RESUMEN
A quantitative determination method of N-acetyl-d-glucosamine (GlcNAc) and N,N'-diacetylchitobiose (GlcNAc)(2) is proposed using a proton nuclear magnetic resonance experiment. N-acetyl groups of GlcNAc and (GlcNAc)(2) are chosen as target signals, and the deconvolution technique is used to determine the concentration of the corresponding compound. Compared to the HPLC method, (1)H-NMR spectroscopy is simple and fast. The method can be used for the analysis of chitin hydrolyzed products with real-time analysis, and for quantifying the content of products using internal standards without calibration curves. This method can be used to quickly evaluate chitinase activity. The temperature dependence of (1)H-NMR spectra (VT-NMR) is studied to monitor the chemical shift variation of acetyl peak. The acetyl groups of products are involved in intramolecular H-bonding with the OH group on anomeric sites. The rotation of the acetyl group is closely related to the intramolecular hydrogen bonding pattern, as suggested by the theoretical data (molecular modeling).
Asunto(s)
Acetilglucosamina/análisis , Quitina/química , Disacáridos/análisis , Espectroscopía de Protones por Resonancia Magnética/métodos , Acetilglucosamina/química , Conformación de Carbohidratos , Quitina/metabolismo , Quitinasas/metabolismo , Cromatografía Líquida de Alta Presión , Disacáridos/química , Enlace de Hidrógeno , Hidrólisis , Modelos Moleculares , Estructura Molecular , Reproducibilidad de los Resultados , TemperaturaRESUMEN
Reactive oxygen species and granule proteases produced by neutrophils contribute to the pathogenesis of inflammatory diseases. The extracts of the roots and the leaves of Salvia nipponica var. formosana were showed potent inhibitory effects on superoxide anion production in fMLP/CB-activated human neutrophils as well as other anti-inflammatory effects, and led to the isolation of 25 compounds. Among them, compounds 8, 12, 13, 14, 15, 17 and 20 were exhibited more potent inhibitory effect on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Moreover, those isolated compounds also showed significant anticholinesterase and antioxidative activities. To the best of our knowledge, this is the first report of phytochemical and biological activity study on S. nipponica var. formosana.
Asunto(s)
Antiinflamatorios/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Inhibidores de la Colinesterasa/aislamiento & purificación , Elastasa Pancreática/metabolismo , Extractos Vegetales/farmacología , Salvia/química , Superóxidos/metabolismo , Antiinflamatorios/farmacología , Antioxidantes/farmacología , Línea Celular , Inhibidores de la Colinesterasa/farmacología , Humanos , Neutrófilos/efectos de los fármacos , Neutrófilos/metabolismo , Extractos Vegetales/química , Hojas de la Planta , Raíces de PlantasRESUMEN
The present investigation on the chemical constituents of the roots of Stellaria dichotoma var. lanceolata has resulted in the isolation of 21 ß-carboline alkaloids, including 13 new compounds, dichotomides III-XIV (1-12) and dichotomine E (13), and eight known compounds. The structures of the new compounds were established on the basis of spectroscopic data analysis. Among these isolated alkaloids, five compounds were examined for their anti-inflammatory potential for the inhibition of NO production in LPS-treated RAW 264.7 cells. All compounds tested exhibited significant inhibition of NO production, with IC(50) values in the range of 11.3 to 19.3 µM.
Asunto(s)
Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Antiinflamatorios no Esteroideos/aislamiento & purificación , Antiinflamatorios no Esteroideos/farmacología , Carbolinas/aislamiento & purificación , Carbolinas/farmacología , Stellaria/química , Alcaloides/química , Animales , Antiinflamatorios no Esteroideos/química , Carbolinas/química , Glicósidos/química , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Concentración 50 Inhibidora , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Ratones , Estructura Molecular , Óxido Nítrico/biosíntesis , Raíces de Plantas , Estereoisomerismo , TaiwánRESUMEN
Chemical investigation on the whole plant of Houttuynia cordata has resulted in the isolation of two new compounds, named as houttuynoside A (1) and houttuynamide A (2), together with thirty-eight known compounds. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis. In the inhibitory effects on herpes simplex virus type 1 (HSV-1) assay, norcepharadione B (10) showed good inhibitory activity against the replication of HSV-1. In addition, the antioxidant and antityrosinase activities of some isolated compounds were also evaluated. Among these compounds, quercitrin (25) and quercetin-3-O-beta-D-galactopyranoside (26) showed excellent 2,2-diphenyl-1-picrylhydrazyl radical-scavenging property with IC50 values of 31 and 63 microM, respectively. Cepharadione B (9) exhibited strong tyrosinase inhibitory activity with an IC50 value of 170 microM.
