Effect of Food Processing on Flavanols

Year 2013, Volume: 11 Issue: 2, 70 - 79, 01.06.2013

Zeynep Aksoylu Sibel Karakaya

Abstract

The strong correlation between dietary habits and some chronic diseases have been reported in numerous studies. In recent years, compounds with functional properties that provide specific health benefits to human have become popular. Flavanols, a subgroup of phenolic compounds, are generally found in green tea, cocoa, coffee, red grapes and apples. These monomeric bioactives are known as potent antioxidants. During various food processes these compounds expose to certain thermal or mechanical treatments and biochemical reactions. All of these applications lead to reversible/irreversible alterations in the structure of flavanols. Mainly the conversions affect appearance and sensorial characteristics of foods. On the other hand, bioavailability of flavanols is also influenced depending on structural changes of monomeric units. In this review, the effect of prominent processing techniques on flavanol contents of several foods is discussed

Keywords

Catechin, Fermentation, Thermal treatment, Non-thermal treatment

Gıda İşlemenin Flavanoller Üzerine Etkileri

Abstract

Sağlık üzerine belirli yararlar sağlayan fonksiyonel özelliklere sahip bileşikler son yıllarda popüler hale gelmiştir. Fenolik bileşiklerin bir alt grubu olan flavanoller genellikle yeşil çay, kakao, kahve, kırmızı üzüm ve elmada bulunmaktadır. Bu monomerik biyoaktifler güçlü antioksidanlar olarak bilinmektedir. Çeşitli gıda işlemleri sırasında bu bileşikler bazı ısıl veya mekaniksel uygulamalara ve biyokimyasal tepkimelere maruz kalmaktadır. Bu uygulamaların tümü flavanollerin yapısında geri dönüşümlü/geri dönüşümsüz değişimlere yol açmaktadır. Değişimler esas olarak gıdaların görünüşünü ve duyusal özelliklerini etkilemektedir. Diğer yandan flavanollerin biyoyararlılığı da monomerik birimlerdeki yapısal değişimlere bağlı olarak etkilenmektedir. Bu derlemede önemli gıda işleme yöntemlerinin, çeşitli gıdaların flavanol içeriği üzerine etkileri ele alınmıştır

