Synthesis and Antimicrobial Activity of Novel 1,3-Oxazolidine Nucleoside Analogues

Sriharsha, S. N.; Shashikanth, S.

doi:10.1515/hc.2006.12.3-4.213

Cited by 13 publications

(12 citation statements)

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“…3-Dichloroacetyl-2,2-dimethyl-4-ethyl-1,3-oxazolidine is an anlogue of R-28725 with one chiral center. Most enzymatic reactions in plants are stereoselective; thus, the biological activity of the two optically active enantiomers of 3-dichloroacetyl-2,2-dimethyl-4-ethyl-1,3-oxazolidine and racemate could be different because of their chirality (Kang et al 2005;Sriharsha and Shashikanth 2006). However, few studies have investigated the detoxification mechanisms of chiral safener (Jablonkai 2013).…”

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confidence: 99%

Alleviation of injury from chlorimuron-ethyl in maize treated with safener 3-dichloroacetyl oxazolidine

ZhaoLi-Xia¹,

QuHai-Tao²,

FuYing³

et al. 2015

Can. J. Plant Sci.

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. 2015. Alleviation of injury from chlorimuron-ethyl in maize treated with safener 3-dichloroacetyl oxazolidine. Can. J. Plant Sci. 95: 897Á903. The protective effects of herbicide safeners, including 3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine (R-28725), 3-dichloroacetyl-2,2-dimethyl-4-ethyl-1,3-oxazolidine (Racemate), and its two enantiomers (R)-3-dichloroacetyl-2,2-dimethyl-4-ethyl-1,3-oxazolidine (R-enantiomer) and (S)-3-dichloroacetyl-2,2-dimethyl-4-ethyl-1,3-oxazolidine (S-enantiomer), on reducing the phytotoxicity of chlorimuronethyl to maize were investigated. Soaking the seeds in safeners increased the endogenous glutathione (GSH) content and glutathione-S-transferase (GST) activity of maize. When induced by R-enantiomer, the GST activity in vivo and in vitro increased 180 and 192% compared with control, respectively. R-28725 and R-enantiomer also increased the acetolactate synthase (ALS) activity inhibited by chlorimuron-ethyl from 45 to 100 and 97% compared with the control, respectively. The kinetic parameter V max of GST in the maize treated with R-28725 and R-enantiomer increased by 103 and 92%, respectively, compared with the control. Our results suggest that R-28725 and R-enantiomer could significantly improve the GSH content, GST activity, and ALS activity of maize. Overall, maize could be protected from the injury caused by chlorimuron-ethyl.Key words: Herbicide injury, safener, 3-dichloroacetyl oxazolidine Zhao, L.-X., Qu, H.-T., Fu, Y., Gao, S. et Ye, F. 2015. Atte´nuation des dommages re´sultant du chlorimuron Á e´thyle chez le maı¨s traite´avec le phytoprotecteur 3-dichloroace´tyl oxazolidine. Can. J. Plant Sci. 95: 897Á903. Les auteurs ont examineć omment divers phytoprotecteurs, notamment la 3-dichloroace´tyl-2,2-dime´thyl-1,3-oxazolidine (R-28725), la 3-dichloroace´tyl-2, 2-dime´thyl-4-e´thyl-1,3-oxazolidine (Racemate) et leurs isome`res optiques (R)-3-dichloroace´tyl-2,2-dime´thyl-4-e´thyl-1,3-oxazolidine (isome`re optique R) et (S)-3-dichloroace´tyl-2,2-dime´thyl-4-e´thyl-1,3-oxazolidine (isome`re optique S), atte´nuent la toxicite´du chlorimuronÁe´thyle pour le maı¨s. Tremper les semences dans le phytoprotecteur augmente la concentration de glutathion endoge`ne (GSH) et l'activite´de la glutathion-S-transfe´rase (GST) du maı¨s. L'isome`re optique R augmente respectivement l'activite´in vivo et in vitro de la GST de 180 % et de 192 % comparativement aux te´moins. Le R-28725 et son isome`re optique R accroissent aussi l'activite´de l'ace´tolactate synthe´tase (ALS) inhibe´e par le chlorimuronÁe´thyle de 45 % a`100 % et de 97 %, respectivement, par rapport aux te´moins. Chez le maı¨s traite´avec du R-28725 et son isome`re optique R, le parame`tre cine´tique V max de la GST augmente respectivement de 103 % e de 92 % comparativement aux te´moins. Ces re´sultats donnent a`penser que le R-28725 et son isome`re optique R pourraient sensiblement augmenter la teneur en GSH, l'activite´de la GST et l'activite´de l'ALS chez le maı¨s. Dans l'ensemble, le maı¨s serait ainsi prote´ge´contre les do...

