Mangiferin and hesperidin metabolites are absorbed from the gastrointestinal tract of pigs after oral ingestion of a Cyclopia genistoides (honeybush tea) extract

Nutrition Research

Volumn 28, Issue 12, 2008, Pages 879-891

  Bock, Constance ^a   Waldmann, Karl Heinz ^b   Ternes, Waldemar ^a  

^a UNIVERSITY OF VETERINARY MEDICINE HANNOVER   (Germany)

^b Small Ruminants   (Germany)

Author keywords

Feces; Gastrointestinal tract; Hesperidin; Mangiferin; Pigs; Plasma; Urine

Indexed keywords

CYCLOPIA GENISTOIDES EXTRACT; DRUG METABOLITE; ERIODICTYOL MONOGLUCURONIDE; HESPERETIN; HESPERETIN MONOGLUCURONIDE; HESPERIDIN; MANGIFERIN; METHYLMANGIFERIN; NORATHYRIOL; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BIOLOGICAL ACTIVITY; BLOOD SAMPLING; CONTROLLED STUDY; CYCLOPIA GENISTOIDES; DIETARY INTAKE; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG MECHANISM; DRUG METABOLISM; DRUG URINE LEVEL; FEMALE; FRACTIONATION; GASTROINTESTINAL ABSORPTION; IN VIVO STUDY; INGESTION; MEDICINAL PLANT; NONHUMAN; PRIORITY JOURNAL; SWINE;

ADMINISTRATION, ORAL; ANIMALS; GASTROINTESTINAL TRACT; HESPERIDIN; INTESTINAL ABSORPTION; PLANT EXTRACTS; SWINE; TEA; XANTHONES;

CYCLOPIA GENISTOIDES; SUIDAE;

EID: 59549084963     PISSN: 02715317     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nutres.2008.08.001     Document Type: Article

References (46)

