RESUMO
Leishmaniasis belongs to a complex of zoonotic disease caused by protozoa of the genus Leishmania and is considered a major public health problem. Several essential oil chemical components have inhibitory effect against protozoa, including Leishmania donovani. Thus, the aim of this study was to evaluate for the first time the anti-Leishmania activity of two p-menthane monoterpene isomers (EPER-1: perillaldehyde 1,2-epoxide and EPER-2: perillaldehyde 8,9-epoxide) against L. donovani promastigotes as well as evaluating cytotoxic effect on mononuclear peripheral blood cells. Results of anti-Leishmania assay revealed that EPER-2 (IC50 = 3.8 µg.mL-1) was 16-fold more potent than its isomer EPER-1 (IC50 = 64.6 µg.mL-1). In contrast to PBMC cells, EPER-2 was not cytotoxic (IC50 > 400 µg.mL-1) when compared to positive control. These data suggest that the disposition of epoxide group into the p-menthane skeleton affects the anti-Leishmania activity, being that the presence of the exocyclic epoxide group considerably increased potency. Thus, it was possible to observe that the location of the epoxide group into the p-menthane skeleton resulted in different potencies.
Assuntos
Antiprotozoários/química , Leucócitos Mononucleares/efeitos dos fármacos , Monoterpenos/farmacologia , Óleos Voláteis , Animais , Antiprotozoários/isolamento & purificação , Antiprotozoários/farmacologia , Compostos de Epóxi/química , Compostos de Epóxi/isolamento & purificação , Compostos de Epóxi/farmacologia , Humanos , Isomerismo , Leishmania donovani/efeitos dos fármacos , Leishmaniose/tratamento farmacológico , Monoterpenos/química , Monoterpenos/isolamento & purificação , Óleos Voláteis/farmacologia , Relação Estrutura-AtividadeRESUMO
A fungal strain of Aspergillus niger was recovered from sediments collected in the Northeast coast of Brazil (Pecém's offshore port terminal). Cultivation in different growth media yielded a new ester furan derivative, 1, along with malformin A1, malformin C, cyclo (trans-4-hydroxy-L-Pro-L-Leu), cyclo (trans-4-hydroxy-L-Pro-L-Phe), cyclo (L-Pro-L-Leu), cyclo (L-Pro-L-Phe), pseurotin D, pseurotin A, chlovalicin, cyclo (L-Pro-L-Tyr) and cyclo (L-Pro-L-Val). Compound 1 was cytotoxic against HCT-116 cell line, showing IC50 = 2.9 µg/mL (CI 95% from 1.8 to 4.7 µg/mL).
Assuntos
Antineoplásicos/farmacologia , Aspergillus niger/química , Antineoplásicos/química , Brasil , Cicloexanonas/isolamento & purificação , Cicloexanonas/farmacologia , Dipeptídeos/isolamento & purificação , Dipeptídeos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Compostos de Epóxi/isolamento & purificação , Compostos de Epóxi/farmacologia , Furanos/química , Sedimentos Geológicos/microbiologia , Células HCT116 , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Peptídeos Cíclicos/química , Peptídeos Cíclicos/isolamento & purificação , Peptídeos Cíclicos/farmacologia , Pirrolidinonas/isolamento & purificação , Pirrolidinonas/farmacologiaRESUMO
O objetivo deste trabalho é analisar o discurso do excesso sexual produzido pelo pensamento social brasileiro das décadas de 1920 e 1930 na sua interlocução com o discurso médico da época. De inspiração foucaultiana, o texto inscreve-se no campo da história dos saberes e está subsidiado por documentos sociológicos e médicos do período de referência. No quadro da recodificação vintecentista sobre o imaginário da brasilidade, o tema do excesso sexual foi revisitado pelo pensamento sociológico local, forjando-o ora como um perturbador do projeto civilizatório nacional, ora como um traço que deveria ser positivado por ter sido a condição de possibilidade da hibridização cultural de suas matrizes identitárias.
The objective of this article is to analyze the discourse of sexual excess produced by Brazilian social thinking in the 1920s and 1930s and its dialog with the medical discourse at the time. Inspired by Foucault, it is within the field of the history of knowledge and is supported by sociology and medical documents from the period in question.Within the framework of the twentieth century re-codification of the imagery of Brazilianness, the topic of sexual excess was revisited by local thinkers in the field of sociology and seen either as disturbing the national civilizing project, or as a trait that should be seen in a positive light because it permitted the cultural hybridization of its sources of identity.
