Phytochemistry and antimicrobial activity of Campomanesia adamantium

ABSTRACT Campomanesia adamantium (Cambess.) O. Berg., Myrtaceae, is a plant popularly used for its anti-inflammatory, anti-diarrhoeal and urinary antiseptic activities. The aims of this study were to obtain the crude ethanolic extract and the hexane, dichloromethane, ethyl acetate, aqueous and concentrated aqueous tannin fractions from C. adamantium leaves, perform biomonitored fractionation to isolate and identify chemical compounds, study the chemical composition of the volatile oils of the leaves and flowers and test the antimicrobial activity of the ethanolic extract, fractions, isolated substances and volatile oils. Phytochemical screening and chromatographic and spectrometric techniques were used. Volatile oils were isolated by hydrodistillation in a Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. The antimicrobial activity was tested by a broth microdilution test. The component stictane-3,22-diol was isolated and identified from the hexane fraction, while valoneic and gallic acid were isolated and identified from the concentrated aqueous tannin fraction. The major constituents of the volatile oils of the leaves were verbenene (13.91%), β-funebrene (12.05%) and limonene (10.32%), while those of the volatile oils of the flowers were sabinene (20.45%), limonene (19.33%), α-thujene (8.86%) and methyl salicylate (8.66%). Antibacterial activity was verified for the hexane fraction, while antifungal activity was observed for the aqueous fraction and concentrated aqueous tannin fraction and for vanoleic acid. These results may justify the popular use of C. adamantium.

Chemical composition and seasonality variability of the Spiranthera odoratissima volatile oils leaves

ABSTRACT Spiranthera odoratissima A. St.-Hil., Rutaceae, known as "manacá" is a shrub native of the Brazilian Cerrado. Their leaves and roots are popularly used to treat rheumatism, infection and abdominal pain. This study analyzed the chemical composition of volatile oils from leaves of S. odoratissima and verified the seasonal variability of its chemical composition. The volatile oils were obtained by hydrodistillation using a Clevenger type apparatus and analyzed by gas chromatography coupled to mass spectrometry. The main chemical components found in samples of volatile oils were β-caryophyllene, bicyclogermacrene, δ-cadinene, amorphous-4,7(11)-diene, α-epi-muurolol, α-cadinol, α-muurolol and γ-cadinene. The hierarchical clustering identified three groups: the first was characterized by α-epi-muurolol, the second by amorphous-4,7(11)-diene and the third group was characterized by α-muurolol. The discriminant canonical analysis was used to differentiate between clusters on the basis of oil composition. The results suggest that the rainfall presented a relationship with the chemical composition of the volatile oil. This is the first study conducted on the seasonal behavior of the chemical constituents in volatile oil from leaves of S. odoratissima.

Chemical composition and seasonal variation of the volatile oils from Trembleya phlogiformis leaves

ABSTRACT Trembleya phlogiformis DC., Melastomataceae, is a shrub whose leaves are used as a dye for dyeing wool and cotton. The present article aimed to carry out the morphological description of the species, to study the chemical composition of volatile oils from the leaves and flowers and the seasonal variability from the leaves during a year. Macroscopic characterization was carried out with the naked eye and with a stereoscopic microscope. Volatile oils were isolated by hydrodistillation in Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. The major components of the volatile oil of T. phlogiformis flowers were: n-heneicosane (33.5%), phytol (12.3%), n-tricosane (8.4%) and linoleic acid (6.1%). It was verified the existence of a large chemical variability of the volatile oils from the leaves of T. phlogiformis over the months, with the majority compound (oleic alcohol, ranging from 5.7 to 26.8%) present in all samples. A combination of Cluster Analysis and Principal Component Analysis showed the existence of three main clusters, probably related to the seasons. The results suggested that the volatile oils of T. phlogiformis leaves possess high chemical variability, probably related to variation associated with rainfall and the variation in the behavior of specimens throughout the year. This research provides insights for future studies on the volatile oils obtained from the T. phlogiformis leaves and flowers, mainly related to biological markers of applications monitored in the leaves and flowers of this species.

