Antiproliferative activity from five Myrtaceae essential oils

Authors

DOI:

https://doi.org/10.33448/rsd-v12i3.40536

Keywords:

Myrcia spp. and Eugenia spp.; Essential oil, GC-MS; in vitro antiproliferative assay.

Abstract

The Myrtaceae plants are cultivated for their edible fruits and folk medicinal uses. Likewise, their leaves, flowers, and fruit essential oils (EOs) are described to have antiproliferative, antimicrobial, and antioxidant activities. This work analyzed the chemical compositions and evaluated the antiproliferative activities of essential oils (EO) of Myrcia bella Cambess, Myrcia fallax (Rich.) DC., Myrcia guianensis (Aubl.) DC., Eugenia aurata O. Berg, and Eugenia punicifolia (Kunth) DC, from the Brazilian Cerrado. EOs were obtained by leaf hydrodistillation and analyzed by Gas Chromatography-Mass Spectrometry (GC-MS) plus Gas Chromatography-Flame Ionization Detector (GC-FID). The major component in M. bella was α-cadinol (14.4%); in Myrcia fallax (Rich.) DC., guaiol acetate (14.4%); and in M.guianensis, (E)-iso-g‑bisabolene (17.5%). For E. aurata and E. punicifolia, bicyclogermacrene (25.3%) and (E)-caryophyllene (18%), respectively, were the most relevant chemical constituents. The EOs were tested against the human tumor cell lines UACC-62 (melanoma), MCF7 (breast), 786-0 (kidney), NCI-H460 (lung), OVCAR-3 (ovarian), HT29 (colon), and K562 (leukemia) and one non-tumor cell line (VERO). Eugenia aurata presented the most promising effect against HT29 (TGI = 1.5 mg/mL), K562 (TGI = 5.0 mg/mL), and no toxicity against non-tumor VERO cells (TGI> 250 mg/mL). For the other EOs, moderate to no activity was observed. So, in conclusion, E. aurata EOs revealed a good potential for anticancer applications.

Author Biographies

Catarina dos Santos, University of São Paulo State

Laboratory of Chemistry of UNESP-Assis (LAQUA) , Department of Biological Sciences

Natalia Covre de Melo, São Paulo State University

Laboratory of Chemistry of UNESP-Assis (LAQUA) , Department of Biological Sciences

Ana Lucia Tasca Gois Ruiz, University of Campinas

LAFTEx, Faculty of Pharmaceutical Sciences

Mary Ann Floglio, University of Campinas

LAFTEx, Faculty of Pharmaceutical Sciences

References

Abu-Izneid, T., Rauf, A., Shariati, M. A., Khalil, A. A., Imran, M., Rebezov, M., Uddin, Md. S., Mahomoodally, M. F., & Rengasamy, K. R. R. (2020). Sesquiterpenes and their derivatives-natural anticancer compounds: An update. Pharmacological Research, 161, 105165. https://doi.org/10.1016/j.phrs.2020.105165

Adams, R. P. (2007). Identification of essential oil components by gas chromatography/mass spectorscopy (4th ed). Allured Pub. Corp.

Alves, C. C. F., Oliveira, J. D., Estevam, E. B. B., Xavier, M. N., Nicolella, H. D., Furtado, R. A., Tavares, D. C., & Miranda, M. L. D. (2020). Antiproliferative activity of essential oils from three plants of the Brazilian Cerrado: Campomanesia adamantium (Myrtaceae), Protium ovatum (Burseraceae) and Cardiopetalum calophyllum (Annonaceae). Brazilian Journal of Biology, 80(2), 290–294. https://doi.org/10.1590/1519-6984.192643

Aranha, E. S. P., de Azevedo, S. G., dos Reis, G. G., Silva Lima, E., Machado, M. B., & de Vasconcellos, M. C. (2019). Essential oils from Eugenia spp.: In vitro antiproliferative potential with inhibitory action of metalloproteinases. Industrial Crops and Products, 141, 111736. https://doi.org/10.1016/j.indcrop.2019.111736

Barbosa, L. C. A., Filomeno, C. A., & Teixeira, R. R. (2016). Chemical Variability and Biological Activities of Eucalyptus spp. Essential Oils. Molecules, 21, 1671. https://doi.org/10.3390/molecules21121671

