RESUMEN
Three new spermidine alkaloids and two known compounds were isolated from the leaves of Androya decaryi. Their structures were elucidated on the basis of their spectroscopic data (NMR and mass spectrometry), by X-Ray diffraction and by comparison with literature values. Evaluation of the in vitro antiplamosdial properties of the isolated compounds revealed they did not possess any significant activity.
Asunto(s)
Alcaloides/química , Loganiaceae/química , Extractos Vegetales/química , Espermidina/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Hojas de la Planta/química , Difracción de Rayos XRESUMEN
GC-FID and GC-MS analysis of essential oil from oregano leaves (Origanum compactum) resulted in the identification of 46 compounds, representing more than 98% of the total composition. Carvacrol was the predominant compound (36.46%), followed by thymol (29.74%) and p-cymene (24.31%). Serial extractions with petroleum ether, ethyl acetate, ethanol, and water were performed on aerials parts of Origanum compactum. In these extracts, different chemical families were characterized: polyphenols (gallic acid equivalent 21.2 to 858.3 g/kg), tannins (catechin equivalent 12.4 to 510.3 g/kg), anthocyanins (cyanidin equivalent 0.38 to 5.63 mg/kg), and flavonoids (quercetin equivalent 14.5 to 54.7 g/kg). The samples (essential oil and extracts) were subjected to a screening for antioxidant (DPPH and ABTS assays) and antimalarial activities and against human breast cancer cells. The essential oil showed a higher antioxidant activity with an IC50=2±0.1 mg/L. Among the extracts, the aqueous extract had the highest antioxidant activity with an IC50=4.8±0.2 mg/L (DPPH assay). Concerning antimalarial activity, Origanum compactum essential oil and ethyl acetate extract showed the best results with an IC50 of 34 and 33 mg/mL, respectively. In addition, ethyl acetate extract (30 mg/L) and ethanol extract (56 mg/L) showed activity against human breast cancer cells (MCF7). The oregano essential oil was considered to be nontoxic.
Asunto(s)
Antimaláricos , Antineoplásicos Fitogénicos , Antioxidantes , Descubrimiento de Drogas , Aceites Volátiles , Origanum/química , Extractos Vegetales , Antocianinas/análisis , Antimaláricos/química , Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Neoplasias de la Mama/tratamiento farmacológico , Línea Celular Tumoral , Femenino , Ionización de Llama , Flavonoides/análisis , Cromatografía de Gases y Espectrometría de Masas , Humanos , Concentración 50 Inhibidora , Medicinas Tradicionales Africanas , Marruecos , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Aceites Volátiles/farmacología , Fenoles/análisis , Componentes Aéreos de las Plantas/química , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Plasmodium falciparum/efectos de los fármacos , Polifenoles , Solventes/química , Taninos/análisisRESUMEN
The aim of this work is the isolation of anti-leishmanial compounds from the ethyl acetate extracts of the bark of HEDYOSMUM ANGUSTIFOLIUM. We have successfully isolated and characterized five sesquiterpenes: one new compound (oxyonoseriolide, 1), one compound isolated for the first time from a natural source (hedyosmone, 2), and three known sesquiterpenes (onoseriolide, 3; chloranthalactone A, 4; and spathulenol, 5) that had not been previously isolated from H. ANGUSTIFOLIUM. The biological activities of 1- 5 showed that onoseriolide ( 3) was the most active compound against axenic amastigotes from LEISHMANIA AMAZONENSIS and L. INFANTUM. Moreover, it was still active on the intramacrophagic amastigotes of L. INFANTUM. The isolated compounds have also been tested on PLASMODIUM FALCIPARUM and against various mammalian cell lines.
