{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,24]],"date-time":"2026-06-24T12:41:22Z","timestamp":1782304882328,"version":"3.54.5"},"reference-count":35,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2018,5,16]],"date-time":"2018-05-16T00:00:00Z","timestamp":1526428800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002923","name":"CONICET","doi-asserted-by":"publisher","award":["PIP 444-CONICET"],"award-info":[{"award-number":["PIP 444-CONICET"]}],"id":[{"id":"10.13039\/501100002923","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004442","name":"National Science Centre","doi-asserted-by":"publisher","award":["2013\/09\/B\/NZ7\/00423"],"award-info":[{"award-number":["2013\/09\/B\/NZ7\/00423"]}],"id":[{"id":"10.13039\/501100004442","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100015352","name":"Faculty of Pharmacy of Comenius University","doi-asserted-by":"publisher","award":["FaF UK\/37\/2018"],"award-info":[{"award-number":["FaF UK\/37\/2018"]}],"id":[{"id":"10.13039\/100015352","id-type":"DOI","asserted-by":"publisher"}]},{"name":"SANOFI-AVENTIS Pharma Slovakia, s.r.o.","award":["SANOFI-AVENTIS research grant"],"award-info":[{"award-number":["SANOFI-AVENTIS research grant"]}]},{"DOI":"10.13039\/100009571","name":"Universidad Nacional de San Luis","doi-asserted-by":"publisher","award":["CICITCA-UNSJ"],"award-info":[{"award-number":["CICITCA-UNSJ"]}],"id":[{"id":"10.13039\/100009571","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Annona emarginata (Schltdl.) H. Rainer, commonly known as \u201carachich\u00fa\u201d, \u201caratic\u00fa\u201d, \u201caratig\u00fa\u201d, and \u201cyerba mora\u201d, is a plant that grows in Argentina. Infusions and decoctions are used in folk medicine as a gargle against throat pain and for calming toothache; another way to use the plant for these purposes is chewing its leaves. Extracts from bark, flowers, leaves, and fruits from A. emarginata were subjected to antibacterial assays against a panel of Gram (+) and Gram (\u2212) pathogenic bacteria according to Clinical and Laboratory Standards Institute protocols. Extracts from the stem bark and leaves showed moderate activity against the bacteria tested with values between 250\u20131000 \u00b5g\/mL. Regarding flower extracts, less polar extracts (hexane, dichloromethane) showed very strong antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus ATCC 43300 with values between 16\u2013125 \u00b5g\/mL. Additionally, hexane extract showed activity against Klebsiella pneumoniae (MIC = 250 \u00b5g\/mL). The global methanolic extract of the fruits (MeOHGEF) was also active against the three strains mentioned above, with MICs values 250\u2013500 \u00b5g\/mL. Bioassay-guided fractionation of MeOHGEF led to the isolation of a new main compound\u2014(R)-2-(4-methylcyclohex-3-en-1-yl)propan-2-yl (E)-3-(4-hydroxyphenyl)acrylate (1). The structure and relative configurations have been determined by means of 1D and 2D NMR techniques, including COSY, HMQC, HMBC, and NOESY correlations. Compound 1 showed strong antimicrobial activity against all Gram (+) species tested (MICs = 3.12\u20136.25 \u00b5g\/mL). In addition, the synthesis and antibacterial activity of some compounds structurally related to compound 1 (including four new compounds) are reported. A SAR study for these compounds was performed based on the results obtained by using molecular calculations.<\/jats:p>","DOI":"10.3390\/molecules23051187","type":"journal-article","created":{"date-parts":[[2018,5,17]],"date-time":"2018-05-17T03:49:29Z","timestamp":1526528969000},"page":"1187","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["The Antimicrobial Activity of Annona emarginata (Schltdl.) H. Rainer and Most Active Isolated Compounds against Clinically Important Bacteria"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4372-1214","authenticated-orcid":false,"given":"Juan G.","family":"Dolab","sequence":"first","affiliation":[{"name":"Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Beatriz","family":"Lima","sequence":"additional","affiliation":[{"name":"Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ewelina","family":"Spaczynska","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Silesia, 75 Pulku Piechoty 1, 41500 Chorzow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiri","family":"Kos","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Natividad H.","family":"Cano","sequence":"additional","affiliation":[{"name":"Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4076-3999","authenticated-orcid":false,"given":"Gabriela","family":"Feresin","sequence":"additional","affiliation":[{"name":"Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alejandro","family":"Tapia","sequence":"additional","affiliation":[{"name":"Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francisco","family":"Garibotto","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina"},{"name":"Multidisciplinary