Combining FTIR-ATR and OPLS-DA methods for magic mushrooms discrimination

Forensic Chemistry - Tập 29 - Trang 100421 - 2022
Cátia S.M. Esteves1, Elena M.M. de Redrojo2, José Luis García Manjón3, Gabriel Moreno3, Filipe E. Antunes1, Gemma Montalvo2,4, Fernando E. Ortega-Ojeda2,5,4
1CQC, Department of Chemistry, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal
2Universidad de Alcalá, Departamento de Química Analítica, Química Física e Ingeniería Química, Ctra. Madrid-Barcelona km 33.6, Alcalá de Henares, Madrid 28864, Spain
3Universidad de Alcalá, Departamento de Ciencias de la Vida, Ctra. Madrid-Barcelona km 33.6, Alcalá de Henares, Madrid 28864, Spain
4Universidad de Alcalá, Instituto Universitario de Investigación en Ciencias Policiales, Libreros 27, Alcalá de Henares, Madrid 28801, Spain
5Universidad de Alcalá, Departamento de Ciencias de la Computación, Ctra. Madrid-Barcelona km 33.6, Alcalá de Henares, Madrid 28864, Spain

Tài liệu tham khảo

Shirota, 2003, Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of “magic mushroom”, J. Nat. Prod., 66, 885, 10.1021/np030059u K. Stebelska, Chapter 84 - Assays for Detection of Fungal Hallucinogens Such as Psilocybin and Psilocin, in: Neuropathology of Drug Addictions and Substance Misuse, Academic Press, San Diego (2016), pp. 909–926. Feng, 2017, New psychoactive substances of natural origin: a brief review, J. Food Drug Anal., 25, 461, 10.1016/j.jfda.2017.04.001 G. Moreno, J.L. Manjón Guía de hongos de la Península Ibérica, Omega(2010). C. Andersson, J. Kristinsson, J. Gry, Occurrence and use of hallucinogenic mushrooms containing psilocybin alkaloids, Nordic Concil of Ministers, Copenhagen, Denmark (2009). United Nations Office on Drugs Crime, Final act of the United Nations Conference for the adoption of a protocol on psychotropic substances, in: The International Drug Control Conventions, United Nations(2013). T. Mishraki-Berkowitz, E. Kochelski, P. Kavanagh, J. O'Brien, C. Dunne, B. Talbot, P. Ennis, U.E. Wolf The Psilocin (4-hydroxy-N,N-dimethyltryptamine) and Bufotenine (5-hydroxy-N,N-dimethyltryptamine) Case: Ensuring the Correct Isomer has Been Identified Journal of Forensic Sciences, 65(5) (2020), pp.1450-1457. Solano, 2019, Psychedelic fungus (Psilocybe sp.) authentication in a case of illegal drug traffic: sporological, molecular analysis and identification of the psychoactive substance, Sci. Justice, 59, 102, 10.1016/j.scijus.2018.08.005 A.R. Winstock, M.J. Barratt, A. Aldridge, A. Zhuparris, E. Davies, C. Hughes, M. Johnson, M. Kowalski, J.A. Ferris, Global Drug Survey (GDS) Key Findings Report, 2019. M. Farré, E. Papaseit, F. Fonseca, M. Torrens, Addiction of Hallucinogens, Dissociatives, Designer Drugs and “Legal Highs”: Update on Potential Therapeutic Use, in: Textbook of Addiction Treatment: International Perspectives, Springer International Publishing, Cham (2021), pp. 259-279. Tsujikawa, 2003, Morphological and chemical analysis of magic mushrooms in Japan, Forensic Sci. Int., 138, 85, 10.1016/j.forsciint.2003.08.009 I. Morita, H. Oyama, Y. Kiguchi, A. Oguri, N. Fujimoto, A. Takeuchi, R. Tanaka, J. Ogata, R. Kikura-Hanajiri, N. Kobayashi Immunochemical monitoring of psilocybin and psilocin to identify hallucinogenic mushrooms Journal of Pharmaceutical and Biomedical Analysis, 190 (2020), p.113485. Kallifatidis, 2014, Fluorescent