Microbial production of O-methylated flavanones from methylated phenylpropanoic acids in engineered Escherichia coli

J Ind Microbiol Biotechnol. 2019 Dec;46(12):1707-1713. doi: 10.1007/s10295-019-02239-6. Epub 2019 Oct 8.

Abstract

Methylated flavonoids possess improved bioactivities compared to their unmethylated counterparts. In this study, for the efficient production of O-methylated flavonoids from simple methylated phenylpropanoic acids, a recombinant Escherichia coli strain expressing 4-coumarate:coenzyme A ligase (4CL) from Oryza sativa and chalcone synthase (CHS) from Hordeum vulgare was constructed; this strain produced significant amount of homoeriodictyol (~ 52 mg/L) as well as a few amount of hesperetin (0.4 mg/L), respectively, from ferulic acid and 4-methylcaffeic acid. This demonstrates, for the first time, that the scarce but valuable methylated flavanones can be successfully produced from methylated phenylpropanoic acids in a microbial host via an artificial biosynthetic pathway consisting of 4CL and CHS that can accept O-methylated precursors.

Keywords: Escherichia coli; Homoeriodictyol; Methylated flavanone; Microbial production; Phenylpropanoic acid.

MeSH terms

  • Acids, Carbocyclic / metabolism*
  • Acyltransferases / metabolism
  • Biosynthetic Pathways
  • Coenzyme A Ligases / metabolism
  • Coumaric Acids / metabolism
  • Escherichia coli / genetics
  • Escherichia coli / metabolism*
  • Flavanones / biosynthesis*

Substances

  • Acids, Carbocyclic
  • Coumaric Acids
  • Flavanones
  • ferulic acid
  • Acyltransferases
  • flavanone synthetase
  • Coenzyme A Ligases