Open AccessNovel polyunsaturated n ‐alkenes in the marine diatom Rhizosolenia setigera
Author(s) -
Damsté Jaap S. Sinninghe,
Schouten Stefan,
Rijpstra W. Irene C.,
Hopmans Ellen C,
Peletier Harry,
Gieskes Winfried W. C.,
Geenevasen Jan A. J.
Publication year - 2000
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1046/j.1432-1327.2000.01636.x
Subject(s) - double bond , diatom , polyunsaturated fatty acid , stereochemistry , methylene , elongation , decarboxylation , chemistry , fatty acid , biology , botany , biochemistry , materials science , organic chemistry , ultimate tensile strength , metallurgy , catalysis
Four previously unknown n ‐C 25 and n ‐C 27 heptaenes of the marine diatom Rhizosolenia setigera were isolated and identified using NMR spectroscopy. They possess six methylene interrupted ( Z )‐double bonds starting at C‐3 and an additional terminal or n ‐2 ( Z )‐double bond. Structural and stable carbon isotopic evidence suggests that these polyenes are biosynthesized by chain elongation of the C22:6 n ‐3 fatty acid, followed by decarboxylation and introduction of double bonds at specific positions.