{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T03:58:18Z","timestamp":1760241498704,"version":"build-2065373602"},"reference-count":52,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2018,3,29]],"date-time":"2018-03-29T00:00:00Z","timestamp":1522281600000},"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 seriated extracts of petroleum ether (PE-E), dichloromethane (DCM-E) and methanol extracts (MeOH-E) from the aerial parts of the native South American plant Tetraglochin ameghinoi (Rosaceae), were evaluated regarding their antioxidant and antibacterial activities. The antioxidant properties were evaluated by free radical scavenging methods (DPPH and TEAC), ferric-reducing antioxidant power (FRAP) and lipoperoxidation in erythrocytes (LP), while the antibacterial activity was performed against Gram-positive and Gram-negative bacteria according to the Clinical and Laboratory Standards Institute (CLSI) guidelines. The chemical and biological analyses of this plant are very important since this bush is currently used in traditional medicine as a cholagogue and digestive. The polar MeOH-E showed the highest antioxidant activities (17.70 \u00b5g\/mL in the DPPH assay, 381.43 \u00b1 22.38 mM TE\/g extract in the FRAP assay, 387.76 \u00b1 91.93 mg TE\/g extract in the TEAC assay and 93.23 + 6.77% in the LP assay) and it was selected for chromatographic isolation of its components. These components were found to be four acetophenones, including the new phloracetophenone glucoside: 4\u2032,6\u2032,-dihydroxy-2\u2032-O-(6\u2033-acetyl)-\u03b2-d-glucopyranosylacetophenone or IUPAC name: (6-(2-acetyl-3,5-dihydroxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl acetate, whose structure was elucidated by NMR and MS methods. In addition, twenty-six compounds, including five of these acetophenone derivatives, two sugars, six flavonoids, eleven phenolic acids and two triterpenes, were identified based on UHPLC-OT-MS and PDA analysis on the MeOH-E. The results support the medicinal use of the plant.<\/jats:p>","DOI":"10.3390\/molecules23040793","type":"journal-article","created":{"date-parts":[[2018,3,29]],"date-time":"2018-03-29T12:51:56Z","timestamp":1522327916000},"page":"793","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["UHPLC-MS Metabolome Fingerprinting: The Isolation of Main Compounds and Antioxidant Activity of the Andean Species Tetraglochin ameghinoi (Speg.) Speg."],"prefix":"10.3390","volume":"23","author":[{"given":"Lorena","family":"Luna","sequence":"first","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas, Universidad Nacional de San Juan, Av. Li bertador General San Mart\u00edn 1109 (O), San Juan CP5400, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4552-3123","authenticated-orcid":false,"given":"Mario","family":"Simirgiotis","sequence":"additional","affiliation":[{"name":"Instituto de Farmacia, Facultad de Ciencias, Universidad Austral de Chile, Campus Isla Teja, Valdivia 5090000, Chile"},{"name":"Center for Interdisciplinary Studies on the Nervous System (CISNe), Universidad Austral de Chile, Valdivia 5090000, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Beatriz","family":"Lima","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas, Universidad Nacional de San Juan, Av. Li bertador General San Mart\u00edn 1109 (O), San Juan CP5400, Argentina"},{"name":"CONICET (Consejo Nacional de Ciencia y Tecnolog\u00eda), CABA, Buenos Aires C1405DJR, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jorge","family":"B\u00f3rquez","sequence":"additional","affiliation":[{"name":"Laboratorio de Productos Naturales Depto. de Qu\u00edmica, Facultad de Ciencias, Universidad de Antofagasta, Av. Coloso S-N, Antofagasta 1240000, Chile"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4076-3999","authenticated-orcid":false,"given":"Gabriela","family":"Feresin","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas, Universidad Nacional de San Juan, Av. Li bertador General San Mart\u00edn 1109 (O), San Juan CP5400, Argentina"},{"name":"CONICET (Consejo Nacional de Ciencia y Tecnolog\u00eda), CABA, Buenos Aires C1405DJR, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alejandro","family":"Tapia","sequence":"additional","affiliation":[{"name":"Instituto de Biotecnolog\u00eda-Instituto de Ciencias B\u00e1sicas, Universidad Nacional de San Juan, Av. Li bertador General San Mart\u00edn 1109 (O), San Juan CP5400, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2018,3,29]]},"reference":[{"key":"ref_1","unstructured":"(2018, January 30). The Plant List. Available online: http:\/\/www.theplantlist.org\/1.1\/browse\/A\/Rosaceae\/Tetraglochin\/."