化学学报 ›› 2005, Vol. 63 ›› Issue (1): 44-50. 上一篇    下一篇

研究论文

藏药五脉绿绒蒿碱结构和性质的理论研究

易平贵*1,胡瑞定2,俞庆森2,商志才2   

  1. (1湖南科技大学化学化工学院 湘潭 411201)
    (2浙江大学化学系 杭州 310027)
  • 投稿日期:2004-06-04 修回日期:2004-09-12 发布日期:2010-12-10
  • 通讯作者: 易平贵

Theoretical Study on the Structures and Properties of a Tibetan Medicine Meconoquintupline

YI Ping-Gui*1, HU Rui-Ding2, YU Qing-Sen2, SHANG Zhi-Cai2   

  1. (1 School of Chemistry and Chemical Engineering, Hunan University of Science and Technology,
    Xiangtan 411201)
    (2 Department of Chemistry, Zhejiang University, Hangzhou 310027)
  • Received:2004-06-04 Revised:2004-09-12 Published:2010-12-10

五脉绿绒蒿碱是一种从藏药五脉绿绒蒿中提取并已确认结构的新的生物碱. 采用密度泛函理论(DFT)和从头算(ab initio)方法, 在HF/6-31G*和B3LYP/6-31G*水平下全优化计算了该化合物的分子几何构型和电子结构; 依据Onsager自恰反应场(SCRF)模型考察了五脉绿绒蒿碱在氯仿、丙酮、二甲亚砜及水等溶剂中的溶剂化作用; 基于气相优化结构进行了B3LYP/6-31G*振动分析与红外光谱计算, 进一步按照统计力学原理求得了298~1500 K温度范围内该化合物的热力学性质. 此外, 还讨论了五脉绿绒蒿碱的分子结构与药效的关系.

关键词: 五脉绿绒碱, 密度泛函理论, 从头计算, 分子几何, 溶剂化作用, 红外光谱, 热力学性质

Meconoquintupline is a new alkaloid, the molecular structure of which has been determined, and may be extracted from Meconopis quintuplinervia Regel, a traditional Tibetan medicine. In this work, a full optimal calculation on the molecular geometry and electronic structure of meconoquintupline has been performed using ab initio and density functional theory (DFT) methods at HF/6-31G* and B3LYP/6-31G* level, respectively. The solvent effects of meconoquintupline have also been investigated based on Onsager self-consistent reaction field (SCRF) model in chloroform, acetone, DMSO and water. On the basis of the vibration analysis and statistical thermodynamic theory, the IR spectrum and thermodynamic parameters (enthalpy, entropy and heat capacity) for the titled compound from 298 to 1500 K have been obtained according to the B3LYP/6-31G* optimized geometry in gas phase. At the same time, the relationship between molecular structure and medicine efficacy for meconoquintupline has also been analyzed.

Key words: meconoquintupline, density functional theory (DFT), ab initio, molecular geometry, solvent effect, IR spectrum, thermodynamic property