Phenolic compounds present in nearly all parts of grape berries are increasingly believed to exhibit antioxidant and antimicrobial activities and to play a significant role in the prevention of diseases including cancer and cardiovascular diseases (Bagchi et al. 2000, Ariga 2004). The majority of studies on grape phenolics properties has been conducted using proanthocyanidin-rich seeds extracts (GSEs).
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Agarwal C, Veluri R, Kaur M, Chou SC, Thompson JA, Agarwal R (2007) Fractionation of high molecular weight tannins in grape seed extract and identification of procyanidin B2-3,3′-di-Ogallate as a major active constituent causing growth inhibition and apoptotic death of DU145 human prostate carcinoma cells. Carcinogenesis 28:1478-1484
Alonso ÁM, Guillén DA, Barroso CG, Puertas B, García A (2002) Determination of antioxidant activity of wine byproducts and its correlation with polyphenolic content. J Agric Food Chem 50:5832-5836
Ariga T (2004) The antioxidative function, preventive action on disease and utilization of proanthocyanidins. Biofactors 21:197-2001
Auger C, Gérain P, Lurent-Bichon F, Portet K, Bornet A, Caporiccio B, Cros G, Teissédre PL, Rouanet JM (2004) Phenolics from commercialized grape extracts prevent early atherosclerotic lesions in hamsters by mechanisms other than antioxidant effect. J Agric Food Chem 52:5297-5302
Bagchi D, Garg A, Krohn RL, Bagchi M, Bagchi DJ, Balmoori J, Stohs SJ (1998) Protective effects of grape seed proanthocyanidins and selected antioxidants against TPA-induced hepatic and brain lipid peroxidation and DNA fragmentation, and peritoneal macrophage activation in mice. Gen Pharm 30:771-776
Bagchi D, Bagchi M, Stohs SJ, Das DK, Ray SD, Kuszynski CA, Joshi SS, Pruess HG (2000) Free radicals and grape seed proanthocyanidin extract: importance in human health and disease prevention. Toxicology 148:187-197
Bagchi D, Sen CK, Ray SD, Das DK, Baghi M, Preuss HG, Vinson JA (2003) Molecular mechanisms of cardioprotection by a novel grape seed proanthocyanidin extract. Mutat Res 523-524:87-89
Caderni G, De Filippo C, Luceri C, Salvadori M, Gianinni A, Biggeri A, Remy S, Cheynier V, Dolara P (2000) Effects of black tea and wine extracts on intestinal carcinogenesis induced by azoxymethane in F344 rats. Carcinogenesis 21:1965-1969
Cruz JM, Domínguez H, Parajó JC (2004) Assessment of the production of antioxidant from winemaking waste solids. J Agric Food Chem 52:5612-5620
Du Y, Guo H, Lou H (2007) Grape seed polyphenols protect cardiac cells from apoptosis via in duction of endogenous antioxidant enzymes. J Agric Food Chem 55:1695-1701
Eng ET, Ye J, Williams D, Phung S, Moore RE, Young MK, Gruntmanis U, Braunstein G, Chen S (2003) Suppression of estrogen biosynthesis by procyanidin dimers in red wine and grape seeds. Cancer Res 63:8516-8522
Engelbrecht AM, Mattheyse M, Ellis B, Loos B, Thomas M, Smith C, Myburgh K (2007) Proanthocyanidin from grape seeds inactivates the PI3-kinase/PKB pathway and induces apoptosis in a colon cancer cell line. Cancer Lett 258:144-153
Faria A, Calhau C, De Freitag V, Mateus N (2006) Pricyanidins as antioxidants and tumor cell growth modulators. J Agric Food Chem 54:2392-2397
Fauconneau B, Waffo TP, Huguet F, Barrier L, Decendit A, Merillon J-M (1997) Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests. Life Sci 61:2103-2110
Figueiredo AR, Campos F, De Freitas V, Hogg T, Couto JA (2008) Effect of phenolic aldehydes and flavonoids on growth and inactivation of Oenococcus oeni and Lactobacillus hilgardii. Food Microb 25:105-112
Frederiksen H, Mortensen A, Schroder M, Frandsen H, Bysted A, Knuthsen P, Ramissen SE (2007) Effects of red grape skin and seed extract supplementation on atherosclerosis in Watanabe heritable hyperlipidemic rabbits. Mol Nutr Food Res 51:564-571
