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The Protium heptaphyllum species, also known as Almécega, produces an oily resin, used in folk medicine as an analgesic and anti-inflammatory agent, in healing, and as an expectorant, which is rich in pentacyclic triterpenes and essential oils. In this study, the essential oil obtained by hydrodistillation of Almécega’s resin was analyzed by gas ch...
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ABSTRACT
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Citations
... The same happened with white rosin oil, which had ρ-cymene as its main compound, which is a monoterpene, corroborating Mobin et al. (2017). This monoterpene, in addition to having antioxidant properties, has important actions on the cardiovascular system, being able to promote hypotension, vasorelaxation and decreased heart rate . ...
... The assumption for the actions of vasorelaxation, decreased heart rate and hypotension comes from the probability of an inhibition of the vasomotor center, which may result in a decrease in sympathetic blood flow, thus reaching both the peripheral blood vessels and the heart, resulting in in reductions in blood pressure and heart rate (El Tahir et al., 1993). In this way, p-cement can be listed as a favorable agent for the prevention and/or intervention in diseases of the cardiovascular system (Mobin et al., 2017). ...
Autism is a neuropsychiatric disorder that develops in childhood and may have associated comorbidities, such as heart disease. As a treatment, alternative therapy means are being sought to conventional methods. For study purposes, autism has been induced through gestational exposure to valproic acid. With the aim of evaluating the vascular and cardiac effects of treatment with copaiba essential oil and white pitch caused by gestational exposure to valproic acid, on the 13th day of pregnancy, the rats in the negative control group received water and those in the experimental groups received valproic acid (600 mg/kg), intraperitoneally, once. The male puppies were divided into six groups: negative and positive controls; vehicle; treated with copaiba oil; with white pitch oil and copaiba oil associated with white pitch. TERRA® oils were administered via gavage for 30 consecutive days. As a result, a reduction in superoxide dismutase, catalase and creatine kinase and an increase in total antioxidant activity and malondialdehyde were verified. Presence of myocarditis, vacuolation and necrosis of cardiomyocytes. There was no significant change in area and diameter, but there was an increase in the volume density and length of cardiomyocytes and a decrease in the volume density of blood vessels and interstices and the length density of blood vessels. Thus, exposure to valproic acid during the intrauterine period caused changes in the cardiac microstructure. However, the use of copaíba and white pitch essential oils led to oxidative and nitrosative stress, and the combination of the two oils has promising results in reversing this condition.
... In intact pre-contracted rings with phenylephrine (Phe 1 μm), EOPH (3-750 μg/ mL) induced relaxation, and essential oil had a concentration-dependent vasorelaxant effect, without the involvement of endothelial mediators [90] Essential Oils of the Leaves of Ripe and Green Fruits Myrcene (59.0%), β-element (17.2%), limonene (12.9%), spathulenol (12.6%), αcubebene (11.6%), Germacrene D (10.6%), transnerolidol (9.8%) and αcadinol (8.8%) ...
... A fraction of the extract showed antioxidant activity to repair oxidative stress and, the extract showed a hepatoprotective effect and demonstrated a possible hypoglycemic effect of the plant. The authors believe that the antioxidant effects may be due to the presence of flavonoids identified by in vitro tests such as Quercetin-3-β-D-glucosylated, Myricetin, and Quercetin, which are already well known for their antioxidant properties [90][91][92][93]. Bandeira et al. [68], also observed in vitro antioxidant activity of the essential oil of P. heptaphyllum ( Table 3). ...
Background
Oxidative stress occurs when the cell's antioxidant defense system is insufficient. This can be corrected by active antioxidant substances, which help to eliminate the consequences of the damage caused or prevent the system from reaching the stress level.
Objective
The actions of antioxidants can inhibit or delay tumor cells' appearance, delaying aging, and preventing other cellular damage resulting from the redox imbalance. Therefore, the present work aimed to research studies already published on Protium heptaphyllum (P. heptaphyllum) and its biological activities, mainly antioxidant effects once resulting from phenolic compounds, such as flavonoids, present in the plant.
