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Absorption and metabolism of red orange juice anthocyanins in rats

Published online by Cambridge University Press:  08 March 2007

Catherine Felgines ,
Séverine Talavéra ,
Odile Texier ,
Catherine Besson ,
Vincenzo Fogliano ,
Jean-Louis Lamaison ,
Luca la Fauci ,
Giacomo Galvano ,
Christian Rémésy  and
Fabio Galvano
Catherine Felgines*
Affiliation:
Laboratoire de PharmacognosieFaculté de Pharmacie Clermont-Ferrand, France
Séverine Talavéra
Affiliation:
Laboratoire de PharmacognosieFaculté de Pharmacie Clermont-Ferrand, France
Odile Texier
Affiliation:
Laboratoire de PharmacognosieFaculté de Pharmacie Clermont-Ferrand, France
Catherine Besson
Affiliation:
Laboratoire des Maladies Métaboliques et des Micronutriments, Institut National de la Recherche Agronomique de Clermont-Ferrand/Theix, France
Vincenzo Fogliano
Affiliation:
Department of Food Science, University of Naples ‘Federico II‘, NaplesItaly
Jean-Louis Lamaison
Affiliation:
Laboratoire de PharmacognosieFaculté de Pharmacie Clermont-Ferrand, France
Luca la Fauci
Affiliation:
Department of Agro-forestry and Environmental Science, Mediterranean University of Reggio Calabria, Italy
Giacomo Galvano
Affiliation:
Department of Agronomical, Agrochemical and Animal Production Science, University of CataniaItaly
Christian Rémésy
Affiliation:
Laboratoire des Maladies Métaboliques et des Micronutriments, Institut National de la Recherche Agronomique de Clermont-Ferrand/Theix, France
Fabio Galvano
Affiliation:
Department of Agro-forestry and Environmental Science, Mediterranean University of Reggio Calabria, Italy
*
*Corresponding author: Dr. C. Felgines, fax +33 4 73 28 28 49, email Catherine.felgines@u-clermontl.fr
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Abstract

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Anthocyanins are natural pigments that could be involved in various health effects. Red oranges are an important dietary source of anthocyanins, including cyanidin 3-glucoside (Cy 3-glc) and an acylated derivative, cyanidin 3-(600-malonyl)-glucoside (Cy 3-malglc). The aim of this study was to evaluate the absorption and metabolism of red orange anthocyanins in rats fed an anthocyanin-enriched diet for 12 d (approximately 2·8 μmol anthocyanins/d). Furthermore, the absorption of these anthocyanins was studied in both the stomach and intestine using in situ models in rats. Anthocyanin metabolites were identified and quantified by HPLC–electrospray ionization tandem MS and HPLC–diode array detection, respectively. The red orange anthocyanins, Cy 3-glc and Cy 3-malglc, as well as their respective methylated derivatives, were recovered in urine after red orange juice intake. The 24 h urinary excretion of total anthocyanins was low (0·081 (SEM 0·009) % of the ingested amount). However, a high proportion (about 20 %) of red orange anthocyanins was absorbed from the stomach. More Cy 3- malglc than Cy 3-glc was absorbed in the intestine. This study thus indicated that red orange juice anthocyanins were rapidly absorbed from both stomach and small intestine, and then excreted in the urine as intact and methylated forms. Moreover, the absorption and metabolism of acylated anthocyanins and non-acylated anthocyanins were similar.

Keywords

Red orange anthocyaninsRatAbsorptionMetabolismAcylation
Type
Research Article
Information
British Journal of Nutrition , Volume 95 , Issue 5 , May 2006 , pp. 898 - 904
Copyright
Copyright © The Nutrition Society 2006

