A lipoxygenase-divinyl ether synthase pathway in flax (Linum usitatissimum L.) leaves.
Incubation of linoleic acid with an enzyme preparation from leaves of flax (Linum usitatissimum L.) led to the formation of a divinyl ether fatty acid, i.e. (9Z,11E,1'Z)-12-(1'-hexenyloxy)-9,11-dodecadienoic [(omega5Z)-etheroleic] acid, as well as smaller amounts of 13-hydroxy-9(Z),11(E)-octadecadienoic acid. The 13-hydroperoxide of linoleic acid afforded the same set of products, whereas incubations of alpha-linolenic acid and its 13-hydroperoxide afforded the divinyl ether (9Z,11E,1'Z,3'Z)-12-(1',3'-hexadienyloxy)-9,11-dodecadienoic [(omega5Z)-etherolenic] as the main product. Identification of both divinyl ethers was substantiated by their UV, mass-, (1)H NMR and COSY spectral data. In addition to the 13-lipoxygenase and divinyl ether synthase activities demonstrated by these results, flax leaves also contained allene oxide synthase activity as judged by the presence of endogenously formed (15Z)-cis-12-oxo-10,15-phytodienoic acid in all incubations.
Kazan Institute of Biochemistry and Biophysics, Russian Academy of Sciences, Kazan, Russia.
Ivan R
IR
Chechetkin
Alexander
A
Blufard
Mats
M
Hamberg
Alexander N
AN
Grechkin
D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D019597:Flax / Q000201:enzymology* / Q000235:genetics; D008401:Gas Chromatography-Mass Spectrometry; D008084:Lipoxygenase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D054883:Oxylipins / Q000737:chemistry / Q000378:metabolism; D010802:Phylogeny; D018515:Plant Leaves / Q000201:enzymology; D010940:Plant Proteins / Q000378:metabolism*; D015398:Signal Transduction
D054883:Oxylipins; D010940:Plant Proteins; D003577:Cytochrome P-450 Enzyme System; C100485:divinyl ether synthase; D008084:Lipoxygenase