In vivo effect of essential oil of Mentha x villosa and its active compound against Schistosoma mansoni (Sambon, 1907) / Efeito in vivo do óleo essencial de Mentha x villosa e seu composto ativo sobre Schistosoma mansoni (Sambon, 1907)

Abstract Schistosomiasis treatment is dependent on a single drug, praziquantel (PZQ). The development of resistance of PZQ has drawn the attention of many researchers to alternative drugs. One viable and promising treatment is the study of medicinal plants as a new approach to the experimental treatment for Schistosomiasis. The present work aimed to evaluate in vivo antischistosomal activity of effect of Mentha x villosa Oil Essential (Mv-EO) and rotundifolone (ROT) against Schistosoma mansoni. Thirty-day-old female Swiss webster mice (Mus musculus) weighing 50 grams were used. Mice were infected with 80 cercariae of S. mansoni (BH strain) and orally administered Mv-EO (50, 100 and 200 mg/Kg) and ROT (35.9, 70.9 and 141.9 mg/Kg) at 45-days post infection for 5 consecutive days. All mice were euthanized 60 days after infection. Praziquantel was the positive control in the experiment. Doses of 200 mg/kg (Mv-EO) and ROT (141.9 mg/Kg) resulted in a significant reduction in fluke burden (72.44% and 74.48%, respectively). There was also marked reduction in liver, intestinal and faecal and changed oogram pattern, compared to infected untreated mice. Considering the results obtained, further biological studies are required in order to elucidate the mechanism of schistosomicidal action on against adult S. mansoni.

Resumo O tratamento da esquistossomose é dependente de uma única droga, praziquantel (PZQ). O desenvolvimento da resistência de PZQ tem atraído atenção de muitos pesquisadores por medicamentos alternativos. Um tratamento viável e promissor é o estudo das plantas medicinais como uma nova abordagem para o tratamento experimental para esquistossomose. O presente trabalho objetivou avaliar a atividade esquistossomicida in vivo óleo essencial de Mentha x villosa (OE-Mv) e rotundifolona (ROT) contra Schistosoma mansoni. Foram utilizados camundongos Swiss webster (Mus musculus) fêmea de trinta dias de idade pesando 50 gramas. Os camundongos foram infectados com 80 cercárias de S. mansoni (cepa BH) e administrado por via oral OE-Mv (50, 100 e 200 mg/Kg) e ROT (35,9, 70,9 e 141,9 mg/Kg) apos 45 dias de infecção durante 5 dias consecutivos. Todos os animais foram eutanasiados 60 dias após a infecção. Praziquantel foi o controle positivo no experimento. O tratamento dos camundongos infectados com doses de 200 mg/kg (OE-Mv) e rotundifolona (141,9 mg/Kg) resultaram em redução significativa dos vermes (72.44% e 74.48%, respectivamente). Foi observado também redução no fígado, intestino e fecal e alteração no padrão do oograma, em comparação aos camundongos infectados e não tratados. Considerando os resultados obtidos, mais estudos biológicos são necessários a fim de elucidar o mecanismo de ação esquistossomicida contra adultos de S. mansoni.

In vivo effect of essential oil of Mentha x villosa and its active compound against Schistosoma mansoni (Sambon, 1907)

Abstract Schistosomiasis treatment is dependent on a single drug, praziquantel (PZQ). The development of resistance of PZQ has drawn the attention of many researchers to alternative drugs. One viable and promising treatment is the study of medicinal plants as a new approach to the experimental treatment for Schistosomiasis. The present work aimed to evaluate in vivo antischistosomal activity of effect of Mentha x villosa Oil Essential (Mv-EO) and rotundifolone (ROT) against Schistosoma mansoni. Thirty-day-old female Swiss webster mice (Mus musculus) weighing 50 grams were used. Mice were infected with 80 cercariae of S. mansoni (BH strain) and orally administered Mv-EO (50, 100 and 200 mg/Kg) and ROT (35.9, 70.9 and 141.9 mg/Kg) at 45-days post infection for 5 consecutive days. All mice were euthanized 60 days after infection. Praziquantel was the positive control in the experiment. Doses of 200 mg/kg (Mv-EO) and ROT (141.9 mg/Kg) resulted in a significant reduction in fluke burden (72.44% and 74.48%, respectively). There was also marked reduction in liver, intestinal and faecal and changed oogram pattern, compared to infected untreated mice. Considering the results obtained, further biological studies are required in order to elucidate the mechanism of schistosomicidal action on against adult S. mansoni.

