Identification of descarbonsildenafil in an adulterated dietary supplement and evaluation of its inhibitory activity for phosphodiesterase type 5 (PDE5)
2020
Ichikawa-Kaji, Y. ((Tokyo Metropolitan Institute of Public Health, Shinjuku-ku, Tokyo (Japan)), (University of Tsukuba, Tsukuba, Ibaraki (Japan))) | Nakajima, J. | Kikkawa, S. | Ishizawa, F. | Nishiyama, R. | Kishimoto, K. | Uemura, N. | Satoh, M. | Suzuki, J. | Inomata, A. | Nakae, D. | Azumaya, I. | Honda, K. | Moriyasu, T.
Some illegal dietary supplements contain phosphodiesterase type 5 (PDE5) inhibitors, such as sildenafil, for exerting "therapeutic" effects in erectile dysfunction. This is apparently dangerous, and thus, should be appropriately regulated. Identification of descarbonsildenafil was first reported in Singapore in a coffee sample labeled to exert male sexual performance enhancement effects. However, it is unclear whether the compound possesses PDE5 inhibitory activity. We encountered during our survey of dietary supplements, a sexual enhancement product commercially available in Tokyo, in which a peak presumed to be of descarbonsildenafil was detected by LC-UV and electrospray ionization-tandem MS (ESI-MS/MS). The compound was isolated and identified as descarbonsildenafil with liquid chromatography-quadrupole time-of-flight-mass spectrometry (LC-QTOF-MS), NMR, and X-ray crystal structural analysis. In addition, descarbonsildenafil showed PDE5 inhibitory activity in PDE5 inhibition assay, and its IC sub (50) value for PDE5A1 was found to be 30 nmol/L. The results of INADEQUATE NMR and X-ray crystal structural analysis in this study provide information for the identification of descarbonsildenafil. Since this study indicates that this compound is a PDE5 inhibitor having adequate activity, it is regulated as a drug component in Japan.
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