Identification of Descarbonsildenafil in an Adulterated Dietary Supplement and Evaluation of Its Inhibitory Activity for Phosphodiesterase Type 5 (PDE5)
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...
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| Veröffentlicht in: | Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) 2020/02/25, Vol.61(1), pp.34-40 |
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| creator | 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 |
| description | 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 IC50 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. |
| doi_str_mv | 10.3358/shokueishi.61.34 |
| format | Article |
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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 IC50 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.</description><identifier>ISSN: 0015-6426</identifier><identifier>EISSN: 1882-1006</identifier><identifier>DOI: 10.3358/shokueishi.61.34</identifier><identifier>PMID: 32336717</identifier><language>eng ; jpn</language><publisher>Japan: Japanese Society for Food Hygiene and Safety</publisher><subject>Coffee ; Crystal structure ; descarbonsildenafil ; Diet ; dietary supplement product ; Dietary supplements ; Erectile dysfunction ; Identification ; INADEQUATE NMR ; Ionization ; Ions ; Liquid chromatography ; Mass spectrometry ; Mass spectroscopy ; NMR ; Nuclear magnetic resonance ; Performance enhancement ; Phosphodiesterase ; phosphodiesterase type 5 inhibitor ; Quadrupoles ; Sildenafil ; Structural analysis ; Surveying ; X rays ; X-ray crystal structural analysis</subject><ispartof>Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi), 2020/02/25, Vol.61(1), pp.34-40</ispartof><rights>2020 Japanese Society for Food Hygiene and Safety</rights><rights>Copyright Japan Science and Technology Agency 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c544t-7cfe98f8fcdc2b7ce2f2d5cb195cd0311240fcb811cd935af2c02625d4aabea93</citedby><cites>FETCH-LOGICAL-c544t-7cfe98f8fcdc2b7ce2f2d5cb195cd0311240fcb811cd935af2c02625d4aabea93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32336717$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ichikawa-Kaji, Yoko</creatorcontrib><creatorcontrib>Nakajima, Jun’ichi</creatorcontrib><creatorcontrib>Kikkawa, Shoko</creatorcontrib><creatorcontrib>Ishizawa, Fujio</creatorcontrib><creatorcontrib>Nishiyama, Rei</creatorcontrib><creatorcontrib>Kishimoto, Kiyoko</creatorcontrib><creatorcontrib>Uemura, Nozomi</creatorcontrib><creatorcontrib>Satoh, Miki</creatorcontrib><creatorcontrib>Suzuki, Jin</creatorcontrib><creatorcontrib>Inomata, Akiko</creatorcontrib><creatorcontrib>Nakae, Dai</creatorcontrib><creatorcontrib>Azumaya, Isao</creatorcontrib><creatorcontrib>Honda, Katsuya</creatorcontrib><creatorcontrib>Moriyasu, Takako</creatorcontrib><creatorcontrib>Tokyo Metropolitan Institute of Public Health</creatorcontrib><creatorcontrib>Toho University</creatorcontrib><creatorcontrib>University of Tsukuba</creatorcontrib><creatorcontrib>Tokyo University of Agriculture</creatorcontrib><title>Identification of Descarbonsildenafil in an Adulterated Dietary Supplement and Evaluation of Its Inhibitory Activity for Phosphodiesterase Type 5 (PDE5)</title><title>Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)</title><addtitle>Food Hyg. Saf. Sci.</addtitle><description>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 IC50 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.</description><subject>Coffee</subject><subject>Crystal structure</subject><subject>descarbonsildenafil</subject><subject>Diet</subject><subject>dietary supplement product</subject><subject>Dietary supplements</subject><subject>Erectile dysfunction</subject><subject>Identification</subject><subject>INADEQUATE NMR</subject><subject>Ionization</subject><subject>Ions</subject><subject>Liquid chromatography</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Performance enhancement</subject><subject>Phosphodiesterase</subject><subject>phosphodiesterase type 5 inhibitor</subject><subject>Quadrupoles</subject><subject>Sildenafil</subject><subject>Structural analysis</subject><subject>Surveying</subject><subject>X rays</subject><subject>X-ray crystal structural analysis</subject><issn>0015-6426</issn><issn>1882-1006</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpdkctuEzEUhkcIRKPSPStkiQ1dTPB1LssoSdtIlahEWVse-5hxmYwH21Mpb8Lj4igllVjYZ3H-853LXxQfCV4yJpqvsfe_ZnCxd8uKLBl_UyxI09CSYFy9LRYYE1FWnFYXxVWMrsMU85rWbfW-uGCUsaom9aL4szMwJmedVsn5EXmLNhC1Cp0foxtyUlk3IDciNaKVmYcEQSUwaOMgqXBA3-dpGmCfIVlh0PZZDfMZtUsR7cbedS75rF3p5J5dOiDrA3rofZx6bxzEIzMCejxMgAT68rDZiusPxTurhghXL_Gy-HGzfVzflfffbnfr1X2pBeeprLWFtrGN1UbTrtZALTVCd6QV2mBGCOXY6q4hRJuWCWWpxrSiwnClOlAtuyw-n7hT8L_nPIt88nMYc0tJWctZS6umyip8UungYwxg5RTcPu8vCZZHN-SrG7IikvFc8ukFPHd7MOeCf7fPgtuTIGfz-Qc_Dm6E1_bghfXe9JJm62Q2lWByDPkxnj9OGG8EbppMWp9ITzGpn3BupUJyeoD_ZiOnAc9Z3asgYWR_AQymuwQ</recordid><startdate>20200225</startdate><enddate>20200225</enddate><creator>Ichikawa-Kaji, Yoko</creator><creator>Nakajima, Jun’ichi</creator><creator>Kikkawa, Shoko</creator><creator>Ishizawa, Fujio</creator><creator>Nishiyama, Rei</creator><creator>Kishimoto, Kiyoko</creator><creator>Uemura, Nozomi</creator><creator>Satoh, Miki</creator><creator>Suzuki, Jin</creator><creator>Inomata, Akiko</creator><creator>Nakae, Dai</creator><creator>Azumaya, Isao</creator><creator>Honda, Katsuya</creator><creator>Moriyasu, Takako</creator><general>Japanese