Random Amplified Microsatellites (F-RAMS) analysis of mushrooms as a forensic investigative tool, Forensic Sci. Int. Genet., 9, 25, 10.1016/j.fsigen.2013.10.009 Gambaro, 2016, DNA-based taxonomic identification of basidiospores in hallucinogenic mushrooms cultivated in “grow-kits” seized by the police: LC-UV quali-quantitative determination of psilocybin and psilocin, J. Pharm. Biomed. Anal., 125, 427, 10.1016/j.jpba.2016.03.043 Kamata, 2005, Liquid chromatography-mass spectrometric and liquid chromatography-tandem mass spectrometric determination of hallucinogenic indoles psilocin and psilocybin in “Magic Mushroom” Samples, J. Forensic Sci., 50, 336, 10.1520/JFS2004276 Kikura-Hanajiri, 2005, Simultaneous determination of nineteen hallucinogenic tryptamines/β-calbolines and phenethylamines using gas chromatography–mass spectrometry and liquid chromatography–electrospray ionisation-mass spectrometry, J. Chromatogr. B, 825, 29, 10.1016/j.jchromb.2005.01.041 Keller, 2006, Application of ion mobility spectrometry in cases of forensic interest, Forensic Sci. Int., 161, 130, 10.1016/j.forsciint.2006.03.032 Borovička, 2014, Phylogenetic and chemical studies in the potential psychotropic species complex of Psilocybe atrobrunnea with taxonomic and nomenclatural notes, Persoonia, 34, 1, 10.3767/003158515X685283 Saito, 2005, Determination of psilocybin in hallucinogenic mushrooms by reversed-phase liquid chromatography with fluorescence detection, Talanta, 66, 562, 10.1016/j.talanta.2004.11.031 J.R. Stenzel, W.S. Patrol, G. Jiang, C. Loran, Identification of Psychotropic Substances in Mushrooms and Chocolate by UHPLC/MS, Thermo Fisher Scientific Inc, 2008. [21] J. Nagy, T. Veress. Nagy, 2016, HPLC analysis of hallucinogenic mushroom alkaloids (Psilocin and Psilocybin) applying hydrophilic interaction chromatography (HILIC), J. Forensic Res., 07, 10.4172/2157-7145.1000356 Zhou, 2021, Sensitive quantitative analysis of psilocin and psilocybin in hair samples from suspected users and their distribution in seized hallucinogenic mushrooms, Forensic Toxicol., 39, 464, 10.1007/s11419-020-00566-3 Rácz, 2019, Modeling retention behavior on analysis of hallucinogenic mushrooms using hydrophilic interaction liquid chromatography, J. Chromatogr. Sci., 57, 230, 10.1093/chromsci/bmy104 T. Veress, N. Rácz, J. Nagy, W. Jiang Determination of Psilocin and Psilocybin in Magic Mushrooms Using iHILIC ® -Fusion and MS LC GC Europe, 2019 (2019). Anastos, 2006, The determination of psilocin and psilocybin in hallucinogenic mushrooms by HPLC utilizing a dual reagent acidic potassium permanganate and tris(2,2'-bipyridyl)ruthenium(II) chemiluminescence detection system, J. Forensic Sci., 51, 45, 10.1111/j.1556-4029.2005.00033.x Kysilka, 1990, A novel extraction procedure for psilocybin and psilocin determination in mushroom samples, Planta Medica, 45, 327, 10.1055/s-2006-960970 Y. Chen, B. Chefetz, R. Rosario, J.D.H. van Heemst, C.P. Romaine, P.G. Hatcher Chemical Nature and Composition of Compost During Mushroom Growth Compost Science & Utilization, 8(4) (2000), pp.347-359. Choong, 2016, Differential identification of mushrooms sclerotia by IR macro-fingerprint method, Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 152, 34, 10.1016/j.saa.2015.07.054 Michell, 1967, Composition of extracted fungal cell walls as indicated