References

Bitsch, I, Janssen, M, Netzel, M, Strass, G & Frank, TBioavailability of anthocyanidin-3-glycosides following consumption of elderberry extract and blackcurrant juice. Int J Clin Pharmacol Ther 2004 42, 293 – 300.CrossRefGoogle ScholarPubMed
Bub, A, Watzl, B, Heeb, D, Rechkemmer, G & Briviba, KMalvidin- 3-glucoside bioavailability in humans after ingestion of red wine, dealcoholized red wine and red grape juice. Eur J Nutr 2001 40, 113 – 120.CrossRefGoogle ScholarPubMed
Cao, G, Muccitelli, HU, Sanchez-Moreno, C & Prior, RLAnthocyanins are absorbed in glycated forms in elderly women: a pharmacokinetic study. Am J Clin Nutr 2001 73, 920 – 926.CrossRefGoogle ScholarPubMed
Cooney, JM, Jensen, DJ & McGhie, TKLC-MS identification of anthocyanins in boysenberry extract and anthocyanin metabolites in human urine following dosing. J Sci Food Agric 2004 84, 237 – 245.CrossRefGoogle Scholar
Crespy, V, Morand, C, Besson, C, Manach, C, Demigné, C & Rémésy, CQuercetin, but not its glycosides, is absorbed from the rat stomach. J Agric Food Chem 2002 50, 618 – 621.CrossRefGoogle Scholar
Dugo, P, Mondello, L, Morabito, D & Dugo, GCharacterization of the anthocyanin fraction of Sicilian blood orange juice by micro-HPLC-ESI/MS. J Agric Food Chem 2003 51, 1173 – 1176.CrossRefGoogle ScholarPubMed
Felgines, C, Talavéra, S, Gonthier, MP, Texier, O, Scalbert, A, Lamaison, JL & Rémésy, CStrawberry anthocyanins are recovered in urine as glucuro- and sulfoconjugates in humans. J Nutr 2003 133, 1296 – 1301.CrossRefGoogle ScholarPubMed
Felgines, C, Texier, O, Besson, C, Fraisse, D, Lamaison, JL & Rémésy, FBioavailability of the flavanone naringenin and its glycosides in rats. Am J Physiol 2000 279, G1148 – G1154.Google ScholarPubMed
Fimognari, C, Berti, F, Nusse, M, Cantelli-Forti, G & Hrelia, PInduction of apoptosis in two human leukemia cell lines as well as differentiation in human promyelocytic cells by cyanidin-3-Obeta- glucopyranoside. Biochem Pharmacol 2004 67, 2047 – 2056.CrossRefGoogle ScholarPubMed
Fleschhut, J, Kratzer, F, Rechkemmer, G & Kulling, SEStability and biotransformation of various dietary anthocyanins in vitro. Eur J Nutr, 2006 45, 7 – 18.CrossRefGoogle ScholarPubMed
Frank, T, Netzel, M, Strass, G, Bitsch, R & Bitsch, IBioavailability of anthocyanidin-3-glucosides following consumption of red wine and red grape juice. Can J Physiol Pharmacol 2003 81, 423 – 435.CrossRefGoogle ScholarPubMed
Galvano, F, La Fauci, L, Lazzarino, G, Fogliano, V, Ritieni, A, Ciappellano, S, Battistini, NC, Tavazzi, B & Galvano, GCyanidins: metabolism and biological properties. J Nutr Biochem 2004 15, 2 – 11.CrossRefGoogle ScholarPubMed
Giusti, MM & Wrolstad, REAcylated anthocyanins from edible sources and their applications in food systems. Biochem Eng J 2003 14, 217 – 225.CrossRefGoogle Scholar
Griffiths, LA & Smith, GEMetabolism of myricetin and related compounds in the rat. Metabolite formation in vivo and by the intestinal microflora in vitro. Biochem J 1972 130, 141 – 151.CrossRefGoogle ScholarPubMed
Harada, K, Kano, M, Takayanagi, T, Yamakawa, O & Ishikawa, FAbsorption of acylated anthocyanins in rats and humans after ingesting an extract of Ipomoea batatas purple sweet potato tuber. Biosci Biotechnol Biochem 2004 68, 1500 – 1507.CrossRefGoogle ScholarPubMed
Hillebrand, S, Schwarz, M & Winterhalter, PCharacterization of anthocyanins and pyranoanthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juice. J Agric Food Chem 2004 52, 7331 – 7338.CrossRefGoogle ScholarPubMed
Ichiyanagi, T, Rahman, MM, Kashiwada, Y, Ikeshiro, Y, Shida, Y, Hatano, Y, Matsumoto, H, Hirayama, M, Tsuda, T & Konishi, TAbsorption and metabolism of delphinidin 3-O-beta-D-glucopyranoside in rats. Free Radic Biol Med 2004 36, 930 – 937.CrossRefGoogle ScholarPubMed
Ichiyanagi, T, Shida, Y, Rahman, MM, Hatano, Y, Matsumoto, H, Hirayama, M & Konishi, TMetabolic pathway of cyanidin 3-O-beta-D-glucopyranoside in rats. Agric Food Chem 2005 53, 145–150.CrossRefGoogle ScholarPubMed
Kay, CD, Mazza, G, Holub, BJ & Wang, JAnthocyanin metabolites in human urine and serum. Br J Nutr 2004 91, 933–942.CrossRefGoogle ScholarPubMed
Kühnau, JThe flavonoids. A class of semi-essential food components: their role in human nutrition. World Rev Nutr Diet 1976 24, 117–191.CrossRefGoogle ScholarPubMed
Lee, HSCharacterization of major anthocyanins and the color of red-fleshed Budd Blood orange(Citrus sinensis). J Agric Food Chem 2002 50, 1243–1246.CrossRefGoogle ScholarPubMed
