{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T19:37:10Z","timestamp":1789760230135,"version":"4.0.1"},"reference-count":56,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2023,2,11]],"date-time":"2023-02-11T00:00:00Z","timestamp":1676073600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The Amazonian region of Ecuador has an extremely rich vegetal biodiversity, and its inhabitants have proven to have a millennial ancestral knowledge of the therapeutic and medicinal use of these resources. This work aimed to evaluate the chemical composition and biological activity of the essential oil obtained from the medicinal plant Clinopodium brownei (Sw.) Kuntze, which is widely spread in tropical and subtropical America. This species is traditionally used for treating respiratory and digestive diseases and is also known for its analgesic properties. Most of the molecules detected on a non-polar column were ethyl cinnamate 21.4%, pulegone 20.76%, methyl cinnamate 16.68%, caryophyllene 8.17%, \u03b2-selinene 7.92% and menthone 7.51%, while those detected on a polar column were: pulegone 29.90%, ethyl cinnamate 18.75%, methyl cinnamate 13.82%, caryophyllene 10.0% and menthone 8.04%. The antioxidant activity by the assays, DPPH (2.2-diphenyl-1-picrylhydrazyl) and ABTS (2.2\u2032-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid)), shows the following values of 50% inhibition of oxidation, IC50 DPPH 1.77 mg\/mL, IC50 ABTS 0.06 mg\/mL, which, compared to the essential oil of Thymus vulgaris (natural positive control), turn out to be less active. Bioautography indicates that the molecules responsible for the antioxidant activity are derived from cinnamic acid: ethyl cinnamate and methyl cinnamate, and caryophyllene. The antimicrobial activity on the nine microorganisms evaluated shows bacterial growth inhibitory concentrations ranging from 13.6 mg\/mL for Staphylococcus epidermidis ATCC 14990 to 3.1 mg\/mL for Candida albicans ATCC 10231; the results are lower than those of the positive control. Bioautography assigns antimicrobial activity to caryophyllene. The results indicate a very interesting activity of the essential oil and several of its molecules, validating the traditional use and the importance of this medicinal plant from Ecuador.<\/jats:p>","DOI":"10.3390\/molecules28041741","type":"journal-article","created":{"date-parts":[[2023,2,13]],"date-time":"2023-02-13T02:14:11Z","timestamp":1676254451000},"page":"1741","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Chemical Composition, Antimicrobial and Antioxidant Bioautography Activity of Essential Oil from Leaves of Amazon Plant Clinopodium brownei (Sw.)"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7147-261X","authenticated-orcid":false,"given":"Paco","family":"Noriega","sequence":"first","affiliation":[{"name":"Master Program of Natural Pharmaceutical Products, Universidad Polit\u00e9cnica Salesiana, Avenida 12 de Octubre N2422 y Wilson, Quito 170109, Ecuador"},{"name":"Group of Research and Development in Science Applied to Biological Resourses, Universidad Polit\u00e9cnica Salesiana, Avenida 12 de Octubre N2422 y Wilson, Quito 170109, Ecuador"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4844-8069","authenticated-orcid":false,"given":"Lissette","family":"Calder\u00f3n","sequence":"additional","affiliation":[{"name":"Master Program of Natural Pharmaceutical Products, Universidad Polit\u00e9cnica Salesiana, Avenida 12 de Octubre N2422 y Wilson, Quito 170109, Ecuador"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Ojeda","sequence":"additional","affiliation":[{"name":"Master Program of Natural Pharmaceutical Products, Universidad Polit\u00e9cnica Salesiana, Avenida 12 de Octubre N2422 y Wilson, Quito 170109, Ecuador"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Erika","family":"Paredes","sequence":"additional","affiliation":[{"name":"Group of Research and Development in Science Applied to Biological Resourses, Universidad Polit\u00e9cnica Salesiana, Avenida 12 de Octubre N2422 y Wilson, Quito 170109, Ecuador"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1080\/23766808.2017.1295705","article-title":"Priority areas for biodiversity conservation in mainland Ecuador","volume":"3","author":"Cuesta","year":"2017","journal-title":"Neotrop. Biodivers."