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Lycodine-Type Alkaloids from Lycopodiastrum casuarinoides and Their Acetylcholinesterase Inhibitory Activity
- Source :
- Molecules, Molecules, Vol 19, Iss 7, Pp 9999-10010 (2014), Molecules; Volume 19; Issue 7; Pages: 9999-10010
- Publication Year :
- 2014
- Publisher :
- MDPI, 2014.
-
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 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.
- Subjects :
- Lycopodium
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
Stereochemistry
Pharmaceutical Science
(7S, 12S, 13R)-huperzine D-16-O-β-d-glucopyranoside
Cleavage (embryo)
Inhibitory postsynaptic potential
Ring (chemistry)
Heterocyclic Compounds, 4 or More Rings
Article
Analytical Chemistry
lcsh:QD241-441
chemistry.chemical_compound
Inhibitory Concentration 50
Alkaloids
lcsh:Organic chemistry
Drug Discovery
Physical and Theoretical Chemistry
Nuclear Magnetic Resonance, Biomolecular
chemistry.chemical_classification
biology
Molecular Structure
Plant Extracts
Organic Chemistry
Glycoside
biology.organism_classification
Acetylcholinesterase
chemistry
Chemistry (miscellaneous)
Molecular Medicine
Piperidine
Cholinesterase Inhibitors
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 19
- Issue :
- 7
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....8bc6bdc4888379561a7b89726046f3b5