{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T08:42:55Z","timestamp":1790239375244,"version":"4.1.0"},"reference-count":25,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2015,10,2]],"date-time":"2015-10-02T00:00:00Z","timestamp":1443744000000},"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>Plants from the genus Pterocaulon are popularly used as antifungal and  wound-healing agents. Such activities have been related to coumarins, which are abundant in those plants. Coumarins are soluble in organic solvents, such as hexane and dichloromethane, and some of them are also soluble in hot water. Considering that infusion and decoctions of these plants are used in traditional medicine, the aim of this study was to identify and quantify the coumarins in the aqueous extract of Pterocaulon balansae. The aqueous extract was obtained by dynamic maceration and the compounds were characterized by UPLC-UV-MS analysis. A new coumarin and 5-methoxy-6,7-methylenedioxycoumarin, used for validation of the analytical HPLC method were obtained by partition of the aqueous extract with n-hexane. The HPLC method validated was linear, specific, and precise. Seven coumarins were characterized in the aqueous extract in a range of 0.584\u201354 mg\/g of dry plant material. The main compound, 5,6-dimethoxy-7-(3\u2032-methyl-2\u2032,3\u2032-dihydroxybutyloxy)coumarin, is described for the first time in P. balansae together with a new compound, 5,6-dimethoxy-7-(2\u2032,3\u2032-epoxy-3\u2032-methylbutyloxy)coumarin.<\/jats:p>","DOI":"10.3390\/molecules201018083","type":"journal-article","created":{"date-parts":[[2015,10,2]],"date-time":"2015-10-02T10:05:52Z","timestamp":1443780352000},"page":"18083-18094","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Quantification of Coumarins in Aqueous Extract of  Pterocaulon balansae (Asteraceae) and Characterization of a New Compound"],"prefix":"10.3390","volume":"20","author":[{"given":"Bruna","family":"Medeiros-Neves","sequence":"first","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, Faculdade de Farm\u00e1cia,  Universidade Federal do Rio Grande do Sul, Avenida Ipiranga, 2752, Porto Alegre, RS 90610-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francisco","family":"De Barros","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, Faculdade de Farm\u00e1cia,  Universidade Federal do Rio Grande do Sul, Avenida Ipiranga, 2752, Porto Alegre, RS 90610-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gilsane","family":"Von Poser","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, Faculdade de Farm\u00e1cia,  Universidade Federal do Rio Grande do Sul, Avenida Ipiranga, 2752, Porto Alegre, RS 90610-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Helder","family":"Teixeira","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, Faculdade de Farm\u00e1cia,  Universidade Federal do Rio Grande do Sul, Avenida Ipiranga, 2752, Porto Alegre, RS 90610-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2015,10,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1021\/np200906s","article-title":"Natural products as sources of new drugs over the 30 years from 1981 to 2010","volume":"75","author":"Newman","year":"2012","journal-title":"J. Nat. Prod."},{"key":"ref_2","first-page":"21","article-title":"Etnomedicina veterin\u00e1ria, etnonosotaxia e etnoterap\u00eautica de doen\u00e7as de pele como refer\u00eancia para sele\u00e7\u00e3o e avalia\u00e7\u00e3o preliminar da atividade antibacteriana de plantas nativas no sul do Brasil","volume":"10","author":"Avancini","year":"2008","journal-title":"Rev. Bras. Plantas Med."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.jep.2005.02.011","article-title":"Ethnoveterinary medicine in the search for antimicrobial agents: Antifungal activity of some species of Pterocaulon (Asteraceae)","volume":"99","author":"Stein","year":"2005","journal-title":"J. Ethnopharmacol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"246","DOI":"10.1111\/j.1439-0507.2009.01704.x","article-title":"Antifungal activity of Pterocaulon alopecuroides (Asteraceae) against chromoblastomycosis agents","volume":"53","author":"Daboit","year":"2010","journal-title":"Mycoses"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/j.mycmed.2011.07.002","article-title":"Antifungal activity of Pterocaulon species (Asteraceae) against Sporothrix schenckii","volume":"21","author":"Stopiglia","year":"2011","journal-title":"J. Mycol. Med."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1539","DOI":"10.1021\/np50113a010","article-title":"3-(Methyl-2-butenyloxy)-6,7-methylenedioxy-coumarin, a 5,6,7-trioxygenated coumarin from Pterocaulon virgatum","volume":"57","author":"Debenedetti","year":"1994","journal-title":"J. Nat. Prod."