Polyhydroxylated sterols from the Indonesian soft coral Sinularia sp. and their effect on farnesoid X-activated receptor

Steroids

Volumn 77, Issue 5, 2012, Pages 433-440

  Putra, Masteria Yunovilsa ^a,b   Bavestrello, Giorgio ^b   Cerrano, Carlo ^c   Renga, Barbara ^d   D'Amore, Claudio ^d   Fiorucci, Stefano ^d   Fattorusso, Ernesto ^a   Taglialatela Scafati, Orazio ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^c UNIVERSITY OF GENOA   (Italy)

^d UNIVERSITY OF PERUGIA   (Italy)

Author keywords

24 Methylcholestane; FXR antagonist; Gorgosterol; Nuclear receptors; Soft corals

Indexed keywords

24 METHYLCHOLESTAN 11 ACETOXY 1ALPHA,3BETA,5ALPHA,6BETA TETRAOL; 24 METHYLCHOLESTAN 1ALPHA,3BETA DIOL; 24 METHYLCHOLESTAN 1ALPHA,3BETA,25 TRIOL; 24 METHYLCHOLESTEROL; 24 METHYLENE CHOLESTEROL; 3ALPHA,5BETA DIHYDROXY GORGOSTAN 6 ONE; 3BETA,5ALPHA,25 TRIHYDROXY 24 METHYLCHOLESTAN 6 ONE; FARNESOID X RECEPTOR; GORGOSTEROL; STEROL; UNCLASSIFIED DRUG;

ARTICLE; CHOLESTASIS; CORAL; DRUG ISOLATION; DRUG MECHANISM; DRUG STRUCTURE; GENE EXPRESSION; HUMAN; HUMAN CELL; SINULARIA;

ANIMALS; ANTHOZOA; ATP-BINDING CASSETTE TRANSPORTERS; CELLS, CULTURED; CHOLESTEROL; GENE EXPRESSION; HEP G2 CELLS; HUMANS; HYDROXYLATION; INDONESIA; MEMBRANE TRANSPORT PROTEINS; MOLECULAR STRUCTURE; PRIMARY CELL CULTURE; RECEPTORS, CYTOPLASMIC AND NUCLEAR; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; STEREOISOMERISM; STEROLS; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION;

ALCYONACEA; SINULARIA;

EID: 84858342203     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.12.026     Document Type: Article

References (23)

