
FUTATSUYA Fumio  Nippon Kayaku Co., Ltd., Agrochemicals Division, Group Manager, 農薬研究所, 主任研究員
片山 正人  名古屋大学, 農学部, 助教授 (90177410)
Project Period (FY) 1988 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥11,200,000 (Direct Cost: ¥11,200,000)
Fiscal Year 1990: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 1989: ¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1988: ¥7,300,000 (Direct Cost: ¥7,300,000)
KeywordsAuxin / Antiauxin / 5, 6-dichloroindole--acetic acid / Indole--acetic acid / Floral bud formation / Alpha-(5, 7-Dichloroindole-)isobutyric acid / インド-ル酢酸 / ハロゲノインド-ル酢酸 / 植物培養細胞 / オーキシン / アンチオーキシン / 5,6ージフルオロインドールー3ー酢酸 / 5,7ージフルオロインドールイソ酪酸
Research Abstract

Based on our success in the previous isolation of 4-chloroindole--acetic acid and its methyl ester from immature seeds of Pisum sativum, we synthesized all ten regioisomers of dichloro-derivatives of indole--acetic acid, and measured their auxin activity. Among them, -dichloroindole--acetic acid (5, 6-Cl_2-IAA) showed the strongest auxin activity, and this activity was stronger than all the known natural and synthetic auxins. It induced many lateral roots in mung bean seedlings, and resisted peroxi-dase-catalyzed decomposition. In contrast, 5, 7-dichloroindole--acetic acid (5, 7-Cl_2-IAA) showed much weaker auxin activity than the other dichloro-indole derivatives. Interestingly, when wheat and rice seeds were germinated with 5, 7-Cl_2-IAA their roots curled markedly upwards. This negative geotropism is clearly an antiauxin activity. To eliminate its weak auxinlike activity, we changed the side chain of AA from acetyl to isobutyryl group, which is known to change auxin activity of 2, 4 … More -D to antiauxin of PCIB. alpha-(5, 7-Dichloroindole-3-)isobutyric acid (5, 7-Cl_2-IIBA) thus synthesized showed to inhibit auxin-mediated elongation of avena coleoptiles. Its activity is stronger than that of alpha-(pchlorophenoxy)isobutyric acid and is comparable to that of 2, 3, 5-triiodobenzoic acid, which are typical antiauxins.
5, 6-Cl_2-IAA induced tropane alkaloid production in root cultures of a Duboisia hybrid at 0.01mg/L, which was comparable to 0.5mg/L IAA. By using 5, 6-Cl_2-IAA, the alkaloids were detected not only in the root tissue but also in the medium. An in vitro bioassay system for floral bud formation was established using Nicotiana tabacum explants excised from floral stalks cultured on modified Murashige-Skoog medium containing excess auxin (IAA) and antiauxin (5, 7-Cl_2-IIBA). In this system, 5, 7-Cl_2-IIBA was very effective : leaf exudate from short day-treated plants stimulated floral bud formation. Moreover, the buds produced grew into large, well-developed ones with shapes similar to those of the natural floral buds of intact tobacco plants. Less

Report

(4 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • 1988 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] T.Hatano: "5,6ーDichloroindoleー3ーacetic Acid as a Potent Auxin:its Synthesis and Biological Activity" Experientia. 43. 1237-1239 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T.Hatano: "A New Indolic Antiauxin,αー(5,7ーDichloroindoleー3ー)ーisobutyric Acid:Its Chemical Synthesis and Biological Activity" Experientia. 45. 400-402 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K.Yoshimatsu: "IAA Derivative Induced Tropane Alkaloid Production in Root Cultures of a Duboisia Hybrid" Phytochemistry. 29. 3525-3528 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M.Hatori: "The Effects of Auxin and Antiauxin in an in vitro Bioassay of Flower Reguratory Activity in Leaf Exudate from Tobaco Plants" Physiol.Plantarum. 81. 1-6 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T. Hatano: "5, 6-Dichloroindole--acetic Acid as a Potent Auxin : its Synthesis and Biological Activity" Experientia. 43. 1237-1239 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T. Hatano: "A New Indolic Antiauxin, alpha-(5, 7-Dichloroindole--)isobutyric Acid : Its Chemical Synthesis and Biological Activity" Experientia. 45. 400-402 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K. Yoshimatsu: "IAA Derivative induced Tropane Alkaloid Production in Root Cultures of a Duboisia Hybrid" Phytochemistry. 29. 3525-3528 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M. Hatori: "The Effects of Ausin and Antiauxin in an in vitro Bioassay of Flower Regularatory Activity in Leaf Exudate from Tobaco Plants" Physiol. Plantarum. 81. 1-6 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T.Hatano: "5,6ーDichloroindoleー3ーacetic Acid as a Potent Auxin:its Synthesis and Biological Activity" Experientia. 43. 1237-1239 (1987)

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Hatano: "A New Indolic Antiauxin,αー(5,7ーDichloroindoleー3ー)ーisobutyric Acid: Its Chemical Synthesis and Biological Activity" Experientia. 45. 400-402 (1989)

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Yoshimatsu: "IAA Derivative Induced Tropane Alkaloid Production in Root Cultures of a Duboisia Hybrid" Phytochemistry. 29. 3525-3528 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Hatori: "The Effects of Auxin and Antiauxin in an in vitro Bioassay of Flower Reguratory Activity in Leaf Exudate from Tobaco Plants" Physiol.Plantarum. 81. 1-6 (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Hatano: "α-(5,7-Dichloroindole-3-)isobutyric Acid:Its Chemical Synthesis and Biological Activity" Experientia. 45. 400-402 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] S.Marumo et al.: Experientia. 45. (1988)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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