Polar lipids of a non-alkaliphilic extremely halophilic archaebacterium strain 172: a novel bis-sulfated glycolipid.
Extremely halophilic archaebacteria which require high salt concentrations for growth and survival contain glycerol diether analogues of phospholipids and sulfated glycolipids as major membrane polar lipids. A non-alkaliphilic, non-pigmented rod-shaped extreme halophile, isolated from sea sand in Japan and designated 'strain 172', was found to contain two phospholipids, phosphatidylglycerol (PG) and phosphatidylglyceromethylphosphate (PGP-Me), derived from both C20-C20- and C20-C25-glycerol diethers, and a novel major glycolipid (designated SGL-X). This glycolipid has been identified as a bis-sulfated diglycosyl C20-C20- or C20-C25-glycerol diether, on the basis of its TLC mobility, positive-staining behavior with sugar and sulfate-staining reagents, its mole ratio sulfate/glycolipid = 2.2, and by spectrometric analysis (IR and FAB-MS) of the intact and the desulfated SGL-X. The sugars were identified as mannose and glucose, after acid hydrolysis of SGL-X, by paper chromatography of the free sugars and GC-MS of the derivatized sugars (alditol acetates). Permethylation analysis and 1H- and 13C-NMR analysis established the position and configuration of the sugar linkages and the positions of the sulfate groups. The final structure of SGL-X (now designated S2-DGD-1) is proposed to be: 2,3-diphytanyl- or phytanyl-sesterterpenyl-1-[2,6-(HSO3)2-alpha-Manp-1--> 2- Glcp]-sn-glycerol. This lipid is the first bis-sulfated glycolipid to be reported in extremely halophilic archaebacteria, and is the first in the biosphere that possesses two sulfate groups attached to the same monosaccaride.
Matsubara
T
T
Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan.
Iida-Tanaka
N
N
Kamekura
M
M
Moldoveanu
N
N
Ishizuka
I
I
Onishi
H
H
Hayashi
A
A
Kates
M
M
D001105:Archaea / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D008401:Gas Chromatography-Mass Spectrometry; D005947:Glucose / Q000032:analysis; D006017:Glycolipids / Q000032:analysis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000032:analysis; D008745:Methylation; D008969:Molecular Sequence Data; D010715:Phosphatidylglycerols / Q000032:analysis; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared
D006017:Glycolipids; D010715:Phosphatidylglycerols; C034358:phosphatidylglycerophosphate; C011117:sulfoglycolipids; D005947:Glucose; D008358:Mannose