RESUMO
Triterpenoid biosynthesis is generally anaerobic in bacteria and aerobic in Eukarya. The major class of triterpenoids in bacteria, the hopanoids, is different to that in Eukarya, the lanostanoids, and their 4,4,14-demethylated derivatives, sterols. In the deep sea, the prokaryotic contribution to primary productivity has been suggested to be higher because local environmental conditions prevent classic photosynthetic processes from occurring. Sterols have been used as trophic biomarkers because primary producers have different compositions, and they are incorporated in primary consumer tissues. In the present study, we inferred food supply to deep sea, sponges, cnidarians, mollusks, crustaceans, and echinoderms from euphotic zone production which is driven by phytoplankton eukaryotic autotrophy. Sterol composition was obtained by gas chromatography and mass spectrometry. Moreover, we compared the sterol composition of three phyla (i.e., Porifera, Cnidaria, and Echinodermata) collected between a deep and cold-water region and a shallow tropical area. We hypothesized that the sterol composition of shallow tropical benthic organisms would better reflect their photoautotrophic sources independently of the taxonomy. Shallow tropical sponges and cnidarians from environments showed plant and zooxanthellae sterols in their tissues, while their deep-sea counterparts showed phytoplankton and zooplankton sterols. In contrast, echinoids, a class of echinoderms, the most complex phylum along with hemichordates and chordates (deuterostomes), did not show significant differences in their sterol profile, suggesting that cholesterol synthesis is present in deuterostomes other than chordates.
Assuntos
Artrópodes/metabolismo , Cnidários/metabolismo , Equinodermos/metabolismo , Moluscos/metabolismo , Poríferos/metabolismo , Esteróis/metabolismo , Animais , Oceano Atlântico , Dieta , Ecossistema , Cromatografia Gasosa-Espectrometria de Massas , Golfo do México , Especificidade da Espécie , Esteróis/isolamento & purificaçãoRESUMO
Malva parviflora is used as food in the gastronomy of some regions of Mexico and, also, in Mexican traditional medicine for inflammation-related conditions like rheumatoid arthritis. The objective of this work was to evaluate its antiarthritic activity in a mice model. In ICR, female mice were tested the dichloromethane extract (MpD) and fractions MpF4 (extracted with a dichoromethane:methanol system) and MpFphy (a precipitate by acetone:methanol) by using the mono-arthritis with kaolin/carrageenan model. During the treatment, joint inflammation was measured daily, and hyperalgesia was measured using the hot plate test. The treatments diminished both joint inflammation and pain. At the end of the evaluation, the left joint and spleen were extracted for determination of pro- and anti-inflammatory cytokines. The results showed that the MpD, MpF4, and MpFphy treatments modulated the concentration of these proteins. Specifically, MpFphy at 1.0 mg/kg increased IL-4 and IL-10 and decreased IL-17, IL-1ß, and TNF-α. GC-MS analysis showed that MpF4 contained a mixture of a total of nine compounds, three of them newly reported for the species. The studies confirmed the presence of five sterols in the MpFphy fraction, including stigmasterol and ß-sitosterol. These results confirm the anti-rheumatoid and anti-inflammatory activities of a fraction rich in sterols from Malva parviflora. Graphical abstract.
