Research progress on interactions between luteolin (glucosides) and drug-metabolizing enzyme

Yaoxue Xuebao

Volumn 43, Issue 4, 2008, Pages 335-342

  Ying, Jing Yan ^a   Gu, Shao Jun ^a   Yao, Tong Wei ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Caco 2 cells; Cytochrome P450; Drug metabolism; Luteolin

Indexed keywords

ABC TRANSPORTER; GLUCURONOSYLTRANSFERASE; LUTEOLIN; SULFOTRANSFERASE; UNSPECIFIC MONOOXYGENASE;

ANIMAL; DRUG INTERACTION; ENZYME INDUCTION; HUMAN; LIVER MICROSOME; METABOLISM; REVIEW;

ANIMALS; ARYL HYDROCARBON HYDROXYLASES; ATP-BINDING CASSETTE TRANSPORTERS; DRUG INTERACTIONS; ENZYME INDUCTION; GLUCURONOSYLTRANSFERASE; HUMANS; LUTEOLIN; MICROSOMES, LIVER; SULFOTRANSFERASES;

EID: 44649099520     PISSN: 05134870     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (42)

1. Ko WG, Kang TH, Lee SJ, et al. Effects of luteolin on the inhibition of proliferation and induction of apoptosis in human myeloid leukaemia cells [J]. Phytother Res, 2002, 16:295-298.
2. Kimata M, Shichijo M, Miura T, et al. Effects of luteolin, quercetin and baicalein on immunoglobulin E-mediated mediator release from human cultured mast cells [J]. Clin Ex Allergy, 2000, 30:501-508.
3. Nielsen SE, Breinholt V, Justesen U, et al. In vitro biotransformation of flavonoids by rat liver microsomes [J]. Xenobiotica, 1998, 28:389-401.
4. Xu YP, Yao TW. Study and Application of Chinese Herbal Medicine Fingerprints in Quality Control and in vitro Absorption and Metabolism [d]. Hangzhou: Zhejiang University, 2005.
5. Williamson G, Day AJ, Plumb GW, et al. Human metabolic pathways of dietary flavonoids and cinnamates [J]. Biochem Soc Trans, 2000, 28:16-22.
6. Boersma MG, Woude H, Bogaards J, et al. Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases [J]. Chem Res Toxicol, 2002, 15:662-670.
7. Shimoi K, Nakayama T. Glucuronidase deconjugation in inflammation [J]. Methods Enzymol, 2005, 400:263-272
8. Ng SP, Wong KY, Zhang L, et al. Evaluation of the first-pass glucuronidation of selected flavones in gut by Caco-2 monolayer model [J]. J Pharm Pharm Sci, 2004, 8:1-9.
9. Gradolatto A, Canivenc-Lavier MC, Basly JP, et al. Metabolism of apigenin by rat liver phase I and phase II enzymes and by isolated perfused rat liver [J]. Drug Metab Dispos, 2004, 32:58-65.
10. Spencer JP, Chowrimootoo G, Choudhury R, et al. The small intestine can both absorb and glucuronidate luminal flavonoids [J]. FEBS Lett, 1999, 458:224-230.
11. Oliverira EJ, Watson DG. In vitro glucuronidation of kaempferol and quercetin by human UGT-1A9 microsomes [J]. FEBS Lett, 2000, 471:1-6.
12. Li LP, Jiang HD. Determination and assay validation of luteolin and apigenin in human urine after oral administration of tablet of Chrysanthemum morifolium extract by HPLC [J]. J Pharm Biomed Anal, 2006, 41:261-265.
13. Zimmermann C, Gutmann H, Hruz P, et al. Mapping of multidrug resistance gene 1 and multidrug resistance-associated protein isoform 1 to 5 mRNA expression along the human intestinal tract [J]. Drug Metab Dispos, 2005, 33:219-224.
14. Hu M, Chen J, Lin H. Metabolism of flavonoids via enteric recycling: mechanistic studies of disposition of apigenin in the Caco-2 cell culture model [J]. J Pharmacol Exp Ther, 2003, 307:314-321.
15. Ebert B, Seidel A, Lampen A. Identification of BCRP as transporter of benzo [a] pyrene conjugates metabolically formed in Caco-2 cells and its induction by Ah-receptor agonists [J]. Carcinogenesis, 2005, 26:1754-1763.
16. Shimoi K, Okada H, Furugori M. Intestinal absorption of luteolin and luteolin 7-0-beta-glucoside in rats and humans [J]. FEBS Lett, 1998, 438:220-224.
17. Walgren RA, Lin JT, Kinne RK, et al. Cellular uptake of dietary flavonoid quercetin 4′-beta-glucoside by sodium-dependent glucose transporter SGLT1 [J]. J Pharmacol Exp Ther, 2000, 294:837-843.
18. Arts IC, Sesink AL, Hollman PC. Quercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine [J]. J Nutr, 2002, 132:630-632.
19. Berrin JG, McLauchlan WR, Needs P, et al. Functional expression of human liver cytosolic beta-glucosidase in Pichia pastoris. Insights into its role in the metabolism of dietary glucosides [J]. Eur J Biochem, 2002, 269:249-258.
