Degradation of 2,5-dimethylpyrazine by Rhodococcus erythropolis strain DP-45 isolated from a waste gas treatment plant of a fishmeal processing company
Tóm tắt
A bacterium, strain DP-45, capable of degrading 2,5-dimethylpyrazine (2,5-DMP) was isolated and identified as Rhodococcus erythropolis. The strain also grew on many other pyrazines found in the waste gases of food industries, like 2,3-dimethylpyrazine (2,3-DMP), 2,6-dimethylpyrazine (2,6-DMP), 2-ethyl-5(6)-dimethylpyrazine (EMP), 2-ethylpyrazine (EP), 2-methylpyrazine (MP), and 2,3,5-trimethylpyrazine (TMP). The strain utilized 2,5-DMP as sole source of carbon and nitrogen and grew optimally at 25°C with a doubling time of 7.6 h. The degradation of 2,5-DMP was accompanied by the growth of the strain and by the accumulation of a first intermediate, identified as 2-hydroxy-3,6-dimethylpyrazine (HDMP). The disappearance of HDMP was accompanied by the release of ammonium into the medium. No other metabolite was detected. The degradation of 2,5-DMP and HDMP by strain DP-45 required molecular oxygen. The expression of the first enzyme in the pathway was induced by 2,5-DMP and HDMP whereas the second enzyme was constitutively expressed. The activity of the first enzyme was inhibited by diphenyliodonium (DPI), a flavoprotein inhibitor, methimazole, a competitive inhibitor of flavin-containing monooxygenases, and by cytochrome P450 inhibitors, 1-aminobenzotriazole (ABT) and phenylhydrazine (PHZ). The activity of the second enzyme was inhibited by DPI, ABT, and PHZ. Sodium tungstate, a specific antagonist of molybdate, had no influence on growth and consumption of 2,5-DMP by strain DP-45. These results led us to propose that a flavin-dependent monooxygenase or a cytochrome P450-dependent monooxygenase rather than a molybdenum hydroxylase catalyzed the initial hydroxylation step and that a cytochrome P450 enzyme is responsible for the transformation of HDMP in the second step.
Tài liệu tham khảo
Arthurs CE, Lloyd D (1999) Kinetics, stereospecificity, and expression of the malolactic enzyme. Appl Environ Microbiol 65:3360–3363
Baker R, Saunders J, Street LJ (1989) Pyrazines, pyrimidines and pyridazines useful in the treatment of senile dementia. European Patent Appl 0327155
Besson I, Creuly C, Gros JB, Larroche C (1997) Pyrazine production by Bacillus subtilis in solid-state fermentation on soybeans. Appl Microbiol Biotechnol 47:489–495
Bhushan B, Trott S, Spain JC, Halasz A, Paquet L, Hawari J (2003) Biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by a rabbit liver cytochrome P450: Insight into the mechanism of RDX biodegradation by Rhodococcus sp. strain DN22. Appl Environ Microbiol 69:1347–1351
Brown DJ (2002) The pyrazines supplement I. John Willey & Sons Inc., New York
Bruce J (1996) Automated system rapidly identifies and characterizes microorganisms in food. Food Technol 50:77–81
de Wever H, Vereecken K, Stolz A, Veractert H (1998) Initial transformations in the biodegradation of benzothiazoles by Rhodococcus isolates. Appl Environ Microbiol 64:3270–3274
Fetzner S (1998) Bacterial degradation of pyridine, indole, quinoline, and their derivatives under different redox conditions. Appl Microbiol Biotechnol 49:237–250
Fetzner S (2000) Enzymes involved in the aerobic bacterial degradation of N-heteroaromatic compounds: molybdenum hydroxylase and ring-opening 2,4-dioxygenases. Naturwissenschften 87:59–69
Fetzner S (2002) Oxygenases without requirement for cofactors or metal ions. Appl Microbiol Biotechnol 60:243–257
