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Application of NMR techniques to the determination of the composition of tobacco, coffee, and tea products

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Abstract

The application of NMR spectroscopy, including its up-to-date versions (correlation homo- and heteronuclear spectroscopy, Overhauser effect, solid-state NMR, etc.), to the analysis of tobacco and tobacco products, tea, and coffee is considered. The advantages and limitations of NMR techniques in the analysis of complex mixtures, as compared with chromatography-mass spectrometry and other instrumental techniques, are discussed based on particular examples.

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References

  1. Roberts, J.D., Organic Chemistry Application, in Encyclopedia of Nuclear Magnetic Resonance, Grant, D.M. and Harris, R.K., Eds., Wiley and Sons, 2003, vols. 1–9, 8603 p.

  2. Pelczer, I., Magn. Reson. Chem., 2009, vol. 47, no. S1, p. S1.

    CAS  Google Scholar 

  3. Emsley, J.W. and Feeney, J., Prog. Nucl. Magn. Reson. Spectrosc., 2007, vol. 50, p. 179.

    CAS  Google Scholar 

  4. Wei, F., Furihata, K., Hu, F., Miyakawa, T., and Tanokura, M., Magn. Reson. Chem., 2010, vol. 48, no. 11, p. 857.

    CAS  Google Scholar 

  5. Gil, A.M., Duarte, I.F., Godejohann, M.U., Braumann, U., Maraschin, M., and Spraul, M., Anal. Chim. Acta, 2003, vol. 488, p. 35.

    CAS  Google Scholar 

  6. Kwan, E.I. and Huang, S.G., Eur. J. Org. Chem., 2008, no. 16, p. 2671.

    Google Scholar 

  7. Claridge, T.D.W., High Resolution NMR Techniques, in Tetrahedron Organic Chemistry Series, Amsterdam: Elsevier, 2009, vol. 27.

    Google Scholar 

  8. Elipe, M.V.S., Anal. Chim. Acta, 2003, vol. 497, p. 1.

    Google Scholar 

  9. Mannina, L., Sobolev, A. P., Proietti, N., and Capitani, D., Abstracts of Papers, EUROMAR 2010 and 17th ISMAR Conf. World Wide Magnetic Resonance 2010, Firenze, 2010.

    Google Scholar 

  10. Mannina, L., Sobolev, A.P., and Viel, S., Prog. Nucl. Magn. Reson. Spectrosc., 2012, vol. 66, p. 1.

    CAS  Google Scholar 

  11. Savorani, F., Dottorato: Scienze degli Alimenti (XIX Ciclo). Applicazione del Metodi Chemometrici alla Spectroscopia di Risonanza Magnetica Nucleare (NMR) per la Valutazione della Qualita dei Prodotti Ortofrutticoli e per l’Individuazione della Loro Origine Geografica (A Case Study Development of Chemical Indexes, Originated from the Application of Chemometric Methods to the Nuclear Magnetic Resonance, in the Assessment of the Quality and of the Geographical Origin of Vegetable Products), Doctoral Dissertation, Bologna: Univ. di Bologna, 2007.

    Google Scholar 

  12. Vershinin, V.I., J. Anal. Chem., 2011, vol. 66, no. 11, p. 1124.

    Google Scholar 

  13. McKenzie, J.S., Donarski, J.A., Wilson, J.C., and Charlton, A.J., Prog. Nucl. Magn. Reson. Spectrosc., 2011, vol. 59, p. 336.

    CAS  Google Scholar 

  14. Tatarchenko, I.I., Mokhnachev, I.G., and Kas’yanov, G.I., Khimiya subtropicheskikh i pishchevkusovykh produktov (Chemistry of Subtropical and Flavor-Generating Products), Moscow: Academia, 2003.

