Enzymatic production of 3,6-anhydro-L-galactose from agarose and its purification and in vitro skin whitening and anti-inflammatory activities

Appl Microbiol Biotechnol. 2013 Apr;97(7):2961-70. doi: 10.1007/s00253-012-4184-z. Epub 2012 Jun 8.

Abstract

3,6-Anhydro-L-galactose (L-AHG) constitutes 50% of agarose, which is the main component of red macroalgae. No information is currently available on the mass production, metabolic fate, or physiological effects of L-AHG. Here, agarose was converted to L-AHG in the following three steps: pre-hydrolysis of agarose into agaro-oligosaccharides by using acetic acid, hydrolysis of the agaro-oligosaccharides into neoagarobiose by an exo-agarase, and hydrolysis of neoagarobiose into L-AHG and galactose by a neoagarobiose hydrolase. After these three steps, L-AHG was purified by adsorption and gel permeation chromatographies. The final product obtained was 95.6% pure L-AHG at a final yield of 4.0% based on the initial agarose. In a cell proliferation assay, L-AHG at a concentration of 100 or 200 μg/ mL did not exhibit any significant cytotoxicity. In a skin whitening assay, 100 μg/ mL of L-AHG showed significantly lower melanin production compared to arbutin. L-AHG at 100 and 200 μg/ mL showed strong anti-inflammatory activity, indicating the significant suppression of nitrite production. This is the first report on the production of high-purity L-AHG and its physiological activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid / metabolism*
  • Animals
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / metabolism
  • Anti-Inflammatory Agents / pharmacology*
  • Anti-Inflammatory Agents / toxicity
  • Cell Line
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Disaccharidases / metabolism*
  • Galactose / analogs & derivatives*
  • Galactose / isolation & purification
  • Galactose / metabolism
  • Galactose / pharmacology
  • Galactose / toxicity
  • Glycoside Hydrolases / metabolism*
  • Hydrolysis
  • Macrophages / drug effects
  • Melanins / biosynthesis
  • Melanocytes / drug effects
  • Mice
  • Sepharose / metabolism*
  • Skin Lightening Preparations / isolation & purification
  • Skin Lightening Preparations / metabolism
  • Skin Lightening Preparations / pharmacology*
  • Skin Lightening Preparations / toxicity

Substances

  • Anti-Inflammatory Agents
  • Melanins
  • Skin Lightening Preparations
  • 3,6-anhydrogalactose
  • Sepharose
  • Disaccharidases
  • Glycoside Hydrolases
  • neoagarobiose hydrolase
  • agarase
  • Acetic Acid
  • Galactose