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http://hdl.handle.net/1843/77499| Tipo: | Artigo de Periódico |
| Título: | An efficient synthesis of deoxyrhapontigenin-3-o-β-d-glucuronide, a brain-targeted derivative of dietary resveratrol, and Its precursor 4′-o-me-resveratrol |
| Autor(es): | Ângelo de Fátima Maite Loreto Docampo-Palacios Anislay Alvarez-Hernandez Giulio Maria Pasinetti Richard Arthur Dixon |
| Resumen: | Bioactive 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. |
| Asunto: | Metabolismo Alzheimer, Doença de Cromatografia liquida de alta eficiência Sistema nervoso central Fenóis Química vegetal |
| Idioma: | eng |
| País: | Brasil |
| Editor: | Universidade Federal de Minas Gerais |
| Sigla da Institución: | UFMG |
| Departamento: | ICX - DEPARTAMENTO DE QUÍMICA |
| Tipo de acceso: | Acesso Aberto |
| Identificador DOI: | https://doi.org/10.1021/acsomega.9b00722 |
| URI: | http://hdl.handle.net/1843/77499 |
| Fecha del documento: | 2019 |
| metadata.dc.url.externa: | https://pubs.acs.org/doi/10.1021/acsomega.9b00722 |
| metadata.dc.relation.ispartof: | ACS Omega |
| Aparece en las colecciones: | Artigo de Periódico |
archivos asociados a este elemento:
| archivo | Descripción | Tamaño | Formato | |
|---|---|---|---|---|
| docampo-palacios-et-al-2019-an-efficient-synthesis-of-deoxyrhapontigenin-3-o-β-d-glucuronide-a-brain-targeted-1.pdf | 1.45 MB | Adobe PDF | Visualizar/Abrir | |
| docampo-palacios-et-al-2019-correction-to-an-efficient-synthesis-of-deoxyrhapontigenin-3-o-β-d-glucuronide-a-brain (1).pdf | 208.41 kB | Adobe PDF | Visualizar/Abrir |
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