{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,24]],"date-time":"2026-06-24T14:29:57Z","timestamp":1782311397349,"version":"3.54.5"},"reference-count":57,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2023,12,15]],"date-time":"2023-12-15T00:00:00Z","timestamp":1702598400000},"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>Alzheimer\u2019s disease is a global health problem due to the scarcity of acetylcholinesterase inhibitors, the basis for symptomatic treatment of this disease; this requires new approaches to drug discovery. In this study, we investigated the chemical composition and anticholinesterase activity of Eugenia valvata McVaugt (Myrtaceae) collected in southern Ecuador, which was obtained as an essential oil (EO) with a yield of 0.124 \u00b1 0.03% (w\/w); as a result of the chemical composition analysis, a total of 58 organic compounds were identified\u2014representing 95.91% of the total volatile compounds\u2014using a stationary phase based on 5% phenyl-methylpolysiloxane, as analyzed via gas chromatography coupled to mass spectrometry (GC-MS) and flame ionization detection (GC-FID). The main groups were hydrocarbon sesquiterpenes (37.43%), oxygenated sesquiterpenes (31.08%), hydrocarbon monoterpenes (24.14%), oxygenated monoterpenes (0.20%), and other compounds (3.058%). Samples were characterized by the following compounds: \u03b1-pinene (22.70%), \u03b1-humulene (17.20%), (E)-caryophyllene (6.02%), citronellyl pentanoate (5.76%), 7-epi-\u03b1-eudesmol (4.34%) and 5-iso-cedranol (3.64%); this research was complemented with an enantioselective analysis carried out using 2,3-diethyl-6-tert-butyldimethylsilyl-\u03b2-cyclodextrin as a stationary phase chiral selector. As a result, \u03b1-pinene, limonene, and \u03b1-cadinene enantiomers were identified; finally, in the search for new active principles, the EO reported strong anticholinesterase activity with an IC50 of 53.08 \u00b1 1.13 \u00b5g\/mL, making it a promising candidate for future studies of Alzheimer\u2019s disease.<\/jats:p>","DOI":"10.3390\/molecules28248112","type":"journal-article","created":{"date-parts":[[2023,12,15]],"date-time":"2023-12-15T11:26:52Z","timestamp":1702639612000},"page":"8112","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Composition and Anti-Acetylcholinesterase Properties of the Essential Oil of the Ecuadorian Endemic Species Eugenia valvata McVaugh"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0608-8990","authenticated-orcid":false,"given":"James","family":"Calva","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad T\u00e9cnica Particular de Loja (UTPL), Loja 1101608, Ecuador"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maricarmen","family":"Silva","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad T\u00e9cnica Particular de Loja (UTPL), Loja 1101608, Ecuador"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5156-0700","authenticated-orcid":false,"given":"Vladimir","family":"Morocho","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad T\u00e9cnica Particular de Loja (UTPL), Loja 1101608, Ecuador"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,12,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.4103\/0973-7847.95849","article-title":"Historical review of medicinal plants\u2019 usage","volume":"6","author":"Petrovska","year":"2012","journal-title":"Pharmacogn. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"284","DOI":"10.4314\/ajtcam.v8i3.65276","article-title":"Traditional medicine: Past, present and future research and development prospects and integration in the National Health System of Cameroon","volume":"8","author":"Fokunang","year":"2011","journal-title":"Afr. J. Tradit. Complement. Altern. Med."},{"key":"ref_3","unstructured":"Badal McCreath, S., and Delgoda, R. (2017). Pharmacognosy, Fundamentals, Applications and Strategies, Academic Press."},{"key":"ref_4","first-page":"348","article-title":"Cuban scientific production about medicinal plants and natural products from PlantMedCUBA database","volume":"18","author":"Elizagaray","year":"2013","journal-title":"Rev. Cub. Plant. Med."},{"key":"ref_5","first-page":"609","article-title":"Social impact of an intervention strategy for the rational prescription of natural medicines implemented in C\u00e9spedes during 2011","volume":"18","year":"2013","journal-title":"Rev. Cub. Plant. Med."},{"key":"ref_6","unstructured":"(2023, August 10). Ministerio del Ambiente del Ecuador.2015.Quinto Informe Nacional Para el Convenio Sobre la Diversidad Biol\u00f3gica. Available online: https:\/\/www.ambiente.gob.ec\/wp-content\/uploads\/downloads\/2015\/06\/QUINTO-INFORME-BAJA-FINAL-19.06.2015.pdf."