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Planta Med 2016; 82(01/02): 138-146
DOI: 10.1055/s-0035-1558088
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Sesquiterpene Lactones from Cynara cornigera: Acetyl Cholinesterase Inhibition and In Silico Ligand Docking

Mohamed-Elamir F. Hegazy
1   Phytochemistry Department, National Research Centre, Giza, Egypt
2   Center of Excellence for Advanced Sciences, National Research Centre, Giza, Egypt
,
Abeer Y. Ibrahim
3   Medicinal and Aromatic Plants Researches Department, Pharmaceutical and Drug Industries Researches Division, National Research Centre, Giza, Egypt
,
Tarik A. Mohamed
1   Phytochemistry Department, National Research Centre, Giza, Egypt
,
Abdelaaty A. Shahat
1   Phytochemistry Department, National Research Centre, Giza, Egypt
4   Pharmacognosy Department, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia
,
Ali M. El Halawany
5   Faculty of Pharmacy, King Abdulaziz University, Jeddah, Saudi Arabia
6   Department of Pharmacognosy, Cairo University, Cairo, Egypt
,
Nahla S. Abdel-Azim
1   Phytochemistry Department, National Research Centre, Giza, Egypt
,
Mansour S. Alsaid
4   Pharmacognosy Department, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia
,
Paul W. Paré
7   Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA
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Publikationsverlauf

received 21. April 2015
revised 31. Juli 2015

accepted 10. August 2015

Publikationsdatum:
05. Oktober 2015 (online)

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Erratum zu diesem Artikel:

Erratum for: Sesquiterpene Lactones from Cynara cornigera: Acetyl Cholinesterase Inhibition and In Silico Ligand DockingPlanta Med 2016; 82(01/02): E3-E3
DOI: 10.1055/s-0035-1558179

Abstract

Wild artichoke (Cynara cornigera), a thistle-like perennial belonging to the Asteraceae family, is native to the Mediterranean region, northwestern Africa, and the Canary Islands. While the pleasant, albeit bitter, taste of the leaves and flowers is attributed to the sesquiterpene lactones cynaropicrin and cynarin, a comprehensive phytochemical investigation still needs to be reported. In this study seven sesquiterpene lactones were isolated from an aqueous methanol plant extract, including a new halogenated metabolite (1), the naturally isolated compound sibthorpine (2), and five metabolites isolated for the first time from C. cornigera. Structures were established by spectroscopic methods, including HREIMS, 1 H, 13 C, DEPT, 1 H-1 H COSY, HMQC, and HMBC-NMR experiments as well as by X-ray analysis. The isolated bioactive nutrients were analyzed for their antioxidant and metal chelating activity. Compound 1 exhibited a potent metal chelating activity as well as a high antioxidant capacity. Moreover, select compounds were effective as acetyl cholinesterase inhibitors presenting the possibility for such compounds to be examined for anti-neurodegenerative activity. A computational pharmacophore elucidation and docking study was performed to estimate the pharmacophoric features and binding conformation of isolated compounds in the acetyl cholinesterase active site.

Key words

Cynara cornigera - Asteraceae - sesquiterpene lactones - acetyl cholinesterase inhibition - in silico ligand docking
 

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