Huellas dactilares y perfiles de metabolitos: Experimentos de RMN y análisis multivariado
Palabras clave:
Huellas dactilares, Perfiles de metabolitos, Análisis multivariante, Análisis de componentes principalesSinopsis
La espectroscopía de RMN es una técnica poderosa para el estudio de propiedades y composición de alimentos y plantas. Las propiedades pueden estudiarse a través de experimentos de RMN en el dominio del tiempo. Mientras que el estudio de la composición y cuantificación de metabolitos se puede llevar a cabo a partir experimentos de RMN en el dominio de la frecuencia. Esto se puede lograr a partir de dos enfoques generales. El primero consiste en adquirir las huellas dactilares de metabolitos a partir de un análisis multivariante de datos de RMN en 1D y 2D ya sea en el dominio del tiempo o frecuencia. La adquisición de huellas dactilares por RMN suele ser una herramienta rápida y eficaz para discriminar entre grupos de muestras relacionadas a partir de la identificación de las regiones espectrales más distintivas. Un segundo enfoque consiste en realizar perfiles de metabolitos con los espectros de RMN, principalmente de 1H, a partir de extractos de muestras. Esto normalmente permite identificar alrededor de 40 metabolitos en un extracto sin fraccionar. Los perfiles también se utilizan para realizar tanto análisis cualitativos como cuantitativos para comparar grupos de muestras. Los perfiles de metabolitos permiten explorar los orígenes de la variabilidad entre los grupos de muestras estudiadas. Los dos enfoques conjuntamente generan el fenotipo metabólico de una planta. En el presente capítulo se describen las técnicas más representativas para la obtención de huellas dactilares en el dominio del tiempo y la frecuencia, y los métodos de procesado de espectros para la generación de perfiles metabólicos. Así como la descripción del análisis de componentes principales, uno de los métodos de análisis multivariante más empleado para el estudio de perfiles metabólicos en RMN incluyendo el procesamiento previo de los datos espectrales.
Capítulos
-
Huellas dactilares y perfiles de metabolitos: Experimentos de RMN y análisis multivariado
Citas
Anderson, Paul E., Nicholas V. Reo, Nicholas J. DelRaso, Travis E. Doom y Michael L. Raymer. 2008. “Gaussian Binning: A New Kernel-Based Method for Processing NMR Spectroscopic Data for Metabolomics.” Metabolomics 4 (3): 261-72. https://doi.org/10.1007/s11306-008-0117-3.
Berg, Robert A. van den, Huub C. J. Hoefsloot, Johan A. Westerhuis, Age K. Smilde y Mariët J. van der Werf. 2006. “Centering, Scaling, and Transformations: Improving the Biological Information Content of Metabolomics Data.” BMC Genomics 7: 1-15. https://doi.org/10.1186/1471-2164-7-142.
Besghini, Denise, Michele Mauri y Roberto Simonutti. 2019. “Time Domain NMR in Polymer Science: From the Laboratory to the Industry.” Applied Sciences (Switzerland) 9 (9). https://doi.org/10.3390/app9091801.
Bro, Rasmus y Age K. Smilde. 2003. “Centering and Scaling in Component Analysis.” Journal of Chemometrics 17 (1): 16-33. https://doi.org/10.1002/cem.773.
Brown, Geoffrey D., Julia Bauer, Helen M.I. Osborn y Rainer Kuemmerle. 2018. “A Solution NMR Approach to Determine the Chemical Structures of Carbohydrates Using the Hydroxyl Groups as Starting Points.” ACS Omega 3 (12): 17957-75. https://doi.org/10.1021/acsomega.8b02136.
Chemat, Farid, Maryline Abert Vian, Harish Karthikeyan Ravi, Boutheina Khadhraoui, Soukaina Hilali, Sandrine Perino y Anne Sylvie Fabiano Tixier. 2019. “Review of Alternative Solvents for Green Extraction of Food and Natural Products: Panorama, Principles, Applications and Prospects.” Molecules 24 (16): 3007. https://doi.org/10.3390/molecules24163007.
Clarke, Christopher J. y John N. Haselden. 2008. “Metabolic Profiling as a Tool for Understanding Mechanisms of Toxicity.” Toxicologic Pathology 36 (1): 140-47. https://doi.org/10.1177/0192623307310947.
