Abstract
The matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry (MALDI-TOF) and micellar electrokinetic chromatography (MEKC) methods were used to identify and quantify five tannins, (+)-catechin, (−)-epigallocatechin, (−)-epigallocatechin gallate, (−)-epicatechin gallate and (−)-epicatechin, from aqueous, ethanolic and acetonic extracts of Calendula officinalis, Hy-pericum, perforatum, Galium verum and Origanum vulgare. The MALDI-TOF technique was used for screening tannins monomers and oligomers in plant extracts. The sandwich method and matrix 2,5-dihydroxybenzoic acid with a concentration of 10 mg mL−1 in acetonitrile/ultrapure water/trifluoroacetic acid (20: 80: 0.1, vol.) were used. The electrophoretic method developed for the separation and quantification of 5 catechins in 15 min exhibited good efficiency and precision, low limits of detection (0.0032–0.0153 μ.g mL-1) and quantification (0.0096–0.0466 μ.g mL−1). The correlation coefficients (R2) exceeded 0.9986 and the recovery values ranged between 94.25 % and 102.50 %. The present work provides new information on some of the less studied compounds present in plants frequently used in traditional medicine.
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Ananingsih, V. K., Sharma, A., & Zhou, W. B. (2013). Green tea catechins during food processing and storage: A review on stability and detection. Food Research International, 50, 469–479. DOI: 10.1016/j.foodres.2011.03.004.
Arce, L., Rios, A., & Valcarcel, M. (1998). Determination of anti-carcinogenic polyphenols present in green tea using capillary electrophoresis coupled to a flow injection system. Journal of Chromatography A, 827, 113–120. DOI: 10.1016/s0021-9673(98)00737-7.
Bilia, A. R., Bergonzi, M. C., Morgenni, F., Mazzi, G., & Vincieri, F. F. (2001). Evaluation of chemical stability of St. John’s wort commercial extract and some preparations. In-ternational Journal of Pharmaceutics, 213, 199–208. DOI: 10.1016/s0378-5173(00)00660-8.
Bonoli, M., Colabufalo, P., Pelillo, M., Toschi, T. G., & Lercker, G. (2003). Fast determination of catechins and xanthines in tea beverages by micellar electrokinetic chromatography. Journal of Agricultural and Food Chemistry, 51, 1141–1147. DOI: 10.1021/jf020907b.
Chang, C. L., & Wu, R. T. (2011). Quantification of (+)–catechin and (−)-epicatechin in coconut water by LC-MS. Food Chemistry, 126, 710–717. DOI: 10.1016/j.foodchem. 2010.11.034.
Chen, Q. S., Zhao, J. W., Chaitep, S. P., & Guo, Z. M. (2009). Simultaneous analysis of main catechins contents in green tea (Camellia sinensis (L.)) by Fourier transform near in-frared reflectance (FT-NIR) spectroscopy. Food Chemistry, 113, 1272–1277. DOI: 10.1016/j.foodchem.2008.08.042.
Council of Europe (2010). European pharmacopoeia, (7th ed.) Strasbourg, France: Council of Europe.
Danila, A. O., Gatea, F., & Radu, G. L. (2011). Polyphenol composition and antioxidant activity of selected medicinal herbs. Chemistry of Natural Compounds, 47, 22–26. DOI: 10.1007/s10600-011-9822-7.
De Falco, E., Mancini, E., Roscigno, G., Mignola, E., Taglialatela-Scafati, O., & Senatore, F. (2013). Chemical composi-tion and biological activity of essential oils of Origanum vulgare L. subsp. vulgare L. under different growth conditions. Molecules, 18, 14948–14960. DOI: 10.3390/molecules181214 948.
Del Rio, D., Stewart, A. J., Mullen, W., Burns, J., Lean, M. E. J., Brighenti, F., & Crozier, A. (2004). HPLC-MS n analysis of phenolic compounds and purine alkaloids in green and black tea. Journal of Agricultural and Food Chemistry, 52, 2807–2815. DOI: 10.1021/jf0354848.
Flamini, R. (2003). Mass spectrometry in grape and wine chemistry. Part I: Polyphenols. Mass Spectrometry Reviews, 22, 218–250. DOI: 10.1002/mas.10052.
Glavnik, V., Simonovska, B., & Vovk, I. (2009). Densitometric determination of (+)-catechin and (−)-epicatechin by 4-dimethylaminocinnamaldehyde reagent. Journal of Chromatography A, 1216, 4485–4491. DOI: 10.1016/j.chroma. 2009.03.026.
Gürbüz, O., Göçmen, D., Dağdelen, F., Gursoy, M., Aydin, S., Şahin, I., Büyükuysal, L., & Usta, M. (2007). Determination of flavan-3-ols and trans-resveratrol in grapes and wine using HPLC with fluorescence detection. Food Chemistry, 100, 518–525. DOI: 10.1016/j.foodchem.2005.10.008.