Goodfellow M (1989) Genus Rhodococcus Zopf 1891. In: Holt JG (ed.) Bergey’s manual of systematic bacteriology 4. Williams & Wilkinson. Baltimore, pp. 2362–2371
Kaiser JP, Feng Y, Bollag JM (1996) Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions. Microbial Rev 60:483–498
Kämpfer P, Dott W, Kroppenstedt RM (1990) Numerical classification and identification of some nocardioform bacteria. J Gen Microbiol 36:309–331
Kiener A (1992) Enzymatic oxidation of methyl groups on aromatic heterocycles: a versatile method for the preparation of heteroaromatic carboxylic acids. Angew Chem Int Ed Engl 31:774–775
Kiener A, Van Gameren Y, Bokel M (1993) Microbiological process for the production of hydroxylated heterocycles. US Patent 5229278
Kiener A, Van Gameren Y, Bokel M (1994) Microorganisms useful for the production of hydroxylated heterocycles. US Patent 5284767
Kim ND, Kwak MK, Kim SG (1997) Inhibition of cytochrome P450 2E1 expression by 2-(allylthio)pyrazine, a potential chemoprotective agent: hepatoprotective effects. Biochem Pharmacol 53:261–269
Klatte S, Jahnke KD, Kroppenstedt RM, Rainey F, Stackebrandt E (1994) Rhodococcus luteus is a later subjective synonym of Rhodococcus fascians. Int J Syst Bacteriol 44:627–630
Krivobok S, Kuony S, Meyer C, Louwaie M, Willison JC, Jouanneau Y (2003) Identification of pyrene-induced protein in Mycobacterium sp. Strain 6PY1: evidence for two ring-hydroxylation dioxygenases. J Bacteriol 185:3828–3841
Maarse H (1991) Volatile compounds in food and beverages. Marcel Dekker Inc., New York, USA
MacDonald JC (1973) Toxicity, analyses, and production of aspergillic acid and its analogues. Can J Biochem 51:1311–1315
Maidak BL, Cole JR, Parker Jr CT, Garrity GM, Larsen N, Li B, Lilburn TG, McCaughey MJ, Olsen GJ, Overveek R, Pramanik S, Smidt TM, Tiedje JM, Woese CR (1999) A new version of the R2,5-DP (Ribosomal Database Project). Nucleic Acids Res 27:171–173
Mattey M, Harle EM (1976) Aerobic metabolism of pyrazine compounds by a Pseudomonas species. Biochem Soc Trans 4:492–494
Miller L, Berger T (1985) Bacterial identification by gas chromatography of whole cell fatty acids. Hewlett-Packard Gas chromatography Application note 228–241, Hewlett-Packard Co., Avondale, PA, California, pp. 1–8
Nagorny S, Francke W (2005) Identification, structure elucidation, and synthesis of volatile compounds in the exhaust gas of food factories. Waste Manage 25:880–886
Ohta A, Akita Y, Hara M (1979) Syntheses and reactions of some 2,5-disubstituted pyrazine monoxides. Chem Pharm Bull 27:2027–2041
Poupin P, Truffaut N, Combourieu B, Besse P, Sancelme M, Veschambre H, Delort AM (1998) Degradation of morpholine by an environmental Mycobacterium strain involves a cytochrome P-450. Appl Environ Microbiol 64:159–165
Rainey FA, Ward-Rainey N, Kroppenstedt RM, Stackenbrandt E (1996) The genus Nocardiopolis represents a phylogenetically coherent taxon and a distinct actinomycete lineage; proposal of Nocardiopsaceae fam. Nov. Int J Syst Bacteriol 46:1088–1092
Ranau R, Steinhart H (2004) Bewertung und Quantifizierung von Leitsubstanzen aus der geruchstragenden Abluft von Lebensmittelbetrieben und der Ferkelaufzucht. Erfassung und Minimierung von Gerüchen. In: Niemeyer B, Robers A, Thiesen P (eds) Messung und Minimierung von Gerüchen, Hamburger Berichte 23. Verlag Abfall aktuell, Stuttgart, Germany, pp. 147–165
Ranau R, Kleeberg KK, Schlegelmilch M, Streese J, Stegmann R, Steinhart H (2005) Analytical determination of the suitability of different processes for the treatment of odorous waste gas. Waste Manage 25:908–916
