Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two dose of orange juice

European Journal of Clinical Nutrition

Volumn 57, Issue 2, 2003, Pages 235-242

  Manach, C ^a   Morand, C ^a   Gil Izquierdo, A ^b   Bouteloup Demange, C ^c   Remesy C ^a  

^a CEMAGREF   (France)

^b RESEARCH GROUP ON QUALITY   (Spain)

^c CRNH AUVERGNE   (France)

Author keywords

Bioavailability in humans; Flavanone; Hesperetin; Naringerin; Orange juice

Indexed keywords

ANTIOXIDANT; FLAVANONE DERIVATIVE; GLUCURONIDE; HESPERETIN; HESPERIDIN; NARINGENIN; NARIRUTIN; POLYPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ADULT; ANTIOXIDANT ACTIVITY; ARTICLE; BIOAVAILABILITY; BLOOD LEVEL; BLOOD SAMPLING; CITRUS FRUIT; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIET RESTRICTION; FOOD INTAKE; HUMAN; HUMAN EXPERIMENT; MALE; NORMAL HUMAN; ORANGE JUICE; URINALYSIS; URINARY EXCRETION;

ADULT; BEVERAGES; BIOLOGICAL AVAILABILITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS; DOSE-RESPONSE RELATIONSHIP, DRUG; FLAVANONES; FLAVONOIDS; HESPERIDIN; HUMANS; MALE; REFERENCE VALUES; TIME FACTORS;

CITRUS;

EID: 0037327340     PISSN: 09543007     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.ejcn.1601547     Document Type: Article

References (53)

