Nine new lycopodine-type alkaloids from Lycopodium japonicum Thunb.

Nine new alkaloids (1-9) with lycopodine-related structures, i.e., 6 alpha,8 beta-dihydroxylycopodine, 4 alpha,8 beta-dihydroxylycopodine, alongside thirteen known compounds (10-22), were isolated from the club moss Lycopodium japonicum Thunb. The structures of the new alkaloids including their absolute configurations were elucidated by extensive spectroscopic analysis, CD method, and by comparison with known analogs. Six of the alkaloids isolated displayed moderate activities against lipopolysaccharide (LPS)-induced pro-inflammatory factors in BV2 macrophages with IC50 values of 4.23-49.03 mu M. (C) 2013 Elsevier Ltd. All rights reserved.