title: Isolation and structural elucidation of a new sildenafil analogue from a functional coffee.
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 ionization-tandem mass spectrometry; and nuclear magnetic resonance spectroscopy, ultraviolet spectroscopy, and infrared spectroscopy. Compared with sildenafil, instead of an N-methylpiperazinyl 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.
authors: Department of Pharmacy, Faculty of Science, National University of Singapore, Singapore.
authors: Lin
authors: L
authors: Li
authors: Min-Yong
authors: MY
authors: Low
authors: Xiaowei
authors: X
authors: Ge
authors: Bosco C
authors: BC
authors: Bloodworth
authors: Hwee-Ling
authors: HL
authors: Koh
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003069:Coffee / Q000737:chemistry*; D013058:Mass Spectrometry / Q000379:methods; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry* / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry*; D011687:Purines / Q000737:chemistry / Q000302:isolation & purification; D000068677:Sildenafil Citrate; D013449:Sulfonamides / Q000737:chemistry* / Q000302:isolation & purification; D013450:Sulfones / Q000737:chemistry* / Q000302:isolation & purification; D014665:Vasodilator Agents / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D003069:Coffee; D010879:Piperazines; D010936:Plant Extracts; D011687:Purines; D013449:Sulfonamides; D013450:Sulfones; D014665:Vasodilator Agents; D000068677:Sildenafil Citrate