RESUMEN
An extract of Galtonia regalis from the Natural Products Discovery Institute showed moderate antiplasmodial activity, with an IC50 value less than 1.25 µg/mL. The two known cholestane glycosides 1 and 2 and the five new cholestane glycosides galtonosides A-E (3-7) were isolated after bioassay-directed fractionation. The structures of the new compounds were determined by interpretation of their NMR and mass spectra. Among these compounds, galtonoside B (4) displayed the most potent antiplasmodial activity, with an IC50 value of 0.214 µM against the drug-resistant Dd2 strain of Plasmodium falciparum.
Asunto(s)
Antimaláricos/química , Colestanos/farmacología , Glicósidos/farmacología , Asparagales/química , Colestanos/química , Colestanos/aislamiento & purificación , Glicósidos/química , Glicósidos/aislamiento & purificación , Humanos , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Plasmodium falciparum/químicaRESUMEN
Three new cholestane-type sterols bearing an unusual ∆22-24-oxo side chain, namely, dictyoptesterols A-C (1-3), were isolated from the brown alga Dictyopteris undulata Holmes, together with five known strutural analogues (4-8). Their structures were elucidated on the basis of by extensive spectroscopic analysis. The absolute configurations of the steroidal nuclei of the new compounds were proposed by a comparison of NMR data with those of related known compounds as well as biogenetic considerations. All of the isolates were evaluated in vitro for their potential to inhibit protein tyrosine phosphatase-1B (PTP1B) activity. The results showed that compounds 1-5 exhibited different levels of PTP1B inhibitory activities with IC50 values ranging from 3.03⯱â¯0.76 to 15.01⯱â¯2.88⯵M. In particular, compounds 3 and 4 showed promising inhibitory effects towards PTP1B with IC50 values of 3.03⯱â¯0.76 and 3.72⯱â¯0.40⯵M, respectively, when compared to the positive control oleanolic acid (IC50, 2.83⯱â¯0.39⯵M). The chemotaxonomic significance of these isolated ∆22-24-oxo cholestanes has also been discussed.
Asunto(s)
Colestanos/aislamiento & purificación , Inhibidores Enzimáticos/aislamiento & purificación , Phaeophyceae/química , Fitosteroles/aislamiento & purificación , Proteína Tirosina Fosfatasa no Receptora Tipo 1/antagonistas & inhibidores , China , Colestanos/farmacología , Inhibidores Enzimáticos/farmacología , Estructura Molecular , Fitosteroles/farmacologíaRESUMEN
Phytochemical investigation of the tubers of Ophiopogon japonicus led to the isolation of five previously undescribed steroidal saponins, ophiojaponins A-E, together with twelve known ones. The structures of these isolated compounds were elucidated by detailed spectroscopic analyses and chemical methods. Ophiojaponins A-C are rare naturally occurring C29 steroidal glycosides possessing a homo-cholestane skeleton with an aromatized ring E. Ruscogenin 1-O-α-L-rhamnopyranosyl-(1 â 2)-4-O-sulfo-ß-D-fucopyranosido-3-O-ß-D-glucopyranoside was isolated as single component and its full spectroscopic data was reported for the first time. The isolated steroidal saponins were evaluated for their cytotoxicities against two human tumor cell lines MG-63 and SNU387. Among them, five known spirostane-type glycosides showed cytotoxic activity against both MG-63 and SNU387 cell lines with IC50 values ranging from 0.76 to 27.0 µM.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Colestanos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Ophiopogon/química , Tubérculos de la Planta/química , Saponinas/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Colestanos/química , Colestanos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Estructura Molecular , Saponinas/química , Saponinas/farmacología , EstereoisomerismoRESUMEN
Six new spirostane glycosides (1-6), named polygodosides A-F, one new furostanol glycoside, polygodoside G (7), one new cholestane glycoside, polygodoside H (8), and one new steroidal sapogenin, polygodosin A (9), together with thirteen known compounds (10-22) were isolated from a 90% MeOH extract of the fibrous roots of Polygonatum odoratum (Mill.) Druce. The structures of new compounds were elucidated by extensive 1D and 2D NMR spectroscopic analyses and mass spectrometry. The effects on TF procoagulant activity in THP-1 cells were tested for most of the compounds.
