Galloylation of polyphenols alters their biological activity

Food and Chemical Toxicology

Volumn 105, Issue , 2017, Pages 223-240

  Karas, Daniel ^a   Ulrichová, Jitka ^a   Valentová, Kateřina ^b  

^a PALACKÝ UNIVERSITY   (Czech Republic)

^b INSTITUTE OF MATHEMATICS   (Czech Republic)

Author keywords

Angiogenesis; Gallic acid; Galloylation; Natural gallates; Polyphenols; Synthetic galloyl esters

Indexed keywords

CATECHIN; ELLAGIC ACID; ELLAGITANNIN; EPICATECHIN; EPICATECHIN GALLATE; EPIGALLOCATECHIN; EPIGALLOCATECHIN GALLATE; FLAVONOL; FLAVONOLIGNAN; GLUCOSE PENTAGALLATE; POLYPHENOL; PROANTHOCYANIDIN; SILIBININ; TANNIN; THEAFLAVIN;

ANALYTIC METHOD; ANGIOGENESIS; ANTIOXIDANT ACTIVITY; APOPTOSIS; BIOLOGICAL ACTIVITY; CELL ADHESION; CELL MIGRATION; CHEMICAL STRUCTURE; GALLOYLATION; MITOGENESIS; REVIEW; SILYBUM MARIANUM; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; HUMAN;

ANIMALS; CATECHIN; HUMANS; POLYPHENOLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85018579633     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2017.04.021     Document Type: Review

References (255)

1. Actis-Goretta, L., Romanczyk, L.J., Rodriguez, C.A., Kwik-Uribe, C., Keen, C.L., Cytotoxic effects of digalloyl dimer procyanidins in human cancer cell lines. J. Nutr. Biochem. 19 (2008), 797–808, 10.1016/j.jnutbio.2007.10.004.
2. Agarwal, C., Veluri, R., Kaur, M., Chou, S.C., Thompson, J.A., Agarwal, R., Fractionation of high molecular weight tannins in grape seed extract and identification of procyanidin B2-3,3'-di-O-gallate as a major active constituent causing growth inhibition and apoptotic death of DU145 human prostate carcinoma cells. Carcinogenesis 28 (2007), 1478–1484, 10.1093/carcin/bgm045.
3. Agarwal, C., Wadhwa, R., Deep, G., Biedermann, D., Gažák, R., Křen, V., Agarwal, R., Anti-cancer efficacy of silybin derivatives – a structure-activity relationship. PLoS One, 8, 2013, e60074, 10.1371/journal.pone.0060074.
4. Agarwal, R., Agarwal, C., Ichikawa, H., Singh, R.P., Aggarwal, B.B., Anticancer potential of silymarin: from bench to bed side. Anticancer Res. 26 (2006), 4457–4498.
5. Alzoubi, K., Honisch, S., Abed, M., Lang, F., Triggering of suicidal erythrocyte death by penta-O-galloyl-beta-D-glucose. Toxins 6 (2014), 54–65, 10.3390/toxins6010054.
6. Amakura, Y., Kawada, K., Hatano, T., Agata, I., Sugaya, T., Nishibe, S., Okuda, T., Yoshida, T., Four new hydrolyzable tannins and an acylated flavonol glycoside from Euphorbia maculata. Can. J. Chem. 75 (1997), 727–733, 10.1139/V97-088.
7. Antonopoulou, I., Varriale, S., Topakas, E., Rova, U., Christakopoulos, P., Faraco, V., Enzymatic synthesis of bioactive compounds with high potential for cosmeceutical application. Appl. Microbiol. Biotechnol. 100 (2016), 6519–6543, 10.1007/s00253-016-7647-9.
8. Ascacio-Valdes, J.A., Buenrostro-Figueroa, J.J., Aguilera-Carbo, A., Prado-Barragan, A., Rodriguez-Herrera, R., Aguilar, C.N., Ellagitannins: biosynthesis, biodegradation and biological properties. J. Med. Plants Res. 5 (2011), 4696–4703.
9. Babich, H., Zuckerbraun, H.L., Weinerman, S.M., In vitro cytotoxicity of (-)-catechin gallate, a minor polyphenol in green tea. Toxicol. Lett. 171 (2007), 171–180, 10.1016/j.toxlet.2007.05.125.
10. Badhani, B., Sharma, N., Kakkar, R., Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications. RSC Adv. 5 (2015), 27540–27557, 10.1039/c5ra01911g.
11. Baratto, M.C., Tattini, M., Galardi, C., Pinelli, P., Romani, A., Visioli, F., Basosi, R., Pogni, R., Antioxidant activity of galloyl quinic derivatives isolated from P. lentiscus leaves. Free Radic. Res. 37 (2003), 405–412 http://dx.doi.org/10.1080/1071576031000068618.
12. Basu, A., Sanchez, K., Leyva, M.J., Wu, M., Betts, N.M., Aston, C.E., Lyons, T.J., Green tea supplementation affects body weight, lipids, and lipid peroxidation in syndrome. J. Am. Coll. Nutr. 29 (2010), 31–40 http://dx.doi.org/10.1080/07315724.2010.10719814.
13. Baxter, N.J., Lilley, T.H., Haslam, E., Williamson, M.P., Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation. Biochemistry 36 (1997), 5566–5577, 10.1021/bi9700328.
14. Berciano, S., Ordovas, J.M., Nutrition and cardiovascular health. Rev. Esp. Cardiol. Engl. Ed. 67 (2014), 738–747, 10.1016/j.rec.2014.05.003.
15. Bernhaus, A., Fritzer-Szekeres, M., Grusch, M., Saiko, P., Krupitza, G., Venkateswarlu, S., Trimurtulu, G., Jaeger, W., Szekeres, T., Digalloylresveratrol, a new phenolic acid derivative induces apoptosis and cell cycle arrest in human HT-29 colon cancer cells. Cancer Lett. 274 (2009), 299–304, 10.1016/j.canlet.2008.09.020.
16. Bettuzzi, S., Brausi, M., Rizzi, F., Castagnetti, G., Peracchia, G., Corti, A., Chemoprevention of human prostate cancer by oral administration of green tea catechins in volunteers with high-grade prostate intraepithelial neoplasia: a preliminary report from a one-year proof-of-principle study. Cancer Res. 66 (2006), 1234–1240, 10.1158/0008-5472.can-05-1145.
17. Bhadoriya, U., Sharma, P., Solanki, S.S., In vitro free radical scavenging activity of gallic acid isolated from Caesalpinia decapetala wood. Asian Pac. J. Trop. Dis. 2 (2012), S833–S836, 10.1016/S2222-1808(12)60274-6.
18. Bibby, M.C., Combretastatin anticancer drugs. Drugs Future 27 (2002), 475–480, 10.1358/dof.2002.027.05.668645.
19. Boots, A.W., Haenen, G.R.M.M., Bast, A., Health effects of quercetin: from antioxidant to nutraceutical. Eur. J. Pharmacol. 585 (2008), 325–337, 10.1016/j.ejphar.2008.03.008.
20. Borges, G., Roowi, S., Rouanet, J.M., Duthie, G.G., Lean, M.E.J., Crozier, A., The bioavailability of raspberry anthocyanins and ellagitannins in rats. Mol. Nutr. Food Res. 51 (2007), 714–725, 10.1002/mnfr.200700024.
21. Bowsher, C., Steer, M., Tobin, A., Plant Biochemistry. Garland Science. 2008, Taylor & Francis Group, New York & Abigdon.
22. Bozorgi, M., Memariani, Z., Mobli, M., Salehi Surmaghi, M.H., Shams-Ardekani, M.R., Rahimi, R., Five Pistacia species (P. vera, P. atlantica, P. terebinthus, P. khinjuk, and P. lentiscus): a review of their traditional uses, phytochemistry, and pharmacology. ScientificWorldJournal, 2013, 2013, 219815, 10.1155/2013/219815.
23. Butt, M.S., Imran, A., Sharif, M.K., Ahmad, R.S., Xiao, H., Imran, M., Rsool, H.A., Black tea polyphenols: a mechanistic treatise. Crit. Rev. Food Sci. Nutr. 54 (2014), 1002–1011, 10.1080/10408398.2011.623198.
24. Cao, Z.X., Li, Y.B., Potent induction of cellular antioxidants and phase 2 enzymes by resveratrol in cardiomyocytes: protection against oxidative and electrophilic injury. Eur. J. Pharmacol. 489 (2004), 39–48, 10.1016/j.cjphar.2004.02.031.
25. Caturla, N., Vera-Samper, E., Villalain, J., Mateo, C.R., Micol, V., The relationship between the antioxidant and the antibacterial properties of galloylated catechins and the structure of phospholipid model membranes. Free Radic. Bio. Med. 34 (2003), 648–662, 10.1016/S0891-5849(02)1366-7.
26. Chai, Y., Lee, H.J., Shaik, A.A., Nkhata, K., Xing, C., Zhang, J., Jeong, S.J., Kim, S.H., Lu, J., Penta-O-galloyl-beta-D-glucose induces G1 arrest and DNA replicative S-phase arrest independently of cyclin-dependent kinase inhibitor 1A, cyclin-dependent kinase inhibitor 1B and P53 in human breast cancer cells and is orally active against triple negative xenograft growth. Breast Cancer Res., 12, 2010, R67, 10.1186/bcr2634.
27. Chavez, J.H., Leal, P.C., Yunes, R.A., Nunes, R.J., Barardi, C.R., Pinto, A.R., Simoes, C.M., Zanetti, C.R., Evaluation of antiviral activity of phenolic compounds and derivatives against rabies virus. Vet. Microbiol. 116 (2006), 53–59, 10.1016/j.vetmic.2006.03.019.
28. Chen, A., Zhang, L., The antioxidant (-)-epigallocatechin-3-gallate inhibits rat hepatic stellate cell proliferation in vitro by blocking the tyrosine phosphorylation and reducing the gene expression of platelet-derived growth factor-beta receptor. J. Biol. Chem. 278 (2003), 23381–23389, 10.1074/jbc.M212042200.
29. Chen, C.H., Chen, P.Y., Lee, C.K., Rapid identification of the antioxidant constituent of Koelreuteria henryi. J. Chin. Chem. Soc. 57 (2010), 404–410 http://dx.doi.org/10.1002/jccs.201000060.
