Abstract
Anthocyanins are naturally occurring compounds widespread in plant-derived foodstuffs and therefore abundant in our diet. There are evidences regarding the positive association of their intake with healthy biological effects displayed in vivo. This chapter aims to review some concepts regarding anthocyanins’ bioavailability. It summarizes the latest advances on the ingestion, absorption, bioavailability, and biotransformation of these compounds through different approaches. Attention is also given to the role of microbiota in anthocyanin metabolism and bioavailability.
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References
Mazza G, Miniati E (1993) Anthocyanins in fruits, vegetables, and grains. CRC Press, Boca Raton
Markakis P (1982) Stability of anthocyanins in foods. In: Markakis P (ed) Anthocyanins as food colors. Academic, London, pp P163–P180
Mazza GJ (2007) Anthocyanins and heart health. Ann Ist Super Sanita 43:369–374
Wang LS, Stoner GD (2008) Anthocyanins and their role in cancer prevention. Cancer Lett 269:281–290
Dell'Agli M, Busciala A, Bosisio E (2004) Vascular effects of wine polyphenols. Cardiovasc Res 63:593–602
Han KH, Matsumoto A, Shimada K, Sekikawa M, Fukushima M (2007) Effects of anthocyanin-rich purple potato flakes on antioxidant status in F344 rats fed a cholesterol-rich diet. Br J Nutr 98:914–921
Liu LK, Lee HJ, Shih YW, Chyau CC, Wang CJ (2008) Mulberry anthocyanin extracts inhibit LDL oxidation and macrophage-derived foam cell formation induced by oxidative LDL. J Food Sci 73:H113–H121
Faria A, Pestana D, Teixeira D, de Freitas V, Mateus N, Calhau C (2010) Blueberry anthocyanins and pyruvic acid adducts: anticancer properties in breast cancer cell lines. Phytother Res 24:1862–1869
Shin DY, Ryu CH, Lee WS, Kim DC, Kim SH, Hah YS, Lee SJ, Shin SC, Kang HS, Choi YH (2009) Induction of apoptosis and inhibition of invasion in human hepatoma cells by anthocyanins from meoru. Ann N Y Acad Sci 1171:137–148
Li L, Adams LS, Chen S, Killian C, Ahmed A, Seeram NP (2009) Eugenia jambolana Lam. berry extract inhibits growth and induces apoptosis of human breast cancer but not non-tumorigenic breast cells. J Agric Food Chem 57:826–831
Matsubara K, Kaneyuki T, Miyake T, Mori M (2005) Antiangiogenic activity of nasunin, an antioxidant anthocyanin, in eggplant peels. J Agric Food Chem 53:6272–6275
Hammerstone JF, Lazarus SA, Schmitz HH (2000) Procyanidin content and variation in some commonly consumed foods. J Nutr 130:2086S–2092S
Francis FJ (1989) Food colorants: anthocyanins. Crit Rev Food Sci Nutr 28:273–314
Andersen OM, Jordheim M (2005) The anthocyanins. In: Andersen OM, Markham KR (eds) Flavonoids: chemistry, biochemistry and applications. CRC Press, Boca Raton, pp 471–552
Brouillard R, Delaporte B (1977) Chemistry of anthocyanin pigments. 2. Kinetic and thermodynamic study of proton-transfer, hydration and tautomeric reactions of malvidin 3-glucoside. J Am Chem Soc 99:8461–8468
Brouillard R, Dubois JE (1977) Mechanism of structural transformations of anthocyanins in acidic media. J Am Chem Soc 99:1359–1364
Brouillard R, Lang J (1990) The hemiacetal-cis-chalcone equilibrium of malvidin, a natural anthocyanin. Can J Chem - Revue Canadienne De Chimie 68:755–761
Mazza G, Brouillard R (1990) The mechanism of copigmentation of anthocyanins in aqueous-solutions. Phytochemistry 29:1097–1102
Davies AJ, Mazza G (1993) Copigmentation of simple and acylated anthocyanins with colorless phenolic-compounds. J Agric Food Chem 41:716–720
Brouillard R, Dangles O (1994) Anthocyanin molecular-interactions – the first step in the formation of new pigments during wine aging. Food Chem 51:365–371
Furtado P, Figueiredo P, Dasneves HC, Pina F (1993) Photochemical and thermal-degradation of anthocyanidins. J Photochem Photobiol A Chem 75:113–118
Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D et al (2010) Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford) 2010:bap024
Scalbert A, Williamson G (2000) Dietary intake and bioavailability of polyphenols. J Nutr 130:2073S–2085S
Perez-Jimenez J, Fezeu L, Touvier M, Arnault N, Manach C, Hercberg S, Galan P, Scalbert A (2011) Dietary intake of 337 polyphenols in French adults. Am J Clin Nutr 93:1220–1228
Mazza G, Velioglu YS (1992) Anthocyanins and other phenolic-compounds in fruits of red-fleshed apples. Food Chem 43:113–117
Clifford MN (2000) Anthocyanins - nature, occurrence and dietary burden. J Sci Food Agric 80:1063–1072
Perez-Jimenez J, Neveu V, Vos F, Scalbert A (2010) Systematic analysis of the content of 502 polyphenols in 452 foods and beverages: an application of the phenol-explorer database. J Agric Food Chem 58:4959–4969
He J, Santos-Buelga C, Silva AMS, Mateus N, De Freitas V (2006) Isolation and structural characterization of new anthocyanin-derived yellow pigments in aged red wines. J Agric Food Chem 54:9598–9603
Oliveira J, de Freitas V, Silva AMS, Mateus N (2007) Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins. J Agric Food Chem 55:6349–6356
Pissarra J, Lourenco S, Gonzalez-Paramas AM, Mateus N, Buelga CS, Silva AMS, De Freitas V (2004) Structural characterization of new malvidin 3-glucoside-catechin aryl/alkyl-linked pigments. J Agric Food Chem 52:5519–5526
Sousa C, Mateus N, Silva AMS, Gonzalez-Paramas AM, Santos-Buelga C, de Freitas V (2007) Structural and chromatic characterization of a new malvidin 3-glucoside-vanillyl-catechin pigment. Food Chem 102:1344–1351
Byers JP, Sarver JG (2009) Pharmacokinetic modeling. In: Hacker M, Bachmann K, Messer W (eds) Pharmacology: principles and practice. Academic Press, London, pp 201–277
Faria A, Pestana D, Azevedo J, Martel F, Vd F, Azevedo I, Mateus N, Calhau C (2009) Absorption of anthocyanins through intestinal epithelial cells – putative involvement of GLUT2. Mol Nutr Food Res 53:1430–1437
McGhie TK, Walton MC (2007) The bioavailability and absorption of anthocyanins: towards a better understanding. Mol Nutr Food Res 51:702–713
Walle T (2004) Absorption and metabolism of flavonoids. Free Radic Biol Med 36:829–837
Vanzo A, Terdoslavich M, Brandoni A, Torres AM, Vrhovsek U, Passamonti S (2008) Uptake of grape anthocyanins into the rat kidney and the involvement of bilitranslocase. Mol Nutr Food Res 52:1106–1116
Wiese S, Gärtner S, Rawel HM, Winterhalter P, Kulling SE (2009) Protein interactions with cyanidin-3-glucoside and its influence on α-amylase activity. J Sci Food Agric 89:33–40
Matsui T, Ueda T, Oki T, Sugita K, Terahara N, Matsumoto K (2001) α-glucosidase inhibitory action of natural acylated anthocyanins. 1. Survey of natural pigments with potent inhibitory activity. J Agric Food Chem 49:1948–1951
Walle T, Browning AM, Steed LL, Reed SG, Walle UK (2005) Flavonoid glucosides are hydrolyzed and thus activated in the oral cavity in humans. J Nutr 135:48–52
Mallery SR, Budendorf DE, Larsen MP, Pei P, Tong M, Holpuch AS, Larsen PE, Stoner GD, Fields HW, Chan KK et al (2011) Effects of human oral mucosal tissue, saliva and oral microflora on intraoral metabolism and bioactivation of black raspberry anthocyanins. Cancer Prev Res 8:1209–1221
Cao G, Prior RL (1999) Anthocyanins are detected in human plasma after oral administration of an elderberry extract. Clin Chem 45:574–576
Cao G, Muccitelli HU, Sanchez-Moreno C, Prior RL (2001) Anthocyanins are absorbed in glycated forms in elderly women: a pharmacokinetic study. Am J Clin Nutr 73:920–926
Milbury PE, Cao G, Prior RL, Blumberg J (2002) Bioavailability of elderberry anthocyanins. Mech Ageing Dev 123:997–1006
Mulleder U, Murkovic M, Pfannhauser W (2002) Urinary excretion of cyanidin glycosides. J Biochem Biophys Methods 53:61–66
Piskula MK, Yamakoshi J, Iwai Y (1999) Daidzein and genistein but not their glucosides are absorbed from the rat stomach. FEBS Lett 447:287–291
