{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,26]],"date-time":"2026-05-26T12:06:45Z","timestamp":1779797205443,"version":"3.53.1"},"reference-count":38,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2026,5,26]],"date-time":"2026-05-26T00:00:00Z","timestamp":1779753600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Argentina and Chile","award":["1500-23-R"],"award-info":[{"award-number":["1500-23-R"]}]},{"name":"Argentina and Chile","award":["1499-23-R"],"award-info":[{"award-number":["1499-23-R"]}]},{"name":"Fondecyt","award":["1260005"],"award-info":[{"award-number":["1260005"]}]},{"name":"Fondequip","award":["EQM170172"],"award-info":[{"award-number":["EQM170172"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Antioxidants"],"abstract":"<jats:p>Larrea ameghinoi Speg., an endemic species of Argentine Patagonia traditionally used in folk medicine to treat fever, stomach disorders, respiratory conditions, back pain, and as an emmenagogue, among others, still remains chemically and biologically underexplored compared to the other four members of the genus. This study aimed to perform a comprehensive metabolomic characterization of methanolic extracts from two populations (EMLaSAO and EMLaMAQ) using ultra-high-resolution liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry (UHPLC\u2013ESI\u2013QTOF\u2013MS) and to evaluate their antioxidant, antimicrobial, and enzyme-inhibitory activities of relevance to human health. Thirty-three compounds were tentatively identified by extensive UHPLC\u2013MS analysis, including flavones, two major lignans, and oleanane-type triterpenes. Both extracts exhibited high phenolic content (215\u2013239 mg of gallic acid equivalents (GAE)\/g extract) and strong free radical scavenging activity, as evidenced by 2,2-diphenyl-1-picrylhydrazyl (DPPH, EC50 \u2248 10 \u03bcg\/mL), ferric-reducing antioxidant power (FRAP), and Trolox equivalent antioxidant activity (TEAC) assays. In addition, significant inhibition of butyrylcholinesterase (IC50 \u2248 50 \u03bcg extract\/mL) and \u03b1-glucosidase, together with selective antibacterial activity against methicillin-sensitive and resistant Staphylococcus aureus (MIC = 125 \u03bcg extract\/mL), were recorded. These findings suggest that L. ameghinoi possesses a distinctive phytochemical composition conferring multitarget bioactivity, differing from other Larrea species dominated by lignans such as nordihydroguaiaretic acid (NDGA) and its derivatives. Overall, this work supports the potential of L. ameghinoi as a novel source of bioactive metabolites for managing oxidative stress-related disorders and opportunistic infections. This warrants future in vivo studies investigating biological activities associated with oxidative stress and their relevance to human health.<\/jats:p>","DOI":"10.3390\/antiox15060668","type":"journal-article","created":{"date-parts":[[2026,5,26]],"date-time":"2026-05-26T11:02:51Z","timestamp":1779793371000},"page":"668","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Larrea ameghinoi Speg. (Zygophyllaceae) \u201cJarilla Rastrera\u201d: UHPLC-ESI-QTOF-MS Analysis, Antioxidant, Antimicrobial Properties, and Inhibition of Enzymes of Interest to Human Health"],"prefix":"10.3390","volume":"15","author":[{"given":"Jessica","family":"G\u00f3mez","sequence":"first","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas-Departamento de Ingenier\u00eda Agron\u00f3mica, Universidad Nacional de San Juan (UNSJ), San Juan J5400ARL, Argentina"},{"name":"Consejo Nacional de Investigaciones Cient\u00edficas y T\u00e9cnicas (CONICET), Ciudad Aut\u00f3noma de Buenos Aires C1425FQB, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6694-8791","authenticated-orcid":false,"given":"Silvana M.","family":"Sede","sequence":"additional","affiliation":[{"name":"Consejo Nacional de Investigaciones Cient\u00edficas y T\u00e9cnicas (CONICET), Ciudad Aut\u00f3noma de Buenos Aires C1425FQB, Argentina"},{"name":"Instituto de Bot\u00e1nica Darwinion CONICET-ANCEFN Labard\u00e9n 200, San Isidro B1642HYD, Buenos Aires, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bel\u00e9n Ariza","family":"Sampietro","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas-Departamento