Analytical methods applied for the characterization and the determination of bioactive compounds in coffee

European Food Research and Technology

Volumn 240, Issue 1, 2015, Pages 19-31

  Jeszka Skowron, Magdalena ^a   Zgoła Grześkowiak, Agnieszka ^a   Grześkowiak, Tomasz ^a  

^a POZNAN UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Caffeine; Chlorogenic acids; Coffee; Diterpenes; Nicotinic acid; Trigonelline

Indexed keywords

CAFFEINE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

ANTIOXIDATIVE PROPERTY; CHLOROGENIC ACIDS; DITERPENES; HYPHENATED TECHNIQUES; NICOTINIC ACID; SHORT-CHAIN CARBOXYLIC ACIDS; TRIGONELLINE; ULTRAVIOLET SPECTROPHOTOMETRY;

COFFEE;

EID: 84925465103     PISSN: 14382377     EISSN: 14382385     Source Type: Journal    
DOI: 10.1007/s00217-014-2356-z     Document Type: Review

References (104)

1. Wolf A, Bray GA, Popkin BM (2008) A short history of beverages and how our body treats them. Obes Rev 9:151–164
2. Agritrade. Informed Analysis, Expert Opinions. Executive Brief. (2013) Technical Centre for Agricultural and Rural Cooperation. Wageningen, The Netherlands
3. International Coffee Organization (2013) Annual Review 2011/12. London, United Kingdom
4. Esquivel P, Jiménez VM (2012) Functional properties of coffee and coffee by-products. Food Res Int 46:488–495
5. Bhupathiraju SN, Pan A, Malik VS, Manson JE, Willett WC, van Dam RM, Hu FB (2013) Caffeinated and caffeine-free beverages and risk of type 2 diabetes. Am J Clin Nutr 97:155–166
6. Cano-Marquina A, Tarín JJ, Cano A (2013) The impact of coffee on health. Maturitas 75:7–21
7. Gómez-Ruiz JA, Leake DS, Ames JM (2007) In vitro antioxidant activity of coffee compounds and their metabolites. J Agric Food Chem 55:6962–6969
8. Motilva M-J, Serra A, Macià A (2013) Analysis of food polyphenols by ultra high-performance liquid chromatography coupled to mass spectrometry: an overview. J Chromatogr A 1292:66–82
9. Shrivas K, Wu HF (2007) Rapid determination of caffeine in one drop of beverages and foods using drop-to-drop solvent microextraction with gas chromatography/mass spectrometry. J Chromatogr A 1170:9–14
10. Araujo JMA, Sandi D (2006) Extraction of coffee diterpenes and coffee oil using supercritical carbon dioxide. Food Chem 101:1087–1094
11. Alonso-Salces RM, Guillou C, Berrueta LA (2009) Liquid chromatography coupled with ultraviolet absorbance detection, electrospray ionisation, collision-induced dissociation and tandem mass spectrometry for the on-line characterization of polyphenols and methylxanthines in green coffee beans. Rapid Commun Mass Spectrom 23:363–383
12. n identification of chlorogenic acids. J Agric Food Chem 51:2900–2911
13. Farah A, de Paulis T, Moreira DP, Trugo LC, Martin PR (2006) Chlorogenic acids and lactones in regular and water-decaffeinated arabica coffees. J Agric Food Chem 54:374–381
14. Iwai K, Kishimoto N, Kakino Y, Mochida K, Fujita T (2004) In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans. J Agric Food Chem 52:4893–4898
15. Farah A, Monteiro MC, Calado V, Franca AS, Trugo LC (2006) Correlation between cup quality and chemical attributes of Brazilian coffee. Food Chem 98:373–380
16. Farah A, de Paulis T, Trugo LC, Martin PR (2005) Effect of roasting on the formation of chlorogenic acids lactones in coffee. J Agric Food Chem 53:1505–1513
17. Monteiro MC, Farah A (2012) Chlorogenic acids in Brazilian Coffea arabica cultivars from various consecutive crops. Food Chem 134:611–614
