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

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

Journal

Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434

Informations de publication

Date de publication:
Jun 2019
Historique:
received: 23 01 2019
revised: 22 02 2019
accepted: 20 03 2019
pubmed: 1 4 2019
medline: 17 5 2019
entrez: 1 4 2019
Statut: ppublish

Résumé

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

Identifiants

DOI: 10.1016/j.phytochem.2019.03.015 PMID: 30928888
pubmed: 30928888
pii: S0031-9422(19)30060-3
doi: 10.1016/j.phytochem.2019.03.015
pii:
doi:

Substances chimiques

Alkaloids 0
Cholinesterase Inhibitors 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

183-192

Informations de copyright

Copyright © 2019 Elsevier Ltd. All rights reserved.

Auteurs

Juan Xiong (J)

Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, PR China.

Wei-Jia Meng (WJ)

Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, PR China.

Hai-Yan Zhang (HY)

CAS Key Laboratory of Receptor Research, Shanghai Institute of Material Medica, Chinese Academy of Sciences, Shanghai, 201203, PR China. Electronic address: hzhang@simm.ac.cn.

Yike Zou (Y)

Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA, 19104-6323, United States.

Wen-Xuan Wang (WX)

School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, Hubei, 430074, PR China.

Xin-Yi Wang (XY)

Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, PR China.

Qi-Lian Yang (QL)

Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, PR China. Electronic address: yangql@fudan.edu.cn.

Ezzat E A Osman (EEA)

Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, PR China; Laboratory of Medicinal Chemistry, Theodor Bilharz Research Institute, Kornaish El-Nile St., Giza, 12411, Egypt.

Jin-Feng Hu (JF)

Minhang Hospital & Department of Natural Products Chemistry at School of Pharmacy, Fudan University, Shanghai, 201199, PR China. Electronic address: jfhu@fudan.edu.cn.

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Classifications MeSH

questionsmedicales.fr › Composés hétérocycliques › Alcaloïdes › Lycofargesiines A-F, further Lycopodium...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Agents neuromédiateurs › Agents cholinergiques › Anticholinestérasiques › Lycofargesiines A-F, further Lycopodium...
questionsmedicales.fr › Eucaryotes › Viridiplantae › Streptophyta › Embryophyta › Lycopodiaceae › Lycopodium › Lycofargesiines A-F, further Lycopodium...
questionsmedicales.fr › Techniques d'investigation › Modèles théoriques › Modèles moléculaires › Lycofargesiines A-F, further Lycopodium...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes biochimiques › Conformation moléculaire › Lycofargesiines A-F, further Lycopodium...