by infrared spectroscopy, Arch. Biochem. Biophys., 120, 628, 10.1016/0003-9861(67)90528-0 Mohaček-Grošev, 2001, Vibrational spectroscopic characterization of wild growing mushrooms and toadstools, Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 57, 2815, 10.1016/S1386-1425(01)00584-4 Ma, 2018, Assessment of polysaccharides from mycelia of genus ganoderma by mid-infrared and near-infrared spectroscopy, Sci. Rep., 8, 1 Synytsya, 2009, Glucans from fruit bodies of cultivated mushrooms Pleurotus ostreatus and Pleurotus eryngii: structure and potential prebiotic activity, Carbohydr. Polym., 76, 548, 10.1016/j.carbpol.2008.11.021 Leung, 1968, Baeocystin and norbaeocystin: new analogs of psilocybin from psilocybe baeocystis, J. Pharm. Sci., 57, 1667, 10.1002/jps.2600571007 Koçak, 2010, Comparative study of ATR and transflection IR spectroscopic techniques for the analysis of hallucinogenic mushrooms, Forensic Sci. Int., 195, 36, 10.1016/j.forsciint.2009.11.002 Kalač, 2009, Chemical composition and nutritional value of European species of wild growing mushrooms: a review, Food Chem., 113, 9, 10.1016/j.foodchem.2008.07.077 Gomba, 2015, Distinction of fungal polysaccharides by N/C ratio and mid infrared spectroscopy, Int. J. Biol. Macromol., 80, 271, 10.1016/j.ijbiomac.2015.05.059 Kulmyrzaev, 2007, Infrared and fluorescence spectroscopic techniques for the determination of nutritional constituents in foods, Int. J. Food Prop., 10, 299, 10.1080/10942910601045305 O'Gorman, 2010, Use of fourier transform infrared spectroscopy and chemometric data analysis to evaluate damage and age in mushrooms (Agaricus bisporus) grown in Ireland, J. Agric. Food. Chem., 58, 7770, 10.1021/jf101123a Hirri, 2016, FTIR spectroscopy and PLS-DA classification and prediction of four commercial grade virgin olive oils from morocco, Food Anal. Methods, 9, 974, 10.1007/s12161-015-0255-y Yao, 2018, Geographic identification of Boletus mushrooms by data fusion of FT-IR and UV spectroscopies combined with multivariate statistical analysis, Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 198, 257, 10.1016/j.saa.2018.03.018 Wang, 2019, Attenuated total reflection-fourier transform infrared spectroscopy (ATR-FTIR) combined with chemometrics methods for the classification of lingzhi species, Molecules, 24, 10.3390/molecules24122210 Li, 2020, A new analytical method for discrimination of species in Ganodermataceae mushrooms, Int. J. Food Prop., 23, 227, 10.1080/10942912.2020.1722159 Baeva, 2020, Evaluation of the cultivated mushroom pleurotus ostreatus basidiocarps using vibration spectroscopy and chemometrics, Appl. Sci., 10, 8156, 10.3390/app10228156 T. Segelke, S. Schelm, C. Ahlers, M. Fischer Food Authentication: Truffle (Tuber spp.) Species Differentiation by FT-NIR and Chemometrics Foods, 9(7) (2020). Meenu, 2019, Application of vibrational spectroscopy for classification, authentication and quality analysis of mushroom: a concise review, Food Chem., 289, 545, 10.1016/j.foodchem.2019.03.091 G. Socrates Infrared and Raman Characteristic Group Frequencies, Wiley-Blackwell(2004). Larkin, 2018 Barth, 2002, What vibrations tell about proteins, Q. Rev. Biophys., 35, 369, 10.1017/S0033583502003815 Bylesjö, 2006, OPLS discriminant analysis: combining the strengths of PLS-DA and SIMCA classification, J. Chemom., 20, 341, 10.1002/cem.1006