18. Campa C, Doulbeau S, Dussert S, Hamon S, Noirot M (2005) Qualitative relationship between caffeine and chlorogenic acid contents among wild Coffea species. Food Chem 93:135–139
19. DIN-10767 (1992) Analysis of coffee and coffee products: determination of chlorogenic acids content—HPLC method
20. Rakotomalala JJR (1992) Diversité biochimique des caféiers: analyse des acides hydroxycinnamiques, bases puriques et diterpènes glycosides. Particularités des caféiers sauvages de la region malgache (Mascarocoffea Chev.). Université Sciences et Techniques du Languedoc, Montpellier II, France, Montpellier, France, p 219
21. Bicchi CP, Binello AE, Pellegrino GM, Vanni AC (1995) Characterization of green and roasted coffees through the chlorogenic acid fraction by HPLC–UV and principal component analysis. J Agric Food Chem 43:1549–1555
22. Suárez-Quiroz ML, Alonso Campos A, Valerio Alfaro G, González-Ríos O, Villeneuve P, Figueroa-Espinoza MC (2014) Isolation of green coffee chlorogenic acids using activated carbon. J Food Compos Anal 33:55–58
23. Balyaya KJ, Clifford MN (1995) Individual chlorogenic acids and caffeine contents in commercial grades of wet and dry processed Indian green Robusta coffee. J Food Sci Technol Mys 32:104–108
24. Trugo LC, Macrae R (1984) A study of the effect of roasting on the chlorogenic acid composition of coffee using HPLC. Food Chem 15:219–227
25. Alonso-Salces RM, Serra F, Reniero F, Héberger K (2009) Botanical and geographical characterization of green coffee (Coffea arabica and Coffea canephora): chemometric evaluation of phenolic and methylxanthine contents. J Agric Food Chem 57:4224–4235
26. Upadhyay R, Ramalakshmi K, Rao LJM (2012) Microwave-assisted extraction of chlorogenic acids from green coffee beans. Food Chem 130:184–188
27. Budryn G, Nebesny E, Podsędek A, Żyżelewicz D, Materska M, Jankowski S, Janda B (2009) Effect of different extraction methods on the recovery of chlorogenic acids, caffeine and Maillard reaction products in coffee beans. Eur Food Res Technol 228:913–922
28. Ky C-L, Noirot M, Hamon S (1997) Comparison of five purification methods for chlorogenic acids in green coffee beans (Coffea sp.). J Agric Food Chem 45:786–790
29. Perrone D, Farah A, Donangelo CM, de Paulis T, Martin PR (2008) Comprehensive analysis of major and minor chlorogenic acids and lactones in economically relevant Brazilian coffee cultivars. Food Chem 106:859–867
30. Kuhnert N, Jaiswal R, Eravuchira P, El-Abassy RM, Kammer B, Materny A (2011) Scope and limitations of principal component analysis of high resolution LC–TOF MS data: the analysis of the chlorogenic acid fraction in green coffee beans as a case study. Anal Methods 3:144–155
31. Risso EM, Péres RG, Amaya-Farfan J (2007) Determination of phenolic acids in coffee by micellar electrokinetic chromatography. Food Chem 105:1578–1582
32. Belay A, Gholap AV (2009) Characterization and determination of chlorogenic acids (CGA) in coffee beans by UV–Vis spectroscopy. Afr J Pure Appl Chem 3:234–240
33. Caprioli G, Cortese M, Odello L, Ricciutelli M, Sagratini G, Tomassoni G, Vittori S (2013) Importance of espresso coffee machine parameters on the extraction of chlorogenic acids in a certified Italian Espresso by using SPE-786 HPLC–DAD. J Food Res 2:55–64
