Intestinal absorption of γ-Tocotrienol is mediated by Niemann-Pick C1-like 1: In situ rat intestinal perfusion studies

Drug Metabolism and Disposition

Volumn 38, Issue 6, 2010, Pages 939-945

  Abuasal, Bilal ^a   Sylvester, Paul W ^a   Kaddoumi, Amal ^a  

^a UNIVERSITY OF LOUISIANA AT MONROE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,7,8 TRIMETHYL 2 (BETA CARBOXYETHYL) 6 HYDROXYCHROMAN; CARRIER PROTEIN; CHROMAN DERIVATIVE; DRUG METABOLITE; GAMMA TOCOTRIENOL; NIEMANN PICK C1 LIKE 1 PROTEIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL STRAIN; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG TRANSPORT; DRUG UPTAKE; ILEUM; INTESTINE ABSORPTION; INTESTINE MUCOSA PERMEABILITY; INTESTINE PERFUSION; JEJUNUM; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; RAT;

ANIMALS; ANTICHOLESTEREMIC AGENTS; AZETIDINES; BIOLOGICAL TRANSPORT; CHROMANS; ILEUM; INTESTINAL ABSORPTION; INTESTINES; JEJUNUM; MALE; NIEMANN-PICK DISEASES; PERFUSION; RATS; RATS, SPRAGUE-DAWLEY; VITAMIN E;

RATTUS;

EID: 77952294329     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.031567     Document Type: Article

References (40)

