Diethoxyphosphoryloxy-oleanolic acid is a nanomolar-inhibitor of butyrylcholinesterase

Chem Biol Drug Des. 2024 Mar;103(3):e14506. doi: 10.1111/cbdd.14506.

Abstract

A series of new betulin, lupeol, erythrodiol, and oleanolic acid phosphoryloxy- and furoyloxy-derivatives has been synthesized and their structure was confirmed by NMR spectroscopy. Synthesized compounds were subjected to Ellman's assays to determine their ability to inhibit the enzymes AChE and BChE. Among them, diethoxyphosphoryloxy-oleanolic acid inhibited BChE with a value of 99%, thereby acting as a mixed-type inhibitor holding very low Ki values of Ki = 6.59 nM and Ki ' = 1.97 nM, respectively.

Keywords: butyrylcholinesterase; furoyl; lupane; oleanane; phosphate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism
  • Butyrylcholinesterase / chemistry
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Oleanolic Acid* / pharmacology
  • Structure-Activity Relationship
  • Triterpenes* / chemistry
  • Triterpenes* / pharmacology

Substances

  • Butyrylcholinesterase
  • Cholinesterase Inhibitors
  • Acetylcholinesterase
  • Oleanolic Acid
  • Triterpenes

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