The selective obtaining of amyrins from Amazonian Protium oleoresins / La obtención selectiva de amirinas a partir de oleorresinas de Protium amazónicas

SUMMARY The oleoresin produced by species of genus Protium sp. is rich in alpha and betaamyrins, two triterpenes with many pharmacogical activities. Considering the need to make the improved obtainment of these products feasible, this study sought to optimize techniques for the extraction and isolation of amyrins from resin. Two methods of extraction (maceration and sonication) with different solvents were compared to direct isolation from crude resin. The isolation of triterpenes was performed by chromatographic columns and the yields of extracts and fractions were analyzed by analysis of variance. The best extraction solvent for amyrins was hexane for both maceration and sonication methods (38.16±2.06% and 37.67±8.21%, respectively). There was no statistical difference between these methods and the direct method (32.05±2.40%). Additionally, the direct method is cheaper and more environmentally friendly. Thus, this study showed that it is possible to obtain a large quantity of amyrins by means of cheap, fast and ecological methods.

RESUMEN La oleorresina producida por especies del género Protium sp. es rica en amirinas alfa y beta, dos triterpenos con muchas actividades farmacológicas. Esta investigación buscó optimizar las técnicas de extracción y aislamiento de amirinas de la resina para hacer factible la obtención mejorada de esos productos. Se compararon dos métodos de extracción (maceración y sonicación) con diferentes solventes con aislamiento directo de la resina cruda. El aislamento de los triterpenos se realizó mediante columnas cromatográficas y los rendimientos de extractos y fracciones fueron hechos mediante análisis de varianza. El mejor solvente para la extracción de amirinas fue el hexano para ambos métodos de maceración y sonicación (38,16±2,06% y 37,67±8,21%, respectivamente). No hubo diferencia estadística entre estos métodos y el método directo (32,05±2,40%). Además, el método directo es más barato y ecológico. De este modo, esta investigación demostró que es posible obtener una gran cantidad de amirinas a través de métodos rápidos, baratos y ecológicos.

Antibacterial substances from leaves of Protium spruceanum (Burseraceae): in vitro and in silico evaluation

Due to the increase of bacterial resistance, the search for new antibiotics is necessary and the medicinal plants represent its most important source. The aim of this study was to evaluate the antibacterial property of extract and fractions from Protium spruceanum leaves, against pathogenic bacteria. By means of diffusion and microdilution assays, the crude extract was active against the nine bacteria tested being the hydromethanolic fraction the most active. During phytochemical procedures, procyanidin (1) and catechin (2) were identified as the main antibacterial constituents of this fraction. In silico results obtained using PASSonline tool indicated 1 and 2 as having good potential to interact with different targets of currently used antibiotics. These results no indicated potential to none DNA effect and indicated the cell wall as mainly target. Electrophoresis result supported that had no DNA damage. Cell wall damage was confirmed by propidium iodide test that showed increased membrane permeability and by cell surface deformations observed in scanning electronic microscopy. The in vitro assays together with the in silico prediction results establish the potential of P. spruceanum as source of antibacterial compounds that acts on important bacterial targets. These results contribute to the development of natural substances against pathogenic bacteria and to discovery of new antibiotics.

In vitro antiparasitic activity and chemical composition of the essential oil from Protium ovatum leaves (Burceraceae)

ABSTRACT Leishmaniasis and trypanosomiasis are globally widespread parasitic diseases which have been responsible for high mortality rates. Since drugs available for their treatment are highly hepatotoxic, nephrotoxic and cardiotoxic, adherence to therapy has been affected. Thus, the search for new, more effective and safer drugs for the treatment of these diseases is necessary. Natural products have stood out as an alternative to searching for new bioactive molecules with therapeutic potential. In this study, the chemical composition and antiparasitic activity of the essential oil from Protium ovatum leaves against trypomastigote forms of Trypanosoma cruzi and the promastigote forms of Leishmania amazonensis were evaluated. The essential oil was promising against trypomastigote forms of T. cruzi (IC50= 28.55 μg.mL-1) and L. amazonensis promastigotes (IC50 = 2.28 μg.mL-1). Eighteen chemical constituents were identified by Gas Chromatography coupled to Mass Spectrometry (GC-MS) in the essential oil, whose major constituents were spathulenol (17.6 %), caryophyllene oxide (16.4 %), β-caryophyllene (14.0 %) and myrcene (8.4 %). In addition, the essential oil from P. ovatum leaves had moderate cytotoxicity against LLCMK2 adherent epithelial cell at the concentration range under analysis (CC50 = 150.9 μg.mL-1). It should be highlighted that this is the first report of the chemical composition and anti-Trypanosoma cruzi and anti-Leishmania amazonensis activities of the essential oil from Protium ovatum leaves.

