应用氧化偶联反应制备二苯乙烯类低聚化合物  

PREPARATION OF STILBENE OLIGOMER BY OXIDATIVE COUPLING REACTION

作　　者：周立新[1] 林茂[1] 

机构地区：[1]中国医学科学院

出　　处：《药学学报》2000年第9期669-674,共6页Acta Pharmaceutica Sinica

基　　金：国家自然科学基金!(395 70 836 )

摘　　要：目的　以异丹叶大黄素 (isorhapontigenin)为反应物、FeCl3 为氧化剂进行氧化偶联反应 ,以期获得多种偶合产物 ,供观察其类似物的活性。方法　以FeCl3 为氧化剂进行反应 ,用硅胶低压正相柱色谱、反相色谱以及半制备高压液相色谱等手段对反应物进行分离 ,经IR ,UV ,EI MS ,FAB MS ,1HNMR ,13CNMR及13C 1HCOSY ,HMBC等光谱方法鉴定化合物的结构。结果　获得 10种异丹叶大黄素聚合物 ,其中以射干素B(4 ) ,双异丹叶大黄素A(2 )和B(3)为反应主产物 ,它们得率分别是 9 5 7% ,2 8 15 %和 6 31%。结论　双异丹叶大黄素A(2 )和B(3)为新化合物 ,初步药理筛选结果表明 ,双异丹叶大黄素A和B 。AIM Study the oxidative coupling reaction of isorhapontigenin using FeCl 3 as oxidant in order to obtain multiple isorhapontigenin oligomer for pharmacological tests. METHODS The products were isolated by silica gel chromatography, flash chromatography ODS Rp 18 and semipreparative HPLC. The structures of three major products have been established by spectroscopic evidence (IR, UV, EI MS, FAB MS, 1HNMR , 13 CNMR , 13 C 1H COSY, HMBC spectrum). RESULTS Shegansu B(4), bisisorhapontigenin A(2) and B(3) were obtained as major products and determined as isorhapontigenin dimers which resulted from β 6,β 4 and β 5′ coupling, respectively.CONCLUSION Bisisorhapontigenin A and B were new compounds. Pharmacological tests showed that shegansu B and bisisorhapontigenin A had inhibitiory effect on leukotriene B4 and antogonistic action on leukotriene D4 receptor respectively. Bisisorhapontigenin B showed inhibitiory effect of TNF α.

关 键 词：二苯乙烯低聚体 异丹叶大黄素 氧化偶联反应 

分 类 号：R284[医药卫生—中药学]