Identification of nicotine biotransformation intermediates by Agrobacterium tumefaciens strain S33 suggests a novel nicotine degradation pathway

Applied Microbiology and Biotechnology

Volumn 95, Issue 6, 2012, Pages 1567-1578

  Wang, Shuning ^a   Huang, Haiyan ^b   Xie, Kebo ^a   Xu, Ping ^a  

^a SHANDONG UNIVERSITY   (China)

^b BEIJING HOSPITAL   (China)

Author keywords

Agrobacterium tumefaciens; Biodegradation; Biotransformation; Functionalized pyridine; Intermediate; Nicotine; Pathway

Indexed keywords

AGROBACTERIUM TUMEFACIENS; BIOTRANSFORMATION; FUNCTIONALIZED PYRIDINES; INTERMEDIATE; PATHWAY;

BACTERIA; BIODEGRADATION; HYDROXYLATION; PYRIDINE; TOBACCO;

NICOTINE;

2,5 DIHYDROXYPYRIDINE; 6 HYDROXY 3 SUCCINOYLPYRIDINE; 6 HYDROXY LEVO NICOTINE; NICOTINE; NICOTINE DERIVATIVE; OXYGENASE; PYRIDINE; UNCLASSIFIED DRUG; ALKANONE; BACTERIAL PROTEIN; DRUG DERIVATIVE; PSEUDOOXYNICOTINE;

BIOTRANSFORMATION; ENZYME ACTIVITY; GROWTH RATE; INSECTICIDE; MICROBIAL ACTIVITY; REACTION RATE; TOBACCO; TOXIC MATERIAL;

ARTHROBACTER; ARTICLE; BACTERIAL CELL; BACTERIAL GROWTH; BACTERIAL STRAIN; BIOTRANSFORMATION; DEGRADATION; ENZYME ACTIVITY; MASS FRAGMENTOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; OXIDATION; PSEUDOMONAS; RHIZOBIUM RADIOBACTER; BIOREMEDIATION; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; GROWTH, DEVELOPMENT AND AGING; METABOLISM;

AGROBACTERIUM TUMEFACIENS; ARTHROBACTER; NICOTIANA OBTUSIFOLIA; NICOTIANA TABACUM; PSEUDOMONAS;

AGROBACTERIUM TUMEFACIENS; BACTERIAL PROTEINS; BIODEGRADATION, ENVIRONMENTAL; BIOTRANSFORMATION; BUTANONES; MOLECULAR STRUCTURE; NICOTINE;

EID: 84872042028     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-012-4007-2     Document Type: Article

References (36)

