Chemical constituents of extracts, circadian variation of essential oil chemical composition and antioxidant activity of Plectranthus neochilus

Authors

DOI:

https://doi.org/10.5902/2179460X87721

Keywords:

Boldo, Flavonoid, Natural products

Abstract

This work describes the phytochemical study of the extracts, the circadian variation of volatile compounds and the antioxidant activity of the leaves of the plant species Plectranthus neochilus Schltr. (Lamiaceae). The phytochemical study of the hexane extract provided two triterpenes: α-amyrin esterified and friedelin. A mixture of the steroids sitosterol and stigmasterol was also obtained from this extract. From the ethyl acetate extract, the methoxylated flavone at positions C-6 and C-7, cirsimaritin, was obtained. All the compounds obtained were described for the first time in the species, with the structural elucidation of the isolated compounds being based on spectroscopic analysis of 1D NMR, HPLC, ESI and comparison with data found in the literature. By evaluating the circadian variation in the composition of the essential oil, it was observed that the major compounds (E)-caryphyllene (21.55%, 24.06% and 17.53%) and methyl communate (19.72%; 11.09% and 26.88%) showed significant variations in the three collection periods (8h, 13h and 18h), with the diterpene methyl communate identified for the first time in the essential oil of Plectranthus, as well as the species P. neochilus. The RSA of the essential oil at 13h showed the highest average among the three times evaluated (19.94%). Regarding the extracts, the extraction method with MeOH from the leaves (EMA) proved to be the most efficient in the RSA (10.46%) and RP (0.737) tests, confirmed by the greatest accumulation of total phenolics (466.67 mg.g-1).

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Author Biographies

Abraão José Silva Viana, Federal University of the Jequitinhonha and Mucuri Valleys

Graduated in Agronomy from the Federal Rural University of Rio de Janeiro (UFRRJ, 2008) and Master in Organic Chemistry/Natural Products Chemistry from the Federal University of Jequitinhonha and Mucuri Valleys (UFVJM, 2011). PhD from the Federal University of Lavras (UFLA) in the Postgraduate Program in Medicinal, Aromatic and Condiment Plants. He is a Laboratory Technician/Chemistry (Multiuser Laboratory LIPEMVALE-UFVJM), working mainly in the areas of Agronomy and Organic Chemistry/Medicinal Plants. Has experience in the techniques of high performance liquid chromatography (HPLC), X-ray fluorescence (XRF), elemental analysis CHNS/O and flame atomic absorption.

Alyson Tôrres de Barros, Federal University of the Jequitinhonha and Mucuri Valleys

Graduated in Chemistry from the Federal University of Jequitinhonha and Mucuri Valleys (UFVJM), Bachelor's Degree in Biological Sciences from the Single Faculty of Ipatinga, Master's Degree in Organic Chemistry with an emphasis on Chemistry of Natural Products from the Federal University of Jequitinhonha and Mucuri Valleys (UFVJM), specialized in LIBRAS from Cândido Mendes University (UCAM). Currently a doctoral student in Chemistry at the Federal University of Espírito Santo (UFES) research line in Chemometrics.

Deilson de Almeida Alves, Federal University of the Jequitinhonha and Mucuri Valleys

He holds a master's, doctorate, and postdoctorate from the Graduate Program in Plant Production at the Federal University of Jequitinhonha and Mucuri Valleys (UFVJM). He holds a degree in Agricultural Engineering from the Federal Institute of Education, Science, and Technology of Minas Gerais (IFMG). During his graduate studies, he received a Capes and CNPq scholarship, working on research projects in the areas of fruit growing, dragon fruit, liming and fertilization, plant nutrition, pests and diseases, pollination, soils, and the environment. During his undergraduate studies, he participated in research projects with an institutional scholarship from IFMG. He was a member of research groups registered with CNPq, such as GEFRUT and Meio Ambiente.

