RESUMEN
The Machilus genus (Lauraceae) had been extensively utilized in folk medicine due to its broad range of bioactivities. In the present study, a series of chromatographic separations of the methanol extract of stems of M. philippinensis led to the identification of thirty eight compounds totally. Among these, biscinnamophilin (1), machilupins A-C (2-4), machilutone A (5), and machilusoxide A (6) were new compounds reported for the first time. In addition, 5 was characterized with a unprecedented carbon skeleton. Other known compounds, including the major compounds cinnamophilin (7) and meso-dihydroguaiaretic acid (8), are identified by comparison of their physical and spectroscopic data with reported values. One of the reported compounds, cinnamophilin A (10), should be revised as dehydroguaiaretic acid (9) after careful comparison of all the 1H and 13C NMR data. Moreover, the neuroprotective activity of cinnamophilin (7) was examined in a primary cortical neuron culture and the results indicated that 7 was effective against glutamate induced excitotoxicity.
RESUMEN
In the dimethylnitrosamine (DMN)-induced hepatic fibrosis Wistar rat model, the mycelium extract of Phellinus linteus (PLE) (20 mg/Kg) displayed significant protection against hepatic fibrosis. The present investigation characterized eleven new ionone derivatives, phellinulins Dâ»N (4â»14), from the P. linteus mycelium extract and the relative stereochemical structures were constructed according to the spectroscopic and spectrometric analytical results. Some purified compounds were examined for their inhibitory effects on activated rat hepatic stellate cells (HSCs) and several isolates did exhibit significant protection. The results indicated that the mycelium of P. linteus could be explored as a hepatoprotective drug or healthy food candidate in the near future.
Asunto(s)
Basidiomycota/química , Mezclas Complejas/farmacología , Cirrosis Hepática/prevención & control , Micelio/química , Animales , Mezclas Complejas/química , Dimetilnitrosamina/toxicidad , Células Estrelladas Hepáticas/metabolismo , Células Estrelladas Hepáticas/patología , Cirrosis Hepática/inducido químicamente , Cirrosis Hepática/metabolismo , Cirrosis Hepática/patología , Masculino , Ratas , Ratas WistarRESUMEN
A series of chromatographic separations performed on the ethanol extracts of the peels of Citrus grandis has led to the characterization of forty compounds, including seventeen coumarins, eight flavonoids, two triterpenoids, four benzenoids, two steroids, one lignan, one amide, and five other compounds, respectively. The chemical structures of the purified constituents were identified on the basis of spectroscopic elucidation, including 1D- and 2D-NMR, UV, IR, and mass spectrometric analysis. Most of the isolated compounds were examined for their inhibition of superoxide anion generation and elastase release by human neutrophils. Among the isolates, isomeranzin (3), 17,18-dihydroxybergamottin (12), epoxybergamottin (13), rhoifolin (19), vitexicarpin (22) and 4-hydroxybenzaldehyde (29) displayed the most significant inhibition of superoxide anion generation and elastase release with IC50 values ranged from 0.54 to 7.57 µM, and 0.43 to 4.33 µM, respectively. In addition, 7-hydroxy-8-(2'-hydroxy-3'-methylbut-3'-enyl)coumarin (8) and 17,18-dihydroxybergamottin (12) also exhibited the protection of neurons against A-mediated neurotoxicity at 50 µM.