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1016\/S0031-9422(98)00460-9","article-title":"A hydroxy-beta-caryophyllene from Pterocaulon serrulatum","volume":"50","author":"Macleod","year":"1999","journal-title":"Phytochemistry"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1055\/s-2006-960786","article-title":"6,7-Dioxygenated and 5,6,7-trioxygenated coumarins from Pterocaulon polystachyum","volume":"63","author":"Palacios","year":"1999","journal-title":"Planta Med."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"183","DOI":"10.3987\/COM-03-S16","article-title":"Chemical constituents of Pterocaulon redolens","volume":"61","author":"Kanlayavattanakul","year":"2003","journal-title":"Heterocycles"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1007\/s10600-007-0231-x","article-title":"Distribution of coumarins in the tribe Plucheeae, genus Pterocaulon","volume":"43","author":"Stein","year":"2007","journal-title":"Chem. Nat. Compd."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1016\/j.canlet.2004.03.015","article-title":"Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon polystachyum","volume":"210","author":"Riveiro","year":"2004","journal-title":"Cancer Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1016\/j.ejmech.2012.09.007","article-title":"Selective cytotoxicity and apoptosis induction in glioma cell lines by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon species","volume":"57","author":"Vianna","year":"2012","journal-title":"Eur. J. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"277","DOI":"10.1016\/0015-6264(79)90289-X","article-title":"Critical review of the toxicology of coumarin with special reference to interspecies differences in metabolism and hepatotoxic response and their significance to man","volume":"17","author":"Cohen","year":"1978","journal-title":"Food Chem. Toxicol."},{"key":"ref_14","unstructured":"Murray, R.D.H., M\u00e9ndez, J., and Brown, S.A. (1982). The Natural Coumarins: Occurrence, Chemistry, and Biochemistry, Wiley."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1369","DOI":"10.1016\/0031-9422(81)80042-8","article-title":"Coumarins from Pterocaulon balansae and P. lanatum","volume":"20","author":"Junior","year":"1981","journal-title":"Phytochemistry"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"585","DOI":"10.1590\/S1516-93322006000400014","article-title":"Estudo fitoqu\u00edmico da esp\u00e9cie Pterocaulon interruptum DC. (Asteraceae)","volume":"42","author":"Heemann","year":"2006","journal-title":"Rev. Bras. Cienc. Farm."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"959","DOI":"10.1016\/j.jep.2006.02.009","article-title":"Antifungal activity of some coumarins obtained from species of Pterocaulon (Asteraceae)","volume":"107","author":"Stein","year":"2006","journal-title":"J. Ethnopharmacol."},{"key":"ref_18","first-page":"1487","article-title":"Spectrophotometric determination of coumarins incorporated into nanoemulsions containg Pterocaulon balansae extract","volume":"30","author":"Vianna","year":"2011","journal-title":"Lat. Am. J. Pharm."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"8615","DOI":"10.3390\/ijms13078615","article-title":"Green extraction of natural products: Concept and principles","volume":"13","author":"Chemat","year":"2012","journal-title":"Int. J. Mol. Sci."},{"key":"ref_20","unstructured":"Barros, S.M.G. (1981). As Cumarinas do Pterocaulon balansae Chodat. [Master\u2019s Thesis, Universidade Estadual de Campinas]."},{"key":"ref_21","unstructured":"Vallejo, S.B. Identificaci\u00f3n de Cumarinas en Esp\u00e9cies Aut\u00f3ctonas del G\u00eanero Pterocaulon ell.. Available online: http:\/\/www.ub.edu.ar\/investigaciones\/tesinas\/311_Tesina_Barata_Vallejo.pdf."},{"key":"ref_22","unstructured":"Zhao, W. (2012). Introduction to Natural Products Chemistry, CRC Press."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"674","DOI":"10.1055\/s-2001-17365","article-title":"New coumarins from Pterocaulon polystachyum","volume":"67","author":"Vera","year":"2001","journal-title":"Planta Med."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1181","DOI":"10.1016\/0031-9422(95)00166-5","article-title":"Highly oxygenated coumarins from Pelargonium sidoides","volume":"39","author":"Kayser","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_25","unstructured":"ICH Q2 (R1) Validation of Analytical Procedures: Text and Methodology. Available online: http:\/\/www.ich.org\/products\/guidelines\/quality\/article\/quality-guidelines.html."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/10\/18083\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T20:49:40Z","timestamp":1760215780000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/10\/18083"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,10,2]]},"references-count":25,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2015,10]]}},"alternative-id":["molecules201018083"],"URL":"https:\/\/doi.org\/10.3390\/molecules201018083","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,10,2]]}}}