Application of Separated Leaf Cell Suspension to Xenobiotic Metabolism in Plant

Fujisawa, Takuo; Matoba, Yoshihide; Katagi, Toshiyuki

doi:10.1021/jf901245t

Cited by 7 publications

(11 citation statements)

References 52 publications

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“…The first pathway is the ester cleavage that results in the formation of corresponding acid and alcohol (Products I a and II a ), which is a well known enzymatic hydrolysis pathway for most pyrethroids having an ester linkage in plants (Katagi, 2012 It is speculated that the NO 3 -induced cleavage of OAC(CN) bond occurs first and then the 3-phenoxybenzyl moiety generated could be finally oxidized to Product I c via elimination of hydrogen cyanide. Product I c may transform into Products II c and III c , and the similar pathway has been reported elsewhere (Akhtar, 1983;Katagi, 1992;Fujisawa et al, 2009). Product II c might also be formed directly via the NO 3 -induced 3-phenoxyphenyl cleavage from fenvalerate.…”

Section: Degradation Pathwayssupporting

confidence: 76%

“…wt 62) to the furan ring of resmetrhin. Lee, 1985, 6 is the Lee et al, 1988, 7 is the Katagi, 1992, and 8 is the Fujisawa et al, 2009. The molecular structures of the products are as shown in Fig.…”

Section: Reaction Productsmentioning

confidence: 99%

“…shown to be probably formed by the enzymatic oxidation of Product I c in leaf cell and chicken liver (Akhtar, 1983;Fujisawa et al, 2009). Both Products I c and III c are the principle soil degradation products of fenvalerate and have a lesser accumulation potential than the parent molecule (Lee, 1985).…”

Section: Reaction Products Of Fenvalerate Particlesmentioning

confidence: 99%

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Kinetic and product study of the heterogeneous reactions of NO3 radicals with suspended resmethrin, phenothrin, and fenvalerate particles

et al. 2013

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Section: Degradation Pathwayssupporting

confidence: 76%

Section: Reaction Productsmentioning

confidence: 99%

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Kinetic and product study of the heterogeneous reactions of NO3 radicals with suspended resmethrin, phenothrin, and fenvalerate particles

et al. 2013

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“…The conjugation with organic acids is widely known in plant metabolism. Abdel-Farid et al [36], for example, described malate conjugates of cinnamic acid derivatives in Brassica rapa leaves and Fujisawa et al [37] elucidated a malate conjugate of a pesticide in leaf cell suspension of Brassica oleracea .…”

Section: Resultsmentioning

confidence: 99%

Metabolism of HT-2 Toxin and T-2 Toxin in Oats

Meng-Reiterer

Bueschl

Rechthaler³

et al. 2016

Toxins

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The Fusarium mycotoxins HT-2 toxin (HT2) and T-2 toxin (T2) are frequent contaminants in oats. These toxins, but also their plant metabolites, may contribute to toxicological effects. This work describes the use of 13C-assisted liquid chromatography–high-resolution mass spectrometry for the first comprehensive study on the biotransformation of HT2 and T2 in oats. Using this approach, 16 HT2 and 17 T2 metabolites were annotated including novel glycosylated and hydroxylated forms of the toxins, hydrolysis products, and conjugates with acetic acid, putative malic acid, malonic acid, and ferulic acid. Further targeted quantitative analysis was performed to study toxin metabolism over time, as well as toxin and conjugate mobility within non-treated plant tissues. As a result, HT2-3-O-β-d-glucoside was identified as the major detoxification product of both parent toxins, which was rapidly formed (to an extent of 74% in HT2-treated and 48% in T2-treated oats within one day after treatment) and further metabolised. Mobility of the parent toxins appeared to be negligible, while HT2-3-O-β-d-glucoside was partly transported (up to approximately 4%) through panicle side branches and stem. Our findings demonstrate that the presented combination of untargeted and targeted analysis is well suited for the comprehensive elucidation of mycotoxin metabolism in plants.

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“…While conjugates of xenobiotic compounds with malonic and pyruvic acid are common, conjugates with malic acid are less frequently observed [62] and the pathway for their formation remains elusive.…”

Section: Resultsmentioning

confidence: 99%

Bikinin-like inhibitors targeting GSK3/Shaggy-like kinases: characterisation of novel compounds and elucidation of their catabolism in planta

Rozhon¹,

Wang²,

Berthiller³

et al. 2014

BMC Plant Biol

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BackgroundPlant GSK-3/Shaggy-like kinases are key players in brassinosteroid (BR) signalling which impact on plant development and participate in response to wounding, pathogens and salt stress. Bikinin was previously identified in a chemical genetics screen as an inhibitor targeting these kinases. To dissect the structural elements crucial for inhibition of GSK-3/Shaggy-like kinases by bikinin and to isolate more potent compounds we synthesised a number of related substances and tested their inhibitory activity in vitro and in vivo using Arabidopsis thaliana.ResultsA pyridine ring with an amido succinic acid residue in position 2 and a halogen in position 5 were crucial for inhibitory activity. The compound with an iodine substituent in position 5, denoted iodobikinin, was most active in inhibiting BIN2 activity in vitro and efficiently induced brassinosteroid-like responses in vivo. Its methyl ester, methyliodobikinin, showed improved cell permeability, making it highly potent in vivo although it had lower activity in vitro. HPLC analysis revealed that the methyl residue was rapidly cleaved off in planta liberating active iodobikinin. In addition, we provide evidence that iodobikinin and bikinin are inactivated in planta by conjugation with glutamic acid or malic acid and that the latter process is catalysed by the malate transferase SNG1.ConclusionBrassinosteroids participate in regulation of many aspects of plant development and in responses to environmental cues. Thus compounds modulating their action are valuable tools to study such processes and may be an interesting opportunity to modify plant growth and performance in horticulture and agronomy. Here we report the development of bikinin derivatives with increased potency that can activate BR signalling and mimic BR action. Methyliodobikinin was 3.4 times more active in vivo than bikinin. The main reason for the superior activity of methyliodobikinin, the most potent compound, is its enhanced plant tissue permeability. Inactivation of bikinin and its derivatives in planta involves SNG1, which constitutes a novel pathway for modification of xenobiotic compounds.

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Application of Separated Leaf Cell Suspension to Xenobiotic Metabolism in Plant

Cited by 7 publications

References 52 publications

Kinetic and product study of the heterogeneous reactions of NO3 radicals with suspended resmethrin, phenothrin, and fenvalerate particles

Kinetic and product study of the heterogeneous reactions of NO3 radicals with suspended resmethrin, phenothrin, and fenvalerate particles

Metabolism of HT-2 Toxin and T-2 Toxin in Oats

Bikinin-like inhibitors targeting GSK3/Shaggy-like kinases: characterisation of novel compounds and elucidation of their catabolism in planta

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