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Carbazomycins, Antifungal Carbazole-Antibiotics Active Against Phytopathogenic Fungi. -Biosynthesis of Carbazomycin B and Structure Elucidation of the Congeners-

Research Project

Project/Area Number 61571004
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionHiroshima University

Principal Investigator

KANEDA Miyuki  Hiroshima Univ., School of Medicine Associate Professor, 医学部, 助教授 (40019675)

Co-Investigator(Kenkyū-buntansha) NAKAMURA Shoshiro  Hiroshima Univ., School of Medicine Professor, 医学部, 教授 (40013304)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 1987: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1986: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsCarbazomycins / Antifungal antibiotics / Biosynthesis of carbazomycin B / Incorporation of pyruvate / Carbazomycin C / Carbazomycin D / Carbazomycin G / Carbazomycin H / 酢酸導入の配列方向性 / 〔2-^<13>C, ^2H_3〕酢酸の投与 / ^2Hアイソトープシフト / X線結晶解析 / カルバゾール系抗生物質 / 【^(13)C】-NMR
Research Abstract

Carbazomycins A (II) and B (I) were isolated from Streptoverticillium ehimense as the first antibiotics having a carbazole nucleus and inhibit mainly the growth of phytopathogenic fungi.
In our previous biosynthetic studies of I, we found that the origin of all carbon atoms of the carbazole nucleus except C-1 and C-2 are derived from tryptophan, C-12 from methionine and the C^2 unit, C-1 and C-10, from acetate. In this project, we attempted to determine the origin of the unsolved C_2 unit, C-2 and C-11, by feeding experiments with ^<14>C- and ^<13>C-labeled compounds followed by measurement of radioactivity and ^<13>C NMR spectra. The results has indicated that the intact C_2 unit of C-2 and C-3 of pyruvate is incorporated into C-2 and C- 11 of I and that this C_2 unit of pyruvate is also incorporated into C-1 and C-10 probably by way of acetyl-CoA. Hence, the origin of the all carbon atoms of I has been established as shown in Fig. 1.
During the biosynthetic studies, we found six minor components, carbazomycins C (III), D (IV), E (V), F (VI), G (VII) and H (VIII). Their structures have been elucidated as shown in Fig. 2 and Fig. 3 by ^1H and ^<13>C NMR, chemical correlation and X-ray analyses.

Report

(3 results)
  • 1990 Final Research Report Summary
  • 1987 Annual Research Report
  • 1986 Annual Research Report
  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] 金田 幸: "Biosynthesis of Carbazomycin B.II.Origin of the Whole Carbon Skeleton." The Journal Antibiotics. 43. 1623-1626 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Tadjuddin Naid: "Carbazomycins C,D,E and F,Minor Components of the Carbazomycin Complex." The Journal of Antibiotics. 40. 157-164 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 金田 幸: "Carbazomycins G and H,Novel Carbazomycinーcongeners Containing a Quinol Moiety." The Jouranl of Antibiotics. 41. 602-608 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Miyuki Kaneda: "Biosynthesis of Carbazomycin B. II. Origin of the Whole Carbon Skeleton." J. Antibiotics. 43. 1623-1626 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Tadjuddin Naid: "Cardazomycins C, D, E and F, Minor Components of the Carbazomycin Complex." J. Antibiotics. 40. 157-164 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Miyuki Kanaba: "Carbazomycins G and H, Novel Carbazomycin-congeners Containing a Quinol Moiety." J. Antibiotics. 41. 602-608 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Miyuki Kaneda: The Journal of Antibiotics. 41. (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] Miyuki Kaneda: The Journal of Antibiotics.

    • Related Report
      1987 Annual Research Report
  • [Publications] Tadjuddin Naid: The Journal of Antibiotics. 40. 157-164 (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Miyuki Kaneda: The Journal of Antibiotics.

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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