13459-13-7Relevant academic research and scientific papers
Regiospecific synthesis of three quercetin O-β-glucosides of N-acetylglucosamine
Cao, Zhiling,Chen, Jing,Zhu, Dandan,Yang, Zongnan,Teng, Wenqi,Liu, Gaofeng,Liu, Bing,Tao, Chuanzhou
, p. 189 - 193 (2018)
The regiospecific synthesis of three quercetin O-β-glucosides of N-acetylglucosamine has been achieved in good yield. Selective di- and tri-O-benzylation of quercetin followed by O-glycosylation with 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride under phase-transfer catalysis conditions yielded, after deacetylation and debenzylation, 3-, 3′- and 4′-glycosylated quercetin.
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.
Flavone glycoside derivatives, and preparation method and application thereof
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, (2016/10/08)
The invention discloses flavone glycoside derivatives which are compounds with a general structural formula I shown in the description, and pharmaceutically acceptable salts or hydrates thereof, including racemates, optical isomers and epimers of the deri
Stereoselective Synthesis of Quercetin 3-O-Glycosides of 2-Amino-2-Deoxy-d-Glucose under Phase Transfer Catalytic Conditions
Cao, Zhiling,Qu, Yingying,Zhou, Jiexing,Liu, Weiwei,Yao, Guowei
, p. 28 - 40 (2015/10/20)
This article describes the stereoselective synthesis of quercetin 3-O-glycosides of 2-amino-2-deoxy-d-glucose. Efficient 1,2-trans-glycosylation of protected quercetin with N-acetyl-protected 2-amino-2-deoxy-d-glucose chloride was achieved under phase transfer catalytic conditions in a 0.15 M aqueous K2CO3/chloroform system using tetrabutylammonium bromide as the catalyst. On the contrary, glycosylation with the N-phthalimido-protected bromide donor under the same conditions was found to give predominantly 1,2-cis-glycoside product.
Synthesis of quercetin 3-O-[6"-O-(trans-p-coumaroyl)]-β-D- Glucopyranoside
Ren, Xuhong,Shen, Liu-Lan,Muraoka, Osamu,Cheng, Maosheng
, p. 119 - 131 (2012/01/13)
This report describes the efficient synthesis of quercetin 3-O-[6"-O-(trans-pcoumaroyl)]- β-D-glucopyranoside 1 (isoquercitrin coumarate), an acylated quercetin glycoside possessing antihypertensive, antidiabetic, and tyrosinase inhibitory activities. The synthesis is initiated from commercially available quercetin via regioselective benzylation of quercetin to produce 4', 7-di-O-benzylquercetin (4). Through 4, 1 was successfully achieved via selective β-glycosylation of the 3-OH, acylation of 6"-OH, and finally debenzylation via catalytic transfer hydrogenation. Taylor & Francis Group, LLC.
STRUCTURAL ASPECTS OF ANTHOCYANIN-FLAVONOID COMPLEX FORMATION AND ITS ROLE IN PLANT COLOR
Chen, Lao-Jer,Hrazdina, Geza
, p. 297 - 304 (2007/10/02)
Key Word Index - Anthocyanin; flavonoid glycosides; synthesis; complex formation; plant color; spectral properties. The complex formation of flavonoids with anthocyanins, resulting in increase in both absorbance and in a bathochromic shift of the visible absorption maximum of the latter, is based mainly on hydrogen bond formation between the carbonyl group of the anthocyanin anhydrobase and aromatic hydroxyl groups of the complex-forming flavonoids.The larger the number of hydroxyl groups in the flavonoid molecule, the strongr the complex formation.The presence of a 3-hydroxyl group in the flavonoid molecule has little effect on the complex-forming ability.The nature of the sugar substituent of the complex-forming flavonoid compound has no influence on the reaction.The 5-hydroxyl group of flavonoids is strongly bound by intramolecular hydrogen bond to the 4-carbonyl and does not participate in the complex formation.The most important hydroxyl group in the flavonoid molecule is one in the 7-position.Unsaturation at C2-C3 in the heterocyclic ring is an important factor for complex formation.Aromatic hydroxyl groups in the flavonoid system alone cannot account for all the complex-forming ability, suggesting additional involvment by electrostatic forces and configurational or steric effects.
