Efficient chemical synthesis of (epi)catechin glucuronides: brain-targeted metabolites for treatment of alzheimer's disease and other neurological disorders

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dc.creatorMaite Loreto Docampo-Palacios
dc.creatorAnislay Alvarez-Hernandez
dc.creatorÂngelo de Fátima
dc.creatorLuciano Morais Lião
dc.creatorGiulio Maria Pasinetti
dc.creatorRichard Arthur Dixon
dc.date.accessioned2024-10-30T22:59:27Z
dc.date.accessioned2025-09-08T23:31:07Z
dc.date.available2024-10-30T22:59:27Z
dc.date.issued2020
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.0c04512
dc.identifier.issn2470-1343
dc.identifier.urihttps://hdl.handle.net/1843/77735
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofACS Omega
dc.rightsAcesso Aberto
dc.subjectFarmacologia
dc.subjectAlzheimer, Doença de
dc.subjectUva
dc.subjectFlavonóides
dc.subjectEspectroscopia de ressonância nuclear
dc.subject.otherCatechin Glucuronides
dc.subject.otherCatechin
dc.subject.otherEpicatechin Glucuronides
dc.subject.otherEpicatechin
dc.subject.otherAlzheimer's disease
dc.titleEfficient chemical synthesis of (epi)catechin glucuronides: brain-targeted metabolites for treatment of alzheimer's disease and other neurological disorders
dc.typeArtigo de periódico
local.citation.epage30110
local.citation.issue46
local.citation.spage30095
local.citation.volume5
local.description.resumoGrape seed extract (GSE) is rich in flavonoids and has been recognized to possess human health benefits. Our group and others have demonstrated that GSE is able to attenuate the development of Alzheimer’s disease (AD). Moreover, our results have disclosed that the anti-Alzheimer’s benefits are not directly/solely related to the dietary flavonoids themselves, but rather to their metabolites, particularly to the glucuronidated ones. To facilitate the understanding of regioisomer/stereoisomer-specific biological effects of (epi)catechin glucuronides, we here describe a concise chemical synthesis of authentic standards of catechin and epicatechin metabolites 3–12. The synthesis of glucuronides 9 and 12 is described here for the first time. The key reactions employed in the synthesis of the novel glucuronides 9 and 12 include the regioselective methylation of the 4′-hydroxyl group of (epi)catechin (≤1.0/99.0%; 3′-OMe/4′-OMe) and the regioselective deprotection of the tert-butyldimethylsilyl (TBS) group at position 5 (yielding up to 79%) over the others (3, 7 and 3′ or 4′).
local.identifier.orcidhttps://orcid.org/0000-0001-5205-3989
local.identifier.orcidhttps://orcid.org/0000-0002-9962-3456
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttp://orcid.org/0000-0001-9985-2980
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.0c04512

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