de Ingenier\u00eda Agron\u00f3mica, Universidad Nacional de San Juan (UNSJ), San Juan J5400ARL, Argentina"},{"name":"Consejo Nacional de Investigaciones Cient\u00edficas y T\u00e9cnicas (CONICET), Ciudad Aut\u00f3noma de Buenos Aires C1425FQB, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5767-8400","authenticated-orcid":false,"given":"Daniel","family":"Zaragoza-Puchol","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas-Departamento de Ingenier\u00eda Agron\u00f3mica, Universidad Nacional de San Juan (UNSJ), San Juan J5400ARL, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mar\u00eda Elisa","family":"Bressan Merlo","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas-Departamento de Ingenier\u00eda Agron\u00f3mica, Universidad Nacional de San Juan (UNSJ), San Juan J5400ARL, Argentina"},{"name":"Consejo Nacional de Investigaciones Cient\u00edficas y T\u00e9cnicas (CONICET), Ciudad Aut\u00f3noma de Buenos Aires C1425FQB, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4508-5488","authenticated-orcid":false,"given":"Duilio","family":"Caballero","sequence":"additional","affiliation":[{"name":"Laboratorio Hospital Marcial Quiroga, Av. Libertador General San Mart\u00edn 5401 (O), Rivadavia CP 5407, San Juan, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5851-5582","authenticated-orcid":false,"given":"Beatriz","family":"Lima","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas-Departamento de Ingenier\u00eda Agron\u00f3mica, Universidad Nacional de San Juan (UNSJ), San Juan J5400ARL, Argentina"},{"name":"Consejo Nacional de Investigaciones Cient\u00edficas y T\u00e9cnicas (CONICET), Ciudad Aut\u00f3noma de Buenos Aires C1425FQB, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1955-4850","authenticated-orcid":false,"given":"Alejandro","family":"Tapia","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas-Departamento de Ingenier\u00eda Agron\u00f3mica, Universidad Nacional de San Juan (UNSJ), San Juan J5400ARL, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4552-3123","authenticated-orcid":false,"given":"Mario J.","family":"Simirgiotis","sequence":"additional","affiliation":[{"name":"Instituto de Farmacia, Facultad de Ciencias, Campus Isla Teja, Universidad Austral de Chile, Valdivia 5090000, Chile"},{"name":"Center for Interdisciplinary Studies on the Nervous System (CISNe), Universidad Austral de Chile, Valdivia 5090000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,5,26]]},"reference":[{"key":"ref_1","unstructured":"Mabry, T.J., Hunziker, J., and DiFeo, D.R. (1977). Geographic Distribution, Morphology, Hybridization and Evolution. Creosote Bush: Biology and Chemistry of Larrea in New World Deserts, Dowden, Hutchinson, and Ross."},{"key":"ref_2","unstructured":"World Flora Online (2025, December 12). Larrea. Available online: https:\/\/www.worldfloraonline.org\/search?query=Larrea+&limit=24&start=0&sort=."},{"key":"ref_3","unstructured":"Kiesling, R. (2003). Flora de San Juan, Rep\u00fablica Argentina, Estudio Sigma."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"G\u00f3mez, J., Simirgiotis, M.J., Manrique, S., Pi\u00f1eiro, M., Lima, B., B\u00f3rquez, J., Feresin, G.E., and Tapia, A. (2021). UHPLC-ESI-OT-MS phenolics profiling, free radical scavenging, antibacterial and nematicidal activities of \u201cyellow-brown resins\u201d from Larrea spp.. Antioxidants, 10.","DOI":"10.3390\/antiox10020185"},{"key":"ref_5","unstructured":"CONICET (2026, February 09). Cient\u00edficos Desarrollan un Producto para la Calvicie que ya Est\u00e1 Disponible en Farmacias, Available online: https:\/\/www.conicet.gov.ar\/cientificos-desarrollan-un-producto-para-la-calvicie-que-ya-esta-disponible-en-farmacias\/."},{"key":"ref_6","unstructured":"(2026, February 09). Available online: https:\/\/sib.gob.ar\/especies\/larrea-ameghinoi?tab=sitios."},{"key":"ref_7","first-page":"473","article-title":"Observaciones sobre la taxonom\u00eda del g\u00e9nero Larrea (Zygophyllaceae)","volume":"17","author":"Palacios","year":"1972","journal-title":"Darwiniana"},{"key":"ref_8","unstructured":"Cabrera, A.A. (2023). Valorizaci\u00f3n de la \u201cJarilla rastrera\u201d (Larrea ameghinoi Speg.): Introducci\u00f3n al Cultivo de Tejidos in vitro y Bioprospecci\u00f3n Qu\u00edmica. [Doctoral Thesis, Universidad Nacional de R\u00edo Negro]."