Asunto(s)
Antioxidantes/farmacología , Antivirales/farmacología , Benzamidas/farmacología , Benzoatos/farmacología , Inhibidores Enzimáticos/farmacología , Glucósidos/farmacología , Herpesvirus Humano 1/efectos de los fármacos , Houttuynia/química , Animales , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antivirales/química , Antivirales/aislamiento & purificación , Benzamidas/química , Benzamidas/aislamiento & purificación , Benzoatos/química , Benzoatos/aislamiento & purificación , Chlorocebus aethiops , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Glucósidos/química , Glucósidos/aislamiento & purificación , Isoquinolinas/química , Isoquinolinas/aislamiento & purificación , Isoquinolinas/farmacología , Pruebas de Sensibilidad Microbiana , Monofenol Monooxigenasa/antagonistas & inhibidores , Plantas Medicinales/química , Quercetina/análogos & derivados , Quercetina/química , Quercetina/aislamiento & purificación , Quercetina/farmacología , Relación Estructura-Actividad , Células VeroRESUMEN
Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human cancer cell lines (A549, MCF7, KB, and KB-VIN). To explore the SAR of 1-4, 17 pyranocoumarin analogues (5-21) were designed and synthesized. Among these analogues, 5 and 10 were the most potent against hepatitis B virus with EC(50) values of 1.14 and 1.34microM, respectively. The most interesting result in the cytotoxicity assay was the significant activity of 1, 5, and 6 against the multi-drug resistant cell line, KB-VIN, without activity against the KB cell line. These data suggest that these three compounds could be useful hits for developing MDR-inverse drugs.
Asunto(s)
Antineoplásicos/química , Antivirales/química , Virus de la Hepatitis B/efectos de los fármacos , Piranocumarinas/química , Antineoplásicos/síntesis química , Antineoplásicos/toxicidad , Antivirales/síntesis química , Antivirales/toxicidad , Línea Celular Tumoral , Clausena/química , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Plantas Medicinales/química , Piranocumarinas/síntesis química , Piranocumarinas/farmacología , Relación Estructura-ActividadRESUMEN
Activity-monitored fractionation of the CHCl3 solubles of the MeOH extract of the roots of Ficus septica using cytotoxicity assay led to the isolation of twenty phenanthroindolizidine alkaloids, including ten new ficuseptines E-N and ten known compounds. The cytotoxic effects of some of the isolates were tested on gastric adenocarcinoma (NUGC) and nasopharyngeal carcinoma (HONE-1) cell lines and the results demonstrated that, with the exception of dehydrotylophorine, all the tested compounds displayed pronounced cytotoxic activity with significant cell growth inhibitory effects. In addition, 13a R-antofine was found to be highly effective with ED(50) values of < 0.1 microg/mL against L-1210, P-388, A-549 and HCT-8 cell lines in another assay.
Asunto(s)
Alcaloides/farmacología , Antineoplásicos Fitogénicos/farmacología , Ficus/química , Raíces de Plantas/química , Alcaloides/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Análisis Espectral/métodosRESUMEN
A phytochemical investigation of the leaves of Erythrophleum fordii Oliv. has led to the isolation of three new cassaine-type diterpenoids, erythrofordin A (1), erythrofordin B (2) and erythrofordin C (3), as well as a norcassaine diterpenoid with a novel skeleton, norerythrofordin A (4), and 27 known compounds (5-31). The structures of 1-4 were elucidated on the basis of spectroscopic analysis. Selected compounds from this plant were examined for anti-inflammatory activity. Taraxerol (16) displayed potent NO-reducing activity in microglial cells, and gallic acid (27) exhibited excellent DPPH radical-scavenging effects.
