Determination of a New Type of Phosphodiesterase-5 Inhibitor, Thioquinapiperifil, in a Dietary Supplement Promoted for Sexual Enhancement

Uchiyama, Nahoko; Saisho, Kazuhiro; Kikura‐Hanajiri, Ruri; Haishima, Yuji; Goda, Yukihiro

doi:10.1248/cpb.56.1331

Cited by 25 publications

(7 citation statements)

References 23 publications

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“…Furthermore, another new type of PDE-5 inhibitor, thioquinapiperifil, an imidazoquinazoline derivative, was also detected in a dietary supplement. 26) This compound was first synthesized as KF31327 by Kyowa Hakko Kogyo Co., Ltd., and Hirose et al reported that it was a more potent and selective PDE-5 inhibitor than sildenafil. [27][28][29] In this paper, we report the analysis and structural elucidation of a new sildenafil analogue, cyclopentynafil and a new tadalafil analogue, N-octylnortadalafil, that were isolated from a dietary supplement illegally marketed for erectile dysfunction.…”

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Isolation and Structural Elucidation of Cyclopentynafil and N-Octylnortadalafil Found in a Dietary Supplement

Hasegawa

Takahashi

Saijo

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new sildenafil analogue, cyclopentynafil (1) and a new tadalafil analogue, N-octylnortadalafil (2) were isolated from a dietary supplement illegally marketed for erectile dysfunction. The structures of the sildenafil and tadalafil analogues were elucidated by using HPLC-photodiode array (PDA), LC-MS, high-resolution MS, NMR and circular dichroism (CD). These compounds were determined to be 5- In this paper, we report the analysis and structural elucidation of a new sildenafil analogue, cyclopentynafil and a new tadalafil analogue, N-octylnortadalafil, that were isolated from a dietary supplement illegally marketed for erectile dysfunction. ExperimentalChemicals and Reagents HPLC-grade acetonitrile and all other reagents (analytical grade) were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan).Sample The examined product was purchased as a processed food composed mainly of walnuts through the Internet and was composed of four pieces of ivory tablets (400 mg). The product properties were as follows: product name; Highperwalnup 2, producing company; Art Creation Co., Ltd., sales company; Ogawa Planning Co., Ltd., date of purchase; December 28, 2007.Preparation of Sample Solution One tablet was finely powdered, and 100 mg of the powder was ultrasonically extracted in 10 ml of 70% methanol for 15 min. The extract was centrifuged at 1700ϫg. The supernatant was filtered through a 0.45 mm filter. The filtrate was used for HPLC, and a portion of it was diluted 10-fold with methanol for liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) analysis.HPLC Analysis HPLC analysis was performed using a JASCO PU-2089 apparatus equipped with a photodiode array (PDA) detector model MD-2015 (JASCO Corporation, Tokyo, Japan). The sample solution was separated by using a TSK-GEL ODS-80Ts column (150ϫ4.6 mm i.d., 5 mm, Tosoh Co., Tokyo, Japan). The mobile phase was an acetonitrile/water/phosphoric acid (100 : 900 : 1) mixture solution containing 5 mmol/l sodium hexanesulfonate (eluent A) and an acetonitrile/water/phosphoric acid (900 : 100 : 1) mixture solution containing 5 mmol/l sodium hexanesulfonate (eluent B). The gradient elution was started at 90% eluent A, and was linearly decreased to 55% A in 25 min and to 10% A in 44-49 min. The flow rate of the mobile phase was set at 1.0 ml/min, and the injection volume was 20 ml. The column temperature was maintained at 40°C. The PDA detection wavelength was set from ultraviolet (UV) 200 to 400 nm, and max-plot chromatographic monitoring was performed (200-400 nm).LC-ESI-MS Analysis LC-ESI-MS analysis was performed using a Waters alliance 2695 separation module and ZQ mass spectrometer (Waters Corporation, Milford, MA, U.S.A.). The sample solution was separated by using an Atlantis dC18 column (150ϫ2.1 mm i.d., 3 mm, Waters Corporation). The mobile phase was 0.1% formic acid aqueous solution (eluent A) and acetonitrile containing 0.1% formic acid (eluent B). The gradient elution began at 95% eluent A, and linearly decreased to 80% A in 15 min and ...

