Identification and quantification of the main organic components in artisanal apple vinegars from Iraq Kurdistan region by 1H NMR spectroscopy

Lana H. Chawishli

doi:10.21271/ZJPAS.36.2.10

Authors

Lana H. Chawishli Department of Chemistry, College of Education, Salahaddin University-Erbil, Kurdistan Region, Iraq

DOI:

https://doi.org/10.21271/ZJPAS.36.2.10

Keywords:

1H NMR spectroscopy, apple vinegars, quantitative; component analysis

Abstract

The proton NMR spectra of apple vinegar samples obtained from the farms of Kurdistan region-Iraq, have been thoroughly examined and reported. Many organic molecules from various classes were assigned, including organic acids, alcohols, volatile compounds, and amino acids. Without extraction or pre-concentration processes, the possibility of quantifying the compounds that were present in the whole vinegar sample was also investigated. The results showed that ¹H NMR with water suppression allows a quick simultaneous determination of acetic, formic, lactic, malic, succinic, tartaric acids, ethanol, methanol, acetoin, 2,3-butanediol, glucose and fructose, by using dimethyl sulfone (DMSO₂) or potassium hydrogen phthalate (KHP) as internal standards. The ¹H NMR method was applied to differentiation of the various samples of apple vinegar.

References

Amin, N. & Claridge, T. 2017. Quantitative NMR Spectroscopy. oxford university.

Andreotti, G., Lamanna, R., Trivellone, E. & Motta, A. 2002. 13C NMR spectra of TAG: an easy way to distinguish milks from different animal species. Journal of the American Oil Chemists' Society, 79, 123-127.

Andreotti, G., Trivellone, E., Lamanna, R., Di Luccia, A. & Motta, A. 2000. Milk identification of different species: 13C-NMR spectroscopy of triacylglycerols from cows and buffaloes’ milks. Journal of Dairy Science, 83, 2432-2437.doi: 10.3168/jds.S0022-0302(00)75133-2.

Belloque, J. and Ramos, M. 1999. Application of NMR spectroscopy to milk and dairy products. Trends Food Sci. Technol, 10, 313–320 https://doi.org/10.1016/S0924-2244(00)00012-1

Boffo, E. F., Tavares, L. A., Ferreira, M. M. & Ferreira, A. G. 2009. Classification of Brazilian vinegars according to their 1H NMR spectra by pattern recognition analysis. LWT - Food Science and Technology, 42,1455–1460. doi:10.1016/j.lwt.2009.05.008

Budak, N. H., Doguc, D.K., Savas, C. M., Seydim, A. C., Kok Tas, T., Ciris, M. I. & Guzel-Seydim, Z. B. 2011. Effects of apple cider vinegars produced with different techniques on blood lipids in high-cholesterol-fed rats. Journal of Agricultural and Food Chemistry, 59, 6638-6644. https://doi.org/10.1021/jf104912h

Caligiani, A., Acquotti, D., Palla, G. & Bocchi, V. 2007. Identification and quantification of the main organic components of vinegars by high resolution 1H NMR spectroscopy. Analytica Chimica Acta, 585, 110-119. https://doi.org/10.1016/j.aca.2006.12.016

Chen, T., Gui, Q., Shi, J. J., Zhang, X. Y. & Chen, F. S. 2013. Analysis of variation of main components during aging process of Shanxi Aged Vinegar, Acetic Acid Bacteria, 2, 31–38 https://doi.org/10.4081/aab. 2013.s1.e6

Cocchi, M., Lambertini, P., Manzini, D., Marchetti, A. & ulrici, A. 2002. Determination of carboxylic acids in vinegars and in Aceto Balsamico Tradizionale di Modena by HPLC and GC methods, J. Agric.Food Chem., 50, 5255-5261. https://doi.org/10.1021/jf020155l

Consonni, R. And Gatti, A., 2004, 1H NMR Studies on Italian Balsamic and Traditional Balsamic Vinegars, J. Agric. Food Chem. 52, 3446-3450

De las Heras, E., Z uriarrain-Ocio, A., Zuriarrain J., Bordagaray, A., Dueñas, M. T. & Berregi, I. J. F. 2020. Quantitative determination of acrolein in cider by 1H NMR spectrometry, Foods, 9, 1820. doi:10.3390/foods9121820

Erbe, T. & Brückner, H. 1998. Chiral amino acid analysis of vinegars using gas chromatography–selected ion monitoring mass spectrometry, Z Lebensm Unters Forsch A, 207, 400-409. https://doi.org/10.1007/s002170050352

Gil, A., Belton, P. & Hills, B. 1996. Applications of NMR to Food Science. Annual reports on NMR spectroscopy,32, 1-49 ,Elsevier. https://doi.org/10.1016/S0066-4103(08)60077-0

Gunduz, S., Yilmaz, H. & Goren, A. C. 2013. Halal food and metrology: Ethyl alcohol contents of beverages, J. Chem. Metrol., 7, 7-9.

