LC–MS/MS based-comparative study of (S)-nicotine metabolism by microorganisms, mushroom and plant cultures: Parallels to its mammalian metabolic fate

Venisetty, 2003, Application of microbial biotransformation for the new drug discovery using natural drugs as substrates, Curr Pharm Biotechnol, 4, 153, 10.2174/1389201033489847 Asha, 2009, Cunninghamella – a microbial model for drug metabolism studies – a review, Biotechnol Adv, 27, 16, 10.1016/j.biotechadv.2008.07.005 Ibrahim, 1999, Stereoselective hydroxylation of (+)-dihydroperfamine Cunninghamella echinulata, Pharm Biol, 37, 123, 10.1076/phbi.37.2.123.6089 Longo, 2006, Production of food aroma compounds: microbial and enzymatic methodologies, Food Technol Biotech, 44, 335 Kelly, 2003, The biodiversity of microbial cytochromes P450, Adv Microb Physiol, 47, 131, 10.1016/S0065-2911(03)47003-3 Smith, 1975, Microbial models of mammalian metabolism, J Pharm Sci, 64, 1737, 10.1002/jps.2600641104 Pras, 1995, The power of plant enzymes in bioconversions, AgBiotech News Info, 231, 231 Moyer, 2002, Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles, Clin Chem, 48, 1460, 10.1093/clinchem/48.9.1460 Hukkanen, 2005, Metabolism and disposition kinetics of nicotine, Pharmacol Rev, 57, 79, 10.1124/pr.57.1.3 Upadhyaya, 2002, Metabolism and pharmacokinetics of N′-nitrosonornicotine in the patas monkey, Drug Metab Dispos, 30, 1115, 10.1124/dmd.30.10.1115 Meng, 2010, A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated form tobacco leaves, Res Microbiol, 161, 626, 10.1016/j.resmic.2010.05.017 Uchida, 1983, Conversion of nicotine into nornicotine and N-methylmyosmine by Fungi, Agric Biol Chem, 47, 1949, 10.1271/bbb1961.47.1949 Sindelar, 1977, N-demethylation of nicotine and reduction of nicotine-1′-N-oxide by Microsporum gypseum, Appl Environ Microbiol, 38, 836, 10.1128/AEM.38.5.836-839.1979 Hobbs, 1991, Biotransformation of nicotine to nornicotine by cell suspensions of Nicotiana tabacum L. cv. Wisconsin-38, New Phytol, 119, 477, 10.1111/j.1469-8137.1991.tb01038.x Sarangi, 2006, Anti-tumor and immunomodulating effects of Pleurotus ostreatus mycelia-derived proteoglycans, Int Immunopharmacol, 6, 1287, 10.1016/j.intimp.2006.04.002 Sakamoto, 1994, Biotransformation of germacrone by suspension cultured cells, Phytochemistry, 35, 1215, 10.1016/S0031-9422(00)94823-4 Hodgson, 1965, Two dimensional thin layer chromatography of tobacco alkaloids and related compounds, J Chromatogr, 20, 176, 10.1016/S0021-9673(01)97388-1 Smyth, 2007, Characterisation of nicotine and related compounds using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their detection by liquid chromatography/electrospray ionization mass spectrometry, Rapid Commun Mass Spectrom, 21, 557, 10.1002/rcm.2871 Luo, 2007, Study on streptomycetes degradation of nicotine and chlorogenic acid in tobacco, Acta Microbiol. Sinica, 47, 1095 Hoofnagle, 2006, Specific detection of anabasine, nicotine, and nicotine metabolites in urine by liquid chromatography–tandem mass spectrometry, Am J Clin Pathol, 126, 880, 10.1309/LQ8U3UL956ET324X Liang, 2013, Online monitoring oxidative products and metabolites of nicotine by free radicals generation with fenton reaction in tandem mass spectrometry, Sci World J, 13, 1 Liu, 1999, Studies on the pyrrolinone metabolites derived from the tobacco alkaloid 1-methyl-2-(3-pyridinyl) pyrrole (β-nicotyrine), Chem Res Toxicol, 12, 508, 10.1021/tx990019j Jenner, 1973, Comparative in vitro hepatic metabolism of some tertiary N-methyl tobacco alkaloids in various species, Res Commun Chem Pathol Pharmacol, 6, 829 Janne, 2005, Metabolism and disposition kinetics of nicotine, Pharmacol Rev, 57, 79, 10.1124/pr.57.1.3 Wishart, 2009, HMDB: a knowledgebase for the human metabolome, Nucleic Acids Res, 37, D603, 10.1093/nar/gkn810 Hecht, 1981, Mass spectra of tobacco alkaloid-derived nitrosamines, their metabolites and related compounds, Beitrage zur Tabakforschung, 11, 57