1H-NMR profile of mezcal and its distillation fractions using two sample preparation methods: direct analysis and solid-phase extraction

Chemical Papers - Tập 75 - Trang 4249-4259 - 2021
Alejandra del C. Pineda-Amaya1, Iran Ocaña-Rios2, Martha E. García-Aguilera2, Hipócrates Nolasco-Cancino3, Beatriz Quiroz-García2, Nuria Esturau-Escofet2, Francisco Ruiz-Terán1
1Facultad de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico
2Instituto de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico
3Facultad de Ciencias Químicas, Universidad Autónoma Benito Juárez de Oaxaca, Oaxaca, Mexico

Tóm tắt

Distillation fractions (head, body, and tail) and mezcal samples were analyzed by proton nuclear magnetic resonance spectroscopy (1H-NMR). Samples were obtained from five rural producers in Oaxaca State, Mexico, where the distilled beverage was produced using as raw material Agave angustifolia, commonly known as “Espadín”. The distillation cuts were done by the producers according to their experience and samples were taken from each distillation fraction. 1H-NMR spectra were acquired by two sample preparation methods: direct analysis (DA) and solid-phase extraction (SPE) using styrene–divinylbenzene sorbent to concentrate aromatic compounds. When DA-NMR was used, fifteen compounds were identified and quantitated at mg/L level, including higher alcohols, aldehydes, esters, and organic acids. On the other hand, nine compounds were identified by SPE-NMR, including fatty acids, aromatic alcohols, aldehydes, and polycyclic aromatic hydrocarbons. The study showed that 1H-NMR can be done by DA and with SPE as a complementary method for analysis of mezcal and its distillation fractions. These methodologies are useful for both research and industrial purposes.

