Journal of Lipid Research, Vol 27, 724-730, Copyright © 1986 by Lipid Research, Inc.
A diphytanyl ether analog of phosphatidylserine from a methanogenic bacterium, Methanobrevibacter arboriphilus
H Morii, M Nishihara, M Ohga and Y Koga
Several ninhydrin-positive lipids were found in methanogenic bacteria and
the structure of one of them, designated as PNL2 from Methanobrevibacter
arboriphilus, was identified as a diphytanyl ether analog of
phosphatidylserine. The chromatographic behavior of the lipid on thin-layer
plates and on a DEAE-cellulose column was identical to the ester form of
phosphatidylserine. The infrared spectra showed the presence of amino,
carboxyl, ether, and phosphate groups, and the absence of an ester linkage.
The hydrophobic portion of the lipid was identified as diphytanyl glycerol
diether on the basis of the mass spectrum of the acetolysis product and
gas-liquid chromatography of the iodinated alkyl chain prepared by
hydroiodic acid cleavage of PNL2. The fast atom bombardment-ionization and
field desorption mass spectrum provided a molecular weight of 819 and
several fragment ions consistent with the proposed structure. Hydrofluoric
acid hydrolysis resulted in water-soluble products including serine,
phosphoserine, and ammonia, which accounted for 95% of hydrolyzed PNL2. The
lipid product of the hydrolysis was mainly the diether form of phosphatidic
acid. This is the first report on the structural characterization of an
amino- containing phospholipid in archaebacteria. Amino lipids have been
found in many other methanogenic bacteria.
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