30. Chen, H.D., Hayek, S., Guzman, J.R., Gillitt, N.D., Ibrahim, S.A., Jobin, C., Sang, S.M., The microbiota is essential for the generation of black tea theaflavins-derived metabolites. PLoS One, 7, 2012, 10, 10.1371/journal.pone.0051001.
31. Chen, Y., Hagerman, A.E., Reaction pH and protein affect the oxidation products of beta-pentagalloyl glucose. Free Radic. Res. 39 (2005), 117–124, 10.1080/10715760400013789.
32. Chia, Y.C., Rajbanshi, R., Calhoun, C., Chiu, R.H., Anti-neoplastic effects of gallic acid, a major component of Toona sinensis leaf extract, on oral squamous carcinoma cells. Molecules 15 (2010), 8377–8389, 10.3390/molecules15118377.
33. Chiang, L.C., Chiang, W., Chang, M.Y., Ng, L.T., Lin, C.C., Antiviral activity of Plantago major extracts and related compounds in vitro. Antivir. Res. 55 (2002), 53–62, 10.1016/S0166-3542(02)00007-4.
34. Chira, K., Schmauch, G., Saucier, C., Fabre, S., Teissedre, P.L., Grape variety effect on proanthocyanidin composition and sensory perception of skin and seed tannin extracts from bordeaux wine grapes (Cabernet Sauvignon and Merlot) for two consecutive vintages (2006 and 2007). J. Agric. Food Chem. 57 (2009), 545–553, 10.1021/jf802301g.
35. Chung, K.-T., Wei, C.-I., Johnson, M.G., Are tannins a double-edged sword in biology and health?. Trends Food Sci. Technol. 9 (1998), 168–175, 10.1016/S0924-2244(98)00028-4.
36. Chyu, K.Y., Babbidge, S.M., Zhao, X., Dandillaya, R., Rietveld, A.G., Yano, J., Dimayuga, P., Cercek, B., Shah, P.K., Differential effects of green tea-derived catechin on developing versus established atherosclerosis in apolipoprotein E-null mice. Circulation 109 (2004), 2448–2453, 10.1161/01.CIR.0000128034.70732.C2.
37. Clifford, M.N., Scalbert, A., Ellagitannins – nature, occurrence and dietary burden. J. Sci. Food Agric. 80 (2000), 1118–1125, 10.1002/(SICI)1097-0010(20000515)80 7<1118::AID-JSFA570>3.0.CO;2–9.
38. Clifford, M.N., Stoupi, S., Kuhnert, N., Profiling and characterization by LC-MSn of the galloylquinic acids of green tea, tara tannin, and tannic acid. J. Agric. Food Chem. 55 (2007), 2797–2807, 10.1021/jf063533l.
39. Clifford, M.N., van der Hooft, J.J.J., Crozier, A., Human studies on the absorption, distribution, metabolism, and excretion of tea polyphenols. Am. J. Clin. Nutr. 98 (2013), 1619S–1630S, 10.3945/ajcn.113.058958.
40. Colon, M., Nerin, C., Synergistic, antagonistic and additive interactions of green tea polyphenols. Eur. Food Res. Technol. 242 (2016), 211–220, 10.1007/s00217-015-2532-9.
41. Cook, K.M., Figg, W.D., Angiogenesis inhibitors: current strategies and future prospects. CA Cancer J. Clin. 60 (2010), 222–243, 10.3322/caac.20075.
42. Danesi, F., Kroon, P.A., Saha, S., de Biase, D., D'Antuono, L.F., Bordoni, A., Mixed pro- and anti-oxidative effects of pomegranate polyphenols in cultured cells. Int. J. Mol. Sci. 15 (2014), 19458–19471, 10.3390/ijms151119458.
43. Dell'Eva, R., Pfeffer, U., Vene, R., Anfosso, L., Forlani, A., Albini, A., Efferth, T., Inhibition of angiogenesis in vivo and growth of Kaposi's sarcoma xenograft tumors by the anti-malarial artesunate. Biochem. Pharmacol. 68 (2004), 2359–2366, 10.1016/j.bcp.2004.08.021.
44. Dorsch, W., Bittinger, M., Kaas, A., Muller, A., Kreher, B., Wagner, H., Antiasthmatic effects of Galphimia glauca, gallic acid, and related compounds prevent allergen- and platelet-activating factor-induced bronchial obstruction as well as bronchial hyperreactivity in Guinea pigs. Int. Arch. Allergy Immunol. 97 (1992), 1–7, 10.1159/000236088.
45. Duluc, L., Jacques, C., Soleti, R., Andriantsitohaina, R., Simard, G., Delphinidin inhibits VEGF induced-mitochondrial biogenesis and Akt activation in endothelial cells. Int. J. Biochem. Cell Biol. 53 (2014), 9–14, 10.1016/j.biocel.2014.03.030.
46. Eng, E.T., Ye, J., Williams, D., Phung, S., Moore, R.E., Young, M.K., Gruntmanis, U., Braunstein, G., Chen, S., Suppression of estrogen biosynthesis by procyanidin dimers in red wine and grape seeds. Cancer Res. 63 (2003), 8516–8522.
47. Erlejman, A.G., Fraga, C.G., Oteiza, P.I., The interaction of flavonoids with membranes: potential determinant of flavonoid antioxidant effects. Free Radic. Res. 38 (2004), 1311–1320, 10.1080/10715760400016105.
48. Ersan, S., Guclu Ustundag, O., Carle, R., Schweiggert, R.M., Identification of phenolic compounds in red and green pistachio (Pistacia vera L.) hulls (exo- and mesocarp) by HPLC-DAD-ESI-(HR)-MS(n). J. Agric. Food Chem. 64 (2016), 5334–5344, 10.1021/acs.jafc.6b01745.
49. Espin, J.C., Gonzalez-Barrio, R., Cerda, B., Lopez-Bote, C., Rey, A.I., Tomas-Barberan, F.A., Iberian pig as a model to clarify obscure points in the bioavailability and metabolism of ellagitannins in humans. J. Agr. Food Chem. 55 (2007), 10476–10485, 10.1021/jf0723864.
50. Espin, J.C., Larrosa, M., Garcia-Conesa, M.T., Tomas-Barberan, F., Biological significance of urolithins, the gut microbial ellagic acid-derived metabolites: the evidence so far. Evid.-Based Compl. Alt., 2013, 10.1155/2013/270418.
51. Faria, A., Calhau, C., de Freitas, V., Mateus, N., Procyanidins as antioxidants and tumor cell growth modulators. J. Agric. Food Chem. 54 (2006), 2392–2397, 10.1021/jf0526487.
52. FDA, revised 2016. Code of Federal Regulations Title 21. Chapter I-Food and Drug Administration, Department of Health and Human Services. Subchapter B-Food for human consumption, Part 184 – Direct food substances affirmed as generally recognized as safe, Subpart B–Listing of specific substances affirmed as GRAS, Sec. 184.1097 Tannic acid. 21CFR184.1097.
53. Feldman, K.S., Sahasrabudhe, K., Lawlor, M.D., Wilson, S.L., Lang, C.H., Scheuchenzuber, W.J., In vitro and in vivo inhibition of LPS-stimulated tumor necrosis factor-alpha secretion by the gallotannin beta-D-pentagalloylglucose. Bioorg. Med. Chem. Lett. 11 (2001), 1813–1815, 10.1016/S0960-894x(01)00332-8.
54. Feldman, K.S., Sahasrabudhe, K., Smith, R.S., Scheuchenzuber, W.J., Immunostimulation by plant polyphenols: a relationship between tumor necrosis factor-alpha production and tannin structure. Bioorg. Med. Chem. Let. 9 (1999), 985–990, 10.1016/S0960-894x(99)00110-9.
55. Feng, W., Cherednichenko, G., Ward, C.W., Padilla, I.T., Cabrales, E., Lopez, J.R., Eltit, J.M., Allen, P.D., Pessah, I.N., Green tea catechins are potent sensitizers of ryanodine receptor type 1 (RyR1). Biochem. Pharmacol. 80 (2010), 512–521, 10.1016/j.bcp.2010.05.004.
56. Folkman, J., Tumor angiogenesis: therapeutic implications. N. Engl. J. Med. 285 (1971), 1182–1186, 10.1056/NEJM197111182852108.
57. Folkman, J., Shing, Y., Angiogenesis. J. Biol. Chem. 267 (1992), 10931–10934.
58. Gao, D.F., Xu, M., Yang, C.R., Xu, M., Zhang, Y.J., Phenolic antioxidants from the leaves of Camellia pachyandra Hu. J. Agric. Food. Chem. 58 (2010), 8820–8824, 10.1021/jf101490r.
59. Gao, M., Chen, C., Fan, A., Zhang, J., Kong, D., Wang, Z., Zhao, Y., Covalent and non-covalent curcumin loading in acid-responsive polymeric micellar nanocarriers. Nanotechnology, 26, 2015, 275101, 10.1088/0957-4484/26/27/275101.
60. Gažák, R., Svobodová, A., Psotová, J., Sedmera, P., Přikrylová, V., Walterová, D., Křen, V., Oxidised derivatives of silybin and their antiradical and antioxidant activity. Bioorg. Med. Chem. 12 (2004), 5677–5687, 10.1016/j.bmc.2004.07.064.
61. Gažák, R., Valentová, K., Fuksová, K., Marhol, P., Kuzma, M., Medina, M.A., Oborná, I., Ulrichová, J., Křen, V., Synthesis and antiangiogenic activity of new silybin galloyl esters. J. Med. Chem. 54 (2011), 7397–7407, 10.1021/Jm201034h.
62. Gažák, R., Walterová, D., Křen, V., Silybin and silymarin–new and emerging applications in medicine. Curr. Med. Chem. 14 (2007), 315–338, 10.2174/092986707779941159.
63. Gonzalez-Abuin, N., Martinez-Micaelo, N., Margalef, M., Blay, M., Arola-Arnal, A., Muguerza, B., Ardevol, A., Pinent, M., A grape seed extract increases active glucagon-like peptide-1 levels after an oral glucose load in rats. Food Funct. 5 (2014), 2357–2364, 10.1039/c4fo00447g.