34. Niseteo T, Komes D, Belščak-Cvitanović A, Horžić D, Budeč M (2012) Bioactive composition and antioxidant potential of different commonly consumed coffee brews affected by their preparation technique and milk addition. Food Chem 134:1870–1877
35. Vignoli JA, Viegas MC, Bassoli DG, de Benassi M (2014) Roasting process affects differently the bioactive compounds and the antioxidant activity of arabica and robusta coffees. Food Res Int 61:279–285
36. n. J Food Compos Anal 32:105–115
37. Alves RC, Almeida IMC, Casal S, Oliveira MBPP (2010) Method development and validation for isoflavones quantification in coffee. Food Chem 122:914–919
38. Jaiswal R, Matei MF, Subedi P, Kuhnert N (2014) Does roasted coffee contain chlorogenic acid lactones or/and cinnamoylshikimate esters? Food Res Int 61:214–227
39. Kaiser N, Birkholz D, Colomban S, Navarini L, Engelhardt UH (2013) A new method for the preparative isolation of chlorogenic acid lactones from coffee and model roasts of 5-caffeoylquinic acid. J Agric Food Chem 61:6937–6941
40. de Araújo TA, Cardoso JC, Barbosa AM, Ferreira VS (2009) Influence of the surfactant bromide of cetyltrimetyl ammonium in the determination of chlorogenic acid in instant coffee and mate tea samples. Colloids Surf B 73:408–414
41. de Carvalho ML, Santhiago M, Peralta RA, Neves A, Micke GA, Vieira IC (2008) Determination of chlorogenic acid in coffee using a biomimetic sensor based on a new tetranuclear copper(II) complex. Talanta 77:394–399
42. Fernandes SC, Moccelini SK, Scheeren CW, Migowski P, Dupont J, Heller M, Vieira IC (2009) Biosensor for chlorogenic acid based on an ionic liquid containing iridium nanoparticles and polyphenol oxidase. Talanta 79:222–228
43. Santos WJR, Santhiago M, Yoshida IVP, Kubota LT (2011) Novel electrochemical sensor for the selective recognition of chlorogenic acid. Anal Chim Acta 695:44–50
44. Yardım Y, Keskin E, Şentürk Z (2013) Voltammetric determination of mixtures of caffeine and chlorogenic acid in beverage samples using a boron-doped diamond electrode. Talanta 116:1010–1017
45. Ziyatdinova G, Aytuganova I, Nizamova A, Budnikov H (2013) Differential pulse voltammetric assay of coffee antioxidant capacity with MWNT-modified electrode. Food Anal Methods 68:132–139
46. Murkies AL, Wilcox G, Davis SR (1998) Phytoestrogens. J Clin Endocrinol Metab 83:297–303
47. Alves RC, Almeida IMC, Casal S, Oliveira MBPP (2010) Isoflavones in coffee: influence of species, roast degree, and brewing method. J Agric Food Chem 58:3002–3007
48. Mazur W, Fotsis T, Wahala K, Ojala S, Salakka A, Adlercreutz H (1996) Isotope dilution gas chromatographic–mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples. Anal Biochem 233:169–180
49. Thompson LU, Boucher BA, Liu Z, Cotterchio M, Kreiger N (2006) Phytoestrogen content of food consumed in Canada, including isoflavones, lignans and coumestan. Nutr Cancer 54:184–201
50. Kuhnle GG, Dell’Aquila C, Low Y-L, Kussmaul M, Bingham SA (2007) Extraction and quantification of phytoestrogens in food using automated SPE and LC/MS/MS. Anal Chem 79:9234–9239
51. Oomah BD, Hosseinian FS (2007) In: W. J. Hurst (Ed.), Methods of analysis for functional foods and nutraceuticals (2nd ed.). Phytoestrogens. Boca Raton, FL: Taylor and Francis Group LLC
52. Kuhnle GGC, Dell’Aquila C, Aspinall SM, Runswick SA, Mulligan AA, Bingham SA (2008) Phytoestrogen content of beverages, nuts, seeds, and oils. J Agric Food Chem 56:7311–7315
