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Articles

Nicotine in the button mushroom Agaricus bisporus, endogenous biosynthesis?

, ORCID Icon, , ORCID Icon, & ORCID Icon
Pages 902-916 | Received 30 Mar 2023, Accepted 04 Jun 2023, Published online: 16 Jun 2023

References

  • Anastassiades M, Lehotay SJ, Štajnbaher D, Schenck FJ. 2003. Fast and easy multiresidue method employing acetonitrile extraction/partitioning and "dispersive solid-phase extraction" for the determination of pesticide residues in produce. J AOAC Int. 86(2):412–431. doi: 10.1093/jaoac/86.2.412.
  • Ares AM, Bernal J. 2012. Hydrophilic interaction chromatography in drug analysis. Cent Eur J Chem. 10(3):534–553.
  • Baldwin IT, Halitschke R, Kessler A, Schittko U. 2001. Merging molecular and ecological approaches in plant-insect interactions. Curr Opin Plant Biol. 4(4):351–358. doi: 10.1016/s1369-5266(00)00184-9.
  • Benowitz NL. 2009. Pharmacology of nicotine: addiction, smoking-induced disease, and therapeutics. Annu Rev Pharmacol Toxicol. 49:57–71. doi: 10.1146/annurev.pharmtox.48.113006.094742.
  • Benton M, Chua MJ, Gu F, Rowell F, Ma J. 2010. Environmental nicotine contamination in latent fingermarks from smoker contacts and passive smoking. Forensic Sci Int. 200(1-3):28–34. doi: 10.1016/j.forsciint.2010.03.022.
  • BfR Opinion No. 009/2009 2009. Nicotine in dried boletus mushrooms: Causes for contamination must be determined. [accessed 2023 Mar 1] https://www.bfr.bund.de/cm/349/nicotine_in_dried_boletus_mushrooms_causes_for_contamination_must_be_determined.pdf.
  • Biastoff S, Reinhardt N, Reva V, Brandt W, Dräger B. 2009. Evolution of putrescine N-methyltransferase from spermidine synthase demanded alterations in substrate binding. FEBS Lett. 583(20):3367–3374. doi: 10.1016/j.febslet.2009.09.043.
  • Buszewski B, Noga S. 2012. Hydrophilic interaction liquid chromatography (HILIC)—a powerful separation technique. Anal Bioanal Chem. 402(1):231–247. doi: 10.1007/s00216-011-5308-5.
  • Cavalieri C, Bolzoni L, Bandini M. 2010. Nicotine determination in mushrooms by LC-MS/MS with preliminary studies on the impact of drying on nicotine formation. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 27(4):473–477. doi: 10.1080/19440040903479768.
  • Chang YW, Nguyen HP, Chang M, Burket SR, Brooks BW, Schug KA. 2015. Determination of nicotine and its metabolites accumulated in fish tissue using hydrophilic interaction liquid chromatography coupled with tandem mass spectrometry. J Sep Sci. 38(14):2414–2422. doi: 10.1002/jssc.201500235.
  • Commission Decision 2002/657/EC 2002. of 12 August implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. OJ L221:8–36.
  • Curwin BD, Hein MJ, Sanderson WT, Nishioka MG, Buhler W. 2005. Nicotine exposure and decontamination on tobacco harvesters’ hands. Ann Occup Hyg. 49(5):407–413.
  • Dadáková E, Pelikánová T, Kalač P. 2009. Content of biogenic amines and polyamines in some species of European wild-growing edible mushrooms. Eur Food Res Technol. 230(1):163–171. doi: 10.1007/s00217-009-1148-3.
  • Deventer K, Pozo OJ, Verstraete AG, Van Eenoo P. 2014. Dilute-and-shoot-liquid chromatography-mass spectrometry for urine analysis in doping control and analytical toxicology. Trends Anal Chem. 55:1–13. doi: 10.1016/j.trac.2013.10.012.