64. Gonzalez-Barrio, R., Truchado, P., Ito, H., Espin, J.C., Tomas-Barberan, F.A., UV and MS identification of urolithins and nasutins, the bioavailable metabolites of ellagitannins and ellagic acid in different mammals. J. Agr. Food Chem. 59 (2011), 1152–1162, 10.1021/jf103894m.
65. Gorlach, S., Fichna, J., Lewandowska, U., Polyphenols as mitochondria-targeted anticancer drugs. Cancer Lett. 366 (2015), 141–149, 10.1016/j.canlet.2015.07.004.
66. Gorlach, S., Wagner, W., Podsedek, A., Szewczyk, K., Koziolkiewicz, M., Dastych, J., Procyanidins from Japanese quince (Chaenomeles japonica) fruit induce apoptosis in human colon cancer Caco-2 cells in a degree of polymerization-dependent manner. Nutr. Cancer 63 (2011), 1348–1360, 10.1080/01635581.2011.608480.
67. Goss, R.J.M., Shankar, S., Abou Fayad, A., The generation of “unNatural” products: synthetic biology meets synthetic chemistry. Nat. Prod. Rep. 29 (2012), 870–889, 10.1039/C2np00001f.
68. Gottlieb, O.R., Kaplan, M.A.C., Kubitzki, K., A suggested role of galloyl esters in the evolution of dicotyledons. Taxon 42 (1993), 539–552, 10.2307/1222533.
69. Grasser, G., Synthetic Tannins. Their Synthesis, Industrial Production and Application. 1922, Crosby Lockwood and Son, London.
70. Griffioen, A.W., Molema, G., Angiogenesis: potentials for pharmacologic intervention in the treatment of cancer, cardiovascular diseases, and chronic inflammation. Pharmacol. Rev. 52 (2000), 237–268.
71. Gupta, S.C., Kim, J.H., Prasad, S., Aggarwal, B.B., Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals. Cancer Metastasis Rev. 29 (2010), 405–434, 10.1007/s10555-010-9235-2.
72. Gust, J., Wawer, I., Relationship between radical scavenging effects and anticorrosive properties of polyphenols. Corrosion 51 (1995), 37–44, 10.5006/1.3293574.
73. Gyemant, G., Zajacz, A., Becsi, B., Ragunath, C., Ramasubbu, N., Erdodi, F., Batta, G., Kandra, L., Evidence for pentagalloyl glucose binding to human salivary alpha-amylase through aromatic amino acid residues. Biochim. Biophys. Acta 1794 (2009), 291–296, 10.1016/j.bbapap.2008.10.012.
74. Hagerman, A.E., Riedl, K.M., Rice, R.E., Tannins as biological antioxidants. Basic Life Sci. 66 (1999), 495–505, 10.1007/978-1-4615-4139-4_27.
75. Haslam, E., 22nd Procter memorial lecture Vegetable tannins - renaissance and reappraisal. J. Soc. Leath. Tech. Ch. 72 (1988), 45–64.
76. Hassan, L.E.A., Ahamed, M.B.K., Majid, A.S.A., Baharetha, H.M., Muslim, N.S., Nassar, Z.D., Majid, A.M.S.A., Correlation of antiangiogenic, antioxidant and cytotoxic activities of some Sudanese medicinal plants with phenolic and flavonoid contents. BMC Complem. Altern., 2014, 10.1186/1472-6882-14-406 M. 14.
77. Heim, K.E., Tagliaferro, A.R., Bobilya, D.J., Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J. Nutr. Biochem. 13 (2002), 572–584, 10.1016/S0955-2863(02)00208-5.
78. Ho, Y.-C., Yang, S.-F., Peng, C.-Y., Chou, M.-Y., Chang, Y.-C., Epigallocatechin-3-gallate inhibits the invasion of human oral cancer cells and decreases the productions of matrix metalloproteinases and urokinase-plasminogen activator. J. Oral Pathol. Med. 36 (2007), 588–593, 10.1111/j.1600-0714.2007.00588.x.
79. Hofmann, T., Glabasnia, A., Schwarz, B., Wisman, K.N., Gangwer, K.A., Hagerman, A.E., Protein binding and astringent taste of a polymeric procyanidin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose, castalagin, and grandinin. J. Agric. Food Chem. 54 (2006), 9503–9509, 10.1021/jf062272c.
80. Honda, N.K., Vilegas, W., The chemistry of lichens. Quimica Nova 22 (1999), 110–125, 10.1590/s0100-40421999000100018.
81. Hsieh, S.R., Cheng, W.C., Su, Y.M., Chiu, C.H., Liou, Y.M., Molecular targets for anti-oxidative protection of green tea polyphenols against myocardial ischemic injury. Biomed. (Taipei), 4, 2014, 23, 10.7603/s40681-014-0023-0.
82. Hsu, J.D., Kao, S.H., Ou, T.T., Chen, Y.J., Li, Y.J., Wang, C.J., Gallic acid induces G2/M phase arrest of breast cancer cell MCF-7 through stabilization of p27(Kip1) attributed to disruption of p27(Kip1)/Skp2 complex. J. Agric. Food Chem. 59 (2011), 1996–2003, 10.1021/jf103656v.
83. Hsu, S., Compounds derived from epigallocatechin-3-gallate (EGCG) as a novel approach to the prevention of viral infections. Inflamm. Allergy Drug Targets 14 (2015), 13–18, 10.2174/1871528114666151022150122.
84. Hu, H.B., Zhang, J.H., Lee, H.J., Kim, S.H., Lu, J.X., Penta-O-galloyl-beta-D-glucose induces S- and G(1)-cell cycle arrests in prostate cancer cells targeting DNA replication and cyclin D1. Carcinogenesis 30 (2009), 818–823, 10.1093/carcin/bgp059.
85. Huang, W.Y., Cai, Y.Z., Zhang, Y.B., Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention. Nutr. Cancer 62 (2010), 1–20, 10.1080/01635580903191585.
86. Huang, Y.L., Tsujita, T., Tanaka, T., Matsuo, Y., Kouno, I., Li, D.P., Nonaka, G., Triterpene hexahydroxydiphenoyl esters and a quinic acid purpurogallin carbonyl ester from the leaves of Castanopsis fissa. Phytochemistry 72 (2011), 2006–2014, 10.1016/j.phytochem.2011.07.007.
87. Huber, A., Thongphasuk, P., Erben, G., Lehmann, W.D., Tuma, S., Stremmel, W., Chamulitrat, W., Significantly greater antioxidant anticancer activities of 2,3-dehydrosilybin than silybin. BBA-Gen. Subjects 1780 (2008), 837–847, 10.1016/j.bbagen.2007.12.012.
88. Huh, J.E., Lee, E.O., Kim, M.S., Kang, K.S., Kim, C.H., Cha, B.C., Surh, Y.J., Kim, S.H., Penta-O-galloyl-beta-D-glucose suppresses tumor growth via inhibition of angiogenesis and stimulation of apoptosis: roles of cyclooxygenase-2 and mitogen-activated protein kinase pathways. Carcinogenesis 26 (2005), 1436–1445, 10.1093/carcin/bgi097.
89. Hussain, S., Schonbichler, S.A., Guzel, Y., Sonderegger, H., Abel, G., Rainer, M., Huck, C.W., Bonn, G.K., Solid-phase extraction of galloyl- and caffeoylquinic acids from natural sources (Galphimia glauca and Arnicae flos) using pure zirconium silicate and bismuth citrate powders as sorbents inside micro spin columns. J. Pharm. Biomed. Anal. 84 (2013), 148–158, 10.1016/j.jpba.2013.05.029.
90. Hussein, A., Gomez, B., Ramos, M., Heller, M., Coley, P., Solis, P., Gupta, M., Constituents of Hiraea reclinata and their anti-HIV activity. Rev. Latinoam. Quím. 31 (2003), 74–77.
91. Iglesias, J., Pazos, M., Lois, S., Medina, I., Contribution of galloylation and polymerization to the antioxidant activity of polyphenols in fish lipid systems. J. Agr. Food Chem. 58 (2010), 7423–7431, 10.1021/Jf100832z.
92. Ikeda, I., Multifunctional effects of green tea catechins on prevention of the metabolic syndrome. Asia Pac. J. Clin. Nutr. 17:Suppl. 1 (2008), 273–274, 10.6133/apjcn.2008.17.s1.65.
93. Ikeda, I., Tsuda, K., Suzuki, Y., Kobayashi, M., Unno, T., Tomoyori, H., Goto, H., Kawata, Y., Imaizumi, K., Nozawa, A., Kakuda, T., Tea catechins with a galloyl moiety suppress postprandial hypertriacylglycerolemia by delaying lymphatic transport of dietary fat in rats. J. Nutr. 135 (2005), 155–159.
94. Inoue, M., Sakaguchi, N., Isuzugawa, K., Tani, H., Ogihara, Y., Role of reactive oxygen species in gallic acid-induced apoptosis. Biol. Pharm. Bull. 23 (2000), 1153–1157 http://doi.org/10.1248/bpb.23.1153.
95. Iwashina, T., The structure and distribution of the flavonoids in plants. J. Plant Res. 113 (2000), 287–299, 10.1007/pl00013940.
96. Jana, A., Halder, S.K., Banerjee, A., Paul, T., Pati, B.R., Mondal, K.C., Das Mohapatra, P.K., Biosynthesis, structural architecture and biotechnological potential of bacterial tannase: a molecular advancement. Bioresour. Technol. 157 (2014), 327–340, 10.1016/j.biortech.2014.02.017.
97. Jatoi, A., Ellison, N., Burch, P.A., Sloan, J.A., Dakhil, S.R., Novotny, P., Tan, W., Fitch, T.R., Rowland, K.M., Young, C.Y., Flynn, P.J., A phase II trial of green tea in the treatment of patients with androgen independent metastatic prostate carcinoma. Cancer 97 (2003), 1442–1446, 10.1002/cncr.11200.
98. Jiang, X., Liu, Y., Li, W., Zhao, L., Meng, F., Wang, Y., Tan, H., Yang, H., Wei, C., Wan, X., Gao, L., Xia, T., Tissue-specific, development-dependent phenolic compounds accumulation profile and gene expression pattern in tea plant [Camellia sinensis]. PLoS One, 8, 2013, e62315, 10.1371/journal.pone.0062315.
