Chemical characterization of ceramides isolated from a gliding marine bacterium Aureispira marina

Biosci Biotechnol Biochem. 2022 Jul 22;86(8):1136-1143. doi: 10.1093/bbb/zbac086.

Abstract

Ceramides containing 2-hydroxy fatty acids were purified from a gliding marine bacterium Aureispira marina, and their chemical structure was investigated. The ceramide molecules contained 2-hydroxy-15-methyl-hexadecanoic acid and 2-hydroxy-15-methyl-hexadecenoic acid, and the double bond of the latter fatty acid was proved to be located between the positions C3 and C4. The major portion of these 2-hydroxy fatty acids was determined to have D-configuration (S-configuration) after diastereomeric derivatization. Three carbon skeletons were found in sphingosines from ceramides, ie (1) 1,3-dihydroxy-2-amino-4-octadecen, (2) 1,3-dihydroxy-2-amino-17-methyl-4-octadecen, and (3) 1,3-dihydroxy-2-amino-9-methyl-4-octadecen. Molecules with additional double bonds were found in sphingosines with structures 1 and 3. The presence of ceramides with these chemical characteristics would be a significant feature for the taxonomy of A. marina and related bacteria.

Keywords: Aureispira marina; 2-hydroxy fatty acid; ceramide; sphingosine.

MeSH terms

  • Bacteroidetes*
  • Ceramides*
  • Fatty Acids

Substances

  • Ceramides
  • Fatty Acids

Supplementary concepts

  • Aureispira marina