Lycopodiastrum Research Articles

Casuarines A and B, Lycopodium alkaloids from Lycopodium casuarinoides

A phytochemical study on Lycopodium casuarinoides has led to the isolation of two new C16N2-type Lycopodium alkaloids, casuarine A (1), a cage-like structure featured with a fused 6/6/6/6/6 pentacyclic ring system, and casuarine B (2). Their structures were elucidated based on the spectroscopic data and further confirmed by X-ray analysis. In vitro acetylcholinesterase (AChE) inhibitory activity assay showed that compound 2 exhibited moderate anti-AChE activity with IC50 46.40 μM.

Development of a Sensitive High-Performance Liquid Chromatographic Method with Simple Extraction for Simultaneous Determination of Huperzine A and Huperzine B in the Species Containing Lycopodium Alkaloids

A sensitive HPLC method with simple extraction was developed for simultaneous determination of huperzine A (HupA) and huperzine B (HupB) in Huperzia serrata, H. crispata, H. miyoshiana, and Lycopodiastrum casuarinoides. In order to avoid conventional multiple-step and time-consuming sample preparation methods, direct reflux extraction with alkaline chloroform was adopted. The quantitative determination was conducted by reversed-phase HPLC with a photodiode array detector set at 308 nm. Separation was performed on a Luna C18 column (250 x 4.6 mm id, 5 microm) with methanol-0.2% aqueous acetic acid (18 + 82, v/v) mobile phase. The method was validated for accuracy, reproducibility, precision, and limits of detection and quantification. Quantification of the two active compounds in the samples was performed by this newly developed method, and the content of HupA and HupB varied substantially among four different species. The satisfactory results indicated that the developed method can readily be utilized for quality control of the species of Huperziaceae and Lycopodiaceae containing the two compounds.

Lycoparins A–C, new alkaloids from Lycopodium casuarinoides inhibiting acetylcholinesterase

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.

Lycodine-Type Alkaloids fromLycopodium casuarinoides

Two new lycodine-type alkaloids, huperzinine N-oxide (1) and 8,15-dihydrohuperzinine (2) as well as five known compounds, huperzinine (3), huperzine B (4), huperzine D (5), N-demethylhuperzinine (6), and β-obscurine (7), were isolated from the club moss Lycopodium casuarinoides. The structures of 1 and 2 were elucidated by spectroscopic methods and chemical transformation. The absolute configuration of 1 was established by chemical correlation with 3, and that of 2 was determined by its CD spectrum.

The alkaloids huperzines C and D and huperzinine from Lycopodiastrum casuarinoides

Two new Lycopodium alkaloids, huperzines C and D, were isolated from Lycopodiastrum casuarinoides along with huperzinine. The structures, inclu

Alkaloids from Lycopodium casuarinoides.

In addition to huperzinine [1], a new alkaloid, N-demethylhuperzinine [2], was isolated from the aerial parts of Lycopodium casuarinoides by bioassay-directed fractionation. The structure of 2 was established by spectral analysis and extensive nOe difference nmr studies as well as spectral comparison with huperzinine. N-Demethylhuperzinine [2] exhibited anticholinesterase activity in pharmacological studies.

Karyomorphology of the genusLycopodium sensu stricto and relationships among species

Karyomorphological comparisons were made of six species of JapaneseLycopodium sensu stricto. There were no marked differences at interphase and prophase among the six species.Lycopodium annotinum had 2n=68 and the formula of its metaphase karyotype was 18m(median centromeric chromosomes)+12sm(submedian)+12st(subterminal)+26t(terminal).Lycopodium casuarinoides had 2n=68=16m+10sm+18st+24t,L. clavatum 2n=68=22m+12sm+18st+16t, andL. obscurum 2n=68=10m+22sm+20st+16t. Each of these species, which belong to different sections, displayed several karyomorphological differences. Among themL. casuarinoides differs largely from the others in its mean chromosome length, ratio of the longest chromosome to the shortest, and frequency of m+sm chromosomes. BothLycopodium complanatum andL. nikoense, belonging to sectionComplanata, had a common karyotype 2n=46=10m+12sm+18st+6t. This section displayed a low differentiation in its karyotype. In the wholeLycopodium s.s., the ratios of m+sm in a complement varied from 38 to 50%, being higher among pteridophytes.