AS  Vol.4 No.8 , August 2013
Quality aspects of coffees and teas: Application of electron paramagnetic resonance (EPR) spectroscopy to the elucidation of free radical and other processes.
ABSTRACT

Coffees and teas are beverages that are both exceptionally rich in antioxidant molecules, and are also both associated with beneficial health effects. Thus although the quality characteristics of these beverages are conventionally assessed on the basis of their sensory properties, their antioxidant contents represent an additional and increasingly valued attribute of quality based on their contributions to healthy diets. Both beverages are prepared by hot water extraction of a pure plant-derived product, and thus their compositions can potentially change quite rapidly as a result of oxidation in contact with air. Oxidative processes often proceed via free radical intermediates, and sometimes also result in the formation of stable radical end-products; thus EPR spectroscopy is a convenient technique for investigating some of the various free radical reactions that occur in these beverages. This paper reviews progress that has been made in elucidating free radical processes that occur during the preparation and storage of coffees and teas, and the results are discussed in terms of quality criteria of the beverages.


Cite this paper
Goodman, B. , Yeretzian, C. , Stolze, K. and Wen, D. (2013) Quality aspects of coffees and teas: Application of electron paramagnetic resonance (EPR) spectroscopy to the elucidation of free radical and other processes.. Agricultural Sciences, 4, 433-442. doi: 10.4236/as.2013.48058.
References
[1]   Pulido, R., Hernández-García, M. and Saura-Calixto, F. (2003) Contribution of beverages to the intake of lipophilic and hydrophilic antioxidants in the Spanish diet. European Journal of Clinical Nutrition, 57, 1275-1282. doi:10.1038/sj.ejcn.1601685

[2]   Svilaas, A., Kaur Sakhi, A., Frost Andersen, L., Svilaas, T., Strom, E.C., Jacobs Jr., D.R. Ose, L. and Blomhoff , R. (2004) Intakes of antioxidants in coffee, wine, and vegetables are correlated with plasma carotenoids in humans. Journal of Nutrition, 134, 562-567.

[3]   Stadler, R.H. and Fay, L.B. (1995) Antioxidative reactions of caffeine: Formation of 8-oxocaffeine (1,3,7-trimethyluric acid) in coffee subjected to oxidative stress. Journal of Agricultural and Food Chemistry, 43, 1332-1338. doi:10.1021/jf00053a038

[4]   Zhao, Y.K., Cao, Q.E., Liu, H.T., Wang, K.T., Yan, A.X. and Hu, Z.D. (2000) Determination of baicalin, chlorogenic acid and caffeic acid in traditional Chinese medicinal preparations by capillary zone electrophoresis. Chromatographia, 51, 483-486. doi:10.1007/BF02490489

[5]   Chen, X.F., Zhang, J.U., Xue, C.X., Chen, X.G. and Hu, Z.D. (2004) Simultaneous determination of some active ingredients in anti-viral preparations of traditional Chinese medicine by micellar electrokinetic chromatography. Biomedical Chromatography, 18, 673-680. doi:10.1002/bmc.373

[6]   Higdon, J.V. and Frei, B. (2006) Coffee and health: A review of recent human research. Critical Reviews in Food Science and Nutrition, 46, 101-123. doi:10.1080/10408390500400009

[7]   Clifford, M.N. (1999) Chlorogenic acids and other cinnamates—Nature, occurrence and dietary burden. Journal of the Science of Food and Agriculture, 79, 362-372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D

[8]   Clifford, M.N. (2000) Chlorogenic acids and other cinnamates—Nature, occurrence, dietary burden, absorption and metabolism. Journal of the Science of Food and Agriculture, 80, 1033-1043. doi:10.1002/(SICI)1097-0010(20000515)80:7<1033::AID-JSFA595>3.0.CO;2-T

[9]   Kuhnert, N. and Jaiswal, R. (2012) Occurrence and identification of chlorogenic acids in green and roasted coffee beans. In: Goodman, B.A., Ed., Coffee Consumption and Health, Nova Science Publishers, New York, 65-97.