Keywords

Kateşin, Fermantasyon, Isıl işlem, Isıl olmayan işlem

References

• Berk, Z. 2009. Food Process Engineering and Technnology. Academic Press, USA.
• Van Boekel M., Fogliano, V., Pellegrini, N., Stanton, C., Scholz, G., Lalljie, S., Somoza, V., Knorr, D., Jasti, P.R., Eisenbrand, G. 2010. A review on the beneficial aspects of food processing. Mol. Nutr. Food Res. 54(9): 1215-1247.
• Kitts, D.D.1994. Bioactive substances in food: identification and potential uses. Can. J. Physiol. Pharmacol. 72: 423-424.
• Pennington, J.A.T., 2002. Food composition databases for bioactive food components. J. Food Comp. Anal. 15: 419-434.
• Erbaş, M. 2006. Yeni Bir Gıda Grubu Olarak Fonksiyonel Gıdalar. Türkiye 9. Gıda Kongresi, 24- 26 Mayıs 2006, Bolu, Türkiye, Bildiriler Kitabı, 791- 794p.
• Shahidi, F. 2004. Functional foods: their role in health promotion and disease prevention. J. Food Sci. 69(5): R146-R149.
• Shahidi, F., Naczk, M. 2004. Phenolics in Food and Nutraceuticals. CRC Press LLC, USA.
• Cemeroğlu, B., 2004. Meyve ve Sebze İşleme Teknolojisi 1. Cilt. Gıda Teknolojisi Derneği Yayınları No:35, Ankara.
• Eruçar, S. 2006. Bazı Bitkisel Çayların Fenolik Madde Profili ve Antioksidan Aktivitelerinin İncelenmesi. Yüksek lisans tezi. İstanbul Teknik Üniversitesi Fen Bilimleri Enstitüsü, İstanbul.
• Michalak, A. 2006. Phenolic compounds and their antioxidant activity in plants growing under heavy metal stress. Polish J. of Environ. Stud. 15(4): 523- 530.
• Acar, J., Gökmen, V. 2007. Fenolik Bileşikler ve Doğal Renk Maddeleri. In Gıda Kimyası, Edited by İ.Saldamlı, Ankara, 587p. Yayınları
• Turhan, S., Üstün, N.Ş. 2006. Doğal Antioksidanlar ve Gıdalarda Kullanımları. Türkiye 9.Gıda Kongresi. 24-26 Mayıs, Bolu, Türkiye,Bildiriler Kitabı, 273- 276p.
• Seyoum, A. Asres, K., El-Fiky, F.K. 2006. Structure- radical scavenging activity relationships of flavonoids. Phytochemistry 67: 2058-2070.
• Karadeniz, F., Ekşi, A. 2002. Gıdalardaki başlıca fenolik bileşikler. Dünya Gıda 1: 80-85.
• De Pascual-Teresa, S.; Moreno, D. A.; García- Viguera, C. 2010. Flavanols and anthocyanins in cardiovascular health: a review of current evidence. Int. J. Mol. Sci. 11(4): 1679-1703.
• Hollman, P.C., Arts, I.C. 2000. Flavonols, flavones and flavanols – nature, occurrence and dietary burden. J. Sci. Food Agric. 80: 1081-1093.
• Saldamlı, İ., 2007. Gıda Kimyası. Hacettepe Üniversitesi Yayınları. Ankara.
• Hackman, R. M., Polagruto, J. A., Zhu, Q. Y., Sun, B., Fujii, H.; Keen, C.L. 2008. Flavanols: digestion, absorption and bioactivity. Phytochem. Rev. 7: 195- 208.
• Wang, H., Provan, G.J., Halliwell, K., 2000. Tea Flavonoids: Their functions, utilisation and analysis. Trends in Food Science & Technology 11, 152-160.
• Graham, H.N., 1999. Tea. In Wiley Encyclopedia of Food Science and Technology. Edited by F.J. Francis, Wiley Interscience, New York, 2724p.
• Hilal, Y., Engelhardt, U., 2007. Characterization of white tea – comparison to green and black tea. J. Verbr. Lebensm. 2: 414-421.
• Wiseman, S.A., Balentine, D.A., Frei, B., 1997. Antioxidants in tea. Crit. Rev. Food Sci. 37(8): 705- 718.
• Kim, Y., Goodner, K.L., Park, J., Choi, J., Talcott, S.T., 2011. Changes in antioxidant phytochemicals and volatile composition of Camellia sinensis by oxidation during tea fermentation. Food Chem. 129: 1331-1342.
• Zuo, Y., Chen, H., Deng, Y., 2002. Simultaneous determination of catechins, caffeine and gallic acids in green, Oolong, black and puerh teas using HPLC with a photodiode array detector. Talanta 57: 307- 316.