    Google Scholar 

  15. Russian Federation Federal Law no. 268-F3: Technical Regimen to Tobacco Articles.

  16. Hounsome, N., Hounsome, B., Tomos, D., and Edwards-Jones, G., J. Food Sci., 2008, vol. 73, no. 4, p. R48.

    CAS  Google Scholar 

  17. Powers, R., Magn. Reson. Chem., 2009, vol. 47, no. S1, p. S2.

    CAS  Google Scholar 

  18. Shachar-Hill, Y., Metab. Eng., 2002, vol. 4, no. 1, p. 90.

    CAS  Google Scholar 

  19. Ratcliffe, R.G., Roscher, A., and Shachar-Hill, Y., Prog. Nucl. Magn. Reson. Spectrosc., 2001, vol. 39, p. 267.

    Google Scholar 

  20. Soininen, P., Quantitative 1H NMR Spectroscopy — Chemical and Biological Applications, in Natural and Environmental Sciences 240, Kuopio: Kuopio Univ., 2008.

    Google Scholar 

  21. Tang, H., Xiao, C., and Wanga, Y., Magn. Reson. Chem., 2009, vol. 47, no. S1, p. S157.

    CAS  Google Scholar 

  22. Martin, G.E., Cryogenic NMR Probes: Application, in Encyclopedia of Nuclear Magnetic Resonance, Grant, D.M. and Harris, R.K., Eds., Wiley, 2003.

    Google Scholar 

  23. Schroeder, M.A., Atherton, H.J., Ball, D.R., Cole, L.M.A., Heather, C., Griffin, J.L., Clarke, K., Radda, G.K., and Tyler, D., FASEB J., 2009, vol. 23, p. 2529.

    CAS  Google Scholar 

  24. Rastrelli, F., Schievano, E., Bagno, A., and Mammi, S., Magn. Reson. Chem., 2009, vol. 47, no. 10, p. 868.

    CAS  Google Scholar 

  25. Kaiser, K.A., Barding, G.A., Jr., and Larive, C.K., Magn. Reson. Chem., 2009, vol. 47, no. S1, p. 147.

    Google Scholar 

  26. Mashkovtsev, M.F., Khimiya tabaka (Chemistry of Tobacco), Moscow: Pishchevaya promyshlennost’, 1971.

    Google Scholar 

  27. Shmuk, A.A., Khimiya i tekhnologiya tabaka (Chemistry and technology of Tobacco), Moscow: Pishchepromizdat, 1953.

    Google Scholar 

  28. Green, C.R. and Rodgman, A., Rec. Adv. Tob., 1996, vol. 22, p. 131.

    Google Scholar 

  29. Centre de Cooperation pour les Recherches Scientifiques relatives au Tabac.

  30. Perfetti, T.A. and Rodgman, A., The Chemical Components of Tobacco and Tobacco Smoke, CRC Press, 2008.

    Google Scholar 

  31. Uryupin, A.B., Kochetkov, K.A., and Nekrasov, Yu.S., Tobacco Rev., 2009, no. 3, p. 24.

    Google Scholar 

  32. The Scientific Basis of Tobacco Product Regulation, in WHO technical Report Series no. 945, World Health Organization, 2007.

  33. Friebolin, H., Basic One- and Two-Dimensional NMR-Spectroscopy, Weinheim: Wiley-VCH, 1997.

    Google Scholar 

  34. Analytical Determination of Nicotine and Related Compounds and their Metabolites, Gorrod, J.W. and Jacob III, P., Eds., Amsterdam: Elsevier, 1999.

    Google Scholar 

  35. Whidgby, J.F. and Seeman, J.I., J. Org. Chem., 1976, vol. 41, p. 1585.

    Google Scholar 

  36. Seeman, J.I., Secor, H.V., Chavdarian, C.G., Sanders, E.B., Bassfield, R.L., and Whidgby, J.F., J. Org. Chem., 1981, vol. 46, p. 3040.