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"839","DOI":"10.1600\/036364416X693946","article-title":"Molecular Phylogeny and Morphological Analysis of Tetraglochin (Rosaceae: Rosoideae: Sanguisorbeae) and Recognition of the New Species T. andina","volume":"41","author":"Acosta","year":"2016","journal-title":"Syst. Bot."},{"key":"ref_3","first-page":"411","article-title":"Ethnopharmacobotanical survey of Bauchazeta district, San Juan Province, Argentina","volume":"67","author":"Bustos","year":"1996","journal-title":"Fitoterapia"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2061","DOI":"10.3390\/molecules18022061","article-title":"Antioxidant Capacity and HPLC-DAD-MS Profiling of Chilean Peumo (Cryptocarya alba) Fruits and Comparison with German Peumo (Crataegus monogyna) from Southern Chile","volume":"18","author":"Simirgiotis","year":"2013","journal-title":"Molecules"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1016\/j.foodchem.2013.01.089","article-title":"Antioxidant capacity, polyphenolic content and tandem HPLC-DAD-ESI\/MS profiling of phenolic compounds from the South American berries Luma apiculata and L. chequen","volume":"139","author":"Simirgiotis","year":"2013","journal-title":"Food Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"368","DOI":"10.1016\/j.indcrop.2016.08.037","article-title":"High resolution metabolite fingerprinting of the resin of Baccharis tola Phil. from the Atacama Desert and its antioxidant capacities","volume":"94","author":"Simirgiotis","year":"2016","journal-title":"Ind. Crops Prod."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1016\/j.bjp.2016.10.002","article-title":"UHPLC high resolution orbitrap metabolomic fingerprinting of the unique species Ophryosporus triangularis Meyen from the Atacama Desert, Northern Chile","volume":"27","author":"Simirgiotis","year":"2017","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Cornejo, A., Salgado, F., Caballero, J., Vargas, R., Simirgiotis, M.J., and Areche, C. (2016). Secondary Metabolites in Ramalina terebrata Detected by UHPLC\/ESI\/MS\/MS and Identification of Parietin as Tau Protein Inhibitor. Int. J. Mol. Sci., 17.","DOI":"10.3390\/ijms17081303"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"245","DOI":"10.3390\/molecules21030245","article-title":"Phenolic compounds in Chilean Mistletoe (Quintral, Tristerix tetrandus) analyzed by UHPLC\u2013Q\/Orbitrap\/MS\/MS and its antioxidant properties","volume":"21","author":"Simirgiotis","year":"2016","journal-title":"Molecules"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"169","DOI":"10.2174\/138955711794519546","article-title":"Flavonoids Health Benefits and Their Molecular Mechanism","volume":"11","author":"Xiao","year":"2011","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_11","first-page":"1874","article-title":"Dietary flavonoid aglycones and their glycosides: Which show better biological significance","volume":"57","author":"Xiao","year":"2017","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2539","DOI":"10.1007\/s00705-017-3417-y","article-title":"Flavonoids: Promising natural compounds against viral infections","volume":"162","author":"Zakaryan","year":"2017","journal-title":"Arch. Virol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"572","DOI":"10.1016\/S0955-2863(02)00208-5","article-title":"Flavonoids antioxidants: Chemistry, metabolism and structure-activity relationships","volume":"13","author":"Heim","year":"2002","journal-title":"J. Nutr. Biochem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"274","DOI":"10.1161\/01.ATV.0000149143.04821.eb","article-title":"ATVB in focus: Redox mechanisms in blood vessels","volume":"25","author":"Mueller","year":"2005","journal-title":"Arterioscler. Thromb. Vasc. Biol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"483","DOI":"10.1016\/j.redox.2013.07.006","article-title":"Biological markers of oxidative stress: Applications to cardiovascular research and practice","volume":"1","author":"Ho","year":"2013","journal-title":"Redox Biol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"840","DOI":"10.1111\/j.1582-4934.2009.00897.x","article-title":"Chemical and molecular mechanisms of antioxidants: Experimental approaches and model systems","volume":"14","author":"Lin","year":"2010","journal-title":"J. Cell. Mol. Med."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Ekinci Akdemir, F.N., Albayrak, M., \u00c7alik, M., Bayir, Y., and G\u00fcl\u00e7in, \u0130. (2017). The Protective Effects ofp-Coumaric Acid on Acute Liver and Kidney Damages Induced by Cisplatin. Biomedicines, 5.","DOI":"10.3390\/biomedicines5020018"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/s12906-017-1604-8","article-title":"Hepatoprotective effect of Coreopsis tinctoria flowers against carbon tetrachloride-induced liver damage in mice","volume":"17","author":"Tsai","year":"2017","journal-title":"Complement. Altern. Med."