Synthesis and physicochemical characterization of acyl myricetins as potential anti-neuroexocytotic agents

Sora Cho, Byoungjae Kong, Younghun Jung, Jonghyeok Shin, Myungseo Park, Woo Jae Chung, Choongjin Ban, Dae Hyuk Kweon

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Acyl myricetins (monopropionyl-, dipropionyl-, and monooctanoyl-myricetin, termed as MP1, MP2, and MO1, respectively) were synthesized through enzymatic or non-enzymatic esterification reaction of myricetin aglycone. Structure study indicated the hydroxyl group at C4′ in B-ring was highly susceptible to acylation. Over its parental myricetin, acylated compounds showed enhanced lipophilicity (from 7.4- to 26.3-fold) and oxidative stability (from 1.9- to 3.1-fold) on the basis of logP and decay rate, respectively. MO1, presenting the physicochemical superiority compared to the others, provided lowest EC50 value of 2.51 μM on inhibition of neutrotransmitter release and CC50 value of 59.0 μM, leading to widest therapeutic window. All myricetin esters did not show any irritation toxicity when assessed with a chicken embryo assay. This study describes information on acylation of myricetin that has not yet been explored, and suggests that MO1 has membrane fusion-arresting and anti-neuroexocytotic potential for industrial application due to its enhanced biological properties.

Original languageEnglish
Article number5136
JournalScientific Reports
Volume13
Issue number1
DOIs
StatePublished - Dec 2023

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