    CAS  Google Scholar 

  37. Pittner, P., Seeman, J.I., and Whidgby, J.F., J. Heterocycl. Chem., 1978, vol. 15, p. 585.

    Google Scholar 

  38. Perfetti, T.A., Beitr. Tabakforsch. Int., 1983, vol. 12, no. 2, p. 43.

    CAS  Google Scholar 

  39. Pretsch, E. and Clerc, J.T., Spectra Interpretation of Organic Compounds, Wiley-VCH, 1997.

    Google Scholar 

  40. Berger, S. and Braun, S., 200 and more NMR Experiments, Wiley-VCH, 2004.

    Google Scholar 

  41. Derome, E., Modern NMR Techniques for Chemistry Research, Pergamon, 1987.

    Google Scholar 

  42. Uryupin, A.B., Petrovskii, P.V., and Peregudov, A.S., Abstracts of Papers, II Mezhdunarodnogo Foruma Analitika i analitiki (Proc. II Int. Conf. Analytics and Analysts), Voronezh, 2008.

    Google Scholar 

  43. Uryupin, A.B. and Peregudov, A.S., Tobacco Rev., 2009, no. 3, p. 18.

    Google Scholar 

  44. Liu, B., Wei, Y., Wu, D., Jin, J., and Zhang, Y., Abstracts of Papers, CORESTA Congress, Shanghai, China, 2008.

    Google Scholar 

  45. Berger, S. and Sicker, D., Classics in Spectroscopy. Isolation and Structure Elucidation of Natural Products, Weinheim: Wiley, 2009.

    Google Scholar 

  46. Zhao, M., Wang, H., Yang, B., and Tao, H., Food Chem., 2010, vol. 120, no. 4, p. 1138.

    CAS  Google Scholar 

  47. Hecht, S.S., Spratt, T.E., and Trushin, N., Carcinogenesis, 1997, vol. 18, no. 9, p. 1851.

    CAS  Google Scholar 

  48. Pankow, J.F., Barsant, K.C., and Peyton, D.H., Chem. Res. Toxicol., 2003, vol. 16, p. 23.

    CAS  Google Scholar 

  49. Barsanti, K.C., Luo, W., Isabelle, L.M., Pankow, J.F., and Peyton, D.H., Magn. Reson. Chem., 2007, vol. 45, no. 2, p. 167.

    CAS  Google Scholar 

  50. Coleman, W.M., Abstracts of Papers, CORESTA Congress, Shanghai, 2008.

    Google Scholar 

  51. Coleman, W.M., Beitr. Tabakforsch. Int., 2008, vol. 23, no. 3, p. 121.

    CAS  Google Scholar 

  52. Bartalis, J., Zhao, Y.-L., Flora, J.W., Paine III, J.B., and Wooten, J.B., Anal. Chem., 2009, vol. 81, no. 2, p. 631.

    CAS  Google Scholar 

  53. Krishnan, P., Kruger, N.J., and Ratcliffe, R.G., J. Exp. Bot., 2005, vol. 56, no. 410, p. 255.

    CAS  Google Scholar 

  54. Bart, J., Kolkman, A.J., Oosthoek-de Vries, A.J., Koch, K., Nieuwland, P.J., Janssen, H.(J.W.G.), van Bentum, J.(P.J.M.), Ampt, K.A.M., Rutjes, P.J.T., Wijmenga, S.S., Gardeniers, H.(J.G.E.), and Kentgens, A.P.M., J. Am. Chem. Soc., 2009, vol. 131, no. 14, p. 5014.

    CAS  Google Scholar 

  55. Izotopnaya mass-spektrometriya legkikh gazoobrazuyushchikh elementov (Isotope Mass Spectrometry of Light Gas-Forming Elements), Sevast’yanov, V.S., Ed., Moscow: Fizmatlit, 2011.

    Google Scholar 

  56. Martin, G.J. and Martin, G.J., Isot. Environ. Health Stud., 1998, vol. 34, no. 3, p. 233.

    CAS  Google Scholar 

  57. Albert, K., On-line LC-NMR and Related Techniques, Chichester: Wiley, 2002.

    Google Scholar 

  58. Alberti, E., Belton, P.S., and Gil, A.M., Ann. Rep. NMR Spectrosc., 2002, vol. 47, p. 109.

    CAS  Google Scholar 

  59. LC-NMR/MS. Jeol Technical Note, 2009.

  60. Peregudov, A.S., Uryupin, A.B., Kachala, V.V., Braumann, U., and Kochetkov, K.A., Tobacco Rev., 2011, no. 2, p. 16.

    Google Scholar 

  61. Neidig, P., Spraul, M., Han, D.-Y., Lee, E.I., Zurek, G., Baessmann, C., Ingendoh, A., and Wetter, A., Combined Principle Component Analysis (PCR) of LC/MS and NMR: Observations in Urine Samples from a Lifestyle Study, Montreux, 2009.

