A novel LXR-α activator identified from the natural product Gynostemma pentaphyllum

Biochemical Pharmacology

Volumn 70, Issue 9, 2005, Pages 1298-1308

  Huang, Tom Hsun Wei ^a   Razmovski Naumovski, Valentina ^a   Salam, Noeris K ^a   Duke, Rujee K ^a   Tran, Van Hoan ^a   Duke, Colin C ^a   Roufogalis, Basil D ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

ABCA1; Apolipoprotein E; Gynosaponin; Gynostemma pentaphyllum; Gypenoside; Liver X receptor

Indexed keywords

2ALPHA,3BETA,12BETA PENTAHYDROXYDAMMAR 25 ENE 20 O BETA DEXTRO GLUCOPYRANOSIDE; ABC TRANSPORTER A1; APOLIPOPROTEIN E; DAMMARANE DERIVATIVE; LIVER X RECEPTOR ALPHA; LIVER X RECEPTOR BETA; PLANT EXTRACT; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; ATHEROSCLEROSIS; DRUG ISOLATION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; EMBRYO; GENE EXPRESSION; GYNOSTEMMA; HERBAL MEDICINE; HUMAN; HUMAN CELL; HUMAN TISSUE; MACROPHAGE; PRIORITY JOURNAL; PROTEIN EXPRESSION; RECEPTOR UPREGULATION; TRANSCRIPTION INITIATION;

APOLIPOPROTEINS E; ATP-BINDING CASSETTE TRANSPORTERS; CELL LINE; DNA-BINDING PROTEINS; GYNOSTEMMA; HUMANS; LIGANDS; MODELS, MOLECULAR; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RNA, MESSENGER; SAPONINS; TETRADECANOYLPHORBOL ACETATE;

EID: 25644435506     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2005.07.033     Document Type: Article

References (64)