Crespy V, Morand C, Besson C, Manach C, Demigne C, Remesy C (2001) Quercetin, but not its glycosides, is absorbed from the rat stomach. J Agric Food Chem 50:618–621
Strassburg CP, Oldhafer K, Manns MP, Tukey RH (1997) Differential expression of the UGT1A locus in human liver, biliary, and gastric tissue: identification of UGT1A7 and UGT1A10 transcripts in extrahepatic tissue. Mol Pharmacol 52:212–220
Strassburg CP, Nguyen N, Manns MP, Tukey RH (1998) Polymorphic expression of the UDP-glucuronosyltransferase UGT1A gene locus in human gastric epithelium. Mol Pharmacol 54:647–654
Harris RM, Picton R, Singh S, Waring RH (2000) Activity of phenolsulfotransferases in the human gastrointestinal tract. Life Sci 67:2051–2057
Karhunen T, Tilgmann C, Ulmanen I, Julkunen I, Panula P (1994) Distribution of catechol-O-methyltransferase enzyme in rat tissues. J Histochem Cytochem 42:1079–1090
Déchelotte P, Varrentrapp M, Meyer HJ, Schwenk M (1993) Conjugation of 1-naphthol in human gastric epithelial cells. Gut 34:177–180
Talavera S, Felgines C, Texier O, Besson C, Manach C, Lamaison JL, Remesy C (2004) Anthocyanins are efficiently absorbed from the small intestine in rats. J Nutr 134:2275–2279
Miyazawa T, Nakagawa K, Kudo M, Muraishi K, Someya K (1999) Direct intestinal absorption of red fruit anthocyanins, cyanidin-3-glucoside and cyanidin-3,5-diglucoside, into rats and humans. J Agric Food Chem 47:1083–1091
Tsuda T, Horio F, Osawa T (1999) Absorption and metabolism of cyanidin 3-O-b-D-glucoside in rats. FEBS Lett 449:179–182
Talavera S, Felgines C, Texier O, Besson C, Lamaison JL, Remesy C (2003) Anthocyanins are efficiently absorbed from the stomach in anesthetized rats. J Nutr 133:4178–4182
McGhie TK, Ainge GD, Barnett LE, Cooney JM, Jensen DJ (2003) Anthocyanin glycosides from berry fruit are absorbed and excreted unmetabolized by both humans and rats. J Agric Food Chem 51:4539–4548
Ichiyanagi T, Shida Y, Rahman MM, Hatano Y, Konishi T (2005) Extended glucuronidation is another major path of cyanidin 3-O-b-D-glucopyranoside metabolism in rats. J Agric Food Chem 53:7312–7319
Ichiyanagi T, Rahman MM, Kashiwada Y, Ikeshiro Y, Shida Y, Hatano Y, Matsumoto H, Hirayama M, Tsuda T, Konishi T (2004) Absorption and metabolism of delphinidin 3-O-b-glucopyranoside in rats. Free Radic Biol Med 36:930–937
Ichiyanagi T, Shida Y, Rahman MM, Hatano Y, Matsumoto H, Hirayama M, Konishi T (2005) Metabolic pathway of cyanidin 3-O-b-D-glucopyranoside in rats. J Agric Food Chem 53:145–150
Woodward G, Kroon P, Cassidy A, Kay C (2009) Anthocyanin stability and recovery: implications for the analysis of clinical and experimental samples. J Agric Food Chem 57:5271–5278
Vitaglione P, Donnarumma G, Napolitano A, Galvano F, Gallo A, Scalfi L, Fogliano V (2007) Protocatechuic acid is the major human metabolite of cyanidin-glucosides. J Nutr 137:2043–2048
Riso P, Visioli F, Gardana C, Grande S, Brusamolino A, Galvano F, Galvano G, Porrini M (2005) Effects of blood orange juice intake on antioxidant bioavailability and on different markers related to oxidative stress. J Agric Food Chem 53:941–947
Nurmi T, Mursu J, Heinonen M, Nurmi A, Hiltunen R, Voutilainen S (2009) Metabolism of berry anthocyanins to phenolic acids in humans. J Agric Food Chem 57:2274–2281
Bò CD, Ciappellano S, Klimis-Zacas D, Martini D, Gardana C, Riso P, Porrini M (2009) Anthocyanin absorption, metabolism, and distribution from a wild blueberry-enriched diet (Vaccinium angustifolium) is affected by diet duration in the sprague–dawley rat. J Agric Food Chem 58:2491–2497
Williamson G, Clifford MN (2010) Colonic metabolites of berry polyphenols: the missing link to biological activity? Br J Nutr 104:S48–S66
Woodward GM, Needs PW, Kay CD (2011) Anthocyanin-derived phenolic acids form glucuronides following simulated gastrointestinal digestion and microsomal glucuronidation. Mol Nutr Food Res 55:378–386