Daniel José Silva Viana, Federal University of the Jequitinhonha and Mucuri Valleys

He holds a degree in Agronomy from the Federal University of Jequitinhonha and Mucuri Valleys (2006) and a Master's degree in Plant Production from the Federal University of Jequitinhonha and Mucuri Valleys (2009). He holds a PhD in Biofuels from UFVJM. I am currently a technician in the Microbiology/Parasitology/Genetics Laboratory at UFVJM. I have experience in Agronomy and Biology, with an emphasis on Agronomy, working mainly on the following topics: sweet potato, biofuels, pepper, vegetables, vegetable breeding, entomology, microbiology, parasitology, molecular biology, genetics, distance learning, environmental education, mineral resources, agroecology, microbiological water analysis, and experimental statistics. I currently work in the laboratory with Canine Visceral Leishmaniasis, insect identification, mounting and collecting sand flies, and mounting and preserving bees. microbiology laboratory and molecular biology laboratory of the Department of Biological Sciences at UFVJM.

Paulo Henrique Fidêncio, Federal University of the Jequitinhonha and Mucuri Valleys

Graduated in Chemistry, Bachelor's and Licentiate degrees from the Federal University of Viçosa (1994), Master's degree in Agrochemistry from the Federal University of Viçosa (1997) with an area of ​​concentration in Analytical Chemistry, PhD in Chemistry from the State University of Campinas (2001), concentrating in Analytical Chemistry and post-doctorate at the Federal University of Viçosa (2002) and at the Federal University of Minas Gerais (2005-2006). He has experience in Chemistry, with an emphasis on Analytical Chemistry, working mainly in the following topics: near-infrared spectroscopy, potentiometry, multivariate analysis: Principal Component Analysis (PCA), Hierarchical Cluster Analysis (AHA), Kohonen Networks, Counter-Propagation Networks, Partial Least Squares (PLS), Artificial Neural Networks (ANN) and Radial Basis Function Networks (RBFN). Full Professor at the Federal University of the Jequitinhonha and Mucuri Valleys (UFVJM).

Patrícia Machado de Oliveira, Federal University of the Jequitinhonha and Mucuri Valleys

I have a bachelor's degree in Chemistry from the Federal University of Minas Gerais (1999), a master's degree in Chemistry from the Federal University of Minas Gerais (2002), and a PhD in Chemistry from the Federal University of Minas Gerais (2006). I am currently an associate professor II at the Federal University of Jequitinhonha and Mucuri Valleys - JK Campus, affiliated with the Chemistry Department, and a collaborator in the Graduate Program in Chemistry (PPGQ). I work as Coordinator and Supervised Curricular Internship of the Undergraduate Course in Chemistry - Licentiate Degree and am currently responsible for the institutional coordination of the Pedagogical Residency Program at UFVJM. I have experience in Chemistry, with an emphasis on Chemistry, working mainly on the following topics: Phytochemistry, Medicinal Plants, Chemistry of Natural Products.

References

Abdallah, H. A., Afifi, N., Mohamed, E. I., Sebak, M., Mohammed, R., & Zaki, M. A. (2025). A comparative study of the essential oil extracts of Centaurea alexanderina different parts: GC-MS analysis, antimicrobial, antioxidant, and anti-hyperglycemic activities. BMC Complementary Medicine and Therapies, 25(1), 90. doi: 10.1186/s12906-025-04805-1 DOI: https://doi.org/10.1186/s12906-025-04805-1

Abdel-Mogib, M., Albar, H. A., & Batterjee, S. M. (2002). Chemistry of the genus Plectranthus. Molecules, 7(2), 271-301. doi: 10.3390/70200271 DOI: https://doi.org/10.3390/70200271

Adams, R. P. (2007). Identification of essential oil components by gas chromatography/mass.

Alara, O. R., Abdurahman, N. H., & Ukaegbu, C. I. (2021). Extraction of phenolic compounds: A review. Current research in food science, 4, 200-214. doi: 10.1016/j.Crfs.2021.03.011 DOI: https://doi.org/10.1016/j.crfs.2021.03.011

Albuquerque, R. D. D. G., Venegas-Casanova, E. A., Gavídia-Valencia, J. G., Rubio-López, F. R., Rengifo-Penadillos, R. A., Roldán-Rodriguez, J. E., Quintana-Díaz, A. (2024). Review on selected essential oils from america as applied resources to control Bemisia Tabaci, an important agronomical pest. Journal Of Applied Biology And Biotechnology, 12(1), 10-16. doi: 10.7324/Jabb.2024.157409 DOI: https://doi.org/10.7324/JABB.2024.157409

Antão, A. R., Bangay, G., Domínguez-Martín, E. M., Díaz-Lanza, A. M., & Ríjo, P. (2021). Plectranthus ecklonii benth: a comprehensive review into its phytochemistry and exerted biological activities. Frontiers in Pharmacology, 12, 768268. doi: 10.3389/Fphar.2021.768268 DOI: https://doi.org/10.3389/fphar.2021.768268