Assuntos
Animais , Bovinos , Adenina/metabolismo , Adutos de DNA/metabolismo , Compostos de Epóxi/metabolismo , Guanina/metabolismo , Mutagênicos/metabolismo , Adutos de DNA/química , Adutos de DNA/isolamento & purificação , Compostos de Epóxi/química , Compostos de Epóxi/isolamento & purificação , Guanosina/metabolismo , Mutagênicos/química , Mutagênicos/isolamento & purificaçãoRESUMO
Papulaspora immersa H.â H. Hotson was isolated from roots and leaves of Smallanthus sonchifolius (Poepp. and Endl.) H. Rob. (Asteraceae), traditionally known as Yacon. The fungus was cultured in rice, and, from the AcOEt fraction, 14 compounds were isolated. Among them, (22E,24R)-8,14-epoxyergosta-4,22-diene-3,6-dione (4), 2,3-epoxy-1,2,3,4-tetrahydronaphthalene-c-1,c-4,8-triol (10), and the chromone papulasporin (13) were new secondary metabolites. The spectral data of the known natural products were compared with the literature data, and their structures were established as the (24R)-stigmast-4-en-3-one (1), 24-methylenecycloartan-3ß-ol (2), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (3), (-)-(3R,4R)-4-hydroxymellein (5), (-)-(3R)-5-hydroxymellein (6), 6,8-dihydroxy-3-methylisocoumarin (7), (-)-(4S)-4,8-dihydroxy-α-tetralone (8), naphthalene-1,8-diol (9), 6,7,8-trihydroxy-3-methylisocoumarin (11), 7-hydroxy-2,5-dimethylchromone (12), and tyrosol (14). Compound 4 showed the highest cytotoxic activity against the human tumor cell lines MDA-MB435 (melanoma), HCT-8 (colon), SF295 (glioblastoma), and HL-60 (promyelocytic leukemia), with IC50 values of 3.3, 14.7, 5.0 and 1.6â µM, respectively. Strong synergistic effects were also observed with compound 5 and some of the isolated steroidal compounds.
Assuntos
Asteraceae/química , Cromonas/química , Compostos de Epóxi/química , Ergosterol/análogos & derivados , Naftóis/química , Linhagem Celular Tumoral , Cromonas/isolamento & purificação , Cromonas/toxicidade , Ensaios de Seleção de Medicamentos Antitumorais , Compostos de Epóxi/isolamento & purificação , Compostos de Epóxi/toxicidade , Ergosterol/química , Ergosterol/isolamento & purificação , Ergosterol/toxicidade , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Naftóis/isolamento & purificação , Naftóis/toxicidade , Folhas de Planta/química , Raízes de Plantas/químicaRESUMO
A pharmacological screening of the ethanol extract and fractions of two Peruvian medicinal plants, Plagiochila disticha and Ambrosia peruviana, led to the isolation and characterization of three ENT-2,3-secoaromadendrane-type sesquiterpenoids, named plagiochiline A ( 1), I ( 2), and R ( 3), as well as of two pseudoguaianolids, damsin ( 4) and confertin ( 5), which exhibited significant cytotoxic activity against a panel of human tumor cell lines. Compounds 1, 4, and 5 were also investigated for their in vitro antileishmanial, trypanocidal, and antituberculosis activity against Leishmania amazonensis axenic amastigotes and Trypanosoma cruzi trypomastigotes, as well as against MDR and sensitive strains of Mycobacterium tuberculosis, respectively.
Assuntos
Anti-Infecciosos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Asteraceae/química , Azulenos/isolamento & purificação , Compostos de Epóxi/isolamento & purificação , Piranos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos , Humanos , Peru , Plantas Medicinais/químicaRESUMO
Chemical investigation of the mycelium of Edenia gomezpompae, a newly discovered endophytic fungus isolated from the leaves of Callicarpa acuminata (Verbenaceae) collected from the ecological reserve El Eden, Quintana Roo, Mexico, resulted in the isolation of four naphthoquinone spiroketals, including three new compounds and palmarumycin CP2 (4). We elucidated the structures of the metabolites by extensive NMR spectroscopy studies, including DEPT, COSY, NOESY, HSQC, HMBC, and chiroptical methods. The trivial names proposed for these compounds are preussomerin EG1 (1), preussomerin EG2 (2) and preussomerin EG3 (3). In addition, the X-ray data for 4 were obtained. The bioactivity of the mycelial organic extracts and the pure compounds was tested against three endophytic fungi (Colletotrichum sp., Phomopsis sp., and Guignardia manguifera) isolated from the same plant species (C. acuminata, Verbenaceae) and against four economically important phytopathogenic microorganisms (two fungoid oomycetes, Phythophtora capsici and Phythophtora parasitica, and the fungi Fusarium oxysporum and Alternaria solani). Spiroketals 1-3 displayed significant growth inhibition against all the phytopathogens. IC50 values for the four phytopathogens were from 20 to 170 microg/ml. Palmarumycin CP2 (4) was not bioactive against any of the fungi tested. Compound 1 showed the strongest bioactivity. The acetylated derivatives of preussomerin EG1 (1), 1a and 1b, were obtained and their biological activity was tested on endophytes and phytopathogens. Preussomerin EG1 1, 1a and 1b exhibited significant bioactivity against all microorganisms tested with the exception of Alternaria solani. This is the first report of allelochemicals with antifungal activity from the newly discovered endophytic fungus E. gomezpompae.