1. Abe C, Uchida T, Ohta M, Ichikawa T, Yamashita K, and Ikeda S (2007) Cytochrome P450-dependent metabolism of vitamin E isoforms is a critical determinant of their tissue concentrations in rats. Lipids 42:637-645.
2. Altmann SW, Davis HR Jr, Zhu LJ, Yao X, Hoos LM, Tetzloff G, Iyer SP, Maguire M, Golovko A, Zeng M, et al. (2004) Niemann-Pick C1 Like 1 protein is critical for intestinal cholesterol absorption. Science 303:1201-1204.
3. Amidon GL, Sinko PJ, and Fleisher D (1988) Estimating human oral fraction dose absorbed: a correlation using rat intestinal membrane permeability for passive and carrier-mediated compounds. Pharm Res 5:651-654.
4. Anwar K, Iqbal J, and Hussain MM (2007) Mechanisms involved in vitamin E transport by primary enterocytes and in vivo absorption. J Lipid Res 48:2028-2038.
5. Brisson L, Castan S, Fontbonne H, Nicoletti C, Puigserver A, and Ajandouz el H (2008) Alpha-tocopheryl acetate is absorbed and hydrolyzed by Caco-2 cells comparative studies with alpha-tocopherol. Chem Phys Lipids 154:33-37.
6. Davis HR Jr, Zhu LJ, Hoos LM, Tetzloff G, Maguire M, Liu J, Yao X, Iyer SP, Lam MH, Lund EG, et al. (2004) Niemann-Pick C1 Like 1 (NPC1L1) is the intestinal phytosterol and cholesterol transporter and a key modulator of whole-body cholesterol homeostasis. J Biol Chem 279:33586-33592.
7. Ehehalt R, Jochims C, Lehmann WD, Erben G, Staffer S, Reininger C, and Stremmel W (2004) Evidence of luminal phosphatidylcholine secretion in rat ileum. Biochim Biophys Acta 1682: 63-71.
8. Fagerholm U, Johansson M, and Lennernäs H (1996) Comparison between permeability coefficients in rat and human jejunum. Pharm Res 13:1336-1342.
9. Freiser H and Jiang Q (2009) Gamma-tocotrienol and gamma-tocopherol are primarily metabolized to conjugated 2-(beta-carboxyethyl)-6-hydroxy-2,7,8- trimethylchroman and sulfated long-chain carboxychromanols in rats. J Nutr 139:884-889.
10. Garcia-Calvo M, Lisnock J, Bull HG, Hawes BE, Burnett DA, Braun MP, Crona JH, Davis HR Jr, Dean DC, Detmers PA, et al. (2005) The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1). Proc Natl Acad Sci USA 102:8132-8137.
11. Hayes KC, Pronczuk A, and Liang JS (1993) Differences in the plasma transport and tissue concentrations of tocopherols and tocotrienols: observations in humans and hamsters. Proc Soc Exp Biol Med 202:353-359. (Pubitemid 23073473)
12. Ikeda I, Imasato Y, Sasaki E, and Sugano M (1996) Lymphatic transport of alpha-, gamma- and delta-tocotrienols and alpha-tocopherol in rats. Int J Vitam Nutr Res 66:217-221.
13. Jiang Q, Elson-Schwab I, Courtemanche C, and Ames BN (2000) Gamma-tocopherol and its major metabolite, in contrast to alpha-tocopherol, inhibit cyclooxygenase activity in macrophages and epithelial cells. Proc Natl Acad Sci USA 97:11494-11499.
14. Kaddoumi A, Fleisher D, Heimbach T, Li LY, and Cole S (2006) Factors influencing regional differences in intestinal absorption of UK-343,664 in rat: possible role in dose-dependent pharmacokinetics. J Pharm Sci 95:435-445. (Pubitemid 43241984)
15. Kayden HJ and Traber MG (1993) Absorption, lipoprotein transport, and regulation of plasma concentrations of vitamin E in humans. J Lipid Res 34:343-358.
16. Kikuta Y, Miyauchi Y, Kusunose E, and Kusunose M (1999) Expression and molecular cloning of human liver leukotriene B4 omega-hydroxylase (CYP4F2) gene. DNA Cell Biol 18:723-730. (Pubitemid 29439224)
17. Kimura T, Nakamura J, and Sezaki H (1985) Effect of synthetic surfactants on drug absorption in the presence of a physiologic surfactant, sodium taurocholate, in rats. J Pharmacobiodyn 8:661-668. (Pubitemid 15229846)
18. Lennernäs H (2007) Intestinal permeability and its relevance for absorption and elimination. Xenobiotica 37:1015-1051. (Pubitemid 350035536)
19. Li YJ, Luo SC, Lee YJ, Lin FJ, Cheng CC, Wein YS, Kuo YH, and Huang CJ (2008) Isolation and identification of alpha-CEHC sulfate in rat urine and an improved method for the determination of conjugated alpha-CEHC. J Agric Food Chem 56:11105-11113.
20. McIntyre BS, Briski KP, Gapor A, and Sylvester PW (2000) Antiproliferative and apoptotic effects of tocopherols and tocotrienols on preneoplastic and neoplastic mouse mammary epithelial cells. Proc Soc Exp Biol Med 224:292-301. (Pubitemid 30643508)
21. Narushima K, Takada T, Yamanashi Y, and Suzuki H (2008) Niemann-pick C1-like 1 mediates α-tocopherol transport. Mol Pharmacol 74:42-49. (Pubitemid 351872157)
22. Reboul E, Klein A, Bietrix F, Gleize B, Malezet-Desmoulins C, Schneider M, Margotat A, Lagrost L, Collet X, and Borel P (2006) Scavenger receptor class B type I (SR-BI) is involved in vitamin E transport across the enterocyte. J Biol Chem 281:4739-4745. (Pubitemid 43847734)
23. Shah SJ and Sylvester PW (2005) Gamma-tocotrienol inhibits neoplastic mammary epithelial cell proliferation by decreasing Akt and nuclear factor kB activity. Exp Biol Med (Maywood) 230:235-241.
24. Singhal D, Ho NF, and Anderson BD (1998) Absorption and intestinal metabolism of purine dideoxynucleosides and an adenosine deaminase-activated prodrug of 2′,3′-dideoxyinosine in the mesenteric vein cannulated rat ileum. J Pharm Sci 87:569-577. (Pubitemid 28225621)
25. Song BL and DeBose-Boyd RA (2006) Insig-dependent ubiquitination and degradation of 3-hydroxy-3-methylglutaryl coenzyme a reductase stimulated by delta- and gammatocotrienols. J Biol Chem 281:25054-25061.
26. Sontag TJ and Parker RS (2002) Cytochrome P450 ω-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem 277:25290-25296.
27. Sontag TJ and Parker RS (2007) Influence of major structural features of tocopherols and tocotrienols on their omega-oxidation by tocopherol-omega- hydroxylase. J Lipid Res 48: 1090-1098.
28. Sookwong P, Nakagawa K, Murata K, Kojima Y, and Miyazawa T (2007) Quantitation of tocotrienol and tocopherol in various rice brans. J Agric Food Chem 55:461-466. (Pubitemid 46586333)
29. Sundram K, Thiagarajan T, Gapor A, and Basiron Y (2002) Palm tocotrienols: new antioxidants for the new millennium. Inform 13:634-640.
30. Swanson JE, Ben RN, Burton GW, and Parker RS (1999) Urinary excretion of 2,7, 8-trimethyl-2-(beta-carboxyethyl)-6-hydroxychroman is a major route of elimination of gamma-tocopherol in humans. J Lipid Res 40:665-671.
31. Sylvester PW and Shah SJ (2005) Mechanisms mediating the antiproliferative and apoptotic effects of vitamin E in mammary cancer cells. Front Biosci 10:699-709.
32. Thelen K and Dressman JB (2009) Cytochrome P450-mediated metabolism in the human gut wall. J Pharm Pharmacol 61:541-558.
33. Tomeo AC, Geller M, Watkins TR, Gapor A, and Bierenbaum ML (1995) Antioxidant effects of tocotrienols in patients with hyperlipidemia and carotid stenosis. Lipids 30:1179-1183.
34. Tsuzuki W, Yunoki R, and Yoshimura H (2007) Intestinal epithelial cells absorb γ-tocotrienol faster than α-tocopherol. Lipids 42:163-170. (Pubitemid 351912044)
35. Weinglass AB, Köhler MG, Nketiah EO, Liu J, Schmalhofer W, Thomas A, Williams B, Beers L, Smith L, Hafey M, et al. (2008a) Madin-Darby canine kidney II cells: a pharmacologically validated system for NPC1L1-mediated cholesterol uptake. Mol Pharmacol 73:1072-1084.
36. Weinglass AB, Kohler M, Schulte U, Liu J, Nketiah EO, Thomas A, Schmalhofer W, Williams B, Bildl W, McMasters DR, et al. (2008b) Extracellular loop C of NPC1L1 is important for binding to ezetimibe. Proc Natl Acad Sci USA 105:11140-11145.
37. Yap SP, Yuen KH, and Lim AB (2003) Influence of route of administration on the absorption and disposition of α-, γ-, and δ-tocotrienols in rats. J Pharm Pharmacol 55:53-58. (Pubitemid 36142081)
38. Yap SP, Yuen KH, and Wong JW (2001) Pharmacokinetics and bioavailability of alpha-,gamma- and delta-tocotrienols under different food status. J Pharm Pharmacol 53:67-71.
39. You CS, Sontag TJ, Swanson JE, and Parker RS (2005) Long-chain carboxychromanols are the major metabolites of tocopherols and tocotrienols in A549 lung epithelial cells but not HepG2 cells. J Nutr 135:227-232.
40. Yu L (2008) The structure and function of Niemann-Pick C1-like 1 protein. Curr Opin Lipidol 19:263-269. (Pubitemid 351653564)