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Antitumor Antibiotics from Fungi

Research Project

Project/Area Number 01560154
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionDepartment of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture

Principal Investigator

NAKAYAMA Mitsuru  University of Osaka Prefecture College of Agriculture Professor, 農学部, 教授 (20033821)

Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1990: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1989: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsAntitumor antibiotics / Myrocin B / Myrocin C / Pimaran-type antitumor diterpene / Chlorine-containing shikimate / 3ーメトキシー2,5ートルキノン / Myrothecium verrucaria / ピラマン型ジテルペノイド
Research Abstract

During the course of our screening program for novel antitumor antibiotics, we have recently isolated two new pimarane-type antitumor antibiotics named myrocin C and B from the culture filtrate of a soil fungus, Myrothecium verrucaria strain No. 55. The structures of myrocin C and B were characteriz
ed as a pentacyclic pimarane diterpene composed of a gamma -lactol group and a unique cyclopropane ring on the basis of its physico-chemical properties and spectroscopic data as well as a single-crystal X-ray diffraction analysis of myrocin C monoacetyl derivative, namely 1, 20-cyclo-6, 6, 9-trihydroxy-19-oic-7-oxo-8, 15-pimaradiene-19, 6-gamma -lactone and its 11-oxo derivative. In addition to a related compound named 55-0 substance was isolated from the same metabolite. Mainly, from the comparison of various spectral data between myrocin C, B and 55-0, its structure was proposed as 9-hydroxy7-oxo-1, 5, 8, 15-pimaratetraene-19, 6-gamma -lactone.
From the other fungus, new active substances, a chlorine-containing shikimate-related metabolite and 3-methoxy-2, 5-toluquinine, were isolated from soil collected near Sakai City. The structure including absolute stereochemistry of the chlorine-containing metabolite was established by spectroscopic and X-ray crystallographic studies as (1R, 6R, 9S, 10S)-9-chloro-10-hydroxy-8-methoxycarbony1-4-methylene-2, 5-di-oxabicyclo[4.4.0] dec-3-one-7-ene.
These antibiotics were effective against some Gram-positive bacteria, fungi and yeasts. It is particularly noteworthy that myrocin B and C had a good therapeutic effect on mice infected with Ehrlich ascites carcinoma, with the prolongation rate (T/C) of 169% at a dose of 2.4 m g/kg being significantly higher that than of myrocin C (130%). Cytotoxic effect of chlorine-containing metabolite against murine lymphocytic leukemia P-388 cells is a comparable effect to that obtained for 5-fluorouracil.

Report

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

    (3 results)

All Other

All Publications (3 results)

  • [Publications] E. Kitamura: "(1R,6R,9S,10S)ー9ーChloroー10ーhydroxyー8ーmethoxycarbonylー4ーmethyleneー2.5ーdioxabicyclo[4.4.0]decー3ーoneー7ーene. A First Chlorineーcontaining Shikimate related Metabolite from Fungi." Tetrahedron Lett.31. 4605-4608 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Eiji Kitamura: "(1R, 6R, 9S, 10S)-9-Chloro-10-hydroxy-8-methoxycarbony1-4-methylene-2, 5-dioxabicyclo-[4.4.0]dec-3-one-7-ene, A First Chlorine-containing Shikimate-related Metabolite from Fungi" Tetrahedron Lett.31. 4605-4608 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] E.Kitamura: "(1R,6R,9S,10S)ー9ーChloroー10ーhydroxyー8ーmethoxycarbonylー4ーmethleneー2,5ーdioxabicyclo[4.4.0]decー3ーoneー7ーene.A First Chlorineーcontaining Shikimate related Metabolite from Fungi." Tetrahedron Lett.31. 4605-4608 (1990)

    • Related Report
      1990 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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