Synthesis of Alkylpolyphenols Glycosides and the Inhibitory Effects on Superoxide Anion Production by Macrophages

烷基多酚苷的合成及其对巨噬细胞产生超氧阴离子的抑制作用

基本信息

批准号：
04660136
负责人：
HIROTA Mitsuru
金额：
$ 1.34万
依托单位：
Shinshu university
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1992
资助国家：
日本
起止时间：
1992 至 1993
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-04660136/
关键词：
Active oxygen Superoxide anion Macrophages Inflammation Polyphenols Glycoside

项目摘要

Superoxide anion is produced by macrophages in vivo. It is a causative agent of several diseases and also promotes inflammation. We synthesized alkylpolyphenol glycosides and examined effects of the synthetic compounds on superoxide anion production by macrophages. We also investigated anti-inflammatory activity of the synthetic compounds. Alkylcatechol xylopyranosides with various carbon chains (carbon numbers from 2 to 18), octylresorcinol xylopyranoside, octylhydroquinone xylopyranoside and octylphenol xylopyranoside were synthesized. Examining the effect of the synthetic compounds on superoxide anion production by macrophages with the modified NBT method, we found that octylcatechol xylopyranoside strongly suppressed superoxide anion production in a concentration of 50 mug/ml. Octylhydroquinone xylopyranoside and octylphenol xylopyranoside also showed similar strong activity. Using mouse ear inflammation test, we also examined anti-inflammatory activity of the synthetic compounds. Octylcatechol xylopyranoside, octylhydroquinone xylopyranoside, octylphenol xylopyranoside showed strong inhibitory activity. A sugar moiety and an alkyl chain with proper length are important structural factors for the presence of both effects on superoxide anion production and inflammation. Furthermore, we examined the reactivity of decylcatechol xylopyranoside with radicals using anti-oxidation test. It markedly suppressed autooxidation of linoleic acid in a concentration of 1Oppm. These compounds may directly react with superoxide anion (radical).

超氧阴离子由体内巨噬细胞产生。它是多种疾病的病原体，也会促进炎症。我们合成了烷基多酚糖苷，并检查了合成化合物对巨噬细胞产生超氧阴离子的影响。我们还研究了合成化合物的抗炎活性。合成了具有各种碳链（碳数为2至18）的烷基儿茶酚木吡喃糖苷、辛基间苯二酚木吡喃糖苷、辛基氢醌吡喃木糖苷和辛基苯酚吡喃木糖苷。使用改良的NBT方法检查合成化合物对巨噬细胞产生超氧阴离子的影响，我们发现辛基儿茶酚木吡喃糖苷在50μg/ml的浓度下强烈抑制超氧阴离子的产生。辛基氢醌吡喃木糖苷和辛基苯酚吡喃木糖苷也表现出类似的强活性。通过小鼠耳炎症测试，我们还检查了合成化合物的抗炎活性。辛基儿茶酚吡喃木糖苷、辛基氢醌吡喃木糖苷、辛基酚吡喃木糖苷表现出较强的抑制活性。糖部分和适当长度的烷基链是对超氧阴离子产生和炎症产生影响的重要结构因素。此外，我们使用抗氧化测试检查了癸基儿茶酚木吡喃苷与自由基的反应性。在1Oppm的浓度下它显着抑制了亚油酸的自氧化。这些化合物可以直接与超氧阴离子（自由基）反应。