Inhibition of trans-cinnamate 4-hydroxylase by 4-amino-5-aryl-2,3-dihydro- 3H-1,2,4-triazole-3-thiones

Soonsung Hong, Naotaka Yamada, Akiko Harada, Shinya Kawai, Eiichi Kuwano

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A number of 4-amino-5-aryl-2,3-dihydro-3H-1,2,4-triazole-3-thiones were synthesized and tested for inhibitory activity against franj-cinnamate 4-hydroxylase (C4H) from Populus kitakamiensis, which was expressed in yeast. Of the compounds tested, 4-amino-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (1) was the most effective, having an IC50 value of 0.32 ̈M. Replacement of the phenyl group with heterocycles or substituted phenyl groups drastically reduced the activity. Compound 1 behaved as a mixed-inhibitor of C4H. When potato tuber disks were treated with 1 (0.2-20 ng/disk) in the presence of laminarin, a β-1,3-glu-cooligosaccharide elicitor, trans-cinnamic acid was accumulated at levels 3 times higher than in disks treated with laminarin alone.

Original languageEnglish
Pages (from-to)406-408
Number of pages3
JournalJournal of Pesticide Science
Volume30
Issue number4
DOIs
Publication statusPublished - Dec 1 2005

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Trans-Cinnamate 4-Monooxygenase
trans-cinnamate 4-monooxygenase
Thiones
triazoles
Populus
cinnamic acid
Solanum tuberosum
Inhibitory Concentration 50
inhibitory concentration 50
tubers
Yeasts
potatoes
yeasts
1,2,4-triazole
laminaran

All Science Journal Classification (ASJC) codes

  • Insect Science
  • Health, Toxicology and Mutagenesis

Cite this

Inhibition of trans-cinnamate 4-hydroxylase by 4-amino-5-aryl-2,3-dihydro- 3H-1,2,4-triazole-3-thiones. / Hong, Soonsung; Yamada, Naotaka; Harada, Akiko; Kawai, Shinya; Kuwano, Eiichi.

In: Journal of Pesticide Science, Vol. 30, No. 4, 01.12.2005, p. 406-408.

Research output: Contribution to journalArticle

Hong, Soonsung ; Yamada, Naotaka ; Harada, Akiko ; Kawai, Shinya ; Kuwano, Eiichi. / Inhibition of trans-cinnamate 4-hydroxylase by 4-amino-5-aryl-2,3-dihydro- 3H-1,2,4-triazole-3-thiones. In: Journal of Pesticide Science. 2005 ; Vol. 30, No. 4. pp. 406-408.
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