1. Hertog M.G.L., Feskens E.J.M., Hollman P.C.H., Katan M.B., and Kromhout D. Dietary antioxidant flavonoids and risk of coronary heart-disease-the Zutphen Elderly Study. Lancet 342 (1993) 1007-1011
2. Arts I.C.W., and Hollman P.C.H. Polyphenols and disease risk in epidemiologic studies. Am J Clin Nutr 81 (2005) 317S-325S
3. Vita J.A. Polyphenols and cardiovascular disease: effects on endothelial and platelet function. Am J Clin Nutr 81 (2005) 292S-297S
4. Kamara B.I., Brandt E.V., Ferreira D., and Joubert E. Polyphenols from honeybush tea (Cyclopia intermedia). J Agric Food Chem 51 (2003) 3874-3879
5. Joubert E., Otto F., Gruener S., and Weinreich B. Reversed-phase HPLC determination of mangiferin, isomangiferin and hesperidin in Cyclopia and the effect of harvesting date on the phenolic composition of C. genistoides. Eur Food Res Technol 216 (2003) 270-273
6. Sanugul K., Akao T., Li Y., Kakiuchi N., Nakamura N., and Hattori M. Isolation of a human intestinal bacterium that transforms mangiferin to norathyriol and inducibility of the enzyme that cleaves a C-glucosyl bond. Biol Pharm Bull 28 (2005) 1672-1678
7. Guha S., Ghosal S., and Chattopadhyay U. Antitumor, immunomodulatory and anti-HIV effect of mangiferin, a naturally occurring glucosylxanthone. Chemotherapy 42 (1996) 443-451
8. Ichiki H., Miura T., Kubo M., Ishihara E., Komatsu Y., Tanigawa K., et al. New antidiabetic compounds, mangiferin and its glucoside. Biol Pharm Bull 21 (1998) 1389-1390
9. Sanchez G.M., Re L., Giuliani A., Nunez-Selles A.J., Davison G.P., and Leon-Fernandez O.S. Protective effects of Mangifera indica L. extract, mangiferin and selected antioxidants against TPA-induced biomolecules oxidation and peritoneal macrophage activation in mice. Pharmacol Res 42 (2000) 565-573
10. Yoshikawa M., Ninomiya K., Shimoda H., Nishida N., and Matsuda H. Hepatoprotective and antioxidative properties of Salacia reticulata: preventive effects of phenolic constituents on CCl4-induced liver injury in mice. Biol Pharm Bull 25 (2002) 72-76
11. Garcia D., Leiro J., Delgado R., Sanmartin M.L., and Ubeira F.M. Mangifera indica L. extract (Vimang) and mangiferin modulate mouse humoral immune responses. Phytother Res 17 (2003) 1182-1187
12. Lee H.Z., Lin W.C., Yeh F.T., Lin C.N., and Wu C.H. Decreased protein kinase C activation mediates inhibitory effect of norathyriol on serotonin-mediated endothelial permeability. Eur J Pharmacol 353 (1998) 303-313
13. Wang J.P., Ho T.F., Lin C.N., and Teng C.M. Effect of norathyriol, isolated from Tripterospermum lanceolatum, on A 23 187-induced pleurisy and analgesia in mice. Naunyn-Schmiedebergs Arch Pharmacol 350 (1994) 90-95
14. Ko F.N., Lin C.N., Liou S.S., Huang T.F., and Teng C.M. Vasorelaxation of rat thoracic aorta caused by norathyriol isolated from Gentianaceae. Eur J Pharmacol 192 (1991) 133-139
15. Teng C.M., Lin C.N., Ko F.N., Cheng K.L., and Huang T.F. Novel inhibitory actions on platelet thromboxane and inositolphosphate formation by xanthones and their glycosides. Biochem Pharmacol 38 (1989) 3791-3795
16. Geodakyan S.V., Voskoboinikova I.V., Tjukavkina N.A., Kolhir V.K., Kolesnik Y.A., Zjuzin V.A., et al. Experimental pharmacokinetics of biologically active plant phenolic compounds. 1. Pharmacokinetics of mangiferin in the rat. Phytother Res 6 (1992) 332-334
17. Dai R., Gao J., and Bi K. High-performance liquid chromatographic method for the determination and pharmacokinetic study of mangiferin in plasma of rats having taken the traditional Chinese medicinal preparation Zi-Shen pill. J Chromatogr Sci 42 (2004) 88-90
18. Lai L., Lin L.C., Lin J.H., and Tsai T.H. Pharmacokinetic study of free mangiferin in rats by microdialysis coupled with microbore high-performance liquid chromatography and tandem mass spectrometry. J Chromatogr A 987 (2003) 367-374
19. Gao K., Xu A.L., Krul C., Venema K., Liu Y., Niu Y.T., et al. Of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements, only 3,4-dihydroxyphenylacetic acid has antiproliferative activity. J Nutr 136 (2006) 52-57
20. Borradaile N.M., Carroll K.K., and Kurowska E.M. Regulation of HepG2 cell apolipoprotein B metabolism by the citrus flavanones hesperetin and naringenin. Lipids 34 (1999) 591-598
