Composición química y actividad AChE-BuChE del aceite esencial de palo santo Bursera graveolens (Kunth) Triana & Planch de Jipijapa, Ecuador / Chemical composition and AChE-BuChE activities of the essential oil of palo santo Bursera graveolens (Kunth) Tr iana & Planch from Jipijapa, Ecuador

Abstract: This article describes the chemical composition, physical properties and acetylcholinesterase (A ChE) and butyrylcholinesterase (BuChE) activity of stem - distilled essential oil (E O ) from Bursera graveolens wood chips, Burseraceae. The plant material was acquired in Quimis (Bosque de Sancán), city of Jipijapa in the province of Manabí, coastal region o f Ecuador. Thirty - six components were identified by CG - MS, which represented 98.54% of the volatile oil. The main components were limonene (68.52%) and mentofuran (20.37%). The hydrocarbon monoterpenes constituted the most abundant fractions. The average y ield of the E O was 1.26%. Regarding the physical properties of E O , the following values were obtained: relative density (1,029 g/mL), refractive index (1,477) and specific rotation (+4,567). The E O presented IC 50 inhibition values of 47.2 and 51.9 µg/mL fo r the enzymes AChE and BuChE, respectively.

Resumen: Este artículo describe la composición química, propiedades físicas y actividad acetilcolinesterasa (AChE) y butirilcolinesterasa (BuChE) del aceite esencial (AE) destilado a vapor de astillas de madera de Bursera graveolens , Burseraceae. La materia vegetal fue adquirida en Quimis (Bosque de Sancán), ciudad de Jipijapa en la provincia de Manabí, región costera d e Ecuador. Treinta y seis componentes fueron identificados por CG - MS, que representaron al 98.54 % del aceite volátil. Los componentes principales fueron limoneno (68.52%) y mentofurano (20.37%). Los monoterpenos hidrocarburos constituyeron las fracciones m ás abundantes. El rendimiento medio del AE fue de 1.26%. Con respecto a las propiedades físicas del AE se obtuvo los siguientes valores, densidad relativa (1.029 g/mL), índice de refracción (1.477) y rotación específica (+4.567). El AE presentó valores de inhibición IC 50 de 47.2 y 51.9 µg/mL para las enzimas AChE y BuChE, respectivamente.

Volatile chemical composition of essential oil from Bursera graveolens (Kunth) Triana & Planch and their fumigant and repellent activities

The objectives of this work were the study of the volatile chemical composition of essential oils (EO’s) from Bursera graveolens obtained in the locality of Malagana, municipality of Mahates, Bolívar, Colombia, as well as to evaluate their repellent and fumigant properties. EO’s were extracted by hydro-distillation and characterized by gas chromatography-mass spectrometry (GC-MS). The major compounds found in B. graveolens were limonene (42.2%), pulegone (20.9%), carvone (7.5%), caryophyllene (4.1%), and trans-carveol (3.8%). The repellent activity of EO’s was determined by the area preference method, where the EO of B. graveolens presented repellent activity against the Tribolium castaneum weevil at a concentration of 1 at 2% and 4 hours of exposure (88.1 and 88.6% respectively). B. graveolens essential oil was more effective in its fumigant activity with LC50 of 108.2 μg oil mL-1. Also, the fumigant and repellent activities of two individual compounds present in the oil were evaluated, that is, limonene (majority) and caryophyllene. The results indicated that B. graveolens essential oil could be a promising alternative to new natural repellents and biocides.

Análisis multivariable y variabilidad química de los metabolitos volátiles presentes en las partes aéreas y la resina de Bursera graveolens (Kunth) Triana & Planch. de Soledad (Atlántico, Colombia) / Multivariate analysis and chemical variability of the volatile metabolites present in the aerial parts and the resin of Bursera graveolens (Kunth) Triana & Planch from Soledad (Atlántico, Colombia)

