1. 1. Synthesis of selenated hydroxy fatty acids BRASINOE U

2. 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 1 H, 13 C and 77 Se NMR. We use hydroxylated and selenated standards obtained from trioleic and trilinolenic glycerides. BRASINOE U

3. formulamass*error, ppm triglyceridemodification* theoreticalexperimental C 57 H 100 O 12 Se 2 C 57 H 100 O 11 Se C 57 H 100 O 9 Se C 57 H 100 O 10 Se C 57 H 98 O 9 Se C 57 H 98 O 8 Se C 57 H 102 O 12 Se 2 C 57 H 10 2O 9 Se 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 OOO LLO LOO 41323323 41323323 Species identification * masses correspond to [M+Na] + except C 57 H 98 O 8 Se ** modifications: In selol molecules we have observed 4 repetitive modifications of structures containing selenium. BRASINO EU

4. 0510152025 0510152025 0510152025 0102030405060 C 57 H 98 O 9 Se C 57 H 100 O 10 Se C 57 H 100 O 11 Se trilinoleate derivatives Retention time, min (a) The panel presents HPLC-ICP MS chromatogram in order to demonstrate the matching of peaks obtained using elemental and molecular MS detection. Extracted ion chromatograms (XICs) corresponding to the pseudomolecular ions containing one or more selenium atoms Putative formula supported by MS2 and MS3 analysis. BRASINOE U

5. 0102030405060 dilinoleate-monooleate derivatives 0510152025 0510152025 C 57 H 100 O 9 Se C 57 H 100 O 12 Se 2 C 57 H 102 O 10 Se Retention time, min (b) The panel presents HPLC-ICP MS chromatogram in order to demonstrate matching of peaks obtained using elemental and molecular MS detection. Extracted ion chromatograms (XICs) corresponding to the pseudomolecular ions containing one or more selenium atoms Putative formula supported by MS2 and MS3 analysis. BRASINOE U

6. 0102030405060 Retention time, min 0510152025 C 57 H 104 O 9 Se monolinoleate-dioleate derivatives trioleate derivative C 57 H 102 O 9 Se C 57 H 102 O 9 Se 2 (c) The panel presents HPLC-ICP MS chromatogram in order to demonstrate matching of peaks obtained using elemental and molecular MS detection. Putative formula supported by MS2 and MS3 analysis. Extracted ion chromatograms (XICs) corresponding to the pseudomolecular ions containing one or more selenium atoms BRASINOE U

7. C 57 H 104 O 9 Se[M+H] + C 57 H 96 O 7 Se[M+Na] + C 18 H 30 O 3 Se[M+ Na] + MS 3 C 39 H 64 O 5 Se[M+Na] + C 39 H 68 O 6 Se[M+H] + C 18 H 32 O 4 Se[M+Na] + MS 3 C 56 H 96 O 9 Se[M+H] + MS 2 C 57 H 106 O 5 Se[M+H] + MS 2 C 39 H 68 O 8 Se[M+H ] + MS 2 C 18 H 32 O 3 Se[M+H ] + C 31 H 50 O 5 Se[M+ Na] + C 21 H 36 O 3 Se[M+Na ] + C 18 H 30 O 3 Se[M+H] + MS 3 An example of the fragmentation cascade for species m/z 1013.6913 (C 57 H 104 O 9 Se) BRASINO EU

8. Income Received amount StayPersonsExpenses 21-02-2013 € 21 954.4114-21 May 2015 Prof. Ricardo Bentez Azevedo € 546.00 Remaining amount Prof. Zulmira Marquez Lacava € 546.00 € 20 862.41 Total € 1 092.00 Balance sheet BRASINO EU

9. Our plans for the visit at the University of Brasilia PersonsArrivalDeparture Anna Flis-Borsuk - PhD student Lidia Śliwka - PhD student 1 May 201630 June 2016 Prof. Zbigniew Fijałek Prof. Piotr Suchocki 1 June 201630 June 2016 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. BRASINOE U