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Phenolic and Anthocyanin Profile of Valea Calugareasca Red Wines by HPLC-PDA-MS and MALDI-TOF Analysis

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Abstract

The quality of red wines is given by phenolic compounds and anthocyanins and is associated with colour, taste and therapeutic effects on human health. This work aims to provide a detailed profile of phenolic compounds and anthocyanins that are found in five red wine samples from Dealu Mare-Valea Calugareasca region. The phenolic and anthocyanin profiles of the red wine samples were determined by high-performance liquid chromatography-photodiode array-mass spectrometry and matrix-assisted laser desorption/ionisation–time of flight, respectively. The results obtained showed that Feteasca Neagra had the highest content of phenolic compounds followed by Pinot Noir while the preponderant compound was gallic acid. Amongst anthocyanins, malvidin was found to be the major compound and the highest anthocyanin content was found also for Feteasca Neagra wine. A simple high-performance liquid chromatography-photodiode array-mass spectrometry method was developed, optimised and applied for the quantification of phenolic compounds in red wine samples from Dealu Mare-Valea Calugareasca region. In the same time, a rapid matrix-assisted laser desorption/ionisation–time of flight method that does not need sample preparation was applied for the identification of anthocyanins. Moreover, the phenolic and anthocyanin composition of red wines from Dealu Mare-Valea Calugareasca region is reported for the first time. The phenolic and anthocyanin profile determination will be beneficial for the Romanian winemakers to produce high-quality red wines.

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References

  • Barreiros ALBS, David JM, David JP (2006) Oxidative stress: relations between the formation of reactive species and the organism’s defense. Quim Nova. 29:113–123. doi:10.1590/S0100-40422006000100021

    Article  CAS  Google Scholar 

  • Berente B, Reichenbächer M, Danzer K (2001) Improvement of the HPLC analysis of anthocyanins in red wines by use of recently developed columns. Fresenius J Anal Chem 371:68–72. doi:10.1007/s002160100940

    Article  CAS  Google Scholar 

  • Boulton R (2001) The copigmentation of anthocyanins and its role in the color of red wine: A critical review. Am J Enol Vitic 52:67–87

    CAS  Google Scholar 

  • Burin VM, Arcari SG, Costa LL, Bordignon-Luiz MT (2011) Determination of some phenolic compounds in red wine by RP-HPLC: method development and validation. J Chromatogr Sci 49:647–651

  • Castañeda-Ovando A, Sedo O, Havel J, Pacheco L, Galán-Vidal CA, Contreras López E (2012) Identification of anthocyanins in red grape, plum and capulin by MALDI-ToF MS. J Mex Chem Soc 56:378–383

    Google Scholar 

  • Cliff MA, King MC, Schlosser J (2007) Anthocyanin, phenolic composition, colour measurement and sensory analysis of BC commercial red wines. Food Res Int 40:92–100. doi:10.1016/j.foodres.2006.08.002

    Article  CAS  Google Scholar 

  • Clifford AJ, Ebeler SE, Ebeler JD, Bills ND, Hinrichs SH, Teissedre P-L, Waterhouse AL (1996) Delayed tumor onset in transgenic mice fed an amino acid-based diet supplemented with red wine solids. Am J Clin Nutr 64:748–756

    CAS  Google Scholar 

  • Das S, Santani DD, Dhalla NS (2007) Experimental evidence for the cardioprotective effects of red wine. Exp Clin Cardiol 12:5–10

    CAS  Google Scholar 

  • de Quirós AR-B, Lage-Yusty MA, López-Hernández J (2009) HPLC-analysis of polyphenolic compounds in Spanish white wines and determination of their antioxidant activity by radical scavenging assay. Food Res Int 42:1018–1022. doi:10.1016/j.foodres.2009.04.009

    Article  Google Scholar 

  • De Rosso M, Tonidandel L, Larcher R, Nicolini G, DallaVedova A, De Marchi F, Gardiman M, Giust M, Flamini R (2014) Identification of new flavonols in hybrid grapes by combined liquid chromatography–mass spectrometry approaches. Food Chem 163:244–251. doi:10.1016/j.foodchem.2014.04.110

    Article  Google Scholar 

  • De Villiers A, Cabooter D, Lynen F, Desmet G, Sandra P (2011) High-efficiency high performance liquid chromatographic analysis of red wine anthocyanins. J Chromatogr A 1218:4660–4670. doi:10.1016/j.chroma.2009.02.038

