HaiFeng Qian, Tao Lu, XiaoFeng Peng, Xiao Han, ZhengWei Fu, WeiPing Liu
Index: PLoS ONE 6(5) , e19451, (2011)
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The enantiomers of a chiral compound possess different biological activities, and one of the enantiomers usually shows a higher level of toxicity. Therefore, the exploration of the causative mechanism of enantioselective toxicity is regarded as one of primary goals of biological chemistry. Imazethapyr (IM) is an acetolactate synthase (ALS)-inhibiting chiral herbicide that has been widely used in recent years with racemate. We investigated the enantioselectivity between R- and S-IM to form reactive oxygen species (ROS) and to regulate antioxidant gene transcription and enzyme activity.Dramatic differences between the enantiomers were observed: the enantiomer of R-IM powerfully induced ROS formation, yet drastically reduced antioxidant gene transcription and enzyme activity, which led to an oxidative stress. The mechanism by which IM affects carbohydrate metabolism in chloroplasts has long remained a mystery. Here we report evidence that enantioselectivity also exists in starch metabolism. The enantiomer of R-IM resulted in the accumulation of glucose, maltose and sucrose in the cytoplasm or the chloroplast and disturbed carbohydrates utilization.The study suggests that R-IM more strongly retarded plant growth than S-IM not only by acting on ALS, but also by causing an imbalance in the antioxidant system and the disturbance of carbohydrate metabolism with enantioselective manner.
Structure | Name/CAS No. | Molecular Formula | Articles |
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Imazethapyr
CAS:81335-77-5 |
C15H19N3O3 |
Enantioselective phytotoxicity of the herbicide imazethapyr ...
2011-08-15 [Environ. Sci. Technol. 45(16) , 7036-43, (2011)] |
Molecular mechanism of enantioselective inhibition of acetol...
2010-04-14 [J. Agric. Food Chem. 58(7) , 4202-6, (2010)] |
Abiotic degradation (photodegradation and hydrolysis) of imi...
2008-02-01 [J. Environ. Sci. Health B 43(2) , 105-12, (2008)] |
Photodegradation of the herbicide imazethapyr in aqueous sol...
2011-07-13 [J. Agric. Food Chem. 59(13) , 7277-85, (2011)] |
Unraveling the role of fermentation in the mode of action of...
2011-09-01 [J. Plant Physiol. 168(13) , 1568-75, (2011)] |
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