{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:57:12Z","timestamp":1787029032482,"version":"build-2736575974"},"reference-count":20,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2016,9,12]],"date-time":"2016-09-12T00:00:00Z","timestamp":1473638400000},"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>Chemical investigation of the leaves from Ageratina glabrata yielded four new thymol derivatives, namely: 10-benzoyloxy-8,9-dehydro-6-hydroxythymol isobutyrate (4), 10-benzoyloxy-8,9-dehydrothymol (5), 10-benzoyloxythymol (6) and 10-benzoyloxy-6,8-dihydroxy-9-isobutyryl-oxythymol (7). In addition, (8S)-10-benzoyloxy-8,9-epoxy-6-hydroxythymol isobutyrate (1), together with other two already known thymol derivatives identified as 10-benzoyloxy-8,9-epoxy-6-methoxythymol isobutyrate (2) and 10-benzoyloxy-8,9-epoxythymol isobutyrate (3) were also obtained. In this paper, we report the structures and complete assignments of the 1H and 13C-NMR data of compounds 1\u20137, and the absolute configuration for compound 1, unambiguously established by single crystal X-ray diffraction, and evaluation of the Flack parameter. The in vitro antiprotozoal assay showed that compound 1 and its derivative 1a were the most potent antiamoebic and antigiardial compounds. Both compounds showed selectivity and good antiamoebic activity comparable to emetine and metronidazole, respectively, two antiprotozoal drugs used as positive controls. In relation to anti-propulsive effect, compound 1 and 1a showed inhibitory activity, with activities comparable to quercetin and compound 9, two natural antipropulsive compounds used as positive controls. These data suggest that compound 1 may play an important role in antidiarrheal properties of Ageratina glabrata.<\/jats:p>","DOI":"10.3390\/molecules21091132","type":"journal-article","created":{"date-parts":[[2016,9,12]],"date-time":"2016-09-12T10:24:41Z","timestamp":1473675881000},"page":"1132","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Antidiarrheal Thymol Derivatives from Ageratina glabrata. Structure and Absolute Configuration of 10-Benzoyloxy-8,9-epoxy-6-hydroxythymol Isobutyrate"],"prefix":"10.3390","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9976-5251","authenticated-orcid":false,"given":"Celia","family":"Bustos-Brito","sequence":"first","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Valeria","family":"V\u00e1zquez-Heredia","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fernando","family":"Calzada","sequence":"additional","affiliation":[{"name":"UIM en Farmacolog\u00eda, 2o Piso CORCE, UMAE Hospital de Especialidades, Centro M\u00e9dico Nacional Siglo XXI, IMSS, Av. Cuauht\u00e9moc 330, Col. Doctores, M\u00e9xico, D.F. 06725, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lilian","family":"Y\u00e9pez-Mulia","sequence":"additional","affiliation":[{"name":"UIM en Enfermedades Infecciosas y Parasitarias, UMAE Hospital de Pediatr\u00eda, Centro M\u00e9dico Nacional Siglo XXI, IMSS, Av. Cuauht\u00e9moc 330, Col. Doctores, M\u00e9xico, D.F. 06725, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9","family":"Calder\u00f3n","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sim\u00f3n","family":"Hern\u00e1ndez-Ortega","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Baldomero","family":"Esquivel","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6021-8309","authenticated-orcid":false,"given":"Normand","family":"Garc\u00eda-Hern\u00e1ndez","sequence":"additional","affiliation":[{"name":"UIM en Gen\u00e9tica Humana, UMAE Hospital de Pediatr\u00eda, Centro M\u00e9dico Nacional Siglo XXI, IMSS, Centro M\u00e9dico Nacional Siglo XXI, IMSS, Av. Cuauht\u00e9moc 330, Col. Doctores, M\u00e9xico, D.F. 06725, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4804-3013","authenticated-orcid":false,"given":"Leovigildo","family":"Quijano","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, D.F. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2016,9,12]]},"reference":[{"key":"ref_1","first-page":"32","article-title":"Eupaglabrina, un nuevo terpeno aislado de Eupatorium glabratum","volume":"2","author":"Cuevas","year":"1971","journal-title":"Rev. Latinoam. Chem."},{"key":"ref_2","first-page":"71","article-title":"Acido eupaglabrico un Nuevo compuesto aislado de Eupatorium glabratum H.B.K","volume":"9","author":"Guerrero","year":"1978","journal-title":"Rev. Latinoam. