Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects

European Journal of Clinical Nutrition

Volumn 61, Issue 4, 2007, Pages 472-477

  Kanaze, F I ^a   Bounartzi, M I ^a   Georgarakis, M ^a   Niopas, I ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

AGLYCONE; FLAVANONE DERIVATIVE; GLYCOSIDE; HESPERETIN; NARINGENIN; PHENOL DERIVATIVE;

ADULT; AREA UNDER THE CURVE; ARTICLE; CITRUS FRUIT; CONTROLLED STUDY; DIET RESTRICTION; DOSE TIME EFFECT RELATION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CAPSULE; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG URINE LEVEL; FEMALE; FIRST PASS EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN EXPERIMENT; HYDROLYSIS; INTESTINE FLORA; MALE; MAXIMUM PLASMA CONCENTRATION; MEAN RESIDENCE TIME; NORMAL HUMAN; PLASMA CONCENTRATION-TIME CURVE; SINGLE DRUG DOSE; TIME TO MAXIMUM PLASMA CONCENTRATION;

ADMINISTRATION, ORAL; ADULT; AREA UNDER CURVE; BIOLOGICAL AVAILABILITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS; DIETARY SUPPLEMENTS; FEMALE; FLAVANONES; HESPERIDIN; HUMANS; INTESTINAL ABSORPTION; MALE;

CITRUS;

EID: 34247212317     PISSN: 09543007     EISSN: 14765640     Source Type: Journal    
DOI: 10.1038/sj.ejcn.1602543     Document Type: Article

References (37)

