Zhang Dong-Bo, Chen Jian-Jun, Song Qiu-Yan, Zhang Li, Gao Kun
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
Molecules. 2014 Jul 10;19(7):9999-10010. doi: 10.3390/molecules19079999.
Four new lycodine-type alkaloids, namely 16-hydroxyhuperzine B (1), N-methyl-11-acetoxyhuperzine B (2), 8,15-dihydrolycoparin A (3) and (7S,12S,13R)-huperzine D-16-O-β-d-glucopyranoside (4), along with ten known analogues 5-14, were isolated from the whole plant of Lycopodiastrum casuarinoides. The structures of the new compounds were elucidated by means of spectroscopic techniques (IR, MS, NMR, and CD) and chemical methods. Compounds 1 and 2 possessed four connected six-membered rings, while compounds 3 and 4 were piperidine ring cleavage products. In particular, compound 4 was a lycopodium alkaloidal glycoside which is reported for the first time. Among the isolated compounds N-demethylhuperzinine (7), huperzine C (8), huperzine B (9) and lycoparin C (13) possessed significant inhibitory activity against acetylcholinesterase, and the new compound 1 showed moderate inhibitory activity. The structure activity relationships were discussed.
从华南石松全草中分离得到4个新的石松碱型生物碱，即16-羟基石杉碱乙（1）、N-甲基-11-乙酰氧基石杉碱乙（2）、8,15-二氢石松灵碱A（3）和(7S,12S,13R)-石杉碱D-16-O-β-D-吡喃葡萄糖苷（4），以及10个已知类似物5-14。通过光谱技术（红外光谱、质谱、核磁共振光谱和圆二色谱）和化学方法对新化合物的结构进行了确证。化合物1和2具有四个相连的六元环，而化合物3和4是哌啶环裂解产物。特别地，化合物4是首次报道的石松生物碱糖苷。在分离得到的化合物中，去甲基石杉碱甲（7）、石杉碱丙（8）、石杉碱乙（9）和石松灵碱C（13）对乙酰胆碱酯酶具有显著的抑制活性，新化合物1表现出中等抑制活性。并对构效关系进行了讨论。
