Simultaneous determination of the flavonoid aglycones diosmetin and hesperetin in human plasma and urine by a validated GC/MS method: In vivo metabolic reduction of diosmetin to hesperetin

Biomedical Chromatography

Volumn 23, Issue 2, 2009, Pages 124-131

  Spanakis, Marios ^a   Kasmas, Stamatis ^a   Niopas, Ioannis ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Diosmetin; Diosmin; GC MS determination; Hesperetin; Metabolic reduction; Pharmacokinetics

Indexed keywords

BODY FLUIDS; CITRUS FRUITS; FLAVONOIDS; MASS SPECTROMETRY; SUGARS;

DIOSMETIN; DIOSMIN; FLAVONOID GLYCOSIDES; GC/MS DETERMINATION; HESPERETIN; HUMAN PLASMAS; HUMAN URINE; METABOLIC REDUCTION; PLASMA SAMPLES; SIMULTANEOUS DETERMINATIONS;

METABOLISM;

DIOSMETIN; DIOSMIN; HESPERETIN; HESPERIDIN; NARINGENIN;

ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG ELIMINATION; DRUG METABOLISM; DRUG STRUCTURE; DRUG URINE LEVEL; HUMAN; IN VIVO STUDY; MALE; MASS FRAGMENTOGRAPHY; NORMAL HUMAN; QUANTITATIVE ANALYSIS; REDUCTION KINETICS; SINGLE DRUG DOSE; STRUCTURE ANALYSIS; VALIDATION STUDY;

CITRUS;

EID: 65349171986     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1092     Document Type: Article

References (64)