Bakhtiar, Z., Hassandokht, M., Fozi, V., & Mirjalili, M. H. (2025). Agro-morphological yield-attributed traits, essential oil content, phytochemical composition, and biological activities of some Medicago species. Chemical and Biological Technologies in Agriculture, 12(1), 25. doi: 10.1186/s40538-025-00740-y DOI: https://doi.org/10.1186/s40538-025-00740-y

Bandeira, J. M., Barbosa, F. F., Barbosa, L. M. P., Rodrigues, I. C. S., Bacarin, M. A., Peters, J. A., & Braga, E. J. B. (2011). Composição do óleo essencial de quatro espécies do gênero Plectranthus. Revista Brasileira de Plantas Medicinais, 13, 157-164. doi: 10.1590/S1516-05722011000200006 DOI: https://doi.org/10.1590/S1516-05722011000200006

Basist, P., Parveen, B., Zahiruddin, S., Gautam, G., Parveen, R., Khan, M. A., ... & Ahmad, S. (2022). Potential nephroprotective phytochemicals: Mechanism and future prospects. Journal of ethnopharmacology, 283, 114743. doi: 10.1016/j.Jep.2021.114743 DOI: https://doi.org/10.1016/j.jep.2021.114743

Benali, T., Jaouadi, I., Ghchime, R., El Omari, N., Harboul, K., Hammani, K., ... & Bouyahya, A. (2022). The current state of knowledge in biological properties of cirsimaritin. Antioxidants, 11(9), 1842. doi: 10.3390/Antiox11091842 DOI: https://doi.org/10.3390/antiox11091842

Blois, M. S. (1958). Antioxidant Determination By The Use Of a Stable Free Radical. Nature, 181(4617), 1199-1200. doi: 10.1038/1811199a0 DOI: https://doi.org/10.1038/1811199a0

Bonoli, M., Marconi, E., & Caboni, M. F. (2004). Free and bound phenolic compounds in barley (Hordeum vulgare L.) flours: Evaluation of the extraction capability of different solvent mixtures and pressurized liquid methods by micellar electrokinetic chromatography and spectrophotometry. Journal of Chromatography A, 1057(1-2), 1-12. doi: 10.1016/j.Chroma.2004.09.024 DOI: https://doi.org/10.1016/j.chroma.2004.09.024

Borges, G. A., Ferreira, J. F., Elias, S. T., Guerra, E. N. S., & Simeoni, L. A. (2016). Cytotoxic effect of Plectranthus neochilus extracts in head and neck carcinoma cell lines. African Journal of Pharmacy and Pharmacology, 10(10), 157-163. doi: 10.5897/Ajpp2015.4355 DOI: https://doi.org/10.5897/AJPP2015.4355

Câmara, C. C., Nascimento, N. R., Macêdo-Filho, C. L., Almeida, F. B., & Fonteles, M. C. (2003). Antispasmodic effect of the essential oil of Plectranthus barbatus and some major constituents on the guinea-pig ileum. Planta Medica, 69(12), 1080-1085. doi: 10.1055/s-2003-45186 DOI: https://doi.org/10.1055/s-2003-45186

Crevelin, E. J., Caixeta, S. C., Dias, H. J., Groppo, M., Cunha, W. R., Martins, C. H. G., & Crotti, A. E. M. (2015). Antimicrobial activity of the essential oil of Plectranthus neochilus against cariogenic bacteria. Evidence-Based Complementary and Alternative Medicine, 2015(1), 102317. doi: 10.1155/2015/102317 DOI: https://doi.org/10.1155/2015/102317

Gáborová, M., Šmejkal, K., & Kubínová, R. (2021). Abietane diterpenes of the genus Plectranthus sensu lato. Molecules, 27(1), 166. doi: 10.3390/Molecules27010166 DOI: https://doi.org/10.3390/molecules27010166

Galbiatti, M. I., Cassola, F., Mesquita, A. T., Pinheiro, G. P., Mayer, J. L. S., & Sawaya, A. C. H. F. (2021). Plectranthus neochilus Schltr.: Anatomic and cytogenetic analyses and chemical characterization of its essential oil. South African Journal of Botany, 143, 97-106. doi: 10.1016/j.Sajb.2021.07.035 DOI: https://doi.org/10.1016/j.sajb.2021.07.035

