Low molecular weight phenolics of grape juice and winemaking byproducts: Antioxidant activities and inhibition of oxidation of human low-density lipoprotein cholesterol and DNA strand breakage

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 50, 2014, Pages 12159-12171

  De Camargo, Adriano Costa ^a,b   Regitano D'Arce, Marisa Aparecida Bismara ^b   Biasoto, Aline Camarão Telles ^c   Shahidi, Fereidoon ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c EMBRAPA SEMIÁRIDO   (Brazil)

Author keywords

DNA; Flavonoids; LDL cholesterol; Phenolic acids; Proanthocyanidin; Processing byproduct

Indexed keywords

ANTIOXIDANTS; CHOLESTEROL; DNA; ESTERS; FLAVONOIDS; FRUIT JUICES; ORGANIC ACIDS; PHENOLS;

ANTI-OXIDANT ACTIVITIES; BIOACTIVE COMPOUNDS; LOW DENSITY LIPOPROTEINS; LOW MOLECULAR WEIGHT; PHENOLIC ACIDS; PHENOLIC COMPOUNDS; PROANTHOCYANIDINS; SCAVENGING ACTIVITIES;

BYPRODUCTS;

CORA; VITACEAE;

ANTIOXIDANT; LOW DENSITY LIPOPROTEIN CHOLESTEROL; PHENOL DERIVATIVE; PLANT EXTRACT; WASTE;

ANALYSIS; CHEMISTRY; DNA STRAND BREAKAGE; DRUG EFFECTS; HUMAN; MOLECULAR WEIGHT; OXIDATION REDUCTION REACTION; VITIS; WASTE;

ANTIOXIDANTS; CHOLESTEROL, LDL; DNA BREAKS; HUMANS; MOLECULAR WEIGHT; OXIDATION-REDUCTION; PHENOLS; PLANT EXTRACTS; VITIS; WASTE PRODUCTS;

EID: 84918497421     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf504185s     Document Type: Article

References (43)