    Google Scholar 

  62. Finster, P., Hollweg, J., and Seehofer, F., Beitr. Tabakforsc., 1986, vol. 13, no. 5, p. 255.

    CAS  Google Scholar 

  63. Schramm, S., Carre, V., Scheffler, J.-L., and Aubriet, F., Anal. Chem., 2011, vol. 83, no. 1, p. 133.

    CAS  Google Scholar 

  64. Fattorusso, E. and Taglialatela-Scafati, O., Modern Alkaloids, Weinheim: Wiley, 2008.

    Google Scholar 

  65. Armstrong, D.A., Wang, X., and Ercal, N., Chirality, 1998, vol. 10, p. 587.

    CAS  Google Scholar 

  66. Xie, W., Liu, B., Gu, W., Shen, Y., and Lu, Y., Abstracts of Papers, CORESTA Congress, Shanghai, 2008.

    Google Scholar 

  67. Ravard, A. and Crooks, P.A., Chirality, 1995, vol. 8, p. 295.

    Google Scholar 

  68. Wenzel, T.J., Discrimination of Chiral Compounds using NMR Spectroscopy, New Jersey: Wiley and Sons, 2007.

    Google Scholar 

  69. Jaroszewski, J.W. and Oleson, A., J. Pharm. Biomed. Anal., 1994, vol. 12, no. 3, p. 295.

    CAS  Google Scholar 

  70. Al Deen, T.S., Hibbert, D.B., Hook, J.M., and Wells, R.J., Anal. Chim. Acta, 2002, vol. 474, p. 125.

    Google Scholar 

  71. Sviridov, A.V., Shushkova, T.V., Ermakova, N.T., and Leont’evskii, A.A., Abstracts of Papers, Tez. dokl. Mezhdunarodnoi shkoly-konferentsii Genetika Mikroorganizmov i biotekhnologiya (Proc. Int. School-Conf. Genetics of Microorganisms and Biotechnology, Pushchino, 2008.

    Google Scholar 

  72. Danova-Alt, R., Dijema, C., and De Waard, P., Plant Cell Environ., 2008, vol. 31, no. 10, p. 1510.

    CAS  Google Scholar 

  73. Ellington, J.J., Wolfe, N.L., Garrison, A.W., Evans, J.J., Avants, J.K., Teng, Q., Environ. Sci. Technol., 2001, vol. 35, p. 3213.

    CAS  Google Scholar 

  74. Murav’eva, D.A., Tropicheskie i subtropicheskie lekarstvennye rasteniya (Tropical and Subtropical Medicinal Plants), Moscow: Meditsina, 1983.

    Google Scholar 

  75. Yilmaz, A., Nyberg, N.T., Molgaard, P., Asili, J., and Jaroshewski, J.W., Metabolomics, 2010, vol. 6, p. 511.

    CAS  Google Scholar 

  76. Ordoudi, S.A. and Tsimidou, M.S., Saffron Quality: Effect on Agricultural Practices, Processing and Storage, in Production Practices and Quality Assessment of Food Crops, Dris, R. and Jain, S.M., Eds., Kluwer Academic Publishers, 2004, vol. 1.

  77. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, World Health Organization, 2007, vol. 89.

  78. Jalali-Heravi, M., Parastar, H., and Ebrahimi-Najafabadi, H., Anal. Chim. Acta, 2010, vol. 662, p. 143.

    CAS  Google Scholar 

  79. Axelson, D.A. and Wooten, J.B., J. Agric. Food Chem., 2000, vol. 48, no. 6, p. 2199.

    CAS  Google Scholar 

  80. Manz, B., Mueller, K., Kucera, B., Volre, F., and Lehbner, G., Plant Physiol., 2005, vol. 138, no. 3, p. 1538.

    CAS  Google Scholar 

  81. Ma, Z., Barich, D.H., Solum, M.S., and Pugmire, R.J., J. Agric. Food Chem., 2004, vol. 52, no. 2, p. 215.

    CAS  Google Scholar 

  82. Sharma, R.K., Wooten, J.B., Baliga, V.L., Martoglio-Smith, P.A., and Hajaligol, M.R., J. Agric. Food Chem., 2002, vol. 50, no. 4, p. 771.