},{"key":"ref_7","unstructured":"Le\u00f3n, S., Valencia, R., Pitman, N., Endara, L., Ulloa, C.U., and Navarrete, H. (2023, August 09). Libro Rojo de Plantas End\u00e9micas del Ecuador, 2a edici\u00f3n. In Publicaciones del Herbario QCA, Pontificia Universidad Cat\u00f3lica del Ecuador 2011. Available online: https:\/\/ddrn.dk\/wp-content\/uploads\/2018\/01\/LIBRO_ROJO_de_las_plantas_endemicas_del-1.pdf."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"499","DOI":"10.1080\/10412905.2005.9698977","article-title":"Essential oils from leaves of two Eugenia brasiliensis specimens from southeastern Brazil","volume":"17","author":"Fischer","year":"2005","journal-title":"J. Essent. Oil Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"752","DOI":"10.12705\/674.5","article-title":"Phylogeny and biogeography of the hyper\u2013diverse genus Eugenia (Myrtaceae: Myrteae), with emphasis on E. sect. Umbellatae, the most unmanageable clade","volume":"67","author":"Giaretta","year":"2018","journal-title":"Taxon"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"110182","DOI":"10.1016\/j.foodres.2021.110182","article-title":"Plants from the genus Eugenia as promising therapeutic agents for the management of diabetes mellitus: A review","volume":"142","author":"Araujo","year":"2021","journal-title":"Food Res. Int."},{"key":"ref_11","unstructured":"Kubitzki, K. (2011). The Families and Genera of Vascular Plants, Springer Press."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"104500","DOI":"10.1016\/j.jfca.2022.104500","article-title":"Chemical composition, bioactive compounds, and perspectives for the industrial formulation of health products from uvaia (Eugenia pyriformis Cambess\u2013Myrtaceae): A comprehensive review","volume":"109","author":"Sganzerla","year":"2022","journal-title":"J. Food Compos. Anal."},{"key":"ref_13","first-page":"159","article-title":"The Anti-Inflammatory Activity of Eugenia Caryophllata Essential Oil: An animal model of anti-inflammatory activity","volume":"2","year":"2005","journal-title":"Eur. J. Gen. Med."},{"key":"ref_14","first-page":"S126","article-title":"Anti-inflammatory compounds of Eugenia jambos","volume":"10","author":"Slowing","year":"1996","journal-title":"Phytother. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"147","DOI":"10.20473\/j.djmkg.v41.i3.p147-150","article-title":"The use of bay leaf (Eugenia polyantha Wight) in dentistry","volume":"41","author":"Sumono","year":"2008","journal-title":"Dent. J. (Majalah Kedokteran Gigi)."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"996","DOI":"10.1016\/j.fct.2017.02.032","article-title":"Assessment of anti-cholinesterase activity and cytotoxicity of cagaita (Eugenia dysenterica) leaves","volume":"109","author":"Gasca","year":"2017","journal-title":"Food Chem. Toxicol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1002\/ptr.2124","article-title":"The chemical composition and biological activity of clove essential oil, Eugenia caryophyllata (Syzigium aromaticum L. Myrtaceae): A short review","volume":"21","author":"Chaieb","year":"2007","journal-title":"Phytother. Res."},{"key":"ref_18","first-page":"149","article-title":"Chemical constituents of Eugenia caryophyllata","volume":"41","author":"Park","year":"1997","journal-title":"Pharmaceut. Soc. Korea"},{"key":"ref_19","first-page":"263","article-title":"Constituents from Syzygium aromaticum Merr. et Perry","volume":"4","author":"Son","year":"1998","journal-title":"Nat. Prod. Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1345","DOI":"10.1016\/S0031-9422(96)00508-0","article-title":"Syzyginins A and B, two ellagitannins from Syzygium aromaticum","volume":"43","author":"Tanaka","year":"1996","journal-title":"Phytochemistry"},{"key":"ref_21","first-page":"373","article-title":"Flavonoids from Calycorectes, Campomanesia, Eugenia and Hexachlamys species","volume":"66","year":"1995","journal-title":"Fitoterapia"},{"key":"ref_22","first-page":"5","article-title":"Revisi\u00f3n de constituyentes qu\u00edmicos y propiedades biol\u00f3gicas en especies del g\u00e9nero Eugenia (Myrtaceae) Review of chemical constituents and biological properties in species of the genus Eugenia (Myrtaceae)","volume":"37","author":"Bravi","year":"2021","journal-title":"Dominguezia"},{"key":"ref_23","unstructured":"Jorgensen, P., and Leon-Yanez, S. (1999). Catalogue of the Vascular Plants of Ecuador, Missouri Botanical Garden Press."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"300","DOI":"10.1002\/ffj.2045","article-title":"Actions of essential oils on the central nervous system: An updated review","volume":"26","author":"Dobetsberger","year":"2011","journal-title":"Flavour Fragr. J."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1002\/ffj.1288","article-title":"Essential oils and fragrance compounds: Bioactivity and mechanisms of action","volume":"19","author":"Lahlou","year":"2004","journal-title":"Flavour Fragr. J."