Asunto(s)
Diterpenos/farmacología , Fabaceae/química , Animales , Antiinflamatorios/química , Antiinflamatorios/farmacología , Células Cultivadas , Diterpenos/química , Diterpenos/aislamiento & purificación , Depuradores de Radicales Libres/metabolismo , Ratones , Óxido Nítrico/metabolismo , Extractos Vegetales/administración & dosificación , Extractos Vegetales/química , Extractos Vegetales/farmacologíaRESUMEN
Five new furanoditerpenoids, epi-8-hydroxycolumbin (1), fibaruretin B (2), C (3), E (5), and F (6), were isolated from the stems of Fibraurea tinctoria, as well as fibaruretin D (4) from the natural source for the first time, and 39 known compounds. The structures (1-6) were elucidated on the basis of spectroscopic analysis. All the isolated furanoditerpenoids (1-16) were examined for their in vitro activity and some were in vivo anti-inflammatory activity. Compounds 8 and 9 showed significant anti-inflammatory action administered at a dose of 100mg/kg of reducing carrageenan mice paw edema, whereas compound 7, 9, 10, 14, and 16 were more potent to inhibit NO production. The inhibitory effects of these compounds are dose-dependent (1-4 microg/ml).
Asunto(s)
Antiinflamatorios/farmacología , Diterpenos/farmacología , Edema/tratamiento farmacológico , Menispermaceae/química , Plantas Medicinales/química , Animales , Antiinflamatorios/aislamiento & purificación , Células Cultivadas , Diterpenos/aislamiento & purificación , Macrófagos/efectos de los fármacos , Ratones , Ratones Endogámicos ICR , Estructura Molecular , Óxido Nítrico/metabolismo , Tallos de la Planta/químicaRESUMEN
The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC(50) values ranging from 0.03 to 3.80 microg/mL. Structure-activity relationships (SAR) are also discussed.
Asunto(s)
Antineoplásicos/química , Antineoplásicos/farmacología , Chalconas/química , Chalconas/farmacología , Línea Celular Tumoral , Diseño de Fármacos , Humanos , Bases de Mannich , Estructura Molecular , Relación Estructura-ActividadRESUMEN
Due to their limited natural abundance and significant biochemical effects, we synthesized the alkaloids (+/-)-antofine (1a), (+/-)-deoxypergularinine (1b), and their dehydro congeners (2 and 3) starting from the corresponding phenanthrene-9-carboxaldehydes. We also evaluated their in vitro cytotoxic activity. Compounds 1a and 1b showed significant potency against various human tumor cell lines, including a drug-resistant variant, with EC(50) values ranging from 0.16 to 16ng/mL. Structure-activity correlations of these alkaloids and some of their synthetic intermediates were also ascertained. The non-planar structure between the two major moieties, phenanthrene and indolizidine, plays a crucial role in the cytotoxic activity of phenanthroindolizidines. Increasing the planarity and rigidity of the indolizidine moiety significantly reduced potency. A methoxy group at the 2-position (1a) was more favorable for cytotoxic activity than a hydrogen atom (1b).
Asunto(s)
Indoles/síntesis química , Indoles/toxicidad , Indolizinas/síntesis química , Indolizinas/toxicidad , Isoquinolinas/síntesis química , Isoquinolinas/toxicidad , Fenantrolinas/síntesis química , Fenantrolinas/toxicidad , Alcaloides/síntesis química , Alcaloides/toxicidad , Bromuros/síntesis química , Bromuros/toxicidad , Línea Celular Tumoral , Cloruros/síntesis química , Cloruros/toxicidad , Resistencia a Antineoplásicos , Humanos , Células KBRESUMEN
Two new flavones, designated as andropaniculosin A (1) and andropaniculoside A (2), and 30 known compounds were isolated as a result of detailed chemical examination on the whole plants of Andrographis paniculata. Their structures have been elucidated mainly by 1D and 2D NMR, and MS spectroscopic methods. Among them, four flavonoids showed potent inhibition of collagen, arachidonic acid, thrombin, and platelet activation factor induced platelet aggregation. Furthermore, a diterpenoid demonstrated moderate vasorelaxing effect in isolated rat thoracic aorta.