Bernardes, R. S. A., Sarrazin, S. L. F., dos Santos, F. A., Melo Rego, M. J. B. de, Rocha Pitta, M. G. da, Cordeiro, M. F., Almeida, P. D. O. de, Oliveira, R. B. de, Maduro Bouillet, L. E., Soares Maia, J. G., & Veras Mourao, R. H. (2018). Antioxidant Capacity and Cytotoxicity of the Aqueous Extract of Myrcia guianensis (Aubl.) DC. Pharmacognosy Journal, 10(6s), s135–s140. https://doi.org/10.5530/pj.2018.6s.25

Cardoso, C. A. L., & Ré-Poppi, N. (2009). Identification of the Volatile Compounds of Flower Oil of Campomanesia pubescens (Myrtaceae). Journal of Essential Oil Research, 21(5), 433–434. https://doi.org/10.1080/10412905.2009.9700210

Cascaes, M., Guilhon, G., Andrade, E., Zoghbi, M., & Santos, L. (2015). Constituents and Pharmacological Activities of Myrcia (Myrtaceae): A Review of an Aromatic and Medicinal Group of Plants. International Journal of Molecular Sciences, 16(10), 23881–23904. https://doi.org/10.3390/ijms161023881

Cerqueira, M. D. de, Souza-Neta, L. C., Passos, M. das G. V. M., Lima, E. de O., Roque, N. F., Martins, D., Guedes, M. L. S., & Cruz, F. G. (2007). Seasonal variation and antimicrobial activity of Myrcia myrtifolia essential oils. Journal of the Brazilian Chemical Society, 18(5), 998–1003. https://doi.org/10.1590/S0103-50532007000500018

Costa, M. F., Jesus, T. I., Lopes, B. R. P., Angolini, C. F. F., Montagnolli, A., Gomes, L. de P., Pereira, G. S., Ruiz, A. L. T. G., Carvalho, J. E., Eberlin, M. N., dos Santos, C., & Toledo, K. A. (2016). Eugenia aurata and Eugenia punicifolia HBK inhibit inflammatory response by reducing neutrophil adhesion, degranulation and NET release. BMC Complementary and Alternative Medicine, 16(1), 403. https://doi.org/10.1186/s12906-016-1375-7

de Melo, J. G., Santos, A. G., de Amorim, E. L. C., Nascimento, S. C. do, & de Albuquerque, U. P. (2011). Medicinal Plants Used as Antitumor Agents in Brazil: An Ethnobotanical Approach. Evidence-Based Complementary and Alternative Medicine, 2011, 1–14. https://doi.org/10.1155/2011/365359

de Souza, A., de Oliveira, C., de Oliveira, V., Betim, F., Miguel, O., & Miguel, M. (2018). Traditional Uses, Phytochemistry, and Antimicrobial Activities of Eugenia Species – A Review. Planta Medica, 84(17), 1232–1248. https://doi.org/10.1055/a-0656-7262

Durazzini, A. M. S., Machado, C. H. M., Fernandes, C. C., Willrich, G. B., Crotti, A. E. M., Candido, A. C. B. B., Magalhães, L. G., Squarisi, I. S., Ribeiro, A. B., Tavares, D. C., Martins, C. H. G., & Miranda, M. L. D. (2019). Eugenia pyriformis Cambess: A species of the Myrtaceae family with bioactive essential oil. Natural Product Research, 1–5. https://doi.org/10.1080/14786419.2019.1669031

Farag, N. F., El-Ahmady, S. H., Abdelrahman, E. H., Naumann, A., Schulz, H., Azzam, S. M., & El-Kashoury, E.-S. A. (2018). Characterization of essential oils from Myrtaceae species using ATR-IR vibrational spectroscopy coupled to chemometrics. Industrial Crops and Products, 124, 870–877. https://doi.org/10.1016/j.indcrop.2018.07.066

Fernandes, Y., Matos, J., Lima, C., Tardini, A., Viera, F., Maia, J., Monteiro, O., Longato, G., & Rocha, C. (2021). Essential Oils Obtained from Aerial Eugenia punicifolia Parts: Chemical Composition and Antiproliferative Potential Evidenced through Cell Cycle Arrest. Journal of the Brazilian Chemical Society. https://doi.org/10.21577/0103-5053.20210036

