RESUMO
Seven known and six new tetranortriterpenoids, cineracipadesins A-F (1-6), were isolated from the leaves of Cipadessa cinerascens. Compound 1 has a mexicanolide-type structural skeleton with a rare 9alpha,11alpha-epoxide ring; compound 2 has a methyl angolensate-type structure with 9,11-dihydroxy groups, representing the first example of a precursor of a trijugin-type limonoid; and 3 is the first reported methyl angolensate-type limonoid with a ketone group at ring C. Their structures were determined with extensive spectroscopic analysis. X-ray crystallography confirmed the structure of 1. The ability of compounds 1-7 to inhibit the growth of the P-388 murine leukemia cell line was evaluated.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Limoninas/isolamento & purificação , Meliaceae/química , Animais , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Leucemia P388 , Limoninas/química , Limoninas/farmacologia , Camundongos , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/químicaRESUMO
Five new benzylphenethylamine alkaloids, hostasine (1), 8-demethoxyhostasine, 8-demethoxy-10-O-methylhostasine, 10-O-methylhostasine, and 9-O-demethyl-7-O-methyllycorenine, along with 12 known compounds, were isolated from Hosta plantaginea by bioassay-guided fractionation. The structures of the new alkaloids were established by means of extensive spectroscopic methods, and the relative configuration of 1 was further confirmed by single-crystal X-ray diffraction. 7-Deoxy-trans-dihydronarciclasine (IC(50) = 1.80 microM), a known alkaloid, showed strong activity against tobacco mosaic virus by the half-leaf method. Some of these alkaloids were also evaluated for their inhibitory activity against acetylcholinesterase. 8-Demethoxy-10-O-methylhostasine was found to possess significant activity, with an IC(50) of 2.32 microM.
Assuntos
Acetilcolinesterase/efeitos dos fármacos , Antivirais/isolamento & purificação , Antivirais/farmacologia , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Hosta/química , Plantas Medicinais/química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antivirais/química , Inibidores da Colinesterase/química , Cristalografia por Raios X , Conformação Molecular , Estrutura MolecularRESUMO
[structure: see text] Two novel nortriterpenoid compounds, sphenadilactones A (1) and B (2), have been isolated from the leaves and stems of Schisandrasphenanthera. The structural elucidation of 1 and 2 was accomplished by extensive NMR analysis. The relative stereochemistry of 1 was established by single-crystal X-ray crystallography. Both compounds were tested for their cytotoxicities against K562, A549, and HT-29, and compound 1 was further tested for its anti-HIV-1 activity.
Assuntos
Fármacos Anti-HIV/isolamento & purificação , Plantas Medicinais/química , Schisandra/química , Triterpenos/isolamento & purificação , Fármacos Anti-HIV/química , Fármacos Anti-HIV/farmacologia , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Caules de Planta/química , Triterpenos/química , Triterpenos/farmacologia , Células Tumorais CultivadasRESUMO
Rubriflordilactones A (1) and B (2), two novel highly unsaturated rearranged bisnortriterpenoids possessing a biosynthetically modified aromatic D-ring, were isolated from the leaves and stems of Schisandra rubriflora. Their structures were established on the basis of extensive spectroscopic methods, including two-dimensional NMR techniques, and confirmed by X-ray crystallographic analysis. Compound 1 showed weak anti-HIV-1 activity, and compound 2 exhibited an EC50 value of 9.75 microg/mL (SI=12.39) against HIV-1 replication with low cytotoxicity.
