Inhibitory activity of 2-aryl-1,3,4-oxadiazole-5-thiols and 4-amino-5-aryl-4H-1,2,4-triazole-3-thiols on cinnamic acid 4-hydroxylase

DOI
  • Harada Akiko
    Kyushu University, Graduate School of Bioresource and Bioenviromental Sciences
  • Kataoka Yuki
    Kyushu University, Graduate School of Bioresource and Bioenviromental Sciences
  • Yamada Naotaka
    Kyushu University, Graduate School of Bioresource and Bioenviromental Sciences
  • Kuwano Eiichi
    Kyushu University, Graduate School of Bioresource and Bioenviromental Sciences
  • Kawai Shinya
    Tokyo University of Agriculture and Technology, Faculty of Agriculture

Bibliographic Information

Other Title
  • 52 2-aryl-1,3,4-oxadiazole-5-thiol および 4-amino-5-aryl-4H-1,2,4-triazole-3-thiol の cinnamic acid 4-hydroylase 阻害活性

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Description

Previous studies indicate that 2-phenyl-1,3,4-oxadiazole-5-thiol (HA-43) has inhibitory activity on cinnamic acid 4-hydroxylase(CA4H) from Populus kitakamiensis, Kinetic analysis of inhibitory mode was examined, and it was revealed that HA-43 was competitive inhibitor of CA4H. To test whether HA-43 was an alternate substrate of CA4H, HA-43 was incubated in the presence of CA4H and cinnamic acid. HA-43 was metabolized to 2-(4-hydroxyphenyl)-1,3,4-oxadiazole-5-thiol by CA4H, but cinnamic acid was nearly did to p-cumaric acid. On the other hand, we have found that 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol (HA-54) showed the inhibitory activity. Studies on the structure-activity relationship about 4-amino-5-aryl-4H-1,2,4-triazole-3-thiols indicated that the introduction of some substitute on the benzene ring decreased the inhibitory activity. The examination in metabolism of HA-54 by CA4H indicated that HA-54 was not metabolized to 4-amino-5-(4-hydroxyphenyl)-4H-1,2,4-triazole-3-thiols.

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Details 詳細情報について

  • CRID
    1390282679401305728
  • NII Article ID
    110001867887
  • DOI
    10.18978/jscrpanb.37.0_113
  • ISSN
    21896313
    09191887
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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