Asunto(s)
Trastornos de la Coagulación Sanguínea/tratamiento farmacológico , Colestanos/química , Glicósidos/química , Sapogeninas/química , Esteroles/química , Tromboplastina/metabolismo , Trastornos de la Coagulación Sanguínea/metabolismo , Colestanos/aislamiento & purificación , Medicamentos Herbarios Chinos/química , Glicósidos/aislamiento & purificación , Humanos , Estructura Molecular , Raíces de Plantas/química , Polygonatum/química , Sapogeninas/aislamiento & purificación , Esteroides/química , Esteroides/aislamiento & purificación , Esteroles/aislamiento & purificación , Tromboplastina/antagonistas & inhibidores , Tromboplastina/químicaRESUMEN
Much attention has been paid to cholestane-type steroidal glycosides because of their importance from the perspectives of both chemical diversity and significant biological activities. A phytochemical investigation of the rhizomes of Polygonatum odoratum (Liliaceae) resulted in the isolation of three novel cholestane-type steroidal glycosides (1-3) with unique Δ(14,16)-unsaturated D-ring structures as well as two novel spirostane-type steroidal saponins (4 and 5) and three known steroidal glycosides (6-8). Their structures were determined by various spectroscopic methods and chemical reactions. Steroidal saponin 7 showed significant antifungal activity against Candida albicans JCM1542 (MIC 3.1 µg/mL) and Aspergillus fumigatus JCM1738 (MIC 6.3 µg/mL).
Asunto(s)
Colestanos/química , Glicósidos/química , Extractos Vegetales/química , Polygonatum/química , Saponinas/química , Espirostanos/química , Colestanos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Estructura Molecular , Saponinas/aislamiento & purificación , Espirostanos/aislamiento & purificación , EstereoisomerismoRESUMEN
Three new unusual 23-spirocholestane derivatives, ypsilanogenin (1), ypsilanogenin 3-O-ß-D-glucopyranoside (2), and 4'-acetylypsilanogenin 3-O-ß-D-glucopyranoside (3), were isolated from the whole plants of Ypsilandra thibetica. The structures of compounds 1-3 were deduced by spectroscopic and chemical methods, and the structure of 1 was further confirmed by a single-crystal diffraction analysis. All isolates were evaluated for their inhibitory activities against HIV-1.
Asunto(s)
Fármacos Anti-VIH/farmacología , Glicósidos/farmacología , Liliaceae/química , Fármacos Anti-VIH/química , Fármacos Anti-VIH/aislamiento & purificación , Colestanos/química , Colestanos/aislamiento & purificación , Colestanos/farmacología , Cristalografía por Rayos X , Glicósidos/química , Glicósidos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Plantas Medicinales , Saponinas/química , Saponinas/aislamiento & purificación , Saponinas/farmacología , Compuestos de Espiro/química , Compuestos de Espiro/aislamiento & purificación , Compuestos de Espiro/farmacologíaRESUMEN
Phytochemical investigation of the ethanol extract obtained from the aerial parts of the Euphorbia altotibetic PAULS. Grown in China resulted in the isolation of three new cholestane-type and three new ergostane-type steroids (cholest-5-en-2ß, 4ß-diol; cholest-5-en-1ß, 4ß-diol; cholest-5-en-1α, 3ß, 4α -triol; (22E)-ergosta-7,9,22-trien- 3ß-ol ß-D-glucoside; 5α-methoxy-(22E)-ergosta-7,9,22-trien-3ß-ol ß-D-glucoside; 6ß- methoxy-(22E)-ergosta-7,9,22-trien-3ß-ol ß-D-glucoside), along with seven known compounds. Their structures were established by extensive one- and two-dimensional NMR spectroscopy, as well as other spectrum and chemical analysis. The isolated new steroids exhibited potent anti-tumor activity against the HeLa cell and Hep-G2 cell with the 50% inhibiting concentration values ranging from 1.9 to 9.2 µg/mL.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Colestanos/farmacología , Ergosterol/análogos & derivados , Ergosterol/farmacología , Euphorbia/química , Componentes Aéreos de las Plantas/química , Extractos Vegetales/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Supervivencia Celular/efectos de los fármacos , Colestanos/química , Colestanos/aislamiento & purificación , Ergosterol/química , Ergosterol/aislamiento & purificación , Células HeLa , Células Hep G2 , Humanos , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificaciónRESUMEN
Six new cholestane glycosides (1, 5, 6, 10, 12, and 13) and two new sterols (9 and 11), along with five known compounds (2-4, 7, and 8), were isolated from the underground parts of Chamaelirium luteum (Liliaceae). The structures of these new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds and aglycones were evaluated for their cytotoxic activity against HL-60 human leukemia cells. Compounds 6a, 10a, 12a, 13, and 13a were cytotoxic to HL-60 cells, with IC50 values of 12.8, 9.8, 15.3, 6.2, and 10.2 µM, respectively.