[10]   Powrie, W.D., Wu, C.H. and Molund, V.P. (1986) Browning reaction systems as sources of mutagens and antimutagens. Environmental Health Perspectives, 67, 47-54. doi:10.1289/ehp.866747

[11]   Kitts, D.D., Wu, C.H., Kopec, A. and Nagasawa, T. (2006) Chemistry and genotoxicity of caramelized sucrose. Molecular Nutrition & Food Research, 50, 1180-1190. doi:10.1002/mnfr.200600181

[12]   Casal, S. (2012) Coffee roasting; Accurate control for increased bioactivity. In Goodman, B.A., Ed., Coffee Consumption and Health, Nova Science Publishers, New York, 99-119.

[13]   Yanagimoto, K., Lee, K.G., Ochi, H. and Shibamoto, T. (2002) Antioxidative activity of heterocyclic compounds found in coffee volatiles produced by Maillard reaction. Journal of Agricultural and Food Chemistry, 50, 5480-5484. doi:10.1021/jf025616h

[14]   Obana, H., Nakamura, S. and Tanaka, R. (1986) Suppressive effects of coffee on the SOS responses induced by UV and chemical mutagens. Mutation Research Letters, 175, 47-50. doi:10.1016/0165-7992(86)90124-7

[15]   Malaveille, C., Hautefeuille, A., Pignatelli, B., Talaska, G., Vineis, P. and Bartsch, H. (1996) Dietary phenolics as anti-mutagens and inhibitors of tobacco-related DNA adduction in the urothelium of smokers. Carcinogenesis, 17, 2193-2200. doi:10.1093/carcin/17.10.2193

[16]   Perrone, D., Farah, A. and Donangelo, C.M. (2012) Influence of Coffee Roasting on the Incorporation of Phenolic Compounds into Melanoidins and Their Relationship with Antioxidant Activity of the Brew. Journal of Agricultural and Food Chemistry, 60, 4265-4275. doi:10.1021/jf205388x

[17]   Del Castillo, M.D., Ames, J.M. and Gordon, M.H. (2002) Effect of roasting on the antioxidant activity of coffee brews. Journal of Agricultural and Food Chemistry, 50, 3698-3703. doi:10.1021/jf011702q

[18]   Sacchetti, G., Di Mattia, C., Pittia, P. and Mastrocola, D. (2009) Effect of roasting degree, equivalent thermal effect and coffee type on the radical scavenging activity of coffee brews and their phenolic fraction. Journal of Food Engineering, 90, 74-80. doi:10.1016/j.jfoodeng.2008.06.005

[19]   O’Meara, J.P., Truby, F.K. and Shaw, T.M. (1957) Free radicals in roasted coffee. Food Research, 22, 96-101. doi:10.1111/j.1365-2621.1957.tb16988.x

[20]   Nebesny, E. and Budryn, G. (2006) Changes in free radicals content in coffee beans throughout convective roasting and microwaving and during storage. Deutsche Lebensmittel-Rundschau, 102, 526-530.

[21]   Goodman, B.A., Pascual, E.C. and Yeretzian, C. (2011) Real-time monitoring of free radical processes during the roasting of coffee beans using electron paramagnetic resonance spectroscopy. Food Chemistry, 125, 248-254. doi:10.1016/j.foodchem.2010.07.072

[22]   Pascual, E.C., Yeretzian, C., Pirker, K.F. and Goodman, B.A. (2005) Antioxidant, pro-oxidant and free radical processes in coffee. In: Zhao, B., Liu, G. and Packer, L., Eds., Natural Antioxidants and Micronutrients, Medimond, Bologna, 119-125.

[23]   Nicoli, M.C., Innocente, N., Pittia, P. and Lerici, C.R. (1993) Staling of roasted coffee: Volatile release and oxidation reactions during storage. ASIC 15th International Scientific Colloquium on Coffee, 15, 557-566.

[24]   Vila, M.A., Andueza, S., Paz de Pena, M. and Cid, C. (2005) Fatty acid evolution during the storage of ground, roasted coffees. Journal of the American Oil Chemists’ Society, 82, 639-646.

