Isolation and identification of three thio-sildenafil analogues in dietary supplements

Lai, Kuo-Chih; Liu, Yi-Chu; Liao, Yung-Chih; Lin, Yun-Lian; Tsai, Li-Yao; Lin, Jer-Huei; Lo, Chi-Fang

doi:10.38212/2224-6614.2226

Cited by 2 publications

(3 citation statements)

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“…This peak was confirmed as the peak for hydroxythiohomosildenafil based on its similarity to a published MS/MS fragmentation pattern. 30 The assignments of the NMR spectra for the hydroxythiohomosildenafil Figure 3. Second derivative of NIR spectra of authentic (red line) and counterfeit (blue line) Viagra.…”

Section: Identification Of Herbal Product -Pronotonmentioning

confidence: 99%

Use of near infrared spectroscopy and spectral databases to assess the quality of pharmaceutical products and aid characterization of unknown components

Said

Gibbons

Moffat

et al. 2019

Journal of Near Infrared Spectroscopy

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This research was initiated as part of the fight against public health problems of rising counterfeit, substandard and poor quality medicines and herbal products. An effective screening strategy using a two-step combination approach of an incremental near infrared spectral database (step 1) followed by principal component analysis (step 2) was developed to overcome the limitations of current procedures for the identification of medicines by near infrared spectroscopy which rely on the direct comparison of the unknown spectra to spectra of reference samples or products. The near infrared spectral database consisted of almost 4000 spectra from different types of medicines acquired and stored in the database throughout the study. The spectra of the test samples (pharmaceutical and herbal formulations) were initially compared to the reference spectra of common medicines from the database using a correlation algorithm. Complementary similarity assessment of the spectra was conducted based on the observation of the principal component analysis score plot. The validation of the approach was achieved by the analysis of known counterfeit Viagra samples, as the spectra did not fully match with the spectra of samples from reliable sources and did not cluster together in the principal component analysis score plot. Pre-screening analysis of an herbal formulation (Pronoton) showed similarity with a product containing sildenafil citrate in the database. This finding supported by principal component analysis has indicated that the product was adulterated. The identification of a sildenafil analogue, hydroxythiohomosildenafil, was achieved by mass spectrometry and Nuclear Magnetic Resonance (NMR) analyses. This approach proved to be a suitable technique for quick, simple and cost-effective pre-screening of products for guiding the analysis of pharmaceutical and herbal formulations in the quest for the identification of potential adulterants.

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Section: Identification Of Herbal Product -Pronotonmentioning

confidence: 99%

Use of near infrared spectroscopy and spectral databases to assess the quality of pharmaceutical products and aid characterization of unknown components

Said

Gibbons

Moffat

et al. 2019

Journal of Near Infrared Spectroscopy

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“…This is what makes jamu manufacturers to add BKO into their products, with the aim of speeding up the desired therapeutic reactions [5]. In several studies that have been done, it was found that the presence of synthetic compounds that have similarities in chemical structure with sildenafil and often identified in small quantities contained in jamu (herbal medicine) special for men who circulate in the market or purchase online [6,7]. Generally the modification of this sildenafil structure lies in the piperazine ring and the presence of position exchange in the lactam portion between sulfur and oxygen.…”

Section: Introductionmentioning

confidence: 99%

“…Structure of (a) sildenafil, (b) thiosildenafil, dan (c) propoxyphenylhidroxyethylthiosildenafil[6,12] Analysis of Sildenafil and It's Derivatives In Jamu (Herbal Medicine)...(Rina Kurniaty, Khairan and Lelifajri) …”

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confidence: 99%

Analysis of Sildenafil and Its Derivatives in Jamu (Herbal Medicines) Using Lc/MS/MS Spectroscopy

Kurniaty

Khairan

Lelifajri

2018

J. Nat.

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Jamu (herbal medicine) is a traditional Indonesian medicine used to nourish, treat, and restore of health, as well as for beauty and fitness. A healthy Jamu is safe when consumed and free from chemicals (in Indonesia it’s called BKO). BKO is a medicinal chemical compound which is intentionally added in jamu (herbal medicine), which aims to increase the accelerate effects of Jamu or herbal medicine from the usual. The aims of this study are to extract, isolate, identify and elucidate the structure of the BKO of sildenafil and it’s derivatives in two herbal preparations circulating in the city of Banda Aceh. Extraction, isolation and identification of sildenafil BKO and its derivatives in jamu were done by using column chromatography (CC) and thin layer chromatography (TLC) meanwhile, the structure elucidation of sildenafil and it’s derivatives were done by Fourier-Transform Infra-Red (FT-IR) and liquid chromatography/mass spectroscopy (LC/MS/MS). The results of extraction, isolation and identification with a solvent ethyl acetate: methanol: ammonium hydroxide (25%) (100: 15: 1.5 v/v showed that two jamu circulating in Banda Aceh positively contained BKO sildenafil derivatives, namely thiosildenafil. The FT-IR analysis showed a strong absorption of thiocarbonyl (C=S) group at 1288-1242 cm-1, which is a typical uptake of the thiosildenafil compound. The Spectroscopy LC/MS/MS analysis using electron spray ionization (ESI-MS/MS) showed that the isolate have a similar spectra with thiosildenafil compound [TSLD+H]+ at 491 m/z and [TSLD+Na]+ at 513 m/z and other derivate of thiosildenafil, namely propoxyphenylhydroxylethylthiosildenafil [PHTSLD+H]+ at 533 m/z.

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Isolation and identification of three thio-sildenafil analogues in dietary supplements

Cited by 2 publications

References 1 publication

Use of near infrared spectroscopy and spectral databases to assess the quality of pharmaceutical products and aid characterization of unknown components

Use of near infrared spectroscopy and spectral databases to assess the quality of pharmaceutical products and aid characterization of unknown components

Analysis of Sildenafil and Its Derivatives in Jamu (Herbal Medicines) Using Lc/MS/MS Spectroscopy

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