Alpha-terpineol prevents myocardial damage against isoproterenol-MI induced in Wistar-Kyoto rats: new possible to promote cardiovascular integrity.

Alpha-terpineol (TPN) is one of the major components of the resin obtained from Protium heptaphyllum. This plant has been utilized as medicine by Brazilian indigenous tribes to treat cardiovascular diseases. Scientific reports have shown that the TPN possesses vasorelaxant and antihypertensive effects. This study was conducted to assess the cardioprotective action of TPN against isoproterenol (ISO)-induced cardiotoxicity. Wistar rats were randomly divided into six groups. Rats were orally administered with TPN (25, 50, and 75 mg/kg, respectively) for 15 days, and ISO was administered (85 mg/kg, subcutaneously) on the 14th and 15th days. At the end of the experiment, the hemodynamic, baroreflex test, ECG, biochemical, histological, and morphometric changes were monitored from control and experimental groups, i.e., on the 15th day. ISO-induced myocardial infarcted rats showed an increase in mortality rates, cardiac marker enzymes, tachycardia, hypertrophy, myocardium necrosis, edema, hemorrhagic areas, infiltration of inflammatory cells like lymphocytes, and increased myocardial infarct size. However, pretreatment with TPN significantly inhibited these effects of ISO. The histopathological findings obtained for the myocardium further confirmed the biochemical results. Thus, the present study provides evidence for the efficacy of TPN against ISO-induced myocardial infarction in rats.

Biocidal Activity of a Nanoemulsion Containing Essential Oil from Protium heptaphyllum Resin against Aedes aegypti (Diptera: Culicidae).

This work aimed to prepare a nanoemulsion containing the essential oil of the Protium heptaphyllum resin and evaluate its biocidal activities against the different stages of development of the Aedes aegypti mosquito. Ovicide, pupicide, adulticide and repellency assays were performed. The main constituents were p-cymene (27.70%) and α-pinene (22.31%). The developed nanoemulsion showed kinetic stability and monomodal distribution at a hydrophilic-lipophilic balance of 14 with a droplet size of 115.56 ± 1.68 nn and a zeta potential of -29.63 ± 3.46 mV. The nanoemulsion showed insecticidal action with LC50 0.404 µg·mL-1 for the ovicidal effect. In the pupicidal test, at the concentration of 160 µg·mL-1, 100% mortality was reached after 24 h. For adulticidal activity, a diagnostic concentration of 200 µg·mL-1 (120 min) was determined. In the repellency test, a concentration of 200 µg·mL-1 during the 180 min of the test showed a protection index of 77.67%. In conclusion, the nanobiotechnological product derived from the essential oil of P. heptaphyllum resin can be considered as a promising colloid that can be used to control infectious disease vectors through a wide range of possible modes of applications, probably as this bioactive delivery system may allow the optimal effect of the P. heptaphyllum terpenes in aqueous media and may also induce satisfactory delivery to air interfaces.

Quali-Quantitative Characterization of Volatile and Non-Volatile Compounds in Protium heptaphyllum (Aubl.) Marchand Resin by GC-MS Validated Method, GC-FID and HPLC-HRMS2.

Protium heptaphyllum (Aubl.) Marchand (PH) trees are endemic to the tropical region of South America, mostly Brazil. Antibacterial, antinociceptive, anti-inflammatory, anxiolytic, antidepressant and anti-hyperlipidemic/anti-hypercholesterolemic effects were reported for its resinous exudate Protiumheptaphyllum resin (PHR). This work aims to provide a qualitative and quantitative consistent chemical profiling of the major constituents of this resin and two extracts enriched in acid (acidic triterpene concentrated extract, ATCE) and neutral triterpenes (α and ß-amyrin concentrated extract, AMCE). GC-MS/GC-FID was used for volatile terpene fraction, a validated GC-MS method was developed for quantification of neutral α and ß-amyrin and HPLC-APCI HRMS2 was used for acidic triterpenes analysis. The chemical investigation reported 29 molecules, including 14 volatile terpenes, 6 neutral triterpenes and 11 acid triterpenes. The most abundant compounds were α-amyrin (251.28 g kg-1, 123.98 g kg-1 and 556.82 g kg-1 in PHR, ATCE and AMCE, respectively), ß-amyrin (172.66 g kg-1, 95.39 g kg-1 and 385.58 g kg-1 in PHR, ATCE and AMCE, respectively), 3-oxo-tirucalla-7,24-dien-21-oic acid (80.64 g kg-1, 157.10 g kg-1 and 15.31 g kg-1 in PHR, ATCE and AMCE, respectively) and 3α-hydroxy-tirucalla-8,24-dien-21-oic acid (77.71 g kg-1, 130.40 g kg-1 and 11.64 g kg-1 in PHR, ATCE and AMCE, respectively). Results showed specific enrichment of acidic and neutral triterpenoids in the two respective extracts.

Chemical composition of essential oils from different parts of Protium heptaphyllum (Aubl.) Marchand and their in vitro antibacterial activity.

