Production of Bacterial Quorum Sensing Antagonists, Caffeoyl- and Feruloyl-HSL, by an Artificial Biosynthetic Pathway

J Microbiol Biotechnol. 2017 Dec 28;27(12):2104-2111. doi: 10.4014/jmb.1705.05033.

Abstract

A new series comprising phenylacetyl-homoserine lactones (HSLs), caffeoyl-HSL and feruloyl-HSL, was biologically synthesized using an artificial de novo biosynthetic pathway. We developed an Escherichia coli system containing artificial biosynthetic pathways that yield phenylacetyl-HSLs from simple carbon sources. These artificial biosynthetic pathways contained the LuxI-type synthase gene (rpaI) in addition to caffeoyl-CoA and feruloyl-CoA biosynthetic genes, respectively. Finally, the yields for caffeoyl-HSL and feruloyl-HSL were 97.1 ± 10.3 and 65.2 ± 5.7 mg/l, respectively, by tyrosine-overproducing E. coli with a L-methionine feeding strategy. In a quorum sensing (QS) competition assay, feruloyl-HSL and p-coumaroyl-HSL antagonized the QS receptor TraR in Agrobacterium tumefaciens NT1, whereas caffeoyl-HSL did not.

Keywords: Artificial biosynthesis; caffeoyl-HSL; feruloyl-HSL; phenylacetyl homoserine lactone.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / biosynthesis
  • Agrobacterium tumefaciens / drug effects
  • Biosynthetic Pathways
  • Escherichia coli / genetics
  • Escherichia coli / metabolism*
  • Escherichia coli Proteins / genetics
  • Gene Expression Regulation, Bacterial
  • Lactones / metabolism
  • Quorum Sensing / drug effects*
  • Transcription Factors / genetics

Substances

  • Escherichia coli Proteins
  • Lactones
  • Transcription Factors
  • homoserine lactone
  • 4-Butyrolactone