},{"key":"ref_9","unstructured":"Heldrich, K. (1990). Official Methods of Analysis of the Association of Official Analytical Chemists, Association of Official Chemists."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/S0023-6438(95)80008-5","article-title":"Use of a free radical method to evaluate antioxidant activity","volume":"28","author":"Cuvelier","year":"1995","journal-title":"LWT Food Sci. Technol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1006\/abio.1996.0292","article-title":"The ferric reducing ability of plasma (FRAP) as a measure of \u201cantioxidant power\u201d: The FRAP assay","volume":"239","author":"Benzie","year":"1996","journal-title":"Anal. Biochem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1039\/b009171p","article-title":"Methods for testing antioxidant activity","volume":"127","author":"Antolovich","year":"2002","journal-title":"Analyst"},{"key":"ref_13","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."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1016\/j.jep.2006.04.004","article-title":"\u03b1-Amylase inhibitory activity of some Malaysian plants used to treat diabetes; with particular reference to Phyllanthus amarus","volume":"107","author":"Ali","year":"2006","journal-title":"J. Ethnopharmacol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1016\/j.foodchem.2010.11.041","article-title":"Investigation of \u03b1-glucosidase inhibitory activity of wheat bran and germ","volume":"126","author":"Liu","year":"2011","journal-title":"Food Chem."},{"key":"ref_16","unstructured":"Clinical and Laboratory Standards Institute (CLSI) (2013). Performance Standards for Antimicrobial Susceptibility Testing, Twenty-Third Informational Supplement, CLSI Document M100-S23, CLSI."},{"key":"ref_17","unstructured":"Clinical and Laboratory Standards Institute (CLSI) (2008). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, Approved Standard. CLSI Document M27-A3, CLSI. [3rd ed.]."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1970","DOI":"10.1016\/j.fct.2011.05.008","article-title":"Argentinean propolis from Larrea nitida Cav. (Zygophyllaceae) exudates: Phytochemical characterization and antifungal activity","volume":"49","author":"Svetaz","year":"2011","journal-title":"Food Chem. Toxicol."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Yokosuka, A., Iguchi, T., Jitsuno, M., and Mimaki, Y. (2021). Structure and cytotoxicity of novel lignans and lignan glycosides from the aerial parts of Larrea tridentata. Molecules, 26.","DOI":"10.3390\/molecules26206186"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"666","DOI":"10.1016\/j.phymed.2015.04.004","article-title":"Synergistic antifungal fixed-ratio combinations ofZuccagnia punctata Cav. and Larrea nitida Cav., using mixed-effects loewe (MixLow) method","volume":"22","author":"Butassi","year":"2015","journal-title":"Phytomedicine"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"17543","DOI":"10.1021\/acs.jafc.3c04022","article-title":"The Chemistry Behind the Folin\u2013Ciocalteu Method for the Estimation of (Poly)phenol Content in Food: Total Phenolic Intake in a Mediterranean Dietary Pattern","volume":"71","year":"2023","journal-title":"J. Agric. Food Chem."},{"key":"ref_22","unstructured":"Walley, J., and Wright, J. (2010). Noncommunicable diseases. Public Health: An Action Guide to Improving Health, Oxford University Press."},{"key":"ref_23","unstructured":"WHO (2019). Noncommunicable Diseases, WHO."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2352","DOI":"10.2174\/1568026621666210727170908","article-title":"Larrea tridentata and its biological activities","volume":"21","year":"2021","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Lee, K.H., Cha, M., and Lee, B.H. (2020). Neuroprotective effect of antioxidants in the brain. Int. J. Mol. Sci., 21.","DOI":"10.3390\/ijms21197152"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"e14529","DOI":"10.1111\/cbdd.14529","article-title":"Diosmetin derivatives as multifunctional anti-AD ligands: Design, synthesis, and biological evaluation","volume":"103","author":"Yang","year":"2024","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"9966750","DOI":"10.1155\/2022\/9966750","article-title":"Flavonols and flavones as potential anti-inflammatory, antioxidant, and antibacterial compounds","volume":"2022","author":"Chagas","year":"2022","journal-title":"Oxid. Med. Cell Longev."