Report on the Malungo expedition to the Erepecuru river, Oriximiná, Brazil. Part I: is there a difference between black and white breu?

ABSTRACT Species belonging to Burseraceae produce an oleoresin known in the north of Brazil as breu. They comprise an essential oil with a complex composition, and are used in Amazonia for smoking the environment, to caulk boats and for medicinal purposes. Depending on its organoleptic characteristics and on the breu-producing species, they are called white or black breu. In this work, we provide data about the breu-producing species occurring in the quilombola region of the Erepecuru river, the chemical composition, and whether it is possible to differentiate them based on their chemical composition and/or botanical identification. Aerial samples from breu trees and oleoresins were collected from 10 different individuals at 6 different sites on the Erepecuru river under the guidance of the quilombolas. Essential oils were extracted by hydrodistillation and characterized by GC–MS. From the analysis, 126 different substances were identified, with a large quantitative and qualitative variation. To better understand the chemical variations within the samples and to sort the variation into the categories of white or black breu as identified by the quilombola, we sorted the oil samples into five different sets according to their major compounds (A: δ-3-carene; B: p-cymene; C: γ-cadinene/p-cymene; D: limonene, β-phellandrene/α-terpineol; E: α-pinene/limonene). Essential oils from samples of white breu had the highest concentration of α-pinene, while a similarity in chemical composition could not be established for the black breu samples (sets A, B and C). Furthermore, a chemical similarity between a black breu (Protium heptaphyllum (Aubl.) Marchand) and a white breu (Protium decandrum (Aubl.) Marchand) sample was evidenced. In conclusion, it is difficult to establish definitions for white and black breu based on chemical, botanical or regional names. This designation is more cultural and regional than scientific and is based on the oleoresin production volume, its color aspect and scent.

Antityrosinase, antioxidative activities, and brine shrimp lethality of ethanolic extracts from Protium serratum (Wall. ex Colebr.) Engl

Objective To evaluate all parts of Protium serratum (Wall. ex Colebr.) Engl. (P. serratum) for their phytochemistry and biological activities including antityrosinase, antioxidant, and brine shrimp lethality. Methods Nine ethanolic extracts from different P. serratum parts such as twig, whole fruit, pericarp, and root were investigated for their phytochemical screening and biological activities in terms of tyrosinase inhibition, antioxidant against 1,1-diphenyl-2-picrylhydrazyl and hydroxyl radicals, and lethality to brine shrimp larvae. Results Phytochemical screening also revealed the presence of flavonoids, condensed tannins, alkaloids, triterpenoids, steroids, and sugars in P. serratum. The root extract was the most effective for antityrosinase activity with IC

MDGC-MS analysis of essential oils from Protium heptaphyllum (Aubl. ) and their antifungal activity against Candida specie / Análise MDGC-MS de óleos essenciais de Protium heptaphyllum (Aubl. ) e sua atividade antifúngica contra espécies de Candida

ABSTRACT Protium heptaphyllum is found in the Amazon region, and in various Brazilian states and South American countries. Also Known as almecega, it produces an oil resin used in traditional medicine as analgesic, anti-inflammatory, cicatrizant and expectorant, it is rich in pentacyclic triterpenes and essential oil. The main objective of this study was to analyze the chemical composition of P. heptaphyllumresin (OEPh) over different extraction times and to evaluate their antifungal activity against Candida species, obtained from gardeners with onychomycosis, using the disk diffusion method. The OEPh was obtained by hydrodistillation and analyzed by Multidimensional Gas Chromatography coupled with Mass Spectrometry (MDGC / MS). Candida species were obtained from lesions on the nails of horticulturist from a community garden in the city of Teresina, Piauí, Brazil. The antifungal activity in concentrations of 1000 µg/L, 500 µg/L and 250 µg/L, PROTOCOL M44-A2 (CLSI 2009) OEPh was tested. The main constituents identified were: l-limonene, α-terpineol, p-cineol, o-cymene and α-phellandrene, however, its composition varies significantly with extraction time. All species, except C. rugosa, were inhibited with halo (≥ 14 mm) at 1000 μg / L. C. krusei is naturally resistant to the drug fluconazole, but when tested with OEPh the clinical species (case 9) demonstrated sensitivity in three dilutions (halo ≤ 10 ≥ 14) and the standard strain was inhibited at concentration of 1000 μg/Lg / L (halo 14mm). A similar situation also occurred with the standard strain of C. parapsilosis (halo ≥ 11mm). OEPh has considerable antifungal activity, which merits further investigation for alternative clinical applications, since this species is widely distributed in our community, and it presents good yields, and also has important therapeutic applications.

