Flavonoid Basics: Chemistry, Sources, Mechanisms of Action, and Safety

REFERENCES

• Visioli F , De La Lastra CA , Andres-Lacueva C , Aviram M , Calhau C , et al. Polyphenols and human health: a prospectus . Crit Rev Food Sci Nutr . 2011 ; 51 : 524 – 46 .
   PubMed Web of Science ®Google Scholar
• Spencer JPE . Flavonoids and brain health: Multiple effects underpinned by common mechanisms . Genes Nutr . 2009 ; 4 : 243 – 50 .
   PubMed Web of Science ®Google Scholar
• Blanco-Colio LM , Valderrama M , Alvarez-Sala LA , Bustos C , Ortego M , et al. . Red wine intake prevents nuclear factor κB activation in peripheral blood mononuclear cells of health volunteers during postprandial lipemia . Circulation . 2000 ; 102 : 1020 – 6 .
   PubMed Web of Science ®Google Scholar
• Surh Y-J. Cancer chemoprevention with dietary phytochemicals . Nature Rev. 2003 ; 768 – 80 .
   Web of Science ®Google Scholar
• Atmani D , Chaher N , Atmani D , Berboucha M , Debbache N , Boudaoud H . Flavonoids in human health: from structure to biological activity . Curr Nutr Food Sci . 2009 ; 5 : 225 – 37 .
   Google Scholar
• Mladenka P , Macakova K , Filipsky T , Zatloukalova L , Jahodar L , et al. . In vitro analysis of iron chelating activity of flavonoids . J Inorg Biochem . 2011 ; 105 : 693 – 701 .
   PubMed Web of Science ®Google Scholar
• Yazaki K , Sasaki K , Tsurumaru Y. Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochem . 2009; 70:1739–45.
   PubMed Web of Science ®Google Scholar
• Lopez M , Martinez F , Del Valle C , Orte C , Miro M . Analysis of phenolic constituents of biological interest in red wines by high-performance liquid chromatography . J Chromat A . 2001 ; 922 : 359 – 63 .
   PubMed Web of Science ®Google Scholar
• Prior RL , Lazarus SA , Cao G , Muccitelli H , Hammerstone JF . Identification of procyanidins and anthocyanins in blueberries and cranberries (Vaccinium spp.) using high-performance liquid chromatography/mass spectrometry . J Agric Food Chem . 2001 ; 49 : 1270 – 6 .
   PubMed Web of Science ®Google Scholar
• Bolling BW , Chen C-YO , McKay DL , Blumberg JB . The phytochemical composition of tree nuts . Nutr Res Rev . 2011 ; 24 : 244 – 75 .
   PubMed Web of Science ®Google Scholar
• Gu L , Kelm MA , Hammerstone JF , Beecher G , Holden J , et al. . Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation . J Agric Food Chem . 2003 ; 51 : 7513 – 21 .
   PubMed Web of Science ®Google Scholar
• Miglio C , Chiavara E , Visconti A , Fogliano V , Pellegrini N . Effects of different cooking methods on nutritional and physicochemical characteristics of selected vegetables . J Agric Food Chem . 2008 ; 56 : 139 – 47 .
   PubMed Web of Science ®Google Scholar
• Napolitano A , Cascone A , Graziani G , Ferracane R , Scalfi L , et al. . Influence of variety and storage on the polyphenol composition of apple flesh . J Agric Food Chem . 2004 ; 52 : 6526 – 31 .
   PubMed Web of Science ®Google Scholar
• Price KR , Colquhoun IJ , Barnes KA , Rhodes MJC . Composition and content of flavonol glycosides in green beans and their fate during processing . J Agric Food Chem . 1998 ; 46 : 4898 – 903 .
   Web of Science ®Google Scholar
• Price KR , Bacon JR , Rhodes MJC . Effect of storage and domestic processing on the content and composition of flavonol glucosides in onion (Allium cepa) . J Agric Food Chem . 1997 ; 45 : 938 – 42 .
   Web of Science ®Google Scholar
• Wu X , Beecher GR , Holden JM , Haytowitz DB , Gebhardt SE , Prior RL . Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption . J Agric Food Chem . 2006 ; 54 : 4069 – 75 .
   PubMed Web of Science ®Google Scholar
• Neveu V , Perez-Jiménez J , Vos F , Crespy V , du Chaffaut L , et al. Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. 10.1093/database/bap024. 2010. Version 1.5.2. Accessed at http://www.phenol-explorer.eu .
   Google Scholar
• Manach C , Williamson G , Morand C , Scalbert A , Remesy C . Bioavailability and bioefficacy of polyphenols in humans . I. Review of 97 bioavailability studies. Am J Clin Nutr . 2005 ; 81 : 230S – 42S .
   PubMed Web of Science ®Google Scholar
• Barnes S , Prasain J , D'Alessandro T , Arabshahi A , Botting N , et al. . The metabolism and analysis of isoflavones and other dietary polyphenols in foods and biological systems . Food Funct . 2011 ; 2 : 235 – 44 .
   PubMed Web of Science ®Google Scholar
• Nurmi T , Mursu J , Heinonen M , Nurmi A , Hiltunen R , Voutilainen S . Metabolism of berry anthocyanins to phenolic acids in humans . J Agric Food Chem . 2009 ; 57 : 2274 – 81 .
   PubMed Web of Science ®Google Scholar
• Ortega N , Reguant J , Romero MP , Macia A , Motilva MJ . Effect of fat content on the digestibility and bioaccessibility of cocoa polyphenol by an in vitro digestion model . J Agric Food Chem . 2009 ; 57 : 5743 – 9 .
