Two unusual glycerophospholipids from a filamentous fungus, Absidia corymbifera

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids
2001.0

Abstract

The chloroform-methanol extractable lipids of the soil filamentous fungus Absidia corymbifera VKMF-965 account for about 20% by weight of dry cells and are composed of low-polarity constituents (about 75% of the total lipids), such as triacylglycerols (mainly), diacylglycerols, sterols and free fatty acids, as well as of glycolipids (about 3%) and phospholipids. The last consist largely of components common to the fungal lipids, namely, phosphatidylethanolamine (38% of the total phospholipids), phosphatidyl-myo-inositol (16%), diphosphatidylglycerol (12%), phosphatidylcholine (7%), phosphatidic acid (6%) and phosphatidylglycerol (3%), and two unusual phospholipids, PL1 (6%) and PL2 (9%). Based on the infrared (IR), (1)H-nuclear magnetic resonance (NMR), (13)C-NMR and mass spectra along with the results of degradation experiment, these two phospholipids have been established to be 1,2-diacyl-sn-glycero-3-phospho(N-acetylethanolamine), or N-acetyl phosphatidylethanolamine, and 1,2-diacyl-sn-glycero-3-phospho(N-ethoxycarbonyl-ethanolamine), respectively. These structures have been confirmed by preparing similar phospholipids from the phosphatidylethanolamine isolated from the same fungus and correlating their chromatographic behaviour, IR and (1)H-NMR spectra with those of PL1 and PL2. So far N-acetyl phosphatidylethanolamine has been detected only in cattle and human brains and a human placenta but its structure was not rigorously proved. PL2 is a novel lipid; to our knowledge no natural phospholipid with an urethane group has yet been found. The main fatty acids of both the phospholipids are n-hexadecanoic, octadecanoic and octadecadienoic ones; PL2 contains in addition a considerable amount of octadecatrienoic acid with its greater portion located at the sn-1 position.

Knowledge Graph

Similar Paper

Two unusual glycerophospholipids from a filamentous fungus, Absidia corymbifera
Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids 2001.0
Isolation of 2-Aminoethylphosphonic Acid from Phospholipids of the Abalone (Haliotis midae)
Nature 1966.0
Isolation and Structure Elucidation of Cerebrosides from Euphorbia Platyphyllos L.
Scientia Pharmaceutica 2008.0
1-O-(13-Methyl-1-Z-tetradecenyl)-2-O-(13-methyItetradecanoyl)- glycero-3-phospho-ethanolamin, ein Plasmalogen aus Myxococcus stipitatus/ 1-O-(13-Methyl-1-Z-tetradecenyl)-2-O-(13-methyltetradecanoyl)-glycero-3-phosphoethanolamine, a Plasmalogen from Myxococcus stipitatus
Zeitschrift für Naturforschung B 1987.0
Structural Elucidation of Novel Phosphocholine-Containing Glycosylinositol-Phosphoceramides in Filamentus Fungi: (2). Spectral Analysis of the Sugar-Inositol Portion by 2D-NMR
Chemical and Pharmaceutical Bulletin 2004.0
Novel Glycerolipids and Glycolipids from the Surface Lipids of<i>Nicotiana benthamiana</i>
Bioscience, Biotechnology, and Biochemistry 1992.0
Two 1-Alkyl-2-acyl Choline Glycerophospholipids Having an Arachidonoyl or Eicosapentaenoyl Group, from the Clam Worm (Marphysa sanguinea).
Chemical and Pharmaceutical Bulletin 1995.0
New Glycosphingolipids from the Fungus <i>Catathelasma </i><i>v</i><i>entricosa</i>
Journal of Natural Products 2003.0
New Sphingolipids with a Previously Unreported 9‐Methyl‐C<sub>20</sub>‐sphingosine Moiety from a Marine Algous Endophytic Fungus <i>Aspergillus niger</i> EN‐13
Lipids 2007.0
A novel glycosphingolipid from Gram-negative aquatic bacteria
Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids 1999.0