Chemical composition and seasonal variability of the essential oils of leaves and morphological analysis of Hyptis carpinifolia

ABSTRACT Hyptis carpinifolia Benth., Lamiaceae, is a species known popularly as "rosmaninho" and "mata-pasto", and leaves are employed in Brazilian folk medicine to treat colds, flu, and rheumatism. The aim of this study was to perform a morphological description of H. carpinifolia and to evaluate the seasonal chemical variability of the leaf essential oils during 12 months. Macroscopic characterization of H. carpinifolia was carried out with the naked eye and with a stereoscopic microscope. Essential oils were isolated from leaves by hydrodistillation in Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. Major compounds were found to be 1,8-cineole (39.6-61.8%), trans-cadina-1(6),4-diene (2.8-17.5%), β-caryophyllene (4.4-10.0%), prenopsan-8-ol (4.2-9.6%) and β-pinene (2.9-5.3%). Results of essential oils compositions were processed by cluster analysis and principal component analysis. Data showed high variability in the concentration of the components. Besides, there was a seasonal variability of chemical composition, probably related mainly to the rainfall regime.

Chemical composition of essential oils of leaves, flowers and fruits of Hortia oreadica

Abstract Hortia oreadica Groppo, Kallunki & Pirani, Rutaceae, known as “para-tudo”, “quina”, and “quina-do-campo”, is used in traditional medicine locally to treat stomach pain and fevers. The aims of this study were: analyze the chemical composition of essential oils from leaves, flowers and fruits of H. oreadica and verify the seasonal variation of the chemical components of essential oils from leaves. The essential oils were obtained by hydrodistillation using a Clevenger type apparatus and analyzed by GC/MS. The major components found in the samples of the essential oils were the amorpha-4,7(11)-diene (29.27% – flowers, 20.26% – fruits, 27.66–37.89% – leaves), bicyclogermacrene (23.28% – flowers, 20.64% – fruits, 14.71% to 31.37% – leaves). This work represents the first study of the chemical composition of essential oils from leaves, flowers and fruits and seasonal variation in the essential oils from leaves of H. oreadica.

Influence of environmental factors on the composition of essential oils from leaves of Myrcia tomentosa (Aubl) DC / Influencia de los factores ambientales sobre la composición de los aceites esenciales de hojas de Myrcia tomentosa (Aubl) DC

The leaves of Myrcia tomentosa were collected from five sites and four different months in the Brazilian Cerrado and their essential oils were obtained by hidrodistillation and analyzed by GC/MS. The aim of this work was to evaluate the influence of environmental factors on essential oils composition in the leaves of M. tomentosa. The results were submitted to stepwise Multiple Regression and Canonical Correlation Analysis that indicated a relationship between compounds in essential oils and some environmental factors (foliar nutrients, soil nutrients and climatic data). Cluster Analysis indicated a high chemovariability in the essential oils from different sites, also showed that the collection time had a minor effect on oil composition.

Las hojas de Myrcia tomentosa se obtuvieron de cinco sitios diferentes y cuatro meses en el Cerrado brasileño y sus aceites esenciales fueron obtenidos por hidrodistillation y analizados por GC/MS. El objetivo de este trabajo fue evaluar la influencia de los factores ambientales sobre la composición de los aceites esenciales en las hojas de M. tomentosa. Los resultados fueron sometidos a múltiples etapas de regresión y análisis de correlación canónica indicó que la relación entre los compuestos en los aceites esenciales y algunos factores ambientales (nutrientes foliares, fertilizantes y datos climáticos). El análisis de agrupamiento indicó chemovariability un alto en los aceites esenciales de diferentes sitios, también mostró que el equipo de recolección tuvo un efecto menor sobre la composición del aceite.

