Constructing Microbial Hosts for the Production of Benzoheterocyclic Derivatives

ACS Synth Biol. 2020 Sep 18;9(9):2282-2290. doi: 10.1021/acssynbio.9b00405. Epub 2020 Aug 20.

Abstract

Natural products containing benzoheterocyclic skeletons are widely found in plants and exhibit various pharmacological activities. To address the current limited availability of these compounds, we herein demonstrate the production of benzopyran, furanocoumarins, and pyranocoumarins in Streptomyces xiamenensis by employing prenyltransferases and two substrate-promiscuous enzymes, XimD and XimE. To avoid the degradation in S. xiamenensis, furanocoumarins and pyranocoumarins were also successfully produced in Escherichia coli. The production of linear furanocoumarins (marmesin) and angular pyranocoumarins (decursinol) reached 3.6 and 3.7 mg/L in shake flasks, respectively. To the best of our knowledge, this is the first report of the microbial production of the plant metabolites furanocoumarins and pyranocoumarins. Our study complements the missing link in the biosynthesis of pyranocoumarins by leveraging the catalytic promiscuity of microbial enzymes.

Keywords: Escherichia coli; Streptomyces; benzopyran; furanocoumarin; pyranocoumarin; synthetic biology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemistry
  • Benzopyrans / metabolism
  • Biocatalysis
  • Biological Products / chemistry
  • Biological Products / metabolism
  • Dimethylallyltranstransferase / genetics
  • Dimethylallyltranstransferase / metabolism
  • Escherichia coli / chemistry
  • Escherichia coli / metabolism
  • Furocoumarins / biosynthesis
  • Furocoumarins / chemistry
  • Genetic Engineering
  • Heterocyclic Compounds / chemistry*
  • Heterocyclic Compounds / metabolism
  • Plant Proteins / genetics
  • Plant Proteins / metabolism
  • Pyranocoumarins / chemistry
  • Pyranocoumarins / metabolism
  • Streptomyces / chemistry
  • Streptomyces / genetics
  • Streptomyces / metabolism*
  • Substrate Specificity

Substances

  • Benzopyrans
  • Biological Products
  • Furocoumarins
  • Heterocyclic Compounds
  • Plant Proteins
  • Pyranocoumarins
  • Dimethylallyltranstransferase

Supplementary concepts

  • Streptomyces xiamenensis