A new version of this entry is available:
Loading...
Article
2023
Enrichment and structural assignment of geometric isomers of unsaturated furan fatty acids
Enrichment and structural assignment of geometric isomers of unsaturated furan fatty acids
Abstract (English)
Furan fatty acids (FuFAs) are valuable minor fatty acids, which are known for their excellent radical scavenging properties. Typically, the furan moiety is embedded in an otherwise saturated carboxyalkyl chain. Occasionally, these classic FuFAs are accompanied by low amounts of unsaturated furan fatty acids (uFuFAs), which additionally feature one double bond in conjugation with the furan moiety. A recent study produced evidence for the occurrence of two pairs of E -/ Z -uFuFA isomers structurally related to saturated uFuFAs. Here, we present a strategy that allowed such trace compounds to be enriched to a level suited for structure determination by NMR. Given the low amounts and the varied abundance ratio of the four uFuFA isomers, the isolation of individual compounds was not pursued. Instead, the entire isomer mixture was enriched to an amount and purity suitable for structure investigation with contemporary NMR methods. Specifically, lipid extracted from 150 g latex, the richest known source of FuFAs, was subsequently fractionated by countercurrent chromatography (CCC), silver ion, and silica gel column chromatography. Analysis of the resulting mixture of four uFuFAs isomers (2.4 mg in an abundance ratio of 56:23:11:9) by different NMR techniques including PSYCHE verified that the structures of the two most abundant isomers were E -9-(3-methyl-5-pentylfuran-2-yl)non-8-enoic acid and E -9-(3-methyl-5-pent-1-enylfuran-2-yl)nonanoic acid. Additionally, we introduced a computer-based method to generate an averaged chromatogram from freely selectable GC/MS runs of CCC fractions without the necessity of pooling aliquots. This method was found to be suitable to simplify subsequent enrichment steps.
File is subject to an embargo until
This is a correction to:
A correction to this entry is available:
This is a new version of:
Other version
Notes
Publication license
Publication series
Published in
Analytical and bioanalytical chemistry, 415 (2023), 25, 6333-6343.
https://doi.org/10.1007/s00216-023-04908-z.
ISSN: 1618-2650
Other version
Faculty
Institute
Examination date
Supervisor
Cite this publication
Müller, F., Conrad, J., Hammerschick, T., & Vetter, W. (2023). Enrichment and structural assignment of geometric isomers of unsaturated furan fatty acids. Analytical and bioanalytical chemistry, 415(25). https://doi.org/10.1007/s00216-023-04908-z
Edition / version
Citation
DOI
ISSN
ISBN
Language
English
Publisher
Publisher place
Classification (DDC)
540 Chemistry
Original object
University bibliography
Standardized keywords (GND)
Sustainable Development Goals
BibTeX
@article{Müller2023,
doi = {10.1007/s00216-023-04908-z},
author = {Müller, Franziska and Conrad, Jürgen and Hammerschick, Tim et al.},
title = {Enrichment and structural assignment of geometric isomers of unsaturated furan fatty acids},
journal = {Analytical and Bioanalytical Chemistry},
year = {2023},
volume = {415},
number = {25},
pages = {6333--6343},
}