{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,22]],"date-time":"2025-05-22T04:11:02Z","timestamp":1747887062812,"version":"3.41.0"},"reference-count":24,"publisher":"Oxford University Press (OUP)","issue":"6","license":[{"start":{"date-parts":[[2025,3,10]],"date-time":"2025-03-10T00:00:00Z","timestamp":1741564800000},"content-version":"vor","delay-in-days":2,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["24K17837"],"award-info":[{"award-number":["24K17837"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2025,5,21]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>We synthesized a vitetrifolin analog in which the A-ring was replaced with a benzene ring, in 6 steps from commercially available 2-methyl-1-tetralone. Similarly to vitetrifolin D, this analog suppressed the phorbol ester\u2013induced epithelial-mesenchymal transition. This tetralone-based structural simplification strategy is expected to be applicable to studies on not only vitetrifolins but also other halimane-type diterpenoids.<\/jats:p>","DOI":"10.1093\/bbb\/zbaf030","type":"journal-article","created":{"date-parts":[[2025,3,10]],"date-time":"2025-03-10T01:23:06Z","timestamp":1741569786000},"page":"805-810","source":"Crossref","is-referenced-by-count":0,"title":["Six-step synthesis and epithelial-mesenchymal transition\u2013inhibitory activity of a tetralone-based vitetrifolin analog"],"prefix":"10.1093","volume":"89","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0591-3429","authenticated-orcid":false,"given":"Yusuke","family":"Hanaki","sequence":"first","affiliation":[{"name":"Faculty of Agriculture, Kagawa University Department of Applied Biological Science, , Kagawa ,","place":["Japan"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yasunori","family":"Sugiyama","sequence":"additional","affiliation":[{"name":"Faculty of Agriculture, Kagawa University Department of Applied Biological Science, , Kagawa ,","place":["Japan"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9217-5507","authenticated-orcid":false,"given":"Ryo C","family":"Yanagita","sequence":"additional","affiliation":[{"name":"Faculty of Agriculture, Kagawa University Department of Applied Biological Science, , Kagawa ,","place":["Japan"]}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"286","published-online":{"date-parts":[[2025,3,8]]},"reference":[{"key":"2025052105572049700_bib1","doi-asserted-by":"publisher","first-page":"1012","DOI":"10.1039\/c3mb25567k","article-title":"Hh signaling inhibitors from Vitex negundo; naturally occurring inhibitors of the GLI1-DNA complex","volume":"9","author":"Arai","year":"2013","journal-title":"Mol BioSyst"},{"key":"2025052105572049700_bib2","doi-asserted-by":"publisher","first-page":"5669","DOI":"10.1016\/S0040-4039(00)00885-6","article-title":"Total synthesis of (\u00b1)-nakamurol-A and its 13-epimer: tentative assignment of the C-13 relative configuration","volume":"41","author":"Bonjoch","year":"2000","journal-title":"Tetrahedron Lett"},{"key":"2025052105572049700_bib3","doi-asserted-by":"publisher","first-page":"6686","DOI":"10.1021\/acs.joc.6b01332","article-title":"Stereoselective synthesis of 1-tuberculosinyl adenosine: a virulence factor of Mycobacterium tuberculosis","volume":"81","author":"Buter","year":"2016","journal-title":"J Org Chem"},{"key":"2025052105572049700_bib4","doi-asserted-by":"publisher","first-page":"571","DOI":"10.1002\/ptr.7330","article-title":"Traditional uses, phytochemistry, and pharmacology of genus Vitex (Lamiaceae)","volume":"36","author":"Das","year":"2022","journal-title":"Phytother Res"},{"key":"2025052105572049700_bib5","doi-asserted-by":"publisher","first-page":"7400","DOI":"10.1021\/jo034838r","article-title":"Synthesis of (-)-nakamurol A and assignment of absolute configuration of diterpenoid (+)-nakamurol A","volume":"68","author":"D\u00edaz","year":"2003","journal-title":"J Org Chem"},{"key":"2025052105572049700_bib6","doi-asserted-by":"publisher","first-page":"105248","DOI":"10.1016\/j.fitote.2022.105248","article-title":"Diterpenoids with \u03b1-glucosidase inhibitory activities from the fruits of Vitex trifolia","volume":"161","author":"Djimabi","year":"2022","journal-title":"Fitoterapia"},{"key":"2025052105572049700_bib7","doi-asserted-by":"publisher","first-page":"103","DOI":"10.4103\/phrev.phrev_22_17","article-title":"Pharmacological and therapeutic effects of Vitex agnus-castus L.: a review","volume":"12","author":"Farzaei","year":"2018","journal-title":"Pharmacogn Rev"},{"key":"2025052105572049700_bib8","doi-asserted-by":"publisher","first-page":"101512","DOI":"10.1016\/j.rechem.2024.101512","article-title":"A new labdane-type diterpenoid from leaves of Vitex rotundifolia","volume":"7","author":"Hanaki","year":"2024","journal-title":"Results Chem"},{"key":"2025052105572049700_bib9","doi-asserted-by":"publisher","first-page":"103","DOI":"10.1248\/bpbreports.6.3_103","article-title":"Cell morphology-based screening identified vitetrifolin D from Vitex rotundifolia as an inhibitor of phorbol ester-induced downregulation of E-cadherin in HHUA endometrial cells","volume":"6","author":"Hanaki","year":"2023","journal-title":"BPB