RESUMEN
Four new compounds (1-4) were isolated along with 16 known compounds from whole plants of Peperomia duclouxii. The new structures were elucidated as 4-hydroxy-2-[(3,4-methylenedioxyphenyl)nonanoyl]cyclohexane-1,3-dione (1), 4-hydroxy-2-[(3,4-methylenedioxyphenyl)undecanoyl]cyclohexane-1,3-dione (2), 4-hydroxy-2-[(3,4-methylenedioxyphenyl)tridecanoyl]cyclohexane-1,3-dione (3), and 2-[(3,4-methylenedioxyphenyl)dodecyl]-4-hydroxy-2,3,4,6,7,8-hexahydro-2H-1-benzopyran-5-one (4), by analysis of their spectroscopic data. The known polyketides, surinone A and oleiferinone, showed cell growth inhibitory activity against the WI-38, VA-13, and HepG2 cell lines with IC50 values that ranged from 4.4 to 9.6 microg/mL. The known sesquiterpenoid, sinugibberodiol, showed a more potent effect on calcein accumulation than verapamil at 2.5 and 25 microg/mL. Compounds 3 and 4, surinone A, and oleiferinone showed moderate to weak inhibitory activity on the induction of the intercellular adhesion molecule-1 (ICAM-1) in the presence of IL-1alpha or TNF-alpha.
Asunto(s)
Ciclohexanonas/aislamiento & purificación , Ciclohexanonas/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Peperomia/química , Plantas Medicinales/química , Ciclohexanonas/química , Medicamentos Herbarios Chinos/química , Femenino , Fluoresceínas/farmacología , Humanos , Concentración 50 Inhibidora , Molécula 1 de Adhesión Intercelular/efectos de los fármacos , Interleucina-1alfa/metabolismo , Estructura Molecular , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Células Tumorales Cultivadas , Factor de Necrosis Tumoral alfa/metabolismo , Verapamilo/farmacologíaRESUMEN
Six new lignans (1-6), along with 14 known compounds, were obtained from Peperomia duclouxii. The new structures were elucidated mainly by the analysis of their NMR and MS data. The absolute configurations of 1-6 were determined by comparing their optical rotations or CD spectra with those of known compounds. In cytotoxic and MDR reversal cell activity assays, compound 3 showed cancer cell growth inhibitory activity against VA-13 and HepG2 cells, with IC50 values of 5.3 and 13.2 microg/mL, and more potent effects on calcein accumulation in MDR 2780AD cells than verapamil, a positive control. Compound 6 showed anti-inflammatory activity using an ICAM-1 assay (induction of the intercellular adhesion molecule-1), stimulated by IL-1alpha and TNF-alpha.
Asunto(s)
Antiinflamatorios no Esteroideos , Antineoplásicos Fitogénicos , Medicamentos Herbarios Chinos , Lignanos , Peperomia/química , Plantas Medicinales/química , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Femenino , Humanos , Molécula 1 de Adhesión Intercelular/efectos de los fármacos , Interleucina-1alfa/farmacología , Lignanos/química , Lignanos/aislamiento & purificación , Lignanos/farmacología , Células Tumorales Cultivadas , Factor de Necrosis Tumoral alfa/farmacologíaRESUMEN
Six new dibenzylbutyrolactone (6-11) and two new dibenzylbutanediol lignans (12, 13) were obtained from Peperomia duclouxii. The structures were elucidated mainly by the analysis of NMR and MS data. The anticancer activity against a normal (WI-38) and a simian virus 40-transformed human lung fibroblast cell (VA-13) and a hepatoma G2 cell (HepG2) and the MDR reversal activity of the isolated compounds were examined. Compound 7 showed moderate inhibitory activity against VA-13 and HepG2 with IC(50) values of 23.2 and 26.4 microM, respectively. Compound 2 inhibited the growth of HepG2 cells with an IC(50) of 42.8 microM. Compounds 2 and 13 exhibited stronger MDR reversal activity than verapamil, at 25 and 2.5 microg/mL, respectively, and 4, 5, and 7 showed comparable activity with verapamil, at 25, 25, and 2.5 microg/mL, respectively.
Asunto(s)
Antineoplásicos Fitogénicos , Medicamentos Herbarios Chinos , Lignanos , Peperomia/química , Plantas Medicinales/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Humanos , Concentración 50 Inhibidora , Lignanos/química , Lignanos/aislamiento & purificación , Lignanos/farmacología , Estructura Molecular , Células Tumorales Cultivadas , Verapamilo/farmacologíaRESUMEN
Five new tetrahydrofuran lignans (1-5), accompanied by four known compounds, were isolated from the ethyl acetate extract of Peperomia dindygulensis. Structures were elucidated mainly using 1D NMR, 2D NMR, and mass spectroscopic studies. The relative configurations of 1-5 were determined by NOE correlations. Several of the compounds showed weak growth inhibitory activity against three cell lines (WI-38, VA-13, and HepG2). Compound 5 exhibited stronger MDR (multidrug resistance) reversal activity than verapamil at 2.5 microg/mL in a cellular calcein accumulation assay. Compounds 4 and 5 showed weak inhibitory activity against induction of the intercellular adhesion molecule-1 (ICAM-1) in anti-inflammatory activity experiments.