Biosynthesis of polyunsaturated short chain aldehydes in the diatom Thalassiosira rotula.
The diatom Thalassiosira rotula releases polyunsaturated short chain aldehydes (PUA) such as 2E,4Z,7-octatrienal (7a) and 2E,4Z,7Z-decatrienal (3a) upon wounding. Using labeling experiments and synthetic standards, we demonstrate that the mechanism of fatty acid transformation does not follow established lipoxygenase/hydroperoxide lyase pathways known from higher plants or mammals but rather relies on a unique transformation of polyunsaturated hydroperoxy fatty acids. These intermediates are transformed to PUA and short chain hydroxylated fatty acids, which are novel oxylipins. [reaction: see text]
Barofsky
Alexandra
A
Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des sciences et ingénierie chimiques, LECH, Batochimie, CH-1015 Lausanne, Switzerland.
Pohnert
Georg
G
D000446:Aldehyde-Lyases / Q000737:chemistry / Q000378:metabolism; D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism*; D000475:Alkenes / Q000737:chemistry / Q000378:metabolism*; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry / Q000378:metabolism; D017377:Diatoms / Q000737:chemistry*; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000378:metabolism*; D008084:Lipoxygenase / Q000737:chemistry / Q000378:metabolism; D008386:Marine Biology; D008956:Models, Chemical
C508576:2E,4Z,7Z-decatrienal; D000447:Aldehydes; D000475:Alkenes; D004952:Esters; D005231:Fatty Acids, Unsaturated; D003577:Cytochrome P-450 Enzyme System; D008084:Lipoxygenase; D000446:Aldehyde-Lyases; C054540:hydroperoxide lyase