Chemical variability in the essential oils from leaves of Syzygium jambos

Syzygium jambos (L.) Alston, Myrtaceae, occurs in tropical regions and is a widespread medicinal plant used to treat several diseases, such as hemorrhage, dysentery, diabetes, inflammation, diabetes and gastrointestinal disorders. Leaf essential oils of ten specimens of S. jambos collected from two localities of Central Brazilian Cerrado were investigated by GC-MS. Soil and foliar nutrients were analyzed to determine the mineral compositions. The aims of this study was to evaluate the influence of environmental factors on chemical composition of leaf essential oils of S. jambos. Studies on the influence of environmental factors over composition of essential oils are important because they contribute data for its cultivation, harvest and establish parameters to essential oil components. The data were analyzed using stepwise Multiple Regression and Cluster Analysis, and the results suggest that the main factor capable to influence the chemical composition of leaf essential oils was the collection period and the collection site had a minor effect. The results also suggest that the leaf essential oils composition was influenced mainly by foliar nutrients (N, Mn, Co, Fe, S and Mg) and soil nutrients (Na, Al, S and H+Al). The compound with the best model obtained was the (E)-caryophyllene, with a coefficient of determination equal 0.8113.

Chemical variability of the essential oils from fruits of Pterodon emarginatus in the Brazilian Cerrado

Pterodon emarginatus Vogel, Fabaceae, is a tree species commonly known as "sucupira-branca". It is a popular medicinal plant in the Brazilian cerrado (Savanna). This study investigates the chemical variability of the essential oils from fruits of P. emarginatus. The fruits were collected from five sites in the Brazilian Cerrado and their essential oils were analyzed by GC/MS. The results obtained by Principal Component and Cluster Analysis identified two groups: cluster I containing β-caryophyllene and δ-elemene and cluster II containing α-copaene, β-cubebene, allo-aromadendrene, α-cubebene and γ-muurulene. The Canonical Discriminant Analysis was used to differentiate between clusters on the basis of essential oil composition. The results showed high variability in the composition of the essential oils from fruits of P. emarginatus, contributing to studies of domestication of this species.

Essential oils in aerial parts of Myrcia tomentosa: composition and variability

Species in the Myrtaceae family are used in folk medicine to treat gastrointestinal disorders, infectious diseases and hemorrhagic conditions and are known for their essential oil contents. Gas chromatography coupled with mass spectrometry (GC-MS) was used to characterize the chemical composition of essential oils of the leaves, stem bark and flowers of Myrcia tomentosa (Aubl.) DC., as well as to assess the chemical variability in the constituents of the essential oils of the leaf. Soil and foliar analyses were also performed to determine the mineral compositions. Principal component analysis (PCA) was used to examine the interrelationships between the obtained data. The most abundant component in the essential oils of the flowers was (2E,6E)-methyl farnesoate, whereas hexadecanoic acid was the most abundant essential oil component in the stem bark. The leaf essential oils showed seasonal variation in their chemical composition, with bicyclogermacrene and (2E,6E)-methyl farnesoate as the major chemical components. Forty-four constituents were identified, and only nine compounds were found in all of the samples. Sesquiterpenes were mainly produced in the flowers and leaves. The PCA showed a positive correlation between the oxygenated sesquiterpenes and the foliar nutrients Cu and P. Significant statistical correlations were verified between the climatic data, foliar nutrients and essential oil compositions.

