Isolation and identification of bioactive substance 1‐hydroxyphenazine from
            <i>Pseudomonas aeruginosa</i>
            and its antimicrobial activity

Liu, T.T.; Ye, F.C.; Pang, Caoping; Yong, Tian; Tang, Wen; Xiao, Jun; Shang, Changhua; Lu, Zujun

doi:10.1111/lam.13332

Cited by 19 publications

(15 citation statements)

References 31 publications

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“…The 13 C-NMR of SF-1 provided the signals of 12 C. Of these, the C atom (δC: 151.7) was assigned to the C of hydroxyl group (C-OH) in the aromatic rings, while other C atoms were assigned to aromatic rings at 2, 3, 4, 4a, 5a, 6, 7, 8, 9, 9a, 10a with δC: 144.3, 144.5, 141.2, 134.7, 131.9, 130.8, 130.5, 129.7, 129.2, 119.9 and 108.9, respectively. In addition, the 13 C-NMR chemical shift coupling with spectra of DEPT 135, DEPT 90, and DEPT 45 ( Figures S4–S6 ) also indicated that this compound contained seven groups of CH and 5 C. These observations allowed us to identify this compound as hemi-pyocyanin (also known as 1-hydroxyphenazine); the NMR spectra of this compound corresponded to that of 1-hydrophenazine, identified in an earlier report [ 53 ].…”

Section: Resultssupporting

confidence: 66%

“…vesicatoria [ 55 , 56 , 57 ], and anti-inflammatory activities [ 58 ]. HPC has also reportedly been used in agriculture against various fungal and bacterial strains [ 53 , 59 ]. However, to the best of our knowledge and as per our review of the literature, no report has been published to date on the α-amylase inhibitory activity of HPC.…”

Section: Resultsmentioning

confidence: 99%

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Novel α-Amylase Inhibitor Hemi-Pyocyanin Produced by Microbial Conversion of Chitinous Discards

et al. 2022

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α-Amylase inhibitors (aAIs) have been applied for the efficient management of type 2 diabetes. The aim of this study was to search for potential aAIs produced by microbial fermentation. Among various bacterial strains, Pseudomonas aeruginosa TUN03 was found to be a potential aAI-producing strain, and shrimp heads powder (SHP) was screened as the most suitable C/N source for fermentation. P. aeruginosa TUN03 exhibited the highest aAIs productivity (3100 U/mL) in the medium containing 1.5% SHP with an initial pH of 7–7.5, and fermentation was performed at 27.5 °C for two days. Further, aAI compounds were investigated for scaled-up production in a 14 L-bioreactor system. The results revealed a high yield (4200 U/mL) in a much shorter fermentation time (12 h) compared to fermentation in flasks. Bioactivity-guided purification resulted in the isolation of one major target compound, identified as hemi-pyocyanin (HPC) via gas chromatography-mass spectrometry and nuclear magnetic resonance. Its purity was analyzed by high-performance liquid chromatography. HPC demonstrated potent α-amylase inhibitory activity comparable to that of acarbose, a commercial antidiabetic drug. Notably, HPC was determined as a new aAI. The docking study indicated that HPC inhibits α-amylase by binding to amino acid Arg421 at the biding site on enzyme α-amylase with good binding energy (−9.3 kcal/mol) and creating two linkages of H-acceptors.

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Section: Resultssupporting

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Novel α-Amylase Inhibitor Hemi-Pyocyanin Produced by Microbial Conversion of Chitinous Discards

et al. 2022

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“…1-Hydroxyphenazine together with cereusitin was also produced, as the main metabolite, from a strain P. aeruginosa 2016NX1, isolated from the root of Millettia specisoa . 1-Hydroxyphenazine strongly inhibited the growth of several common plant-pathogenic fungi and bacteria such as Cochliobolus miyabeanus , Diaporthe citri , Salmonella sp., and Klebsiella oxytoca, and its potential as a biocontrol agent was evaluated [ 36 ]. Instead, 2-hydrophenazine ( 4 ) as reported above exhibited only slight antifungal activity.…”

Section: Resultsmentioning

confidence: 99%

Pseudomonas fluorescens Showing Antifungal Activity against Macrophomina phaseolina, a Severe Pathogenic Fungus of Soybean, Produces Phenazine as the Main Active Metabolite