• Muthumani, T., Kumar, R.S.S., 2007. Influence of fermentation time on the development of compounds responsible for quality in black tea. Food Chem. 101: 98-102.
• Obanda, M., Owuor, P.O., Mang’oka, R., 2001. Changes in the chemical and sensory quality parameters of black tea due to variations of fermentation time and temperature. Food Chem. 75: 395-404.
• Dou, J., Lee, V.S.Y., Tzen, J.T.C., Lee, M., 2007. Identification compounds in the preparation of oolong tea manufactured by semifermentation and drying processes. J. Agr. Food Chem. 55: 7462-7468.
• Hii, C.L., Law, C.L., Suzannah, S., Misnawi, Cloke, M., 2009. Polyphenols in cocoa (Theobroma cacao L.). As. J. Food Ag-Ind. 2(4): 702-722.
• Wollgast, J., Anklam, E., 2000. Review on polyphenols in Theobroma cacao: changes in composition during the manufacture of chocolate and quantification. Food Res. Int. 33: 423-447. identification and
• Lima, L.J.R., Almeida, M.H., Nout, M.J.R., Zwietering, M.H. 2011. Theobroma cacao L., “The Food of the Gods”: quality determinants of commercial cocoa beans, with particular reference to the impact of fermentation. Crit. Rev. Food Sci. 51: 731-761.
• Jespersen, L., Nielsen, D.S., Hİnholt, S., Jakobsen, M., 2005. Occurrence and diversity of yeasts involved in fermentation of West African cocoa beans. FEMS Yeast Res. 5: 441-453.
• Zhu, Q.Y., Zhang, A., Tsang, D., Huang, Y., Chen, Z., 1997. Stability of green tea catechins. J. Agr. Food Chem. 45: 4624-4628.
• Schinella, G., Mosca, S., Cienfuegos-Jovellanos, E., Pasamar, M.Á., Muguerza, B., Ramón, D., Rίos, J.L., 2010. Antioxidant properties of polyphenols – rich cocoa products industrially processed. Food Res. Int. 43: 1614-1623.
• Dixon, R.A., Xie, D., Sharma, S.B. 2005. Proanthocyanidins – a final frontier in flavonoid research? New Phytol. 165: 9-28.
• Martens, S., Preuß, A., Matern, U. 2010. Multifunctional flavonoid dioxygenases: Flavonol and anthocyanin biosynthesis in Arabidopsis thaliana L. Phytochemistry 71: 1040-1049.
• Hurst, W.J., Krake, S.H., Bergmeier, S.C., Payne, M.J., Miller, K.B., Stuart, D.A., 2011. Impact of fermentation, drying, roasting and Dutch processing on flavan-3-ol stereochemistry in cacao beans and cocoa ingredients. Chem. Cent. J. 5: 53.
• Donovan, J.L., Crespy, V., Oliveira, M., Cooper, K.A., Gibson, B.B., Williamson, G., 2006. (+) – catechin is more bioavailable than (-) – catechin: Relevance to the bioavailability of catechin from cocoa. Free Rad. Res. 40: 1029-1034.
• Payne, M.J., Hurst, W.J., Miller, K.B., Rank, C., Stuart, D.A., 2010. Impact of fermentation, drying, roasting and Dutch processing on epicatechin and catechin content of cacao beans and cocoa ingredients. J. Agr. Food Chem. 58: 10518-10527.
• Aikpokpodion, P.E., Dongo, L.N., 2010. Effects of fermentation intensity on polyphenols and antioxidant capacity of cocoa beans. Int. J. Sustain. Crop. Prod. 5(4): 66-70.
• Gil, A., Rojas, L.F., Atehortua, L., Londoṅo, J., 2011. Effect of Fermentation and Sun Drying on Phytochemical Composition of Native Colombian Cocoa. 2011 CIGR Section VI International Symposium on Towards a Sustainable Food Chain Food Process, Bioprocessing and Food Quality Management, April 18-20 2011, Nantes, France, 1- 6p.
• Camu, N., De Winter, T., Addo, S.K., Takrama, J.S., Bernaert, H., De Vuyst, L., 2008. Fermentation of cocoa beans: Influence of microbial activities and polyphenol concentrations on the flavour of chocolate. J. Sci. Food Agric. 88: 2288-2297.
