CHROMATOGRAPHIC METHODS OF ISOLATION AND IDENTIFICATION OF PHENOLIC ACIDS
DOI:
https://doi.org/10.56782/pps.91Abstract
Phenolic acids are a group of compounds widely distributed in the world of plants. They are characterized by diversified chemical structure and pharmacological properties. Due to their health potency, associated mainly with antioxidative action, they are currently of interest as bioactive food components and supplements. This work provides an overview about the reported isolation procedures of phenolic acids from plant material and food products. The chromatographic and spectroscopic identification methods of these compounds are discussed.
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References
Kohlmünzer, S. Farmakognozja. Wydawnictwo Lekarskie PZWL, 2007.
Clifford, M.N. Chlorogenic acid and other cinnamates – nature, occurence, dietary burden, absorption and metabolism. J. Sci. food Agric., 2000, 80, 1033 – 1042. DOI: https://doi.org/10.1002/(SICI)1097-0010(20000515)80:7<1033::AID-JSFA595>3.0.CO;2-T
King, A.; Young, G. Characteristics and occurance of phenolic phytochemicals. J. Am. Diet. Assoc., 1999, 2, 213 – 218. DOI: https://doi.org/10.1016/S0002-8223(99)00051-6
Nardini, M.; d’Aquino, M.; Tomassi, G.; Gentil, V.; di felice, M.; Scaccini, C. Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Rad. Biol. Med., 1995, 19, 541 – 552. DOI: https://doi.org/10.1016/0891-5849(95)00052-Y
Lodovici, M.; Guglielmi, F.; Meoni, M.; Dolara, P. Effect of natural phenolic acids on DNA oxidation in vitro. Food Chem. Toxicol., 2001; 39, 1205 – 1210. DOI: https://doi.org/10.1016/S0278-6915(01)00067-9
Masella, R.; Vari, R.; d'Archivio, M.; di Benedetto, R.; Matarrese, P.; Malorni, W.; Scazzocchio, B.; Giovannini, C. Extra virgin olive oil biophenols inhibit cell-mediated oxidation of LDL by increasing the mRNA transcription of glutathione-related enzymes. J. Nutr., 2004, 134, 785 – 791. DOI: https://doi.org/10.1093/jn/134.4.785
Masella, R.; Cantafora, A.; Modesti, D.; Cardilli, A.; Gennaro, L.; Bocca, A.; Coni, E. Antioxidant activity of 3,4-DHPEA-EA and protocatechuic acid: a comparative assessment with other olive oil biophenols. Redox Rep., 1999, 4, 113 – 121. DOI: https://doi.org/10.1179/135100099101534792
Rice-Evans, C.A.; Miller, N.J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Rad. Biol. Med., 1996, 20, 933 – 956. DOI: https://doi.org/10.1016/0891-5849(95)02227-9
Rice-Evans, C.A.; Miller N.J.; Paganga G. Antioxidant properties of phenolic compounds. Trends Plant Sci., 1997, 2, 152 – 159. DOI: https://doi.org/10.1016/S1360-1385(97)01018-2
Lamer-Zarawska, E.; Oszmiański, J. Rola niektórych substancji roślinnych w profilaktyce przeciwnowotworowej. Wiad. Ziel., 1998, 5, 1 – 4.
Slavin, J.; Marquart, L.; Jacobs, D. Jr. Consumption of whole-grain food and decreased risk of cancer: proposed mechanisms. Cereal Foods World, 2000, 45, 54 – 58.
