Chemical-functional space exploration of plant N-alkylamides

N-Alkylamides are widely present in different plant families like Asteraceae, Piperaceae, Rutaceae and Solanaceae. These compounds have been shown to possess a broad functional spectrum: anti-inflammatory, immune-modulatory, diuretic, vasorelaxant, analgetic, anti-insecticidal, antiviral and aphrodisiac [1, 2]. Also different toxic end points, e.g. associated with the respiratory tract, eyes and skin, have been reported [3]. N-Alkylamides are thus a new group of drugs, related to peptides due to their amide structure. However, up till now, no structured overview of N-alkylamides is yet available. Therefore, we performed a classification of these N-alkylamides, including their structural relationships and bio-functionality. A database was first constructed, and each N-alkylamide was converted into molecular descriptors. Multi-variate analysis was performed for clustering and modelling [4, 5]. References [1]J. Boonen, B. Baert, N. Roche, C. Burvenich and B. De Spiegeleer. Transdermal behaviour of the Nalkylamide spilanthol (affinin) from Spilanthesacmella (Compositae) extracts, Journal ofEthnopharmacology 127(1) (2010) 77-84. [2]V. Sharma, J. Boonen, M. Thakur, B. De Spiegeleer, V.K. Dixit. Spilanthes acmella ethanolic flowerextract: LC-MS alkylamide profiling and its effects on sexual behaviour in male rats, Phytomedicine(2011), accepted for publication. [3]M. Pesonen, K. Vähäkangas, M. Halme, P. Vanninen, H. Seulanto et. al. Capsaicinoids, chloropicrin and sulfur mustard: Possibilities for exposure biomarkers, Frontiers in Pharmacology (2010). [4]S. Van Dorpe, V. Vergote, A. Pezeshki, C. Burvenich, K. Peremans, B. De Spiegeleer, Hydrophilicinteraction LC of peptides: Columns comparison and clustering, 33(6-7) (2010) 728-739. [5]B. Baert, E. De Coninck, M. Van Gele, M. Slodicka, P. Stoppie, S. Bodé, G. Slegers, Y. Vander Heyden, J. Lambert, J. Beetens, B. De Spiegeleer. Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds, Bioorganic & medicinal chemistry 15(22) (2007) 6943-6955.N-Alkylamides are widely present in different plant families like Asteraceae, Piperaceae, Rutaceae and Solanaceae. These compounds have been shown to possess a broad functional spectrum: anti-inflammatory, immune-modulatory, diuretic, vasorelaxant, analgetic, anti-insecticidal, antiviral and aphrodisiac [1, 2]. Also different toxic end points, e.g. associated with the respiratory tract, eyes and skin, have been reported [3]. N-Alkylamides are thus a new group of drugs, related to peptides due to their amide structure. However, up till now, no structured overview of N-alkylamides is yet available. Therefore, we performed a classification of these N-alkylamides, including their structural relationships and bio-functionality. A database was first constructed, and each N-alkylamide was converted into molecular descriptors. Multi-variate analysis was performed for clustering and modelling [4, 5]. References [1]J. Boonen, B. Baert, N. Roche, C. Burvenich and B. De Spiegeleer. Transdermal behaviour of the Nalkylamide spilanthol (affinin) from Spilanthesacmella (Compositae) extracts, Journal ofEthnopharmacology 127(1) (2010) 77-84. [2]V. Sharma, J. Boonen, M. Thakur, B. De Spiegeleer, V.K. Dixit. Spilanthes acmella ethanolic flowerextract: LC-MS alkylamide profiling and its effects on sexual behaviour in male rats, Phytomedicine(2011), accepted for publication. [3]M. Pesonen, K. Vähäkangas, M. Halme, P. Vanninen, H. Seulanto et. al. Capsaicinoids, chloropicrin and sulfur mustard: Possibilities for exposure biomarkers, Frontiers in Pharmacology (2010). [4]S. Van Dorpe, V. Vergote, A. Pezeshki, C. Burvenich, K. Peremans, B. De Spiegeleer, Hydrophilicinteraction LC of peptides: Columns comparison and clustering, 33(6-7) (2010) 728-739. [5]B. Baert, E. De Coninck, M. Van Gele, M. Slodicka, P. Stoppie, S. Bodé, G. Slegers, Y. Vander Heyden, J. Lambert, J. Beetens, B. De Spiegeleer. Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds, Bioorganic & medicinal chemistry 15(22) (2007) 6943-6955.C