Chemical composition and larvicidal activity of the essential oil of Pimenta dioica leaves / Composición química y actividad larvicida del aceite esencial de hojas de Pimenta dioica

In this study, we investigated the main constituent, the predominant class and biological activity of the essential oil extracted from the leaves of Pimenta dioica and the pattern of the major constituent against larvae in the third stage of Aedes aegypti. For this reason, we extracted the oil by hydrodistillation, identified its components by gas chromatography coupled with mass spectrometry (GC/MS) and calculated the lethal concentration (LC50) of the larvicidal activity using the Reed-Muench method. The results show that the oil consists mainly of eugenol, in which the phenylpropanoid class predominated and the lethal concentration, LC50, was 38.86 µg mL-1at a confidence level of 2.25 µg mL-1, while the eugenol standard presented LC5079.75 µg mL-1at a confidence level of 2.10 µg mL-1. Given the facts, we conclude that the oil is more active than the standard and that it has the potential to replace chemical larvicides.

En este estudio, investigamos el constituyente principal, la clase predominante y la actividad biológica del aceite esencial extraído de las hojas de Pimenta dioica y el patrón del constituyente principal contra las larvas en la tercera etapa de Aedes aegypti. Por este motivo, extrajimos el aceite por hidrodestilación, identificamos sus componentes mediante cromatografía de gases acoplada a espectrometría de masas (GC/MS) y calculamos la concentración letal (CL50) de la actividad larvicida mediante el método Reed-Muench. Los resultados muestran que el aceite está constituido principalmente por eugenol, en el que predominó la clase fenilpropanoide y la concentración letal, CL50, fue de 38,86 µg.mL-1 a un nivel de confianza de 2,25 µg.mL-1, mientras que el estándar de eugenol presentó CL50 79,75 µg.mL -1 a un nivel de confianza de 2,10 µg.mL-1. Dados los hechos, concluimos que el aceite es más activo que el estándar y que tiene el potencial de reemplazar los larvicidas químicos.

Leaf and fruit essential oil compositions of Pimenta guatemalensis (Myrtaceae) from Costa Rica / Aceites volátiles de hojas y frutos de Pimenta guatemalensis (Myrtaceae) de Costa Rica

Pimenta is a genus of flowering plants in the Myrtaceae family, which has about 15 species, mostly found in the Caribbean region of the Americas. Commonly used for culinary and medicinal purposes, the best known commercial species are allspice, P. dioica (P. officinalis) and bay rum, P. racemosa, but there is little information concerning P. guatemalensis. The aim of the present study was to identify the chemical composition of the leaf and fruit essential oils of P. guatemalensis. The extraction of essential oils of P. guatemalensis growing wild in Costa Rica was carried out by the hydrodistillation method at atmospheric pressure, using a modified Clevenger type apparatus. The chemical composition of the oils was analyzed by capillary gas chromatographyflame ionization detector (GC/FID) and gas chromatography-mass spectrometry (GC/MS) using the retention indices on DB-5 type capillary column. A total of 103 and 63 compounds were identified in the leaf and fruit oils, respectively, corresponding to 96.8% and 86.1% of the total amount of the oils. The leaf oil consisted mainly of eugenol (72.8%), and mono- and sesquiterpene hydrocarbons (18.2%). Among terpenes the major components were β-caryophyllene (8.2%) and terpinolene (3.0%). The fruit oil also consisted mainly of eugenol (74.7%) and minor amounts of oxygenated mono- and sesquiterpenes (7.3%), mainly caryophyllene oxide (3.3%). This is the first report of the chemical composition of the essential oils obtained from this plant species. Rev. Biol. Trop. 63 (1): 303-311. Epub 2015 March 01.