Sreejayan, N.; Rao, M.N.A. Nitric oxide scavening by curcuminoids. J. Pharm. Pharmacol., 1997, 49, 105 – 107. DOI: https://doi.org/10.1111/j.2042-7158.1997.tb06761.x
Fernández, M.A.; García, M.D.; Sáenz, M.T. Antibacterial activity of the phenolic acid fraction of Scrophularia frutescens and Scrophularia sambucifolia. J. Ethnopharm, 1996, 53, 11 – 14. DOI: https://doi.org/10.1016/0378-8741(96)01419-5
Itoh, A.; Isoda, K.; Kondoh, M.; Kawase, M.; Watari, A.; Kobayashi, M.; Tamesada, M.; Yagi, K. Hepatoprotective effect of syringic acid and vanillic acid on CCl4-induced liver injury. Biol. Pharm. Bull., 2010, 33, 983 – 987. DOI: https://doi.org/10.1248/bpb.33.983
Yu-Shan, Y.; Chin-Lin, H., Gow-Chin Y. Anti-inflammatory effects of the roots of Alpinia pricei Hayata and its phenolic compounds. J. Agric. Food Chem. 2009, 57, 7673 – 7680. DOI: https://doi.org/10.1021/jf901327g
Robbins, R.J. Phenolic acids in food: an overview of analytical methodology. J. Agric. Food Chem., 2003, 51, 2866 – 2877. DOI: https://doi.org/10.1021/jf026182t
Mišan, A.Č.; Mimica-Dukić, N.M.; Mandić, A.I.; Sakač, M.B.; Milovanović, I.L.; Sedej, I.J. Development of rapid resolution HPLC method for the separation and determination of 17 phenolic compounds in crude plant extracts. Cent. Eur. J. Chem, 2011, 9, 133 – 142. DOI: https://doi.org/10.2478/s11532-010-0126-8
Ross, K.A.; Beta, T.; Arntfield, S.D. A comparative study of phenolic acids identified and quantified in dry beans using HPLC as affected by different extraction and hydrolysis methods. Food Chem., 2009, 113, 336 – 344. DOI: https://doi.org/10.1016/j.foodchem.2008.07.064
Skalicka-Woźniak, K.; Głowniak, K. Quantitive analysis of phenolic acids in extracts obtained from the fruits of Peucedanum alsaticum L. and Peucedanum cervaria L. Lap. Chromatographia, 2008, 68, 85 – 90. DOI: https://doi.org/10.1365/s10337-008-0671-x
Wang, J.; Sun, B.; Cao, Y.; Tian, Y.; Li, X. Optimalization of ultrasound-assisted extraction of phenolic compounds from wheat bran. Food Chem., 2008, 106, 804 – 810. DOI: https://doi.org/10.1016/j.foodchem.2007.06.062
Štĕrbová, D.; Matĕjíček, D.; Vlček, J.; Kubáň, V. Combined microvave-assisted isolation and solid-phase purification procedures prior to the chromatographic determination of phenolic compounds in plant materials. Analytica Chimica Acta, 2004, 513, 435 – 444. DOI: https://doi.org/10.1016/j.aca.2004.03.031
Vichapong, J.; Sookserm, M.; Srijesdaruk, V.; Swatsitang, P.; Srijananai, S. High performance liquid chromatographic analysis of phenolic compounds and their antioxidant activities in rice varieties, LWT-Food Sci. Technol. 2010, 43, 1325 – 1330. DOI: https://doi.org/10.1016/j.lwt.2010.05.007
Rangsiwrong, P.; Rangkadilok, N.; Satayavivad, J.; Goto, M.; Shotipruk, A. Subcritical water extraction of polyphenolic compounds from Terminalia chebula Retz. Fruits. Sep. Purif. Technol., 2009, 66, 51 – 56. DOI: https://doi.org/10.1016/j.seppur.2008.11.023
Žiaková, A.; Brandštetrová, E.; Blahová, E. Matrix solid-phase dispersion for the liquid chromatographic determination of phenolic acids in Melissa officinalis. J. Chromatogr. A, 2003, 983, 271 – 275. DOI: https://doi.org/10.1016/S0021-9673(02)01712-0
