RESUMEN
Ornithogalum thyrsoides Jacq belongs to the Asparagaceae family and is cultivated for ornamental purposes. The authors have previously reported several cholestane- and spirostan-type steroidal glycosides from O. thyrsoides. Conventional TLC analysis of the methanolic bulb extract of O. thyrsoides suggested the presence of unprecedented compounds; therefore, a detailed phytochemical investigation of the extract was performed and 35 steroidal glycosides (1-35), including 21 previously undescribed ones (1-21) were collected. The structures of 1-21 were determined mainly by analyses of their 1H and 13C NMR spectra with the aid of two-dimensional NMR spectroscopy. The isolated compounds were classified into three distinct groups: furostan-type (1, 2, 8-12, and 22), spirostan-type (3-7 and 23-26), and cholestane-type (13-21 and 27-35). Although the C/D-ring junction of the steroidal skeleton is typically trans-oriented, except for some cardiotonic and pregnane-type steroidal derivatives, 7 possess a cis C/D-ring junction. This is the first reported instance of such a configuration in spirostan-type steroidal derivatives, marking it as a finding of significant interest. Compounds 1-35 were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells and SBC-3 human small-cell lung cancer cells. Compounds 3-6, 9, 17-21, 23-25, and 30-35 demonstrated cytotoxicity in a dose-dependent manner with IC50 values ranging from 0.000086 to 18 µM and from 0.00014 to 37 µM toward HL-60 and SBC-3 cells, respectively. Compound 19, which is obtained in a good yield and shows relatively potent cytotoxicity among the undescribed compounds, induces apoptosis in HL-60 cells, accompanied by arresting the cell cycle of HL-60 cells at the G2/M phase. In contrast, 19 causes oxidative stress-associated necrosis in SBC-3 cells. The cytotoxic mechanism of 19 is different between HL-60 and SBC-3 cells.
Asunto(s)
Colestanos , Leucemia , Neoplasias Pulmonares , Ornithogalum , Espirostanos , Humanos , Células HL-60 , Ornithogalum/química , Glicósidos/química , Colestanos/química , Esteroides/farmacología , Esteroides/química , Extractos Vegetales/farmacologíaRESUMEN
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
Ganoderic Acids (GAs) are the major medicinal compounds in Ganoderma lucidum used as traditional Chinese medicine since ancient times. Ganoderic acid A (GAA) is the first discovered ganoderic acids reported in the literature, which is also one of most abundant triterpenoids of Ganoderma lucidum. Especially, GAA has been extensively investigated in recent decades for its positive medicinal activities. However, the vibrational properties of GAs have rarely been studied or reported. In this work, we focused on the typical GAA and studied the infrared (IR) and Raman spectra based on both experiments and DFT calculations. As such, we could not only achieve the assignments of the vibrational modes, but also from the IR and Raman spectra, we found that the spectral region from 1500â¯cm-1 to 1800â¯cm-1 is particularly useful for distinguishing different types of GAs. In addition, its dehydrogenated derivative ganoderenic acid A (GOA) was also studied, which could be identified due to its spectral feature of strong IR and Raman bands around 1620â¯cm-1. This work therefore may facilitate the application of IR and Raman spectroscopies in the inspection and quality control of Ganoderma lucidum.
Asunto(s)
Ácidos Heptanoicos/química , Lanosterol/análogos & derivados , Espectrofotometría Infrarroja/métodos , Espectrometría Raman/métodos , Colestanos/química , Teoría Funcional de la Densidad , Lanosterol/química , Estructura Molecular , Reishi/química , Espectroscopía Infrarroja por Transformada de Fourier , VibraciónRESUMEN
A search for cytotoxic cholestane glycosides from Ornithogalum saundersiae bulbs resulted in the isolation of three new OSW-1 analogues (1-3), a new cholestane bisdesmoside (4), a 5ß-cholestane diglycoside (5), and four new 24(23 â 22)-abeo-cholestane glycosides (6-9), together with 11 known cholestane glycosides (10-20), including OSW-1 (11). The structures of 1-9 were determined based on conventional spectroscopic analysis and chemical evidence. As expected, based on previous data, 1-3 exhibited potent cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells. Furthermore, the ability of OSW-1 to induce apoptosis in HL-60 cells was examined. Aggregation of nuclear chromatin, accumulation of the sub-G1 cells, DNA fragmentation, and caspase-3 activation were assessed in HL-60 cells treated with OSW-1, providing evidence for OSW-1-induced apoptosis in HL-60 cells. No mitochondrial membrane potential or release of cytochrome c into the cytoplasm were observed in the OSW-1-treated apoptotic HL-60 cells, indicating that a mitochondria-independent signaling pathway is involved in apoptotic cell death.