Fouche, G., Cragg, G. M., Pillay, P., Kolesnikova, N., Maharaj, V. J., & Senabe, J. (2008). In vitro anticancer screening of South African plants. Journal of Ethnopharmacology, 119(3), 455–461. https://doi.org/10.1016/j.jep.2008.07.005

Franco, C. de J. P., Ferreira, O. O., Antônio Barbosa de Moraes, Â., Varela, E. L. P., Nascimento, L. D. do, Percário, S., de Oliveira, M. S., & Andrade, E. H. de A. (2021). Chemical Composition and Antioxidant Activity of Essential Oils from Eugenia patrisii Vahl, E. punicifolia (Kunth) DC., and Myrcia tomentosa (Aubl.) DC., Leaf of Family Myrtaceae. Molecules, 26(11), 3292. https://doi.org/10.3390/molecules26113292

Franco, C. de J. P., Ferreira, O. O., Cruz, J. N., Varela, E. L. P., de Moraes, Â. A. B., Nascimento, L. D. do, Cascaes, M. M., Souza Filho, A. P. da S., Lima, R. R., Percário, S., Oliveira, M. S. de, & Andrade, E. H. de A. (2022). Phytochemical Profile and Herbicidal (Phytotoxic), Antioxidants Potential of Essential Oils from Calycolpus goetheanus (Myrtaceae) Specimens, and in Silico Study. Molecules, 27(15), 4678. https://doi.org/10.3390/molecules27154678

Furtado, F., Borges, B., Teixeira, T., Garces, H., Almeida Junior, L., Alves, F., Silva, C., & Fernandes Junior, A. (2018). Chemical Composition and Bioactivity of Essential Oil from Blepharocalyx salicifolius. International Journal of Molecular Sciences, 19(1), 33. https://doi.org/10.3390/ijms19010033

Gatto, L. J., Fabri, N. T., Souza, A. M. de, Fonseca, N. S. T. da, Furusho, A. dos S., Miguel, O. G., Dias, J. de F. G., Zanin, S. M. W., & Miguel, M. D. (2020). Chemical composition, phytotoxic potential, biological activities and antioxidant properties of Myrcia hatschbachii D. Legrand essential oil. Brazilian Journal of Pharmaceutical Sciences, 56, e18402. https://doi.org/10.1590/s2175-97902019000318402

Jerônimo, L. B., da Costa, J. S., Pinto, L. C., Montenegro, R. C., Setzer, W. N., Mourão, R. H. V., da Silva, J. K. R., Maia, J. G. S., & Figueiredo, P. L. B. (2021). Antioxidant and Cytotoxic Activities of Myrtaceae Essential Oils Rich in Terpenoids From Brazil. Natural Product Communications, 16(2), 1934578X2199615. https://doi.org/10.1177/1934578X21996156

Mazutti da Silva, S., Rezende Costa, C., Martins Gelfuso, G., Silva Guerra, E., de Medeiros Nóbrega, Y., Gomes, S., Pic-Taylor, A., Fonseca-Bazzo, Y., Silveira, D., & Magalhães, P. (2018). Wound Healing Effect of Essential Oil Extracted from Eugenia dysenterica DC (Myrtaceae) Leaves. Molecules, 24(1), 2. https://doi.org/10.3390/molecules24010002

Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., Hose, C., Langley, J., Cronise, P., Vaigro-Wolff, A., Gray-Goodrich, M., Campbell, H., Mayo, J., & Boyd, M. (1991). Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. JNCI Journal of the National Cancer Institute, 83(11), 757–766. https://doi.org/10.1093/jnci/83.11.757

Oliveira, M. S., & Souza Filho, A. P. (2022). Terpenoids. Bentham Science Publishers.

Périco, L. L., Rodrigues, V. P., Ohara, R., Nunes, V. V. A., da Rocha, L. R. M., Vilegas, W., dos Santos, C., & Hiruma-Lima, C. A. (2019). Can the gastric healing effect of Eugenia punicifolia be the same in male and female rats? Journal of Ethnopharmacology, 235, 268–278. https://doi.org/10.1016/j.jep.2019.02.012

Ramos, M. F. de S., Monteiro, S. da S., da Silva, V. P., Nakamura, M. J., & Siani, A. C. (2010). Essential Oils From Myrtaceae Species of the Brazilian Southeastern Maritime Forest (Restinga). Journal of Essential Oil Research, 22(2), 109–113. https://doi.org/10.1080/10412905.2010.9700275

