The Biological Degradation of Nicotine by Nicotinophilic Microorganisms

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Abstract

Various microorganisms are capable of breaking down tobacco alkaloids by different biochemical processes and possess characteristic enzymatic systems for the catabolism of nicotine. Bacteria of the genus Pseudomonas and the fungus Cunninghamellaechinulata degrade nicotine via N-methylmyosmine and pseudooxynicotine which is linked to the opening of the pyrrolidine ring (pyrrolidine pathway), whereas Arthrobacteroxidanshydroxylates the pyridine ring in the 6-position. 6-hydroxynicotine is produced as a primary product (pyridine pathway). Tobacco plants, and some fungi (e.g. Pelliculariafilamentosa) degrade nicotine via demethylation to nornicotine (methyl pathway). As a result of the microbial degradation of nicotine and other tobacco alkaloids, carbon and nitrogen are made bioavailable. Following metabolic conversion to carboxylic acids, the reaction products are used by unicellular organisms as primary nutrients and a source of energy for the synthesis of new cell compounds.

1. Barz, W., Kettner, M. and W. Hiisemann: On the degradation of nicotine in Nicotiana cell suspension cultures; Planta medica 34 (1978) 73-78.

2. Bernauer, H., Mauch, L. and R. Brandsch: Interaction of the regulatory protein Nic R 1 with the promoter region of the pAOl-encoded 6-hydroxy-D-nicotine oxidase gene of Artbrobacter oxidant; Molecular Microbiology 6 (1992) 1809 -1820.

3. Brandsch, R. and V. Bichler: Riboflavin-dependent expression of flavoenzymes of the nicotine regulon of Artbrobacter oxidant; Biochem. J. 270 (1990) 673 -678.

4. Brandsch, R., Bichler, V., Mauch, L. and K. Decker: Cysteine to serine replacements in 6-hydroxy-D-nicotine oxidase; The Journal of Biological Chemistry 268 (1993) 12724-12729.

5. Brandsch, R., Bichler, V. and H. Nagursky: Covalent flavinylation of 6-hydroxy-D-nicotine oxidase by partial deletions of the gene; Eur. J. Biochem. 165 (1987) 559-564.

6. Brandsch, R., Bichler, V., Schmidt, M. and J. Buchner: Gro E dependence of refolding and holoenzyme formation of 6-hydroxy-D-nicotine oxidase; The Journal of Biological Chemistry 267 (1992) 20844-20849.

7. Brandsch, R. and K. Decker: The effect of gyrase inhibitors and cyclic AMP on induction and glucose repression of the 6-hydroxy-nicotine oxidases tn Ar-throbacter oxidant; Arch. Microbiol. 133 (1982) 274-277.

8. Brandsch, R. and K. Decker: Isolation and partial characterization of plasmid DNA from Artbrobacter oxidant; Arch. Microbiol. 138 (1984) 15-17.

9. Brandsch, R., Faller, W. and K. Schneider: Plasmid pAO1 of Artbrobacter oxidans encodes 6-hydroxy-D-nicotine oxidase: cloning and expression of the gene in Escherichia coli; Mol. Gen. Genet. 202 (1986) 96-101.

10. Brandsch, R., Hinkkanen, A.E. and K. Decker: Plasm id-mediated nicotine degradation in Ar-throbacter oxidant; Arch. Microbiol. 132 (1982) 26-30.

11. Brandsch, R., Hinkkanen, A.E., Mauch, L., Nagursky, H. and K. Decken 6-Hydroxy-D-nicotine oxidase of Artbrobacter oxidans. Gene structure of the flavoenzyme and its relationship to 6-hydroxy-L-nicotine oxidase; Eur, J. Biochem. 167 (1987) 315-320.

12. Bucherer, H.: Über den mikrobiellen Abbau von Giftstoffen. I, Mitteilung: Über den mikrobiellen Abbau von Nikotin; Zbl. Bakteriologie 105 (1942) 166-173

13. Coussirat, J.-C.: Influence of tobacco epiphytic bacteria on biodegradation and production of alkaloids; A. du Tabac, Sect. 2, 15 (1978) 5-134.

14. Decker, K. and H. Bleeg: Induction and purification of sterospecific nicotine oxidizing enzymes from Artbrobacter oxidans; Biochimica et Biophysica Acta 105 (1965) 313-324.

15. Decker, K. and R. Brandsch: Flavoproteins with a covalent histidyl (N3)-8L-riboflavin linkage; Bio Factors 3 (1991) 69-81.

16. Decker, K., Eberwein, H., Gries, F.A. and M. Brühmüller: Über den Abbau des Nicotins durch Bakterienenzyme; 2. Phys. Chem. 319 (1960) 279-282.

17. De Lorenzo, V., Herrero, M., Metzke, M. and K.N. Timmis: An upstream XylR- and IHF-induced nucleoprotein complex regulates the sigma 54 dependent Pu promoter of TOL plasmid; The EMBO Journal 10 (1991) 1159 -1167.

18. De Traglia, M.C. and A.M. Tometsko: Separation of D-(+)-nicotine from a racemic mixture by stereospecific degradation of the L-(-)isomer with Pseudomonas putida; Applied and Environmental Microbiology 39 (1980) 1067-1069.