RESUMO Protium heptaphyllum é encontrada na região amazônica, em vários estados do Brasil e países da América do Sul. Conhecida como almecega produz uma resina oleosa usada na medicina popular como analgésica, antiinflamatória, cicatrizante e expectorante, é rica em triterpenos pentaciclicos e óleo essencial. O objetivo principal do presente trabalho foi analisar a composição química do óleo essencial da resina P. heptaphyllum (OEPh) em diferentes tempo de extração e avaliarsuaatividade antifúngica contra espécies de Candida, isoladas de horticultores com onicomicoses, por método de disco-difusão. O OEPh foi obtido por hidrodestilação, analisado por Cromatografia Gasosa Multidimensinal Acoplada a Espectrometria de Massas (MDGC/MS). As espécies de Candida foram obtidas de lesões nas unhas de horticultores de uma horta comunitária na cidade de Teresina, Piauí, Brasil. Testou-se a atividade antifúngica do OEPhnas concentrações de 1000 μg/L, 500 μg/L e 250 μg/L, protocolo M44-A2 (CLSI 2009). Os principais constituintes identificados foram l- limoneno, α-terpineol, p-cineol, o-cimeno e α-felandreno, entretanto, sua composição varia significativamente em decorrência do tempo de extração. Todas as espécies, exceto a C. rugosa, foram inibidas com halo ( Χ ≥ 14 mm) na concentração de 1000 μg/L. C. krusei é naturalmente resistente ao fármaco fluconazol, mas quando testado com OEPh,a espécie clínico (caso 9) demonstrou sensibilidade nas três diluições (halo Χ ≤ 10 ≥ 14) e a cepa padrão foi inibida na concentração de 1000 μg/L (halo Χ 14mm). Fato semelhante também ocorreu com a cepa padrão de C. parapsilosis (halo Χ ≥ 11mm). O OEPh possui atividade antifúngica considerável, merecendo uma investigação mais aprofundada para aplicações clínicas alternativas, uma vez que esta espécie é amplamente distribuída em nossa comunidade, apresenta bom rendimento e, ainda, aplicações terapêuticas importantes.

A resina de protium heptaphyllum e seu principal constituinte, a mistura de triterpenosalfa e beta-amirina, previnem a obesidade induzida por dieta em camundongos: evidências e potenciais mecanismos

A obesidade, que se caracterizada pelo acúmulo excessivo de gordura corporal decorrente principalmente do aumento do consumo de alimentos calóricos e do sedentarismo, está associada a várias condições patológicas como doenças cardiovasculares, diabetes,desordens musculoesqueléticas e câncer. As opções farmacológicas para o tratamento da obesidade são limitadas e apresentam diversos efeitos colaterais. No Brasil apenas dois fármacos estão disponíveis, sibutramina e orlistate. Na busca de novas opções terapêuticas para o tratamento da obesidade, as plantas medicinais têm sido uma importante fonte de pesquisa, em especial os compostos terpênicos, conhecidos reguladores da glicemia e do metabolismo lipídico. O presente estudo investigou o efeito anti-obesidade da resina do Protium heptaphyllum (RPH) e de seu principal constituinte, a mistura de triterpenos alfa ebeta-amirina (AMI), na obesidade induzida por dieta hipercalórica em camundongos e seus possíveis mecanismos de ação. Foram utilizados camundongos Swiss, albinos, machos,pesando entre 20-25g, que após uma semana de livre acesso a ração padrão (Purina®,Brasil) foram divididos em 7 grupos de 10 animais e tratados com dieta padrão (DP), dieta hipercalórica (DH), DH+RPH 10mg/kg, DH+RPH 20mg/kg, DH+AMI 10mg/kg, DH+AMI 20mg/kg ou DH+sibutramina 10mg/kg (SIB) por 15 semanas. RPH e AMI foram inicialmente diluídas em 2% Tween 80 em água...

