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首页> 外文期刊>Journal of environmental science and health >Metabolism of the~(14)C-labeled herbicide clodinafop-propargyl in plant cell cultures of wheat and tobacco
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Metabolism of the~(14)C-labeled herbicide clodinafop-propargyl in plant cell cultures of wheat and tobacco

机译：〜（14）C标记的除草剂clodinafop-炔丙基在小麦和烟草植物细胞培养物中的代谢

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摘要

The metabolism of ~(14)C-clodinafop-propargyl (CfP) was examined in cell cultures of wheat (Triticum aestivum L. cv. 'Heines Koga Ⅱ') and tobacco (Nicotiana tabacum L.). Besides the non-transgenic tobacco culture, cultures transformed separately with cDNA of human cytochrome P450-monooxygenases (P450s) CYP1A1, CYP1A2, CYP3A4, CYP2B6 and CYP2C19 were examined. Experiments with wheat were executed in the presence and absence of safener cloquintocet-mexyl (CqM). After 48 h of incubation, only about 10% of applied ~(14)C was found in media (both tobacco and wheat). Non-extractable residues of ~(14)C-CfP in wheat cells were 16.54% (without CqM) and 30.87% (with CqM). In all tobacco cultures, 82.41-92.46% of applied radioactivity was recovered in cell extracts. In contrast to wheat, non-extractable residues amounted only to 1.50-2.82%. As determined by radio-thin layer chromatography (TLC) and -high-performance liquid chromatography (HPLC), the parent CfP was not found in the cell extracts of wheat; in tobacco cell extracts, only traces of CfP were detected. After a hydrolysis of assumed carbohydrate conjugates of CfP derived polar ~(14)C-labeled compounds, TLC and HPLC analysis showed that in wheat, a more complex pattern of metabolites of CfP were observed as compared to all tobacco cultures. In hydrolysates resulting from wheat, the identity of three primary products was confirmed by means of GC-EI-MS: free acid clodinafop (Cf), hydroxy-Cf hydroxylated at the pyridinyl moiety, and 4-(5-chloro-3-fluoropyridin-2-yloxy) phenol. In hydrolysates derived from all tobacco cultures, main metabolite was Cf besides only traces of further unidentified products. Differences among the different tobacco cultures (non-transgenic, transgenic) did not emerge. According to kinetics of disappearance of primary metabolite Cf as well as formation of polar soluble products and non-extractable residues, metabolization of CfP proceeded at a noticeably higher rate in wheat cells treated with safener CqM than in cells without CqM treatment. Thus, these results indicated a stimulation of CfP's metabolism by CqM, although metabolic profiles observed in CqM treated and non-treated cells (after hydrolysis) were qualitatively similar. The findings obtained from all tobacco cultures suggested that with the exception of ester cleavage to Cf, CfP cannot be metabolized by tobacco itself or by the human P450s examined.
机译：在小麦（Triticum aestivum L. cv。'Heines KogaⅡ'）和烟草（Nicotiana tabacum L.）的细胞培养物中检测了〜（14）C-clodinafop-propargyl（CfP）的代谢。除非转基因烟草培养物外，还检测了分别用人细胞色素P450单加氧酶（P450s）CYP1A1，CYP1A2，CYP3A4，CYP2B6和CYP2C19 cDNA转化的培养物。在存在和不存在更安全的cloquintocet-mexyl（CqM）的情况下进行了小麦实验。孵育48小时后，在培养基（烟草和小麦）中仅发现约10％的应用〜（14）C。小麦细胞中〜（14）C-CfP的不可提取残基为16.54％（无CqM）和30.87％（有CqM）。在所有烟草培养物中，从细胞提取物中回收到82.41-92.46％的应用放射性。与小麦相比，不可提取的残留量仅为1.50-2.82％。通过放射薄层色谱法（TLC）和高效液相色谱法（HPLC）测定，在小麦的细胞提取物中未发现母体CfP。在烟草细胞提取物中，仅检测到痕量的CfP。在假定的CfP衍生的极性（14）C标记的化合物的碳水化合物缀合物水解后，TLC和HPLC分析表明，与所有烟草培养物相比，在小麦中观察到的CfP代谢产物模式更为复杂。在小麦产生的水解物中，通过GC-EI-MS确认了三种主要产物的身份：游离酸clodinafop（Cf），在吡啶基部分羟基化的羟基-Cf和4-（5-氯-3-氟吡啶） -2-基氧基）苯酚。在来自所有烟草文化的水解产物中，主要代谢产物为Cf，仅含有痕量的其他未知产品。没有出现不同烟草文化（非转基因，转基因）之间的差异。根据主要代谢产物Cf消失的动力学以及极性可溶产物和不可提取残留物的形成，用安全的CqM处理的小麦细胞中CfP的代谢速率明显高于未使用CqM处理的细胞。因此，这些结果表明，尽管在经CqM处理和未处理的细胞（水解后）中观察到的代谢特征在质量上相似，但CqM刺激了CfP的代谢。从所有烟草文化中获得的发现表明，除酯裂解成Cf外，CfP不能被烟草本身或被检测的人P450代谢。

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