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Metadados | Descrição | Idioma |
---|---|---|
Autor(es): dc.contributor | University of North Texas | - |
Autor(es): dc.contributor | Universidade Estadual Paulista (Unesp) | - |
Autor(es): dc.contributor | University of Coimbra | - |
Autor(es): dc.contributor | University of Georgia | - |
Autor(es): dc.contributor | Universidade Federal de Minas Gerais (UFMG) | - |
Autor(es): dc.contributor | The Mount Sinai School of Medicine | - |
Autor(es): dc.creator | Docampo-Palacios, Maite L. | - |
Autor(es): dc.creator | Alvarez-Hernández, Anislay | - |
Autor(es): dc.creator | Adiji, Olubu | - |
Autor(es): dc.creator | Gamiotea-Turro, Daylin [UNESP] | - |
Autor(es): dc.creator | Valerino-Diaz, Alexander B. [UNESP] | - |
Autor(es): dc.creator | Viegas, Luís P. | - |
Autor(es): dc.creator | Ndukwe, Ikenna E. | - |
Autor(es): dc.creator | De Fátima, Ângelo | - |
Autor(es): dc.creator | Heiss, Christian | - |
Autor(es): dc.creator | Azadi, Parastoo | - |
Autor(es): dc.creator | Pasinetti, Giulio M. | - |
Autor(es): dc.creator | Dixon, Richard A. | - |
Data de aceite: dc.date.accessioned | 2022-02-22T00:44:49Z | - |
Data de disponibilização: dc.date.available | 2022-02-22T00:44:49Z | - |
Data de envio: dc.date.issued | 2021-06-25 | - |
Data de envio: dc.date.issued | 2021-06-25 | - |
Data de envio: dc.date.issued | 2020-12-15 | - |
Fonte completa do material: dc.identifier | http://dx.doi.org/10.1021/acs.jafc.0c04500 | - |
Fonte completa do material: dc.identifier | http://hdl.handle.net/11449/205611 | - |
Fonte: dc.identifier.uri | http://educapes.capes.gov.br/handle/11449/205611 | - |
Descrição: dc.description | Botanical 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.description | BioDiscovery Institute Department of Biological Sciences University of North Texas | - |
Descrição: dc.description | Chemistry Institute-Araraquara UNESP-São Paulo State University | - |
Descrição: dc.description | Coimbra Chemistry Center Chemistry Department University of Coimbra | - |
Descrição: dc.description | Complex Carbohydrate Research Center University of Georgia, 315 Riverbend Rd | - |
Descrição: dc.description | Department of Chemistry Federal University of Minas Gerais | - |
Descrição: dc.description | Department of Psychiatry The Mount Sinai School of Medicine | - |
Descrição: dc.description | Chemistry Institute-Araraquara UNESP-São Paulo State University | - |
Formato: dc.format | 14790-14807 | - |
Idioma: dc.language | en | - |
Relação: dc.relation | Journal of Agricultural and Food Chemistry | - |
???dc.source???: dc.source | Scopus | - |
Palavras-chave: dc.subject | glucuronidation | - |
Palavras-chave: dc.subject | glucuronosyltransferases | - |
Palavras-chave: dc.subject | intrinsic reaction coordinate | - |
Palavras-chave: dc.subject | methoxylated quercetin | - |
Palavras-chave: dc.subject | molecular modelling | - |
Palavras-chave: dc.subject | phase II metabolites | - |
Palavras-chave: dc.subject | semi-synthesis | - |
Título: dc.title | Glucuronidation of Methylated Quercetin Derivatives: Chemical and Biochemical Approaches | - |
Tipo de arquivo: dc.type | livro digital | - |
Aparece nas coleções: | Repositório Institucional - Unesp |
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