Methods
The methodology used was a literature review where information was collected from several studies related to P. heptaphyllum, oxidative stress, polyphenols, and flavonoids in databases, such as Scielo, PubMed, Google Scholar, LILACS, Chemical Abstract, ScienceDirect, among others in the period from 2002 to 2021.
Results
The main studies carried out with metabolites of P. heptaphyllum demonstrated several biological activities such as antioxidant, gastroprotective, anti-inflammatory, analgesic, anxiolytic, antihyperglycemic, hyperlipidemic, among others. Although P. heptaphyllum has been little investigated by pharmacological studies, the results reported in this work may contribute to this plant species' chemical/pharmacological knowledge. Therefore, the secondary metabolites present in the plant may become test targets in future clinical trials for the drug arsenal.
Conclusion
It can be observed that P. heptaphyllum is a promising source of secondary compounds, mainly flavonoids.
... Os componentes majoritários das resinas velhas (comercial) foram os monoterpenos limoneno, 1,8-cineol e p-cimeno, enquanto nas resinas frescas foram o limoneno, p-cimeno e α-terpineol. O óleo de resinas velhas mostrou ainda efeito vasorelaxante em bioensaios com ratos, sugerindo uma possível forma de tratamento alternativo para hipertensão(Mobin et al., 2017).A empresa Laszlo Aromaterapia Ltda. também extraiu óleos voláteis de resinas de P. heptaphyllum do Brasil (G-Br8) e obtiveram como componentes majoritários os monoterpenos β-felandreno e p-cimeno (Tabela 1). ...
Protium heptaphyllum, conhecida como amescla, amelcegueira e breu-branco, possui ampla distribuição nacional, encontrada especialmente na Amazônia e Mata Atlântica. É uma espécie rica em óleo essencial, porém destaca-se o uso da resina como medicinal. Diante disso, este estudo teve como objetivo levantar a variabilidade química entre óleos essenciais de Protium hepthaphylum de diferentes localidades. Trata-se de uma revisão sistemática nas bases de dados SciElo, PubMed e Google Scholar, tendo como estratégia de busca os descritores “essential oil” e “Protium heptaphyllum”, nos idiomas português e inglês, publicados entre os anos de 2000 a 2020. Um total de 10 artigos foram selecionados para a análise do perfil químico e de variabilidade química do óleo essencial de P. heptaphyllum, entretanto, foi possível levantar 28 análises químicas diferentes para 10 acessos distintos de coletas. Das 28 análises químicas, 21 foram realizadas de óleos extraídos da resina, 03 de folhas e 04 de frutos e um total de 145 substâncias foram levantadas. A variabilidade química dos óleos essenciais entre cada localidade foi evidente, com destaque para 21 substâncias majoritárias. Os grupos dos monoterpenos foi o mais representativo, com destaque para o limoneno, α-terpineol, 1,8-cineol, p-cimeno, α e β-felandreno. Conclui-se que as alterações ambientais podem ser as responsáveis por essa variabilidade não descartando a possibilidade de algum acesso se tratar de quimiotipo.
... It is also important to mention that the essential oil obtained from Protium heptaphyllum showed cardiovascular effects. This oil has TPN as its main constituent [17]. Nevertheless, the cardioprotective effect of TPN in isoproterenol-induced MI in rats has not been documented to date. ...
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.
... Similar results have been described for other species of Protium spp. and for different shoot parts, which include resin, leaves, and fruits (Carvalho et al., 2013;Mobin et al., 2016;Mobin et al., 2017;Moraes et al., 2013;Pinto et al., 2010;Pontes et al., 2010Pontes et al., , 2007Siani et al;, 2004;Silva et al., 2016;Silva et al., 2013;Souza et al., 2016;Zoghbi et al., 2005). ...
