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Directed biosynthesis of avermectins.

T S Chen1, E S Inamine, O D Hensens

  • 1Department of Fermentation Microbiology, Merck Sharp & Dohme Research Laboratories, Rahway, New Jersey 07065.

Archives of Biochemistry and Biophysics
|March 1, 1989
PubMed
Summary
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New avermectin homologs, designated "c" and "d" components, were produced by modifying Streptomyces avermitilis fermentation. These novel avermectins exhibit potent anthelmintic and insecticidal properties.

Area of Science:

  • Microbial biochemistry
  • Natural product synthesis
  • Agricultural science

Background:

  • Avermectins are potent antiparasitic compounds produced by Streptomyces avermitilis.
  • Natural avermectins possess specific alkyl groups at the C-25 position of the aglycone moiety.
  • Modifying the fermentation process can lead to novel avermectin analogs with potentially altered properties.

Purpose of the Study:

  • To investigate the production of novel avermectin homologs by supplementing Streptomyces avermitilis cultures.
  • To characterize the structural modifications and biological activities of these new avermectin components.

Main Methods:

  • Fermentation of Streptomyces avermitilis with specific precursor molecules (sodium 2-methylpentanoate and sodium 2-methylhexanoate).
  • Structural analysis of the produced avermectin homologs.

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  • Evaluation of anthelmintic and insecticidal activities of the novel compounds.

    • Main Results:

    • Successful production of avermectin homologs designated as
    • c
    • and
    • d
    • components.
    • These new homologs feature 2-pentyl and 2-hexyl groups at C-25, differing from natural avermectins' 2-butyl (
    • a
    • ) and isopropyl (
    • b
    • ) groups.
    • Both avermectin
    • c
    • and
    • d
    • components demonstrated potent anthelmintic and insecticidal activities.

    Conclusions:

    • Supplementation of Streptomyces avermitilis fermentation with specific fatty acid precursors is an effective strategy for generating novel avermectin analogs.
    • The introduction of different alkyl chains at the C-25 position significantly influences the structure of avermectin homologs.
    • The newly synthesized avermectin
    • c
    • and
    • d
    • components represent promising candidates for developing new anthelmintic and insecticidal agents.