Fritzpatrick DF, Hirschfield SL, Coffey RG (1993) Endothelium-dependent vasorelaxing activity of wine and other grape products. Am J Physiol 265:H774-H778
Fritzpatrick DF, Fleming RC, Bing B, Maggi DA, O’Malley R (2000) Isolation and characterization of endothelium-dependent vasorelaxing compounds from grape seeds. J Agric Food Chem 48:6384-6390
Fujime H, Nakagawa T, Nishioka H, Sato E, Hirose A, Ueno, Y, Sun B, Yokozawa T, Nonaka GI (2007) Preparation, characterization, and antioxidative effects of oligomeric proanthocyanidin-L-cystein complexes. J Agric Food Chem 55:1525-1531
Fuhrman B, Volkova N, Coleman R, Aviram M (2006) Grape powder polyphenols attenuate atherosclerosis development in apolipoprotein E deficient (E0) mice and reduce macrophage atherogenicity. J Nutr 136:722-728
Gámez-Meza N, Noriega-Rodríguez JA, Medina-Juárez LA, Ortega-García J, Cázarez-Casanova R, Angulo-Guerrero O (1999) Antioxidant activity in soybean oil of extracts from Thompson grape bagasse. J Am Oil Chem Soc 76:1445-1447
Giovannelli L, Testa G, De Filippo C, Cheynier V, Clifford MN, Dolara P (2000) Effect of complex polyphenols and tannins from red wine on DNA oxidative damage of rat colon mucosa in vivo. Eur J Nutr 39:207-212
Hu, H, Qin YM (2006) Grape seed proanthocyanidin extract induced mitochondria-associated apoptosis in human acute myeloid leukaemia 143D10 cells. Chin Med J 119:417-421
Huang TT, Shang XJ, Yao GH, Ge JP, Teng WH, Sun Y, Huang YF (2008) Grape seed extract inhibits the growth of prostate cancer PC-3 cells. Zhonghua Nan Ke Xue (National Journal of Andrology) 14:331-333
Jayaprakasha GK, Singh RP, Sakariah KK (2001) Antioxidant activity of grape seed (Vitis vinifera) extracts on peroxidation models in vitro. Food Chem 73:285-290
Jayaprakasha GK, Dselvi T, Sakariah KK (2003) Antibacterial and antioxidant activities of grape (Vitis vinifera) seed extracts. Food Res Int 36:117-122
Johnson BJ, Delehanty JB, Lin B, Ligler FS (2008) Immobilized proanthocyanidins for the capture of bacterial lipopolysaccharides. Anal Chem 80:2113-2117
Kalhithraka S, Viguera G, Bridle P, Bakker J (1995) Survey of solvents for the extraction of grape seed phenolics. Phytochem Anal 6:265-267
Katiyar SK (2006) Matrix metalloproteinases in cancer metastasis: molecular targets for prostate cancer prevention by green tea polyphenols and grape seed proanthocyanidins. Endocr Metab Immune Disord Drug Targets 6:17-24
Katiyar SK (2007) UV-induced immune suppression and photocarcinogenesis: chemoprevention by dietary botanical agents. Cancer Lett 255:1-11
Katiyar SK (2008) Grape seed proanthocyanidines and skin cancer prevention: Inhibition of oxidative stress and protection of immune system. Mol Nutr Food Res 52S1:S71-S76
Kaur M, Singh RP, Gu M, Agarwal R, Agarwal C (2006a) Grape seed extract inhibits in vitro and in vivo growth of human colorectal carcinoma cells. Clin Cancer Res 15:6194-6202
Kaur M, Agarwal R, Agarwal C (2006b) Grape seed extract induces anoikis and caspasemediated apoptosis in human prostate carcinoma LNCaP cells: possible role of ataxia telangiectasia mutated-p53 activation. Mol Cancer Ther 5:1265-1274
Kijima I, Phung S, Hur G, Kwok SL, Chen S (2006) Grape seed extract is an aromatase inhibitor and a suppressor of aromatase expression. Cancer Res 66:5960-5967
Kim H, Hall P, Smith M, Kirk M, Prasain JK, Grubbs C (2004) Chemoprevention by grape seed extract and genistein in carcinogen-induced mammary cancer in rats is diet dependent. J Nutr 134S:3445S-3452S
Lizarraga D, Lozano C, Briedé JJ, Van Delft JH, Touriño S, Centelles JJ, Torres JL, Cascante M (2007) The importance of polymerization and galloylation for the antiproliferative properties of procyanidin-rich natural extracts. FEBS J 274:4802-4811
Mantena SK, Baliga MS, Katiyar SK (2006) Grape seed proanthocyanidins induce apoptosis and inhibit metastasis of highly metastatic breast carcinoma cells. Carcinogenesis 27:1682-1691
