RESUMEN

BACKGROUND: Terpinolene, a monoterpene that is naturally found in a variety of herbs, is widely used as a flavoring agent in the industry. Although it's well established in the literature that terpinolene is an important component of plant extracts, the biological properties and the potential therapeutic use of this compound remain poorly explored. PURPOSE: This work aimed to answer the following guiding question: "What are the biological activities of terpinolene demonstrated through in silico, in vitro, and in vivo assays?". STUDY DESIGN AND METHODOLOGY: A systematic review was carried out in four electronic databases (Embase, Web of Science, Scopus, and PubMed) according to the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) guidelines, using the following search terms: terpinolene "AND" activity "OR" properties "OR" therapeutic "OR" treatment. This search included manuscripts published between 1960 and June 2020. Study selection was conducted by two independent reviewers according to predefined criteria. RESULTS: The initial search found a total of 2449 articles. However, only 57 of them were selected as they met the inclusion criteria and answered the guiding question. The analysis of these studies indicated that terpinolene presents a series of biological effects, from which the antioxidant, larvicide, and insecticide activities stand out. Despite the evidence demonstrating that terpinolene has the potential to be used in a broad pharmacological context, the mechanisms underlying its cellular and molecular effects remain to be better elucidated. In addition, the in vivo efficacy and safety of the administration of this compound have been poorly evaluated through either preclinical and clinical trials. Therefore, this study highlights the importance of characterizing the biological aspects and mechanisms of action of this natural compound. CONCLUSION: The data summarized in the present systematic review demonstrates the pharmacological potential of terpinolene. Nevertheless, most studies included in this review provide a superficial characterization of terpinolene biological effects and therefore, further research elucidating its mechanism of action and potential therapeutic benefits through preclinical and clinical trials are required. Nevertheless, due to its wide range of different biological activities, terpinolene will certainly attract the interest of scientific research, which could significantly contribute to the development of new products with both therapeutic and environmental applications.

Asunto(s)

Publicaciones , Simulación por Computador , Monoterpenos Ciclohexánicos

RESUMEN

Protium heptaphyllum (Burseraceae) oleoresins are rich in volatile monoterpenes, exhibiting a chemical composition that can be strongly altered with time. The present work aimed to discuss the temporal change of the volatile composition of these oleoresins, and search for related supporting evidence. Samples of P. heptaphyllum oleoresin were collected separately for fresh (n = 10) and aged (n = 8) oleoresins, with the essential oils obtained by hydrodistillation analyzed by GC-FID and GC-MS. Fresh oleoresins were characterized by a high content of terpinolene (28.2-69.7%), whereas aged ones contained large amounts of p-cymene (18.7-43.0%) and p-cymen-8-ol (8.2-31.8%). Multivariate analyses were performed based on the yield and major essential oil components to clearly demonstrate the existence of two subsets (fresh and aged oleoresins). In addition, an analysis of the partial genome sequencing of the species was carried out, producing the largest amount of data for the genus Protium. Subsequently, were searched for nucleotide sequences responsible for the enzymes involved in the biosynthesis of monoterpenes. Two hypotheses were formulated to understand the oxidation process during aging of the oleoresins: (i) a natural chemical oxidation of terpenes and (ii) an oxidation catalyzed by enzymes produced by microorganisms associated with the plant. The results suggested that terpinolene was most likely oxidized to p-cymene, which, in turn, was oxidized into p-cymen-8-ol during natural aging of the exudate due to abiotic factors.

Asunto(s)

Burseraceae/química , Monoterpenos/aislamiento & purificación , Extractos Vegetales/química , Monoterpenos Ciclohexánicos , Cimenos , Cromatografía de Gases y Espectrometría de Masas , Monoterpenos/química , Monoterpenos/metabolismo , Aceites Volátiles/química , Oxidación-Reducción , Terpenos/análisis , Terpenos/metabolismo

RESUMEN

Pharmacological treatment of inflammatory pain is usually done by administration of non-steroidal anti-inflammatory drugs (NSAIDs). These drugs present high efficacy, although side effects are common, especially gastrointestinal lesions. One of the pharmacological strategies to minimize such effects is the combination of drugs and natural products with synergistic analgesic effect. The monoterpene terpinolene (TPL) is a chemical constituent of essential oils present in many plant species, which have pharmacological activities, such as analgesic and anti-inflammatory. The association of ineffective doses of TPL and diclofenac (DCF) (3.125 and 1.25 mg/kg po, respectively) presented antinociceptive and anti-inflammatory effects in the acute (0, 1, 2, 3, 4, 5 and 6 h, after treatment) and chronic (10 days) inflammatory hyperalgesia induced by Freund's complete adjuvant (CFA) in the right hind paw of female Wistar rats (170-230 g, n=6-8). The mechanical hyperalgesia was assessed by the Randall Selitto paw pressure test, which determines the paw withdrawal thresholds. The development of edema was quantified by measuring the volume of the hind paw by plethismography. The TPL/DCF association reduced neutrophils, macrophages and lymphocytes in the histological analysis of the paw, following a standard staining protocol with hematoxylin and eosin and the counts were performed with the aid of optical microscopy after chronic oral administration of these drugs. Moreover, the TPL/DCF association did not induce macroscopic gastric lesions. A possible mechanism of action of the analgesic effect is the involvement of 5-HT2A serotonin receptors, because ketanserin completely reversed the antinociceptive effect of the TPL/DCF association. These results suggest that the TPL/DCF association had a synergistic anti-inflammatory and analgesic effect without causing apparent gastric injury, and that the serotonergic system may be involved in the antinociceptive effect of this association.

Asunto(s)

Animales , Femenino , Analgésicos/farmacología , Antiinflamatorios no Esteroideos/farmacología , Diclofenaco/farmacología , Inflamación/tratamiento farmacológico , Dolor/tratamiento farmacológico , Terpenos/farmacología , Enfermedad Crónica , Combinación de Medicamentos , Sinergismo Farmacológico , Edema/tratamiento farmacológico , Adyuvante de Freund , Hiperalgesia/tratamiento farmacológico , Hiperalgesia/patología , Inflamación/inducido químicamente , Inflamación/patología , Dimensión del Dolor , Dolor/patología , Ratas Wistar , Reproducibilidad de los Resultados , Estómago/efectos de los fármacos , Factores de Tiempo , Resultado del Tratamiento

RESUMEN

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.

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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.

Asunto(s)

Frutas/química , Aceites Volátiles/química , Pimenta/química , Hojas de la Planta/química , Aceites de Plantas/química , Costa Rica , Cromatografía de Gases y Espectrometría de Masas , Pimenta/clasificación

RESUMEN

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.

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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.

Asunto(s)

Aceites Volátiles/química , Burseraceae/química , Terpenos/análisis , Cimenos/análisis

RESUMEN

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% (PHU) and 11.3% (PHH); the main components were terpinolene (42.31%) and p-cymene (39.93%) for subspecies ulei (PHU) and heptaphyllum (PHH), respectively.

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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% para PHU e 11,3% para PHH. Os monoterpenos terpinoleno (42.31%) e p-cimeno (39.93%) foram os constituintes principais para PHU e PHH, respectivamente.