Clendinen, Chaevien S., Brittany Lee-McMullen, Caroline M. Williams, Gregory S. Stupp, Krista Vandenborne, Daniel A. Hahn, Glenn A. Walter y Arthur S. Edison. 2014. “13C NMR Metabolomics: Applications at Natural Abundance.” Analytical Chemistry 86 (18): 9242-50. https://doi.org/10.1021/ac502346h.
Colnago, Luiz Alberto, Tiago Bueno Moraes y Tatiana Monaretto. 2017. “Modern Magnetic Resonance.” In Modern Magnetic Resonance. https://doi.org/10.1007/978-3-319-28275-6.
Craig, Andrew, Olivier Cloarec, Elaine Holmes, Jeremy K. Nicholson y John C. Lindon. 2006. “Scaling and Normalization Effects in NMR Spectroscopic Metabonomic Data Sets.” Analytical Chemistry 78 (7): 2262-67. https://doi.org/10.1021/ac0519312.
Davis, Richard A., Adrian J. Charlton, John Godward, Stephen A. Jones, Mark Harrison y Julie C. Wilson. 2007. “Adaptive Binning: An Improved Binning Method for Metabolomics Data Using the Undecimated Wavelet Transform.” Chemometrics and Intelligent Laboratory Systems 85 (1): 144-54. https://doi.org/10.1016/j.chemolab.2006.08.014.
Dieterle, Frank, Alfred Ross y Hans Senn. 2006. “Probabilistic Quotient Normalization as Robust Method to Aacount for Dilution of Complex Biuological Mixtures.” Anal. Chem. 78 (13): 4281-90.
Dona, Anthony C., Michael Kyriakides, Flora Scott, Elizabeth A. Shephard, Dorsa Varshavi, Kirill Veselkov y Jeremy R. Everett. 2016. “A Guide to the Identification of Metabolites in NMR-Based Metabonomics/Metabolomics Experiments.” Computational and Structural Biotechnology Journal 14: 135-53. https://doi.org/10.1016/j.csbj.2016.02.005.
Durbin, B. P., J. S. Hardin, D. M. Hawkins y D. M. Rocke. 2002. “A Variance-Stabilizing Transformation for Gene-Expression Microarray Data.” Bioinformatics 18 (SUPPL. 1): 105-10. https://doi.org/10.1093/bioinformatics/18.suppl_1.S105.
Duynhoven, J. van, A. Voda, M. Witek y H. Van As. 2010. “Time-Domain NMR Applied to Food Products.” In Annual Reports on NMR Spectroscopy, 1st ed., 69: 145-97. Elsevier Ltd. https://doi.org/10.1016/S0066-4103(10)69003-5.
Ebbels, Timothy M.D., John C. Lindon y Muireann Coen. 2011. “Processing and Modeling of Nuclear Magnetic Resonance (NMR) Metabolic Profiles.” In Methods in Molecular Biology (Clifton, N.J.), 708: 365-88. Humana Press. https://doi.org/10.1007/978-1-61737-985-7_21.
Ebrahimi, Parvaneh, Nanna Viereck, Rasmus Bro y Søren B. Engelsen. 2017. “Modern Magnetic Resonance.” In Modern Magnetic Resonance, 1-20. https://doi.org/10.1007/978-3-319-28275-6.
Eilers, Paul H.C. 2003. “A Perfect Smoother.” Analytical Chemistry 75 (14): 3631-36. https://doi.org/10.1021/ac034173t.
Eilers, Paul H.C. 2004. “Parametric Time Warping.” Analytical Chemistry 76 (2): 404–11. https://doi.org/10.1021/ac034800e.
Eilers, Paul H.C. y Brian D. Marx. 1996. “Flexible Smoothing with B-Splines and Penalties.” Statistical Science 11 (2): 89–102. https://doi.org/10.1214/ss/1038425655.
Ellis, David I., Warwick B. Dunn, Julian L. Griffin, J. William Allwood y Royston Goodacre. 2007. “Metabolic Fingerprinting as a Diagnostic Tool.” Pharmacogenomics 8 (9): 1243-66. https://doi.org/10.2217/14622416.8.9.1243.
Emwas, Abdul Hamid, Raja Roy, Ryan T. McKay, Leonardo Tenori, Edoardo Saccenti, G. A. Nagana Gowda, Daniel Raftery, et al. 2019. “Nmr Spectroscopy for Metabolomics Research.” Metabolites 9 (7). https://doi.org/10.3390/metabo9070123.
