RESUMO
Two new acorane-type sesquiterpenoids, harzianes A and B (1 and 2), together with two known cyclonerodiol-type sesquiterpenoids (3-4) and four known sterols (5-8) were isolated from the endophytic Trichoderma harzianum, associated with the medicinal plant Paeonia lactiflora Pall. Compounds 1 and 2 were identified as a pair of heterotropic isomers by spectroscopic analysis (HR-ESI-MS, 1D and 2D NMR), and their absolute configurations were determined by ECD calculations. All compounds were tested for anti-inflammatory activity, however, none demonstrated such activity.
RESUMO
Eupatorium (family: Compositae), which comprises nearly 1200 species, is distributed throughout tropical America, Europe, Africa, and Asia. Up to now, the reported constituents from the genus Eupatorium involve flavonoids, terpenoids, pyrrolizidine alkaloids, phenylpropanoids, quinonoids, essential oils, and some others, altogether more than 300 compounds. Studies have shown that Eupatorium and its active principles possess a wide range of pharmacological activities, such as cytotoxic, antifungal, insecticidal, antibacterial, anti-inflammatory, and antinociceptive activities. Currently, effective monomeric compounds or active parts have been screened for pharmacological activities from Eupatorium in vivo and in vitro. Increasing amount of data supports application and exploitation for new drug development.
Assuntos
Analgésicos/farmacologia , Anti-Infecciosos/farmacologia , Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Eupatorium/química , Compostos Orgânicos/farmacologia , Extratos Vegetais/farmacologia , Analgésicos/química , Analgésicos/isolamento & purificação , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Humanos , Compostos Orgânicos/química , Compostos Orgânicos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificaçãoRESUMO
A rapid and sensitive high-performance liquid chromatographic (HPLC) method was developed for the simultaneous separation and determination of chlorogenic acid, caffeic acid, alantolactone and isoalantolactone in Inula helenium. The HPLC separation was performed on an Elite Hypersil C18 column (200 × 4.6 mm i.d., 5 µm particle size) with a gradient elution of solvent A (acetonitrile) and solvent B (0.1% phosphoric acid in water) at a flow rate of 1.0 mL/min. Detection was monitored at 225 nm. The recovery of chlorogenic acid ranged from 95.6 to 107.7%, the recovery of caffeic acid ranged from 95.4 to 104.2%, the recovery of alantolactone ranged from 95.8 to 100.8% and the recovery of isoalantolactone ranged from 96.5 to 102.3%. The retention times for chlorogenic acid, caffeic acid, alantolactone and isoalantolactone were 5.2, 7.1, 25.6 and 26.6 min with the limits of detection of 0.069, 0.021, 0.039 and 0.051 µg/mL, respectively. Relative standard deviation for the intra-day and inter-day was ≤2.5%. The validated method is reliable for the routine control of these four compounds in I. helenium.
Assuntos
Ácidos Cafeicos/análise , Ácido Clorogênico/análise , Cromatografia Líquida de Alta Pressão/métodos , Inula/química , Lactonas/análise , Extratos Vegetais/química , Sesquiterpenos de Eudesmano/análise , Limite de Detecção , Modelos Lineares , Reprodutibilidade dos TestesRESUMO
OBJECTIVE: To study the chemical constituents in the needles of Taxus cuspidata collected from Japan. METHODS: Chemical constituents were isolated by column chromatography, TLC and preparative HPLC. The structures were identified on the basis of NMR spectral analysis. RESULTS: Six non-taxoids were isolated and identified as: 4-[(1E)-3-hydroxy-1-buten-1-yl]-3,5,5-trimethyl-2-cyclohexen-1-one (1), megastigm-5-ene-3, 9-diol (2), 6alpha-epoxy-7-megastigmen-9-one (3), 4-(4-hydroxyphenyl)-2-butanone (4), 12-hydroxy-alpha-cyperone (5), scutellarein-7-O-alpha-L-rhamnoside (6). CONCLUSION: Compounds 2 - 6 are isolated from Taxus genus for the first time. Compound 1 is obtained from Taxus cuspidata for the first time.
Assuntos
Taxus/química , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , TaxoidesRESUMO
A phytochemical investigation of Chromolaena odorata resulted in the isolation of five new compounds, 5aα,6,9,9aß,10-pentahydro-10ß-hydroxy-7-methylanthra[1,2-d][1,3]dioxol-5-one (1), 1,2-methylenedioxy-6-methylanthraquinone (2), 3-hydroxy-1,2,4-trimethoxy-6-methylanthraquinone (3), 3-hydroxy-1,2-dimethoxy-6-methylanthraquinone (4), and 7-methoxy-7-epi-medioresinol (5), together with 12 known compounds, odoratin (6), 3ß-acetyloleanolic acid (7), ursolic acid (8), ombuin (9), 4,2'-dihydroxy-4',5',6'-trimethoxychalcone (10), (-)-pinoresinol (11), austrocortinin (12), tianshic acid (13), cleomiscosin D (14), (-)-medioresinol (15), (-)-syringaresinol (16), and cleomiscosin A (17). All the compounds were evaluated for their PPARγ transactivation activity, and compound 6 showed moderate activity with an EC(50) value of 3.10 µM.
