RESUMO
Artaboterpenoids A and B (1 and 2), two novel bisabolene-derived sesquiterpenoids, were isolated from the roots of Artabotrys hexapetalus. Their structures with absolute configurations were elucidated by spectroscopic methods, and electronic circular dichroism (ECD) analyses. Notably, 1 featured a novel carbon skeleton with a new C-2-C-10 linkage, and 2a and 2b, a pair of enantiomers, represented the first examples of 1,2-seco-bisabolene-type sesquiterpene lactones. 2a exhibited cytotoxic effects against HCT-116, HepG2, A2780, NCI-H1650, and BGC-823 cell lines with IC50 values of 1.38-8.19 µM. Plausible biogenetic pathways for artaboterpenoids A and B were proposed.
Assuntos
Annonaceae/química , Antineoplásicos Fitogênicos/química , Sesquiterpenos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Células Hep G2 , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Raízes de Plantas/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , EstereoisomerismoRESUMO
One new bithiophenes, 5-(but-3-yne-1,2-diol)-50-hydroxy-methyl-2,20-bithiophene (2), two new polyacetylenic glucosides, 3-O-b-D-glucopyranosyloxy-1-hydroxy-4E,6E-tetradecene-8,10,12-triyne (8), (5E)-trideca-1,5-dien-7,9,11-triyne-3,4-diol-4-O-b-D-glucopyranoside (9), six new terpenoid glycosides, rel-(1S,2S,3S,4R,6R)-1,6-epoxy-menthane-2,3-diol-3-O-b-D-glucopyranoside (10), rel-(1S,2S,3S,4R,6R)-3-O-(6-O-caffeoyl-b-D-glucopyranosyl)-1,6-epoxy menthane-2,3-diol (11), (2E,6E)-2,6,10-trimethyl-2,6,11-dodecatriene-1,10-diol-1-O-b-D-glucopyranoside (12), 3b,16b,29-trihydroxy oleanane-12-ene-3-O-b-D-glucopyranoside (13), 3,28-di-O-b-D-glucopyranosyl-3b,16b-dihydroxy oleanane-12-ene-28-oleanlic acid (14), 3-O-b-D-glucopyranosyl-(1?2)-b-D-glucopyranosyl oleanlic-18-ene acid-28-O-b-D-glucopyranoside (15), along with fifteen known compounds (1, 37, and 1624), were isolated from the aerial parts of Eclipta prostrata. Their structures were established by analysis of the spectroscopic data. The isolated compounds 19 were tested for activities against dipeptidyl peptidase IV (DPP-IV), compound 7 showed significant antihyperglycemic activities by inhibitory effects on DPP-IV in human plasma in vitro, with IC50 value of 0.51 lM. Compounds 1024 were tested in vitro against NF-jB-luc 293 cell line induced by LPS. Compounds 12, 15, 16, 19, 21, and 23 exhibited moderate anti-inflammatory activities.
Assuntos
Anti-Inflamatórios/química , Eclipta/química , Hipoglicemiantes/química , Poli-Inos/química , Terpenos/química , Tiofenos/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/metabolismo , Dipeptidil Peptidase 4/química , Dipeptidil Peptidase 4/metabolismo , Eclipta/metabolismo , Células HEK293 , Humanos , Hipoglicemiantes/isolamento & purificação , Hipoglicemiantes/metabolismo , Espectroscopia de Ressonância Magnética , Conformação Molecular , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Poli-Inos/isolamento & purificação , Ligação Proteica , Terpenos/isolamento & purificação , Tiofenos/isolamento & purificaçãoRESUMO
Three new olean-type triterpenoid saponins, namely 3-O-(2-O-acetyl-ß-D-glucopyranosyl) oleanolic acid-28-O-(ß-D-glucopyranosyl) ester (1), 3-O-(6-O-acetyl-ß-D-glucopyranosyl) oleanolic acid-28-O-(ß-D-glucopyranosyl) ester (2) and 3-O-(ß-D-glucopyranosyl) oleanolic acid-28-O-(6-O-acetyl-ß-D-glucopyranosyl) ester (3), were isolated from the aerial parts of Eclipta prostrata (L.). Their structures were elucidated based on 1D and 2D NMR and MS spectroscopic data.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Eclipta/química , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/isolamento & purificação , Saponinas/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Ácido Oleanólico/química , Saponinas/químicaRESUMO
Six new 9,19-cycloartane triterpene glycosides, heracleifolinosides A-F (1-6), and one new chromone, norkhelloside (7), were isolated from the rhizome of Cimicifuga heracleifolia, together with 15 known compounds (8-22). The structures of the new compounds were elucidated by means of spectroscopic methods including 2D NMR and mass spectrometry. The extracts of C. heracleifolia and all the isolated compounds were tested for activities against hypoxia and reoxygenation injury in human umbilical vein endothelial cells. Heracleifolinoside B (2) is effectively resistant to hypoxia and reoxygenation-induced human umbilical vein endothelial cell injury, with cell viabilities of 61.95 ± 2.04 %, 77.04 ± 4.44 %, and 83.65 ± 3.29 % at concentrations of 1, 10, and 100 µM, respectively.
