Abstract
Considering the potential of applying grape skin extract (GSE) as functional ingredients in products that must be thermally processed, the aim of this study was to evaluate the stability of individual polyphenols in grape skin extracts submitted to heating at different temperatures. Polyphenolic compounds were extracted by applying 20% aqueous ethanol containing 1% acetic acid for 1 h at 50 °C on a magnetic stirrer. The obtained extract was divided into aliquots and submitted to heating at different temperatures for a various time. The content of individual phenolic compounds in all incubated extract was determined by the HPLC method. All studied compounds were very stable during heating at 40 °C. Among analyzed anthocyanins, diglucosides were more stable than corresponding monoglucosides. Gallocatechin and procyanidins B1 and B2 contents were decreased, while catechin and epicatechin contents were increased during thermal treatments. At both incubation temperature contents of caftaric and coutaric acid were decreased, while in the same time contents of caffeic and coumaric acids were raised which could be due to hydrolysis. A significant increase of gallic, protocatechuic, vanillic, and syringic acid contents was due to thermal degradation of delphinidin-3-O-glucoside, cyanidin-3-O-glucoside, peonidin-3-O-glucoside, and malvidin-3-O-glucoside, respectively. trans-Piceid showed high stability toward thermal treatments.
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References
Amendola D, De Faveri DM, Spigno G (2010) Grape marc phenolics: extraction kinetics, quality, and stability of extracts. J Food Eng 97:384–392. https://doi.org/10.1016/j.jfoodeng.2009.10.033
Appel HM, Govenor H, D’Ascenzo M, Siska E, Schultz JC (2001) Limitations of folin assays of foliar phenolics in ecological studies. J Chem Ecol 27:761–778. https://doi.org/10.1023/A:1010306103643
Bener M, Shen YX, Apak R, Finley JW, Xu ZM (2013) Release and degradation of anthocyanins and phenolics from blueberry pomace during thermal acid hydrolysis and dry heating. J Agric Food Chem 61:6643–6649. https://doi.org/10.1021/jf401983c
Brauch JE, Kroner M, Schweiggert RM, Carle R (2015) Correction to studies into the stability of 3-O-Glycosylated and 3,5-O-diglycosylated anthocyanins in differently purified liquid and dried maqui (Aristotelia chilensis (Mol.) Stuntz) preparations during storage and thermal treatment. J Agric Food Chem 63:8705–8714. https://doi.org/10.1021/acs.jafc.5b03471
Budryn G, Nebesny E, Rachwal-Rosiak D (2013) Stability of hydroxycinnamic acids and caffeine from green coffee extracts after heating in food model systems. Eur Food Res Technol 236:969–978. https://doi.org/10.1007/s00217-013-1956-3
Calvi JP, Francis FJ (1978) Stability of concord grape (V. labrusca) anthocyanins in model systems. J Food Sci 43:1448–1456
Chen J, Sun H, Wang Y, Wang S, Tao X, Sun A (2014) Stability of apple polyphenols as a function of temperature and pH. Int J Food Prop 17:1742–1749
Davidov-Pardo G, Arozarena I, Marin-Arroyo MR (2011) Stability of polyphenolic extracts from grape seeds after thermal treatments. Eur Food Res Technol 232:211–220. https://doi.org/10.1007/s00217-010-1377-5
de Ferrars RM, Czank C, Zhang Q, Botting NP, Kroon PA, Cassidy A, Kay CD (2014) The pharmacokinetics of anthocyanins and their metabolites in humans. Br J Pharmacol 171:3268–3282. https://doi.org/10.1111/bph.12676
Dyrby M, Westergaard N, Stapelfeldt H (2001) Light and heat sensitivity of red cabbage extract in soft drink model systems. Food Chem 72:431–437. https://doi.org/10.1016/S0308-8146(00)00251-X
Jin Y, Zhang WY, Meng QF, Li DH, Garg S, Teng LR, Wen JY (2013) Forced degradation of flavonol glycosides extracted from Ginkgo biloba. Chem Res Chin Univer 29:667–670. https://doi.org/10.1007/s40242-013-2352-z
Kern M, Fridrich D, Reichert J, Skrbek S, Nussher A, Hofem S, Vatter S, Pahlke G, Rufer C, Marko D (2007) Limited stability in cell culture medium and hydrogen peroxide formation affect the growth inhibitory properties of delphinidin and its degradation product gallic acid. Mol Nutri Food Res 51:1163–1172. https://doi.org/10.1002/mnfr.200700004
Kim YC, Higuchi R, Kitamura Y, Komori T (1991) Defradation of Flavonoid Glycosides. Lebigs Ann Chem 1991:1285–1289
