Isolation and Structural Elucidation of Cyclopentynafil and N-Octylnortadalafil Found in a Dietary Supplement
| Autor: | Yuji Haishima, Yukihiro Goda, Masaaki Kurihara, Toshiyasu Ishii, Kazunaga Takahashi, Masaaki Saijo, Takashi Hasegawa, Tomoko Nagata, Nobuo Kawahara |
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| Rok vydání: | 2009 |
| Předmět: |
Male
Spectrometry Mass Electrospray Ionization Circular dichroism Magnetic Resonance Spectroscopy medicine.drug_mechanism_of_action Phosphodiesterase Inhibitors Sildenafil Chemical structure Dietary supplement Pharmacology Piperazines Tadalafil chemistry.chemical_compound Erectile Dysfunction Liquid chromatography–mass spectrometry Drug Discovery medicine Humans Sulfones Chromatography High Pressure Liquid Chromatography Illicit Drugs Circular Dichroism General Chemistry General Medicine chemistry Dietary Supplements Indicators and Reagents Phosphodiesterase 5 inhibitor Carbolines Cyclopentynafil medicine.drug |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 57:185-189 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.57.185 |
| Popis: | 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-[2-ethoxy-5-(4-cyclopentylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one and (6R,12aR)-2-octyl-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, respectively. Recently, a large number of phosphodiesterase-5 (PDE-5) inhibitors, including their analogues, have been isolated from dietary supplements, while cyclopentynafil and N-octylnortadalafil are the first compounds reported to be new sildenafil and tadalafil analogues, respectively. Quantitative HPLC analysis showed that the contents of 1 and 2 in the product were about 130 mg/tablet (301 microg/mg) and about 27 mg/tablet (64.1 microg/mg), respectively. |
| Databáze: | OpenAIRE |
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