Identification of a new tadalafil analogue in an adulterated dietary supplement: trans-Bisprehomotadalafil.
A new tadalafil analogue was identified along with homotadalafil during routine screening of an adulterated dietary supplement using HPLC-DAD. The UV spectrum of this analogue was almost identical with that of tadalafil. This compound was isolated from the supplement by using semi-preparative HPLC and its structure was subsequently elucidated by performing Q-TOF/MS/MS and NMR spectroscopic experiments. The spectral data indicate that this tadalafil analogue is a dimeric compound that consists of an ethylamino group and two pretadalafil moieties. NOE experiments and comparison with (1)H NMR spectra of tadalafil and trans-tadalafil suggested the trans-relationship between the substituents on piperidine rings in the pretadalafil moieties.
Advanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Cheongju-si 363-700, Chungcheongbuk-do, Republic of Korea.
Ji Hyun
JH
Lee
Advanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Cheongju-si 363-700, Chungcheongbuk-do, Republic of Korea.
Hyung Joo
HJ
Kim
College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon 200-701, Kangwon-do, Republic of Korea.
Suresh
S
Mandava
College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon 200-701, Kangwon-do, Republic of Korea.
Jungjoong
J
Hwang
Advanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Cheongju-si 363-700, Chungcheongbuk-do, Republic of Korea.
Hyoung Joon
HJ
Park
Advanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Cheongju-si 363-700, Chungcheongbuk-do, Republic of Korea.
Sooyeul
S
Cho
Advanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Cheongju-si 363-700, Chungcheongbuk-do, Republic of Korea. Electronic address: stepany9838@korea.kr.
Sun Young
SY
Baek
College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon 200-701, Kangwon-do, Republic of Korea. Electronic address: jkl@kangwon.ac.kr.
Jongkook
J
Lee
D002851:Chromatography, High Pressure Liquid; D019587:Dietary Supplements / Q000032:analysis*; D004340:Drug Contamination; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D058986:Phosphodiesterase 5 Inhibitors / Q000032:analysis*; D013056:Spectrophotometry, Ultraviolet; D000068581:Tadalafil / Q000031:analogs & derivatives* / Q000032:analysis*; D053719:Tandem Mass Spectrometry
D058986:Phosphodiesterase 5 Inhibitors; D000068581:Tadalafil; C000608783:bisprehomotadalafil
Dietary supplement; Homotadalafil; PDE-5 inhibitor; Tadalafil analogue; Trans-Bisprehomotadalafil