Microextracción líquido-líquido dispersiva en la determinación de compuestos fenólicos en miel de abejas

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Lázaro Armando Pérez Acosta

Resumen

Los componentes minoritarios en la miel de abejas constituyen una fuente nutricional y terapéutica para los seres humanos. Estos alcanzan más de 200 compuestos, y sus propiedades físico-químicas dependen del origen botánico y geográfico. Los compuestos fenólicos son productos naturales fitoquímicos del metabolismo secundario de las plantas. Estos son los responsables de la mayor parte de la actividad antioxidante en la miel de abejas. La determinación de los mismos es una pieza clave en la caracterización de las mieles, lo que incrementa el valor agregado de las mismas. En la actualidad, existen diferentes técnicas para la determinación de estos analitos en esta matriz apícola. Sin embargo, la microextracción líquido-líquido dispersiva resulta una técnica de preparación de muestras selectiva y sensible para la realización de este análisis. Los detectores que se emplean con frecuencia en el análisis de compuestos fenólicos son los espectrofotométricos (UV y arreglo de diodos) y de masas. Los analizadores de masas que se utilizan son el analizador de trampa de iones, el triple cuadrupolo, así como el analizador híbrido de masas Orbitrap.

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Microextracción líquido-líquido dispersiva en la determinación de compuestos fenólicos en miel de abejas. (2022). Apiciencia, 24(3). https://apiciencia.edicionescervantes.com/index.php/apiciencia/article/view/9
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Microextracción líquido-líquido dispersiva en la determinación de compuestos fenólicos en miel de abejas. (2022). Apiciencia, 24(3). https://apiciencia.edicionescervantes.com/index.php/apiciencia/article/view/9

Referencias

Ahmed, A. Y. B. H., Obbed, M. S., Wabaidur, S. M., AlOthman, Z. A., & Al-Shaalan, N. H. (2014). High-Performance Liquid Chromatography analysis of phenolic acid, flavonoid, and phenol contents in various natural Yemeni honeys using multi-walled carbon nanotubes as a Solid-Phase Extraction adsorbent. Journal of Agricultural and Food Chemistry, 62, 5443−5450. doi:10.1021/ jf5011758

Albaridi, N. A. (2019). Antibacterial Potency of Honey. International Journal of Microbiology, 1-11. doi:https://doi.org/10.1155/2019/2464507

Aljadi, A. M., & Kamaruddin, M. Y. (2004). Evaluation of the phenolic contents and antioxidant capacities of two Malaysian floral honeys. Food Chemistry, 85 513–518. doi:10.1016/S0308-8146(02)00596-4

Andruch, V., Balogh, I. S., Kocúrová, L., & Šandrejová, J. (2013). Five years of Dispersive Liquid–Liquid Microextraction. Applied Spectroscopy Reviews, 48(3), 161–259. doi:10.1080/05704928.2012.697087

Biesaga, M., & Pyrzynska, K. (2009). Liquid chromatography/tandem mass spectrometry studies of the phenolic compounds in honey. 1216(38 ), 6620-6626. doi:10.1016/j.chroma.2009.07.066

Cabras, P., Angioni, A., Tuberoso, C., Floris, I., Reniero, F., Guillou, C., & Ghelli|, S. (1999). Homogentisic acid: A phenolic acid as a marker of strawberry-tree (Arbutus unedo) honey. Journal of Agricultural and Food Chemistry, 47(10), 4064−4067. doi:10.1021/jf990141o

Campillo, N., Viñas, P., Férez-Melgarejo, G., & Hernández-Córdoba, M. (2015). Dispersive liquid–liquid microextraction for the determination of flavonoid aglycone compounds in honey using liquid chromatography with diode array detection and time-of-flight mass spectrometry. Talanta, 131, 185-191. doi:10.1016/j.talanta.2014.07.083

Campone, L., Piccinelli, A. L., Pagano, I., Carabetta, S., Sanzo, R. D., Russo, M., & Rastrelli, L. (2014). Determination of phenolic compounds in honey using dispersive liquid–liquid microextraction. Journal of Chromatography A, 1334, 9-15. doi:10.1016/ j.chroma.2014.01.081