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1016\/S0169-2046(02)00006-3","article-title":"Assessing biodiversity conservation priorities: Ecosystem risk and representativeness in continental Ecuador","volume":"59","author":"Sierra","year":"2002","journal-title":"Landsc. Urban Plan."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Mestanza-Ram\u00f3n, C., Henkanaththegedara, S.M., V\u00e1sconez Duchicela, P., Vargas Tierras, Y., S\u00e1nchez Capa, M., Constante Mej\u00eda, D., and Mestanza Ram\u00f3n, P. (2020). In-situ and ex-situ biodiversity conservation in Ecuador: A review of policies, actions and challenges. Diversity, 12.","DOI":"10.3390\/d12080315"},{"key":"ref_4","unstructured":"De la Torre, L., Navarrete, H., Mac\u00eda, M., Balslev, H., and Muriel, P. (2008). Enciclopedia de las Plantas \u00datiles del Ecuador (con Extracto de Datos), Herbario QCA de la Escuela de Ciencias Biol\u00f3gicas de la Pontificia Universidad Cat\u00f3lica del Ecuador & Herbario AAU del Departamento de Ciencias Biol\u00f3gicas de la Universidad de Aarhus. [1st ed.]."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/j.jep.2015.01.038","article-title":"Medicinal plants of the Achuar (Jivaro) of Amazonian Ecuador: Ethnobotanical survey and comparison with other Amazonian pharmacopoeias","volume":"164","author":"Giovannini","year":"2015","journal-title":"J. Ethnopharmacol."},{"key":"ref_6","first-page":"9105746","article-title":"Ethnobotanical research at the Kutuk\u00fa Scientific Station, Morona-Santiago, Ecuador","volume":"2016","author":"Ballesteros","year":"2016","journal-title":"BioMed Rev. Int."},{"key":"ref_7","first-page":"109","article-title":"Etnobot\u00e1nica Ts\u00e1chila, Pichincha-Ecuador","volume":"5","author":"Montalvo","year":"2004","journal-title":"Cinchonia"},{"key":"ref_8","first-page":"1","article-title":"El uso de la etnobot\u00e1nica como cura de eruptivas de la infancia por la etnia chachi. Esmeraldas. Ecuador","volume":"3","author":"Moreira","year":"2016","journal-title":"Rev. Investig. Talentos"},{"key":"ref_9","first-page":"66","article-title":"Parches de bosque y etnobot\u00e1nica Shuar en Palora, Morona Santiago-Ecuador","volume":"8","author":"Reyes","year":"2007","journal-title":"Cinchonia"},{"key":"ref_10","first-page":"1","article-title":"Etnobot\u00e1nica y derechos de la naturaleza en el aja shuar: Caso de estudio parroquia Nankais, cant\u00f3n Nangaritza, provincia Zamora Chinchipe, Ecuador","volume":"8","author":"Poma","year":"2021","journal-title":"Siembra"},{"key":"ref_11","first-page":"64","article-title":"Etnobot\u00e1nica Huaorani de Tivacuno-Tiputini Parque Nacional Yasun\u00ed","volume":"3","year":"2002","journal-title":"Cinchonia"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3","DOI":"10.17163\/lgr.n10.2009.01","article-title":"Extracci\u00f3n, qu\u00edmica, actividad biol\u00f3gica, control de calidad y potencial econ\u00f3mico de los aceites esenciales","volume":"10","author":"Noriega","year":"2009","journal-title":"La Granja"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0021-9673(01)01314-0","article-title":"Gas chromatographic technologies for the analysis of essential oils","volume":"936","author":"Marriott","year":"2001","journal-title":"J. Chromatogr. A"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1080\/10412905.2020.1746698","article-title":"The progress of essential oils as potential therapeutic agents: A review","volume":"32","author":"Baptista","year":"2020","journal-title":"J. Essent. Oil Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1100","DOI":"10.2174\/1389200219666180723144850","article-title":"Essential oils: Extraction techniques, pharmaceutical and therapeutic potential-a review","volume":"19","author":"Aziz","year":"2018","journal-title":"Curr. Drug Metab."