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Isolation and structural elucidation of a new sildenafil analogue from a functional coffee

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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.

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Acknowledgments

The financial support from the Health Sciences Authority Reinvestment Fund, the National University of Singapore Academic Research Fund (KHL R-148-000-137-112), and the National University of Singapore research scholarship (LL) are acknowledged.

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Authors and Affiliations

  1. Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore, 117543, Singapore

    Lin Li & Hwee-Ling Koh

  2. Pharmaceutical Division, Applied Sciences Group, Health Sciences Authority, 11 Outram Road, Singapore, 169078, Singapore

    Min-Yong Low, Xiaowei Ge & Bosco C. Bloodworth

Authors
  1. Lin Li
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  2. Min-Yong Low
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  3. Xiaowei Ge
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  4. Bosco C. Bloodworth
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  5. Hwee-Ling Koh
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Corresponding author

Correspondence to Hwee-Ling Koh.

Additional information

Published in the topical collection Nutraceuticals with guest editors Melissa M. Philipps and Catherine A. Rimmer.

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Li, L., Low, MY., Ge, X. et al. Isolation and structural elucidation of a new sildenafil analogue from a functional coffee. Anal Bioanal Chem 405, 4443–4450 (2013). https://doi.org/10.1007/s00216-012-6236-8

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  • DOI: https://doi.org/10.1007/s00216-012-6236-8

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