1. Baitsch D, Sandu C, Brandsch R, Igloi GL (2001) Gene cluster on pAO1 of Arthrobacter nicotinovorans involved in degradation of the plant alkaloid nicotine: cloning, purification, and characterization of 2,6-dihydroxypyridine 3-hydroxylase. J Bacteriol 183:5262-5267
2. Brandsch R (2006) Microbiology and biochemistry of nicotine degradation. Appl Microbiol Biotechnol 69:493-498
3. Brühmüller M, Möhler H, Decker K (1972) Covalently bound flavin in d-6-hydroxynicotine oxidase from Arthrobacter oxidans. Purification and properties of d-6-hydroxynicotine oxidase. Eur J Biochem 29:143-151
4. Bush L, Hempfling WP, Burton H (1999) Biosynthesis of nicotine and related compounds. In: Gorrod JW, Jacob PIII (eds) Analytical determination of nicotine and related compounds and their metabolites. Elsevier, Amsterdam
5. Campain JA (2004) Nicotine: potentially a multifunctional carcinogen? Toxicol Sci 79:1-3
6. Civilini M, Domenis C, Sebastianutto N, de Berfoldi M (1997) Nicotine decontamination of tobacco agro-industrial waste and its degradation by micro-organisms. Waste Manage Res 15:349-358
7. Crooks PA, Pool WF (1988) N-methyl-N′-oxonicotinium ion: synthesis and stereochemistry. Chem Ind 1:95-96
8. Decker K, Bleeg H (1965) Induction and purification of steteospecific nicotine oxidizing enzymes from Arthrobacter oxidans. Biochim Biophys Acta 105:313-324
9. Díaz E, Ferrández A, Prieto MA, García JL (2001) Biodegradation of aromatic compounds by Escherichia coli. Microbiol Mol Biol Rev 65:523-569
10. Freudenberg W, König K, Andreesen JR (1988) Nicotine dehydrogenase from Arthrobacter oxidans: a molybdenum-containing hydroxylase. FEMS Microbiol Lett 52:13-18
11. Gherna RL, Richardson SH, Rittenberg SC (1965) The bacterial oxidation of nicotine. VI. The metabolism of 2,6-dihydroxypseudooxynicotine. J Biol Chem 240:3669-3674
12. Grether-Beck S, Igloi GL, Pust S, Schilz E, Decker K, Brandsch R (1994) Structural analysis and molybdenum-dependent expression of the pAO1-encoded nicotine dehydrogenase genes of Arthrobacter nicotinovorans. Mol Microbiol 13:929-936
13. Hinkkanen A, Lilius EM, Nowack J, Maas R, Decker K (1983) Purification of the flavoproteins 6-hydroxy-d- and 6-hydroxy-L-nicotine oxidase using hydrophobic affinity chromatography. Hoppe-Seyler's Z Physiol Chem 364:801-806
14. Hochstein LI, Rittenberg SC (1959) The bacterial oxidation of nicotine. II. The isolation of the first oxidative product and its identification as (1)-6-hydroxynicotine. J Biol Chem 234:156-160
15. Holmes PE, Rittenberg SC (1972) The bacterial oxidation of nicotine. VII. Partial purification and properties of 2,6-dihydroxypyridine oxidase. J Biol Chem 247:7622-7627
16. Kagarlitskii AD, Iskakova MK, Turmukhambetov AZh (2002) Catalytic conversion of nicotine into nicotinonitrile - a pharmaceutical intermediate product. Pharma Chem J 36:26-27
17. Kaiser JP, Feng Y, Bollag JM (1996) Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions. Microbiol Rev 60:483-498
18. Li H, Li X, Duan Y, Zhang KQ, Yang J (2010) Biotransformation of nicotine by microorganism: the case of Pseudomonas spp. Appl Microbiol Biotechnol 86:11-17
19. Nakano H, Wieser M, Hurh B, Kawai T, Yoshida T, Yamane T, Nagasawa T (1999) Purification, characterization and gene cloning of 6-hydroxynicotinate 3-monooxygenase from Pseudomonas fluorescens TN5. Eur J Biochem 260:120-126
20. Novotny TE, Zhao F (1999) Consumption and production waste: another externality of tobacco use. Tob Control 8:5-80
21. Ondachi PW, Comins DL (2010) Synthesis of fused-ring nicotine derivatives from (S)-nicotine. J Org Chem 75:1706-1716
22. Piotrowska-Cyplik A, Olejnik A, Cyplik P, Dach J, Czarnecki Z (2009) The kinetics of nicotine degradation, enzyme activities and genotoxic potential in the characterization of tobacco waste composting. Bioresour Technol 100:5037-5044
23. Roduit JP, Wellig A, Kiener A (1997) Renewable functionalized pyridines derived from microbial metabolites of the alkaloid (S)-nicotine. Heterocycles 45:1687-1702
24. Sachelaru P, Schiltz E, Igloi GL, Brandsch R (2005) An α/β-fold C-C bond hydrolase is involved in a central step of nicotine catabolism by Arthrobacter nicotinovorans. J Bacteriol 187:8516-8519
25. Schievelbein H (1982) Nicotine, resorption and fate. Pharmacol Ther 18:233-248
26. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Industrial biocatalysis today and tomorrow. Nature 409:258-268
27. Sguros PL (1955) Microbial transformations of the tobacco alkaloids. I. Cultural and morphological characteristics of a nicotinophile. J Bacteriol 69:28-37
28. Spande TF, Garraffo HM, Edwards MW, Yeh HJC, Pannell L, Daly JW (1992) Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog. J Am Chem Soc 114:3475-3478
29. Tang HZ, Wang SN, Ma LY, Meng XZ, Deng ZX, Zhang DK, Ma CQ, Xu P (2008) A novel gene encoding 6-hydroxy-3-succinoylpyridine hydroxylase in nicotine degradation by Pseudomonas putida strain S16. Appl Environ Microbiol 74:1567-1574
30. Tang HZ, Wang LJ, Meng XZ, Ma LY, Wang SN, He XF, Wu G, Xu P (2009) A novel gene, encoding a nicotine oxidoreductase, involved in nicotine degradation by Pseudomonas putida strain S16. Appl Environ Microbiol 75:772-778
31. Wang SN, Xu P, Tang HZ, Meng J, Liu XL, Huang J, Chen H, Du Y, Blankespoor HD (2004) Biodegradation and detoxification of nicotine in tobacco solid waste by a Pseudomonas sp. Biotechnol Lett 26:1493-1496
32. Wang SN, Xu P, Tang HZ, Meng J, Liu XL, Ma CQ (2005) "Green" route to 6-hydroxy-3-succinoyl-pyridine from (S)-nicotine of tobacco waste by whole cells of a Pseudomonas sp. Environ Sci Technol 39:6877-6880
33. Wang SN, Liu Z, Tang HZ, Meng J, Xu P (2007) Characterization of environmentally friendly nicotine degradation by Pseudomonas putida biotype A strain S16. Microbiology 153:1556-1565
34. Wang SN, Liu Z, Xu P (2009) Biodegradation of nicotine by a newly isolated Agrobacterium sp. strain S33. J Appl Microbiol 107:838-847
35. Xun L, Webster CM (2004) A monooxygenase catalyzes sequential dechlorinations of 2,4,6-trichlorophenol by oxidative and hydrolytic reactions. J Biol Chem 279:6696-6700
36. Zhong W, Zhu C, Shu M, Sun K, Zhao L, Wang C, Ye Z, Chen J (2010) Degradation of nicotine in tobacco waste extract by newly isolated Pseudomonas sp. ZUTSKD. Bioresour Technol 101:6935-6941