Oxygenated polyketides from Plakinastrella mamillaris as a new chemotype of PXR agonists

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...

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Published in:Marine drugs 2013-07, Vol.11 (7), p.2314-2327
Main Authors: Festa, Carmen, D'Amore, Claudio, Renga, Barbara, Lauro, Gianluigi, De Marino, Simona, D'Auria, Maria Valeria, Bifulco, Giuseppe, Zampella, Angela, Fiorucci, Stefano
Format: Article
Language:English
Subjects:
Animals
anti-inflammatory activity
Anti-Inflammatory Agents - chemistry
Anti-Inflammatory Agents - pharmacology
Biological Factors
Cell Line, Tumor
Hep G2 Cells
Humans
marine sponge
Molecular Structure
nuclear receptors
oxygenated polyketide
Plakinastrella mamillaris
Polyketides - chemistry
Polyketides - pharmacology
Porifera - chemistry
pregnane-X-receptor
Receptors, Steroid - agonists
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Summary: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.
ISSN:1660-3397
1660-3397
DOI:10.3390/md11072314