Journal
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
Volume 407, Issue 9, Pages 2519-2528Publisher
SPRINGER HEIDELBERG
DOI: 10.1007/s00216-015-8480-1
Keywords
HCD; Linear ion trap; Lysylcardiolipin; Anteiso- and iso-branched fatty acids; Microbial lipids; Lipidomics
Funding
- US Public Health Service [P41-GM103422, P60-DK-20579, P30-DK56341, 5R01AI063428-09, 5T32AR007530-30]
- NIH [1R21HL120760-01]
- NATIONAL HEART, LUNG, AND BLOOD INSTITUTE [R21HL120760] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES [R01AI028973, R01AI063428] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF ARTHRITIS AND MUSCULOSKELETAL AND SKIN DISEASES [T32AR007530] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES [P30DK020579, P30DK056341, P60DK020579] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [P41GM103422] Funding Source: NIH RePORTER
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Listeria monocytogenes (L. monocytogenes) is a facultative, Gram-positive, food-borne bacterium, which causes serious infections. Although it is known that lipids play important roles in the survival of Listeria, the detailed structures of these lipids have not been established. In this contribution, we described linear ion-trap multiple-stage mass spectrometric approaches with high-resolution mass spectrometry toward complete structural analysis including the identities of the fatty acid substituents and their position on the glycerol backbone of the polar lipids, mainly phosphatidylglycerol, cardiolipin (CL), and lysyl-CL from L. monocytogenes. The location of the methyl side group along the fatty acid chain in each lipid family was characterized by a charge-switch strategy. This is achieved by first alkaline hydrolysis to release the fatty acid substituents, followed by tandem mass spectrometry on their N-(4-aminomethylphenyl) pyridinium (AMPP) derivatives as the M+ ions. Several findings in this study are unique: (1) we confirm the presence of a plasmalogen PG family that has not been previous reported; (2) an ion arising from a rare internal loss of lysylglycerol residue was observed in the MS2 spectrum of lysyl-CL, permitting its distinction from other CL subfamilies.
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