Ichikawa-Kaji Yoko, Nakajima Jun'ichi, Kikkawa Shoko, Ishizawa Fujio, Nishiyama Rei, Kishimoto Kiyoko, Uemura Nozomi, Satoh Miki, Suzuki Jin, Inomata Akiko, Nakae Dai, Azumaya Isao, Honda Katsuya, Moriyasu Takako
Tokyo Metropolitan Institute of Public Health.
Shokuhin Eiseigaku Zasshi. 2020;61(1):34-40. doi: 10.3358/shokueishi.61.34.
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 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.
一些非法膳食补充剂含有5型磷酸二酯酶（PDE5）抑制剂，如西地那非，用于在勃起功能障碍中发挥“治疗”作用。这显然很危险，因此应进行适当监管。去碳西地那非的鉴定首次在新加坡被报道，在一个标有增强男性性功能作用的咖啡样品中。然而，尚不清楚该化合物是否具有PDE5抑制活性。在我们对膳食补充剂的调查过程中，我们在东京发现了一种市售的性增强产品，通过液相色谱-紫外检测（LC-UV）和电喷雾电离串联质谱（ESI-MS/MS）检测到一个推测为去碳西地那非的峰。该化合物通过液相色谱-四极杆飞行时间质谱（LC-QTOF-MS）、核磁共振（NMR）和X射线晶体结构分析进行分离和鉴定。此外，去碳西地那非在PDE5抑制试验中显示出PDE5抑制活性，其对PDE5A1的半数抑制浓度（IC）值为30 nmol/L。本研究中INADEQUATE NMR和X射线晶体结构分析的结果为去碳西地那非的鉴定提供了信息。由于本研究表明该化合物是一种具有足够活性的PDE5抑制剂，因此在日本它被作为药物成分进行监管。
