Please use this identifier to cite or link to this item: https://doi.org/10.1007/s00216-012-6236-8
Title: Isolation and structural elucidation of a new sildenafil analogue from a functional coffee
Authors: Li, L.
Low, M.-Y.
Ge, X.
Bloodworth, B.C.
Koh, H.-L. 
Keywords: Adulteration
Coffee
Erectile dysfunction
Food contaminants
Functional food
Sildenafil
Issue Date: 2013
Citation: Li, L., Low, M.-Y., Ge, X., Bloodworth, B.C., Koh, H.-L. (2013). Isolation and structural elucidation of a new sildenafil analogue from a functional coffee. Analytical and Bioanalytical Chemistry 405 (13) : 4443-4450. ScholarBank@NUS Repository. https://doi.org/10.1007/s00216-012-6236-8
Abstract: A sildenafil analogue was detected in a functional coffee sample labelled to have male sexual performance enhancement effects. This analogue was isolated and purified by flash chromatography and preparative high-performance liquid chromatography. Its structure was elucidated using high-resolution mass spectrometry; electrospray ionizationtandem mass spectrometry; and nuclear magnetic resonance spectroscopy, ultraviolet spectroscopy, and infrared spectroscopy. Compared with sildenafil, instead of an Nmethylpiperazinyl moiety, ring opening of the piperazine ring with the loss of a carbon atom resulted in a substituted benzenesulfonamide. The chemical name of this analogue is N-[2-(dimethylamino)ethyl]-4-ethoxy-3- (1-methyl-7-oxo-3-propyl-6,7-dihydro-1H- pyrazolo[4,3- d]pyrimidin-5-yl)benzenesulfonamide. It is named descarbonsildenafil because it has one less carbon atom when compared with sildenafil. © Springer-Verlag 2012.
Source Title: Analytical and Bioanalytical Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/106098
ISSN: 16182642
DOI: 10.1007/s00216-012-6236-8
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