RESUMO
A novel biphenylneolignan, 2,6,2',6'-tetramethoxy-4,4'-bis(2,3-epoxy-1-hydroxypropyl)biphenyl (1), and two new glycosides named atratoglaucosides A (2) and B (3), were isolated from the roots of Cynanchum atratum, and their structures were determined on the basis of chemical and spectroscopic evidence. The aglycons of 2 and 3 were identified as glaucogenin C and 7-desoxyneocynapanogenin A, a new disecopregnane. A known compound, glaucogenin C 3-O-beta-D-cymaropyranosyl-(1-->4)-alpha-L-diginopyranosyl-(1-->4)-beta-D-thevetopyranoside (4), isolated from the same source, showed a significant cytotoxic effect against 212 cells. This substance also gave a significant inhibitory effect on TNF-alpha (tumor necrosis factor-alpha) formation from the RAW 264.7 mouse macrophage-like cell line stimulated with LPS (lipopolysaccharide) and on the N9 microglial cell line stimulated with LPS/IFN-gamma (interferon-gamma).
Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Plantas Medicinais/química , Animais , Anti-Inflamatórios não Esteroides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , China , Macrófagos/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Microglia/efeitos dos fármacos , Raízes de Plantas/química , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria InfravermelhoRESUMO
Two new lignan glycosides, 4-O-[alpha-L-arabinopyranosyl-(1' "-->2' ')-beta-D-xylopyranosyl-(1' " '-->5' ')-beta-D-apiofuranosyl]diphyllin (1), named ciliatoside A (1), and 4-O-¿[beta-D-apiofuranosyl-(1' " "-->3' ")-alpha-L-arabinopyranosyl-(1' "-->2' ')][beta-D-xylopyranosyl-(1' " '-->5' ')]-beta-D-apiofuranosyl¿diphyllin (2), named ciliatoside B (2), were isolated from the whole plant of Justicia ciliata. The structures of 1 and 2 were determined by spectral and chemical methods. Compounds 1 and 2 strongly inhibited the accumulation of NO(2)(-) in lipopolysaccharide-stimulated RAW 264.7 cells in a concentration-dependent manner with IC(50) values of 27.1 +/- 1.6 and 29.4 +/- 1.4 microM, respectively.
Assuntos
Anti-Inflamatórios não Esteroides/isolamento & purificação , Glicosídeos/isolamento & purificação , Plantas Medicinais/química , Animais , Anti-Inflamatórios não Esteroides/farmacologia , Linhagem Celular , China , Depressão Química , Glicosídeos/farmacologia , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Microglia/efeitos dos fármacos , Microglia/metabolismo , Óxido Nítrico/biossíntese , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria UltravioletaRESUMO
Two new naturally occurring 1-aryl-2,3-naphthalide lignans, cilinaphthalide A (1) and cilinaphthalide B (2), and nine known compounds were isolated from the whole plant of Justicia ciliata. Their structures were established by spectral analysis, and their cytotoxic activity was evaluated against several different cell lines. The known compound, justicidin A, showed potent cytotoxic effects against T-24, CaSki, SiHa, HT-3, PLC/PRF/5, and 212 cells in vitro.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Naftalenos/isolamento & purificação , Plantas Medicinais/química , Antineoplásicos Fitogênicos/farmacologia , China , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Naftalenos/farmacologia , Espectrofotometria Ultravioleta , Células Tumorais CultivadasRESUMO
The stereochemistry of new acetophenones, cynandione B-D (2-4), isolated from Cynanchum taiwanianum, elucidated by computer modelling calculation and NOESY spectrum. It establishes the absolute configurations of cynandiones B-D (2-4) as 7R; 7"S, 7S; 7"S and 7R; 7"R, respectively. Cynandione B (2) strongly inhibited the release of beta-glucuronidase and lysozyme in formyl-methionyl-leucyl-phenylalanine (fMLP)-stimulated rat neutrophils in a concentration-dependent manner with IC50 values of 1.5 +/- 0.2 and 1.6 +/- 0.2 microM, respectively. 2,5-Dihydroxyacetophenone (6) strongly inhibited the aggregation of washed rabbit platelets induced by arachidonic acid in a concentration-dependent manner with an IC50 value of about 4.8 microM. In human citrated platelet-rich plasma, 2,5-dihydroxyacetophenone (6) inhibited the secondary phase, but not the primary phase, of aggregation induced by adrenaline and ADP. These results suggest that the antiplatelet effect of 2,5-dihydroxyacetophenone (6) is due to inhibition of the formation of thromboxane A2.