Glucuronidation of methylated quercetin derivatives: chemical and biochemical approaches

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dc.creatorMaite Loreto Docampo-Palacios
dc.creatorParastoo Azadi
dc.creatorGiulio Maria Pasinetti
dc.creatorRichard Arthur Dixon
dc.creatorAnislay Alvarez-Hernandez
dc.creatorOlubu Adiji
dc.creatorDaylin Gamiotea-Turro
dc.creatorAlexander Barbaro Valerino-Diaz
dc.creatorLuís Pedro Viegas
dc.creatorIkenna E. Ndukwe
dc.creatorÂngelo de Fátima
dc.creatorChristian Heiss
dc.date.accessioned2024-10-29T23:49:29Z
dc.date.accessioned2025-09-08T23:47:35Z
dc.date.available2024-10-29T23:49:29Z
dc.date.issued2020
dc.description.sponsorshipOutra Agência
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.1021/acs.jafc.0c04500
dc.identifier.issn0021-8561
dc.identifier.urihttps://hdl.handle.net/1843/77712
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of Agricultural and Food Chemistry
dc.rightsAcesso Restrito
dc.subjectUva
dc.subjectAnions
dc.subjectFlavonóides
dc.subjectCromatografia liquida de alta eficiencia
dc.subjectMisturas
dc.subjectSolventes
dc.subject.otherMethoxylated quercetin
dc.subject.otherGlucuronidation
dc.subject.otherGlucuronosyltransferases
dc.subject.otherPhase II metabolites
dc.titleGlucuronidation of methylated quercetin derivatives: chemical and biochemical approaches
dc.typeArtigo de periódico
local.citation.epage14807
local.citation.issue50
local.citation.spage14790
local.citation.volume68
local.description.resumoBotanical supplements derived from grapes are functional in animal model systems for the amelioration of neurological conditions, including cognitive impairment. Rats fed with grape extracts accumulate 3′-O-methyl-quercetin-3-O-β-d-glucuronide (3) in their brains, suggesting 3 as a potential therapeutic agent. To develop methods for the synthesis of 3 and the related 4′-O-methyl-quercetin-7-O-β-d-glucuronide (4), 3-O-methyl-quercetin-3′-O-β-d-glucuronide (5), and 4′-O-methyl-quercetin-3′-O-β-d-glucuronide (6), which are not found in the brain, we have evaluated both enzymatic semisynthesis and full chemical synthetic approaches. Biocatalysis by mammalian UDP-glucuronosyltransferases generated multiple glucuronidated products from 4′-O-methylquercetin, and is not cost-effective. Chemical synthetic methods, on the other hand, provided good results; 3, 5, and 6 were obtained in six steps at 12, 18, and 30% overall yield, respectively, while 4 was synthesized in five steps at 34% overall yield. A mechanistic study on the unexpected regioselectivity observed in the quercetin glucuronide synthetic steps is also presented.
local.identifier.orcidhttps://orcid.org/0000-0001-5205-3989
local.identifier.orcidhttps://orcid.org/0000-0002-1524-5196
local.identifier.orcidhttps://orcid.org/0000-0001-8393-9408
local.identifier.orcidhttps://orcid.org/0000-0002-9962-3456
local.identifier.orcidhttps://orcid.org/0000-0001-8293-4461
local.identifier.orcidhttp://orcid.org/0000-0001-7600-8429
local.identifier.orcidhttp://orcid.org/0000-0002-6368-3086
local.identifier.orcidhttp://orcid.org/0000-0003-2312-990X
local.identifier.orcidhttps://orcid.org/0000-0003-2412-6970
local.identifier.orcidhttp://orcid.org/0000-0003-3010-695X
local.identifier.orcidhttp://orcid.org/0000-0003-1118-8953
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://pubs.acs.org/doi/10.1021/acs.jafc.0c04500#

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