PA317

Anti-Glycative and Anti-Inflammatory Effects of Macamides Isolated from Tropaeolum tuberosum in Skin Cells

Tropaeolum tuberosum, commonly known as Mashua, is an herbal remedy used on the skin in order to treat local pain and to heal wounds. Ticona et al. aimed to evaluate the extracts and isolated compounds from T. tuberosum with anti-glycative and anti-inflammatory activities.

The isolated compounds were identified as (S)-(-)-N-(α-methylbenzyl)-oleamide (1) and (S)-(-)-N-(α-methylbenzyl)-linoleamide (2) (Fig. 1). These compounds were previously described by D'Oca et al. Their cytotoxicity was assessed using the XTT assay in NIH/3T3 and PA317 cells for 12 hours. The results showed that neither compound significantly reduced cell viability. The CC₅₀ values for compound 1 were 90.15 µM (NIH/3T3) and 91.15 µM (PA317), while for compound 2, they were 88.71 µM (NIH/3T3) and 90.49 µM (PA317), all higher than the positive control actinomycin D (ACT, CC₅₀ = 0.008 µM). This indicates that compounds 1 and 2 were less cytotoxic than ACT. The lower cytotoxicity of compounds 1 and 2 is attributed to their increased lipophilicity due to the presence of double bonds in the side chain, confirming the relationship between cytotoxicity and lipophilic capacity. Lipophilicity is measured as LogP, where higher LogP values enhance cell permeability. Compound 2 had a cLogP of 8.20, allowing it to cross cell membranes more easily than compound 1 (cLogP of 7.22). Thus, compounds with more double bonds in their side chains can more readily diffuse across cell barriers.