Essential Oils Obtained from Aerial Eugenia punicifolia Parts: Chemical Composition and Antiproliferative Potential Evidenced through Cell Cycle Arrest

Abstract

Essential oils (EOs) of the leaves of three Eugenia punicifolia specimens from two different Reservation Parks, namely Parque Nacional das Nascentes do Rio Parnaíba (EpNRP-I and EpNRP-II) and Parque Nacional da Chapada das Mesas (EpCM), in the state of Maranhão, Brazil, were extracted by hydrodistillation and investigated by gas chromatography coupled to mass spectrometry. Principal component and hierarchical cluster analyses indicated differences between the samples. Antiproliferative EOs activity was determined for U-251 (glioblastoma), MCF-7 (breast adenocarcinoma), NCI/ADR-RES (multidrug-resistant ovarian adenocarcinoma), OVCAR-3 (ovarian adenocarcinoma), HT-29 (colorectal adenocarcinoma), and HaCaT (non‑tumor keratinocyte) cell lines applying the colorimetric method using 3-(4,5-dimethyl- 2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) to determine the GI50 (50% growth inhibition) concentration. The extraction yields of the analyzed EOs were 0.58, 1.42 and 0.84%. The main constituents identified in two samples were α-pinene (49.75%), 1,8-cineole (13.77%) and α-terpineol (7.32%), and in the third sample, germacrene B (16.25%), (E)-caryophyllene (13.21%) and β-pinene (12.81%). The main GI50 results for sample EpNRP-I were noted for the U-251 (2.13 μg mL−1) and MCF-7 (6.72 μg mL−1) tumor lines. For the non-tumoral line HaCaT, the calculated GI50 was higher than the positive control comprising doxorubicin hydrochloride (13.35 μg mL−1). In addition, a flow cytometry analysis revealed that this same sample arrests the cell cycle of the MCF-7 line in the second interphase stage.

Comparative study of the chemical composition, larvicidal, antimicrobial and cytotoxic activities of volatile oils from E. punicifolia leaves from Minas Gerais and Goiás

“…Geracrene D was found in volatile oils of E. punicifolia from MA (5.3%) (Fernandes, et al, 2021), PA (5.39%) (Pereira, et al, 2010), RJ (1.9 %) (Ramos, et al, 2010), PA (2.05%) (Franco, et al, 2021), as well as in MG (1.62%). Its isomer germacrene B was also found in samples of Pernambuco (PE) (1.3%) (Oliveira, et al, 2005), PA (0.8%) (Pereira, et al, 2010), RJ (1.9%) (Ramos, et al, 2010), MA (16.3%) (Fernandes, et al, 2021b) and PA (1.1%) (Franco, et al, 2021). Bicyclogermacrene was identified in the samples of PA (8.75%) (Pereira et al, 2010), MA (7.0%) (Fernandes et al, 2021b) and PA (9.88 and 5.86%) (Franco, et al, 2021) and MG (2.99%).…”

“…Its isomer germacrene B was also found in samples of Pernambuco (PE) (1.3%) (Oliveira, et al, 2005), PA (0.8%) (Pereira, et al, 2010), RJ (1.9%) (Ramos, et al, 2010), MA (16.3%) (Fernandes, et al, 2021b) and PA (1.1%) (Franco, et al, 2021). Bicyclogermacrene was identified in the samples of PA (8.75%) (Pereira et al, 2010), MA (7.0%) (Fernandes et al, 2021b) and PA (9.88 and 5.86%) (Franco, et al, 2021) and MG (2.99%).…”

“…The volatile oil yields for specimens from Hidrolândia -GO and São Gonçalo do Abaté -MG were 0.21 and 0.26%, respectively for leaves. In the literature, the yield of oils from E. punicifolia leaves ranged from 0.79% and 0.82% in mountainous regions of Pernambuco (PE) (Oliveira, et al, 2005), 0.18% in Macaé, Rio de Janeiro (RJ) (Ramos, et al, 2010), 0.58, 1.42 and 0.84% of the aerial parts of three specimens collected in different locations in the city of Carolina -Maranhão (MA) (Fernandes, et al, 2021b) and 0.26 and 0, 14% of the leaves of 2 specimens collected in Magalhães Barata, Pará (PA) (Franco, et al, 2021). Variations in volatile oil yields of the same species in different regions of Brazil can be attributed to climatic, geographical, ecological, and physiological factors (Oliveira, et al, 2005, Fernandes, et al, 2021.…”

“…The predominant class of terpenes in the GO sample were sesquiterpenes (89.23%), while for those from MG it was oxygenated sesquiterpenes (59.46%). In the literature, there was a prevalence of the class of sesquiterpene hydrocarbons (including oxygenated ones) in volatile oils from the leaves of E. punicifolia in Amazonas (AM) (70.6 and 65.8%) (Maia, et al, 1997), Rio de Janeiro (55.5 and 44%) (Ramos, et al, 2010), Pará (70.70%) (Pereira, et al, 2010), Maranhão (60.2%) (Fernandes, et al, 2021b), Pará (88.4 and 71.83%) (Franco, et al, 2021). However, there was a predominance of monoterpene hydrocarbons in Pernambuco (66 and 76.6%) (Oliveira, et al, 2005) and in two specimens from Maranhão (81.8 and 86.2%) (Fernandes, et al, 2021b).…”

“…In the present work, it was verified in the sample of MG βcaryophyllene (1.41%) and its isomers (Z)-caryophyllene (8.92%), caryophyllene oxide (5.57%), and α-humulene (2.72%) and the GO sample the caryophyllene oxide (0.29%) and αhumulene (3.2%). β-carophyllene was identified as the majority compound in volatile oils from leaves collected in Caracaraí and Itacoatiara -AM (32.9 and 23.6%) (Maia, et al, 1997), in Serra Negra and Brejo da Madre de Deus -PE (22.7 and 16.2 %) (Oliveira, et al, 2005), in Macaé-RJ (6.5%) (Ramos, et al, 2010), in Maracanã-PA (9.87%) and in the aerial parts of E. punicifolia in Carolina -MA (3.2 to 13.21%) (Fernandes, et al, 2021b) and Magalhães Barata-PA (13.11 and 11.47%) (Franco, et al, 2021).…”