53. Gloess A, Schönbächler B, Klopprogge B, D`Ambrosio L, Chatelain K, Bongartz A, Strittmatter A, Rast M, Yeretzian C (2013) Comparison of nine common coffee extraction methods: instrumental and sensory analysis. Eur Food Res Technol 236:607–627
54. Hečimović I, Belščak-Cvitanović A, Horžić D, Komes D (2011) Comparative study of polyphenols and caffeine in different coffee varieties affected by the degree of roasting. Food Chem 129:991–1000
55. Carrillo JA, Benitez J (2000) Clinically significant pharmacokinetic interactions between dietary caffeine and medications. Clin Pharmacokinet 39:127–153
56. Ky C-L, Louarn J, Dussert S, Guyot B, Hamon S, Noirot M (2001) Caffeine, trigonelline, chlorogenic acids and sucrose diversity in wild Coffea arabica L. and C. canephora P. accessions. Food Chem 75:223–230
57. Bispo MS, Veloso MCC, Pinhero HLC, De Oliveira RFS, Reis JON, De Andrade JB (2002) Simultaneous determination of caffeine, theobromine, and theophylline by high-performance liquid chromatography. J Chromatogr Sci 40:45–48
58. Casal S, Beatriz Oliveira M, Ferreira MA (2000) HPLC/diode-array applied to the thermal degradation of trigonelline, nicotinic acid and caffeine in coffee. Food Chem 68:481–485
59. Perrone D, Donangelo CM, Farah A (2008) Fast simultaneous analysis of caffeine, trigonelline, nicotinic acid and sucrose in coffee by liquid chromatography–mass spectrometry. Food Chem 110:1030–1035
60. Rodrigues CI, Marta L, Maia R, Miranda M, Ribeirinho M, Máguas C (2007) Application of solid-phase extraction to brewed coffee caffeine and organic acid determination by UV/HPLC. J Food Compos Anal 20:440–448
61. Meinhart AD, Schaper Bizzotto C, Ballus CA, Prado MA, Bruns RE, Teixeira Filho J, Teixeira Godoy H (2010) Optimisation of a CE method for caffeine analysis in decaffeinated coffee. Food Chem 120:1155–1161
62. Danhelova H, Hradecky J, Pronosilova S, Cajka T, Riddellova K, Vaclavik L, Hajslova J (2012) Rapid analysis of caffeine in various coffee samples employing direct analysis in real-time ionization-high-resolution mass spectrometry. Anal Bioanal Chem 403:2883–2889
63. Singh BR, Wechter MA, Hu Y, Lafontaine C (1998) Determination of caffeine content in coffee using Fourier transform infra-red spectroscopy in combination with attenuated total reflectance technique: a bioanalytical chemistry experiment for biochemists. Biochem Educ 26:243–247
64. Belay A, Ture K, Redi M, Asfaw A (2008) Measurement of caffeine in coffee beans with UV/vis spectrometer. Food Chem 108:310–315
65. 18 minicolumn coupled to a flow injection system for determination of caffeine in green and roasted coffee beans. Food Chem 147:182–188
66. Aklilu M, Tessema M, Redi-Abshiro M (2008) Indirect voltammetric determination of caffeine content in coffee using 1,4-benzoquinone modified carbon paste electrode. Talanta 76:742–746
67. Chuan D, Yan-Li W, Shao-Min S (2003) Study on the paper substrate room temperature phosphorescence of theobromine, caffeine and theophylline and analytical application. Spectrochim Acta, Part A 59:1469–1476
68. Mersal GAM (2012) Experimental and computational studies on the electrochemical oxidation of caffeine at pseudo carbon paste electrode and its voltammetric determination in different real samples. Food Anal Methods 5:520–529
69. Bicho NC, Leitao AE, Ramalho JC, Lidon FC (2011) Identification of chemical clusters discriminators of the roast degree in Arabica and Robusta coffee beans. Eur Food Res Technol 233:303–311
