Enantioseparation and Enantioselective Phytotoxicity of Glufosinate Ammonium on Catechin Biosynthesis in Wheat

Khodadady, Mohammad; Ramezani, Mohammad Kazem; Mahdavi, Vahideh; Ghassempour, Alireza; Aboul‐Enein, Hassan Y.

doi:10.1007/s12161-013-9677-6

Cited by 7 publications

(10 citation statements)

References 20 publications

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“…a Significant difference as compared with the control (p < 0.05). b Significant difference between Racglufosinate treatment and Lglufosinate treatment groups (p < 0.05) Table 1 The variation of the shoot height, shoot weight, root weight, and root length of maize seedlings exposed to Racand L-glufosinate with the concentration of 0, 1, 5, 10, and 20 mg/L for 5 days analysis showed that the inhibition of the L-glufosinate treatment groups were 4.2 times than that of the D-glufosinate treatment groups in wheat seedlings (Khodadady et al 2014). In our study, the growth of maize seedlings was also inhibited.…”

Section: Discussionmentioning

confidence: 99%

“…The enzymic detoxification system can preserve the metabolism of cells and alleviate oxidative stress injuries. This important antioxidant enzyme system was stimulated, as well as auxiliary detoxify enzymes such as ascorbate peroxidase (APX) and GR, which also play crucial roles in preventing ROS from exploding, protecting the plasma membrane from oxidation, and maintaining the normal growth and metabolism of plant cells (Schopfer 2001 (Khodadady et al 2014). The increase of these antioxidant enzyme activities revealed that glufosinate induced the increasing ROS level in maize seedlings.…”

Section: Discussionmentioning

confidence: 99%

“…Lglufosinate was phytotoxic and its herbicidal effect was twice more than that of the racemic mixture (Willms and Bartsch 1997). The recent study also indicated that the Lglufosinate treatment group exerted more inhibition in the plant growth than that of D-glufosinate (Khodadady et al 2014). Up to date, there were few researches on the enantioselectivity of Racand L-glufosinate against crops.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective effect of glufosinate on the growth of maize seedlings

Zhang

Cui

Yue

et al. 2018

Environ Sci Pollut Res

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Glufosinate is a non-selective chiral herbicide, which has been used extensively around the world. However, limited information on the enantioselectivity of Racand L-glufosinate against crops. In this study, the enantioselective effects on the growth, antioxidant, and targeted enzyme activities of maize seedlings of chiral glufosinate were investigated. The results showed the enantioselective growth inhibitions were observed at both 1 and 5 mg/L concentration levels. L-Glufosinate induced more growth rate reduction in shoot height and weight compared to Rac-glufosinate. All of the antioxidant enzyme activities increased obviously in the leaves of maize seedlings treated by 1 mg/L of glufosinate. Superoxide dismutase (SOD) activity, catalase (CAT) activity, peroxidase (POD) activity, glutathione reductase (GR) activity, and malondialdehyde (MDA) content induced by L-glufosinate were 1.36, 1.16, 1.51, 1.65, and 1.65 times higher than those by Rac-glufosinate, respectively Notably, the glutamine synthetase (GS) activity was significantly reduced to 80% and 57% in the control group at 1 mg/L treated with Racand L-glufosinate, respectively. Our results indicated that Racand L-glufosinate showed the obvious enantioselectivity in the growth of maize seedlings, which has shed light on the potential enantioselective phytotoxicity of glufosinate. Data provided here will be helpful to develop the environmentally friendly herbicides.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enantioselective effect of glufosinate on the growth of maize seedlings

Zhang

Cui

Yue

et al. 2018

Environ Sci Pollut Res

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“…However, decomposition of the substrate is a recurring problem when high temperatures are required. Glufosinate (PPT) is an amino acid derivative with effective herbicidal properties exclusively in the L‐form, while the enantiomeric D‐form is ineffective . Compared with glyphosate, PPT has better herbicidal effects on some perennial malignant weeds and is more competitive for crops of high economic value.…”

Section: Introductionmentioning

confidence: 99%

“…Glufosinate (PPT) is an amino acid derivative with effective herbicidal properties exclusively in the L-form, while the enantiomeric D-form is ineffective. 12 Compared with glyphosate, PPT has better herbicidal effects on some perennial malignant weeds and is more competitive for crops of high economic value. The key enzyme involved in PPT synthesis is glutamine synthetase, which can eliminate the toxicity of ammonium released from nitrate reduction, amino acid degradation, and photorespiration.…”

Section: Introductionmentioning

confidence: 99%

Efficient racemization of N‐phenylacetyl‐D‐glufosinate for L‐glufosinate production

Xue

et al. 2019

Chirality

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Most amino acids contain chiral centres and exist as both D‐enantiomer and L‐enantiomer. The optically pure enantiomer is often more valuable than the racemate. Enzymatic resolution provides an effective strategy to obtain optically pure amino acids but often results in large amounts of unwanted isomer. In this study, optically pure L‐glufosinate (L‐PPT) was obtained by coupling amidase‐mediated hydrolysis of N‐phenylacetyl‐D,L‐glufosinate with racemization of N‐phenylacetyl‐D‐glufosinate (NPDG), which exclusively exhibits effective herbicidal properties compared with its D‐enantiomer. To improve the yield of L‐PPT, the racemization reaction conditions were optimized, and through single‐factor experiments, the optimal reaction temperature, reaction time, and mole ratio of phenylacetic acid to NPDG were determined to be 150°C, 30 minutes, and 1.5, respectively. The response surface methodology was applied to further optimize the racemization conditions, and the final yield of L‐PPT reached 96.13% with optimum reaction temperature of 154°C, reaction time of 23 minutes, and phenylacetic acid/NPDG mole ratio of 1.7, respectively. Moreover, adding a small amount of acetic anhydride further raised the yield of L‐PPT to 97.02%.

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