RESUMO
Investigation of the contents of the scent glands of the heliconiine butterfly Heliconius erato phyllis via gas chromatography/electroantennography revealed an unprecedented active compound. The males transfer this compound to females during mating. The structure of (2R,6E,10R)-2,6-dimethyl-6-undecen-10-olide, a derivative of geranylacetone, was proposed on the basis of infrared and mass spectrometry spectra and microderivatization and confirmed by racemic and stereoselective syntheses. Bioassays with the synthetic macrolide showed the repellency of this compound, termed phyllisolide, when applied to scent glands of females, identifying it as an anti-aphrodisiac pheromone.
Assuntos
Borboletas , Macrolídeos , Feromônios , Glândulas Odoríferas , Animais , Afrodisíacos/química , Borboletas/química , Feminino , Macrolídeos/química , Masculino , Feromônios/química , Glândulas Odoríferas/químicaRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Piper auritum Kunth is employed as an aphrodisiac in the traditional medicine, but corroborative evidence for such effect is scarce. AIM OF THE STUDY: The pro-sexual effect of an aqueous extract of P. auritum and its possible mechanisms were analyzed in two paradigms of male sexual function. MATERIAL AND METHODS: Effects of an aqueous extract of P. auritum (PA, single administration) were investigated in the fictive ejaculation, and copulatory behavior paradigms in sexually sluggish male rats. WAY 100635 (antagonist of 5-HT1A receptors), atosiban (antagonist of oxytocinergic receptors), L-NAME (inhibitor of the nitric oxide synthase) and baclofen (antagonist of GABAB receptors) were used as pre-treatments in order to investigate the role of different neurotransmitter systems in PA actions. Chemical profile of PA was determined by Gases Chromatography and Ultra Performance Chromatography-Electrospray Ionization-Masses Spectrometry (UPLC-ESI-MS). RESULTS: In males with retarded ejaculation, PA stimulated ejaculatory behavior and recovered electromyographic activity of pelvic musculature participating in seminal emission and ejaculation. All pre-treatments blocked stimulating effects of PA on the fictive ejaculation; additionally WAY 100635 interfered with PA actions on ejaculatory behavior. Safrol, apigenin dimethylether, myristicin, vaccihein A, sakuranin and sakuranetin flavonoids, were main constituents of PA, with possible participation in its pro-sexual effects. CONCLUSIONS: Pro-sexual effects of P. auritum elicited at level of ejaculation were mediated by several neurotransmitter systems, among which serotonin and its 5-HT1A receptors play an important role. Present findings support P. auritum reputation as an aphrodisiac, with potential use in delayed ejaculation disorder.
Assuntos
Afrodisíacos/farmacologia , Piper , Extratos Vegetais/farmacologia , Comportamento Sexual/efeitos dos fármacos , Animais , Afrodisíacos/química , Comportamento Animal/efeitos dos fármacos , Ejaculação/efeitos dos fármacos , Feminino , Masculino , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/farmacologia , Piper/química , Piperazinas/farmacologia , Extratos Vegetais/química , Folhas de Planta/química , Piridinas/farmacologia , Ratos Wistar , Receptor 5-HT1A de Serotonina/fisiologia , Antagonistas do Receptor 5-HT1 de Serotonina/farmacologiaRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Selected Peruvian Amazon plants are macerated into sugar cane distillates to prepare alcoholic beverages used to improve male sexual performance. The tree bark from Campsiandra angustifolia Spruce ex Benth (Fabaceae), Swartzia polyphylla DC (Fabaceae), Minquartia guianensis Aubl. (Olacaceae) and Thynantus panurensis (Bureau) Sandwith (Bignoniaceae) usually are used as crude drugs in mixtures of several ingredients. AIM OF STUDY: Describe the chemical composition of the most traded traditional male enhancer beverages, namely "Levántate Lazaro" and "Siete veces sin sacarla", and their single crude drug constituents, as well as their inhibitory activity towards the enzyme phosphodiesterase-5. The presence of pro-sexual drugs such as Sildenafil® and derivatives was assessed in the samples. MATERIALS AND METHODS: Single plant