Rappert S, Ayoub R, Li R, Botsch K, Obi I, Müller R (2004) Biologischer Abbau von geruchsaktiven Einzelstoffen und von realen Vielstoffgemischen. Erfassung und Minimierung von Gerüchen. In: Niemeyer B, Robers A, Thiesen P (eds) Messung und Minimierung von Gerüchen, Hamburger Berichte 23. Verlag Abfall aktuell, Stuttgart, Germany, pp. 203–220
Rappert S, Müller R (2005a) Odor compounds in waste gas emissions from agricultural operations and food industries. Waste Manage 25:887–907
Rappert S, Müller R (2005b) Microbial degradation of selected odorous substances. Waste Manage 25:940–954
Rappert S, Botsch KC, Nagorny S, Francke W, Müller R (2006) Degradation of 2,3-diethyl-5-methylpyrazine by a newly discovered bacterium Mycobacterium sp. strain DM-11. Appl Environ Microbiol 72:1437–1444
Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Industrial biocatalysis today and tomorrow. Nature 409:258–268
Schräder T, Schuffenhauer G, Sielaff B, Andreesen JR (2000) High morpholine degradation rates and formation of cytochrome P450 during growth on different cyclic amines by newly isolated Mycobacterium sp. strain HE5. Microbiology 146:1091–1098
Shiemke AK, Arp DJ, Sayavedra-Soto LA (2004) Inhibition of membrane-bound methane monooxygenase and ammonia monooxygenase by diphenyliodonium: Implications for electron transfer. J Bacteriol 186:928–937
Siegmund I, Koenig K, Andreesen R (1990) Molybdenum involvement in aerobic degradation of picolinic acid by Arthrobacter picolinophilus. FEMS Microbiol Lett. 67:281–284
Sielaff B, Andreesen JR, Schräder T (2001) A cytochrome P450 and a ferredoxin isolated from Mycobacterium sp. strain HE5 after growth on morpholine. Appl Microbiol Biotechnol 56:458–464
Stephan I, Tshisuaka B, Fetzner S, Lingens F (1996) Quinaldine 4-oxidase from Arthrobacter sp. Rü61a, a versatile prokaryotic molybdenum-containing hydroxylase active towards N-containing heterocyclic compounds and aromatic aldehydes. Eur J Biochem 236:155–162
Street LJ, Baker R, Book T, Reeve AJ, Saunders J, Willson T, Marwood RS, Patel S, Freedman SB (1992) Synthesis and muscarinic activity of quinuclidinyl- and (1-azanorbornyl) pyrazine derivatives. J Med Chem 35:295–305
Tinschert A, Kiener A, Heizmann K, Tschech A (1997) Isolation of new 6-methylnicotinic-acid-degrading bacteria, one of which catalyses the regioselective hydroxylation of nicotinic acid at position C2. Arch Microbiol 168:355–361
Tinschert A, Tschech A, Heinzmann K, Kiener A (2000) Novel regioselective hydroxylations of pyridine carboxylic acids at position C2 and pyrazine carboxylic acids at position C3. Appl Microbiol Biotechnol 53:185–195
Tomasi I, Artaud I, Bertheau Y, Mansuy D (1995) Metabolism of polychlorinated phenols by Pseudomonas cepacia AC1100: determination of the first two steps and specific inhibitory effect of methimazole. J Bacteriol 177:307–311
Uchida A, Ogawa M, Yoshida T, Nagasawa T (2003) Quinolinate dehydrogenase and 6-hydroxyquinolinate decarboxylase involved in the conversion of quinolinic acid to 6-hydroxypicolinic acid by Alcaligenes sp. strain UK21. Arch Microbiol 180:81–87
Van Scoy RE, Wilkowske CJ (1992) Antituberculous agents. Mayo Clin Proc 67:179–187
Van Zyl C, Prior BA, Kilian SG, Brant EV (1993) Role of d-ribose as a cometabolite in d-xylose metabolism by Saccharomyces cerevisiae. Appl Environ Microbiol 59:1487–1494
Wieser M, Heinzmann K, Kiener A (1997) Bioconversion of 2-cyanopyrazine to 5-hydroxypyrazine-2-carboxylic acid with Agrobacterium sp. DSM 6336. Appl Microbiol Biotechnol 48:174–176