Chlorogenic acids – their properties, occurrence and analysis

Marta Gil, Dorota Wianowska

Abstract


Chlorogenic acids (CQAs), the esters of caffeic acid and quinic acid, are biologically important phenolic compounds present in many plant species. Nowadays much is known from their pro-health properties, including anti-cancer activity. Yet, the supposition that they may be helpful in fighting obesity and modify glucose-6-phosphatase involved in glucose metabolism have led to a revival of research on CQAs properties and their natural occurrence. Much attention is also paid to the proper analysis of CQAs content in plants and plant products due to the fact that the main CQAs representative in nature i.e. 5-O-caffeoylquinic acid (5-CQA) is commonly employed as a quality marker in the control of various natural products.

The common procedures used so far for CQAs determination in plants involve conventional long lasting solvent extraction realized at higher temperatures prior to chromatographic analysis. The drawbacks associated to the conventional extraction techniques have led to the search for new alternative extraction processes that additionally could improve extracts quality. The latter is particularly important as regards CQAs applications, and the fact that these compounds easily transform/degrade to others. According to reports, the conventional heating of 5-CQA in the presence of water causes its isomerization and transformation. The reports prove that 5-CQA not only isomerizes to 3- and 4-O-caffeoylquinic acid, but also undergoes other transformations such as esterification and reactions with water. Hence, in the attempt to improve the process of chlorogenic acids extraction and to make it more effective and environmentally friendly, innovative so-called "enhanced" techniques of extraction have been recently developed and applied. To guarantee the proper analysis of compounds with very similar properties forming the chlorogenic acids family and their numerous transformation/degradation products, hyphenated techniques, in particular LC-MS, are currently being used.


Keywords


Chlorogenic acids, caffeoylquinic acids, properties, occurrence, analysis

Full Text:

PDF

References


M.N. Clifford. Review: Chlorogenic acids and other cinnamates-nature, occurrence and dietary burden. Journal of the Science of Food and Agriculture, 79:326–372 (1999).

M.N. Clifford. Review – Chlorogenic acids and other cinnamates – nature, occurrence, dietary burden, absorption and metabolism. Journal of the Science of Food and Agriculture, 80:1033–1043 (2000).

A. Farah, T. De Paulis, L.C. Trugo, P.R Martin. Effect of roasting on the formation of chlorogenic acid lactones in coffee. Journal of Agriculture and Food Chemistry, 53:1505−1513 (2005).

M.H.Kweon, H.J. Hwang, H.C. Sung. Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis). Journal of Agriculture and Food Chemistry, 49:4646−4655 (2001).

W.E. Robinson, M.G. Reinecke, S. Abdel-Malek, Q. Jia, S.A. Chow. Inhibitors of HIV-1 replication that inhibit HPV integrase. Proceedings of the National Academy of Science U.S.A., 93:6326−6331 (1996).

H.C. Kwon, C.M.Jung, C.G. Shin, J.K. Lee, S.U. Choi, S.Y. Kim, K.R Lee. A new caffeoyl quinic acid from Aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase. Chemical and Pharmaceutical Bulletin, 48:1796−1798 (2000).

L.A. Ludwig, M.N. Clifford, M.E.J. Lean, H. Ashihara, A. Crozier. Coffee: biochemistry and potential impact on health, Food and Function, 5:1695–1717 (2014).

T. Tanaka, T. Kojima, T. Kawamori, A. Wang, M. Suzui, K. Okamoto, H. Mori, Inhibition of 4-nitro-quinoline-1-oxide-induced rat tongue carcinogenesis by the naturally occurring plant phenolics caffeic, ellagic, chlorogenic, and ferulic acids. Carcinogenesis, 14:1321–1325 (1993).

M. Ohnish, H. Morishita, H. Iwahashi, S. Toda, Y. Shirataki, M. Kimura, R. Kido. Inhibitory effects of chlorogenic acids on linoleic acid peroxidation and hemolytic. Phytochemistry, 36:579–583 (1994).

H. Kasai, Z. Fukada, S. Yamaizumi, S. Sugie, H. Mori. Action of chlorogenic acid in vegetables and fruits as an inhibitor of 8-hydroxydeoxyguanosine formation in vitro and in a rat carcinogenesis model. Food and Chemical Toxicology, 38:467–471 (2000).

