{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,15]],"date-time":"2026-08-15T03:14:18Z","timestamp":1786763658523,"version":"build-2736575974"},"reference-count":57,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2019,4,16]],"date-time":"2019-04-16T00:00:00Z","timestamp":1555372800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["633738"],"award-info":[{"award-number":["633738"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["0226165"],"award-info":[{"award-number":["0226165"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Annona purpurea, known in Mexico as \u201ccabeza de negro\u201d or \u201cilama\u201d, belongs to the Annonaceae family. Its roots are employed in folk medicine in several regions of Mexico. Taking that information into account, a chemical and biological analysis of the components present in the roots of this species was proposed. Our results demonstrated that the dichloromethane (DCM) extract was exclusively constituted by a mixture of five new acetogenins named annopurpuricins A\u2013E (1\u20135). These compounds have an aliphatic chain of 37 carbons with a terminal \u03b1,\u03b2 unsaturated \u03b3-lactone. Compounds 1 and 2 belong to the adjacent bis-THF (tetrahydrofuran) \u03b1-monohydroxylated type, while compounds 3 and 4 belong to the adjacent bis-THF \u03b1,\u03b1\u2019-dihydroxylated type; only compound 5 possesses a bis-epoxide system. Complete structure analysis was carried out by spectroscopy and chemical methods. All compounds were evaluated for their antiproliferative activity on three human tumor cell lines (MSTO-211H, HeLa and HepG2). Compounds 1\u20134 inhibited significantly the growth of HeLa and HepG2 cells, showing GI50 values in the low\/subnanomolar range, while 5 was completely ineffective under the tested conditions. The investigation of the mechanism of action responsible for cytotoxicity revealed for the most interesting compound 1 the ability to block the complex I activity on isolated rat liver mitochondria (RLM).<\/jats:p>","DOI":"10.3390\/ijms20081870","type":"journal-article","created":{"date-parts":[[2019,4,17]],"date-time":"2019-04-17T03:02:01Z","timestamp":1555470121000},"page":"1870","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Cytotoxic Acetogenins from the Roots of Annona purpurea"],"prefix":"10.3390","volume":"20","author":[{"given":"Gustavo Alejandro","family":"Hern\u00e1ndez-Fuentes","sequence":"first","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad de Colima, Carretera Colima-Coquimatl\u00e1n km 9, 28400 Coquimatl\u00e1n, Colima, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"A\u00edda Nelly","family":"Garc\u00eda-Arg\u00e1ez","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze del Farmaco, Universit\u00e0 degli Studi di Padova, Via F. Marzolo 5, 35131 Padova, Italy"},{"name":"Fondazione per la Biologia e la Medicina della Rigenerazione T.E.S.-Tissue Engineering and Signalling Onlus, Via F. Marzolo, 13, 35131 Padova, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana Lilia","family":"Peraza Campos","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad de Colima, Carretera Colima-Coquimatl\u00e1n km 9, 28400 Coquimatl\u00e1n, Colima, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9848-862X","authenticated-orcid":false,"given":"Iv\u00e1n","family":"Delgado-Enciso","sequence":"additional","affiliation":[{"name":"Facultad de Medicina, Universidad de Colima, Av. Universidad 333, Las V\u00edboras, 28040 Colima, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8678-9289","authenticated-orcid":false,"given":"Roberto","family":"Mu\u00f1iz-Valencia","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad de Colima, Carretera Colima-Coquimatl\u00e1n km 9, 28400 Coquimatl\u00e1n, Colima, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6951-9837","authenticated-orcid":false,"given":"Francisco Javier","family":"Mart\u00ednez-Mart\u00ednez","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad de Colima, Carretera Colima-Coquimatl\u00e1n km 9, 28400 Coquimatl\u00e1n, Colima, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antonio","family":"Toninello","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Biomediche, Universit\u00e0 degli Studi di Padova, Via G. Colombo 3, 35121, Padova, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6670-6311","authenticated-orcid":false,"given":"Zeferino","family":"G\u00f3mez-Sandoval","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad de Colima, Carretera Colima-Coquimatl\u00e1n km 9, 28400 Coquimatl\u00e1n, Colima, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2561-9689","authenticated-orcid":false,"given":"Juan Pablo","family":"Mojica-S\u00e1nchez","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad de Colima, Carretera Colima-Coquimatl\u00e1n km 9, 28400 Coquimatl\u00e1n, Colima, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9828-9388","authenticated-orcid":false,"given":"Lisa","family":"Dalla Via","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze del Farmaco, Universit\u00e0 degli Studi di Padova, Via F. Marzolo 5, 35131 Padova, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4375-6217","authenticated-orcid":false,"given":"Hortensia","family":"Parra-Delgado","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad de Colima, Carretera Colima-Coquimatl\u00e1n km 9, 28400 Coquimatl\u00e1n, Colima, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,4,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"434","DOI":"10.1055\/s-2006-960143","article-title":"Antiparasitic activity of Annona muricata and Annona cherimolia seeds","volume":"57","author":"Bories","year":"1991","journal-title":"Planta Med."},{"key":"ref_2","first-page":"106","article-title":"A preliminary study of the sedative effects of Annona muricata (sour sop)","volume":"28","author":"Bourne","year":"1979","journal-title":"West Indian Med. 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