高等学校化学学报 ›› 2005, Vol. 26 ›› Issue (12): 2247.

• 研究论文 • 上一篇    下一篇

双甲基化大豆苷元磺酸盐的合成、晶体结构及活性研究

张尊听1,2,王秋亚1,贺云1,王小兵1,薛东1,郑建斌2   

  1. 1.陕西师范大学化学与材料科学学院,西安710062;2.西北大学分析科学研究所,西安710069
  • 收稿日期:2004-12-08 出版日期:1905-03-14 发布日期:1905-03-14
  • 通讯作者: 张尊听(1965年出生),男,教授,主要从事有机分析及新药开发研究.E-mail:zhangzt@snnu.edu.cn
  • 基金资助:

    陕西省自然科学基金(批准号:2004B06)资助.

Syntheses,Crystal Structures and Biological Activity of Bimethylation Daidzein Sulfonates

ZHANG Zun-Ting1,2*, WANG Qiu-Ya1, HE Yun1, WANG Xiao-Bing1, XUE Dong1,ZHENG Jian-Bin2   

  1. 1.  School of Chemistry and Materials Science,  Shaanxi Normal University,  Xi′an 710062,  China;
    2.  Institute of Analytical Science,  Northwest University,  Xi′an 710069,  China
  • Received:2004-12-08 Online:1905-03-14 Published:1905-03-14
  • Contact: ZHANG Zun-Ting;E-mail:zhangzt@snnu.edu.cn

摘要:

以大豆苷元为原料合成了强水溶性异黄酮类化合物7,4′-二甲氧基异黄酮-3′-磺酸钠(1)和7,4′-二甲氧基异黄酮-3′-磺酸铜(2).X射线单晶衍射分析表明,化合物1的分子组成为[Na(H2O)2](C17H13O4SO3),Na的配位数为6,且相邻钠离子以7,4′-二甲氧基异黄酮-3′-磺酸根氧原子桥连,与两个磺酸根的3个氧原子和1个S原子组成六元环,六元环通过Na—O配位键彼此稠合,在晶体结构中形成延伸的锯齿状聚合八面体配位钠离子链;这些钠离子链之间又通过配位水与配位水、磺酸根之间的氢键作用自组装成二维结构的超分子离子聚合物.化合物2的分子组成为[Cu(H2O)6](C17H13O4SO3)2·8H2O,Cu(Ⅱ)位于对称中心上.[Cu(H2O)6]2+,C17H13O4SO-3和H2O之间存在多种氢键;并且异黄酮环反平行排列存在π…π的堆积作用.氢键和π…π的堆积作用使化合物2自组装成三维结构的超分子.抗缺氧缺血活性试验结果表明,它们的抗缺氧缺血活性比大豆苷元的高.

关键词: 大豆苷元;7,4′-二甲氧基异黄酮-3′-磺酸钠;7,4′-二甲氧基异黄酮-3′-磺酸铜;抗缺氧缺血活性, 大豆苷元, 7, 4'-二甲氧基异黄酮-3'-磺酸钠, 7, 4'-二甲氧基异黄酮-3'-磺酸铜, 抗缺氧缺血活性

Abstract:

The water soluble derivatives of daidzein sodium 7,4′-bimethoxylisoflavone-3′-sulfonate(1) and copper(Ⅱ) 7,4′-bimethoxylisoflavone-3′-sulfonate(2)  were synthesized and their structures were characterized by IR,  NMR,  ESI-MS and X-ray diffraction analyses.  In the crystal structure of compound 1,  each sodium ion is six-coordinated by oxygens from the methoxyl and suflo-group of 7,4′-bimethoxylisoflavone-3′-sulfonate and H2O.  Two adjacent sodium ions were bridged by the oxygen atoms from suflo-group and a six-membered ring is formed.  The six-membered ring consists of two sodium ions,  three oxygen atoms from two suflo-groups and a sulfur atom.  The Na—O bonds of adjacent rings are paralleled with each other and form an one-dimensional zigzag sodium polyion chain along  axis c of the unit cell.  The sodium ions chains are also connected by the hydrogen bonds among coordination water molecules,  between coordination water molecules and oxygen from suflo-group.  The coordination interaction,  hydrogen bonds and the electrostatic interaction between sodium ion and —SO-3 made compound 1 assemble supramolecular ion polymer with two-dimensional structure.  The crystal of compound 2 consists of [Cu(H2O)6]2+,  C17H13O4SO-3 and H2O.  Cu(Ⅱ) is at the symmetry center of structure of compound 2 and octahedrally coordinated by six water molecule. [Cu(H2O)6]2+,  C17H13O4SO-3 and H2O form several kinds of hydrogen bonds.  The distance of 0.358 2 nm between anti-parallel isoflavone rings shows a π…π stacking interaction.  The hydrogen bonds and π…π stacking interaction lead to supramolecular formation with three-dimensional network structure.  The biological activities of resistance to hypoxia and anoxemia were tested,  the results show that the biological activities of resistance to hypoxia and anoxemia of compounds 1 and 2 were better than that of daidzein.

Key words: Daidzein; Sodium 7,4′-bimethoxylisoflavone-3′-sulfonate; Copper(Ⅱ) 7,4′-bimethoxylisoflavone-3′-sulfonate;  Crystal structure; Resistance to hypoxia and anoxemia, Daidzein, Sodium 7,4'-bimethoxylisoflavone-3'-sulfonate, Copper(Ⅱ) 7,4'-bimethoxylisoflavone-3'-sulfonate, Crystal structure, Resistance to hypoxia and anoxemia

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