| Literature DB >> 20189404 |
Hiroko Arai1, Yusuke Hirasawa1, Abdul Rahman2, Idha Kusumawati2, Noor Cholies Zaini2, Seizo Sato3, Chihiro Aoyama3, Jiro Takeo3, Hiroshi Morita1.
Abstract
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. Copyright 2010 Elsevier Ltd. All rights reserved.Entities:
Mesh：
Substances：
Year: 2010 PMID： 20189404 DOI： 10.1016/j.bmc.2010.01.077
Source DB: PubMed Journal: Bioorg Med Chem ISSN： 0968-0896 Impact factor: 3.641