Casuarinines A-J, lycodine-type alkaloids from Lycopodiastrum casuarinoides.
Ten new lycodine-type alkaloids, named casuarinines A-J (1-10), along with eight known analogues (11-18), were isolated from the whole plant of Lycopodiastrum casuarinoides . The new structures were established by spectroscopic methods and chemical transformations. Casuarinines A-D (1-4) and J (10) are common lycodine alkaloids possessing four connected six-membered rings, while tricyclic casuarinines E-H (5-8) are the piperidine ring cleavage products. In particular, casuarinine I (9) has an unprecedented five-membered tetrahydropyrrole ring instead of the piperidine ring. A plausible biosynthetic pathway to 9 is proposed. Among the compounds reported, casuarinine H (8) exhibited significant neuroprotective effect against hydrogen peroxide (H₂O₂)-induced neuronal cell damage in human neuroblastoma SH-SY5Y cells, while casuarinines C (3) and I (9) showed moderate inhibitory activity against acetylcholinesterase (AChE).
Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, People's Republic of China.
Yu
Y
Tang
Yan
Y
Fu
Juan
J
Xiong
Ming
M
Li
Guang-Lei
GL
Ma
Guo-Xun
GX
Yang
Bang-Guo
BG
Wei
Yun
Y
Zhao
Hai-Yan
HY
Zhang
Jin-Feng
JF
Hu
D000110:Acetylcholinesterase / Q000187:drug effects; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D006861:Hydrogen Peroxide / Q000494:pharmacology; D029542:Lycopodiaceae / Q000737:chemistry*; D015394:Molecular Structure; D009447:Neuroblastoma / Q000188:drug therapy; D018696:Neuroprotective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010880:Piperidines / Q000737:chemistry
D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D018696:Neuroprotective Agents; D010880:Piperidines; C584596:casuarinine H; C032727:piperidine; D006861:Hydrogen Peroxide; D000110:Acetylcholinesterase