20. Day AJ, Cañada FJ, Díaz JC, et al. Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase [J]. FEBS Lett, 2000, 468:166-170.
21. Németh K, Plumb GW , Berrin JG, et al. Deglycosylation by small intestinal epithelial cell beta-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans [J]. Eur J Nutr, 2003, 42:29-42.
22. Li LP, Jiang HD. Metabolism of Chrysanthemum morifolium extract by intestinal tract flora [J]. Chin Tradit Herb Drugs, 2006, 37:1001-1004.
23. Chen T, Li LP, Lu XY. Absorption and excretion of luteolin and apigenin in rats after oral administration of Chrysanthemum morifolium extract [J]. J Agric Food Chem, 2007, 55:273-277.
24. Dimmock JR, Elias DW, Beazely MA, et al. Bioactivities of chalcones [J]. Curr Med Chem, 1999, 6:1125-1149.
25. Lin YT, Hsiu SL, Hou YC, et al. Degradation of flavonoid aglycones by rabbit, rat and human fecal flora [J]. Biol Pharm Bull, 2003, 26:747-751.
26. Kim HJ, Lee SB, Park SK, et al. Effects of hydroxyl group numbers on the B-ring of 5, 7-dihydroxyflavones on the differential inhibition of human CYP1A and CYP1B1 enzymes [J]. Arch Pharm Res, 2005, 28:1114-1121.
27. Foti RS, Wahlstrom JL, Wienkers LC. The in vitro drug interaction potential of dietary supplements containing multiple herbal components [J]. Drug Metab Dispos, 2007, 35:185-188.
28. Zhang S, Qin CH, Safe SH. Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context [J]. Environ Health Perspect, 2003, 111:1877-1882
29. Maliakal PP, Wanwimolruk S. Effect of herbal teas on hepatic drug metabolizing enzymes in rats [J]. J Pharm Pharmacol, 2001, 53:1323-1329.
30. Walle UK, Walle T. Induction of human UDP-Glucuronosyltransferase UGT1A1 by flavonoids-structural requirements [J]. Drug Metab Dispos, 2002, 30: 564-569.
31. Morimitsu Y, Sugihara N, Furuno K. Inhibitory effect of flavonoids on sulfo- and glucurono-conjugation of acetaminophen in rat cultured hepatocytes and liver subcellular preparations [J]. Biol Pharm Bull, 2004, 27:714-717.
32. Junko S, Kasumi Y, Eri T, et al. The induction of human UDP-glucuronosyltransferase 1A1 mediatedthrough a distal enhancer module by flavonoids and xenobiotics [J]. Biochem Pharmacol, 2004, 67:989-1000.
33. Molnár J, Gyémant N, Mucsi I, et al. Modulation of multidrug resistance and apoptosis of cancer cells by selected carotenoids [J]. In Vivo, 2004, 18:237-244.
34. Ugocsai K, Varga A, Molnár P, et al. Effects of selected flavonoids and carotenoids on drug accumulation and apoptosis induction in multidrug-resistant colon cancer cells expressing MDR1/LRP [J]. In Vivo, 2005, 19:433-438.
35. Zhang S, Yang X, Morris ME. Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport [J]. Mol Pharmacol, 2004, 65:1208-1216.
36. van Zanden JJ, Wortelboer HM, Bijlsma S, et al. Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2 [J]. Biochem Pharmacol, 2005, 69:699-708.
37. Boumendjel A, Di Pietro A, Dumontet C, et al. Recent advances in the discovery of flavonoids and analogs with high-affinity binding to P-glycoprotein responsible for cancer cell multidrug resistance [J]. Med Res Rev, 2002, 22:512-529.
38. Di Pietro A, Conseil G, Pérez-Victoria JM, et al. Modulation by flavonoids of cell multidrug resistance mediated by P-glycoprotein and related ABC transporters [J]. Cell Mol Life Sci, 2002, 59:307-322.
39. van Zanden JJ, Geraets L, Wortelboer HM, et al. Structural requirements for the flavonoid-mediated modulation of glutathione S-transferase P1-1 and GS-X pump activity in MCF7 breast cancer cells [J]. Biochem Pharmacol, 2004, 67:1607-1617.
40. Nissler L, Gebhardt R, Berger S. Flavonoid binding to a multi-drug-resistance transporter protein; an STD-NMR study [J]. Anal Bioanal Chem, 2004, 379:1045-1049.
41. Walle T. Absorption and metabolism of flavonoids [J]. Free Radic Biol Med, 2004, 36:829-837.
42. Spencer JP, Abd-el-Mohsen MM, Rice-Evans C, et al. Cellular uptake and metabolism of flavonoids and their metabolites; implications for their bioactivity [J]. Arch Biochem Biophys, 2004, 423:148-161.