Development of bioactive functions in Hydrangeae dulcis folium. VI. Syntheses of thunberginols A and F and their 3'-deoxy-derivatives using regiospecific lactonization of stilbene carboxylic acid: structures and inhibitory activity on histamine release of hydramacrophyllols A and B.
Development of bioactive functions in Hydrangeae dulcis folium. VI. Syntheses of thunberginols A and F and their 3'-deoxy-derivatives using regiospecific lactonization of stilbene carboxylic acid: structures and inhibitory activity on histamine release of hydramacrophyllols A and B.
复制标题
绣球花生物活性功能的开发。
DOI：
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发表时间：
1996
影响因子：
1.7
通讯作者：
H. Matsuda
中科院分区：
文献类型：
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作者：
M. Yoshikawa;H. Shimada;N. Yagi;N. Murakami;H. Shimoda;J. Yamahara;H. Matsuda
2-羧基二苯乙烯在氯化铜作用下发生内酯化反应，区域专一性地得到五元内酯，而用N-溴代丁二酰亚胺和阳极氧化进行溴化内酯化反应，得到六元内酯。利用这些区域特异性内酯化反应作为关键步骤，从叶甜素和八仙花烯醇合成了抗过敏和抗菌的异香豆素和苯亚甲基苯酞类thunberginol A和F及其3 '-脱氧类似物。从甜绣球中分离得到两个苯酞类化合物，分别命名为HydramacrophyllolsA和B，并根据理化和化学证据确定了它们的立体结构，其中包括应用氯化铜内酯化法从绣球烯醇合成HydramacrophyllolsA和B。此外，水大叶醇A和B对抗原抗体反应诱导的大鼠腹腔渗出细胞组胺释放有抑制作用。
Lactonization reaction of 2-carboxystilbene mediated by copper(II) chloride proceeded regiospecifically to give the five-membered lactone, while the bromolactonizations using N-bromosuccinimide and anodic oxidation were found to furnish the six-membered lactone. Using these regiospecific lactonization reactions as a key step, antiallergic and antimicrobial isocoumarins and the benzylidenephthalides thunberginols A and F and their 3'-deoxyanalogs were synthesized from phyllodulcin and hydrangenol. Two phthalides called hydramacrophyllols A and B were isolated from Hydrangeae Dulcis Folium and their stereostructures were determined on the basis of physicochemical and chemical evidence, which included the syntheses of hydramacrophyllols A and B from hydrangenol by the application of the lactonization method using copper(II) chloride. In addition, hydramacrophyllols A and B were found to exhibit an inhibitory effect on the histamine release from rat peritoneal exudate cells induced by antigen-antibody reaction.