Isolation and biosynthesis of preussin B, a pyrrolidine alkaloid from Simplicillium lanosoniveum

J Nat Prod. 2014 Apr 25;77(4):813-7. doi: 10.1021/np400910r. Epub 2014 Mar 4.

Abstract

A new pyrrolidine alkaloid, preussin B (1), was isolated from the culture extract of the fungus Simplicillium lanosoniveum TAMA 173 along with the known congener preussin (2). The structure and absolute configuration of 1 were determined by spectroscopic analysis and spectral comparison with 2. Feeding experiments with 13C-labeled precursors revealed that the pyrrolidine ring of 1 was assembled from acetate and l-phenylalanine by a PKS-NRPS hybrid biosynthetic pathway.

MeSH terms

  • Alkaloids / biosynthesis
  • Alkaloids / metabolism
  • Anisomycin / analogs & derivatives*
  • Anisomycin / chemistry
  • Anisomycin / isolation & purification
  • Hypocreales / chemistry*
  • Molecular Structure
  • Multienzyme Complexes / biosynthesis
  • Multienzyme Complexes / metabolism
  • Peptide Synthases / biosynthesis
  • Peptide Synthases / chemistry
  • Peptide Synthases / metabolism
  • Phenylalanine / biosynthesis
  • Phenylalanine / metabolism
  • Stereoisomerism
  • Streptomyces / metabolism

Substances

  • Alkaloids
  • Multienzyme Complexes
  • preussin B
  • preussin
  • Phenylalanine
  • Anisomycin
  • Peptide Synthases