1. Amiel M and Barbe R. Study of the pharmacodynamic activity of Daflon 500 mg. Annalesde Cardiologie et d'Angéilogie 1998; 47: 185.
2. Anila L and Vijayalakshmi NR. Beneficial effects of flavonoids from Sesamum indicum, Emblica officinalis and Momordica charantia. Phytotherapy Research 2000; 14: 592.
3. Bernatova I, Pechanova O, Babal P, Kysela S, Stvrtina S and Andriantsitohaina R. Wine polyphenols improve cardiovascular remodeling and vascular function in NO- deficient hypertension. American Journal of Physiology and Heart Circulation Physiology 2002; 282: H942.
4. Bok SH, Lee SH, Park YB, Bae KH, Son KH, Jeong TS and Choi MS. 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. Journal of Nutrition 1999; 129: 1182.
5. Borradaile NM, Carroll KK and Kurowska EM. Regulation of HepG2 cell apolipoprotein B metabolism by the citrus flavanones hesperetin and naringenin. Lipids 1999; 34: 591.
6. Bouskela E, Cyrino FZ and Lerond L. Effects of oral administration of different doses of purified micronised flavonoid fraction on microvascular reactivity after ischaemia/reperfusion in the hamster cheek pouch. British Journal of Pharmacology 1997; 122: 1611.
7. Boutin JA, Meunier F, Lambert PH, Henning P, Bertin D, Serkiz B and Volland JP. In vivo and in vitro glucuronidation of the flavonoid diosmetin in rats. Drug Metabolism and Disposition 1993; 21: 1157.
8. Braune A, Gutschow M, Engst W and Blaut M. Degradation of quercetin and luteolin by Eubacterium ramulus. Applied Environmental Microbiology 2001; 67: 5558.
9. Buckshee K, Takkar D and Aggarwal N. Micronised flavonoid therapy in internal hemorrhoids of pregnancy. International Gynaecology and Obstetrics 1997; 57: 145.
10. Crespo ME, Galvez J, Cruz T, Ocete MA and Zarzuelo A. Anti-inflammatory activity of diosmin and hesperidin in rat colitis induced by TNBS. Planta Medica 1999; 65: 651.
11. Di Perri T and Auteri A. Action of S 5682 on the complement system. International Angiology 1988; 7 (suppl. 2): 11.
12. Erlund I, Meririnne A, Alfthan G and Aro A. Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice. Journal of Nutrition 2001; 131, 235.
13. Erlund I. Review of the flavonoids quercetin, hesperetin and naringenin. Dietatry sources, bioactivities, bioavailability and epidemiology. Nutrition Research 2004; 24: 851.
14. Felgines C, Texler O, Morand C, Manach C, Scalbert A, Regerat F and Remesy C. Bioavailability of the flavanone naringenin and its glycosides in rats. American Journal of Physiology. Gastrointestinal and Liver Physiology 2000; 279: G1148.
15. Franke AA, Cooney RV, Henning SM and Custer LJ. Bioavailability and antioxidant effects of orange juice components in humans. Journal of Agricultural Food Chemistry 2005; 53: 5170.
16. Galley P and Thiollet M. A double-blind, placebo-controlled trial of a new veno-active flavonoid fraction (S 5682) in the treatment of symptomatic capillary fragility. International Angiology 1993; 12: 69.
17. Gardana C, Guarnieri S, Riso P, Simonetti P and Porrini M. Flavanone plasma pharmacokinetics from blood orange juice in human subjects. British Journal of Nutrition 2007; 98: 165.
18. Gibaldi M and Perrier D. Pharmacokinetics, 2nd edn. Marcel Dekker: New York, 1982.
19. Gova D, De Angelis L, Giavarini F, Palladini G and Perego R. Pharmacokinetics and metabolism of oral diosmin in healthy volunteers. International Journal of Clinical Pharmacology and Therapeutic Toxicology 1992; 30: 29.
20. Gradolatto A, Canivenc-Lavier MC, Basly JP, Siess MH and Teyssier C. Metabolism of apigenin by rat phase I and phase II enzymes and by isolated perfused rat liver. Drug Metabolism and Disposition 2004; 32: 58.
21. Guilhou JJ, Dereure O, Marzin L, Ouvry P, Zuccarelli F, Debure C, Van Landuyt H, Gillet-Terver MN, Guillot B, Levesque H, Mignot J, Pillion G, Fevrier B and Dubeaux D. Efficacy of Daflon 500 mg in venous leg ulcer healing: a double-blind, randomized, controlled versus placebo trial in 107 patients. Angiology 1997; 48: 77.
22. Guillot B. Techniques used to evaluate the cutaneous microcirculation: application of photoplethysmography to the assessment of a phlebotropic agent in the treatment of leg ulcers. Angiology 1994; 45: 542.
23. Havsteen BH. The biochemistry and medicinal significance of the flavonoids. Pharmacological Therapy 2002; 96: 67.
24. Hertog MGL, Kromhout D, Aravanis C, Blackburn H, Buzina R, Fidanza F, Giampaoli S, Jansen A, Menotti A, Nedeljkovic S, Pekkarinen M, Simic BS, Toshima H, Feskens EIM, Hollman PCH and Katan MB. Flavonoid intake and long-term risk of coronary-heart-disease and cancer in the 7 countries study. Archives of Internal Medicine 1995; 155: 381.
25. Izzo AA, Di Carlo G, Mascolo N, Capasso F and Autore G. Antiulcer effect of flavonoids - role of endogenous PAF. Phytotherapy Research 1994; 8: 179.
26. Justesen U, Knuthsen P and Leth T. Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables and beverages by high-performance liquid chromatography with photo-diode array and mass spectrometric detection. Journal of Chromatography A 1998; 799: 101.
27. Kanaze FI, Gabrieli C, Kokkalou E, Georgarakis M and Niopas I. Simultaneous reversed-phase high-performance liquid chromatographic method for the determination of diosmin, hesperidin and naringin in different citrus fruit juices and pharmaceutical formulations. Journal of Pharmaceutical Biomedical Analysis 2003; 33: 243.
28. Kanaze FI, Kokkalou E, Georgarakis M and Niopas I. A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. Journal of Pharmaceutical and Biomedical Analysis 2004a; 36: 175.
29. Kanaze FI, Bounartzi MI and Niopas I. A validated HPLC determination of the flavone aglycone diosmetin in human plasma Biomedical Chromatography 2004b; 18: 800.
30. Kanaze FI, Kokkalou E, Georgarakis M and Niopas I. A validated high performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous determination of naringenin and hesperetin in human plasma. Journal of Chromatography B 2004c; 801: 363.
31. Kanaze FI, Bounartzi MI, Georgarakis M and Niopas I. Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects. European Journal of Clinical Nutrition 2007; 61: 472.