Obesity which is characterized by excessive accumulation of body fat mainly due to theincreased consumption of high-calorie foods and sedentary lifestyle is associated withvarious pathological conditions such as cardiovascular disease, diabetes, musculoskeletaldisorders and cancer. Pharmacologic options for the treatment of obesity are limited andhave many side effects. In Brazil only two drugs are available, sibutramine and orlistat. In thesearch for new therapeutic options for the treatment of obesity, medicinal plants have beenan important source of research, particularly the terpene compounds, known regulators ofblood glucose and lipid metabolism. This study investigated the antiobesity effect of Protiumheptaphyllum resin (RPH) and its main constituent, the mixture of triterpenes alpha and betaamyrin(AMY), in obesity induced by high calorie diet in mice and its possible mechanisms ofaction. Swiss albino male mice were used, weighing between 20-25g, which after a week offree access to standard chow (Purina®, Brazil) were divided into 7 groups of 10 animals eachand treated with standard diet (SD), high-fat diet (HFD), HFD+RPH 10mg/kg, HFD+RPH20mg/kg, HFD+AMY 10mg/kg, HFD+AMY 20 mg/kg or HFD+sibutramine 10mg/kg (SIB) for15 weeks. RPH and AMY were initially diluted in 2% Tween 80 in water...

Antibacterial activity and chemical compounds of leaves and branches of Protium hebetatum / Atividade anti bacteriana e compostos químicos das folhas e ramos de Protium hebetatum

ABSTRACT The extracts and fractions of leaves and branches of Protium hebetatum D. C. Daly (Burseraceae) were investigated for their antibacterial activity and chemical composition. The methanol extract of branches (EMG) was considered active against the Escherichia coli and the Proteus vulgaris, showing an inhibition zone of 13 mm, and was selected for bioassay-guided phytochemical fractionation. From the technique of broth microdilution, the extract was considered a moderate inhibitor against Staphylococcus aureus, Pseudomonas aeruginosa and Enterococcus faecalis, with a minimum inhibitory concentration (MIC) of 1 mg/mL. The dichloromethane fraction was considered a moderate inhibitor against S. aureus (MIC of 1 mg/mL) and a potent inhibitor against E. faecalis (MIC of 0.5 mg/mL). F1, F2, F5 and F6 from chromatographic column of dichloromethane fraction were considered moderate inhibitors against S. aureus (MIC of 1 mg/mL). Through analysis by a gas chromatography mass spectrometry, eighteen compounds were identified, from which thirteen (isoeugenol, p-vinylguaiacol, metoxyeugenol, coumarin, 5-hydroxy-scopoletin, 4,7-dihydroxy-6-metoxicromam-2-one, 4[(1E]-3-hydroxy-1-propenyl)-2-methoxyphenol, piperonal, scoparon, o-guaiacol, spathulenol, seringol and antiarol) are unprecedented in these species. We also identified the triterpenes α-amyrin and β-amyrin, the steroids stigmasterol and sitosterol and the coumarin scopoletin, which was closely linked to the antibacterial activity of the samples.

RESUMO Atividade antibacteriana e compostos químicos de folhas e galhos de Protium hebetatum. Extratos e frações de folhas e galhos de Protium hebetatum D. C. Daly (Burseraceae) foram investigados quanto sua atividade antibacteriana e composição química. O extrato metanólico dos galhos (EMG) foi considerado ativo contra Escherichia coli e Proteus vulgaris, apresentando um halo de inibição de 13 mm, sendo selecionado para um fracionamento fitoquímico biomonitorado. A partir da técnica de microdiluição em caldo o EMG foi considerado um inibidor moderado contra Staphylococcus aureus, Pseudomonas aeruginosa e Enterococcus faecalis, apresentando uma concentração inibitória mínima (CIM) de 1mg/mL. A fração diclorometânica foi considerada inibidora moderada contra S. aureus (CIM de 1 mg/mL) e inibidora potente contra E. faecalis (CIM de 0,5 mg/mL). F1, F2, F5 e F6 provenientes da fração diclorometânica foram consideradas inibidoras moderadas contra S. aureus (CIM de 1 mg/mL). Através da análise por cromatografia gasosa acoplada a espectrometria de massa, foram identificados dezoitos compostos, dos quais treze (isoeugenol, p-vinilguaiacol, metoxieugenol, cumarina, 5-hidroxi-escopoletina, 4,7-dihidroxi-6-metoxicromam-2-ona, 4[(1E]-3-hidroxi-1-propenil)-2-methoxifenol, piperonal, escoparona, o-guaiacol, espatulenol, seringol e antiarol) foram identificados pela primeira vez nesta espécie. Foram também identificados os triterpenos α-amirina e β-amirina, os esteroides estigmasterol e sitosterol e a cumarina escopoletina, que estão intimamente ligados à atividade antibacteriana da espécie.