Assuntos
Anti-Inflamatórios/farmacologia , Antirreumáticos/farmacologia , Malva/química , Extratos Vegetais/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Antirreumáticos/isolamento & purificação , Artrite Experimental/tratamento farmacológico , Artrite Experimental/patologia , Artrite Reumatoide/tratamento farmacológico , Artrite Reumatoide/patologia , Carragenina , Citocinas/metabolismo , Feminino , Inflamação/tratamento farmacológico , Inflamação/patologia , Caulim , Camundongos , Camundongos Endogâmicos ICR , Esteróis/isolamento & purificação , Esteróis/farmacologiaRESUMO
Manilkara zapota (Sapotaceae), commonly known as Sapodilla, is widely known for its delicious fruit. Various parts of this plant are also used in folk medicine to treat a number of conditions including fever, pain, diarrhoea, dysentery, haemorrhage and ulcers. Scientific studies have demonstrated analgesic, anti-inflammatory, antioxidant, cytotoxic, antimicrobial, antidiarrheal, anti-hypercholesteremic, antihyperglycemic and hepatoprotective activities in several parts of the plant. Phytochemical studies have revealed the presence of phenolic compounds including protocatechuic acid quercitrin, myricitrin, catechin, gallic acid, vanillic acid, caffeic acid, syringic acid, coumaric acid, ferulic acid, etc. as main constituents of the plant. Several fatty acids, carotenoids, triterpenes, sterols, hydrocarbons and phenylethanoid compounds have also been isolated from M. zapota. The present review is a comprehensive description focused on pharmacological activities and phytochemical constituents of M. zapota.
Manilkara zapota (Sapotaceae), comuÌnmente conocida como Sapodilla, es ampliamente conocida por su delicioso fruto. Variadas partes de esta planta se usan en medicina popular para tratar una serie de afecciones, como fiebre, dolor, diarrea, disenteriÌa, hemorragia y uÌlceras. Estudios cientiÌficos han demostrado actividad analgeÌsica, antiinflamatoria, antioxidante, citotoÌxica, antimicrobiana, antidiarreica, antihipercolesteroleÌmica, antihipergluceÌmica y hepatoprotectora en diferentes partes de la planta. Los estudios fitoquiÌmicos han revelado la presencia de compuestos fenoÌlicos que incluyen aÌcido protocatechuÌico, quercitrina, miricitrina, catequina, aÌcido galico, aÌcido vaniÌlico, aÌcido cafeico, aÌcido siriÌnico, aÌcido cumaÌrico, aÌcido fuÌnico y aÌcido feruÌlico como componentes principales de la planta. Varios aÌcidos grasos, carotenoides, triterpenos, esteroles, hidrocarburos y compuestos feniletanoides tambieÌn han sido aislados de M. zapota. La presente revisioÌn es una descripcioÌn exhaustiva centrada en las actividades farmacoloÌgicas y los constituyentes fitoquiÌmicos de M. zapota.
Assuntos
Extratos Vegetais/farmacologia , Manilkara/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Saponinas/isolamento & purificação , Saponinas/farmacologia , Esteróis/isolamento & purificação , Esteróis/farmacologia , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Carotenoides/isolamento & purificação , Carotenoides/farmacologia , Sapotaceae/química , Compostos Fenólicos/análise , Medicina TradicionalRESUMO
Sterol profiles were obtained from cyanobacteria Phormidium autumnale, cultivated in a heterotrophic system using three distinct sources of carbon: glucose, sucrose, and agroindustrial slaughterhouse wastewater. A simultaneous saponification-extraction ultrasound-assisted method was performed to determine sterol and other non-saponified compounds in the dry biomasses. A total of 24 compounds were observed in the biomasses, including hope-22,29-en-3-one, squalene, and 22 other sterols. Using wastewater as a carbon source, the microalgae biomass produced a diversity of sterols such as stigmasterol (455.3⯵gâ¯g-1) and ß-sitosterol (279.0⯵gâ¯g-1). However, with glucose it is possible to produce ergosterol (1033.3⯵gâ¯g-1). Squalene was found in all the cultures, with 1440.4⯵gâ¯g-1, 225.4⯵gâ¯g-1, and 425.6⯵gâ¯g-1 for glucose, sucrose, and slaughterhouse wastewater biomasses, respectively. Several intermediate compounds from those sterols were found. These data provide the construction of the sterol metabolism according to the literature for P. autumnale heterotrophically cultured.