Pimenta es un género de plantas perteneciente a la familia Myrtaceae que contiene cerca de 15 especies, la mayoría ubicadas en las regiones del Caribe del Continente Americano, donde es utilizado con propósitos culinarios y medicinales. Las especies comerciales mejor conocidas son “pimienta de Jamaica” (P. dioica o P. officinalis) y “bay-rum” (P. racemosa) y existe muy poca información científica acerca de la especie P. guatemalensis. Cuando las hojas y frutos son triturados, desprenden un aroma de composición desconocida. El objetivo del presente estudio fue identificar la composición química de los aceites esenciales de las hojas y frutos de P. guatemalensis. La extracción de los aceites esenciales de P. guatemalensis, una especie arbórea silvestre en Costa Rica, se efectuó mediante el método de hidrodestilación a presión atmosférica, empleando un aparato de vidrio de tipo Clevenger. Se analizó la composición química de los aceites esenciales mediante cromatografía de gases con detector de ionización de flama (GC/FID) y cromatografía de gases acoplada a un detector de masas (GC/MS) y, utilizando índices de retención en una columna cromatográfica capilar tipo DB-5. En los aceites de hojas se identificaron 103 y en los de frutos 63 compuestos, correspondiendo a 96.8% y 86.1%, respectivamente, de los constituyentes totales. El aceite de las hojas está constituido principalmente por compuestos de naturaleza fenilpropanoide (72.9%) y de hidrocarburos monoterpénicos y sesquiterpénicos (18.2%). Los componentes mayoritarios del aceite de las hojas se identificaron como eugenol (72.8%), β-cariofileno (8.2%) y terpinoleno (3.0%). El aceite de los frutos está constituido principalmente por eugenol (74.7%), monoterpenos y sesquiterpenos oxigenados (7.3%) principalmente óxido de cariofileno (3.3%). Este es el primer informe acerca de la composición química de aceites esenciales obtenidos a partir de esta especie vegetal.

Pimenta pseudocaryophyllus inhibits virulence factors and promotes metabolic changes in Candida yeast

Introduction This is the first study to examine the in vitro susceptibility and the expression of virulence factors in Candida species in the presence of Pimenta pseudocaryophyllus (Gomes) L.R. Landrum (Myrtaceae), a Brazilian plant known as paucravo. Additionally, the mechanisms of action of the crude ethanol extract and the ethyl acetate and aqueous fractions of this plant were investigated. Methods The in vitro susceptibility of Candida was tested using the broth microdilution method, whereas an XTT reduction assay was used for biofilms. Adherence was determined by counting the number of yeast cells that adhered to 100 oral epithelial cells, and hyphal formation was verified in the hyphal induction medium M199. Flow cytometry with propidium iodide and FUN-1 was performed to assess the mechanism of action. Results The results revealed that the crude ethanol extract and the ethyl acetate and aqueous fractions of P. pseudocaryophyllus inhibited the growth of Candida isolates at a minimal inhibitory concentration (MIC) ranging from 64 to 256µg/mL, whereas the 50% sessile minimal inhibitory concentration (SMIC50) ranged from 512 to >1,024µg/mL. Adherence and hyphal formation were significantly reduced in the presence of the crude ethanol extract and both fractions. Although cell membrane injury was detected, the predominant mechanism of action appeared to be the alteration of yeast metabolism, as demonstrated by flow cytometry. Conclusions Our results indicated that antifungal activity reduced the expression of virulence factors in yeast via the alteration of yeast metabolism, suggesting that the crude extract of P. pseudocaryophyllus and its fractions may contain novel antifungal agents. .

Componentes volátiles de las hojas de Pimenta racemosa var racemosa(Mill. ) JW Moore (Myrtaceae) de Táchira – Venezuela / Volatile compounds of Pimenta racemosa var racemosa (Mill. ) JW Moore (Myrtaceae) leaves from Táchira-Venezuela

Pimenta racemosa var. racemosa (Mill.) J.W. Moore, is a Caribbean arboreal plant belonging to the family Myrtaceae with a special interest in their leaves for the production of essential oil, commonly known as "Bay-Rum". Steam distillation of fresh leaves collected in April 2012 produced two types of essential oil, one of these resulted lighter than water and was named (AL) and the other one heavier than water (AP). Gas chromatography/mass spectrometry analysis showed the presence of 17 components constituting 99.9 percent for AL, being the major compounds: eugenol (60.4 percent), myrcene (11.7 percent), chavicol (6.0 percent), limonene (5.4 percent) and linalool (4.4 percent); for the AP, 13components were identified (98.3 percent) from which eugenol (82.9 percent) and chavicol (9.3 percent) were in major proportions.

