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 endpoints, 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 (Fig.1). However, up till now, no structured overview of N-alkylamides is yet available. Therefore, we performed a chemical classification of 260 of these N-alkylamides. A database was constructed and each N-alkylamide was converted into molecular descriptors. Multi-variate analysis was performed for clustering and modelling [4, 5]. Later on, this chemical classification will be extended with bio-functional data. References: [1] J. Boonen, B. Baert, N. Roche, et al. Transdermal behaviour of the N-alkylamide spilanthol (affinin) from Spilanthes acmella (Compositae) extracts, Journal of Ethnopharmacology 127(1) (2010) 77-84. [2] V. Sharma, J. Boonen, M. Thakur, et al. Spilanthes acmella ethanolic flower extract: 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, et. al. Capsaicinoids, chloropicrin and sulfur mustard: Possibilities for exposure biomarkers, Frontiers in Pharmacology (2010). [4] S. Van Dorpe, V. Vergote, A. Pezeshki, et al. Hydrophilic interaction LC of peptides: Columns comparison and clustering, 33(6-7) (2010) 728-739. [5] B. Baert, E. De Coninck, M. Van Gele, M., et al. Transdermal penetration behaviour of drugs: CART clustering, QSPR and selection of model compounds, Bioorganic & medicinal chemistry 15(22) (2007) 6943-6955