Assuntos
Antifúngicos/farmacologia , Ascomicetos/química , Compostos de Epóxi/farmacologia , Fungos/efeitos dos fármacos , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Naftalenos/farmacologia , Compostos de Espiro/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/metabolismo , Ascomicetos/metabolismo , Bioensaio , Cristalografia por Raios X , Meios de Cultivo Condicionados/química , Relação Dose-Resposta a Droga , Compostos de Epóxi/isolamento & purificação , Compostos de Epóxi/metabolismo , Fungos/crescimento & desenvolvimento , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/metabolismo , Espectroscopia de Ressonância Magnética/métodos , Modelos Moleculares , Conformação Molecular , Naftalenos/isolamento & purificação , Naftalenos/metabolismo , Doenças das Plantas/microbiologia , Folhas de Planta/microbiologia , Compostos de Espiro/isolamento & purificação , Compostos de Espiro/metabolismo , Estereoisomerismo , Verbenaceae/microbiologiaRESUMO
In addition to the known cilistol A, two new withanolides have been isolated from leaves and stem of Solanum sisymbiifolium, and assigned the structures 1-oxo-5,6; 22,26; 24,25-triepoxy-17,26-dihydroxyergost-2-ene and 1-oxo-22,26; 24,25-diepoxy-5,6,17,26-tetrahydroxy ergost-2-ene, namely cilistepoxide and cilistadiol.
Assuntos
Compostos de Epóxi/isolamento & purificação , Ergosterol/análogos & derivados , Extratos Vegetais/química , Solanum/química , Brasil , Compostos de Epóxi/química , Ergosterol/química , Ergosterol/isolamento & purificação , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Caules de Planta/química , Espectrometria de Massas por Ionização por Electrospray , Espectroscopia de Infravermelho com Transformada de FourierRESUMO
This work evaluates the feasibility of reacting tannins isolated from Pinus radiata D. Don bark with epoxide resins of the diglycidyl and polyglycidyl ether type. To this end, gel times of aqueous tannin dispersions (40% w/w) with every one of nine selected resins (5% w/w), at previously established pH values (initial equal to 3.3, 4, 7 and 10), have been determined. Products of these reactions were analyzed by FT-IR spectroscopy, and the results were compared with those obtained from tannin-p-formaldehyde and (+)-catechin-p-formaldehyde systems, at the same pH values. Their mechanical properties were evaluated, by dynamic mechanical analysis, at two pH values (3.3 and 10). In general, it was concluded that tannin-epoxide resin systems behave similarly to tannin-paraformaldehyde systems, especially at basic pH values.
Assuntos
Compostos de Epóxi/metabolismo , Pinus/química , Casca de Planta/química , Resinas Vegetais/metabolismo , Taninos/metabolismo , Catequina/metabolismo , Compostos de Epóxi/química , Compostos de Epóxi/isolamento & purificação , Formaldeído/metabolismo , Concentração de Íons de Hidrogênio , Extratos Vegetais/química , Resinas Vegetais/química , Resinas Vegetais/isolamento & purificação , Espectroscopia de Infravermelho com Transformada de Fourier , Taninos/química , Taninos/isolamento & purificação , Temperatura , Fatores de TempoRESUMO
A method to determine the absolute configuration of 2,3-epoxy-2-methylbutanoate ester residues in natural products is presented, based on (i) the reduction of the ester function to yield a 2-methyl-1,2-butanediol, (ii) esterification of the obtained primary alcohol with either (R)-(+)- or (S)-(-)-Mosher's acid to afford the corresponding Mosher's ester, and (iii) 1H-NMR spectral comparison of the final product with that of the Mosher's esters prepared from 2-methyl-1,2-butanediols of known stereochemistry.
