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

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.

SUBMITTER: Festa C

PROVIDER: S-EPMC3736425 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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

Festa Carmen C D'Amore Claudio C Renga Barbara B Lauro Gianluigi G De Marino Simona S D'Auria Maria Valeria MV Bifulco Giuseppe G Zampella Angela A Fiorucci Stefano S

Marine drugs 20130702 7

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 ...[more]

PMID: 23820629

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