Synthesis, Isolation of Phenazine Derivatives and Their Antimicrobial Activities

Authors

  • Aunchalee NANSATHIT Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002
  • Chanokporn PHAOSIRI Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002
  • Paweena PONGDONTRI Department of Biochemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002
  • Saksit CHANTHAI Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002
  • Chalerm RUANGVIRIYACHAI Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002

Keywords:

Phenazine-1-carboxylic acid (PCA), antimicrobial activity, phenazine-5, 10-dioxide (PDO), disc diffusion method, minimal inhibitory concentration (MIC) method

Abstract

Antimicrobial activity of natural phenazine-1-carboxylic acid (PCA) from Pseudomonas aeruginosa TISTR 781 and synthetic phenazine-5,10-dioxide (PDO), prepared by oxidation of the phenazine, were evaluated by in vitro disc diffusion and minimal inhibitory concentration (MIC) methods. The results indicated that both phenazine derivatives differed clearly in their antimicrobial activity. PCA showed better efficacy against growth of Acidovorax avenae subsp. citrulli, Bacillus subtilis, Candida albicans, Escherichia coli and Xanthomonas campestris pv. vesicatoria than PDO at low concentrations of PCA (MIC; 17.44 - 34.87 ppm) as an antimicrobial agent. In contrast, PDO acted as a stronger inhibitor than PCA when tested against Pseudomonas syringae and Enterobacter aerogenes. The last bacterial strain, Ralstonia solanacearum, can be suppressed by the same concentration of PCA and PDO (MIC; 62.50 ppm). The data provided beneficial information for choosing phenazine types to inhibit some general strains and plant pathogenic bacteria.

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References

GM Denning, SS Iyer, KJ Reszka, YO Malley, GT Rasmussen and BE Britigan. Phenazine-1-carboxylic acid, a secondary metabolite of Pseudomonas aeruginosa, alters expression of immunomodulatory proteins by human airway epithelial cells. Am. J. Physiol-Lung. C. 2003; 285, L584-L592.

R Wilson, T Pitt, G Taylor, D Watson, J MacDermot, D Sykes, D Roberts and P Cole. Pyocyanin and 1-hydroxyphenazine produced by Pseudomonas aeruginosa inhibit the beating of human respiratory cilia in vitro. J. Clin. Invest. 1987; 79, 221-9.

TFC Chin-A-Woeng, GV Bloemberg, AJ Van der Bij, KMGM Van der Drift, J Schripsema, B Kroon, RJ Scheffer, C Keel, PAHM Bakker, H Tichy, FJ De Bruijn, JE Thomas-Oates and BJJ Lugtenberg. Biocontrol by Phenazine-1-carboxamide producing Pseudomonas chlororaphis PCL 1391 of tomato root rot caused by Fusarium oxysporum f. sp. Radicis-lycopersici. Mol. Plant Microbe In. 1998; 11, 1069-77.

SM Delaney, DV Mavrodi, RF Bonsall and LS Thomashow. phzO, a gene for biosynthesis of 2-hydroxylated phenazine compounds in Pseudomonas aureofaciens 30-84. J. Bacteriol. 2001; 183, 318-27.

GS Byng, DC Eustice and RA Jensen. Biosynthesis of phenazine pigments in mutant and wild-type cultures of Pseudomonas aeruginosa. J. Bacteriol. 1979; 138, 846-52.

C Darby, CL Cosma, JH Thomas and C Manoil. Lethal paralysis of Caenorhabditis elegans by Pseudomonas aeruginosa. Proc. Natl. Acad. Sci. 1999; 96, 15202-207.

JR Kerr. Phenazine pigments: antibiotics and virulence factors. Infect. Dis. Rev. 2000; 2, 184-94.

M González, H Cerecetto and A Monge. Quinoxaline-1,4-dioxide and phenazine-5,10 dioxide: chemistry and biology. Top. Heterocycl. Chem. 2007; 11, 179-211.

S Caron, NM Do and JE Sieser. A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide–urea complex. Tetrahedron Lett. 2000; 41, 2299-302.

X Zhu, KD Kreutter, H Hu, MR Player and MD Gaul. A novel reagent combination for the oxidation of highly electron deficient pyridines to N-oxides: trifluoromethanesulfonic anhydride/sodium percarbonate. Tetrahedron Lett. 2008; 49, 832-4.

JB Laursen and J Nielsen. Phenazine natural products: Biosynthesis, synthetic analogues, and biological activity. Chem. Rev. 2004; 104, 1663-85.

