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Oxygenated Polyketides from Plakinastrella mamillaris as a New Chemotype of PXR Agonists
Department of Pharmacy, University of Naples "Federico II", via D. Montesano 49, Naples 80131, Italy
Department of Clinical and Experimental Medicine, Faculty of Medicine, University of Perugia, via Gerardo Dottori 1, S. Andrea Delle Fratte, Perugia 06132, Italy
Department of Pharmacy, University of Salerno, via Ponte don Melillo, Fisciano (SA) 84084, Italy
* Author to whom correspondence should be addressed.
Received: 24 April 2013; in revised form: 27 May 2013 / Accepted: 28 May 2013 / Published: 2 July 2013
Abstract: Further purification of the apolar extracts of the sponge Plakinastrella mamillaris, afforded a new oxygenated polyketide named gracilioether K, together with the previously isolated gracilioethers E–G and gracilioethers I and J. The structure of the new compound has been elucidated by extensive NMR (1H and 13C, COSY, HSQC, HMBC, and ROESY) and ESI-MS analysis. With the exception of gracilioether F, all compounds are endowed with potent pregnane-X-receptor (PXR) agonistic activity and therefore represent a new chemotype of potential anti-inflammatory leads. Docking calculations suggested theoretical binding modes of the identified compounds, compatible with an agonistic activity on hPXR, and clarified the molecular basis of their biological activities.
Keywords: marine sponge; Plakinastrella mamillaris; oxygenated polyketide; nuclear receptors; pregnane-X-receptor; anti-inflammatory activity
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MDPI and ACS Style
Festa, C.; D'Amore, C.; Renga, B.; Lauro, G.; Marino, S.D.; D'Auria, M.V.; Bifulco, G.; Zampella, A.; Fiorucci, S. Oxygenated Polyketides from Plakinastrella mamillaris as a New Chemotype of PXR Agonists. Mar. Drugs 2013, 11, 2314-2327.
Festa C, D'Amore C, Renga B, Lauro G, Marino SD, D'Auria MV, Bifulco G, Zampella A, Fiorucci S. Oxygenated Polyketides from Plakinastrella mamillaris as a New Chemotype of PXR Agonists. Marine Drugs. 2013; 11(7):2314-2327.
Festa, Carmen; D'Amore, Claudio; Renga, Barbara; Lauro, Gianluigi; Marino, Simona D.; D'Auria, Maria V.; Bifulco, Giuseppe; Zampella, Angela; Fiorucci, Stefano. 2013. "Oxygenated Polyketides from Plakinastrella mamillaris as a New Chemotype of PXR Agonists." Mar. Drugs 11, no. 7: 2314-2327.