Ciulu, M., Spano, N., Pilo, M. I., & Sanna, G. (2016). Recent advances in the analysis of phenolic compounds in unifloral honeys. Molecules, 21(451). doi:10.3390/molecules21040451

Cuyckens, F., & Claeys, M. (2005 ). Determination of the glycosylation site in flavonoid mono-O-glycosides by collision-induced dissociation of electrospray-generated deprotonated and sodiated molecules. Journal of Mass Spectrometry, 40, 364–372. doi:10.1002/jms.794

Chan, C. W., Deadman, B. J., Manley-Harris, M., & Wilkins, A. (2013). Analysis of the flavonoid component of bioactive New Zealand mānuka (Leptospermum scoparium) honey and the isolation, characterisation and synthesis of an unusual pyrrole. Food Chemistry, 141 1772–1781.

Dimitrova, B., Gevrenova, R., & Anklam, E. (2007). Analysis of phenolic acids in honeys of different floral origin by Solid-phase Extraction and High-performance Liquid Chromatography. Phytochemical Analysis, 18, 24-32. doi:10.1002/pca.948

Fabre, N., Rustan, I., Hoffmann, E. d., & Quetin-Leclercq, J. (2001). Determination of flavone, flavonol, and flavanone aglycones by negative ion Liquid Chromatography Electrospray Ion Trap Mass Spectrometry. Journal of American Society for Mass Spectrometry, 12, 707–715. doi:10.1016/S1044-0305(01)00226-4

Ferreres, F., Andrade, P., Gil, M. L., & Tomás-Barberán, F. A. (1996 ). Floral nectar phenolics as biochemical markers for the botanical origin of heather honey. Z Lebensm Unters Forsch, 202, 40-44.

Ferreres, F., García-Viguera, C., Tomás-Lorente, F., & TomásBarberán, F. A. (1993). Hesperetin: A marker of the floral origin of Citrus honey. Journal of the Science of Food and Agriculture, 61, 121-123.

Ferreres, F., Llorach, R., & Gil-Izquierdo, A. (2004 ). Characterization of the interglycosidic linkage in di-, tri-, tetra- and pentaglycosylated flavonoids and differentiation of positional isomers by liquid chromatography/electrospray ionization tandem mass spectrometry. Journal of Mass Spectrometry, 39, 312–321. doi:10.1002/jms.586

Ferreres, F., Tomás-Berberán, F. A., Gil, M. I., & Tomás-Lorente, F. (1991). An HPLC technique for flavonoids analysis in honey. Journal of the Sciense of Food and Agriculture, 56, 49-56.

Gašić, U., Kecěkeš, S., Dabić, D., Trifković, J., Milojković-Opsenica, D., Natić, M., & Tešić, Ž. (2014). Phenolic profile and antioxidant activity of Serbian polyfloral honeys. Food Chemistry, 145 599–607. doi:10.1016/j.foodchem.2013.08.088

Gašić, U., Šikoparija, B., TosTi, T., Trifković, J., MiloJković-Opsenica, D., Natić, M., & Tešić, Ž. (2014 ). Phytochemical fingerprints of Lime honey collected in Serbia. Journal of AoAC International, 97 (5), 1259-1267. doi:10.5740/jaoacint.SGEGasic

Gašić, U. M., Milojković-Opsenica, D. M., & Tešić, Ž. l. (2017). Polyphenols as possible markers of botanical origin of honey. Journal of AoAC International, 100 (4), 1-10. doi:10.5740/ jaoacint.17-0144

Gheldof, N., Wang, X.-H., & Engeseth, N. J. (2002). Identification and quantification of antioxidant components of honeys from various floral sources. Journal of Agricultural and Food Chemistry, 50, 5870−5877. doi:10.1021/jf0256135

Gomez-Caravaca, A. M., Gómez-Romero, M., Arráez-Román, D., Segura-Carretero, A., & Fernandez-Gutiérrez, A. (2006). Advances in the analysis of phenolic compounds in products derived from bees. Journal of Pharmaceutical and Biomedical Analysis, 41 1220–1234. doi:10.1016/j.jpba.2006.03.002

Havsteen, B. H. (2002). The biochemistry and medical significance of the flavonoid. Pharmacology & Therapeutics, 96 67–202.