   PubMed Web of Science ®Google Scholar
• Perez-Jimenez J , Serrano J , Tabernero M , Arranz S , Diaz-Rubio ME , et al.. Bioavailability of phenolic antioxidants associated with dietary fiber: Plasma antioxidant capacity after acute and long-term intake in humans. Plant Foods Hum Nutr . 2009; 64:102–7.
   PubMed Web of Science ®Google Scholar
• Porrini M , Riso P . Factors influencing the bioavailability of antioxidants in foods: a critical appraisal . Nutr Metabol Cardiovasc Dis . 2008 ; 18 : 647 – 50 .
   PubMed Web of Science ®Google Scholar
• Zhang Y , Gordon GB . A strategy for cancer prevention: stimulation of the Nrf2-ARE signaling pathway . Mol Cancer Ther . 2004 ; 3 : 885 – 93 .
   PubMed Web of Science ®Google Scholar
• Guan S , Ge D , Liu TQ , Ma XH , Cui ZF . Protocatechuic acid promotes cell proliferation and reduces basal apoptosis in cultured neural stem cells . Toxicol In Vitro . 2009 ; 23 : 201 – 8 .
   PubMed Web of Science ®Google Scholar
• Grimm T , Schäfer A , Hogger P . Antioxidant activity and inhibition of matrix metalloproteinases by metabolites of maritime pine bark extract (pycnogenol) . Free Radic Biol Med . 2004 ; 36 : 811 – 22 .
   PubMed Web of Science ®Google Scholar
• Joy S , Siow RC , Rowlands DJ , Becker M , Wyatt AW , et al. . The isoflavone equol mediates rapid vascular relaxation: Ca2+-independent activation of endothelial nitric-oxide synthase/Hsp90 involving ERK1/2 and Akt phosphorylation in human endothelial cells . J Biol Chem . 2006 ; 281 : 27335 – 45 .
   PubMed Web of Science ®Google Scholar
• Lotito SB , Zhang WJ , Yang CS , Crozier A , Frei B . Metabolic conversion of dietary flavonoids alters their anti-inflammatory and antioxidant properties . Free Radic Biol Med . 2011 ; 51 : 454 – 63 .
   PubMed Web of Science ®Google Scholar
• Donnini S , Finetti F , Lusini L , Morbidelli L , Cheynier V , et al. . Divergent effects of quercetin conjugates on angiogenesis . Br J Nutr . 2006 ; 95 : 1016 – 23 .
   PubMed Web of Science ®Google Scholar
• Harwood M , Danielewska-Nikiel B , Borzelleca JF , Flamm GW , Williams GM , Lines TC . A critical review of the data related to the safety of quercetin and lack of evidence of in vivo toxicity, including lack of genotoxic/carcinogenic properties . Food Chem Toxicol . 2007 ; 45 : 2179 – 205 .
   PubMed Web of Science ®Google Scholar
• Erdman JW Jr. , Balentine D , Arab L , Beecher G , Dwyer JT , et al. . Flavonoids and heart health: proceedings of the ILSI North America Flavonoids Workshop, May 31–June 1, 2005, Washington, DC . J Nutr . 2007 ; 137 : 718S – 37S .
   PubMed Web of Science ®Google Scholar
• Hooper L , Kroon PA , Rimm EB , Cohn JS , Harvey I , et al. . Flavonoids, flavonoid-rich foods, and cardiovascular risk: a meta-analysis of randomized controlled trials . Am J Clin Nutr . 2008 ; 88 : 38 – 50 .
   PubMed Web of Science ®Google Scholar
• Lambert JD , Sang S , Yang CS . Possible controversy over dietary polyphenols: benefits vs . risks. Toxicol . 2007 ; 20 : 583 – 5 .
   PubMed Web of Science ®Google Scholar
• Egert S , Rimbach G . Which sources of flavonoids: complex diets or dietary supplements? Adv Nutr (Bethesda) . 2011 ; 2 : 8 – 14 .
   PubMed Web of Science ®Google Scholar
• Hurrell RF , Reddy M , Cook JD . Inhibition of non-heme iron absorption in man by polyphenolic-containing beverages . Br J Nutr . 1999 ; 81 : 289 – 95 .
   PubMed Web of Science ®Google Scholar
• Temme EH , van Hoydonck PG . Tea consumption and iron status . Eur J Clin Nutr . 2002 ; 56 : 379 – 86 .
   PubMed Web of Science ®Google Scholar
• Moon YJ , Wang X , Morris ME . Dietary flavonoids: effects on xenobiotic and carcinogen metabolism . Toxicol In Vitro . 2006 ; 20 : 187 – 210 .
   PubMed Web of Science ®Google Scholar
• Messina M , Redmond G . Effects of soy protein and soybean isoflavones on thyroid function in healthy adults and hypothyroid patients: a review of the relevant literature . Thyroid . 2006 ; 16 : 249 – 58 .
   PubMed Web of Science ®Google Scholar
• Bitto A , Polito F , Atteritano M , Altavilla D , Mazzaferro S , et al.. Genistein aglycone does not affect thyroid function: results from a three-year, randomized, double-blind, placebo-controlled trial. J Clin Endocrinol Metab . 2010; 95:3067–72.
   PubMed Web of Science ®Google Scholar
• Jerome-Morais A , Diamond AM , Wright ME . Dietary supplements and human health: For better or for worse? Mol Nutr Food Res . 2011 ; 55 : 122 – 35 .
   PubMed Web of Science ®Google Scholar
• Prasain JK , Carlson SH , Wyss JM . Flavonoids and age-related disease: risk, benefits and critical windows . Maturitas . 2010 ; 66 : 163 – 71 .
   PubMed Web of Science ®Google Scholar