Asunto(s)
Andrographis/química , Diterpenos/farmacología , Flavonoides/farmacología , Inhibidores de Agregación Plaquetaria/farmacología , Vasodilatación/efectos de los fármacos , Animales , Aorta/efectos de los fármacos , Diterpenos/química , Flavonoides/química , Estructura Molecular , Inhibidores de Agregación Plaquetaria/química , RatasRESUMEN
Four new furanoditerpenoids, fibrauretin A ( 1), fibrauretinoside A ( 2), epi-fibrauretinoside A ( 3), and epi-12-palmatoside G ( 4), and a new ecdysteroid glucoside, fibraurecdyside A ( 5), together with seven known compounds including two furanoditerpenoids ( 6 and 7), an ecdysteroid ( 8), and four quaternary protoberberine alkaloids ( 9- 12) were isolated from the stems of Fibraurea tinctoria. The structures of 1- 5 were established on the basis of spectroscopic evidence. Among these compounds, palmatine ( 9) and jatrorrhizine ( 10) showed inhibitory effects against cytochrome P450 3A4 (CYP3A4) with IC 50 values of 0.9 and 2.1 microM, respectively.
Asunto(s)
Inhibidores Enzimáticos del Citocromo P-450 , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Inhibidores Enzimáticos/aislamiento & purificación , Inhibidores Enzimáticos/farmacología , Furanos/aislamiento & purificación , Furanos/farmacología , Menispermaceae/química , Plantas Medicinales/química , Citocromo P-450 CYP3A , Diterpenos/química , Inhibidores Enzimáticos/química , Furanos/química , Estructura Molecular , Tallos de la Planta/química , VietnamRESUMEN
Phytochemical investigation of Physalis angulata was initiated following primary biological screening. Fractionation of CHCl3 and n-BuOH solubles of the MeOH extract from the whole plant was guided by in vitro cytotoxic activity assay using cultured HONE-1 and NUGC cells and led to the isolation of seven new withanolides, withangulatins B-H (1-7), and a new minor physalin, physalin W (8), along with 14 known compounds, including physaprun A, withaphysanolide, dihydrowithanolide E, physanolide A, withaphysalin A, and physalins B, D, F, G, I, J, T, U, and V. New compounds (1-8) were fully characterized by a combination of spectroscopic methods (1D and 2D NMR and MS) and the relative stereochemical assignments based on NOESY correlations and analysis of coupling constants. Biological evaluation of these compounds against a panel of human cancer cell lines showed broad cytotoxic activity. Withangulatin B (1) and physalins D (10) and F (11) displayed potent cytotoxic activity against a panel of human cancer cell lines with EC50 values ranging from 0.2 to 1.6 microg/mL. Structure-activity relationship analysis indicated that withanolides and physalins with 4beta-hydroxy-2-en-1-one and 5beta,6beta-epoxy moieties are potential cytotoxic agents.
Asunto(s)
Antineoplásicos Fitogénicos , Ergosterol , Physalis/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Ergosterol/análogos & derivados , Ergosterol/química , Ergosterol/aislamiento & purificación , Ergosterol/farmacología , Humanos , Células KB , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Relación Estructura-Actividad , TaiwánRESUMEN
Total synthesis of viscolin, an anti-inflammatory 1,3-diphenylpropane isolated from Viscum coloratum, employing the Wittig reaction is reported. Key steps in the synthesis of viscolin depend on the selection of protecting groups to maintain the para hydroxyl group that is the most critical chemical structure influencing the biological activity of viscolin and the utilization of microwave-assisted Wittig olefination reaction. Anti-inflammatory potency of the synthetic viscolin, its precursor product 16, and its analogue 17, through their effects on reactive oxygen species (ROS), nitric oxide (NO), and pro-inflammatory cytokine production in leukocytes and microglial cells were evaluated. Excellent inhibition of ROS and NO production in inflammatory cells could confer the synthetic viscolin to be a potent anti-inflammatory agent for the treatment of oxidative stress-induced diseases.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Compuestos de Bifenilo/síntesis química , Propano/análogos & derivados , Animales , Antiinflamatorios no Esteroideos/farmacología , Compuestos de Bifenilo/aislamiento & purificación , Compuestos de Bifenilo/farmacología , Citocinas/metabolismo , Humanos , Leucocitos/efectos de los fármacos , Leucocitos/fisiología , Ratones , Microglía/efectos de los fármacos , Microglía/fisiología , NG-Nitroarginina Metil Éster/farmacología , Propano/síntesis química , Propano/aislamiento & purificación , Propano/farmacología , ViscumRESUMEN
[reaction: see text] A novel withasteroid, physanolide A (1), with an unprecedented skeleton containing a seven-membered ring, and two new physalins, physalins U (2) and V (3), were isolated from Physalis angulata. The structures were elucidated from spectroscopic analysis, and plausible biosynthetic pathways were postulated. Physalins B (4), D (5), and F (6) showed strong cytotoxicity against multiple tumor cell lines, including KB, A431, HCT-8, PC-3, and ZR751, with EC(50) values less than 4 microg/mL.
