RESUMEN
Chemical investigation of the roots of Entandrophragma congoënse (Meliaceae) led to the isolation of two new 3,4-seco-tirucallane triterpenes, namely seco-tiaminic acids B and C (1 and 2) together with nine known compounds: 3,4-secotirucalla-21-formyl-23-oxo-4(28),7,24-trien-3-oic acid (3), methyl angolensate (4), molucensin N (5), molucensin O (6), piscidinol A (7), 7α,20(S)-dihydroxy-4,24(28)-ergostadien-3-one (8), 24-methylene-cholest-5-en-3ß,7α-diol (9), entilin A (10), and entilin B (11). Their structures were determined using extensive spectroscopic methods including 1D and 2D NMR, HRMS, and CD analyses; new results were compared to existing data in the literature. The two newly identified seco-tiaminic acids showed moderate antiplasmodial and cytotoxic activities against a chloroquine-sensitive strain of the malaria parasite (Plasmodium falciparum NF54) and were cytotoxic toward an L6 rat skeletal myoblast cell line, respectively.
Asunto(s)
Antimaláricos/química , Meliaceae/química , Triterpenos/química , Animales , Antimaláricos/aislamiento & purificación , Línea Celular , Estructura Molecular , Raíces de Plantas/química , Plasmodium falciparum/efectos de los fármacos , Ratas , Triterpenos/aislamiento & purificaciónRESUMEN
INTRODUCTION: The genus Quassia is a promising source of secondary metabolites with biological potential including antimalarial and cytotoxic activities. Limited data are available on the phytochemistry and pharmacology of Quassia silvestris Cheek & Jongkind, a Cameroonian medicinal plant used to treat various ailments. OBJECTIVES: To carry out the bioassay-guided fractionation and LC-HR-ESI-MS analyses of the leaves extract from Q. silvestris; to purify the active fractions and isolate the major compounds using different chromatographic and spectroscopic methods. The obtained compounds will be evaluated for their biological activity. MATERIAL AND METHODS: Following the cytotoxic screening and LC-HR-ESI-MS profiling of fractions obtained from partition of the methanolic extract of Q. silvestris leaves, the CH2 Cl2 -soluble fraction which exhibited the highest cytotoxicity was retained for further investigations. RESULTS: Sixteen squalene-derived metabolites were identified with oxasqualenoid derivatives being the most predominant. Among the isolates, structure elucidation of two new oxasqualenoids quassiols E (1) and F (2), were achieved by NMR (one-dimensional (1D) and two-dimensional (2D)) and MS methods. The newly characterised compounds 1 and 2, together with the known tetraol (3) and 3-oxo-oleanoic acid (16) displayed moderate cytotoxicity. CONCLUSION: The identification and structural characterisation of highly oxidised squalene derived metabolites from this plant may provide important insight data for further pharmacological investigations. The LC-HR-ESI-MSn method reported here could be developed as a rapid and efficient tool for the analyses of structurally related compounds in the genera Quassia, Simarouba, and Eurycoma of the subfamily Simarouboideae. Copyright © 2016 John Wiley & Sons, Ltd.
Asunto(s)
Antineoplásicos Fitogénicos/química , Cromatografía Liquida/métodos , Quassia/química , Espectrometría de Masa por Ionización de Electrospray/métodos , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Fraccionamiento Químico , Furanos/química , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/análisis , Hojas de la Planta/química , Plantas Medicinales/química , Piranos/química , Quassia/clasificación , Escualeno/químicaRESUMEN
Eight new triterpenoids, prototiamins A-G (1-6, 9) and seco-tiaminic acid A (10), were isolated along with four known compounds from the bark of Entandrophragma congoënse. Their structures were elucidated by means of HRMS and different NMR techniques and chemical transformations. Assignments of relative and absolute configurations for the new compounds were achieved using NOESY experiments and by chemical modification including the advanced Mosher's method. Additionally, the structure and relative configuration of compound 3 were confirmed by single-crystal X-ray diffraction analysis. Compounds 1, 3, and 5 displayed significant in vitro antiplasmodial activity against the erythrocytic stages of chloroquine-sensitive Plasmodium falciparum strain NF54. Prototiamin C (3) was the most potent of the compounds isolated, with an IC50 value of 0.44 µM. All compounds tested showed low cytotoxicity for the L6 rat skeletal myoblast cell line.
