Five previously undescribed lycodine-type alkaloids, named huperzine Y (1), 8,15-epoxy-N-demethylhuperzinine (2), 7-hydroxyl-huperzinine (3), huperzine Z (4), and huperzine D N-oxide (5), were isolated from the whole plants of Lycopodiastrum casuarinoides (Lycopodiaceae), along with ten known analogues. The structures of the new compounds were elucidated by means of spectroscopic technique (IR, UV, MS and NMR). The absolute configurations of the new compounds were established on the basis of comparison of their experimental and TD-DFT (time-dependent density functional theory) calculated ECD spectra. Moreover, all the isolates were evaluated for acetylcholinesterase (AChE) inhibitory activity. Only huperzine C showed moderate activity, with an IC50 value of 0.525+/-0.140muM, which was comparable with the positive control, huperzine A (IC50=0.143+/-0.029muM).
Four new trace alkaloids with lycodine-related structures, Lycocasuarinines A-D (1-4), together with seven known analogues (5-11), were isolated from the chloroform extract of Lycopodiastrum casuarinoides. The structures and stereochemistry of 1-4 were elucidated by spectroscopic analysis (IR, UV, MS, NMR, HRESIMS and CD) and comparison with known ones. The acetylcholinesterase (AChE) and butyrocholinesterase (BuChE) inhibitory activities of nine isolates were evaluated. Lycocasuarinine D (4) showed the most potent AChE inhibitory effect. In addition, a plausible biogenetic pathway of compound 4 was proposed.
Title: Alkaloids from Lycopodium casuarinoides Shen YC, Chen CH Ref: Journal of Natural Products, 57:824, 1994 : PubMed
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.
Five previously undescribed lycodine-type alkaloids, named huperzine Y (1), 8,15-epoxy-N-demethylhuperzinine (2), 7-hydroxyl-huperzinine (3), huperzine Z (4), and huperzine D N-oxide (5), were isolated from the whole plants of Lycopodiastrum casuarinoides (Lycopodiaceae), along with ten known analogues. The structures of the new compounds were elucidated by means of spectroscopic technique (IR, UV, MS and NMR). The absolute configurations of the new compounds were established on the basis of comparison of their experimental and TD-DFT (time-dependent density functional theory) calculated ECD spectra. Moreover, all the isolates were evaluated for acetylcholinesterase (AChE) inhibitory activity. Only huperzine C showed moderate activity, with an IC50 value of 0.525+/-0.140muM, which was comparable with the positive control, huperzine A (IC50=0.143+/-0.029muM).
Four new trace alkaloids with lycodine-related structures, Lycocasuarinines A-D (1-4), together with seven known analogues (5-11), were isolated from the chloroform extract of Lycopodiastrum casuarinoides. The structures and stereochemistry of 1-4 were elucidated by spectroscopic analysis (IR, UV, MS, NMR, HRESIMS and CD) and comparison with known ones. The acetylcholinesterase (AChE) and butyrocholinesterase (BuChE) inhibitory activities of nine isolates were evaluated. Lycocasuarinine D (4) showed the most potent AChE inhibitory effect. In addition, a plausible biogenetic pathway of compound 4 was proposed.
Title: Lycodine-type alkaloids from Lycopodium casuarinoides Yin S, Fan CQ, Wang XN, Yue JM Ref: Helv Chim Acta, 89:138, 2006 : PubMed
Two new lycodine-type alkaloids, huperzinineN-oxide (1) and 8,15-dihydrohuperzinine (2) as well asfive known compounds, huperzinine (3), huperzine B (4), huperzine D (5),N-demethylhuperzinine (6),and b-obscurine (7), were isolated from the club mossLycopodium casuarinoides. The structures of 1 and 2 were elucidated by spectroscopic methods and chemical transformation. The absolute configuration of 1was established by chemical correlation with 3, and that of 2 was determined by its CD spectrum.
Title: Alkaloids from Lycopodium casuarinoides Shen YC, Chen CH Ref: Journal of Natural Products, 57:824, 1994 : PubMed
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.
