Anti-glycative and anti-inflammatory effects of macamides isolated from Tropaeolum tuberosum in skin cells

Abstract

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 IC₅₀ 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.

Graphical Abstract

Keywords:

• Tropaeolaceae
• Tropaeolum tuberosum
• macamides
• glycoxidation
• anti-inflammatory

Disclosure statement

The authors declare no conflict of interest.

Additional information

Funding

This work was supported by the Fundación de la Universidad Autónoma de Madrid (FUAM).