Emwas, Abdul Hamid, Edoardo Saccenti, Xin Gao, Ryan T. McKay, Vitor A.P. Martins dos Santos, Raja Roy y David S. Wishart. 2018. “Recommended Strategies for Spectral Processing and Post-Processing of 1D 1 H-NMR Data of Biofluids with a Particular Focus on Urine.” Metabolomics 14 (3): 1-23. https://doi.org/10.1007/s11306-018-1321-4.
Engelsen, Søren B y Frans W J Van Den Berg. 2017. “Modern Magnetic Resonance.” Modern Magnetic Resonance. https://doi.org/10.1007/978-3-319-28275-6.
English, A. E., K. P. Whittall, M. L.G. Joy y R. M. Henkelman. 1991. “Quantitative Two?Dimensional Time Correlation Relaxometry.” Magnetic Resonance in Medicine 22 (2): 425-34. https://doi.org/10.1002/mrm.1910220250.
Filzmoser, P. y B. Walczak. 2014. “What Can Go Wrong at the Data Normalization Step for Identification of Biomarkers?” Journal of Chromatography A 1362: 194-205. https://doi.org/10.1016/j.chroma.2014.08.050.
Fukushima, Atsushi, Mami Iwasa, Ryo Nakabayashi, Makoto Kobayashi, Tomoko Nishizawa, Yozo Okazaki, Kazuki Saito y Miyako Kusano. 2017. “Effects of Combined Low Glutathione with Mild Oxidative and Low Phosphorus Stress on the Metabolism of Arabidopsis Thaliana.” Frontiers in Plant Science 8 (August). https://doi.org/10.3389/fpls.2017.01464.
Gan, Feng, Guihua Ruan y Jinyuan Mo. 2006. “Baseline Correction by Improved Iterative Polynomial Fitting with Automatic Threshold.” Chemometrics and Intelligent Laboratory Systems 82 (1-2 SPEC. ISS): 59-65. https://doi.org/10.1016/j.chemolab.2005.08.009.
Ghosh, Soumita, Arjun Sengupta y Kousik Chandra. 2017. “SOFAST-HMQC-an Efficient Tool for Metabolomics.” In Analytical and Bioanalytical Chemistry, 409: 6731-38. https://doi.org/10.1007/s00216-017-0676-0.
Giacomoni, Franck, Gildas Le Corguillé, Misharl Monsoor, Marion Landi, Pierre Pericard, Mélanie Pétéra, Christophe Duperier, et al. 2015. “Workflow4Metabolomics: A Collaborative Research Infrastructure for Computational Metabolomics.” Bioinformatics 31 (9): 1493-95. https://doi.org/10.1093/bioinformatics/btu813.
Giraudeau, Patrick. 2020. “NMR-Based Metabolomics and Fluxomics: Developments and Future Prospects.” Analyst 145 (7): 2457-72. https://doi.org/10.1039/d0an00142b.
Giraudeau, Patrick, Illa Tea, Gérald S. Remaud y Serge Akoka. 2014. “Reference and Normalization Methods: Essential Tools for the Intercomparison of NMR Spectra.” Journal of Pharmaceutical and Biomedical Analysis 93: 3-16. https://doi.org/10.1016/j.jpba.2013.07.020.
Giskeødegård, Guro F., Tom G. Bloemberg, Geert Postma, Beathe Sitter, May Britt Tessem, Ingrid S. Gribbestad, Tone F. Bathen y Lutgarde M.C. Buydens. 2010. “Alignment of High Resolution Magic Angle Spinning Magnetic Resonance Spectra Using Warping Methods.” Analytica Chimica Acta 683 (1): 1-11. https://doi.org/10.1016/j.aca.2010.09.026.
Gostan, Thierry, Céline Moreau, Alexandre Juteau, Elisabeth Guichard y Marc André Delsuc. 2004. “Measurement of Aroma Compound Self-Diffusion in Food Models by DOSY.” Magnetic Resonance in Chemistry 42 (6): 496-99. https://doi.org/10.1002/mrc.1383.
Gottwald, Antje, Lawrence K. Creamer, Penny L. Hubbard y Paul T. Callaghan. 2005. “Diffusion, Relaxation, and Chemical Exchange in Casein Gels: A Nuclear Magnetic Resonance Study.” Journal of Chemical Physics 122 (3). https://doi.org/10.1063/1.1825383.