1. P. Libby Inflammation in atherosclerosis Nature 420 2002 868 8674
2. M. Aikawa, and P. Libby Atherosclerotic plaque inflammation: the final frontier? Can J Cardiol 20 2004 631 634
3. W.E. Stehbens Anitschkow and the cholesterol over-fed rabbit Cardiovasc Pathol 8 1999 177 178
4. S. Sugiyama, Y. Okada, G.K. Sukhova, R. Virmani, J.W. Heinecke, and P. Libby Macrophage myeloperoxidase regulation by granulocyte macrophage colony-stimulating factor in human atherosclerosis and implications in acute coronary syndromes Am J Cardiovasc Pathol 158 2001 879 891
5. M. Jaye LXR agonists for the treatment of atherosclerosis Curr Opin Investig Drugs 4 2003 1053 1058
6. J.J. Repa, and D.J. Mangelsdorf The liver X receptor gene team: potential new players in atherosclerosis Nat Med 8 2002 1243 1248
7. P. Tontonoz, and D.J. Mangelsdorf Liver X receptor signaling pathways in cardiovascular disease Mol Endocrinol 17 2003 985 993
8. T. Kino, and G.P. Chrousos Combating atherosclerosis with LXR{alpha} and PPAR{alpha} agonists: is rational multitargeted polypharmacy the future of therapeutics in complex diseases? Mol Interv 4 2004 254 257
9. S.B. Joseph, and P. Tontonoz LXRs: new therapeutic targets in atherosclerosis? Curr Opin Pharmacol 3 2003 192 197
10. B.A. Janowski, M.J. Grogan, S.A. Jones, G.B. Wisely, S.A. Kliewer, and E.J. Corey Structural requirements of ligands for the oxysterol liver X receptors LXRalpha and LXRbeta Proc Natl Acad Sci USA 96 1999 266 271
11. T. Ide, H. Shimano, T. Yoshikawa, N. Yahagi, M. Amemiya-Kudo, and T. Matsuzaka Cross-talk between peroxisome proliferator-activated receptor (PPAR) alpha and liver X receptor (LXR) in nutritional regulation of fatty acid metabolism. Part II: LXRs suppress lipid degradation gene promoters through inhibition of PPAR signalling Mol Endocrinol 17 2003 1255 1267
12. J.L. Collins Therapeutic opportunities for liver X receptor modulators Curr Opin Drug Discov Dev 7 2004 692 702
13. B.A. Laffitte, J.J. Repa, S.B. Joseph, D.C. Wilpitz, H.R. Kast, and D.J. Mangelsdorf LXRs control lipid-inducible expression of the apolipoprotein E gene in macrophages and adipocytes Proc Natl Acad Sci USA 98 2001 507 512
14. C.P. Sparrow, J. Baffic, M.H. Lam, E.G. Lund, A.D. Adams, and X. Fu A potent synthetic LXR agonist is more effective than cholesterol loading at inducing ABCA1 mRNA and stimulating cholesterol efflux J Biol Chem 277 2002 10021 10027
15. S. Svensson, T. Ostberg, M. Jacobsson, C. Norstrom, K. Stefansson, and D. Hallen Crystal structure of the heterodimeric complex of LXRalpha and RXRbeta ligand-binding domains in a fully agonistic conformation EMBO J 22 2003 4625 4633
16. S. Williams, R.K. Bledsoe, J.L. Collins, S. Boggs, M.H. Lambert, and A.B. Miller X-ray crystal structure of the liver X receptor beta ligand binding domain: regulation by a histidine-tryptophan switch J Biol Chem 278 2003 27138 27143
17. S. Hoerer, A. Schmid, A. Heckel, R.M. Budzinski, and H. Nar Crystal structure of the human liver X receptor beta ligand-binding domain in complex with a synthetic agonist J Mol Biol 334 2003 853 861
18. M. Wang, J. Thomas, T.P. Burris, J. Schkeryantz, and L.F. Michael Molecular determinants of LXRalpha agonism J Mol Graph Model 22 2003 173 181
19. M. Farnegardh, T. Bonn, S. Sun, J. Ljunggren, H. Ahola, and A. Wilhelmsson The three-dimensional structure of the liver X receptor beta reveals a flexible ligand-binding pocket that can accommodate fundamentally different ligands J Biol Chem 278 2003 38821 38828
20. R. Mohan, and R.A. Heyman Orphan nuclear receptor modulators Curr Top Med Chem 3 2003 1637 1647
21. A. Brooks-Wilson, M. Marcil, S.M. Clee, L.H. Zhang, K. Roomp, and M. van Dam Mutations in ABC1 in Tangier disease and familial high-density lipoprotein deficiency Nat Genet 22 1999 336 345
22. J. Stefkova, R. Poledne, and J.A. Hubacek ATP-binding cassette (ABC) transporters in human metabolism and diseases Physiol Res 53 2004 235 243
