Novel polyunsaturated n-alkenes in the marine diatom Rhizosolenia setigera.
Four previously unknown n-C25 and n-C27 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 C22:6n-3 fatty acid, followed by decarboxylation and introduction of double bonds at specific positions.
Damsté
J S
JS
Netherlands Institute for Sea Research (NIOZ), Department of Marine Biogeochemistry and Toxicology, Department of Marine Biology, University of Groningen, the Netherlands. damste@nioz.nl
Schouten
S
S
Rijpstra
W I
WI
Hopmans
E C
EC
Peletier
H
H
Gieskes
W W
WW
Geenevasen
J A
JA
D000475:Alkenes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D002244:Carbon / Q000737:chemistry; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D017377:Diatoms / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D006536:Heptanes / Q000737:chemistry; D006838:Hydrocarbons; D008055:Lipids / Q000096:biosynthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008956:Models, Chemical; D013696:Temperature; D013997:Time Factors
D000475:Alkenes; D006536:Heptanes; D006838:Hydrocarbons; D008055:Lipids; C030011:carbene; D002244:Carbon; D008697:Methane