Asunto(s)
Antiinflamatorios/farmacología , Citrus/química , Cumarinas/farmacología , Flavonoides/farmacología , Fármacos Neuroprotectores/farmacología , Triterpenos/farmacología , Péptidos beta-Amiloides/antagonistas & inhibidores , Péptidos beta-Amiloides/toxicidad , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Muerte Celular/efectos de los fármacos , Corteza Cerebral/citología , Corteza Cerebral/efectos de los fármacos , Mezclas Complejas/química , Cumarinas/química , Cumarinas/aislamiento & purificación , Flavonoides/química , Flavonoides/aislamiento & purificación , Frutas/química , Humanos , Elastasa de Leucocito/antagonistas & inhibidores , Elastasa de Leucocito/metabolismo , Lignanos/química , Lignanos/aislamiento & purificación , Lignanos/farmacología , Neuronas/citología , Neuronas/efectos de los fármacos , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/aislamiento & purificación , Neutrófilos/citología , Neutrófilos/efectos de los fármacos , Neutrófilos/metabolismo , Fragmentos de Péptidos/antagonistas & inhibidores , Fragmentos de Péptidos/toxicidad , Cultivo Primario de Células , Ratas , Ratas Sprague-Dawley , Esteroides/química , Esteroides/aislamiento & purificación , Esteroides/farmacología , Superóxidos/antagonistas & inhibidores , Superóxidos/química , Triterpenos/química , Triterpenos/aislamiento & purificación , ResiduosRESUMEN
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
Five new acyclic amides, clausenalansamides C-G (1-5), clausenaline G (6) and (±)-5-(4-methylphenyl)-γ-valerolactone (7) reported from the natural source for the first time, were characterized from the leaves of Clausena lansium. Their structures were established by spectroscopic and spectrometric methods, and the absolute configurations of new compounds 1-5 were determined by electronic circular dichroism and single-crystal X-ray diffraction analyses. Eighteen compounds were evaluated for their anti-inflammatory activity and only imperatorin (11) and wampetin (12) displayed significant inhibition of fMLP/CB-induced superoxide anion generation with IC50 values of 1.7 ± 0.3 and 6.8 ± 1.1 µM, respectively.
Asunto(s)
Antiinflamatorios/química , Clausena/química , Hojas de la Planta/química , Antiinflamatorios/farmacología , Estructura MolecularRESUMEN
Three new γ-ionylideneacetic acid derivatives, phellinulins A-C (1-3), were characterized from the mycelium extract of Phellinus linteus. The chemical structures were established based on the spectroscopic analysis. In addition, phellinulin A (1) was subjected to the examination of effects on activated rat hepatic stellate cells and exhibited significant inhibition of hepatic fibrosis.
Asunto(s)
Células Estrelladas Hepáticas/efectos de los fármacos , Extractos Vegetales/química , Ácido Abscísico/análogos & derivados , Ácido Abscísico/química , Animales , Basidiomycota/química , Células Hep G2 , Humanos , Norisoprenoides/química , Norisoprenoides/farmacología , Phellinus , Extractos Vegetales/farmacología , RatasRESUMEN
Eight new carbazole alkaloids, claulamines C (1), D (2), and E (5) and clausenalines B-F (3, 4, 6-8), four new coumarins, clausemarins A-D (9-12), and 43 known compounds were isolated from the roots of Clausena lansium. The structures of the new compounds were established on the basis of 2D-NMR spectroscopic analysis, and their absolute configurations were established from their ECD spectra. The configuration of wampetin was revised as E using a NOESY experiment. Most of the isolated compounds were evaluated for their potential anti-inflammatory activity. The results showed that compounds 9, 13-18, and 20-22 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 1.9 to 8.4 µM, while compounds 18, 19, and 21 inhibited elastase release with IC50 values in the range from 2.0 to 6.9 µM.
