{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T01:43:34Z","timestamp":1792460614408,"version":"4.5.0"},"reference-count":51,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2020,2,10]],"date-time":"2020-02-10T00:00:00Z","timestamp":1581292800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["2015\/15431-2"],"award-info":[{"award-number":["2015\/15431-2"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Natural triterpenes exhibit a wide range of biological activities. Since this group of secondary metabolites is structurally diverse, effects may vary due to distinct biochemical interactions within biological systems. In this work, we investigated the anticancer-related activities of the quinone-methide triterpene maytenin and its derivative compound 22-\u03b2-hydroxymaytenin, obtained from Maytenus ilicifolia roots cultivated in vitro. Their antiproliferative and pro-apoptotic activities were evaluated in monolayer and three-dimensional cultures of immortalized cell lines. Additionally, we investigated the toxicity of maytenin in SCID mice harboring tumors derived from a squamous cell carcinoma cell line. Both isolated molecules presented pronounced pro-apoptotic activities in four cell lines derived from head and neck squamous cell carcinomas, including a metastasis-derived cell line. The molecules also induced reactive oxygen species (ROS) and down-regulated microRNA-27a and microRNA-20a\/miR-17-5p, corroborating with the literature data for triterpenoids. Intraperitoneal administration of maytenin to tumor-bearing mice did not lead to pronounced histopathological changes in kidney tissue, suggesting low nephrotoxicity. The wide-ranging activity of maytenin and 22-\u03b2-hydroxymaytenin in head and neck cancer cells indicates that these molecules should be further explored in plant biochemistry and biotechnology for therapeutic applications.<\/jats:p>","DOI":"10.3390\/molecules25030760","type":"journal-article","created":{"date-parts":[[2020,2,11]],"date-time":"2020-02-11T11:45:30Z","timestamp":1581421530000},"page":"760","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Anticancer Activities of the Quinone-Methide Triterpenes Maytenin and 22-\u03b2-hydroxymaytenin Obtained from Cultivated Maytenus ilicifolia Roots Associated with Down-Regulation of miRNA-27a and miR-20a\/miR-17-5p"],"prefix":"10.3390","volume":"25","author":[{"given":"Camila","family":"Hernandes","sequence":"first","affiliation":[{"name":"Albert Einstein Research and Education Institute, Hospital Israelita Albert Einstein, S\u00e3o Paulo 05652-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2604-5210","authenticated-orcid":false,"given":"Lucyene","family":"Miguita","sequence":"additional","affiliation":[{"name":"Department of Stomatology, School of Dentistry, University of S\u00e3o Paulo, S\u00e3o Paulo 05508-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Romario Oliveira","family":"de Sales","sequence":"additional","affiliation":[{"name":"Albert Einstein Research and Education Institute, Hospital Israelita Albert Einstein, S\u00e3o Paulo 05652-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elisangela de Paula","family":"Silva","sequence":"additional","affiliation":[{"name":"Albert Einstein Research and Education Institute, Hospital Israelita Albert Einstein, S\u00e3o Paulo 05652-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pedro Omori Ribeiro de","family":"Mendon\u00e7a","sequence":"additional","affiliation":[{"name":"Albert Einstein Research and Education Institute, Hospital Israelita Albert Einstein, S\u00e3o Paulo 05652-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bruna","family":"Lorencini da Silva","sequence":"additional","affiliation":[{"name":"Albert Einstein Research and Education Institute, Hospital Israelita Albert Einstein, S\u00e3o Paulo 05652-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9989-1653","authenticated-orcid":false,"given":"Maria de Fatima Guarizo","family":"Klingbeil","sequence":"additional","affiliation":[{"name":"Nuclear and Energy Research Institute IPEN-CNEN\/SP, S\u00e3o Paulo 05508-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7294-9106","authenticated-orcid":false,"given":"Monica Beatriz","family":"Mathor","sequence":"additional","affiliation":[{"name":"Nuclear and Energy Research Institute IPEN-CNEN\/SP, S\u00e3o Paulo 05508-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0982-2484","authenticated-orcid":false,"given":"Erika Bevilaqua","family":"Rangel","sequence":"additional","affiliation":[{"name":"Albert Einstein Research and Education Institute, Hospital Israelita Albert Einstein, S\u00e3o Paulo 05652-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3890-0827","authenticated-orcid":false,"given":"Luciana Cavalheiro","family":"Marti","sequence":"additional","affiliation":[{"name":"Albert Einstein Research and Education Institute, Hospital Israelita Albert Einstein, S\u00e3o Paulo 05652-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juliana da Silva","family":"Coppede","sequence":"additional","affiliation":[{"name":"Unidade de Biotecnologia, Universidade de Ribeir\u00e3o Preto, Ribeir\u00e3o Preto 14096-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7785-6785","authenticated-orcid":false,"given":"Fabio Daumas","family":"Nunes","sequence":"additional","affiliation":[{"name":"Department of Stomatology, School of Dentistry, University of S\u00e3o Paulo, S\u00e3o Paulo 05508-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3478-4718","authenticated-orcid":false,"given":"Ana Maria Soares","family":"Pereira","sequence":"additional","affiliation":[{"name":"Unidade de Biotecnologia, Universidade de Ribeir\u00e3o Preto, Ribeir\u00e3o Preto 14096-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6682-9343","authenticated-orcid":false,"given":"Patricia","family":"Severino","sequence":"additional","affiliation":[{"name":"Albert Einstein Research and Education Institute, Hospital Israelita Albert Einstein, S\u00e3o Paulo 05652-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,2,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3","DOI":"10.2174\/138527281801140121122330","article-title":"Quinone methides: Photochemical generation and its application in biomedicine","volume":"18","author":"Basaric","year":"2014","journal-title":"Curr. 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