Assuntos
Biomassa , Cianobactérias/metabolismo , Lipidômica/métodos , Esteróis/análise , Esteróis/biossíntese , Carbono/metabolismo , Meios de Cultura/química , Cianobactérias/crescimento & desenvolvimento , Ergosterol/biossíntese , Redes e Vias Metabólicas , Microalgas/metabolismo , Phormidium , Sitosteroides/análise , Esqualeno/análise , Esteróis/isolamento & purificação , Estigmasterol/análise , Águas Residuárias/microbiologiaRESUMO
Luehea species are found in almost all Central and South American countries. The present work describes the phytochemical study, isolation, and structural characterisation of friedelin, ß-friedelinol, lupeol, pseudotaraxasterol, ß-sitosterol, betulinic acid, taraxasterol, (-)-epicatechin, ß-sitosterol-3-O-ß-d-glucopyranoside, and (+)-epicatechin-(4ßâ8)-epicatechin from stem barks of Luehea ochrophylla Mart. The structural identification of the isolated compounds was mainly performed by NMR analyses and comparison with the data from literature. These compounds were isolated for the first time in the genus Luehea, except ß-sitosterol glucopyranoside, (-)-epicatechin, and lupeol. Hexane extract (HE) and dichloromethane (DF) and ethyl acetate (AF) fractions exhibited antiparasitic activity against amastigote (intracellular) and trypomastigote culture forms of Trypanosoma cruzi. The ethanol extract (EE), DF, and ethanol fraction (EF) exhibited considerable antifungal activity against Candida albicans. Moreover, extracts and fractions exhibited significant percentage of capture free radicals of 2,2-diphenyl-picrylhydrazyl (DPPH) when compared to the standard of ascorbic acid.
Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Antiparasitários/farmacologia , Malvaceae/química , Animais , Anti-Infecciosos/química , Antioxidantes/química , Antiparasitários/química , Chlorocebus aethiops , Avaliação Pré-Clínica de Medicamentos/métodos , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Triterpenos Pentacíclicos/isolamento & purificação , Triterpenos Pentacíclicos/farmacologia , Casca de Planta/química , Extratos Vegetais/química , Sitosteroides/isolamento & purificação , Sitosteroides/farmacologia , Esteróis/isolamento & purificação , Esteróis/farmacologia , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Células Vero , Ácido BetulínicoRESUMO
Two ergostanes, 5α,8α-epidioxy-22E-ergosta-6,22-dien-3ß-ol (1) and 5α-ergost-7,22-dien-3ß-ol (2), and a lanostane, 3ß-hydroxylanostan-8,24-diene-21-oic acid (trametenolic acid) (3), were isolated from an n-hexane extract prepared from the fruiting body of Trametes versicolor (Bres. Rivarden). The activity of the isolated sterols was evaluated against promastigotes and amastigotes of Leishmania amazonensis Lainson and Shaw, 1972. The lanostane, compound (3), showed the best inhibitory response (IC50 promastigotes 2.9 ± 0.1 µM and IC50 amastigotes 1.6 ± 0.1 µM). This effect was 25-fold higher compared with its cytotoxic effect on peritoneal macrophages from BALB/c mice. Therefore, trametenolic acid could be regarded as a promising lead for the synthesis of compounds with antileishmanial activity.
Assuntos
Esteróis/farmacologia , Trametes/química , Tripanossomicidas/farmacologia , Animais , Sobrevivência Celular/efeitos dos fármacos , Carpóforos/química , Leishmania/efeitos dos fármacos , Macrófagos Peritoneais/efeitos dos fármacos , Camundongos , Estrutura Molecular , Esteróis/química , Esteróis/isolamento & purificação , Tripanossomicidas/química , Tripanossomicidas/isolamento & purificaçãoRESUMO
Various species of the genus Ganoderma have been used for centuries according to oriental tradition as a source of medicines and nutrients. A chemical study of the fruiting bodies and mycelial culture of G. oerstedii was carried out with the idea of isolating and characterizing active natural components present to make use of their potential pharmaceutical application in Mexico. The fruiting bodies and mycelial culture of G. oesrtedii were lyophylized and extracted one after the other with hexane, chloroform, and methanol. Following this process, each substance was extracted separately by using column chromatography. From fruiting bodies eight metabolites, five sterols (ergosta-7,22-dien-3ß-ol, ergosterol peroxide, ergosterol, cerevisterol, and ergosta-7,22-dien-3-one) as well as three terpene compounds (ganodermanondiol, ganoderic acid Sz, and ganoderitriol M) were obtained from fruiting bodies. From the mycelial culture three metabolites, two sterols (ergosterol and cerevisterol), and a new terpene compound (ganoderic acetate from the acid) were obtained. These structures were established based on a spectroscopic analysis mainly using nuclear magnetic resonance and a comparison with data already established.
