Isolation and structural characterisation of a propoxyphenyl-linked thiohomosildenafil analogue found in a herbal product

Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(10):1693-700. doi: 10.1080/19440049.2013.823571. Epub 2013 Aug 28.

Abstract

A propoxyphenyl-linked thiohomosildenafil analogue, one of the sildenafil analogues, was found in an herbal product. It was isolated by semi-preparative high-performance liquid chromatography (HPLC). The structure was established based on a comparison of chromatographic and spectroscopic behaviour with other sildenafil analogues using HPLC with diode array detection, quadrupole time-of-flight mass spectrometry (Q-TOF/MS), and nuclear magnetic resonance (NMR) spectroscopy. The HPLC analysis showed separation from known sildenafil analogues with a similar chromatographic retention time. An [M + H](+) ion at m/z 519.22 was detected by mass spectrometry corresponding to an empirical formula of C24H34N6O3S2. The structure was similar to that of thiohomosildenafil, except that the ethoxy group attached to the phenyl ring was substituted for a propoxy group. It was assigned as 5-[2-propoxy-5-(4-ethylpiperazin-4-ylsulfonyl)phenyl]-3-methyl-1-n-propyl-4,5,dihydro-1H-pyrazole[7,1,d]pyrimidin-4-thione and named as propoxyphenyl-thiohomosildenafil because the structure was considerably similar to thiohomosildenafil.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Dietary Supplements / adverse effects
  • Dietary Supplements / analysis
  • Food Contamination / analysis*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Phosphodiesterase 5 Inhibitors / chemistry*
  • Piperazines / chemistry*
  • Plant Preparations / chemistry*
  • Purines / chemistry
  • Sildenafil Citrate
  • Sulfones / chemistry*

Substances

  • Phosphodiesterase 5 Inhibitors
  • Piperazines
  • Plant Preparations
  • Purines
  • Sulfones
  • Sildenafil Citrate