Institute of Biological Research IMIBIO-CONICET, Chacabuco 917, 5700 San Luis, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5036-8060","authenticated-orcid":false,"given":"Elisa","family":"Petenatti","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monica","family":"Olivella","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"Musiol","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Silesia, 75 Pulku Piechoty 1, 41500 Chorzow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2003-9052","authenticated-orcid":false,"given":"Josef","family":"Jampilek","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, Slovakia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ricardo D.","family":"Enriz","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina"},{"name":"Multidisciplinary Institute of Biological Research IMIBIO-CONICET, Chacabuco 917, 5700 San Luis, Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,5,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"828","DOI":"10.1590\/S0103-50532003000500020","article-title":"Antifungal aromadendrane sesquiterpenoids from the leaves of Xylopia brasiliensis","volume":"14","author":"Moreira","year":"2003","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1080\/14786410412331280087","article-title":"Antibacterial activity of eight Brazilian Annonaceae plants","volume":"20","author":"Takahashi","year":"2006","journal-title":"Nat. Prod. Res."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1078\/094471103321659960","article-title":"Biological screening of Annonaceous Brazilian Medicinal Plants using Artemia salina (Brine Shrimp Test)","volume":"10","author":"Pinto","year":"2003","journal-title":"Phytomedicine"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1007\/s40415-015-0225-z","article-title":"Biological activities of Annonaceae species extracts from Cerrado","volume":"39","author":"Novaes","year":"2016","journal-title":"Braz. J. Bot."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1590\/S0100-29452014000500038","article-title":"Plants of the Annonaceae traditionally used as antimalarials: A review","volume":"36","author":"Frausin","year":"2014","journal-title":"Rev. Bras. Frutic."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1002\/(SICI)1099-1573(199903)13:2<175::AID-PTR395>3.0.CO;2-N","article-title":"Antiprotozoal activity of aporphine alkaloids isolated from Unonopsis buchtienii (Annonaceae)","volume":"13","author":"Waechter","year":"1999","journal-title":"Phytotherapy Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1016\/j.jep.2012.05.019","article-title":"Anti-tumor activity of Annona squamosa seeds extract containing annonaceous acetogen in compounds","volume":"142","author":"Chen","year":"2012","journal-title":"J. Ethnopharmacol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1076\/phbi.40.8.603.14658","article-title":"Anti-tumour screening of Brazilian plants","volume":"40","author":"Monks","year":"2002","journal-title":"Pharm. Biol."},{"key":"ref_9","first-page":"7","article-title":"Medicinal plants: A general review and a phytochemical and ethnopharmacological screening of the native Argentine flora","volume":"34","author":"Barboza","year":"2009","journal-title":"Kurtziana"},{"key":"ref_10","unstructured":"Martinez Crovetto, R. (1981). Plantas Utilizadas en Medicina en el NO de Corrientes."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1055\/s-1999-13961","article-title":"Acetogenins and other compounds from Rollinia emarginata and their antiprotozoal activities","volume":"65","author":"Fevrier","year":"1999","journal-title":"Planta Med."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1080\/14786410500462819","article-title":"Bioactive constituents from Rollinia emarginata (Annonaceae)","volume":"21","author":"Colom","year":"2007","journal-title":"Nat. Prod. Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"624","DOI":"10.1124\/jpet.111.184564","article-title":"Isolation of modulators of the liver-specific organic anion-transporting polypeptides (OATPs) 1B1 and 1B3 from Rollinia emarginata Schltdl. (Annonaceae)","volume":"339","author":"Roth","year":"2011","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"717","DOI":"10.1021\/np50046a037","article-title":"Alkaloids from Rollinia emarginata","volume":"49","author":"Nieto","year":"1986","journal-title":"J. Nat. Prod."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2783","DOI":"10.1016\/0031-9422(80)85046-1","article-title":"The phytochemistry of the Annonaceae","volume":"21","author":"Leboeuf","year":"1982","journal-title":"Phytochem"},{"key":"ref_16","unstructured":"O\u2019Neill, J. (2016). Tackling Drug-Resistant Infections Globally: Final Report and Recommendations."