Asunto(s)
Antimaláricos/farmacología , Leishmania/efectos de los fármacos , Magnoliopsida/química , Extractos Vegetales/farmacología , Plasmodium falciparum/efectos de los fármacos , Sesquiterpenos/farmacología , Tripanocidas/farmacología , Animales , Antimaláricos/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/uso terapéutico , Chlorocebus aethiops , Humanos , Neoplasias/tratamiento farmacológico , Pruebas de Sensibilidad Parasitaria , Corteza de la Planta , Extractos Vegetales/química , Extractos Vegetales/uso terapéutico , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/uso terapéutico , Tripanocidas/aislamiento & purificación , Células VeroRESUMEN
INTRODUCTION: In our work, we evaluate the potential antioxidant, antimalarial activity and also activity against human breast cancer cells (MCF7) of Argan fruit extracts using in vitro models to validate the traditional use of this plant. Its chemical composition was also studied to begin the understanding of its activities, waiting to find the structure-activity relationship. RESULTS: Polyphenols (89.4-218.5 eqGallic acid (mg/g dry)), tannins (39.3-214.0 eqCatechin (mg/g dry)), flavonoids (3.4-11.1 eqQuercetin (mg/g dry)) and anthocyanins (0.74-10.92 eqCyanindin (mug/g dry)) were quantified. A good (ethyl acetate and decoction) and moderate (petroleum ether) antioxidant activity were obtained for DPPH (IC(50) 32.3-600.8 microg/ml) and ABTS (IC(50) 11.9-988.8 microg/ml) assays. In addition, we found a good antimalarial activity (IC(50) 35 to >100 microg/ml) and human breast cancer cells activity (IC(50) 42 to >100 microg/ml). CONCLUSIONS: The ethyl acetate extract and the decoction show interesting antimalarial and antioxidant activities. The results indicate a good correlations between anthocyanins quantitiy and the potential antioxidant (R(2)=0.9867) and also to antimalarial activity (R(2)=0.8175).
Asunto(s)
Antimaláricos/farmacología , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/farmacología , Neoplasias de la Mama/tratamiento farmacológico , Fitoterapia , Extractos Vegetales/farmacología , Sapotaceae/química , Antimaláricos/análisis , Antimaláricos/uso terapéutico , Antineoplásicos Fitogénicos/análisis , Antineoplásicos Fitogénicos/uso terapéutico , Antioxidantes/análisis , Antioxidantes/uso terapéutico , Benzotiazoles , Compuestos de Bifenilo , Línea Celular Tumoral , Femenino , Flavonoides/análisis , Flavonoides/farmacología , Flavonoides/uso terapéutico , Frutas , Humanos , Concentración 50 Inhibidora , Fenoles/análisis , Fenoles/farmacología , Fenoles/uso terapéutico , Picratos , Extractos Vegetales/química , Extractos Vegetales/uso terapéutico , Plasmodium falciparum/efectos de los fármacos , Ácidos Sulfónicos , Taninos/análisis , Taninos/farmacología , Taninos/uso terapéuticoRESUMEN
Tapirira guianensis is a common tree used in traditional medicine in French Guiana against several infectious diseases (malaria, leishmaniasis, bacteria, etc.). The bioassay-guided purification of CH(2)Cl(2) bark extract led to the isolation of four cyclic alkyl polyol derivatives: 4,6,2'-trihydroxy-6-[10'(Z)-heptadecenyl]-1-cyclohexen-2-one (1a), 1,4,6-trihydroxy-1,2'-epoxy-6-[10'(Z)-heptadecenyl]-2-cyclohexene (1b), 1,4,5,2'-tetrahydroxy-1-[10'(Z)-heptadecenyl]-2-cyclohexene (2), and 1,3,4,6-tetrahydroxy-1,2'-epoxy-6-[10'(Z)-heptadecenyl]-cyclohexane (3). The structures were established on the basis of 1D and 2D NMR analyses. The anti-leishmanial, anti-plasmodial, anti-bacterial (on Staphylococcus aureus, Staphylococcus epidermidis and Escherichia coli), and anti-fungal (on Candida albicans) activities of the extracts and of these original compounds were evaluated. Two showed medicinal interest supporting the traditional uses of the plant. The structures were established through spectral analyses of the isolates and their derivatives.
