{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T05:03:09Z","timestamp":1792040589990,"version":"4.4.0"},"reference-count":40,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2020,3,27]],"date-time":"2020-03-27T00:00:00Z","timestamp":1585267200000},"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":["2019\/11563-2"],"award-info":[{"award-number":["2019\/11563-2"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","award":["2014\/01283-9"],"award-info":[{"award-number":["2014\/01283-9"]}],"id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The research of natural products has allowed for the discovery of biologically relevant compounds inspired by plant secondary metabolites, which contributes to the development of many chemotherapeutic drugs used in cancer treatment. Psidium guajava leaves present a diverse phytochemical composition including flavonoids, phenolics, meroterpenoids, and triterpenes as the major bioactive constituents. Guajadial, a caryophyllene-based meroterpenoid, has been studied for potential anticancer effects tested in tumor cells and animal experimental models. Moreover, guajadial has been reported to have a mechanism of action similar to tamoxifen, suggesting this compound as a promisor phytoestrogen-based therapeutic agent. Herein, the anti-estrogenic action and anti-proliferative activity of guajadial is reported. The enriched guajadial fraction was obtained by sequential chromatographic techniques from the crude P. guajava dichloromethane extract showing promising anti-proliferative activity in vitro with selectivity for human breast cancer cell lines MCF-7 and MCF-7 BUS (Total Growth Inhibition = 5.59 and 2.27 \u00b5g\u00b7mL\u22121, respectively). Furthermore, evaluation of anti-estrogenic activity in vivo was performed demonstrating that guajadial enriched fraction inhibited the proliferative effect of estradiol on the uterus of pre-pubescent rats. These results suggest a relationship between anti-proliferative and anti-estrogenic activity of guajadial, which possibly acts in tumor inhibition through estrogen receptors due to the compounds structural similarity to tamoxifen.<\/jats:p>","DOI":"10.3390\/molecules25071525","type":"journal-article","created":{"date-parts":[[2020,4,3]],"date-time":"2020-04-03T05:55:16Z","timestamp":1585893316000},"page":"1525","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Anti-Estrogenic Activity of Guajadial Fraction, from Guava Leaves (Psidium guajava L.)"],"prefix":"10.3390","volume":"25","author":[{"given":"Jaqueline Moraes","family":"Bazioli","sequence":"first","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, University of Campinas, 13083-859 Campinas, SP, Brazil"},{"name":"Institute of Chemistry, University of Campinas, P.O.Box 6154, 13083-970 Campinas, SP, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonas Henrique","family":"Costa","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Campinas, P.O.Box 6154, 13083-970 Campinas, SP, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Larissa","family":"Shiozawa","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, University of Campinas, 13083-859 Campinas, SP, Brazil"},{"name":"Postgraduate program in Dentistry, Piracicaba Dental School, University of Campinas, 13 414-903, Piracicaba, SP, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0844-8702","authenticated-orcid":false,"given":"Ana L\u00facia Tasca Gois","family":"Ruiz","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, University of Campinas, 13083-859 Campinas, SP, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mary Ann","family":"Foglio","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, University of Campinas, 13083-859 Campinas, SP, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jo\u00e3o Ernesto de","family":"Carvalho","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, University of Campinas, 13083-859 Campinas, SP, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,3,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3389\/fphar.2019.01614","article-title":"Phytochemicals in Cancer Treatment: From Preclinical Studies to Clinical Practice","volume":"10","author":"Choudhari","year":"2020","journal-title":"Front. 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