Influence of foliar nutrients on phenol levels in leaves of Eugenia uniflora

Eugenia uniflora L., Myrtaceae, leaves contain high amounts of phenolic compounds which are responsible for several pharmacological activities. In order to evaluate the phenolics seasonal variation leaves were analysed on a monthly basis during the period of two years for the contents of hydrolysable tannins, total phenols, flavonoids, and nutrients (N, P, K, S, Ca, Mg, Mn, Zn, Cu, and Fe). Results were correlated with climate conditions (rainfall, humidity, and mean temperature) by Principal Component and ClusterAnalysis which allowed four groups to be distinguished with respect to the age of the leaves and the content of some metals. Young leaves were characterised by high levels of Zn and nitrogen whereas old leaves contained high levels of Fe and calcium, and both groups had moderate amounts of phenolics. Adult leaves were divided in two groups and results revealed that while one group had the highest levels of all phenols and lowest amounts of Mn and Cu, the other showed opposite quantities. The Canonical Correlation Analysis confirmed a highly significant negative correlation between phenol contents and Mn and Cu. These facts suggested that flavonoids and tannins production depends of the amounts of foliar nutrients, Cu and Mn in particular, which are cofactors of enzymes involved in phenol degradation and lignin biosynthesis. This knowledge can improve this specie cultivation in order to enhance the phenolic compounds concentration.

Composição química, atividade antimicrobiana do óleo essencial e ocorrência de esteróides nas folhas de Pterodon emarginatus Vogel, Fabaceae / Chemical composition, antimicrobial activity of essential oil and the occurrence of steroids in the leaves of Pterodon emarginatus Vogel, Fabaceae

Pterodon emarginatus Vogel, Fabaceae, conhecida popularmente como sucupira-branca, é uma espécie arbórea que possui interesse como planta medicinal e fonte de madeira. Vários estudos com o óleo e extratos dos seus frutos demonstraram atividades cercaricida, antimicrobiana e antiinflamatória. Tendo em vista a importância de P. emarginatus como planta medicinal o presente trabalho analisou a composição química, a atividade antifúngica e antibacteriana do óleo essencial de suas folhas, isolou e identificou compostos do extrato etanólico bruto das folhas. A análise do óleo essencial das folhas permitiu a identificação de 9 hidrocarbonetos sesquiterpênicos, sendo os majoritários o γ-muuroleno (48,79 por cento) e o biciclogermacreno (22,66 por cento). O óleo essencial apresentou atividade frente a bactérias Gram-positivas, sendo inativo sobre isolados clínicos de Candida. O estudo fitoquímico do extrato etanólico das folhas permitiu o isolamento da mistura dos esteróides estigmasterol e β-sitosterol. Todos os resultados obtidos contribuem para a ampliação de informações sobre essa planta amplamente utilizada pela população.

Pterodon emarginatus Vogel, Fabaceae, known as "sucupira-branca", is a tree specie with interest as medicinal plant and source of wood. Several studies with the oil and fruit's extracts have been showed cercaricid, antimicrobial and antiinflamatory activities. The importance of P. emarginatus conducted the present study to realize evaluated antifungal and antibacterial activity of essential oil of their leaves, and isolated some compounds of ethanolic extract of the leaves. The analysis of the essential oil from leaves allowed the identification of nine sesquiterpenics hydrocarbons, with the majority γ-muurolene (48.79 percent) and biciclogermacrene (22.66 percent). The essential oil showed activity against the Gram-positive bacteria, and inactive on clinical isolates of Candida. The phytochemical study of the ethanol extract of the leaves allowed the isolation of the mixture of stigmasterol and β-sitosterol steroids. All results contribute to the expansion of information about this plant widely used by the population.

Avaliação da eficácia de extratos oleosos de frutos verdes e maduros de cinamomo (Melia azedarach) sobre Rhipicephalus (Boophilus) microplus (Acari: Ixodidae) / Evaluation of efficacy of ripe and unripe fruit oil extracts of Melia azedarach against Rhipicephalus (Boophilus) microplus (Acari: ixodidae)