    CAS  Google Scholar 

  83. Sinnolt, K., The Art and Craft of Coffee: an Enthusiast’s Guide to Selecting Roasting and Brewing Exquisite Coffee, Beverly: Querry Books, 2010.

    Google Scholar 

  84. Flament, I., Coffee Flavor Chemistry, Chichester: Wiley, 2002.

    Google Scholar 

  85. Amorim, A.C.L., Hovell, A.M.C., Pinto, A.C., Eberlin, M.N., Arruda, N.P, Pereira, E.J., Bizzo, H.R., Catharino, R.R., Filho, Z.B.M., and Rezende, C.M., J. Brazil. Chem. Soc., 2009, vol. 20, no. 2, p. 313.

    CAS  Google Scholar 

  86. Maeztu, L., Sanz, C., Andueza, S., De Pena, M.P., Bello, J., and Cid, C., Food Chem., 2001, vol. 49, no. 11, p. 5437.

    CAS  Google Scholar 

  87. Briandet, R., Kemsley, E.K., and Wilson, R.H., J. Agric. Food Chem., 1996, vol. 44, no. 1, p. 170.

    CAS  Google Scholar 

  88. Tavares, L.A. and Ferreira, A.G., Quim. Nova, 2006, vol. 29, no. 5, p. 911.

    CAS  Google Scholar 

  89. Del Campo, G., Berregi, I., Caracena, R., and Zurriarrain, J., Talanta, 2010, vol. 81, nos. 1–2, p. 367.

    Google Scholar 

  90. Horman, I. and Viani, R., J. Food. Sci., 1972, vol. 37, no. 6, p. 925.

    CAS  Google Scholar 

  91. D’Amelio, N., Fontanive, L., Uggeri, F., Suggi-Liverani, F., and Navarini, L., Food Biophys., 2009, vol. 4, p. 321.

    Google Scholar 

  92. Capek, P., Matulova, M., Navarini, L., and Livarani, F.S., J. Agric. Food Chem., 2009, vol. 48, no. 2, p. 80.

    CAS  Google Scholar 

  93. Boosfeld, J. and Vitzthum, O.G., J. Food Sci., 1995, vol. 60, no. 5, p. 1092.

    CAS  Google Scholar 

  94. Bosco, M., Toffanin, R., de Palo, D., Zatti, L., and Segre, A., J. Sci. Food Agric., 1999, vol. 79, p. 869.

    CAS  Google Scholar 

  95. Charlton, A.J., Farrington, W.H.H., and Brereton, P., J. Agric. Food Chem., 2002, vol. 50, no. 11, p. 3098.

    CAS  Google Scholar 

  96. Madhava Naidu, M., Sulochanamma, G., Sampathu, S.R., and Srinivas, P., Food Chem., 2008, vol. 107, p. 377.

    CAS  Google Scholar 

  97. Nakatani, N., Kayano, S., Kikuzaki, H., Sumino, K., Katagiri, K., and Mitani, T., J. Agric. Food Chem., 2000, vol. 48, no. 11, p. 5512.

    CAS  Google Scholar 

  98. Danho, D., Naulet, N., and Martin, G.I., Analusis, 1992, vol. 20, no. 3, p. 179.

    CAS  Google Scholar 

  99. Toffanin, R.A., Piras, A., Szomolanyi, P., Vittur, F., Pacorini, R., Schillani, F., and Piran, A., Abstracts of Papers, ASIC 19eme Colloque Scientifique International sur le Cafe, Trieste, Italy, 2001. Chemistry: Proceeding № 20.