Protium ovatum is a Brazilian endemic species widely distributed between the Cerrado and Amazon biomes. Here, we evaluate the chemical composition of the essential oils (EO) of different shoot organs from P. ovatum including stems, petioles, leaves, flowers, ripe and unripe fruits, and investigate their antifungal potential against Sclerotinea sclerotiorum. The EO were obtained by hydrodistillation in a Clevenger-type apparatus and analysed by GC-MS, followed by PCA analysis. The antifungal activity was performed by agar diffusion. Fruits had the highest essential oil contents among the shoot parts. The constituents were found varyingin the different organs: α-Pinene (0.80-18.3%), β-Pinene (0.58-5.17%), Myrcene (0.52-27.3%), Limonene (3.15-59.7%), Caryophyllene E (3.67-16.4%), Germacrene D (6.34-27.4%), and δ-Cadinene (2.29-7.63%). The essential oil from ripe fruit showed the strongest antifungal activity, with the highest Inhibition of Mycelial Growth (IMG) (50.11%) at the lowest concentration assayed (18.75μg.mL-1). This is the first report on the chemical composition of the essential oils from stems, petioles, flowers, and ripe fruits of P. ovatum and their antifungal activity against S. sclerotiorum, making it a potential source of antimicrobial agents
... To our knowledge, this is the first report showing the qualitative and quantitative analyses of VOCs from PHR by using solvent extraction, while all previous investigations showed the qualitative percentage of volatiles in PHR essential oil. However, the present data on VOC content in PHR oleum resin confirm the previously published reports, regarding which monoterpenes are the main chemical constituents of volatile fraction in the range between the 85% and the 98% [9,21,22]. The higher percentage of monoterpenes in the analyzed PHR samples were α-pinene (24.85%), p-cymene (21.85%), 3-carene (13.90%), β-phellandrene (13.33%) and α-phellandrene (8.30%). ...
... In previously published studies, p-cymene and β-phellandrene were reported as the main volatile constituents of P. heptaphyllum essential oil (13.63% and 60.68% respectively) [21], whereas α-pinene and α-phellandrene were reported among the most abundant VOCs in essential oil reaching the 10.5% and the 16.70%, respectively, with terpinolene (28.50%) and limonene (16.9%) as main compounds [9]. The compound 3-carene was also reported among the characteristic P. heptaphyllum monoterpenes in essential oil (4.00%) from mechanically wounded tree [23] and commercial resin (5.11%) [22]. Few sesquiterpenes were reported in literature on P. heptaphyllum essential oil: β-(E)-caryophyllene was reported in two previously published reports at the percentage of 1.5% and 1%, respectively [9,11], whereas other notable reported sesquiterpenes were α-ylangene at 0.47% [21,23], α-cubebene (3.30%) [11] and α-gurjunene (0.30%) [9]. ...
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 β-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 β-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), β-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.
... Protium heptaphyllum (Aubl.) is a tree which belongs to the Burseraceae family that produces an amorphous and aromatic resin with pharmacological activities in nervous and immunological systems and gastrointestinal tract [1]. In addition, it is used in folk medicine as an analgesic and antiinflammatory agent, in healing, and as an expectorant, which is rich in pentacyclic triterpenes and essential oils [2]. ...
... EOPH from Ceará (Brazil) presented lower amount of monoterpenes (86.4%), and terpinolene (28.5%) was the main constituent, followed by α-pinene (10.5%) and α-phellandrene (16.7%) [15]. Mobin et al. [2] reported the main constituents of EOPH determined by gas chromatographytriple quadrupole mass spectrometry were limonene, p-cineole, and o-cymene. In the EOPH from Acre (Brazil), twentyone constituents (98.53%) were identified, and p-cymene (39.93%) was the main constituent followed by n-tetradecane (13.38%), dihydro-4-carene (11.69%), and α-phellandrene (7.41%) [15]. ...
Protium heptaphyllum is a plant widely distributed in Brazilian ecosystems that produce a resin which has pharmacological activities. In this study, the chemical composition, antimicrobial and antibiofilm activity, and the possible mechanism of action against the bacterium V. parahaemolyticus of essential oil from P. heptaphyllum (EOPH) were investigated. Twenty-two components were detected in EOPH, and β -phellandrene (60.68%) had the majority. The inhibition halo, MIC, and MBC values were 11 mm, 2 mg/mL, and 8 mg/mL, respectively. Biofilm biomass inhibition and biomass reduction of the preformed biofilm were detected at 4 mg/mL EOPH concentration. The assays of cell constituent release and membrane permeability indicated that EOPH may disrupt the cell membrane, leading to leakage of intracellular constituent as reducing sugars and materials with an absorbance of 260 nm.
