Novel Cyclohexyl Meroterpenes Produced by Combinatorial Biosynthesis

Chem Pharm Bull (Tokyo). 2021;69(5):444-446. doi: 10.1248/cpb.c21-00123.

Abstract

Structurally diverse fungal meroterpenoids are promising drug seed compounds. To obtain unnatural, novel meroterpene scaffolds, we tested combinatorial biosynthesis by co-expressing functionally distinct terpene cyclase (TPC) genes, pyr4, ascF, andB, or cdmG, with the biosynthetic genes for the production of a TPC substrate, (10'R)-epoxyfarnesyl-dimethylorsellinic acid-3,5-methyl ester, in Aspergillus oryzae NSAR1 as a heterologous host. As a result, all of the tested TPCs afforded the same two novel mono-cyclization products. This study provides important information on the substrate scope of the TPCs, and will contribute to the production of unnatural, novel molecules for future drug discovery.

Keywords: biosynthesis; drug seed; enzyme; meroterpenoid; microbial; production.

MeSH terms

  • Alkyl and Aryl Transferases / genetics
  • Alkyl and Aryl Transferases / metabolism*
  • Aspergillus oryzae / enzymology
  • Biocatalysis
  • Cyclopentanes / chemistry
  • Cyclopentanes / metabolism*
  • Molecular Structure
  • Terpenes / chemistry
  • Terpenes / metabolism*

Substances

  • Cyclopentanes
  • Terpenes
  • Alkyl and Aryl Transferases