Jerković, I., Marijanović, Z., Kezić, J., & Gugić, M. (2009). Headspace, volatile and semi-volatile organic compounds diversity and radical scavenging activity of ultrasonic solvent extracts from Amorpha Fruticosa honey samples. Molecules, 14, 2717-2728. doi:10.3390/molecules14082717

Kecěkeš, S., Gašić, U., Veličković, T. Ć., Milojković-Opsenica, D., Natić, M., & Tešić, Ž. (2013). The determination of phenolic profiles of Serbian unifloral honeys using ultra-highperformance liquid chromatography/high resolution accurate mass spectrometry. Food Chemistry, 138(1), 32–40. doi:10.1016/j.foodchem.2012.10.025

Kečkeš, J., Trifković, J., Andrić, F., Jovetić, M., Tešić, Ž., & MilojkovićOpsenica, D. (2013). Amino acids profile of Serbian unifloral honeys. Journal of the Science of Food and Agriculture, 93, 3368 –3376. doi:10.1002/jsfa.6187

Lee, J. S., Kim, D. H., Liu, K.-H., Oh, T. K., & Lee, C. H. (2005). Identification of flavonoids using liquid chromatography with electrospray ionization and ion trap tandem mass spectrometry with an MS/MS library. Rapid Communications in Mass Spectrometry, 19, 3539–3548. doi:10.1002/rcm.2230

Liu, H., & Dasgupta, P. K. (1996). Analytical chemistry in a Drop. Solvent Extraction in a Microdrop. Analytical Chemistry, 68 (11), 1817-1821.

Luengo, T. L. (2002). Flavonoides. OFFARM ELSEVIER, 21 (4), 108114.

Martos, I., Ferreres, F., & Tomás-Barberán, F. A. (2000). Identification of flavonoid markers for the botanical origin of Eucalyptus honey. Journal of Agricultural and Food Chemistry, 48(5), 1498−1502. doi:10.1021/jf991166q

Meda, A., Lamien, C. E., Romito, M., Millogo, J., & Nacoulma, O. G. (2005). Determination of the total phenolic, flavonoid and proline contents in Burkina Fasan honey, as well as their radical scavenging activity. Food Chemistry, 91, 571–577. doi:10.1016/j.foodchem.2004.10.006

Michalkiewicz, A., Biesaga, M., & Pyrzynska, K. (2008). Solid-phase extraction procedure for determination of phenolic acids and some flavonols in honey. Journal of Chromatography A, 1187, 18-24. doi:10.1016/j.chroma.2008.02.001

Mondello, L. (2013). Nutraceuticals and separations. Analytical and Bioanalytical Chemistry, 405, 4589–4590. doi:10.1007/s00216013-6845-x

Moniruzzaman, M., Rodríguez, I., Rodríguez-Cabo, T., Cela, R., Sulaiman, S. A., & Gan, S. H. (2014). Assessment of dispersive liquid–liquid microextraction conditions for gas chromatography time-of-flight mass spectrometry identification of organic compounds in honey. Journal of Chromatography A, 1368 26– 36. doi:10.1016/j.chroma.2014.09.057

Natić, M. M., Gašić, U. M., Mišić, D. M., Lušićc, D. V., MilojkovićOpsenica, D. M., Tešić, Ž. L., & Lušić, D. (2015). Chemical markers for the authentication of unifloral Salvia officinalis L. honey. Journal of Food Composition and Analysis, 44, 1-39. doi:10.1016/j.jfca.2015.08.008

Oelschlaegel, S., Gruner, M., Wang, P.-N., Boettcher, A., KoellingSpeer, I., & Speer, K. (2012). Classification and characterization of Manuka honeys based on phenolic compounds and methylglyoxal. Journal of Agricultural and Food Chemistry, 60, 7229−7237. doi:10.1021/jf300888q

