化学学报 ›› 1979, Vol. 37 ›› Issue (4): 289-296. 上一篇    下一篇

论文

甘草查耳酮的分离、结构与全合成

徐任生1, 文广玲2, 江树发1, 王长根1, 蒋福祥1, 谢毓元1, 高怡生1   

  1. 1. 中国科学院上海药物研究所;
    2. 中国人民解放军军事医学科学院药理毒理研究所 北京 中国
  • 投稿日期:1979-04-28 发布日期:2013-06-03

THE ISOLATION, STRUCTURE AND TOTAL SYNTHESIS OF LICOCHALCONE

XU REN-SHENG1, WEN KUNG-LING2, JIANG SHU-FA1, WANG CHANG-GEN1, JIANG FU-XIANG1, XIE YU-YUAN1, GAO YI-SHENG1   

  1. 1. Shanghai Institute of Materia Medica, Academia Sinica;
    2. Institute of Pharmacology and Toxicology Academy of Military Medical Sciences, P. L. A., Peking China
  • Received:1979-04-28 Published:2013-06-03

从新疆产胀果甘草(Glycyrrhiza inflata But)中分得甘草查耳酮(1),C21 H22 O4,熔点136~138℃,经光谱分析及碱裂解产物的分析与合成以及1的全合成证明为一新型查耳酮——2-甲氧基-4,4'-二羟基-5-α,α-二甲烯丙基查耳酮.碱裂解产物为对羟基苯乙酮与3-α,α-二甲烯丙基-4-羟基-6-甲氧基苯甲醛(2),C13 H16 O3,熔点187~188℃.后者经甲基化、氢化与高锰酸钾氧化得3-α,α-二甲丙基-4,6-二甲氧基苯甲酸(3),C14 H20 O4,熔点124~125℃.1,2,3的结构均经合成证明.2-甲氧基-4-羟基-苯甲醛与溴代异戊烯作用得异戊烯醚(4),再经Claisen 重排得2.2与对羟基苯乙酮缩合成1.探索了提高 Claisen 重排产率的较佳条件.

Gan-Cao(Glycyrrhiza uralrrnsis Fisch),a famous Chinese traditional medicinal herb,is generally used in our country as an antitoaio,antitnssive and expectorant agent.Six different species of Glycyrrhiza are available in China antiussive all are spited for medicinal use.Among which the roots of Glycyrrhiza vrcflatd Bat,natively grown in Autonomous Region Xin jiang,has the finest quality and thus attracted our attention to study its chemical constituents.A new type of chaloone(1),named licochaloone,was isolated from its chloroform extract followed by chromatography successively on polyamide and aluminum oxide columns.Its structure was elucidated as 2-methoxy-4,4'-dihydrogy-5-α,α-dimethyl allyl chaloone(1) by alkaline degradation,spectral analyses and total synthesis.