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O-Methylation steps during strobilurin and bolineol biosynthesis.

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Two O-methyltransferase enzymes, Str2 and Str3, regioselectively methylate precursors in strobilurin biosynthesis. Str2 acts first on the carboxyl group, followed by Str3 on the enol group, yielding potent antifungal strobilurin A 1.

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Area of Science:

  • Biochemistry
  • Mycology
  • Natural Product Biosynthesis

Background:

  • Strobilurins are potent antifungal polyketides synthesized by fungi.
  • The biosynthetic gene cluster for strobilurin A 1 contains two O-methyltransferase (O-MeT) genes, Str2 and Str3.
  • Previous work identified Str2 and Str3 as key enzymes in the final steps of strobilurin A 1 biosynthesis.

Purpose of the Study:

  • To elucidate the regioselectivity of O-methylation in strobilurin biosynthesis.
  • To determine the specific roles of O-methyltransferases Str2 and Str3 in the pathway.
  • To evaluate the antifungal activity of strobilurin biosynthetic intermediates.

Main Methods:

  • In vivo expression experiments to analyze enzyme activity.
  • Regiospecificity assays for O-methylation reactions.
  • Antifungal toxicity tests using minimum inhibitory concentration (MIC) determination.

Main Results:

  • O-methylation during strobilurin biosynthesis is regiospecific.
  • O-MeT Str2 selectively methylates the carboxyl group of strobilurin and bolineol precursors.
  • Str3 catalyzes subsequent methylation of the enol group to form strobilurin A 1, but not bolineol 4.
  • Antifungal activity increased through the pathway, with bolineol 4 showing significant activity (MIC 0.1 mg/ml) against Aspergillus oryzae.

Conclusions:

  • Str2 and Str3 act sequentially and regioselectively in strobilurin A 1 biosynthesis.
  • The sequential action of Str2 and Str3 is crucial for generating the final antifungal compound.
  • Strobilurin biosynthetic intermediates possess notable antifungal properties, highlighting their potential.