498548-16-6Relevant academic research and scientific papers
Glucuronidation of Methylated Quercetin Derivatives: Chemical and Biochemical Approaches
Docampo-Palacios, Maite L.,Alvarez-Hernández, Anislay,Adiji, Olubu,Gamiotea-Turro, Daylin,Valerino-Diaz, Alexander B.,Viegas, Luís P.,Ndukwe, Ikenna E.,De Fátima, ?ngelo,Heiss, Christian,Azadi, Parastoo,Pasinetti, Giulio M.,Dixon, Richard A.
, p. 14790 - 14807 (2020/12/23)
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.
Quercetin derivative and its preparation method and application
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Paragraph 0083, (2018/01/19)
The invention discloses a quercetin derivative and a preparation method and application thereof. The preparation method comprises the following steps: firstly using dichlorodiphenylmethane to protect quercetin o-diphenol hydroxyl, combining a benzyl protection group to obtain the selectively protected quercetin derivative, and then independently reacting with dimethyl sulfate, diethyl sulfate, allyl bromide, paratoluensulfonyl chloride and acetic anhydride respectively to generate corresponding quercetin derivatives. All of the prepared derivative compounds have NRK-49F proliferation activity inhibition superior to that of quercetin. The quercetin derivatives 20a-1, 14a-1 and 23d-1 compositely replaced by methyl and p-tosyl have higher inhibition NRK-49F proliferation activity, and the inhibition ratio respectively reaches 86.33%, 78.04% and 75.91%. Thus, the currently obtained quercetin derivative compounds have obvious inhibition effect on kidney fibroblast NRK-49F proliferation.
Hemisynthesis of all the O-monomethylated analogues of quercetin including the major metabolites, through selective protection of phenolic functions
Bouktaib, Mohamed,Lebrun, Stéphane,Atmani, Aziz,Rolando, Christian
, p. 10001 - 10009 (2007/10/03)
A new methodology for the hemisynthesis of all the five O-monomethylated analogues of quercetin (3′-O-methylquercetin (isorhamnetin), 4′-O-methylquercetin (tamarixetin), 3-O-methylquercetin, 5-O-methylquercetin (azaleatin) and 7-O-methylquercetin (rhamnetin)) through sequential protection of the different phenolic functions of quercetin is reported.