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4290","DOI":"10.1021\/jf0502698","article-title":"Standardized Methods for the Determination of Antioxidant Capacity and Phenolics in Foods and Dietary Supplements","volume":"53","author":"Prior","year":"2005","journal-title":"J. Agric. Food Chem."},{"key":"ref_20","first-page":"137289","article-title":"Oxidative Stress and Lipid Peroxidation Products in Cancer Progression and Therapy","volume":"2012","author":"Barrera","year":"2012","journal-title":"ISRN Oncol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"55","DOI":"10.4067\/S0716-97602000000200004","article-title":"Plant polyphenol antioxidant and oxidative stress","volume":"33","author":"Urquiaga","year":"2000","journal-title":"Biol. Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"5","DOI":"10.12816\/0003082","article-title":"The Role of Oxidative Stress and Antioxidants in Diabetic Complications","volume":"12","author":"Matough","year":"2012","journal-title":"Sultan Qaboos Univ. Med. J."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1590\/0037-8682-0139-2014","article-title":"Emergence of antibiotic-resistant bacterial strains, methicillin-resistant Staphylococcus aureus, extended spectrum beta lactamases, and multi-drug resistance is a problem similar to global warming","volume":"47","author":"Bhattacharya","year":"2014","journal-title":"Rev. Soc. Bras. Med. Trop."},{"key":"ref_24","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":"Recio","year":"2005","journal-title":"J. Ethnopharmacol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1186\/1746-4811-6-14","article-title":"Rapid metabolic profiling of Nicotiana tabacum defence responses against Phytophthora nicotianae using direct infrared laser desorption ionization mass spectrometry and principal component analysis","volume":"6","author":"Ibanez","year":"2010","journal-title":"Plant Methods"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1515\/znb-2004-0113","article-title":"A new eudesmane derivative from Leontodon tuberosus","volume":"59","author":"Spitaler","year":"2004","journal-title":"Z. Naturforsch."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/S0031-9422(96)00778-9","article-title":"A phloracetophenone glucoside with choleretic activity from Curcuma comosa","volume":"45","author":"Suksamrarn","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1016\/S0014-2999(99)00743-8","article-title":"Choleretic activity of phloracetophenone in rats: Structure-function studies using acetophenone analogues","volume":"387","author":"Piyachaturawat","year":"2000","journal-title":"Eur. J. Pharmacol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1016\/S0014-2999(02)01453-X","article-title":"Cholesterol lowering effects of a choleretic phloracetophenone in hypercholesterolemic hamsters","volume":"439","author":"Piyachaturawat","year":"2002","journal-title":"Eur. J. Pharmacol."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1016\/j.foodchem.2016.06.097","article-title":"Co-pigmentation of pelargonidin derivatives in strawberry and red radish model solutions by the addition of phenolic fractions from mango peels","volume":"213","author":"Bechtold","year":"2016","journal-title":"Food Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1016\/j.intimp.2012.01.013","article-title":"Inhibitory effects of an ellagic acid glucoside, okicamelliaside, on antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells and passive cutaneous anaphylaxis reaction in mice","volume":"12","author":"Agarie","year":"2012","journal-title":"Int. Immunopharmacol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1007\/s10600-015-1204-0","article-title":"Isolation, Characterization, Bioassay and X-ray Crystallographic Study of Phytoconstituents from Bixaorellana Leaves","volume":"51","author":"Parveen","year":"2015","journal-title":"Chem. Nat. Compd."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jchromb.2016.09.033","article-title":"A novel method for the quantitation of gingerolglucuronides in human plasma or urine based on stable isotope dilution assays","volume":"1036","author":"Schoenknecht","year":"2016","journal-title":"J. Chromatogr. B Anal. Technol. Biomed. Life Sci."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"27540","DOI":"10.1039\/C5RA01911G","article-title":"Gallic acid: A versatile antioxidant with promising therapeutic and industrial applications","volume":"5","author":"Badhani","year":"2015","journal-title":"RSC Adv."