Synthesis and Antioxidant Properties of (3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and Its Derivatives

ÇETİNKAYA Y., GOCER H., MENZEK A., Gulcin I.

ARCHIV DER PHARMAZIE, cilt.345, sa.4, ss.323-334, 2012 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 345 Sayı: 4
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1002/ardp.201100272
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.323-334
  • Anahtar Kelimeler: Antioxidant activity, Bromination, Bromophenols, Phenols, Radical scavenging, IN-VITRO ANTIOXIDANT, RADICAL SCAVENGING ACTIVITY, LYOPHILIZED AQUEOUS EXTRACT, POLYPHENOL CONTENTS, ANTIMICROBIAL ACTIVITIES, ANTIRADICAL ACTIVITIES, DIETARY POLYPHENOLS, BROMOPHENOLS, CAPACITY, SUPEROXIDE
  • Atatürk Üniversitesi Adresli: Evet

Özet

(3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone (5) and its two derivatives with bromine were synthesized from reactions such as bromination and demethylation of (3,4-dimethoxyphenyl)(2,3,4-trimethoxyphenyl)methanone (6). The Wolf-Kishner reduction product (9) of 6 and its three derivatives with bromine were obtained. 4-(3,4-Dihydroxybenzyl)benzene-1,2,3-triol and its dibromide derivative (16) were also synthesized from 9 and the corresponding dibromide derivative. The in vitro antioxidant activities of nine new compounds synthesized in these reactions were determined by analyzing the radical scavenging activities of bromophenols for 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), 1,1-diphenyl-2-picryl-hydrazyl (DPPH), N,N-dimethyl-p-phenylenediamine (DMPD), and the superoxide anion radical (O-2(center dot-) and examining the total reducing power through Fe3+-Fe2+ transformation, FRAP and CUPRAC assays and the ferrous ions (Fe2+) chelating activities. Moreover, the results of these activities were compared to those of standard antioxidant compounds such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), a-tocopherol, and trolox. The results showed that the synthesized bromophenols had effective antioxidant power. The phenol 5 with two phenolic rings and five phenolic hydroxyl groups was the most potent antioxidant and radical scavenger. In conclusion, the new compounds are promising molecules to be used owing to their potential antioxidant properties.