70. De Maria CAB, Trugo LC, Aquino FR, Moreira RFA, Alviano CS (1996) Composition of green coffee water-soluble fractions and identification of volatiles formed during roasting. Food Chem 55:203–207
71. de Oliveira AL, Ceuz PM, Eberlin MN, Cabral FA (2005) Brazilian roasted coffee oil obtained by mechanical expelling: compositional analysis by GC-MS. Cienc Tecnol Alimentos 25:677–682
72. Somoza V, Lindenmeier M, Wenzel E, Frank O, Erbersdobler HF, Hofmann T (2003) Activity-guided identification of a chemopreventive compound in coffee using in vitro and in vivo techniques. J Agric Food Chem 51:6861–6869
73. Boettler U, Sommerfeld K, Volz N, Pahlke G, Teller N, Somoza V, Lang R, Hofmann T, Marko D (2011) Coffee constituents as modulators of Nrf2 nuclear translocation and ARE (EpRE)-dependent gene expression. J Nutr Biochem 22:426–440
74. Boettler U, Volz N, Pahlke G, Teller N, Kotyczka C, Somoza V, Stiebitz H, Bytof G, Lantz I, Lang R, Hofmann T, Marko D (2011) Coffees rich in chlorogenic acid or N-methylpyridinium induce chemopreventive phase II-enzymes via the Nrf2/ARE pathway in vitro and in vivo. Mol Nutr Food Res 55:S143–S153
75. Allred KF, Yackley KM, Vanamala J, Allred CD (2009) Trigonelline is a novel phytoestrogen in coffee beans. J Nutr 139:1833–1838
76. Liu H, Shao J, Li Q, Li Y, Yan HM, He L (2012) Determination of trigonelline, nicotinic acid, and caffeine in Yunnan Arabica coffee by microwave-assisted extraction and HPLC with two columns in series. J AOAC Int 95:1138–1141
77. Lang R, Yagar EF, Wahl A, Beusch A, Dunkel A, Dieminger R, Eggers R, Bytof G, Stiebitz H, Lantz I, Hofmann T (2013) Quantitative studies on roast kinetics for bioactives in coffee. J Agric Food Chem 61:12123–12128
78. Charlton AJ, Farrington WHH, Bereton P (2002) Application of 1H NMR and multivariate statistics for screening complex mixtures: quality control and authenticity of instant coffee. J Agric Food Chem 50:3098–3103
79. Consonni R, Cagliani LR, Cogliati C (2012) NMR based geographical characterization of roasted coffee. Talanta 88:420–426
80. 1H NMR spectrometry. Talanta 81:367–371
81. Cai L, Ma D, Zhang Y, Liu Z, Wang P (2012) The effect of coffee consumption on serum lipids: a meta-analysis of randomized controlled trials. Eur J Clin Nutr 66:872–877
82. Jee SH, He J, Appel LJ, Whelton PK, Suh I, Klag MJ (2001) Coffee consumption and serum lipids: a meta-analysis of randomized controlled clinical trials. Am J Epidemiol 153:353–362
83. Lee KA, Chae JI, Shim JH (2012) Natural diterpenes from coffee, cafestol and kahweol induce apoptosis through regulation of specificity protein 1 expression in human malignant pleuralmesothelioma. J Biomed Sci 19:1–10
84. Pacetti D, Boselli E, Balzano M, Frega NG (2012) Authentication of Italian Espresso coffee blends through the GC peak ratio between kahweol and 16-O-methylcafestol. Food Chem 135:1569–1574
85. Urgert R, van der Weg G, Kosmeijer-Schuil TG, van de Bovenkamp P, Hovenier R, Katan MB (1995) Levels of the cholesterol-elevating diterpenes cafestol and kahweol in various coffee brews. J Agric Food Chem 43:2167–2172
86. Chartier A, Beaumesnil M, Lopes de Oliveira A, Elfakir C, Bostyn S (2013) Optimization of the isolation and quantitation of kahweol and cafestol in green coffee oil. Talanta 117:102–111
87. Gross G, Jaccaud E, Huggett AC (1997) Analysis of the content of the diterpenes cafestol and kahweol in coffee brews. Food Chem Toxicol 35:547–554
