human monoamine oxidase (hMAO) A and hMAO B inhibitors from Artemisia dracunculus L. herniarin and skimmin: human mononamine oxidase A and B inhibitors from A. dracunculus L

Z Naturforsch C J Biosci. 2020 Nov 26;75(11-12):459-466. doi: 10.1515/znc-2019-0227.

Abstract

The aim of this study was to investigate the effects of extracts and pure Artemisia dracunculus L. (tarragon) metabolites on the antimonoamine oxidase and anticholinesterase activities. The compounds were characterized as stigmasterol (1), herniarin (2), (2E,4E)-1-(piperidin-1-yl)undeca-2,4-diene-8,10-diyn-1-one (3), (2E,4E)-N-isobutylundeca-2,4-dien-8,10-diynamide (4), 3,4-dehydroherniarin (5) and skimmin (6) by 1H-NMR, 13C-NMR, 1D and 2D NMR methods. The compounds 5 and 6 were isolated from tarragon for the first time. The extracts and pure compounds have inhibitory effects on the human monoamine oxidase (hMAO) A and B enzymes, whereas they did not exhibit any anticholinesterase activities. Among the tarragon compounds, only 2 and 6 compounds showed the inhibitory effects against hMAO A (IC50 = 51.76 and 73.47 μM, respectively) and hMAO B (IC50 = 0.84 and 1.63 mM, respectively). In the study, herniarin content in the extracts was also analysed by high-performance liquid chromatography and it was found that there was a relationship between the inhibition effects of the extracts and their herniarin content.

Keywords: Artemisia dracunculus L.; cholinesterase; herniarin; monoamine oxidase; skimmin.

MeSH terms

  • Artemisia / chemistry*
  • Coumarins / pharmacology*
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Monoamine Oxidase / drug effects*
  • Monoamine Oxidase Inhibitors / pharmacology
  • Umbelliferones / pharmacology*

Substances

  • Coumarins
  • Enzyme Inhibitors
  • Monoamine Oxidase Inhibitors
  • Umbelliferones
  • herniarin
  • Monoamine Oxidase
  • monoamine oxidase A, human
  • skimmin