Castaldi

Masi²,

Sautua

et al. 2021

Biomolecules

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Pseudomonas fluorescens 9 and Bacillus subtilis 54, proposed as biofungicides to control Macrophomina phaseolina, a dangerous pathogen of soybean and other crops, were grown in vitro to evaluate their ability to produce metabolites with antifungal activity. The aim of the manuscript was to identify the natural compounds responsible for their antifungal activity. Only the culture filtrates of P. fluorescens 9 showed strong antifungal activity against M. phaseolina. Its organic extract contained phenazine and mesaconic acid (1 and 2), whose antifungal activity was tested against M. phaseolina, as well as Cercospora nicotianae and Colletotrichum truncatum, other pathogens of soybean; however, only compound 1 exhibited activity. The antifungal activity of compound 1 was compared to phenazine-1-carboxylic acid (PCA, 3), 2-hydroxyphenazine (2-OH P, 4), and various semisynthetic phenazine nitro derivatives in order to perform a structure–activity relationship (SAR) study. PCA and phenazine exhibited the same percentage of growth inhibition in M. phaseolina and C. truncatum, whereas PCA (3) showed lower activity against C. nicotianae than phenazine. 2-Hydroxyphenazine (4) showed no antifungal activity against M. phaseolina. The results of the SAR study showed that electron attractor (COOH and NO2) or repulsor (OH) groups significantly affect the antifungal growth, as well as their α- or β-location on the phenazine ring. Both PCA and phenazine could be proposed as biopesticides to control the soybean pathogens M. phaseolina, C. nicotianae, and C. truncatum, and these results should prompt an investigation of their large-scale production and their suitable formulation for greenhouse and field applications.

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“…Moreover, WGS analysis showed that strain YY322 contains phzABDEFGIMRS genes, which prove it can produce phenazines with obvious antifungal effects. Liu's study demonstrated that 1-hydroxyphenazine from P. aeruginosa could strongly inhibit the growth of plant pathogenic fungi and bacteria [28]. In addition, strain YY322 could endow host plants with resistance to pathogens, as HCN (hcnABC), surfactin (srfAA), and salicylate (pchA) genes were found in its genome [29,30].…”

Section: Discussionmentioning

confidence: 99%

In Vitro Study of Biocontrol Potential of Rhizospheric Pseudomonas aeruginosa against Pathogenic Fungi of Saffron (Crocus sativus L.)

Wang

Sun

et al. 2021

Pathogens

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Plant rhizosphere soil contains a large number of plant-growth promoting rhizobacteria, which can not only resist the invasion of pathogenic microorganisms and protect plants from damage, but also promote the growth and development of plants. In this study, Pseudomonas aeruginosa strain YY322, isolated and screened from the rhizosphere soil of saffron (Crocus sativus L.), was found through a plate confrontation experiment to show highly effectual and obvious antagonistic activity against the pathogens of saffron, including Fusarium oxysporum, Fusarium solani, Penicillium citreosulfuratum, Penicillium citrinum and Stromatinia gladioli. In addition, the volatile organic compounds of strain YY322 had great antagonistic activity against these pathogens. Observation under a scanning electron microscope and transmission electron microscope reflected that strain YY322 had a significant effect on the hyphae and conidia of F. oxysporum and F. solani. Through the detection of degrading enzymes, it was found that P. aeruginosa can secrete protease and glucanase. The plant growth promoting performance was evaluated, finding that strain YY322 had the functions of dissolving phosphorus, fixing nitrogen, producing siderophore and producing NH3. In addition, whole genome sequencing analysis indicated that the YY322 genome is comprised of a 6,382,345-bp circular chromosome, containing 5809 protein-coding genes and 151 RNA genes. The P. aeruginosa YY322 genome encodes genes related to phenazine (phzABDEFGIMRS), hydrogen cyanide(HCN) (hcnABC), surfactin (srfAA), salicylate (pchA), biofilm formation (flgBCDEFGHIJKL, motAB, efp, hfq), and colonization (minCDE, yjbB, lysC). These results collectively indicated the role of P. aeruginosa YY322 in plant growth enhancement and biocontrol mechanisms. All in all, this study provides a theoretical basis for P. aeruginosa as the PGPR of saffron, paving the way for the subsequent development and utilization of microbial fertilizer.

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Isolation and identification of bioactive substance 1‐hydroxyphenazine from Pseudomonas aeruginosa and its antimicrobial activity

Cited by 19 publications

References 31 publications

Novel α-Amylase Inhibitor Hemi-Pyocyanin Produced by Microbial Conversion of Chitinous Discards

Novel α-Amylase Inhibitor Hemi-Pyocyanin Produced by Microbial Conversion of Chitinous Discards

Pseudomonas fluorescens Showing Antifungal Activity against Macrophomina phaseolina, a Severe Pathogenic Fungus of Soybean, Produces Phenazine as the Main Active Metabolite

In Vitro Study of Biocontrol Potential of Rhizospheric Pseudomonas aeruginosa against Pathogenic Fungi of Saffron (Crocus sativus L.)

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