    Article  Google Scholar 

  • Dimitrovska M, Tomovska E, Bocevska M (2013) Characterisation of Vranec, Cabernet Sauvignon and Merlot wines based on their chromatic and anthocyanin profiles. J Serb Chem Soc 78:1309–1322. doi:10.2298/JSC130101026D

    Article  CAS  Google Scholar 

  • Downey MO, Rochfort S (2008) Simultaneous separation by reversed-phase high-performance liquid chromatography and mass spectral identification of anthocyanins and flavonols in Shiraz grape skin. J Chromatogr A 1201:43–47. doi:10.1016/j.chroma.2008.06.002

    Article  CAS  Google Scholar 

  • Fang F, Li JM, Pan QH, Huang WD (2007) Determination of red wine flavonoids by HPLC and effect of aging. Food Chem 101:428–433. doi:10.1016/j.foodchem.2005.12.036

    Article  CAS  Google Scholar 

  • Fang F, Li J-M, Zhang P, Tang K, Wang W, Pan Q-H, Huang WD (2008) Effects of grape variety, harvest date, fermentation vessel and wine ageing on flavonoid concentration in red wines. Food Res Int 41:53–60. doi:10.1016/j.foodres.2007.09.004

    Article  CAS  Google Scholar 

  • Flamini R (2003) Mass spectrometry in grape and wine chemistry. Part I: Polyphenols. Mass Spectrom Rev 22:218–250. doi:10.1002/mas.10052

    Article  CAS  Google Scholar 

  • Flamini R, Traldi P (2010) Grape and wine poliphenols. In: Desiderio DM, Nibbering NM (eds) Mass spectrometry in grape and wine chemistry. Wiley, New Jersey, pp 163–225

    Chapter  Google Scholar 

  • Galanakis CM, Markouli E, Gekas V (2013) Recovery and fractionation of different phenolic classes from winery sludge using ultrafiltration. Sep Purif Technol 107:245–251. doi:10.1016/j.seppur.2013.01.034

    Article  CAS  Google Scholar 

  • Ghosh D, Konishi T (2007) Anthocyanins and anthocyanin-rich extracts: role in diabetes and eye function. Asia Pac J Clin Nutr 16:200–208

    CAS  Google Scholar 

  • Ginjom I, D'Arcy B, Caffin N, Gidley M (2011) Phenolic compound profiles in selected Queensland red wines at all stages of the wine-making process. Food Chem 125:823–834. doi:10.1016/j.foodchem.2010.08.062

    Article  CAS  Google Scholar 

  • Grant DC, Helleur RJ (2008) Rapid screening of anthocyanins in berry samples by surfactant-mediated matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 22:156–164. doi:10.1002/rcm

    Article  CAS  Google Scholar 

  • Guidance for Industry Analytical Procedures and Methods Validation for Drugs and Biologics, (2014) http://www.fda.gov/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/default.htm

  • He F, Liang N-N, Mu L, Pan Q-H, Wang J, Reeves MJ, Duan C-Q (2012) Anthocyanins and their variation in red wines I. Monomeric anthocyanins and their color expression. Molecules 17:1571–1601. doi:10.3390/molecules17021571

    Article  CAS  Google Scholar 

  • Huang Z, Wang B, Williams P, Pace RD (2009) Identification of anthocyanins in muscadine grapes with HPLC-ESI-MS. LWT-Food Sci Technol 42:819–824. doi:10.1016/j.lwt.2008.11.005

    Article  CAS  Google Scholar 

  • Ivanova V, Dörnyei Á, Stefova M, Stafilov T, Vojnoski B, Kilár F, Márk L (2011) Rapid MALDI-TOF-MS detection of anthocyanins in wine and grape using different matrices. Food Anal Method 4:108–115. doi:10.1007/s12161-010-9143-7

    Article  Google Scholar 

  • Jackson RS (2008) Wine science. Principles and applications, 3rd edn. Elsevier, Amsterdam, pp 686–706

    Google Scholar 

  • Jaitz L, Siegl K, Eder R, Rak G, Abranko L, Koellensperger G, Hann S (2010) LC-MS/MS analysis of phenols for classification of red wine according to geographic origin, grape variety and vintage. Food Chem 122:366–372. doi:10.1016/j.foodchem.2010.02.053

    Article  CAS  Google Scholar 

  • Jang YJ, Kang NJ, Lee KW, Lee HJ (2009) Protective effects of red wine flavonols on 4-hydroxynonenal-induced apoptosis in PC12 cells. Ann N Y Acad Sci 1171:170–175. doi:10.1111/j.1749-6632.2009.04720.x

