M. Iannone, F. Botré, S. Parenti
Oct 15, 2019
Citations
1
Influential Citations
4
Citations
Quality indicators
Journal
Rapid communications in mass spectrometry : RCM
Abstract
RATIONALE Isoflavones are a group of flavonoids that may be of interest in sport doping because they can be used by athletes in the recovering periods after the administration of anabolic steroids, with the aim of increasing the natural production of luteinizing hormone (LH) and, consequently, the biosynthesis of endogenous androgens. METHODS The in vivo metabolism of methoxyisoflavone (5-methyl-7-methoxy-isoflavone) and ipriflavone (7-isopropoxy-isoflavone), respectively present in a dietary supplement and in a pharmaceutical preparation, was investigated. The study was carried out by the analysis of urinary samples collected from male caucasian subjects before, during and after the oral administration of methoxyisoflavone or ipriflavone. After enzymatic hydrolysis and liquid-liquid extraction, all urinary samples were analyzed by GC/qTOF electron ionization MS. RESULTS Eight metabolites of methoxyisoflavone and six metabolites of ipriflavone were isolated. The corresponding accurate mass spectra are specific of isoflavone structures and revealed also a retro Diels-Alder fragmentation. CONCLUSION When excreted in large amounts, the urinary metabolites of methoxyisoflavone and ipriflavone can be traced to potential confounding factors in doping analysis. As methoxyisoflavone and ipriflavone have been shown to inhibit the enzyme aromatase, thus interfering with the normal metabolic pathways of testosterone, the detection of their intake, by screening for the presence of their main metabolites in urine, might be helpful in routine doping control analysis.