Asunto(s)
Antineoplásicos/farmacología , Colestanos/farmacología , Glicósidos/farmacología , Liliaceae/química , Fitosteroles/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Supervivencia Celular/efectos de los fármacos , Colestanos/química , Colestanos/aislamiento & purificación , Ensayos de Selección de Medicamentos Antitumorales , Glicósidos/química , Glicósidos/aislamiento & purificación , Células HL-60 , Humanos , Hidrólisis , Concentración 50 Inhibidora , Leucemia Promielocítica Aguda , Espectroscopía de Resonancia Magnética , Estructura Molecular , Fitosteroles/química , Fitosteroles/aislamiento & purificación , Fitoterapia , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Raíces de Plantas/química , Plantas MedicinalesRESUMEN
The chloroform/methanol extract of the red alga, Laurencia papillosa, collected from the Red Sea in Saudi Arabia, was found to contain two cholestane derivatives: 3alpha, 6alpha-dihydroxy-5beta-cholestan-12-one (1) and the known, 6beta-hydroxycholest-4-en-3-one (2), which was isolated separately in a pure form for the first time. In addition to these compounds, a new aldehyde derivative, (E)-2-{(E) tridec-2-en-2-yl} heptadec-2-enal (3), was isolated. The structures of all compounds were established based on extensive spectroscopic (1D and 2D NMR, UV, IR) and mass spectrometric studies. All compounds, except 2, were tested for their antifungal activity. Significant activities were associated with 1 and 3 against Candida albicans, Aspergillus fumigatus, and A. flavus.
Asunto(s)
Aldehídos/aislamiento & purificación , Antifúngicos/aislamiento & purificación , Colestanos/aislamiento & purificación , Rhodophyta/química , Aldehídos/química , Aldehídos/farmacología , Antifúngicos/química , Antifúngicos/farmacología , Colestanos/química , Colestanos/farmacología , Espectroscopía de Resonancia MagnéticaRESUMEN
Two new steroidal glycosides, named dioseptemlosides I (1) and J (2), along with two known trihydroxy fatty acids, (12 Z,15 Z)-9,10,11-trihydroxy-12,15-octadecadienoic acid (3) and (12 Z)-9,10,11-trihydroxy-12-octadecenoic acid (4), were isolated from the rhizomes of Dioscorea septemloba. Their structures were determined by HRESIMS, 1D and 2D NMR experiments, physical data, and chemical methods. The antitumor activity of compounds 1-4 was evaluated against three tumor cell lines and all of them were inactive at a concentration of 10 microM.
