三种典型手性污染物对绿藻和拟南芥的毒性效应研究
摘要
化学农药主要是人工合成的生物外源性物质,流失的农药不仅造成生态环境的严重威胁,甚至会进入人类食物链,构成对人类健康的严重威胁。现在施用的农药中有很大一部分是手性农药,手性农药的对映体中,往往只有一种对映体是具有除草或杀虫活性的,外消旋体的施用使得没有除草杀虫活性的对映体在环境中大量残留,手性化合物的化学行为往往相似但是生物行为却相差巨大,所以研究手性农药不同对映体的环境行为具有重要的环境意义。考虑到环境污染的复杂性,环境中其他污染物对手性农药环境行为可能存在一定的影响,尤其是环境中的非手性污染物,因此研究非手性污染物对手性污染物环境行为的影响也是非常必要的。随着科学研究的发展,一些新兴的手性物质不断出现,手性离子液体就是这样一类手性物质,对这类物质的毒性大小进行评估可以为它们的安全使用提供依据。本文的主要内容如下：
(1)手性除草剂2,4-滴丙酸(DCPP)对斜生栅藻的毒性以及与重金属Cu对其对映体选择性的影响。DCPP能够刺激斜生栅藻细胞产生过量的ROS,进而激活抗氧化系统的活性,但是两者之间的平衡被打破使得细胞的叶绿素含量降低,亚细胞结构受损。DCPP的不同对映体处理后细胞内ROS的产生量表现出了对映体差异,ROS产生量多的R-对映体毒性也较大,亚细胞结构受损严重。DCPP和Cu的复合处理毒性要远大于单独处理的毒性,两者之间的作用方式会影响DCPP毒性的对映体选择性。因此在评估复合毒性时要充分考虑两者的相互作用方式。
(2)手性除草剂咪唑乙烟酸(IM)对斜生栅藻的毒性以及与重金属的复合毒性。IM对斜生栅藻的毒性不具有对映体选择性,Cu和IM对斜生栅藻的复合毒性要远远小于Cu的单独毒性。原因可能是：首先IM和Cu能形成螯合物,该螯合物具有分解H202的作用,减少了H202对细胞的危害；其次,IM和Cu形成螯合物后减少了离子形态的Cu和斜生栅藻细胞壁的相互作用,进而减少了毒性；Cu单独处理时可以改变斜生栅藻细胞内微量元素Fe的分布,但是螯合物IM-Cu不会。
(3)乳酸根手性离子液体对斜生栅藻的毒性。乳酸根手性离子液体对斜生栅藻的毒性具有对映体选择性,并且随着阳离子碳链长度的增加对映体选择性变得不明显。不同构型的手性离子液体可以选择性的改变斜生栅藻的细胞通透性,并且可以导致细胞内产生不同量的ROS,此外,不同构型的手性离子液体的聚集行为不同,以上这些可能是导致手性离子液体毒性具有对映体选择性的原因。随着阳离子碳链长度的增加,阴离子在毒性中所占的比重减小,所以对映体选择性变得不明显。但是乳酸根手性离子液体对裸藻的毒性不具有对映体选择性。斜生栅藻和裸藻细胞结构的差异以及营养方式的不同可能导致了两者对手性离子液体的敏感性不同。
(4)手性除草剂DCPP对拟南芥的毒性。DCPP对拟南芥的毒性表现出了明显的对映体差异性,叶片的鲜重以及根的长度都存在对映体差异,其中R-DCPP的毒性最大,其次为Rac-DCPP, S-DCPP的毒性最小。DCPP作为一种植物激素类除草剂其R-对映体能够和植物生长素一样,过量时诱导细胞内产生ROS,抑制生长,造成植株死亡,S-对映体没有该作用。而且DCPP的不同对映体对抗氧化系统激活能力不同,对气孔细胞的调控节奏也不同。
(5)手性除草剂M对拟南芥的毒性。IM对拟南芥的毒性表现出了明显的对映体差异性,而且不同的对映体可以引起拟南芥叶片内微量元素分布的不同,其中R-对映体会引起微量元素明显的聚集,但是S-对映体不会；但是M不同对映体不会引起根内微量元素分布的改变,这说明M对元素的吸收过程影响可能较小。Cu对拟南芥的毒性较小时仍旧可以改变叶片内微量元素的改变,当cu和IM同时处理拟南芥时毒性趋势以及微量元素的分布趋势和M单独处理时相似。
As a great agricultural country, pesticides has been used extensively in China, therefore the environmental pollution resulted from pesticides usage was significant. It is well known that as many as25%of all pesticide active ingredients are chiral, and this ratio is increasing as compounds with more complex structures are introduced into use. Enantiomers of a chiral chemical generally undergo the same physical and chemical processes and reactions in the environment, however, the enantiomers may behave differently in biologically mediated environmental processes and their biological effects (e.g., toxicity, mutagenicity, carcinogenicity, endocrine-disrupting activity) are typically enantioselective. Some studies also found that environmental factors can affect the chiral preference of pesticides.
