Chemical variability of the volatiles from the leaves of Eugenia protenta McVaugh (Myrtaceae) growing wild in the North of Brazil

Zoghbi, M.G.B.; Guilhon, Giselle Maria Skelding Pinheiro; Sarges, Flávio N; Pereira, Raimunda A.; Oliveira, Jadson José Souza de

doi:10.1016/j.bse.2011.05.019

Cited by 15 publications

(7 citation statements)

References 19 publications

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“…To our knowledge, it is the first study on the composition of the E. egensis and E. polystachya oils, and the first report on the occurrence of 5-hydroxy-cis-calemenene as a significant constituent in Eugenia essential oils. Other sesquiterpenes with a germacrane skeleton have been reported in E. protenta [ 27 ] and E. uniflora [ 28 ].…”

Section: Resultsmentioning

confidence: 99%

Chemical Composition of Four Essential Oils of Eugenia from the Brazilian Amazon and Their Cytotoxic and Antioxidant Activity

et al. 2017

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Background: Eugenia species are appreciated for their edible fruits and are known as having anticonvulsant, antimicrobial and insecticidal actions. Methods: The plant material was collected in the southeastern Pará state of Brazil and submitted to hydrodistillation. GC-MS analyzed the oils, and their antioxidant and cytotoxic activities were evaluated by the DPPH and MTT assays. Results: The main components identified in the Eugenia oils were 5-hydroxy-cis-calemene, (2E,6E)-farnesol, (2E,6Z)-farnesol, caryophylla-4(12),8(13)-dien-5α-ol-5β-ol, E-γ-bisabolene, β-bisabolene, germacrene D, and ishwarane. The oil of E. egensis showed the most significant antioxidant activity (216.5 ± 11.6 mg TE/mL), followed by the oils of E. flavescens (122.6 ± 6.8 mg TE/mL) and E. patrisii (111.2 ± 12.4 mg TE/mL). Eugenia oils were cytotoxic to HCT-116 (colon cancer) cells by the MTT assay, where the most active was the oil of E. polystachya (10.3 µg/mL), followed by the oils of E. flavescens (13.9 µg/mL) and E. patrisii (16.4 µg/mL). The oils of E. flavescens and E. patrisii showed the highest toxicity for MRC5 (human fibroblast) cells, with values of 14.0 µg/mL and 18.1 µg/mL, respectively. Conclusions: These results suggest that Eugenia oils could be tested in future studies for the treatment of colon cancer and oxidative stress management.

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Section: Resultsmentioning

confidence: 99%

Chemical Composition of Four Essential Oils of Eugenia from the Brazilian Amazon and Their Cytotoxic and Antioxidant Activity

et al. 2017

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“…Eugenia essential oils are characterized by intra- and interspecific chemical diversity, with the predominance of cyclic sesquiterpenes, follow by monoterpenes, and without phenylpropanoids as the main compound (See Appendix A and Appendix B ) [ 22 ]. However, dimethylxanthoxylin (73.2 and 83.0%), an acetophenone derivative, was identified by GC–MS and NMR techniques as the major constituent in EOs of two specimens of E. protenta McVaugh collected in Santarém Novo, western Pará state located in the Brazilian Amazon [ 23 ].…”

Section: Volatile Profilesmentioning

confidence: 99%

“…Some essential oils of Eugenia species have shown great interspecific chemical variation. For example, Eugenia protenta EOs from Pará state (Brazil) occurring at three chemical profiles rich in the cyclic sesquiterpenes with eudesmane, elemane, and germacrane skeletons as selin-11-en-4α-ol (14.4–18.3%) and β-elemene (12.3–18.3%) (profile I); germacrene D (15.1–15.6%), bicyclogermacrene (5.8–11.8%), δ-elemene (8.5%), and β-elemene (9.2–12.8%) (profile II); or characterized by the presence of dimethylxanthoxylin (73.2–83.0%) (profile III) [ 23 ]. E. biflora (L.) DC.…”