DV Mavrodi, W Blankenfeldt and LS Thomashow. Phenazine compounds in fluorescent Pseudomonas spp. biosynthesis and regulation. Annu. Rev. Phytopathol. 2006; 44, 417-45.

D Dwivedi and BN Johri. Antifungals from fluorescent pseudomonads: Biosynthesis and regulation. Curr. Sci. India 2003; 85, 1693-703.

TFC Chin-A-Woeng, GV Bloemberg and BJJ Lugtenberg. Phenazines and their role in biocontrol by Pseudomonas bacteria. New Phytol. 2003; 157, 503-23.

TJ Burr, MN Schroth and T Suslow. Increased potato yields by treatment of seed pieces with specific strains of Pseudomonas fluorescens and P. putida. Phytopathol. 1978; 68, 1377-83.

TV Suslow and MN Schroth. Rhizobacteria of sugar beets: effects of seed application and root colonization on yield. Phytopathol. 1982; 72, 199-206.

FP Geels and B Schippers. Reduction of yield depressions in high frequency potato cropping soil after seed tuber treatments with antagonistic fluorescent Pseudomonas spp. Phytopathol. Z. 1983; 108, 207-14.

PG Brisbane, LJ Janik, ME Tate and RFO Warren. Revised structure for the phenazine antibiotic from Pseudomonas fluorescens 2-79 (NRRL B-15132). Antimicrob. Agents Chemo. 1987; 31, 1967-71.

KJ Kim. Phenazine 1-carboxylic acid resistance in phenazine 1-carboxylic acid producing Bacillus sp. B-6. J. Biochem. Mol. Biol. 2000; 33, 332-6.

M Oda, Y Sekizawa and T Watanabe. Phenazines as disinfectants against bacterial leaf blight of the rice plant. Appl. Microbiol. 1966; 14, 365-7.

ME Hernandez, A Kappler and DK Newman. Phenazines and other redox-active antibiotics promote microbial mineral reduction. Appl. Environ. Microbiol. 2004; 70, 921-8.

K Saosoong, S Tongtumma, S Chanthai, W Wongphathanakul, W Bunyatratchata and C Ruangviriyachai. Isolation and study of chemical properties of pyocyanin produced from Pseudomonas aeruginosa TISTR 781 (ATCC 9027). KKU Res. J. 2007; 12, 24-32.

MS Abd EI-Halim, AS EI-Ahl, HA Etman, MM Ali, A Fouda and AA Fadda. A new route for the synthesis of phenazine di-N-oxides. Monatsh. Chem. 1995; 126, 1217-23.

SA Nakai and KJ Siebert. Validation of bacterial growth inhibition models based on molecular properties of organic acids. Int. J. Food Microbiol. 2003; 86, 249-55.

RO Fernández and RA Pizarro. High-performance liquid chromatographic analysis of Pseudomonas aeruginosa phenazines. J. Chromatogr. A 1997; 771, 99-104.

VP Andreev, EG Batotsyrenova, AV Ryzhakov and LL Rodina. Intramolecular charge transfer processes in a series of styryl derivatives of pyridine and quinoline-N-oxides. Chem. Heterocycl. Comp. 1998; 34, 941-9.

H Hikoharu, O Reiichi, S Masatoshi and H Tadao. Processing of photographic silver halide light-sensitive materials. US Patent 3,642,481, 2008.

RJ Lambert and M Stratford. Weak-acid preservatives: modelling microbial inhibition and response. J. Appl. Microbiol. 1999; 86, 157-64.

R Wilson, DA Sykes, D Watson, A Rutman, GW Taylor and PJ Cole. Measurement of Pseudomonas aeruginosa phenazine pigments in sputum and assessment of their contribution to sputum sol toxicity for respiratory epithelium. Infect. Immun. 1988; 56, 2515-17.

J Nutman, M Berger, PA Chase, DG Dearborn, KM Miller, RL Waller and RU Sorensen. Studies on the mechanism of T cell inhibition by the Pseudomonas aeruginosa phenazine pigment pyocyanine. J. Immunol. 1987; 138, 3481-87.

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Published

2011-11-08

How to Cite

NANSATHIT, A., PHAOSIRI, C., PONGDONTRI, P., CHANTHAI, S., & RUANGVIRIYACHAI, C. (2011). Synthesis, Isolation of Phenazine Derivatives and Their Antimicrobial Activities. Walailak Journal of Science and Technology (WJST), 6(1), 79–91. Retrieved from https://wjst.wu.ac.th/index.php/wjst/article/view/74

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Research Article