红曲黄色素降低胆固醇能力的DFT研究
Cholesterol-lowering capability of monascus pigments based on DFT calculation
刘轶 1吕庆章1
作者信息
- 1. 河南师范大学化学化工学院,河南省新乡市,453007
- 折叠
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(△G).这些分子的水解△G数据顺序与它们的降低胆固醇的能力一致,△G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.
Abstract
We presume that the hydroxy-acid forms of monascin and ankaflavin obtained through the catalytic hydrolysis of their γ-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 B3LYP-D3(BJ)/6-31 l+G(d,p) level has been used to calculate the hydrolytic activation free energies (△G) of monascin,ankaflavin,rubropunctamine,rubropunctatin and three amino acids (threonine,leucine and glycine) derivatives of rubropunctatin.The order of the calculated data of △Gs agrees with the sequence of their practical cholesterol-lowering capability.The △G 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.
关键词
红曲素/安卡红曲黄素/降胆固醇机理/DFT/活化能Key words
monascin/ankaflavin/cholesterol-lowering mechanism/DFT/activation free energy引用本文复制引用
基金项目
国家自然科学基金资助项目(21472036)
出版年
2019
NETL
NSTL
万方数据