An efficient synthesis of deoxyrhapontigenin-3-o-β-d-glucuronide, a brain-targeted derivative of dietary resveratrol, and Its precursor 4′-o-me-resveratrol

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dc.creatorÂngelo de Fátima
dc.creatorMaite Loreto Docampo-Palacios
dc.creatorAnislay Alvarez-Hernandez
dc.creatorGiulio Maria Pasinetti
dc.creatorRichard Arthur Dixon
dc.date.accessioned2024-10-17T23:33:29Z
dc.date.accessioned2025-09-08T22:55:36Z
dc.date.available2024-10-17T23:33:29Z
dc.date.issued2019
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipOutra Agência
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.1021/acsomega.9b00722
dc.identifier.issn2470-1343
dc.identifier.urihttps://hdl.handle.net/1843/77499
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofACS Omega
dc.rightsAcesso Aberto
dc.subjectMetabolismo
dc.subjectAlzheimer, Doença de
dc.subjectCromatografia liquida de alta eficiência
dc.subjectSistema nervoso central
dc.subjectFenóis
dc.subjectQuímica vegetal
dc.subject.otherDeoxyrhapontigenin-3-O-beta-D-glucuronide
dc.subject.otherResveratrol
dc.subject.otherAlzheimer's disease
dc.subject.otherGlucuronides
dc.subject.otherTotal synthesis
dc.titleAn efficient synthesis of deoxyrhapontigenin-3-o-β-d-glucuronide, a brain-targeted derivative of dietary resveratrol, and Its precursor 4′-o-me-resveratrol
dc.typeArtigo de periódico
local.citation.epage8230
local.citation.issue5
local.citation.spage8222
local.citation.volume4
local.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.
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0001-5205-3989
local.identifier.orcidhttps://orcid.org/0000-0002-9962-3456
local.identifier.orcidhttps://orcid.org/0000-0002-1524-5196
local.identifier.orcidhttps://orcid.org/0000-0001-8393-9408
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://pubs.acs.org/doi/10.1021/acsomega.9b00722

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