A dihydrochalcone and several homoisoflavonoids from Polygonatum odoratum are activators of adenosine monophosphate-activated protein kinase

Bioorg Med Chem Lett. 2013 Jun 1;23(11):3137-9. doi: 10.1016/j.bmcl.2013.04.027. Epub 2013 Apr 17.

Abstract

Adenosine monophosphate (AMP)-activated protein kinase (AMPK) is a major cellular energy sensor and master regulator of metabolic homeostasis; thus, AMPK plays a central role in studies on diabetes and related metabolic diseases. From the rhizomes of Polygonatum odoratum (Mill.) Druce, six homoisoflavonoids (1-6) and one dihydrochalcone (7) were isolated, and the structures of polygonatones A-D (4-7) were elucidated by various spectroscopic analyses. Compounds 1-7 were evaluated for their effect on AMPK activation. The amount of active phosphorylated AMPK and acetyl-CoA carboxylase in rat liver epithelial IAR-20 cells increased when the cells were incubated with the aforementioned compounds. Specifically, (3R)-5,7-dihydroxyl-6-methyl-8-methoxyl-3-(4'-hydroxylbenzyl)-chroman-4-one (1), (3R)-5,7-dihydroxyl-6,8-dimethyl-3-(4'-hydroxylbenzyl)-chroman-4-one (2), (3R)-5,7-dihydroxyl-6-methyl-3-(4'-hydroxylbenzyl)-chroman-4-one (3), and polygonatone D (7) exhibited significant activation effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3-L1 Cells
  • AMP-Activated Protein Kinases / chemistry
  • AMP-Activated Protein Kinases / metabolism*
  • Acetyl-CoA Carboxylase / chemistry
  • Acetyl-CoA Carboxylase / metabolism
  • Animals
  • Cell Line
  • Chalcones / chemistry*
  • Chalcones / isolation & purification
  • Chalcones / pharmacology
  • Isoflavones / chemistry*
  • Isoflavones / isolation & purification
  • Isoflavones / pharmacology
  • Mice
  • Phosphorylation / drug effects
  • Polygonatum / chemistry*
  • Rats
  • Rhizome / chemistry

Substances

  • Chalcones
  • Isoflavones
  • AMP-Activated Protein Kinases
  • Acetyl-CoA Carboxylase
  • dihydrochalcone