Phallusiasterols A and B: Two New Sulfated Sterols from the Mediterranean Tunicate Phallusia fumigata and Their Effects as Modulators of the PXR Receptor

Purification of the apolar extracts of the marine ascidian Phallusia fumigata, afforded two new sulfated sterols, phallusiasterols A (1) and B (2). The structures of the new compounds have been elucidated using mass spectrometry and NMR experiments. The effects of phallusiasterols A and B as modulat...

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Autores principales: Imperatore, Concetta, D’Aniello, Filomena, Aiello, Anna, Fiorucci, Stefano, D’Amore, Claudio, Sepe, Valentina, Menna, Marialuisa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4012412/
https://www.ncbi.nlm.nih.gov/pubmed/24705503
http://dx.doi.org/10.3390/md12042066
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author Imperatore, Concetta
D’Aniello, Filomena
Aiello, Anna
Fiorucci, Stefano
D’Amore, Claudio
Sepe, Valentina
Menna, Marialuisa
author_facet Imperatore, Concetta
D’Aniello, Filomena
Aiello, Anna
Fiorucci, Stefano
D’Amore, Claudio
Sepe, Valentina
Menna, Marialuisa
author_sort Imperatore, Concetta
collection PubMed
description Purification of the apolar extracts of the marine ascidian Phallusia fumigata, afforded two new sulfated sterols, phallusiasterols A (1) and B (2). The structures of the new compounds have been elucidated using mass spectrometry and NMR experiments. The effects of phallusiasterols A and B as modulators of pregnane-X-receptor (PXR) have been investigated. These studies revealed that phallusiasterol A induces PXR transactivation in HepG2 cells and stimulates the expression of the PXR target genes CYP3A4 and MDR1 in the same cell line. Molecular docking calculations suggested the theoretical binding mode of phallusiasterol A with hPXR and revealed that phallusiasterol A fitted well in the LBD of PXR.
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spelling pubmed-40124122014-05-07 Phallusiasterols A and B: Two New Sulfated Sterols from the Mediterranean Tunicate Phallusia fumigata and Their Effects as Modulators of the PXR Receptor Imperatore, Concetta D’Aniello, Filomena Aiello, Anna Fiorucci, Stefano D’Amore, Claudio Sepe, Valentina Menna, Marialuisa Mar Drugs Article Purification of the apolar extracts of the marine ascidian Phallusia fumigata, afforded two new sulfated sterols, phallusiasterols A (1) and B (2). The structures of the new compounds have been elucidated using mass spectrometry and NMR experiments. The effects of phallusiasterols A and B as modulators of pregnane-X-receptor (PXR) have been investigated. These studies revealed that phallusiasterol A induces PXR transactivation in HepG2 cells and stimulates the expression of the PXR target genes CYP3A4 and MDR1 in the same cell line. Molecular docking calculations suggested the theoretical binding mode of phallusiasterol A with hPXR and revealed that phallusiasterol A fitted well in the LBD of PXR. MDPI 2014-04-03 /pmc/articles/PMC4012412/ /pubmed/24705503 http://dx.doi.org/10.3390/md12042066 Text en © 2014 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Imperatore, Concetta
D’Aniello, Filomena
Aiello, Anna
Fiorucci, Stefano
D’Amore, Claudio
Sepe, Valentina
Menna, Marialuisa
Phallusiasterols A and B: Two New Sulfated Sterols from the Mediterranean Tunicate Phallusia fumigata and Their Effects as Modulators of the PXR Receptor
title Phallusiasterols A and B: Two New Sulfated Sterols from the Mediterranean Tunicate Phallusia fumigata and Their Effects as Modulators of the PXR Receptor
title_full Phallusiasterols A and B: Two New Sulfated Sterols from the Mediterranean Tunicate Phallusia fumigata and Their Effects as Modulators of the PXR Receptor
title_fullStr Phallusiasterols A and B: Two New Sulfated Sterols from the Mediterranean Tunicate Phallusia fumigata and Their Effects as Modulators of the PXR Receptor
title_full_unstemmed Phallusiasterols A and B: Two New Sulfated Sterols from the Mediterranean Tunicate Phallusia fumigata and Their Effects as Modulators of the PXR Receptor
title_short Phallusiasterols A and B: Two New Sulfated Sterols from the Mediterranean Tunicate Phallusia fumigata and Their Effects as Modulators of the PXR Receptor
title_sort phallusiasterols a and b: two new sulfated sterols from the mediterranean tunicate phallusia fumigata and their effects as modulators of the pxr receptor
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4012412/
https://www.ncbi.nlm.nih.gov/pubmed/24705503
http://dx.doi.org/10.3390/md12042066
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