Asunto(s)
Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Meliaceae/química , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Animales , Antimaláricos/química , Camerún , Cloroquina/farmacología , Resistencia a la Enfermedad/efectos de los fármacos , Eritrocitos/efectos de los fármacos , Estructura Molecular , Músculo Esquelético/efectos de los fármacos , Resonancia Magnética Nuclear Biomolecular , Pruebas de Sensibilidad Parasitaria , Corteza de la Planta/química , Tallos de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Ratas , Triterpenos/químicaRESUMEN
Bioassay guided fractionation of Hypericum riparium leaves extract has resulted in the isolation and characterization of three new compounds namely chipericumin E (1), hyperenone C (3), and hyperixanthone (5), together with twenty known compounds. Their structures were elucidated based on comprehensive interpretation of spectroscopic and spectrometric data. Compounds 1-4, and 6-8 displayed moderate antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxic effects on the human gastric cell line BGC-823 with IC50 values ranging from 6.54 to 18.50µM.
Asunto(s)
Antibacterianos/química , Antineoplásicos Fitogénicos/química , Hypericum/química , Extractos Vegetales/química , Xantonas/química , Antibacterianos/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Lactonas/química , Lactonas/aislamiento & purificación , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Estructura Molecular , Hojas de la Planta/química , Plantas Medicinales/química , Compuestos de Espiro/química , Compuestos de Espiro/aislamiento & purificación , Xantonas/aislamiento & purificaciónRESUMEN
Two new tirucallane-type triterpenoids were isolated from the bark of Entandrophragma congoënse (Meliaceae) along with five known compounds gladoral A, bipendensin, 4-hydroxymethyl-3,5-dimethyldihydrofuran-2(3H)-one, scopoletin and 5,7-dimethoxy-6-hydroxycoumarin. Their structures were elucidated by means of spectroscopic analyses including 1D and 2D-NMR spectroscopy, high resolution mass spectrometric data as well as the comparison of data with those reported in the literature. The tested compounds (1-4) displayed moderated antiplasmodial activity against erythrocytic stages of chloroquine-resistant Plasmodium falciparum strain NF54 and low cytotoxicity on L6 cell lines. All the isolated compounds are reported for the first time from the genus Entandrophragma.
Asunto(s)
Meliaceae/química , Corteza de la Planta/química , Triterpenos/química , Animales , Antimaláricos/química , Antimaláricos/aislamiento & purificación , Línea Celular , Estructura Molecular , Plasmodium falciparum/efectos de los fármacos , Ratas , Triterpenos/aislamiento & purificaciónRESUMEN
The stem bark of Polyalthia oliveri was screened for its chemical constituents using liquid chromatography high resolution mass spectrometry resulting in the isolation of three indolosesquiterpene alkaloids named 8α-polyveolinone (1), N-acetyl-8α-polyveolinone (2) and N-acetyl-polyveoline (3), together with three known compounds, dehydro-O-methylisopiline (4), N-methylurabaine (5) and polycarpol (6). The structures of the compounds were elucidated by means of high resolution mass spectrometry and different NMR techniques and chemical transformations. Their absolute configurations were assigned by ab-initio calculation of CD and ORD data (for 2 and 3) and X-ray diffraction analysis (for 2). Compounds 2 and 3 exhibited moderate antiplasmodial activity against erythrocytic stages of chloroquine-sensitive Plasmodium falciparum NF54 strain and low cytotoxicity on rat skeletal myoblast (L6) cell line.