23. E. Orso, C. Broccardo, W.E. Kaminski, A. Bottcher, G. Liebisch, and W. Drobnik Transport of lipids from golgi to plasma membrane is defective in tangier disease patients and Abc1-deficient mice Nat Genet 24 2000 192 196
24. L. Bocksch, T. Stephens, A. Lucas, and B. Singh Apolipoprotein E: possible therapeutic target for atherosclerosis Curr Drug Targets Cardiovasc Haematol Disord 1 2001 93 106
25. S. Bellosta, R.W. Mahley, D.A. Sanan, J. Murata, D.L. Newland, and J.M. Taylor Macrophage-specific expression of human apolipoprotein E reduces atherosclerosis in hypercholesterolemic apolipoprotein E-null mice J Clin Invest 96 1995 2170 2179
26. M.F. Linton, J.B. Atkinson, and S. Fazio Prevention of atherosclerosis in apolipoprotein E-deficient mice by bone marrow transplantation Science 267 1995 1034 1037
27. E.G. Lund, J.G. Menke, and C.P. Sparrow Liver X receptor agonists as potential therapeutic agents for dyslipidemia and atherosclerosis Arterioscler Thromb Vasc Biol 23 2003 1169 1177
28. T.H. Huang, B.P. Kota, V. Razmovski, and B.D. Roufogalis Herbal or natural medicines as modulators of peroxisome proliferator activated receptors and related nuclear receptors for therapy of metabolic syndrome Basic Clin Pharmacol Toxicol 96 2005 3 14
29. K.S. Bramlett, K.A. Houck, K.M. Borchert, M.S. Dowless, P. Kulanthaivel, and Y. Zhang A natural product ligand of the oxysterol receptor, liver X receptor J Pharmacol Exp Ther 307 2003 291 296
30. M. Blumert, and J.L. Liu Jiaogulan China's "immortality" herb 1999 Torchlight Publishing Inc. Badger, USA
31. L. Li, L. Jiao, and B.H. Lau Protective effect of gypenosides against oxidative stress in phagocytes, vascular endothelial cells and liver microsomes Cancer Biother 8 1993 263 272
32. M.A. Tanner, X. Bu, J.A. Steimle, and P.R. Myers The direct release of nitric oxide by gypenosides derived from the herb Gynostemma pentaphyllum Nitric Oxide 3 1999 359 365
33. Jian Su, New Medical College. The dictionary of Chinese medicine (Zhong Yao Da Ci Dian). Shanghai, China: Shanghai Science and Technology Press; 1986.
34. A. Attawish, S. Chivapat, S. Phadungpat, J. Bansiddhi, Y. Techadamrongsin, and O. Mitrijit Chronic toxicity of Gynostemma pentaphyllum Fitoterapia 75 2004 539 551
35. B. la Cour, P. Molgaard, and Z. Yi Traditional Chinese medicine in treatment of hyperlipidaemia J Ethnopharmacol 46 1995 125 129
36. K. Yoshikawa, T. Takemoto, and S. Arihara Studies on the constituents of Cucurbitaceae plants. Part XVI: on the saponin constituents of Gynostemma pentaphyllum Makino (II) Yakugaku Zasshi 107 1987 262 267
37. A. Perez, J.L. Thuillard, C.L. Bentzen, and E.J. Niesor Expression of nuclear receptors and apoE secretion during the differentiation of monocytic THP-1 cells into macrophages Cell Biol Toxicol 19 2003 95 105
38. E.M. Quinet, D.A. Savio, A.R. Halpern, L. Chen, C.P. Miller, and P. Nambi Gene-selective modulation by a synthetic oxysterol ligand of the liver X receptor J Lipid Res 45 2004 1929 1942
39. A. Pawar, J. Xu, E. Jerks, D.J. Mangelsdorf, and D.B. Jump Fatty acid regulation of liver X receptors (LXR) and peroxisome proliferator-activated receptor alpha (PPARalpha) in HEK293 cells J Biol Chem 277 2002 39243 39250
40. A. Abe, Y. Kiriyama, M. Hirano, T. Miura, H. Kamiya, and H. Harashima Troglitazone suppresses cell growth of KU812 cells independently of PPARgamma Eur J Pharmacol 436 2002 7 13
41. G.F. Davies, P.J. McFie, R.L. Khandelwal, and W.J. Roesler Unique ability of troglitazone to up-regulate peroxisome proliferator-activated receptor-gamma expression in hepatocytes J Pharmacol Exp Ther 300 2002 72 77
42. D. Wagsater, J. Dimberg, and A. Sirsjo Induction of ATP-binding cassette A1 by all-trans retinoic acid: possible role of liver X receptor-α Int J Mol Med 11 2003 419 423
43. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of dye-binding Anal Biochem 72 1976 248 254
