摘要
甘草次酸是甘草中的活性成分之一,具有广泛的药理活性,尤其是其衍生物具有显著的抗炎、抗过敏、止痛、抗癌、抗乙肝病毒、抗艾滋病毒等活性。但临床上长期应用该类药物常伴有假醛固酮增多症的副作用,限制了其在临床上的广泛应用。药理研究表明:甘草次酸的11-位羰基还原后将会降低其副作用,为了给11-脱氧甘草次酸的结构衍生化及构效关系研究提供了依据,本研究以18β-甘草次酸为原料,采用经典的克莱门森还原制备了11-脱氧甘草次酸,通过IR、~1H NMR、^(13)C NMR、HRMS等方法对其进行了表征。接着应用量子化学中的密度泛涵理论(DFT),在B3LYP/6-31G(d)水平下优化了其空间构型,计算了其结构参数、单点能、前线轨道能量和Mulliken电荷布局分布。
Glycyrrhetinic acid is one of the most important active ingredients in the Licorice root, possessing the broad spectrum biological activities, especially its derivatives showing the remarkable anti-inflammatory, anti-allergic, anti-nociceptive, anti-tumor, anti-hepatic and anti-HIV viruses. However, a side-effect （induction of edema and hypertension） has been observed in patients given high doses of glycyrrhetinic acid and its derivatives for prolonged period in clinical. It has been reported that this side-effect will be reduced while reduction the 11-ketone group of glycyrrhetinic acid. In order to provide the scientific evidence for the structure modification and QSAR of 11-deoxylglycyrrhetinic acid, 11-deoxylglycyrrhetinic acid was synthesized by Clemmensen reduction using 18[3-glycyrrhetinic acid as starting material, and confirmed by IR, 1^H NMR,13^C NMR and MS. Subsequently, the structure was optimized and the bond lengths, bond angles, dihedral angels, charge distribution, molecular total energy, HOMO and LUMO energy were calculated at DFT-B3LYP/6-31G（d） basis.
出处
《计算机与应用化学》
CAS
CSCD
北大核心
2011年第10期1325-1329,共5页
Computers and Applied Chemistry
基金
宁夏自然科学基金资助项目(NZ10108)
宁夏医科大学面上项目(XM201010)和宁夏医科大学博士建设开放基金(KF2010-12)资助