1. J.M. Pascussi, S. Gerbal-Chaloin, C. Duret, M. Daujat-Chavanieu, M.J. Vilarem, and P. Maurel The tangle of nuclear receptors that controls xenobiotic metabolism and transport: crosstalk and consequences Annu Rev Pharmacol Toxicol 48 2008 1 32 (Pubitemid 351738147)
2. S. Fiorucci, A. Mencarelli, E. Distrutti, G. Palladino, and S. Cipriani Targeting farnesoid-X-receptor: from medicinal chemistry to disease treatment Curr Med Chem 17 2010 139 159
3. A. Ward, R.N. Brogden, R.C. Hell, T.M. Speight, and G.S. Avery Ursodeoxycholic acid: a review of its pharmacological properties and therapeutic efficacy Drugs 27 1984 95 131 (Pubitemid 14223113)
4. J. Cui, L. Huang, A. Zhao, J.L. Lew, J. Yu, S. Sahoo, P.T. Meinke, I. Royo, F. Pelaez, and S.D. Wright Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pump J Biol Chem 278 2003 10214 10220 (Pubitemid 36800282)
5. S.-J. Nam, H. Ko, M. Shin, J. Ham, J. Chin, Y. Kim, H. Kim, K. Shin, H. Choi, and H. Kang Farnesoid X-activated receptor antagonists from a marine sponge Spongia sp Bioorg Med Chem Lett 16 2006 5398 5402 (Pubitemid 44332211)
6. V. Sepe, G. Bifulco, B. Renga, C. D'Amore, S. Fiorucci, and A. Zampella Discovery of sulfated sterols from marine invertebrates as a new class of marine natural antagonists of farnesoid-X-receptor J Med Chem 54 2011 1314 1320
7. N.S. Sarma, M.S. Krishna, S.G. Pasha, T.S.P. Rao, Y. Venkateswarlu, and P.S. Parameswaran Chem Rev 109 2009 2803 2828
8. E. Fattorusso, A. Romano, O. Taglialatela-Scafati, C. Irace, C. Maffettone, G. Bavestrello, and C. Cerrano Oxygenated cembranoids of the decaryiol type from the Indonesian soft coral Lobophytum sp Tetrahedron 65 2009 2898 2904
9. C. Fattorusso, M. Persico, B. Calcinai, C. Cerrano, S. Parapini, and D. Taramelli Manadoperoxides A-D from the Indonesian sponge Plakortis cfr. simplex. Further insights on the structure-activity relationships of simple 1,2-dioxane antimalarials J Nat Prod 73 2010 1138 1145
10. 2 receptor ligand Steroids 76 2011 998 1002
11. E. Fattorusso, P. Luciano, M.Y. Putra, O. Taglialatela-Scafati, A. Ianaro, and E. Panza Chloroscabrolides, chlorinated norcembranoids from the Indonesian soft coral Sinularia sp Tetrahedron 67 2011 7983 7988
12. W. Lu, C. Zhang, L. Zeng, and J. Su Synthesis of polyhydroxysterols (V): efficient and stereospecific synthesis of 24-methylene-cholest-5-ene-3β, 7α-diol and its C-7 epimer Steroids 69 2004 803 808 (Pubitemid 39593393)
13. N. Koizumi, Y. Fujimoto, T. Takeshita, and N. Ikekawa Studies on steroids. Part 49. Carbon-13 nuclear magnetic resonance of 24-substituted steroids Chem Pharm Bull 27 1979 38 42 (Pubitemid 9114494)
14. Musmar MJ, Weinheimer AJ, Martin GE, Hurd RE. Assignment of the high field resonances of a gorgosterol derivative through the use of autocorrelated two-dimensional proton NMR spectroscopy. J Org Chem 1983;48:3580-1 and references cited therein.
15. M. Kobayashi, T. Hayashi, K. Hayashi, M. Tanabe, T. Nakagawa, and H. Mitsuhashi Polyhydroxysterols of the soft coral Sarcophytum glaucum: isolation and synthesis of 5α-cholestane 1β,3β,5,6β-tetrol Chem Pharm Bull 31 1983 1848 1855
16. P. Ramesh, and Y. Venkateswarlu Novel steroid constituents of the soft coral Sinularia dissecta Steroids 64 1999 785 789 (Pubitemid 29461012)
17. A. Rueda, E. Zubia, M.J. Ortega, and J. Salva Structure and cytotoxicity of new polyhydroxylated sterols from the Caribbean gorgonian Plexaurella grisea Steroids 76 2001 897 904 (Pubitemid 33064432)
18. 28 polyhydroxysterols from two Sclerophytum sp. soft corals Chem Pharm Bull 39 1991 297 300
19. A.D. Wright, E. Goclik, and G.M. Koenig Oxygenated analogues of gorgosterol and ergosterol from the soft coral Capnella lacertiliensis J Nat Prod 66 2003 157 160 (Pubitemid 36278224)
20. S.W. Rampen, J.K. Volkman, S.B. Hur, B.A. Abbas, S. Schouten, and I.D. Jameson Occurrence of gorgosterol in diatoms of the genus Delphineis Org Geochem 40 2009 144 147
21. T. Terasawa, Y. Hirano, Y. Fujimoto, and N. Ikekawa Stereocontrolled synthesis of gorgosterol J Chem Soc Chem Commun 20 1983 1180 1182
22. B. Renga, A. Mencarelli, S. Cipriani, C. D'Amore, A. Zampella, and M.C. Monti The nuclear receptor FXR regulates hepatic transport and metabolism of glutamine and glutamate Biochim Biophys Acta 1812 2011 1522 1531
23. S. De Marino, R. Ummarino, M.V. D'Auria, M.G. Chini, G. Bifulco, and B. Renga Theonellasterols and conicasterols from Theonella swinhoei. Novel marine natural ligands for human nuclear receptors J Med Chem 54 2011 3065 3075