Asunto(s)
Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Carbazoles/aislamiento & purificación , Clausena/química , Cumarinas/aislamiento & purificación , Cumarinas/farmacología , Accidentes por Caídas , Alcaloides/química , Antiinflamatorios/química , Carbazoles/química , Carbazoles/farmacología , Cumarinas/química , Estructura Molecular , Raíces de Plantas/química , Tallos de la Planta/químicaRESUMEN
A facile high-performance liquid chromatography (HPLC) method for the resolution and quantitative measurement of nine marker substances, the active ingredients in patch preparations of Ru-Yi-Jin-Huang-San, was established using gradient elution in the reversed-phase mode. These marker substances included berberine (Phellodendri Cortex), curcumin (Curcumae Rhizoma), imperatorin (Angelicae Dahuricae Radix), magnolol (Magnoliae Cortex), hesperidin (Citri Leiocarpae Exocarpium), glycyrrhizin (Glycyrrhizae Radix), and emodin, sennoside A, sennoside B (Rhei Rhizoma). The ingredients in the water-based and oil-based patches of the formula from different manufactures were also analyzed for quality evaluation. Extracted samples were analyzed by HPLC using a reversed-phase column (Inertsil 5 ODS-2, 4.6-mm I.D. x 250 mm) at 30 degrees C and eluted with a mixture of 20 and 70% acetonitrile aqueous solution in gradient manner at a flow rate of 1.0 ml/min. The detection wavelength varied with time as follows: 275 nm, 0-72 min; 250 nm, 72-105 min; 220 nm, 105-145 min. Relative coefficients of variations of intra- and interday analysis were less than 5%. All the recoveries were 93.30-113.63%. This method could be applied for the simultaneous determination of nine marker substances in Ru-Yi-Jin-Huang-San.
Asunto(s)
Química Farmacéutica , Medicamentos Herbarios Chinos/análisis , Medicamentos Herbarios Chinos/química , Química Farmacéutica/métodos , Cromatografía Líquida de Alta Presión/métodosRESUMEN
The Chinese herb DongChong-XiaCao originating from Cordyceps sinensis is widely used as a traditional medicine in China for treatment of a wide variety of diseases. The extracts of Cordyceps sinensis (CSE) and Cordyceps militaris (CME) are well-known for their biological effects. In the present study, the antioxidant efficiency of CME and CSE in protecting lipid, protein, and low-density lipoprotein (LDL) against oxidative damage was investigated. CME and CSE showed weakly inhibitory effect on liposome oxidation, that of CME being superior to that of CSE. As for the protein oxidation model system, the inhibitory effect of CME on protein oxidation was inferior to that of CSE. CME and CSE at 1.0 mg/mL showed 50.5 and 67.1% inhibition of LDL oxidation, respectively. The contents of bioactive ingredients cordycepin and adenosine in CME are higher than those of CSE; however, both cordycepin and adenosine showed no significant antioxidant activity as determined by the Trolox equivalent antioxidant capacity method. Polyphenolic and flavonoid contents are 60.2 and 0.598 microg/mL in CME and 31.8 and 0.616 microg/mL in CSE, respectively, which may in part be responsible for their antioxidant activities. In addition, a polysaccharide present in CME and CSE displayed antioxidant activity, which suggested that the activity might be derived partly from polysaccharides of CME and CSE. The tendency to scavenge the ABTS(*)(+) free radical and the reducing ability of CME and CSE display concentration-dependent manners, suggesting that CME and CSE may be potent hydrogen donators. On the basis of the results obtained, the protective effects of CME and CSE against oxidative damage of biomolecules are a result of their free radical scavenging abilities.
Asunto(s)
Antioxidantes/farmacología , Cordyceps/química , Estrés Oxidativo/efectos de los fármacos , Extractos Vegetales/farmacología , Antioxidantes/análisis , Flavonoides/análisis , Peroxidación de Lípido/efectos de los fármacos , Oxidación-Reducción , Fenoles/análisis , Polisacáridos/análisis , Proteínas/químicaRESUMEN
The antioxidant activity and identification of the antioxidant component of peanut seed testa were investigated. The antioxidant activity of peanut seed testa was studied in the linoleic acid model system by using the ferric thiocyanate method. Among the five organic solvent extracts, the ethanolic extracts of peanut seed testa (EEPST) produced higher yields and stronger antioxidant activity than other organic solvent extracts. EEPST was separated into 17 fractions on silica gel column chromatography. Fraction 17, which showed the largest yield and significant antioxidant activity, was separated by thin-layer chromatography. Four major antioxidative subfractions were present. Subfraction 17-2 was found to be effective in preventing oxidation of linoleic acid. This subfraction was further fractionated and isolated and characterized by UV, MS, IR, and (1)H NMR techniques. The active compound was identified as ethyl protocatechuate (3,4-dihydroxybenzoic acid ethyl ester).