Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum |
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Authors: | Kan’ichiro IshiuchiTakaaki Kubota Haruaki IshiyamaShigeki Hayashi Toshiro ShibataJun’ichi Kobayashi |
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Institution: | a Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan b Hokkaido Division, Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation, Nayoro, 096-0065, Japan |
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Abstract: | New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C16N2-type Lycopodium alkaloid possessing unique fused-tetracyclic ring system consisting of a cycloheptene ring fused to a decahydroquinoline and pyridone rings. Lyconadin F (2) possesses a primary amide moiety in its molecular, which is the first example of Lycopodium alkaloids. Biogenetically, lyconadins C (1) and F (2) might be related to lyconadins A (4) and B (5). The structures and relative stereochemistry of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute stereochemistry of 2 was elucidated by chemical correlations with lyconadin B (5) through hemiaminal form of lyconadin F (3). |
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Keywords: | Lycopodium alkaloids Lycopodium complanatum Lyconadin C Lyconadin F |
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