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Isolation and Structural Elucidation of Cyclopentynafil and N-Octylnortadalafil Found in a Dietary Supplement

Hasegawa

Takahashi

Saijo

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Except for the mobile phase A and the flow rate, chromatographic conditions were based on the methods of the National Institute of Health Sciences in Japan 5) . The method has previously been used to analyze 20 different medicinal ingredients and analogs using 5 mM ammonium formate (pH 3. .…”

Section: Optimization Of Chromatographic Separation Conditionsmentioning

confidence: 99%

Simultaneous Identification of Hydroxythiohomosildenafil, Aminotadalafil, Thiosildenafil, Dimethylsildenafil, and Thiodimethylsildenafil in Dietary Supplements Using High-Performance Liquid Chromatography-Mass Spectrometry

貴臣

章弘

安紀子

et al. 2013

Journal of the Food Hygienics Society of Japan

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We developed a method for the separation and identification of illegal adulterants (hydroxythiohomosildenafil, aminotadalafil, thiosildenafil, dimethylsildenafil, and thiodimethylsildenafil) from dietary supplements using high-performance liquid chromatography-mass spectrometry. The separation was achieved on a C 18 column: the mobile phase consisted of 5 mM ammonium formate (pH 6.3)-acetonitrile (75 : 25, v/v) and acetonitrile, with gradient elution at a flow rate of 0.2 mL/ min. The proposed method could also be used to separate vardenafil, homosildenafil, and dimethylsildenafil, all of which have the same molecular weight. Furthermore, the proposed method could simultaneously separate hydroxythiohomosildenafil, aminotadalafil, thiosildenafil, dimethylsildenafil, thiodimethylsildenafil, vardenafil, and homosildenafil. Thus, this method may be useful to identify medicinal ingredients for erectile dysfunction and their analogs and to control the quality of dietary supplements.

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“…Various illegal adulterants, such as pharmaceuticals and their derivatives, continue to be detected in health foods and herbal medicines . Many new methods have been developed to determine these substances , especially HPLC–MS, e.g.…”

Section: Introductionmentioning

confidence: 99%

Novel strategy for the determination of illegal adulterants in health foods and herbal medicines using high‐performance liquid chromatography with high‐resolution mass spectrometry

Wang

et al. 2015

J of Separation Science

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The detection, confirmation, and quantification of multiple illegal adulterants in health foods and herbal medicines by using a single analytical method are a challenge. This paper reports on a new strategy to meet this challenge by employing high-performance liquid chromatography coupled with high-resolution mass spectrometry and a mass spectral tree similarity filter technique. This analytical method can rapidly collect high-resolution, high-accuracy, optionally multistage mass data for compounds in samples. After a preliminary screening by retention time and high-resolution mass spectral data, known illegal adulterants can be detected. The mass spectral tree similarity filter technique has been applied to rapidly confirm these adulterants and simultaneously discover unknown ones. By using full-scan mass spectra as stem and data-dependent subsequent stage mass spectra to form branches, mass spectrometry data from detected compounds are converted into mass spectral trees. The known or unknown illegal adulterants in the samples are confirmed or discovered based on the similarity between their mass spectral trees and those of the references in a library, and they are finally quantified against standard curves. This new strategy has been tested by using 50 samples, and the illegal adulterants were rapidly and effectively detected, confirmed and quantified.

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Determination of a New Type of Phosphodiesterase-5 Inhibitor, Thioquinapiperifil, in a Dietary Supplement Promoted for Sexual Enhancement

Cited by 25 publications

References 23 publications

Isolation and Structural Elucidation of Cyclopentynafil and N-Octylnortadalafil Found in a Dietary Supplement

Isolation and Structural Elucidation of Cyclopentynafil and N-Octylnortadalafil Found in a Dietary Supplement

Simultaneous Identification of Hydroxythiohomosildenafil, Aminotadalafil, Thiosildenafil, Dimethylsildenafil, and Thiodimethylsildenafil in Dietary Supplements Using High-Performance Liquid Chromatography-Mass Spectrometry

Novel strategy for the determination of illegal adulterants in health foods and herbal medicines using high‐performance liquid chromatography with high‐resolution mass spectrometry

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