K.L. Johnston, M.N. Clifford, L.M. Morgan. Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine. The American Journal of Clinical Nutrition, 78:728–733 (2003).

H. Hemmerle, H. Burger, P. Below, G. Schubert, R. Rippel, P.W. Schindler, E. Paulus, A.W. Herling. Chlorogenic acid and synthetic chlorogenic acid derivatives: novel inhibitors of hepatic glucose-6-phosphate translocase. Journal of Medicinal Chemistry, 40:137−145 (1997).

J. Shearer, A. Farah, T. de Paulis, D.P .Bracy, R.R. Pencek, T.E. Graham. Quinides of roasted coffee enhance insulin action in conscious rats. Journal of Nutrition, 133:3529−3532 (2003).

R. Jaiswal, M.F. Matei, A. Golon, M. Witt, N. Kuhnert. Understanding the fate of chlorogenic acids in coffee roasting using mass spectrometry based targeted and non-targeted analytical strategies. Food and Function, 3:976−984 (2012).

A.L. Dawidowicz, R. Typek. Thermal Stability of 5-O-Caffeoylquinic Acid in Aqueous Solutions at Different Heating Conditions. Journal of Agricultural and Food Chemistry, 58:12578–12584 (2010).

A.L. Dawidowicz, R.. Typek. Transformation of chlorogenic acids during the coffee beans roasting process. European Food Research & Technology, 243:379−390 (2017).

K. Schutz, D. Kammerer, R. Carle, A. Schieber. Identification and Quantification of Caffeoylquinic Acids and Flavonoids from Artichoke (Cynara scolymus L.) Heads, Juice, and Pomace by HPLC-DAD-ESI/MSn. Journal of Agricultural and Food Chemistry, 52:4090–4096 (2004).

A. Kim, H. Kim, W.L. Kerr, S. Choi. The effect of grinding at various vacuum levels on the color, phenolics, and antioxidant properties of apple. Food Chemistry, 216:234–242 (2017).

H.D. Mosel, K. Herrmann. The contents of catechins and hydroxycinnamic acids in pome and stone fruits. Z Lebensm Unters Forsch, 154:6–11 (1974).

G.A. Spanos, R.E. Wrolstad. Phenolics of apple, pear, and white grape juices and their changes with processing and storage - a review. Journal of Agricultural and Food Chemistry, 40:1478–1487 (1992).

B. Risch, K . Herrmann. Die Gehalte an Hydroxyzimtsaure-Verbindungenund Catechinen in Kernund Steinobst. Z Lebensm Unters Forsch, 186:225–230 (1988).

Y. Lu, Y. Foo. Identification and quantification of major polyphenols in apple pomace. Food Chemistry, 59:187–194 (1997).

S. Burda, W. Oleszek, C.Y. Lee. Phenolic compounds and their changes in apples during maturation and cold storage. Journal of Agricultural and Food Chemistry, 38:945–948 (1998).

G. Ritter, U. Hagenauer-Hener, H. Dietrich. The phenolic substances of Sorbus domestica L and their importance for the quality of apple wines, in Polyphenols 94. XVIIe Journees Internationales Groupe Polyphenols, Ed by R. Brouillard, M. Jay, A. Scalbert, INRA Editions, Paris, France, 235–236 (1995).

A.G. Malmberg, O. Theander. Free and conjugated phenolic acids and aldehydes in potato tubers. Swedish Journal of Agricultural Research, 14:119–125 (1984).

A.G. Malmberg, O. Theander Determination of chlorogenic acid in potato tubers. Journal of Agricultural Food and Chemistry, 33:549–551 (1985).

S.N. Onyencho, N.S. Hettiarachchy. Antioxidant activity, fatty acids and phenolic acids composition of potato peels. Journal of the Science of Food and Agricultural, 62:345–350 (1993).

M.N. Clifford, R. Walker. Letter to the editor: Chlorogenic acids – confounders of coffee-serum cholesterol relationship. Food Chemistry, 24:77–80 (1987).