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confidence: 99%

Alleviation of injury from chlorimuron-ethyl in maize treated with safener 3-dichloroacetyl oxazolidine

ZhaoLi-Xia¹,

QuHai-Tao²,

FuYing³

et al. 2015

Can. J. Plant Sci.

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“…Data collection: APEX2 ; cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 ; program(s) used to refine structure: SHELXL97 ; molecular graphics: ORTEP-3 for Windows (Farrugia,1997) and PLATON ; software used to prepare material for publication: WinGX . (Madhusudhan et al 2004); (Sriharsha & Shashikanth, 2006), antiviral (Wilhelmsson, et al 2008), anti-tumor (Soad et al2006),and anti-inflammatory (Menoret et al 2009). Our investigation is intended to increase the biological activity of such molecules.…”

Section: Special Detailsmentioning

confidence: 99%

Bis[2-(cyclopropyliminomethyl)-5-methoxyphenolato]zinc(II)

Bai¹

2010

Acta Cryst E

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“…Studies indicated that some 3-dichloroacetylsubstituted oxazolidines with a chiral center often have different biological activities (Sriharsha & Shashikanth 2006;Zhao et al 2015). One of the most widely used dichloroacetamide safeners in maize was 3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine (R-29148).…”

Section: Introductionmentioning

confidence: 99%

Effects of Chiral 3-Dichloroacetyl Oxazolidine on Glutathione S-Transferase and Antioxidant Enzymes Activity in Maize Treated with Acetochlor

Cao

Chen

et al. 2018

Tarım Bilimleri Dergisi

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The objective of this paper was to investigate the protective effect of three potential herbicide safeners (3-dichloroacetyl oxazolidine and its two optical isomers) on detoxifying to chloroacetanilide herbicide acetochlor in maize. In this study, physiological and biochemical tests were conducted under laboratory condition in 2015. All safeners increased the expression levels of herbicide detoxifying enzymes, including glutathione S-transferases (GST), catalase (CAT) and peroxidase (POD) to reduce chloroacetanilide herbicide phytotoxicity in maize seedlings. Our results suggest that the R-isomer of R-29148 can induce glutathione (GSH) expression, GST activity, and affinity for the 1-chloro-2,4-dinitrobenzene (CDNB) substrate in maize, which can protect maize from injury by chloroacetanilide herbicide acetochlor. Further information on the chiral safener role in antioxidative enzymes activation was obtained from CAT and POD activity to overcome oxidative stress caused by the herbicide.

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Synthesis and Antimicrobial Activity of Novel 1,3-Oxazolidine Nucleoside Analogues

Cited by 13 publications

References 11 publications

Alleviation of injury from chlorimuron-ethyl in maize treated with safener 3-dichloroacetyl oxazolidine

Alleviation of injury from chlorimuron-ethyl in maize treated with safener 3-dichloroacetyl oxazolidine

Bis[2-(cyclopropyliminomethyl)-5-methoxyphenolato]zinc(II)

Effects of Chiral 3-Dichloroacetyl Oxazolidine on Glutathione S-Transferase and Antioxidant Enzymes Activity in Maize Treated with Acetochlor

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