99. Jiang, X., Liu, Y., Wu, Y., Tan, H., Meng, F., Wang, Y.S., Li, M., Zhao, L., Liu, L., Qian, Y., Gao, L., Xia, T., Analysis of accumulation patterns and preliminary study on the condensation mechanism of proanthocyanidins in the tea plant [Camellia sinensis]. Sci. Rep., 5, 2015, 8742, 10.1038/srep08742.
100. Jimenez, N., Esteban-Torres, M., Mancheno, J.M., de Las Rivas, B., Munoz, R., Tannin degradation by a novel tannase enzyme present in some Lactobacillus plantarum strains. Appl. Environ. Microbiol. 80 (2014), 2991–2997, 10.1128/aem.00324-14.
101. Jurgens, T.M., Whelan, A.M., Killian, L., Doucette, S., Kirk, S., Foy, E., Green tea for weight loss and weight maintenance in overweight or obese adults. Cochrane Database Syst. Rev., 12, 2012, CD008650, 10.1002/14651858.CD008650.pub2.
102. Kadota, S., Takamori, Y., Nyein, K.N., Kikuchi, T., Tanaka, K., Ekimoto, H., Constituents of the leaves of Woodfordia fruticosa Kurz. I. Isolation, structure, and proton and carbon-13 nuclear magnetic resonance signal assignments of woodfruticosin (woodfordin C), an inhibitor of deoxyribonucleic acid topoisomerase II. Chem. Pharm. Bull. (Tokyo) 38 (1990), 2687–2697 http://doi.org/10.1248/cpb.38.2687.
103. Kajimoto, O., Kajimoto, Y., Yabune, M., Nakamura, T., Kotani, K., Suzuki, Y., Nozawa, A., Nagata, K., Unno, T., Sagesaka, Y.M., Kakuda, T., Yoshikawa, T., Tea catechins with a galloyl moiety reduce body weight and fat. J. Health Sci. 51 (2005), 161–171, 10.1248/jhs.51.161.
104. Kakumu, A., Ninomiya, M., Efdi, M., Adfa, M., Hayashi, M., Tanaka, K., Koketsu, M., Phytochemical analysis and antileukemic activity of polyphenolic constituents of Toona sinensis. Bioorg. Med. Chem. Lett. 24 (2014), 4286–4290, 10.1016/j.bmcl.2014.07.022.
105. Kandra, L., Gyemant, G., Zajacz, A., Batta, G., Inhibitory effects of tannin on human salivary alpha-amylase. Biochem. Bioph. Res. Co. 319 (2004), 1265–1271, 10.1016/j.bbrc.2004.05.122.
106. Kang, D.G., Moon, M.K., Choi, D.H., Lee, J.K., Kwon, T.O., Lee, H.S., Vasodilatory and anti-inflammatory effects of the 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (PGG) via a nitric oxide-cGMP pathway. Eur. J. Pharmacol. 524 (2005), 111–119, 10.1016/j.ejphar.2005.08.061.
107. Karas, D., Gažák, R., Valentová, K., Chambers, C.S., Pivodová, V., Biedermann, D., Křenková, A., Oborná, I., Kuzma, M., Cvačka, J., Ulrichová, J., Křen, V., Effects of 2,3-dehydrosilybin and its galloyl ester and methyl ether derivatives on human umbilical vein endothelial cells. J. Nat. Prod. 79 (2016), 812–820, 10.1021/acs.jnatprod.5b00905.
108. Kato, K., Ninomiya, M., Tanaka, K., Koketsu, M., Effects of functional groups and sugar composition of quercetin derivatives on their radical scavenging properties. J. Nat. Prod. 79 (2016), 1808–1814, 10.1021/acs.jnatprod.6b00274.
109. Kennedy, D.O., Wightman, E.L., Herbal extracts and phytochemicals: plant secondary metabolites and the enhancement of human brain function. Adv. Nutr. 2 (2011), 32–50, 10.3945/an.110.000117.
110. Kerbel, R.S., Inhibition of tumor angiogenesis as a strategy to circumvent acquired resistance to anti-cancer therapeutic agents. Bioessays 13 (1991), 31–36, 10.1002/bies.950130106.
111. Kilani-Jaziri, S., Neffati, A., Limem, I., Boubaker, J., Skandrani, I., Sghair, M.B., Bouhlel, I., Bhouri, W., Mariotte, A.M., Ghedira, K., Dijoux Franca, M.G., Chekir-Ghedira, L., Relationship correlation of antioxidant and antiproliferative capacity of Cyperus rotundus products towards K562 erythroleukemia cells. Chem. Biol. Interact. 181 (2009), 85–94, 10.1016/j.cbi.2009.04.014.
112. Kim, H.P., Son, K.H., Chang, H.W., Kang, S.S., Anti-inflammatory plant flavonoids and cellular action mechanisms. J. Pharmacol. Sci. 96 (2004), 229–245 http://doi.org/10.1254/jphs.CRJ04003X.
113. Kim, H.S., Montana, V., Jang, H.J., Parpura, V., Kim, J.A., Epigallocatechin gallate (EGCG) stimulates autophagy in vascular endothelial cells: a potential role for reducing lipid accumulation. J. Biol. Chem. 288 (2013), 22693–22705, 10.1074/jbc.M113.477505.
114. Kim, H.S., Quon, M.J., Kim, J.A., New insights into the mechanisms of polyphenols beyond antioxidant properties; lessons from the green tea polyphenol, epigallocatechin 3-gallate. Redox Biol. 2 (2014), 187–195, 10.1016/j.redox.2013.12.022.
115. Kim, J.A., Mechanisms underlying beneficial health effects of tea catechins to improve insulin resistance and endothelial dysfunction. Endocr. Metab. Immune Disord. Drug Targets 8 (2008), 82–88 http://doi.org/10.2174/187153008784534349.
116. Kim, J.A., Formoso, G., Li, Y., Potenza, M.A., Marasciulo, F.L., Montagnani, M., Quon, M.J., Epigallocatechin gallate, a green tea polyphenol, mediates NO-dependent vasodilation using signaling pathways in vascular endothelium requiring reactive oxygen species and Fyn. J. Biol. Chem. 282 (2007), 13736–13745, 10.1074/jbc.M609725200.
117. Kiss, A., Becsi, B., Kolozsvari, B., Komaromi, I., Kover, K.E., Erdodi, F., Epigallocatechin-3-gallate and penta-O-galloyl-beta-D-glucose inhibit protein phosphatase-1. FEBS J. 280 (2013), 612–626, 10.1111/j.1742-4658.2012.08498.x.
118. Kobayashi, M., Ichitani, M., Suzuki, Y., Unno, T., Sugawara, T., Yamahira, T., Kato, M., Takihara, T., Sagesaka, Y., Kakuda, T., Ikeda, I., Black-tea polyphenols suppress postprandial hypertriacylglycerolemia by suppressing lymphatic transport of dietary fat in rats. J. Agr. Food Chem. 57 (2009), 7131–7136, 10.1021/jf900855v.
119. Kondo, T., Ohta, T., Igura, K., Hara, Y., Kaji, K., Tea catechins inhibit angiogenesis in vitro, measured by human endothelial cell growth, migration and tube formation, through inhibition of VEGF receptor binding. Cancer Lett. 180 (2002), 139–144 (doi).
120. Krook, M.A., Hagerman, A.E., Stability of polyphenols epigallocatechin gallate and pentagalloyl glucose in a simulated digestive system. Food Res. Int. 49 (2012), 112–116, 10.1016/j.foodres.2012.08.004.
121. Kumazoe, M., Sugihara, K., Tsukamoto, S., Huang, Y., Tsurudome, Y., Suzuki, T., Suemasu, Y., Ueda, N., Yamashita, S., Kim, Y., Yamada, K., Tachibana, H., 67-kDa laminin receptor increases cGMP to induce cancer-selective apoptosis. J. Clin. Invest. 123 (2013), 787–799, 10.1172/JCI64768.
122. Kuntz, S., Rudloff, S., Asseburg, H., Borsch, C., Frohling, B., Unger, F., Dold, S., Spengler, B., Rompp, A., Kunz, C., Uptake and bioavailability of anthocyanins and phenolic acids from grape/blueberry juice and smoothie in vitro and in vivo. Br. J. Nutr. 113 (2015), 1044–1055, 10.1017/S0007114515000161.
123. Kwon, T.-R., Lee, M.h., Jeong, S.J., Sohn, E.J., Lee, D., Shin, E.A., Lee, H.-J., Lee, E.-O., Jung, J.H., Kim, J.-H., Jung, D.-B., Kim, S.-H., Penta-O-galloyl-beta-D-glucose enhances antitumor activity of imatinib and suppresses the growth of K562 cells in mice. Afr. J. Pharm. Pharmacol. 7 (2013), 552–559, 10.5897/AJPP12.1058.
124. Lamoral-Theys, D., Pottier, L., Kerff, F., Dufrasne, F., Proutiere, F., Wauthoz, N., Neven, P., Ingrassia, L., Van Antwerpen, P., Lefranc, F., Gelbcke, M., Pirotte, B., Kraus, J.L., Neve, J., Kornienko, A., Kiss, R., Dubois, J., Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli. Bioorgan. Med. Chem. 18 (2010), 3823–3833, 10.1016/j.bmc.2010.04.047.
125. Lee, H.H., Ho, C.T., Lin, J.K., Theaflavin-3,3'-digallate and penta-O-galloyl-beta-D-glucose inhibit rat liver microsomal 5alpha-reductase activity and the expression of androgen receptor in LNCaP prostate cancer cells. Carcinogenesis 25 (2004), 1109–1118, 10.1093/carcin/bgh106.
126. Lee, M.-J., Maliakal, P., Chen, L., Meng, X., Bondoc, F.Y., Prabhu, S., Lambert, G., Mohr, S., Yang, C.S., Pharmacokinetics of tea catechins after ingestion of green tea and (−)-epigallocatechin-3-gallate by humans. Cancer Epidemiol. Biomarkers. Prev. 11 (2002), 1025–1032.
127. Lee, S.J., Lee, H.K., Jung, M.K., Mar, W., In vitro antiviral activity of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose against hepatitis B virus. Biol. Pharm. Bull. 29 (2006), 2131–2134, 10.1248/bpb.29.2131.
