Low-Field NMR for Quality Control and Fraud Detection: Application to the Analysis of Dietary Supplements and E-Liquids

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Low-Field NMR for Quality Control and Fraud Detection: Application to the Analysis of Dietary Supplements and E-Liquids Low-field NMR for quality control and fraud detection : application to the analysis of dietary supplements and e-liquids Nao Wu To cite this version: Nao Wu. Low-field NMR for quality control and fraud detection : application to the analysis ofdietary supplements and e-liquids. Food engineering. Université Paul Sabatier - Toulouse III, 2020. English. NNT : 2020TOU30044. tel-02979720 HAL Id: tel-02979720 https://tel.archives-ouvertes.fr/tel-02979720 Submitted on 27 Oct 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Acknowledgments First, my deepest gratitude goes to my supervisors Prof. Véronique Gilard and Dr. Stéphane Balayssac. Thanks for their supervision and careful guidance in my personal development and academic research over the past three years. I would like to thank also Prof. Myriam Martino for welcoming me into the Biomedical NMR group of SPCMIB. Their profound knowledge and philosophy in science have led me into the door of this research area and will always accompany me in my career. Here, I would like to extend my sincere respect and gratitude to my three tutors. I would like to thanks Dr. Gaetan Assemat for his patient and professional advice, which helps me adapt my doctoral life quickly in the first year. Special thanks to all my committee members, Christine Enjalbal, Guilhem Pagès, Ariane Angeloff and Franck Jolibois, for their attending and meaningful comments. Thanks for Ph.D. funding from the Chinese Scholarship Council (CSC). Last but most importantly, I’d like to thanks my family, especially my parents, for their supports during this period which inspire me to keep going forward. July 2020 Toulouse, France List of Abbreviations General Abbreviations API Active pharmaceutical ingredients C. cassia Cinnamomum cassia C. verum Cinnamomum verum CNS Central nervous system DS Dietary supplements E-liquid Liquid mixture for electronic cigarette EI Electron ionization ESI Electrospray ionization FA Fatty acids FDA Food and Drug Administration GC Gas chromatography HPLC High performance liquid chromatography MS Mass spectrometry NIST National Institute of Standards and Technology PG Propylene glycol PCA Principal component analysis PLS-DA Partial least squares to latent structures-discriminant analysis OPLS-DA Orthogonal PLS-DA OTC Over the counter RT Retention time SCs Synthetic cannabinoids THC Tetrahydrocannabinol TLC Thin layer chromatography TDI Tolerable daily intake TOF Time of flight UNODC United Nations Office on Drugs and Crime UPLC Ultra performance liquid chromatography UV Ultraviolet spectroscopy IR Infrared spectroscopy VG Vegetable glycerol NMR-Specific abbreviations AQ Acquisition time Cr(ACAC)3 Chromium(III) acetylacetonate COSY Correlation spectroscopy D1 Relaxation delay DOSY Diffusion ordered spectroscopy FID Free induction decay HF High field HETCOR Heteronuclear correlation HMBC Heteronuclear multiple bond correlation HSQC Heteronuclear single quantum coherence spectroscopy LB Line broadening LF Low field LOD Limit of detection LOQ Limit of quantification NMR Nuclear magnetic resonance NS Scan numbers P90 Pulse 90° ppm Parts per million qNMR Quantitative NMR RF Radio frequency S/N Signal to noise ratio SW Spectral width T1 Longitudinal relaxation time T2 Transverse relaxation time TD Time domain TSP 3-(Trimethylsilyl)propionic-2,2,3,3-d4 acid sodium salt TXO Triple resonance probe with specific nuclei TFT α,α,α-Trifluorotoluene Table of Content General Introduction ................................................................................ 1 Chapter I Bibliography ............................................................................ 6 1. Introduction ............................................................................................................ 6 2. Quality control assessed by NMR, and the use of low-field spectroscopy ............ 7 2.1 Analytical methods used for quality control of complex samples and the application of NMR ................................................................................................ 7 2.2 Recent Low-Field NMR ................................................................................... 9 2.3 Low-field NMR spectroscopy in food, pharmacy and forensic ..................... 10 2.4 Application of chemometrics in LF benchtop analysis .................................. 12 3. Cinnamon: From the composition to the authentication ...................................... 16 3.1 Overview on species of cinnamon .................................................................. 17 3.2 Functional activities of cinnamon................................................................... 19 3.3 Chemical compositions of cinnamon ............................................................. 20 3.4 Analytical approaches for analysis and authentification of raw cinnamon .... 22 4. Herbal slimming supplements and adulteration ................................................... 25 4.1 Illegal adulterations in herbal slimming supplements .................................... 26 4.2 Sibutramine and its analogues ........................................................................ 27 4.3 Phenolphthalein .............................................................................................. 28 4.4 Other synthetic slimming adulterants ............................................................. 28 4.5 Analytical approaches for screening adulterants in herbal slimming supplements. ......................................................................................................... 29 5. Synthetic cannabinoids: Illicit drugs in commercial products ............................. 32 5.1 Introduction of SCs;........................................................................................ 33 5.2 Structure of SCs and their development ......................................................... 34 5.3 Formulations of SCs commercial products .................................................... 39 5.4 Analytical methods for identification SCs in commercials ............................ 40 6. Conclusion ............................................................................................................ 42 Reference .................................................................................................................. 44 Chapter II Evaluation of Low-field versus High-field Proton NMR Spectroscopy for Quality Control of Cinnamon Samples................... 64 1. Introduction .......................................................................................................... 64 2. Materials and Methods ......................................................................................... 64 2.1 Materials ......................................................................................................... 64 2.2 Samples Preparation for NMR analysis.......................................................... 65 2.3 NMR analysis ................................................................................................. 67 2.4 HF NMR quantification .................................................................................. 71 2.5 Chemometric analysis of LF spectra .............................................................. 72 3. Results and discussion .......................................................................................... 73 3.1 HF and LF NMR assignment of signals ......................................................... 73 3.2 Implementation of the experimental conditions ............................................. 76 3.3 Analysis of commercial samples .................................................................... 81 4. Conclusion ............................................................................................................ 89 References ................................................................................................................ 90 Chapter III Chemometric Analysis of Low-field 1H NMR Spectra for Unveiling Adulteration of Slimming Dietary Supplements by Pharmaceutical Compounds .................................................................. 92 1. Introduction .......................................................................................................... 92 2. Materials and Methods ......................................................................................... 92 2.1 Sampling and preparation ............................................................................... 92 2.2 HF 1H NMR analysis ...................................................................................... 93 2.3 LF 1H NMR analysis ...................................................................................... 93 2.4 LF 1H NMR Data analysis and chemometrics ................................................ 94 3. Results and discussion .......................................................................................... 94 3.1 HF 1H NMR analysis ...................................................................................... 94 3.2
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