Resumo O tratamento da esquistossomose é dependente de uma única droga, praziquantel (PZQ). O desenvolvimento da resistência de PZQ tem atraído atenção de muitos pesquisadores por medicamentos alternativos. Um tratamento viável e promissor é o estudo das plantas medicinais como uma nova abordagem para o tratamento experimental para esquistossomose. O presente trabalho objetivou avaliar a atividade esquistossomicida in vivo óleo essencial de Mentha x villosa (OE-Mv) e rotundifolona (ROT) contra Schistosoma mansoni. Foram utilizados camundongos Swiss webster (Mus musculus) fêmea de trinta dias de idade pesando 50 gramas. Os camundongos foram infectados com 80 cercárias de S. mansoni (cepa BH) e administrado por via oral OE-Mv (50, 100 e 200 mg/Kg) e ROT (35,9, 70,9 e 141,9 mg/Kg) apos 45 dias de infecção durante 5 dias consecutivos. Todos os animais foram eutanasiados 60 dias após a infecção. Praziquantel foi o controle positivo no experimento. O tratamento dos camundongos infectados com doses de 200 mg/kg (OE-Mv) e rotundifolona (141,9 mg/Kg) resultaram em redução significativa dos vermes (72.44% e 74.48%, respectivamente). Foi observado também redução no fígado, intestino e fecal e alteração no padrão do oograma, em comparação aos camundongos infectados e não tratados. Considerando os resultados obtidos, mais estudos biológicos são necessários a fim de elucidar o mecanismo de ação esquistossomicida contra adultos de S. mansoni.

Atividade anti-helmíntica de plantas nativas do continente americano: uma revisão / Anthelmintic activity of native American plants: a review

O presente trabalho faz uma revisão de plantas nativas do continente americano com atividade anti-helmíntica com a finalidade de subsidiar pesquisas e o desenvolvimento de novos medicamentos na área de produtos naturais. Na literatura, foram citadas 22 famílias de plantas, tais como: Moraceae, Asteraceae e Cucurbitaceae, e estudadas cerca de 35 espécies, como a Ficus sp, Cucurbita máxima, e Ruta graveolens, usadas por sua alegada atividade anti-helmíntica. Destas espécies, 26 foram ativas contra alguns helmintos: Strongyloides stercolaris, Ancylostomidae, Trichostrongylus sp, Capillaria sp, Ascaris lumbricoides, Taenia saginata, Haemonchus contortus, e Hymenolepsis diminuta. Foi verificado maior número de estudos com parasitas de animais, possivelmente devido ao desenvolvimento de resistência dos helmintos aos tratamentos convencionais disponíveis.

This paper is a review of native American plants showing anthelmintic activity in order to give support to research and development of new drugs in the field of natural products. In the literature, 22 plant families were cited, such as: Moraceae, Asteraceae and Cucurbitaceae, and around 35 species were studied, including Ficus sp, Cucurbita maxima and Ruta graveolens, used for their putative anthelmintic activity. From these species, 26 were active against some helminthes: Strongyloides stercolaris, Ancylostomidae, Trichostrongylus sp, Capillaria sp, Ascaris lumbricoides, Taenia saginata, Haemonchus contortus and Hymenolepsis diminuta. Data indicated a larger number of studies with animal parasites, probably due to the resistance of these helminthes to the conventional treatments available.