Metabolitos volátiles presentes en Protium heptaphyllum (Aubl.) March. colectado en Tame (Arauca - Colombia) / Volatil metabolites of Protium heptaphyllum (Aubl.) March. from Tame (Arauca-Colombia)

This paper reports the identification of volatile components of the leaves, flowers, resin of the stem, and bark of the branches of the tree Protium heptaphyllum (Aubl.) March. collected from East Plains, Orinoquia, Colombia. The main constituents identified by GC-MS in the volatile fraction of the leaves were guaiol (14,4 percent), alpha-copaene (8,6 percent), 1,10-di-epi-cubenol (8,1 percent), beta-cariophyllene (5,7 percent), and gamma-cadinene (5,4 percent). Germacrene D (13,9 percent), germacrene B (13,4 percent), bicyclogermacrene (11,8 percent), and limonene (8,3 percent) were determined in the flowers, while p-cymene (30,1 percent), alpha-pinene (22,1 percent), and limonene (14,4 percent) were identified in the resin; finally, germacrene D (27,7 percent), 1,10-di-epi-cubenol (7,9 percent), guaiol (7,4 percent), and gamma-cadinene (6,9 percent) were found in the bark. The analysis of the resin showed a high percent of monoterpenes (- 60 percent); while the leaves presented a high content of oxygenated sesquiterpenes (- 60 percent); flowers and bark showed a high composition of sesquiterpenes (40-50 percent).

En este trabajo se reporta la identificación de los componentes volátiles de hojas, flores, resina del tallo y corteza de las ramas del árbol Protium heptaphyllum (Aubl.) March. recolectado en los Llanos Orientales, Orinoquía, Colombia. Los constituyentes mayoritarios identificados por GC-MS en la fracción volátil de las hojas fueron guaiol (14,4 por ciento), alfa-copaeno (8,6 por ciento), 1,10-di-epi-cubenol (8,1 por ciento), trans-beta-cariofileno (5,7 por ciento) gamma -cadineno (5,4 por ciento). Germacreno D (13,9 por ciento), germacreno B (13,4 por ciento), biciclogermacreno (11,8 por ciento) y limoneno (8,3 por ciento) se determinaron en las flores, mientras que, p-cimeno (30,1 por ciento), alfa-pineno (22,1 por ciento) y limoneno (14,4 por ciento) se identificaron en la resina; finalmente, germacreno D (27,7 por ciento), 1,10-di-epi-cubenol (7,9 por ciento), guaiol (7,4 por ciento) gamma -cadineno (6,9 por ciento) se encontraron en la corteza. El análisis de la resina mostró un alto porcentaje de monoterpenos (- 60 por ciento); mientras que, las hojas presentaron una alta proporción de sesquiterpenos oxigenados (- 60 por ciento); las flores y la corteza mostraron una alta composición de sesquiterpenos (40-50 por ciento).

