Monoacylglycerol of 7,10-Dihydroxy-8(E)-octadecenoic Acid Enhances Antibacterial Activities against Food-Borne Bacteria

J Agric Food Chem. 2019 Jul 24;67(29):8191-8196. doi: 10.1021/acs.jafc.9b03063. Epub 2019 Jul 11.

Abstract

Conversion of free fatty acids into monoacylglycerol gives rise to new structural properties, particularly amphipathic property. Therefore, monoacylglycerols are widely used in pharmaceutical and food industries and are also reported to facilitate better absorption into the human body. A functional fatty acid when transformed into a monoacylglycerol will possibly conserve both the original functionality and amphipathic property. The compound 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) was generated from oleic acid by Pseudomonas aeruginosa PR3 and was known to contain antimicrobial activities against a broad range of food-borne and plant pathogenic bacteria. Here, we attempted to convert DOD into its monoacylglycerol form using lipase for producing an amphipathic antibacterial agent. Consequently, the monoacylglycerol of DOD (DOD-MAG) was successfully produced by coincubating DOD, glycerol, and lipase at 30 °C. The maximum conversion yield reached 70% after 12 h of incubation. Antibacterial activity of DOD-MAG was enhanced by 8 times from the original activity of DOD against food-borne bacteria.

Keywords: antibacterial activity; dihydroxy fatty acid; lipase; monoacylglycerol.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology*
  • Food Microbiology
  • Monoglycerides / chemistry*
  • Oleic Acids / chemistry*
  • Oleic Acids / metabolism
  • Oleic Acids / pharmacology*
  • Pseudomonas aeruginosa / chemistry*
  • Pseudomonas aeruginosa / metabolism
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / growth & development

Substances

  • 7,10-dihydroxy-8-octadecenoic acid
  • Anti-Bacterial Agents
  • Monoglycerides
  • Oleic Acids