With the wide applications of chiral ionic liquids (CILs), the development of knowledge for the prospective design of inherently.safe CILs has become more urgent. However, enantioselective differences in CILs toxicities are poorly understood. The main conclusions of this work are drawn.
(1) Individual and combined presence of dichlorprop (DCPP) and Cu provoked a boom in ROS, which in turn stimulated the response of antioxidant defences, impaired subcellular structure and physiological function, finally resulted in the increase of cell grow inhibition rate. In absence of Cu, the ROS contents of the herbicidally active (R)-enantiomer was higher than that of (S)-enantiomer, suggesting an (R)-enantiomer preferential production of ROS. When treated with DCPP and Cu simultaneously,(R)-DCPP preferential production of ROS was observed. However, when DCPP was interacted with Cu for24h before adding into the algae solution, this interaction reversed the enantioselective production of ROS. It was interestedly found that the enantioselective generation of ROS was compatible with response of antioxidant defences and the inhibition rate in Scenedesmus obliquus. This finding implied that ROS play a primary role in chemical contaminant toxicity to Scenedesmus obliquus and the interaction between contaminants can tune the enantioselectivity of chiral herbicide dichlorprop and should be considered in future risk assessment.
(2) The effects of herbicide imazethapyr (IM) on the Cu(II) ecotoxicity to the aquatic unicellular alga Scenedesmus obliquus were investigated. It was found that the toxicity of Cu can be mediated by IM. In order to explore the mechanisms involved, complex formation, its catalytic activity, Cu species and the distribution of Cu and Fe in the algal cell were characterized. These results showed that Cu(II) and IM formed an octahedral complex with the mole ratio of IM:Cu=2:1. Such complex did have the role of catalytic the disproportionation of hydrogen peroxide. By the analysis of Cu K-edge XAFS spectroscopy, it indicated that when treated with Cu, the Cu was bound to polygalacturonic acid (on cell wall) and once inside the cell, they may complex with GSH (in cell). As far as the cell was treated by IM and Cu simultaneously (IM-Cu), the IM-Cu interaction may be the main form. Once Cu combined with IM, it will be difficult to interact with cell wall. In addition, using scanning transmission soft X-ray microscopy, it was interestingly found that Cu can induce the change of the distribution of essential trace element Fe while IM-Cu not. This finding implied importance of interactions between heavy metals and organic contaminants, which can mediate toxicity of heavy metals and should be considered in future risk assessment.
