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Separation and structural elucidation of a novel vardenafil analogue as an adulterant in a natural health care dietary supplement.

ABSTRACT: A novel vardenafil analogue was identified in dietary supplement as an adulterant in herbal formulations. The structure of this analogue was elucidated using HRMS, NMR after extraction from the pulverized powder. It was named morphardenafil as a morpholine ring has replaced the N-ethyl piperazine ring in vardenafil. A tablet of this dietary supplement contained about 50 mg of unspecified morphardenafil, which is 2.5 - 20-times the prescriptive dosage of Levetra, the commercial formulation of the vardenafil monohydrochloride salt in the market and probably places unwary consumers at risk for potentially serious adverse effects or drug-drug interaction (DDI).

SUBMITTER: Li C

PROVIDER: S-EPMC10147979 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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Separation and structural elucidation of a novel vardenafil analogue as an adulterant in a natural health care dietary supplement.

Li Chunzheng C Wang Xinzheng X Wu Shengming S Zhao Junqing J Fang Junjian J Li Hui H Zhu Yingjie Y Zhang Kang K Peng Jing J Mao Jie J Li Weihua W He Kun K Wang Na N Dong Fangting F

Heliyon 20230412 4

A novel vardenafil analogue was identified in dietary supplement as an adulterant in herbal formulations. The structure of this analogue was elucidated using HRMS, NMR after extraction from the pulverized powder. It was named morphardenafil as a morpholine ring has replaced the <i>N</i>-ethyl piperazine ring in vardenafil. A tablet of this dietary supplement contained about 50 mg of unspecified morphardenafil, which is 2.5 - 20-times the prescriptive dosage of Levetra, the commercial formulation ...[more]

PMID: 37128339

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Project description:The proliferation of adulterated health foods and beverages in the market demands a comprehensive analytical strategy to identify the adulterants, particularly those of isomeric phosphodiesterase 5 (PDE5) inhibitors. An instant coffee premix (ICP) purchased from an online retailer was flagged for suspected adulteration through PDE5 inhibition assay. The ICP was then analysed using suspected-target and non-targeted screenings of a liquid chromatography-quadrupole time-of-flight mass spectrometry. Based on these findings, a PDE5 inhibitor initially assigned as compound X was isolated from the ICP by employing a liquid chromatography-diode array detection before its structural elucidation with liquid chromatography-ultraviolet (LC-UV) spectroscopy and nuclear magnetic resonance (NMR) spectroscopy. The suspected-target screening matched the protonated molecule ([M + H]+) precursor ion of compound X at m/z 499.2310 with two suspected analytes that are structural isomers of one another. The fragmentation patterns of compound X were comparable to those analogues in the dithiocarbodenafil group through the non-targeted screening. These findings, complemented by the LC-UV and NMR spectroscopy data, together with the chromatographic separation of related structural isomers, conclude the identity of compound X. To our best knowledge, this is the first study to report the presence of 3,5-dimethylpiperazinyl-dithiodesmethylcarbodenafil in an ICP sample.Key pointsThe herbal-based male sexual performance products' lucrative market has instigated their rampant adulteration, particularly with PDE5 inhibitors.The adulterated products may also contain analogues of the approved PDE5 inhibitors, which usually passed into the market undetected as they are not included in the routine targeted screening procedure.The present study detected, isolated, and identified an isomeric sildenafil analogue from an instant coffee premix sample using rapid qualitative assay and comprehensive analytical analysis.This paper highlighted the applicability of the established strategies for routine casework, particularly in a forensic drug testing laboratory.

Project description:BackgroundUsing sports supplements is common among athletes. The presence of anabolic steroids in sports supplements as a hormonal contaminant can increase production efficiency. Since anabolic steroids cause health problems and result in positive doping tests in athletes, it is important to investigate their presence in the supplement preparations consumed by athletes.ObjectivesThis paper aims to simultaneously determine ten anabolic steroids by high-performance thin-layer chromatography (HPTLC) method in sports supplements.MethodsChromatographic analysis was conducted on glass silica gel 60F254 plates. The extracts loaded on silica gel plates are subjected to programed multiple development (PMD) to separate anabolic androgenic steroids (AASs). Densitometric scanning is carried out at the wavelength of 245 and 366nm. The method was validated according to the ICH guidelines.ResultsSpots at retardation factor (Rf) 0.72 (elution system 1), 0.4 (elution system 1), 0.29 (elution system 2), 0.25 (elution system 2), 0.1 (elution system 1), 0.65 (elution system 2), 0.59 (elution system 1), 0.44 (elution system 1), 0.8 (elution system 3), and 0.82 (elution system 3) values were recognized as 19-nor androstenedione, 19-nortestosterone, methyl testosterone, clostebol, stanozolol, trenbolone enanthate, oxymetholone, oxandrolone, testosterone enanthate, and nandrolone decanoate, respectively. The linear ranges were 25 - 250 μg/mL for oxymetholone, 7 - 50 μg/mL for 19-nor androstenedione, 19-nortestosterone, and oxandrolone, and 3 - 20 μg/mL for methyl testosterone, clostebol, stanozolol, trenbolone enanthate, testosterone enanthate, and nandrolone decanoate. The developed method is validated by acceptable precision (CV < 20%) and good accuracy (94% < R < 114%). The value of limit of detection (LOD) for all derivatives was in the range of 0.02 - 0.16 μg/spot (20-160 μg/g of supplement), while limit of quantitation (LOQ) was found to be in the range of 0.06 - 0.5 μg/spot (60 - 500 μg/g of supplement). Fifty sports supplement samples as real sample were collected and analyzed. None of the samples screened positive using the HPTLC method.ConclusionsIn the present study, the fast, cheap, and simple HPTLC method could be used for the multi-residue analysis of ten anabolic androgenic steroids in sports supplements.

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Separation and structural elucidation of a novel vardenafil analogue as an adulterant in a natural health care dietary supplement.

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Separation and structural elucidation of a novel vardenafil analogue as an adulterant in a natural health care dietary supplement.

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