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Biosynthesis of sespendole.

Ryuji Uchida1, Hiroshi Tomoda, Satoshi Omura

  • 1School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.

The Journal of Antibiotics
|August 4, 2006
PubMed
Summary

Researchers investigated the biosynthesis of sespendole, a unique fungal metabolite. Feeding experiments revealed its indolosesquiterpene core originates from mevalonate and anthranilate pathways.

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Area of Science:

  • Natural Product Chemistry
  • Mycology
  • Biochemistry

Background:

  • Sespendole is the first identified fungal metabolite featuring an indolosesquiterpene core.
  • Understanding the biosynthesis of novel natural products is crucial for drug discovery and chemical biology.

Purpose of the Study:

  • To elucidate the biosynthetic pathway of sespendole.
  • To identify the precursor molecules and key enzymatic steps involved in forming the indolosesquiterpene core.

Main Methods:

  • Metabolic labeling experiments using isotopically labeled precursors: [13C]acetate, [15N]anthranilic acid, and [13C]tryptophan.
  • Analysis of incorporation patterns to trace the origin of atoms within the sespendole structure.

Main Results:

  • Feeding experiments demonstrated that the sesquiterpene moiety of sespendole is derived from the mevalonate pathway via a farnesyl pyrophosphate intermediate.
  • The indole moiety is derived from anthranilic acid, specifically through indole-3-glycerol phosphate.
  • Data suggests a condensation reaction between the farnesyl residue and the indole precursor, followed by cyclization and rearrangement to form the core structure.

Conclusions:

  • The biosynthesis of sespendole involves the convergence of the mevalonate and anthranilate pathways.
  • A novel mechanism for forming the indolosesquiterpene core structure in fungi has been proposed.

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