Isolation of four new pterocarpans from Zygophyllum eurypterum (Syn. Z. atriplicoides) with enzyme-inhibition properties

Chem Biodivers. 2006 Sep;3(9):996-1003. doi: 10.1002/cbdv.200690109.

Abstract

Four new pterocarpans, atricarpan A (=(-)-1,2-dihydroxy-4-(hydroxymethyl)-3,9-dimethoxypterocarpan; 1), atricarpan B (=(-)-2,3-ethylenedioxy)-1,4-dihydroxy-9-methoxypterocarpan; 2), atricarpan C (=(-)-1,9-dimethoxypterocarpan-3-carboxylic acid; 3), and atricarpan D (=(-)-2,9-dimethoxy-4-(5-oxohexyl)pterocarpan; 4) were isolated from the BuOH extract of the whole plant of Zygophyllum eurypterum. The structure elucidations of those compounds were based primarily on 1D- and 2D-NMR analysis, including COSY, HMBC, and HMQC correlations. Compounds 1-4 also inhibited butyrylcholinesterase (BChE; EC 3.1.1.8) enzyme in a concentration-dependent manner with IC(50) values between 12.5-65.0 microM. Similarly, compounds 1 and 4 inhibited lipoxygenase (LOX; EC 1.13.11.12) and acetylcholinesterase (AChE; EC 3.1.1.7) enzymes with IC50 values of 13.5 and 20.5 muM, respectively.

MeSH terms

  • Butyrylcholinesterase / chemistry
  • Cholinesterase Inhibitors* / chemistry
  • Cholinesterase Inhibitors* / isolation & purification
  • Cholinesterase Inhibitors* / pharmacology
  • Lipoxygenase Inhibitors* / chemistry
  • Lipoxygenase Inhibitors* / isolation & purification
  • Lipoxygenase Inhibitors* / pharmacology
  • Molecular Structure
  • Pterocarpans* / chemistry
  • Pterocarpans* / isolation & purification
  • Pterocarpans* / pharmacology
  • Structure-Activity Relationship
  • Zygophyllum / chemistry*

Substances

  • Cholinesterase Inhibitors
  • Lipoxygenase Inhibitors
  • Pterocarpans
  • Butyrylcholinesterase