Karlsen A, Retterstøl L, Laake P, Paur I, Kjølsrud-Bøhn S, Sandvik L, Blomhoff R (2007) Anthocyanins inhibit nuclear factor-kappaB activation in monocytes and reduce plasma concentrations of Pro-inflammatory mediators in healthy adults. J Nutr 137:1951–1954
DeFuria J, Bennett G, Strissel KJ, Perfield JW, Milbury PE, Greenberg AS, Obin MS (2009) Dietary blueberry attenuates whole-body insulin resistance in high fat-fed mice by reducing adipocyte death and its inflammatory sequelae. J Nutr 8:1510–1516
Talavera S, Felgines C, Texier O, Besson C, Gil-Izquierdo A, Lamaison JL, Remesy C (2005) Anthocyanin metabolism in rats and their distribution to digestive area, kidney, and brain. J Agric Food Chem 53:3902–3908
Kalt W, Blumberg JB, McDonald JE, Vinqvist-Tymchuk MR, Fillmore SAE, Graf BA, O’Leary JM, Milbury PE (2008) Identification of anthocyanins in the liver, eye, and brain of blueberry-fed pigs. J Agric Food Chem 56:705–712
Felgines C, Texier O, Garcin P, Besson C, Lamaison J-L, Scalbert A (2009) Tissue distribution of anthocyanins in rats fed a blackberry anthocyanin-enriched diet. Mol Nutr Food Res 53:1098–1103
Passamonti S, Vrhovsek U, Vanzo A, Mattivi F (2005) Fast access of some grape pigments to the brain. J Agric Food Chem 53:7029–7034
Passamonti S, Vrhovsek U, Mattivi F (2002) The interaction of anthocyanins with bilitranslocase. Biochem Biophys Res Commun 296:631–636
Hollman PC, Bijsman MN, van Gameren Y, Cnossen EP, de Vries JH, Katan MB (1999) The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free Radic Res 31:569–573
Gee JM, DuPont MS, Day AJ, Plumb GW, Williamson G, Johnson IT (2000) Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. J Nutr 130:2765–2771
Vitrac X, Krisa S, Decendit A, Vercauteren J, Nuhrich A, Monti JP, Deffieux G, Merillon JM (2002) Carbon-14 biolabelling of wine polyphenols in vitis vinifera cell suspension cultures. J Biotechnol 95:49–56
Fernandes I, Azevedo J, Faria A, Calhau C, de Freitas V, Mateus N (2008) Enzymatic hemisynthesis of metabolites and conjugates of anthocyanins. J Agric Food Chem 57:735–745
Cani PD, Delzenne NM (2009) The role of the gut microbiota in energy metabolism and metabolic disease. Curr Pharm Des 15:1546–1558
Goldberg DM, Yan J, Soleas GJ (2003) Absorption of three wine-related polyphenols in three different matrices by healthy subjects. Clin Biochem 36:79–87
Rechner AR, Smith MA, Kuhnle G, Gibson GR, Debnam ES, Srai SK, Moore KP, Rice-Evans CA (2004) Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Free Radic Biol Med 36:212–225
Slimestad R, Fossen T, Vagen IM (2007) Onions: a source of unique dietary flavonoids. J Agric Food Chem 55:10067–10080
Aura AM, Martin-Lopez P, O'Leary KA, Williamson G, Oksman-Caldentey KM, Poutanen K, Santos-Buelga C (2005) In vitro metabolism of anthocyanins by human gut microflora. Eur J Nutr 44:133–142
Gonthier MP, Cheynier V, Donovan JL, Manach C, Morand C, Mila I, Lapierre C, Remesy C, Scalbert A (2003) Microbial aromatic acid metabolites formed in the gut account for a major fraction of the polyphenols excreted in urine of rats fed red wine polyphenols. J Nutr 133:461–467
Selma MV, Espin JC, Tomas-Barberan FA (2009) Interaction between phenolics and gut microbiota: role in human health. J Agric Food Chem 57:6485–6501
Ley RE, Backhed F, Turnbaugh P, Lozupone CA, Knight RD, Gordon JI (2005) Obesity alters gut microbial ecology. Proc Natl Acad Sci USA 102:11070–11075
Cani PD, Delzenne NM (2011) The gut microbiome as therapeutic target. Pharmacol Ther 130:202–212
Verstraeten S, Fraga C, Oteiza P (2010) Flavonoids–membrane interactions: consequences for biological actions. In: Fraga C (ed) Plant phenolics and human health. Wiley, Hoboken NJ, pp 107–136
Daayf F, Lattanzio V (2008) Recent advances in polyphenol research. Wiley-Blackwell/Oxford, Chichester/Ames, pp 1–379
