Koninklijke Bibliotheek, National Library of the Netherlands
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Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals
Komaszylo née Siedlecka, Joanna
Kania, Magdalena
Masnyk, Marek
Cmoch, Piotr
Lozinska, Iwona
Czarnocki, Zbigniew
Skorupinska-Tudek, Karolina
Danikiewicz, Witold
Swiezewska, Ewa
text
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monographic
Lipids
continuing
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EWTIJ
10.1007/s11745-015-4104-y
urn:nbn:nl:kb-1454493458176
Automatisch gegenereerd op basis van de EWTIJ XML in release 1.5 van het digitaal magazijn.
Springer Berlin Heidelberg
Berlin/Heidelberg
Springer
11745
10.1007/11745.1558-9307
0024-4201
1558-9307
Lipids
Lipids
Life Sciences
Lipidology
Neurochemistry
Medical Biochemistry
Nutrition
Medicinal Chemistry
Microbial Genetics and Genomics
SC3
51
51
12
2
2
12
2016
2
1
2016
2
1
2016
2
2016
AOCS
2016
4104
10.1007/s11745-015-4104-y
9
Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals
Original Article
229
244
2015
11
21
2015
1
30
2015
11
19
2015
12
30
National Science Centre of Poland
UMO-2012/07/B/NZ3/02437
Polish National Cohesion Strategy Innovative Economy
UDA-POIG 01.03.01-14-036/09
The Author(s)
2015
Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (
http://creativecommons.org/licenses/by/4.0/
), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
Joanna
Komaszylo née Siedlecka
+48225923501
joannas@ibb.waw.pl
Magdalena
Kania
+48223432219
kaniam@icho.edu.pl
Marek
Masnyk
Piotr
Cmoch
Iwona
Lozinska
Zbigniew
Czarnocki
Karolina
Skorupinska-Tudek
Witold
Danikiewicz
Ewa
Swiezewska
Department of Lipid Biochemistry, Institute of Biochemistry and Biophysics
Polish Academy of Sciences (PAS)
Pawinskiego 5a
02-106
Warsaw
Poland
Laboratory of Mass Spectrometry, Institute of Organic Chemistry
Polish Academy of Sciences (PAS)
Kasprzaka 44/52
01-224
Warsaw
Poland
Faculty of Chemistry
University of Warsaw
Warsaw
Poland
Abstract
Isoprenoids, as common constituents of all living cells, are exposed to oxidative agents—reactive oxygen species, for example, singlet oxygen or hydroxyl radicals. Despite this fact, products of oxidation of polyisoprenoids have never been characterized. In this study, chemical oxidation of isoprenoid alcohols (Prenol-2 and -10) was performed using singlet oxygen (generated in the presence of hydrogen peroxide/molybdate or upon photochemical reaction in the presence of porphyrin), oxygen (formed upon hydrogen peroxide dismutation) or hydroxyl radical (generated by the hydrogen peroxide/sonication, UV/titanium dioxide or UV/hydrogen peroxide) systems. The structure of the obtained products, hydroxy-, peroxy- and heterocyclic derivatives, was studied with the aid of mass spectrometry (MS) and nuclear magnetic resonance (NMR) methods. Furthermore, mass spectrometry with electrospray ionization appeared to be a useful analytical tool to detect the products of oxidation of isoprenoids (ESI–MS analysis), as well as to establish their structure on the basis of the fragmentation spectra of selected ions (ESI–MS/MS analysis). Taken together, susceptibility of polyisoprenoid alcohols to various oxidizing agents was shown for the first time.
Keywords
Isoprenoid oxidation
Singlet oxygen
Hydrogen peroxide
Sodium molybdate
Porphyrin
Hydroxyl radical
Oxygen
UV irradiation
Abbreviations
AOP
Advanced oxidation process
CE
Collision energy
CID
Collision-induced dissociation
D or Dol
Dolichol
EI
Electron impact
ESI–MS
Electrospray coupled with mass spectrometry
ESI–MS/MS
Electrospray coupled with tandem mass spectrometry
GC/FID
Gas chromatography coupled with flame ionization detector
GC/MS
Gas chromatography coupled with mass spectrometry
4-HNE
4-Hydroxynonenal
HPLC/ESI–MS
High-performance liquid chromatography coupled with electrospray ionization–mass spectrometry
HPLC/UV
High-performance liquid chromatography coupled with ultraviolet absorption detector
LC/ESI–MS
Liquid chromatography coupled with electrospray ionization-mass spectrometry
MDA
Malondialdehyde
NMR
Nuclear magnetic resonance spectroscopy
P or Pren
Prenol
P-2
Prenol-2
P-10
Prenol-10
ROS
Reactive oxygen species
TLC
Thin-layer chromatography
UV
Ultraviolet radiation
Electronic supplementary material
The online version of this article (doi:
10.1007/s11745-015-4104-y
) contains supplementary material, which is available to authorized users.
