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, and T. F. Solov’eva

# Phone: (4232) 31-0719; fax: (4232) 31-4050; e-mail
Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, pr. 100-letiya Vladivostoka 159, Vladivostok, 690022 Russia

Received October 11, 2005; in final form, December 13, 2005

Abstract: The hydrolysis of defatted cells of the marine bacterium Chryseobacterium scophtalmum CIP 104199T with 10% acetic acid (3 h, 100C) 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-methyltetradecanoic 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 scophtalmum, lipid A, lipid X, lipopolysaccharide

Russian Journal of Bioorganic Chemistry 2006, 32 (5):485-491