RESUMEN
Six new isochroman derivatives (annulohypoxylomans A-C, 1-3; annulohypoxylomanols A and B, 6 and 7; and annulohypoxyloside, 8), an isocoumarin (annulohypoxylomarin A, 4), and an azaphilone derivative (xylariphilone, 5) were isolated from an ethyl acetate extract derived from cultures of the endophytic fungus JS540 found in the leaves of Zizania caduciflora. The JS540 strain was identified as Annulohypoxylon truncatum. The structures of the isolated compounds were elucidated by one- and two-dimensional nuclear magnetic resonance and mass spectrometry and by comparison with related compounds from the literature. The anti-inflammatory activities of the isolated compounds were evaluated in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells. Xylariphilone (5) exhibited significant inhibitory effects on LPS-induced interleukin (IL)-6, IL-12 p40, and tumor necrosis factor (TNF)-α production with IC50 values of 5.3, 19.4, and 37.6 µM, respectively.
Asunto(s)
Antiinflamatorios/aislamiento & purificación , Benzopiranos/aislamiento & purificación , Benzopiranos/farmacología , Cromanos/aislamiento & purificación , Células Dendríticas/efectos de los fármacos , Interleucina-12/agonistas , Interleucina-12/metabolismo , Interleucina-6/agonistas , Interleucina-6/metabolismo , Isocumarinas/aislamiento & purificación , Lipopolisacáridos/farmacología , Hojas de la Planta/química , Poaceae/química , Xylariales/química , Animales , Antiinflamatorios/química , Antiinflamatorios/farmacología , Benzopiranos/química , Cromanos/química , Cromanos/farmacología , Células Dendríticas/citología , Concentración 50 Inhibidora , Interleucina-12/química , Interleucina-6/química , Isocumarinas/química , Isocumarinas/farmacología , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Factor de Necrosis Tumoral alfa/química , Factor de Necrosis Tumoral alfa/efectos de los fármacos , Factor de Necrosis Tumoral alfa/metabolismoRESUMEN
Two sesquiterpenoids, annulohpoxylotol A and B, were isolated along with five sterols from an ethyl acetate extract of cultures of the endophytic fungus Annulohypoxylon truncatum growing on leaves of Zizania caduciflora. The structures of the isolated compounds were established using one-dimensional (1D) and two-dimensional (2D)-NMR and mass spectrometry. The nuclear factor-kappa B (NF-κB) inhibitory activities of the isolated compounds stimulated with tumor necrosis factor-alpha (TNF-α) were measured using a luciferase reporter system. Annulohpoxylotol A (1) significantly inhibited NF-κB activation in a dose-dependent manner, with an IC50 of 7.11 µM, whereas annulohpoxylotol B (2) and ergone (7) moderately inhibited NF-κB transcriptional activity, with IC50 values of 19.24 and 17.51 µM, respectively.