Meeran SM, Katiyar SK (2007) Grape seed proanthocyanidins promote apoptosis in human epidermoid carcinoma A431 cells through alterations in Cdki-Cdk-cyclin cascade, and caspase-3 activation via loss of mitochondrial membrane potential. Exp Dermatol 16:405-415
Meeran SM, Katiyar SK (2008) Proanthocyanidins inhibit mitogenic and survival-signalling in vitro and tumor growth in vivo. Front Sci 13:887-897
Meyer AS, Yi O-S, Pearson DA, Waterhouse AL, Frankel EN (1997) Inhibition of human lowdensity lipoproteins oxidation in relation to composition of phenolic antioxidants in grapes (Vitis vinifera). J Agric Food Chem 45:1638-1643
Mitjans M, Del Campo J, Abaji C, Martínez V, Selga A, Lozano C, Torres JL, Vinardell MP (2004) Immunomodulatory activity of new family of antioxidants obtained from grape polyphenols. J Agric Food Chem 52:7297-7299
Mittal A, Elments CA, Katiyar SK (2003) Dietary feeding of proanthocynidins from grape seeds prevents photocarcinogenesis in SKH-1 hairless mice: relationship to decreased fat and lipid peroxidation. Carcinogenesis 24:1379-1388
Monagas M, Hernández-Ledesman B, Garrido IG, Martín-Álvarez PJ, Gómez-Cordovés P, Bartolomé B (2005) Quality assessment of commercial dietary antioxidant products from Vitis vinifera L grape seeds. Nutr Cancer 53:244-254
Morin B, Narbonne J-F, Ribera D, Badouard C, Ravant J-L (2008) Effect of dietary fat-soluble vitamins A and E and proanthocyanidin-rich extract from grape seeds on oxidative DNS damage in rats. Food Chem Toxicol 46:787-796
Nandakumar V, Singh T, Katiyar SK (2008) Multi-targeted prevention and therapy of cancer by proanthocyanidins. Cancer Lett (in press)
Natella F, Belelli F, Gentili V, Ursini F, Scaccini C (2002) Grape seed proanthocyanidins prevent plasma prostprandial oxidative stress in humans. J Agric Food Chem 50:7720-7725
Nikitina NA, Sobenin IA, Myasoedova VA, Korennaya VV, Melnichenko AA, Khalilo EM, Orekhov AN (2006) Antiatherogenic effect of grape flavonoids in an ex vivo model. Bull Exp Biol Med 141:712-715
Nuttal SL, Kendall MJ, Bombardelli E, Morazzoni P (1998) An evaluation of the antioxidant activity of a standardized grape seed extract. Leucoselect J Clin Pharm Ther 23:323-325
Osman HE, Maalej N, Shanmunganayagam D, Folts JD (1998) Grape juice but not orange or grapefruit juice inhibits platelet activity in dogs and monkeys. J Nutr 128:2307-2312
Parry J, Su L, Moore J, Cheng Z, Luther M, Rao JN, Wang JY, Yu LL (2006) Chemical compositions, antioxidant capacities, and antiproliferative activities of selected fruit seed flours. J Agric Food Chem 54:3773-3778
Pazos M, Lois S, Torres JL, Medina I (2006) Inhibition of hemoglobin- and iron-promoted oxidation in fish microsomes by natural phenolics. J Agric Food Chem 54:4417-4423
Prieur C, Rigaud J, Cheynier V, Moutounet M (1994) Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36:781-784
Rhodes, PL, Mitchell JW, Wilson MW, Melton LD (2006) Antilisterial activity of grape juice and grape extracts derived from Vitis vinifera variety Ribier. Int J Microb 107:281-286
Shafiee M, Carbonneau MA, Urban N, Descomps B, Leger CL (2003) Grape and grape seed extract capacities at protecting LDL against oxidation generated by Cu2+, AAPH or SIN-1 and at decreasing superoxide THP-1 cell production A comparison to other extracts or compounds. Free Radic Res 37:573-584
Shanmunganayagam D, Warner TF, Krueger CG, Reed JD, Folts JD (2007) Concord grape juice attenuates platelet aggregation, serum cholesterol and development of atheroma in hypercholesterolemic rabbits. Atherosclerosis 190:135-142
Sharma SD, Meeran SM, Katiyar SK (2007) Dietary grape seed proanthocyanidins inhibit UVBinduced oxidative stress and activation of mitogen-activated protein kinases and nuclear factor-kappaB signalling in in vivo SKH-1 hairless mice. Mol Cancer Ther 6:995-1005
Shoko T, Soichi T, Megumi MM, Eri F, Jun K, Michaiko W (1999) Isolation and identification of an antibacterial compound from grape and its application to foods. Nippon Nogeikagaku Kaishi 73:125-128