W. Boerjan, J. Ralph, M. Baucher. Lignin biosynthesis. Annual Review of Plant Biology, 54:519-546 (2003).

A. Furrer, D.P. Cladis, A. Kurilich, R. Manoharan, M.G. Ferruzzi. Changes in phenolic content of commercial potato varieties through industrial processing and fresh preparation. Food Chemistry, 218:47–55 (2017).

V. Lattanzio, P.A Kroon, V. Linsalata, A. Cardinali. Globe Artichoke: A functional food and source of nutraceutical ingredients. Journal of Functional Foods, 1:131–144 (2009).

V. Lattanzio, I. Morone. Variations of the orthodiphenol content in Cynara scolymus L. during the plant growing season. Experientia, 35:993–994 (1979).

V. Lattanzio, C.F. Van Sumere. Changes in phenolic compounds during the development and cold storage of artichoke (Cynara scolymus L.) heads. Food Chemistry, 24:37–50 (1987).

V. Lattanzio, N. Cicco, V. Linsalata. Antioxidant activities of artichoke phenolics. Acta Horticulturae, 681:421–428 (2005).

R. Upadhyay, L.J.M. Rao. An Outlook on Chlorogenic Acids – Occurrence, Chemistry, Technology, and Biological Activities. Critical Reviews in Food Science and Nutrition, 53: 968–984 (2013).

I.M. Abu-Reidah, D. Arraez-Roman, A. Segura-Carretero, A. Fernandez-Gutierrez. Extensive characterization of bioactive phenolic constituents from globe artichoke (Cynara scolymus L.) by HPLC-DAD-ESI-QTOF-MS. Food Chemistry, 141:2269–2277 (2013).

M.N. Clifford, R.J. Ramirez-Martinez. Chlorogenic acids and purine alkaloid content of Mate (Ilex paraguariensis) leaf and beverage. Food Chemistry, 35:13–21 (1990).

P. Mazzafera. Mate drinking: caffeine and phenolic acid intake. Food Chemistry, 60:67–71 (1997).

M.I. Dias, L. Barros, M. Duenas, E. Pereira, A.M. Carvalho, R.C. Alves, M.B.P.P. Oliveira, C. Santos-Buelga, I.C.F.R. Ferreira. Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction. Food Chemistry, 141:4152–40 (2013).

A. Raal, A. Orav, T. Pussa, C. Valner, B. Malmiste, E. Arak. Content of essential oil, terpenoids and polyphenols in commercial chamomile (Chamomilla recutita L. Rauschert) teas from different countries. Food Chemistry, 131:632–638 (2012).

S. Vitalini, G. Beretta, M. Iriti, S. Orsenigo, N. Basilico, S. Dall’Acqua, M. Iorizzi, G. Fico. Phenolic compounds from Achillea millefolium L. and their bioactivity. Acta Biochimica Polonica, 58:203–209 (2011).

B. Benedek, N. Gjoncaj, J. Saukel, B. Kopp. Distribution of Phenolic Compounds in Middleeuropean Taxa of the Achillea millefolium L. Aggregate. Chemistry & Biodiveristy, 4:849–856 (2007).

R. Jaiswal, J. Kiprotich, N. Kuhnert. Determination of the hydroxycinnamate of 12 members of the Asteraceae family. Phytochemistry, 72:781–790 (2011).

M. Lutz, C. Henriquez, M. Escobar. Chemical composition and antioxidant properties of mature and baby artichokes (Cynara scolymus L.), raw and cooked. Journal of Food Composition and Analysis, 24:49–54 (2011).

L. Panizzi, M. L. Scarpati. Constitution of cynarine, the active principle of the artichoke. Nature, 174:1062–1063 (1954).

M.N. Clifford, S. Knight, N. Kuhnert. Discriminating between the Six Isomers of Dicaffeoylquinic Acid by LC-MSn. Journal of Agricultural and Food Chemistry, 53:3821–3832 (2005).

S. Deshpande, R. Jaiswal, M.F. Matei, N. Kuhnert. Investigation of Acyl Migration in Mono- and Dicaffeoylquinic Acids under Aqueous Basic, Aqueous Acidic, and Dry Roasting Conditions. Journal of Agricultural and Food Chemistry, 62:9160–9170 (2014).