Pascual-Maté, A., Osés, S. M., Fernández-Muiño, M. A., & Sancho, M. T. (2018). Analysis of polyphenols in honey: Extraction, separation and quantification procedures. Separation & Purification Reviews, 47, 142–158. doi:10.1080/15422119.2017.1354025

Pasini, F., Gardini, S., Marcazzan, G. L., & Caboni, M. F. (2013). Buckwheat honeys: Screening of composition and properties. Food Chemistry, 141 (3), 2802–2811. doi:10.1016/ j.foodchem.2013.05.102

Pawliszyn, J. (2003). Sample preparation: Quo vadis? Analytical Chemistry, 75 (11), 2543-2558. doi:10.1021/ac034094h

Petretto, G. L., Cossu, M., & Alamanni, M. C. (2014). Phenolic content, antioxidant and physico-chemical properties of Sardinian monofloral honey. International Journal of Food Science and Technology. doi:10.1111/ijfs.12652

Pyrzynska, K., & Biesaga, M. (2009). Analysis of phenolic acids and flavonoids in honey. Trends in Analytical Chemistry, 28(7 ). doi:10.1016/j.trac.2009.03.015

Pyrzyńska, K., & Biesaga, M. (2013). Stability of bioactive polyphenols from honey during different extraction methods. Food Chemistry, 136(1), 46-54. doi:10.1016/j.foodchem.2012.07.095

Ranneh, Y., Ali, F., Zareia, M., Akim, A. M., Hamid, H. A., & Khazaai, H. (2018 ). Malaysian stingless bee and Tualang honeys: A comparative characterization of total antioxidant capacity and phenolic profile using liquid chromatography-mass spectrometry. LWT-Food Science and Technology, 89 1–9. doi:http:// dx.doi.org/10.1016/j.lwt.2017.10.020

Rezaee, M., Assadi, Y., Hosseini, M.-R. M., Aghaee, E., Ahmadi, F., & Berijani, S. (2006). Determination of organic compounds in water using dispersive liquid–liquid microextraction. Journal of Chromatography A, 1116 1–9. doi:10.1016/j.chroma.2006.03.007

Ridgway, K., Lalljie, S. P. D., & Smith, R. M. (2007). Sample preparation techniques for the determination of trace residues and contaminants in foods. Journal of Chromatography A, 1153, 36–53. doi:10.1016/j.chroma.2007.01.134

Rijke, E. d., Out, P., Niessen, W. M. A., Ariese, F., Gooijer, C., & Brinkman, U. A. T. (2006). Analytical separation and detection methods for flavonoids. Journal of Chromatography A, 1112, 31–63. doi:10.1016/j.chroma.2006.01.019

Rutkowska, M., Płotka-Wasylka, J., Sajid, M., & Andruch, V. (2019). Liquid–phase microextraction: A review of reviews. Microchemical Journal, 149 103989. doi:10.1016/j.microc.2019.103989

Scanu, R., Spano, N., Panzanelli, A., Pilo, M. I., Piu, P. C., Sanna, G., & Tapparo, A. (2005). Direct chromatographic methods for the rapid determination of homogentisic acid in strawberry tree (Arbutus unedo L.) honey. Journal of Chromatography A, 1090 76–80. doi:10.1016/j.chroma.2005.06.092

Sergiel, I., Pohl, P., & Biesaga, M. (2014). Characterisation of honeys according to their content of phenolic compounds using high performance liquid chromatography/tandem mass spectrometry. Food Chemistry, 145 404–408. doi:10.1016/ j.foodchem.2013.08.068

Shalash, M., Makahleh, A., Salhimi, S. M., & Saad, B. (2017). Vortexassisted liquid-liquid–liquid microextraction followed by high performance liquid chromatography for the simultaneous determination of fourteen phenolic acids in honey, iced tea and canned coffee drinks. Talanta, 1-37. doi:http://dx.doi.org/10.1016/j.talanta.2017.06.039

Silva, T. M. S., Santos, F. P. d., Evangelista-Rodrigues, A., Silva, E. M. S. d., Silva, G. S. d., Novais, J. S. d., . . . Camara, C. A. (2013). Phenolic compounds, melissopalynological, physicochemical analysis and antioxidant activity of jandaíra (Melipona subnitida) honey. Journal of Food Composition and Analysis, 29 10–18. doi:http://dx.doi.org/10.1016/j.jfca.2012.08.010

Tomás-Barberán, F. A., Martos, I., Ferreres, F., Radovic, B. S., & Anklam, E. (2001). HPLC flavonoid profiles as markers for the botanical origin of European unifloral honeys. Journal of the Science of Food and Agriculture, 81, 485-496.

