4-Methylenesterols from Theonella swinhoei sponge are natural pregnane-X-receptor agonists and farnesoid-X-receptor antagonists that modulate innate immunity

[1]  M. Trauner,et al.  Role of nuclear receptors in the adaptive response to bile acids and cholestasis: pathogenetic and therapeutic considerations. , 2006, Molecular pharmaceutics.

[2]  G. Bifulco,et al.  Solomonamides A and B, new anti-inflammatory peptides from Theonella swinhoei. , 2011, Organic letters.

[3]  S. Kliewer,et al.  Complementary Roles of Farnesoid X Receptor, Pregnane X Receptor, and Constitutive Androstane Receptor in Protection against Bile Acid Toxicity* , 2003, Journal of Biological Chemistry.

[4]  N. Nakayama,et al.  Structures of nine oxygenated 4-methylene sterols from Hachijo marine sponge Theonella swinhoei , 1995, Steroids.

[5]  Shigeki Matsunaga,et al.  Polytheonamides A and B, highly cytotoxic, linear polypeptides with unprecedented structural features, from the marine sponge, Theonella swinhoei. , 2005, Journal of the American Chemical Society.

[6]  Roberto Pellicciari,et al.  Structural basis for bile acid binding and activation of the nuclear receptor FXR. , 2003, Molecular cell.

[7]  C. Djerassi,et al.  Sterols in marine invertebrates. 22. Isolation and structure elucidation of conicasterol and theonellasterol, two new 4-methylene sterols from the Red Sea sponges Theonella conica and Theonella swinhoei , 1981 .

[8]  V. Sepe,et al.  Perthamides C and D, two new potent anti-inflammatory cyclopeptides from a Solomon Lithistid sponge Theonella swinhoei , 2009 .

[9]  D. Borderie,et al.  Effects of bile acids on the humoral immune response: a mechanistic approach. , 2001, Life sciences.

[10]  Marco Migliorati,et al.  Farnesoid X receptor suppresses constitutive androstane receptor activity at the multidrug resistance protein-4 promoter. , 2011, Biochimica et biophysica acta.

[11]  R. Soest The Indonesian sponge fauna: a status report , 1989 .

[12]  K. Lindor,et al.  Current concepts in the pathogenesis of primary biliary cirrhosis. , 2005, Annals of hepatology.

[13]  Gabriele Costantino,et al.  Farnesoid X receptor: from structure to potential clinical applications. , 2005, Journal of medicinal chemistry.

[14]  M. K. Harper,et al.  Aurantosides G, H, and I: three new tetramic acid glycosides from a Papua New Guinea Theonella swinhoei. , 2005, Journal of natural products.

[15]  U. Beuers,et al.  Ursodeoxycholic acid in cholestatic liver disease: Mechanisms of action and therapeutic use revisited , 2002, Hepatology.

[16]  Sean Ekins,et al.  Challenges Predicting Ligand-Receptor Interactions of Promiscuous Proteins: The Nuclear Receptor PXR , 2009, PLoS Comput. Biol..

[17]  E. Distrutti,et al.  Pregnane-X-receptor mediates the anti-inflammatory activities of rifaximin on detoxification pathways in intestinal epithelial cells. , 2010, Biochemical pharmacology.

[18]  E. Riley,et al.  IL-10: The Master Regulator of Immunity to Infection , 2008, The Journal of Immunology.

[19]  G. Bifulco,et al.  Theonellasterols and conicasterols from Theonella swinhoei. Novel marine natural ligands for human nuclear receptors. , 2011, Journal of medicinal chemistry.

[20]  K. Lindor,et al.  Latest and Emerging Therapies for Primary Biliary Cirrhosis and Primary Sclerosing Cholangitis , 2010, Current gastroenterology reports.

[21]  M F Sanner,et al.  Python: a programming language for software integration and development. , 1999, Journal of molecular graphics & modelling.

[22]  M. Voiculescu,et al.  New therapeutical indications of ursodeoxycholic acid. , 2005, Romanian journal of gastroenterology.

[23]  T. Kodama,et al.  Therapeutic Role of Rifaximin in Inflammatory Bowel Disease: Clinical Implication of Human Pregnane X Receptor Activation , 2010, Journal of Pharmacology and Experimental Therapeutics.

[24]  S. Arihara,et al.  Swinhosterols A−C, 4-Methylene Secosteroids from the Marine Sponge Theonella swinhoei , 1997 .

[25]  Malcolm R. Davidson,et al.  A Model Analysis of Arterial Oxygen Desaturation during Apnea in Preterm Infants , 2009, PLoS Comput. Biol..

[26]  V. Sepe,et al.  Total synthesis and pharmacological characterization of solomonsterol A, a potent marine pregnane-X-receptor agonist endowed with anti-inflammatory activity. , 2011, Journal of medicinal chemistry.

[27]  P. Crews,et al.  A serendipitous discovery of isomotuporin-containing sponge populations of Theonella swinhoei. , 2007, Journal of natural products.