(3) The investigation into the toxicities of lactate chiral ionic liquids toward two green algae, Scenedesmus·obliqnus and Euglena gracilis. For S. obliquus, there is a distinct difference between the toxicities of L-(+)-EMIM L and D-(-)-EMIM L; the EC50value of L-(+)-EMIM L was more than5000μM, while EC50value of D-(-)-EMIM L was2255.21μM. Thus, D-(-)-EMIM L is more toxic to S. obliqnus than L-(+)-EMIM L. This trend was maintained with L-(+)-BMIM L and D-(-)-BMIM L but was not observed with increases in carbon chain lengths. This finding may be due to the changes of the toxicity weights of the cations and anions, as the toxicity weights of the cations increase with increasing carbon chain lengths. The results of ROS showed that the D-(-)-lactate ionic liquids may produce more ROS than the L-(+)-lactate ionic liquids, besides, the L-(+)-EMIM L and D-(+)-EMIM L with the same concentration showed different degree of aggregation per unit area. The D-(+)-EMIM L showed stronger aggregation and the particle size was relatively bigger, and this may be the reasons of the enantioselective toxicity. However, the phenomenon described above was not observed for E. gracilis. E. gracilis is different from S. obliquus in subcellular structure, lacking cell walls. Moreover, the nutrient means of the two algae are also varied. These results indicate that we should be able to scale the effects of CILs across organisms more accurately and improve our ability to predict their effects in natural environments. In the meantime, to minimize the potential for environmental harm, the enantioselective toxicities of CILs with short alkyl chains should be taken into consideration.
(4) Dramatic differences between the toxicity of the enantiomers of DCPP to Arabidopsis thaliana were observed:the enantiomer of R-DCPP shows a higher level of toxicity. The assessment of plant growth was carried out by measuring the fresh weight of leaves and the length of root after exposure to the DCPP enantiomers and the results showed that fresh weight of control treatment was16.9mg, R-DCPP treatment was6.32, S-DCPP14.36and Rac-DCPP8.35mg. The root length of control treatment was49.53mm and for R-DCPP, S-DCPP, Rac-DCPP was4.87,34.2and7.7, respectively. The enantiomers of DCPP also stimulated the response of antioxidant defences and the activity of SOD of R-DCPP treatment was higher than the S-DCPP treatment while the activity of CAT, POD was lower than the S-DCPP treatment and the GSH content was also lower and all the treatments were lower than the control treatment. These results indicate that the antioxidant system was damaged and may not scavenge the excess ROS.
(5) The toxicity of IM to Arabidopsis thaliana also showed enantioselective differences. The fresh weight of leaves of control treatment was17.21, and for R-IM, S-IM, Rac-IM was5.25,15.36,7.36mg, respectively. The length root was51.42,4.21,43.2and7.62mm, respectively. The distribution of trace elements in leaves and roots were also determined when treated with IM. The results of leaves showed that the trace elements in control leaf were evenly distributed and the S-IM treated showed the same trend, while the R-IM and Rac-IM treated leaf was aggregated distributed and the expression of gene related to trace elements did not show significant enantioselective differences. However, the distribution of trace elements in root did not show difference.