Assuntos
Fármacos Anti-HIV/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , HIV-1/efeitos dos fármacos , Plantas Medicinais/química , Schisandra/química , Triterpenos/isolamento & purificação , Fármacos Anti-HIV/química , Fármacos Anti-HIV/farmacologia , Cristalografia por Raios X , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Triterpenos/química , Triterpenos/farmacologia , Células Tumorais CultivadasRESUMO
[structure: see text] Two novel triterpene dilactones with an unprecedented rearranged hexacyclic skeleton, kadlongilactones A (1) and B (2), have been isolated from the leaves and stems of Kadsura longipedunculata Finet et Gagnep (Schisandraceae). Their structures were established by comprehensive 1D and 2D NMR spectroscopic analysis, coupled with single-crystal X-ray crystallographic diffraction. Compounds 1 and 2 exerted significant inhibitory effects against human tumor K562 cells with IC(50) = 1.40 and 1.71 microg/mL, respectively.
Assuntos
Lactonas/química , Schisandraceae/química , Triterpenos/química , Linhagem Celular Tumoral , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Concentração Inibidora 50 , Células K562 , Lactonas/farmacologia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Triterpenos/farmacologiaRESUMO
[structures: see text] Lancifodilactone F (1), possessing an unprecedented rearranged pentanortriterpenoid backbone derived from cycloartane, was isolated from the leaves and stems of Schisandra lancifolia (Rehd. et Wils) A. C. Smith. Its structure was established by comprehensive NMR and MS spectroscopic analysis, coupled with single-crystal X-ray experiment. Compound 1 exerted minimal cytotoxicity against C8166 cells (CC50 > 200 microg/mL) and showed anti-HIV activity with EC50 = 20.69 +/- 3.31 microg/mL and a selectivity index > 6.62.
Assuntos
Fármacos Anti-HIV/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Plantas Medicinais/química , Schisandra/química , Triterpenos/isolamento & purificação , Fármacos Anti-HIV/química , Fármacos Anti-HIV/farmacologia , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Caules de Planta/química , Triterpenos/química , Triterpenos/farmacologiaRESUMO
Maoecrystal V (1), a novel C(19) diterpenoid possessing a unique 6,7-seco-6-nor-15(8-->9)-abeo-5,8-epoxy-ent-kaurane skeleton, was isolated from the leaves of a Chinese medicinal herb, Isodon eriocalyx. Its structure was determined by comprehensive NMR and MS spectroscopic analysis and confirmed by single-crystal X-ray diffraction study. Compound 1 showed remarkable inhibitory activity toward HeLa cells with IC(50) = 0.02 microg/mL (cis-platin: IC(50) = 0.99 microg/mL).
Assuntos
Diterpenos/química , Isodon/química , Cristalografia por Raios X , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Modelos MolecularesRESUMO
Five new ent-kaurane diterpenoids, ludongnins F-J (1-5), along with 10 known compounds, guidongnins A-C (6-8), angustifolin (9), 6-epiangustifolin (10), sculponeatin J (11), gardenin D, 5,3',4'-trihydroxy-6,7,8-trimethoxyflavone, pedalitin, and quercetin, were isolated from the leaves of Isodon rubescens var. lushiensis. The structures of 1-5 were determined by spectroscopic analysis, as well as X-ray crystallographic analysis of 1. Compounds 1-11 were evaluated against K562 leukemia cells for their cytotoxic effects.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos do Tipo Caurano/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Isodon/química , Plantas Medicinais/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Diterpenos do Tipo Caurano/química , Diterpenos do Tipo Caurano/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Células K562/efeitos dos fármacos , Conformação Molecular , Estrutura Molecular , Células Tumorais Cultivadas/efeitos dos fármacos , Difração de Raios XRESUMO
OBJECTIVE: To study the selective isolation of a single chemical component from volatile oil of Fructus foeniculi by inclucion method. METHOD: The host molecule was selected and a single chemical component isolated from volatile oil by the host-guest recognition. RESULT: X-ray single crystal analysis showed that 1,1,6,6-tetraphenylhexa-2, 4-diyne-1, 6-diol could successfully include 4-[1-propenyl] benzaldehyde from volatile oil of Fructus foeniculi. CONCLUSION: The host-guest inclusion technology can be used to isolate a single component selectively from mixture.