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Biotransformation of Citrinin to Decarboxycitrinin Using an Organic Solvent-Tolerant Marine Bacterium, Moraxella sp. MB1

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Abstract

Organic solvent tolerant microorganisms (OSTMs) are novel group of extremophilic microorganisms that have developed resistance to withstand solvent toxicity. These organisms play an important role in biotransformation of organic compounds. In the present study, we used an organic solvent-tolerant marine bacterium, Moraxella sp. MB1. 16S rRNA sequencing revealed that the bacterium shows 98% similarity with an uncultured marine bacterium with GenBank accession no. AY936933. This bacterium was used for the transformation of a toxin, citrinin, into decarboxycitrinin in a biphasic system. This transformation was affected by decarboxylase enzyme produced by MB1. Transformation of citrinin to decarboxycitrinin was monitored by thin-layer chromatography (TLC) and spectrophotometrically. Citrinin decarboxylase activity responsible for transformation was studied in cell-free growth medium and cell lysate of Moraxella sp. MB1. Citrinin decarboxylase was found to be intracellular in nature. The biotransformed product was purified and identified as decarboxycitrinin using electrospray ionization mass spectrometry (ESI-MS/MS) and nuclear magnetic resonance (NMR) spectrometry. The antibiotic activity of both citrinin and decarboxycitrinin is also reported.

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References

  • A Abe I Inove R Usami K Moriya K Horikoshi (1995) ArticleTitleProperties of newly isolated polyaromatic hydrocarbons marine bacterium that can degrade in the presenceof organic solvents J Mar Biotechnol 2 182–186

    Google Scholar 

  • R Aono M Ito A Inoue K Horkoshi (1992) ArticleTitleIsolation of novel toluene tolerant strain of Pseudomonas aeruginosa Biosci Biotechnol Biochem 56 145–146

    Google Scholar 

  • R Aono N Doukyu H Kobayashi H Nakajima K Horikoshi (1994) ArticleTitleOxidative bioconversion of cholesterol by Pseudomonas sp. strain ST-200 in a water-organic solvent two-phase system Appl Environ Microbiol 60 2518–2523

    Google Scholar 

  • KS Bilgrami SP Sinha P Jewal (1998) ArticleTitleNephrotoxic and hepatoxic effects of citrinin in mice (Mus musculus) Proc Indian Natl Sci Acad B 54 35–37

    Google Scholar 

  • JAM Bont (1998) ArticleTitleSolvent tolerant bacteria in biocatalysis Trends Biotechnol 16 493–499

    Google Scholar 

  • M Chandrasekaran (1997) ArticleTitleIndustrial enzymes from marine microorganisms: the Indian scenario J Mar Biotechnol 5 86–89

    Google Scholar 

  • L Cornec J Robineau JL Rolland J Dietrich G Barbier (1998) ArticleTitleThermostable esterases screened on hyperthermophilic archaeal and bacterial strains isolated from deep-sea hydrothermal vents: characterization of esterase activity of a hydrothermophilic archaeum, Pyrococcus abyssi J Mar Biotechnol 6 104–110

    Google Scholar 

  • DL Cruden JH Wolfram RD Rogers DT Gibson (1992) ArticleTitlePhysiological properties of a Pseudomonas strain which grows with p-xylene in a two-phase (organic-aqueous) medium Appl Environ Microbial 58 2723–2729

    Google Scholar 

  • RF Curtis CH Hassall M Nazar (1968) ArticleTitleThe biosynthesis of phenols. XV. Some metabolites of Penicillium citrinum related to citrinin J Chem Soc 1 85–93

    Google Scholar 

  • N Doukyu R Aono (1998) ArticleTitlePurification of extracellular cholesterol oxidase with high activity in the presence of organic solvents from Pseudomonas sp. strain ST-200 Appl Environ Microbiol 64 1929–1932

    Google Scholar 

  • U Hentschel M Schmid M Wagner L Fieseler C Gernert J Hacker (2001) ArticleTitleIsolation and phylogenetic analysis of bacteria with antibacterial activities from the Mediterranean sponges Aplysina aerophoba and Aplysina cavernicola FEMS Microbiol Ecol 35 305–312

    Google Scholar 

  • AC Hetherington H Raistrick (1931) ArticleTitleStudies in the biochemistry of micro-organisms. XI. On the production and chemical constitution of a new yellow coloring matter, citrinin, produced from glucose by Penicillium citrinum Thom Philos Trans R Soc Lond B 220 267–297

    Google Scholar 

  • A Inoue K Horikoshi (1989) ArticleTitlePseudomonas thrives in high concentrations of toluene Nature (Lond) 338 264–266

    Google Scholar 

  • IY Lee TG Volm JPN Rosazza (1998) ArticleTitleDecarboxylation of ferulic acid to 4-vinylguaiacol by Bacillus pumilus in aqueous-organic solvent two-phase systems Enzyme Microbiol Technol 23 261–266

    Google Scholar 

  • S Isken A Derks PFG Wolffs JAM Bont Particlede (1999) ArticleTitleEffects of organic solvents on the yield of solvent-tolerant Pseudomonas putida S12 Appl Environ Microbiol 65 2631–2635