Milbury PE, Vita JA, Blumberg JB (2010) Anthocyanins are bioavailable in humans following an acute dose of cranberry juice. J Nutr 140:1099–1104
Ohnishi R, Ito H, Kasajima N, Kaneda M, Kariyama R, Kumon H, Hatano T, Yoshida T (2006) Urinary excretion of anthocyanins in humans after cranberry juice ingestion. Biosci Biotechnol Biochem 70:1681–1687
Kay CD, Mazza GJ, Holub BJ (2005) Anthocyanins exist in the circulation primarily as metabolites in adult men. J Nutr 135:2582–2588
Felgines C, Talavera S, Texier O, Gil-Izquierdo A, Lamaison JL, Remesy C (2005) Blackberry anthocyanins are mainly recovered from urine as methylated and glucuronidated conjugates in humans. J Agric Food Chem 53:7721–7727
Frank T, Janßen M, Netzel M, Straß G, Kler A, Kriesl E, Bitsch I (2005) Pharmacokinetics of anthocyanidin-3-glycosides following consumption of Hibiscus sabdariffa L. extract. J Clin Pharmacol 45:203–210
Bitsch I, Janssen M, Netzel M, Strass G, Frank T (2004) Bioavailability of anthocyanidin-3-glycosides following consumption of elderberry extract and blackcurrant juice. Int J Clin Pharmacol Ther 42:293–300
Bitsch R, Netzel M, Frank T, Strass G, Bitsch I (2004) Bioavailability and biokinetics of anthocyanins from red grape juice and red wine. J Biomed Biotechnol 5:293–298
Bitsch R, Netzel M, Sonntag S, Strass G, Frank T, Bitsch I (2004) Urinary excretion of cyanidin glucosides and glucuronides in healthy humans after elderberry juice ingestion. J Biomed Biotechnol 5:343–345
Kay CD, Mazza G, Holub BJ, Wang J (2004) Anthocyanin metabolites in human urine and serum. Br J Nutr 91:933–942
Frank T, Netzel M, Strass G, Bitsch R, Bitsch I (2003) Bioavailability of anthocyanidin-3-glucosides following consumption of red wine and red grape juice. Can J Physiol Pharmacol 81:423–435
Felgines C, Talavera S, Gonthier MP, Texier O, Scalbert A, Lamaison JL, Remesy C (2003) Strawberry anthocyanins are recovered in urine as glucuro- and sulfoconjugates in humans. J Nutr 133:1296–1301
Nielsen IL, Dragsted LO, Ravn-Haren G, Freese R, Rasmussen SE (2003) Absorption and excretion of black currant anthocyanins in humans and Watanabe heritable hyperlipidemic rabbits. J Agric Food Chem 51:2813–2820
Mazza G, Kay CD, Cottrell T, Holub BJ (2002) Absorption of anthocyanins from blueberries and serum antioxidant status in human subjects. J Agric Food Chem 50:7731–7737
Wu X, Cao G, Prior RL (2002) Absorption and metabolism of anthocyanins in elderly women after consumption of elderberry or blueberry. J Nutr 132:1865–1871
Bub A, Watzl B, Heeb D, Rechkemmer G, Briviba K (2001) Malvidin-3-glucoside bioavailability in humans after ingestion of red wine, dealcoholized red wine and red grape juice. Eur J Nutr 40:113–120
Matsumoto H, Inaba H, Kishi M, Tominaga S, Hirayama M, Tsuda T (2001) Orally administered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. J Agric Food Chem 49:1546–1551
Murkovic M, Mülleder U, Adam U, Pfannhauser W (2001) Detection of anthocyanins from elderberry juice in human urine. J Sci Food Agric 81:934–937
Netzel M, Strass G, Janssen M, Bitsch I, Bitsch R (2001) Bioactive anthocyanins detected in human urine after ingestion of blackcurrant juice. J Environ Pathol Toxicol Oncol 20:7
Lapidot T, Harel S, Granit R, Kanner J (1998) Bioavailability of red wine anthocyanins as detected in human urine. J Agric Food Chem 46:4297–4302
Acknowledgments
This work was supported by Fundação para a Ciência e Tecnologia (FCT) – Fundo Social Europeu, Programa Operacional Potencial Humano da EU and by studentship grants (SFRH/BPD/75294/2010 and SFRH/BD/38883/2007) and one research grant (PTDC/QUI/65501/2006).
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Faria, A., Fernandes, I., Mateus, N., Calhau, C. (2013). Bioavailability of Anthocyanins. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_75
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