},{"key":"ref_17","first-page":"7","article-title":"Actualizaci\u00f3n en Staphylococcus aureus resistente a meticilina de la comunidad","volume":"193","author":"Gagetti","year":"2011","journal-title":"Bol. Assoc. Argent. Microbiol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"611","DOI":"10.1016\/j.fitote.2007.06.006","article-title":"New phenolic esters from the resinous exudate of Haplopappus taeda","volume":"78","author":"Faini","year":"2007","journal-title":"Fitoterapia"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1016\/S0378-8741(03)00259-9","article-title":"Constituents of the Argentinean medicinal plant Baccharis grisebachii and their antimicrobial activity","volume":"89","author":"Feresin","year":"2003","journal-title":"J. Ethnopharmacol."},{"key":"ref_20","first-page":"1","article-title":"Constituents from Bacccharis grisebachii","volume":"75","author":"Gianello","year":"1987","journal-title":"An. Assoc. Qu\u00edm. Argent."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"10635","DOI":"10.1021\/jf0729098","article-title":"Structure-antifungal activity relationship of related cinnamic acid derivatives","volume":"55","author":"Bisogno","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"424","DOI":"10.1021\/np990393j","article-title":"Antifungal and larvicidal compounds from the root bark of Cordia alliodora","volume":"63","author":"Ioset","year":"2000","journal-title":"J. Nat. Prod."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7814","DOI":"10.1021\/jf0487093","article-title":"Identification of phenolics for control of Aspergillus flavus using Saccharomyces cerevisiae in a model target-gene bioassay","volume":"52","author":"Kim","year":"2004","journal-title":"J. Agric. Food Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"613","DOI":"10.3390\/molecules17010613","article-title":"Investigating the spectrum of biological activity of substituted quinoline-2-carboxamides and their isosteres","volume":"17","author":"Gonec","year":"2012","journal-title":"Molecules"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2035","DOI":"10.1016\/j.bmc.2015.03.018","article-title":"Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides","volume":"23","author":"Kos","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"4188","DOI":"10.1016\/j.bmc.2015.06.047","article-title":"Ring-substituted 8-Hydroxyquinoline-2-carboxanilides as potential antimycobacterial agents","volume":"23","author":"Kos","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"ref_27","unstructured":"Polilzer, P., and Truhlar, D.G. (1991). Chemical Applications of Atomic and Molecular Electrostatic Potentials, Plenum Publishing."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"638","DOI":"10.1016\/0076-6879(91)03033-D","article-title":"Molecular electrostatic potentials for characterizing drug-biosystem interactions","volume":"202","author":"Carrupt","year":"1991","journal-title":"Methods Enzymol."},{"key":"ref_29","first-page":"587","article-title":"Molecular electrostatic potentials vs. DFT descriptors of reactivity","volume":"Volume 3","author":"Politzer","year":"1996","journal-title":"Molecular Electrostatic Potentials: Concepts and Applications. Theoretical and Computational Chemistry"},{"key":"ref_30","unstructured":"Clinical and Laboratory Standards Institute (2012). Performance Standards for Antimicrobial Susceptibility Testing, CLSI. M100-S22."},{"key":"ref_31","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2009). Gaussian 09, Gaussian, Inc."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1998","journal-title":"Phys. Rev. B"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"5618","DOI":"10.1063\/1.464913","article-title":"Density-functional thermochemistry. III. The role of exact exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1103\/PhysRevA.38.3098","article-title":"Density-functional exchange-energy approximation with correct asymptotic behavior","volume":"38","author":"Becke","year":"1998","journal-title":"Phys. Rev. A"},{"key":"ref_35","unstructured":"Flukiger, P., Luthi, H.P., Portmann, S., and Weber, J. (2000). MOLEKEL 4.0, Swiss Center for Scientific Computing."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/5\/1187\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:04:25Z","timestamp":1760195065000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/5\/1187"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,5,16]]},"references-count":35,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2018,5]]}},"alternative-id":["molecules23051187"],"URL":"https:\/\/doi.org\/10.3390\/molecules23051187","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,5,16]]}}}