Assuntos
Produtos Biológicos/isolamento & purificação , Carpóforos/química , Ganoderma/química , Micélio/química , Produtos Biológicos/química , Espectroscopia de Ressonância Magnética , México , Modelos Moleculares , Estrutura Molecular , Esteróis/química , Esteróis/isolamento & purificação , Terpenos/química , Terpenos/isolamento & purificaçãoRESUMO
The use of biofilms for adsorption of sterols was investigated for the first time to evaluate sewage contamination in the Barigüi River, Curitiba (Brazil). The characteristics of a biofilm that favor its use in monitoring include the relatively rapid development of biofilms and their capacity to sorb hydrophobic compounds. Some fecal sterols considered to be biomarkers for human and animal feces have relatively high octanol-water partitioning coefficients (log KOW); thus, sterols were expected to be readily sorbed in the biofilms. The biofilms were developed on glass plates (0.48 m(2)) previously coated with a fine layer of stearic acid and supported by a PVC tube that was submersed in the river 20 cm above the river bottom. After a certain period of incubation time, the biofilm growth was scraped from the plates and analyzed for the following fecal steroids: coprostanol (5ß-cholestan-3ß-ol), epicoprostanol (5ß-cholestan-3α-ol), cholesterol (5,6-cholesten-3ß-ol), cholestanol (5α-cholestan-3ß-ol), stigmastanol (24ß-ethyl-5α-cholestan-3ß-ol) and coprostanone (5ß-cholestan-3-one). Six samples were collected between March 2012 and June 2012. All analyzed compounds were detected, and in general, cholesterol was present in high amounts (23 160-41.9 ng g(-1) dry biofilm). Variation among campaigns was observed in the distribution of sterols, with cholestanol showing the least variation among the samples. Sterol ratios that are commonly used for evaluating sewage contamination were calculated; these ratios indicated some periods of potential sewage influence. However, these sterol ratios are intended to be applied primarily for sediments and not for biological compartments; thus, the results must be carefully interpreted. Biofilms developed under natural conditions can be a tool for monitoring some important sterols that are used as biomarkers of fecal pollution.
Assuntos
Monitoramento Ambiental/instrumentação , Poluentes Ambientais/isolamento & purificação , Fezes/química , Esgotos/análise , Esteróis/isolamento & purificação , Adsorção , Animais , Biofilmes , Brasil , Desenho de Equipamento , HumanosRESUMO
The need to develop novel antiviral agents encouraged us to assess the antiviral activity of synthetic sterol analogues with a diamide side chains. Cytotoxicity and antiviral activity of a family of azasterol previously synthesized was evaluated against herpes simplex virus 1 (HSV-1) (KOS and B2006) and vesicular stomatitis virus (VSV). This family of compounds was extended by the synthesis of novel analogs using an Ugi multicomponent reaction and their ability to inhibit viral multiplication was also evaluated. The results show that some of the compounds tested exert an antiviral activity. Besides, the effect of the azasterols on the intracellular localization of viral glycoproteins was examined. Strikingly, alteration on the glycoprotein D (gD) of HSV-1 fluorescence pattern was observed with both the antiherpetic compounds and the inactive azasterols.