128. Leung, L.K., Su, Y., Chen, R., Zhang, Z., Huang, Y., Chen, Z.Y., Theaflavins in black tea and catechins in green tea are equally effective antioxidants. J. Nutr. 131 (2001), 2248–2251.
129. Lewandowska, U., Fichna, J., Gorlach, S., Enhancement of anticancer potential of polyphenols by covalent modifications. Biochem. Pharmacol. 109 (2016), 1–13, 10.1016/j.bcp.2015.12.019.
130. Lewandowska, U., Szewczyk, K., Hrabec, E., Janecka, A., Gorlach, S., Overview of metabolism and bioavailability enhancement of polyphenols. J. Agric. Food Chem. 61 (2013), 12183–12199, 10.1021/jf404439b.
131. Lewandowska, U., Szewczyk, K., Owczarek, K., Hrabec, Z., Podsedek, A., Koziolkiewicz, M., Hrabec, E., Flavanols from Japanese quince (Chaenomeles japonica) fruit inhibit human prostate and breast cancer cell line invasiveness and cause favorable changes in Bax/Bcl-2 mRNA ratio. Nutr. Cancer 65 (2013), 273–285, 10.1080/01635581.2013.749292.
132. Lewandowska, U., Szewczyk, K., Owczarek, K., Hrabec, Z., Podsedek, A., Koziolkiewicz, M., Hrabec, E., Flavanols from evening primrose (Oenothera paradoxa) defatted seeds inhibit prostate cells invasiveness and cause changes in Bcl-2/Bax mRNA ratio. J. Agr. Food Chem. 61 (2013), 2987–2998, 10.1021/Jf304269x.
133. Lewandowska, U., Szewczyk, K., Owczarek, K., Hrabec, Z., Podsedek, A., Sosnowska, D., Hrabec, E., Procyanidins from evening primrose (Oenothera paradoxa) defatted seeds inhibit invasiveness of breast cancer cells and modulate the expression of selected genes involved in angiogenesis, metastasis, and apoptosis. Nutr. Cancer 65 (2013), 1219–1231, 10.1080/01635581.2013.830314.
134. Li, B.H., Ma, X.F., Wang, Y., Tian, W.X., Structure-activity relationship of polyphenols that inhibit fatty acid synthase. J. Biochem. 138 (2005), 679–685, 10.1093/Jb/Mvi171.
135. Li, M., Kai, Y., Qiang, H., Dongying, J., Biodegradation of gallotannins and ellagitannins. J. Basic Microbiol. 46 (2006), 68–84, 10.1002/jobm.200510600.
136. Li, X., Feng, Y., Liu, J., Feng, X., Zhou, K., Tang, X., Epigallocatechin-3-gallate inhibits IGF-I-stimulated lung cancer angiogenesis through downregulation of HIF-1alpha and VEGF expression. J. Nutr. Nutr. 6 (2013), 169–178, 10.1159/000354402.
137. Liang, C.Z., Zhang, X., Li, H., Tao, Y.Q., Tao, L.J., Yang, Z.R., Zhou, X.P., Shi, Z.L., Tao, H.M., Gallic acid induces the apoptosis of human osteosarcoma cells in vitro and in vivo via the regulation of mitogen-activated protein kinase pathways. Cancer Biother. Radiopharm. 27 (2012), 701–710, 10.1089/cbr.2012.1245.
138. Liao, C.L., Lai, K.C., Huang, A.C., Yang, J.S., Lin, J.J., Wu, S.H., Wood, W.G., Lin, J.G., Chung, J.G., Gallic acid inhibits migration and invasion in human osteosarcoma U-2 OS cells through suppressing the matrix metalloproteinase-2/-9, protein kinase B (PKB) and PKC signaling pathways. Food Chem. Toxicol. 50 (2012), 1734–1740, 10.1016/j.fct.2012.02.033.
139. Lin, L., Ni, B., Lin, H., Zhang, M., Li, X., Yin, X., Qu, C., Ni, J., Traditional usages, botany, phytochemistry, pharmacology and toxicology of Polygonum multiflorum Thunb.: a review. J. Ethnopharmacol. 159 (2015), 158–183, 10.1016/j.jep.2014.11.009.
140. Liu, G., Xiong, S., Xiang, Y.F., Guo, C.W., Ge, F., Yang, C.R., Zhang, Y.J., Wang, Y.F., Kitazato, K., Antiviral activity and possible mechanisms of action of pentagalloylglucose (PGG) against influenza A virus. Arch. Virol. 156 (2011), 1359–1369, 10.1007/s00705-011-0989-9.
141. Liu, K.C., Huang, A.C., Wu, P.P., Lin, H.Y., Chueh, F.S., Yang, J.S., Lu, C.C., Chiang, J.H., Meng, M.H., Chung, J.G., Gallic acid suppresses the migration and invasion of PC-3 human prostate cancer cells via inhibition of matrix metalloproteinase-2 and-9 signaling pathways. Oncol. Rep. 26 (2011), 177–184, 10.3892/or.2011.1264.
142. Lizarraga, D., Lozano, C., Briede, J.J., van Delft, J.H., Tourino, S., Centelles, J.J., Torres, J.L., Cascante, M., The importance of polymerization and galloylation for the antiproliferative properties of procyanidin-rich natural extracts. FEBS J. 274 (2007), 4802–4811, 10.1111/j.1742-4658.2007.06010.x.
143. Lizarraga, D., Tourino, S., Reyes-Zurita, F.J., de Kok, T.M., van Delft, J.H., Maas, L.M., Briede, J.J., Centelles, J.J., Torres, J.L., Cascante, M., Witch hazel (Hamamelis virginiana) fractions and the importance of gallate moieties-electron transfer capacities in their antitumoral properties. J. Agr. Food Chem. 56 (2008), 11675–11682, 10.1021/Jf802345x.
144. Lopez-Lazaro, M., Calderon-Montano, J.M., Burgos-Moron, E., Austin, C.A., Green tea constituents (-)-epigallocatechin-3-gallate (EGCG) and gallic acid induce topoisomerase I- and topoisomerase II-DNA complexes in cells mediated by pyrogallol-induced hydrogen peroxide. Mutagenesis 26 (2011), 489–498, 10.1093/mutage/ger006.
145. Ma, Y., Shang, Y., Zhu, D., Wang, C., Zhong, Z., Xu, Z., Facile separation of 5-O-galloylquinic acid from Chinese green tea extract using mesoporous zirconium phosphate. Phytochem. Anal. 27 (2016), 153–157, 10.1002/pca.2610.
146. Madlener, S., Saiko, P., Vonach, C., Viola, K., Stark, N.H.N., Popescu, R., Gridling, M., Vo, N.T.P., Herbacek, I., Davidovits, A., Giessrigl, B., Venkateswarlu, S., Geleff, S., Jager, W., Grusch, M., Kerjaschki, D., Mikulits, W., Golakoti, T., Fritzer-Szekeres, M., Szekeres, T., Krupitza, G., Multifactorial anticancer effects of digalloyl-resveratrol encompass apoptosis, cell-cycle arrest, and inhibition of lymphendothelial gap formation in vitro. Br. J. Cancer 102 (2010), 1361–1370, 10.1038/sj.bjc.6605656.
147. Maestre, R., Pazos, M., Iglesias, J., Medina, I., Capacity of reductants and chelators to prevent lipid oxidation catalyzed by fish hemoglobin. J. Agr. Food Chem. 57 (2009), 9190–9196, 10.1021/jf901727x.
148. Malini, P., Kanchana, G., Rajadurai, M., Antidiabetic efficacy of ellagic acid in streptozotocin-induced diabates mellitus in albino wistar rats. Asian J. Pharm. Clin. Res. 4 (2011), 124–128.
149. Matic, S., Stanic, S., Mihailovic, M., Bogojevic, D., Cotinus coggygria Scop.: an overview of its chemical constituents, pharmacological and toxicological potential. Saudi J. Biol. Sci. 23 (2016), 452–461, 10.1016/j.sjbs.2015.05.012.
150. Maurya, D.K., Nandakumar, N., Devasagayam, T.P.A., Anticancer property of gallic acid in A549, a human lung adenocarcinoma cell line, and possible mechanisms. J. Clin. Biochem. Nutr. 48 (2011), 85–90, 10.3164/jcbn.11-004FR.
151. Mehansho, H., Hagerman, A., Clements, S., Butler, L., Rogler, J., Carlson, D.M., Modulation of proline-rich protein biosynthesis in rat parotid glands by sorghums with high tannin levels. Proc. Natl. Acad. Sci. U. S. A. 80 (1983), 3948–3952 http://doi.org/10.1073/pnas.80.13.3948.
152. Meselhy, M.R., Nakamura, N., Hattori, M., Biotransformation of (-)-epicatechin 3-O-gallate by human intestinal bacteria. Chem. Pharm. Bull. 45 (1997), 888–893, 10.1248/cpb.45.888.
153. Miliauskas, G., van Beek, T.A., Venskutonis, P.R., Linssen, J.P.H., P., d.W, Antioxidative activity of Geranium macrorrhizum. Eur. Food Res. Technol. 218 (2004), 253–261, 10.1007/s00217-003-0836-7.
154. Minami, K., Nakasugi, T., Sun, H.D., Hou, A.J., Ihara, M., Morimoto, M., Komai, K., Isolation and identification of histamine-release inhibitors from Pistacia weinmannifolia J. Pisson ex. Franch. J. Nat. Med. 60 (2006), 138–140, 10.1007/s11418-005-0017-z.
155. Mohan, C.G., Viswanatha, G.L., Savinay, G., Rajendra, C.E., Halemani, P.D., 1,2,3,4,6 Penta-O-galloyl-beta-D-glucose, a bioactivity guided isolated compound from Mangifera indica inhibits 11beta-HSD-1 and ameliorates high fat diet-induced diabetes in C57BL/6 mice. Phytomedicine 20 (2013), 417–426, 10.1016/j.phymed.2012.12.020.
156. Moore, J.P., Westall, K.L., Ravenscroft, N., Farrant, J.M., Lindsey, G.G., Brandt, W.F., The predominant polyphenol in the leaves of the resurrection plant Myrothamnus flabellifolius, 3,4,5 tri-O-galloylquinic acid, protects membranes against desiccation and free radical-induced oxidation. Biochem. J. 385 (2005), 301–308, 10.1042/BJ20040499.
