{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T16:02:41Z","timestamp":1790697761802,"version":"4.1.0"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"38","license":[{"start":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T00:00:00Z","timestamp":1789171200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002322","name":"Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gico","doi-asserted-by":"publisher","award":["306586\/2023-1"],"award-info":[{"award-number":["306586\/2023-1"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004586","name":"Funda??o Carlos Chagas Filho de Amparo ? i Pesquisa do Estado do Rio de Janeiro","doi-asserted-by":"publisher","award":["E-26\/210.678\/2024"],"award-info":[{"award-number":["E-26\/210.678\/2024"]}],"id":[{"id":"10.13039\/501100004586","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,29]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Sporotrichosis caused by Sporothrix brasiliensis represents an emerging public health challenge in Brazil, with increasing therapeutic limitations and antifungal resistance. This study investigated Brazilian geopropolis produced by Melipona quadrifasciataanthidioides as a potential source of antifungal bioactive compounds. Bioassay-guided fractionation of the ethanolic extract led to the isolation of three constituents, identified by NMR, Fourier transform infrared spectroscopy (FTIR)-ATR, and LC-HRMS analyses as kaurenoic acid, cinnamoylgrandifloric acid, and 3S(+)-vestitol, the latter two being reported for the first time in this matrix. The dichloromethane fraction exhibited the best antioxidant capacity among the tested fractions (EC50 = 200.22 \u03bcg mL\u20131). In vitro assays against clinical isolates of S. brasiliensis revealed minimum inhibitory concentration (MIC) values ranging from 170.18 to 567.11 \u03bcg mL\u20131 for the extract and isolated compounds. Among them, 3S(+)-vestitol showed the strongest antifungal activity (MIC = 170.18 \u03bcg mL\u20131). These findings demonstrate that M. quadrifasciata geopropolis contains bioactive diterpenes and isoflavonoids with significant antifungal activity, highlighting its potential as a source of lead compounds for developing new therapeutic strategies against endemic sporotrichosis.<\/jats:p>","DOI":"10.1021\/acsomega.6c05995","type":"journal-article","created":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T15:01:44Z","timestamp":1789225304000},"page":"57498-57506","source":"Crossref","is-referenced-by-count":0,"title":["Bioactive Constituents\nof\n                    <i>Melipona quadrifasciata<\/i>\n                    <i>anthidioides<\/i>\n                    Geopropolis\nwith Antifungal Activity against\n                    <i>Sporothrix brasiliensis<\/i>"],"prefix":"10.1021","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7943-8467","authenticated-orcid":true,"given":"Gabriel F.","family":"dos Santos","sequence":"first","affiliation":[{"name":"Universidade Federal Rural do Rio de Janeiro , , BR 465-Km7 , , ,","place":["Serope\u0301dica, Rio de Janeiro, Brazil, 23897-000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria Clara N.","family":"Sampaio","sequence":"additional","affiliation":[{"name":"Universidade Federal Rural do Rio de Janeiro , , BR 465-Km7 , , ,","place":["Serope\u0301dica, Rio de Janeiro, Brazil, 23897-000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1842-2039","authenticated-orcid":true,"given":"Rafael F.","family":"dos Santos","sequence":"additional","affiliation":[{"name":"Universidade Federal Rural do Rio de Janeiro , , BR 465-Km7 , , ,","place":["Serope\u0301dica, Rio de Janeiro, Brazil, 23897-000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aguida A.","family":"de Oliveira","sequence":"additional","affiliation":[{"name":"Universidade Federal Rural do Rio de Janeiro , , BR 465-Km 7 , , ,","place":["Serope\u0301dica, Rio de Janeiro, Brazil, 23897-000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8983-3786","authenticated-orcid":true,"given":"Rosane N.","family":"Castro","sequence":"additional","affiliation":[{"name":"Universidade Federal Rural do Rio de Janeiro , , BR 465-Km7 , , ,","place":["Serope\u0301dica, Rio de Janeiro, Brazil, 23897-000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,12]]},"reference":[{"issue":"3","key":"2026092911085878900_cit1","doi-asserted-by":"publisher","first-page":"389","DOI":"10.1016\/j.bjp.2018.11.007","article-title":"Brazilian\nStingless Bee Propolis and Geopropolis: Promising Sources of Biologically\nActive Compounds","volume":"29","author":"Lavinas","year":"2019","journal-title":"Rev. 