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"735","DOI":"10.1111\/j.1472-8206.2009.00722.x","article-title":"Hepatoprotective activity of picroliv, curcumin and ellagic acid compared to silymarin on paracetamol induced liver toxicity in mice","volume":"23","author":"Girish","year":"2009","journal-title":"Fundam. Clin. Pharmacol."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1016\/S0031-9422(99)00262-9","article-title":"Polyphenolic metabolites of Rhamnus disperma","volume":"52","author":"Marzouk","year":"1999","journal-title":"Phytochemistry"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"933","DOI":"10.1016\/0891-5849(95)02227-9","article-title":"Structure-antioxidant activity relationships of flavonoids and phenolic acids","volume":"20","author":"RiceEvans","year":"1996","journal-title":"Free Radic. Biol. Med."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"298","DOI":"10.2174\/138955711795305335","article-title":"A Review on the Dietary Flavonoid Kaempferol","volume":"11","year":"2011","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"310","DOI":"10.1016\/j.jfda.2014.10.002","article-title":"Hepatoprotective effects of kaempferol 3-O-rutinoside and kaempferol 3-O-glucoside from Carthamus tinctorius-induced oxidative liver injury in mice","volume":"23","author":"Wang","year":"2015","journal-title":"J. Food Drug Anal."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"33370","DOI":"10.1039\/C4RA02784A","article-title":"Multifunctional pentacyclictriterpenoids as adjuvants in cancer chemotherapy: A review","volume":"4","author":"Kamble","year":"2014","journal-title":"RSC Adv."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"436","DOI":"10.1002\/pca.2578","article-title":"Seasonal Variation of Triterpenes and Phenolic Compounds in Australian Centella asiatica (L.) Urb","volume":"26","author":"Alqahtani","year":"2015","journal-title":"Phytochem. Anal."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"796","DOI":"10.1002\/ptr.2176","article-title":"Inhibition of alpha-glucosidase and amylase by bartogenic acid isolated from Barringtonia racemosa Roxb. seeds","volume":"21","author":"Gowri","year":"1997","journal-title":"Phytother. Res."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1055\/s-0029-1186142","article-title":"Anti-inflammatory Effects of Madecassic Acid via the Suppression of NF-\u03baB Pathway in LPS-Induced RAW 264.7 Macrophage Cells","volume":"76","author":"Won","year":"2010","journal-title":"Planta Med."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1185","DOI":"10.1016\/0031-9422(79)80131-4","article-title":"Neuecadinan-derivateaus Heterotheca subaxillaris","volume":"18","author":"Bohlmann","year":"1979","journal-title":"Phytochemistry"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2841","DOI":"10.1016\/S0031-9422(00)83754-1","article-title":"Diterpene glycosides and other constituents from argentinian baccharis species","volume":"25","author":"Zdero","year":"1986","journal-title":"Phytochemistry"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/S0031-9422(97)00475-5","article-title":"A phloracetophenone glucoside from Rhododendron ferrugineum","volume":"47","author":"Chosson","year":"1998","journal-title":"Phytochemistry"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1016\/j.foodchem.2014.12.039","article-title":"Anthocyanins and antioxidant capacities of six Chilean berries by HPLC-HR-ESI-ToF-MS","volume":"176","author":"Ramirez","year":"2015","journal-title":"Food Chem."},{"key":"ref_48","first-page":"178","article-title":"Estimation of total flavonoid content in propolis by two complementary colorimetric methods","volume":"10","author":"Chang","year":"2002","journal-title":"J. Food Drug Anal."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.jep.2004.06.035","article-title":"Free radical scavengers and antioxidants from Baccharis grisebachii","volume":"95","author":"Tapia","year":"2004","journal-title":"J. Ethnopharmacol."},{"key":"ref_50","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_51","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 Radic. Biol. Med."},{"key":"ref_52","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"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/4\/793\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T14:59:00Z","timestamp":1760194740000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/4\/793"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,3,29]]},"references-count":52,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2018,4]]}},"alternative-id":["molecules23040793"],"URL":"https:\/\/doi.org\/10.3390\/molecules23040793","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2018,3,29]]}}}