[25]   Nicoli, M., Calligaris, S. and Manzocco, L. (2009) Shelflife testing of coffee and related products: Uncertainties, pitfalls, and perspectives. Food Engineering Reviews, 1, 159-168. doi:10.1007/s12393-009-9010-8

[26]   Yeretzian, C., Pascual, E.C. and Goodman, B.A. (2012) Effect of roasting conditions and grinding on free radical contents of coffee beans stored in air. Food Chemistry, 131, 811-816. doi:10.1016/j.foodchem.2011.09.048

[27]   Baesso, M. L., Da Silva, E. C., Vargas, H., Cortez, J. G. and Pelzl, J. (1990). Use of electron spin resonance for the determination of staling of roast coffee in polyethylene bag packs. Zeitschrift für Lebensmittel-Untersuchung und Forschung A, 191, 24-27. doi:10.1007/BF01202360

[28]   Winterbourn, C.C. (1995) Toxicity of iron and hydrogen peroxide: the Fenton reaction. Toxicology Letters, 82-83, 969-974. doi:10.1016/0378-4274(95)03532-X

[29]   Pascual, E.C., Goodman, B.A. and Yeretzian, C. (2002) Characterisation of free radicals in soluble coffee by electron paramagnetic resonance spectroscopy. Journal of Agricultural and Food Chemistry, 50, 6114-6122. doi:10.1021/jf020352k

[30]   Hofmann, T., Bors, W. and Stettmaier, K. (1999) Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids. Journal of Agricultural and Food Chemistry, 47, 379-390. doi:10.1021/jf980626x

[31]   Obinger, C., Burner, U. and Ebermann, R. (1997) Generation of hydrogen peroxide by plant peroxidases mediated thiol oxidation. Phyton, 37, 219-226.

[32]   Buettner, G.R. and Mason, R.P. (1990) Spin-trapping methods for detecting superoxide and hydroxyl free radicals in vitro and in vivo. In: Packer, L. and Glazer, A.N., Eds., Oxygen Radicals in Biological Systems, Part B, Oxygen Radicals and Antioxidants (Methods in Enzymology, Vol. 186), Academic Press, Inc., San Diego, 127-133.

[33]   Pascual, E.C., Yeretzian, C. and Goodman, B.A. (2013) Probing free radical processes during storage of extracts from whole roasted coffee beans: Impact of O2 exposure during extraction and storage. Journal of Agricultural and Food Chemistry (submitted for publication).

[34]   Yeretzian, C., Pascual, E.C. and Goodman, B.A. (2013). Effects of O2 during various processing steps on free radical concentrations in hot aqueous extracts of R&G coffee and their changes during storage. Proceedings of the PACCON International Conference, Bangsaen (accepted for publication).

[35]   Grosch, W. (2001) Chemistry III: Volatile compounds. In: Clark, R.J. and Vitzthum, O.G., Eds., Coffee: Recent Developments, Blackwell Science, Oxford, 68-89.

[36]   Blank, I., Pascual, E.C., Devaud, S., Fay, L.B., Stadler, R.H., Yeretzian, C. and Goodman, B.A. (2002) Degradation of the coffee flavor compound furfuryl mercaptan in model Fenton-type reaction systems. Journal of Agricultural and Food Chemistry, 50, 2356-2364. doi:10.1021/jf011329m

[37]   Munro, L.J., Curioni, A., Andreoni, W., Yeretzian, C. and Watzke, H. (2003) The elusiveness of coffee aroma: New insights from a non-empirical approach. Journal of Agricultural and Food Chemistry, 51, 3092-3096. doi:10.1021/jf0261607

[38]   Ho, C.-T. and Zhu, N. (2000). The chemistry of tea. In: Parliament, Ho, C.-T. and Schieberle, P., Eds., Caffeinated Beverages, Health Benefits, Physiological Effects, and Chemistry, ACS Symposium Series 754, ACS, Washington DC, 316-326. doi:10.1021/bk-2000-0754.ch032

[39]   Yang, C.S. (1997) Inhibition of carcinogenesis by tea. Nature, 389, 134-135. doi:10.1038/38154

[40]   Mukhtar, H. and Ahmad, N. (2000) Tea polyphenols: prevention of cancer and optimizing health. American Journal of Clinical Nutrition, 71, 1698S-1702S.