    Google Scholar 

  • LK Jackson A Ciegler (1978) ArticleTitleProduction and analysis of citrinin in corn Appl Environ Microbiol 36 408–411

    Google Scholar 

  • K Moriya S Yanigitani R Usami K Horikoshi (1995) ArticleTitleIsolation and some properties of an organic-solvent-tolerant marine bacterium degrading cholesterol J Mar Biotechnol 2 131–133

    Google Scholar 

  • H Nakajima H Kobayashi R Aono K Horikoshi (1992) ArticleTitleEffective isolation and identification of toluene-tolerant Pseudomonas strains Biosci Biotechnol Biochem 56 1872–1873

    Google Scholar 

  • H Ogino K Miyamoto H Ishikawa (1994) ArticleTitleOrganic solvent-tolerant bacterium which secretes organic solvent-stable lipolytic enzymes Appl Environ Microbial 60 3884–3886

    Google Scholar 

  • H Ogino K Yasui T Shiotani T Ishiwara H Ishikawa (1995) ArticleTitleOrganic solvent tolerant bacteria which secretes an organic solvent stable proteolytic enzyme Appl Environ Microbiol 61 4258–4262

    Google Scholar 

  • H Ogino T Uchiho J Yokoo R Kobayashi R Ichise H Ishikawa (2001) ArticleTitleRole of intermolecular disulfide bonds of the organic solvent-stable PST-01 protease in its organic solvent stability Appl Environ Microbiol 67 942–947 Occurrence Handle10.1128/AEM.67.2.942-947.2001

    Article  Google Scholar 

  • RN Patel (2000) Stereoselective biocatalysis for synthesis of some chiral pharmaceutical intermediates RN Patel (Eds) Stereoselective Biocatalysis Marcel Dekker New York 87–130

    Google Scholar 

  • U Sankawa Y Ebizuka H Noguchi Y Isikawa S Kitaghawa Y Yamamoto T Kobayashi Y Iitak (1983) ArticleTitleBiosynthesis of citrinin in Aspergillus terreus Tetrahedron 39 3583–3591 Occurrence Handle10.1016/S0040-4020(01)88669-5

    Article  Google Scholar 

  • Y Sardessai S Bhosle (2003) ArticleTitleIsolation of an organic-solvent-tolerant cholesterol-transforming Bacillus species, BC1, from coastal sediment Mar Biotechnol 5 116–118

    Google Scholar 

  • B Schulze MG Wubbolts (1999) ArticleTitleBiocatalysis for industrial production of fine chemicals Curr Opin Biotechnol 10 609–615 Occurrence Handle10.1016/S0958-1669(99)00042-7

    Article  Google Scholar 

  • NL Thakur AC Anil WEG Muller (2004) ArticleTitleCulturable epibacteria of the marine sponge Ircinia fusca: temporal variations and their possible role in the epibacterial defense of the host Aquat Microb Ecol 37 295–304

    Google Scholar 

  • OP Ward A Singh (2000) ArticleTitleEnzymatic asymmetric synthesis by decarboxylases Curr Opin Biotechnol 11 520–526 Occurrence Handle10.1016/S0958-1669(00)00139-7

    Article  Google Scholar 

  • FJ Weber LP Ooijkaas RMW Schemen S Hartmans JAM Bont (1993) ArticleTitleAdaptations of Pseudomonas putida S12 to high concentrations of styrene and other organic solvents Appl Environ Microbiol 59 3502–3504

    Google Scholar 

  • FJ Weber S Isken JAM Bont (1994) ArticleTitleCis/trans isomerization of fatty acids as a defence mechanism of Pseudomonas putida strains to toxic concentrations of toluene Microbiology 140 2013–2017

    Google Scholar 

Download references

Acknowledgments

The authors are grateful to Dr. S. R. Shetye, Director, NIO, for constant encouragement. The authors also wish to thank Dr. N.B. Bhosle (Scientist, NIO), Dr. C. Raghukumar (Scientist, NIO), and Irene Furtado (Reader, Goa University) for their valuable suggestions and guidance. Thanks are also extended to Dr. Loka Bharathi (Scientist, NIO) for identifying the bacterial culture and Dr. N. Thakur (Scientist, NPRC, Mumbai) for providing the 16S rRNA data. C.R. is grateful to DOD for the fellowship award and P.D. is particularly indebted to the Council of Scientific and Industrial Research (CSIR), New Delhi, for a Research Associateship award. Sincere thanks are expressed to the dean, Goa Medical College, for providing the clinical pathogens. This manuscript has NIO contribution no. 4059.

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  1. Chemical Oceanography Division, National Institute of Oceanography, Dona Paula, Goa, 403 004, India

    Prabha Devi, Chandrakant Govind Naik & Celina Rodrigues

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  1. Prabha Devi
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  2. Chandrakant Govind Naik
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  3. Celina Rodrigues
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Correspondence to Prabha Devi.

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Devi, P., Naik, C.G. & Rodrigues, C. Biotransformation of Citrinin to Decarboxycitrinin Using an Organic Solvent-Tolerant Marine Bacterium, Moraxella sp. MB1. Mar Biotechnol 8, 129–138 (2006). https://doi.org/10.1007/s10126-005-5021-5

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