title: Five new Lycopodium alkaloids from the aerial parts of Phlegmariurus henryi.
abstract: A series of new Lycopodium alkaloids, namely 1-epi-malycorin A (1), 1-epi-17S-hydroxymalycorin A (2), 6α-hydroxyphlegmariurine A (3), 2S,4R-dihydroxyfawcettimine (4), and 16-hydroxylycodine (5), together with 24 known ones, have been isolated from the club moss Phlegmariurus henryi. The structures of the new compounds were determined by extensive spectroscopic analysis, including 1D and 2D NMR, as well as X-ray crystallographic analysis. Among them, the absolute configurations of 1, 2, and 4 and the structure of 3 were confirmed on the basis of the single-crystal X-ray diffraction analysis. 1-Epi-17S-hydroxymalycorin A (2) was a unique C19N-type Lycopodium alkaloid consisting of a serratinine skeleton with 1,2-propanediol unit. 2S,4R-dihydroxyfawcettimine (4) was a 2,4-dihydroxy derivative of fawcettimine. 16-Hydroxylycodine (5) was the oxidative product of lycodine with an unusual hydroxymethyl group at C-15. All new compounds were evaluated for in vitro acetylcholinesterase (AChE) inhibitory activity and cytotoxicity against four human cancer cell lines.
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China; University of the Chinese Academy of Sciences, Beijing 100049, PR China.
authors: Yu-Chen
authors: YC
authors: Liu
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
authors: Jia
authors: J
authors: Su
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
authors: Xing-De
authors: XD
authors: Wu
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China; University of the Chinese Academy of Sciences, Beijing 100049, PR China.
authors: Zhi-Jun
authors: ZJ
authors: Zhang
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China; University of the Chinese Academy of Sciences, Beijing 100049, PR China.
authors: Min
authors: M
authors: Fan
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China; University of the Chinese Academy of Sciences, Beijing 100049, PR China.
authors: Qin-Feng
authors: QF
authors: Zhu
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
authors: Juan
authors: J
authors: He
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
authors: Xiao-Nian
authors: XN
authors: Li
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
authors: Li-Yan
authors: LY
authors: Peng
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
authors: Xiao
authors: X
authors: Cheng
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China. Electronic address: qinshizhao@mail.kib.ac.cn.
authors: Qin-Shi
authors: QS
authors: Zhao
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D045744:Cell Line, Tumor; D002800:Cholinesterase Inhibitors / Q000737:chemistry; D006801:Humans; D007212:Indolizines / Q000737:chemistry / Q000302:isolation & purification; D029542:Lycopodiaceae / Q000737:chemistry*; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry
chemical_list: D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D007212:Indolizines; C524731:fawcettimine; C009245:serratinine
keywords: Anti-AChE activity; Cytotoxicity; Lycopodium alkaloids; Phlegmariurus henryi