Assuntos
Antivirais/química , Diamida/química , Herpesvirus Humano 1/efeitos dos fármacos , Esteróis/química , Proteínas do Envelope Viral/metabolismo , Antivirais/isolamento & purificação , Antivirais/farmacologia , Herpesvirus Humano 1/metabolismo , Humanos , Espaço Intracelular/metabolismo , Esteróis/isolamento & purificação , Esteróis/farmacologia , Replicação Viral/efeitos dos fármacosRESUMO
OBJECTIVES: An aqueous extract and fraction from the marine sponge Petromica citrina have antibacterial activity. We performed a chemical and biological characterization of the antibiotic substance from P. citrina and investigated its mode of action on Staphylococcus aureus cells. METHODS: The inhibitory activity of the aqueous extract of P. citrina was determined against 14 bacteria belonging to type strains and clinical antibiotic-resistant strains. The aqueous extract was fractionated under bioassay guidance and the bioactive substance was identified by its (1)H-NMR, (13)C-NMR and mass spectra. The MIC and the MBC of this substance were determined. This substance was also subjected to cytotoxic bioassays. The mode of action on S. aureus cells was investigated by light and transmission electron microscopy analysis. RESULTS: P. citrina showed a large spectrum of activity against type strains and resistant-bacteria such as S. aureus, Staphylococcus epidermidis, Enterococcus faecalis, Mycobacterium fortuitum and Neisseria gonorrhoeae. The aqueous extract was fractionated and halistanol trisulphate (24ε,25-dimethylcholestane-2ß,3α,6α-triol trisodium sulphate) was isolated for the first time from P. citrina. Halistanol trisulphate had a bactericidal effect on exponentially growing S. aureus cells at the MIC (512 mg/L). Cytotoxicity biossays showed moderate toxicity against cancer cell line L929 (fibrosarcoma). This substance apparently acts by damaging the cell membrane, with subsequent cell lysis. CONCLUSIONS: Halistanol trisulphate is a broad-spectrum antibiotic isolated from P. citrina with a mode of action involving disruption of the cytoplasmic membrane. It is a new candidate for research on antibacterial substances.
Assuntos
Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Poríferos/química , Esteróis/isolamento & purificação , Esteróis/farmacologia , Animais , Antibacterianos/química , Bactérias/citologia , Extratos Celulares/química , Extratos Celulares/isolamento & purificação , Extratos Celulares/farmacologia , Linhagem Celular Tumoral/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Fracionamento Químico , Espectroscopia de Ressonância Magnética , Camundongos , Testes de Sensibilidade Microbiana , MicroscopiaRESUMO
A whole-cell-based assay using Saccharomyces cerevisiae strains that overexpress Candida albicans CDR1 and MDR1 efflux pumps has been employed to screen natural product extracts for reversal of fluconazole resistance. The tropical green alga Penicillus capitatus was selected for bioassay-guided isolation, leading to the identification of capisterones A and B (1 and 2), which were recently isolated from this alga and shown to possess antifungal activity against the marine pathogen Lindra thallasiae. Current work has assigned their absolute configurations using electronic circular dichroism and determined their preferred conformations in solution based on detailed NOE analysis. Compounds 1 and 2 significantly enhanced fluconazole activity in S. cerevisiae, but did not show inherent antifungal activity when tested against several opportunistic pathogens or cytotoxicity to several human cancer and noncancerous cell lines (up to 35 microM). These compounds may have a potential for combination therapy of fungal infections caused by clinically relevant azole-resistant strains.