1. Ameer B, Weintraub RA, Johnson JV, Yost RA, Rouseff RL (1996). Flavanone absorption after naringin, hesperidin, and citrus administration. Clin Pharmacol Ther 60, 34-40.
2. Berkarda B, Koyuncu H, Soybir G, Baykut F (1998). Inhibitory effect of hesperidin on tumour initiation and promotion in mouse skin. Res Exp Med (Berlin) 98, 93-99.
3. Bok SH, Lee SH, Park YB, Bae KH, Son KH, Jeong TS et al. (1999). Plasma and hepatic cholesterol and hepatic activities of 3-hydroxy-3-methyl-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.
4. Bokkenheuser VD, Shackleton CH, Winter J (1987). Hydrolysis of dietary flavonoids glycosides by strains of intestinal bacteroides from humans. Biochem J 1248, 953-956.
5. Booth AN, Jones FT, De Eds F (1958). Metabolic and glucosuria studies on naringin and phloridizin. J Biol Chem 233, 280-282.
6. Choudhury R, Chowrimootoo G, Stal K, Debnam E, Rice-Evans CA (1999). Interactions of the flavonoids naringenin in the gastrointestinal tract and the influence of glycosylation. Biochem Biophys Res Commun 265, 410-415.
7. Crespo ME, Galvez J, Cruz T, Ocete MA, Zarzuelo A (1999). Anti-inflammatory activity of diosmin and hesperidin in rat colitis induced by TNBS. Planta Med 65, 651-653.
8. 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.
9. Felgines C, Texler O, Morand C, Manach C, Scalbert A, Regerat F et al. (2000). Bioavailability of the flavanone naringenin and its glycosides in rats. Am J Physiol Gastroentest Liver Physiol 279 G1148-G1154.
10. Franke AA, Cooney RV, Henning SM, Custer LJ (2005). Bioavailability and antioxidant effects of orange juice components in humans. J Agric Food Chem 53, 5170-5178.
11. Fuhr U, Kummert AL (1995). The fate of naringin in humans: A key to grapefruit juice-drug interactions? Clin Pharmacol Ther 58, 365-573.
12. Gibaldi M, Perrier D (1982). Pharmacokinetics, 2nd edn. Marcel Dekker: New York.
13. Ghosal A, Saroh H, Thomas PE, Bush E, Moore D (1996). Inhibition and kinetics of cytochrome P450. Drug Metab Dispos 24, 940-947.
14. Hacket AM, Marsh I, Barrow A, Griffiths LA (1979). The biliary excretion of flavanones in the rat. Xenobiotica 9, 491-501.
15. Havsteen B (1983). Flavonoids, a class of natural products of high pharmacological potency. Biochem Pharmacol 32, 1141-1148.
16. Hollman PCH, Bijsman MNCP, van Gameren Y, Cnossen EP, de Vries JH, Katan MB (1999). The sugar moiety is a major determinant of the absorption of dietary flavonoids glycosides in man. Free Rad Res 31, 569-573.
17. Ishii K, Furuta T, Kasuya Y (2000). Mass spectrometric identification and high-performance liquid chromatographic determination of a flavonoids glycoside naringin in human urine. J Agric Food Chem 48, 56-59.
18. Jang IS, Kim DH (1996). Purification and characterization of alpha-L-rhamnosidase JK-6, a hyman intestinal bacterium. Biol Pharm Bull 19, 1546-1549.
19. Joshipura KJ, Ascherio A, Manson JE, Stampfer MJ, Rimm EB, Speizer FE et al. (1999). Fruit and vegetable intake in relation to risk of ischemic stroke. JAMA 282, 1233-1239.
20. Kanaze FI, Gabrieli C, Kokkalou E, Georgarakis M, Niopas I (2003). Simultaneous reversed-phase high-performance liquid chromatographic method for the determination of diosmin, hesperidin and naringin in different citrus fruit juices and pharmaceutical formulations. J Pharm Biomed Anal 33, 243-249.
21. Kanaze FI, Kokkalou E, Georgarakis M, Niopas I (2004a). A validated high performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous determination of naringenin and hesperetin in human plasma. J Chromatogr B 801, 363-367.
22. Kanaze FI, Kokkalou E, Georgarakis M, Niopas I (2004b). A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. J Pharm Biomed Anal 36, 175-181.
23. Kanaze FI, Kokkalou E, Niopas I, Georgarakis M, Stergiou A, Bikiaris D (2006a). Thermal analysis study of flavonoid solid dispersions having enhanced solubility. J Therm Anal Cal 83, 283-290.
24. Kanaze FI, Kokkalou E, Niopas I, Georgarakis M, Stergiou A, Bikiaris D (2006b). Dissolution enhancement of flavonoids by solid dispersions in PVP and PEG matrices. A comparative study. J Appl Polym Sci 102 460-471.
25. Kim DH, Jung EA, Sohng IS, Han JA, Kim TH, Han MJ (1998). Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Arch Pharm Res 21, 17-23.
26. Lee SH, Park YB, Bae KH, Bok SH, Kwon YK, Lee ES et al. (1999). Cholesterol-lowering activity of naringenin via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A:cHolesterol acyltransferase in rats. Ann Nutr Metab 43, 173-180.
27. 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.
28. Manach C, Morand C, Gil-Izquierdo A, Bouteloup-Demange C, Remesy C (2003). Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. Eur J Clin Nutr 57, 235-242.
29. Miyake Y, Yamamoto K, Tsujihara N, Osawa T (1998). Protective effects of lemon flavonoids on oxidative stress in diabetic rats. Lipids 33, 689-695.
30. Montforte MT, Trovato A, Kirjavainen S, Forestieri AM, Galati EM, Lo Cutro RB (1995). Biological effects of hesperidin a citrus flavonoid hypolipidemic activity on experimental hypercholesterolemia in rat. Il Farmaco 50, 595-599.
31. Nielsen ILF, Chee WSS, Poulsen L, Offord-Cavin E, Rasmussen SE, Frederiksen H et al. (2006). Bioavailability is improved by enzymatic modification of the citrus flavonoid hesperidin in humans: A randomized, double-blind, crossover trial. J Nutr 136, 404-408.
32. Rice-Evans C, Miller NG, Paganga G (1996). Structure antioxidant activity relationships of flavonoids and phenolic acids. Free Rad Biol Med 20, 833-956.
33. Rouseff RL, Martin SF, Youtsey CO (1987). Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in citrus. J Agric Food Chem 35, 1027-1030.
34. Rowland M, Tozer TN (1995). Clinical Pharmacokinetics: Concepts and Applications, 3rd edn. Lea & Febiger: Baltimore.
35. Santos KF. Oliveira TT, Nagem TJ, Pinto AS, Oliveira MG (1999). Hypolipidaemic effects of naringenin, rutin, nicotinic acid and their associations. Pharmacol Res 40, 493-496.
36. Tanaka T, Makita H, Kawabata K, Mori H, Kakumoto M, Satoh K et al. (1997). Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin. Carcinogenesis 18, 957-965.
37. 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.