Ba. Wolucka et al., ISOLATION AND CHARACTERIZATION OF A NOVEL GLUCURONOSYL DIACYLGLYCEROLFROM MYCOBACTERIUM-SMEGMATIS, Biochimica et biophysica acta, 1170(2), 1993, pp. 131-136
A glucuronic acid-containing diacylglycerol was isolated from exponent
ially growing Mycobacterium smegmatis. Structural analysis of the puri
fied glycolipid, performed by gas chromatography-mass spectrometry, fa
st atom bombardment-mass spectrometry, and high resolution proton NMR,
indicated the structure lpha-D-glucuronopyranosyl)-1,2-diacyl-sn-glyc
erol. Two forms of the glycolipid were observed differing in fatty aci
d composition. Both molecular species contained a hexadecanoic acid re
sidue, whereas the second acyl group was either tuberculostearic acid
(10-methylstearic acid) or octadecenoic acid. The inherent antigenicit
y of the glycolipid was shown by its ability to bind to anti-Mycobacte
rium avium (serovar 26) and anti-Mycobacterium tuberculosis sera by We
stern blot-type thin-layer chromatography. This is the second instance
of the isolation of a glycosyl diacylglycerol from members of the Myc
obacterium genus, further confirming its close relationship to Gram-po
sitive bacteria.