44. F. Mohamadi, N.G.J. Richard, W.C. Guida, R. Liskamp, M. Lipton, and C. Caufield MacroModel - an integrated software system for modeling organic and bioorganic molecules using molecular mechanics J Comput Chem 11 1990 440
45. R.A. Friesner, J.L. Banks, R.B. Murphy, T.A. Halgren, J.J. Klicic, and D.T. Mainz Glide: a new approach for rapid, accurate docking and scoring. Part 1: method and assessment of docking accuracy J Med Chem 47 2004 1739 1749
46. T. Takemoto, S. Arihara, K. Yoshikawa, J. Kawasaki, T. Nakajima, and M. Okuhira Studies on the constituents of Cucurbitaceae plants. Part XI: on the saponin constituents of Gynostemma pentaphyllum Makino (7) Yakugaku Zasshi 104 1984 1043 1049
47. J.J. Repa, S.D. Turley, J.A. Lobaccaro, J. Medina, L. Li, and K. Lustig Regulation of absorption and ABC1-mediated efflux of cholesterol by RXR heterodimers Science 289 2000 1524 1529
48. K. Schwartz, R.M. Lawn, and D.P. Wade ABC1 gene expression and ApoA-I-mediated cholesterol efflux are regulated by LXR Biochem Biophys Res Commun 274 2000 794 802
49. A. Venkateswaran, B.A. Laffitte, S.B. Joseph, P.A. Mak, D.C. Wilpitz, and P.A. Edwards Control of cellular cholesterol efflux by the nuclear oxysterol receptor LXR alpha Proc Natl Acad Sci USA 97 2000 12097 12102
50. K.D. Whitney, M.A. Watson, B. Goodwin, C.M. Galardi, J.M. Maglich, and J.G. Wilson Liver X receptor (LXR) regulation of the LXRalpha gene in human macrophages J Biol Chem 276 2001 43509 43515
51. Y. Watanabe, T. Tanaka, Y. Uchiyama, T. Takeno, A. Izumi, and H. Yamashita Establishment of a monoclonal antibody for human LXRalpha: detection of LXRalpha protein expression in human macrophages Nucl Recept 1 2003 1 6
52. E. Kaneko, M. Matsuda, Y. Yamada, Y. Tachibana, I. Shimomura, and M. Makishima Induction of intestinal ATP-binding cassette transporters by a phytosterol-derived liver X receptor agonist J Biol Chem 278 2003 36091 36098
53. Y. Sun, J. Yao, T.W. Kim, and A.R. Tall Expression of liver X receptor target genes decreases cellular amyloid beta peptide secretion J Biol Chem 278 2003 27688 27694
54. Y. Wang, B. Kurdi-Haidar, and J.F. Oram LXR-mediated activation of macrophage stearoyl-CoA desaturase generates unsaturated fatty acids that destabilize ABCA1 J Lipid Res 45 2004 972 980
55. S. Alberti, G. Schuster, P. Parini, D. Feltkamp, U. Diczfalusy, and M. Rudling Hepatic cholesterol metabolism and resistance to dietary cholesterol in LXRbeta-deficient mice J Clin Invest 107 2001 565 573
56. D.S. Lala Liver X receptors and atherosclerosis IDrugs 7 2004 563 569
57. G.U. Schuster, P. Parini, L. Wang, S. Alberti, K.R. Steffensen, and G.K. Hansson Accumulation of foam cells in liver X receptor-deficient mice Circulation 106 2002 1147 1153
58. Y. Li, C. Bolten, B.G. Bhat, J. Woodring-Dietz, S. Li, and S.K. Prayaga Induction of human liver X receptor alpha gene expression via an autoregulatory loop mechanism Mol Endocrinol 16 2002 506 514
59. A. Castrillo, S.B. Joseph, C. Marathe, D.J. Mangelsdorf, and P. Tontonoz Liver X receptor-dependent repression of matrix metalloproteinase-9 expression in macrophages J Biol Chem 278 2003 10443 10449
60. S.B. Joseph, A. Castrillo, B.A. Laffitte, D.J. Mangelsdorf, and P. Tontonoz Reciprocal regulation of inflammation and lipid metabolism by liver X receptors Nat Med 9 2003 213 219
61. N. Terasaka, A. Hiroshima, A. Ariga, S. Honzumi, T. Koieyama, and T. Inaba Liver X receptor agonists inhibit tissue factor expression in macrophages FEBS J 272 2005 1546 1556
62. H.N. Ginsberg New perspectives on atherogenesis: role of abnormal triglyceride-rich lipoprotein metabolism Circulation 106 2002 2137 2142
63. P. Tontonoz, and D.J. Mangelsdorf Liver X receptor signaling pathways in cardiovascular disease Mol Endocrinol 17 2003 985 993
64. N. Guex, and M.C. Peitsch SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modelling Electrophoresis 18 1997 2714 2723