Transport and metabolism of flavonoids from Chinese herbal remedy Xiaochaihu-tang across human intestinal Caco-2 cell monolayers

Acta Pharmacologica Sinica

Volumn 29, Issue 9, 2008, Pages 1086-1093

  Dai, Jie Yu ^a   Yang, Jun Ling ^a   Li, Chuan ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Caco 2 cell monolayer; Chemoinformatics; Efflux; Flavonoid; Metabolism; Transport; Xiaochaihu tang

Indexed keywords

AGLYCONE; BAICALEIN; BAICALIN; FLAVONOID; FLAVONOID GLYCOSIDE; GLYCOPROTEIN P; HERBACEOUS AGENT; ISOLIQUIRITIGENIN; ISOLIQUIRITIN; ISOLIQUIRITIN APIOSIDE; LIQUIRITIGENIN; LIQUIRITIN; LIQUIRITIN APIOSIDE; MULTIDRUG RESISTANCE PROTEIN; OROXYLIN A; OROXYLIN A 7 O BETA DEXTRO GLUCOPYRANOSIDURONIDE; UNCLASSIFIED DRUG; WOGONIN; WOGONOSIDE;

ARTICLE; CELL STRAIN CACO 2; CHINESE HERB; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG CONJUGATION; DRUG GLUCURONIDATION; DRUG METABOLISM; DRUG PENETRATION; DRUG STRUCTURE; DRUG SULFATION; DRUG TRANSPORT; HUMAN; HUMAN CELL; HYDROGEN BOND; INTESTINE CELL; MEMBRANE PERMEABILITY; MEMBRANE TRANSPORT; MONOLAYER CULTURE; TRANSPORT KINETICS; XIAOCHAIHU TANG;

BIOLOGICAL TRANSPORT, ACTIVE; BIOTRANSFORMATION; CACO-2 CELLS; CELL MEMBRANE PERMEABILITY; COMPUTATIONAL BIOLOGY; DRUGS, CHINESE HERBAL; FLAVONOIDS; GLUCURONIDES; HUMANS; INDICATORS AND REAGENTS; SOLUBILITY; SULFATES;

EID: 51349086819     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1111/j.1745-7254.2008.00850.x     Document Type: Article

References (37)

