RESUMO
In this study, limonoids isolated from Xylocarpus plants were tested for their in vitro anti-inflammatory effects. The results demonstrated that only 7-deacetylgedunin (1), a gedunin-type limonoid, significantly inhibited lipopolysaccharide- and interferon-γ-stimulated production of nitric oxide in murine macrophage RAW 264.7 cells. The suppression of nitric oxide production by 1 was correlated with the downregulation of mRNA and protein expression of inducible nitric oxide synthase. Mechanistic studies revealed that the transcriptional activity of nuclear factor-κB, IκBα degradation, and the activation of mitogen-activated protein kinases, stimulated with lipopolysaccharide and interferon-γ, were suppressed by 1.
Assuntos
Anti-Inflamatórios/farmacologia , Mediadores da Inflamação/metabolismo , Limoninas/farmacologia , Meliaceae/química , Óxido Nítrico Sintase Tipo II/metabolismo , Óxido Nítrico/metabolismo , Extratos Vegetais/farmacologia , Animais , Anti-Inflamatórios/uso terapêutico , Regulação para Baixo , Proteínas I-kappa B/metabolismo , Inflamação/tratamento farmacológico , Inflamação/metabolismo , Interferon gama/metabolismo , Limoninas/uso terapêutico , Lipopolissacarídeos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Proteínas Quinases Ativadas por Mitógeno/metabolismo , Inibidor de NF-kappaB alfa , NF-kappa B/metabolismo , Óxido Nítrico Sintase Tipo II/genética , Fitoterapia , Extratos Vegetais/uso terapêutico , Células RAW 264.7 , RNA Mensageiro/metabolismo , Transdução de Sinais , Fator de Necrose Tumoral alfa/metabolismoRESUMO
Seven new limonoids, namely, xylorumphiins E-J (1-2 and 4-7) and 2-hydroxyxylorumphiin F (3), along with three known derivatives (8-10), were isolated from the seeds of Xylocarpus rumphii. 2-Hydroxyxylorumphiin F (3) and xylorumphiin I (6) displayed moderate inhibitory activity against nitric oxide production from lipopolysaccharide-activated macrophages with IC50 values of 24.5 and 31.3 µM, respectively.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Limoninas/isolamento & purificação , Limoninas/farmacologia , Sementes/química , Anti-Inflamatórios/química , Concentração Inibidora 50 , Limoninas/química , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Estrutura Molecular , Óxido Nítrico/biossíntese , Ressonância Magnética Nuclear Biomolecular , TailândiaRESUMO
Four new mexicanolide limonoids, named xylorumphiins A-D (1-4), were isolated from the seed kernels of Xylocarpus rumphii, together with three known limonoids. Their structures and configurations were established on the basis of spectroscopic data.
Assuntos
Limoninas/isolamento & purificação , Meliaceae/química , Limoninas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sementes/química , TailândiaRESUMO
The title compound (also known as phragmalin triacetate), C(35)H(42)O(14), is a phragmalin-type limonoid extracted from X. rumphii. The mol-ecule consists of eight rings with the orthoacetate group bridged at positions 1, 8 and 9. The two five-carbocyclic rings (A(1) and A(2)) and the dioxolane ring (G) adopt a distorted envelope conformation. The 1,3-dioxane ring (E) exists in a chair conformation. The six-carbocyclic rings (B and C) exhibit a twisted-boat conformation. The lactone ring has a half-chair conformation and the furan ring is planar (r.m.s. deviation = 0.002â Å). Rings A(1)/B, A(2)/B, B/C, C/D and C/G are all cis-fused. The two acet-oxy groups attached to ring B and the furan ring attached to the lactone ring are in equatorial positions. The porous crystal packing exhibits voids of 688â Å(3) and weak inter-molecular C-Hâ¯O inter-actions. The absolute configuration was assigned on the basis of literature data.