Asunto(s)
Anacardiaceae/química , Antibacterianos/química , Antibacterianos/farmacología , Antiprotozoarios/química , Antiprotozoarios/farmacología , Espectroscopía de Resonancia Magnética , Viabilidad Microbiana/efectos de los fármacos , Estructura MolecularRESUMEN
The fragmentations of hydroxylated flavanones, chalcones and dihydrochalcones were investigated by direct loop injection using an ion trap mass spectrometry equipped with atmospheric pressure chemical ionization (APCI) probe. Some of them have been isolated from the leaves of Piper hostmannianum var. berbicense and standards were used to confirm their fragmentation behaviour. In negative ion mode, fragmentations of these three types of flavonoids revealed specific diagnostic ions which allowed us to identify aglycones in a crude plant extract. The major fragment ion obtained in MS/MS experiment for methoxylated chalcones is the neutral loss of a methyl radical whereas a H(2)O molecule is lost in the case of methoxylated dihydrochalcones. Methoxylated chalcones and flavanones isomers could be differentiated by the relative intensity ratio of [M-H-CH(3)]*(-) and [M-H-C(2)H(2)O](-) ions. Based on UV and MS data, a decision tree that includes UV lambda(max) absorptions and MS/MS diagnostic ions was built in order to obtain structural information of unknown compounds present in the extract. This tree was used to identify flavonoids in the ethyl acetate extract of P. hostmannianum var. berbicense leaves after analysis by high-performance liquid chromatography-diode array detection-atmospheric pressure chemical ionization ion trap multistage mass spectrometry. A total of 11 flavonoids were tentatively characterized based on the MS fragmentations pattern observed in MS(n) experiments.
Asunto(s)
Cromatografía Liquida/métodos , Flavonoides/química , Piper/química , Espectrometría de Masa por Ionización de Electrospray/métodos , Extractos Vegetales/químicaRESUMEN
Twelve naturally occurring glucosinolates displaying alkenyl, hydroxylated, methylsulphinyl, aromatic and indole side chains were investigated by both negative and positive ion electrospray ionisation-tandem mass spectrometry (ESI-MS/MS). In order to resolve the MS/MS spectra obtained from the anion and cation molecular ions of glucosinolates, the different fragments were investigated by MSn experiments using an ion trap spectrometer. The MS3 spectra obtained permitted possible fragmentation schemes to be proposed. These were supported by accurate mass measurements of some characteristic diagnostic ions with the help of a quadrupole time-of-flight instrument. The negative ion ESI-MS/MS behaviour of the different glucosinolates investigated in this study confirmed previously described patterns and revealed new interesting structural informative fragments. Some are common to all the glucosinolates and others are highly specific for a type of variable side chain. The positive ion ESI-MS/MS fragments obtained from the [MNa+Na]+ or [MK+K]+ molecular ions did not provide complementary specific diagnostic ions. Nevertheless, when compared with the negative ion mode, the daughter ions appeared more homogenous and with a better relative abundance for all of the 12 compounds studied. Moreover, the positive ion mode appeared to be more efficient than the negative mode for the study of methoxylated glucosinolates and should be useful to detect the glucosinolates present as organic salts in crude plant extracts.
Asunto(s)
Glucosinolatos/análisis , Glucosinolatos/química , Estructura Molecular , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Liquid chromatography (LC) coupled to negative electrospray ionisation (ESI) tandem mass spectrometry (MS/MS) was used for the rapid and sensitive identification of flavonoid compounds in Agauria salicifolia. The leaf flavonoid content in individual of A. salicifolia originating from population with contrasted ecogeographical situation and morphological characteristics was found to be variable qualitatively and highly variable quantitatively. Identification of the compounds was carried out by interpretation of UV, MS and MS/MS spectra. Fourteen flavonoids were identified, all of which had not previously been reported in Agauria spp. Two flavonol-O-glucuronides were found to differentiate the two populations.