The aim of this study was to determine the chemical compositions of the volatile fractions from the immature fruits, leaves, branches, stem bark and resin of Bursera graveolens (Kunth) Triana & Planch. by SDE-GC/MS and their relationship through the multivariate statistical analysis. The most abundant constituents found in the volatile fractions were: (a). Fruits – 3-hydroxy-mint furanone (6.7 percent), mint furanone (6.4 percent), carvone (5.3 percent), limonene (4.2 percent), trans-carveol (4.1), limonene-1,2-diol (3.8 percent), limonene dioxide derivative (3.7 percent), 2-hydroperoxide-2S,4R-p-mentha-6,8-diene (3.4 percent) and caryophyllene oxide (3.0 percent); (b). Leaves – germacrene D (20.7 percent), -caryophyllene (18.0 percent), viridiflorol (8.0 percent), limonene (6.6 percent), linalool (6.5 percent) and dendrolasin (5.3 percent); (c). Branches – mint furanone (43.9 percent), iso-mint furanone (6.8 percent), 3-hydroxy mint furanone (6.2 percent); (d.) Stem bark – mint furanone (44.6 percent), 3-hydroxy-mint furanone (16.2 percent), iso-mint furanone (6.4 percent); and, (e.) Resin – limonene (23.2 percent), mint furanone (15.9 percent), mint furanone derivative (14.8 percent), pulegone (12.1 percent), 3-hydroxy-mint furanone (8.6 percent), and menthofuran (6.2 percent). The principal component analysis (70 percent of related information) and cluster analysis applied to the data allowed to find 3 groups: I. – fruits; II. – leaves; and, III. – resin, stem bark and branches; the latter group showed a close compositional relationship. Thus, the volatile fractions in the branches and stem bark were represented by benzofuranoids compounds (60-69 percent); in the leaves by sesquiterpenoids (60 percent); in the fruits by monoterpenoids (54 percent); and, in the resin by benzofuranoids (48 percent) and monoterpenoids (42 percent).

El objetivo de este estudio fue determinar las composiciones químicas de las fracciones volátiles de los frutos inmaduros, hojas, ramas, corteza del tallo y resina de Bursera graveolens (Kunth) Triana & Planch. mediante SDE-GC/MS y su relación a través de análisis estadístico multivariable. Los constituyentes más abundantes encontrados en las fracciones volátiles fueron: (a). Frutos – 3-hidroxi-mentofuranona (6.7 por ciento), mentofuranona (6.4 por ciento), carvona (5.3 por ciento), limoneno (4.2 por ciento), trans-carveol (4.1 por ciento), limonen-1,2-diol (3.8 por ciento), derivado de dióxido de limoneno (3.7 por ciento), 2-hidroperóxido-2S,4R-p-menta-6,8-dieno (3.4 por ciento) y óxido de cariofileno (3.0 por ciento); (b). Hojas – germacreno D (20.7 por ciento), trans--cariofileno (18.0 por ciento), viridiflorol (8.0 por ciento), limoneno (6.6 por ciento), linalol (6.5 por ciento) y dendrolasina (5.3 por ciento); (c). Ramas – mentofuranona (43.9 por ciento), iso-mentofuranona (6.8 por ciento), 3-hidroxi-mentofuranona (6.2 por ciento); (d.) Corteza del tallo – mentofuranona (44.6 por ciento), 3-hidroxi-mentofuranona (16.2 por ciento), iso-mentofuranona (6.4 por ciento); y, (e.) Resina – limoneno (23.2 por ciento), mentofuranona (15.9 por ciento), mentofuranona derivado (14.8 por ciento), pulegona (12.1 por ciento), 3-hidroxi-mentofuranona (8.6 por ciento) y mentofurano (6.2 por ciento). El análisis de componentes principales (70 por ciento de información relacionada) y de conglomerado, aplicado a los datos permitió encontrar 3 grupos: I. – frutos; II. – hojas; y, III. – resina, corteza del tallo y ramas; este último grupo mostró estrecha relación composicional. Así, las fracciones volátiles estuvieron representadas por compuestos benzofuranoides (60-69 por ciento) en las ramas y corteza del tallo; por sesquiterpenoides (60 por ciento) en las hojas; por monoterpenoides (54 por ciento) en los frutos; y, por benzofuranoides (48 por ciento) y monoterpenoides...

