Russian Journal of Bioorganic Chemistry

, Volume 32, Issue 5, pp 485–491

An unusual lipid a from a marine bacterium Chryseobacterium scophtalmum CIP 104199T

  • E. V. Vorobeva
  • I. N. Krasikova
  • A. S. Dmitrenok
  • P. S. Dmitrenok
  • V. V. Isakov
  • O. I. Nedashkovskaya
  • T. F. Solov’eva
Article

DOI: 10.1134/S1068162006050128

Cite this article as:
Vorobeva, E.V., Krasikova, I.N., Dmitrenok, A.S. et al. Russ J Bioorg Chem (2006) 32: 485. doi:10.1134/S1068162006050128

Abstract

The hydrolysis of defatted cells of the marine bacterium Chryseobacterium scophtalmum CIP 104199T with 10% acetic acid (3 h, 100°C) led to an unusual lipid A (LA) (yield 0.6%), obtained for the first time. Using chemical analysis, FAB MS, and NMR spectroscopy, it was shown to be D-glucosamine 1-phosphate acylated with (R)-3-hydroxy-15-methylhexadecanoic and (R)-3-hydroxy-13-methyltetroadecanoic acids at the C2 and C3 atoms, respectively. It is similar to the monosaccharide biosynthetic precursor of lipopolysaccharide (LPS), so-called lipid X (LX). Unlike LX, LA can be isolated by the treatment of bacteria with organic solvents only after the preliminary acidic hydrolysis of the cells, which suggests that LA might be strongly, probably chemically, linked to other components of the outer membrane. However, LPS cannot be such a component, because extraction with phenol-water or phenol-chloroform-petroleum ether mixtures in high yields (5.34% and 0.5%, respectively) leads to preparations that do not contain 3-deoxy-D-manno-oct-2-ulopyranosonic acid, 3-hydroxyalkanoic acids, or LA.

Key words

Chryseobacterium scophtalmumlipid Alipid Xlipopolysaccharide

Abbrevations

FAB MS

fast atom bombardment mass-spectrometry

Kdo

3-deoxy-D-manno-oct-2-ulopyranosonic acid

LA

Lipid A

LX

lipid X

LPS

lipopolysaccharide

O-PS

O-specific polysaccharide

PL

phospholipid

PE

phosphatidylethanolamine

PG

phosphatidylglycerol

Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • E. V. Vorobeva
    • 1
  • I. N. Krasikova
    • 1
  • A. S. Dmitrenok
    • 1
  • P. S. Dmitrenok
    • 1
  • V. V. Isakov
    • 1
  • O. I. Nedashkovskaya
    • 1
  • T. F. Solov’eva
    • 1
  1. 1.Pacific Institute of Bioorganic Chemistry, Far East DivisionRussian Academy of SciencesVladivostokRussia