RESUMEN
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.
Asunto(s)
Analgésicos/farmacología , Antiinfecciosos/farmacología , Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Eupatorium/química , Compuestos Orgánicos/farmacología , Extractos Vegetales/farmacología , Analgésicos/química , Analgésicos/aislamiento & purificación , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Humanos , Compuestos Orgánicos/química , Compuestos Orgánicos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificaciónRESUMEN
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.
Asunto(s)
Ácidos Cafeicos/análisis , Ácido Clorogénico/análisis , Cromatografía Líquida de Alta Presión/métodos , Inula/química , Lactonas/análisis , Extractos Vegetales/química , Sesquiterpenos de Eudesmano/análisis , Límite de Detección , Modelos Lineales , Reproducibilidad de los ResultadosRESUMEN
A new sesquiterpene, eudesm-11-ene-4alpha,7beta,9beta-triol, was isolated from the EtOH extract of aerial parts of Dichrocephala integrifolia. Its structure was determined on the basis of spectral analysis of 1D and 2D NMR data.
Asunto(s)
Asteraceae/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Sesquiterpenos de Eudesmano/químicaRESUMEN
A series of new taxanes, 1-93, have been isolated, together with 37 known taxoids including Taxol(®) (paclitaxel) and cephalomannine, from the Canadian yew, Taxus canadensis (Taxaceae) in the past 30 years. These new taxoids possess various skeletons containing 5/7/6, 6/10/6, 6/5/5/6, 6/8/6, and 6/12 ring systems and six new taxanes with four novel skeletons, i.e., a taxane with a 6/6/8/6 ring system, a taxane with a [3.3.3] propellane skeleton, three taxanes with [3.3.3] [3.4.5] dipropellane sytems, as well as a novel taxane with a unique 5/5/4/6/6/6 hexacyclic skeleton, containing a unique [3.3.2] propellane, were isolated for the first time from natural sources. It should be emphasized that 13-acetyl-9-dihydrobaccatin III, a very useful starting material for the semisynthesis of Taxol(®) and Taxotere(®) , represents the most abundant taxane in the needles of this yew tree. These findings establish the above mentioned yew tree as significantly different from the remaining species. On the other hand, some chemical modifications on the taxanes isolated from this plant were carried out.
Asunto(s)
Extractos Vegetales/química , Taxus/química , Supervivencia Celular/efectos de los fármacos , Resistencia a Antineoplásicos/efectos de los fármacos , Humanos , Isomerismo , Células MCF-7 , Conformación Molecular , Taxoides/química , Taxoides/aislamiento & purificación , Taxoides/toxicidad , Taxus/metabolismoRESUMEN
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.
Asunto(s)
Taxus/química , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética , Extractos Vegetales/química , TaxoidesRESUMEN
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.
Asunto(s)
Antraquinonas/aislamiento & purificación , Chromolaena/química , Dioxoles/aislamiento & purificación , Dioxoles/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Lignanos/aislamiento & purificación , Lignanos/farmacología , PPAR gamma/agonistas , Antraquinonas/química , Antraquinonas/farmacología , Dioxoles/química , Medicamentos Herbarios Chinos/química , Flavonoides/química , Furanos/química , Furanos/aislamiento & purificación , Hepatocitos/efectos de los fármacos , Humanos , Lignanos/química , Luciferasas/metabolismo , Estructura Molecular , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , EstereoisomerismoAsunto(s)
Extractos Vegetales/farmacología , Estructuras de las Plantas/química , Salvia/química , Antiinfecciosos/farmacología , Antioxidantes/farmacología , Bacterias/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Humanos , Sesquiterpenos/química , Sesquiterpenos de Germacrano/química , Virus/efectos de los fármacosRESUMEN
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.
Asunto(s)
Antineoplásicos/análisis , Extractos Vegetales/análisis , Taxoides/análisis , Taxus/química , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Neoplasias de la Mama/tratamiento farmacológico , Neoplasias de la Mama/patología , Línea Celular Tumoral , Femenino , Humanos , Espectroscopía de Resonancia Magnética , Masculino , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Hojas de la Planta/química , Neoplasias de la Próstata/tratamiento farmacológico , Neoplasias de la Próstata/patología , Taxoides/química , Taxoides/aislamiento & purificación , Taxoides/farmacología , Insuficiencia del Tratamiento , Neoplasias del Cuello Uterino/tratamiento farmacológico , Neoplasias del Cuello Uterino/patologíaRESUMEN
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.