Efecto antiinflamatorio y composición química del aceite de ramas de bursera graveolens triana & planch. (palo santo) de Ecuador / Antinflammatory effect and chemical composition of bursera graveolens triana & planch. branch oil (palo santo) from Ecuador

INTRODUCCIÓN: la especie Bursera graveolens Triana & Planch, comúnmente llamada palo santo, es una planta nativa de las costas ecuatorianas y peruanas. OBJETIVOS: contribuir al estudio fitoquímico y farmacológico de la especie B. graveolens, nativa de San José de Ancón, provincia de Santa Elena, Ecuador. MÉTODOS: se empleó el extracto hidroalcohólico 50 porciento de ramas secas. Se realizó un estudio fitoquímico a través del sistema acoplado de cromatografía gaseosa-espectrometría de masas y se determinó el efecto antiinflamatorio en el modelo de edema de la oreja inducido por aceite de Crotón en ratones albinos de la línea OF1. RESULTADOS: el tamizaje fitoquímico mostró presencia de aceites esenciales, triterpenos-esteroides, compuestos fenólicos, flavonoides, quinonas, antocianidinas, saponinas y compuestos reductores. Se determinó estructuras a 11 componentes del aceite esencial extraído de las ramas y el sesquiterpeno denominado viridiflorol resultó el componente mayoritario con 70,82 porciento, este compuesto se informa por primera vez en esta especie. El extracto hidroalcohólico (25 mL a cada lado de las orejas tratadas) inhibió significativamente la inflamación comparado con la bencidamina. CONCLUSIONES: los extractos hidroalcohólicos mostraron un efecto antiinflamatorio en las condiciones experimentales del estudio y se determinó la composición química del aceite de ramas de B. graveolens de Ecuador.

INTRODUCTION: Bursera graveolens Triana & Planch. species, commonly called palo santo, is an indigenous plant from Ecuadorian and Peruvian coasts. OBJECTIVES: to contribute to the phytochemical and pharmacological study of B. graveolens species from San José de Ancon, Santa Elena province, Ecuador. METHODS: 50 percent hydroalcoholic extract from dry branches was used. The phytochemical study was based on a combined system of gas chromatography-mass spectrometry and the antinflammatory effect was determined in the model of ear edema induced by Croton oil in albino OF1 mice. RESULTS: phytochemical screening showed the existence of essential oils, triterpen-steroids, phenolic compounds, flavonoids, quinones, antocyanidines, saponins and reducing compounds. The structures of eleven essential oil components from branches were determined whereas sesquiterpene called viridiflorol turned out to be the main component with 70,82 percent; this is the first time that this compound is reported in this species. The hydroalcoholic extract (25 mL applied at each side of the treated ears) significantly inhibited the inflammation compared with the effect of benzydamine. CONCLUSIONS: hydroalcoholic extracts showed antinflammatory effect under experimental study conditions and the chemical composition of branch oil from B. graveolens from Ecuador was determined.

Triterpenos aislados de corteza de Bursera graveolens (Burseraceae) y su actividad biologica

Bursera graveolens (Burseraceae), known in Colombia as "sasafrás", is useful for its medicinal properties and is rich in secondary metabolites. In our research, we carried out antimicrobial tests of several fractions and ethanolic extracts from aerial parts against Bacillus subtilis and Staphylococcus aureus, that showed growth inhibitory activity when applied at 250 mg/mL for extracts and 150 mg/mL for fractions. We carried out an antiinflamatory assay also, that showed 71 por ciento of inhibition by extracts (81 por ciento of Indomethacin) and 70 por ciento of inhibition by fractions (78 por ciento of Indomethacin). Phytochemical investigation of the bark of Bursera graveolens (Burseraceae) yielded three tetracyclic triterpene acids that have oxygenation in C-3, carboxylic acid in C-21 and unsaturation in C-24 and have been identified as 3-oxotirucalla-8,24-dien-21-oic acid (b-elemonic acid), 3a-hydroxytirucalla-8,24-dien-21-oic acid (a-elemolic acid) and 3a-hydroxytirucalla-7,24-dien-21-oic acid. The isolated compounds were identified using spectroscopic methods including one and two-dimensional Nuclear Magnetic Resonance (COSY, HMQC, HMBC, NOESY) experiments and comparison with published data. This is the first report of the isolated compounds in Bursera graveolens and they have a very important chemotaxonomic significance within the Burseraceae family and related families from the order Rutales.