RESUMO
Two new isoxazoline compounds, 1-oxa-2-azaspiro[4.5]dec-2-ene-8ß-ol (1) and 1-oxa-2-azaspiro[4.5]dec-2-ene-8α-ol (2), were isolated from the husks of fruits of Xanthoceras sorbifolia Bunge and their structures were determined by spectroscopic analyses, including X-ray crystallography, HRESI-MS, UV, IR, and 1D and 2D NMR (HSQC, HMBC, NOESY) methods. Neither compound showed significant inhibitory effects on butyrylcholinesterase (BuchE) and acetylcholinesterase (AChE), nor the selected tumor cells growth. Based on an online activity prediction program (PASS ONLINE), the structures with isoxazoline skeletons were found to show potential anti-asthmatic (AM) and anti-anaphylaxis (AP) activities; moreover, compounds 1 and 2 were predicted to possess high affinities for many enzymes involved in AM and AP according to the RCSB Protein Data Bank. High-affinity binding to phosphodiesterase IV (PDE-4), an important inflammatory modulator in asthma, was demonstrated experimentally, beside that, the predicted structures based on compounds 1 and 2 were analyzed for PDE-4 interactions using the molecular docking methodology of Discovery Studio 3.0 (DS 3.0). The predicted structure 2A-6 exhibited much higher affinity and stability of PDE-4 binding than the clinical PDE-4 inhibitor rolipram.
Assuntos
Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Isoxazóis/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Inibidores da Colinesterase/química , Cristalografia por Raios X , Medicamentos de Ervas Chinesas/química , Humanos , Isoxazóis/química , Simulação de Acoplamento Molecular , Estrutura Molecular , Ácido Oleanólico/química , Sapindaceae/química , Saponinas/química , Estereoisomerismo , Triterpenos/químicaRESUMO
Three new triterpenoid derivatives, 3-O-ß-D-glucopyranosyl-20(S)-protopanaxtriol (1), 3-formyloxy-20-O-ß-D-glucopyranosyl-20(S)-protopanaxtriol (2) and 26-hydroxyl-24(E)-20(S)-protopanaxtriol (3), along with six known ginsenosides, were isolated from leaves of Panax ginseng. Their structures were established on the basis of spectral analysis (IR, 1D and 2D NMR, HRESI-MS). Compounds 1-3 exhibited various degree of cytotoxicity towards human A549 pulmonary carcinoma cells and Hep3B hepatoma cells.
Assuntos
Ginsenosídeos/farmacologia , Panax/química , Triterpenos/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Ginsenosídeos/química , Humanos , Estrutura Molecular , Folhas de Planta/química , Triterpenos/farmacologiaRESUMO
From the nuts of Castanea mollissima Blume, a new kauranoid diterpene glycoside, named mollioside (1), was isolated. Its structure was established as (4R, 5S, 6R, 8R, 9S, 10S, 13R, 16R) 17-O-beta-D-glucopyranoside, ent-6,7-epoxy-6alpha-hydroxyl-6,7-secokaur-19-oic acid, 6, 19-lactone-16beta, 17-diol on the basis of HR-FAB-MS, 1D, 2D-NMR and CD spectral analysis. The aglycone (1a, named mollissin), also as a new compound, was obtained after enzymatic hydrolysis of 1. Both compounds exhibited significant growth inhibitory activity on HeLa tumor cells, but no activity on A375-S2.