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Diniz do Nascimento, L., Moraes, A.A., Costa, K.S., Pereira, J.M., Taube, P.S., Costa, C.M., and Faria, L.J. (2020). Bioactive natural compounds and antioxidant activity of essential oils from spice plants: New findings and potential applications. Biomolecules, 10.","DOI":"10.3390\/biom10070988"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1046\/j.0412-5463.2001.00113.x","article-title":"Preservative systems containing essential oils in cosmetic products","volume":"24","author":"Maccioni","year":"2002","journal-title":"Int. J. Cosmet. Sci."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1007\/BF02834854","article-title":"Essential oils and fragrances from natural sources","volume":"9","author":"Vankar","year":"2004","journal-title":"Resonance"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1016\/j.foodchem.2003.07.019","article-title":"Chemical composition and biological activities of Ishpingo essential oil, a traditional Ecuadorian spice from Ocotea quixos (Lam.) Kosterm. (Lauraceae) flower calices","volume":"85","author":"Bruni","year":"2004","journal-title":"Food Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"674","DOI":"10.1002\/ffj.1648","article-title":"Essential oil of wild ocotea quixos (lam.) kosterm. (lauraceae) leaves from amazonian Ecuador","volume":"21","author":"Sacchetti","year":"2006","journal-title":"Flavour Fragr. J."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1556\/1006.2018.31.2.11","article-title":"Antimicrobial and antioxidant bioautography activity of bark essential oil from Ocotea quixos (Lam.) kosterm","volume":"31","author":"Noriega","year":"2018","journal-title":"J. Planar Chromatogr.-Mod. TLC"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.etap.2008.08.002","article-title":"Bioactivities of Piper aduncum L. and Piper obliquum Ruiz & Pavon (Piperaceae) essential oils from eastern Ecuador","volume":"27","author":"Guerrini","year":"2009","journal-title":"Environ. Toxicol. Pharmacol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1051\/parasite\/2019024","article-title":"Larvicidal activity of Ocimum campechianum, Ocotea quixos and Piper aduncum essential oils against Aedes aegypti","volume":"26","author":"Scalvenzi","year":"2019","journal-title":"Parasite"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"6194640","DOI":"10.1155\/2019\/6194640","article-title":"Rediscovering medicinal Amazonian aromatic plants: Piper carpunya (Piperaceae) essential oil as paradigmatic study","volume":"2019","author":"Ballesteros","year":"2019","journal-title":"Evid. Based Complement. Altern. Med."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Valarezo, E., Rivera, J.X., Coronel, E., Barzallo, M.A., Calva, J., Cartuche, L., and Meneses, M.A. (2021). Study of volatile secondary metabolites present in Piper carpunya leaves and in the traditional ecuadorian beverage Guaviduca. Plants, 10.","DOI":"10.3390\/plants10020338"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Noriega, P., Guerrini, A., Sacchetti, G., Grandini, A., Ankuash, E., and Manfredini, S. (2019). Chemical composition and biological activity of five essential oils from the Ecuadorian Amazon rain forest. Molecules, 24.","DOI":"10.3390\/molecules24081637"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"149","DOI":"10.5897\/JPP2017.0467","article-title":"Clinopodium nubigenum (Kunth) Kuntze essential oil: Chemical composition, antioxidant activity, and antimicrobial test against respiratory pathogens","volume":"10","author":"Noriega","year":"2018","journal-title":"J. Pharmacogn. Phytother."