Synthesis, characterization and antioxidant activity of chitosan Schiff base derivatives bearing (-)-gossypol.

Neslihan Beyazit, Halide Sinem Çakran, Ali Cabir, Yaşar Akışcan, Cahit Demetgül

Carbohydrate polymers 2020 Jul 15

filter terms:

In this work, two new chitosan-Schiff base derivatives (HCS-GSP and LCS-GSP) were synthesized by the condensation reaction of high molecular weight chitosan (HCS) and low molecular weight chitosan (LCS) with (-)-gossypol (GSP), respectively. For this purpose, racemic gossypol was isolated from cotton seeds and it was further enantiomerically purified by diastereomeric resolution technique using l-tryptophan methyl ester hydrochloride. Then, chitosan polymers were derivatized with (-)-gossypol by the condensation reaction. The isolated and synthesized coumpounds were characterized by physical measurements and spectroscopic methods (elemental analysis C,H,N, Uv-vis, FT-IR, 1H&13C NMR and TG/DTG/DTA). The antioxidant activity of high molecular weight chitosan (HCS), low molecular weight chitosan (LCS) and their gossypol derivatives was evaluated as radical scavengers against 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH). The results showed that both of the chitosan-gossypol derivatives (HCS-GSP and LCS-GSP) had a better ability to scavenging DPPH radical (IC50, 12 μg/mL and 16 μg/mL, respectively) than its unmodified chitosan. Copyright © 2020 Elsevier Ltd. All rights reserved.

Citation

Neslihan Beyazit, Halide Sinem Çakran, Ali Cabir, Yaşar Akışcan, Cahit Demetgül. Synthesis, characterization and antioxidant activity of chitosan Schiff base derivatives bearing (-)-gossypol. Carbohydrate polymers. 2020 Jul 15;240:116333