Triterpenes from the Protium heptaphyllum resin – chemical composition and cytotoxicity

Lima, Ewelyne Miranda de; Nascimento, Andrews Marques do; Lenz, Dominik; Scherer, Rodrigo; Meyrelles, Silvana S.; Boëchat, Giovanna Assis Pereira; Andrade, Tadeu Uggere de; Endringer, Denise Coutinho

doi:10.1016/j.bjp.2014.06.003

Cited by 19 publications

(15 citation statements)

References 38 publications

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“…[ 9 ] However, the use of resin extract produced by different solvents showed activity against C. albicans (MIC values: 1000 μg/ml), E. coli (MIC values: 1000 μg/ml), and S. aureus 125 (MIC values: µg/mL for E. coli ). [ 33 ] The results obtained in the cellular cytotoxicity assay with colorimetric method of the MTT showed that the essential oil was not effective against the cancer cells at a concentration of 40.0 µg/mL, in agreement with the results of a study carried out with the crude resin of P. heptaphyllum [ 21 ] with the same concentration against MCF-7 tumor cells.…”

Section: Discussionsupporting

confidence: 79%

“…The analysis of the chemical constituents of the essential oil of the resin of P. heptaphyllum was performed using a gas chromatograph (Trace Ultra, Thermo Scientific®) coupled to a mass spectrometer (DSQII, Thermo Scientific®) as previously described. [ 21 ]…”

Section: Methodsmentioning

confidence: 99%

“…Apoptosis was carried out using an annexin V-FITC Kit (Sigma Aldrich, St. Louis, MO). [ 21 ] Briefly, MCF-7 cells were plated in a sterile 24-well plate at a concentration of 5 × 10 6 cells/mL. Then, 10 µL of the oil essential sample (final concentration of 40 µg/mL) was added.…”

Section: Methodsmentioning

confidence: 99%

“…The percentage of positive cells determined over 10,000 acquired events was analyzed by a FACSCalibur system equipped with a 488 nm argon laser and FCS Express 4 Flow Cytometry software ( De Novo Software, Los Angeles, CA). [ 21 ]…”

Section: Methodsmentioning

confidence: 99%

“…To quantify the levels of tumor necrosis factor-alpha (TNF-α), MCF-7 tumor cells were plated in a sterile 24-well plate at a concentration of 1 × 10 6 cells/mL. [ 21 ] Then, 10 µL of sample of essential oil (final concentration 40 µg/mL) was added, and the plate was incubated at 37°C in 5% CO 2 for 72 h. As a positive control, we used DOX (final concentration of 0.9 µM). After this period, we proceeded to read the plate in an ELISA reader (TP-Thermoplate Reader at 450 nm) using a commercial kit (Invitrogen, San Jose, USA) according to the manufacturer's instructions.…”

Section: Methodsmentioning

confidence: 99%

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Essential oil from the resin of Protium heptaphyllum: Chemical composition, cytotoxicity, antimicrobial activity, and antimutagenicity

et al. 2016

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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

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Section: Discussionsupporting

confidence: 79%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Essential oil from the resin of Protium heptaphyllum: Chemical composition, cytotoxicity, antimicrobial activity, and antimutagenicity

et al. 2016

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Engineering amino acid residues of pentacyclic triterpene synthases for improving the activity

Guo,

Chen,

Zhu

et al. 2024

Appl Microbiol Biotechnol

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Pentacyclic triterpenoids exhibit a wide range of biological activities which have wide applications in the food, cosmetics, and pharmaceutical industries. High-performance chassis strains have been developed for the production of various pentacyclic triterpenoids, e.g., lupane-type and oleanane-type triterpenoids. The production of common pentacyclic triterpenes and their derivatives is limited by the poor activity of typical pentacyclic triterpene synthases (PTSs). However, a general strategy applicable to typical PTSs is still lacking. As typical pentacyclic triterpenes are derived from the baccharenyl cation, engineering the non-active-site residues in the MXXXXR motif might be beneficial for the catalytic efficiencies of typical PTSs by the stabilization of the baccharenyl cation. Here, we develop a general strategy for improving the activity of typical PTSs. As a proof of concept, the activity of three PTSs such as lupeol synthase, β-amyrin synthase, and α-amyrin synthases was significantly increased up to 7.3-fold by site-directed saturation mutagenesis. This strategy could be applied to improve the activity of various typical PTSs. Key points • The strategy could be applied to typical PTSs for improving the activity. • The catalytic activity of typical PTSs was significantly increased.

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An overview on plants cannabinoids endorsed with cardiovascular effects

Dimmito

Stefanucci

Valle

et al. 2021

Biomedicine & Pharmacotherapy

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Triterpenes from the Protium heptaphyllum resin – chemical composition and cytotoxicity

Cited by 19 publications

References 38 publications

Essential oil from the resin of Protium heptaphyllum: Chemical composition, cytotoxicity, antimicrobial activity, and antimutagenicity

Essential oil from the resin of Protium heptaphyllum: Chemical composition, cytotoxicity, antimicrobial activity, and antimutagenicity

Engineering amino acid residues of pentacyclic triterpene synthases for improving the activity

An overview on plants cannabinoids endorsed with cardiovascular effects

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