Y.J. Li, C.-F. Zhang, G. Ding, W.-Z. Huang, Z.-Z. Wang, Y.-A. Bi, W. Xiao. Investigating the thermal stability of six caffeoylquinic acids employing rapid-resolution liquid chromatography with quadrupole time-of-flight tandem mass spectrometry. European Food Research and Technology, 240:1225–1234 (2015).

C. Xie, K. Yu, D. Zhong, T. Yuan, F. Ye, J.A. Jarrel, A. Millar, X. Chen. Investigation of isomeric transformations of chlorogenic acid in buffers and biological matrixes by ultraperformance liquid chromatography coupled with hybrid quadrupole/ion mobility/orthogonal acceleration time-of-flight mass spectrometry, Journal of Agriculture and Food Chemistry, 59:11078–11087 (2011).

M. Xue, H. Shi, J. Zhang, Q.-Q. Liu, J. Guan, J.-Y. Zhang, Q. Ma. Stability and Degradation of Caffeoylquinic Acids under Different Storage Conditions Studied by High-Performance Liquid Chromatography with Photo Diode Array Detection and High-Performance Liquid Chromatography with Electrospray Ionization Collision-Induced Dissociation Tandem Mass Spectrometry. Molecules, 21:948 (2016).

A. Farah, C.M. Donangelo. Phenolic compounds in coffee. Brazilian Journal of Plant Physiology, 18:23–36 (2006).

Z. Hu, D. Chen, L. Dong, W.M. Southerland. Prediction of the interaction of HIV-1 integrase and its dicaffeoylquinic acid inhibitor through molecular modeling approach. Ethnicity & Disease, 20:S−45-9 (2010).

D. Srinath, U.K. Maheswari. Ultrasound Technology in Food Processing: A Review. International Journal of Current Advanced Research, 5:778−783 (2016).

M. Dent, V. Dragovic-Uzelac, I. Elez Garofulic, T. Bosiljkov, D. Jezek, M. Brncic. Comparison of Conventional and Ultrasound-assisted Extraction Techniques on Mass Fraction of Phenolic Compounds from Sage (Salvia officinalis L.). Chemical and Biochemical Engineering Quarterly, 29:475–484 (2015).

M.T. Tena, M.P. Martinez-Moral, P.W. Cardozo. Determination of caffeoylquinic acids in feed and related products by focused ultrasound solid-liquid extraction and ultra-high performance liquid chromatography-mass spectrometry. Journal of Chromatography A, 1400:1–9 (2015).

M.P. Martinez-Moral, M.T. Tena. Focused ultrasound solid-liquid extraction and selective pressurized liquid extraction to determine bisphenol A and alylphenols in sewage sludge by gas chromatography-mass spectrometry. Journal of Separation Science, 34:2513–2522 (2011).

H. Li, B. Chen, S. Yao. Application of ultrasonic technique for extraction chlorogenic acid from Eucommia umodies Oliv. (E. ulmodies). Ultrasonics Sonochemistry, 12:295–300 (2005).

C.S. Eskilsson, E. Bjorklund. Analytical-scale microwave-assisted extraction. Journal of Chromatography A, 902:227–250 (2000).

B. Kaufmann, P. Christen. Recent extraction techniques for natural products: microwave-assisted extraction and pressurised solvent extraction. Phytochemical Analysis, 13:105–113 (2002).

S. Hemwimon, P. Pavasant, A. Shotipruk. Microwave-assisted extraction of antioxidative anthraquinones from roots of Morinda citrifolia. Separation and Purification Technology, 54;44–50 (2007).

R. Upadhyay, K. Ramalakshmi, L.J.M. Rao. Microwave-assisted extraction of chlorogenic acids from green coffee beans. Food Chemistry, 130:184–188 (2012).

H. Li, B. Chen, Z. Zhang, S. Yao. Focused microwave-assisted solvent extraction and HPLC determination of effective constituents in Eucommia ulmodies Oliv. (E. ulmodies). Talanta, 63:659–665 (2004).

W. Routray, V. Orsat. Microwave-Assisted Extraction of Flavonoids: A Review. Food and Bioprocess Technology, 5:409–424 (2012).