Asunto(s)
Colestanos/aislamiento & purificación , Dioscorea/química , Ácidos Grasos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Extractos Vegetales/química , Línea Celular Tumoral , Colestanos/química , Ácidos Grasos/química , Glicósidos/química , Humanos , Estructura Molecular , RizomaRESUMEN
The Neoproterozoic era (1,000-542 Myr ago) was an era of climatic extremes and biological evolutionary developments culminating in the emergence of animals (Metazoa) and new ecosystems. Here we show that abundant sedimentary 24-isopropylcholestanes, the hydrocarbon remains of C(30) sterols produced by marine demosponges, record the presence of Metazoa in the geological record before the end of the Marinoan glaciation ( approximately 635 Myr ago). These sterane biomarkers are abundant in all formations of the Huqf Supergroup, South Oman Salt Basin, and, based on a new high-precision geochronology, constitute a continuous 100-Myr-long chemical fossil record of demosponges through the terminal Neoproterozoic and into the Early Cambrian epoch. The demosponge steranes occur in strata that underlie the Marinoan cap carbonate (>635 Myr ago). They currently represent the oldest evidence for animals in the fossil record, and are evidence for animals pre-dating the termination of the Marinoan glaciation. This suggests that shallow shelf waters in some late Cryogenian ocean basins (>635 Myr ago) contained dissolved oxygen in concentrations sufficient to support basal metazoan life at least 100 Myr before the rapid diversification of bilaterians during the Cambrian explosion. Biomarker analysis has yet to reveal any convincing evidence for ancient sponges pre-dating the first globally extensive Neoproterozoic glacial episode (the Sturtian, approximately 713 Myr ago in Oman).
Asunto(s)
Evolución Biológica , Colestanos/análisis , Colestanos/química , Fósiles , Sedimentos Geológicos/química , Poríferos/fisiología , Animales , Arabia , Biomarcadores/análisis , Biomarcadores/química , Colestanos/aislamiento & purificación , Cromatografía de Gases y Espectrometría de Masas , Historia Antigua , Hidrocarburos/análisis , Hidrocarburos/química , Cubierta de Hielo , Océanos y Mares , Oxígeno/análisis , Agua de Mar/químicaRESUMEN
The methanol extract of the whole parts of Tribulus macropterus Boiss. (family Zygophyllaceae) showed cytotoxic activity against a human tumour cell line (hepatocyte generation 2, HepG2) (IC50 = 2.9 microg/ml). The n-butanolic fraction obtained from successive fractionation of the methanolic extract exhibited activity against HepG2 (IC50 = 2.6 microg/ml). Therefore, this fraction was subjected to separation using different chromatographic techniques. Five compounds, 1-5, were isolated and identified as: (22S,25S)-16beta,22,26-trihydroxy-cholest-4-en-3-one-16-O-beta-D-glucopyranosyl-(1-->3)-beta-D-xylopyranoside (1), (22S,25S)-16beta,22,26-trihydroxy-cholest-4-en-3-one-16-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside (2), sucrose (3), D-pinitol (4) and 3beta-hydroxy-5a-pregn-16(17)en-20-one-3-O-beta-D-xylopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-ga-lactopyranoside (5) on the basis of spectroscopic and chemical data. The three steroidal compounds 1, 2 and 5 were also tested against the same cell line HepG2 and their IC50 values were 2.4, 2.2 and 1.1 microg/ml, respectively.
Asunto(s)
Supervivencia Celular/efectos de los fármacos , Colestanos/toxicidad , Pregnanos/toxicidad , Tribulus/química , Carcinoma Hepatocelular , Línea Celular Tumoral , Colestanos/química , Colestanos/aislamiento & purificación , Glicósidos/química , Glicósidos/aislamiento & purificación , Glicósidos/toxicidad , Humanos , Neoplasias Hepáticas , Modelos Moleculares , Extractos Vegetales/química , Pregnanos/química , Pregnanos/aislamiento & purificaciónRESUMEN
A phytochemical investigation of the stems of the South Brazilian endemic species Raulinoa echinata has led to the isolation of two new methoxylated protolimonoid epimers (1 and 2) together with the known melianone and melianodiol. The leaves afforded three glabretal-type triterpene derivatives esterified by N-methylanthranilic acid (3-5). Compounds 1 and 2 displayed weak inhibitory activity when assayed in vitro against trypomastigote forms of Trypanosoma cruzi. Compounds 1-5 were inactive in a brine shrimp (Artemia salina) lethality test.
