Sun Jingyong, Lou Hongxiang, Dai Shengjun, Xu Hui, Zhao Feng, Liu Ke
School of Pharmacy, Shandong University, Jinan 250012, People's Republic of China.
Phytochemistry. 2008 Apr;69(6):1405-10. doi: 10.1016/j.phytochem.2008.01.008. Epub 2008 Mar 6.
Five indole alkaloids (naucleofficines A-E) were isolated from the stems (with bark) of Nauclea officinalis: (E)-2-(1-beta-d-glucopyranosyloxybut-2-en-2-yl)-3-(hydroxymethyl)-6,7-dihydro-indolo[2,3-a]quinolizin-4(12H)-one (1), (E)-1-propenyl-12-beta-d-glucopyranosyloxy-2,7,8-trihydro-indolo[2,3-a]pyran[3,4-g]quinolizin-4,5(13H)-dione (2), (E)-2-(1-hydroxybut-2-en-2-yl)-11-beta-d-glucopyranosyloxy-6,7-dihydro-indolo[2,3-a]quinolizin-4(12H)-one (3), (E)-1-propenyl-4-hydroxy-2,4a,7,8,13b,14,14a-hepthydro-(4alpha,4abeta,13balpha,14abeta)indolo[2,3-a]pyran[3,4-g]quinolizin-5(13H)-one (4) and 1-(1-hydroxyethyl)-10-hydroxy-7,8-dihydro-indolo[2,3-a]pirydine[3,4-g]quinolizin-5(13H)-one (10-hydroxyangustoline) (5), together with two known compounds, naucleidinal (6) and angustoline (7). All of the structures of the seven compounds above were elucidated by spectroscopic methods including use of 1D- and 2D-NMR spectroscopic analyses. Compounds 2 and 3 are rare examples of monoterpene indole alkaloids with a glucopyranosyloxy group attached to position C-12. In vitro activity screening of the above seven compounds showed weak to moderate inhibitory activity against Plasmodium falciparum.
从乌檀的茎（带树皮）中分离出5种吲哚生物碱（乌檀碱A - E）：(E)-2-(1-β-D-吡喃葡萄糖氧基丁-2-烯-2-基)-3-(羟甲基)-6,7-二氢吲哚并[2,3-a]喹嗪-4(12H)-酮（1）、(E)-1-丙烯基-12-β-D-吡喃葡萄糖氧基-2,7,8-三氢吲哚并[2,3-a]吡喃[3,4-g]喹嗪-4,5(13H)-二酮（2）、(E)-2-(1-羟基丁-2-烯-2-基)-11-β-D-吡喃葡萄糖氧基-6,7-二氢吲哚并[2,3-a]喹嗪-4(12H)-酮（3）、(E)-1-丙烯基-4-羟基-2,4a,7,8,13b,14,14a-七氢-(4α,4aβ,13bα,14aβ)吲哚并[2,3-a]吡喃[3,4-g]喹嗪-5(13H)-酮（4）和1-(1-羟乙基)-10-羟基-7,8-二氢吲哚并[2,3-a]吡啶[3,4-g]喹嗪-5(13H)-酮（10-羟基狭叶鸭脚木碱）（5），以及两种已知化合物，乌檀啶（6）和狭叶鸭脚木碱（7）。上述7种化合物的结构均通过光谱方法（包括一维和二维核磁共振光谱分析）得以阐明。化合物2和3是罕见的在C-12位连接有吡喃葡萄糖氧基的单萜吲哚生物碱实例。对上述7种化合物进行的体外活性筛选显示，它们对恶性疟原虫具有弱至中等程度的抑制活性。
