Protection of free radical-induced cytotoxicity by 2-O-α-D-glucopyranosyl-L-ascorbic acid in human dermal fibroblasts

Biosci Biotechnol Biochem. 2014;78(2):301-6. doi: 10.1080/09168451.2014.882756. Epub 2014 May 2.

Abstract

The stable ascorbic acid (AA) derivative, 2-O-α-D-glucopyranosyl-L-ascorbic acid (AA-2G), exhibits vitamin C activity after enzymatic hydrolysis to AA. The biological activity of AA-2G per se has not been studied in detail, although AA-2G has been noted as a stable source for AA supply. The protective effect of AA-2G against the oxidative cell death of human dermal fibroblasts induced by incubating with 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH) for 24 h was investigated in this study. AA-2G showed a significant protective effect against the oxidative stress in a concentration-dependent manner. AA-2G did not exert a protective effect during the initial 12 h of incubation, but had a significant protective effect in the later part of the incubation period. Experiments using a α-glucosidase inhibitor and comparative experiments using a stereoisomer of AA-2G confirmed that AA-2G had a protective effect against AAPH-induced cytotoxicity without being converted to AA. Our results provide an insight into the efficacy of AA-2G as a biologically interesting antioxidant and suggest the practical use of AA-2G even before being converted into AA as a beneficial antioxidant.

Keywords: 2-O-α-d-glucopyranosyl-l-ascorbic acid; AAPH; oxidative stress; stable vitamin C derivative; water-soluble antioxidant.

MeSH terms

  • Amidines / toxicity*
  • Ascorbic Acid / analogs & derivatives*
  • Ascorbic Acid / chemistry
  • Ascorbic Acid / pharmacology
  • Cytotoxins / toxicity*
  • Drug Stability
  • Fibroblasts / cytology*
  • Fibroblasts / drug effects*
  • Fibroblasts / metabolism
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology*
  • Free Radicals / toxicity
  • Humans
  • Oxidative Stress / drug effects
  • Skin / cytology*
  • Time Factors

Substances

  • Amidines
  • Cytotoxins
  • Free Radical Scavengers
  • Free Radicals
  • ascorbic acid 2-O-glucoside
  • 2,2'-azobis(2-amidinopropane)
  • Ascorbic Acid