Biosynthesis of p-Terphenyls in Aspergillus ustus Implies Enzymatic Reductive Dehydration and Spontaneous Dibenzofuran Formation

Org Lett. 2023 Sep 1;25(34):6311-6316. doi: 10.1021/acs.orglett.3c02234. Epub 2023 Aug 22.

Abstract

p-Terphenyls contain a central benzene ring substituted with two phenyl residues at its para positions. Heterologous expression of a biosynthetic gene cluster from Aspergillus ustus led to the formation of four new p-terphenyl derivatives. Gene deletion experiments proved the formation and reductive dehydration of the terphenylquinone atromentin, followed by O-methylation and prenylation. Spontaneous dibenzofuran formation led to the final products. These results provide new insights into the biosynthesis of p-terphenyls in fungi and dibenzofuran formation in the biosynthesis of numerous natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus
  • Dehydration*
  • Dibenzofurans
  • Prenylation
  • Terphenyl Compounds*

Substances

  • Terphenyl Compounds
  • Dibenzofurans

Supplementary concepts

  • Aspergillus ustus