Hoong, Y. B., Pizzi, A., Tahir, P. M., & Pasch, H. (2010). Characterization of Acacia mangium polyflavonoid tannins by MALDI-TOF mass spectrometry and CP-MAS 13C NMR. European Polymer Journal, 46, 1268–1277. DOI: 10.1016/j.eurpolymj.2010.03.002.
Horie, H., & Kohata, K. (2000). Analysis of tea compo-nents by high-performance liquid chromatography and high-performance capillary electrophoresis. Journal of Chromatography A, 881, 425–438. DOI: 10.1016/s0021-9673(99) 01345-x.
Horie, N., Hirabayashi, N., Takahashi, Y., Miyauchi, Y., Taguchi, H., & Takeishi, K. (2005). Synergistic effect of green tea catechins on cell growth and apoptosis induction in gastric carcinoma cells. Biological & Pharmaceutical Bulletin, 28, 574–579. DOI: 10.1248/bpb.28.574.
Jáč, P., Polášek, M., & Pospíšilová, M. (2006). Recent trends in the determination of polyphenols by electromigration methods. Journal of Pharmaceutical and Biomedical Analysis, 40, 805–814. DOI: 10.1016/j.jpba.2005.12.008.
Khan, N., & Mukhtar, H. (2008). Multitargeted therapy of can-cer by green tea polyphenols. Cancer Letters, 269, 269–280. DOI: 10.1016/j.canlet.2008.04.014.
Khanbabaee, K., & van Ree, T. (2001). Tannins: Classification and definition. Natural Product Reports, 18, 641–649. DOI: 10.1039/b101061l.
Kolouchová-Hanzlíková, I., Melzoch, K., Filip, V., & Smidrkal, J. (2004). Rapid method for resveratrol determination by HPLC with electrochemical and UV detections in wines. Food Chemistry, 87, 151–158. DOI: 10.1016/j.foodchem. 2004.01.028.
Lakić, N., Mimica-Dukić, N., Isak, J., & Božin, B., (2010). Antioxidant properties of Galium verum L. (Rubiaceae) ex-tracts. Open Life Sciences, 5, 331–337. DOI: 10.2478/s11535-010-0022-4.
Li, Y. G., Tanner, G., & Larkin, P. (1996). The DMACA-HCl protocol and the threshold proanthocyanidin content for bloat safety in forage legumes. Journal of the Science of Food and Agriculture, 70, 89–101. DOI: 10.1002/(sici)1097-0010(199601)70:1<89::aid-jsfa470>3.0.co;2-n.
Liu, C. M., Chen, C. Y., & Lin, Y. M. (2014). Estimation of tea catechin levels using micellar electrokinetic chromatogra-phy: A quantitative approach. Food Chemistry, 150, 145–150. DOI: 10.1016/j.foodchem.2013.10.140.
López, M. M. C., Vilarino, J. M. L., Rodriguez, M. V. G., & Losada, L. F. B. (2011). Development, validation and ap-plication of micellar electrokinetic capillary chromatography method for routine analysis of catechins, quercetin and thymol in natural samples. Microchemical Journal, 99, 461–469. DOI: 10.1016/j.microc.2011.06.023.
Matei, A. O., Gatea, F., & Radu, G. L. (2015). Analysis of phenolic compounds in some medicinal herbs by LC-MS. Journal of Chromatographic Science, 53, 1147–1154. DOI: 10.1093/chromsci/bmu177.
Menet, M. C., Sang, S. M., Yang, C. S., Ho, C. T., & Rosen, R. T. (2004). Analysis of theaflavins and thearubigins from black tea extract by MALDI-TOF mass spectrometry. Journal of Agricultural and Food Chemistry, 52, 2455–2461. DOI: 10.1021/jf035427e.
Merken, H. M., & Beecher, G. R. (2000). Liquid chromato-graphic method for the separation and quantification of prominent flavonoid aglycones. Journal of Chromatography A, 897, 177–184. DOI: 10.1016/s0021-9673(00)00826-8.
Mirza, M., Najafpour, N. M., & Dini, M. (2004). Essential oil of Galium verum L. from Iran. Iranian Journal of Pharmaceutical Research, 3, 88–88.
Navarrete, P., Pizzi, A., Pasch, H., Rode, K., & Delmotte, L. (2010). MALDI-TOF and 13C NMR characterization of maritime pine industrial tannin extract. Industrial Crops and Products, 32, 105–110. DOI: 10.1016/j.indcrop.2010.03.010.
Olofson, T. C., Alstefjord, M., Nilson, B., Butler, E., & Vasquez, A. (2014). Lactobacillus apinorum sp. nov., Lactobacillus mellifer sp. nov., Lactobacillus mellis sp. nov., Lactobacillus melliventris sp. nov., Lactobacillus kimbladii sp. nov., Lactobacillus helsingborgensis sp. nov. and Lactobacillus kullabergensis sp. nov., isolated from the honey stomach of the honeybee Apis mellifera. International Journal of Systematic and Evolutionary Microbiology, 64, 3109–3119. DOI: 10.1099/ijs.0.059600-0.