21. Chiba H., Uehara M., Wu J., Wang X.X., Masuyama R., Suzuki K., et al. Hesperidin, a citrus flavonoid, inhibits bone loss and decreases serum and hepatic lipids in ovariectomized mice. J Nutr 133 (2003) 1892-1897
22. Garg A., Garg S., Zaneveld L.J.D., and Singla A.K. Chemistry and pharmacology of the citrus bioflavonoid hesperidin. Phytother Res 15 (2001) 655-669
23. Zhang M., Zhang J.P., Ji H.T., Wang J.S., and Qian D.H. Effect of six flavonoids on proliferation of hepatic stellate cells in vitro. Acta Pharmacol Sin 21 (2000) 253-256
24. Booth A.N., Jones F.T., and DeEds F. Metabolic fate of hesperidin, eriodictyol, homoeriodictyol, and diosmin. J Biol Chem 230 (1958) 661-668
25. Hackett A.M., Marsh I., Barrow A., and Griffiths L.A. The biliary excretion of flavanones in the rat. Xenobiotica 9 (1979) 491-502
26. Bokkenheuser V.D., Shackleton C.H.L., and Winter J. Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans. Biochem J 248 (1987) 953-956
27. Manach C., Morand C., Gil-Izquierdo A., Bouteloup-Demange C., and Remesy C. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. Eur J Clin Nutr 57 (2003) 235-242
28. Ameer B., Weintraub R.A., Johnson J.V., Yost R.A., and Rouseff R.L. Flavanone absorption after naringin, hesperidin, and citrus administration. Clin Pharmac Ther 60 (1996) 34-40
29. Baba S., Osakabe N., Natsume N., Muto Y., Takizawa T., and Terao J. In vivo comparison of the bioavailability of (+)-catechin, (-)-epicatechin and their mixture in orally administered rats. J Nutr 131 (2001) 2885-2891
30. Walton C.W., McGhie T.K., Reynolds G.W., and Hendriks W.H. The flavonoid quercetin-3-glucoside inhibits cyaniding-3-glucoside absorption. J Agric Food Chem 54 (2006) 4913-4920
31. Miller E.R., and Ullrey D.E. The pig as a model for human nutrition. Ann Rev Nutr 7 (1987) 361-382
32. Erlund I., Kosonen T., Alfthan G., Maeenpaeae J., Perttunen K., Kenraali J., et al. Pharmacokinetics of quercetin from quercetin aglycone and rutin in healthy volunteers. Eur J Clin Pharm 56 (2000) 545-553
33. Cuyckens F., and Claeys M. Mass spectrometry in the structural analysis of flavonoids. J Mass Spectrom 39 (2004) 1-15
34. Frey H.H., and Löscher W. Lehrbuch der Pharmakologie und Toxikologie für die Veterinärmedizin (1996), Ferdinand Enke Verlag, Stuttgart
35. Hattori M., Shu Y.Z., Tomimori T., Kobashi K., and Namba T. A bacterial cleavage of the C-glucosyl bond of mangiferin and bergenin. Phytochemistry 28 (1989) 1289-1290
36. Papadopoulou A., and Frazier R.A. Characterization of protein-polyphenol interactions. Trends Food Sci Technol 15 (2004) 186-190
37. Spencer C.M., Cai Y., Martin R., Gaffney S.H., Goulding P.N., Magnolato D., et al. Polyphenol complexation-some thoughts and observations. Phytochemistry 27 (1988) 2397-2409
38. Brunet A.J., Blade C., Salvado M.J., and Arola L. Human apo A-I and rat transferrin are the principal plasma proteins that bind wine catechins. J Agric Food Chem 50 (2002) 2708-2712
39. Nielsen S.E., Breinholt V., Justesen U., Cornett C., and Dragsted L.O. In vitro biotransformation of flavonoids by rat liver microsomes. Xenobiotica 28 (1998) 389-401
40. Miyake Y., Shimoi K., Kumazawa S., Yamamoto K., Kinae N., and Osawa T. Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats. J Agric Food Chem 48 (2000) 3217-3224
41. Walle T., Walle U.K., and Halushka P.V. Carbon dioxide is the major metabolite of quercetin in humans. J Nutr 131 (2001) 2648-2652
42. Honohan T., Hale R.L., Brown J.P., and Wingard R.E. Synthesis and metabolic fate of hesperetin-3-C-14. J Agric Food Chem 24 (1976) 906-911
43. Olthof M.R., Hollman P.C.H., Buijsman M., van Amelsvoort J.M.M., and Katan M.B. Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. J Nutr 133 (2003) 1806-1814
44. Schneider H., and Blaut M. Anaerobic degradation of flavonoids by Eubacterium ramulus. Arch Microbiol 173 (2000) 71-75
45. Schoefer L., Mohan R., Schwiertz A., Braune A., and Blaut M. Anaerobic degradation of flavonoids by Clostridium orbiscindens. Appl Environ Microbiol 69 (2003) 5849-5854
46. Williamson G., Day A.J., Plumb G.W., and Couteau D. Human metabolic pathways of dietary flavonoids and cinnamates. Biochem Soc Trans 28 (2000) 16-22