  100. Miglietti, M.L., Lamanna, R., Bonnilaender, B.R., and Toffanin, R., Abstracts of Papers, ASIC 21eme Colloque Scientifique International sur le Cafe, Montpellier, 2006.

  101. Wei, F., Furihata, K., Hu, F., Miyakawa, T., and Tanokura, M., J. Agric. Food Chem., 2011, vol. 59, no. 17, p. 9065.

    CAS  Google Scholar 

  102. Caligiani, A., Acquoti, D., Cirlini, M., and Palla, G., J. Agric. Food Chem., 2010, vol. 58, no. 23, p. 12105.

    CAS  Google Scholar 

  103. Kidric, J., Ann. Rep. NMR Spectrosc., 2008, vol. 54, p. 161.

    Google Scholar 

  104. Harbowy, M.E., Balentine, D.A., Davies, A.P., and Cai, Y., Crit. Rev. Plant Sci., 1997, vol. 16, no. 5, p. 415.

    CAS  Google Scholar 

  105. Sakata, K., Sakuraba, S., Yagi, A., Ina, K., Hara, T., and Tadakazu, T., Agric. Biol. Chem., 1986, vol. 50, no. 7, p. 1919.

    CAS  Google Scholar 

  106. Sakata, K., Yamauchi, H., Yagi, A., and Ina, K., Agric. Biol. Chem., 1987, vol. 51, no. 6, p. 1737.

    CAS  Google Scholar 

  107. Sakata, K., Yamauchi, H., Yagi, A., Ina, K., Parkanyi, L., and Clardy, J., Agric. Biol. Chem., 1989, vol. 53, no. 11, p. 2975.

    CAS  Google Scholar 

  108. Le Gall, G.L., Colquhoun, I.J., and Defernez, M., J. Agric. Food Chem., 2004, vol. 52, no. 4, p. 692.

    Google Scholar 

  109. Otto, M., Analytische Chemie, Weinheim: Wiley-VCH, 2000.

    Google Scholar 

  110. Kajiya, K., Kumazawa, S., Naito, A., and Nakayama, T., Magn. Reson. Chem., 2008, vol. 46, no. 2, p. 174.

    CAS  Google Scholar 

  111. Nagata, T., Hayatsu, M., and Kosuge, N., Phytochemistry, 1992, vol. 31, no. 4, p. 1215.

    CAS  Google Scholar 

  112. Chen, Y.,M., Wang, M.K., and Huang, P.M., J. Agric. Food Chem., 2006, vol. 54, no. 1, p. 212.

    CAS  Google Scholar 

  113. Daykin, C.A., van Duynoven, J.P.M., Groenewegen, A., Dachtler, M., van Amelsvoort, J.M.M., and Mulder, T.P.J., J. Agric. Food Chem., 2005, vol. 53, no. 5, p. 1428.

    CAS  Google Scholar 

  114. Fujiwara, M., Ando, I., and Arifuku, K., Anal. Sci., 2006, vol. 22, p. 1307.

    CAS  Google Scholar 

  115. Fan, I.W.M., Prog. Nucl. Magn. Reson. Spectrosc., 1996, vol. 28, p. 161.

    CAS  Google Scholar 

  116. Tarachiwin, L., Ute, K., Kobayashi, K., and Fukusaki, E., J. Agric. Food Chem., 2007, vol. 55, no. 23, p. 9330.

    CAS  Google Scholar 

  117. Lee, J.-E., Lee, B.-M., Chung, J.-O., Hwang, J.-A., Lee, S.-J., Lee, C.-H., and Hong, Y.-S., J. Agric. Food Chem., 2010, vol. 58, no. 19, p. 10582.

    CAS  Google Scholar 

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  1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    A. B. Uryupin & A. S. Peregudov

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Original Russian Text ¢ A.B. Uryupin, A.S. Peregudov, 2013, published in Zhurnal Analiticheskoi Khimii, 2013, Vol. 68, No. 12, pp. 1148–1159.

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Uryupin, A.B., Peregudov, A.S. Application of NMR techniques to the determination of the composition of tobacco, coffee, and tea products. J Anal Chem 68, 1021–1032 (2013). https://doi.org/10.1134/S1061934813120125

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