Asunto(s)
Antiprotozoarios/aislamiento & purificación , Colestanos/aislamiento & purificación , Plantas Medicinales/química , Rutaceae/química , Triterpenos/aislamiento & purificación , ortoaminobenzoatos/aislamiento & purificación , Animales , Antiprotozoarios/química , Antiprotozoarios/farmacología , Artemia/efectos de los fármacos , Brasil , Colestanos/química , Colestanos/farmacología , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Tallos de la Planta/química , Triterpenos/química , Triterpenos/farmacología , Trypanosoma cruzi/efectos de los fármacos , ortoaminobenzoatos/química , ortoaminobenzoatos/farmacologíaRESUMEN
Further search for cytotoxic compounds contained in the bulbs of Galtonia candicans (Liliaceae) led to the isolation of four potent cytotoxic cholestane glycosides (1-4) based upon 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one, three of which (2-4) have not been reported previously. A new cholestane bisdesmoside (5) and a new rearranged cholestane glycoside (6) were also isolated. The structural assignment of the new constituents was carried out by spectroscopic analysis and a few chemical transformations.
Asunto(s)
Colestanos/toxicidad , Citotoxinas/toxicidad , Glicósidos/toxicidad , Liliaceae/toxicidad , Colestanos/química , Colestanos/aislamiento & purificación , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Glicósidos/química , Glicósidos/aislamiento & purificación , Células HL-60 , Humanos , Concentración 50 Inhibidora , Liliaceae/química , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Estructuras de las Plantas/química , Estructuras de las Plantas/toxicidadRESUMEN
Two new cholestane bisdesmosides (1, 2) based upon (22S)-cholest-5-ene-3 beta,16 beta,22-triol with an acetyl group at the sugar moiety and three new ones (3-5) based upon (22S)-cholest-5-ene-1 beta,3 beta,16 beta,22-tetrol, along with a known cholestane glycoside, were isolated from the bulbs of Galtonia candicans. The structures of the new compounds were determined by spectroscopic analysis and chemical transformations.
Asunto(s)
Colestanos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Liliaceae/química , Plantas Medicinales/química , Colestanos/química , Colestanos/farmacología , Cromatografía Líquida de Alta Presión , Relación Dosis-Respuesta a Droga , Glicósidos/química , Glicósidos/farmacología , Células HL-60/efectos de los fármacos , Humanos , Japón , Espectroscopía de Resonancia Magnética , Estructura Molecular , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Further phytochemical analysis of the bulbs of Ornithogalum saundersiae has yielded two new cytotoxic cholestane triglycosides (1 and 2). The structures of these compounds were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and the results of hydrolytic cleavage. Compounds 1 and 2 and several analogues were evaluated for their cytotoxicity against HL-60 cells.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Colestanos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Liliaceae/química , Raíces de Plantas/química , Plantas Medicinales/química , Antineoplásicos Fitogénicos/farmacología , Colestanos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Glicósidos/farmacología , Células HL-60 , Humanos , Hidrólisis , Espectrometría de Masa Bombardeada por Átomos Veloces , Células Tumorales CultivadasRESUMEN
A new lanostanoid ester glucoside, 3 alpha-acetoxy-5 alpha-lanosta-8,24-dien-21-oic acid ester beta-d-glucoside (1), and a known steroid, 2 beta,3 alpha,9 alpha-trihydroxy-5 alpha-ergosta-7,22-diene (2), were isolated from the fruit bodies of Ganoderma tsugae and their structures determined by spectroscopic methods. To study the cytotoxicity of 1 and 2, the changes of DNA content in human hepatocytes (Hep 3B) were studied. A sub-G1 cell stage was drastically increased after 24-h incubation with 1 (24 micrograms/mL). Compound 2 (100 micrograms/mL) inhibited the cell cycle progression of Hep 3B cells at the G2/M phase with an IC50 value of about 87.1 micrograms/mL. These results indicate that 1 causes cell death by apoptosis and 2 may possess the activity of cell cycle inhibition.