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

Simona De Marino; Valentina Sepe; Maria Valeria D'Auria; Giuseppe Bifulco; Barbara Renga; Sylvain Petek; Stefano Fiorucci; Angela Zampella

doi:10.1039/C1OB05378G

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Organic & Biomolecular Chemistry

Issue 13, 2011

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

Simona De Marino , Valentina Sepe , Maria Valeria D'Auria , Giuseppe Bifulco , Barbara Renga , Sylvain Petek , Stefano Fiorucci and Angela Zampella

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

DOI: 10.1039/C1OB05378G
Received 10 Mar 2011, Accepted 08 Apr 2011
First published on the web 11 Apr 2011

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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.