Assuntos
Antraquinonas/isolamento & purificação , Chromolaena/química , Dioxóis/isolamento & purificação , Dioxóis/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Lignanas/isolamento & purificação , Lignanas/farmacologia , PPAR gama/agonistas , Antraquinonas/química , Antraquinonas/farmacologia , Dioxóis/química , Medicamentos de Ervas Chinesas/química , Flavonoides/química , Furanos/química , Furanos/isolamento & purificação , Hepatócitos/efeitos dos fármacos , Humanos , Lignanas/química , Luciferases/metabolismo , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , EstereoisomerismoRESUMO
A novel 6/8/6-membered taxane with a rare C-12(13)-double bond and rare 2(3â20)abeotaxane were isolated from the needles of Taxus canadensis. Their structures were characterized as 7ß,9α,10ß-triacetoxytaxa-4(20),12-diene-2α,5α,11ß-triol (1) and 2α,7ß,10ß-triacetoxy-5α-hydroxy-2(3â20)abeotaxa-4(20),11-diene-9,13-dione (2) on the basis of 1D and 2D spectroscopic data. 1 is the first example of a natural taxane without substitution at both C-13 and C-14.
Assuntos
Antineoplásicos/análise , Extratos Vegetais/análise , Taxoides/análise , Taxus/química , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Neoplasias da Mama/tratamento farmacológico , Neoplasias da Mama/patologia , Linhagem Celular Tumoral , Feminino , Humanos , Espectroscopia de Ressonância Magnética , Masculino , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/química , Neoplasias da Próstata/tratamento farmacológico , Neoplasias da Próstata/patologia , Taxoides/química , Taxoides/isolamento & purificação , Taxoides/farmacologia , Falha de Tratamento , Neoplasias do Colo do Útero/tratamento farmacológico , Neoplasias do Colo do Útero/patologiaRESUMO
Achillinin A (2ß,3ß-epoxy-1α,4ß,10α-trihydroxyguai-11(13)-en-12,6α-olide, 1), a new guaianolide isolated from the flower of Achillea millefolium, exhibited potential antiproliferative activity to A549, RERF-LC-kj and QG-90 cells with 50% inhibitory concentration (IC(50)) values of 5.8, 10 and 0.31 µM, respectively.
Assuntos
Achillea/química , Adenocarcinoma/tratamento farmacológico , Antineoplásicos Fitogênicos/farmacologia , Carcinoma Pulmonar de Células não Pequenas/tratamento farmacológico , Neoplasias Pulmonares/tratamento farmacológico , Fitoterapia , Extratos Vegetais/farmacologia , Sesquiterpenos/farmacologia , Carcinoma de Pequenas Células do Pulmão/tratamento farmacológico , Adenocarcinoma/patologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/uso terapêutico , Carcinoma Pulmonar de Células não Pequenas/patologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Flores/química , Humanos , Concentração Inibidora 50 , Neoplasias Pulmonares/patologia , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Sesquiterpenos/química , Sesquiterpenos/uso terapêutico , Carcinoma de Pequenas Células do Pulmão/patologiaRESUMO
Three new taxanes, 2 α,9 α,10 ß-triacetoxy-13 α-( ß-D-glucopyranosyloxy)taxa-4(20),11-dien-5 α-ol, 5 α,10 ß,13 α-triacetoxytax-11-ene-2 α,7 ß,9 α,20-tetraol, and 5 α,10 ß,13 ß-triacetoxy-2 α,7 ß-dihydroxy-2(3â20) abeotaxa-4(20),11-dien-9-one, were isolated from the leaves of the Japanese yew, Taxus cuspidata. Compound 1 is the first example of a taxane with 13-glycosidic linkage.
Assuntos
Glucosídeos/isolamento & purificação , Extratos Vegetais , Taxoides/isolamento & purificação , Taxus/química , Glucosídeos/química , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta , Taxoides/químicaAssuntos
Asteraceae/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Cumarínicos/química , Extratos Vegetais/química , Alcaloides de Pirrolizidina/química , Terpenos/químicaAssuntos
Produtos Biológicos/química , Diterpenos/química , Plantas Medicinais/química , Produtos Biológicos/farmacologia , Compostos Bicíclicos com Pontes/química , Compostos Bicíclicos com Pontes/isolamento & purificação , Compostos Bicíclicos com Pontes/farmacologia , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Estrutura Molecular , Taxoides/química , Taxoides/isolamento & purificação , Taxoides/farmacologiaRESUMO
Two new mexicanolide-type limonoids, named xylomexicanin A (1) and xylomexicanin B (2), were isolated from seeds of the Chinese mangrove Xylocarpus granatum. Their structures were elucidated on the basis of spectroscopic methods. Compound 1 exhibited antiproliferative activity against human breast carcinoma cells (KT), while 2 did not show inhibitory effects on eleven human tumour cell lines tested.
Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Neoplasias da Mama/tratamento farmacológico , Limoninas/química , Limoninas/farmacologia , Meliaceae/química , Neoplasias/tratamento farmacológico , Sementes/química , Antineoplásicos/isolamento & purificação , Sudeste Asiático , Linhagem Celular Tumoral/efeitos dos fármacos , Feminino , Humanos , Limoninas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Medicina TradicionalRESUMO
The plants of genus Celastrus, distributed in Asia, have been used as natural insecticides and folk medicines to treat fever, chill, joint pain, edema, rheumatoid arthritis, and bacterial infection in China for a long time. This contribution reviews the chemical constituents, isolated from the plants in genus Celastrus in the past few decades, and their biological activities. The compounds listed are sesquiterpenes (beta-agarofurans), diterpenes, triterpenes, alkaloids, and flavonoids.
Assuntos
Celastrus/química , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Medicina Tradicional Chinesa , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologiaRESUMO
OBJECTIVE: To study the non-taxoids in the leaves of Taxus mairei. METHOD: The chemical constituents were isolated by chromatography and identified by spectral data. RESULT: Five compounds, taxamairin A (1), taxamairin B (2), sciadopitysin (3), ( - ) matairesinol (4), ponasterone A (5) were isolated and identified. CONCLUSION: Compounds 3-5 were isolated from this plant for the first time, compounds 1 and 2 were isolated from the leaves of T. mairei for the first time.