Gushiken, L. F. S., Beserra, F. P., Hussni, M. F., Gonzaga, M. T., Ribeiro, V. P., De Souza, P. F., ... & Pellizzon, C. H. (2022). Beta-caryophyllene as an antioxidant, anti-inflammatory and re-epithelialization activities in a rat skin wound excision model. Oxidative medicine and cellular longevity, 2022(1), 9004014. doi: 10.1155/2022/9004014 DOI: https://doi.org/10.1155/2022/9004014

Lawal, O. A., Hutchings, A. H., & Oyedeji, O. (2010). Chemical Composition of the Leaf Oil of Plectranthus neochilus Schltr. Journal of Essential Oil Research, 22(6), 546-547. doi: 10.1080/10412905.2010.9700396 DOI: https://doi.org/10.1080/10412905.2010.9700396

Lorenzi, H., Matos, F. J. A. (2002). Plantas Medicinais No Brasil: Nativas e Exóticas.

Luz, T. R. S. A., Leite, J. A. C., de Mesquita, L. S. S., Bezerra, S. A., Ribeiro, E. C. G., Silveira, D. P. B., ... & Coutinho, D. F. (2022). Seasonal variation in the chemical composition and larvicidal activity against Aedes aegypti L. of essential oils from Brazilian Amazon. Experimental. Parasitology, 243, 108405. doi: 10.1016/j.Exppara.2022.108405 DOI: https://doi.org/10.1016/j.exppara.2022.108405

Malavolta, E. (2006). Manual de nutrição mineral de plantas. Agronômica Ceres.

Mamoudou, H., Abdoulaye, A. H., Ditchou, N. Y. O., Olumasai, J. N., Adissa, R. M. Z. K., & Mune, M. A. M. (2025). Computational investigation of Plectranthus neochilus essential oil phytochemicals interaction with dipeptidyl peptidase 4: A potential avenue for antidiabetic drug discovery. Current Pharmaceutical Analysis, 21(3), 169-178. doi: 10.1016/j.Cpan.2025.03.002 DOI: https://doi.org/10.1016/j.cpan.2025.03.002

Mesquita, L. S. F., Matos, T. S., do Nascimento Ávila, F., da Silva Batista, A., Moura, A. F., de Moraes, M. O., ... & Pessoa, O. D. L. (2021). Diterpenoids from leaves of cultivated Plectranthus ornatus. Planta Medica, 87(01/02), 124-135. doi: 10.1055/a-1209-3252 DOI: https://doi.org/10.1055/a-1209-3252

Mota, L., Figueiredo, A. C., Pedro, L. G., Barroso, J. G., Miguel, M. G., Faleiro, M. L., & Ascensao, L. (2014). Volatile-Oils Composition, and Bioactivity of the Essential Oils of Plectranthus barbatus, P. neochilus, and P. ornatus Grown in Portugal. Chemistry & biodiversity, 11(5), 719-732. doi: 10.1002/Cbdv.201300161 DOI: https://doi.org/10.1002/cbdv.201300161

Munteanu, I. G., & Apetrei, C. (2021). Analytical methods used in determining antioxidant activity: A review. International journal of molecular sciences, 22(7), 3380. doi: 10.3390/Ijms22073380 DOI: https://doi.org/10.3390/ijms22073380

Napagoda, M., Gerstmeier, J., Butschek, H., Lorenz, S., De Soyza, S., Qader, M., ... & Werz, O. (2022). Plectranthus zeylanicus: a rich source of secondary metabolites with antimicrobial, disinfectant and anti-inflammatory activities. Pharmaceuticals, 15(4), 436. doi: 10.3390/Ph15040436 DOI: https://doi.org/10.3390/ph15040436

Oliveira, P. M., Alves, R. B. N., Ferreira, A. A., Brasileiro, E. G., Takahashi, J. A., Lage, G. L. C., Ferraz V. P., Silveira, D., Raslan, D. S., Singh, V. K., Govil, J. N., Chinnathambi, A. Composition and antimicrobial activity of essential oil from Plectranthus Ornatus Codd. Phytochemistry And Pharmacology: Recent Progress In Medicinal Plants (v. 17, chapter. 10, pp. 395-409). 2007a. Https://Www.Cabidigitallibrary.Org/doi/Full/10.5555/20083101868

Oliveira, P. M., Souza, J. N. C., Lage, G. L. C., Alves, R. B., Silveira, D., Raslan, D. S. Ethnobotany, Pharmacology And Phytochemistry Of Plectranthus (Lamiaceae). Phytochemistry And Pharmacology: Recent Progress In Medicinal Plants (v. 17, chapter. 10, pp. 363-393). 2007b.

