ABSTRACT
A new C27N3-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.
Subject(s)
Alkaloids , Lycopodium , Lycopodium/chemistry , Acetylcholinesterase , Alkaloids/pharmacology , Alkaloids/chemistryABSTRACT
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.
Subject(s)
Lycopodium/chemistry , Alkaloids/chemistry , Molecular StructureABSTRACT
Five new Lycopodium alkaloids, huperzine Y1 (1), huperzine Y2 (2), huperzine Y3 (3), (+)-huperzine Z (4a) and (-)-huperzine Z (4b) as well as ten known alkaloids (5-14) were isolated from Huperzia serrata. The structures of the new compounds were established using extensive spectroscopic (1D and 2D NMR, IR, and HRESIMS) and calculated electronic circular dichroism (ECD) methods. Compounds 4a and 4b were a pair of enantiomers successfully separated by chiral HPLC resolution. Compounds 2 and 3 indicated inhibitory activities against acetylcholinesterase with IC50 value of 57.1⯱â¯1.6 and 32.7⯱â¯1.0 µΜ, respectively. However, no compound showed inhibitory effect on butyrocholinesterase at the concentration of 100 µΜ.
Subject(s)
Alkaloids/pharmacology , Huperzia/chemistry , Acetylcholinesterase , Alkaloids/isolation & purification , Butyrylcholinesterase , China , Cholinesterase Inhibitors/isolation & purification , Cholinesterase Inhibitors/pharmacology , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacologyABSTRACT
Two novel Lycopodium alkaloids, huperphlegmines A and B (1 and 2), were isolated from the aerial parts of Huperzia phlegmaria collected in Vietnam, together with the five known compounds lycophlegmariol A (3), phlegmariurine B (4), 5-hydroxymethyl-2-furaldehyde (5), rhemanone C (6), and loliolide (7). The chemical structures of the present compounds were elucidated by means of 1D and 2D NMR and HRESIMS spectroscopy, and by comparisons to the reported data in the literature. Compounds 1 and 2 showed moderate acetylcholinesterase inhibitory activities, with IC50 values of 25.95⯱â¯0.67 and 29.14⯱â¯0.77⯵g/mL, respectively.