Hasin, Yehudit, Marcus Seldin y Aldons Lusis. 2017. “Multi-Omics Approaches to Disease.” Genome Biology 18 (1): 1-15. https://doi.org/10.1186/s13059-017-1215-1.
Hochrein, Jochen, Helena U. Zacharias, Franziska Taruttis, Claudia Samol, Julia C. Engelmann, Rainer Spang, Peter J. Oefner y Wolfram Gronwald. 2015. “Data Normalization of 1H NMR Metabolite Fingerprinting Data Sets in the Presence of Unbalanced Metabolite Regulation.” Journal of Proteome Research 14 (8): 3217-28. https://doi.org/10.1021/acs.jproteome.5b00192.
Hürlimann, M. D. y D. D. Griffin. 2000. “Spin Dynamics of Carr-Purcell-Meiboom-Gill-like Sequences in Grossly Inhomogeneous B0 and B1 Fields and Application to NMR Well Logging.” Journal of Magnetic Resonance 143 (1): 120-35. https://doi.org/10.1006/jmre.1999.1967.
Izquierdo-García, Jose L., Ignacio Rodríguez, Angelos Kyriazis, Palmira Villa, Pilar Barreiro, Manuel Desco y Jesús Ruiz-Cabello. 2009. “A Novel R-Package Graphic User Interface for the Analysis of Metabonomic Profiles.” BMC Bioinformatics 10: 1-10. https://doi.org/10.1186/1471-2105-10-363.
Izquierdo-García, Jose L., Palmira Villa, Angelos Kyriazis, Laura Del Puerto-Nevado, Sandra Pérez-Rial, Ignacio Rodriguez, Natalia Hernandez y Jesús Ruiz-Cabello. 2011. “Descriptive Review of Current NMR-Based Metabolomic Data Analysis Packages.” Progress in Nuclear Magnetic Resonance Spectroscopy 59 (3): 263-70. https://doi.org/10.1016/j.pnmrs.2011.02.001.
Jackson, J. Edward. 1980. “Principal Components and Factor Analysis: Part I-Principal Components.” Journal of Quality Technology 12 (4): 201-13. https://doi.org/10.1080/00224065.1980.11980967.
Kirtil, Emrah, Sevil Cikrikci, Michael J. McCarthy y Mecit Halil Oztop. 2017. “Recent Advances in Time Domain NMR & MRI Sensors and Their Food Applications.” Current Opinion in Food Science 17: 9-15. https://doi.org/10.1016/j.cofs.2017.07.005.
Kohl, Stefanie M., Matthias S. Klein, Jochen Hochrein, Peter J. Oefner, Rainer Spang y Wolfram Gronwald. 2012. “State-of-the Art Data Normalization Methods Improve NMR-Based Metabolomic Analysis.” Metabolomics 8 (June 2014): 146-60. https://doi.org/10.1007/s11306-011-0350-z.
Kruger, Nicholas J., M. Adrian Troncoso-Ponce y R. George Ratcliffe. 2008. “1H NMR Metabolite Fingerprinting and Metabolomic Analysis of Perchloric Acid Extracts from Plant Tissues.” Nature Protocols 3 (6): 1001-12. https://doi.org/10.1038/nprot.2008.64.
Kruk, Joanna, Marek Doskocz, El?bieta Jod?owska, Anna Zacharzewska, Joanna ?akomiec, Kornelia Czaja y Jacek Kujawski. 2017. “NMR Techniques in Metabolomic Studies: A Quick Overview on Examples of Utilization.” Applied Magnetic Resonance 48 (1): 1-21. https://doi.org/10.1007/s00723-016-0846-9.
Kumar, Keshav, Ralf Schweiggert y Claus Dieter Patz. 2020. “Introducing a Novel Procedure for Peak Alignment in One-Dimensional 1H-NMR Spectroscopy: A Prerequisite for Chemometric Analyses of Wine Samples.” Analytical Methods 12 (28): 3626-36. https://doi.org/10.1039/d0ay01011a.
Kvalheim, Olav M., Frode Brakstad y Yi zeng Llang. 1994. “Preprocessing of Analytical Profiles in the Presence of Homoscedastic or Heteroscedastic Noise.” Analytical Chemistry 66 (1): 43-51. https://doi.org/10.1021/ac00073a010.