Section: Volatile Profilesmentioning

confidence: 99%

Essentials Oils from Brazilian Eugenia and Syzygium Species and Their Biological Activities

et al. 2020

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The Eugenia and Syzygium genera include approximately 1000 and 1800 species, respectively, and both belong to the Myrtaceae. Their species present economic and medicinal importance and pharmacological properties. Due to their chemical diversity and biological activity, we are reporting the essential oils of 48 species of these two genera, which grow in South America and found mainly in Brazil. Chemically, a total of 127 oil samples have been described and displayed a higher intraspecific and interspecific diversity for both Eugenia spp. and Syzygium spp., according to the site of collection or seasonality. The main volatile compounds were sesquiterpene hydrocarbons and oxygenated sesquiterpenes, mainly with caryophyllane and germacrane skeletons and monoterpenes of mostly the pinane type. The oils presented many biological activities, especially antimicrobial (antifungal and antibacterial), anticholinesterase, anticancer (breast, gastric, melanoma, prostate), antiprotozoal (Leishmania spp.), antioxidant, acaricidal, antinociceptive and anti-inflammatory. These studies can contribute to the rational and economic exploration of Eugenia and Syzygium species once they have been identified as potent natural and alternative sources to the production of new herbal medicines.

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“…Leaf essential oils from E. protenta , collected from Northeastern Pará State, were rich in sesquiterpene hydrocarbons, such as germacrene D, β-elemene, δ-cadinene, or keto-phenolic ethers, as dimethylxanthoxylin. 19 Similarly, oils of E. flavescens , from different regions of Pará State, were rich in sesquiterpenes with the germacrane skeleton (germacrene D and bicyclogermacrene), or the bisabolane skeleton (β-, ( E )- iso -γ- and ( E )-γ-bisabolene) 10,15.…”

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confidence: 99%

Variability in the Chemical Composition of Eugenia biflora Essential Oils from the Brazilian Amazon

Figueiredo

Fernandes

Silva

et al. 2019

Natural Product Communications

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Eugenia species are well known for their great economic potential as edible fruits. The leaves of 4 Eugenia biflora specimens (Ebi-1 to Ebi-4) were sampled in the Caratateua Island, Pará state, Brazilian Amazon. Then, the essential oils were hydrodistilled, analyzed by gas chromatography (GC) and GC mass spectroscopy, and their volatile compositions submitted to multivariate analysis (principal component analysis and hierarchical cluster analysis). Ebi-1 and Ebi-2 specimens were classified in the caryophyllene group, with significant content for the sesquiterpenes ( E)-caryophyllene (16.8% and 11.4%) and caryophyllene oxide (28.6% and 20.5%). Ebi-3 specimen was grouped into the cadinane group, characterized by the presence of α-cadinol (14.7%), an oxygenated sesquiterpene. EBI-4 specimen was inserted into the aromadendrane group, with the predominance of the sesquiterpenes globulol (9.8%), germacrene B (7.9%), and γ-elemene (3.1%). Based on the results, a remarkable chemical variability was observed in the oils of Eugenia biflora with occurrence in Pará state, North Brazil. This work is presenting for the first time its caryophyllene, cadinane, and aromadendrane profiles.

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Chemical variability of the volatiles from the leaves of Eugenia protenta McVaugh (Myrtaceae) growing wild in the North of Brazil

Cited by 15 publications

References 19 publications

Chemical Composition of Four Essential Oils of Eugenia from the Brazilian Amazon and Their Cytotoxic and Antioxidant Activity

Chemical Composition of Four Essential Oils of Eugenia from the Brazilian Amazon and Their Cytotoxic and Antioxidant Activity

Essentials Oils from Brazilian Eugenia and Syzygium Species and Their Biological Activities

Variability in the Chemical Composition of Eugenia biflora Essential Oils from the Brazilian Amazon

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