Asunto(s)
Antineoplásicos Fitogénicos , Medicamentos Herbarios Chinos , Lactonas , Physalis/química , Plantas Medicinales/química , Esteroides , Animales , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Humanos , Células KB , Lactonas/química , Lactonas/aislamiento & purificación , Lactonas/farmacología , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Esteroides/química , Esteroides/aislamiento & purificación , Esteroides/farmacologíaRESUMEN
Aristolochia is an important genus widely used in traditional medicine. During the past two decades, this genus has attracted much interest and has been the subject of numerous chemical and pharmacological studies. It is a rich source of aristolochic acids, which are unique to this genus, and of terpenoids. The nature of these terpenoids are reviewed in this article together with some bioactivity data in an effort to highlight the rapid development in the field of phytochemistry of the Aristolochia species.
Asunto(s)
Aristolochia/química , Medicina Tradicional , Terpenos , Terpenos/química , Terpenos/aislamiento & purificación , Terpenos/farmacologíaRESUMEN
Phytochemical investigation on the ethanol extract from the stems of Spiraea formosana has resulted in the isolation of four new neolignans, named spiraformin-A, -B, -C and -D (1-4), together with thirty five known compounds. Their structures were established primarily on the basis of 1D and 2D NMR spectral and chemical transformation methods.
Asunto(s)
Lignanos/química , Spiraea , Medicamentos Herbarios Chinos/química , Lignanos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Tallos de la PlantaRESUMEN
Three new compounds, phellodensin G, phellodenols D and E have been isolated from the leaves of Phellodendron chinense Schneid (Rutaceae), together with thirteen known compounds. Their structures were established by means of spectroscopic analysis, including extensive 2D NMR and mass spectra.
Asunto(s)
Phellodendron , Fitoterapia , Extractos Vegetales/química , Cumarinas/química , Flavonoides/química , Humanos , Espectroscopía de Resonancia Magnética , Hojas de la PlantaRESUMEN
Three new [n-pentyl beta-carboline-1-propionate (1), 5-hydroxymethyl-9-methoxycanthin-6-one (2), and 1-hydroxy-9-methoxycanthin-6-one (3)] and 19 known beta-carboline alkaloids were isolated from the roots of Eurycoma longifolia. The new structures were determined by comprehensive analyses of their 1D and 2D NMR and mass spectral data and by chemical transformation. These compounds were screened for in vitro cytotoxic and antimalarial activities, and 9-methoxycanthin-6-one (4) and canthin-6-one (5) demonstrated significant cytotoxicity against human lung cancer (A-549) and human breast cancer (MCF-7) cell lines.
Asunto(s)
Alcaloides/aislamiento & purificación , Fármacos Anti-VIH/aislamiento & purificación , Antimaláricos/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Carbolinas/aislamiento & purificación , Eurycoma/química , Plantas Medicinales/química , Alcaloides/química , Alcaloides/farmacología , Fármacos Anti-VIH/química , Fármacos Anti-VIH/farmacología , Antimaláricos/química , Antimaláricos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Neoplasias de la Mama , Carbolinas/química , Carbolinas/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Humanos , Neoplasias Pulmonares , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Raíces de Plantas/química , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Two new dihydroflavonols, phellodensin-A (1) and phellodensin-C (2); three new coumarins, phellodenol-A (3), phellodenol-B (4), and phellodenol-C (5); one new chlorophyll, phellophyll-a (6); and one new phenyllactate, (2R)-sodium 3-phenyllactate (7), in addition to 35 known compounds have been isolated from the leaves of Phellodendron amurense var. wilsonii. The structures of the new compounds were established based on 1D, 2D NMR and mass spectral analyses. The stereochemistry at the C-2, C-3, and C-2' ' positions of new dihydroflavonol 1 was determined by CD spectroscopy. The known compounds were identified by comparison with authentic samples. The antioxidant and antityrosinase activities were also described.