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http://hdl.handle.net/1843/77712| Type: | Artigo de Periódico |
| Title: | Glucuronidation of methylated quercetin derivatives: chemical and biochemical approaches |
| Authors: | Maite Loreto Docampo-Palacios Parastoo Azadi Giulio Maria Pasinetti Richard Arthur Dixon Anislay Alvarez-Hernandez Olubu Adiji Daylin Gamiotea-Turro Alexander Barbaro Valerino-Diaz Luís Pedro Viegas Ikenna E. Ndukwe Ângelo de Fátima Christian Heiss |
| Abstract: | 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. |
| Subject: | Uva Anions Flavonóides Cromatografia liquida de alta eficiencia Misturas Solventes |
| language: | eng |
| metadata.dc.publisher.country: | Brasil |
| Publisher: | Universidade Federal de Minas Gerais |
| Publisher Initials: | UFMG |
| metadata.dc.publisher.department: | ICX - DEPARTAMENTO DE QUÍMICA |
| Rights: | Acesso Restrito |
| metadata.dc.identifier.doi: | https://doi.org/10.1021/acs.jafc.0c04500 |
| URI: | http://hdl.handle.net/1843/77712 |
| Issue Date: | 2020 |
| metadata.dc.url.externa: | https://pubs.acs.org/doi/10.1021/acs.jafc.0c04500# |
| metadata.dc.relation.ispartof: | Journal of Agricultural and Food Chemistry |
| Appears in Collections: | Artigo de Periódico |
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