Analysis of a series of chlorogenic acid isomers using differential ion mobility and tandem mass spectrometry

Analytica Chimica Acta

Volumn 933, Issue , 2016, Pages 164-174

  Willems, Jamie L ^a   Khamis, Mona M ^a   Mohammed Saeid, Waleed ^a   Purves, Randy W ^a   Katselis, George ^b   Low, Nicholas H ^a   El Aneed, Anas ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Chlorogenic acid isomers; Differential ion mobility; Tandem mass spectrometry

Indexed keywords

DISSOCIATION; ELECTROSPRAY IONIZATION; FRUIT JUICES; FRUITS; IONIZATION; IONS; MASS SPECTROMETRY; NEGATIVE IONS; SPECTROMETRY;

CHLOROGENIC ACIDS; DISSOCIATION PATHWAYS; ELECTROSPRAY IONIZATION (ESI); HIGH-FIELD ASYMMETRIC WAVEFORM ION MOBILITY SPECTROMETRIES; ION MOBILITY; SEPARATION AND IDENTIFICATION; TANDEM MASS SPECTROMETRIC; TANDEM MASS SPECTROMETRY;

ISOMERS;

4 O CAFFEOYLQUINIC ACID; CHLOROGENIC ACID; NEOCHLOROGENIC ACID; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CONTROLLED STUDY; DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; HYDROLYSIS; ION MOBILITY SPECTROMETRY; MEASUREMENT ACCURACY; MOLECULAR WEIGHT; PRIORITY JOURNAL; PROTON TRANSPORT; SENSITIVITY AND SPECIFICITY; CHEMICAL STRUCTURE; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

CHLOROGENIC ACID; ION MOBILITY SPECTROMETRY; MOLECULAR STRUCTURE; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 84973473720     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2016.05.041     Document Type: Article

References (51)