Lee, Geun Cheol y David L. Woodruff. 2004. “Beam Search for Peak Alignment of NMR Signals.” Analytica Chimica Acta 513 (2): 413-16. https://doi.org/10.1016/j.aca.2004.02.068.
Lu, Wenyun, Xiaoyang Su, Mathias S. Klein, Ian A. Lewis, Oliver Fiehn y Joshua D. Rabinowitz. 2017. “Metabolite Measurement: Pitfalls to Avoid and Practices to Follow.” Physiology & Behavior 86: 277-304. https://doi.org/10.1146/annurev-biochem-061516-044952.
Ludwig, Christian y Mark R. Viant. 2010. “Two-Dimensional J-Resolved NMR Spectroscopy: Review of a Key Methodology in the Metabolomics Toolbox.” Phytochemical Analysis 21 (1): 22-32. https://doi.org/10.1002/pca.1186.
Mahrous, Engy A., y Mohamed A. Farag. 2015. “Two Dimensional NMR Spectroscopic Approaches for Exploring Plant Metabolome: A Review.” Journal of Advanced Research 6 (1): 3-15. https://doi.org/10.1016/j.jare.2014.10.003.
Maier, Tanja S., Jürgen Kuhn y Caroline Müller. 2010. “Proposal for Field Sampling of Plants and Processing in the Lab for Environmental Metabolic Fingerprinting.” Plant Methods 6 (1): 1-14. https://doi.org/10.1186/1746-4811-6-6.
Mannu, Alberto, Ioannis K. Karabagias, Maria Enrica Di Pietro, Salvatore Baldino, Vassilios K. Karabagias y Anastasia V. Badeka. 2020. “13C NMR-Based Chemical Fingerprint for the Varietal and Geographical Discrimination of Wines.” Foods 9 (8): 1040. https://doi.org/10.3390/foods9081040.
Mckay, Ryan T. 2011. “How the 1D-NOESY Suppresses Solvent Signal in Metabonomics NMR Spectroscopy: An Examination of the Pulse Sequence Components and Evolution.” Concepts in Magnetic Resonance Part A: Bridging Education and Research 38 A (5): 197-220. https://doi.org/10.1002/cmr.a.20223.
Meyer, Tim De, Davy Sinnaeve, Bjorn Van Gasse, Ernst R. Rietzschel, Marc L. De Buyzere, Michel R. Langlois, Sofie Bekaert, José C. Martins y Wim Van Criekinge. 2010. “Evaluation of Standard and Advanced Preprocessing Methods for the Univariate Analysis of Blood Serum 1H-NMR Spectra.” Analytical and Bioanalytical Chemistry 398 (4): 1781-90. https://doi.org/10.1007/s00216-010-4085-x.
Misra, Biswapriya B., Sarah M. Assmann y Sixue Chen. 2014. “Plant Single-Cell and Single-Cell-Type Metabolomics.” Trends in Plant Science 19 (10): 637-46. https://doi.org/10.1016/j.tplants.2014.05.005.
Moraes, Tiago Bueno, Tatiana Monaretto y Luiz Alberto Colnago. 2019. “Applications of Continuous Wave Free Precession Sequences in Low-Field, Time-Domain NMR.” Applied Sciences (Switzerland) 9 (7). https://doi.org/10.3390/app9071312.
Muncey, Harriet J., Rebecca Jones, Maria De Iorio y Timothy M.D. Ebbels. 2010. “MetAssimulo: Simulation of Realistic NMR Metabolic Profiles.” BMC Bioinformatics 11: 496. https://doi.org/10.1186/1471-2105-11-496.
Mushtaq, Mian Yahya, Young Hae Choi, Robert Verpoorte y Erica G. Wilson. 2014. “Extraction for Metabolomics: Access to the Metabolome.” Phytochemical Analysis 25 (4): 291-306. https://doi.org/10.1002/pca.2505.
Musse, Maja, Mireille Cambert y François Mariette. 2010. “NMR Study of Water Distribution inside Tomato Cells: Effects of Water Stress.” Applied Magnetic Resonance 38 (4): 455-69. https://doi.org/10.1007/s00723-010-0139-7.
Nielsen, Niels-Peter Vest, Jens Michael Carstensen y Jørn Smedsgaard. 1998. “Aligning of Single and Multiple Wavelength Chromatographic Profiles for Chemometric Data Analysis Using Correlation Optimised Warping.” Journal of Chromatography A 805 (1-2): 17-35. https://doi.org/10.1016/S0021-9673(98)00021-1.
