Lycofargesiines A–F, further Lycopodium alkaloids from the club moss Huperzia fargesii. (June 2019)

• Record Type: Journal Article
• Authors: Xiong, Juan; Meng, Wei-Jia; Zhang, Hai-Yan; Zou, Yike; Wang, Wen-Xuan; Wang, Xin-Yi; Yang, Qi-Lian; Osman, Ezzat E.A.; Hu, Jin-Feng
• Is Part Of: Phytochemistry. Volume 162(2019)
• Page Start: 183
• Page End: 192
• Publication Date: 2019-06
• Subjects: Huperzia fargesii -- Lycopodiaceae -- Lycopodium alkaloids -- Lycofargesiines -- anti-AChE; N-methylhuperzine B (PubChem CID: 5489404) -- huperzine A (PubChem CID: 854026) -- lycopodine (PubChem CID: 5462445) -- 6α-hydroxylycopodine (PubChem CID: 21576178) -- lycoposerramine J (PubChem CID: 11021729) -- flabelline (PubChem CID: 101289809) -- lycoposerramine X (PubChem CID: 101424895) -- lycoposerramine Z (PubChem CID: 44550887) -- luciduline (PubChem CID: 442480); Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2019.03.015
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Six undescribed Lycopodium alkaloids (LAs) comprising four lycodine-type (lycofargesiines A–D), one lycopodine-type (lycofargesiine E), and a phlegmarine-type (lycofargesiine F), together with 16 known ones were isolated from the club moss Huperzia fargesii . Their structures and absolute configurations were determined by extensive spectroscopic methods, electronic circular dichroism (ECD) analysis, and density functional theory (DFT) calculations. (7 S, 8 R, 12 R, 13 R )-Lycofargesiine A is a rare naturally occurring LA possessing an exocyclic double bond between C-15 and C-16, with ring A being a rare 2, 3-dihyropyridone motif. Lycofargesiine D is an uncommon lycodine-type alkaloid featuring a unique N -acetylated tetrahydropyridinyl segment (ring A), whereas lycofargesiine F is the first phlegmarane-type LA bearing two nitrone moieties. In addition to the isolated huperzine A in this study, another two isolates (lycofargesiine C and 16-hydroxyhuperzine A) were also found to show inhibitory activities against acetylcholinesterase (AChE), with IC50 values of 8.63 and 5.18 μ M, respectively. Graphical abstract: Six (lycofargesiines A–F) undescribed Lycopodium alkaloids were isolated from Huperzia fargesii . Lycofargesiine C and 16-hydroxyhuperzine A showed anti-AChE activities.Image 1 Highlights: Six undescribed Lycopodium alkaloids (LAs) were isolated from Huperzia fargesii. Lycofargesiine A represents the first LA featuring an exocyclic Δ 15 double bond. N -Acetylated lycodine-type lycofargesiine D has a rare tetrahydropyridinyl motif. Lycofargesiine F is an unusual phlegmarane-type LA possessing two nitrone moieties. Lycofargesiine C and 16-hydroxyhuperzine A showed remarkable anti-AChE activities.