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Technol."},{"key":"2026092911085878900_cit5","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1007\/978-1-4614-4960-7_1","article-title":"The Meliponini","volume-title":"In Pot-Honey","author":"Michener","year":"2013"},{"key":"2026092911085878900_cit6","doi-asserted-by":"crossref","DOI":"10.1007\/978-3-030-60090-7","volume-title":"Stingless\nBees: Their Behaviour, Ecology and Evolution","author":"Gru\u0308ter","year":"2020"},{"key":"2026092911085878900_cit7","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2025.116674","article-title":"Propolis and Geopropolis from Stingless\nBees as a Source of Bioactive Compounds with Antioxidant and Antimicrobial\nAction: A Review","volume":"214","author":"Silva","year":"2025","journal-title":"Food Res. 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Sci."},{"key":"2026092911085878900_cit27","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2025.116674","article-title":"Propolis and Geopropolis from Stingless\nBees as a Source of Bioactive Compounds with Antioxidant and Antimicrobial\nAction: A Review","volume":"214","author":"Silva","year":"2025","journal-title":"Food Res. Int."},{"key":"2026092911085878900_cit28","doi-asserted-by":"publisher","DOI":"10.1016\/j.microc.2020.105031","article-title":"Could Antioxidant\nCapacity and Flavonoid Content of Ethanolic Extracts of Geopropolis\nfrom Brazilian Native Bees Be Estimated from Digital Photos and NIR\nSpectra?","volume":"157","author":"Turco","year":"2020","journal-title":"Microchem. J."},{"key":"2026092911085878900_cit29","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2022.132531","article-title":"Plant Flavonoids: Classification,\nDistribution, Biosynthesis, and\nAntioxidant Activity","volume":"383","author":"Shen","year":"2022","journal-title":"Food Chem."},{"issue":"6","key":"2026092911085878900_cit30","doi-asserted-by":"publisher","first-page":"1626","DOI":"10.1080\/14786419.2021.1892101","article-title":"The Chemical\nComposition and Antioxidant Activity of Mandac\u0327aia (Melipona Quadrifasciata) Geopropolis Varies More Due to Region than Month of Collection","volume":"36","author":"Gabriel","year":"2022","journal-title":"Nat. Product Res."},{"issue":"1","key":"2026092911085878900_cit31","doi-asserted-by":"publisher","DOI":"10.1155\/2017\/1038153","article-title":"Antioxidant, Cytotoxic, and Toxic\nActivities of Propolis from Two Native Bees in Brazil: Scaptotrigona Depilis and Melipona QuadrifasciataAnthidioides","volume":"2017","author":"Bonamigo","year":"2017","journal-title":"Oxidative Med. Cell. Longevity"},{"issue":"10","key":"2026092911085878900_cit32","doi-asserted-by":"publisher","first-page":"3209","DOI":"10.1016\/0031-9422(88)80027-X","article-title":"New Diterpenoids from Croton Argyrophylloides","volume":"27","author":"Monte","year":"1988","journal-title":"Phytochemistry"},{"issue":"4","key":"2026092911085878900_cit33","doi-asserted-by":"publisher","first-page":"869","DOI":"10.1002\/jccs.200400131","article-title":"Chemical Constituents\nfrom Annona Glabra","volume":"51","author":"Hsieh","year":"2004","journal-title":"J. Chin. 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Technol."},{"key":"2026092911085878900_cit46","article-title":"Reference Method for Broth Dilution\nAntifungal Susceptibility Testing of Filamentous Fungi, Approved Standard,\nM38-A2","author":"Clinical and Laboratory Standards Institute (CLSI).","year":"2008","edition":"2"}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.6c05995","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/38\/57498\/68490900\/acsomega.6c05995.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/38\/57498\/68490900\/acsomega.6c05995.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T15:16:01Z","timestamp":1790694961000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/11\/38\/57498\/5428834\/Bioactive-Constituents-of-Melipona"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,12]]},"references-count":46,"journal-issue":{"issue":"38","published-online":{"date-parts":[[2026,9,12]]},"published-print":{"date-parts":[[2026,9,29]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.6c05995","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,12]]}}}