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Use este identificador para citar o ir al link de este elemento: http://hdl.handle.net/1843/77499
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Campo DCValorIdioma
dc.creatorÂngelo de Fátimapt_BR
dc.creatorMaite Loreto Docampo-Palaciospt_BR
dc.creatorAnislay Alvarez-Hernandezpt_BR
dc.creatorGiulio Maria Pasinettipt_BR
dc.creatorRichard Arthur Dixonpt_BR
dc.date.accessioned2024-10-17T23:33:29Z-
dc.date.available2024-10-17T23:33:29Z-
dc.date.issued2019-
dc.citation.volume4pt_BR
dc.citation.issue5pt_BR
dc.citation.spage8222pt_BR
dc.citation.epage8230pt_BR
dc.identifier.doihttps://doi.org/10.1021/acsomega.9b00722pt_BR
dc.identifier.issn2470-1343pt_BR
dc.identifier.urihttp://hdl.handle.net/1843/77499-
dc.description.resumoBioactive dietary polyphenols have health benefits against a variety of disorders, but some benefits of polyphenols may be not directly related to them but rather to their metabolites. Recently, we have identified the brain-available phenol glucuronide metabolite deoxyrhapontigenin-3-O-β-d-glucuronide (5) in perfused rat brains following subacute treatment with the stilbene resveratrol (1). However, the role of such a metabolite in the neuroprotective activity of resveratrol (1) is not understood, in part due to the noncommercial availability of 5 for performing biological evaluation in animal models of Alzheimer’s disease or other neurological disorders. Here, we describe a concise chemical synthesis of deoxyrhapontigenin-3-O-β-d-glucuronide (5) and its precursor 4-O-Me-resveratrol (2), accomplished in four and six steps with 74 and 21% overall yields, respectively, starting from commercially available 3,5-dihydroxybenzaldehyde. Pivotal reactions employed in the synthesis include the palladium-catalyzed C–C coupling between 3,5-di-tert-butyldiphenylsilyloxystyrene and p-iodoanisole in the presence of tributylamine and the acid-catalyzed glucuronidation between the trichloroacetimidate-activated glucuronic acid and 4-O-Me-resveratrol.pt_BR
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológicopt_BR
dc.description.sponsorshipOutra Agênciapt_BR
dc.format.mimetypepdfpt_BR
dc.languageengpt_BR
dc.publisherUniversidade Federal de Minas Geraispt_BR
dc.publisher.countryBrasilpt_BR
dc.publisher.departmentICX - DEPARTAMENTO DE QUÍMICApt_BR
dc.publisher.initialsUFMGpt_BR
dc.relation.ispartofACS Omegapt_BR
dc.rightsAcesso Abertopt_BR
dc.subjectDeoxyrhapontigenin-3-O-beta-D-glucuronidept_BR
dc.subjectResveratrolpt_BR
dc.subjectAlzheimer's diseasept_BR
dc.subjectGlucuronidespt_BR
dc.subjectTotal synthesispt_BR
dc.subject.otherMetabolismopt_BR
dc.subject.otherAlzheimer, Doença dept_BR
dc.subject.otherCromatografia liquida de alta eficiênciapt_BR
dc.subject.otherSistema nervoso centralpt_BR
dc.subject.otherFenóispt_BR
dc.subject.otherQuímica vegetalpt_BR
dc.titleAn efficient synthesis of deoxyrhapontigenin-3-o-β-d-glucuronide, a brain-targeted derivative of dietary resveratrol, and Its precursor 4′-o-me-resveratrolpt_BR
dc.typeArtigo de Periódicopt_BR
dc.url.externahttps://pubs.acs.org/doi/10.1021/acsomega.9b00722pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-2344-5590pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0001-5205-3989pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-9962-3456pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-1524-5196pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0001-8393-9408pt_BR
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