Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum

Kan'ichiro Ishiuchi; Takaaki Kubota; Haruaki Ishiyama; Shigeki Hayashi; Toshiro Shibata; Jun'ichi Kobayashi

doi:10.1016/j.tetlet.2010.11.024

Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum

Kan'ichiro Ishiuchi, Takaaki Kubota, Haruaki Ishiyama, Shigeki Hayashi, Toshiro Shibata, Jun'ichi Kobayashi

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C ₁₆N₂-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).

Original language	English
Pages (from-to)	289-292
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2010.11.024
Publication status	Published - Jan 12 2011
Externally published	Yes

Keywords

Lyconadin C
Lyconadin F
Lycopodium alkaloids
Lycopodium complanatum

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.11.024

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title = "Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum",

abstract = "New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C 16N2-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).",

keywords = "Lyconadin C, Lyconadin F, Lycopodium alkaloids, Lycopodium complanatum",

author = "Kan'ichiro Ishiuchi and Takaaki Kubota and Haruaki Ishiyama and Shigeki Hayashi and Toshiro Shibata and Jun'ichi Kobayashi",

note = "Funding Information: The authors thank Ms. S. Oka, Center for Equipment Management Center, Hokkaido University, for measurements of ESIMS. This work was partly supported by a research fellowship for young scientists from the Japan Society for the Promotion of Science (to K.I.), and a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan. ",

year = "2011",

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doi = "10.1016/j.tetlet.2010.11.024",

language = "English",

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T1 - Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum

AU - Ishiuchi, Kan'ichiro

AU - Kubota, Takaaki

AU - Ishiyama, Haruaki

AU - Hayashi, Shigeki

AU - Shibata, Toshiro

AU - Kobayashi, Jun'ichi

N1 - Funding Information: The authors thank Ms. S. Oka, Center for Equipment Management Center, Hokkaido University, for measurements of ESIMS. This work was partly supported by a research fellowship for young scientists from the Japan Society for the Promotion of Science (to K.I.), and a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

PY - 2011/1/12

Y1 - 2011/1/12

N2 - New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C 16N2-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).

AB - New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C 16N2-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).

KW - Lyconadin C

KW - Lyconadin F

KW - Lycopodium alkaloids

KW - Lycopodium complanatum

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Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum

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