Hemke, J., Rasane, P., Kaur, S., Kumbhar, P. & Singh, J. 2019. Vinegar a traditional functional food, Think India Journal ,22, 581-629.

Johnston, C.S. Steplewska, I. Long, C.A. Harris, L.N. & Ryals, R.H. 2010. Examination of the antiglycemic properties of vinegar in healthy adults. Annals of Nutrition and Metabolism,56, 74-79. https://doi.org/10.1159/000272133

Košir e, I. J. & Kidricˇ, J. J. 2001. Identification of amino acids in wines by one-and two-dimensional nuclear magnetic resonance spectroscopy. J. Agric. Food Chem., 49, 50-56. https://doi.org/10.1021/jf0008137

Le Gall L, G., Colquhoun, I. J. & Defernez, M. 2004. Metabolite profiling using 1H NMR spectroscopy for quality assessment of green tea, Camellia sinensis (L.). J. Agric. Food Chem., 52, 692-700. https://doi.org/10.1021/jf034828r

Masino, F., Chinnici, F., Franchini, G. C., Ulrici, A. & Antonelli, A. 2005. A study of the relationships among acidity, sugar and furanic compound concentrations in set of casks for Aceto Balsamico Tradizionale of Reggio Emilia by multivariate techniques. Food Chem., 92, 673-679. https://doi.org/10.1016/j.foodchem.2004.08.029

Nagashima, M. & Saito, K. 2010. Antioxidant activity of the new black vinegar “IZUMI”. The Journal of Nutrition, Health & Aging, 14, 845-849. https://doi.org/10.1007/s12603-010-0138-2

Nishikawa, Y., Takata, Y., Nagai, Y., Mori, T., Kawada, T.& Ishihara, N. 2001. Antihypertensive effect of Kurosu extract, a traditional vinegar produced from unpolished rice, in the SHR rats. Nippon Shokuhin Kagaku Kogaku Kaishi, 48, 73-75 https://doi.org/10.3136/nskkk.48.73

Nord, L. I., Vaag, P. & Duus, J. Ø. 2004. Quantification of organic and amino acids in beer by 1H NMR spectroscopy. Anal. Chem., 76, 4790-4798. doi: 10.1021/ac0496852.

Pauli, G. F., Chen, S.N., Simmler, C., Lankin, D. C., Gödecke, T., Jaki, B. U., Friesen, J. B., McAlpine, J. B. & Napolitan, J. G. 2014. Importance of purity evaluation and the potential of quantitative 1H NMR as a purity assay: miniperspective, J. Med. Chem., 57, 9220-9231. https://doi.org/10.1021/jm500734a

Pereira, G. E., Gaudillere, J., Van Leeuwen, C., Hilbert, G., Lavialle, O., Maucourt, M., Deborde, C., Moing, A. & Rolin, D.. 2005. 1H NMR and chemometrics to characterize mature grape berries in four wine-growing areas in Bordeaux, France. J. Agric. Food Chem., 53, 6382-6389. https://doi.org/10.1021/jf058058q

Perumpuli, P. A.B.N. & Dilruksh, D.M.N. 2022. Vinegar: A functional ingredient for human health. International Food Research Journal, 29, 959 - 974 https://doi.org/10.47836/ifrj.29.5.01

Plessi, M., Monzani, A. & Coppini, D. 1989. Quantitative determination of acids and derivatives in balsamic and other vinegars. Sciences des Aliments., 9, 179-183.

Sobolev, A. P., Segre, A.L. & Lamanna, R. M. 2003. Proton high‐field NMR study of tomato juice. Reson. Chem., 41, 237-245. https://doi.org/10.1002/mrc.1176

Wang, X., Wang, J., Kamal, G. M., Jiang, B., Sun, P., Zhang, X. & Liu, M. C. 2016. Characterization and comparison of commercial Chinese cereal and European grape vinegars using 1H NMR spectroscopy combined with multivariate analysis. Chin. J. Chem., 34, 1183-1193. http://dx.doi.org/10.1002/cjoc.201600365

Westwood, S., Yamazaki, T., Huang, T., Garrido, B., Ün, I., Zhang, W., Martos, G., Stoppacher, N., Saito, T. & Wielgosz, R. 2019. Development and validation of a suite of standards for the purity assignment of organic compounds by quantitative NMR spectroscopy. Metrologia, 56, 064001. DOI 10.1088/1681-7575/ab45cb

Woodams, E.E. & Hang Y. D. , 2010 Influence of apple cultivar and juice pasteurization on hard cider and eau-de-vie methanol content, Bioresource Technology 101 ,1396–1398.