157. Mosele, J.I., Macia, A., Motilva, M.J., Understanding of human metabolic pathways of different sub-classes of phenols from Arbutus unedo fruit after an acute intake. Food Funct. 7 (2016), 1700–1710, 10.1039/c6fo00181e.
158. Mulder, T.P.J., van Platerink, C.J., Wijnand Schuyl, P.J., van Amelsvoort, J.M.M., Analysis of theaflavins in biological fluids using liquid chromatography–electrospray mass spectrometry. J. Chromatogr. B 760 (2001), 271–279, 10.1016/S0378-4347(01)00285-7.
159. Naasani, I., Oh-hashi, F., Oh-hara, T., Feng, W.Y., Johnston, J., Chan, K., Tsuruo, T., Blocking telomerase by dietary polyphenols is a major mechanism for limiting the growth of human cancer cells in vitro and in vivo. Cancer Res. 63 (2003), 824–830 (doi).
160. Nakai, M., Fukui, Y., Asami, S., Toyoda-Ono, Y., Iwashita, T., Shibata, H., Mitsunaga, T., Hashimoto, F., Kiso, Y., Inhibitory effects of oolong tea polyphenols on pancreatic lipase in vitro. J. Agr. Food Chem. 53 (2005), 4593–4598, 10.1021/jf047814+.
161. Neszmelyi, A., Kreher, B., Muller, A., Dorsch, W., Wagner, H., Tetragalloylquinic acid, the major antiasthmatic principle of Galphimia glauca. Planta Med. 59 (1993), 164–167, 10.1055/s-2006-959635.
162. Newman, D.J., Cragg, G.M., Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 75 (2012), 311–335, 10.1021/np200906s.
163. Nishizawa, M., Yamagishi, T., Dutschman, G.E., Parker, W.B., Bodner, A.J., Kilkuskie, R.E., Cheng, Y.C., Lee, K.H., Anti-AIDS agents, 1. Isolation and characterization of four new tetragalloylquinic acids as a new class of HIV reverse transcriptase inhibitors from tannic acid. J. Nat. Prod. 52 (1989), 762–768, 10.1021/np50064a016.
164. Nishizawa, M., Yamagishi, T., Nonaka, G., Nishioka, I., Quantitative determination of gallotannin in paeoniae radix. Yakugaku Zasshi 104 (1984), 1244–1250 http://doi.org/10.1248/yakushi1947.104.12_1244.
165. Nkhili, E., Tomao, V., El Hajji, H., El Boustani, E.S., Chemat, F., Dangles, O., Microwave-assisted water extraction of green tea polyphenols. Phytochem. Anal. 20 (2009), 408–415, 10.1002/pca.1141.
166. Ortholand, J.-Y., Ganesan, A., Natural products and combinatorial chemistry: back to the future. Curr. Opin. Chem. Biol. 8 (2004), 271–280, 10.1016/j.cbpa.2004.04.011.
167. Ou, K.Q., Gu, L.W., Absorption and metabolism of proanthocyanidins. J. Funct. Foods 7 (2014), 43–53, 10.1016/j.jff.2013.08.004.
168. Ou, T.T., Wang, C.J., Lee, Y.S., Wu, C.H., Lee, H.J., Gallic acid induces G2/M phase cell cycle arrest via regulating 14-3-3 beta release from Cdc25C and Chk2 activation in human bladder transitional carcinoma cells. Mol. Nutr. Food Res. 54 (2010), 1781–1790, 10.1002/mnfr.201000096.
169. Ozdal, T., Capanoglu, E., Altay, F., A review on protein–phenolic interactions and associated changes. Food Res. Int. 51 (2013), 954–970, 10.1016/j.foodres.2013.02.009.
170. Palafox-Carlos, H., Gil-Chavez, J., Sotelo-Mundo, R.R., Namiesnik, J., Gorinstein, S., Gonzalez-Aguilar, G.A., Antioxidant interactions between major phenolic compounds found in 'Ataulfo' mango pulp: chlorogenic, gallic, protocatechuic and vanillic acids. Molecules 17 (2012), 12657–12664, 10.3390/molecules171112657.
171. Pan, M.H., Lin, J.H., Lin-Shiau, S.Y., Lin, J.K., Induction of apoptosis by penta-O-galloyl-beta-D-glucose through activation of caspase-3 in human leukemia HL-60 cells. Eur. J. Pharmacol. 381 (1999), 171–183, 10.1016/S0014-2999(99)00549-X.
172. Pandareesh, M.D., Mythri, R.B., Srinivas Bharath, M.M., Bioavailability of dietary polyphenols: factors contributing to their clinical application in CNS diseases. Neurochem. Int. 89 (2015), 198–208, 10.1016/j.neuint.2015.07.003.
173. Pazos, M., Lois, S., Torres, J.L., Medina, I., Inhibition of hemoglobin- and iron-promoted oxidation in fish microsomes by natural phenolics. J. Agr. Food Chem. 54 (2006), 4417–4423, 10.1021/Jf0530300.
174. Pazos, M., Torres, J.L., Andersen, M.L., Skibsted, L.H., Medina, I., Galloylated polyphenols efficiently reduce alpha-tocopherol radicals in a phospholipid model system composed of sodium dodecyl sulfate (SDS) micelles. J. Agr. Food Chem. 57 (2009), 5042–5048, 10.1021/Jf900437m.
175. Perumalla, A.V.S., Hettiarachchy, N.S., Green tea and grape seed extracts - potential applications in food safety and quality. Food Res. Int. 44 (2011), 827–839, 10.1016/j.foodres.2011.01.022.
176. Perveen, R., Funk, K., Thuma, J., Wulf Ridge, S., Cao, Y., Akkerman, J.W., Chen, X., Akbar, H., A novel small molecule 1,2,3,4,6-penta-O-galloyl-alpha-D-glucopyranose mimics the antiplatelet actions of insulin. PLoS One, 6, 2011, e26238, 10.1371/journal.pone.0026238.
177. Piao, M.J., Kang, K.A., Zhang, R., Ko, D.O., Wang, Z.H., Lee, K.H., Antioxidant properties of 1,2,3,4,6-penta-O-galloyl-β-D-glucose from Elaeocarpus sylvestris var. ellipticus. Food Chem. 115 (2009), 412–418 (doi).
178. Pivodová, V., Zahler, S., Karas, D., Valentová, K., Ulrichova, J., In vitro study of 2,3-dehydrosilybin and its galloyl esters as potential inhibitors of angiogenesis. Pharmazie 71 (2016), 478–483, 10.1691/ph.2016.6579.
179. Plundrich, N., Grace, M.H., Raskin, I., Lila, M.A., Bioactive polyphenols from muscadine grape and blackcurrant stably concentrated onto protein-rich matrices for topical applications. Int. J. Cosmet. Sci. 35 (2013), 394–401, 10.1111/ics.12057.
180. Potente, M., Gerhardt, H., Carmeliet, P., Basic and therapeutic aspects of angiogenesis. Cell 146 (2011), 873–887, 10.1016/j.cell.2011.08.039.
181. Potenza, M.A., Marasciulo, F.L., Tarquinio, M., Tiravanti, E., Colantuono, G., Federici, A., Kim, J.A., Quon, M.J., Montagnani, M., EGCG, a green tea polyphenol, improves endothelial function and insulin sensitivity, reduces blood pressure, and protects against myocardial I/R injury in SHR. Am. J. Physiol. Endocrinol. Metab. 292 (2007), E1378–E1387, 10.1152/ajpendo.00698.2006.
182. Prieur, C., Rigaud, J., Cheynier, V., Moutounet, M., Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36 (1994), 781–784, 10.1016/S0031-9422(00)89817-9.
183. Quideau, S., Deffieux, D., Douat-Casassus, C., Pouysegu, L., Plant polyphenols: chemical properties, biological activities, and synthesis. Angew. Chem. Int. Ed. Engl 50 (2011), 586–621, 10.1002/anie.201000044.
184. Rahman, I., Biswas, S.K., Kirkham, P.A., Regulation of inflammation and redox signaling by dietary polyphenols. Biochem. Pharmacol. 72 (2006), 1439–1452, 10.1016/j.bcp.2006.07.004.
185. Ramljak, D., Romanczyk, L.J., Metheny-Barlow, L.J., Thompson, N., Knezevic, V., Galperin, M., Ramesh, A., Dickson, R.B., Pentameric procyanidin from Theobroma cacao selectively inhibits growth of human breast cancer cells. Mol. Cancer Ther. 4 (2005), 537–546, 10.1158/1535-7163.mct-04-0286.
186. Rawat, G., Tripathi, P., Saxena, R.K., Expanding horizons of shikimic acid. Recent progresses in production and its endless frontiers in application and market trends. Appl. Microbiol. Biotechnol. 97 (2013), 4277–4287, 10.1007/s00253-013-4840-y.
187. Reynertson, K.A., Wallace, A.M., Adachi, S., Gil, R.R., Yang, H., Basile, M.J., D'Armiento, J., Weinstein, I.B., Kennelly, E.J., Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora). J. Nat. Prod. 69 (2006), 1228–1230, 10.1021/np0600999.
188. Rezende, C.O.J., Rigotto, C., Caneschi, W., Rezende, C.A.M., Le Hyaric, M., Couri, M.R.C., Simões, C.M.O., de Almeida, M.V., Anti-HSV-1 and antioxidant activities of dicaffeoyl and digalloyl esters of quinic acid. Biomed. Prev. Nutr. 4 (2014), 35–38, 10.1016/j.bionut.2013.09.007.
189. Rizvi, S.I., Zaid, M.A., Impairment of sodium pump and Na/H exchanger in erythrocytes from non-insulin dependent diabetes mellitus patients: effect of tea catechins. Clin. Chim. Acta 354 (2005), 59–67, 10.1016/j.cccn.2004.11.008.
190. Rohdewald, P., A review of the French maritime pine bark extract (Pycnogenol (R)), a herbal medication with a diverse clinical pharmacology. Int. J. Clin. Pharm. Th 40 (2002), 158–168, 10.5414/CPP40158.
191. Roowi, S., Stalmach, A., Mullen, W., Lean, M.E., Edwards, C.A., Crozier, A., Green tea flavan-3-ols: colonic degradation and urinary excretion of catabolites by humans. J. Agr. Food Chem. 58 (2010), 1296–1304, 10.1021/jf9032975.