Extratos hexânicos obtidos dos frutos de Melia azedarach foram testados sobre fêmeas ingurgitadas e larvas de Rhipicephalus (Boophilus) microplus. Foram produzidos quatro extratos: um de frutos verdes e três com frutos maduros, sendo um com os frutos imediatamente processados, outro com frutos armazenados por cinco meses e um testado após armazenamento do extrato por 2 (dois) anos a 4ºC. Os testes foram feitos em triplicata, em diluições de 0,25 por cento a 0,0156 por cento. A eficácia dos extratos foi avaliada através da comparação da Reprodução Estimada dos lotes "controle e tratado" para fêmeas, da mortalidade para as larvas, e do cálculo das DL50 e da potência relativa para larvas e fêmeas. O extrato de frutos verdes apresentou uma eficácia variando de 3,6 por cento a 100 por cento para fêmeas, e o de frutos maduros variou de 5,2 por cento a 99,7 por cento. Os dois extratos causaram uma mortalidade de 100 por cento das larvas nas maiores concentrações. O extrato de frutos armazenados apresentou eficácia de 14 por cento a 83 por cento sobre fêmeas, enquanto o extrato armazenado em geladeira apresentou eficácia de 8,4 por cento a 100 por cento e ambos não apresentaram efeito larvicida. Os resultados obtidos demonstram uma superioridade do extrato verde, com uma menor DL50 e potência 1,497 vezes superior ao extrato de frutos maduros.

Hexanic extracts gotten of the fruits of cinamomo (Melia azedarach) were tested on engourged females and larvae of Rhipicephalus (Boophilus) microplus. Four extracts were produced: one of unripe fruits and three of ripe fruits, being one with the fruits immediately processed, another one with fruits stored for five months and one tested after storage of the extract for 2 (two) years at 4ºC. The tests were made in triplicate, in 0.25 percent- 0.0156 percent dilutions. The effectiveness of extracts was evaluated through the comparison of the Reproduction Estimate of the groups "controlled and treated" for females, of mortality for the larvae, and of the calculation of the DL50 and the relative power for larvae and females. The extract of unripe fruits presented the effectiveness varying the 3.6 percent - 100 percent for females, and of ripe fruits it varied of 5.2 percent - 99.7 percent. The two extracts caused a mortality of 100 percent of the larvae in the highest concentrations. The extract of stored fruits presented effectiveness of 14 percent - 83 percent on females, while the extract stored in refrigerator presented effectiveness of 8.4 percent 100 percent and both did not present larvicidal effect. The results demonstrate a superiority of the unripe extract, with a minor DL50 and superior power 1.497 times to the extract of ripe fruits.

Seasonal variation in the content of tannins in barks of barbatimão species

The contents of tannins in the barks of barbatimão species, Stryphnodendron adstringens (Mart.) Cov. and S. polyphyllum (Mart.), were analysed monthly during one year. Results were correlated with climate conditions (rainfall, humidity and mean temperature) by chemometric methods. Principal component analysis of the data showed a tendency for higher production of tannins in the warm and wet season, suggesting that environmental factors can affect the levels of tannins in those plants.

A composição de taninos em cascas de espécies de barbatimão, Stryphnodendron adstringens (Mart.) Cov. and S. polyphyllum (Mart.), foi analisada mensalmente durante um ano. Os resultados foram correlacionados com as condições climáticas do período de coleta (precipitação, umidade e temperatura média) através de métodos quimiométricos. Análise de componentes principais dos dados mostrou uma tendência de maior produção de taninos na estação quente e chuvosa, sugerindo que os fatores ambientais podem afetar os teores de taninos nestas espécies.

Avaliação da atividade larvicida de plantas fitoterápicas do cerrado do gênero Stryphnodendron spp. sobre miracídios e cercárias de Schistosoma mansoni / Evaluation of the larvicidal activity of phytotherapic brazilian savannah plants of the genus Stryphnodendron spp. on Schistosoma mansoni miracidia and cercariae