constituents and the preparation mixtures were purchased in the Mercado Belen (Iquitos, Peru). Chemical profiling was carried out by HPLC-DAD-ESI-MS/MS. The extracts were assessed for phosphodiesterase-5 inhibition. The occurrence of pro-sexual drugs was determined by HPLC-DAD-ESI-MS/MS. RESULTS: Chemical profiling allowed the identification of condensed tannins as the main constituents of C. angustifolia and S. polyphylla, hydrolysable tannins for M. guianensis, and C-glycosides for T. panurensis. The traditional preparations showed similar composition compared to the crude drugs. At 200⯵g/mL, the traditional preparation "Levántate Lázaro" and "Siete veces sin sacarla" inhibited the phosphodiesterase-5 by 49.88% and 27.90%, respectively. No adulterations with pro-sexual drugs were found in the samples. From the crude drugs, low effect was found for the extracts of S. polyphylla and T. panurensis and high activity for C. angustifolia which inhibited the enzyme by 89.37% and 81.32% at 200 and 100⯵g/mL, respectively. CONCLUSION: The traditional preparations used to improve sexual performance in the Peruvian Amazon showed activity as phosphodiesterase-5 inhibitors. The most active ingredient of the traditional preparations was C. angustifolia, with some contribution from T. panurensis. These results encourage additional studies, including animal models to confirm the male enhancer effect of the preparations.
Assuntos
Afrodisíacos/farmacologia , Magnoliopsida , Inibidores da Fosfodiesterase 5/farmacologia , Preparações de Plantas/farmacologia , Afrodisíacos/química , Nucleotídeo Cíclico Fosfodiesterase do Tipo 5/metabolismo , Etanol/farmacologia , Humanos , Masculino , Peru , Inibidores da Fosfodiesterase 5/química , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/farmacologia , Casca de Planta , Preparações de Plantas/químicaRESUMO
For over a century, Catuaba has been used in Brazilian folk medicine as an aphrodisiac even though the identity of the plant material employed is often uncertain. The species recommended by the Brazilian Pharmacopeia is Anemopaegma arvense (Bignoniaceae), but many other plants, regionally known as Catuaba, are commercialised. Frequently, the quality control of such a complex system is based on chemical markers that do not supply a general idea of the system. With the advent of the metabolomics approach, a global analysis of samples becomes possible. It appears that (1)H-NMR is the most useful method for such application, since it can be used as a wide-spectrum chemical analysis technique. Unfortunately, the generated spectra is complex so a possible approach is to look at the metabolite profile as a whole using multivariate methods, for example, by application of principal component analysis (PCA). In the present paper, we describe for the first time a proton high-resolution magic angle spinning nuclear magnetic resonance ((1)H-HR-MAS NMR) method coupled with PCA for the metabolomic analysis of some commercial Catuaba samples, which provided a reduction in the time required for such analysis. A comparative study of HPLC, HR-MAS and liquid-NMR techniques is also reported.
Assuntos
Bignoniaceae/química , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Meliaceae/química , Afrodisíacos/química , Bignoniaceae/classificação , Medicina Tradicional , Meliaceae/classificação , Análise Multivariada , Casca de Planta/química , Folhas de Planta/química , Raízes de Plantas/químicaRESUMO
OBJECTIVE: The present study was undertaken to investigate the effect of Tribulus alatus extracts on free serum testosterone in male rats. MATERIALS AND METHODS: Free serum testosterone level was measured in male rats treated with alcoholic extracts of the aerial part without fruits, fruits of Tribulus alatus and their fractions. RESULTS: All tested extracts showed significant increase in the level of free serum testosterone when compared to that of corresponding control, p < 0.05. Statistical comparison of all groups revealed that the maximum level was found in groups treated with chloroformic and ethanolic fractions of fruits extract. CONCLUSION: Tribulus alatus extract appears to possess aphrodisiac activity due to its androgen increasing property.