Alkaloids and volatile constituents from the stem of Fusaea longifolia (Aubl.) Saff. (Annonaceae)

A phytochemical study of the ethanol extract and an extraction of the volatile compounds, performed by means of Clevenger apparatus were carried out with the stem of Fusaea longifolia (Aubl.) Saff. (Annonaceae). The ethanol extract yielded O-methylmoschatoline, isolated for the first time in this species, and stepholidine, reported for the first time in genus Fusaea. The structural identification of the alkaloids was made based on the analysis of their NMR spectra. Through the use of GC and GC-MS, two sesquiterpenoids, a-cadinol (12.5 percent) and spatulenol (12.0 percent) were identified as the major constituents of the essential oil.

Flavonóides glicosilados de Herissantia tiubae (K. Schum) Brizicky (Malvaceae) e testes farmacológicos preliminares do canferol 3,7-di-O-a-L-ramnopiranosídeo / Glycosyl flavonoids from Herissantia tiubae (K. Schum) Brizicky (Malvaceae) and preliminary tests of kaempferol 3,7-di-O-a-L-rhamnopyranoside

Das partes aéreas de Herissantia tiubae (K. Schum.) Brizicky foram isolados, através de métodos cromatográficos, dois flavonóides glicosilados, canferol 3,7-di-O-a-L-ramnopiranosídeo e canferol 3-b-O-D-(6’’-E-p-cumaroil) glicosídeo. As estruturas foram identificadas com o uso de técnicas espectroscópicas de IV, RMN ¹H e 13C incluindo métodos bidimensionais, além de comparações com dados da literatura. O canferol 3,7-di-O-a-L-ramnopiranosídeo foi submetido a testes farmacológicos preliminares com a finalidade de avaliar o seu efeito sobre o sistema cardiovascular.

From the aerial parts of Herissantia tiubae (K. Schum.) Brizicky two flavonol glycosides were isolated by means of chromatographic methods, kaempferol 3,7-di-O-a-L-rhamnopyranoside and kaempferol 3-O-b-D-(6’’-E-p-coumaroyl) glucoside. Their structural identification was made by IV, ¹H and 13C NMR spectroscopy, including two dimensional techniques, together with comparison with literatura data. Preliminary tests were carried out with kaempferol 3,7-di-O-a-L-rhamnopyranoside in order to study its possible cardiovascular effect.

Ecdisteróide e iridóide glicosilado de Vitex gardneriana Schauer (Verbenaceae) / Ecdysteroid and iridoid glycoside from Vitex gardneriana Schauer (Verbenaceae)

O extrato metanólico das cascas do caule de Vitex gardneriana Schauer forneceu o ecdisteróide, 20-hidroxi-ecdisona e o iridóide glicosilado, aucubina. As estruturas foram caracterizadas por métodos químicos e espectroscópicos.

The methanolic extract of the stem bark of Vitex gardneriana Schauer afforded the ecdysteroid, 20-hydroxy-ecdysone and the iridoid glycoside, aucubin. Their structures were established on the basis of chemical and spectroscopic studies.

Calcium antagonism and the vasorelaxation of the rat aorta induced by rotundifolone

The vasorelaxing activity of rotundifolone (ROT), a major constituent (63.5 percent) of the essential oil of Mentha x villosa, was tested in male Wistar rats (300-350 g). In isolated rat aortic rings, increasing ROT concentrations (0.3, 1, 10, 100, 300, and 500 æg/ml) inhibited the contractile effects of 1 æM phenylephrine and of 80 or 30 mM KCl (IC50 values, reported as means ± SEM = 184 ± 6, 185 ± 3 and 188 ± 19 æg/ml, N = 6, respectively). In aortic rings pre-contracted with 1 æM phenylephrine, the smooth muscle-relaxant activity of ROT was inhibited by removal of the vascular endothelium (IC50 value = 235 ± 7 æg/ml, N = 6). Furthermore, ROT inhibited (pD2 = 6.04, N = 6) the CaCl2-induced contraction in depolarizing medium in a concentration-dependent manner. In Ca2+-free solution, ROT inhibited 1 æM phenylephrine-induced contraction in a concentration-dependent manner and did not modify the phasic contractile response evoked by caffeine (20 mM). In conclusion, in the present study we have shown that ROT produces an endothelium-independent vasorelaxing effect in the rat aorta. The results further indicated that in the rat aorta ROT is able to induce vasorelaxation, at least in part, by inhibiting both: a) voltage-dependent Ca² channels, and b) intracellular Ca2+ release selectively due to inositol 1,4,5-triphosphate activation. Additional studies are required to elucidate the mechanisms underlying ROT-induced relaxation.