88. Sridevi V, Giridhar P, Ravishankar GA (2011) Evaluation of roasting and brewing effect on antinutritional diterpenes-cafestol and kahweol in coffee. Glob J Med Res 11:1–7
89. Oigman SS, de Souza R, dos Santos Júnior HM, Hovell AMC, Hamerski L, Rezende CM (2012) Microwave-assisted methanolysis of green coffee oil. Food Chem 134:999–1004
90. Tsukui A, Santos Júnior HM, Oigman SS, De Souza ROMA, Bizzo HR, Rezende CM (2014) Microwave-assisted extraction of green coffee oil and quantification of diterpenes by HPLC. Food Chem 164:266–271
91. Barbosa HMA, de Melo MMR, Coimbra MA, Passos CP, Silva CM (2014) Optimization of the supercritical fluid coextraction of oil and diterpenes from spent coffee grounds using experimental design and response surface methodology. J Supercrit Fluids 85:165–172
92. Scharnhop H, Winterhalter P (2009) Isolation of coffee diterpenes by means of high-speed countercurrent chromatography. J Food Comp Anal 22:233–237
93. D’Amelio N, De Angelis E, Navarini L, Schievano E, Mammi S (2013) Green coffee oil analysis by high-resolution nuclear magnetic resonance spectroscopy. Talanta 110:118–127
94. De Roos B, vander Weg G, Grdert R, van de Bovenkamp P, Charrier A, Katan MB (1997) Levels of cafestol, kahweol and related diterpenoids in wild species of the coffee plant. J Agric Food Chem 45:3065–3069
95. Dias RCE, de Faria-Machado AF, Mercadante AZ, Bragagnolo N, Benassi MT (2014) Roasting process affects the profile of diterpenes in coffee. Eur Food Res Technol. doi:10.1007/s00217-014-2293-x
96. Galli V, Barbas C (2004) Capillary electrophoresis for the analysis of short-chain organic acids in coffee. J Chromatogr A 1032:299–304
97. Rogers WJ, Michaux S, Bastin M, Bucheli P (1999) Changes to the content of sugars, sugar alcohols, myo-inositol, carboxylic acids and inorganic anions in developing grains from different varieties of Robusta (Coffea canephora) and Arabica (C. arabica) coffees. Plant Sci 149:115–123
98. Verardo G, Cecconi F, Geatti P, Giumanini AG (2002) New procedures for determination of acids in coffee extracts, and observations on the development of acidity upon ageing. Anal Bioanal Chem 374:879–885
99. Bähre F, Maier HG (1996) Electrophoretic clean-up of organic acids from coffee for the GC/MS analysis. Fresenius J Anal Chem 355:190–193
100. Quiroz MLS, Campos AA, Alfaro GV, R´ios OG, Villeneuve P, Figueroa-Espinoza M-C (2013) Isolation of green coffee chlorogenic acids using activated carbon. J Food Comp Anal. doi:10.1016/j.jfca.2013.10.005
101. Chu Y-F, Brown PH, Lyle BJ, Chen Y, Black RM, Williams CE, Cheng IH (2009) Roasted coffees high in lipophilic antioxidants and chlorogenic acid lactones are more neuroprotective than green coffees. J Agric Food Chem 57:9801–9808
102. Duarte GS, Pereira AA, Farah A (2010) Chlorogenic acids and other relevant compounds in Brazilian coffees processed by semi-dry and wet post-harvesting methods. Food Chem 118:851–855
103. Jaiswal R, Matei MF, Golon A, Witt M, Kuhnert N (2012) Understanding the fate of chlorogenic acids in coffee roasting using mass spectrometry based targeted and nontargeted analytical strategies. Food Funct 3:976–984
104. De Maria CAB, Trugo LC, Moreira RFA (1995) Simultaneous determination of total chlorogenic acid, trigonelline and caffeine in green coffee samples by high performance gel filtration chromatography. Food Chem 2:447–449