Asunto(s)
Antimaláricos/aislamiento & purificación , Alcaloides Indólicos/aislamiento & purificación , Plantas Medicinales/química , Polyalthia/química , Sesquiterpenos/aislamiento & purificación , Animales , Antimaláricos/química , Antimaláricos/farmacología , Camerún , Cloroquina/farmacología , Alcaloides Indólicos/química , Alcaloides Indólicos/farmacología , Masculino , Estructura Molecular , Mioblastos Esqueléticos/efectos de los fármacos , Resonancia Magnética Nuclear Biomolecular , Pruebas de Sensibilidad Parasitaria , Corteza de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Hidrocarburos Policíclicos Aromáticos/aislamiento & purificación , Ratas , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
Six labdane diterpene derivatives, named turraeanins F-J (3-6, 8) and epi-turraeanin J (7), and a pregnane steroid derivative named turraeasterodionene (2), were isolated by preparative high performance liquid chromatography together with thirteen known compounds from the Cameroonian medicinal plant Turraeanthus africanus. Their structures were elucidated by means of nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry in conjunction with the published data for the analogs, as well as the fragmentation patterns of each compound. Most of the known compounds were obtained for the first time from this plant. The compounds (2-7) were tested for their antibacterial efficacies against both Gram-positive and Gram-negative bacteria, including some clinically-important Risk group 2 human pathogens. Compound 4 exhibited the most pronounced antibacterial effectiveness comparable to standard reference streptomycin, with more potency against Gram-positive than Gram-negative bacteria. By comparing compounds 3, 4 and 5, a tentative structure-activity relationship could be drawn; selected oxidations at C-16 and C-18 drastically reduced the antibacterial efficacy of the parent compound (4). These results revealed the potential of compound 4 as a suitable antibacterial lead compound that might be used for further development of other derivatives to increase the antimicrobial efficacy.
Asunto(s)
Antibacterianos/química , Diterpenos/química , Meliaceae/química , Pregnanos/química , Antibacterianos/farmacología , Diterpenos/farmacología , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Pregnanos/farmacologíaRESUMEN
Two unusual dibenzofurans, preussiafurans A-B (1-2), together with six known compounds have been isolated from the fungus Preussia sp. occurring in Enantia chlorantha Oliv. The structures were established on the basis of 1D and 2D NMR spectroscopy and MS analysis. Compounds 1-4 showed antiplasmodial activity against erythrocytic stages of chloroquine-resistant Plasmodium falciparum (NF54) and moderate cytotoxicity on L6 cell lines with IC50 values of 8.67 and 14.8 µM, respectively.
Asunto(s)
Annonaceae/microbiología , Antimaláricos/aislamiento & purificación , Ascomicetos/química , Benzofuranos/aislamiento & purificación , Animales , Antimaláricos/química , Ascomicetos/clasificación , Ascomicetos/metabolismo , Benzofuranos/química , Benzofuranos/toxicidad , Línea Celular , Concentración 50 Inhibidora , Estructura Molecular , Ratas , Metabolismo SecundarioRESUMEN
Si-enterobactin (2a), a hexacoordinated complex of the siderophore enterobactin (2b) with silicon as the central atom, was isolated from an endophytic Streptomyces sp. occurring in Piper guinensis roots. The structure and absolute configuration were determined from NMR and MS data, and by X-ray diffraction. The orientation of the molecule along the pseudo-3-fold axis shows that the coordination environment of the silicon atom complexed with three bidentate ligands is Δ. We assume that 2a or related complexes may be involved in the transport of silicon in plants, diatoms, or other silicon-dependent organisms.