Novoselov, K S, H L Stormer, P Kim, A Bostwick, T Seyller, K Horn, E Rotenberg, et al. 2009. “Sensitivity by Polarization Transfer.” Science 323 (March): 1708-11. https://doi.org/10.1126/science.1168877.
Öman, Tommy, May Britt Tessem, Tone F. Bathen, Helena Bertilsson, Anders Angelsen, Mattias Hedenström y Trygve Andreassen. 2014. “Identification of Metabolites from 2D H-C HSQC NMR Using Peak Correlation Plots.” BMC Bioinformatics 15 (1): 1-8. https://doi.org/10.1186/s12859-014-0413-z.
Parkinson, John A. 2018. “NMR Spectroscopy Methods in Metabolic Phenotyping.” In The Handbook of Metabolic Phenotyping, 53-96. Elsevier Inc. https://doi.org/10.1016/B978-0-12-812293-8.00002-5.
Parsons, Helen M., Christian Ludwig, Ulrich L. Günther, and Mark R. Viant. 2007. “Improved Classification Accuracy in 1- and 2-Dimensional NMR Metabolomics Data Using the Variance Stabilising Generalised Logarithm Transformation.” BMC Bioinformatics 8: 1-16. https://doi.org/10.1186/1471-2105-8-234.
P?owa?-Korus, Iwona, ?ukasz Masewicz, Artur Szwengiel, Adam Rachocki, Hanna Maria Baranowska y Wojciech Medycki. 2018. “A Novel Method of Recognizing Liquefied Honey.” Food Chemistry 245 (November): 885-89. https://doi.org/10.1016/j.foodchem.2017.11.087.
Prange, Michael y Yi Qiao Song. 2009. “Quantifying Uncertainty in NMR T2 Spectra Using Monte Carlo Inversion.” Journal of Magnetic Resonance 196 (1): 54-60. https://doi.org/10.1016/j.jmr.2008.10.008.
Prieto, Jose M., Maria Mellinas-Gomez y Mire Zloh. 2016. “Application of Diffusion-Edited and Solvent Suppression 1H-NMR to the Direct Analysis of Markers in Valerian-Hop Liquid Herbal Products.” Phytochemical Analysis 27 (2): 100-106. https://doi.org/10.1002/pca.2603.
Raffo, Antonio, Raffaella Gianferri, Renato Barbieri y Elvino Brosio. 2005. “Ripening of Banana Fruit Monitored by Water Relaxation and Diffusion 1H-NMR Measurements.” Food Chemistry 89 (1): 149–58. https://doi.org/10.1016/j.foodchem.2004.02.024.
Roberts, Lee D., Amanda L. Souza, Robert E. Gerszten y Clary B. Clish. 2012. Targeted Metabolomics NIH Public Access. https://doi.org/10.1002/0471142727.mb3002s98.Targeted.
Rodriguez-Martinez, Andrea, Rafael Ayala, Joram M. Posma, Nikita Harvey, Beatriz Jiménez, Kazuhiro Sonomura, Taka Aki Sato, et al. 2019. “PJRES Binning Algorithm (JBA): A New Method to Facilitate the Recovery of Metabolic Information from PJRES 1H NMR Spectra.” Bioinformatics 35 (11): 1916-22. https://doi.org/10.1093/bioinformatics/bty837.
Rooi, Johan J. de y Paul H.C. Eilers. 2012. “Mixture Models for Baseline Estimation.” Chemometrics and Intelligent Laboratory Systems 117: 56-60. https://doi.org/10.1016/j.chemolab.2011.11.001.
Sacchi, Raffaele y Livio Paolillo. 2007. “NMR for Food Quality and Traceability.” Advances in Food Diagnostics, no. November: 101–17. https://doi.org/10.1002/9780470277805.ch5.
Sauerschnig, Claudia, Maria Doppler, Christoph Bueschl y Rainer Schuhmacher. 2018. “Methanol Generates Numerous Artifacts during Sample Extraction and Storage of Extracts in Metabolomics Research.” Metabolites 8 (1): 1-19. https://doi.org/10.3390/metabo8010001.