Truchado, P., Vit, P., Heard, T. A., Tomás-Barberán, F. A., & Ferreres, F. (2015). Determination of interglycosidic linkages in Oglycosyl flavones by high-performance liquid chromatography/ photodiode-array detection coupled to electrospray ionization ion trap mass spectrometry. Its application to Tetragonula carbonaria honey from Australia. Rapid Communcations in Mass Spectrometry, 29 948–954. doi:10.1002/rcm.7184

Viñas, P., & Campillo, N. (2019). Gas Chromatography: Mass Spectrometry analysis of polyphenols in foods Analysis Techniques for Polyphenols (pp. 285-316): Elsevier Inc.

Vukics, V., & Guttman, A. (2010). Structural characterization of flavonoid glycosides by multi-stage mass spectrometry. Mass Spectrometry Reviews, 29 1– 16. doi:10.1002/mas.20212

Wabaidur, S. M., Ahmed, Y. B. H., Alothman, Z. A., Obbed, M. S., AL -Harbi, N. M., & AL-Turki, T. M. (2015). Ultra high performance liquid chromatography with mass spectrometry method for the simultaneous determination of phenolic constituents in honey from various floral sources using multiwalled carbon nanotubes as extraction sorbents. Journal of Separation Science, 38 (15), 2597–2606. doi:10.1002/jssc.201500386

Yacuzzi, E., Martín, F., Quiñones, H. M., & Popovsky, M. J. (2004). El diseño experimental y los métodos de Taguchi: Conceptos y aplicaciones en la industria farmacéutica. Serie Documentos de Trabajo, University of CEMA, Buenos Aires (258), 1-32. doi:http://hdl.handle.net/10419/84374

Yang, W.-Z., Ye, M., Qiao, X., Wang, Q., Bo, T., & Guo, D.-A. (2012). Collision-induced dissociation of 40 flavonoid aglycones and differentiation of the common flavonoid subtypes using electrospray ionization ion-trap tandem mass spectrometry and quadrupole timeof-flight mass spectrometry. European Journal of Mass Spectrometry, 18, 493–503. doi:10.1255/ejms.1206

Yao, L., Datta, N., Tomás-Barberán, F. A., Ferreres, F., Martos, I., & Singanusong, R. (2003). Flavonoids, phenolic acids and abscisic acid in Australian and New Zealand Leptospermum honeys,. Food Chemistry,, 81(2), 159-168. doi:https://doi.org/10.1016/ S0308-8146(02)00388-6

Yao, L., Jiang, Y., D’Arcy, B., Singanusong, R., Datta, N., Caffin, N., & Raymont, K. (2004). Quantitative High-Performance Liquid Chromatography analyses of flavonoids in Australian Eucalyptus honeys. Journal of the Science of Food and Agriculture, 52, 210−214. doi:10.1021/jf034990u

Zhang, X.-H., Wu, H.-L., Wang, J.-Y., Tu, D.-Z., Kang, C., Zhao, J., . . . Yu, R.-Q. (2013). Fast HPLC-DAD quantification of nine polyphenols in honey by using second-order calibration method based on trilinear decomposition algorithm. Food Chemistry, 138 62–69. doi:http://dx.doi.org/10.1016/j.foodchem.2012.10.033

Zhou, J., Yao, L., Li, Y., Chen, L., Wu, L., & Zhao, J. (2014). Floral classification of honey using liquid chromatography–diode array detection–tandem mass spectrometry and chemometric analysis. Food Chemistry, 145 941–949. doi:10.1016/ j.foodchem.2013.08.117