{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:35:52Z","timestamp":1786977352107,"version":"build-2736575974"},"reference-count":32,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2025,9,25]],"date-time":"2025-09-25T00:00:00Z","timestamp":1758758400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2025,9,25]],"date-time":"2025-09-25T00:00:00Z","timestamp":1758758400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp;amp; Biodiversity"],"published-print":{"date-parts":[[2025,12]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    <jats:italic>Eperua oleifera<\/jats:italic>\n                    Ducke, commonly known as \u201ccopa\u00edba\u2010jacar\u00e9,\u201d produces oilresins traditionally used in folk medicine for wound healing and as antifungal and antibacterial agents, similar to those of\n                    <jats:italic>Copaifera<\/jats:italic>\n                    species. However, its chemical composition remains poorly characterized. This study investigated the oilresin of\n                    <jats:italic>E. oleifera<\/jats:italic>\n                    collected in the Brazilian Amazon region. After derivatization, the sample was analyzed by GC\u2013MS, with data compared to literature, mass spectral libraries, and standards previously isolated. In addition, neutral and acidic fractions were separated using ion\u2010exchange open\u2010column chromatography with silica modified with KOH\u2010impregnated silica as the stationary phase. Twelve diterpenes were identified, including nine carboxylic acids and three alcohols. Hardwickiic acid and copalic acid were the major components, fully characterized by NMR. The most abundant compound in the neutral fraction was isolated and identified by HRMS and NMR as the methyl ester of hardwickiic acid\u2014a compound not previously reported in oilresins. The application of GC\u2013MS enabled the identification of diterpenes based on known fragmentation patterns. In addition, the direct infusion experiment detected a methyl ester that, to our knowledge, has not been previously reported in oilresins.\n                  <\/jats:p>","DOI":"10.1002\/cbdv.202501730","type":"journal-article","created":{"date-parts":[[2025,9,25]],"date-time":"2025-09-25T17:32:01Z","timestamp":1758821521000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["<i>Eperua oleifera<\/i>\n                    Ducke (Fabaceae) Oilresin Chemical Composition and the Isolation of a Natural Diterpenic Acid Methyl Ester"],"prefix":"10.1002","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6533-3530","authenticated-orcid":false,"given":"Rayssa","family":"Ribeiro","sequence":"first","affiliation":[{"name":"Department of Chemical Engineering Military Institute of Engineering  Rio De Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8597-416X","authenticated-orcid":false,"given":"Henrique M. G.","family":"Pereira","sequence":"additional","affiliation":[{"name":"Chemistry Institute, Brazilian Doping Control Laboratory (LBCD\/IQ\u2013UFRJ) Federal University of Rio de Janeiro  Rio de Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7439-8400","authenticated-orcid":false,"given":"Alvicler","family":"Magalh\u00e3es","sequence":"additional","affiliation":[{"name":"Chemistry Institute (IQ\u2013UFRJ) Federal University of Rio de Janeiro  Rio de Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8304-1427","authenticated-orcid":false,"given":"Fernando","family":"Hallwass","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering Military Institute of Engineering  Rio De Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monica C.","family":"Padilha","sequence":"additional","affiliation":[{"name":"Chemistry Institute, Brazilian Doping Control Laboratory (LBCD\/IQ\u2013UFRJ) Federal University of Rio de Janeiro  Rio de Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1365-7602","authenticated-orcid":false,"given":"Valdir F.","family":"Veiga\u2010Junior","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering Military Institute of Engineering  Rio De Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,9,25]]},"reference":[{"key":"e_1_2_9_2_1","first-page":"18","article-title":"Chemistry and Biosynthesis Pathways of Plant Oleoresins: Important Drug Sources","volume":"12","author":"Shahzadi I.","year":"2017","journal-title":"International Journal of Chemical and Biochemical Sciences"},{"key":"e_1_2_9_3_1","first-page":"93","article-title":"The Chemistry and Pharmacology of the South America genus Protium Burm. f. (Burseraceae)","volume":"1","author":"R\u00fcdiger A. L.","year":"2007","journal-title":"Pharmacognosy Reviews"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fbio.2023.102668"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms19051511"},{"key":"e_1_2_9_6_1","first-page":"14","article-title":"O G\u00eanero Eperua Aublet: Uma Revis\u00e3o","volume":"1","author":"Leandro L. M.","year":"2012","journal-title":"Scientia Amazonia"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.201200315"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1590\/S0100-40422005000300026"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.5962\/bhl.title.122509"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.2307\/2806078"},{"key":"e_1_2_9_11_1","unstructured":"L. M.Leandro \u201cEstudo fitoqu\u00edmico e atividades biol\u00f3gicas de Eperua duckeana e Eperua glabriflora (Fabaceae). Disserta\u00e7\u00e3o (Mestrado em Qu\u00edmica) \u2010 Universidade Federal do Amazonas \u201d2011."},{"key":"e_1_2_9_12_1","first-page":"42","article-title":"Composi\u00e7\u00e3o qu\u00edmica e atividade citot\u00f3xica dos \u00f3leos essenciais das folhas e talos de Eperua duckeana Cowan","volume":"14","author":"Leandro L. M.","year":"2015","journal-title":"Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.4103\/pm.pm_552_16"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-971500"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-962686"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/np50015a026"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/jr9550000658"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1590\/S0103-50532000000400005"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1007\/s43450-021-00173-2"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-030-91378-6_19"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.3390\/antibiotics12030509"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2mb25171j"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytol.2014.08.006"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/np50085a002"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/np50099a019"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201402652"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-8741(01)00322-1"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/ptr.2414"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf034682w"},{"key":"e_1_2_9_30_1","article-title":"First Choice in High Resolution Mass Spectrometry with Orbitrap Mass Analyzer Technology for Screening, Confirmative and Quantitative Analyses","author":"Bromirski M.","year":"2018","journal-title":"Thermo Scientific White Paper"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.201100127"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(98)00464-6"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2004.06.013"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.202501730","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbdv.202501730","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.202501730","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,3,14]],"date-time":"2026-03-14T11:54:33Z","timestamp":1773489273000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.202501730"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,9,25]]},"references-count":32,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2025,12]]}},"alternative-id":["10.1002\/cbdv.202501730"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.202501730","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,9,25]]},"assertion":[{"value":"2025-05-20","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-09-15","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-09-25","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e01730"}}