Savorani, F., G. Tomasi y S. B. Engelsen. 2010. “Icoshift: A Versatile Tool for the Rapid Alignment of 1D NMR Spectra.” Journal of Magnetic Resonance 202 (2): 190-202. https://doi.org/10.1016/j.jmr.2009.11.012.
Schripsema, Jan. 2010. “Application of NMR in Plant Metabolomics: Techniques, Problems and Prospects.” Phytochemical Analysis 21 (1): 14-21. https://doi.org/10.1002/pca.1185.
Son, Hong Seok, Myong Kim Ki, Frans Van Den Berg, Geum Sook Hwang, Won Mok Park, Cherl Ho Lee y Young Shick Hong. 2008. “1H Nuclear Magnetic Resonance-Based Metabolomic Characterization of Wines by Grape Varieties and Production Areas.” Journal of Agricultural and Food Chemistry 56 (17): 8007-16. https://doi.org/10.1021/jf801424u.
Todt, Harald, Wolfgang Burk, Gisela Guthausen, Andreas Guthausen, Andreas Kamlowski y Dieter Schmalbein. 2001. “Quality Control with Time-Domain NMR.” European Journal of Lipid Science and Technology 103 (12): 835-40. https://doi.org/10.1002/1438-9312(200112)103:123.0.CO;2-P.
Tønning, Erik, Daniel Polders, Paul T. Callaghan y Søren B. Engelsen. 2007. “A Novel Improved Method for Analysis of 2D Diffusion-Relaxation Data-2D PARAFAC-Laplace Decomposition.” Journal of Magnetic Resonance 188 (1): 10-23. https://doi.org/10.1016/j.jmr.2007.05.018.
Torgrip, Ralf J.O., K. M. Åberg, E. Alm, I. Schuppe-Koistinen y J. Lindberg. 2008. “A Note on Normalization of Biofluid 1D 1H-NMR Data.” Metabolomics 4 (2): 114-21. https://doi.org/10.1007/s11306-007-0102-2.
Ulaszewska, Marynka M., Christoph H. Weinert, Alessia Trimigno, Reto Portmann, Cristina Andres Lacueva, René Badertscher, Lorraine Brennan, et al. 2019. “Nutrimetabolomics: An Integrative Action for Metabolomic Analyses in Human Nutritional Studies.” Molecular Nutrition and Food Research 63 (1): 1-86. https://doi.org/10.1002/mnfr.201800384.
Valentino, Giovanna, Vittoria Graziani, Brigida D’Abrosca, Severina Pacifico, Antonio Fiorentino y Monica Scognamiglio. 2020. “NMR-Based Plant Metabolomics in Nutraceutical Research: An Overview.” Molecules 25 (6). https://doi.org/10.3390/molecules25061444.
Vu, Thao, Eli Riekeberg, Yumou Qiu y Robert Powers. 2018. “Comparing Normalization Methods and the Impact of Noise.” Metabolomics 14 (8): 108. https://doi.org/10.1007/s11306-018-1400-6.
Vu, Trung N., Dirk Valkenborg, Koen Smets, Kim A. Verwaest, Roger Dommisse, Filip Lemière, Alain Verschoren, Bart Goethals y Kris Laukens. 2011. “An Integrated Workflow for Robust Alignment and Simplified Quantitative Analysis of NMR Spectrometry Data.” BMC Bioinformatics 12:405. https://doi.org/10.1186/1471-2105-12-405.
Wagner, Tobias y Simon Wessing. 2012. “On the Effect of Response Transformations in Sequential Parameter Optimization.” Evolutionary Computation 20 (2): 229-48. https://doi.org/10.1162/EVCO_a_00061.
Wang, Jeffrey H., Jaeman Byun y Subramaniam Pennathur. 2010. “Analytical Approaches to Metabolomics and Applications to Systems Biology.” Seminars in Nephrology 30 (5): 500-511. https://doi.org/10.1016/j.semnephrol.2010.07.007.
Wang, Tao, Kang Shao, Qinying Chu, Yanfei Ren, Yiming Mu, Lijia Qu, Jie He, Changwen Jin y Bin Xia. 2009. “Automics: An Integrated Platform for NMR-Based Metabonomics Spectral Processing and Data Analysis.” BMC Bioinformatics 10: 1-15. https://doi.org/10.1186/1471-2105-10-83.
