Theonellasterols and conicasterols from Theonella swinhoei. Novel marine natural ligands for human nuclear receptors.
作者： Simona De Marino , Raffaella Ummarino , Maria Valeria D’Auria , Maria Giovanna Chini , Giuseppe Bifulco
DOI: 10.1021/JM200169T
关键词: Chemistry 、 Pregnane X receptor 、 Receptor 、 Pregnane 、 Carbon-13 NMR 、 Nuclear magnetic resonance spectroscopy 、 Nuclear receptor 、 Heteronuclear single quantum coherence spectroscopy 、 Stereochemistry 、 Docking (molecular)
摘要: Silica gel column chromatography, followed by HPLC purification on the apolar fraction of methanol extract marine sponge Theonella swinhoei, resulted in isolation a library 10 polyhydroxylated steroids which we named theonellasterols B−H (1−7) and conicasterols B-D (8−10). The structures were determined basis extensive spectroscopic data (MS, 1H 13C NMR, COSY, HSQC, HMBC, ROESY) analysis, putative binding mode to nuclear receptors (NRs) has been obtained through docking calculations. Pharmacological structure−activity relationship analysis demonstrate that these natural are potent ligands human pregnane receptor (PXR) modulator farnesoid-X-receptor (FXR). In addition, molecular characterization theonellasterol G allowed identification first FXR PXR ligand so far identified. Exposure liver cells this agent induction PXR-regulated genes modulation FXR-...
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M F Sanner, Python: a programming language for software integration and development. Journal of Molecular Graphics & Modelling. ,vol. 17, pp. 57- 61 ,(1999)
Salvatore Modica, Raffaella M. Gadaleta, Antonio Moschetta, Deciphering the nuclear bile acid receptor FXR paradigm. Nuclear Receptor Signaling. ,vol. 8, ,(2010) , 10.1621/NRS.08005
Haibo Wang, Jasmine Chen, Kevin Hollister, Lawrence C Sowers, Barry M Forman, Endogenous bile acids are ligands for the nuclear receptor FXR/BAR. Molecular Cell. ,vol. 3, pp. 543- 553 ,(1999) , 10.1016/S1097-2765(00)80348-2
Carmen Festa, Simona De Marino, Valentina Sepe, Maria Valeria D’Auria, Giuseppe Bifulco, Cecile Débitus, Mariarosaria Bucci, Valentina Vellecco, Angela Zampella, Solomonamides A and B, new anti-inflammatory peptides from Theonella swinhoei, Organic Letters. ,vol. 13, pp. 1532- 1535 ,(2011) , 10.1021/OL200221N
Li-Zhi Mi, Srikripa Devarakonda, Joel M. Harp, Qing Han, Roberto Pellicciari, Timothy M. Willson, Sepideh Khorasanizadeh, Fraydoon Rastinejad, Structural Basis for Bile Acid Binding and Activation of the Nuclear Receptor FXR Molecular Cell. ,vol. 11, pp. 1093- 1100 ,(2003) , 10.1016/S1097-2765(03)00112-6
Yumi Sugo, Yoshinobu Inouye, Noboru Nakayama, Structures of nine oxygenated 4-methylene sterols from Hachijo marine sponge Theonella swinhoei. Steroids. ,vol. 60, pp. 738- 742 ,(1995) , 10.1016/0039-128X(95)00108-3
Carmen Festa, Simona De Marino, Valentina Sepe, Maria Chiara Monti, Paolo Luciano, Maria Valeria D'Auria, Cecile Débitus, Mariarosaria Bucci, Valentina Vellecco, Angela Zampella, Perthamides C and D, two new potent anti-inflammatory cyclopeptides from a Solomon Lithistid sponge Theonella swinhoei Tetrahedron. ,vol. 65, pp. 10424- 10429 ,(2009) , 10.1016/J.TET.2009.10.026
Yu Xue, Linda B. Moore, Jillian Orans, Li Peng, Sompop Bencharit, Steven A. Kliewer, Matthew R. Redinbo, Crystal structure of the pregnane X receptor-estradiol complex provides insights into endobiotic recognition. Molecular Endocrinology. ,vol. 21, pp. 1028- 1038 ,(2007) , 10.1210/ME.2006-0323
Ryan E Watkins, G Bruce Wisely, Linda B Moore, Jon L Collins, Millard H Lambert, Shawn P Williams, Timothy M Willson, Steven A Kliewer, Matthew R Redinbo, The Human Nuclear Xenobiotic Receptor PXR: Structural Determinants of Directed Promiscuity Science. ,vol. 292, pp. 2329- 2333 ,(2001) , 10.1126/SCIENCE.1060762
Tomofumi Fujino, Mizuho Une, Tsuneo Imanaka, Kazuhide Inoue, Tomoko Nishimaki-Mogami, Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation. Journal of Lipid Research. ,vol. 45, pp. 132- 138 ,(2004) , 10.1194/JLR.M300215-JLR200