Serratezomines D and E, new Lycopodium alkaloids from Lycopodium serratum var. serratum

• Published in: Bioorganic & medicinal chemistry letters 2009-07, Vol.19 (13), p.3577-3580
• Main Authors: Kubota, Takaaki, Yahata, Hiroko, Yamamoto, Sunao, Hayashi, Shigeki, Shibata, Toshiro, Kobayashi, Jun’ichi
• Format: Article
• Language: English
• Subjects: Acetylcholinesterase; Acetylcholinesterase - chemistry; Acetylcholinesterase - metabolism; Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Biological and medical sciences; Cholinesterase Inhibitors - chemistry; Cholinesterase Inhibitors - isolation & purification; Cholinesterase Inhibitors - pharmacology; General pharmacology; Heterocyclic Compounds, 2-Ring - chemistry; Heterocyclic Compounds, 2-Ring - isolation & purification; Heterocyclic Compounds, 2-Ring - pharmacology; Heterocyclic Compounds, 3-Ring - chemistry; Heterocyclic Compounds, 3-Ring - isolation & purification; Heterocyclic Compounds, 3-Ring - pharmacology; Lycopodium - chemistry; Lycopodium alkaloids; Medical sciences; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Extracts - chemistry; Quinolines - chemistry; Quinolines - isolation & purification; Quinolines - pharmacology; Serratezomines D and E; Stereoisomerism
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2009.04.146

Two new Lycopodium alkaloids, serratezomines D ( 1) and E ( 2), were isolated from the club moss Lycopodium serratum var. serratum. Serratezomine D ( 1) is a new lucidine-type alkaloid, while serratezomine E ( 2) is a new phlegmarane-type alkaloid. The structures and relative stereochemistry of 1 and 2 were elucidated on the basis of spectroscopic data. Serratezomine D ( 1) exhibited an inhibitory activity against acetylcholinesterase.