• Nazaruddin, R., Seng, L.K., Hassan, O., Said, M., 2006. Effect of pulp preconditioning on the content of polyphenols in cocoa beans (Theobroma cacao) during fermentation. Ind. Crop Prod. 24: 87-94.
• Kim, H., Keeney, P.G., 1984. (–) – Epicatechin content in fermented and unfermented cocoa beans. J. Food Sci. 49: 1090-1092.
• Ohlsson, T., 2002. Minimal processing of foods with thermal Technologies in the Food Industry. Edited by Ohlsson T. & Bengtsson, N. Woodhead Publishing Limited, Abington Hall, Abington, Cambridge CB1 6AH, England, 288p. Minimal Processing
• Madrau, M.A., Piscopo, A., Sanguinetti, A.M., Del Caro, A., Poiana, M., Romeo, F.V., Piga, A., 2009. Effect of drying temperature on polyphenolic content and antioxidant activity of apricots. Eur. Food Res. Technol. 228: 441-448.
• Pedroza, M.A., Carmona, M., Pardo, F.Salinas, M.R., Zalacain, A., 2012. Waste grape skins thermal dehydration: potential release of colour, phenolic and aroma compounds into wine. TCYT 10(3): 225-234.
• Ferreira, D., Guyot, S., Marnet, N., Delgadillo, I., Renard, Composition of phenolic compounds in a Portuguese pear (Pyrus communis L. Var. S. Bartolomeu) and changes after sun-drying. J. Agr. Food Chem. 50: 4537-4544. M.A., 2002.
• Mohd Zainol, M.K., Abdul-Hamid, A., Abu Bakar, F., Pak Dek, S., 2009. Effect of different drying methods on the degradation of selected flavonoids in Centella asiatica. Int. Food Res. J. 16: 531-537.
• Davey, M.W., Van-Montagu, M., Inze, D., Sanmartin, M., Kanellis, A., Smirnoff, N., Benzie, I.J.J., Strain, J.J., Favell, D., Fletcher, J., 2000. Plant l-ascorbic acid: metabolism, processing. J. Sci. Food Agr. 80: 825-860. and effects of
• Wojdyło, A., Figiel, A., Oszmiański, J., 2009. Effect of drying methods with the application of vacuum microwaves on the bioactive compounds, color, and antioxidant activity of strawberry fruits. J. Agr. Food Chem. 57: 1337-1343.
• Ross, C.F., Hoye, C., Fernandez-Plotka, V.C., 2011. Influence of heating on the polyphenolic content and antioxidant activity of grape seed flour. J. Food Sci. 76(6): C884-C890.
• Kim, S-Y., Jeong, S-M., Park, W-P., Nam, K.C., Ahn, D.U., Lee, S-C., 2006. Effect of heating conditions of grape seeds on the antioxidant activity of grape seed extracts. Food Chem. 97: 472-479.
• Stach, D., Schmitz, O.J., 2001. Decrease in concentration of free catechins in tea over time determined chromatography. J. Chromatogr. A 924: 519-522.
• Wang, R., Zhou, W., Jiang, X., 2008. Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range. J. Agr. Food Chem. 56: 2694-2701.
• Okumura, H., Ichitani, M., Takihara, T., Kunimoto, K-K., 2008. Effect of cyclodextrins on the thermal epimerization of tea catechins. Food Sci. Technol. Res. 14(1): 83-88.
• Kim, E.S., Liang, Y.R., Jin, J., Sun, Q.F., Lu, J.L., Du, Y.Y., Lin, C., 2007. Impact of heating on chemical compositions of green tea liquor. Food Chem. 103: 1263-1267.
• Murakami, I., Nakamura, T., Ishibashi, Y., Shibuya, R., Ayano, E., Morita-Murase, Y., Nagata, Y., Kanazawa, H., 2006. Simultaneous determination of catechins and procyanidins in bottled tea drinks by LC/MS. Chromatography 27(1): 27-33.
• Ito, R., Yamamoto, A., Kodama, S., Kato, K., Yoshimura, Y., Matsunaga, A., Nakazawa, H., 2003. A study on the change of enantiomeric purity of catechins in green tea infusion. Food Chem. 83: 563-568.
