1. Synthesis of selenated hydroxy fatty acids
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O
C
HO
Hydroxylation
(KMnO4; H+ in H2O)
HO
O
C
OH
HO
OH
OH
Esterification
(H2SeO3 in dioxane; catalyst
O
Se
O
O
C
O
HO
O
O
Se
O
)
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2. Speciation of selenium in selol 5%
The second topic researched by our team is to examine the structure
of molecules of hydroxylated triglycerides containing selenium (IV).
In our research we use HPLC-ICP MS/ electrospray - Orbitrap MS/MS
techniques and 1H, 13C and 77Se NMR.
We use hydroxylated and selenated standards obtained from trioleic
and trilinolenic glycerides.
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In selol molecules we have observed 4 repetitive
modifications of structures containing selenium.
Species identification
formula
mass*
theoretical
C57H100O12Se2
C57H100O11Se
C57H100O9Se
C57H100O10Se
C57H98O9Se
C57H98O8Se
C57H102O12Se2
C57H102O9Se
error, triglyceride modification*
experimental ppm
1159.5437
1063.6323
1031.6425
1047.6374
1029.6268
1013.6319
1049.6536
1033.6587
1159,5444
1063,6337
1031.6443
1047,6389
1029.6290
1013,6325
1049,6505
1033,6547
0,08
0,79
1,19
0,96
1,62
-0,01
-2,41
-3,35
LLO
LLL
LLO
LLL
LLL
OOO
LLO
LOO
4
1
3
2
3
3
2
3
*masses correspond to [M+Na]+ except C57H98O8Se
**modifications:
O
1
Se
HO
O
OH O
O
2
3
Se
HO
O
Se
O
O
O
O
O
O
4
Se
Se
O
O
O
O
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(a)
The panel presents HPLC-ICP MS chromatogram in
order to demonstrate the matching of peaks obtained
using elemental and molecular MS detection.
0
10
20
30
40
50
60
trilinoleate derivatives
O
Na
O
H 2C
HO
OH
C
O
HC O
Se
O O
C57H100O11Se
O
C
H 2C
O
C
O
0
5
10
15
20
25
O
+
Na
Se
O
HO
O
O
CH3
O
O
CH3
O
5
10
15
20
25
C57H100O10Se
CH3
O
0
O
O
Se
Na
O
O
O
O
O
O
C57H98O9Se
O
O
0
5
10
15
Retention time, min
20
25
Putative formula supported by MS2 and MS3
analysis.
Extracted ion chromatograms (XICs) corresponding to the
pseudomolecular ions containing one or more selenium atoms
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(b)
The panel presents HPLC-ICP MS chromatogram in
order to demonstrate matching of peaks obtained using
elemental and molecular MS detection.
0
10
20
30
40
50
60
dilinoleate-monooleate derivatives
O
Na
O
H 2C
HO
O
HC O
Se
O
C
O
C57H102O10Se
O
C
H 2C
O
C
O
0
5
10
15
20
25
O
+
Se
Na
O
O
O
O
CH3
O
O
O
CH3
O
0
5
10
15
20
25
O
Na
O
H 2C
O
O
C
HC O
H 2C
C57H100O9Se
CH3
O
O
Se
O
Se
O O
C57H100O12Se2
C
O
C
O
0
5
10
15
Retention time, min
20
25
Putative formula supported by MS2 and MS3
analysis.
Extracted ion chromatograms (XICs) corresponding to the
pseudomolecular ions containing one or more selenium atoms
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(c)
The panel presents HPLC-ICP MS chromatogram in
order to demonstrate matching of peaks obtained
using elemental and molecular MS detection.
0
10
20
30
40
50
60
monolinoleate-dioleate derivatives
O
Na
Se
O
H 2C O
HC O
H 2C
0
5
10
15
20
O
O
C
O
C57H102O9Se
C
O
C
25
O
O
Se
Na
Se
O
H 2C O
HC O
H 2C
O
C
O
C57H102O9Se2
O
C
O
C
O
0
5
10
15
20
25
trioleate derivative
O
Se
O
O
O
O
O
O
C57H104O9Se
O
0
5
10
15
Retention time, min
20
25
O
Putative formula supported by MS2 and MS3
analysis.
Extracted ion chromatograms (XICs) corresponding to the
pseudomolecular ions containing one or more selenium atoms
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An example of the fragmentation cascade
for species m/z 1013.6913 (C57H104O9Se)
O
Se
O
O
O
O
SeH
MS2
O
O
O
O
O
CH3
O
O
O
O
O
O
O
O
MS2
Se
O
C57H104O9Se[M+H]+
O
O
CH3
O
CH3
MS2
O
+
C56H96O9Se[M+H]
+
O
Na
O
MS2
Se
O
O
CH3
O
O
Na
O
O
CH3
O
C57H96O7Se[M+Na]+
O
Na
Se
O
MS3
C57H106O5Se[M+H]+
MS2
Se
O
O
O
O
O
O
O
O
CH3
C39H68O6Se[M+H]+
C39H68O8Se[M+H]+
MS3
MS3
O
Se
+
Na
O
O
Se
Na
O
O
O
O
O
CH3
O
H2C
C18H32O4Se[M+Na]+
MS3
CH3
C39H64O5Se[M+Na]+
Na
O
Se
O
Na
O
O
MS3
O
O
C18H30O3Se[M+H]+
O
Se
Na
O
O
Se
Se
Na
O
MS3
O
O
O
O
C18H30O3Se[M+Na]+
C31H50O5Se[M+Na]+
Na
O
MS3
SeH
C18H32O3Se[M+H]+
O
O
C21H36O3Se[M+Na]+
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Balance sheet
Income
Received
amount
Stay
Persons
Expenses
21-02-2013
€ 21 954.41
14-21 May 2015
Prof. Ricardo Bentez
Azevedo
€ 546.00
Prof. Zulmira Marquez
Lacava
€ 546.00
Remaining
amount
€ 20 862.41
Total
€ 1 092.00
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Our plans for the visit at the University of Brasilia
In May and June, I want to send two of my PhD students to Prof. Zulmira Lacava
and Prof. Ricardo Azevedo, and in June I hope to come with prof. Zbigniew
Fijałek for one month.
Persons
Arrival
Departure
Anna Flis-Borsuk - PhD student
Lidia Śliwka PhD student
1 May 2016
30 June 2016
Prof. Zbigniew Fijałek
Prof. Piotr Suchocki
1 June 2016
30 June 2016