  • Dewey RE, Xie J. 2013. Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Phytochemistry. 94:10–27. doi: 10.1016/j.phytochem.2013.06.002.
  • [EFSA] European Food Safety Authority. 2009. EFSA statement: potential risks for public health due to the presence of nicotine in wild mushrooms. Efsa J. Rn. 286:1–47.
  • Gardini F, Özogul Y, Suzzi G, Tabanelli G, Özogul F. 2016. Technological factors affecting biogenic amine content in foods: a review. Front Microbiol. 7:1218. doi: 10.3389/fmicb.2016.01218.
  • Gosetti F, Mazzucco E, Gennaro MC, Marengo E. 2013. Simultaneous determination of sixteen underivatized biogenic amines in human urine by HPLC-MS/MS. Anal Bioanal Chem. 405(2-3):907–916. doi: 10.1007/s00216-012-6269-z.
  • Grubner O, First MW, Huber GL. 1980. Gas chromatographic determination of nicotine in gases and liquids with suppression of adsorption effects. Anal Chem. 52(11):1755–1758. doi: 10.1021/ac50061a049.
  • Guillamón E, García-Lafuente A, Lozano M, D'Arrigo M, Rostagno MA, Villares A, Martínez JA. 2010. Edible mushrooms: role in the prevention of cardiovascular diseases. Fitoterapia. 81(7):715–723. doi: 10.1016/j.fitote.2010.06.005.
  • Hälvin K, Paalme T, Nisamedtinov I. 2013. Comparison of different extraction methods for simultaneous determination of B complex vitamins in nutritional yeast using LC/MS-TOF and stable isotope dilution assay. Anal Bioanal Chem. 405(4):1213–1222. doi: 10.1007/s00216-012-6538-x.
  • Junker A, Fischer J, Sichhart Y, Brandt W, Dräger B. 2013. Jul. Evolution of the key alkaloid enzyme putrescine N-methyltransferase from spermidine synthase. Front Plant Sci. 4:260. doi: 10.3389/fpls.2013.00260.
  • Kalač P. 2013. A review of chemical composition and nutritional value of wild-growing and cultivated mushrooms. J Sci Food Agric. 93(2):209–218. doi: 10.1002/jsfa.5960.
  • Kalač P, Křižek M. 1997. Formation of biogenic amines in four edible mushroom species stored under different conditions. Food Chem. 58(3):233–236. doi: 10.1016/S0308-8146(96)00170-7.
  • Kang HH, Yun CI, Moon JY, Lee JG, Kim YJ. 2020. Validation and measurement uncertainty of GC-MS quantification method for nicotine in dried mushrooms using QuEChERS extraction. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 37(10):1687–1694. doi: 10.1080/19440049.2020.1800827.
  • Katoh A, Ohki H, Inai K, Hashimoto T. 2005. Molecular regulation of nicotine biosynthesis. Plant Biotechnol. 22(5):389–392. doi: 10.5511/plantbiotechnology.22.389.
  • Katoh A, Shoji T, Hashimoto T. 2007. Molecular cloning of N-methylputrescine oxidase from tobacco. Plant Cell Physiol. 48(3):550–554. doi: 10.1093/pcp/pcm018.
  • Lozano A, Martinez-Uroz MA, Gomez-Ramos MJ, Gomez-Ramos MM, Mezcua M, Fernandez-Alba AR. 2012. Determination of nicotine in mushrooms by various GC/MS- and LC/MS-based methods. Anal Bioanal Chem. 402(2):935–943. doi: 10.1007/s00216-011-5490-5.
  • Marclay F, Grata E, Perrenoud L, Saugy M. 2011. A one-year monitoring of nicotine use in sport: frontier between potential performance enhancement and addiction issues. Forensic Sci Int. 213(1-3):73–84. doi: 10.1016/j.forsciint.2011.05.026.