Pimenta racemosa var. racemosa (Mill.) J.W. Moore, es una planta caribeña, arbórea, perteneciente a la familia Myrtaceae y con un especial interés en sus hojas para la producción del aceite esencial comúnmente conocido como “Bay-Rum”. La destilación por arrastrecon vapor de las hojas frescas colectadas en abril 2012 produjo dos tipos de aceites esenciales, uno ligero (AL) y otro más pesado que elagua (AP). El análisis de sus componentes volátiles por cromatografía de gases/espectrometría de masas mostró 17 componentes lo que constituye el 99,9 por ciento del AL de los cuales los mayoritarios fueron eugenol (60,4 por ciento), mirceno (11,7 por ciento), chavicol (6,0 por ciento), limoneno (5,4 por ciento) ylinalool (4,4 por ciento); para el AP, 13 componentes fueron identificados (98,3 por ciento) de los cuales eugenol (82,9 por ciento) y chavicol (9,3 por ciento) fueron los mayoritarios.

Gênero Pimenta: aspectos botânicos, composição química e potencial farmacológico / Pimenta genus: botanical aspects, chemical composition and pharmacological potential

A família Myrtaceae possui representantes de grande interesse medicinal e o gênero Pimenta é um dos que merecem destaque. A maioria das espécies desse gênero é nativa da América Central, com exceção da Pimenta pseudocaryophyllus (Gomes) L. R. Landrum, nativa nas regiões centro-oeste e sudeste do Brasil. O presente estudo teve como objetivo revisar aspectos botânicos, químicos e farmacológicos descritos na literatura sobre o gênero Pimenta. Os dados foram obtidos de artigos originais e revisões indexadas nas bases Periódicos Capes, ISI Web of Knowledge, Bireme e SciELO. As espécies desse gênero podem ser arbustivas ou arbóreas, possuem pelos unicelulares, folhas usualmente coriáceas, inflorescência em dicásio ou panícula e são distinguidas, principalmente, pela estrutura do ovário. As propriedades farmacológicas são conferidas, principalmente, pelos óleos essenciais que são constituídos, na maioria, por derivados fenilpropanóides, monoterpenos, aldeídos monoterpênicos e alcoóis monoterpênicos. Dentre as propriedades farmacológicas apresentadas por espécies desse gênero destacam-se as anti-hipertensivas, anti-inflamatórias, analgésicas, antimicrobianas e antioxidantes. Das quinze espécies de Pimenta conhecidas, a Pimenta dioica (L.) Merrill e a Pimenta racemosa (Miller) J. Moore são as espécies de maior importância econômica e, por esse motivo são as mais estudadas do ponto de vista químico e farmacológico.

The family Myrtaceae has representatives of great medical interest, and the genus Pimenta deserves attention. Most species of this genus are native to the Central America, except Pimenta pseudocaryophyllus (Gomes) L. R. Landrum, which is native to the Central-West and Southeast Brazilian Regions. This study aimed to review botanical, chemical and pharmacological aspects described in the literature for Pimenta genus. Information was obtained from original papers and reviews indexed in the databases "Periódicos Capes", ISI Web of Knowledge, "Bireme" and SciELO. This genus can present shrubs or trees, which have unicellular hairs, usually coriaceous leaves and dichasium or panicle inflorescence, and are mainly distinguished by the ovary structure. The pharmacological properties are mostly due to essential oils, mainly consisted of phenylpropanoid, monoterpene, monoterpenic aldehyde and alcohol derivatives. Among these properties, antihypertensive, anti-inflammatory, analgesic, antimicrobial and antioxidant ones are highlighted. Of the fifteen known Pimenta species, Pimenta dioica (L.) Merrill and Pimenta racemosa (Miller) J. Moore have the greatest economic importance and consequently have been the most chemically and pharmacologically studied.