Double bond stereochemistry influences the susceptibility of short-chain isoprenoids and polyprenols to decomposition by thermo-oxidation

Lipids
Ewa Molińska Nee SosińskaEwa Swiezewska

Abstract

Isoprenoid alcohols are common constituents of living cells. They are usually assigned a role in the adaptation of the cell to environmental stimuli, and this process might give rise to their oxidation by reactive oxygen species. Moreover, cellular isoprenoids may also undergo various chemical modifications resulting from the physico-chemical treatment of the tissues, e.g., heating during food processing. Susceptibility of isoprenoid alcohols to heat treatment has not been studied in detail so far. In this study, isoprenoid alcohols differing in the number of isoprene units and geometry of the double bonds, β-citronellol, geraniol, nerol, farnesol, solanesol and Pren-9, were subjected to thermo-oxidation at 80 °C. Thermo-oxidation resulted in the decomposition of the tested short-chain isoprenoids as well as medium-chain polyprenols with simultaneous formation of oxidized derivatives, such as hydroperoxides, monoepoxides, diepoxides and aldehydes, and possible formation of oligomeric derivatives. Oxidation products were monitored by GC-FID, GC-MS, ESI-MS and spectrophotometric methods. Interestingly, nerol, a short-chain isoprenoid with a double bond in the cis (Z) configuration, was more oxidatively stable than its trans (E) i...Continue Reading

References

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Citations

Dec 31, 2015·Lipids·Joanna Komaszylo Née SiedleckaEwa Swiezewska
Mar 13, 2016·Lipids·Gabriella CavalliniEttore Bergamini
May 3, 2016·Free Radical Research·Hiroko-Miyuki Mori, Hideo Iwahashi
Jul 26, 2017·Photosynthesis Research·Jessica M WiwczarGary W Brudvig

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Methods Mentioned

BETA
glycosylation
NMR
column chromatography

Software Mentioned

SPSS Statistics
Analyst

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