1. Ameer B, Weintraub RA, Johnson JV, Yost RA & Rouseff RL (1996): Flavanone absorption after naringin, hesperidin, and Citrus administration. Clin. Pharmac. Ther. 60, 34-40.
2. Aziz AA, Edwards CA, Lean MEJ & Crozier A (1998): Absorption and excretion of conjugated flavonols, including quercetin-4′-O-glucoside and isorhamnetin-4′-O-glucoside by human volunteers after the consumption of onions. Free Rad. Res. 29, 257-269.
3. Berkarda B, Koyuncu H, Soybir G & Baykut F (1998): Inhibitory effect of hesperidin on tumour initiation and promotion in mouse skin. Res. Exp. Med. (Berl.) 198, 93-99.
4. Bok SH, Lee SH, Park YB, Bae KH, Son KH, Jeong TS & Choi MS (1999): Plasma and hepatic cholesterol and hepatic activities of 3-hydroxy-3-methyl-glutaryl-CoA reductase and acyl CoA: cholesterol transferase are lower in rats fed citrus peel extract or a mixture of citrus bioflavonoids. J. Nutr. 129, 1182-1185.
5. Bokkenheuser VD, Shackleton CHL & Winter J (1987): Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans. Biochem. J. 248, 953-956.
6. Booth AN, Jones Fr & DeEds F (1958): Metabolic and glucosuria studies on naringin and phloridzin. J. Biol. Chem. 233, 280-282.
7. Borradaile NM, Carroll KK & Kurowska EM (1999): Regulation of HepG2 cell apolipoprotein B metabolism by the citrus flavanones hesperetin and naringenin. Lipids 34, 591-598.
8. Choudhury R, Chowrimootoo G, Srai K, Debnam E & Rice-Evans CA (1999): Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation. Biochem. Biophys. Res. Commun. 265, 410-415.
9. Day AJ, Bao Y, Morgan MR & Williamson G (2000): Conjugation position of quercetin glucuronides and effect on biological activity. Free Rad. Biol. Med. 29, 1234-1243.
10. Donovan JL, Bell JR, Kasim-Karakas S, German JB, Walzem RL, Hansen RJ & Waterhouse AL (1999): Catechin is present as metabolites in human plasma after consumption of red wine. J. Nutr. 129, 1662-1668.
11. Erlund I, Kosonen T, Alfthan G, Maenpaa J, Perttunen K, Kenraali J, Parentainen J & Aro A (2000): Pharmacokinetics of quercetin from quercetin aglycone and rutin in healthy volunteers. Eur. J. Clin. Pharmac. 56, 545-553.
12. Erlund I, Meririnne E, Alfthan G & Aro A (2001): Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice. J. Nutr. 131, 235-241.
13. Felgines C, Texier O, Morand C, Manach C, Scalbert A., Régérat F & Rémésy C (2000): Bioavailability of the flavanone naringenin and its glycosides in rats. Am. J. Physiol. Gastrointest. Liver Physiol. 279, G1148-G1154.
14. Fuhr U (1998): Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance. Drug Saf. 18, 251-272.
15. Fuhr U & Kummert AL (1995): The fate of naringin in humans: a key to grapefruit juice-drug interactions? Clin. Pharmac. Ther. 58, 365-373.
16. Gil-Izquierdo A, Gil MI, Ferreres F & Tomás-Barberán FA (2001): In vitro availability of flavonoids; and other phenolics in orange juice. J. Agric. Food Chem. 49, 1035-1041.
17. Gläßer G, Graefe EU, Struck F, Veit M & Gebhardt R (2002): Comparison of antioxydative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites. Phytomedicine 9, 33-40.
18. Graëfe EU, Wittig J, Mueller S, Riethling AK, Uehleke B, Drewelow B, Pforte H, Jacobasch G, Derendorf H & Veit M (2001): Pharmacokinetics and bioavailability of quercetin glycosides in humans. J. Clin. Pharmac. 41, 492-499.
19. Griffiths LA & Barrow A (1972): Metabolism of flavonoid compounds in germ-free rats. Biochem. J. 130, 1161-1162.
20. Hackett AM, Marsh I, Barrow A & Griffiths LA (1979): The biliairy excretion of flavanones in the rat. Xenobiotica 9, 491-501.
21. Hertog MGL, Hollman PC, Katan MB & Kromhout D (1993): Intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands. Nutr. Cancer 20, 21-29.
22. Hiermann A, Schramm HW & Laufer S (1998): Anti-inflammatory activity of myricetin-3-O-β-D-glucuronide and related compounds. Inflamm. Res. 47, 421-427.
23. Hollman PCH, van Trijp JMP, Buysman MN, van der Gaag MS, Mengelers MJ, de Vries JH & Katan MB (1997): Relative bioavailability of the antioxidant quercetin from various foods in man. FEBS Lett. 418, 152-156.
24. Hollman PCH, Bijsman M, van Gameren Y, Cnossen EPJ, de Vries JHM & Katan MB (1999): The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free Rad. Res. 31, 569-573.
25. Ishii K, Furuka T & Kasuya Y (2000): Mass spectrometric identification and high-performance liquid chromatography determination of a flavonoid glycoside naringin in human urine. J. Agric. Fd Chem. 46, 56-59.
26. Justesen U, Knuthsen P & Leth T (1997): Determination of plant polyphenols in Danish foodstuffs by HPLC-UV and LC-MS detection. Cancer Lett. 114, 165-167.
27. King RA & Bursill DB (1998): Plasma and urinary kinetics of the isoflavones daidzein and genistein after a single soy meal in humans. Am. J. Clin. Nutr. 67, 867-872.
