Photoprotection against UVAR: effective triterpenoids require a lipid raft stabilizing chemical structure

Exp Dermatol. 2011 Nov;20(11):955-8. doi: 10.1111/j.1600-0625.2011.01350.x. Epub 2011 Aug 8.

Abstract

UVA(Ultraviolet A)-induced gene expression is supposed to be a hallmark for inflammation, for immunosuppression and in long-term cancer formation. In previous studies, we have shown for keratinocytes that physiological doses of UVA radiation result in the upregulation of gene expression mediated by ceramide formation from sphingolipids/cholesterol-rich microdomains (rafts), which can be blocked by preloading keratinocytes with cholesterol or plant sterols. Here, we show that besides stigmasterol and ß-sitosterol, also sterols like 14-dehydroergosterol, ergosterol-peroxide and 29-norcycloartenol inhibit the UVA response. Moreover, we present evidence that natural material-derived triterpenoids such as oleanolic acid can abrogate UVA-induced gene expression by raft stabilization. This effect depends on the structure of the molecule, because its isomer ursolic acid also integrates within the rafts without inhibiting ceramide formation and upregulation of gene expression.

Publication types

  • Letter
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cells, Cultured
  • Ceramides / biosynthesis
  • Drug Evaluation, Preclinical
  • Humans
  • Keratinocytes / drug effects
  • Keratinocytes / metabolism
  • Keratinocytes / radiation effects
  • Membrane Microdomains / drug effects*
  • Membrane Microdomains / metabolism
  • Phytosterols / chemistry
  • Phytosterols / pharmacology
  • Sunscreening Agents / chemistry
  • Sunscreening Agents / pharmacology*
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*
  • Ultraviolet Rays / adverse effects*

Substances

  • Ceramides
  • Phytosterols
  • Sunscreening Agents
  • Triterpenes