S. Masala, U. Rannug, R. Westerholm. Pressurized liquid extraction as an alternative to the Soxhlet extraction procedure stated in the US EPA method TO-13A for the recovery of polycyclic aromatic hydrocarbons adsorbed on polyurethane foam plugs. Analytical Methods, 6:8420–8425 (2014).

A. Mustafa, C. Turner. Pressurized liquid extraction as a green approach in food and herbal plants extraction: A review. Analytica Chimica Acta, 703:8–18 (2011).

R. Carabias-Martinez, E. Rodriguez-Gonzalo, P. Revilla-Ruiz, J. Hernandez-Mendez. Pressurized liquid extraction in the analysis of food and biological samples. Journal of Chromatography A, 1089:1–17 (2005).

R. Ibanez,M. Herrero, J.A. Mendiola, M. Castro-Puyana. Extraction and Characterization of Bioactive Compounds with Health Benefits from Marine Resources: Macro and Micro Algae, Cyanobacteria, and Invertebrates. Marine Bioactive Compounds: Sources, Characterization and Applications, Chapter 2:55–98 (2012).

R.M. Alonso-Salces, E. Korta, A. Barranco, L.A. Berrueta, B. Gallo. F. Vincente. Pressurized liquid extraction for the determination of polyphenols in apple. Journal of Chromatography A, 933:37–43 (2001).

X. Lou, H.-G. Janssen, C.A. Crames. Parameters Affecting the Accelerated Solvent Extraction of Polymeric Samples. Analytical Chemistry, 69:1598–1603 (1997).

. D.L. Luthria. Influence of experimental conditions on the extraction of phenolic compounds from parsley (Petroselinum crispum) flakes using a pressurized liquid extractor. Food Chemistry, 107:745–752 (2008).

S. Erdogan, B. Ates, G. Durmaz, I. Yilmaz, T. Seckin. Pressurized liquid extraction of phenolic compounds from Anatolia propolis and their radical scavenging capacities. Food and Chemical Toxicology, 49:1592–1597 (2011).

M. Jeszka-Skowron, A. Zgoła-Grześkowiak, T. Grześkowiak. Analytical method applied for the characterization and the determination of bioactive compounds in coffee. European Food Research and Technology, 240:19–31 (2015).

M. Antolovich, P. Prenzler, K. Robards, D. Ryan. Sample preparation in the determination of phenolic compounds in fruit. The Analyst, 125:989–1009 (2000).

C.D. Stalikas. Extraction, separation, and detection method for phenolic acids and flavonoids. Journal of Separation Science, 30:3268–3295 (2007).

L. Gao, G. Mazza. Quantitation and Distribution of Simple and Acylated Anthocyanins and Other Phenolics in Blueberries. Journal of Food Science, 59:1057–1059 (1994).

J.J. Mangas, R. Rodríguez, B. Suárez, A. Picinelli, E. Dapena. Study of the phenolic profile of cider apple cultivars at maturity by multivariate techniques. Journal of Agricultural and Food Chemistry, 47:4046–4052 (1999).

A. Escarpa, M.C. Gonzalez. Fast separation of (poly)phenolic compounds from apples and pears by high-performance liquid chromatography with diode-array detection. Journal of Chromatography A, 830:301–309 (1999).

M.J. Amiot, M. Tacchini, S. Aubert, J. Nicolas. Phenolic Composition and Browning Susceptibility of Various Apple Cultivars at Maturity. Journal of Food Science, 57: 958–962 (1992).

B. Suárez, A. Picinelli, J.J. Mangas. Solid-phase extraction and high-performance liquid chromatographic determination of polyphenols in apple musts and cider. Journal of Chromatography A, 727:203–209 (1996).

M.J. Amiot, M. Tacchini, S.Y. Aubert, W. Oleszek. Influence of Cultivar, Maturity Stage, and Storage Conditions on Phenolic Composition and Enzymic Browning of Pear Fruits. Journal of Agricultural and Food Chemistry, 43:1132–1137 (1995).

L. Gao, G. Mazza. Characterization, Quantitation, and Distribution of Anthocyanins and Colorless Phenolics in Sweet Cherries. Journal of Agricultural and Food Chemistry, 43:343–346 (1995).