Evaluation of the cardiovascular effects of vasicine, an alkaloid isolated from the leaves of Sida cordifolia L. (Malvaceae)

The cardiovascular effects of vasicine, an alkaloid isolated from the leaves of Sida cordifolia L., were evaluated in this work. In non-anaesthetized rats (n=6), vasicine (1, 2.5, 5 and 10 mg/kg; i.v., randomly) induced hypotension associated with an intense bradycardia. Both responses were completely abolished after atropine (2mg/Kg; i.v.) and attenuated after hexamethonium (20 mg/Kg; i.v.). In isolated rat mesenteric artery rings, vasicine (0.03, 0.1, 0.3, 1, 3, 10, 30, 100 and 300 μg/mL, cumulatively) induced concentration-dependent relaxation of phenylephrine-induced tone (IC50= 3.8±0.9 μg/mL; n = 6). In conclusion, the results show that vasicine produce hypotension and bradycardia which appears to be due to the stimulation of cardiac muscarinic receptors (directly and/or indirectly), and by a decrease of the peripheral resistances.

Os efeitos cardiovasculares de vasicina, um alcalóide isolado das folhas de Sida cordifolia L., foi avaliado neste trabalho. Em ratos não-anestesiados (n=6), vasicina (1, 2.5, 5 e 10 mg/kg; i.v., aleatoriamente) induziu hipotensão associada com uma intensa bradicardia. Ambas as respostas buscaram completamente abolidas após atropina (2 mg/Kg; i.v.) e atenuadas após hexamethonio (20 mg/Kg; i.v.). Em anéis de artéria mesentérica de rato isolada, vasicina (0.03, 0.1, 0.3, 1, 3, 10, 30, 100 e 300 g/mL, cumulativamente) induziu relaxamento concentração-dependente de tônus promovido por fenilefrina (IC50= 3.8 0.9 g/mL; n= 6). Em conclusão, os resultados mostram que vasicina produz hipotensão e bradicardia que parecem ser devidas à excitação de receptores muscarínicos cardíacos (direta e/ou indiretamente) e por uma diminuição das resistências periféricas.

Outros constituintes químicos de Diplotropis ferruginea Benth. (Fabaceae)

O extrato hexânico das cascas do caule de Diplotropis ferruginea Benth (Fabaceae), após procedimentos cromatográficos e fitoquímicos, forneceu o triterpeno lupeol, citado pela primeira vez em Diplotropis ferruginea, e etil-2-hidroxi-4-methoxi-6-propil-benzoate, descrito pela primeira vez em na literatura. As determinações estruturais desses compostos foram realizadas com base em análises espectroscópicas de ¹H e 13C NMR, bem como também por comparação com valores da literatura.

The hexane extract of the stem bark of Diplotropis ferruginea Benth (Fabaceae), after chromatografic and phytochemical procedures, yielded the triterpene lupeol, wich has been cited for the first time on Diplotropis ferruginea, and ethyl-2-hydroxy-4-methoxy-6-propyl-benzoate, described for the first time on literature. The structural determinations of these compounds were performed on the basis of ¹H and 13C NMR spectroscopic analysis as well as comparison with literature values.

Isolamento e identificação de novos alcalóides de Ocotea duckei Vattimo (Lauraceae)

Três alcalóides benzilisoquinolínicos, reticulina, coclaurina e N-acetilnorjuzifina foram isolados das cascas de caule de Ocotea duckei; do cálice foi isolado laureliptina, um alcalóide do tipo aporfínico. Essas substâncias foram isoladas por métodos cromatográficos e identificadas por espectroscopia de 1H e 13C NMR com o auxílio de técnicas 2-D como as de COSY, NOESY, HMQC e HMBC. Comparações com os dados de literatura foram também realizadas.

