Unambiguous Characterization of Commercial Natural (Dihydro)phenanthrene Compounds Is Vital in the Discovery of AMPK Activators

J Agric Food Chem. 2024 Jul 3;72(26):14993-15004. doi: 10.1021/acs.jafc.4c01616. Epub 2024 Jun 19.

Abstract

These days, easy access to commercially available (poly)phenolic compounds has expanded the scope of potential research beyond the field of chemistry, particularly in the area of their bioactivity. However, the quality of these compounds is often overlooked or not even considered. This issue is illustrated in this study through the example of (dihydro)phenanthrenes, a group of natural products present in yams, as AMP-activated protein kinase (AMPK) activators. A study conducted in our group on a series of compounds, fully characterized using a combination of chemical synthesis, NMR and MS techniques, provided evidence that the conclusions of a previous study were erroneous, likely due to the use of a misidentified commercial compound by its supplier. Furthermore, we demonstrated that additional representatives of the (dihydro)phenanthrene phytochemical classes were able to directly activate AMPK, avoiding the risk of misinterpretation of results based on analysis of a single compound alone.

Keywords: AMPK activator; Dioscorea; dihydrophenanthrene; organic synthesis; phenanthrene; quality control; structure characterization; yam.

MeSH terms

  • AMP-Activated Protein Kinases* / genetics
  • AMP-Activated Protein Kinases* / metabolism
  • Biological Products / chemistry
  • Biological Products / pharmacology
  • Humans
  • Molecular Structure
  • Phenanthrenes* / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology

Substances

  • AMP-Activated Protein Kinases
  • Phenanthrenes
  • Biological Products
  • Plant Extracts