Assuntos
Antifúngicos , Clorófitas/química , Fluconazol/farmacologia , Saccharomyces cerevisiae/metabolismo , Esteróis , Triterpenos , Membro 1 da Subfamília B de Cassetes de Ligação de ATP/metabolismo , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Ascomicetos/efeitos dos fármacos , Bahamas , Candida albicans/química , Candida albicans/metabolismo , Farmacorresistência Fúngica , Ensaios de Seleção de Medicamentos Antitumorais , Proteínas Fúngicas/metabolismo , Humanos , Biologia Marinha , Proteínas de Membrana Transportadoras/metabolismo , Estrutura Molecular , Esteróis/química , Esteróis/isolamento & purificação , Esteróis/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologiaRESUMO
Applanoxidic acids and sterols, isolated from Ganoderma spp., were acetylated and/or methylated. The antibacterial activity against Escherichia coli and Staphylococcus aureus and the antifungal activity against Candida albicans and Trichophyton mentagrophytes of the derivatives were investigated by a microdilution method, and compared with those of the natural products. Both natural and modified compounds exhibited comparable antibacterial and antifungal activities in a range of 1.0 to > 2.0 mg/ml minimal inhibitory concentration.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Ganoderma/química , Esteróis/isolamento & purificação , Triterpenos/farmacologia , Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Arthrodermataceae/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Ganoderma/isolamento & purificação , Testes de Sensibilidade Microbiana , Staphylococcus aureus/efeitos dos fármacos , Esteróis/farmacologia , Trichophyton/efeitos dos fármacos , Triterpenos/isolamento & purificaçãoRESUMO
Analysis of the sterol fraction obtained from the Colombian Caribbean sponge Topsentia ophiraphidites revealed that this sponge is a rich source of C30 and C31 sterols. Among them, a new C31 sterol, named ophirasterol, was isolated, and its structure was established as (22E,24R)-24-(1-buten-2-yl)cholesta-5,22-dien-3beta-ol (1) by spectral means and comparison with synthetic C-24 epimers with known configuration. Other isolated C30 and C31 sterols were the known 24-ethyl-24-methyl-22-dehydrocholesterol (2), 24-isopropyl-22-dehydrocholesterol (3), 24-isopropylcholesterol (4), 24-ethyl-24-methylcholesterol (5), 24-isopropenyl-25-methyl-22-dehydrocholesterol (6) and 24-isopropenyl-25-methylcholesterol (7), and 24-isopropenyl-22-dehydrocholesterol (8).
Assuntos
Poríferos/química , Esteróis/química , Animais , Colesterol/análogos & derivados , Colesterol/química , Colesterol/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Estereoisomerismo , Esteróis/isolamento & purificaçãoAssuntos
Antifúngicos/química , Poríferos/química , Esteróis/química , Ésteres do Ácido Sulfúrico/química , Animais , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Bahamas , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Poríferos/metabolismo , Saccharomyces cerevisiae/metabolismo , Espectrometria de Massas por Ionização por Electrospray , Esteróis/isolamento & purificação , Esteróis/farmacologia , Ésteres do Ácido Sulfúrico/isolamento & purificação , Ésteres do Ácido Sulfúrico/farmacologiaRESUMO
Three new sterols, 5alpha,6alpha-epoxy-24R-ethylcholest-8(14)-en-3beta,7alpha-diol (1), 5alpha,6alpha-epoxy-24R-ethylcholest-8-en-3beta,7alpha-diol (2), and 3beta-hydroxy-24R-ethylcholesta-5,8-dien-7-one (3), have been isolated from the marine sponge Polymastia tenax, collected in the Colombian Caribbean, and their structures established on the basis of extensive NMR and MS studies. Compounds 1 and 2 showed antiproliferative activity toward A-549, HT-29, H-116, MS-1, and PC-3 tumor cells in the range 0.5-10 microg/mL.
Assuntos
Poríferos/química , Esteróis/isolamento & purificação , Animais , Região do Caribe , Cromatografia Líquida de Alta Pressão , Colômbia , Neoplasias do Colo , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Neoplasias Pulmonares , Masculino , Espectrometria de Massas , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Neoplasias da Próstata , Estereoisomerismo , Esteróis/química , Esteróis/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacos , Células Tumorais Cultivadas/enzimologia , Células Tumorais Cultivadas/metabolismoRESUMO
In addition to 3'-methoxyluteolin and mixtures of sterols and triterpenes, the leaves of Syphocampylus Verticellatus yielded two piperidine alkaloid hydrochlorides, one of them has a novel structure. The alkaloids exhibit antinociceptive activity.