1. Cheng, V. J.; Bekhit, A. E. A.; McConnell, M.; Mros, S.; Zhao, J. Effect of extraction solvent, waste fraction and grape variety on the antimicrobial and antioxidant activities of extracts from wine residue from cool climate. Food Chem. 2012, 134 (1), 474-482.
2. Chandrasekara, A.; Shahidi, F. Antiproliferative potential and DNA scission inhibitory activity of phenolics from whole millet grains. J. Funct. Foods 2011, 3 (3), 159-170.
3. de Camargo, A.; Vieira, T.; Regitano-D'Arce, M.; Calori-Domingues, M.; Canniatti-Brazaca, S. Gamma radiation effects on peanut skin antioxidants. Int. J. Mol. Sci. 2012, 13 (3), 3073-3084.
4. Shahidi, F.; Alasalvar, C.; Liyana-Pathirana, C. M. Antioxidant phytochemicals in hazelnut kernel (Corylus avellana L.) and hazelnut byproducts. J. Agric. Food Chem. 2007, 55 (4), 1212-1220.
5. Lee, N.; Jo, C.; Sohn, S.; Kim, J.; Byun, M. Effects of gamma irradiation on the biological activity of green tea byproduct extracts and a comparison with green tea leaf extracts. J. Food Sci. 2006, 71 (4), C269-C274.
6. Llobera, A.; Canellas, J. Dietary fibre content and antioxidant activity of Manto Negro red grape (Vitis vinifera): pomace and stem. Food Chem. 2007, 101 (2), 659-666.
7. Shirahigue, L.; Plata-Oviedo, M.; de Alencar, S.; d'Arce, M.; Vieira, T.; Oldoni, T.; Contreras-Castillo, C. Wine industry residue as antioxidant in cooked chicken meat. Int. J. Food Sci. Technol. 2010, 45 (5), 863-870.
8. Jara-Palacios, M. J.; Gonzalez-Manzano, S.; Escudero-Gilete, M. L.; Hernanz, D.; Duenas, M.; Gonzalez-Paramas, A. M.; Heredia, F. J.; Santos-Buelga, C. Study of Zalema grape pomace: phenolic composition and biological effects in Caenorhabditis elegans. J. Agric. Food Chem. 2013, 61 (21), 5114-5121.
9. Evans, M.; Wilson, D.; Guthrie, N. A randomized, double-blind, placebo-controlled, pilot study to evaluate the effect of whole grape extract on antioxidant status and lipid profile. J. Funct. Foods 2014, 7, 680-691.
10. Sandhu, A. K.; Gu, L. W. Antioxidant capacity, phenolic content, and profiling of phenolic compounds in the seeds, skin, and pulp of Vitis rotundifolia (Muscadine grapes) as determined by HPLC-DAD-ESI-MSn. J. Agric. Food Chem. 2010, 58 (8), 4681-4692.
11. González-Centeno, M. R.; Jourdes, M.; Femenia, A.; Simal, S.; Rosselló, C.; Teissedre, P.-L. Proanthocyanidin composition and antioxidant potential of the stem winemaking byproducts from 10 different grape varieties (Vitis vinifera L.). J. Agric. Food Chem. 2012, 60 (48), 11850-11858.
12. Wettasinghe, M.; Shahidi, F. Scavenging of reactive-oxygen species and DPPH free radicals by extracts of borage and evening primrose meals. Food Chem. 2000, 70 (1), 17-26.
13. de Camargo, A. C.; Vieira, T. M. F. S.; Regitano-D'Arce, M. A. B.; de Alencar, S. M.; Calori-Domingues, M. A.; Canniatti-Brazaca, S. G. Gamma radiation induced oxidation and tocopherols decrease in in-shell, peeled and blanched peanuts. Int. J. Mol. Sci. 2012, 13 (3), 2827-2845.
14. Swain, T.; Hillis, W. E. The phenolic constituents of Prunus domestica. I. The quantitative analysis of phenolic constituents. J. Sci. Food Agric. 1959, 10 (1), 63-68.
15. de Camargo, A. C.; Vieira, T. M. F. S.; Regitano-d'Arce, M. A. B.; de Alencar, S. M.; Calori-Domingues, M. A.; Spoto, M. H. F.; Canniatti-Brazaca, S. G. Gamma irradiation of in-shell and blanched peanuts protects against mycotoxic fungi and retains their nutraceutical components during long-term storage. Int. J. Mol. Sci. 2012, 13 (9), 10935-10958.
16. Price, M. L.; Hagerman, A. E.; Butler, L. G. Tannin content of cowpeas, chickpeas, pigeon peas, and mung beans. J. Agric. Food Chem. 1980, 28 (2), 459-461.
17. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol. Med. 1999, 26 (9-10), 1231-1237.
18. Chandrasekara, N.; Shahidi, F. Effect of roasting on phenolic content and antioxidant activities of whole cashew nuts, kernels, and testa. J. Agric. Food Chem. 2011, 59 (9), 5006-5014.
19. Alasalvar, C.; Karamac, M.; Kosinska, A.; Rybarczyk, A.; Shahidi, F.; Amarowicz, R. Antioxidant activity of hazelnut skin phenolics. J. Agric. Food Chem. 2009, 57 (11), 4645-4650.
20. Zadernowski, R.; Naczk, M.; Nesterowicz, J. Phenolic acid profiles in some small berries. J. Agric. Food Chem. 2005, 53 (6), 2118-2124.
21. Lago-Vanzela, E. S.; Rebello, L. P. G.; Ramos, A. M.; Stringheta, P. C.; Da-Silva, R.; García-Romero, E.; Gómez-Alonso, S.; Hermosín-Gutiérrez, I. Chromatic characteristics and color-related phenolic composition of Brazilian young red wines made from the hybrid grape cultivar BRS Violeta ("BRS Rúbea" x "IAC 1398-21"). Food Res. Int. 2013, 54 (1), 33-43.
22. Hanhineva, K.; Rogachev, I.; Kokko, H.; Mintz-Oron, S.; Venger, I.; Kärenlampi, S.; Aharoni, A. Non-targeted analysis of spatial metabolite composition in strawberry (Fragaria x ananassa) flowers. Phytochemistry 2008, 69 (13), 2463-2481.
