RESUMEN
Six new monoterpenoid indole alkaloids, kopsinidines C-E (1-3), 11,12-methylenedioxychanofruticosinic acid (4), 12-methoxychanofruticosinic acid (5), and N(4)-methylkopsininate (7), as well as chanofruticosinic acid (6, as a natural product) and 23 known alkaloids, were obtained from the twigs and leaves of Kopsia officinalis. Their structures were characterized by physical data analysis. All isolated compounds were evaluated for their immunosuppressive activity on human T cell proliferation. Rhazinilam (29) significantly inhibited human T cell proliferation activated by anti-CD3/anti-CD28 antibodies (IC50 = 1.0 µM) and alloantigen stimulation (IC50 = 1.1 µM) without obvious cytotoxicity for naïve human T cells and peripheral blood mononuclear cells (0-320 µM). Although it did not affect T cell activation, it induced T cell cycle arrest in the G2/M phase and inhibited proinflammatory cytokine production in activated T cells.
Asunto(s)
Apocynaceae/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Inmunosupresores/aislamiento & purificación , Inmunosupresores/farmacología , Alcaloides de Triptamina Secologanina/aislamiento & purificación , Alcaloides de Triptamina Secologanina/farmacología , Alcaloides , Ciclo Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Medicamentos Herbarios Chinos/química , Humanos , Inmunosupresores/química , Indolizinas , Lactamas , Leucocitos Mononucleares/efectos de los fármacos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/química , Tallos de la Planta/química , Alcaloides de Triptamina Secologanina/química , Linfocitos T/efectos de los fármacosRESUMEN
Calophyline A (1), a novel unprecedented rearranged monoterpenoid indole alkaloid, along with a new natural product N-methyl aspidodasycarpine (2) and six known analogues, was isolated from the trunk barks of Winchia calophylla. The structure of compound 1 was elucidated on the basis of spectroscopic data and then confirmed by a single-crystal X-ray crystallographic analysis. A hypothetical biogenetic pathway for compound 1 was proposed. All isolated compounds were evaluated for their in vitro cytotoxicity against a small panel of human cancer cell lines.