J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M600034-JLR200 on May 4, 2006

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Journal of Lipid Research, Vol. 47, 1823-1832, August 2006
Copyright © 2006 by American Society for Biochemistry and Molecular Biology

Structural elucidation of phosphoglycolipids from strains of the bacterial thermophiles Thermus and Meiothermus

Yu-Liang Yang*, Feng-Ling Yang*, Shu-Chuan Jao*, Mao-Yen Chen*,{dagger}, San-San Tsay{dagger}, Wei Zou§ and Shih-Hsiung Wu*,**,1

* Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan
{dagger} Department of Life Science and Institute of Plant Biology, National Taiwan University, Taipei 106, Taiwan
§ Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada
** Institute of Biochemical Sciences, National Taiwan University, Taipei 106, Taiwan

Published, JLR Papers in Press, May 4, 2006.

1 To whom correspondence should be addressed. e-mail: shwu{at}gate.sinica.edu.tw

The structures of two major phosphoglycolipids from the thermophilic bacteria Thermus oshimai NTU-063, Thermus thermophilus NTU-077, Meiothermus ruber NTU-124, and Meiothermus taiwanensis NTU-220 were determined using spectroscopic and chemical analyses to be 2'-O-(1,2-diacyl-sn-glycero-3-phospho) -3'-O-({alpha}-N-acetyl-glucosaminyl)-N-glyceroyl alkylamine [PGL1 (1)] and the novel structure 2'-O-(2-acylalkyldio-1-O-phospho)-3'-O-({alpha}-N-acetylglucosaminyl)-N-glyceroyl alkylamine [PGL2 (2)]. PGL2 (2) is the first phosphoglycolipid identified with a 2-acylalkyldio-1-O-phosphate moiety. The fatty acids of the phosphoglycolipids are mainly iso-C15:0, -C16:0, and -C17:0 and anteiso-C15:0 and -C17:0. The ratios of PGL2 (2) to PGL1 (1) are significantly altered when grown at different temperatures for three strains, T. thermophilus NTU-077, M. ruber NTU-124, and M. taiwanensis NTU-220, but not for T. oshimai NTU-063. Accordingly, the ratios of iso- to anteiso-branched fatty acids increase when grown at the higher temperature.

Abbreviations: CE-MS, capillary electrophoresis-mass spectroscopy; DQF-COSY, double quantum filtered-correlation spectroscopy; FAME, fatty acid methyl ester; gHMQC, gradient heteronuclear multiple quantum coherence; HMBC, heteronuclear multiple bond coherence; HPAEC-PAD, high-performance anion-exchange chromatography with pulsed amperometric detection; MALDI, matrix-assisted laser desorption ionization; PGL1, 2'-O-(1,2-diacyl-sn-glycero-3-phospho)-3'-O-({alpha}-N-acetyl-glucosaminyl)-N-glyceroyl alkylamine; PGL2, 2'-O-(2-acylalkyldio-1-O-phospho)-3'-O-({alpha}-N-acetylglucosaminyl)-N-glyceroyl alkylamine; ROESY, rotational frame nuclear Overhauser effect spectroscopy; TOCSY, total correlation spectroscopy; 2D, two-dimensional

Supplementary key words nuclear magnetic resonance spectroscopy • matrix-assisted laser desorption ionization mass spectroscopy • capillary electrophoresis-mass spectroscopy • tandem mass spectrometry • Thermus oshimai NTU-063 • Thermus thermophilus NTU-077 • Meiothermus ruber NTU-124 • Meiothermus taiwanensis NTU-220


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