Gas Chromatography-Triple Quadrupole Mass Spectrometry Analysis and Vasorelaxant Effect of Essential Oil from<i>Protium heptaphyllum</i>(Aubl.) March.

Mobin, Mitra; Lima, Sidney Gonçalo de; Almeida, Lorena T. G. de; Filho, José Carlos Silva Camargo; Rocha, Márcio dos Santos; Oliveira, Aldeídia Pereira de; Mendes, Marcelo Bezerra; Carvalho, Fernando Aécio de Amorim; Melhem, M. S. C.; Costa, José G.M.

doi:10.1155/2017/1928171

Cited by 15 publications

(8 citation statements)

References 26 publications

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“…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%).…”

Section: Discussionsupporting

confidence: 92%

“…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 ].…”

Section: Discussionmentioning

confidence: 99%

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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

et al. 2021

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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.

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Section: Discussionsupporting

confidence: 92%

Section: Discussionmentioning

confidence: 99%

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

et al. 2021

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“…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 chromatography-triple quadrupole mass spectrometry were limonene, p -cineole, and o -cymene. In the EOPH from Acre (Brazil), twenty-one 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].…”

Section: Discussionmentioning

confidence: 99%

“…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 anti-inflammatory agent, in healing, and as an expectorant, which is rich in pentacyclic triterpenes and essential oils [2].…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition and Mechanism of Vibriocidal Action of Essential Oil from Resin of Protium heptaphyllum

Mendes¹,

Araújo

Carvalho

et al. 2019

The Scientific World Journal

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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.

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“…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).…”

Section: Resultsunclassified

Variabilidade química de óleos essenciais de Protium heptaphyllum

Rocha

Santana²,

Müller³

et al. 2022

RSD

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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.

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Gas Chromatography-Triple Quadrupole Mass Spectrometry Analysis and Vasorelaxant Effect of Essential Oil fromProtium heptaphyllum(Aubl.) March.

Cited by 15 publications

References 26 publications

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

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

Chemical Composition and Mechanism of Vibriocidal Action of Essential Oil from Resin of Protium heptaphyllum

Variabilidade química de óleos essenciais de Protium heptaphyllum

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