Society for Food Hygiene and Safety</general><general>Japan Science and Technology Agency</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7T2</scope><scope>7T7</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>FR3</scope><scope>H95</scope><scope>H96</scope><scope>H97</scope><scope>H98</scope><scope>H99</scope><scope>L.F</scope><scope>L.G</scope><scope>P64</scope></search><sort><creationdate>20200225</creationdate><title>Identification of Descarbonsildenafil in an Adulterated Dietary Supplement and Evaluation of Its Inhibitory Activity for Phosphodiesterase Type 5 (PDE5)</title><author>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</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c544t-7cfe98f8fcdc2b7ce2f2d5cb195cd0311240fcb811cd935af2c02625d4aabea93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; jpn</language><creationdate>2020</creationdate><topic>Coffee</topic><topic>Crystal structure</topic><topic>descarbonsildenafil</topic><topic>Diet</topic><topic>dietary supplement product</topic><topic>Dietary supplements</topic><topic>Erectile dysfunction</topic><topic>Identification</topic><topic>INADEQUATE NMR</topic><topic>Ionization</topic><topic>Ions</topic><topic>Liquid chromatography</topic><topic>Mass spectrometry</topic><topic>Mass spectroscopy</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Performance enhancement</topic><topic>Phosphodiesterase</topic><topic>phosphodiesterase type 5 inhibitor</topic><topic>Quadrupoles</topic><topic>Sildenafil</topic><topic>Structural analysis</topic><topic>Surveying</topic><topic>X rays</topic><topic>X-ray crystal structural analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ichikawa-Kaji, Yoko</creatorcontrib><creatorcontrib>Nakajima, Jun’ichi</creatorcontrib><creatorcontrib>Kikkawa, Shoko</creatorcontrib><creatorcontrib>Ishizawa, Fujio</creatorcontrib><creatorcontrib>Nishiyama, Rei</creatorcontrib><creatorcontrib>Kishimoto, Kiyoko</creatorcontrib><creatorcontrib>Uemura, Nozomi</creatorcontrib><creatorcontrib>Satoh, Miki</creatorcontrib><creatorcontrib>Suzuki, Jin</creatorcontrib><creatorcontrib>Inomata, Akiko</creatorcontrib><creatorcontrib>Nakae, Dai</creatorcontrib><creatorcontrib>Azumaya, Isao</creatorcontrib><creatorcontrib>Honda, Katsuya</creatorcontrib><creatorcontrib>Moriyasu, Takako</creatorcontrib><creatorcontrib>Tokyo Metropolitan Institute of Public Health</creatorcontrib><creatorcontrib>Toho University</creatorcontrib><creatorcontrib>University of Tsukuba</creatorcontrib><creatorcontrib>Tokyo University of Agriculture</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Health and Safety Science Abstracts (Full archive)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Engineering Research Database</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 2: Ocean Technology, Policy & Non-Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Aquaculture Abstracts</collection><collection>ASFA: Marine Biotechnology Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Marine Biotechnology Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ichikawa-Kaji, Yoko</au><au>Nakajima, Jun’ichi</au><au>Kikkawa, Shoko</au><au>Ishizawa, Fujio</au><au>Nishiyama, Rei</au><au>Kishimoto, Kiyoko</au><au>Uemura, Nozomi</au><au>Satoh, Miki</au><au>Suzuki, Jin</au><au>Inomata, Akiko</au><au>Nakae, Dai</au><au>Azumaya, Isao</au><au>Honda, Katsuya</au><au>Moriyasu, Takako</au><aucorp>Tokyo Metropolitan Institute of Public Health</aucorp><aucorp>Toho University</aucorp><aucorp>University of Tsukuba</aucorp><aucorp>Tokyo University of Agriculture</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of Descarbonsildenafil in an Adulterated Dietary Supplement and Evaluation of Its Inhibitory Activity for Phosphodiesterase Type 5 (PDE5)</atitle><jtitle>Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)</jtitle><addtitle>Food Hyg. Saf. Sci.</addtitle><date>2020-02-25</date><risdate>2020</risdate><volume>61</volume><issue>1</issue><spage>34</spage><epage>40</epage><pages>34-40</pages><issn>0015-6426</issn><eissn>1882-1006</eissn><abstract>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 IC50 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.</abstract><cop>Japan</cop><pub>Japanese Society for Food Hygiene and Safety</pub><pmid>32336717</pmid><doi>10.3358/shokueishi.61.34</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Coffee Crystal structure descarbonsildenafil Diet dietary supplement product Dietary supplements Erectile dysfunction Identification INADEQUATE NMR Ionization Ions Liquid chromatography Mass spectrometry Mass spectroscopy NMR Nuclear magnetic resonance Performance enhancement Phosphodiesterase phosphodiesterase type 5 inhibitor Quadrupoles Sildenafil Structural analysis Surveying X rays X-ray crystal structural analysis |
| title | Identification of Descarbonsildenafil in an Adulterated Dietary Supplement and Evaluation of Its Inhibitory Activity for Phosphodiesterase Type 5 (PDE5) |
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