Asunto(s)
Colestanos/química , Colestenonas/metabolismo , Glicósidos/química , Células HL-60/metabolismo , Mitocondrias/metabolismo , Ornithogalum/química , Saponinas/metabolismo , Apoptosis , Humanos , Transducción de SeñalRESUMEN
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
A phytochemical investigation of the seeds of Persian leek afforded the isolation of two new spirostane glycosides, persicosides A (1) and B (2), four new furostane glycosides, isolated as a couple of inseparable mixture, persicosides C1/C2 (3a/3b) and D1/D2 (4a/4b), one cholestane glycoside, persicoside E (5), together with the furostane glycosides ceposides A1/A2 and C1/C2 (6a/6b and 7a/7b), tropeosides A1/A2 and B1/B2 (8a/8b and 9a/9b), and ascalonicoside A1/A2 (10a/10b), already described in white onion, red Tropea onion, and shallot, respectively. Structure elucidation of the compounds was carried out by comprehensive spectroscopic analyses, including 2D NMR spectroscopy and MS spectrometry, and by chemical evidences. The chemical structure of new compounds were identified as (25S)-spirostan-2α,3ß,6ß-triol 3-O-[ß-d-glucopyranosyl-(1â3)] [ß-d-xylopyranosyl-(1â2)]-ß-d-glucopyranosyl-(1â4)-ß-d-galactopyranoside (1), (25S)-spirostan-2α,3ß,6ß-triol 3-O-[ß-d-xylopyranosyl-(1â3)] [α-l-rhamnopyranosyl-(1â2)]-ß-d-glucopyranosyl-(1â4)-O-ß-d-galactopyranoside (2), furosta-1ß,3ß,22ξ,26-tetraol 5-en 1-O-ß-d-glucopyranosyl (1â3)-ß-d-glucopyranosyl (1â2)-ß-d-galactopyranosyl 26-O-α-l-rhamnopyranosyl (1â2)-ß-d-galactopyranoside (3a,3b), furosta-2α,3ß,22ξ,26-tetraol 3-O-ß-d-glucopyranosyl (1â3)-ß-d-glucopyranosyl (1â2)-ß-d-galactopyranosyl 26-O-ß-d-glucopyranoside (4a,4b), (22S)-cholesta-1ß,3ß,16ß,22ß-tetraol 5-en 1-O-α-l-rhamnopyranosyl 16-O-α-l-rhamnopyranosyl (1â2)-ß-d-galactopyranoside (5). Antifungal activity of the isolated compounds was evaluated against the fungal pathogens, Penicillium italicum, Aspergillus niger, Trichoderma harzianum and Botrytis cinerea. Persicosides A and B showed the higher activity on the tested fungi highlighting the positive effect of the spirostane skeleton on the antifungal activity.
Asunto(s)
Allium/química , Antifúngicos/farmacología , Colestanos/farmacología , Extractos Vegetales/farmacología , Saponinas/farmacología , Antifúngicos/química , Colestanos/química , Hongos/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Extractos Vegetales/química , Saponinas/químicaRESUMEN
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
Cycloalumination of 3'-methylene-(5α)-spirocholestane-3,1'-cyclobutane with triethylaluminum catalyzed by Cp(2)ZrCl(2) was accomplished for the first time to give (5α)-spirocholestane-3,1'-(6'-ethyl-6'-aluminaspiro [3.4] octane) in 89%. The latter, without isolation, was converted into spirotetrahydroselenophene or spirotetrahydrofuran.
Asunto(s)
Óxido de Aluminio/química , Colestanos/química , Furanos/química , Compuestos de Organoselenio/química , Compuestos de Espiro/química , Esteroides/química , Catálisis , Colestanos/síntesis química , Espectroscopía de Resonancia Magnética , Compuestos de Espiro/síntesis químicaRESUMEN
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
Using tigogenin as starting material, (20S)-20-hydroxycholestane-3,6-dione (1), (16S, 20S)-16,20-dihydroxycholestan-3-one (2), (20S)-20-hydroxycholest-1-ene-3,16-dione (3) and (20S)-20-hydroxycholest-4-ene-3,16-dione (4), natural polyoxygenated steroids from the gorgonian, Leptogorgia sarmentosa, were synthesized in four steps. Antitumor activity against three tumor cell lines (breast cancer, MCF7, lung cancer NCI and oral cancer KB) was evaluated. Two compounds (3 and 4) showed strong activity against NCI (IC(50) 6.16 and 10.51 microM) and moderate activity against MCF7 and KB, the IC(50) being in the range 30.65-47.22 microM. Compound 2 showed moderate activity against NCI (IC(50) 42.68 microM) but was inactive against MCF7 and KB whereas compound 1 showed no activity against all tested cells.
Asunto(s)
Colestanos/síntesis química , Colestanos/toxicidad , Cnidarios/química , Citotoxinas/química , Esteroides/síntesis química , Esteroides/toxicidad , Adenocarcinoma/tratamiento farmacológico , Animales , Antineoplásicos/uso terapéutico , Neoplasias de la Mama/tratamiento farmacológico , Carcinoma de Células Pequeñas/tratamiento farmacológico , Carcinoma de Células Escamosas/tratamiento farmacológico , Línea Celular Tumoral , Colestanos/química , Citotoxinas/aislamiento & purificación , Evaluación Preclínica de Medicamentos , Humanos , Concentración 50 Inhibidora , Neoplasias Pulmonares/tratamiento farmacológico , Estructura Molecular , Neoplasias de la Boca/tratamiento farmacológico , Esteroides/química , Esteroides/aislamiento & purificaciónRESUMEN
In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory activity of the TNF-alpha production by macrophages. A preliminary qualitative structure-activity relationship was established.
Asunto(s)
Androstanos/síntesis química , Androstanos/farmacología , Colestanos/síntesis química , Colestanos/farmacología , Factor de Necrosis Tumoral alfa/antagonistas & inhibidores , Androstanos/química , Animales , Línea Celular , Colestanos/química , Deshidroepiandrosterona/química , Evaluación Preclínica de Medicamentos , Factores Inmunológicos/síntesis química , Factores Inmunológicos/química , Factores Inmunológicos/farmacología , Ratones , Estructura Molecular , Estigmasterol/química , Relación Estructura-ActividadRESUMEN
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.