Insights on the susceptibility of plant pathogenic fungi to phenazine-1-carboxylic acid and its chemical derivatives

Nat Prod Res. 2013;27(11):956-66. doi: 10.1080/14786419.2012.696257. Epub 2012 Jun 25.

Abstract

Pseudomonas chlororaphis subsp. aureofaciens strain M71 produced two phenazine compounds as main secondary metabolites. These metabolites were identified as phenazine-1-carboxylic acid (PCA) and 2-hydroxyphenazine (2-OH P). In this study, the spectrum of the activity of PCA and 2-OH P was evaluated against a group of crop and forestal plant pathogenic fungi by an agar plate bioassay. PCA was active against most of the tested plant pathogens, while 2-OH P slightly inhibited a few fungal species. Furthermore, four semisynthesised derivatives of PCA (phenazine-1-carboxymethyl, phenazine-1-carboxamide, phenazine-1-hydroxymethyl and phenazine-1-acetoxymethyl) were assayed for their antifungal activity against 11 phytopathogenic species. Results showed that the carboxyl group is a structural feature important for the antifungal activity of PCA. Since the activity of phenazine-1-carboxymethyl and phenazine-1-carboxamide, the two more lipophilic and reversible PCA derivatives remained substantially unaltered compared with PCA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fungi / drug effects*
  • Phenazines / toxicity
  • Plants / microbiology*
  • Principal Component Analysis
  • Pseudomonas / metabolism*
  • Spectrum Analysis

Substances

  • Phenazines
  • 1-phenazinecarboxylic acid