H.M. Dawes, J.B. Keene. Phenolic composition of kiwifruit juice. Journal of Agricultural and Food Chemistry, 47:2398–2403 (1999).

Z. Fuzfai, I. Molnar-Perl. Gas chromatographic-mass spectrometric fragmentation study of flavonoids as their trimethylsilyl derivatives: analysis of flavonoids, sugars, carboxylic and amino acids in model systems and in citrus fruits. Journal of Chromatography A, 1149:88–101 (2007).

H. Chen, Y. Zuo, Y. Deng. Separation and determination of flavonoids and other phenolic compounds in cranberry juice by high-performance liquid chromatography. Journal of Chromatography A, 913:387–395 (2001).

D. Jirovsky, D. Horakova, M. Kotoucek, K. Valentova, J. Ulrichova. Analysis of phenolic acids in plant materials using HPLC with amperometric detection at a platinum tubular electrode. Journal of Separation Science, 26:739–742 (2003).

M. Brolis, B. Gabetta, N. Fuzzati, R. .Pace, F. Panzeri, F. Peterlongo. Identification by high-performance liquid chromatography–diode array detection–mass spectrometry and quantification by high-performance liquid chromatography–UV absorbance detection of active constituents of Hypericum perforatum. Journal of Chromatography A, 825:9–16 (1998).

G. Zgorka, S. Dawka. Application of conventional UV, photo-diode array (PDA) and fluorescence (FL) detection to analysis of phenolic acid in plant material and pharmaceutical preparations. Journal of Pharmaceutical and Biomedical Analysis, 24:1065–1072 (2001).

Y. Guan, T. Wu, M. Lin, J. Ye. Determination of Pharmacologically Active Ingredients in Sweet Potato (Ipomoea batatas L.) by Capillary Electrophoresis with Electrochemical Detection. Journal of Agricultural and Food Chemistry, 54:24–28 (2006).

H.-L. Jiang, Y.-Z. He, H.-Z. Zhao, Y.-Y. Hu. Determination of chlorogenic acid and rutin in cigarettes by an improved capillary electrophoresis indirect chemiluminescence system. Analytica Chimica Acta, 512:111–119 (2004).

B. Tang, D. Guo, Y. Li, H. Yang, Y. Huang, H. Li. Separation and quantitation of isomeric caffeoylquinic acids in honeysuckle products by low-pH microemulsion electrokinetic chromatography using tartrate as a chiral selector. Analytical Methods, 8:189–196 (2016).

E. M. Risso, G. R. Peres, J. Amaya-Farfan. Determination of phenolic acids in coffee by micellar electrokinetic chromatography. Food Chemistry, 105:1578–1582 (2007).

E.-H. Liu, L.-W. Qi, J. Cao, P. Li, C.-Y. Li, Y.-B. Peng. Advances of Modern Chromatographic and Electrophoretic Methods in Separation and Analysis of Flavonoids. Molecules, 13:2521–2544 (2008).

E.C. Tatsis, S. Boeren, V. Exarchou. Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS. Phytochemistry 68:383–393 (2007).

G. Miliauskas, T.A. de W. van Beek, P.R.P. Venskutonis; E.J.R. Sudholter. Identification of radical scavenging compounds in Rhaponticum carthamoides by means of LC-DAD-SPE-NMR. Journal of Natural Products, 68:168–172 (2005).

J.-P. Lai, Y.H. Lim, J.Su, H.-M. Shen, C.N. Ong. Identification and characterization of major flavonoids and caffeoylquinic acids in three Compositae plants by LC/DAD-APCI/MS. Journal of Chromatography B, 848:215–225 (2007).

X. Xiao, J. Ma, F. Ge, X. Zhang, H. Yang, Q. Liang, Y. Wang, G. Luo. Application of near-infrared spectroscopy for the rapid analysis of Lonicerae Japonicae Flos solution extracted by water. Journal of Innovative Optical Health Science, 7 (2014).

C.-L. Fan, Y.-M. Liu, Y.-Z. Cao, J.-J. Zhang, X.-M. Li, Z.-Y. Li, Y.-P. Wu, T.-T. Guo. Determination of residues of 446 pesticides in fruits and vegetables by three-cartridge solid-phase extraction-gas chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry. Journal of AOAC International, 89:740-71 (2006).