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"467","DOI":"10.1007\/s12640-020-00306-w","article-title":"Anacardic acid complexes as possible agents against Alzheimer\u2019s disease through their antioxidant, in vitro, and in silico anticholinesterase and anxiolytic actions","volume":"39","author":"Pinheiro","year":"2021","journal-title":"Neurotox. Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"8063","DOI":"10.1038\/s41598-018-26429-x","article-title":"Transcriptomic response of breast cancer cells to anacardic acid","volume":"8","author":"Schultz","year":"2018","journal-title":"Sci. Rep."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"19506","DOI":"10.1021\/acsomega.0c01775","article-title":"Anti-inflammatory, antinociceptive, and antioxidant properties of anacardic acid in experimental models","volume":"5","author":"Islam","year":"2020","journal-title":"ACS Omega"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"80","DOI":"10.1016\/j.jep.2005.04.025","article-title":"Medicinal plants and antimicrobial activity","volume":"100","author":"Rios","year":"2005","journal-title":"J. Ethnopharmacol."},{"key":"ref_32","unstructured":"Tamokou, J.D.D., Mbaveng, A.T., and Kuete, V. (2017). Medicinal spices and vegetables from Africa: Therapeutic potential against metabolic, inflammatory, infectious and systemic diseases. Medicinal Spices and Vegetables from Africa, Academic Press."},{"key":"ref_33","first-page":"385","article-title":"Actividad antimicrobiana de plantas medicinales argentinas sobre bacterias antibi\u00f3tico-resistentes","volume":"41","author":"Zampini","year":"2007","journal-title":"Acta Bioqu\u00edm. Cl\u00edn. Latinoam."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"105595","DOI":"10.1016\/j.foodhyd.2019.105595","article-title":"Activeproperties of edible marine polysaccharide-based coatings containing Larrea nitida polyphenols enriched extract","volume":"102","author":"Moreno","year":"2020","journal-title":"Food Hydrocoll."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"306","DOI":"10.1016\/j.indcrop.2012.04.037","article-title":"Antibacterial activity of crude methanolic extract and fractions obtained from Larrea tridentata leaves","volume":"41","author":"Martins","year":"2013","journal-title":"Ind. Crops Prod."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"110554","DOI":"10.1016\/j.abb.2025.110554","article-title":"L-malic acid: A multifunctional metabolite at the crossroads of redox signaling, microbial symbiosis, and therapeutic innovation","volume":"772","author":"Lu","year":"2025","journal-title":"Arch. Biochem. Biophys."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1016\/S0031-9422(02)00104-8","article-title":"Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives","volume":"60","author":"Ali","year":"2002","journal-title":"Phytochemistry"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"620472","DOI":"10.1155\/2015\/620472","article-title":"Antimicrobial activity of oleanolic and ursolic acids: An update","volume":"2015","author":"Jesus","year":"2015","journal-title":"Evid. Based Complement. Altern. Med."}],"container-title":["Antioxidants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2076-3921\/15\/6\/668\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,5,26]],"date-time":"2026-05-26T11:26:45Z","timestamp":1779794805000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2076-3921\/15\/6\/668"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,5,26]]},"references-count":38,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2026,6]]}},"alternative-id":["antiox15060668"],"URL":"https:\/\/doi.org\/10.3390\/antiox15060668","relation":{},"ISSN":["2076-3921"],"issn-type":[{"value":"2076-3921","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,5,26]]}}}