New C16 fatty-acid-based oxylipin pathway in the marine diatom Thalassiosira rotula.
An unprecedented series of C16 oxylipins (1-8) has been characterized from the marine diatom Thalassiosira rotula. Absolute stereochemistry of the major alcohols 1 and 3 was determined to be 9S by spectroscopic and chemical methods. All the described products are formally derived by unprecedented enzymatic oxidation of C16 fatty acids. Conversion of hexadeca-6,9,12-trienoic acid (C16:3 omega-4) into 3 unequivocally established the occurrence of (at least) a specific 9S-oxygenase activity. To the best of our knowledge, the present data reveal for the first time the existence of an organic network of oxygenase-mediated transformations that require C16 fatty acids as substrates in living cells.
d'Ippolito
Giuliana
G
Istituto di Chimica Biomolecolare (ICB) del CNR, Via Campi Flegrei 34, 80078, Pozzuoli (Napoli), Italy.
Cutignano
Adele
A
Briante
Raffaella
R
Febbraio
Ferdinando
F
Cimino
Guido
G
Fontana
Angelo
A
D017377:Diatoms / Q000378:metabolism*; D004952:Esters / Q000737:chemistry / Q000378:metabolism*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry* / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D007525:Isoelectric Focusing; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009792:Oceans and Seas; D013237:Stereoisomerism
D004952:Esters; D005231:Fatty Acids, Unsaturated