摘要
假设与他汀类的功能机理一样,红曲黄色素monascin和ankaflavin的羟基酸式结构是通过γ-内酯环催化水解获得的,那么内酯环水解的活化能高低直接影响其降低胆固醇的能力大小。水解模型采取了包含6个水分子的连续分子簇模型,采用密度泛函理论方法,在B3LYP-D3(BJ)/6-311+G(d,p)水平计算了monascin,ankaflavin,rubropunctamine,rubropunctatin以及rubropunctatin的三个氨基酸(苏氨酸,亮氨酸和甘氨酸)衍生物的水解活化自由能(ΔG)。这些分子的水解ΔG数据顺序与它们的降低胆固醇的能力一致,ΔG数据表明两个红曲黄色素monascin和ankaflavin有更好的降低胆固醇的能力,氨基酸衍生物降低了红曲色素的降脂能力,该研究结果表明可以使用红曲黄色素monascin和ankaflavin来降低人体胆固醇的水平,还建议合成新的它们的类似物用于治疗高胆固醇症。
We presume that the hydroxy-acid forms of monascin and ankaflavin obtained through the catalytic hydrolysis of theirγ-lactone rings have the same functional mechanism as statins.The hydrolytic activation barriers of lactone rings would influence their cholesterol-lowering capability,a ClusterContinuum Model including up to six explicit water molecules at B3 LYP-D3(BJ)/6-311+G(d,p)level has been used to calculate the hydrolytic activation free energies(ΔG)of monascin,ankaflavin,rubropunctamine,rubropunctatin and three amino acids(threonine,leucine and glycine)derivatives of rubropunctatin.The order of the calculated data ofΔGs agrees with the sequence of their practical cholesterol-lowering capability.TheΔG data indicate monascin and ankaflavin,the two yellow pigments,have distinct advantage in cholesterol-lowering capability.And the amino acid substitution would weaken the cholesterol-lowering capability of the monascus pigments.This suggests people to utilize monascin and ankaflavin and find or synthesis their analogues which could lower the cholesterol levels more effectively.
作者
刘轶
吕庆章
LIU Yi;LV Qingzhang(School of Chemistry and Chemical Engineering,He‘nan Normal University,Xinxiang 453007,He’nan,China)
出处
《计算机与应用化学》
CAS
北大核心
2019年第3期274-285,共12页
Computers and Applied Chemistry
基金
National Natural Science Foundation of China(21472036)~~
关键词
红曲素
安卡红曲黄素
降胆固醇机理
DFT
活化能
monascin
ankaflavin
cholesterol-lowering mechanism
DFT
activation free energy