19. Eberwein, H., Gries, F.A. and K. Decker: Uber den Abbau des Nicotins durch Bakterienenzyme, II. Isolierung und Charakterisierung eines nicotin-abbauenden Bodenbakteriums; Z. Phys. Chem. 323 (1961) 236-248.

20. Edwards, W.B. and R. McCuen: Preparation of optically pure (R)-(+)-nicotine. Studies on the microbial degradation of nicotinoids; J. Org. Chem. 48 (1983) 2484-2487.

21. Frankenburg, W.G. and A.A. Vaitekunas: Chemical studies on nicotine degradation by microorganisms from the surface of tobacco seeds; Arch. Biochem. and Biophys. 58 (1955) 418-425.

22. Freudenberg, W., Koenig, K and J.R. Andreesen: Nicotine dehydrogenase from Artbrobacter oxidans: A molybdenum-containing hydroxylase; FEMS Microbiology Letters 52 (1988) 13-18.

23. Gloger, M. and K. Decker: Zum Mechanismus der Induktion nicotinabbauender Enzyme in Artbrobacter oxydans; Z. Naturforschg. 24b (1969) 1016-1025.

24. Hochstein, L.I, and S.C. Rittenberg: The bacterial oxidation of nicotine. II. The isolation of the first oxidative product and its identification as (l)-6-hydroxynicotine; J. Bio. Chem. 234 (1959) 156-160.

25. Hylin, J.W.: The microbial degradation of nicotine. II. The mode of action of Achromobacter nicotinopbagwn; Archives of Biochemistry and Biophysics 83 (1959) 528-537.

26. Kieslich, K.: Microbial transformation of nonsteroid cyclic compounds. Pyridine alkaloids; Georg Thieme, Stuttgart, p. 205-210, 1976.

27. Maeda, S., Matsushita, H., Mikami, Y. and T. Kisaki: Structural Changes of N-methyl-myosmine based on pH; Agric. Biol. Chem. 44 (1980) 1643-1645.

28. Mauch, L., Bichler, V. and R. Brandsch: Functional analysis of the 5'regulatory region and the UUG translation initiation codon of the Artbrobacter oxidans 6-hydroxy-D-nicotme oxidase gene; Mol. Gen. Genet, 221 (1990) 427-434.

29. Mauch, L., Kraufi, B. and R, Brandsch: Growth stage-dependent expression of 6-hydroxy-D-nicotine oxidase of the nicotine regulon of Artbrobacter oxidans; Arch. Microbiol. 152 (1989) 95-99.

30. Nagel, M., Koenig, K. and J.R. Andreesen: Bactopterin as component of eubacterial dehydrogenases involved in hydroxylation reactions initiating the degradation of nicotine, nicotinate, and 2-furan-carboxylate; FEMS Microbiology Letters 60 (1989) 323-326.

31. Parac Recycling GmbH; Personal communication.

32. Rossi, S., Altieri, P. and L. Barca: Biodegradation of nicotine in waste tobacco dust using nicotinophilous bacteria; CORESTA Information Bulletin, 1994 pp. 158.

33. Scheunert, J.: Mikrobieller Abbau organischer Fremdstoffe im Boden; CHIUZ 2 (1994) 68-78.

34. Sguros, P.L.: Microbial transformation of the tobacco alkaloids. I. Cultural and morphological characteristics of a nicotinophile; J, Bacterid; 69 (1955) 28-37.

35. Sindelar, R.D., Rosazza, J.B. and C.F. Barfknecht: N-Demethylation of nicotine and reduction of nicotine-1'-N-oxide by Microsporum gypseum; Applied and Environmental Microbiology 38 (1979) 836-839.

36. Tabuchi, T,: Microbial degradation of nicotine and nicotinic acid. I. Isolation of nicotine-decomposing bacteria and these morphological and physiological properties; J. Agr. Chem. Soc. Japan 28 (1954) 807-810.

37. Thacker, R., Rorvig, O., Kahlon, P. and I.C. Gunsalus: Nic, a conjugative nicotine-nicotinate degradative plasmid ia Pseudomonas convexa; Journal of Bacteriology 135 (1978) 289-290.

38. Tso, T.C.: Production, physiology and biochemistry of tobacco plant; p. 466 IDEALS Inc., Beltsville, Maryland 1990.

39. Uchida, S., Maeda, S. and T. Kisaki: Conversion of nicotine into nornicotine and N-methylmyosmine by fungi; Agric. Biol. Chem. 47 (1983) 1949-1953.

40. Verdonck, O.; De Boodt, M., Stradiot, P. and R. Penninck: The use of tree bark and tobacco waste in agriculture and horticulture; composting of agricultural and other waste; J.K. Gasser, London, 1985 pp. 203-215.

41. Wackett, L. Sadowsky, M. J., Newman, L.M., Hur, H.-G. and S. Li: Metabolism of polyhalogenated compounds by a genetically engineered bacterium; Nature 368 (1994), 627 - 629.

42. Wada, E.: Microbial degradation of the tobacco alkaloids, and some related compounds; Archives of Biochemistry and Biophysics 72 (1957) 145-162.

43. Wada, E. and K. Yamasaki: Mechanism of microbial degradation of nicotine; Science 117 (1953) 152-153.

44. Weidner, M. et al.; Personal communication.

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