Gastroprotective effects of essential oil from Protium heptaphyllum on experimental gastric ulcer models in rats

Peptic ulcers are a common disorder of the entire gastrointestinal tract, its etiology has not been completely elucidated. The basic physiopathological of peptic ulcers result from an imbalance between some endogenous aggressive factor and cytoprotective factors. The treatment of this disease is usually done with antacids or proton pump, but are currently being used plants derivated compounds. We evaluated the gastroprotective properties and its possible mechanisms of action of the essential oil from Protium heptaphyllum (Aubl.) Marchand, Burseraceae (BB). The formation of ulcers, were evaluated in three experimental models, through the induction of gastric lesions by ethanol, nonsteroidal anti-inflammatory drugs and acetic acid. The mechanisms of action were evaluated through the pylorus ligature experiment, western blot, GSH, GR, SOD, GPx, MDA and MPO activities. BB significantly inhibited the formation of ulcers induced by the three different models, increased the GSH and GR levels and maintained the same levels of SOD and GPx of the sham group, inhibited MPO and MDA, did not produce significant modification in gastric juice content and showed increased COX-2 and EGF. BB exerts its gastroprotective activity, possibly, by increasing COX-2 and EGF expression and due to its possible antioxidant property.

Chemical composition of the essential oils from two subspecies of Protium heptaphyllum / Composição química do óleo essencial de duas subespécies do Protium heptaphyllum

Qualitative and quantitative analyses of the volatile constituents from resin of Protium heptaphyllum (Aubl.) Marchand subsp. ulei (Swat) Daly (PHU), and Protium heptaphyllum (Aubl.) Marchand subsp. heptaphyllum (PHH), Burseraceae were performed using GC-MS and GC-FID. The resins were collected around the city of Cruzeiro do Sul, state of Acre, Brazil. Essential oils from the two subspecies were extracted by hydrodistillation with a yield of 8.6 percent (PHU) and 11.3 percent (PHH); the main components were terpinolene (42.31 percent) and p-cymene (39.93 percent) for subspecies ulei (PHU) and heptaphyllum (PHH), respectively.

As análises qualitativa e quantitativa dos óleos essenciais obtidos das resinas das espécies Protium heptaphyllum (Aubl.) Marchand subespécie ulei (Swat) Daly (PHU) e Protium heptaphyllum (Aubl.) Marchand subespécie heptaphyllum (PHH), Burseraceae, foram realizadas utilizando cromatografia em fase gasosa acoplado a um espectrômetro de massa (CG-EM) e cromatografia a gás com detector de chama (CG-DIC). As resinas foram coletadas no Município de Cruzeiro do Sul, Acre, Brasil. O óleo essencial das oleoresinas foi extraído por hidrodestilação fornecendo rendimento 8,6 por cento para PHU e 11,3 por cento para PHH. Os monoterpenos terpinoleno (42.31 por cento) e p-cimeno (39.93 por cento) foram os constituintes principais para PHU e PHH, respectivamente.

Antibacterial and cytotoxic properties of some plant crude extracts used in Northeastern folk medicine / Propriedades antibacterianas e citotóxicas de alguns extratos de plantas usados na medicina popular nordestina

In the present study, 32 hexane and ethanol extracts of Protium bahianum, P. heptaphyllum, Croton sellowii, C. rhamnifolius, C. jacobinensis, C. micans and Muntingia calabura were screened for antibacterial activity by the disc-diffusion method. Cytotoxicity assays using the brine shrimp Artemia salina Leach as a model were performed to determine lethal doses for 50 percent of individuals (LC50 µg/mL). Antibacterial activity was found in flowers hexane extracts of M. calabura against B. subtilis, and leaves ethanol extracts against S. aureus and B. subtilis at concentration of 1mg/mL. Among 32 extracts, 19 showed low or no toxicity (LC50 > 250 µg/mL), 6 showed moderate toxicity (LC50 between 80 µg/mL and 250µg/mL), and 7 were highly toxic (LC50 < 80 µg/mL).

No presente estudo, 32 extratos hexânicos e etanólicos de Protium bahianum, P. heptaphyllum, Croton sellowii, C. rhamnifolius, C. jacobinensis, C. micans e Muntingia calabura, foram avaliados para atividade antibacteriana, pelo método de difusão em disco. Ensaios de citoxicidade foram realizados com o modelo do microcrustáceo Artemia salina Leach para determinar a concentração letal para 50 por cento dos indivíduos (CL50 µg/mL). A presença de atividade antibacteriana foi observada com os extratos hexânicos das flores de M. calabura contra B. subtilis, e extratos etanólicos das folhas contra S. aureus and B. subtilis na concentração de 1 mg/mL. Dentre os 32 extratos, 19 apresentaram toxicidade baixa ou ausente (CL50 > 250 µg/mL), 6 mostraram toxicidade moderada (CL50 entre 80 µg/mL e 250 µg/mL) e 7 foram muito tóxicos (CL50 < 80 µg/mL).