28. Kumpulainen JT (2001): Intake of flavonoids, phenolic acids and lignans in various populations. In: 3rd International Conference on Natural Antioxidants and Anticarcinogens in Food, Health and Disease, ed. S Voutilainen & JT Salonen, p. 24. Kuopio: Kuopion University Publications D. Medical Sciences.
29. Lee YS & Reidenberg MM (1998): A method for measuring naringenin in biological fluids and its disposition from grapefruit juice by man. Pharmacology 56, 314-317.
30. Lee MJ, Wang ZY, Li H, Chen L, Sun Y, Gobbo S, Balentine DA & Yang CS (1995): Analysis of plasma and urinary tea polyphenols in human subjects. Cancer Epidemiol. Biomark. Prev. 4, 393-399.
31. Manach C, Morand C, Demigné C, Texier O, Régérat F & Rémésy C (1997): Bioavailability of rutin and quercetin in rats. FEBS Lett. 409, 12-16.
32. Manach C, Morand C, Crespy V, Demigné C, Texier O, Régérat F & Rémésy C (1998): Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett. 426, 331-336.
33. Merfort I, Heilmann J, Weiss M, Pietta P & Gardana C (1996): Radical scavenger activity of three flavonoid metabolites studied by inhibition of chemiluminescence in human PMNs. Planta Med. 62, 289-292.
34. Miyake Y, Yamamoto K, Tsujihara N & Osawa T (1998): Protective effects of lemon flavonoids on oxidative stress in diabetic rats. Lipids 33, 689-695.
35. Montforte MT, Trovato A, Kirjavainen S, Forestieri AM, Galati EM & Lo Curto RB (1995): Biological effects of hesperidin, a citrus flavonoid. Hypolipidemic activity on experimental hypercholesterolemia in rat. Il Farmaco 50, 595-599.
36. Moon JH, Tsushida T, Nakahara K & Terao J (2001): Identification of quercetin 3-O-β-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Rad. Biol. Med. 30, 1274-1285.
37. O'Leary KA, Day AJ, Needs PW, Sly, WS, O'Brien NM & Williamson G (2001): Flavonoid glucuronides are substrates for human beraglucuronidase. FEBS Lett. 503, 103-106.
38. Peng HW, Cheng FC, Huang YT, Chen CF & Tsai TH (1998): Determination of naringenin and its glucuronide conjugate in rat plasma and brain tissue by high-performance liquid chromatography. J. Chromatogr. B 714, 369-374.
39. Pietta P, Simonetti P, Roggi C, Brusamolino A, Pellegrini N, Maccarini L & Testolin G (1996): Dietary flavonoids and oxidative stress. In: Natural Antioxidant and Food Quality in Atherosclerosis and Cancer Prevention, ed. JT Kumpulainen & JT Salonen, pp 249-255. Cambridge: The Royal Society of Chemistry.
40. Rein D, Lolito S, Holt RR, Keen CL, Schmitz HH & Fraga CG (2000): Epicatechin in human plasma: in vivo determination and effect of chocolate consumption on plasma oxidation status. J. Nutr. 130, 2109S-2114S.
41. Rice-Evans C, Miller NJ & Paganga G (1996): Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Rad. Biol. Med. 20, 933-956.
42. Richelle M, Tavazzi I, Enslen M & Offord EA (1999): Plasma kinetics in man of epicatechin from black chocolate. Eur. J. Clin. Nutr. 53, 22-26.
43. Scheline RR (1991): Handbook of Mammalian Metabolism of Plant Compounds. Boca Raton, FL: CRC Press.
44. Shimoi K, Saka N, Nozawa R, Sato M, Amano I, Nakayama T & Kinae N (2001): Deglucuronidation of a flavonoid, luteolin monoglu-curonide, during inflammation. Drug Metab. Dispos. 29, 1521-1524.
45. Tanaka T, Makita H. Kawabata K, Mori H, Kakumoto M, Satoh K, Hara A, Sumida T, Tanaka T & Ogawa H (1997): Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin. Carcinogenesis 18, 957-965.
46. Tomás-Barberán FA & Clifford MN (2000): Flavanones, chalcones and dihydrochalcones - nature, occurrence and dietary burden. J. Sci. Fd Agric. 80, 1073-1080.
47. Unno T, Kondo K, Itakura. H & Terao T (1996): Analysis of (-)- epigallocatechin gallate in human serum obtained after ingesting green tea. Biosci. Biotechnol. Biochem. 60, 2068-2099.
48. Wang JF, Schramm DD, Holt RR, Ensunda JL, Fraga CG, Schmitz HH & Keen CL (2000): A dose-response effect from chocolate consumption on plasma epicatechin and oxidative damage. J. Nutr. 130, 2115S-2119S.
49. Watanabe S, Yamaguchi M, Sobue T, Takahashi T, Miura T, Arai Y, Mazur W, Wähälä K & Adlercreutz H (1998): Pharmacokinetics of soybean isoflavones in plasma, urine and feces of man after ingestion of 60g baked soybean powder (Kinako). J. Nutr. 128, 1710-1715.
50. Xu X, Wang HJ, Murphy PA, Cook L & Hendrich S (1994): Daidzein is a more available soymilk isoflavone than is genistein in adult women. J. Nutr. 124, 825-832.
51. Xu X, Wang HJ, Murphy PA & Hendrich S (2000): Neither background diet nor type of soy food affects short-term isoflavone bioavailability in women. J. Nutr. 130, 798-801.
52. Yang M, Tanaka T, Hirose Y, Deguchi T, Mon H & Kawada Y (1997): Chemopreventive effects of diosmin and hesperidin on n-butyl-n-(4-hydroxybutyl)nitrosamine-induced urinary bladder carcinogenesis in male ICR mice. Int. J. Cancer 73, 719-724.
53. Yang CS, Chen L, Lee MJ, Balentine D, Kuo MC & Shantz SP (1998): Blood and urine levels of tea catechins after ingestion of different amounts of green tea by human volunteers. Cancer Epidemiol. Biomark. Prev. 7, 351-354.