(1)手性除草剂2,4-滴丙酸(DCPP)对斜生栅藻的毒性以及与重金属Cu对其对映体选择性的影响。DCPP能够刺激斜生栅藻细胞产生过量的ROS,进而激活抗氧化系统的活性,但是两者之间的平衡被打破使得细胞的叶绿素含量降低,亚细胞结构受损。DCPP的不同对映体处理后细胞内ROS的产生量表现出了对映体差异,ROS产生量多的R-对映体毒性也较大,亚细胞结构受损严重。DCPP和Cu的复合处理毒性要远大于单独处理的毒性,两者之间的作用方式会影响DCPP毒性的对映体选择性。因此在评估复合毒性时要充分考虑两者的相互作用方式。
(2)手性除草剂咪唑乙烟酸(IM)对斜生栅藻的毒性以及与重金属的复合毒性。IM对斜生栅藻的毒性不具有对映体选择性,Cu和IM对斜生栅藻的复合毒性要远远小于Cu的单独毒性。原因可能是：首先IM和Cu能形成螯合物,该螯合物具有分解H202的作用,减少了H202对细胞的危害；其次,IM和Cu形成螯合物后减少了离子形态的Cu和斜生栅藻细胞壁的相互作用,进而减少了毒性；Cu单独处理时可以改变斜生栅藻细胞内微量元素Fe的分布,但是螯合物IM-Cu不会。
(3)乳酸根手性离子液体对斜生栅藻的毒性。乳酸根手性离子液体对斜生栅藻的毒性具有对映体选择性,并且随着阳离子碳链长度的增加对映体选择性变得不明显。不同构型的手性离子液体可以选择性的改变斜生栅藻的细胞通透性,并且可以导致细胞内产生不同量的ROS,此外,不同构型的手性离子液体的聚集行为不同,以上这些可能是导致手性离子液体毒性具有对映体选择性的原因。随着阳离子碳链长度的增加,阴离子在毒性中所占的比重减小,所以对映体选择性变得不明显。但是乳酸根手性离子液体对裸藻的毒性不具有对映体选择性。斜生栅藻和裸藻细胞结构的差异以及营养方式的不同可能导致了两者对手性离子液体的敏感性不同。
(4)手性除草剂DCPP对拟南芥的毒性。DCPP对拟南芥的毒性表现出了明显的对映体差异性,叶片的鲜重以及根的长度都存在对映体差异,其中R-DCPP的毒性最大,其次为Rac-DCPP, S-DCPP的毒性最小。DCPP作为一种植物激素类除草剂其R-对映体能够和植物生长素一样,过量时诱导细胞内产生ROS,抑制生长,造成植株死亡,S-对映体没有该作用。而且DCPP的不同对映体对抗氧化系统激活能力不同,对气孔细胞的调控节奏也不同。
(5)手性除草剂M对拟南芥的毒性。IM对拟南芥的毒性表现出了明显的对映体差异性,而且不同的对映体可以引起拟南芥叶片内微量元素分布的不同,其中R-对映体会引起微量元素明显的聚集,但是S-对映体不会；但是M不同对映体不会引起根内微量元素分布的改变,这说明M对元素的吸收过程影响可能较小。Cu对拟南芥的毒性较小时仍旧可以改变叶片内微量元素的改变,当cu和IM同时处理拟南芥时毒性趋势以及微量元素的分布趋势和M单独处理时相似。
As a great agricultural country, pesticides has been used extensively in China, therefore the environmental pollution resulted from pesticides usage was significant. It is well known that as many as25%of all pesticide active ingredients are chiral, and this ratio is increasing as compounds with more complex structures are introduced into use. Enantiomers of a chiral chemical generally undergo the same physical and chemical processes and reactions in the environment, however, the enantiomers may behave differently in biologically mediated environmental processes and their biological effects (e.g., toxicity, mutagenicity, carcinogenicity, endocrine-disrupting activity) are typically enantioselective. Some studies also found that environmental factors can affect the chiral preference of pesticides.
With the wide applications of chiral ionic liquids (CILs), the development of knowledge for the prospective design of inherently.safe CILs has become more urgent. However, enantioselective differences in CILs toxicities are poorly understood. The main conclusions of this work are drawn.
(1) Individual and combined presence of dichlorprop (DCPP) and Cu provoked a boom in ROS, which in turn stimulated the response of antioxidant defences, impaired subcellular structure and physiological function, finally resulted in the increase of cell grow inhibition rate. In absence of Cu, the ROS contents of the herbicidally active (R)-enantiomer was higher than that of (S)-enantiomer, suggesting an (R)-enantiomer preferential production of ROS. When treated with DCPP and Cu simultaneously,(R)-DCPP preferential production of ROS was observed. However, when DCPP was interacted with Cu for24h before adding into the algae solution, this interaction reversed the enantioselective production of ROS. It was interestedly found that the enantioselective generation of ROS was compatible with response of antioxidant defences and the inhibition rate in Scenedesmus obliquus. This finding implied that ROS play a primary role in chemical contaminant toxicity to Scenedesmus obliquus and the interaction between contaminants can tune the enantioselectivity of chiral herbicide dichlorprop and should be considered in future risk assessment.