  • Martins-Green M, Adhami N, Frankos M, Valdez M, Goodwin B, Lyubovitsky J, Dhall S, Garcia M, Egiebor I, Martinez B, et al. 2014. Cigarette smoke toxins deposited on surfaces: implications for human health. PLOS One. 9(1):e86391. doi: 10.1371/journal.pone.0086391.
  • Mattila P, Könkö K, Eurola M, Pihlava JM, Astola J, Vahteristo L, Hietaniemi V, Kumpulainen J, Valtonen M, Piironen V. 2001. Contents of vitamins, mineral elements, and some phenolic compounds in cultivated mushrooms. J Agric Food Chem. 49(5):2343–2348. doi: 10.1021/jf001525d.
  • Matt GE, Quintana PJE, Zakarian JM, Hoh E, Hovell MF, Mahabee-Gittens M, Watanabe K, Datuin K, Vue C, Chatfield DA. 2016. When smokers quit: exposure to nicotine and carcinogens persists from thirdhand smoke pollution. Tob Control. 26(5):548–556. doi: 10.1136/tobaccocontrol-2016-053119.
  • Merdivan S, Willke C, Lindequist U. 2016. Development and validation of an LC-MS/MS method for the quantification of agaritine in mushrooms. Int J Med Mushrooms. 18(1):13–21. doi: 10.1615/IntJMedMushrooms.v18.i1.30.
  • Miller RD, Collins GB, Davis DL. 1983. Effects of nicotine precursors on nicotine content in callus cultures of Burley tobacco alkaloid lines. Crop Sci. 23(3):561–565. doi: 10.2135/cropsci1983.0011183X002300030027x.
  • Moldoveanu SC, Wayne AS, Lawson MD. 2016. Nicotine analysis in several non-tobacco plant materials. Contrib Tob Res. 27(2):54–59. doi: 10.1515/cttr-2016-0008.
  • Molins-Legua C, Campins-Falcó P. 2005. Solid phase extraction of amines. Anal Chim Acta. 546(2):206–220. doi: 10.1016/j.aca.2005.05.021.
  • Morin E, Kohler A, Baker AR, Foulongne-Oriol M, Lombard V, Nagy LG, Ohm RA, Patyshakuliyeva A, Brun A, Aerts AL, et al. 2012. Genome sequence of the button mushroom Agaricus bisporus reveals mechanisms governing adaptation to a humic-rich ecological niche. Proc Natl Acad Sci U S A. 109(43):17501–17506. doi: 10.1073/pnas.1206847109.
  • Müller C, Bracher F, Plössl F. 2011. Determination of nicotine in dried mushrooms by using a modified QuEChERS approach and GC-MS-MS. Chromatographia. 73(7-8):807–811. doi: 10.1007/s10337-011-1948-z.
  • Noctor G. 2006. Metabolic signaling in defence and stress: the central roles of soluble redox couples. Plant Cell Environ. 29(3):409–425. doi: 10.1111/j.1365-3040.2005.01476.x.
  • Northrup TF, Khan AM, Jacob P, Benowitz NL, Hoh E, Hovell MF, Matt GE, Stotts AL. 2016. Thirdhand smoke contamination in hospital settings: assessing exposure risk for vulnerable paediatric patients. Tob Control. 25(6):619–623. doi: 10.1136/tobaccocontrol-2015-052506.
  • Nugroho LH, Peltenburg-Looman AMG, de Vos H, Verberne MC, Verpoorte R. 2002. Nicotine and related alkaloids accumulation in constitutive salicylic acid producing tobacco plants. Plant Sci. 162(4):575–581. doi: 10.1016/S0168-9452(01)00596-9.
  • RASFF Notification reference - 2013. 0050, Notification reference - 2013.0051 and Notification reference - 2013.0065. [accessed 2016] https://ec.europa.eu/food/safety/rasff_en.) (access date 2016).
  • Regulation (EC) No 1107/2009 of the European Parliament and of the Council of 21 October 2009 concerning the placing of plant protection products on the market and repealing Council Directives 79/117/EEC and 91/414/EEC. OJ L 309:1–50.