192. Roubalová, L., Effect of Quercetin and Taxifolin Gallates on Angiogenesis in Vitro. Thesis, 2013, Department of Medical Chemistry and Biochemistry. Palacký University, Olomouc, Czech Republic, 74.
193. Roubalová, L., Biedermann, D., Papoušková, B., Vacek, J., Kuzma, M., Křen, V., Ulrichová, J., Dinková-Kostová, A.T., Vrba, J., Semisynthetic flavonoid 7-O-galloylquercetin activates Nrf2 and induces Nrf2-dependent gene expression in RAW264.7 and Hepa1c1c7 cells. Chem. Biol. Interact. 260 (2016), 58–66, 10.1016/j.cbi.2016.10.015.
194. Ryu, H.G., Jeong, S.J., Kwon, H.Y., Lee, H.J., Lee, E.O., Lee, M.H., Choi, S.H., Ahn, K.S., Kim, S.H., Penta-O-galloyl-beta-D-glucose attenuates cisplatin-induced nephrotoxicity via reactive oxygen species reduction in renal epithelial cells and enhances antitumor activity in Caki-2 renal cancer cells. Toxicol. In Vitro 26 (2012), 206–214, 10.1016/j.tiv.2011.11.012.
195. Saffari, Y., Sadrzadeh, S.M.H., Green tea metabolite EGCG protects membranes against oxidative damage in vitro. Life Sci. 74 (2004), 1513–1518, 10.1016/j.lfs.2003.08.019.
196. Saiko, P., Graser, G., Giessrigl, B., Steinmann, M.T., Schuster, H., Lackner, A., Grusch, M., Krupitza, G., Jaeger, W., Somepalli, V., Golakoti, T., Fritzer-Szekeres, M., Szekeres, T., Digalloylresveratrol, a novel resveratrol analog inhibits the growth of human pancreatic cancer cells. Invest. New Drugs 31 (2013), 1115–1124, 10.1007/s10637-013-0009-x.
197. 2+, common signals for apoptosis induced by gallic acid. Biochem. Pharmacol. 55 (1998), 1973–1981, 10.1016/S0006-2952(98)00041-0.
198. Sakamoto, Y., Terashita, N., Muraguchi, T., Fukusato, T., Kubota, S., Effects of epigallocatechin-3-gallate (EGCG) on A549 lung cancer tumor growth and angiogenesis. Biosci. Biotechnol. Biochem. 77 (2013), 1799–1803, 10.1271/bbb.120882.
199. Salaga, M., Lewandowska, U., Sosnowska, D., Zakrzewski, P.K., Cygankiewicz, A.I., Piechota-Polanczyk, A., Sobczak, M., Mosinska, P., Chen, C., Krajewska, W.M., Fichna, J., Polyphenol extract from evening primrose pomace alleviates experimental colitis after intracolonic and oral administration in mice. N. S. Arch. Pharmacol. 387 (2014), 1069–1078, 10.1007/s00210-014-1025-x.
200. Salucci, M., Stivala, L.A., Maiani, G., Bugianesi, R., Vannini, V., Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2). Br. J. Cancer 86 (2002), 1645–1651, 10.1038/sj/bjc/6600295.
201. Sang, S., Lambert, J.D., Ho, C.T., Yang, C.S., The chemistry and biotransformation of tea constituents. Pharmacol. Res. 64 (2011), 87–99, 10.1016/j.phrs.2011.02.007.
202. Sannomiya, M., Cardoso, C.R., Figueiredo, M.E., Rodrigues, C.M., dos Santos, L.C., dos Santos, F.V., Serpeloni, J.M., Colus, I.M., Vilegas, W., Varanda, E.A., Mutagenic evaluation and chemical investigation of Byrsonima intermedia A. Juss. leaf extracts. J. Ethnopharmacol. 112 (2007), 319–326, 10.1016/j.jep.2007.03.014.
203. Sannomiya, M., dos Santos, L.C., Carbone, V., Napolitano, A., Piacente, S., Pizza, C., Souza-Brito, A.R., Vilegas, W., Liquid chromatography/electrospray ionization tandem mass spectrometry profiling of compounds from the infusion of Byrsonima fagifolia Niedenzu. Rapid Commun. Mass Spectrom. 21 (2007), 1393–1400, 10.1002/rcm.2971.
204. Santos-Buelga, C., Scalbert, A., Proanthocyanidins and tannin-like compounds - nature, occurrence, dietary intake and effects on nutrition and health. J. Sci. Food Agr. 80 (2000), 1094–1117, 10.1002/(Sici)1097-0010(20000515)80 7<1094::Aid-Jsfa569>3.0.Co;2–1.
205. Saxena, H.O., Faridi, U., Srivastava, S., Kumar, J.K., Darokar, M.P., Luqman, S., Chanotiya, C.S., Krishna, V., Negi, A.S., Khanuja, S.P., Gallic acid-based indanone derivatives as anticancer agents. Bioorg. Med. Chem. Lett. 18 (2008), 3914–3918, 10.1016/j.bmcl.2008.06.039.
206. Scappaticci, F.A., Mechanisms and future directions for angiogenesis-based cancer therapies. J. Clin. Oncol. 20 (2002), 3906–3927, 10.1200/JCO.2002.01.033.
207. Scappaticci, F.A., The therapeutic potential of novel antiangiogenic therapies. Expert Opin. Investig. Drugs 12 (2003), 923–932, 10.1517/13543784.12.6.923.
208. Sepulveda, L., Ascacio, A., Rodriguez-Herrera, R., Aguilera-Carbo, A., Aguilar, C.N., Ellagic acid: biological properties and biotechnological development for production processes. Afr. J. Biotechnol. 10 (2011), 4518–4523, 10.5897/AJB10.2201.
209. Shanafelt, T.D., Call, T.G., Zent, C.S., LaPlant, B., Bowen, D.A., Roos, M., Secreto, C.R., Ghosh, A.K., Kabat, B.F., Lee, M.J., Yang, C.S., Jelinek, D.F., Erlichman, C., Kay, N.E., Phase I trial of daily oral Polyphenon E in patients with asymptomatic Rai stage 0 to II chronic lymphocytic leukemia. J. Clin. Oncol. 27 (2009), 3808–3814, 10.1200/JCO.2008.21.1284.
210. Sharma, A., Gautam, S.P., Gupta, A.K., Surface modified dendrimers: synthesis and characterization for cancer targeted drug delivery. Bioorg. Med. Chem. 19 (2011), 3341–3346, 10.1016/j.bmc.2011.04.046.
211. Shoji, T., Masumoto, S., Moriichi, N., Kobori, M., Kanda, T., Shinmoto, H., Tsushida, T., Procyanidin trimers to pentamers fractionated from apple inhibit melanogenesis in B16 mouse melanoma cells. J. Agric. Food Chem. 53 (2005), 6105–6111, 10.1021/jf050418m.
212. Shu, Z., Yu, M., Zeng, G., Zhang, X., Wu, L., Tan, X., Epigallocatechin-3-gallate inhibits proliferation of human aortic smooth muscle cells via up-regulating expression of mitofusin 2. Eur. J. Cell Biol. 93 (2014), 137–144, 10.1016/j.ejcb.2014.04.001.
213. Singh, R.P., Dhanalakshmi, S., Agarwal, C., Agarwal, R., Silibinin strongly inhibits growth and survival of human endothelial cells via cell cycle arrest and downregulation of survivin, Akt and NF-kappaB: implications for angioprevention and antiangiogenic therapy. Oncogene 24 (2005), 1188–1202, 10.1038/sj.onc.1208276.
214. Skopec, M.M., Hagerman, A.E., Karasov, W.H., Do salivary proline-rich proteins counteract dietary hydrolyzable tannin in laboratory rats?. J. Chem. Ecol. 30 (2004), 1679–1692, 10.1023/B: JOEC.0000042395.31307.be.
215. Sohi, K.K., Mittal, N., Hundal, M.K., Khanduja, K.L., Gallic acid, an antioxidant, exhibits antiapoptotic potential in normal human lymphocytes: a Bcl-2 independent mechanism. J. Nutr. Sci. Vitaminol. (Tokyo) 49 (2003), 221–227, 10.3177/jnsv.49.221.
216. Sohretoglu, D., Sakar, M.K., Sterner, O., New galloylated flavonoid glycosides from Geranium stepporum DAVIS. Helv. Chim. Acta 92 (2009), 520–524, 10.1002/hlca.200800346.
217. Sondheimer, E., Chlorogenic acids and related depsides. Bot. Rev. 30 (1964), 667–712.
218. Soong, Y.Y., Barlow, P.J., Quantification of gallic acid and ellagic acid from longan (Dimocarpus longan Lour.) seed and mango (Mangifera indica L.) kernel and their effects on antioxidant activity. Food Chem. 97 (2006), 524–530, 10.1016/j.foodchem.2005.05.033.
219. Souquet, J.M., Cheynier, V., Brossaud, F., Moutounet, M., Polymeric proanthocyanidins from grape skins. Phytochemistry 43 (1996), 509–512, 10.1016/0031-9422(96)00301-9.
220. Srivastava, V., Negi, A.S., Kumar, J.K., Gupta, M.M., Khanuja, S.P., Plant-based anticancer molecules: a chemical and biological profile of some important leads. Bioorg. Med. Chem. 13 (2005), 5892–5908, 10.1016/j.bmc.2005.05.066.
221. Stagos, D., Kazantzoglou, G., Magiatis, P., Mitaku, S., Anagnostopoulos, K., Kouretas, D., Effects of plant phenolics and grape extracts from Greek varieties of Vitis vinifera on Mitomycin C and topoisomerase I-induced nicking of DNA. Int. J. Mol. Med. 15 (2005), 1013–1022, 10.3892/ijmm.15.6.1013.
222. Subirade, I., Fernandez, Y., Periquet, A., Mitjavila, S., Catechin protection of 3t3 Swiss fibroblasts in culture under oxidative stress. Biol. Trace Elem. Res. 47 (1995), 313–319, 10.1007/Bf02790132.
223. Subramanian, N., Venkatesh, P., Ganguli, S., Sinkar, V.P., Role of polyphenol oxidase and peroxidase in the generation of black tea theaflavins. J. Agr. Food Chem. 47 (1999), 2571–2578, 10.1021/jf981042y.
