{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T20:58:06Z","timestamp":1790542686708,"version":"4.1.0"},"reference-count":57,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,9,10]],"date-time":"2026-09-10T00:00:00Z","timestamp":1788998400000},"content-version":"vor","delay-in-days":9,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"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":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Four principal fractions (\n                    <jats:bold>I<\/jats:bold>\n                    \u2010\n                    <jats:bold>IV<\/jats:bold>\n                    ) were obtained from the\n                    <jats:italic>Melipona beecheii<\/jats:italic>\n                    propolis. GC\u2010MS analysis of these fractions allowed us to recognize 11 pentacyclic triterpenes (PTs), fraction\n                    <jats:bold>I<\/jats:bold>\n                    [\u03b2\u2010amyrin acetate (\n                    <jats:bold>1<\/jats:bold>\n                    ), germanicol acetate (\n                    <jats:bold>2<\/jats:bold>\n                    ), moretenol acetate (\n                    <jats:bold>3<\/jats:bold>\n                    ) and 24\u2010methylencycloartan\u20103\u2010ol acetate (\n                    <jats:bold>4<\/jats:bold>\n                    )]; fraction\n                    <jats:bold>II<\/jats:bold>\n                    [marsformosanone (\n                    <jats:bold>5<\/jats:bold>\n                    ), \u03b2\u2010amyrenone (\n                    <jats:bold>6<\/jats:bold>\n                    ), germanicone (\n                    <jats:bold>7<\/jats:bold>\n                    ) and lupenone (\n                    <jats:bold>8<\/jats:bold>\n                    )]; fraction\n                    <jats:bold>III<\/jats:bold>\n                    [\u03b2\u2010amyrin (\n                    <jats:bold>9<\/jats:bold>\n                    ) and, glutinol (\n                    <jats:bold>10<\/jats:bold>\n                    )]; and fraction\n                    <jats:bold>IV<\/jats:bold>\n                    [\n                    <jats:bold>9<\/jats:bold>\n                    and \u03b1\u2010amyrin (\n                    <jats:bold>11<\/jats:bold>\n                    )]. This is the first time that triterpenes\n                    <jats:bold>7<\/jats:bold>\n                    and\n                    <jats:bold>10<\/jats:bold>\n                    are reported in the propolis of\n                    <jats:italic>M. beecheii<\/jats:italic>\n                    . Three semisynthetic derivatives were prepared: the reduction of fraction\n                    <jats:bold>II<\/jats:bold>\n                    and the acetylation and oxidation of fraction\n                    <jats:bold>IV<\/jats:bold>\n                    . The ethanolic extract of propolis and fraction\n                    <jats:bold>III<\/jats:bold>\n                    presented the highest free DPPH radical scavenging capacity at 53.89 \u00b1 8.39% and 47.77 \u00b1 0.91%, respectively, using a concentration of 10\u00a0mg\/mL. In contrast, the reducing power of Fe (III) analysis showed a strong reducing power of Fe(III) for all fractions and their derivatives with an EC\n                    <jats:sub>50<\/jats:sub>\n                    = 0.8\u20131.0\u00a0mg\/mL.\n                  <\/jats:p>","DOI":"10.1002\/cbdv.71689","type":"journal-article","created":{"date-parts":[[2026,9,10]],"date-time":"2026-09-10T10:26:31Z","timestamp":1789035991000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Antioxidant Activities of Pentacyclic Triterpenes From\n                    <i>Melipona beecheii<\/i>\n                    Propolis and Their Semisynthetic Derivatives"],"prefix":"10.1002","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3821-8385","authenticated-orcid":false,"given":"Aar\u00f3n","family":"Santana\u2010Hern\u00e1ndez","sequence":"first","affiliation":[{"name":"Divisi\u00f3n de Estudios de Posgrado e Investigaci\u00f3n Tecnol\u00f3gico Nacional de M\u00e9xico\/ ITM\u00e9rida  M\u00e9rida Yucat\u00e1n M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1532-2910","authenticated-orcid":false,"given":"Alejandro","family":"Yam\u2010Puc","sequence":"additional","affiliation":[{"name":"Divisi\u00f3n de Estudios de Posgrado e Investigaci\u00f3n Tecnol\u00f3gico Nacional de M\u00e9xico\/ ITM\u00e9rida  M\u00e9rida Yucat\u00e1n M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3640-7307","authenticated-orcid":false,"given":"Pamela","family":"Yah\u2010Nahuat","sequence":"additional","affiliation":[{"name":"Divisi\u00f3n de Estudios de Posgrado e Investigaci\u00f3n Tecnol\u00f3gico Nacional de M\u00e9xico\/ ITM\u00e9rida  M\u00e9rida Yucat\u00e1n M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3497-4319","authenticated-orcid":false,"given":"Mar\u00eda","family":"Vargas\u2010Vargas","sequence":"additional","affiliation":[{"name":"Divisi\u00f3n de Estudios de Posgrado e Investigaci\u00f3n Tecnol\u00f3gico Nacional de M\u00e9xico\/ ITM\u00e9rida  M\u00e9rida Yucat\u00e1n M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4337-0031","authenticated-orcid":false,"given":"Roc\u00edo","family":"Borges\u2010Arg\u00e1ez","sequence":"additional","affiliation":[{"name":"Unidad de Biotecnolog\u00eda  M\u00e9rida Yucat\u00e1n M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-6913-7785","authenticated-orcid":false,"given":"Julio","family":"Aguiar\u2010Pech","sequence":"additional","affiliation":[{"name":"Unidad de Biotecnolog\u00eda  M\u00e9rida Yucat\u00e1n M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7773-190X","authenticated-orcid":false,"given":"Jes\u00fas","family":"Ram\u00f3n\u2010Sierra","sequence":"additional","affiliation":[{"name":"Divisi\u00f3n de Estudios de Posgrado e Investigaci\u00f3n Tecnol\u00f3gico Nacional de M\u00e9xico\/ ITM\u00e9rida  M\u00e9rida Yucat\u00e1n M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2881-2110","authenticated-orcid":false,"given":"Elizabeth","family":"Ortiz\u2010V\u00e1zquez","sequence":"additional","affiliation":[{"name":"Divisi\u00f3n de Estudios de Posgrado e Investigaci\u00f3n Tecnol\u00f3gico Nacional de M\u00e9xico\/ ITM\u00e9rida  M\u00e9rida Yucat\u00e1n M\u00e9xico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,10]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/oxygen2040030"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/fsn3.3217"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-031-86954-9_32"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phymed.2019.153098"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1186\/s43014-023-00146-z"},{"key":"e_1_2_9_7_1","first-page":"1","article-title":"Propolis and Geopropolis From Stingless Bees as Sources of Natural Antioxidant Compounds: A Systematic Review and Meta\u2010Analysis","volume":"64","author":"Rossa L. 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