Głowniak, K.; Zagórka, G.; Kozyra, M. Solid-phase extraction and reversed-phase high-performance liquid chromatography of free phenolic acids in some Echinacea species. J. Chromatogr. A, 1996, 730, 25 – 29. DOI: https://doi.org/10.1016/0021-9673(95)00877-2
Jaroszyńska, J. Isolation of free phenolic compounds from arboreal leaves by use of the Florosil/C18 system. Anal. Bioanal. Chem., 2003, 377, 702 – 708. DOI: https://doi.org/10.1007/s00216-003-2155-z
Saraji, M.; Mousavi, F. Use of hollow fibre-based liquid-liquid-liquid microextraction and high-perfromance liquid chromatography-diode array detection for determination of phenolic acids in fruit juices. Food Chem., 2010, 123, 1310 – 1317. DOI: https://doi.org/10.1016/j.foodchem.2010.06.012
Magalhães, P.J.; Vieira, J.S.; Goncalves, L.M.; Pacheco, J.G.; Guido, L.; Barros, A.A. Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: characterization by high-performance liquid chromatography-diode array detection-electrospray tandem mass spectrometry. J. Chromatogr. A, 2010, 1217, 3258 – 3268. DOI: https://doi.org/10.1016/j.chroma.2009.10.068
Sampietro, D.A.; Vattuone, M.A.; Isla, M.I. Plant growth inhibitors isolated from sugarcane (Saccharum officinarum) Straw. J. Plant Physiol, 2006, 163, 837 – 846. DOI: https://doi.org/10.1016/j.jplph.2005.08.002
Iqbal Z., Hiradate S., Araya H., Fujii Y.; Plant growth inhibitory activity of Ophiophogon japonicus Ker-Gawler and role of phenolic acids and their analogues: a comparative study, Plant Growth Regul., 2004, 43, 245 – 250. DOI: https://doi.org/10.1023/B:GROW.0000045998.68084.4b
Salagoïty, A.; Bertrand, M.H. Wine phenolics-analysis of low molecular weight components by high performance liquid chromatography, J. Sci. Food Agric., 1984, 35, 1242 – 1247. DOI: https://doi.org/10.1002/jsfa.2740351116
Brenes-Balbuena, M.; Gracía, P.; Garrido-Fernandez, A. Phenolic compounds related to the black color formed during the processing of ripe olives. J. Agric. Food Chem., 1992, 40, 1192 – 1196. DOI: https://doi.org/10.1021/jf00019a023
Zgórka, G.; Głowniak, K. Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family. J. Pharm. Biomed. Anal., 2001, 26, 79 – 87. DOI: https://doi.org/10.1016/S0731-7085(01)00354-5
Łuczkiewicz, M.; Cisowski, W.; Kaiser, P.; Ochocka, R.; Piotrowski, A. Comparative analysis of phenolic acids in mistletoe plants from various hosts. Acta Pol. Pharm., 2001, 58, 373 – 377.
Zgórka, G.; Dawka, S. Application of conventional UV, photodiode array (PDA) and fluorescence (FL) detection to analysis of phenolic acids in plant material and pharmaceutical preparations. J. Pharm. Biomed. Anal., 2001, 24, 1065 – 1072. DOI: https://doi.org/10.1016/S0731-7085(00)00541-0
Hung, P.V.; Hatcher, D.W.; Barker, W. Phenolic acid composition of sprouted wheats by ultra-performance liquid chromatography (UPLC) and their antioxidant activities. Food Chem., 2011, 126, 1896 – 1901. DOI: https://doi.org/10.1016/j.foodchem.2010.12.015
Yu, J.; Vasanthan, T.; Temelli, F. Analysis of phenolic acids in barley by high-performacne liquid chromatography. J. Agric. Food Chem., 2001, 49, 4352 – 4358. DOI: https://doi.org/10.1021/jf0013407
Gioacchin, M.A.; Roda, A.; Gellati, C.G.; Bopcchini, P.; Manetta, C.A.; Baraldini, M. High-performance liquid chromatographic-electrospray mass spectrometric analysis of phenolic acids and aldehydes. J. Chromatogr. A, 1996, 730, 31 – 37. DOI: https://doi.org/10.1016/0021-9673(95)01166-8
