Kinetics and molecular docking studies of cholinesterase inhibitors derived from water layer of Lycopodiella cernua (L.) Pic. Serm. (II)

Chem Biol Interact. 2015 Oct 5:240:74-82. doi: 10.1016/j.cbi.2015.07.008. Epub 2015 Aug 20.

Abstract

Acetylcholinesterase (AChE) inhibitors increase the availability of acetylcholine in central cholinergic synapses and are the most promising drugs currently available for the treatment of Alzheimer's disease (AD). Our screening study indicated that the water fraction of the methanolic extract of Lycopodiella cernua (L.) Pic. Serm. significantly inhibited AChE in vitro. Bioassay-guided fractionation led to the isolation of a new lignan glycoside, lycocernuaside A (12), and fourteen known compounds (1-11 and 13-15). Compound 7 exhibited the most potent AChE inhibitory activity with an IC50 value of 0.23 μM. Compound 15 had the most potent inhibitory activity against BChE and BACE1 with IC50 values of 0.62 and 2.16 μM, respectively. Compounds 4 and 7 showed mixed- and competitive-type AChE inhibition. Compound 7 noncompetitively inhibited BChE whereas 15 showed competitive and 8, 13, and 14 showed mixed-type inhibition. The docking results for complexes with AChE or BChE revealed that inhibitors 4, 7, and 15 stably positioned themselves in several pocket/catalytic domains of the AChE and BChE residues.

Keywords: AChEs; Docking; Lignan glycoside; Lycopodiaceae; Lycopodiella cernua.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding, Competitive
  • Biological Assay
  • Chemical Fractionation
  • Cholinesterase Inhibitors* / chemistry
  • Cholinesterase Inhibitors* / pharmacology
  • Enzyme Activation / drug effects
  • Glycosides / chemistry*
  • Glycosides / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Kinetics
  • Lignans / chemistry*
  • Lignans / pharmacology
  • Lycopodiaceae / chemistry*
  • Methanol / chemistry
  • Models, Molecular
  • Molecular Docking Simulation*
  • Plant Extracts* / chemistry
  • Plant Extracts* / pharmacology
  • Protein Binding
  • Water / chemistry*

Substances

  • Cholinesterase Inhibitors
  • Glycosides
  • Lignans
  • Plant Extracts
  • Water
  • Methanol