RESUMEN
Abstract: Cembrane-type diterpenoids are among the most frequently encountered natural products from the soft corals of the genus Lobophytum. In the course of our investigation to identify anti-inflammatory constituents from a wild-type soft coral Lobophytumcrassum, two new cembranoids, lobophyolide A (1) and B (2), along with five known compounds (3-7), were isolated. The structures of these natural products were identified using NMR and MS spectroscopic analyses. Compound 1 was found to possess the first identified α-epoxylactone group among all cembrane-type diterpenoids. The in vitro anti-inflammatory effect of compounds 1-5 was evaluated. The results showed that compounds 1-5 not only reduced IL-12 release, but also attenuated NO production in LPS-activated dendritic cells. Our data indicated that the isolated series of cembrane-type diterpenoids demonstrated interesting structural features and anti-inflammatory activity which could be further developed into therapeutic entities.
Asunto(s)
Antozoos/química , Antiinflamatorios/farmacología , Células Dendríticas/efectos de los fármacos , Diterpenos/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Células Dendríticas/inmunología , Células Dendríticas/metabolismo , Diterpenos/química , Diterpenos/aislamiento & purificación , Interleucina-12/metabolismo , Lipopolisacáridos/farmacología , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Ratones , Ratones Endogámicos C57BL , Estructura Molecular , Óxido Nítrico/metabolismo , Cultivo Primario de Células , Relación Estructura-ActividadRESUMEN
Three new polyoxygenated briarane diterpenoids, briarenols C-E (1-3), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1-3 were elucidated by interpretation of spectroscopic data, and the methylenecyclohexane ring in 1 was found to exist in a twisted boat conformation. Briarenol D (2) displayed an inhibitory effect on the release of elastase by human neutrophils with an IC50 value of 4.65 µM. Briarenol E (3) was found to inhibit the protein expression of pro-inflammatory inducible nitric oxide synthase (iNOS) in a murine macrophage-like cell line, RAW 264.7, stimulated with lipopolysaccharides (LPS).
Asunto(s)
Antozoos/química , Diterpenos/química , Animales , Línea Celular , Humanos , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Espectroscopía de Resonancia Magnética , Ratones , Modelos Moleculares , Conformación Molecular , Estructura Molecular , Neutrófilos/efectos de los fármacos , Neutrófilos/metabolismo , Estrés Oxidativo/efectos de los fármacosRESUMEN
A new polyoxygenated briarane diterpenoid, briarenol B (1), was isolated from the octocoral Briareum excavatun and its structure determined from spectroscopic data. In RAW264.7 cells, a macrophage-like murine cell line, briarane B (1) was found to enhance the protein expression of pro-inflammatory cyclooxygenase (COX-2) and inducible nitric oxide synthase (iNOS) in cells stimulated by lipopolysaccharide (LPS).