Isolation and characterization of the acid and base degradation products of andrographolide

Pharmazie. 2018 Oct 1;73(10):559-562. doi: 10.1691/ph.2018.8082.

Abstract

Andrographolide was subjected to degradation under acidic and basic conditions. Three degradation products including two novel compounds, 8,9-didehydroandrographolide (AG-A) and 15-seco-andrographolide (AG-B2), and a known product, 14-deoxy-11,12-didehydroandrographolide (AG-B1), were isolated by chromatography and identified on the basis of their NMR and MS data. The degradation product, AG-A, may result from the isomerization of andrographolide under acidic conditions whereas the base degradation products, AG-B1 and AG-B2, were formed most likely due to the dehydration of allyl alcohol and the hydrolysis of andrographolide at the lactone ring, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification*
  • Drug Stability
  • Hydrochloric Acid / chemistry
  • Hydrolysis
  • Mass Spectrometry
  • Sodium Hydroxide / chemistry

Substances

  • Diterpenes
  • andrographolide
  • Sodium Hydroxide
  • Hydrochloric Acid