RESUMEN
Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol (3p), displayed the most significant inhibitory effects against NO production. To investigate the mechanism of action, the effects of 3p on iNOS and COX-2 protein expression were studied by immunoblot. The results concluded that 3p is capable of inhibiting iNOS expression in LPS-induced RAW264.7 cells via attenuation of NF-κB signaling by ERK, p38, and JNK.
Asunto(s)
Antiinflamatorios no Esteroideos/farmacología , Chalconas/farmacología , Fenoles/farmacología , Propano/análogos & derivados , Propano/farmacología , Animales , Antiinflamatorios no Esteroideos/síntesis química , Línea Celular , Chalconas/síntesis química , Ciclooxigenasa 2/metabolismo , Quinasas MAP Reguladas por Señal Extracelular/metabolismo , Proteínas Quinasas JNK Activadas por Mitógenos/metabolismo , Ratones , FN-kappa B/metabolismo , Óxido Nítrico/metabolismo , Óxido Nítrico Sintasa de Tipo II/metabolismo , Fenoles/síntesis química , Fosforilación , Propano/síntesis química , Transducción de Señal , Proteínas Quinasas p38 Activadas por Mitógenos/metabolismoRESUMEN
Nine neolignan derivatives (1-9) were characterized from the roots of Magnolia officinalis, and their structures were elucidated based on spectroscopic and physicochemical analyses. Among them, houpulins E (1) and M (9) possess novel homo- and trinor-neolignan skeletons. In addition, 15 known compounds (10-24) were identified by comparison of their spectroscopic and physical data with those reported in the literature. Some of the purified constituents were examined for anti-inflammatory activity and, among the tested compounds, houpulins G (3), I (5), J (6), and 2,2'-dihydroxy-3-methoxy-5,5'-di-(2-propenylbiphenyl) (19) significantly inhibited superoxide anion generation and elastase release with IC50 values ranging from 3.54 to 5.48 µM and 2.16 to 3.39 µM, respectively. Therefore, these neolignan derivatives have tremendous potential to be explored as anti-inflammatory agents.
Asunto(s)
Antiinflamatorios no Esteroideos/farmacología , Lignanos/farmacología , Magnolia/química , Elastasa Pancreática/metabolismo , Raíces de Plantas/química , Superóxidos/metabolismo , Adulto , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Humanos , Lignanos/química , Lignanos/aislamiento & purificación , Estructura Molecular , Neutrófilos/efectos de los fármacos , Neutrófilos/metabolismo , Teoría Cuántica , Relación Estructura-Actividad , Adulto JovenRESUMEN
Eight new clausenamides, including three γ-lactams (1-3), four δ-lactams (4-7), and an amide (8), and seven known lactams, including compounds 9-11, which were purified from natural sources for the first time, were characterized from the leaves of Clausena lansium. Their structures were elucidated using spectroscopic methods, and the absolute configurations were determined using electronic circular dichroism and single-crystal X-ray diffraction analyses with Cu Kα radiation. Compound 2 (50 µM) protected 22.24% of cortical neurons against Aß25-35-induced cell death.
Asunto(s)
Clausena/química , Lactamas/aislamiento & purificación , Lignanos/aislamiento & purificación , Fármacos Neuroprotectores/aislamiento & purificación , Péptidos beta-Amiloides/farmacología , Carbazoles , Lactamas/química , Lignanos/química , Estructura Molecular , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/farmacología , Resonancia Magnética Nuclear Biomolecular , Fragmentos de Péptidos/farmacología , Hojas de la Planta/química , Estereoisomerismo , VietnamRESUMEN
Five new iridoids, salvialosides A-E (compounds 1-5), together with fifty known compounds were isolated from the roots of Salvia digitaloides. The structures of the new compounds were completely elucidated using a combination of 2D NMR techniques (COSY, NOESY, HMQC and HMBC) and HR-ESI-MS analyses. The known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature.
Asunto(s)
Iridoides/química , Raíces de Plantas/química , Salvia/química , Iridoides/aislamiento & purificación , Estructura Molecular , Resonancia Magnética Nuclear BiomolecularRESUMEN
Phytochemical investigation of the roots and stems of Illigera luzonensis afforded two new aporphine alkaloids (1) and (2), one new bisdehydroaporphine alkaloid (3), and one new benzenoid (4), along with 28 known structures. The structures of new compounds were elucidated by spectral and MS analysis. Among the isolated compounds, (1) and (4-13) were subjected into the examination for their inhibitory effects on the aggregation of washed rabbit platelets.