[28]  M. Schmuth,et al.  Modulation of T Lymphocyte Function by the Pregnane X Receptor , 2010, The Journal of Immunology.

[29]  Masahiro Tohkin,et al.  Targeted Disruption of the Nuclear Receptor FXR/BAR Impairs Bile Acid and Lipid Homeostasis , 2000, Cell.

[30]  L. Moore,et al.  Crystal structure of the pregnane X receptor-estradiol complex provides insights into endobiotic recognition. , 2007, Molecular endocrinology.

[31]  Fengchun Zhang,et al.  Primary biliary cirrhosis: what do autoantibodies tell us? , 2010, World journal of gastroenterology.

[32]  G. Bifulco,et al.  Solomonsterols A and B from Theonella swinhoei. The first example of C-24 and C-23 sulfated sterols from a marine source endowed with a PXR agonistic activity. , 2011, Journal of medicinal chemistry.

[33]  R. F. Angawi,et al.  Dehydroconicasterol and aurantoic acid, a chlorinated polyene derivative, from the Indonesian sponge Theonella swinhoei. , 2009, Journal of Natural Products.

[34]  M. Mori,et al.  Nuclear receptors CAR and PXR; therapeutic targets for cholestatic liver disease. , 2011, Frontiers in bioscience.

[35]  L. Moore,et al.  The Human Nuclear Xenobiotic Receptor PXR: Structural Determinants of Directed Promiscuity , 2001, Science.

[36]  G. Bifulco,et al.  Towards new ligands of nuclear receptors. Discovery of malaitasterol A, an unique bis-secosterol from marine sponge Theonella swinhoei. , 2011, Organic & biomolecular chemistry.

[37]  F. Baldelli,et al.  Farnesoid X receptor agonist for the treatment of liver and metabolic disorders: focus on 6-ethyl-CDCA. , 2011, Mini reviews in medicinal chemistry.

[38]  Conrad C. Huang,et al.  UCSF Chimera—A visualization system for exploratory research and analysis , 2004, J. Comput. Chem..

[39]  Giuseppe Bifulco,et al.  Discovery of sulfated sterols from marine invertebrates as a new class of marine natural antagonists of farnesoid-X-receptor. , 2011, Journal of medicinal chemistry.

[40]  C. Selmi,et al.  Infectious Agents and Xenobiotics in the Etiology of Primary Biliary Cirrhosis , 2011, Disease markers.

[41]  G. Bifulco,et al.  Perthamides C-F, potent human antipsoriatic cyclopeptides , 2011 .

[42]  A. Zampella,et al.  Swinholide J, a Potent Cytotoxin from the Marine Sponge Theonella swinhoei , 2011, Marine drugs.

[43]  A. Burroughs,et al.  Meta‐analysis: ursodeoxycholic acid for primary sclerosing cholangitis , 2011, Alimentary pharmacology & therapeutics.

[44]  L. Moore,et al.  2.1 A crystal structure of human PXR in complex with the St. John's wort compound hyperforin. , 2003, Biochemistry.

[45]  E. Distrutti,et al.  Targeting farnesoid X receptor for liver and metabolic disorders. , 2007, Trends in molecular medicine.

[46]  F. Baldelli,et al.  Inhibition of NF-κB by a PXR-dependent pathway mediates counter-regulatory activities of rifaximin on innate immunity in intestinal epithelial cells. , 2011, European journal of pharmacology.

[47]  L. Goad,et al.  The 220 MHz NMR spectra of phytosterols , 1976 .

[48]  Y. Yi,et al.  Oxygenated 4‐Methylidene Sterols from the South China Sea Sponge Theonella swinhoei , 2010 .

[49]  Timothy M Willson,et al.  The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism. , 2002, Endocrine reviews.

[50]  E Jenny Heathcote,et al.  Orphanet Journal of Rare BioMed Central Review Primary biliary cirrhosis , 2008 .

[51]  David S. Goodsell,et al.  AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility , 2009, J. Comput. Chem..

[52]  A. Mcinnes,et al.  Identification of C-24 alkyl epimers of marine sterols by 13C nuclear magnetic resonance spectroscopy , 1978 .

[53]  R. Evans,et al.  Benefit of farnesoid X receptor inhibition in obstructive cholestasis. , 2006, Proceedings of the National Academy of Sciences of the United States of America.

[54]  A. Hofmann Cholestatic liver disease: pathophysiology and therapeutic options. , 2002, Liver.

[55]  R. Evans,et al.  Regulation of a xenobiotic sulfonation cascade by nuclear pregnane X receptor (PXR) , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[56]  W. Alrefai,et al.  Bile Acid Transporters: Structure, Function, Regulation and Pathophysiological Implications , 2007, Pharmaceutical Research.

[57]  M. Trauner,et al.  Principles of hepatic organic anion transporter regulation during cholestasis, inflammation and liver regeneration. , 2007, Biochimica et biophysica acta.