Synthesis and antioxidant activities of benzylic bromophenols inclusive of natural products

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Bayrak C., Uc E. M., Rezaei M., GÜLÇİN İ., MENZEK A.

TURKISH JOURNAL OF CHEMISTRY, cilt.46, sa.5, ss.1405-1428, 2022 (SCI-Expanded) identifier identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 46 Sayı: 5
  • Basım Tarihi: 2022
  • Doi Numarası: 10.55730/1300-0527.3447
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.1405-1428
  • Anahtar Kelimeler: Antioxidant activity, bromination, bromophenol, radical scavenging, natural product, benzylic acid, RADICAL SCAVENGING ACTIVITY, IN-VITRO ANTIOXIDANT, CARBONIC-ANHYDRASE, POLYPHENOL CONTENTS, 1ST SYNTHESIS, ANTICHOLINERGIC ACTIVITIES, SUPEROXIDE-DISMUTASE, II COMPLEXES, COPPER II, DERIVATIVES
  • Atatürk Üniversitesi Adresli: Evet

Özet

The synthesis of natural products 2-(2,3-dibromo-4,5-dihydroxyphenyl)acetic acid (1) and 2-(2,6-dibromo-3,5-dihydroxyphenyl)acetic acid (2) and as well as their derivatives 25 and 26 were carried out by substitution, hydrolysis and demethylation reactions of the corresponding four benzyl bromides. The antioxidant potentials of benzylic acid-derived bromophenols were, for the first time, appraised by several outstanding bioanalytical methods. Besides these, we estimated the antioxidant effects which were studied using the methods of DPPH center dot, ABTS center dot+ scavenging activities, ferric (Fe3+) and cupric (Cu2+) ions and Fe3+-TPTZ reducing capacities. Benzylic acid-derived bromophenols were found as effective DPPH center dot, and ABTS center dot+ scavengers. The potential antioxidant activities of bromophenol derivatives 1, 2 and 17-28 were compared to standard antioxidants including BHA, BHT, alpha-Tocopherol, and Trolox, which is a water-soluble analog of vitamin E. We expect that this innovative work will direct future studies exploring the antioxidant properties of food, medicinal, and industrial applications.