1. [1] Friedman, M., Jürgens, H.S., Effect of pH on the stability of plant phenolic compounds. J. Agric. Food Chem. 48 (2000), 2101–2110.
2. [2] Fernandez de Simon, B., Perez-Ilzarbe, J., Hernandez, T., Gomez-Cordoves, C., Estrella, I., Importance of phenolic compounds for the characterization of fruit juices. J. Agric. Food Chem. 40 (1992), 1531–1535.
3. [3] Shahidi, F., Naczk, M., Phenolics in Food and Nutraceuticals. 2003, CRC Press.
4. [4] Dai, J., Mumper, R.J., Plant phenolics: extraction, analysis and their antioxidant and anticancer properties. Molecules 15 (2010), 7313–7352.
5. [5] Nayak, B., Liu, R.H., Tang, J.M., Effect of processing on phenolic antioxidants of fruits, vegetables, and grains-a review. Crit. Rev. Food Sci. Nutr. 55 (2015), 887–918.
6. [6] Lattanzio, V., Phenolic compounds: introduction. Ramawat, K.G., Mérillon, J.M., (eds.) Natural Products – Phytochemistry, Botany and Metabolism of Alkaloids, 2013, Phenolics and Terpenes, Springer-Verlag, Berlin Heidelberg, 1543–1580.
7. [7] Versari, A., Biesenbruch, S., Barbanti, D., Farnell, P., Adulteration of fruit juices: dihydrochalcones as quality markers for apple juice identification. LWT – Food Sci. Technol. 30 (1997), 585–589.
8. [8] Clifford, M.N., Chlorogenic acids and other cinnamates–nature, occurrence, dietary burden, absorption and metabolism. J. Sci. Food Agric. 80 (2000), 1033–1043.
9. [9] Jaiswal, R., Matei, M.F., Ullrich, F., Kuhnert, N., How to distinguish between cinnamoylshikimate esters and chlorogenic acid lactones by liquid chromatography–tandem mass spectrometry. J. Mass Spectrom. 46 (2011), 933–942.
10. [10] Upadhyay, R., Mohan Rao, L.J., An outlook on chlorogenic acids—occurrence, chemistry, technology, and biological activities. Crit. Rev. Food Sci. Nutr. 53 (2013), 968–984.
11. [11] Iupac, C., Cbn, I.I., The nomenclature of cyclitols. Eur. J. Biochem. 5 (1968), 1–12.
12. [12] Feng, R., Lu, Y., Bowman, L.L., Qian, Y., Castranova, V., Ding, M., Inhibition of activator protein-1, NF-κB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid. J. Biol. Chem. 280 (2005), 27888–27895.
13. [13] Kono, Y., Kobayashi, K., Tagawa, S., Adachi, K., Ueda, A., Sawa, Y., Shibata, H., Antioxidant activity of polyphenolics in diets: rate constants of reactions of chlorogenic acid and caffeic acid with reactive species of oxygen and nitrogen. Biochim. Biophys. Acta BBA – General Subj. 1335 (1997), 335–342.
14. [14] Kweon, M.-H., Hwang, H.-J., Sung, H.-C., Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis). J. Agric. Food Chem. 49 (2001), 4646–4655.
15. [15] Nakatani, N., Kayano, S.-i., Kikuzaki, H., Sumino, K., Katagiri, K., Mitani, T., Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in Prune (Prunus domestica L.). J. Agric. Food Chem. 48 (2000), 5512–5516.
16. [16] Rice-Evans, C.A., Miller, N.J., Paganga, G., Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20 (1996), 933–956.
17. [17] Dos Santos, M.D., Almeida, M.C., Lopes, N.P., De Souza, G.E.P., Evaluation of the anti-inflammatory, analgesic and antipyretic activities of the natural polyphenol chlorogenic acid. Biol. Pharm. Bull. 29 (2006), 2236–2240.
18. [18] McDougall, B., King, P.J., Wu, B.W., Hostomsky, Z., Reinecke, M.G., Robinson, W.E., Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. Antimicrob. Agents Chemother. 42 (1998), 140–146.
19. [19] Mori, H., Tanaka, T., Shima, H., Kuniyasu, T., Takahashi, M., Inhibitory effect of chlorogenic acid on methylazoxymethanol acetate-induced carcinogenesis in large intestine and liver of hamsters. Cancer Lett. 30 (1986), 49–54.
20. [20] Clifford, M.N., Chlorogenic acids—their complex nature and routine determination in coffee beans. Food Chem. 4 (1979), 63–71.
21. [21] Farah, A., Monteiro, M., Calado, V., Franca, A., Trugo, L., Correlation between cup quality and chemical attributes of Brazilian coffee. Food Chem. 98 (2006), 373–380.
22. 1. J. Sci. Food Agric. 79 (1999), 362–372.
23. [23] Spanos, G.A., Wrolstad, R.E., Influence of variety, maturity, processing and storage on the phenolic composition of pear juice. J. Agric. Food Chem. 38 (1990), 817–824.
24. [24] Spanos, G.A., Wrolstad, R.E., Heatherbell, D.A., Influence of processing and storage on the phenolic composition of apple juice. J. Agric. Food Chem. 38 (1990), 1572–1579.
25. [25] Cui, T., Nakamura, K., Ma, L., Li, J.-Z., Kayahara, H., Analyses of arbutin and chlorogenic acid, the major phenolic constituents in oriental pear. J. Agric. Food Chem. 53 (2005), 3882–3887.
26. [26] Jaiswal, R., Matei, M.F., Golon, A., Witt, M., Kuhnert, N., Understanding the fate of chlorogenic acids in coffee roasting using mass spectrometry based targeted and non-targeted analytical strategies. Food Funct. 3 (2012), 976–984.
