Synthesis of conjugated bile acids/azastilbenes as potential antioxidant and photoprotective agents

Steroids. 2015 Jun:98:114-21. doi: 10.1016/j.steroids.2015.03.009. Epub 2015 Mar 23.

Abstract

A series of 14 bile acids/azastilbenes conjugates (1a-g and 2a-g) was prepared through the condensation of bile amides (1 and 2) and aromatic aldehydes. The newly synthesized conjugates were evaluated in vitro for their antioxidant and photoprotective activities. Six compounds (1, 1a, 1b, 2, 2a and 2b) showed promising antioxidant activity with IC50 values of 19.60-31.83 μg mL(-1). The synthesized compounds presented a varied photoprotection profile, with the SPF ranging from 2 to 9. Among the 16 compounds tested for the protection against UVB sunrays, 3 compounds (2c, 2e and 2g) presented more significant protection than resveratrol and the free azastilbene 3; while the UVAPF increased from 2 in resveratrol and 5 in 3 to 5-11 in the majority of the conjugates.

Keywords: Antioxidant activity; Azastilbenes; Bile acids; Photoprotective activity; Schiff bases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants* / chemical synthesis
  • Antioxidants* / chemistry
  • Aza Compounds*
  • Bile Acids and Salts* / chemical synthesis
  • Bile Acids and Salts* / chemistry
  • Stilbenes* / chemical synthesis
  • Stilbenes* / chemistry
  • Sunscreening Agents* / chemical synthesis
  • Sunscreening Agents* / chemistry

Substances

  • Antioxidants
  • Aza Compounds
  • Bile Acids and Salts
  • Stilbenes
  • Sunscreening Agents