Gelegamines A-E: five new oxindole alkaloids from Gelsemium elegans
Gelegamines A-E: five new oxindole alkaloids from Gelsemium elegans
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DOI：
10.1016/j.tet.2009.03.086
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发表时间：
2009-06-06
期刊：
影响因子：
2.1
通讯作者：
Hao, Xiao-Jiang
中科院分区：
文献类型：
--
作者：
Zhang, Zhen;Di, Ying-Tong;Hao, Xiao-Jiang
从钩吻（Gelsemiumelegans）根中分得5个新的氧化吲哚生物碱，命名为gelegamines A-E（1-5）。通过波谱分析，对化合物的结构进行了鉴定。其中，通过ROESY实验和密度泛函方法在B3 LYP/6- 31 g（d）水平上确定了其中的gelegamine A（1）的环氧环（C-19/C-20）为α-取向，gelegamine B（2）是第一个具有19-（E）亚乙基构型的humantenine型生物碱。基于生物合成的考虑，结合圆二色谱实验，确定了gelegamines A-E（1-5）的绝对构型。(C)2009爱思唯尔有限公司保留所有权利。
Five new oxindole alkaloids, gelegamines A-E (1-5), were isolated from the roots of Gelsemium elegans. Their structures were extensively elucidated on the basis of spectroscopic analysis. Among them, the epoxy ring (C-19/C-20) of gelegamine A (1) was assigned as alpha-orientation by ROESY experiment and DFT method at B3LYP/6-31g(d) level, and gelegamine B (2) is the first humantenine-type alkaloid with 19-(E) ethylidene configuration. The absolute configurations of gelegamines A-E (1-5) were established on biosynthetic consideration coupled with CD experiments. (C) 2009 Elsevier Ltd. All rights reserved.