Pizzi, A. (1983). Wood adhesives: Chemistry and technology (pp. 174–244). New York, NY, USA: Marcel Dekker.
Pomponio, R., Gotti, R., Luppi, B., & Cavrini, V. (2003). Microemulsion electrokinetic chromatography for the analysis of green tea catechins: Effect of the cosurfactant on the separation selectivity. Electrophoresis, 24, 1658–1667. DOI: 10.1002/elps.200305391.
Quiroga, R. P., Grosso, N. R., Lante, A., Lomolino, G., Zygadlo, J. A., & Nepote, V. (2013). Chemical composition, antioxidant activity and anti-lipase activity of Origanum vulgare and Lippia turbinata essential oils. International Journal of Food Science & Technology, 48, 642–649. DOI: 10.1111/ijfs. 12011.
Rahim, A. A., Nofrizal, S., & Saad, B. (2014). Rapid tea cate-chins and caffeine determination by HPLC using microwave-assisted extraction and silica monolithic column. Food Chemistry, 147, 262–268. DOI: 10.1016/j.foodchem.2013.09.131.
Re, T. A., Mooney, D., Antignac, E., Dufour, E., Bark, I., Srinivasan, V., & Nohynek, G. (2009). Application of the threshold of toxicological concern approach for the safety evaluation of calendula flower (Calendula officinalis) petals and extracts used in cosmetic and personal care products. Food and Chemical Toxicology, 47, 1246–1254. DOI: 10.1016/j.fct.2009.02.016.
Reed, J. D., Krueger, C. G., & Vestling, M. M. (2005). MALDI-TOF mass spectrometry of oligomeric food polyphenols. Phytochemistry, 66, 2248–2263. DOI: 10.1016/j.phytochem. 2005.05.015.
Sang, S. M., Lambert, J. D., Ho, C. T., & Yang, C. S. (2011). The chemistry and biotransformation of tea constituents. Pharmacological Research, 64, 87–99. DOI: 10.1016/j.phrs.2011.02.007.
Tabrez, S., Priyadarshini, M., Urooj, M., Shakil, S., Ashraf, G. M., Khan, M. S., Kamal, M. A., Alam, Q., Jabir, N. R., Abuzenadah, A. M., Chaudhary, A. G. A., & Damanhouri, G. A. (2013). Cancer chemoprevention by polyphenols and their potential application as nanomedicine. Journal of Environmental Science and Health, Part C, 31, 67–98. DOI: 10.1080/10590501.2013.763577.
Tan, H. P., Xu, W. P., Zhao, A. P., Zhou, L. L., Liu, M. D., Tan, F. Y., Zou, Y., & Wang, Y. J. (2012). Determination of catechins and purine alkaloids in tea by high performance liquid chromatography. Analytical Letters, 45, 2530–2537. DOI: 10.1080/00032719.2012.694130.
Terabe, S., Otsuka, K., Ichikawa, K., Tsuchiya, A., & Ando, T. (1984). Electrokinetic separations with micellar solutions and open-tubular capillaries. Analytical Chemistry, 56, 111–113. DOI: 10.1021/ac00265a031.
Tsanova-Savova, S., Ribarova, F., & Gerova, M. (2005). (+)–Catechin and (−)-epicatechin in Bulgarian fruits. Journal of Food Composition and Analysis, 18, 691–698. DOI: 10.1016/j.jfca.2004.06.008.
Vázquez, G., Pizzi, A., Freire, M. S., Santos, J., Antorrena, G., & González-Álvarez, J. (2012). MALDI-TOF, HPLC-ESI-TOF and 13C-NMR characterization of chestnut (Castanea sativa) shell tannins for wood adhesives. Wood Science and Technology, 47, 523–535. DOI: 10.1007/s00226-012-0513-8.
Weiss, D. J., & Anderton, C. R. (2003). Determination of catechins in matcha green tea by micellar electrokinetic chromatography. Journal of Chromatography A, 1011, 173–180. DOI: 10.1016/s0021-9673(03)01133-6.
Yang, B., Arai, K., & Kusu, F. (2000). Determination of catechins in human urine subsequent to tea ingestion by high-performance liquid chromatography with electrochemical detection. Analytical Biochemistry, 283, 77–82. DOI: 10.1006/abio.2000.4624.
Ye, N. S., Li, J., Wang, Y. X., & Ma, J. C. (2014). Determination of catechins in tea by micellar electrokinetic chromatography with a grapheme oxide-coated capillary. Instrumentation Science & Technology, 42, 605–617. DOI: 10.1080/10739149.2014.930876.
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Matei, A.O., Gatea, F., Teodor, E.D. et al. Tannins analysis from different medicinal plants extracts using MALDI-TOF and MEKC. Chem. Pap. 70, 515–522 (2016). https://doi.org/10.1515/chempap-2015-0222
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DOI: https://doi.org/10.1515/chempap-2015-0222