McGhie, TK, Ainge, GD, Barnett, LE, Cooney, JM & Jensen, DJAnthocyanin glycosides from berry fruit are absorbed and excreted unmetabolized by both humans and rats. J Agric Food Chem 2003 51, 4539–4548.CrossRefGoogle ScholarPubMed
Matsumoto, H, Inaba, H, Kishi, M, Tominaga, S, Hirayama, M & Tsuda, TOrally 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 2001 49, 1546–1551.CrossRefGoogle ScholarPubMed
Mazza, G, Kay, CD, Cottrell, T & Holub, BJAbsorption of anthocyanins from blueberries and serum antioxidant status in human subjects. J Agric Food Chem 2002 50, 7731–7737.CrossRefGoogle ScholarPubMed
Miyazawa, T, Nakagawa, K, Kudo, M, Muraishi, K & Someya, KDirect intestinal absorption of red fruit anthocyanins, cyanidin-3-glucoside and cyanidin-3,5-diglucoside, into rats and humans. J Agric Food Chem 1999 47, 1083–1091.CrossRefGoogle ScholarPubMed
Mulleder, U, Murkovic, M & Pfannhauser, WUrinary excretion of cyanidin glycosides. J Biochem Biophys Methods 2002 53, 61–66.CrossRefGoogle ScholarPubMed
Nielsen, IL, Dragsted, LO, Ravn-Haren, G, Freese, R & Rasmussen, SEAbsorption and excretion of black currant anthocyanins in humans and Watanabe heritable hyperlipidemic rabbits. J Agric Food Chem 2003 51, 2813–2820.CrossRefGoogle ScholarPubMed
Passamonti, S, Vrhovsek, U & Mattivi, FThe interaction of anthocyanins with bilitranslocase. Biochem Biophys Res Commun 2002 296, 631–636.CrossRefGoogle ScholarPubMed
Passamonti, S, Vrhovsek, U, Vanzo, A & Mattivi, FThe stomach as a site for anthocyanins absorption from food. FEBS Lett 2003 544, 210–213.CrossRefGoogle ScholarPubMed
Powell, DW & Malawer, SJRelationship between water and solute transport from isosmotic solutions by rat intestine in vivo. Am J Physiol 1968 215, 49–55.CrossRefGoogle ScholarPubMed
Renaud, S & de Lorgeril, MWine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 1992 339, 1523–1526.CrossRefGoogle ScholarPubMed
Suda, I, Oki, T, Masuda, M, Nishiba, Y, Furuta, S, Matsugano, K, Sugita, K & Terahara, NDirect absorption of acylated anthocyanin in purple-fleshed sweet potato into rats. J Agric Food Chem 2002 50, 1672–1676.CrossRefGoogle ScholarPubMed
Talavéra, S, Felgines, C, Texier, O, Besson, C, Gil-Izquierdo, A, Lamaison, JL & Rémésy, CAnthocyanin metabolism in rats and their distribution to digestive area, kidney, and brain. J Agric Food Chem 2005 53, 3902–3908.CrossRefGoogle ScholarPubMed
Talavéra, S, Felgines, C, Texier, O, Besson, C, Lamaison, JL & Rémésy, CAnthocyanins are efficiently absorbed from the stomach in anesthetized rats. J Nutr 2003 133, 4178–4182.CrossRefGoogle ScholarPubMed
Talavéra, S, Felgines, C, Texier, O, Besson, C, Manach, C, Lamaison, JL & Rémésy, CAnthocyanins are efficiently absorbed from the small intestine in rats. J Nutr 2004 134, 2275–2279.CrossRefGoogle ScholarPubMed
Talavéra, S, Felgines, C, Texier, O, Besson, C, Mazur, A, Lamaison, J-L & Rémésy, CBioavailability of a bilberry anthocyanin extract and its impact on plasma antioxidant capacity in rats. J Sci Food Agric 2006 86, 90–97.CrossRefGoogle Scholar
Tsuda, T, Horio, F & Osawa, TDietary cyanidin 3-O-beta-D-glucoside increases ex vivo oxidation resistance of serum in rats. Lipids 1998 33, 583–588.CrossRefGoogle ScholarPubMed
Tsuda, T, Horio, F & Osawa, TAbsorption and metabolism of cyanidin 3-O-beta-D-glucoside in rats. FEBS Lett 1999 449, 179–182.CrossRefGoogle ScholarPubMed
Walgren, RA, Lin, JT, Kinne, RK & Walle, TCellular uptake of dietary flavonoid quercetin 4-beta-glucoside by sodium-dependent glucose transporter SGLT1. J Pharmacol Exp Ther 2000 294, 837–843.Google Scholar
Wang, J & Mazza, GEffects of anthocyanins and other phenolic compounds on the production of tumor necrosis factor alpha in LPS/IFN-gamma-activated RAW 264.7 macrophages. J Agric Food Chem 2002 50, 4183–4189.CrossRefGoogle ScholarPubMed
Wolffram, S, Block, M & Ader, PQuercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine. J Nutr 2002 132, 630–635.CrossRefGoogle ScholarPubMed
Wu, X, Cao, G & Prior, RLAbsorption and metabolism of anthocyanins in elderly women after consumption of elderberry or blueberry. J Nutr 2002 132, 1865–1871.Google ScholarPubMed
Youdim, KA, McDonald, J, Kalt, W & Joseph, JAPotential role of dietary flavonoids in reducing microvascular endothelium vulnerability to oxidative and inflammatory insults. J Nutr Biochem 2002 13, 282–288.CrossRefGoogle ScholarPubMed