(2) The effects of herbicide imazethapyr (IM) on the Cu(II) ecotoxicity to the aquatic unicellular alga Scenedesmus obliquus were investigated. It was found that the toxicity of Cu can be mediated by IM. In order to explore the mechanisms involved, complex formation, its catalytic activity, Cu species and the distribution of Cu and Fe in the algal cell were characterized. These results showed that Cu(II) and IM formed an octahedral complex with the mole ratio of IM:Cu=2:1. Such complex did have the role of catalytic the disproportionation of hydrogen peroxide. By the analysis of Cu K-edge XAFS spectroscopy, it indicated that when treated with Cu, the Cu was bound to polygalacturonic acid (on cell wall) and once inside the cell, they may complex with GSH (in cell). As far as the cell was treated by IM and Cu simultaneously (IM-Cu), the IM-Cu interaction may be the main form. Once Cu combined with IM, it will be difficult to interact with cell wall. In addition, using scanning transmission soft X-ray microscopy, it was interestingly found that Cu can induce the change of the distribution of essential trace element Fe while IM-Cu not. This finding implied importance of interactions between heavy metals and organic contaminants, which can mediate toxicity of heavy metals and should be considered in future risk assessment.
(3) The investigation into the toxicities of lactate chiral ionic liquids toward two green algae, Scenedesmus·obliqnus and Euglena gracilis. For S. obliquus, there is a distinct difference between the toxicities of L-(+)-EMIM L and D-(-)-EMIM L; the EC50value of L-(+)-EMIM L was more than5000μM, while EC50value of D-(-)-EMIM L was2255.21μM. Thus, D-(-)-EMIM L is more toxic to S. obliqnus than L-(+)-EMIM L. This trend was maintained with L-(+)-BMIM L and D-(-)-BMIM L but was not observed with increases in carbon chain lengths. This finding may be due to the changes of the toxicity weights of the cations and anions, as the toxicity weights of the cations increase with increasing carbon chain lengths. The results of ROS showed that the D-(-)-lactate ionic liquids may produce more ROS than the L-(+)-lactate ionic liquids, besides, the L-(+)-EMIM L and D-(+)-EMIM L with the same concentration showed different degree of aggregation per unit area. The D-(+)-EMIM L showed stronger aggregation and the particle size was relatively bigger, and this may be the reasons of the enantioselective toxicity. However, the phenomenon described above was not observed for E. gracilis. E. gracilis is different from S. obliquus in subcellular structure, lacking cell walls. Moreover, the nutrient means of the two algae are also varied. These results indicate that we should be able to scale the effects of CILs across organisms more accurately and improve our ability to predict their effects in natural environments. In the meantime, to minimize the potential for environmental harm, the enantioselective toxicities of CILs with short alkyl chains should be taken into consideration.
(4) Dramatic differences between the toxicity of the enantiomers of DCPP to Arabidopsis thaliana were observed:the enantiomer of R-DCPP shows a higher level of toxicity. The assessment of plant growth was carried out by measuring the fresh weight of leaves and the length of root after exposure to the DCPP enantiomers and the results showed that fresh weight of control treatment was16.9mg, R-DCPP treatment was6.32, S-DCPP14.36and Rac-DCPP8.35mg. The root length of control treatment was49.53mm and for R-DCPP, S-DCPP, Rac-DCPP was4.87,34.2and7.7, respectively. The enantiomers of DCPP also stimulated the response of antioxidant defences and the activity of SOD of R-DCPP treatment was higher than the S-DCPP treatment while the activity of CAT, POD was lower than the S-DCPP treatment and the GSH content was also lower and all the treatments were lower than the control treatment. These results indicate that the antioxidant system was damaged and may not scavenge the excess ROS.
(5) The toxicity of IM to Arabidopsis thaliana also showed enantioselective differences. The fresh weight of leaves of control treatment was17.21, and for R-IM, S-IM, Rac-IM was5.25,15.36,7.36mg, respectively. The length root was51.42,4.21,43.2and7.62mm, respectively. The distribution of trace elements in leaves and roots were also determined when treated with IM. The results of leaves showed that the trace elements in control leaf were evenly distributed and the S-IM treated showed the same trend, while the R-IM and Rac-IM treated leaf was aggregated distributed and the expression of gene related to trace elements did not show significant enantioselective differences. However, the distribution of trace elements in root did not show difference.
引文
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