Chemical composition and acaricidal activity of the leaf and fruit essential oils of Protium heptaphyllum (Aubl. ) Marchand (Burseraceae)

Essential oils from leaves and fruits of Protiumheptaphyllum collected in Tamandaré beach Pernambuco/Brazil were analysed by GC/MS and tested for toxicity and repellent effect against the two spotted spider mite (Tetranychus urticae). The major constituent identified in the fruits was alpha-terpinene (47.6 percent) whereas oil from leaf contained mainly sesquiterpenes such as 9-epi-caryophyllene (21.4 percent), trans-isolongifolanone (10.7 percent) and 14-hydroxi-9-epi-caryophyllene (16.7 percent). The fruit oil was found to be more effective against the mite when compared to the leaf oil. Both showed mortality properties and oviposition deterrence in higher concentration (10 µl.l-1 air), but only the essential oil from fruits induced repellence on T. urticae.

O óleo essencial das folhas e frutos de Protiumheptaphyllum coletada em Tamandaré-Pernambuco foi analisado por CG/EM e testado sua toxicidade e efeito repelente contra ácaro rajado (Tetranychus urticae). O constituinte majoritário identificado nos frutos foi alfa-terpineno (47,6 por cento) enquanto que nas folhas foram os sesquiterpenos 9-epi-cariofileno (21,4 por cento), trans-isolongifolanona (10,7 por cento) and 14-hidroxi-9-epi-cariofileno (16,7 por cento). O óleo dos frutos foi mais eficiente contra o ácaro, comparado com o óleo das folhas. Ambos os óleos revelaram propriedades de mortalidade e deterrência de oviposição na maior concentração (10 µl.l-1 air) e apenas o óleo essencial dos frutos induziu repelência no T. urticae.

Mel Amargo de Breu (Protium sp., Burseraceae)

A sample of bitter a honey collected in the Mucajaí county (Roraima, Brazil) forest of Apiaú, was analysed. The pollen analysis revealed a predominance of Protium pollen, comprising 60,9% of the total of pollen grains.

Foi analisada uma amostra de mel amargo procedente do Município de Mucajaí (Roraima, Brasil), Floresta de Apiaú. A análise polínica constatou a dominância de pólen de breu (Protium sp.) compreendendo 60,9% do total de grãos de pólen.

CONSTITUÍNTES QUÍMICOS DE Protium paniculatum(BURSERACEAE)

- and -amyrin (0,012%), -sitosterol and stigmasterol (0.003%),3,3'-di-O-methylellagic acid (0.093%) were isolated from the bark wood of Protium paniculatum.The presence of 3,3',4-tri-O-methylellagic acid was postulate on the basis of mass spectral analyses.

Dos extratos etéreo e etanólico da casca da madeira de Protium paniculatumEngl. foram isolados - e -amirina (0,012%), -sitosterol e estigmasterol (0,003%) e o ácido 3,3'-di-O-metilelágico (0,093%0). A presença do ácido 3,3',4-tri-O-metilelágico foi postulada com base na análise do espectro de massas.

ESSENTIAL OIL OF Protium unifoliolatum (BURSERACEAE)

The major constituents of the leaf essential oil of P. unifoliolatumare trans-caryophyllene (37.45%), limonene (24.23%) and -humulene (9.94%).

O óleo essencial obtido das folhas frescas de P. unifoliolatumapresentou como constituintes principais trans-cariofileno (37,45%), limoneno (24,23%) e -humuleno (9,94%).

CONSTITUINTES QUÍMICOS DE Protium paniculatum (BURSERACEAE)

á- e -myrin (0,012%), -sitosterol and stigmasterol (0.003%),3,3'-di-0-methylellagic (0.093%) acid were isolated from the bark wood of Protium paniculatum. The presence of 3.3',4-tri-0-methylellagic acid was postulate on the of mass spectral analyses.

Dos extratos etéreo e etanólico da casca da madeira de Protium paniculatum Engl. foram isolados á e -AMIRINA (0,012%), -sitosiero! e estigmasterol (0,003%) e o ácido 3,3'-di-0-metilelágico (0,093%0). A presença do ácido 3,3',4-tri-0-metileIágico foi postulada com base na análise do espectro de massas.