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

Nat Prod Res. 2022 Nov;36(22):5803-5807. doi: 10.1080/14786419.2021.2016751. Epub 2021 Dec 22.

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.

Keywords: Tropaeolaceae; Tropaeolum tuberosum; anti-inflammatory; glycoxidation; macamides.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / pharmacology
  • Magnesium Oxide
  • Mice
  • Plant Extracts / pharmacology
  • Tropaeolum* / chemistry
  • Tumor Necrosis Factor-alpha

Substances

  • Magnesium Oxide
  • Anti-Inflammatory Agents
  • Plant Extracts
  • Tumor Necrosis Factor-alpha