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The Pharmaceutical Society of Korea (대한약학회)
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Isolation of a Natural Antioxidant, Dehydrozingerone from Zingiber officinale and Synthesis of lts Analogues for Recognition of Effective Antioxidant and Antityrosinase Agents

  • Kuo, Ping-Chung (Department of Biotechnology, National Formosa University) ;
  • Damu, Amooru G. (Department of Chemistry, National Cheng Kung University) ;
  • Cherng, Ching-Yuh (Department of Applied Chemistry, National Chiayi University) ;
  • Jeng, Jye-Fu (Department of Chemistry, National Cheng Kung University) ;
  • Teng, Che-Ming (Pharmacological Institute, College of Medicine, National Taiwan University) ;
  • Lee, E-Jian (Neurophysiology Laboratory, Neurosurgical Service, Departments of Surgery and Anesthesiology, and Institute of Biomedical Engineering, National Cheng Kung University Medical Center and Medical School) ;
  • Wu, Tian-Shung (Department of Chemistry, National Cheng Kung University, National Research Institute of Chinese Medicine)
  • Published : 2005.01.01
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Abstract

In the present study, the antioxidative and inhibitory activity of Zingiber officinale Rosc. Rhizomes-derived materials (on mushroom tyrosinase) were evaluated. The bioactive co mponents 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 Fe$^{2+}$-induced lipid peroxidation in rat brain homogenate with an IC$_{50}$ = 6.3${\pm}$0.4 ${\mu}$M. 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 ${\alpha}$-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.

Keywords

References

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