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. This study aimed to evaluate the extracts and isolated compounds from T. tuberosum with anti-glycative and anti-inflammatory activities. Guided isolation by bioassay led to the isolation and characterisation by NMR and MS of ( S )-(-)- N -( α -methylbenzyl)-oleamide (1 ) and ( S )-(-)- N -( α -methylbenzyl)-linoleamide ( 2 ). Both compounds inhibited the production of TNF-α with IC 50 values of 9.38 µM (NIH/3T3 cells) and 10.06 µM (PA317 cells) for compound 1 , and 5.3 µM (NIH/3T3 cells) and 6.48 µM (PA317 cells) for compound 2 . Compounds 1 and 2 showed the inhibitory effect on the BSA-MGO formation at concentrations of 9.38 µM (3.39%) and 5.30 µM (8.53%), respectively. Moreover, both compounds showed significant breaking properties on the MGO-AGE-protein crosslink with percent modification of 6.58% (9.38 µM) and 18.08% (5.30 µM), respectively.