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1002\/cber.19771100132","article-title":"Naturally Ocurring Terpene Derivatives, 76, On Constituents of the Eupatorium group","volume":"110","author":"Bohlmann","year":"1977","journal-title":"Chem. Ber."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1080\/10412905.2015.1093969","article-title":"Chemical composition and evaluation of the essential oil from Eupatorium glabratum as biopesticide against Sitophilus zeamais and several stored maize fungi","volume":"28","year":"2016","journal-title":"J. Essent. Oil Res."},{"key":"ref_5","first-page":"91","article-title":"Antibacterial activity of some medicinal Eupatorium species against antibiotic resistant pathogenic bacteria","volume":"39","year":"2015","journal-title":"Polibot\u00e1nica"},{"key":"ref_6","first-page":"45","article-title":"Preliminary studies on the analgesic effect of leaf extract from Ageratina glabrata in two thermal models of acute pain","volume":"42","author":"Martinez","year":"2011","journal-title":"Rev. Mex. Cienc. Farm."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"358","DOI":"10.1021\/np400964w","article-title":"Structure, absolute configuration, and antidiarrheal activity of a thymol derivative from Ageratina cylindrica","volume":"77","author":"Esquivel","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2580","DOI":"10.1021\/acs.jnatprod.5b00488","article-title":"ent-Kaurene Glycosides from Ageratina cylindrica","volume":"78","author":"Esquivel","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"629","DOI":"10.1002\/jccs.200400094","article-title":"Chemical Components of Seriphidium santolium Poljak","volume":"51","author":"Deng","year":"2004","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"681","DOI":"10.1002\/chir.20473","article-title":"The use of X-ray chrystallography to determine absolute configuration","volume":"20","author":"Flack","year":"2008","journal-title":"Chirality"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2893","DOI":"10.1016\/0031-9422(88)80681-2","article-title":"Germacranolides and other constituents from Ageratina species","volume":"27","author":"Jakupovic","year":"1988","journal-title":"Phytochemistry"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2527","DOI":"10.1016\/0031-9422(92)83316-Q","article-title":"A thymol derivative from Calea nelsonii","volume":"31","author":"Maldonado","year":"1992","journal-title":"Phytochemistry"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"864","DOI":"10.1002\/cber.19691020319","article-title":"\u00dcber einige thymolderivate aus Gaillardia-und Helenium-arten","volume":"102","author":"Bohlmann","year":"1969","journal-title":"Chem. Ber."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"928","DOI":"10.1590\/S0102-695X2011005000158","article-title":"Analgesic effect of leaf extract from Ageratina glabrata in the hot plate test","volume":"21","author":"Scior","year":"2011","journal-title":"Braz. J. Pharmacog."},{"key":"ref_15","unstructured":"Bruker (2012). SAINT & APEX-2 Programs, Bruker AXS Inc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. C Struct. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","article-title":"WinGX and ORTEP for Windows: An update","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Crystallogr."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1076\/phbi.36.5.305.4653","article-title":"Screening of Mexican medicinal plants from antiprotozoal activity","volume":"36","author":"Calzada","year":"1998","journal-title":"Pharm. Biol."},{"key":"ref_19","unstructured":"(2001). Norma Oficial Mexicana NOM-062-ZOO-1999, Especificaciones T\u00e9cnicas Para la Producci\u00f3n, Cuidado y Uso de Los Animales de Laboratorio, Diario Oficial de la Federaci\u00f3n."},{"key":"ref_20","unstructured":"Williamson, E.M., Okpako, D.T., and Evans, F.J. (1996). Pharmacological Methods in Phytotherapy Research: Selection, Preparation and Pharmacological Evaluation of Plant Material, John Wiley & Sons. [1st ed.]."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/21\/9\/1132\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T19:29:28Z","timestamp":1760210968000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/21\/9\/1132"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,9,12]]},"references-count":20,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2016,9]]}},"alternative-id":["molecules21091132"],"URL":"https:\/\/doi.org\/10.3390\/molecules21091132","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,9,12]]}}}