Tài liệu tham khảo

Abraham PE, Yin H, Borland AM, Weighill D, Lim SD, De Paoli HC, Engle N, Jones PC, Agh R, Weston DJ, Wullschleger SD, Tschaplinski T, Jacobson D, Cushman JC, Hettich RL, Tuskan GA, Yang X (2016) Transcript, protein and metabolite temporal dynamics in the CAM plant Agave. Nat Plants 2:16178. https://doi.org/10.1038/nplants.2016.178 Balcerek M, Pielech-Przybylska K, Patelski P, Dziekońska-Kubczak U, Strąk E (2017) The effect of distillation conditions and alcohol content in ‘heart’ fractions on the concentration of aroma volatiles and undesirable compounds in plum brandies. J Inst Brewing 123:452–463. https://doi.org/10.1002/jib.441 Balderas-Hernández VE, Ornelas-Salas JT, Barba de la Rosa AP, De Leon-Rodriguez A (2020) Diminution of migration of phthalic acid esters in tequila beverage by the year of production. J Environ Sci Heal B 55:148–154. https://doi.org/10.1080/03601234.2019.1674103 Bharti SK, Roy R (2012) Quantitative 1H NMR spectroscopy. Trends Anal Chem 35:5–26. https://doi.org/10.1016/j.trac.2012.02.007 Cacho JI, Campillo N, Viñas P, Hernández-Córdoba M (2016) Evaluation of the contamination of spirits by polycyclic aromatic hydrocarbons using ultrasound-assisted emulsification microextraction coupled to gas chromatography–mass spectrometry. Food Chem 190:324–330. https://doi.org/10.1016/j.foodchem.2015.05.106 De León RA, Escalante-Minakata P, Jiménez-García MI, Ordoñez- Acevedo LG, Flores-Flores JL, Barba de la Rosa AP (2008) Characterization of volatile compounds from ethnic Agave alcoholic beverages by gas chromatography–mass spectrometry. Food Technol Biotechnol 46:448–455 De León-Rodríguez A, González-Hernández L, Barba de la Rosa AP, Escalante-Minakata P, López MG (2006) Characterization of volatile compounds of mezcal, an ethnic alcoholic beverage obtained from Agave salmiana. J Agric Food Chem 54:1337–1341. https://doi.org/10.1021/jf052154+ Fotakis C, Christodouleas D, Kokkotou K, Zervou M, Zoumpoulakis P, Moulos P, Liouni M, Calokerinos A (2013) NMR metabolite profiling of Greek grape marc spirits. Food Chem 138:1837–1846. https://doi.org/10.1016/j.foodchem.2012.11.128 Hernández-Gómez LF, Úbeda-Iranzo J, Garcı́a-Romero E, Briones-Pérez A (2005) Comparative production of different melon distillates: chemical and sensory analyses. Food Chem 90:115–125. https://doi.org/10.1016/j.foodchem.2004.03.033 Jia C, Batterman S (2010) A critical review of naphthalene sources and exposures relevant to indoor and outdoor air. Int J Environ Res Public Health 7:2903–2939. https://doi.org/10.3390/ijerph7072903 Kessler P, Godejohann M (2018) Identification of tentative marker in Corvina and Primitivo wines with CMC-se. Magn Reson Chem 56:480–492. https://doi.org/10.1002/mrc.4712 Kew W, Goodall I, Uhrín D (2019) Analysis of Scotch Whisky by 1H NMR and chemometrics yields insight into its complex chemistry. Food Chem 298:125052. https://doi.org/10.1016/j.foodchem.2019.125052 Kuballa T, Hausler T, Okaru AO, Neufeld M, Abuga KO, Kibwage IO, Rehm J, Luy B, Walch SG, Lachenmeier DW (2018) Detection of counterfeit brand spirits using 1H NMR fingerprints in comparison to sensory analysis. Food Chem 245:112–118. https://doi.org/10.1016/j.foodchem.2017.10.065. https://doi.org/10.1007/s10068-017-0199-7 Medina-Valtierra G, Juárez-Ciprés R, Peña-Álvarez A (2011) Identification and quantification of aldehydes in Mezcal by solid phase microextraction with on-fiber derivatization-gas chromatography. J Mex Chem Soc 55:84–88 Molina-Guerrero JA, Botello-Álvarez JE, Estrada-Baltazar A, Navarrete-Bolaños JL, Jiménez-Islas H, Cárdenas-Manríquez M, Rico-Martínez R (2007) Compuestos volátiles en el mezcal. Rev Mex Ing Quim 6:41–50 Monakhova YB, Schäfer H, Humpfer E, Spraul M, Kuballa T, Lachenmeier DW (2011) Application of automated eightfold suppression of water and ethanol signals in 1H NMR to provide sensitivity for analyzing alcoholic beverages. Magn Reson Chem 49:734–739. https://doi.org/10.1002/mrc.2823 NOM-070-SCFI-2016 (2016) Norma Oficial Mexicana. Bebidas alcohólicas-Mezcal-Especificaciones. https://dof.gob.mx/nota_detalle.php?codigo=5472787&fecha=23/02/2017. Accessed 22 Jan 2021 Plaza-Bolaños P, Garrido-Frenich A, Vidal JLM (2010) Polycyclic aromatic hydrocarbons in food and beverages. J Chromatogr A 1217:6303–6326. https://doi.org/10.1016/j.chroma.2010.07.079 Ramírez-Guzmán KN, Torres-León C, Martinez-Medina GA, de la Rosa O, Hernández-Almanza A, Alvarez-Perez OB, Araujo R, Rodriguez- González L, Londoño L, Ventura J, Rodríguez R, Martínez JL, Aguilar CN (2019) Traditional fermented beverages in Mexico. In: Grumezescu AM, Holban AM (eds) Fermented beverages, 5th edn. Woodhead Publishing, London, pp 605–635 Savage AK, van Duynhoven JPM, Tucker G, Daykin CA (2011) Enhanced NMR-based profiling of polyphenols in commercially available grape juices using solid-phase extraction. Magn Reson Chem 49:S27–S36. https://doi.org/10.1002/mrc.2846 Vera Guzmán AM, Santiago García PA, López MG (2009) Compuestos volátiles aromáticos generados durante la elaboración de mezcal de Agave angustifolia y Agave potatorum. Rev Fitotec Mex 32:273–279 Vera-Guzman AM, Guzmán-Gerónimo RI, López MG (2010) Major and minor compounds in a Mexican spirit, young Mezcal coming from two Agave species. Czech J Food Sci 28:127–132. https://doi.org/10.17221/56/2009-CJFS Vera-Guzmán AM, Guzmán-Gerónimo RI, López MG, Chávez-Servia JL (2018) Volatile compound profiles in Mezcal spirits as influenced by Agave species and production processes. Beverages 4:1–10. https://doi.org/10.3390/beverages4010009 Weber JV, Sharypov VI (2009) Ethyl carbamate in foods and beverages: a review. Environ Chem Lett 7:233–247. https://doi.org/10.1007/s10311-008-0168-8 Xiang XF, Lan YB, Gao XT, Xie H, An ZY, Lv ZH, Yin-Shi Duan CQ, Wu GF (2020) Characterization of odor-active compounds in the head, heart, and tail fractions of freshly distilled spirit from Spine grape (Vitis davidii Foex) wine by gas chromatography–olfactometry and gas chromatography–mass spectrometry. Food Res Int 137:109388. https://doi.org/10.1016/j.foodres.2020.109388