Assuntos
Afrodisíacos/farmacologia , Fitoterapia , Componentes Aéreos da Planta/química , Comportamento Sexual Animal/efeitos dos fármacos , Testosterona/sangue , Tribulus/química , Animais , Afrodisíacos/química , Avaliação Pré-Clínica de Medicamentos , Masculino , Pênis/irrigação sanguínea , Extratos Vegetais/farmacologia , Distribuição Aleatória , Ratos , Ratos WistarRESUMO
OBJECTIVE: The present study was undertaken to investigate the effect of Tribulus alatus extracts on free serum testosterone in male rats. MATERIALS AND METHODS: Free serum testosterone level was measured in male rats treated with alcoholic extracts of the aerial part without fruits, fruits of Tribulus alatus and their fractions. RESULTS: All tested extracts showed significant increase in the level of free serum testosterone when compared to that of corresponding control, p < 0.05. Statistical comparison of all groups revealed that the maximum level was found in groups treated with chloroformic and ethanolic fractions of fruits extract. CONCLUSION: Tribulus alatus extract appears to possess aphrodisiac activity due to its androgen increasing property.
Assuntos
Animais , Masculino , Ratos , Afrodisíacos/farmacologia , Fitoterapia , Componentes Aéreos da Planta/química , Comportamento Sexual Animal/efeitos dos fármacos , Testosterona/sangue , Tribulus/química , Afrodisíacos/química , Avaliação Pré-Clínica de Medicamentos , Pênis/irrigação sanguínea , Extratos Vegetais/farmacologia , Distribuição Aleatória , Ratos WistarRESUMO
Several species of Ferula genus have been used in folk medicine in digestive disorders, rheumatism, headache, arthritis, and as tranquilizers, antispasmodic and aphrodisiac. From the dry and powdered roots of Ferula hermonis Boiss was extracted the oxygenated sesquiterpene 1,5-trans-daucane type: ferutinine (1). The structure of (1) was established by spectroscopic methods as: IR, (1)H RMN, (13)C RMN, COSY, HMBC, HMQC, NOESY, EIMS, and CIMS. The possible signaling pathway of ferutinin (1) in nervous tissue in vitro was assessed and the results showed that this compound is able to increase nitric oxide synthase activity and inositol monophosphate accumulation (49%, each) in the median eminence of the rat brain, suggesting that compound (1) is associated to the activation of phosphoinositide breakdown and nitric oxide production (NO), the last is a gaseous intercellular messenger known to play a broad role in human biology from homeostasis to pathology.
Assuntos
Afrodisíacos/farmacologia , Ferula , Eminência Mediana/efeitos dos fármacos , Óxido Nítrico Sintase/biossíntese , Fitoterapia , Extratos Vegetais/farmacologia , Animais , Afrodisíacos/administração & dosagem , Afrodisíacos/química , Masculino , Eminência Mediana/metabolismo , Extratos Vegetais/administração & dosagem , Extratos Vegetais/química , Raízes de Plantas , Ratos , Ratos Sprague-Dawley , Relação Estrutura-AtividadeRESUMO
Fourteen commercial samples of the popular Brazilian aphrodisiac Catuaba specified as bark drugs of Anemopaegma, Erythroxylum and Trichilia species were examined for identity and purity. Only a minority of the examined Catuaba samples contained the crude drugs claimed on the labels. More than half of the products were adulterated with different crude drugs. The majority of the samples contained a bark originating from Trichilia catigua. The TLC fingerprints confirmed the heterogeneity, in 50% of the samples tropane alkaloids of various concentrations were detected. TLC and HPLC methods for separation and identification of the tropane alkaloids were developed and their analytical data (RF values, retention times, ESI-MS) given. The structure elucidation of the two main alkaloids, catuabine D and its hydroxymethyl derivative, is presented. The 1H- and 13C-NMR assignments of these alkaloids are discussed with regard to literature data. Neither aqueous nor methanolic extracts of the Trichilia catigua reference material nor alkaloid-enriched fractions of commercial samples showed any effect on the rabbit corpus cavernosum in an in vitro test.