Springer Berlin Heidelberg
Berlin/Heidelberg
Springer
11745
10.1007/11745.1558-9307
0024-4201
1558-9307
Lipids
Lipids
Life Sciences
Lipidology
Neurochemistry
Medical Biochemistry
Nutrition
Medicinal Chemistry
Microbial Genetics and Genomics
SC3
51
51
12
2
2
12
2016
2
1
2016
2
1
2016
2
2016
AOCS
2016
4104
10.1007/s11745-015-4104-y
9
Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals
Original Article
229
244
2015
11
21
2015
1
30
2015
11
19
2015
12
30
National Science Centre of Poland
UMO-2012/07/B/NZ3/02437
Polish National Cohesion Strategy Innovative Economy
UDA-POIG 01.03.01-14-036/09
The Author(s)
2015
Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (
http://creativecommons.org/licenses/by/4.0/
), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
Joanna
Komaszylo née Siedlecka
+48225923501
joannas@ibb.waw.pl
Magdalena
Kania
+48223432219
kaniam@icho.edu.pl
Marek
Masnyk
Piotr
Cmoch
Iwona
Lozinska
Zbigniew
Czarnocki
Karolina
Skorupinska-Tudek
Witold
Danikiewicz
Ewa
Swiezewska
Department of Lipid Biochemistry, Institute of Biochemistry and Biophysics
Polish Academy of Sciences (PAS)
Pawinskiego 5a
02-106
Warsaw
Poland
Laboratory of Mass Spectrometry, Institute of Organic Chemistry
Polish Academy of Sciences (PAS)
Kasprzaka 44/52
01-224
Warsaw
Poland
Faculty of Chemistry
University of Warsaw
Warsaw
Poland
Abstract
Isoprenoids, as common constituents of all living cells, are exposed to oxidative agents—reactive oxygen species, for example, singlet oxygen or hydroxyl radicals. Despite this fact, products of oxidation of polyisoprenoids have never been characterized. In this study, chemical oxidation of isoprenoid alcohols (Prenol-2 and -10) was performed using singlet oxygen (generated in the presence of hydrogen peroxide/molybdate or upon photochemical reaction in the presence of porphyrin), oxygen (formed upon hydrogen peroxide dismutation) or hydroxyl radical (generated by the hydrogen peroxide/sonication, UV/titanium dioxide or UV/hydrogen peroxide) systems. The structure of the obtained products, hydroxy-, peroxy- and heterocyclic derivatives, was studied with the aid of mass spectrometry (MS) and nuclear magnetic resonance (NMR) methods. Furthermore, mass spectrometry with electrospray ionization appeared to be a useful analytical tool to detect the products of oxidation of isoprenoids (ESI–MS analysis), as well as to establish their structure on the basis of the fragmentation spectra of selected ions (ESI–MS/MS analysis). Taken together, susceptibility of polyisoprenoid alcohols to various oxidizing agents was shown for the first time.
Keywords
Isoprenoid oxidation
Singlet oxygen
Hydrogen peroxide
Sodium molybdate
Porphyrin
Hydroxyl radical
Oxygen
UV irradiation
Abbreviations
AOP
Advanced oxidation process
CE
Collision energy
CID
Collision-induced dissociation
D or Dol
Dolichol
EI
Electron impact
ESI–MS
Electrospray coupled with mass spectrometry
ESI–MS/MS
Electrospray coupled with tandem mass spectrometry
GC/FID
Gas chromatography coupled with flame ionization detector
GC/MS
Gas chromatography coupled with mass spectrometry
4-HNE
4-Hydroxynonenal
HPLC/ESI–MS
High-performance liquid chromatography coupled with electrospray ionization–mass spectrometry
HPLC/UV
High-performance liquid chromatography coupled with ultraviolet absorption detector
LC/ESI–MS
Liquid chromatography coupled with electrospray ionization-mass spectrometry
MDA
Malondialdehyde
NMR
Nuclear magnetic resonance spectroscopy
P or Pren
Prenol
P-2
Prenol-2
P-10
Prenol-10
ROS
Reactive oxygen species
TLC
Thin-layer chromatography
UV
Ultraviolet radiation
Electronic supplementary material
The online version of this article (doi:
10.1007/s11745-015-4104-y
) contains supplementary material, which is available to authorized users.
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