Reports"},{"key":"2025052105572049700_bib10","doi-asserted-by":"publisher","first-page":"1417","DOI":"10.1093\/bbb\/zbac136","article-title":"12-O-tetradecanoylphorbol 13-acetate promotes proliferation and epithelial-mesenchymal transition in HHUA cells cultured on collagen type I gel: a feasible model to find new therapies for endometrial diseases","volume":"86","author":"Hanaki","year":"2022","journal-title":"Biosci Biotechnol Biochem"},{"key":"2025052105572049700_bib11","doi-asserted-by":"publisher","first-page":"1778","DOI":"10.1002\/chem.200305647","article-title":"Titanocene-catalyzed cascade cyclization of epoxypolyprenes: straightforward synthesis of terpenoids by free-radical chemistry","volume":"10","author":"Justicia","year":"2004","journal-title":"Chem Eur J"},{"key":"2025052105572049700_bib12","doi-asserted-by":"publisher","first-page":"2351","DOI":"10.1021\/jacs.3c13398","article-title":"Alkene hydrobenzylation by a single catalyst that mediates iterative outer-sphere steps","volume":"146","author":"Kong","year":"2024","journal-title":"J Am Chem Soc"},{"key":"2025052105572049700_bib13","doi-asserted-by":"publisher","first-page":"203","DOI":"10.1021\/cb800065s","article-title":"Ester bonds in prodrugs","volume":"3","author":"Lavis","year":"2008","journal-title":"ACS Chem Biol"},{"key":"2025052105572049700_bib14","doi-asserted-by":"publisher","first-page":"6010","DOI":"10.1016\/j.bmcl.2013.08.004","article-title":"Anti-inflammatory constituents from the fruits of Vitex rotundifolia","volume":"23","author":"Lee","year":"2013","journal-title":"Bioorg Med Chem Lett"},{"key":"2025052105572049700_bib15","doi-asserted-by":"publisher","first-page":"6050","DOI":"10.1021\/acs.orglett.9b02204","article-title":"Access to benzylic quaternary carbons from aromatic ketones","volume":"21","author":"Li","year":"2019","journal-title":"Org Lett"},{"key":"2025052105572049700_bib16","doi-asserted-by":"publisher","first-page":"2626","DOI":"10.1021\/ol100832h","article-title":"Synthesis of (\u00b1)-nosyberkol (isotuberculosinol, revised structure of edaxadiene) and (\u00b1)-tuberculosinol","volume":"12","author":"Maugel","year":"2010","journal-title":"Org Lett"},{"key":"2025052105572049700_bib17","first-page":"1","article-title":"Black cohosh and chasteberry: herbs valued by women for centuries","volume":"6","author":"Mayo","year":"1998","journal-title":"Clin Nutr Insight"},{"year":"2025","author":"Molinspiration Cheminformatics","key":"2025052105572049700_bib18"},{"key":"2025052105572049700_bib19","doi-asserted-by":"publisher","first-page":"1220","DOI":"10.1248\/cpb.49.1220","article-title":"Four new halimane-type diterpenes, vitetrifolins D-G, from the fruit of Vitex trifolia","volume":"49","author":"Ono","year":"2001","journal-title":"Chem Pharm Bull"},{"key":"2025052105572049700_bib20","doi-asserted-by":"publisher","first-page":"6103","DOI":"10.1002\/ejoc.201402213","article-title":"Progress in catalytic asymmetric protonation","volume":"2014","author":"Oudeyer","year":"2014","journal-title":"Eur J Org Chem"},{"key":"2025052105572049700_bib21","doi-asserted-by":"publisher","first-page":"13764","DOI":"10.1021\/acs.joc.9b01996","article-title":"Mimicking halimane synthases: monitoring a cascade of cyclizations and rearrangements from epoxypolyprenes","volume":"84","author":"Quilez\u00a0Del\u00a0Moral","year":"2019","journal-title":"J Org Chem"},{"key":"2025052105572049700_bib22","doi-asserted-by":"publisher","first-page":"955","DOI":"10.1039\/C8NP00016F","article-title":"Halimane diterpenoids: sources, structures, nomenclature and biological activities","volume":"35","author":"Roncero","year":"2018","journal-title":"Nat Prod Rep"},{"key":"2025052105572049700_bib23","doi-asserted-by":"publisher","first-page":"367","DOI":"10.1055\/s-0028-1112211","article-title":"Cytotoxic terpenoids from the fruits of Vitex trifolia L","volume":"75","author":"Wu","year":"2009","journal-title":"Planta Med"},{"key":"2025052105572049700_bib24","doi-asserted-by":"publisher","first-page":"41679","DOI":"10.18632\/oncotarget.16472","article-title":"Epithelial-to-mesenchymal transition in the development of endometriosis","volume":"8","author":"Yang","year":"2017","journal-title":"Oncotarget"}],"container-title":["Bioscience, Biotechnology, and Biochemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/academic.oup.com\/bbb\/advance-article-pdf\/doi\/10.1093\/bbb\/zbaf030\/62352524\/zbaf030.pdf","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/bbb\/article-pdf\/89\/6\/805\/62352524\/zbaf030.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/bbb\/article-pdf\/89\/6\/805\/62352524\/zbaf030.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,21]],"date-time":"2025-05-21T09:57:33Z","timestamp":1747821453000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/bbb\/article\/89\/6\/805\/8064770"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3,8]]},"references-count":24,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2025,3,8]]},"published-print":{"date-parts":[[2025,5,21]]}},"URL":"https:\/\/doi.org\/10.1093\/bbb\/zbaf030","relation":{},"ISSN":["1347-6947"],"issn-type":[{"type":"electronic","value":"1347-6947"}],"subject":[],"published-other":{"date-parts":[[2025,6]]},"published":{"date-parts":[[2025,3,8]]}}}