Oliveira, T. A. S., Santiago, M. B., Santos, V. H. P., Silva, E. O., Martins, C. H. G., Crotti, A. E. M. (2022). Antibacterial activity of essential oils against oral pathogens. Chemistry & Biodiversity, 19(4), e202200097. doi: 10.1002/Cbdv.202200097 DOI: https://doi.org/10.1002/cbdv.202200097

Pereira, M., Matias, D., Pereira, F., Reis, C. P., Simões, M. F., & Rijo, P. (2015). Antimicrobial screening of Plectranthus madagascariensis and P. neochilus extracts. Biomedical and Biopharmaceutical Research. doi: 10.19277/Bbr.12.1.111 DOI: https://doi.org/10.19277/BBR.12.1.111

Rodríguez-Ferreiro, A. O., Ochoa-Pacheco, A., Méndez-Rodriguez, D., Ortiz-Beatón, E., Font-Salmo, O., Guisado-Bourzac, F., ... & Setzer, W. N. (2022). LC-MS Characterization and Biological Activities of Cuban Cultivars of Plectranthus neochilus Schltr. Plants, 11(1), 134. doi: 10.3390/Plants11010134 DOI: https://doi.org/10.3390/plants11010134

Sako, K. B., Makhafola, T. J., Antonissen, R., Pieters, L., Verschaeve, L., & Elgorashi, E. E. (2023). Antioxidant, antimutagenic and antigenotoxic properties of Plectranthus species. South African Journal of Botany, 161, 113-125. doi: 10.1016/J.Sajb.2023.07.062 DOI: https://doi.org/10.1016/j.sajb.2023.07.062

Silva, F. C. (2009). Manual de análises químicas de solos, plantas e fertilizantes. Http://Www.Infoteca.Cnptia.Embrapa.Br/Infoteca/Handle/Doc/330496

Singh, R. P., Chidambara Murthy, K. N., & Jayaprakasha, G. K. (2002). Studies on the antioxidant activity of pomegranate (Punica granatum) peel and seed extracts using in vitro models. Journal of agricultural and food chemistry, 50(1), 81-86. doi: 10.1021/Jf010865b DOI: https://doi.org/10.1021/jf010865b

Sun, W., & Shahrajabian, M. H. (2023). Therapeutic potential of phenolic compounds in medicinal plants—Natural health products for human health. Molecules, 28(4), 1845. doi: 10.3390/Molecules28041845 DOI: https://doi.org/10.3390/molecules28041845

Van Den Dool, H. A. N. D., & Kratz, P. D. (1963). A generalization of the retention index system including linear temperature programmed gas—liquid partition chromatography. Journal of Chromatography a, 11, 463-471. doi: 10.1016/S0021-9673(01)80947-X DOI: https://doi.org/10.1016/S0021-9673(01)80947-X

Yıldırım, A., Mavi, A., & Kara, A. A. (2001). Determination of antioxidant and antimicrobial activities doi: 10.1021/Jf0103572 DOI: https://doi.org/10.1021/jf0103572

Zhang, Y., Li, Y., Ren, X., Zhang, X., Wu, Z., & Liu, L. (2023). The positive correlation of antioxidant activity and prebiotic effect about oat phenolic compounds. Food Chemistry, 402, 134231. doi: 10.1016/j.Foodchem.2022.134231 DOI: https://doi.org/10.1016/j.foodchem.2022.134231

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Published

2025-10-24

How to Cite

Viana, A. J. S., Barros, A. T. de, Alves, D. de A., Viana, D. J. S., Fidêncio, P. H., & Oliveira, P. M. de. (2025). Chemical constituents of extracts, circadian variation of essential oil chemical composition and antioxidant activity of Plectranthus neochilus. Ciência E Natura, 47, e87721. https://doi.org/10.5902/2179460X87721

Issue

Vol. 47 (2025): Publicação contínua

Section

Chemistry

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