1. Hirayama C, Okumura M, Tanikawa K, Yano M, Mizuta M, Ogawa N. A multicenter randomized controlled clinical trial of Shosaiko-to in chronic active hepatitis. Gastroenterol Jpn 1989 24 : 715 9.
2. Tajiri H, Kozaiwa K, Ozaki Y, Miki K, Shimizu K, Okada S. Effect of Sho-saiko-to (Xiao-chai-hu-tang) on HBeAg clearance in children with chronic hepatitis B virus infection and with sustained liver disease. Am J Chin Med 1991 19 : 121 9.
3. Oka H, Yamamoto S, Kuroki T, Harihara S, Marumo T, Kim SR, et al. Prospective study of chemoprevention of hepatocellular carcinoma with Sho-saiko-to (TJ-9). Cancer 1995 76 : 743 9.
4. Uchida E, Fukasawa I, Matuszaki Y, Inagaki M, Uchida N, Takeda S, et al. Pharmacokinetics and pharmacodynamics of TJ-9 after single administration in Japanese healthy male volunteers. Jpn Pharmacol Ther 1995 23 : 659 70.
5. Li C, Homma M, Oka K. Chromatographic identification of phenolic compounds in human urine following oral administration of the herbal medicines Daisaiko-to and Shosaiko-to. J Chromatogr B 1997 693 : 191 8.
6. Li C, Homma M, Ohkura N, Oka K. (S)-Dihydrooroxylin A in human urine following oral administration of the traditional Chinese medicines: Daisaiko-to and Shosaiko-to. Tetrahedron Asymmetry 1997 8 : 1145 7.
7. Li C, Homma M, Oka K. Characteristics of delayed excretion of fla-vonoids in human urine after administration of Shosaiko-to, a herbal medicine. Biol Pharm Bull 1998 21 : 1251 7.
8. Woo KJ, Lim JH, Suh SI, Kwon YK, Shin SW, Kim SC, et al. Differential inhibitory effects of baicalein and baicalin on LPS-induced cyclooxygenase-2 expression through inhibition of C/EBPbeta DNA-binding activity. Immunobiology 2006 211 : 359 68.
9. Chang WT, Shao ZH, Yin JJ, Mehendale S, Wang CZ, Qin Y, et al. Comparative effects of flavonoids on oxidant scavenging and isch-emia- reperfusion injury in cardiomyocytes. Eur J Pharmacol 2007 566 : 58 66.
10. Guo O, Zhao L, You O, Yang Y, Gu H, Song G, et al. Anti-hepatitis B virus activity of wogonin in vitro and in vivo. Antiviral Res 2007 74 : 16 24.
11. Ohtake N, Nakai Y, Yamamoto M, Ishige A, Sasaki H, Fukuda K, et al. The herbal medicine Shosaiko-to exerts different modulating effects on lung local immune responses among mouse strains. Int Im-munopharmacol 2002 2 : 357 66.
12. Chao JI, Su WC, Liu HF. Baicalein induces cancer cell death and proliferation retardation by the inhibition of CDC2 kinase and surviving associated with opposite role of p38 mitogen-activated protein kinase and AKT. Mol Cancer Ther 2007 6 : 3039 48.
13. Bao YW, Li C, Shen HW, Nan FJ. Determination of saikosaponin derivatives in Radix bupleuri and in Pharmaceuticals of the Chinese multiherb remedy Xiaochaihu-tang using liquid chromatographic tandem mass spectrometry. Anal Chem 2004 76 : 4208 16.
14. Chen P, Li C, Liang SP, Song GQ, Sun Y, Shi YH, et al. Characterization and quantification of eight water-soluble constituents in tubers of Pinellia ternata and in tea granules from the Chinese multiherb remedy Xiaochaihu-tang. J Chromatogr B 2006 843 : 183 93.
15. Li L, Liang SP, Du FF, Li C. Simultaneous quantification of multiple licorice flavonoids in rat plasma. J Am Soc Mass Spectrom 2007 18 : 778 82.
16. Hollman PCH, Katan MB. Absorption, metabolism, and bioavailability of flavonoids. In : Rice-Evans CA, Packer L, editors. Flavonoids in health and disease. New York, Basel, Hong Kong : Marcel Dekker, Inc 1998. p 483 522.
17. Tetko IV, Gasteiger J, Todeschini R, Mauri A, Livingstone D, Ertl P, et al. Virtual computational chemistry laboratory - design and description. J Comput Aid Mol Des 2005 19 : 453 63.
18. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997 23 : 3 25.
19. US FDA guidance for industry on bioanalytical method validation, 2001 http://www.fda.gov/cder/guidance/index.htm.
20. Li C, Meng XF, Winnik B, Lee MJ, Lu H, Sheng SQ, et al. Analysis of urinary metabolites of tea catechins by liquid chromatography/electrospray ionization mass spectrometry. Chem Res Toxicol 2001 14 : 702 7.
21. Artursson P, Karlsson J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 1991 175 : 880 5.
22. Van de Waterbeemd H, Gifford E. ADMET in silico modelling: towards prediction paradise Nat Rev Drug Discov 2003 2 : 192 204.
23. Hou TJ, Wang JM, Zheng W, Wang W, Xu XJ. Recent advances in computational prediction of drug absorption and permeability in drug discovery. Curr Med Chem 2006 13 : 2653 67.
24. Sabolovic N, Magdalou J, Netter P, Abid A. Nonsteroidal anti-inflammatory drugs and phenols glucuronidation in Caco-2 cells: identification of the UDP-glucuronosyltransferases UGT1A6, 1A3 and 2B7. Life Sci 2000 67 : 185 96.
25. Meinl W, Ebert B, Glatt H, Lampen A. Sulfotransferase forms expressed in human intestinal Caco-2 and TC7 cells at varying stages of differentiation and role in benzo[a]pyrene metabolism. Drug Metab Dispos 2008 36 : 276 83.
26. Walle T. Absorption and metabolism of flavonoids. Free Radic Biol Med 2004 36 : 829 37.
27. Akao T, Kawabata K, Yanagisawa E, Ishihara K, Mizuhara Y, Wakui Y, et al. Baicalin, the predominant flavone glucuronide of scutellariae radix, is absorbed from the rat gastrointestinal tract as the aglycone and restored to its original form. J Pharm Pharmacol 2000 52 : 1563 8.
28. Liu Y, Hu M. Absorption and metabolism of flavonoids in the Caco-2 cell culture model and a perfused rat intestinal model. Drug Metab Dispos 2002 30 : 370 7.
29. Zhang L, Lin G, Kovács B, Jani M, Krajcsi P, Zuo Z. Mechanistic study on the intestinal absorption and disposition of baicalein. Eur J Pharm Sci 2007 31 : 221 31.
30. Akao T, Hanada M, Sakashita Y, Sato K, Morita M, Imanaka T. Efflux of baicalin, a flavone glucuronide of Scutellariae Radix, on Caco-2 cells through multidrug resistance-associated protein 2. J Pharm Pharmacol 2007 59 : 87 93.
31. Asano T, Ishihara K, Morota T, Takeda S, Aburada M. Permeability of the flavonoids liquiritigenin and its glycosides in licorice roots and davidigenin, a hydrogeneted metabolite of liquiritigenin, using human intestinal cell line Caco-2. J Ethnopharmacol 2003 89 : 285 9.
32. Wen X, Walle T. Methylated flavonoids have greatly improved intestinal absorption and metabolic stability. Drug Metab Dispos 2006 34 : 1786 92.
33. Wang Y, Cao J, Zeng S. Involvement of P-glycoprotein in regulating cellular levels of Ginkgo flavonols: quercetin, kaemferol, and isor-hamnetin. J Pharm Pharmacol 2005 57 : 1297 303.
34. König J, Nies AT, Cui Y, Leirer I, Keppler D. Conjugate export pumps of the multidrug resistance protein (MRP) family: localization, substrate specificity, and MRP2 mediated drug resistance. Biochem Biophys Acta 1999 1461 : 377 94.
35. Walle UK, Galijatovic A, Walle T. Transport of the flavonoid Chrysin and its conjugated metabolites by the human intestinal cell line Caco-2. Biochem Pharmacol 1999 58 : 431 8.
36. O'Leary KA, Day AJ, Needs PW, Sly WS, O'Brien NM, Williamson G. Flavonoid glucuronides are substrates for human liver β-glucuronidase. FEBS Lett 2001 503 : 103 6.
37. Shimoi K, Saka N, Nozawa R, Sato M, Amano I, Nakayama T, et al. Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation. Drug Metab Dispos 2001 29 : 1521 4.