Archives of Pharmacal Research

, Volume 28, Issue 5, pp 518-528

Isolation of a Natural Antioxidant, Dehydrozingerone from Zingiber officinale and Synthesis of Its Analogues for Recognition of Effective Antioxidant and Antityrosinase Agents

  • Ping-Chung KuoAffiliated withDepartment of Biotechnology, National Formosa University
  • , Ching-Yuh CherngAffiliated withDepartment of Applied Chemistry, National Chiayi University
  • , Jye-Fu JengAffiliated withDepartment of Chemistry, National Cheng Kung University
  • , Amooru G. DamuAffiliated withDepartment of Chemistry, National Cheng Kung University Email author 
  • , Che-Ming TengAffiliated withPharmacological Institute, College of Medicine, National Taiwan University
  • , E-Jian LeeAffiliated withNeurophysiology Laboratory, Neurosurgical Service, Departments of Surgery and Anesthesiology and Institute of Biomedical Engineering, National Cheng Kung University Medical Center and Medical School
  • , Tian-Shung WuAffiliated withDepartment of Chemistry, National Cheng Kung UniversityNational Research Institute of Chinese Medicine

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In the present study, the antioxidative and inhibitory activity of Zingiber officinale Rosc. rhizomes-derived materials (on mushroom tyrosinase) were evaluated. The bioactive components of Z. officinale rhizomes were characterized by spectroscopic analysis as zingerone and dehydrozingerone, which exhibited potent antioxidant and tyrosinase inhibition activities. A series of substituted dehydrozingerones [(E)-4-phenyl-3-buten-2-ones] were prepared in admirable yields by the reaction of appropriate benzaldehydes with acetone and the products were evaluated in terms of variation in the dehydrozingerone structure. The synthetic analogues were examined for their antioxidant and antityrosinase activities to probe the most potent analogue. Compound 26 inhibited Fe2+-induced lipid peroxidation in rat brain homogenate with an IC50 = 6.3±0.4 μM. In the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical quencher assay, compounds 2, 7, 17, 26, 28, and 29 showed radical scavenging activity equal to or higher than those of the standard antioxidants, like a-tocopherol and ascorbic acid. Compound 27 displayed superior inhibition of tyrosinase activity relative to other examined analogues. Compounds 2, 17, and 26 exhibited non-competitive inhibition against oxidation of 3,4-dihydroxyphenylalanine (L-DOPA). From the present study, it was observed that both number and position of hydroxyl groups on aromatic ring and a double bond between C-3 and C-4 played a critical role in exerting the antioxidant and antityrosinase activity.

Key words

Dehydrozingerone Zingerone Fe2+-lnduced lipid peroxidation Antioxidation Antityrosinase (E)-4-Phenyl-3-buten-2-one