A esquistossomíase é uma doença endêmica causada por parasitos do gênero Schistosoma, sendo somente Schistosoma mansoni observado no Brasil. No presente trabalho, o potencial das plantas do Cerrado brasileiro. Stryphnodendron polyphyllum e Stryphnodendron adstringens, foi testado como fonte alternativa de produtos naturais utilizados contra miracídios e cercárias, as formas infectantes de S. mansoni. A partir dos extratos brutos EAA (extração acetona: água) das cascas dos caules preparam-se soluções-mãe de 400 ppm, que foram diluídas até se obterem as concentrações de 100 e 200 ppm para os bioensaios com miracídios, e de 20, 50, 100 e 200 ppm para os bioensaios com cercárias. Nos testes com miracídios, estas plantas demonstraram atividade somente 5 horas e 30 minutos após o contato inicial com os extratos, enquanto o grupo-controle sobreviveu por oito horas nas mesmas condições. A mortalidade das cercárias ocorreu apenas uma hora após o início dos experimentos em todas as concentrações testadas para as duas espécies vegetais. O grupo-controle sobreviveu, em água, por 36 horas após o início dos experimentos. Estes dados confirmam a presença, no Cerrado brasileiro, de plantas com potencial bioativo no combate às cercárias, forma infectante de S. mansoni para mamíferos.

Antimicrobial activity of Hyptis ovalifolia towards dermatophytes

The essential oil and the aqueous, hexane and methanolic fractions from Hyptis ovalifolia leaves were evaluated for their antifungal activity in vitro against 60 strains of dermatophytes: 10 strains of Microsporum canis, 10 of M. gypseum, 20 of Trichophyton rubrum and 20 of T. mentagrophytes. The extracts inhibited growth of the dermatophytes tested at different concentrations. The most biologically active was the essential oil from the leaves which inhibited 57 isolates (95 percent) at a concentration of ú 500 æg/ml.

Atividade tripanocida in vivo de Stryphnodendron adstringens (barbatimão verdadeiro) e Caryocar brasiliensis (pequi)

O Stryphnodendron adstringens e o Caryocar brasiliensis são espécies nativas do Cerrado e vem sendo testadas como forma alternativa no controle de parasitoses e vetores. Este trabalho avaliou a ação dos extratos bruto etanólicos das cascas destas espécies na concentração de 400 ppm, sobre a parasitemia do Trypanosoma cruzi. Camundongos foram infectados por via intraperitoneal com 1x104 formas tripomastigotas do parasito e após 24 h, inoculados por via intragástrica com dose única diária dos extratos durante dez dias. A avaliação de parasitemia foi efetuada em intervalos de 48 h até a morte dos animais. Os resultados demonstraram que durante as quantificações, os extratos de S. adstringens e de C. brasiliensis apresentaram uma significativa interferência sobre a curva de parasitemia do T. cruzi, reduzindo o número de parasitos no sangue.

Crude extracts from barks of Stryphnodendron adstringens and Caryocar brasiliensis, native species of Cerrado, have been screened at 400 ppm for antiparasitic activity against Trypanosoma cruzi. Mice were inoculated with 1x104 parasites, after 24 h they were treated with one day dose extracts during ten days. The trypanosomicidal activity was evaluated each 48 h until animals death. The extracts of S. adstringens and C. brasiliensis decreased significantly the number of parasites in the blood.

Plantas moluscicidas no controle dos caramuljos transmissores da esquistossomíase, com ênfase na ação de taninos / Molluscicide plants in the control of the snail, intermediate host of Scistosoma, with emphasis in tannins

Um dos alvos no controle da esquistossomíase é o controle dos oluscos, hospedeiros intermediários de Schistosoma spp, interrompendo assim o ciclo de vida do parasito e prevenimdo consequentemente a infecção humana. Várias espécies de vegetais são conhecidas por suas atividades moluscicidas, sendo, portanto, potencialmente úteis no controle das esquistossomíases intestinal e urinária transmitidas por moluscos Biomphalaria, Bulinus e Oncomelania, respectivamente, nas diferentes regiöes do mundo onde ocorrem. Esses moluscos têm sido controlados com a aplicação de substâncias naturais e/ou sintéticas...