Uptake, translocation, and metabolism of sulfamethazine by <i>Arabidopsis thaliana</i>: distinguishing between phytometabolites and abiotic transformation products in the media

Huynh, Khang; Reinhold, David S.

doi:10.1080/15226514.2019.1667952

Cited by 9 publications

(25 citation statements)

References 48 publications

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“…Direct conjugation of TMP without prior modification was expected due to the presence of active groups on the TMP scaffold, and this phenomenon was indeed observed in 6 phase II metabolites: TMP537, TMP447, TMP551, TMP631, TMP319, and TMP453. Glycosidation of ABs in plants, which yielded information on TMP453, has previously been described as the main transformation pathway for sulfamethazine and sulfamethoxazole in A. thaliana [17,30] and for ofloxacin in lettuce [31]. Similarly, TMP319 and TMP349 share metabolic pathways, i.e.…”

Section: Biotransformation Reactionsmentioning

confidence: 95%

“…As with TMP321, methylation has been reported for clindamycin in lettuce [16]. In recent years, several studies have been published dealing with the plant conjugates of various xenobiotics, which could shed light on the fate of ABs in plants including conjugation with sugars, amino acids, a malonyl group, glutathione, glucuronic acid, sulfate, pterin, and methyl salicylate [15,17,30,[52][53][54]. For instance, two studies showed that sulfamethoxazole in Arabidopsis thaliana, alongside glycosylation as the main transformation pathway, underwent conjugation with glutathione and leucine after phase I transformation [15] and direct conjugation with pterin and methylsalicylate [17], which were not observed in this study.…”

Section: Biotransformation Reactionsmentioning

confidence: 99%

“…Indeed, only a few studies on the metabolization of sulfonamides (i.e. sulfamethoxazole, sulfadiazine, and sulfamethazine) [15][16][17]30], clarithromycin [16], and ofloxacin [31] in plants have been reported. For example, clarithromycin follows four major metabolic pathways in lettuce, including cladinose hydrolysis, demethylation, methylation, and oxidation [16].…”

Section: Introductionmentioning

confidence: 99%

“…For example, clarithromycin follows four major metabolic pathways in lettuce, including cladinose hydrolysis, demethylation, methylation, and oxidation [16]. On the other hand, the main transformation pathways reported for sulphonamides are oxidation, hydroxylation, and desulfation during phase I, and conjugation with glucose, N4-glycosyl-glycoside, pterin, methylsalicylate glutathione, glucuronic acid, and leucine during phase II [15][16][17]30]. These studies show that in spite of some common phase I metabolites, AB metabolization in plants is rather diverse and unpredictable.…”

Section: Introductionmentioning

confidence: 99%

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Systematic identification of trimethoprim metabolites in lettuce

et al. 2022

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Antibiotics are some of the most widely used drugs. Their release in the environment is of great concern since their consumption is a major factor for antibiotic resistance, one of the most important threats to human health. Their occurrence and fate in agricultural systems have been extensively investigated in recent years. Yet whilst their biotic and abiotic degradation pathways have been thoroughly researched, their biotransformation pathways in plants are less understood, such as in case of trimethoprim. Although trimethoprim has been reported in the environment, its fate in higher plants still remains unknown. A bench-scale experiment was performed and 30 trimethoprim metabolites were identified in lettuce (Lactuca sativa L.), of which 5 belong to phase I and 25 to phase II. Data mining yielded a list of 1018 ions as possible metabolite candidates, which was filtered to a final list of 87 candidates. Molecular structures were assigned for 19 compounds, including 14 TMP metabolites reported for the first time. Alongside well-known biotransformation pathways in plants, additional novel pathways were suggested, namely, conjugation with sesquiterpene lactones, and abscisic acid as a part of phase II of plant metabolism. The results obtained offer insight into the variety of phase II conjugates and may serve as a guideline for studying the metabolization of other chemicals that share a similar molecular structure or functional groups with trimethoprim. Finally, the toxicity and potential contribution of the identified metabolites to the selective pressure on antibiotic resistance genes and bacterial communities via residual antimicrobial activity were evaluated.

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Section: Biotransformation Reactionsmentioning

confidence: 95%

Section: Biotransformation Reactionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Systematic identification of trimethoprim metabolites in lettuce

et al. 2022

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“…Concentrations of parent antibiotics ( i.e ., original antibiotic compounds) in crop plants are usually negligible, ,, prompting conclusions that antibiotics represent a minimal risk to human health through consumption of the contaminated food crops . However, most of these studies have overlooked the presence of phytometabolites that could be converted to the parent aglycones during human digestion of food materials. , Recently, Huynh and Reinhold investigated the metabolism of sulfamethoxazole (SMX) and sulfamethazine (SMT) by the model plant Arabidopsis thaliana. , The parent sulfonamides in plant tissues accounted for only 1.1 and 1.7% of the SMX and SMT taken up by A. thaliana, respectively.…”

Section: Introductionmentioning

confidence: 99%

Fate of Phytometabolites of Antibiotics during In Vitro Digestion and Implications for Human Health

Keppler

Huynh

Reinhold

et al. 2021

J. Agric. Food Chem.

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Antibiotics are released into the environment as their global consumption increases. Uptake, accumulation, and metabolism of antibiotics by food crops is an emerging health concern as the associated risks of consuming food crops containing antibiotics are still largely unknown. This study investigated the fate of sulfamethazine, sulfamethoxazole, and their phytometabolites during in vitro digestion of the model plantArabidopsis thaliana. The amounts of parent antibiotics released during in vitro digestion were 4–5 times higher than those quantified in plant tissues prior to digestion, which was attributed to back transformation of the phytometabolites into the parent aglycones. These findings demonstrated that overlooking the proportions of phytometabolites in recent health risk assessment studies would considerably underestimate the realistic human exposure through consumption of contaminated food crops. New risk assessment frameworks are necessary to include these critical factors for comprehensively addressing human exposure to emerging contaminants through food chains.

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