224. Sun, Q., Heilmann, J., Konig, B., Natural phenolic metabolites with anti-angiogenic properties - a review from the chemical point of view. Beilstein J. Org. Chem. 11 (2015), 249–264, 10.3762/bjoc.11.28.
225. 2-induced oxidative stress in human keratinocytes and mouse fibroblasts. Burns 32 (2006), 973–979, 10.1016/j.burns.2006.04.004.
226. Symonds, E.L., Konczak, I., Fenech, M., The Australian fruit Illawarra plum (Podocarpus elatus Endl., Podocarpaceae) inhibits telomerase, increases histone deacetylase activity and decreases proliferation of colon cancer cells. Br. J. Nutr. 109 (2013), 2117–2125, 10.1017/S0007114512004333.
227. Taamalli, A., Iswaldi, I., Arraez-Roman, D., Segura-Carretero, A., Fernandez-Gutierrez, A., Zarrouk, M., UPLC-QTOF/MS for a rapid characterisation of phenolic compounds from leaves of Myrtus communis L. Phytochem. Anal. 25 (2014), 89–96, 10.1002/pca.2475.
228. Tasdemir, D., Kaiser, M., Brun, R., Yardley, V., Schmidt, T.J., Tosun, F., Ruedi, P., Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: in vitro, in vivo, structure-activity relationship, and quantitative structure-activity relationship studies. Antimicrob. Agents Chemother. 50 (2006), 1352–1364, 10.1128/AAC.50.4.1352-1364.2006.
229. Thapa, M., Kim, Y., Desper, J., Chang, K.O., Hua, D.H., Synthesis and antiviral activity of substituted quercetins. Bioorg. Med. Chem. Lett. 22 (2012), 353–356, 10.1016/j.bmcl.2011.10.119.
230. Thongphasuk, P., Stremmel, W., Chamulitrat, W., Potent direct or TNF-alpha-promoted anticancer effects of 2,3-dehydrosilybin: comparison study with silybin. Chemotherapy 54 (2008), 23–30, 10.1159/000112314.
231. Thongphasuk, P., Stremmel, W., Chamulitrat, W., 2,3-Dehydrosilybin is a better DNA Topoisomerase I inhibitor than its parental silybin. Chemotherapy 55 (2009), 42–48, 10.1159/000175466.
232. Tourino, S., Selga, A., Jimenez, A., Julia, L., Lozano, C., Lizarraga, D.L., Cascante, M., Torres, J.L., Procyanidin fractions from pine (Pinus pinaster) bark: radical scavenging power in solution, antioxidant activity in emulsion, and antiproliferative effect in melanoma cells. J. Agr. Food Chem. 53 (2005), 4728–4735, 10.1021/Jf050262q.
233. Trouillas, P., Marsal, P., Svobodová, A., Vostalová, J., Gažák, R., Hrbáč, J., Sedmera, P., Křen, V., Lazzaroni, R., Duroux, J.L., Walterová, D., Mechanism of the antioxidant action of silybin and 2,3-dehydrosilybin flavonolignans: a joint experimental and theoretical study. J. Phys. Chem. A 112 (2008), 1054–1063, 10.1021/jp075814h.
234. Truchado, P., Larrosa, M., Garcia-Conesa, M.T., Cerda, B., Vidal-Guevara, M.L., Tomas-Barberan, F.A., Espin, J.C., Strawberry processing does not affect the production and urinary excretion of urolithins, ellagic acid metabolites, in humans. J. Agr. Food Chem. 60 (2012), 5749–5754, 10.1021/jf203641r.
235. Tuominen, A., Sundman, T., Stability and oxidation products of hydrolysable tannins in basic conditions detected by HPLC/DAD-ESI/QTOF/MS. Phytochem. Anal. 24 (2013), 424–435, 10.1002/pca.2456.
236. Tuominen, A., Toivonen, E., Mutikainen, P., Salminen, J.P., Defensive strategies in Geranium sylvaticum. Part 1: organ-specific distribution of water-soluble tannins, flavonoids and phenolic acids. Phytochemistry 95 (2013), 394–407, 10.1016/j.phytochem.2013.05.013.
237. Turk, G., Sonmez, M., Ccedil;eribasi, A.O., Yuce, A., Atessahin, A., Attenuation of cyclosporine A-induced testicular and spermatozoal damages associated with oxidative stress by ellagic acid. Int. Immunopharmacol. 10 (2010), 177–182, 10.1016/j.intimp.2009.10.013.
238. Vacek, J., Zatloukalová, M., Desmier, T., Nezhodová, V., Hrbáč, J., Kubala, M., Křen, V., Ulrichová, J., Trouillas, P., Antioxidant, metal-binding and DNA-damaging properties of flavonolignans: a joint experimental and computational highlight based on 7-O-galloylsilybin. Chem.-Biol. Interact. 205 (2013), 173–180, 10.1016/j.cbi.2013.07.006.
239. Valenti, D., De Rasmo, D., Signorile, A., Rossi, L., de Bari, L., Scala, I., Granese, B., Papa, S., Vacca, R.A., Epigallocatechin-3-gallate prevents oxidative phosphorylation deficit and promotes mitochondrial biogenesis in human cells from subjects with Down's syndrome. Biochim. Biophys. Acta 1832 (2013), 542–552, 10.1016/j.bbadis.2012.12.011.
240. Veluri, R., Singh, R.P., Liu, Z., Thompson, J.A., Agarwal, R., Agarwal, C., Fractionation of grape seed extract and identification of gallic acid as one of the major active constituents causing growth inhibition and apoptotic death of DU145 human prostate carcinoma cells. Carcinogenesis 27 (2006), 1445–1453, 10.1093/carcin/bgi347.
241. Verma, S., Singh, A., Mishra, A., Gallic acid: molecular rival of cancer. Environ. Toxicol. Phar 35 (2013), 473–485, 10.1016/j.etap.2013.02.011.
242. Viswanatha, G.L., Shylaja, H., Mohan, C.G., Alleviation of transient global ischemia/reperfusion-induced brain injury in rats with 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose isolated from Mangifera indica. Eur. J. Pharmacol. 720 (2013), 286–293, 10.1016/j.ejphar.2013.10.016.
243. Vrba, J., Gažák, R., Kuzma, M., Papoušková, B., Vacek, J., Weiszenstein, M., Křen, V., Ulrichová, J., A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway. J. Med. Chem. 56 (2013), 856–866, 10.1021/jm3013344.
244. Wagner, H., Leading structures of plant origin for drug development. J. Ethnopharmacol. 38 (1993), 105–112, 10.1016/0378-8741(93)90004-O.
245. Wang, X., Song, K.S., Guo, Q.X., Tian, W.X., The galloyl moiety of green tea catechins is the critical structural feature to inhibit fatty-acid synthase. Biochem. Pharmacol 66 (2003), 2039–2047, 10.1016/S0006-2952(03)00585-9.
246. Wang, Y., Ho, C.T., Polyphenolic chemistry of tea and coffee: a century of progress. J. Agr. Food Chem. 57 (2009), 8109–8114, 10.1021/jf804025c.
247. Xiao, H.T., Lin, C.Y., Ho, D.H., Peng, J., Chen, Y., Tsang, S.W., Wong, M., Zhang, X.J., Zhang, M., Bian, Z.X., Inhibitory effect of the gallotannin corilagin on dextran sulfate sodium-induced murine ulcerative colitis. J. Nat. Prod. 76 (2013), 2120–2125, 10.1021/np4006772.
248. Xiao, J.B., Ni, X.L., Kai, G.Y., Chen, X.Q., A review on structure-activity relationship of dietary polyphenols inhibiting alpha-amylase. Crit. Rev. Food Sci. Nutr. 53 (2013), 497–506, 10.1080/10408398.2010.548108.
249. Xie, M.H., Hu, B., Wang, Y., Zeng, X.X., Grafting of gallic Acid onto chitosan enhances antioxidant activities and alters rheological properties of the copolymer. J. Agr. Food Chem. 62 (2014), 9128–9136, 10.1021/jf503207s.
250. Yeh, C.W., Chen, W.J., Chiang, C.T., Lin-Shiau, S.Y., Lin, J.K., Suppression of fatty acid synthase in MCF-7 breast cancer cells by tea and tea polyphenols: a possible mechanism for their hypolipidemic effects. Pharmacogenomics J. 3 (2003), 267–276, 10.1038/sj.tpj.6500192.
251. Zatloukalová, M., Křen, V., Gažák, R., Kubala, M., Trouillas, P., Ulrichová, J., Vacek, J., Electrochemical investigation of flavonolignans and study of their interactions with DNA in the presence of Cu(II). Bioelectrochemistry 82 (2011), 117–124, 10.1016/j.bioelechem.2011.06.005.
252. Zhang, J.H., Li, L., Kim, S.H., Hagerman, A.E., Lu, J.X., Anti-cancer, anti-diabetic and other pharmacologic and biological activities of penta-galloyl-glucose. Pharm. Res.-Dord 26 (2009), 2066–2080, 10.1007/s11095-009-9932-0.
253. Zhang, Y., Yang, N.D., Zhou, F., Shen, T., Duan, T., Zhou, J., Shi, Y., Zhu, X.Q., Shen, H.M., (-)-Epigallocatechin-3-gallate induces non-apoptotic cell death in human cancer cells via ROS-mediated lysosomal membrane permeabilization. PLoS One, 7, 2012, e46749, 10.1371/journal.pone.0046749.
254. Zhao, J., Wang, J., Chen, Y., Agarwal, R., Anti-tumor-promoting activity of a polyphenolic fraction isolated from grape seeds in the mouse skin two-stage initiation-promotion protocol and identification of procyanidin B5-3'-gallate as the most effective antioxidant constituent. Carcinogenesis 20 (1999), 1737–1745 (doi).
255. Zielinska, M., Lewandowska, U., Podsedek, A., Cygankiewicz, A.I., Jacenik, D., Salaga, M., Kordek, R., Krajewska, W.M., Fichna, J., Orally available extract from Brassica oleracea var. capitata rubra attenuates experimental colitis in mouse models of inflammatory bowel diseases. J. Funct. Foods 17 (2015), 587–599, 10.1016/j.jff.2015.05.046.