Club Moss Lycopodium Complanatum Research Articles

Complanadine F, a novel dimeric alkaloid from Lycopodium complanatum.

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.

Progress towards the Total Syntheses of Lycopodium Alkaloid, Lycopladine A

AbstractSeveral alkaloids derived from discrete Lycopodium species can treat Alzheimer's disease and increase the efficiency of learning and memory in animals. Thus, Lycopodium alkaloids bearing amazingly unique hetero‐polycyclic ring scaffolds persuaded scientists to look upon its biogenetic and biosynthetic pathways and to design its ambitious total syntheses. Recently, a C16N type Lycopodium alkaloid, (+)‐lycopladine A; isolated from the club moss Lycopodium complanatum, showed selective but modest cytotoxicity towards murine lymphoma L1210 cells (IC50 7 μg/mL). Owing to its dense array of stereochemical features, as well as intriguing biological activity, lycopladine A has been an important synthetic target for last 12 years. An overview of the synthetic studies of lycopladine A is presented, covering literature from 2006 until March 2019.

Abietane diterpenoids from Lycopodium complanatum

Five new abietane diterpenoids (complanatins A-E, 1–5) have been isolated from the club moss Lycopodium complanatum, along with two known abietane diterpenoids (xanthoperol and sugiol). Their structures were determined by comprehensive analysis of 1D, 2D NMR, CD and HRESIMS data. The cytotoxic effects of five compounds (1–4, 7) were evaluated in three human lung cancer cell lines (MSTO-211H, NCI-H2052 and NCI-H226). Compounds 3 and 4 exhibited cytotoxic activities against the three cell lines. In addition, a plausible biogenetic pathway of compounds 1–7 was proposed.

Lycoplanine A, a C16N Lycopodium Alkaloid with a 6/9/5 Tricyclic Skeleton from Lycopodium complanatum.

Lycoplanine A (1), a Lycopodium alkaloid with a 6/9/5 tricyclic ring skeleton fused with the γ-lactone ring and featuring an unusual 1-oxa-6-azaspiro[4.4]nonane moiety and an unprecedented 3-azabicyclo[6.3.1]dodecane unit, was isolated from the club moss Lycopodium complanatum. The structure and absolute configuration of 1 were identified by a combination of NMR spectroscopic analysis and single-crystal X-ray diffraction. Biological studies showed that 1 is a potent Cav3.1 T-type calcium channel (TTCC) inhibitor with an IC50 value of 6.06 μM.

ChemInform Abstract: 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 16 N 2 -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 ).

Lyconadins D and E, and complanadine E, new Lycopodium alkaloids from Lycopodium complanatum

Three new Lycopodium alkaloids, lyconadins D (1) and E (2), and complanadine E (3), were isolated from the club moss Lycopodium complanatum. Lyconadin D (1) was the first example of fastigiatine-type alkaloid isolated from Lycopodium complanatum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Complanadine E (3) enhanced mRNA expression for NGF.

Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum

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).

Lycopladine H, a novel alkaloid with fused-tetracyclic skeleton from Lycopodium complanatum

A novel Lycopodium alkaloid, lycopladine H (1), with a fused-tetracyclic ring system consisting of an azocane ring connected to a [2,2,2]-bicyclooctane ring and a 3-piperidone ring, was isolated from the club moss Lycopodium complanatum. The structure and relative stereochemistry of 1 were elucidated on the basis of spectroscopic data.

Lycopladines F and G, new C 16N 2-type alkaloids with an additional C 4N unit from Lycopodium complanatum

Two new Lycopodium alkaloids, lycopladines F ( 1) and G ( 2), have been isolated from the club moss Lycopodium complanatum, and the structures and relative stereochemistries of 1 and 2 were elucidated on the basis of spectroscopic data. Lycopladine F ( 1) is a rare C 16N 2-type Lycopodium alkaloid possessing an amino acid residue (C 4N).

Lycopladine E, a New C16N1-Type Alkaloid from Lycopodium complanatum

A new C 16 N 1 -type alkaloid, lycopladine E (1), has been isolated from the club moss Lycopodium complanatum, and the structure and absolute stereochemistry were elucidated on the basis of spectroscopic data and chemical correlation.

Complanadines C and D, new dimeric alkaloids from Lycopodium complanatum

Two new dimeric Lycopodium alkaloids, complanadines C ( 1) and D ( 2), have been isolated from the club moss Lycopodium complanatum, and the structures and relative stereochemistry of 1 and 2 were elucidated on the basis of the spectral data. Complanadine D ( 2) enhanced mRNA expression for NGF.

Lycopladine A, a New C16N Alkaloid from Lycopodium complanatum.

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Lycopladines B–D and lyconadin B, new alkaloids from Lycopodium complanatum

Four new alkaloids, lycopladines B–D ( 1– 3) and lyconadin B ( 4), have been isolated from the club moss Lycopodium complanatum and the structures including the stereochemistry were elucidated on the basis of spectral data and modified Mosher’s method. Lyconadin B ( 4) elevated NGF mRNA expression in 1321N1 human astrocytoma cells.

Lycopladine A, a new C 16N alkaloid from Lycopodium complanatum

A new C 16N type alkaloid, lycopladine A ( 1), has been isolated from the club moss Lycopodium complanatum, and the structure and relative stereochemistry of 1 were elucidated on the basis of spectral data.

Complanadine B, Obscurumines A and B, New Alkaloids from Two Species of Lycopodium

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Complanadine B, obscurumines A and B, new alkaloids from two species of Lycopodium

A new dimer of C 16N 2 type alkaloid, complanadine B ( 1 ), and two new C 16N type alkaloids, obscurumines A ( 2 ) and B ( 3 ), have been isolated from the club moss Lycopodium complanatum and L. obscurum, respectively. The structures and stereochemistry of 1– 3 were elucidated by combination of 2D NMR spectra and chemical transformation. Complanadine A ( 4 ) isolated together with 1 induced secretion of neurotrophic factors from human astrocytoma cells.

Complanadine A, a new dimeric alkaloid from Lycopodium complanatum

A new dimeric alkaloid with a lycodine-type skeleton, complanadine A ( 1), has been isolated from the club moss Lycopodium complanatum, and the structure including the absolute stereochemistry was elucidated on the basis of spectroscopic data.