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十员环异喹啉生物碱在植物中广为存在,是一类具有药物学意义的生物碱.一些研究表明,这类生物碱分子的十员环内氮原子和14-(或13-)位羰基碳原子之间有一种类酰胺的相互作用,具有成环的趋向;但对成环的条件及成环后的稳定性均未最终证明.我们对这类生物碱中的原阿片碱(protopine,1)及其盐酸盐的结构进行了研究,并通过 UV、IR、1~(13)CNMR 以及 X 衍射分析,证明1成盐后这种跨环相互作用已使氮原子和14-C 原子间形成稳定的单键,致使十员环变成两个六员环,整个分子变成了氢化原小蘖碱类生物碱基本骨架;当生物碱盐转为游离碱时,分子骨架又变回原来的构型.这种作用推测对十员环异喹啉生物碱具有普遍的意义.
The ten-membered ring isoquinoline alkaloids are widely found in plants and are a class of pharmacologically significant alkaloids. Some studies have shown that the nitrogen atoms in the 10-membered ring of these alkaloids and the 14- (or 13-) There is an amide-like interaction between carbon atoms of carbonyl group, which has the tendency of cyclization; however, the conditions of cyclization and the stability after cyclization are not proved finally.We did not know the protopine , 1) and its hydrochloride were studied. The results of UV, IR, 1 ~ (13) CNMR and X-ray diffraction showed that this cross-ring interaction after salt formation has made the nitrogen atom and 14-C The formation of a stable single bond between atoms, resulting in ten rings into two six-member ring, the entire molecule into hydrogenolide berberine alkaloids basic skeleton; alkaloids salt to free base, the molecular skeleton and change Back to the original configuration.This effect speculated that ten-ring isoquinoline alkaloid has a universal significance.