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Molecules 2014, 19(7), 9999-10010; doi:10.3390/molecules19079999

Lycodine-Type Alkaloids from Lycopodiastrum casuarinoides and Their Acetylcholinesterase Inhibitory Activity

1
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China
2
School of Biotechnology and Chemical Engineering, Ningbo Institute of Technology, Zhejiang University; Ningbo 315100, China
*
Authors to whom correspondence should be addressed.
Received: 23 May 2014 / Revised: 18 June 2014 / Accepted: 27 June 2014 / Published: 10 July 2014
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
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Abstract

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 514, 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. View Full-Text
Keywords: Lycopodiastrum casuarinoides; Lycopodiaceae; lycodine alkaloid; acetylcholinesterase; 16-hydroxyhuperzine B; N-methyl-11-acetoxyhuperzine B; 8,15-dihydrolycoparin A; (7S,12S,13R)-huperzine D-16-O-β-d-glucopyranoside Lycopodiastrum casuarinoides; Lycopodiaceae; lycodine alkaloid; acetylcholinesterase; 16-hydroxyhuperzine B; N-methyl-11-acetoxyhuperzine B; 8,15-dihydrolycoparin A; (7S,12S,13R)-huperzine D-16-O-β-d-glucopyranoside
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MDPI and ACS Style

Zhang, D.-B.; Chen, J.-J.; Song, Q.-Y.; Zhang, L.; Gao, K. Lycodine-Type Alkaloids from Lycopodiastrum casuarinoides and Their Acetylcholinesterase Inhibitory Activity. Molecules 2014, 19, 9999-10010.

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