Rodriguez-Delgado, A.M.; Malovaná, S.; Pérez, P.J.; Borges, T.; Gracía-Montelogo, F.J.; Separation of phenolic compounds by high-performance liquid chromatography with absorbance and fluorimetric detection. J. Chromatogr. A, 2001, 912, 249 – 257. DOI: https://doi.org/10.1016/S0021-9673(01)00598-2
Chang, Y-X.; Ding, X-P.; Qi, J.; Cao, J.; Kang, L-Y.; Zhu, D-N.; Zhang, B-L.; Yu, B-Y. Determination of phenolic acids in Danshen preparations by LC with chemiluminescence detection. Chromatographia, 2009, 69, 319 – 323. DOI: https://doi.org/10.1365/s10337-008-0876-z
Boros, B.; Jakabová, S.; Dörnei, Á.; Horváth, G.; Pluhár, Z.; Kilár, F.; Felinger, A. Determination of polyphenolic compounds by liquid chromatography-mass spectrometry in Thymus species. J. Chromatogr. A, 2010, 1217, 7972 – 7980. DOI: https://doi.org/10.1016/j.chroma.2010.07.042
Neo, Y-P.; Ariffin, A.; Tan, C-P.; Tan, Y-A. Phenolic acid analysis and antioxidant activity assessment of oil palm (E.guineensis) fruit extracts. Food Chem., 2010, 122, 353 – 359. DOI: https://doi.org/10.1016/j.foodchem.2010.02.046
Jung, M.Y.; Jeon, B.S.; Bock, J.Y. Free, esterified and insoluble-bound phenolic acids in white and red Korean ginsengs (Panax ginseng C.A.Meyer). Food Chem., 2002, 79, 105 – 111. DOI: https://doi.org/10.1016/S0308-8146(02)00185-1
Heimler, D.; Pieroni, A. Capillary gas chromatography of plant tissues and soil phenolic acids. Chromatographia, 1994, 38, 475 – 478. DOI: https://doi.org/10.1007/BF02269839
Smolarz, D.H. Application of GC-MS method for analysis of phenolic acids and their esters in chloroformic extracts from some taxons of Polygonum L. genus. Chem.Anal., 2001, 46, 439 – 444.
Kivilompolo, M.; Obürka, V.; Hyötyläinen, T. Comparison of GC-MS methods for the analysis of antioxidant phenolic acids in herbs. Anal. Bioanal. Chem., 2007, 388, 881 – 887. DOI: https://doi.org/10.1007/s00216-007-1298-8
Sharma, O.P.; Bhat, T.K.; Singh, B. Thin-layer chromatography of gallic acid, methyl gallate, pyrogallol, phloroglucinol, catechol, resorcinol, hydroquinone, catechin, epicatechin, cinnamic acid, p-coumaric acid, ferulic acid and tannic acid, J. Chromatogr. A, 1998, 822, 167 – 171. DOI: https://doi.org/10.1016/S0021-9673(98)00490-7
Scampicchio, M.; Wang, J.; Mannio, S.; Chatrathi, M.P. Microchip capillary electrophoresis with amperometric detection for rapid separation and detection of phenolic acids, J. Chromatogr. A, 2004, 1049, 189 – 194. DOI: https://doi.org/10.1016/S0021-9673(04)01275-0
Ferrer-Gallego, R.; Hernández-Hierro, J.M.; Rivas-Gonzalo, J.C.; Escribano-Bailón, M.T. Determination of phenolic compounds of grape skins during ripening by NIR spectroscopy, LTW-Food Sci. Technol., 2011, 44, 847 – 853. DOI: https://doi.org/10.1016/j.lwt.2010.12.001
Nerantzaki, A.A.; Tsiafoulis, C.G.; Charisiadis, P.; Kontogianni, V.G.; Gerothanassis, I.P. Novel determination of the total phenolic content in crude plant extracts by the use of 1H NMR of the –OH spectral region, Anal. Chim. Acta, 2011, 688, 54 – 60. DOI: https://doi.org/10.1016/j.aca.2010.12.027
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