O. Kenny, J.T. Smyth, M.C. Hewage, P. N. Brunton. Quantitative UPLC-MS/MS analysis of chlorogenic acid derivatives in antioxidant fractionates from dandelion (Taraxacum officinale) root. International Journal of Food Science and Technology, 50:766–773 (2015).

R. Gu, G. Dou, J. Wang, J. Dong, Z. Meng. Simultaneous determination of 1,5-dicaffeoylquinic acid and its active metabolites in human plasma by liquid chromatography-tandem mass spectrometry for pharmacokinetic studies. Journal of Chromatography B, 852:85–91 (2007).

G. Dai, S. Ma, B. Sun, T. Gong, S. Liu, C. Li, W. Ju. Simultaneous determination of 1,3-dicaffeoylquinic acid and caffeic acid in rat plasma by liquid chromatography/tandem mass spectrometry and its application to a pharmacokinetic study. Analytical Methods, 7:3587–3592 (2015).

E. Bajko, M. Kalinowska, P. Borowski, L. Siergiejczyk, W. Lewandowski. 5-O-Caffeoylquinic acid: A spectroscopic study and biological screening for antimicrobial activity. LWT – Food Science and Technology, 65:471–479 (2016).

N.M. Clifford, W. Wu, J. Kirkpatrick, R. Jaiswal, N. Kuhnert. Profiling and characterization by liquid chromatography/multi-stage mass spectrometry of the chlorogenic acids in Gardeniae Fructus. Rapid Communications in Mass Spectrometry, 24:3109–3120 (2010).

C.S. Gouveia, C.P. Castilho. Analysis of phenolic compounds from different morphological parts of Helichrysum devium by liquid chromatography with on-line UV and electrospray ionization mass spectrometric detection. Rapid Communications in Mass Spectrometry, 23:3939–3953 (2009).

M.T. Tena, M.P. Martinez-Moral, P.W. Cardozo. Determination of caffeoylquinic acids in feed and related products by focused ultrasound solid-liquid extraction and ultra-high performance liquid chromatography-mass spectrometry. Journal of Chromatography A, 1400:1–9 (2015).

Q. Shen, Z. Dai, Y. Lu. Rapid determination of caffeoylquinic acid derivatives in Cynara scolymus L. by ultra-fast liquid chromatography/tandem mass spectrometry based on a fused core C18 column. Journal of Separation Science, 33:3152–3158 (2010).

W.-B. Zhang, Z.-C. Wang, L.-Y. Zhang. Determination of 10 Caffeoylquinic Acids and 22 Flavonoids in Chrysanthemum Samples by Ultra-high Performance Liquid Chromatography-Diode Array Detection-Tandem Mass Spectrometry. Chinese Journal of Analytical Chemistry, 41:1851–1861 (2013).

P. Paya, M. Anastassiades, D. Mack, I. Sigalova, B. Tasdelen. J. Oliva, A. Barba. Analysis of pesticides residues using the quick easy cheap effective rugged and safe (QuEChERS) pesticide multiresidue method in combination with gas and liquid chromatography and tandem mass spectrometric detection. Analytical and Bioanalytical Chemistry, 389:1697–1714 (2007).

N.I. Urakova, N.O. Pozharitskaya, N.A. Shikov, M.V. Kosman, G.V. Makarov. Comparison of high performance TLC and HPLC for separation and quantification of chlorogenic acid in green coffee bean extracts. Journal of Separation Science, 31:237–241 (2008).

S.-M. Kim, Y.-F. Shang, B.-H. Um. Preparative Separation of Chlorogenic Acid by Centrifugal Partition Chromatography from Highbush Blueberry Leaves (Vaccinium corymbosum L.). Phytochemical Analysis, 21:457–462 (2010).




DOI: http://dx.doi.org/10.17951/aa.2017.72.1.61
Data publikacji: 2017-12-08 10:35:23
Data złożenia artykułu: 2017-05-25 13:35:37

Refbacks

  • There are currently no refbacks.


Copyright (c) 2017 Marta Gil, Dorota Wianowska