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新型长效植物调节剂2-O-β-L-glucopyranoside-4-O-methyl phloracetophenone的全合成

Total Synthesis of a Novel Long-Effect Plant Growth Regulator: 2-O-β-L-Glucopyranoside-4-O-methyl Phloracetophenone

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【作者】 陈靖李晓东孙铁民张蕾吴秀丽王金辉

【Author】 CHEN Jing;LI Xiao-dong;SUN Tie-min;ZHANG Lei;WU Xiu-li;WANG Jin-hui;College of Pharmacy,Ningxia Medical University;School of Traditional Chinese Materia Medica,Shenyang Pharmaceutical University;

【机构】 宁夏医科大学药学院沈阳药科大学中药学院

【摘要】 以β-L-(-)葡萄糖、无水醋酐及吡啶为原料,通过五步反应进行全合成,制备一种新型植物生长调节剂;β-D-葡萄糖水解酶催化下进行水解反应,研究其水解曲线。全合成产物经1H NMR鉴定为2-O-β-L-glucopyranoside-4-O-methyl phloracetophenone(1),总得率17.4%;水解实验表明domesticoside(2)可被β-D-葡萄糖水解酶水解为苷元,而化合物(1)不被水解。本法可作为一种新型长效生长调节剂的制备方法,也为体内快速被β-D-葡萄糖水解酶水解失活药物的结构修饰提供了新的思路。

【Abstract】 In this study,a novel plant growth regulator was totally synthesized by using β-L-(-) glucose,anhydrous acetic anhydride and pyridine as raw materials with five-steps of reaction. The hydrolization of the synthesized product catalyzed by β-D-glucosidase was carried out to investigate its hydrolytic curve. Results showed that the structure of the synthesized product was elucidated to be 2-O-β-L-glucopyranoside-4-O-methyl phloracetophenone( 1) by NMR with a total yield of17. 4%. The hydrolization results showed that domesticoside( 2) can be selectively hydrolyzed by β-D-glucosidase,but compound 1 cannot be hydrolyzed. Hence,it was concluded that the product synthesized in this study was a potential long-effect regulator. The reported synthetic routes can also be used as a novel idea to modify chemical drugs which might be rapidly inactivated by β-D-glucosidase.

  • 【文献出处】 天然产物研究与开发 ,Natural Product Research and Development , 编辑部邮箱 ,2013年11期
  • 【分类号】R284
  • 【被引频次】1
  • 【下载频次】75
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