},{"key":"ref_28","first-page":"2121","article-title":"Phenolic compounds from Clinopodium tomentosum (Kunth) govaerts (Lamiaceae)","volume":"25","author":"Salto","year":"2014","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"749","DOI":"10.1016\/j.bjp.2019.08.001","article-title":"Selective BuChE inhibitory activity, chemical composition, and enantiomer content of the volatile oil from the Ecuadorian plant Clinopodium brownei","volume":"29","author":"Matailo","year":"2019","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Armijos, C., Ram\u00edrez, J., Salinas, M., Vidari, G., and Su\u00e1rez, A.I. (2021). Pharmacology and Phytochemistry of Ecuadorian Medicinal Plants: An Update and Perspectives. Pharmaceuticals, 14.","DOI":"10.3390\/ph14111145"},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Vandebroek, I., and Picking, D. (2020). Popular Medicinal Plants in Portland and Kingston, Jamaica, Kingston. [1st ed.].","DOI":"10.1007\/978-3-030-48927-4"},{"key":"ref_32","first-page":"89","article-title":"Estudio preliminar sobre plantas medicinales utilizadas en algunas comunidades de las provincias de Azuay, Ca\u00f1ar y Loja, para afecciones del aparato gastrointestinal","volume":"23","author":"Ansaloni","year":"2010","journal-title":"Rev. Tecnol\u00f3gica-ESPOL"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1002\/(SICI)1099-1026(200001\/02)15:1<21::AID-FFJ861>3.0.CO;2-G","article-title":"Composition of the essential oil of Satureja brownei (SW.) Briq. from Venezuela","volume":"15","author":"Rojas","year":"2000","journal-title":"Flavour Fragr. J."},{"key":"ref_34","first-page":"52","article-title":"Composici\u00f3n qu\u00edmica vol\u00e1til de Satureja brownei (Sw.) Briq. colombiana y determinaci\u00f3n de su actividad antioxidante","volume":"15","author":"Jaramillo","year":"2010","journal-title":"Rev. Cuba. Plantas Med."},{"key":"ref_35","unstructured":"Adams, R.P. (2012). Identification of Essential Oils by Ion Trap Mass Spectroscopy, Academic Press. [1st ed.]."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"043101","DOI":"10.1063\/1.3653552","article-title":"Retention Indices for Frequently Reported Compounds of Plant Essential Oils","volume":"40","author":"Babushok","year":"2011","journal-title":"J. Phys. Chem. Ref. Data"},{"key":"ref_37","unstructured":"Suryanti, V., Wibowo, F.R., Khotijah, S., and Andalucki, N. (2018). IOP Conference Series: Materials Science and Engineering, IOP Publishing."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"224","DOI":"10.17628\/ecb.2019.8.224-226","article-title":"Evaluation of antioxidant activity of cinnamic acid and some of its derivatives","volume":"8","author":"Oladimeji","year":"2019","journal-title":"Eur. Chem. Bull."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"11808","DOI":"10.3390\/molecules200711808","article-title":"The anticancer, antioxidant and antimicrobial properties of the sesquiterpene \u03b2-caryophyllene from the essential oil of Aquilaria crassna","volume":"20","author":"Dahham","year":"2015","journal-title":"Molecules"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"394","DOI":"10.1017\/S0007114512001298","article-title":"The antioxidant effect of \u03b2-caryophyllene protects rat liver from carbon tetrachloride-induced fibrosis by inhibiting hepatic stellate cell activation","volume":"109","author":"Calleja","year":"2013","journal-title":"Br. J. Nutr."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"9004014","DOI":"10.1155\/2022\/9004014","article-title":"Beta-caryophyllene as an antioxidant, anti-inflammatory and re-epithelialization activities in a rat skin wound excision model","volume":"2022","author":"Gushiken","year":"2022","journal-title":"Oxid. Med. Cell. Longevity."},{"key":"ref_42","unstructured":"Aguilar, I.E., and Galviz, R.A. (2015). Determinaci\u00f3n de la Composici\u00f3n Qu\u00edmica y Actividad Antibacteriana del Aceite Esencial extra\u00eddo de la planta Satureja brownei (Briq.) cultivada en el Jard\u00edn de plantas Medicinales \u201cDr. Luis Ruiz Ter\u00e1n\u201d de la Facultad de Farmacia y Bioan\u00e1lisis, Universidad de los Andes. [Bachelor\u2019s Thesis, Universidad de los Andes]."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/j.archoralbio.2019.02.015","article-title":"Efficacy of \u03b2-caryophyllene for periodontal disease related factors","volume":"100","author":"Yoo","year":"2019","journal-title":"Arch. Oral. Biol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"49","DOI":"10.33073\/pjm-2020-007","article-title":"Antibacterial Activity and Mode of Action of \u03b2-caryophyllene on","volume":"69","author":"Moo","year":"2020","journal-title":"Pol. J. Microbiol."