Asunto(s)
Achillea/química , Adenocarcinoma/tratamiento farmacológico , Antineoplásicos Fitogénicos/farmacología , Carcinoma de Pulmón de Células no Pequeñas/tratamiento farmacológico , Neoplasias Pulmonares/tratamiento farmacológico , Fitoterapia , Extractos Vegetales/farmacología , Sesquiterpenos/farmacología , Carcinoma Pulmonar de Células Pequeñas/tratamiento farmacológico , Adenocarcinoma/patología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/uso terapéutico , Carcinoma de Pulmón de Células no Pequeñas/patología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Flores/química , Humanos , Concentración 50 Inhibidora , Neoplasias Pulmonares/patología , Espectroscopía de Resonancia Magnética , Extractos Vegetales/química , Extractos Vegetales/uso terapéutico , Sesquiterpenos/química , Sesquiterpenos/uso terapéutico , Carcinoma Pulmonar de Células Pequeñas/patologíaRESUMEN
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.
Asunto(s)
Glucósidos/aislamiento & purificación , Extractos Vegetales , Taxoides/aislamiento & purificación , Taxus/química , Glucósidos/química , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta , Taxoides/químicaRESUMEN
The Asteraceae family comprises ca. 1000 genera, mainly distributed in Asia and Europe. Saussurea DC., as the largest subgenus of this family, comprises ca. 400 species worldwide, of which ca. 300 species occur in China. Most plants in China grow wild in the alpine zone of the Qingzang Plateau and adjacent regions at elevations of 4000â m. Plants of the genus Saussurea (Asteraceae) are used in both traditional Chinese folk medicine and Tibet folklore medicine, since they are efficacious in relieving internal heat or fever, harmonizing menstruation, invigorating blood circulation, stopping bleeding, alleviating pain, increasing energy, and curing rheumatic arthritis. A large number of biologically active compounds have been isolated from this genus. This review shows the chemotaxonomy of these compounds (215 compounds) such as sesquiterpenoids (101 compounds), flavonoids (19 compounds), phytosterols (15 compounds), triterpenoids (25 compounds), lignans (32 compounds), phenolics (23 compounds), and chlorophylls (11 compounds). Biological activities (anti-inflammatory, anticancer, antitumor, hepatoprotective, anti-ulcer, cholagogic, immunosuppressive, spasmolytic, antimicrobial, antiparasitic, antifeedant, CNS depressant, antioxidant, etc.) of these compounds, including structure-activity relationships, are also discussed.
Asunto(s)
Saussurea/química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Antiinflamatorios/química , Antiinflamatorios/farmacología , Antiulcerosos/química , Antiulcerosos/farmacología , Antidepresivos/química , Antidepresivos/farmacología , Antineoplásicos/química , Antineoplásicos/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Antiparasitarios/química , Antiparasitarios/farmacología , Colagogos y Coleréticos/química , Colagogos y Coleréticos/farmacología , Inmunosupresores/química , Inmunosupresores/farmacología , Saussurea/metabolismo , Relación Estructura-ActividadAsunto(s)
Asteraceae/química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Cumarinas/química , Extractos Vegetales/química , Alcaloides de Pirrolicidina/química , Terpenos/químicaAsunto(s)
Productos Biológicos/química , Diterpenos/química , Plantas Medicinales/química , Productos Biológicos/farmacología , Compuestos Bicíclicos con Puentes/química , Compuestos Bicíclicos con Puentes/aislamiento & purificación , Compuestos Bicíclicos con Puentes/farmacología , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Estructura Molecular , Taxoides/química , Taxoides/aislamiento & purificación , Taxoides/farmacologíaRESUMEN
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.
Asunto(s)
Antineoplásicos/química , Antineoplásicos/farmacología , Neoplasias de la Mama/tratamiento farmacológico , Limoninas/química , Limoninas/farmacología , Meliaceae/química , Neoplasias/tratamiento farmacológico , Semillas/química , Antineoplásicos/aislamiento & purificación , Asia Sudoriental , Línea Celular Tumoral/efectos de los fármacos , Femenino , Humanos , Limoninas/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Medicina TradicionalRESUMEN
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.
Asunto(s)
Celastrus/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Diterpenos/química , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Medicina Tradicional China , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Triterpenos/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacologíaRESUMEN
Echinopines A (1) and B (2), novel sesquiterpenoids with an unprecedented rearranged skeleton named echinopane, were isolated from the roots of Echinops spinosus. The structures were elucidated by extensive spectroscopic analysis. The relative configuration of 1 was assigned by a combination of NOESY correlations and a simulation analysis. A plausible biosynthetic pathway for echinopane was discussed.
Asunto(s)
Echinops (Planta)/química , Plantas Medicinales/química , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Humanos , Estructura Molecular , Sesquiterpenos/farmacologíaAsunto(s)
Magnoliopsida/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Analgésicos/química , Analgésicos/aislamiento & purificación , Analgésicos/farmacología , Animales , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Células Endoteliales/efectos de los fármacos , Hepatocitos/efectos de los fármacos , Humanos , Factores Inmunológicos/química , Factores Inmunológicos/aislamiento & purificación , Factores Inmunológicos/farmacología , Magnoliopsida/clasificación , Estructura Molecular , Extractos Vegetales/aislamiento & purificación , EstereoisomerismoRESUMEN
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.