Structural Determination, Biological Function, and Molecular Modelling Studies of Sulfoaildenafil Adulterated in Herbal Dietary Supplement.

Kanchanok Kodchakorn,Nawarat Viriyakhasem,Tunchanok Wongwichai,Prachya Kongtawelert

doi:10.3390/molecules26040949

Kanchanok Kodchakorn, Nawarat Viriyakhasem + Show 2 more

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https://doi.org/10.3390/molecules26040949

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Abstract

Unapproved ingredients included in herbal medicines and dietary supplements have been detected as adulterated synthetic drugs used for erectile dysfunction. Extraction from a dietary supplement was performed to isolate the compounds by HPLC analysis. The structural characterization was confirmed using mass spectrometry (ESI-TOF/MS and LC-MS/MS), 1H NMR, and 13C NMR spectroscopy techniques. Results identified the thus-obtained compound to be sulfoaildenafil, a thioketone analogue of sildenafil. The biological activities of this active compound have been focused for the first time by the experimental point of view performance in vitro. The results revealed that sulfoaildenafil can affect the therapeutic level of nitric oxide through the upregulation of nitric oxide synthase and phosphodiesterase type 5 (PDE5) gene expressions. This bulk material, which displays structural similarity to sildenafil, was analyzed for the presence of a PDE5 inhibitor using a theoretical calculation. These unique features of the potential activity of PDE5 protein and its inhibitors, sildenafil and sulfoaildenafil, may play a key consideration for understanding the mode of actions and predicting the biological activities of PDE5 inhibitors.

Highlights

Herbal medicines or dietary supplements have been popularized and advertised as natural and safe for human consumption
The -obtained compound has been characterized in terms of its structure by comparing the 1H Nuclear magnetic resonance (NMR), 13C NMR spectroscopy, and mass spectrometry
The characteristic structure was confirmed by distortionless enhancement by polarization transfer (DEPT) 90◦/135◦ NMR and 1H-13C HSQC as shown in Figures S2 and S3 (Supplementary Information)

Summary

Introduction

Herbal medicines or dietary supplements have been popularized and advertised as natural and safe for human consumption. Current reports have proposed that, in general, analogues of sildenafil display a variety of cellular functions, including muscle relaxation, anti-inflammation, and signal transduction [18], in addition to displaying beneficial effects of sexual endothelial dysfunction and pulmonary hypertension. According to this situation, when sexual stimulation causes a local release of NO, the synthetic inhibitory effects of PDE5 creates a retaining intracellular cyclic guanosine monophosphate (cGMP) levels, resulting in muscle relaxation and an inflow of blood into the corpus cavernosum penis

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