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Synthesis of ellagic acid glucoside using glucansucrase from Leuconostoc and characterization of this glucoside as a functional neuroprotective agent.

ABSTRACT: Ellagic acid glucoside was synthesized via transglucosylation using sucrose and glucansucrase derived from Leuconostoc mesenteroides B-512 FMCM. After such enzymatic synthesis, the product was purified by 50% ethyl acetate fraction and C18 column chromatography. Modification of ellagic acid glucoside was verified by LC-MS/MS at m/z 485.1 (M + Na)^- and m/z 531.1 (M + 3Na)^-. The yield of ellagic acid glucoside was 69% (3.47 mM) by response surface methodology using 150 mM sucrose, 300 mU/mL glucansucrase, and 5 mM ellagic acid. The synthesized ellagic acid glucoside showed improved water solubility, up to 58% higher brain nerve cell (SH-SY5Y) protective effect, threefold higher cortisol reducing effect, and fourfold stronger inhibitory effect on acetylcholinesterase (AChE) than ellagic acid. These results indicate that ellagic acid glucoside could be used as a neuroprotective agent.

SUBMITTER: Yu H

PROVIDER: S-EPMC8295447 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:PurposeAlzheimer's disease (AD) is a multifaceted neurodegenerative disease. To target simultaneously multiple pathological processes involved in AD, natural-origin compounds with unique characteristics are promising scaffolds to develop novel multi-target compounds in the treatment of different neurodegenerative disease, especially AD. In this study, novel chromone-lipoic acid hybrids were prepared to find a new multifunctional lead structure for the treatment of AD.MethodsChromone-lipoic acid hybrids were prepared through click reaction and their neuroprotection and anticholinesterase activity were fully evaluated. The anti-amyloid aggregation, antioxidant and metal-chelation activities of the best compound were also investigated by standard methods to find a new multi-functional agent against AD.ResultsThe primary biological screening demonstrated that all compounds had significant neuroprotection activity against H2O2-induced cell damage in PC12 cells. Compound 19 as the most potent butyrylcholinesterase (BuChE) inhibitor (IC50 = 7.55 μM) having significant neuroprotection activity as level as reference drug was selected for further biological evaluations. Docking and kinetic studies revealed non-competitive mixed-type inhibition of BuChE by compound 19. It could significantly reduce formation of the intracellular reactive oxygen species (ROS) and showed excellent reducing power (85.57 mM Fe+2), comparable with quercetin and lipoic acid. It could also moderately inhibit Aβ aggregation and selectively chelate with copper ions in 2:1 M ratio.ConclusionCompound 19 could be considered as a hopeful multifunctional agent for the further development gainst AD owing to the acceptable neuroprotective and anti-BuChE activity, moderate anti-Aβ aggregation activity, outstanding antioxidant activity as well as selective copper chelation ability. A new chromone-lipoic acid hybrid was synthesized as anti-Alzheimer agent with BuChE inhibitory activity, anti-Aβ aggregation, metal-chelation and antioxidant properties.

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Synthesis of ellagic acid glucoside using glucansucrase from Leuconostoc and characterization of this glucoside as a functional neuroprotective agent.

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