32. Kandaswami C and Middleton E Jr. Free radical scavenging and antioxidant activity of plant flavonoids. Advances in Experimental Medical Biology 1994; 366: 351.
33. Kanes K, Tisserat B, Berhow M and Vandercook C. Phenolic composition of various Rutaceae species. Phytochemistry 1993; 32: 967.
34. Katsenis K. Micronised purified flavonoid fraction (MPFF): a review of its pharmacological effects, therapeutic efficacy and benefits in the management of chronic venous insufficiency. Current Vascular Pharmacology 2005; 3: 1.
35. Kawaii S, Tomono Y, Katase E, Ogawa K and Yano M. Quantitation of flavonoid constituents in citrus fruits. Journal of Agriculture and Food Chemistry 1999; 47: 3565.
36. Knekt P, Jarvinen R, Reunanen A and Maatela J. Flavonoid intake and coronary mortality in Finland: A cohort study. British Medical Journal 1996; 312: 478.
37. Lee SH, Park YB, Bae KH, Bok SH, Kwon YK, Lee ES and Choi MS. Cholesterol-lowering activity of naringenin via inhibition of 3- hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A:cholesterol acyltransferase in rats. Annals of Nutrition and Metabolism 1999; 43: 173.
38. Le Marchand L, Murphy SP, Hankin JH, Wilkens LR and Kolonel LN. Intake of flavonoids and lung cancer. Journal of the National Cancer Institute 2000; 92: 154.
39. Lonchampt M, Guardiola B, Sicot N, Bertrand M, Perdrix L and Duhault J. Protective effect of a purified flavonoid fraction against reactive oxygen radicals. In vivo and in vitro study. Arzneimittel-Forschung Drug Research 1989; 39: 882.
40. Lyseng-Williamson KA and Perry CM. Micronized purified flavonoid fraction. A review of its use in chronic venous insufficiency, venous ulcers and hemorrhoids. Drugs 2003; 63: 75.
41. Manach C, Morand C, Gil-Izquierdo A, Bouteloup-Demange C and Rémésy C. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. European Journal of Clinical Nutrition 2003; 57, 235.
42. Matsumoto H, Ikoma Y, Sugiura M, Yano M and Hasegawa Y. Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma. Journal of Agruculture and Food Chemistry 2004; 52, 6653.
43. Middleton E and Kandaswami C. Effects of flavonoids on immune and inflammatory cell functions. Biochemical Pharmacology 1992; 43: 1167.
44. Middleton E Jr, Kandaswami C and Theoharides TC. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacology Review 2000; 52: 673.
45. Miyake Y, Yamamoto K, Tsujihara N and Osawa T. Protective effects of lemon flavonoids on oxidative stress in diabetic rats. Lipids 1998; 33: 689.
46. Mizrahi S and Baerk Z. Physico-chemical characteristics of orange juice cloud. Journal of Science and Food Agriculture 1970; 21: 250.
47. Montforte MT, Trovato A, Kirjavainen S, Forestieri AM, Galati EM and Lo Cutro RB. Biological effects of hesperidin a citrus flavonoid hypolipidemic activity on experimental hypercholesterolemia in rat. Il Farmaco 1995; 50: 595.
48. Morel I, Lescoat G, Cogrel P, Sergeat O, Pasdeloup N, Brissot P, Cillard P and Cillard J. Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded tar hepatocyte cultures. Biochemical Pharmacology 1992; 45: 13.
49. Nielsen ILF, Chee WSS, Poulsen L, Offord-Cavin E, Rasmussen SE, Frederiksen H, Enslen M, Barron D, Horcajada MN and Williamson G. Bioavailability is improved by enzymatic modification of the citrus flavonoid hesperidin in humans: a randomized, double-blind, crossover trial. Journal of Nutrition 2006; 136: 404.
50. Prasain JK, Wang CC and Barnes S. Mass spectrometric methods for the determination of flavonoids in biological fluids. Free Radical Biology and Medicine 2004; 37: 1324.
51. Rice-Evans CA and Miller NJ. Antioxidant activities of flavonoids as bioactive components of food. Biochemistry Society Transactions 1996; 24: 790.
52. Rice-Evans C, Miller NG and Paganga G. Structure antioxidant activity relationships of flavonoids and phenolic acids. Free Rad Biol Med 1996; 20: 833.
53. Rowland M and Tozer TN. Clinical Pharmacokinetics: Concepts and Applications, 3rd edn. Lea and Febiger: Baltimore, MD, 1995.
54. Roztocil K, Stvrtinova V and Strejcek J. Efficacy of a 6-month treatment with Daflon 500 mg in patients with venous leg ulcers associated with chronic venous insufficiency. International Angiology 2003; 22: 24.
55. Santos KF, Oliveira TT, Nagem TJ, Pinto AS and Oliveira MG. Hypolipidaemic effects of naringenin, rutin, nicotinic acid and their associations. Pharmacology Research 1999; 40: 493.
56. Schoefer L, Mohan R, Schwiertz A, Braune A and Blaut M. Anaerobic degradation of flavonoids by Clostridium orbiscindens. Applied Environmental Microbiology 2003; 69: 5849.
57. Smith PDC. From skin disorders to venous leg ulcers: pathophysiology and efficacy of Daflon 500 mg in ulcer healing. Angiology 2003; 54 (suppl. 1): S45.
58. Struckmann JR. Clinical efficacy of micronized purified flavonoid fraction: an overview. Journal of Vascular Research 1999; 36 (suppl. 1): 37.
59. Tanaka T, Makita H, Kawabata K, Mori H, Kakumoto M, Satoh K, Hara A, Sumida T, Tanaka T and Ogawa H. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin. Carcinogenesis 1997; 18: 957.
60. Taskin O, Uryan I, Buhur A, Burak F, Erden F, Atmaca R and Wheeler M. The effects of Daflon on pelvic pain in women with Taylor syndrome. Journal of the American Association of Gynecology and Laparoscopy 1996; 3 (suppl. 4): S49.
61. Tsimoyiannis EC, Floras G, Antoniou N, Papanikolaou N, Siakas P and Tassis A. Low-molecular-weight heparins and Daflon for prevention of postoperative thromboembolism. World Journal of Surgery 1996; 20: 968.
62. Unlu A, Sucu N, Tamer L, Coskun B, Yucebilgic G, Ercan B, Gul A, Dikmengil M and Atik U. Effects of Daflon on oxidative stress induced by hindlimb ischemia/reperfusion. Pharmacology Research 2003; 48: 11.
63. Wiseman S, Mulder T and Rietveld A. Tea flavonoids: bioavailability in vivo and effects on cell signaling in vitro. Antioxidants and Redox Signaling 2001; 3: 1009.
64. Yochum L, Kushi LH, Meyer K and Folsom AR. Dietary flavonoid intake and risk of cardiovascular disease in postmenopausal women. American Journal of Epidemiology 1999; 149: 943.