[41]   Hara, Y. (2004) Green tea: Health benefits and applications. Marcel Dekker Inc., New York.

[42]   Hodgson, J.M. (2008) Tea flavonoids and cardiovascular disease. Asia Pacific Journal of Clinical Nutrition, 17, 288-290.

[43]   Katiyar, S.K. and Mukhtar, H. (1996) Tea in chemoprevention of cancer: Epidemiologic and experimental studies. International Journal of Oncology, 8, 221-238.

[44]   Vinson, J.A., Teufel, K. and Wu, N. (2004) Green and black teas inhibit atherosclerosis by lipid, antioxidant, and fibrinolytic mechanisms. Journal of Agricultural and Food Chemistry, 52, 3661-3665. doi:10.1021/jf035255l

[45]   Pirker, K.F., Ferreira Severino, J., Reichenauer, T.G. and Goodman, B.A. (2008) Free radical processes in green tea polyphenols (GTP) investigated by electron paramagnetic resonance (EPR) spectroscopy. Biotechnology Annual Review, 14, 349-401. doi:10.1016/S1387-2656(08)00013-6

[46]   Goodman, B.A., Ferreira Severino, J., Reichenauer, T.G. and Pirker, K.F. (2009) Aspects of the antioxidant chemistry of teas investigated by electron paramagnetic resonance (EPR) spectroscopy. In: Winyayong, P., Syers, J.K. and Theppakorn, T., Eds., Tea Production and Tea Products, Mae Fah Luang University, Chiang Rai, 101-117.

[47]   Ferreira-Severino, J., Goodman, B.A., Kay, C.W.M., Stolze, K., Tunega, D., Reichenauer, T.G. and Pirker, K.F. (2009) Free radicals generated during oxidation of green tea polyphenols: Electron paramagnetic resonance spectroscopy combined with density functional theory calculations. Free Radical Biology and Medicine, 46, 1076-1088. doi:10.1016/j.freeradbiomed.2009.01.004

[48]   Taguri, T., Tanaka, T. and Kouno, I. (2004) Antimicrobial activity of 10 different plant polyphenols against bacteria causing food-borne disease. Biological and Pharmaceutical Bulletin, 27, 1965-1969. doi:10.1248/bpb.27.1965

[49]   Moreno, S., Scheyer, T., Romano, C.S. and Vojnov, A.A. (2006) Antioxidant and antimicrobial activities of rosemary extracts linked to their polyphenol composition. Free Radical Research, 40, 223-231. doi:10.1080/10715760500473834

[50]   Oliveira, I., Sousa, A., Ferreira, I.C.F.R., Bemto, A., Estevinho, L. and Pereira, J.A. (2008) Total phenols, antioxidant potential and antimicrobial activity of walnut (Juglans regia L.) green husks. Food and Chemical Toxicology, 46, 2326-2331. doi:10.1016/j.fct.2008.03.017

[51]   Ksouri, R., Falleh, H., Megdiche, W., Trabelsi, N., Mhamdi, B., Chaieb, K.,Bakrouf, A., Magné, C., Abdelly, C. (2009) Antioxidant and antimicrobial activities of the edible medicinal halophyte Tamarix gallica L. and related polyphenolic constituents. Food and Chemical Toxicology, 47, 2083-2091. doi:10.1016/j.fct.2009.05.040

[52]   Yaltirak, T., Aslim, B., Ozturk, S. and Alli, H. (2009) Antimicrobial and antioxidant activities of Russula delica Fr. Food and Chemical Toxicology, 47, 2052-2056. doi:10.1016/j.fct.2009.05.029

