title: Structural characterization of diabolic acid-based tetraester, tetraether and mixed ether/ester, membrane-spanning lipids of bacteria from the order Thermotogales.
abstract: The distribution of core lipids in the membranes of nine different species of the order Thermotogales, one of the early and deep branching lineages in the Bacteria, were examined by HPLC/MS and demonstrated to consist of membrane-spanning diglycerol lipids comprised of diabolic acid-derived alkyl moieties. In the Thermotoga species the core membrane lipids are characterized by the presence of both ester and ether bonds, whereas in the phylogenetically more distinct Thermosipho and Fervidobacterium spp. only ester bonds occur. A tentative biosynthetic route for the biosynthesis of these membrane-spanning lipids is proposed. Since species of the order Thermotogales are assumed to have occurred early during the evolution of life on Earth, as suggested by its position in the phylogenetic tree of life, these data suggest that the ability to produce both ether and ester glycerol membrane lipids developed relatively early during microbial evolution.
authors.affiliation: Department of Marine Biogeochemistry and Toxicology, Royal Netherlands Institute for Sea Research (NIOZ), PO Box 59, 1790 AB, Den Burg, Texel, The Netherlands. damste@nioz.nl
authors.forename: Jaap S Sinninghe
authors.initials: JS
authors.lastname: Damsté
authors.forename: W Irene C
authors.initials: WI
authors.lastname: Rijpstra
authors.forename: Ellen C
authors.initials: EC
authors.lastname: Hopmans
authors.forename: Stefan
authors.initials: S
authors.lastname: Schouten
authors.forename: Melike
authors.initials: M
authors.lastname: Balk
authors.forename: Alfons J M
authors.initials: AJ
authors.lastname: Stams
mesh_terms: D001421:Bacteria, Anaerobic / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003998:Dicarboxylic Acids / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D004952:Esters / Q000032:analysis / Q000378:metabolism; D004987:Ethers / Q000032:analysis / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D008563:Membrane Lipids / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*
chemical_list: D003998:Dicarboxylic Acids; D004952:Esters; D004987:Ethers; D008563:Membrane Lipids; C023457:diabolic acids