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

概要

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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.
植物化学調節学会の論文
2002-10-31