• Seto, R., Nakamura, H., Nanjo, F., Hara, Y., 1997. Preparation of epimers of tea catechins by heat treatment. Biosci. Biotech. Biochem. 61(9): 1434- 1439.
• Chen, Z-Y., Zhu, Q.Y., Tsang, D., Huang, Y., 2001. Degradation of green tea catechins in tea drinks. J. Agr. Food Chem. 49: 477-482.
• Li, N., Taylor, L.S., Ferruzzi, M.G., Mauer, L.J., 2012. Kinetic study of catechin stability: Effects of pH, concentration, and temperature. J. Agr. Food Chem. 60: 12531-12539.
• Vacklavik, V.A., Christian, E.W., 2008. Essentials of Food Science – 3rd Edition. Springer Science + Business Media LLC, USA.
• Xu, B., Chang, S.K.C., 2009. Total phenolic, phenolic acid, anthocyanin, flavan-3-ol, and flavonol profiles and antioxidant properties of pinto and black beans (Phaseolus vulgaris L.) as affected by thermal processing. J. Agr. Food Chem. 57: 4757- 4764.
• Wang, L-F., Kim, D-M., Lee, C.Y., 2000. Effects of heat processing and storage on flavanols and sensory qualities of green tea beverage. J. Agr. Food Chem. 48: 4227-4232.
• Sharma, A., Zhou, W., 2011. A stability study of green tea catechins during the biscuit making process. Food Chem. 126: 568-573.
• Fellows, P., 2000. Food Processing Technology Principles and Practice – 2nd Edition. Woodhead Publishing Limited, England.
• Jolić, S.M., Redovniković, I.R., Marković, K., Šipušić, D.I., Delonga, K., 2011. Changes of phenolic compounds and antioxidant capacity in cocoa beans processing. Int. J. Food Sci. Tech. 46: 1793-1800.
• Kofink, M., Papagiannopoulos, M., Galensa, R., 2007. (-)-Catechin in cocoa and chocolate: occurrence and analysis of an atypical flavan-3-ol enantiomer. Molecules 12: 1274-1288.
• Caligiani, A., Cirlini, M., Palla, G., Ravaglia, R., Arlorio, M., 2007. GC-MS detection of chiral markers in cocoa beans of different quality and geographic origin. Chirality 19: 329-334.
• Oliviero, T., Capuano, E., Cämmerer, B., Fogliano, V., 2009. Influence of roasting on the antioxidant activity and HMF formation of a cocoa bean model systems. J. Agr. Food Chem. 57: 147-152.
• Kendari, T., Harijono, Yuwono, S.S., Estiasih, T.
• Santoso, U., 2012. The change of catechin antioxidant during vacuum roasting of cocoa powder. doi:10.4172/2155-9600.1000174 Food Sci. 2: 174.
• 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.
• Schmitzer, V., Slatnar, A., Veberiz, R., Stampar, F., Solar, A., 2011. Roasting affects phenolic composition and antioxidative activity of hazelnuts (Corylus avellana L.). J. Food Sci. 76(1): S14-S19.
• Chandrasekara, N., Shahidi, F., 2011. Effect of roasting on phenolic content and antioxidant activities of whole cashew nuts, kernels and testa. J. Agr. Food Chem. 59: 5006-5014.
• Belviso, S., Ghirardello, D., Giordano, M., Ribeiro, G.S., Alves, J.S., Parodi, S., Risso, S., Zeppa, G., 2013. Phenolic composition, antioxidant capacity and volatile compounds of licuri (Syagrus coronate (Martius) Beccari) fruits as affected by the traditional roasting process. Food Res. Int. 51(1): 39-45.
• Czyżowska, A., Pogorzelski, E., 2004. Changes to polyphenols in the process of production of must and wines from blackcurrants and cherries. Part II. Anthocyanins and flavanols. Eur. Food Res. Technol. 218: 355-359.
• Fuleki, T., Ricardo-Da-Silva, J.M., 2003. Effects of cultivar and processing method on the contents of catechins and procyanidins in grape juice. J. Agr. Food Chem. 51: 640-646.
