Comparison of glutathione reductase activity and the intracellular glutathione reducing effects of 13 derivatives of 1'-acetoxychavicol acetate in Ehrlich ascites tumor cells.
In a previous study, we showed that (1'S)-acetoxychavicol acetate ((S)-ACA) caused a rapid decrease in glutathione (GSH) levels less than 15 min after exposure. (S)-ACA-induced cell death was reversed by the addition of N-acetylcysteine. In the current study, we investigated the inhibitory activities of 13 derivatives of (S)-ACA on tumor cell viability, intracellular GSH level and GR activity. Correlations were found among a decrease in cell viability, intracellular GSH levels and the activity of GR in Ehrlich ascites tumor cells treated with the various ACA analogues. A test of the 13 derivatives revealed that the structural factors regulating activity were as follows: (1) the para or 1'-position of acetoxyl group (or other acyl group) was essential, (2) the presence of a C2'-C3' double or triple bond was essential, and (3) the S configuration of the 1'-acetoxyl group was preferable.
Xu
Shenghui
S
Department of Food and Human Health Sciences, Graduate School of Human Life Science, Osaka City University, Osaka, Japan.
Kojima-Yuasa
Akiko
A
Azuma
Hideki
H
Kennedy
David Opare
DO
Konishi
Yotaro
Y
Matsui-Yuasa
Isao
I
D000818:Animals; D001592:Benzyl Alcohols / Q000737:chemistry* / Q000494:pharmacology*; D002286:Carcinoma, Ehrlich Tumor / Q000378:metabolism*; D002470:Cell Survival / Q000187:drug effects; D005978:Glutathione / Q000378:metabolism*; D005980:Glutathione Reductase / Q000378:metabolism*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D001592:Benzyl Alcohols; D005980:Glutathione Reductase; D005978:Glutathione; C047948:1'-acetoxychavicol acetate