6533b856fe1ef96bd12b3068

RESEARCH PRODUCT

Perthamides C-F, potent human antipsoriatic cyclopeptides

Miguel PayáAngela ZampellaCécile DebitusMaria Valeria D'auriaRosa María Hernández AndrésGiuseppe BifulcoCarmen FestaValentina SepeSimona De MarinoMaría Carmen Terencio

subject

Quantum chemicalchemistry.chemical_classificationTheonella swinhoeiStereochemistryChemical shiftOrganic ChemistryAbsolute configurationTheonella swinhoeicyclopeptidesBiochemistryCombinatorial chemistryCyclic peptideResidue (chemistry)Anti-Inflammatory activitychemistryinflammationDrug DiscoveryMarine compoundsCyclic peptidesmarine natural product

description

Abstract Two new cyclopeptides, perthamides E and F were isolated from the polar extracts of the sponge Theonella swinhoei . The new structures, featuring an unprecedented β-amino acid unit (AHMOA), were determined by interpretation of NMR and MS data. The absolute configuration of the AHMOA residue was proposed on the basis of quantum chemical calculation of NMR chemical shifts. Perthamides were proved to inhibit TNF-α and IL-8 release in primary human keratinocytes cells and therefore could represent potentially leads for the treatment of psoriasis.

10.1016/j.tet.2011.07.077http://hdl.handle.net/11588/403325