ALSTONIA SCHOLARIS - STRUCTURE OF INDOLE ALKALOID NARELINE
ALSTONIA SCHOLARIS - STRUCTURE OF INDOLE ALKALOID NARELINE
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DOI：
10.1002/hlca.19770600434
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发表时间：
1977-01-01
影响因子：
1.8
通讯作者：
OBERHANSLI, WE
中科院分区：
文献类型：
--
作者：
MORITA, Y;HESSE, M;OBERHANSLI, WE
从紫堇中分离得到一个新的吲哚生物碱，命名为nareline 2（M = 352）。scholaris河Br.，属于夹竹桃科植物。用单晶X射线衍射法确定了它的结构和绝对构型。2及其衍生物的光谱数据，以及它们的化学行为，支持这种结构。在生物发生学意义上，nareline与碱akuammiline和picraline有关。与此相反，C原子5是环外的，代表与N（4）-羟胺基的氧原子一起形成环状半缩醛的醛基。通过2的氧化（CrO 3/CH 3COOH），形成含有环状缩醛作为部分结构元素的奥吲哚衍生物（奥佐那瑞林）。
Besides the known akuammidine, picralinal, picrinine and pseudoakuammigine a new indole alkaloid called nareline 2 (M = 352) was isolated from A. scholaris R. Br., which belongs to the plant family of Apocynaceae. Its structure and absolute configuration was deduced by single crystal X-ray diffraction. The spectroscopic data of 2 and its derivatives, as well as their chemical behavior, support this structure. In biogenetic sense nareline is related to the bases akuammiline and picraline. In contrast to those the C-atom 5 is exocyclic and represents an aldehyde group which forms together with the oxygen atom of the N (4)-hydroxylamine group a cyclic half acetal. By oxidation (CrO3/CH3COOH) of 2 the oxindol derivative (oxonareline) is formed which contains a cyclic acetal as a partial structure element.