3,4,5-Trimethoxycinnamate thymol ester inhibits melanogenesis in normal human melanocytes and 3D human epidermal equivalents via the PGC-1α-independent PPARγ partial agonism

J Dermatol Sci. 2022 Apr;106(1):12-20. doi: 10.1016/j.jdermsci.2022.02.010. Epub 2022 Feb 28.

Abstract

Background: 3,4,5-Trimethoxycinnamate thymol ester (TCTE), an anti-melanogenic cosmetic agent prescribed currently, promotes adiponectin synthesis during adipogenesis in human bone marrow mesenchymal stem cells (hBM-MSCs). Adiponectin inhibits melanin biosynthesis and its biosynthesis is directly regulated by peroxisome proliferator-activated receptor (PPAR) γ. In this regard, TCTE may potentially affect PPARγ activity. However, contradicting effects of PPARγ agonists with different chemical structures on human melanogenesis have been reported.

Objective: A molecular target of TCTE was investigated to elucidate the association of both adiponectin and PPARγ with anti-melanogenic activity.

Methods: The adiponectin secretion-promoting activity of TCTE was tested in an adipogenesis model of hBM-MSCs. A molecular target of TCTE for adiponectin secretion was evaluated via time-resolved fluorescence resonance energy transfer-based receptor binding and transactivation of PPARs.

Results: TCTE significantly promoted adiponectin secretion (EC50, 27.9 μM) during adipogenesis in hBM-MSCs and directly bound to PPARγ (Ki, 13.2 μM). The TCTE-bound PPARγ increased the recruitment of SRC-1, SRC-3, and TRAP220/DRIP-1 coactivator peptides without affecting PGC-1α coactivation. In the docking analysis, the optimal ligand binding mode of TCTE exhibited typical ligand-receptor interactions of PPARγ partial agonists. The PPARγ partial agonism of TCTE was established experimentally and the anti-melanogenic activity of TCTE was decreased by treatment with a PPARγ antagonist in cultured normal human melanocytes and a 3D model of human epidermis.

Conclusion: The anti-melanogenic activity of TCTE was associated with a PGC-1α-independent PPARγ partial agonism.

Keywords: 3; 3D human epidermis model; 4; 5-Trimethoxycinnamate thymol ester; Adiponectin; Melanogenesis; Peroxisome proliferator-activated receptor gamma.

MeSH terms

  • Adiponectin*
  • Epidermis / metabolism
  • Esters
  • Humans
  • Ligands
  • Melanocytes / metabolism
  • PPAR gamma* / metabolism
  • Thymol

Substances

  • Adiponectin
  • Esters
  • Ligands
  • PPAR gamma
  • Thymol