Ky I, Teissedre PL (2015) Characterisation of mediterranean grape pomace seed and skin extracts: polyphenolic content and antioxidant activity. Molecules 20:2190–2207
Li N, Taylor LS, Ferruzzi MG, Mauer LJ (2012) Kinetic study of catechin stability: effects of pH, concentration, and temperature. J Agric Food Chem 60:12531–12539. https://doi.org/10.1021/jf304116s
Makris DP, Boskou D (2014) Plant-derived antioxidants as food additives. Plant as a source of natural antioxidants. CAB International, Boston, pp 169–190
Malien-Aubert C, Dangles O, Amiot MJ (2001) Color stability of commercial anthocyanin-based extracts in relation to the phenolic composition. Protective effects by intra- and intermolecular copigmentation. J Agric Food Chem 49:170–176. https://doi.org/10.1021/jf000791o
Martin KR, Apple CL (2010) Polyphenols as dietary supplements: a double-edged sword. Nutr Diet Suppl 2:1–12
Mattivi F, Vrhovsek U, Masuero D, Trainotti D (2009) Differences in the amount and structure of extractable skin and seed tannins amongst red grape varieties. Austr J Grape Wine Res 15:27–35. https://doi.org/10.1111/j.1755-0238.2008.00027.x
Patras A, Brunton NP, O’Donnell C (2010) Tiwari BK (2010) Effect of thermal processing on anthocyanin stability in foods; mechanisms and kinetics of degradation. Trends Food Sci Tech 21:3–11
Pinelo M, Rubilar M, Sineiro J, Nunez M (2005) A thermal treatment to increase the antioxidant capacity of natural phenols: catechin, resveratrol and grape extract cases. Eur Food Res Technol 221:284–290. https://doi.org/10.1007/s00217-005-1159-7
Prior RL, Wu XL, Schaich K (2005) Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J Agric Food Chem 53:4290–4302. https://doi.org/10.1021/jf0502698
Reyes LF, Cisneros-Zevallos L (2007) Degradation kinetics and colour of anthocyanins in aqueous extracts of purple- and red-flesh potatoes (Solanum tuberosum L.). Food Chem 100:885–894. https://doi.org/10.1016/j.foodchem.2005.11.002
Riehle P, Vollmer M, Rohn S (2013) Phenolic compounds in Cistus incanus herbal infusions—antioxidant capacity and thermal stability during the brewing process. Food Res Int 53:891–899. https://doi.org/10.1016/j.foodres.2012.09.020
Seeram NP, Bourquin LD, Nair MG (2001) Degradation products of cyanidin glycosides from tart cherries and their bioactivities. J Agric Food Chem 49:4924–4929. https://doi.org/10.1021/jf0107508
Su YL, Leung LK, Huang Y, Chen ZY (2003) Stability of tea theaflavins and catechins. Food Chem 83:189–195. https://doi.org/10.1016/S0308-8146(03)00062-1
Tomaz I, Maslov L (2016) Simultaneous determination of phenolic compounds in different matrices using phenyl-hexyl stationary phase. Food Anal Method 9:401–410. https://doi.org/10.1007/s12161-015-0206-7
Tomaz I, Maslov L, Stupic D, Preiner D, Asperger D, Kontic JK (2016) Solid–liquid extraction of phenolics from red grape skins. Acta Chim Slov 63:287–297. https://doi.org/10.17344/acsi.2015.2181
Volf I, Ignat I, Neamtu M, Popa VI (2014) Thermal stability, antioxidant activity, and photo-oxidation of natural polyphenols. Chem Paper 68:121–129
Wang R, Zhou WB, Wen RAH (2006) Kinetic study of the thermal stability of tea catechins in aqueous systems using a microwave reactor. J Agric Food Chem 54:5924–5932. https://doi.org/10.1021/jf0611419
Zhu QY, Zhang AQ, Tsang D, Huang Y, Chen ZY (1997) Stability of green tea catechins. J Agric Food Chem 45:4624–4628. https://doi.org/10.1021/jf9706080
Zillich OV, Schweiggert-Weisz U, Eisner P, Kerscher M (2015) Polyphenols as active ingredients for cosmetic products. Int J Cosmet Sci 37:455–464. https://doi.org/10.1111/ics.12218
Acknowledgments
This research has been funded/supported by the project KK.01.1.1.01.0005 Biodiversity and Molecular Plant Breeding, Centre of Excellence for Biodiversity and Molecular Plant Breeding (CoE CroP-BioDiv), Zagreb, Croatia.
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Tomaz, I., Šikuten, I., Preiner, D. et al. Stability of polyphenolic extracts from red grape skins after thermal treatments. Chem. Pap. 73, 195–203 (2019). https://doi.org/10.1007/s11696-018-0573-9
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DOI: https://doi.org/10.1007/s11696-018-0573-9