Asunto(s)
Ericaceae/química , Flavonoides/análisis , Espectrometría de Masa por Ionización de Electrospray/métodos , Rayos Ultravioleta , Cromatografía Líquida de Alta Presión , Cromatografía Liquida , Flavonoides/química , Glucurónidos/análisis , Glicósidos/análisis , Glicósidos/química , Espectroscopía de Resonancia Magnética , Extractos Vegetales/químicaRESUMEN
A novel and very unusual azaanthracene alkaloid, 1-aza-7,8,9,10-tetramethoxy-4-methyl-2-oxo-1,2-dihydroanthracene ( 1) and a new diastereoisomer of the bis-benzylisoquinoline alkaloid rodiasine, 1 S,1' R-rodiasine ( 2), as well as the alkaloids O-methylpunjabine ( 3) and O-methylmoschatoline ( 4) have been isolated from Pseudoxandra cuspidata bark, used in French Guiana as an antimalarial. Their structures were elucidated by spectroscopic analyses, especially 2D-NMR techniques (ADEQUATE and NOESY). We found that the antimalarial activity of this bark was mostly due to bis-benzylisoquinoline 1 S,1' R-rodiasine ( 2) (IC (50)= 1 microM) also displaying a low cytotoxicity.
Asunto(s)
Alcaloides/farmacología , Annonaceae/química , Antimaláricos/farmacología , Alcaloides/química , Alcaloides/aislamiento & purificación , Animales , Antimaláricos/química , Antimaláricos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Resonancia Magnética Nuclear Biomolecular , Corteza de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Pruebas de ToxicidadRESUMEN
The dried roots of Ferula hermonis yielded three new daucanes, (1R,4R)-4-hydroxydauca-7-ene-6-one (1), (1R,4R)-4-hydroxydauca-7-ene-6,9-dione (2), and (1R,3S,8S)-3-ethoxy-8-angeloyloxydauca-4-en-9-one (3), together with the three known sesquiterpenes, ferutinin, teferidin, and (+)-alpha-bisabolol. The structures of compounds 1-3 were elucidated on the basis of spectroscopic evidence. The effect of these compounds on the proliferation of estrogen-dependent MCF-7 cells was evaluated, and it was found that compounds 1 and 3 exhibited proliferative activity, whereas 2 showed an antiproliferative effect.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Estrógenos/aislamiento & purificación , Ferula/química , Plantas Medicinales/química , Sesquiterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Benzoatos/química , Benzoatos/aislamiento & purificación , Compuestos Bicíclicos con Puentes , Cicloheptanos , Ensayos de Selección de Medicamentos Antitumorales , Estrógenos/química , Estrógenos/farmacología , Líbano , Estructura Molecular , Sesquiterpenos Monocíclicos , Resonancia Magnética Nuclear Biomolecular , Raíces de Plantas/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Células Tumorales CultivadasRESUMEN
A new coumarin glucoside, 3'(S)-hydroxy-2',2'-dimethyl-dihydropyranocoumarin-8-beta-d-glucopyranosyl, one coumarin, five furanocoumarins, three bicoumarins, three quinoline alkaloids and one sinapoyl sucrose derivative have been isolated from the roots of Ruta corsica.
Asunto(s)
Alcaloides/química , Cumarinas/química , Glucósidos/química , Fitoterapia , Extractos Vegetales/química , Ruta , Humanos , Raíces de PlantasRESUMEN
Five new neoclerodane diterpenoids, rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-15,16,12,20-diepoxy-3,4-dihydroxy-20-methoxyneocleroda-13(16),14-diene (1), rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-15,16,12,20-diepoxy-3,4,20-trihydroxyneocleroda-13(16),14-diene (2), rel-(3R,4S,5S,6R,7S,8S, 9R,10S,12R,20S)-6,7-diacetoxy-3,4,15,16,12,20-triepoxy-20-hydroxyneocleroda-13(16),14-diene (3), rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-3,4,15,16,12,20-triepoxy-20-hydroxyneocleroda-13(16),14-diene (4), and rel-(3R,4S,5R,7R,8S,9R,10S,12R,20R)-7,20-diacetoxy-3,4,15,16,12,20-triepoxyneocleroda-13(16),14-diene (5), have been isolated from the bark of Croton eluteria. The structures of the compounds 1-5 (cascarillins E-I) were determined by spectroscopic data interpretation.