RESUMEN
Continued investigation of the polyphenolic pool of the fruits of Mansoa hirsuta afforded four additional members of the new class of glucosylated oligomeric flavonoids comprising a flavanone core linked to 1,3-diarylpropane C6-C3-C6 units. The structures and absolute configurations of mansoins C-F (3-6) were established by analysis of NMR and electronic circular dichroism data. Mansoin C (3) was identified as a diglucosylated heterodimer, whereas mansoins D (4), E (5), and F (6) were identified as triglucosylated heterotrimers, isomeric with mansoin A (1). Mansoin F (6) inhibited TNF-α release by lipopolysaccharide-stimulated THP-1 cells (IC50 of 19.3 ± 1.3 µM) and, as with mansoin A (1), reduced the phosphorylation levels of p-65-NF-κB, when assayed at 50 µM. These results indicate that the potential anti-inflammatory properties of mansoin F (6) are probably due to inhibition of the NF-κB pathway and inhibition of TNF-α release.
Asunto(s)
Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Bignoniaceae/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Glucósidos/aislamiento & purificación , Glucósidos/farmacología , Antiinflamatorios/química , Flavonoides/química , Frutas/química , Glucósidos/química , Humanos , Lipopolisacáridos/farmacología , Estructura Molecular , FN-kappa B/antagonistas & inhibidores , Factor de Necrosis Tumoral alfa/antagonistas & inhibidoresRESUMEN
Mansoins A (1) and B (2) isolated from the fruits of Mansoa hirsuta represent new glucosylated heterotrimeric flavonoids with a flavanone core linked to two 1,3-diarylpropane C6-C3-C6 units. Their structures and absolute configurations were established by analysis of their NMR and electronic circular dichroism spectroscopic data. Compounds 1 and 2 inhibited TNF-α release by LPS-stimulated THP-1 cells with different potencies, with mansoin B (2) being active at lower concentrations than mansoin A (1) (IC50 values 20.0±1.4 and 48.1±1.8 µM, respectively). These results indicate potential anti-inflammatory properties for this structural type of oligoflavonoids, especially for mansoin B (2).