Phenazine-1-carboxylic acid mediated anti-oomycete activity of the endophytic Alcaligenes sp. EIL-2 against Phytophthora meadii

Abstract

The oomycete pathogen, Phytophthora meadii, causes various diseases in Hevea brasiliensis at different stages of its life cycle. The study reports the structural characterization of the active principle from the culture filtrate of Alcaligenes sp. EIL-2 (GenBank ID: HQ641257) offering antagonistic activity against P. meadii. Gas Chromatography Mass Spectroscopy (GC-MS) analysis showed the similarity of the compound with phenazine derivatives. The specific representations of FT-IR spectrum such as 3200 cm(-1) (OH stretching, NH stretching and presence of aromatic ring), 1737 cm(-1) (carboxylic acid), 2200-2400 cm(-1) (conjugated dienes) and 1467 cm(-1), and 1422 cm(-1) (CN bonds) were an indicative of phenazine-1-carboxylic acid (PCA). The structure of the compound was further confirmed by (1)H NMR/(13)C NMR spectroscopy, DEPT experiments, and two-dimensional NMR spectral studies, including (1)H-(1)H COSY and (1)H-(13)C HSQC as PCA with the molecular formula of C₁₃H₈N₂O₂. P. meadii was sensitive to purified PCA extract from the endophyte and a concentration of 5 μg/ml completely inhibited the mycelia growth. PCA also showed zoosporicidal activity against P. meadii zoospores. This is the first study of this kind where PCA from an endophyte of H. brasiliensis is being confirmed to carry antagonistic activity against P. meadii.

Transfer Hydrogenation of Ketones Catalyzed by Surface‐Active Ruthenium and Rhodium Complexes in Water

“…Biosynthesis of phenazine‐derivatives has been well documented, particularly in the representatives of bacterial genus Pseudomonas 1–16. In addition to this, several other bacterial genera including Gram‐negative Sorangium, Alcaligenes, Brevibacterium , Burkholderia , Xanthomonas , and Gram‐positive genera such as Streptomyces, Nocardia and Bacillus have also been reported to be phenazine producers 1–2, 17–18. Out of 6000 phenazine containing compounds described so far, several hundred showed anti‐tumor, anti‐malarial and anti‐parasitic attributes 2.…”

“…Phenazine‐1‐carboxylic acid (PCA), also known as tubermycin B (due to its antibiotic activity against Mycobacterium tuberculosis ), is one simplest form of bacterial phenazines 1–2. PCA‐producing bacterial species have been regarded as effective biocontrol agents in agricultural applications, since they exhibit antagonism against diverse phytopathogenic fungi including the genus Aspergillus, Phytophthora, Alternaria, Rhizoctonia, Sclerotium, Colletoricum , Seiridium, Fusarium and Verticillium 3, 9–12, 17, 22. The antagonism is thought to be due to the redox behavior of PCA 1 which is a property that has also been exploited in the microbial fuel cells 4–5.…”

Phenazine-1-carboxylic acid (PCA) from Cold-Adapted Yeast Glaciozyma antarctica PI12

“…Correlation between H-7 and C-8 also appears in the HMBC spectrum. All correlations showed that the isolated compound is phenazine-1carboxylic acid (PCA) (Abraham et al, 2015). This compound previously isolated from Streptomyces antibioticus strain Tü 2706 (Geiger et al, 1988), Pseudomonas aeruginosa (Jayatilake et al, 1996) and Pseudomonas aeruginosa UPMP3 (Lee et al, 2018) and Streptomyces kebangsaanensis (Remali et al, 2019).…”

Transcriptome alteration in Phytophthora infestans in response to phenazine-1-carboxylic acid production by Pseudomonas fluorescens strain LBUM223

“…PCA is known as an important broad-spectrum antimicrobial compound involved in the biocontrol of various plant pathogens, including Phytophthora spp. [ 22 , 24 , 32 ]. Generally, due to its nitrogen-containing heterocyclic composition, PCA is mainly described as promoting redox reactions and generating reactive oxygen species (ROS), of which the accumulation leads to a reduction in energy production, carbohydrate metabolism, and nutrient uptake [ 33 , 34 ].…”