In Brazilian folk medicine, Protium heptaphyllum is used to treat inflammatory conditions and to hasten wound repair. This paper aims to investigate the chemical composition and the in vitro antibacterial effects of the essential oils (EOs) obtained from P. heptaphyllum leaves and ripe and unripe fruits against a representative panel of oral pathogens. The GC-FID and GC-MS analysis revealed that the major components determined in P. heptaphyllum essential oils were myrcene (59.0%), ß-elemene (17.2%), limonene (12.9%), spathulenol (12.6%), α-cubebene (11.6%), germacrene D (10.6%), trans-nerolidol (9.8%), and α-cadinol (8.8%). The essential oils of the ripe and unripe fruits showed the strongest antibacterial activity against the anaerobic bacteria Prevotella nigrescens (MIC = 50 µg/mL). The leaf essential oil displayed very promising activity against Streptococcus mutans (MIC = 50 µg/mL) and Streptococcus mitis (MIC = 62.5 µg/mL). The antibacterial activity of EOs against oral pathogens is also described for the first time. [Formula: see text].

Pharmacological effects of the isomeric mixture of alpha and beta amyrin from Protium heptaphyllum: a literature review.

Protium heptaphyllum Aubl. belongs to the Burseraceae family. It is commonly called 'almecegueira' and is known to produce an amorphous resin which has constituents such as α- and ß-amyrin, taraxastan-3-oxo-20-ol and sitostenonein. The α- and ß-amyrin from P. heptaphyllum have pharmacological activities in several systems, such as central and peripheral nervous system, gastrointestinal tract and immunological system. In this study, our objective was to review pharmacological activities and to gather more information on the mixture of α- and ß-amyrin obtained from P. heptaphyllum to guide future preclinical and clinical studies using this compound. This review consisted of searches performed using scientific databases such as PubMed, SciELO, LILACS, SciFinder and Science Direct. Some uses of α- and ß-amyrin have been partially confirmed by previous studies demonstrating analgesic, anti-inflammatory, anticonvulsant, antidepressive, gastroprotective, hepatoprotective, antipancreatitic, anticholytic, antihyperglycemic and hypolipidemic effects. It is noteworthy that there are no α- and ß-amirin toxicity tests described in the literature as recommended in the international guidelines, and such tests are one of the research stages to proceed in clinical and preclinical trials if this compound was to be used.

Oxidation of monoterpenes in Protium heptaphyllum oleoresins.

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.

Essential Oil from the Resin of Protium heptaphyllum: Chemical Composition, Cytotoxicity, Antimicrobial Activity, and Antimutagenicity.

BACKGROUND: Protium heptaphyllum (Aubl.) March is popularly used as an analgesic and anti-inflammatory agent. OBJECTIVE: This study aimed to evaluate the chemical composition of P. heptaphyllum essential oil, its cytotoxicity in a breast cancer cell line (MCF-7), antimicrobial activity, and its antimutagenicity in vivo. MATERIALS AND METHODS: The chemical composition of the essential oil collected in three 3 years was determined by gas chromatography-mass spectrometry. The cytotoxicity was evaluated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Annexin V conjugated with fluorescein isothiocyanate, caspase-3, and tumor necrosis factor-alpha (TNF-α) assays were performed to evaluate apoptosis and inflammatory events. The antimutagenic activity at doses of 25, 50, and 100 mg/kg was determined using a micronucleus test in murine bone marrow. RESULTS: The essential oil showed a predominance of monoterpene compounds, being the terpinolene, p-cymene-8-ol, and p-cymene, present in the essential oil extracted in the 3 years. The essential oil showed a protection against cyclophosphamide-induced genotoxicity, and the cytotoxicity index polychromatic erythrocytes/normochromatic erythrocytes ratio in animals treated with oil at all doses (1.34 ± 0.33; 1.15 ± 0.1; 1.11 ± 0.13) did not differ from the negative control animal (1.31 ± 0.33), but from the cyclophosphamide group (0.61 ± 0.12). Cytotoxicity, at a concentration of 40.0 µg/mL, and antimicrobial activity were not observed for the essential oil (minimum inhibitory concentration ≥0.5 mg/mL). The essential oil did not change the levels of caspase-3 in the TNF-α level. CONCLUSION: The essential oil showed antimutagenic activity due to its chemical composition. SUMMARY: Terpinolene, p-cymene-8-ol, and p-cymene are the main constituents of the essential oil of P. heptaphyllum collected within 3-yearsThe essential oil of P. heptaphyllum did not show antimicrobial activity (MIC >0.5 mg/mL) against E. coli, S. aureus, E. faecalis, and C. albicansThe essential oil of P. heptaphyllum has activity against S. mutans (MIC = 0.5 mg/mL)The essential oil showed a protection against cyclophosphamide-induced genotoxicity in the micronuclei assay. Abbreviations used: GC-MS: Gas Chromatography-Mass Spectrometry, MTT: 3-(4,5dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, Annexin V-FITC: Annexin V conjugated with fluorescein isothiocyanate, TNF-α: Tumor necrosis factor alpha, MIC: Minimum Inhibitory Concentration.

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...

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.

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.

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.