RESUMO
Horsfiequinone G (1), a dimeric diarylpropane featuring an unprecedentedly oxo-6/7/6 fused ring system, a new flavane, horsfielenide F (2), three naturally occurring spirocyclic monomers containing all-carbon quaternary centers, horspirotone A (3), horspirotone B (4), and methyl spirobroussonin B (5), along with horsfiequinone A (6) were isolated from Horsfieldia kingii. Their structures and absolute configurations were determined by the inspection of extensive spectroscopic data and electronic circular dichroism (ECD) calculations. Biological evaluations of these isolates revealed that compounds 1 - 3 and 5 - 6 exhibited specifically immunosuppressive activities against Con A-induced T lymphocytes with IC50 values ranging from 2.07 to 12.34 µM (selectivity indices = 2.3-25.2). Compound 1 also suppressed the secretion of inflammatory factors like IL-1ß and IL-6 in RAW264.7 cells which could present a new class of nonsteroidal anti-inflammatory agent. Finally, the primary structure-activity relationship (SAR) was also discussed.
Assuntos
Anti-Inflamatórios não Esteroides , Imunossupressores , Anti-Inflamatórios não Esteroides/farmacologia , Carbono , Dicroísmo Circular , Imunossupressores/farmacologia , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
Horisfieldones A (1) and B (2), two dimeric diarylpropanes featuring an unprecedentedly aromatic ring-contracted framework, were isolated from Horsfieldia kingii. Their structures and absolute configurations were determined by the inspection of extensive spectroscopic data and electronic circular dichroism calculations. Molecular modeling analysis, in vitro enzyme-based bioassays, and structure-activity relationship analysis of these isolates revealed that (+)-1 (IC50 = 35.1 ± 3.9 µM, SI > 11.4) could present a new class of human DOPA decarboxylase inhibitor.
Assuntos
Dopa Descarboxilase/farmacologia , Propano/farmacologia , Dicroísmo Circular , Dopa Descarboxilase/química , Humanos , Concentração Inibidora 50 , Modelos Moleculares , Estrutura Molecular , Propano/análogos & derivados , Propano/química , Relação Estrutura-AtividadeRESUMO
Two new dibenzylbutyrolactol lignans and three known dibenzylbutyrolactone lignans were isolated from the twigs and leaves of Horsfieldia kingii. Their structures were elucidated by spectroscopic analysis. Cytotoxicity evaluation of these compounds against five human tumour lines showed no inhibitory effects.
Assuntos
Lignanas/isolamento & purificação , Myristicaceae/química , Extratos Vegetais/química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lignanas/química , Lignanas/toxicidade , Estrutura Molecular , Folhas de Planta/química , Análise EspectralRESUMO
Five compounds, including a new dimeric diarylpropane, were isolated from the petroleum ether extract of the twigs and leaves of Horsfieldia tetratepala. The structures of these compounds were elucidated by spectroscopic analysis. Moreover, the antiproliferative activities of these compounds were tested on cancer cell lines, but none is active.
