Interdisciplinary Program in BioCosmetics, Sungkyunkwan University, 2066 Seoburo, Suwon, Gyeonggi, 16419, Republic of Korea.
Center for Nanomedicine, Wilmer Eye Institute, Johns Hopkins University School of Medicine, Baltimore, MD, 21231, USA.
Sci Rep. 2023 Mar 29;13(1):5136. doi: 10.1038/s41598-023-32361-6.
Acyl myricetins (monopropionyl-, dipropionyl-, and monooctanoyl-myricetin, termed as MP, MP, and MO, 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. MO, presenting the physicochemical superiority compared to the others, provided lowest EC value of 2.51 μM on inhibition of neutrotransmitter release and CC 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 MO has membrane fusion-arresting and anti-neuroexocytotic potential for industrial application due to its enhanced biological properties.
酰基杨梅素（单丙酰基、二丙酰基和单辛酰基杨梅素，分别称为 MP、MP 和 MO）通过杨梅素苷元的酶促或非酶促酯化反应合成。结构研究表明，B 环上 C4'位的羟基高度易酰化。与母体杨梅素相比，酰化化合物的亲脂性（根据 logP 和衰减率，从 7.4 倍增加到 26.3 倍）和氧化稳定性（从 1.9 倍增加到 3.1 倍）均得到提高。MO 与其他化合物相比具有物理化学优势，在抑制神经递质释放方面的 EC 值最低为 2.51 μM，CC 值为 59.0 μM，治疗窗口最宽。所有的杨梅素酯在鸡胚试验中均未显示出任何刺激性毒性。本研究描述了杨梅素酰化的信息，这方面尚未得到探索，并表明 MO 由于其增强的生物学特性，具有膜融合抑制和抗神经细胞外排作用，可能具有工业应用潜力。
