Alstiphyllanines E-H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter
Alstiphyllanines E-H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter
复制标题
DOI：
10.1016/j.bmc.2010.01.077
复制
发表时间：
2010-03-15
影响因子：
3.5
通讯作者：
Morita, Hiroshi
中科院分区：
文献类型：
--
作者：
Arai, Hiroko;Hirasawa, Yusuke;Morita, Hiroshi
从大叶冬青的叶中分离得到3个新苦皮碱型生物碱，分别为苦皮碱型生物碱E-G(1-3)和新的艾季马林型生物碱(4)，以及相关的16个生物碱(5-20)。1-4的结构和立体化学均通过2D核磁共振分析得到了充分的阐明和表征。叶青素E和F(1和2)对Na+-葡萄糖共转运体(SGLT1和SGLT2)具有中等的抑制活性。一系列苦皮碱型生物碱的C-17位羟基取代衍生物21-28具有较强的SGLT抑制活性。10-Methoxy-N(1)-methylburnamine-17-O-veratrate(6)显示出很强的抑制活性，这表明C-17上的酯侧链的存在可能是显示SGLT抑制活性的重要因素。探讨了马钱子碱对SGLT抑制活性的构效关系。(C)2010爱思唯尔有限公司。保留所有权利。
Three new picraline-type alkaloids, alstiphyllanines E-G (1-3) and a new ajmaline-type alkaloid, alstiphyllanine H (4) were isolated from the leaves of Alstonia macrophylla together with 16 related alkaloids (5-20). Structures and stereochemistry of 1-4 were fully elucidated and characterized by 2D NMR analysis. Alstiphyllanines E and F (1 and 2) showed moderate Na+-glucose cotransporter (SGLT1 and SGLT2) inhibitory activity. A series of a hydroxy substituted derivatives 21-28 at C-17 of the picraline-type alkaloids have been derived as having potent SGLT inhibitory activity. 10-Methoxy-N(1)-methylburnamine-17-O-veratrate (6) exhibited potent inhibitory activity, suggesting that the presence of an ester side chain at C-17 may be important to show SGLT inhibitory activity. Structure activity relationship of alstiphyllanines on inhibitory activity of SGLT was discussed. (C) 2010 Elsevier Ltd. All rights reserved.