    Article  CAS  Google Scholar 

  • Kolouchová-Hanzlíková I, Melzoch K, Filip V, Šmidrkal J (2004) Rapid method for resveratrol determination by HPLC with electrochemical and UV detections in wines. Food Chem 87:151–158. doi:10.1016/j.foodchem.2004.01.028

    Article  Google Scholar 

  • La Torre GL, Saitta M, Vilasi F, Pellicanò T, Dugo G (2006) Direct determination of phenolic compounds in Sicilian wines by liquid chromatography with PDA and MS detection. Food Chem 94:640–650. doi:10.1016/j.foodchem.2005.02.007

    Article  Google Scholar 

  • Lee J, Rennaker C, Wrolstad RE (2008) Correlation of two anthocyanin quantification methods: HPLC and spectrophotometric methods. Food Chem 110:782–786. doi:10.1016/j.foodchem.2008.03.010

    Article  CAS  Google Scholar 

  • Lippi G, Franchini M, Guidi GC (2010) Red wine and cardiovascular health: The “French Paradox” revisited. Int J Wine Res 2:1–7. doi:10.2147/IJWR.S8159

    CAS  Google Scholar 

  • Matthäus B (2002) Antioxidant activity of extracts obtained from residues of different oilseeds. J Agric Food Chem 50:3444–3452. doi:10.1021/jf011440s

    Article  Google Scholar 

  • Minussi RC, Rossi M, Bologna L, Cordi L, Rotilio D, Pastore GM, Durán N (2003) Phenolic compounds and total antioxidant potential of commercial wines. Food Chem 82:409–416. doi:10.1016/S0308-8146(02)00590-3

    Article  CAS  Google Scholar 

  • Mira de Orduña R (2010) Climate change associated effects on grape and wine quality and production. Food Res Int 43:1844–1855. doi:10.1016/j.foodres.2010.05.001

    Article  Google Scholar 

  • Monagas M, Bartolomé B, Gómez-Cordovés C (2005) Updated knowledge about the presence of phenolic compounds in wine. Crit Rev Food Sci Nutr 45:85–118. doi:10.1080/10408690490911710

    Article  CAS  Google Scholar 

  • Mudnic I, Modun D, Rastija V, Vukovic J, Brizic I, Katalinic V, Kozina B, Medic-Saric M, Boban M (2010) Antioxidative and vasodilatory effects of phenolic acids in wine. Food Chem 119:1205–1210. doi:10.1016/j.foodchem.2009.08.038

    Article  CAS  Google Scholar 

  • Muñoz S, Mestres M, Busto O, Guasch J (2008) Determination of some flavan-3-ols and anthocyanins in red grape seed and skin extracts by HPLC-DAD: validation study and response comparison of different standards. Anal Chim Acta 628:04–110. doi:10.1016/j.aca.2008.08.045

    Article  Google Scholar 

  • Nunes C, Ferreira E, Freitas V, Almeida L, Barbosa RM, Laranjinha J (2013) Intestinal anti-inflammatory activity of red wine extract: Unveiling the mechanisms in colonic epithelial cells. Food Funct 4:73–383. doi:10.1039/c2fo30233k

    Article  Google Scholar 

  • Opie LH, Lecour S (2007) The red wine hypothesis: from concepts to protective signalling molecules. Eur Heart J 28:1683–1693. doi:10.1093/eurheartj/ehm149

    Article  CAS  Google Scholar 

  • Peña A, Garcia V, De La Luz Romero M, Capella S (1997) Reversed-phase ion-pair chromatography of anthocyanins in red wines. J Chromatogr Sci 35:161–164. doi:10.1093/chromsci/35.4.161

    Article  Google Scholar 

  • Pérez-Magariño S, González-San José MAL (2006) Polyphenols and colour variability of red wines made from grapes harvested at different ripeness grade. Food Chem 96:197–208. doi:10.1016/j.foodchem.2005.02.021

    Article  Google Scholar 

  • Porgali E, Büyüktuncel E (2012) Determination of phenolic composition and antioxidant capacity of native red wines by high performance liquid chromatography and spectrophotometric methods. Food Res Int 45:145–154. doi:10.1016/j.foodres.2011.10.025

    Article  CAS  Google Scholar 

  • Puškaš V, Miljić U (2012) The application of D-optimal design for modelling the red wine ageing process. Food Control 28:362–367. doi:10.1016/j.foodcont.2012.04.050