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1186\/s12944-015-0145-8","article-title":"Comparative chemical profiling, cholinesterase inhibitions and anti-radicals properties of essential oils from Polygonum hydropiper L.: A preliminary anti-alzheimer\u2019s study","volume":"14","author":"Ayaz","year":"2015","journal-title":"Lipids Health Dis."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"372","DOI":"10.1111\/j.1447-0594.2012.00849.x","article-title":"A Systematic review of the use of aromatherapy in treatment of behavioral problems in dementia","volume":"12","author":"Fung","year":"2012","journal-title":"Geriatr. Gerontol. Int."},{"key":"ref_28","unstructured":"Adams, R.P. (2007). Identification of Essential Oil Components by Gas Chromatography\/Mass Spectrometry, Allured Publishing Corporation. [4th ed.]."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Silva, J., Andrade, E., Barreto, L., Silva, N., Ribeiro, A., Montenegro, R., and Maia, J. (2017). Chemical Composition of Four Essential Oils of Eugenia from the Brazilian Amazon and Their Cytotoxic and Antioxidant Activity. Medicines, 4.","DOI":"10.3390\/medicines4030051"},{"key":"ref_30","first-page":"e796","article-title":"Composici\u00f3n qu\u00edmica y actividad antif\u00fangica del aceite esencial de hojas de Eugenia uniflora L. (Myrtaceae)","volume":"55","author":"Lucena","year":"2022","journal-title":"Rev. Cub. Farm."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Calva, J., Lude\u00f1a, C., Bec, N., Larroque, C., Salinas, M., Vidari, G., and Armijos, C. (2023). Constituents and Selective BuChE Inhibitory Activity of the Essential Oil from Hypericum aciculare Kunth. Plants, 12.","DOI":"10.3390\/plants12142621"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"660","DOI":"10.1016\/j.bse.2011.05.019","article-title":"Variabilidad qu\u00edmica de los vol\u00e1tiles de las hojas de Eugenia protenta McVaugh (Myrtaceae) que crecen de forma silvestre en el norte de Brasil","volume":"39","author":"Zoghbi","year":"2011","journal-title":"Bioqu\u00edm. Sist. Ecol."},{"key":"ref_33","first-page":"1184","article-title":"Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis","volume":"35","author":"Magina","year":"2012","journal-title":"Qu\u0131m. Nova"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1080\/10412905.2002.9699847","article-title":"Chemical composition of the essential oils from southern Brazilian Eugenia species. Part III","volume":"14","author":"Apel","year":"2002","journal-title":"J. Essent. Oil Res."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1080\/10412905.2008.9699427","article-title":"Chemical composition and antimicrobial activity of essential oils of Eugenia chlorophylla (myrtaceae)","volume":"20","author":"Stefanello","year":"2008","journal-title":"J. Essent. Oil Res."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"6305","DOI":"10.3390\/molecules17066305","article-title":"Biological activities of \u03b1-pinene and \u03b2-pinene enantiomers","volume":"17","author":"Lopes","year":"2012","journal-title":"Molecules"},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Allenspach, M., Valder, C., Flamm, D., Grisoni, F., and Steuer, C. (2020). Verification of chromatographic profile of primary essential oil of Pinus sylvestris L. combined with chemometric analysis. Molecules, 25.","DOI":"10.3390\/molecules25132973"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1805","DOI":"10.1007\/s00253-016-8066-7","article-title":"Biotransformation of \u03b1-and \u03b2-pinene into flavor compounds","volume":"101","author":"Vespermann","year":"2017","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"917","DOI":"10.2174\/1568026618666180712093914","article-title":"Antibacterial activity and time-kill kinetics of positive enantiomer of \u03b1-pinene against strains of Staphylococcus aureus and Escherichia coli","volume":"18","author":"Farias","year":"2018","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.fitote.2018.04.013","article-title":"Influence of plant origin natural \u03b1-pinene with different enantiomeric composition on bacteria, yeasts and fungi","volume":"127","author":"Sytar","year":"2018","journal-title":"Fitoterapia"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1007\/s11094-009-0282-3","article-title":"Synthesis and antifungal activity of compounds of the pinane series","volume":"43","author":"Nikitina","year":"2009","journal-title":"Pharm. Chem. J."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1080\/10412905.2006.12067134","article-title":"The biological activities of 20 nature identical essential oil constituents","volume":"18","author":"Seatlholo","year":"2006","journal-title":"J. Essent. Oil Res."