高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (2): 226.doi: 10.7503/cjcu20170576

• 有机化学 • 上一篇    下一篇

八元瓜环与乔松素的主客体作用及对乔松素性质的影响

练小卫1,2, 黄净净2, 陶朱2, 周清娣3, 张前军2(), 卫钢4()   

  1. 1. 贵州大学精细化工中心
    2. 贵州省大环化学及超分子化学重点实验室,贵州大学化学与化工学院, 贵阳 550025
    3. 悉尼大学化学学院, 新南威尔士州 2006
    4. 澳大利亚联邦科学与工业组织(CSIRO), 新南威尔士州 2070
  • 收稿日期:2017-08-24 出版日期:2018-02-10 发布日期:2018-01-10
  • 作者简介:联系人简介: 张前军, 女, 博士, 教授, 主要从事天然有机化学方面的研究. E-mail: qianjunzhang@126.com ; 卫钢, 男, 博士, 教授, 博士生导师, 主要从事超分子化学方面的研究. E-mail: Gang.Wei@csiro.au
  • 基金资助:
    教育部春晖计划项目(批准号: Z2015003)资助

Host-guest Interaction Between Cucurbit[8]uril and Pinocembrin and Its Influence on the Properties of Pinocembrin

LIAN Xiaowei1,2, HUANG Jingjing2, TAO Zhu2, ZHOU Qingdi3, ZHANG Qianjun2,*(), WEI Gang4,*()   

  1. 1. Research and Development Center of Fine Chemicals
    2. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Chemistry and Chemical Engineering College, Guizhou University, Guiyang 550025, China
    3. College of Chemistry, The University of Sydney, NSW 2006, Australia
    4. CSIRO Manufacturing, PO Box 218, NSW 2070, Australia
  • Received:2017-08-24 Online:2018-02-10 Published:2018-01-10
  • Contact: ZHANG Qianjun,WEI Gang E-mail:qianjunzhang@126.com;Gang.Wei@csiro.au

摘要:

利用核磁共振波谱、 紫外吸收光谱和热重分析等方法研究了八元瓜环(Q[8])对乔松素(PCB)的包结作用; 采用紫外吸收光谱法研究了Q[8]对PCB水溶性、 抗氧化活性及在人工胃肠液中稳定性和累积释放量的影响. 结果表明, PCB与Q[8]形成了摩尔比为1∶2的主客体包结配合物(PCB-Q[8]), PCB位于2个瓜环的端口之间, 其稳定结合常数为5.00×109 L2/mol2. 当c(Q[8])=90 μmol/L时, 可使PCB在水中的溶解度增加4.3倍; PCB-Q[8]包合物和PCB均对2,2-联氮基-双-(3-乙基苯并噻唑-6-磺酸)二铵盐(ABTS)自由基具有较好的清除作用, IC50值分别为4.3和3.2 μmol/L. 在人工胃液中, PCB和PCB-Q[8]包合物都较稳定; 而在人工肠液中, PCB于72 h后全部降解, PCB-Q[8]包合物则基本未降解, 表明Q[8]增强了PCB在人工肠液中的稳定性; Q[8]的介入提高了PCB在人工胃液和人工肠液中的累积释放量, 其数值分别提高了5倍和2倍.

关键词: 乔松素, 八元瓜环, 包结配合物, 抗氧化活性

Abstract:

The inclusion interaction between cucurbit [8] uril(Q[8]) and pinocembrin(PCB) was investigated by means of nuclear magnetic resonance spectrometer(NMR), UV-Visible spectrophotometer(UV-Vis) and differential thermal analysis(DTA). The results showed that PCB formed a molar ratio 1∶2 inclusion complex with Q[8] and located between the ports of the two rings. The stable binding constant is 5.00×109 L2/mol2. The effects of Q[8] on water solubility, stability, antioxidant activity and cumulative release of PCB were investigated by means of UV absorption spectroscopy. Phase solubility experiments showed that the solubility of PCB could be increased 4.3 fold by interacting when c(Q[8])=90 μmol/L. Both PCB-Q[8] and PCB had good scavenging effect on 2'-azinobis-(3-ethylbenzthiazoline-6-sulphonate)(ABTS) free radicals, with IC50 values of 4.3 and 3.2 μmol/L, respectively. PCB and PCB-Q[8] were stable in the artificial gastric juice, and PCB was degraded completely after 72 h in the artificial intestinal fluid, but the degradation of PCB-Q[8] was hardly found. Q[8] increased the accumulation degree of PCB in artificial gastric and intestinal fluid by 5 and 2 times, respectively.

Key words: Pinocembrin, Cucurbit[8]uril, Inclusion complex, Antioxidant activity

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