Issue 13, 2011
From the journal:

Organic & Biomolecular Chemistry

Towards new ligands of nuclear receptors. Discovery of malaitasterol A, an unique bis-secosterol from marine sponge Theonella swinhoei†

Simona De Marino,a   Valentina Sepe,a   Maria Valeria D'Auria,a   Giuseppe Bifulco,b   Barbara Renga,c   Sylvain Petek,d   Stefano Fioruccic  and  Angela Zampella*a  

* Corresponding authors

a Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli “Federico II”, via D. Montesano 49, 80131 Napoli, Italy
E-mail: azampell@unina.it
Fax: +39-081676552
Tel: +39-081678525

b Dipartimento di Scienze Farmaceutiche, Università di Salerno, via Ponte don Melillo, 84084 Fisciano (SA), Italy

c Dipartimento di Medicina Clinica e Sperimentale, Università di Perugia, Nuova Facoltà di Medicina e Chirurgia, Via Gerardo Dottori 1, S. Andrea delle Fratte, 06132 Perugia, Italy

d Institut de Recherche pour le Développement (IRD), Polynesian Research Center on Island Biodiversity, BP529, 98713 Papeete, Tahiti, French Polynesia

Abstract

Malaitasterol A, an unprecedented bis-secosterol, was isolated from a Solomon collection of Theonella swinhoei. The structure was elucidated on the basis of a combination of comprehensive 1D and 2D NMR analysis, high-resolution mass spectrometry and DFT 13C chemical shift calculations. The biological characterization of malaitasterol A provided evidence that this compound is a potent agonist of pregnane-X-receptor and its putative binding mode to PXR has been obtained through docking calculations.

Graphical abstract: Towards new ligands of nuclear receptors. Discovery of malaitasterol A, an unique bis-secosterol from marine sponge Theonella swinhoei

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Article information

DOI
https://doi.org/10.1039/C1OB05378G
Article type
Paper
Submitted
10 Mar 2011
Accepted
08 Apr 2011
First published
11 Apr 2011

Org. Biomol. Chem., 2011,9, 4856-4862

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Towards new ligands of nuclear receptors. Discovery of malaitasterol A, an unique bis-secosterol from marine sponge Theonella swinhoei

S. De Marino, V. Sepe, M. V. D'Auria, G. Bifulco, B. Renga, S. Petek, S. Fiorucci and A. Zampella, Org. Biomol. Chem., 2011, 9, 4856 DOI: 10.1039/C1OB05378G

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