Nat Prod Sci.  2019 Jun;25(2):115-121. 10.20307/nps.2019.25.2.115.

Chemical Constituents from Solenostemma argel and their Cholinesterase Inhibitory Activity

• Demmak RG
• Bordage S
• Bensegueni A
• Boutaghane N
• Hennebelle T
• Mokrani EH
• Sahpaz S

• KMID: 2452780
• DOI: http://doi.org/10.20307/nps.2019.25.2.115

Abstract

Alzheimer's disease is a chronic neurodegenerative disorder with no curative treatment. The commercially available drugs, which target acetylcholinesterase, are not satisfactory. The aim of this study was to investigate the cholinesterase inhibitory activity of Solenostemma argel aerial part. Eight compounds were isolated and identified by NMR: kaempferol-3-O-glucopyranoside (1), kaempferol (2), kaempferol-3-glucopyranosyl(1→6)rhamnopyranose (3) p-hydroxybenzoic acid (4), dehydrovomifoliol (5), 14,15-dihydroxypregn-4-ene-3,20-dione (6), 14,15-dihydroxy-pregn-4-ene-3,20-dione-15β-D-glucopyranoside (7) and solargin I (8). Two of them (compounds 2 and 3) could inhibit over 50 % of butyrylcholinesterase activity at 100 µM. Compound (2) displayed the highest inhibitory effect against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with a slight selectivity towards the latter. Molecular docking studies supported the in vitro results and revealed that (2) had made several hydrogen and Ï€-Ï€ stacking interactions which could explain the compound potency to inhibit AChE and BChE.

Keyword

Alzheimer's disease; Cholinesterase; Molecular docking; Solenostemma argel

MeSH Terms

Acetylcholinesterase
Alzheimer Disease
Butyrylcholinesterase
Cholinesterases*
Hydrogen
In Vitro Techniques
Neurodegenerative Diseases
Acetylcholinesterase
Butyrylcholinesterase
Cholinesterases
Hydrogen

Figure

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  Fig. 1 Bioautography showing the inhibition of acetylcholinesterase activity.

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  Fig. 2 Structures of compounds 1 - 8 isolated from Solenostemma argel.

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  Fig. 3 Binding mode prediction of compound 2 into the entire AChE (A) and BChE (B) active pocket. Purple arrows head from the donor to the acceptor of hydrogen bonds and green lines π-π stackings. The gray circle dimensions are proportional to the accessibility to the solvent.

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