黄芩素和黄芩苷抗氧化活性的密度泛函理论研究
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- 英文论文题名：Density functional theory calculations on antioxidation activity of Baicalein and Baicalin
- 论文作者：刘靖丽 ; 张拴 ; 孟庆华 ; 权彦
- 英文论文作者：Jingli Liu ; Shuan Zhang ; Qinghua Meng ; Yan Quan ; College of Pharmacy ; Shaan Xi University of Chinese Medicine
- 年：2016
- 作者机构：陕西中医药大学药学院;
- 论文关键词：黄芩素 ; 黄芩苷 ; 抗氧化活性 ; 密度泛函理论
- 会议召开时间：2016-07-01
- 会议录名称：中国化学会第30届学术年会摘要集-第十八分会：电子结构理论方法的发展与应用
- 语种：中文
- 分类号：R284
- 学会代码：ZGHY
- 会议名称：中国化学会第30届学术年会-第十八分会 ; 电子结构理论方法的发展与应用
- 会议地点：中国辽宁大连
- 主办单位：中国化学会
- 学会名称：中国化学会
- 页数：2
- 文件大小：161k
- 原文格式：D
- 会议级别：全国
摘要
黄芩素是黄芩苷的初级代谢产物,二者的分子结构差别仅在于7-位取代基,前者为酚羟基而后者为糖苷。本文采用密度泛函理论B3LYP方法在6-31G(d,p)水平上对黄芩素和黄芩苷进行了优化计算,从分子的几何结构、酚羟基氢原子上的NBO电荷、酚羟基解离能、HOMO和LUMO能级以及其能级差△E(LUMO-HOMO)等方面分析了两种化合物清除自由基的活性。C5位的酚羟基为黄芩素和黄芩苷的最大可能活性位点,C7位酚羟基也具有一定的活性,可以增加分子本身的抗氧化活性。C5位或C7位上酚羟基氢原子带正电荷越大、酚羟基的解离能越小、E(LUMO-HOMO)越小、HOMO能级相对越高,分子的抗氧化活性越高。糖苷取代C7位酚羟基上的H原子,可以提高HOMO、LUMO的轨道能级,但是分子失去了7位酚羟基,从而降低了黄芩苷分子的抗氧化活性。结果表明,黄芩素的抗氧化活性大于黄芩苷的抗氧化活性。
Baicalein, a primary metabolite of baicalin, differs from its mother compound merely by the 7-substituent(i.e.it possesses a phenolic hydroxyl(7-OH) instead o f a glucuronic acid).The molecular structures of baicalein and baicalin are calculated by using the Density Functional Theory B3 LYP method with 6-31G( d,p) basis set.It is found that the more positive charge on H atom of C5-OH or C7-OH,the lower bond dissociation energy of the hydroxyl,the higher energy level of the HOMO and the smaller △E( LUMO-HOMO) are of benefit to the antioxidant activity of baicalein and baicalin.The C5-OH is the highest active site of baicalein and baicalin,while the C7-OH is also an active site but possessing lower activity relatively.The substitution of the H atom of C7-OH by glucoside decreases the antioxidant activity for losing the phenolic hydroxyl in baicalin.
Baicalein, a primary metabolite of baicalin, differs from its mother compound merely by the 7-substituent(i.e.it possesses a phenolic hydroxyl(7-OH) instead o f a glucuronic acid).The molecular structures of baicalein and baicalin are calculated by using the Density Functional Theory B3 LYP method with 6-31G( d,p) basis set.It is found that the more positive charge on H atom of C5-OH or C7-OH,the lower bond dissociation energy of the hydroxyl,the higher energy level of the HOMO and the smaller △E( LUMO-HOMO) are of benefit to the antioxidant activity of baicalein and baicalin.The C5-OH is the highest active site of baicalein and baicalin,while the C7-OH is also an active site but possessing lower activity relatively.The substitution of the H atom of C7-OH by glucoside decreases the antioxidant activity for losing the phenolic hydroxyl in baicalin.
引文
[1]Kaufmann J A,Blickford P C,Taglialatela G.Neuroreport,2002,13(15):1917.
[2]梁然,陈长慧,艾希成,张建平.波谱学杂志,2010,27(1):132.
[3]荣玉芝,王正武,吴金鸿,赵波.食品与药品,2012,14(9):317.
[4]张鑫,杨英杰,吕庆章.化学研究与应用,2012,24(11):1662.
[5]高志强,徐强,宋仲容,王林.化学世界,2008,7,439.
[6]蒋司同,聂长明,石春雨,林英武.2010,24(4):102.
[2]梁然,陈长慧,艾希成,张建平.波谱学杂志,2010,27(1):132.
[3]荣玉芝,王正武,吴金鸿,赵波.食品与药品,2012,14(9):317.
[4]张鑫,杨英杰,吕庆章.化学研究与应用,2012,24(11):1662.
[5]高志强,徐强,宋仲容,王林.化学世界,2008,7,439.
[6]蒋司同,聂长明,石春雨,林英武.2010,24(4):102.