Glucuronidation of Methylated Quercetin Derivatives: Chemical and Biochemical Approaches

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Autor(es): dc.contributorUniversity of North Texas-
Autor(es): dc.contributorUniversidade Estadual Paulista (Unesp)-
Autor(es): dc.contributorUniversity of Coimbra-
Autor(es): dc.contributorUniversity of Georgia-
Autor(es): dc.contributorUniversidade Federal de Minas Gerais (UFMG)-
Autor(es): dc.contributorThe Mount Sinai School of Medicine-
Autor(es): dc.creatorDocampo-Palacios, Maite L.-
Autor(es): dc.creatorAlvarez-Hernández, Anislay-
Autor(es): dc.creatorAdiji, Olubu-
Autor(es): dc.creatorGamiotea-Turro, Daylin [UNESP]-
Autor(es): dc.creatorValerino-Diaz, Alexander B. [UNESP]-
Autor(es): dc.creatorViegas, Luís P.-
Autor(es): dc.creatorNdukwe, Ikenna E.-
Autor(es): dc.creatorDe Fátima, Ângelo-
Autor(es): dc.creatorHeiss, Christian-
Autor(es): dc.creatorAzadi, Parastoo-
Autor(es): dc.creatorPasinetti, Giulio M.-
Autor(es): dc.creatorDixon, Richard A.-
Data de aceite: dc.date.accessioned2022-02-22T00:44:49Z-
Data de disponibilização: dc.date.available2022-02-22T00:44:49Z-
Data de envio: dc.date.issued2021-06-25-
Data de envio: dc.date.issued2021-06-25-
Data de envio: dc.date.issued2020-12-15-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1021/acs.jafc.0c04500-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/205611-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/205611-
Descrição: dc.descriptionBotanical 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.-
Descrição: dc.descriptionBioDiscovery Institute Department of Biological Sciences University of North Texas-
Descrição: dc.descriptionChemistry Institute-Araraquara UNESP-São Paulo State University-
Descrição: dc.descriptionCoimbra Chemistry Center Chemistry Department University of Coimbra-
Descrição: dc.descriptionComplex Carbohydrate Research Center University of Georgia, 315 Riverbend Rd-
Descrição: dc.descriptionDepartment of Chemistry Federal University of Minas Gerais-
Descrição: dc.descriptionDepartment of Psychiatry The Mount Sinai School of Medicine-
Descrição: dc.descriptionChemistry Institute-Araraquara UNESP-São Paulo State University-
Formato: dc.format14790-14807-
Idioma: dc.languageen-
Relação: dc.relationJournal of Agricultural and Food Chemistry-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectglucuronidation-
Palavras-chave: dc.subjectglucuronosyltransferases-
Palavras-chave: dc.subjectintrinsic reaction coordinate-
Palavras-chave: dc.subjectmethoxylated quercetin-
Palavras-chave: dc.subjectmolecular modelling-
Palavras-chave: dc.subjectphase II metabolites-
Palavras-chave: dc.subjectsemi-synthesis-
Título: dc.titleGlucuronidation of Methylated Quercetin Derivatives: Chemical and Biochemical Approaches-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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