Asunto(s)
Hernandiaceae/química , Extractos Vegetales/farmacología , Agregación Plaquetaria/efectos de los fármacos , Alcaloides/química , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Animales , Aporfinas/química , Hernandiaceae/metabolismo , Espectroscopía de Resonancia Magnética , Conformación Molecular , Extractos Vegetales/química , Raíces de Plantas/química , Raíces de Plantas/metabolismo , Tallos de la Planta/química , Tallos de la Planta/metabolismo , Inhibidores de Agregación Plaquetaria/farmacología , ConejosRESUMEN
Two new glucosides, salviadigitoside A (1) and salviatalin A-19-O-ß-glucoside (2), belonging to the salviatalin type diterpenoids, and a new cyclopenta[c]pyridine, salviadiginine A (3), were isolated from the roots of Salvia digitaloids. Structures of these compounds were determined on the basis of spectroscopic analysis. In addition, compounds 1-3 were evaluated for their anti-inflammatory activity, but the results showed a weak anti-inflammatory activity.
Asunto(s)
Antiinflamatorios/química , Diterpenos/química , Glucósidos/química , Extractos Vegetales/química , Salvia/química , Adulto , Antiinflamatorios/farmacología , Diterpenos/farmacología , Glucósidos/farmacología , Humanos , Neutrófilos/efectos de los fármacos , Extractos Vegetales/farmacología , Raíces de Plantas/químicaRESUMEN
Five new benzenoids, benzocamphorins A-E (1-5), and 10 recently isolated triterpenoids, camphoratins A-J (16-25), together with 23 known compounds including seven benzenoids (6-12), three lignans (13-15), and 13 triterpenoids (26-38) were isolated from the fruiting body of Taiwanofungus camphoratus. Their structures were established by spectroscopic analysis. Selected compounds were examined for cytotoxic and anti-inflammatory activities. Compounds 9 and 21 showed moderate cytotoxicity against MCF-7 and Hep2 cell lines with ED(50) values of 3.4 and 3.0µg/mL, respectively. Compounds 21, 25, 26, 29-31, 33, and 36 demonstrated potent anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production with IC(50) values of 2.5, 1.6, 3.6, 0.6, 4.1, 4.2, 2.5, and 1.5µM, respectively, which were better than those of the nonspecific nitric oxide synthase (NOS) inhibitor N-nitro-l-arginine methyl ester (l-NAME) (IC(50): 25.8µM). These results may substantiate the use of T. camphoratus in traditional Chinese medicine (TCM) for the treatment of inflammation and cancer-related diseases. The newly discovered compounds deserve further development as anti-inflammatory candidates.
Asunto(s)
Cuerpos Fructíferos de los Hongos/química , Polyporales/química , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Ten new triterpenoids, camphoratins A-J (1-10), along with 12 known compounds were isolated from the fruiting body of Taiwanofungus camphoratus. Their structures were established by spectroscopic analysis and chemical methods. Compound 10 is the first example of a naturally occurring ergosteroid with an unusual cis-C/D ring junction. Compounds 2-6 and 11 showed moderate to potent cytotoxicity, with EC(50) values ranging from 0.3 to 3 µM against KB and KB-VIN human cancer cell lines. Compounds 6, 10, 11, 14-16, 18, and 21 exhibited anti-inflammatory NO-production inhibition activity with IC(50) values of less than 5 µM, and were more potent than the nonspecific NOS inhibitor N(ω)-nitro-L-arginine methyl ester.
Asunto(s)
Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Polyporaceae/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Antiinflamatorios/química , Antineoplásicos/química , Ensayos de Selección de Medicamentos Antitumorales , Cuerpos Fructíferos de los Hongos/química , Humanos , Concentración 50 Inhibidora , Estructura Molecular , NG-Nitroarginina Metil Éster/farmacología , Óxido Nítrico Sintasa/antagonistas & inhibidores , Resonancia Magnética Nuclear Biomolecular , Estereoisomerismo , Triterpenos/químicaRESUMEN
Three new arylnaphthalene lignans, namely phyllanthusmins A-C, together with nine known compounds were isolated and characterized from the stems and roots of Phyllanthus oligospermus by a bioassay-guided purification. The structures of the new compounds were elucidated by means of spectroscopic data interpretation. Among them, phyllanthusminA displayed significant cytotoxicity against KB and P-388 cancer cell lines.