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New Acylglycosides Flavones from Fuzhuan Brick Tea and Simulation Analysis of Their Bioactive Effects

1,2,†, 1,2,†, 1,2, 2, 3,* and 1,2,*
1
National Research Center of Engineering Technology for Utilization of Functional Ingredients from Botanicals, Hunan Agricultural University, Changsha 410128, China
2
Horticulture and Landscape College, Hunan Agricultural University, Changsha 410128, China
3
Drinkable Plant Research Institute (Tea Research Center), Guangdong Academy of Agricultural Sciences, Guangzhou 510000, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Int. J. Mol. Sci. 2019, 20(3), 494; https://doi.org/10.3390/ijms20030494
Received: 26 December 2018 / Revised: 19 January 2019 / Accepted: 20 January 2019 / Published: 24 January 2019
(This article belongs to the Section Bioactives and Nutraceuticals)
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PDF [1021 KB, uploaded 24 January 2019]
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Abstract

Four novel acylglycosides flavones (AGFs) including two quercetin acylglycosides and two kaempferol acylglycosides were isolated from Fuzhuan brick tea (FBT) as follows: quercetin 3-O-[α-l-rhamnopyranosyl (1→3)] [2-O’’-(E)-p-coumaroyl] [β-d-glucopyranosyl (1→3)-α-l-rhamnopyranosyl (1→6)]-β-d-galactoside was named as camelliquercetiside E (1), quercetin 3-O-[α-l-rhamnopyranosyl (1→3)] [2-O’’-(E)-p-coumaroyl] [α-l-rhamnopyranosyl (1→6)]-β-d-galactoside was named as camelliquercetiside F (2), kaempferol 3-O-[α-l-arabinopyranosyl (1→3)] [2-O’’-(E)-p-coumaroyl] [β-d-glucopyranosyl (1→3)-α-l-rhamnopyranosyl (1→6)]-β-d-glucoside was named as camellikaempferoside D (3), kaempferol 3-O-[α-l-arabinopyranosyl (1→3)] [2-O’’-(E)-p-coumaroyl] [α-l-rhamnopyranosyl (1→6)]-β-d-glucoside was named as camellikaempferoside E (4). Chemical structures of AGFs were identified by time-of-flight mass (TOF-MS) and NMR spectrometers (1H NMR, 13C NMR, 1H-1H COSY, HMBC and HSQC), and the MS2 fragmentation pathway of AGFs was further investigated. The inhibitory abilities of AGFs and their proposed metabolites on α-glucosidase and HMG-CoA reductase were analyzed by molecular docking simulation, and the results suggested that inhibitory activities of AGFs were significantly affected by acyl structure, number of glycosyl and conformation, and part of them had strong inhibitory activities on α-glucosidase and HMG-CoA reductase, suggesting that AGFs and their metabolites might be important ingredients that participate in the regulation of hypoglycemic and hypolipidemic effects. The results provided new AGFs and research directions for the practical study of FBT health functions in future. View Full-Text
Keywords: Fuzhuan brick tea; acylglycosides flavones; camelliquercetisides; camellikaempferosides; molecular docking simulation Fuzhuan brick tea; acylglycosides flavones; camelliquercetisides; camellikaempferosides; molecular docking simulation
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Lu, Y.; He, Y.; Zhu, S.; Zhong, X.; Chen, D.; Liu, Z. New Acylglycosides Flavones from Fuzhuan Brick Tea and Simulation Analysis of Their Bioactive Effects. Int. J. Mol. Sci. 2019, 20, 494.

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