23. Sarnoski, P. J.; Johnson, J. V.; Reed, K. A.; Tanko, J. M.; O'Keefe, S. F. Separation and characterisation of proanthocyanidins in Virginia type peanut skins by LC-MS n. Food Chem. 2012, 131 (3), 927-939.
24. de Camargo, A. C.; Vidal, C. M. M.; Canniatti-Brazaca, S. G.; Shahidi, F. Fortification of cookies with peanut skin: effects on the composition, polyphenols, antioxidant properties and sensory quality. J. Agric. Food Chem. 2014, 62 (46), 11228-11235.
25. Saint-Cricq de Gaulejac, N.; Provost, C.; Vivas, N. Comparative study of polyphenol scavenging activities assessed by different methods. J. Agric. Food Chem. 1999, 47 (2), 425-431.
26. Weidner, S.; Powałka, A.; Karamać, M.; Amarowicz, R. Extracts of phenolic compounds from seeds of three wild grapevines - comparison of their antioxidant activities and the content of phenolic compounds. Int. J. Mol. Sci. 2012, 13 (3), 3444-3457.
27. Weidner, S.; Rybarczyk, A.; Karamać, M.; Król, A.; Mostek, A.; Gre¸bosz, J.; Amarowicz, R. Differences in the phenolic composition and antioxidant properties between Vitis coignetiae and Vitis vinifera seeds extracts. Molecules 2013, 18 (3), 3410-3426.
28. Ćurko, N.; Kovačević Ganić, K.; Gracin, L.; Crossed D signapić, M.; Jourdes, M.; Teissedre, P. L. Characterization of seed and skin polyphenolic extracts of two red grape cultivars grown in Croatia and their sensory perception in a wine model medium. Food Chem. 2014, 145, 15-22.
29. Vrhovsek, U.; Mattivi, F.; Waterhouse, A. L. Analysis of red wine phenolics: comparison of HPLC and spectrophotometric methods. Vitis 2001, 40 (2), 87-91.
30. Chandrasekara, A.; Shahidi, F. Determination of antioxidant activity in free and hydrolyzed fractions of millet grains and characterization of their phenolic profiles by HPLC-DAD-ESI-MSn. J. Funct. Foods 2011, 3 (3), 144-158.
31. Flachowsky, H.; Halbwirth, H.; Treutter, D.; Richter, K.; Hanke, M.-V.; Szankowski, I.; Gosch, C.; Stich, K.; Fischer, T. C. Silencing of flavanone-3-hydroxylase in apple (Malus x domestica Borkh.) leads to accumulation of flavanones, but not to reduced fire blight susceptibility. Plant Physiol. Biochem. 2012, 51, 18-25.
32. Owens, D. K.; Crosby, K. C.; Runac, J.; Howard, B. A.; Winkel, B. S. J. Biochemical and genetic characterization of Arabidopsis flavanone 3β-hydroxylase. Plant Physiol. Biochem. 2008, 46 (10), 833-843.
33. Xie, D.-Y.; Jackson, L. A.; Cooper, J. D.; Ferreira, D.; Paiva, N. L. Molecular and biochemical analysis of two cDNA clones encoding dihydroflavonol-4-reductase from Medicago truncatula. Plant Physiol. 2004, 134 (3), 979-994.
34. Pfeiffer, J.; Kühnel, C.; Brandt, J.; Duy, D.; Punyasiri, P. A. N.; Forkmann, G.; Fischer, T. C. Biosynthesis of flavan 3-ols by leucoanthocyanidin 4-reductases and anthocyanidin reductases in leaves of grape (Vitis vinifera L.), apple (Malus x domestica Borkh.) and other crops. Plant Physiol. Biochem. 2006, 44 (5-6), 323-334.
35. Xie, D.-Y.; Sharma, S. B.; Dixon, R. A. Anthocyanidin reductases from Medicago truncatula and Arabidopsis thaliana. Arch. Biochem. Biophys. 2004, 422 (1), 91-102.
36. Cerpa-Calderón, F. K.; Kennedy, J. A. Berry integrity and extraction of skin and seed proanthocyanidins during red wine fermentation. J. Agric. Food Chem. 2008, 56 (19), 9006-9014.
37. Meyer, A. S.; Heinonen, M.; Frankel, E. N. Antioxidant interactions of catechin, cyanidin, caffeic acid, quercetin, and ellagic acid on human LDL oxidation. Food Chem. 1998, 61 (1-2), 71-75.
38. Wanasundara, U. N.; Shahidi, F. Antioxidant and pro-oxidant activity of green tea extracts in marine oils. Food Chem. 1998, 63 (3), 335-342.
39. Yilmaz, Y.; Toledo, R. T. Major flavonoids in grape seeds and skins: antioxidant capacity of catechin, epicatechin, and gallic acid. J. Agric. Food Chem. 2004, 52 (2), 255-260.
40. Paiva-Martins, F.; Gordon, M. H. Effects of pH and ferric ions on the antioxidant activity of olive polyphenols in oil-in-water emulsions. J. Am. Oil Chem. Soc. 2002, 79 (6), 571-576.
41. Arranz, S.; Silván, J. M.; Saura-Calixto, F. Nonextractable polyphenols, usually ignored, are the major part of dietary polyphenols: a study on the Spanish diet. Mol. Nutr. Food Res. 2010, 54 (11), 1646-1658.
42. Khan, N.; Monagas, M.; Andres-Lacueva, C.; Casas, R.; Urpi-Sarda, M.; Lamuela-Raventos, R. M.; Estruch, R. Regular consumption of cocoa powder with milk increases HDL cholesterol and reduces oxidized LDL levels in subjects at high-risk of cardiovascular disease. Nutr. Metab. Cardiovasc. Dis. 2012, 22 (12), 1046-1053.
43. Delgado, M. E.; Haza, A. I.; García, A.; Morales, P. Myricetin, quercetin, (+)-catechin and (-)-epicatechin protect against N-nitrosamines-induced DNA damage in human hepatoma cells. Toxicol. in Vitro 2009, 23 (7), 1292-1297.