Wong, Jason W.H., Caterina Durante y Hugh M. Cartwright. 2005. “Application of Fast Fourier Transform Cross-Correlation for the Alignment of Large Chromatographic and Spectral Datasets.” Analytical Chemistry 77 (17): 5655-61. https://doi.org/10.1021/ac050619p.
Workman, Christopher, Lars Juhl Jensen, Hanne Jarmer, Randy Berka, Laurent Gautier, Henrik Bjørn Nielser, Hans Henrik Saxild, Claus Nielsen, Søren Brunak y Steen Knudsen. 2002. “A New Non-Linear Normalization Method for Reducing Variability in DNA Microarray Experiments.” Genome Biology 3 (9): 1-16. https://doi.org/10.1186/gb-2002-3-9-research0048.
Worley, Bradley y Robert Powers. 2013. “Multivariate Analysis in Metabolomics.” Current Metabolomics 1 (1): 92-107. https://doi.org/10.2174/2213235x11301010092.
Worley, Bradley y Robert Powers. 2014a. “MVAPACK?: A Complete Data Handling Package for NMR Metabolomics.” ACS Chemical Biology 9: 1-15.
Worley, Bradley y Robert Powers. 2014b. “Simultaneous Phase and Scatter Correction for NMR Datasets.” Chemometrics and Intelligent Laboratory Systems 131: 1-6. https://doi.org/10.1016/j.chemolab.2013.11.005.
Worley, Bradley y Robert Powers. 2015. “Generalized Adaptive Intelligent Binning of Multiway Data.” Chemometrics and Intelligent Laboratory Systems 146: 42-46. https://doi.org/10.1016/j.chemolab.2015.05.005.
Wu, Wen, Michal Daszykowski, Beata Walczak, Brian C. Sweatman, Susan C. Connor, John N. Haselden, Daniel J. Crowther, Rob W. Gill y Michael W. Lutz. 2006. “Peak Alignment of Urine NMR Spectra Using Fuzzy Warping.” Journal of Chemical Information and Modeling 46 (2): 863-75. https://doi.org/10.1021/ci050316w.
Xi, Yuanxin y David M. Rocke. 2008. “Baseline Correction for NMR Spectroscopic Metabolomics Data Analysis.” BMC Bioinformatics 9: 1-10. https://doi.org/10.1186/1471-2105-9-324.
Xia, Jianguo, Nick Psychogios, Nelson Young y David S. Wishart. 2009. “MetaboAnalyst: A Web Server for Metabolomic Data Analysis and Interpretation.” Nucleic Acids Research 37 (SUPPL. 2): 652-60. https://doi.org/10.1093/nar/gkp356.
Xiao, Jiao, Gang Chen y Ning Li. 2018. “Ionic Liquid Solutions as a Green Tool for the Extraction and Isolation of Natural Products.” Molecules 23 (7): 1765. https://doi.org/10.3390/molecules23071765.
Xu, Zheng, Robert H. Morris, Martin Bencsik y Michael I. Newton. 2014. “Detection of Virgin Olive Oil Adulteration Using Low Field Unilateral NMR.” Sensors (Switzerland) 14 (2): 2028-35. https://doi.org/10.3390/s140202028.
Yang, Li, Kui Shan Wen, Xiao Ruan, Ying Xian Zhao, Feng Wei y Qiang Wang. 2018. “Response of Plant Secondary Metabolites to Environmental Factors.” Molecules 23 (4): 1-26. https://doi.org/10.3390/molecules23040762.
Zhang, Jinsheng, Yuhuan Liu, Na Wang y Roger Ruan. 2012. “NMR Technique Application in Evaluating the Quality of Navel Orange during Storage.” Procedia Engineering 37: 234-39. https://doi.org/10.1016/j.proeng.2012.04.233.
Zhao, Qi, Radka Stoyanova, Shuyan Du, Paul Sajda y Truman R. Brown. 2006. “HiRes - A Tool for Comprehensive Assessment and Interpretation of Metabolomic Data.” Bioinformatics 22 (20): 2562-64. https://doi.org/10.1093/bioinformatics/btl428.
Zou, Pingping, Yuelin Song, Wei Lei, Jun Li, Pengfei Tu y Yong Jiang. 2017. “Application of 1H NMR-Based Metabolomics for Discrimination of Different Parts and Development of a New Processing Workflow for Cistanche Deserticola.” Acta Pharmaceutica Sinica B 7 (6): 647-56. https://doi.org/10.1016/j.apsb.2017.07.003.