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49 .   Comparison study between two modification conditions of rosmarinic acid and amino acids- Identification of formed adducts using FI-ESI-QTOF-mass spectrometry

Authors: Mostafa Ali, Karin Schwarz

Volume 24, Issue 4;
Pages: 301-310; 2018
ISSN: 2069-0053 (print) (former ISSN: 1453-1399), Agroprint;
ISSN (online): 2068-9551



Abstract:

This study was designed to compare and identify the adducts formed between rosmarinic acid and amino acids at two different modification conditions. Covalent interactions between different amino acids, including[L-Lysine (L-Lys) and its derivative,tert-butyloxycarbonyl-L-lysine (N-Boc-Lys) and L-cysteine (L-Cys)] and rosmarinicacid (Ros) were conductedwithtwo different methods;alkaline (pH 9) and enzymatic [in the presence of tyrosinase (polyphenoloxidase, PPO)].The formed adducts were identified and characterized usingflow injection electrospray ionization - quadrupole time of flight (FI-ESI-QTOF) mass spectrometry.Many adducts were identified for the first time. The obtained dataexhibitedslight differences between the adducts formed afteralkaline and enzymatic treatment.In case of the incubation of Roswith both methods without amino acids,numerousadducts, such as Rosquinone, Ros dimer anddecarboxylatedRos at [M−H]-with anm/z of 359.08,719.17 and 313.1 Da, respectively,were identified.Otherwise, in the presence of amino acids, the monomerand dimerof Roswere covalently added to the side chainsof selected amino acids.Additionally, the covalent attachment between oxidized Rosand the side chains of twomolecules of amino acids was also identified.Finally, L-Cys was the most susceptible amino acid to react withoxidized Ros compared to L-Lys and N-Boc-Lys. It could be concluded that, the results show some similarities betweenthe adducts formed at both modification conditions. Moreover, thecovalent interactions between Rosand the side chains of molecules of lysine or cysteine may also be expected to occur in proteins.

Keywords: Covalent interactions,tyrosinase, L-Lysine and L-Cysteine, rosmarinic acid, FI-ESI- QTOF-MS

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