Double Bond Stereochemistry Influences the Susceptibility of Short-Chain Isoprenoids and Polyprenols to Decomposition by Thermo-Oxidation
PBN-AR
Instytucja
Instytut Chemii Organicznej Polskiej Akademii Nauk
Źródłowe zdarzenia ewaluacyjne
Informacje podstawowe
Główny język publikacji
en
Czasopismo
LIPIDS
ISSN
0024-4201
EISSN
1558-9307
Wydawca
SPRINGER HEIDELBERG
DOI
URL
Rok publikacji
2015
Numer zeszytu
4
Strony od-do
359-370
Numer tomu
50
Identyfikator DOI
Liczba arkuszy
Słowa kluczowe
en
Isoprenoid
Oligoprenol
Polyprenol
Thermo-oxidation
Oxidation products
Streszczenia
Język
en
Treść
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) isomer, geraniol. However, the opposite effect was observed for medium-chain polyprenols, since Pren-9 (di-trans-poly-cis-prenol) was more susceptible to thermo-oxidation than its all-trans isomer, solanesol. Taken together, these results experimentally confirm that both short- and long-chain polyisoprenoid alcohols are prone to thermo-oxidation.
Cechy publikacji
ORIGINAL_ARTICLE
Inne
System-identifier
647190
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