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

超氧阴离子是由体内巨噬细胞产生的。它是几种疾病的病原体，也促进炎症。我们合成了烷基多酚糖苷，并检测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。合成了不同碳链(碳数为2~18)的烷基邻苯二酚木糖苷、辛基间苯二酚木糖苷、辛基对苯二酚木糖苷和辛基苯酚木糖苷。用改进的NBT法检测合成化合物对巨噬细胞产生超氧阴离子的影响，发现辛基儿茶酚木吡喃糖苷在50µg/ml时对超氧阴离子产生有强烈的抑制作用，辛基对苯二酚木吡喃糖苷和辛基酚木吡喃糖苷也表现出类似的强烈活性。通过小鼠耳部炎症实验，我们还考察了合成化合物的抗炎活性。辛基儿茶酚木吡喃糖苷、辛基对苯二酚木吡喃糖苷、辛基苯酚木吡喃糖苷具有较强的抑制活性。糖链和适当长度的烷基链是影响超氧阴离子产生和炎症的重要结构因素。此外，我们还通过抗氧化实验考察了十烷基儿茶酚吡喃糖苷与自由基的反应活性。对10ppm的亚油酸自氧化有明显的抑制作用。这些化合物可以直接与超氧阴离子(自由基)反应。

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).