[53]   Cartwright, R.A., Roberts, E.A.H. and Wood, D.J. (1954) Theanine an amino acid of N-ethyl amide present in tea. Journal of the Science of Food and Agriculture, 5, 597-599. doi:10.1002/jsfa.2740051208

[54]   Kato, M., Gyoten, Y., Sakai-Kato, K. and Toyo’oka, T. (2003) Rapid analysis of amino acids in Japanese green tea by microchip electrophoresis using plastic microchip and fluorescence detection. Journal of Chromatography A, 1013, 183-189. doi:10.1016/S0021-9673(03)01037-9

[55]   Kimura, K., Ozeki, M., Juneja, L. and Ohira, H. (2007) L-Theanine reduces psychological and physiological stress responses. Biological Psychology, 74, 39-45. doi:10.1016/j.biopsycho.2006.06.006

[56]   Park, S.K., Jung, I.C., Lee, W.K., Lee, Y.S., Park, H.K., Go, H.J., Kim, K., Lim, N.K., Hong, J.T., Ly, S.Y. and Rho, S.S. (2011) A combination of green tea extract and l-theanine improves memory and attention in subjects with mild cognitive impairment: A double-blind placebocontrolled study. Journal of Medicinal Food, 14, 334-343. doi:10.1089/jmf.2009.1374

[57]   Kakuda, T. (2011) Neuroprotective effects of theanine and its preventive effects on cognitive dysfunction. Pharmacological Research, 64, 162-168. doi:10.1016/j.phrs.2011.03.010

[58]   Mandel, S., Amit, T., Reznichenko, L., Weinreb, O. and Youdim, M.B.H. (2006) Green tea catechins as brainpermeable, natural iron chelators-antioxidants for the treatment of neurodegenerative disorders. Molecular Nutrition & Food Research, 50, 229-234. doi:10.1002/mnfr.200500156

[59]   Pirker, K.F., Baratto, M.C., Basosi, R. and Goodman, B.A. (2012) Influence of pH on the speciation of copper(II) in reactions with the green tea polyphenols, epigallocatechin gallate and gallic acid. Journal of Inorganic Biochemistry, 112, 10-16. doi:10.1016/j.jinorgbio.2011.12.010

[60]   Ferreira-Severino, J., Goodman, B.A., Reichenauer, T.G. and Pirker, K.F. (2011) Is there a redox reaction between Cu(II) and gallic acid? Free Radical Research, 45, 123-132. doi:10.3109/10715762.2010.515220

[61]   Goodman, B.A., Ferreira Severino, J. and Pirker, K.F. (2012). Reactions of green and black teas with Cu(II). Food & Function, 3, 399-409. doi:10.1039/c1fo10086f

[62]   Leung, L. K., Su, Y., Chen, R., Zhang, Z., Huang, Y. and Chen, Z.-Y. (2001) Theaflavins in black tea and catechins in green tea are equally effective antioxidants. Journal of Nutrition, 131, 2248-2251.

[63]   Dorfner, R., Ferge, T., Kettrup, A., Zimmermann, R. and Yeretzian, C. (2003) Real-time monitoring of 4-vinylguaiacol, guaiacol and phenol during roasting by resonant laser ionisation time-of-flight mass-spectrometry. Journal of Agricultural and Food Chemistry, 51, 5768-5773. doi:10.1021/jf0341767

[64]   Dorfner, R., Ferge, T., Yeretzian, C., Kettrup, A. and Zimmermann, R. (2004) Laser mass spectrometry as on-line sensor for industrial process analysis: Process control of coffee roasting. Analytical Chemistry, 76, 1386-1402. doi:10.1021/ac034758n

[65]   Wieland, F., Gloess, A.M., Keller, M., Wetzel, A., Schenker, S. and Yeretzian, C. (2012) On-line monitoring of coffee roasting by proton-transfer-reaction time-of-flight mass-spectrometry (PTR-ToF-MS): Towards a real-time process control for a consistent roast profile. Analytical and Bioanalytical Chemistry, 402, 2531-2543. doi:10.1007/s00216-011-5401-9

 
 
Top