Assuntos
Fatores Biológicos/química , Butileno Glicóis/química , Butiratos/química , Compostos de Epóxi/química , Terpenos/química , Fatores Biológicos/metabolismo , Butileno Glicóis/isolamento & purificação , Butiratos/isolamento & purificação , Compostos de Epóxi/isolamento & purificação , Espectroscopia de Ressonância Magnética/métodos , Conformação Molecular , Fenilacetatos/química , Espectrofotometria Infravermelho , Terpenos/isolamento & purificaçãoRESUMO
The chemical composition of the essential oils of Calea clematidea Baker obtained by hydrodistillation of the leaves and flowers was analysed by GC and GC/MS and the oils were assayed for their antifungal activities. The essential oil of the leaves showed a high content of a new natural epoxy terpenoid, named clemateol (ca. 70 %), with minor amounts of o-vanillin (6.5 %), spathulenol (4.2 %), alpha-terpinene (4.0 %), germacrene B (2.9 %), yomogi alcohol (1.8 %), ( E)-caryophylene (1.7 %), m-cymenene (1.6 %), and alpha-gurjunene (1.5 %), while the essential oil of the flowers was characterized by a higher content of thymol methyl ether (ca. 80 %), with minor amounts of clemateol (4.8 %) and o-cymene (4.7 %). The antimicrobial activity of the oils was also evaluated against dermatophytes for their possible use in pharmaceutical preparations for topical applications. The oil of the leaves (MIC > 3.57 mg/ml), clemateol (MIC > 1.52 mg/ml), and the alcohol 2 (MIC > 2.82 mg/ml) showed a moderate antifungal activity against Trichophyton tonsurans, Trichophyton rubrum, Trichophyton menthagrophytes var. i nterdigitale, Epidermophyton floccosum, Microsporum gypseum, Microsporum canis and Microsporum nanum.
Assuntos
Antifúngicos/farmacologia , Asteraceae , Compostos de Epóxi/farmacologia , Fungos Mitospóricos/efeitos dos fármacos , Óleos Voláteis/farmacologia , Terpenos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Epidermophyton/efeitos dos fármacos , Compostos de Epóxi/química , Compostos de Epóxi/isolamento & purificação , Flores/química , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Microsporum/efeitos dos fármacos , Estrutura Molecular , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/química , Terpenos/química , Terpenos/isolamento & purificação , Trichophyton/efeitos dos fármacosRESUMO
Three cytotoxic withanolides, two with new structures, were isolated from the leaves of Acnistus arborescens and their structures determined by a combination of 1D and 2D NMR, mass spectral, and molecular modeling studies. Dereplication analysis of the ethyl ether extract was useful for evaluating the components showing significant cytotoxic activity.
Assuntos
Antineoplásicos/química , Compostos de Epóxi/química , Lactonas/química , Fitosteróis/química , Solanaceae/química , Células Tumorais Cultivadas/efeitos dos fármacos , Animais , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Indução Enzimática/efeitos dos fármacos , Compostos de Epóxi/isolamento & purificação , Compostos de Epóxi/farmacologia , Humanos , Lactonas/isolamento & purificação , Lactonas/farmacologia , Espectroscopia de Ressonância Magnética , Camundongos , NAD(P)H Desidrogenase (Quinona)/biossíntese , NAD(P)H Desidrogenase (Quinona)/efeitos dos fármacos , Fitosteróis/isolamento & purificação , Fitosteróis/farmacologiaRESUMO
Biological effects on Tribolium castaneum larvae were evaluated for three withanolides isolated from Salpichroa origanifolia (Solanaceae), (20S,22R,24S,25S,26R)-5alpha,6alpha:22,26:24,25-triepoxy-26-hydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide A, 1), (20S,22R,24S,25S,26R)-22,26:24,25-diepoxy-5alpha,6beta,26-trihydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide C, 2), and (20S,22R,24S,25S,26R)-5alpha,6alpha:22,26:24,25-triepoxy-15,26-dihydroxy-17(13-->18)-abeo-ergosta-2,13,15,17-tetraen-1-one (salpichrolide G, 3), and for several chemically modified analogues. The compounds were incorporated into the larval diet at concentrations of 500 and 2000 ppm. Salpichrolide C (2) produced a significant delay in the development of neonate larvae to adults at the highest concentration (2000 ppm); development delays and lethal effects were produced by salpichrolides A (1) and G (3) at both concentrations assayed. The size of surviving adults was used as a criterion for assessing feedant deterrent effects; the results suggest that these compounds act as feeding inhibitors. Influence of chemical modifications in development delay was analyzed.