... heptaphyllum Antibacterial (Streptococcus mutans, MIC 0.13 µg/mL) tricyclene (11.1%), p-cymene (26.7%), terpinolene (35.8%), p-cymen-8-ol (10.1%)[21]P. heptaphyllum Vasorelaxant (rat upper mesenteric artery ring, IC 50 316 µg/mL) δ-3-carene (5.1%), p-cymene (17.0%), limonene (34.5%), 1,8-cineole (20.6%), α-terpineol (9.8%)[22]P. heptaphyllum α-phellandrene (7.0%), p-cymene (26.9%), limonene (28.9%), α-terpineol (18.4%)[22]P. heptaphyllum Fresh resin: α-terpinene (18.0%), p-cymene (36.0%), γ-terpinene (12.0%)[23]P. ...
... heptaphyllum Vasorelaxant (rat upper mesenteric artery ring, IC 50 316 µg/mL) δ-3-carene (5.1%), p-cymene (17.0%), limonene (34.5%), 1,8-cineole (20.6%), α-terpineol (9.8%)[22]P. heptaphyllum α-phellandrene (7.0%), p-cymene (26.9%), limonene (28.9%), α-terpineol (18.4%)[22]P. heptaphyllum Fresh resin: α-terpinene (18.0%), p-cymene (36.0%), γ-terpinene (12.0%)[23]P. heptaphyllum ...
Background: Protium species (Burseraceae) have been used in the treatment of various diseases and conditions such as ulcers and wounds. Methods: The essential oil from the oleoresin of Protium amazonicum was obtained by hydrodistillation and analyzed by GC-MS, GC-FID, and chiral GC-MS. P. amazonicum oleoresin oil was screened for antifungal activity against Candida albicans, Aspergillus niger, and Cryptococcus neoformans. Results: A total of 54 components representing 99.6% of the composition were identified in the oil. The essential oil was dominated by δ-3-carene (47.9%) with lesser quantities of other monoterpenoids α-pinene (4.0%), p-cymene (4.1%), limonene (5.1%), α-terpineol (5.5%) and p-cymen-8-ol (4.8%). Chiral GC-MS revealed most of the monoterpenoids to have a majority of levo enantiomers present with the exceptions of limonene and α-terpineol, which showed a dextro majority. P. amazonicum oleoresin oil showed promising activity against Cryptococcus neoformans, with MIC = 156 μg/mL. Conclusions: This account is the first reporting of both the chemical composition and enantiomeric distribution of the oleoresin essential oil of P. amazonicum from Ecuador. The oil was dominated by (−)-δ-3-carene, and this compound, along with other monoterpenoids, likely accounts for the observed antifungal activity of the oil.
Aims:
We investigated the chemical composition and the in vitro and in vivo antibacterial effects of Protium heptaphyllum essential oil (PHEO) alone and in combination with antibiotics against polymyxin-resistant K. pneumoniae isolates.
Methods and results:
Hydrodistillation was used to obtain PHEO and gas chromatography coupled with mass spectrometry (GC/MS) revealed α-pinene, δ-3-carene, and β-pinene as major components present in PHEO. Minimum Inhibitory Concentration (MIC) was determined using the broth microdilution technique and ranged from 256 to 512 µg.ml-1. The Checkerboard method showed synergy with the combination of PHEO and amikacin (AMK) against the polymyxin-resistant K. pneumoniae isolates. In 8 of the 10 isolates tested, the Fractional Inhibitory Concentration Indexs (FICIs) ranged from 0.06 to 0.5, while in the remaining two isolates, the combination exerted an additive effect (FICI of 0.6 and 1.0), resulting in AMK dose reduce of range 2-to 16-fold, in the presence of PHEO. Analysis using Zero Interaction Potency revealed high synergy score (63.9). In the in vivo assay, the survival of Caenorhabditis elegans was significantly improved in the presence of PHEO (1 µg.ml-1) + AMK (µg.ml-1) combination as compared to 32 µg.ml-1 AMK alone. Furthermore, PHEO concentrations of 256 and 512 µg.ml-1 were found to be non-toxic on the experimental model.
Conclusion:
To our knowledge, this is the first report of such type of synergism demonstrating an antimicrobial effect against polymyxin-resistant K. pneumoniae isolates.