Singletary KW, Jung KJ, Giusti M (2007) Anthocyanin-rich grape extract blocks breast cell DNA damage. J Med Food 10: 44-251
Simonetti P, Ciappellano S, Gardana C, Bramati L, Pietta P (2002) Procyanidins from Vitis vinifera seeds: in vivo effects on oxidative stress. J Agric Food Chem 50:6217-6221
Sivarooban T, Hettiarachychy NS, Johnson MG (2007) Inhibition of Listeria monocytogenes using nisin with grape seed extract on turkey frankfurters stored at 4 and 10 degrees. J Food Prot 70:1017-1020
Smullen J, Koutsou GA, Foster HA, Zumbé A, Storey DM (2007) The antibacterial activity of plant extracts containing polyphenols against Streptococcus mutans. Caries Res 41:342-349
Sun B, Leandro C, da Silva JMR, Spranger I (1998) Separation of grape and wine proanthocyanidins according to their degree of polymerization. J Agric Food Chem 46:1390-1396
Tebib K, Bitri L, Besancon P, Rouanet JM (1994) Polymeric grape seed tannins prevent plasma cholesterol changes in high-cholesterol-fed rats. Food Chem 49:403-406
Thimothe J, Bonsi IA, Padilla-Zakour OI, Koo H (2007) Chemical characterization of red wine grape (Vitis vinifera and Vitis interspecific hybrids) and pomace phenolic extracts and their biological activity against Streptococcus mutans. J Agric Food Chem 55:10200-10207
Thuille N, Fille M, Nagl M (2003) Bactericidal activity of herbal extract. Int J Hyg Environ Health 2006:217-221
Tyagi A, Agarwal R, Agarwal C (2003) Grape seed extract inhibits EGF-induced and constitutively active mitogenic signalling but activates JNK in human prostate carcinoma DU145 cells: possible role in antiproliferation and apoptosis. Oncogene 22:1302-1316
Uchida S, Hirai K, Hatanaka J, Hanato J, Umegaki K, Yamada S (2008) Antinociceptive effect of St John’s wort, Harpagophytum procumbens extract and grape seed proanthocyanidins extract in mice. Biol Pharm Bull 31:240-245
Ugartondo V, Mitjans M, Touriño S, Torres JL, Vinardel MP (2007) Comparative antioxidant and cytotoxic effect of procyanidin fractions from grape and pine. Chem Res Toxicol 20:1543- 1548
Weidner S, Karamać M, Amarowicz R, Szypulska E, Gołgłowska A, (2007) Changes in composition of phenolic compounds and antioxidant properties of Vitis amurensis seeds germinated under osmotic stress. Acta Physiol Plant 29:283-290
Yamakoshi J, Kataoka S, Koga T, Ariga T (2000) Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits. Atherosclerosis 142:139-149
Yamakoshi J, Saito M, Kataoka S, Kikuchi M (2002) Safety evaluation of proanthocyanidins-rich extract from grape seeds. Food Chem Toxicol 40:599-607
Yi OS, Meyer AS, Frankel EN (1997) Antioxidant activity of grape extracts in a lecithin liposome system. J Am Oil Chem Soc 74:1301-1307
Yilmaz Y, Toledo RT (2006) Oxygen radical absorbance capacities of grape/wine industry byproducts and effect of solvent type on extraction of grape seed polyphenols. J Food Comp Analys 19:41-48
Yu H, Wang SE, Zhao C, Xu G (2002) Study of anti-atherosclerosic effect of grape seed extract and its mechanism. Wei Sheng Yam Jin 31:263-265
Vayalil PK, Mittal A, Katiyar SK (2004) Proanthocyanidins from grape seeds inhibit expression of matrix metaloproteinases in human prostate carcinoma cells which is associated with the inhibition of activation of MAPK and NFκB. Carcinogenesis 25:987-995
Zern TL, West KL, Fernandez ML (2003) Grape polyphenols decrease plasma triglycerides and cholesterol accumulation in the aorta of ovariectomized guinea pigs. J Nutr 133:2268-2272
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Amarowicz, R., Weidner, S. (2009). Biological Activity of Grapevine Phenolic Compounds. In: Roubelakis-Angelakis, K.A. (eds) Grapevine Molecular Physiology & Biotechnology. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-2305-6_14
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