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"264","DOI":"10.1021\/np400828x","article-title":"Anti-inflammatory and chondroprotective activity of (+)-\u03b1-pinene: Structural and enantiomeric selectivity","volume":"77","author":"Rufino","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1765","DOI":"10.1021\/jf040019b","article-title":"Inhibition of acetylcholinesterase activity by bicyclic monoterpenoids","volume":"53","author":"Miyazawa","year":"2005","journal-title":"J. Agric. Food Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1044","DOI":"10.3390\/molecules16021044","article-title":"Comparative anti-infectious bronchitis virus (IBV) activity of (-)-pinene: Effect on nucleocapsid (N) protein","volume":"16","author":"Yang","year":"2011","journal-title":"Molecules"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2608","DOI":"10.1080\/14786419.2019.1686369","article-title":"Phenolic profile by HPLC-ESI-MS\/MS of six Brazilian Eugenia species and their potential as cholinesterase inhibitors","volume":"35","author":"Tenfen","year":"2021","journal-title":"Nat. Prod. Res."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"598","DOI":"10.1016\/j.ejmech.2018.07.033","article-title":"Multi-target-directed ligands for treating Alzheimer\u2019s disease: Butyrylcholinesterase inhibitors displaying antioxidant and neuroprotective activities","volume":"156","author":"Knez","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"335","DOI":"10.2174\/1567205012666150325182702","article-title":"Oxidant\/Antioxidant imbalance and the risk of Alzheimer\u2019s disease","volume":"12","author":"Moneim","year":"2015","journal-title":"Curr. Alzheimer Res."},{"key":"ref_49","first-page":"152","article-title":"Chemical composition of essential oils and anticholinesterasic activity of Eugenia sulcata spring ex mart","volume":"31","author":"Lima","year":"2012","journal-title":"Lat. Am. J. Pharm."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1590\/S0102-695X2010000200007","article-title":"Chemical composition and acetylcholinesterase inhibitory activity of essential oils of Myrceugenia myrcioides (Cambess.) O. Berg and Eugenia riedeliana O. Berg, Myrtaceae","volume":"20","author":"Souza","year":"2010","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1080\/14786419.2014.958736","article-title":"Evaluation of seasonal chemical composition, antibacterial, antioxidant and anticholinesterase activity of essential oil from Eugenia brasiliensis Lam","volume":"29","author":"Siebert","year":"2014","journal-title":"Nat. Prod. Res."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"217","DOI":"10.3390\/insects4020217","article-title":"Laboratory and simulated field bioassays to evaluate larvicidal activity of Pinus densiflora hydrodistillate, its constituents and structurally related compounds against Aedes albopictus, Aedes aegypti and Culex pipiens pallens in relation to their inhibitory effects on acetylcholinesterase activity","volume":"30","author":"Lee","year":"2013","journal-title":"Insects"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"677","DOI":"10.1021\/jf960398b","article-title":"Inhibition of acetylcholinesterase activity by monoterpenoids with a p-menthane skeleton","volume":"45","author":"Miyazawa","year":"1997","journal-title":"J. Agric. Food Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"7672","DOI":"10.3390\/molecules16097672","article-title":"Antioxidant and Antiacetylcholinesterase Activities of Some Commercial Essential Oils and Their Major Compounds","volume":"16","author":"Aazza","year":"2011","journal-title":"Molecules"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1080\/10575630108041281","article-title":"Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi","volume":"15","author":"Miyazawa","year":"2001","journal-title":"Nat. Prod. Lett."},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Calva, J., Cartuche, L., Castillo, L.N., and Morocho, V. (2023). Biological Activities and Chemical Composition of Essential Oil from Hedyosmum purpurascens (Todzia)\u2014An Endemic Plant in Ecuador. Molecules, 28.","DOI":"10.3390\/molecules28052366"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/0006-2952(61)90145-9","article-title":"A new and rapid colorimetric determination of acetylcholinesterase activity","volume":"7","author":"Ellman","year":"1961","journal-title":"Biochem. Pharmacol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/24\/8112\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T21:39:32Z","timestamp":1760132372000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/24\/8112"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,12,15]]},"references-count":57,"journal-issue":{"issue":"24","published-online":{"date-parts":[[2023,12]]}},"alternative-id":["molecules28248112"],"URL":"https:\/\/doi.org\/10.3390\/molecules28248112","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,12,15]]}}}