Ether lipids in the cell membrane of Mycoplasma fermentans.
Two new ether lipids, 1-O-alkyl/alkenyl-2-O-acyl-glycero-3-phosphocholine and its lyso form, 1-O-alkyl/alkenyl-glycero-3-phosphocholine, were identified in the cell membrane of Mycoplasma fermentans using chemical analyses, GLC-MS, MALDI-TOF MS, and 1D and 2D NMR spectroscopy. The lipids are heterogeneous with respect to both acyl and alkyl/alkenyl residues. The acyl residues at position 2 of glycerol are hexadecanoyl and octadecanoyl in a molar ratio of 3.6 : 1 with a trace amount of octadecenoyl. The alkyl/alkenyl residues at position 1 of glycerol are hexadecyl (78%), octadecyl (7%), octadecenyl (14%), and hexadecenyl (traces). In the octadecenyl residue, the double bond has a cis configuration and is located at either position 1' (plasmalogen-type lipid) or 9' in a ratio approximately 1 : 1. This is the first report of the presence of alkyl and vinyl (alk-1'-enyl) ether lipids in the cell membrane of aerobically grown mycoplasmas. Lipids of this type have been found in some Gram-positive bacteria, thus supporting the hypothesized close taxonomical relationship of these bacteria to mycoplasmas. The ether lipids of M. fermentans are structurally similar to platelet activating factor; it was demonstrated that the 2-O-acetylated lyso form lipid can mimic platelet-activating factor activity in isolated perfused and ventilated rat lungs.
Wagner
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F
Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany.
Rottem
S
S
Held
H D
HD
Uhlig
S
S
Zähringer
U
U
D000818:Animals; D016084:Bronchoconstriction / Q000187:drug effects; D002462:Cell Membrane / Q000737:chemistry*; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D066298:In Vitro Techniques; D008168:Lung / Q000187:drug effects / Q000502:physiology*; D008246:Lysophospholipids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008563:Membrane Lipids / Q000737:chemistry* / Q000302:isolation & purification; D016858:Mycoplasma fermentans / Q000737:chemistry*; D010742:Phospholipid Ethers / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010972:Platelet Activating Factor / Q000494:pharmacology; D011651:Pulmonary Artery / Q000187:drug effects / Q000502:physiology*; D051381:Rats; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014661:Vasoconstriction / Q000187:drug effects
D008246:Lysophospholipids; D008563:Membrane Lipids; D010742:Phospholipid Ethers; D010972:Platelet Activating Factor