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A new C 27 N 3 -type Lycopodium alkaloid consisting of two decahydroquinolines and a piperidine, cryptadine C (1) was isolated from Lycopodium cryptomerinum. The structure and relative configuration of 1, which is related to those of cryptadines A and B, lycoperine A, and hupercumine A, was elucidated on the basis of spectroscopic data. Cryptadine C showed moderate inhibitory activity against acetylcholinesterase., (© 2023. The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy.)

A novel Lycopodium alkaloid, complanadine F (1), seco-complanadine A type was isolated from the club moss Lycopodium complanatum. The planar structure and relative configuration were elucidated based on spectroscopic data.

A novel class of C 38 N 4 Lycopodium alkaloid, hupercumine A (1), consisting of two octahydroquinolines, a decahydroquinoline, and a piperidine, and a new C 27 N 3 -type alkaloid, hupercumine B (2), were isolated from Huperzia cunninghamioides (Hayata) Holub. The structures and absolute configurations of 1 and 2 were elucidated on the basis of spectroscopic data, chemical means, and biogenetic point of view. Hupercumines A (1) and B (2) showed moderate inhibitory activity against acetylcholinesterase.

A novel C(19)N-type Lycopodium alkaloid, malycorin A (1) consisting of a serratinane skeleton with 2-propanol unit has been isolated from the club moss Lycopodium phlegmaria, together with two new C(16)N-type alkaloids, malycorins B (2) and C (3), and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data.

Three new Lycopodium alkaloids, lycoparins A-C (1-3), have been isolated from the club moss Lycopodium casuarinoides. Structures and stereochemistry of 1-3 were elucidated on the basis of 2D NMR correlations. Lycoparins C (3) exhibited an inhibitory activity against acetylcholinesterase, while lycoparins A (1) and B (2) did not show activity.

Two novel C(27)N(3)-type Lycopodium alkaloids, cryptadines A (1) and B (2) consisting of two octahydroquinoline rings (C(11)N) and a piperidine ring (C(5)N), have been isolated from the club moss Lycopodium cryptomerinum, and their structures and relative stereochemistry were elucidated on the basis of spectroscopic data, chemical transformations, and computational methods. Cryptadines A (1) and B (2) exhibited an inhibitory activity against acetylcholinesterase.

Three new Lycopodium alkaloids, carinatumins A-C (1-3), have been isolated from the club moss Lycopodium carinatum. Structures and stereochemistry of 1-3 were elucidated on the basis of 2D NMR correlations. Carinatumins A (1) and B (2) exhibited a potent inhibitory activity against acetylcholinesterase.

[structure: see text] A novel C(27)N(3)-type pentacyclic Lycopodium alkaloid, lycoperine A (1) consisting of two octahydroquinoline rings and a piperidine ring, was isolated from the club moss Lycopodium hamiltonii. The structure and relative stereochemistry were elucidated on the basis of 2D NMR data and chemical transformation. Lycoperine A (1) exhibited an inhibitory activity against acetylcholinesterase.

Three new alkaloids, lycopodatines A (1), B (2), and C (3), have been isolated from the club moss Lycopodium inundatum, and the structures and absolute configuration were elucidated on the basis of 2D NMR data and chemical transformation.

[sstructure: see text] A novel, fused-tetracyclic Lycopodium alkaloid, nankakurine A (1), consisting of a cyclohexane ring and a 3-aza-bicyclo[3.3.1]nonane ring connected to a piperidine ring through a spiro carbon, was isolated from the club moss Lycopodium hamiltonii. The structure and relative stereochemistry were elucidated on the basis of spectroscopic data.

[structure: see text] A novel Lycopodium alkaloid with an unprecedented fused-tetracyclic ring system consisting of an aza-cyclononane ring having a N-hydroxy group, a cyclohexanone, a cyclopentanone, and a tetrahydrofuran ring, sieboldine A (1), was isolated from the club moss Lycopodium sieboldii. The structure and relative stereochemistry were elucidated on the basis of 2D NMR data and X-ray analysis. Sieboldine A (1) exhibited a potent inhibitory activity against acetylcholinesterase and modest cytotoxicity.

A novel C(27)N(3)-type Lycopodium alkaloid consisting of a fastigiatine-type skeleton (C(16)N(2)) and a quinolizidine moiety (C(11)N), himeradine A (1), has been isolated from the club moss Lycopodium chinense, and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.

Abstract: Two novel C27N3-type Lycopodium alkaloids, cryptadines A (1) and B (2) consisting of two octahydroquinoline rings (C11N) and a piperidine ring (C5N), have been isolated from the club moss Lycopodium cryptomerinum, and their structures and relative stereochemistry were elucidated on the basis of spectroscopic data, chemical transformations, and computational methods. Cryptadines A (1) and B (2) exhibited an inhibitory activity against acetylcholinesterase. [Copyright &y& Elsevier]

Abstract: Seven new Lycopodium alkaloids, lannotinidines A–G (1–7), have been isolated from the club moss Lycopodium annotinum and L. annotinum var. acrifolium. Stereochemistry of 1–7 was elucidated by combination of NOESY correlations and chemical transformation. Lannotinidines B–E (2–5) elevated NGF mRNA expression. [Copyright &y& Elsevier]