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

BEYAZİT N., Çakran H. S., Cabir A., AKIŞCAN Y., DEMETGÜL C.

Carbohydrate Polymers, cilt.240, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 240
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.carbpol.2020.116333
  • Dergi Adı: Carbohydrate Polymers
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, PASCAL, BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chimica, Compendex, EMBASE, Food Science & Technology Abstracts, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: Antioxidant, Chitosan, Gossypol, Schiff base
  • Hatay Mustafa Kemal Üniversitesi Adresli: Evet

Özet

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.