  • Regulation (EC) No 396/ 2005. of the European Parliament and of the Council of 23 February 2005 on maximum residue levels of pesticides in or on food and feed of plant and animal origin and amending Council Directive 91/414/EECText with EEA relevance. OJ L 70:1–16.
  • Sadler M. 2003. Nutritional properties of edible fungi. Nutr Bulletin. 28(3):305–308. doi: 10.1046/j.1467-3010.2003.00354.x.
  • Schindler BK, Bruns S, Lach G. 2015. Biogenic amines – A possible source for nicotine in mushrooms? A discussion of published literature data. Food Chem. 171:379–381. doi: 10.1016/j.foodchem.2014.08.099.
  • Shi Q, Chunjian L, Zhang F. 2006. Nicotine synthesis in Nicotiana tabacum L. induced by mechanical wounding is regulated by auxin. J Exp Bot. 57(11):2899–2907. doi: 10.1093/jxb/erl051.
  • Siegmund B, Leitner E, Pfannhauser W. 1999. Determination of the nicotine content of various edible nightshades (Solanaceae) and their products and estimation of the associated dietary nicotine intake. J Agric Food Chem. 47(8):3113–3120. doi: 10.1021/jf990089w.
  • Sonnenberg ASM, Baars JJP, Gao W, Visser RGF. 2017. Developments in breeding of Agaricus bisporus var. bisporus progress made and technical and legal hurdles to take. Appl Microbiol Biotechnol. 101(5):1819–1829. doi: 10.1007/s00253-017-8102-2.
  • Tomizawa M, Casida JE. 2009. Molecular recognition of neonicotinoid insecticides: the determinants of life or death. Acc Chem Res. 42(2):260–269. doi: 10.1021/ar800131p.
  • Valdés-Santiago L, Ruiz-Herrera J. 2013. Dec. Stress and polyamine metabolism in fungi. Front Chem. 1:42. doi: 10.3389/fchem.2013.00042.
  • Valverde ME, Hernández-Pérez T, Paredes-López O. 2015. Edible mushrooms: improving human health and promoting quality life. Int J Microbiol. 2015(7):1–14. doi: 10.1155/2015/376387.
  • Wang H, Zhao Q, Song WT, Xu Y, Zhang XP, Zeng QL, Chen HY, Ding L, Ren NQ. 2011. High-throughput dynamic microwave-assisted extraction on-line coupled with solid-phase extraction for analysis of nicotine in mushroom. Talanta. 85(1):743–748. doi: 10.1016/j.talanta.2011.04.058.
  • Wang X, Bennetzen JL. 2015. Current status and prospects for the study of Nicotiana genomics, genetics and nicotine biosynthesis genes. Mol Genet Genomics. 290(1):11–21. doi: 10.1007/s00438-015-0989-7.
  • Wasser SP. 2014. Medicinal mushroom science: current perspectives, advances, evidences, and challenges. Biomed J. 37(6):345–356. doi: 10.4103/2319-4170.138318.
  • Wu X, Ge X, Liang S, Sun H. 2014. A highly sensitive method for the determination of thiophanate methyl, cyromazine, and their metabolites in edible fungi by ultra-performance liquid chromatography using accelerated solvent extraction and cleanup with solid-phase extraction. Food Anal Methods. 7(4):774–782. doi: 10.1007/s12161-013-9680-y.
  • Xia E, Tao W, Yao X, Wang J, Tang F. 2016. Effects of processing on carbendazim reside in Pleurotus ostreatus. Food Sci Nutr. 4(4):645–650. doi: 10.1002/fsn3.328.
  • Yamamoto S, Itano H, Kataoka H, Makita M. 1982. Gas-liquid chromatographic method for analysis of di- and polyamines in foods. J Agric Food Chem. 30(3):435–439. doi: 10.1021/jf00111a006.

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