Assuntos
Alcaloides/química , Analgésicos/química , Dor/prevenção & controle , Piperidinas/química , Extratos Vegetais/química , Folhas de Planta/química , Plantas Medicinais/química , Alcaloides/isolamento & purificação , Analgésicos/isolamento & purificação , Animais , Brasil , Formaldeído , Masculino , Medicina Tradicional , Camundongos , Conformação Molecular , Dor/induzido quimicamente , Piperidinas/isolamento & purificação , Esteróis/química , Esteróis/isolamento & purificação , Triterpenos/química , Triterpenos/isolamento & purificaçãoRESUMO
The triterpenes ursolic acid (1), 27-p-Z-coumaroyloxyursolic acid (2), 27-p-E-coumaroyloxyursolic acid, alpha-amyrine-3-palmitate and lupeol-3-palmitate were isolated through a bioactivity-guided fractionation from the acetonic extract of the aerial parts of Viburnum jucundum Morton in addition to amentoflavone, an epimeric mixture at C-2 of 2,3-dihydroamentoflavone, beta-sitosterol and beta-sitosteryl glucopyranoside. Ursolic acid (1) was the only constituent that exhibited cytotoxic activity toward three human cancer cell lines in culture. This is the first phytochemical and cytotoxic analysis performed to this plant species.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Gastroenteropatias/tratamento farmacológico , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , Viburnum/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Humanos , México , Extratos Vegetais/química , Plantas Medicinais , Esteróis/química , Esteróis/isolamento & purificação , Esteróis/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação , Células Tumorais Cultivadas , Ácido UrsólicoRESUMO
Two new steroidal glycosides, 3beta-O-(3'-O-acetyl-beta-D-arabinopyranosyl)-25xi-choles tan e-3beta, 5alpha,6beta,26-tetrol-26-acetate (riisein A, 2) and 3beta-O-(4'-O-acetyl-beta-D-arabinopyranosyl)-25xi-choles tan e-3beta, 5alpha,6beta,26-tetrol-26-acetate (riisein B, 3), were isolated from extracts of the Brazilian telestacean octocoral Carijoa (Telesto) riisei collected near Rio de Janeiro. The new glycosides co-occur with the polyhydroxy sterol, 25xi-cholestane-3beta,5alpha,6beta, 26-tetrol-26-acetate (1), an inseparable diastereomeric mixture previously reported from Telesto riisei collected in Micronesia. The structures of the new glycosides were assigned by spectroscopic methods and by comparison with spectral data for sterol 1. Riiseins A and B showed in vitro cytotoxicity toward HCT-116 human colon adenocarcinoma with IC(50) values of 2.0 microg/mL.
Assuntos
Antineoplásicos/isolamento & purificação , Cnidários/química , Glicosídeos/isolamento & purificação , Esteróis/isolamento & purificação , Animais , Antineoplásicos/química , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Esteróis/químicaRESUMO
The ethanolic extract from the stem of Brosimum potabile afforded (-)-centrolobin (1), isolated for the first time in this genus. The identification of this compound included COSY and NOESY two-dimensional NMR data.
Assuntos
Plantas Medicinais , Piranos/isolamento & purificação , Rosales , Esteróis/isolamento & purificação , Humanos , Espectroscopia de Ressonância Magnética , Caules de Planta , Piranos/química , Esteróis/químicaRESUMO
This study was conducted in order to determine the chemical composition and the possible antinociceptive effects in mice of some species of Phyllanthus in vitro. The methanolic extracts obtained from callus cultures of P. fraternus, P. stipulatus and P. caroliniensis caused significant inhibition in to the late phase of the formalin test, whereas the extract from P. urinaria inhibited both neurogenic and inflammatory phases of the test. Conventional chromatographic methods (TLC, GC) permitted the detection of some steroids or triterpenes, including beta-sitosterol, glochidonol and glochidone, which seem be responsible for the antinociceptive effects of the callus extracts studied.