P-22 新規多環性リコポジウムアルカロイド類の構造と推定生合成経路(ポスター発表の部)

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Plants of Lycopodium species (Lycopodiaceae) produce a number of structurally diverse alkaloids, which often prossess unusual skeletons, and many of them continue to be of interest from biogenetic and biological points of view, as well as challenging targets for total synthesis. Recently we isolated new types of alkaloids such as complanadine A, lyconadin A, senepodine A. himeradine A. lyconesidine A from Lycopodium complanatum and L. chinense. In our search for biogenetically interesting Lycopodium alkaloids, sieboldine A, cermizine A. nankakurines, lycoperine A, and cryptadines, novel alkaloids with an unprecedented fused-polycyclic ring system have been isolated from L. sieboldii, L. cernuum, L. hamiltonii, and L. cryptomerinum. A new C_<16>N_2-type tetracyclic Lycopodium alkaloid, nankakurine B, consisting of a cyclohexane ring and a 3-azabicyclo[3.3.1]nonane ring connected to a piperidine ring through a Spiro carbon, were isolated from the clud moss L. hamiltonii. The structure and relative stereochemistry were elucidated on the basis of spectroscopic data, and structure revision of nankakurine A was based on chemical transformation of nankakurine A to nankakurine B. Three novel C_<27>N_3-type pentacyclic Lycopodium alkaloids, lycoperine A and cryptadines A and B consisting of two octahydroquinoline rings and a piperidine ring, were isolated from the club moss L. hamiltonii and L. cryptomerinum, respectively. The structure and relative stereochemistry were elucidated on the basis of 2D NMR data and chemical transformation. Some of alkaloids induced secretion of neurotrophic factors from human astrocytoma cells. Lycoperine A and cryptadines A and B exhibited an inhibitory activities against acetylcholinesterase.
天然有機化合物討論会の論文
2006-09-15

P-22 新規多環性リコポジウムアルカロイド類の構造と推定生合成経路(ポスター発表の部)

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