Lycofargesiines A–F, further Lycopodium alkaloids from the club moss Huperzia fargesii

Theodor Bilharz Research Institute

Bibliographic Information

Authors: Xiong J.; Meng W.-J.; Zhang H.-Y.; Zou Y.; Wang W.-X.; Wang X.-Y.; Yang Q.-L.; Osman E.E.A.; Hu J.-F.

Journal: Phytochemistry

Publisher: Elsevier Ltd

Publication Date: June 2019

Volume / Issue: Volume 162

Pages: 183–192

ISSN: 319422

DOI: 10.1016/j.phytochem.2019.03.015

Scopus: View on Scopus

PubMed: 30928888

Document Type: Article

Authors and Affiliations

Xiong J., Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, China; Meng W.-J., Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, China; Zhang H.-Y., CAS Key Laboratory of Receptor Research, Shanghai Institute of Material Medica, Chinese Academy of Sciences, Shanghai, 201203, China; Zou Y., Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, 19104-6323, PA, United States; Wang W.-X., School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, 430074, Hubei, China; Wang X.-Y., Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, China; Yang Q.-L., Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, China; Osman E.E.A., Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, China, Laboratory of Medicinal Chemistry, Theodor Bilharz Research Institute, Kornaish El-Nile St., Giza, 12411, Egypt; Hu J.-F., Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, China

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. (7S,8R,12R,13R)-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 IC 50 values of 8.63 and 5.18 μM, respectively. © 2019 Elsevier Ltd

Keywords

6α-hydroxylycopodine (PubChem CID: 21576178); anti-AChE; flabelline (PubChem CID: 101289809); Huperzia fargesii; huperzine A (PubChem CID: 854026); luciduline (PubChem CID: 442480); Lycofargesiines; Lycopodiaceae; lycopodine (PubChem CID: 5462445); Lycopodium alkaloids; lycoposerramine J (PubChem CID: 11021729); lycoposerramine X (PubChem CID: 101424895); lycoposerramine Z (PubChem CID: 44550887); N-methylhuperzine B (PubChem CID: 5489404); Alkaloids; Cholinesterase Inhibitors; Lycopodium; Models, Molecular; Molecular Conformation; alkaloid; cholinesterase inhibitor; chemistry; conformation; molecular model

Citation Information

Scopus Citations: 16

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