27. [27] Ignat, I., Volf, I., Popa, V.I., Analytical Methods of Phenolic Compounds, Natural Products. 2013, Springer, 2061–2092.
28. n of four new classes of chlorogenic acids in green coffee beans: dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycinnamoylquinic acids. J. Agric. Food Chem. 54 (2006), 1957–1969.
29. [29] Marks, S.C., Mullen, W., Crozier, A., Flavonoid and chlorogenic acid profiles of English cider apples. J. Sci. Food Agric. 87 (2007), 719–728.
30. [30] Fang, N., Yu, S., Prior, R.L., LC/MS/MS characterization of phenolic constituents in dried plums. J. Agric. Food Chem. 50 (2002), 3579–3585.
31. [31] Buse, J., Badea, I., Verrall, R.E., El-Aneed, A., Tandem mass spectrometric analysis of novel diquaternary ammonium gemini surfactants and their bromide adducts in electrospray-positive ion mode ionization. J. Mass Spectrom. 46 (2011), 1060–1070.
32. [32] Awad, H., Das, U., Dimmock, J., El-Aneed, A., Establishment of tandem mass spectrometric fingerprint of novel antineoplastic curcumin analogues using electrospray ionization. Rapid Commun. Mass Spectrom. 29 (2015), 1–10.
33. n identification of chlorogenic acids. J. Agric. Food Chem. 51 (2003), 2900–2911.
34. n. J. Agric. Food Chem. 53 (2005), 3821–3832.
35. n of the chlorogenic acids and hydroxycinnamoylshikimate esters in Maté (Ilex paraguariensis)†. J. Agric. Food Chem. 58 (2010), 5471–5484.
36. [36] Schram, K., Miketova, P., Slanina, J., Humpa, O., Taborska, E., Mass spectrometry of 1, 3-and 1, 5-dicaffeoylquinic acids. J. Mass Spectrom. 39 (2004), 384–395.
37. [37] Sakushima, A., Hisada, S., Nishibe, S., Brandenderger, H., Application of fast atom bombardment mass spectrometry to chlorogenic acids. Phytochemistry 24 (1985), 325–328.
38. [38] Verbeck, G., Ruotolo, B., Sawyer, H., Gillig, K., Russell, D., A fundamental introduction to ion mobility mass spectrometry applied to the analysis of biomolecules. J. Biomol. Tech. – JBT, 13, 2002, 56.
39. [39] Kanu, A.B., Dwivedi, P., Tam, M., Matz, L., Hill, H.H., Ion mobility–mass spectrometry. J. Mass Spectrom. 43 (2008), 1–22.
40. [40] Dwivedi, P., Wu, C., Matz, L.M., Clowers, B.H., Siems, W.F., Hill, H.H., Gas-phase chiral separations by ion mobility spectrometry. Anal. Chem. 78 (2006), 8200–8206.
41. [41] Green, R.C., Physicochemical Properties and Phenolic Composition of Selected Saskatchewan Fruits: Buffaloberry, Chokecherry and Sea Buckthorn. 2007, University of Saskatchewan, Saskatoon, SK, Canada.
42. [42] Prasad, S., Belford, M.W., Dunyach, J.-J., Purves, R.W., On an aerodynamic mechanism to enhance ion transmission and sensitivity of FAIMS for nano-electrospray ionization-mass spectrometry. J. Am. Soc. Mass Spectrom. 25 (2014), 2143–2153.
43. [43] Purves, R.W., Ozog, A.R., Ambrose, S.J., Prasad, S., Belford, M., Dunyach, J.-J., Using gas modifiers to significantly improve sensitivity and selectivity in a cylindrical FAIMS device. J. Am. Soc. Mass Spectrom. 25 (2014), 1274–1284.
44. [44] Cuyckens, F., Claeys, M., Mass spectrometry in the structural analysis of flavonoids. J. Mass Spectrom. 39 (2004), 1–15.
45. [45] Vrhovsek, U., Masuero, D., Gasperotti, M., Franceschi, P., Caputi, L., Viola, R., Mattivi, F., A versatile targeted metabolomics method for the rapid quantification of multiple classes of phenolics in fruits and beverages. J. Agric. Food Chem. 60 (2012), 8831–8840.
46. [46] Andrade, P., Carvalho, A., Seabra, R., Ferreira, M., A previous study of phenolic profiles of quince, pear, and apple purees by HPLC diode array detection for the evaluation of quince puree genuineness. J. Agric. Food Chem. 46 (1998), 968–972.
47. [47] Orčić, D., Francišković, M., Bekvalac, K., Svirčev, E., Beara, I., Lesjak, M., Mimica-Dukić, N., Quantitative determination of plant phenolics in Urtica dioica extracts by high-performance liquid chromatography coupled with tandem mass spectrometric detection. Food Chem. 143 (2014), 48–53.
48. [48] Cech, N.B., Enke, C.G., Practical implications of some recent studies in electrospray ionization fundamentals. Mass Spectrom. Rev. 20 (2001), 362–387.
49. [49] Beach, D.G., Melanson, J.E., Purves, R.W., Analysis of paralytic shellfish toxins using high-field asymmetric waveform ion mobility spectrometry with liquid chromatography-mass spectrometry. Anal. Bioanal. Chem. 407 (2015), 2473–2484.
50. [50] Willems, J.L., Low, N.H., Authenticity analysis of pear juice employing chromatographic fingerprinting. J. Agric. Food Chem. 62 (2014), 11737–11747.
51. [51] Kolniak-Ostek, J., Oszmiański, J., Characterization of phenolic compounds in different anatomical pear (Pyrus communis L.) parts by ultra-performance liquid chromatography photodiode detector-quadrupole/time of flight-mass spectrometry (UPLC-PDA-Q/TOF-MS). Int. J. Mass Spectrom. 392 (2015), 154–163.