Russo, R., Corasaniti, M. T., Bagetta, G., & Morrone, L. A. (2015). Exploitation of Cytotoxicity of Some Essential Oils for Translation in Cancer Therapy. Evidence-Based Complementary and Alternative Medicine, 2015, 1–9. https://doi.org/10.1155/2015/397821

Saldanha, L. L., Allard, P.-M., Afzan, A., de Melo, F. P. de S. R., Marcourt, L., Queiroz, E. F., Vilegas, W., Furlan, C. M., Dokkedal, A. L., & Wolfender, J.-L. (2020). Metabolomics of Myrcia bella Populations in Brazilian Savanna Reveals Strong Influence of Environmental Factors on Its Specialized Metabolism. Molecules, 25(12), 2954. https://doi.org/10.3390/molecules25122954

Sales, D. S., Carmona, F., de Azevedo, B. C., Taleb-Contini, S. H., Bartolomeu, A. C. D., Honorato, F. B., Martinez, E. Z., & Pereira, A. M. S. (2014). Eugenia punicifolia (Kunth) DC. as an Adjuvant Treatment for Type-2 Diabetes Mellitus: A non-Controlled, Pilot Study. Phytotherapy Research, 28(12), 1816–1821. https://doi.org/10.1002/ptr.5206

Salvador, M. J., Carvalho, J. E. de, Wisniewski-Jr, A., Kassuya, C. A. L., Santos, É. P., Riva, D., & Stefanello, M. É. A. (2011). Chemical composition and cytotoxic activity of the essential oil from the leaves of Casearia lasiophylla. Revista Brasileira de Farmacognosia, 21(5), 864–868. https://doi.org/10.1590/S0102-695X2011005000073

Santos, P., Gomes, L., Mazzei, J., Fontão, A. P., Sampaio, A., Siani, A., & Valente, L. (2018). Polyphenol and triterpenoid constituents of eugenia florida dc. (myrtaceae) leaves and their antioxidant and cytotoxic potential. Química Nova. https://doi.org/10.21577/0100-4042.20170284

Scalvenzi, L., Grandini, A., Spagnoletti, A., Tacchini, M., Neill, D., Ballesteros, J., Sacchetti, G., & Guerrini, A. (2017). Myrcia splendens (Sw.) DC. (syn. M. fallax (Rich.) DC.) (Myrtaceae) Essential Oil from Amazonian Ecuador: A Chemical Characterization and Bioactivity Profile. Molecules, 22(7), 1163. https://doi.org/10.3390/molecules22071163

Senapati, S., Mahanta, A. K., Kumar, S., & Maiti, P. (2018). Controlled drug delivery vehicles for cancer treatment and their performance. Signal Transduction and Targeted Therapy, 3(1), 7. https://doi.org/10.1038/s41392-017-0004-3

Silva, E. A. J., Estevam, E. B. B., Silva, T. S., Nicolella, H. D., Furtado, R. A., Alves, C. C. F., Souchie, E. L., Martins, C. H. G., Tavares, D. C., Barbosa, L. C. A., & Miranda, M. L. D. (2019). Antibacterial and antiproliferative activities of the fresh leaf essential oil of Psidium guajava L. (Myrtaceae). Brazilian Journal of Biology, 79(4), 697–702. https://doi.org/10.1590/1519-6984.189089

Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., & Boyd, M. R. (1990). New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening. JNCI Journal of the National Cancer Institute, 82(13), 1107–1112. https://doi.org/10.1093/jnci/82.13.1107

Stefanello, M. É. A., Pascoal, A. C. R. F., & Salvador, M. J. (2011). Essential Oils from Neotropical Myrtaceae: Chemical Diversity and Biological Properties. Chemistry & Biodiversity, 8(1), 73–94. https://doi.org/10.1002/cbdv.201000098

Downloads

Published

03/03/2023

How to Cite

SANTOS, C. dos .; MELO, N. C. de .; RUIZ, A. L. T. G. .; FLOGLIO, M. A. . Antiproliferative activity from five Myrtaceae essential oils . Research, Society and Development, [S. l.], v. 12, n. 3, p. e14612340536, 2023. DOI: 10.33448/rsd-v12i3.40536. Disponível em: https://rsdjournal.org/index.php/rsd/article/view/40536. Acesso em: 26 nov. 2024.

Issue

Section

Agrarian and Biological Sciences