Three benzylisoquinoline alkaloids, reticuline, coclaurine, and N-acetyl norjuziphine, where isolated from the stem bark of Ocotea duckei, the calix yielded laurelliptine, an aporphine alkaloid. These substances were isolated by chromatographic methods and identified by 1H and 13C NMR spectroscopy with the aid of 2-D techniques such as COSY, NOESY, HMQC and HMBC. Comparison with literature data was also helpful.

Alcalóides de Duguetia trunciflora Maas (Annonaceae)

From the ethanolic extract of the leaves and thin branches of Duguetia trunciflora Maas (Annonaceae) six alkaloids were isolated, being one benzylisoquinoline: reticuline¹, four tetrahydroprotoberberine:,tetrahydro-palmatine², tetrahydrojathrorrizine³, discretamine4, thaicanine5, and one berberine: jathrorrizine6. These alkaloids were identified through ¹H and 13C NMR spectroscopic technics. The alkaloids 1, 3, 5 and 6 are being cited for the first time on Duguetia genus.

Aplicação da termogravimetria (TG) no controle de qualidade da milona (Cissampelos sympodialis Eichl. ) Menispermaceae

This work proposes the application of the thermogravimetry (TG) in the control of quality of Cissampelos sympodialis, known popularly as 'milona'. After the extraction process, the alkaloids became the majority substances and the extracts showed the kinetic behavior of the bisbenzylisoquinoline alkaloids. This seems to be an important and useful parameter for the quality control of the 'milona' extracts.

Alcalóides isolados Hornschuchia obliqua (Annonaceae)

The genus Hornschuchia obliqua belonging to the Annonaceae family. The family comprising ca 130 genera and 2300 species, located in the Magnoliales, a primitive order of plants, is known to produce isoquinoline alkaloids derivatives1. Indeed the great majority of alkaloidal constituents of these plants are isoquinoline-derived structures, along with a wide range of non-alkaloidal compounds of varied stuctural types2,3. The present paper describes the chemical investigation of the alkaloids from Hornschuchia obliqua, isolated until now.

Isolamento biomonitorado de alcalóides tóxicos de Prosopis juliflora (algaroba) / Bioassay-guided isolation of toxic alkaloids of Prosopis juliflora (mesquite)

Uma investigação fitoquímica das vagens de Prosopis juliflora cultivada na região semi-árida do Estado da Paraíba e monitorada através de testes farmacológicos levou ao isolamento, purificação e identificação do alcalóide principal juliprosopina. A presença de outros constituintes químicos em mistura, tais como juliprosina e juliprosineno, foi verificada na fração dos alcalóides totais através de uma análise do espectro de RMN de 13C. Este trabalho sugere que a toxicidade, observada em animais de laboratório, está quimicamente relacionada com os alcalóides piperidínicos presentes nas vagens desta leguminosa.

A phytochemical investigation of the pods of Prosopis juliflora cultivated in the semi arid region of the State of Paraiba, monitored by pharmacological tests, led to the isolation, purification and identification of its main alkaloid - juliprosopine. The presence of other compounds such as juliprosine and juliprosinene, was observed through analysis of 13C NMR. This work suggests that the toxic activity, observed in laboratory animals, is chemicaly related with the piperidine alkaloids present in the pods of this Leguminosae.

Chemical and pharmacological investigation of Solanum species of Brazil: a search for solasodine and other potentially useful therapeutic agents

A systematic search for solasodine, an important staring material for the partial synthesis of steroidal hormones as well as other potentially bioactive constituents of various Solanum species of Brazil has been undertaken. Thus, the fruits of S. paludosum, S. asperum, S. sessiliforum and Solanum sp. were found to contain significant amounts of solasodine. The root bark of S. paludosum which showe durare like activity yelded tomatidenol and another yet unidentified alkaloid responsible for the biological activity. The fruits of S. asperum yelded a new spirosolane alkaloid, solaparnaine. The stem bark of S. pseudo-quina showed convulsive and exitatory activity from which (25S)-isosolafloridine was identified as the active principle. In addition, the latter alkaloid was also found to show antimicrobial activity.