    Article  Google Scholar 

  • Qin C, Li Y, Niu W, Ding Y, Zhang R, Shang X (2010) Analysis and characterisation of anthocyanins in mulberry fruit. Czech J Food Sci 28:117–126

    CAS  Google Scholar 

  • Rodríguez-Delgado MA, Malovaná S, Pérez JP, Borges T, García Montelongo FJ (2001) Separation of phenolic compounds by high-performance liquid chromatography with absorbance and fluorimetric detection. J Chromatogr A 912:249–257. doi:10.1016/S0021-9673(01)00598-2

    Article  Google Scholar 

  • Sagratini G, Maggi F, Caprioli G, Cristalli G, Ricciutelli M, Torregiani E, Vittori S (2012) Comparative study of aroma profile and phenolic content of Montepulciano monovarietal red wines from the Marches and Abruzzo regions of Italy using HS-SPME–GC–MS and HPLC–MS. Food Chem 132:1592–1599. doi:10.1016/j.foodchem.2011.11.108

    Article  CAS  Google Scholar 

  • Şener A, Canbaş A, Ünal MÜ (2007) The effect of fermentation temperature on the growth kinetics of wine yeast species. Turk J Agric For 31:349–354

    Google Scholar 

  • Šeruga M, Novak I, Jakobek L (2011) Determination of polyphenols content and antioxidant activity of some red wines by differential pulse voltammetry, HPLC and spectrophotometric methods. Food Chem 124:1208–1216. doi:10.1016/j.foodchem.2010.07.047

    Article  Google Scholar 

  • Shipp J, Abdel-Aal E-SM (2010) Food applications and physiological effects of anthocyanins as functional food ingredients. Open Food Sci J 4:7–22. doi:10.2174/1874256401004010007

    Article  CAS  Google Scholar 

  • Stefova M, Ivanova V (2011) Analytical methodology for characterization of grape and wine phenolic bioactives. In: Tokuşoğlu Ö, Hall C III (eds) Fruit and cereal bioactives—sources, chemistry, and applications. CRC Press, USA, pp 409–427

    Chapter  Google Scholar 

  • Tarola AM, Milano F, Giannetti V (2007) Simultaneous determination of phenolic compounds in red wines by HPLC-UV. Anal Lett 40:2433–2445. doi:10.1080/00032710701577666

    Article  CAS  Google Scholar 

  • Valls J, Millán S, Martí MP, Borràs E, Arola L (2009) Advanced separation methods of food anthocyanins, isoflavones and flavanols. J Chromatogr A 1216:7143–7172. doi:10.1016/j.chroma.2009.07.030

    Article  CAS  Google Scholar 

  • Vidal S, Francis L, Noble A, Kwiatkowski M, Cheynier V, Waters E (2004) Taste and mouth-feel properties of different types of tannin-like polyphenolic compounds and anthocyanins in wine. Anal Chim Acta 513:57–65. doi:10.1016/S0003-2670(03)01346-1

    Article  CAS  Google Scholar 

  • Viñas P, López-Erroz C, Marín-Hernández JJ, Hernández-Córdoba M (2000) Determination of phenols in wines by liquid chromatography with photodiode array and fluorescence detection. J Chromatogr A 871:85–93. doi:10.1016/S0021-9673(99)01087-0

    Article  Google Scholar 

  • Wu X, Beecher GR, Holden JM, Haytowitz DB, Gebhardt SE, Prior RL (2006) Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. J Agric Food Chem 54:4069–4075. doi:10.1021/jf060300l

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by a grant of the Romanian National Authority for Scientific Research, CNDI–UEFISCDI, project number PN-II-PT-PCCA-2011-3.1-1809.

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All authors declare that they have no conflict of interest. Andreia Alecu declares that he has no conflict of interest. Camelia Albu declares that he has no conflict of interest. Simona Carmen Litescu declares that he has no conflict of interest. Sandra Anamaria Victoria Eremia declares that he has no conflict of interest. Gabriel Lucian Radu declares that he has no conflict of interest. This article does not contain any studies with human or animal subjects.

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Alecu, A., Albu, C., Litescu, S.C. et al. Phenolic and Anthocyanin Profile of Valea Calugareasca Red Wines by HPLC-PDA-MS and MALDI-TOF Analysis. Food Anal. Methods 9, 300–310 (2016). https://doi.org/10.1007/s12161-015-0197-4

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