Asunto(s)
Enterobactina/metabolismo , Silicio/metabolismo , Streptomyces/metabolismo , Transporte Biológico , Cristalografía por Rayos X , Enterobactina/química , Ligandos , Conformación Molecular , Piper/microbiología , Raíces de Plantas/microbiología , Silicio/químicaRESUMEN
Four new beilschmiedic acid derivatives, cryptobeilic acids A-D (1-4), and tsangibeilin B (5) have been isolated from the bark of Beilschmiedia cryptocaryoides collected from Madagascar. Their structures were elucidated using detailed spectroscopic and spectrometric methods. Cryptobeilic acid A (1) and tsangibeilin B (5) structures were confirmed by single-crystal X-ray diffraction analysis. Compounds 1-5 displayed moderate antibacterial activity against Escherichia coli 6r3, Acinetobacter calcoaceticus DSM 586, and Pseudonamas stutzeri A1501, with the minimum inhibitory concentrations ranging from 10 to 50 µM, respectively. In addition, the compounds exhibited antiplasmodial activity against erythrocytic stages of chloroquine-resistant Plasmodium falciparum strain NF54 and weak cytotoxicity against L6 cell lines.
Asunto(s)
Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Acinetobacter calcoaceticus/efectos de los fármacos , Antibacterianos/química , Antimaláricos/química , Cloroquina/sangre , Cloroquina/farmacología , Resistencia a Medicamentos/efectos de los fármacos , Escherichia coli/efectos de los fármacos , Lauraceae/química , Madagascar , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Corteza de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Pseudomonas stutzeri/efectos de los fármacosRESUMEN
Two polyketides, cryptosporiopsin A (1) and hydroxypropan-2',3'-diol orsellinate (3), and a natural cyclic pentapeptide (4), together with two known compounds were isolated from the culture of Cryptosporiopsis sp., an endophytic fungus from leaves and branches of Zanthoxylum leprieurii (Rutaceae). The structures of these metabolites were elucidated on the basis of their spectroscopic and spectrometric data. Cryptosporiopsin A and the other metabolites exhibited motility inhibitory and lytic activities against zoospores of the grapevine downy mildew pathogen Plasmopara viticola at 10-25µg/mL. In addition, the isolated compounds displayed potent inhibitory activity against mycelial growth of two other peronosporomycete phytopathogens, Pythium ultimum, Aphanomyces cochlioides and a basidiomycetous fungus Rhizoctonia solani. Weak cytotoxic activity on brine shrimp larvae was observed.
Asunto(s)
Aphanomyces/efectos de los fármacos , Artemia/efectos de los fármacos , Ascomicetos/química , Péptidos Cíclicos/farmacología , Policétidos/farmacología , Pythium/efectos de los fármacos , Zanthoxylum/química , Animales , Aphanomyces/crecimiento & desarrollo , Ascomicetos/metabolismo , Conformación Molecular , Péptidos Cíclicos/química , Péptidos Cíclicos/metabolismo , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Policétidos/química , Policétidos/metabolismo , Pythium/crecimiento & desarrollo , Relación Estructura-Actividad , Zanthoxylum/metabolismoRESUMEN
Paeciloside A (1) and eight known compounds, acremoauxin A (2), farinosones A (3) and B (4), 1,5-dideoxy-3-C-methyl-arabitol (5), ergosterol, ergosterol peroxide, cerebroside C, and adenosine, were isolated from cultures of Paecilomyces sp. CAFT156, an endophytic fungus occurring in Enantia chlorantha Oliv (Annonaceae) leaves. The structure of the new compound 1 was elucidated using MS, UV, 1D and 2D NMR experiments, while its absolute configuration was established by subsequent single-crystal X-ray diffraction analysis using copper Kα radiation and invariom nonspherical scattering factors. Paeciloside A (1) and compounds 2, 4, and 5 displayed inhibitory effects on two gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus at a concentration of 40 µg per paper disk and moderate cytotoxicity towards brine shrimp larvae (Artemia salina). This study presents the first report on an endophytic fungus isolated from E. chlorantha Oliv and its natural products.