Stability studies of antiandrogenic compounds in Curcuma aeruginosa Roxb. extract

J Pharm Pharmacol. 2014 Sep;66(9):1282-93. doi: 10.1111/jphp.12216. Epub 2014 Jun 6.

Abstract

Objectives: Curcuma aeruginosa Roxb. extract is a 5α-reductase antagonist that can be used to treat hair loss. We aimed to study the stability of antiandrogenic constituents, germacrone and other sesquiterpene components in the extract.

Methods: Germacrone and the extract were analyzed as solid forms or solublized with polyethylene glycol-40 (PEG-40) or methanol using high-performance liquid chromatography and gas chromatography with flame ionization detector. The effects of pH, temperature and light on their stability were studied.

Key findings: Degradation of antiandrogenic compounds in C. aeruginosa was highly sensitive to temperature especially pure anhydrous germacrone, which was completely lost within 3 days at 45°C. Curiously, degradation was slower than as a dried extract. Paradoxically, when solubilized with PEG-40, it was largely intact even after 90 days at 45°C. The MS spectrum of a major degradation product suggested that it was elemenone probably produced by Cope rearrangement. Two other putative degradation products were germacrone-1,10-epoxide and germacrone-4,5-epoxide suggesting that oxidation of double bonds was an important mechanism. Germacrone stability was unaffected by pH (2.0-9.0) but only as dried extract it was slightly degraded by light.

Conclusion: Antiandrogenic constituents of C. aeruginosa were instable at high temperature and in solid form. Thus, the extract would be optimately stored as a solution or otherwise as solid form at low temperature.

Keywords: Curcuma aeruginosa; antiandrogen; degradation; germacrone; stability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androgens / metabolism*
  • Chromatography, High Pressure Liquid
  • Curcuma / chemistry*
  • Drug Stability
  • Hot Temperature
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • Polyethylene Glycols / chemistry
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes, Germacrane / chemistry*
  • Sesquiterpenes, Germacrane / pharmacology
  • Solubility

Substances

  • Androgens
  • Plant Extracts
  • Sesquiterpenes
  • Sesquiterpenes, Germacrane
  • Polyethylene Glycols
  • germacrone