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"224","DOI":"10.2174\/2211352517666190528114041","article-title":"Chemical composition, antioxidant, antibacterial, cytotoxicity, and hemolyses activity of essential oils from flower of Matricaria chamomilla var. chamomilla","volume":"18","author":"Mahdavi","year":"2020","journal-title":"Anti-Infect. Agents"},{"key":"ref_46","first-page":"167","article-title":"Characterization of antioxidant and antimicrobial compounds of cinnamon and ginger essential oils","volume":"4","author":"Farag","year":"2010","journal-title":"Afr. J. Biochem. Res."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Garzoli, S., Laghezza Masci, V., Franceschi, S., Tiezzi, A., Giacomello, P., and Ovidi, E. (2021). Headspace\/GC\u2013MS analysis and investigation of antibacterial, antioxidant and cytotoxic activity of essential oils and hydrolates from Rosmarinus officinalis L. and Lavandula angustifolia Miller. Foods, 10.","DOI":"10.3390\/foods10081768"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2469","DOI":"10.1016\/j.phytochem.2006.08.003","article-title":"Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: Chemical characterization and antimicrobial activity","volume":"67","author":"Sabulal","year":"2006","journal-title":"Phytochemistry"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1002\/ffj.993","article-title":"Essential oils of different cultivars of Cannabis sativa L. and their antimicrobial activity","volume":"16","author":"Novak","year":"2001","journal-title":"Flavour Fragr. J."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1550","DOI":"10.1590\/S0100-40422011000900013","article-title":"Chemical composition and antibacterial activity of essential oils from Verbenaceae species: Alternative sources of (E)-caryophyllene and germacrene-D","volume":"34","author":"Montanari","year":"2011","journal-title":"Quim. Nova"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"125283","DOI":"10.1016\/j.foodchem.2019.125283","article-title":"Minor constituents of essential oils and aromatic extracts. Oximes derived from natural flavor and fragrance raw materials\u2013Sensory evaluation, spectral and gas chromatographic characteristics","volume":"301","author":"Balcerzak","year":"2019","journal-title":"Food Chem."},{"key":"ref_52","unstructured":"(2022, December 22). Mass Spectral Library, Available online: https:\/\/chemdata.nist.gov."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"795","DOI":"10.2116\/analsci.18P014","article-title":"Based DPPH assay for antioxidant activity analysis","volume":"34","author":"Sirivibulkovit","year":"2018","journal-title":"Anal. Sci."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1016\/S0891-5849(98)00315-3","article-title":"Antioxidant activity applying an improved ABTS radical cation decolorization assay","volume":"26","author":"Re","year":"1999","journal-title":"Free Radical Biol. Med."},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Noriega, P., Ballesteros, J., De la Cruz, A., and Veloz, T. (2020). Chemical composition and preliminary antimicrobial activity of the hydroxylated sesquiterpenes in the essential oil from Piper barbatum Kunth leaves. Plants, 9.","DOI":"10.3390\/plants9020211"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/s13104-021-05838-8","article-title":"Validation of a method of broth microdilution for the determination of antibacterial activity of essential oils","volume":"14","author":"Vanegas","year":"2021","journal-title":"BMC Res. Notes"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/4\/1741\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:31:58Z","timestamp":1760121118000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/4\/1741"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,11]]},"references-count":56,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["molecules28041741"],"URL":"https:\/\/doi.org\/10.3390\/molecules28041741","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,11]]}}}