• Hernandez, T., Ausín, N., Bartolomé, B., Bengoechea, L., Estrella, I., Gómez-Cordovés, C., 1997. Variations in the phenolic composition of fruit juices with different treatments. Z. Lebensm. Unters. F. A 204: 151-155.
• Spanos, G.A., Wrolstad, R.E., Heatherbell, D.A., 1990a. Influence of processing and storage on the phenolic composition of apple juice. J. Agr. Food Chem. 38: 1572-1579.
• Spanos, G.A., Wrolstad, R.E., 1990b. Influence of processing and storage on the phenolic composition of Thompson seedless grape juice. J. Agr. Food Chem. 38: 1565-1571.
• Spanos, G.A., Wrolstad, R.E., 1990. Influence of variety, maturity, processing, and storage on the phenolic composition of pear juice. J. Agr. Food Chem. 38: 817-824.
• Hogan, E., Kelly, A.L., Sun, D-W., 2005. High Pressure processing of foods: an overview. In Emerging Technologies for Food Processing. Edited by D-W. Sun, Elsevier Academic Press, California, US, 768p.
• Ohlsson, T., Bengtsson, N. 2002. Minimal Processing of Foods with Non – Thermal Methods. In Minimal Processing Technologies in The Food Industry. Edited by T. Ohlsson & N. Bengtsson, Woodhead Publishing Limited, England, 288p.
• Park, J-H., Lee, J-M., Cho, Y-J., Kim, C-T., Kim, C- J., Nam, K-C., Lee, S-C., 2009. Effect of far – infrared characteristics of green tea during processing. J. Food Biochem. 33: 149-162.
• physicochemical 2003. Application of microwave energy in the manufacture of enhanced – quality green tea. J. Agr. Food Chem. 51: 4764-4768.
• Kim, S-Y., Jeong, S-M., Jo, S-C., Lee, S-C., 2006. Application of far – infrared irradiation in the manufacturing process of green tea. J. Agr. Food Chem. 54: 9943-9947.
• Lee, S-C., Kim, S-Y., Jeong, S-M., Park, H-J., 2006. Effect of far – infrared irradiation on catechins and nitrite scavenging activity of green tea. J. Agr. Food Chem. 54: 399-403.
• Lee, J-M., Lee, S-C., 2010. The effects of far – infrared irradiation on the antioxidant activity of licorice (Glycyrrhiza uralensis fisch) root. J. Food Biochem. 34: 172-181.
• Hayat, K., Zhang, X., Farooq, Um., Abbas, S., Xia, S., Jia, C., Zhong, F., Zhang, J., 2010. Effects of microwave treatment on phenolic content and antioxidant activity of citrus mandarin pomace. Food Chem. 123: 423-429.
• Hayat, K., Zhang, X., Chen, H., Xia, S., Jia, C., Zhong, F., 2010. Liberation and separation of phenolic compounds from citrus mandarin peels by microwave heating and its effect on antioxidant activity. Sep. Purif. Technol. 73: 371-376.
• Breitfellner, F., Solar, S., Sontag, G., 2002. Effect of gamma irradiation on flavonoids in strawberries. Eur Food Res. Technol. 215: 28-31.
• Schilling, S., Alber, T., Toepfl, S., Neidhart, S., Knorr, D., Schieber, A., Carle, R., 2007. Effects of pulsed electric field treatment of apple mash on juice yield and quality attributes of apple juices. Innov. Food Sci. Emerg. 8: 127-134.
• Puértolas, E., Saldaṅa, G., Álvarez, I., Raso, J., 2010. Effect of pulsed electric field processing of red grapes on wine chromatic and phenolic characteristics during aging in oak barrels. J. Agr. Food Chem. 58: 2351-2357.
• Baron, A., Dénes, J-M., Durier, C., 2006. High- pressure treatment of cloudy apple juice. LWT Food Sci. Technol. 39: 1005-1013.
• Andres-Lacueva, C., Monagas, M., Khan, N., Izquierdo-Pulido, M., Urpi-Sarda, M., Permanyer, J., Lamuela-Raventós, R.M., 2008. Flavanol and flavonol contents of cocoa powder products: Influence of the manufacturing process. J. Agr. Food Chem. 56: 3111-3117.