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Identification and screening of a tadalafil analogue found in adulterated herbal products
Ji Hyun Lee1, Hyung Joo Kim1, Eunyoung Noh1
1Advanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osong-eup, Heungdeok-gu, Cheongju-si, Chungcheongbuk-do 363-700, Republic of Korea.
Abstract:
A tadalafil analogue was detected in an herbal product by high performance liquid chromatography-diode array detector (HPLC-DAD) with a similar chromatographic retention time to tadalafil. The compounds were separated using semi-preparative HPLC. The structure of the detected tadalafil analogue was elucidated by LC-quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS) and nuclear magnetic resonance (NMR) spectroscopy. A positive ion at m/z 404.1644 was detected by LC-Q-TOF/MS, corresponding to a molecular formula of C23H22N3O4. This unknown compound was identified as an analogue of tadalafil containing an additional methylene group and named homotadalafil. Homotadalafil was detected in 10 of 91 herbal products at concentrations of 0.058mgg(-1) to 8.735mgg(-1).
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