Glycosyltransferases: managers of small molecules

Bowles, Dianna J.; Isayenkova, Judith; Lim, Eng‐Kiat; Poppenberger, Brigitte

doi:10.1016/j.pbi.2005.03.007

Cited by 442 publications

(339 citation statements)

References 55 publications

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“…The rest is either conjugated with sulfate (20-46%) or cysteine (3%) (Bertolini et al 2006). A fraction of 5-15% is further oxidized by enzymes of the P450 mixed-function oxidase system to N-acetyl-p-benzoquinoneimine [NAPQI] (Bowles et al 2005;Corcoran et al 1980) that quickly reacts with glutathione. The resulting paracetamol-glutathione complex is converted to the non-toxic cysteine or mercapturate conjugates, which are eliminated in the urine (Miller et al 1976).…”

Section: Discussionmentioning

confidence: 99%

“…Potential acceptor molecules can be plant hormones (Hou et al 2004), endogenous synthesized secondary metabolites (Richman et al 2005) as well as xenobiotics (Messner et al 2003). With their multiple functions and the variety of possible substrates, glycosyltransferases play a major role in buffering the impacts of either biotic or abiotic challenges on the plant (Bowles et al 2005). The present study aimed at comparing the detoxification mechanisms for acetaminophen in mammals and plants by studying its fate and metabolism in the hairy root cell culture of Armoracia rusticana L. as a model system, and to give recommendations for the removal of the pharmaceutical from waste water by phytotechniques.…”

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confidence: 99%

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Metabolism of acetaminophen (paracetamol) in plants—two independent pathways result in the formation of a glutathione and a glucose conjugate

Huber¹,

Bartha²,

Harpaintner³

et al. 2009

Environ Sci Pollut Res

120

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Background, aim, and scope Pharmaceuticals and their metabolites are detected in the aquatic environment and our drinking water supplies. The need for high quality drinking water is one of the most challenging problems of our times, but still only little knowledge exists on the impact of these compounds on ecosystems, animals, and man. Biological waste water treatment in constructed wetlands is an effective and low-cost alternative, especially for the treatment of non-industrial, municipal waste water. In this situation, plants get in contact with pharmaceutical compounds and have to tackle their detoxification. The mechanisms for the detoxification of xenobiotics in plants are closely related to the mammalian system. An activation reaction (phase I) is followed by a conjugation (phase II) with hydrophilic molecules like glutathione or glucose. Phase III reactions can be summarized as storage, degradation, and transport of the xenobiotic conjugate. Until now, there is no information available on the fate of pharmaceuticals in plants. In this study, we want to investigate the fate and metabolism of N-acetyl-4-aminophenol (paracetamol) in plant tissues using the cell culture of Armoracia rusticana L. as a model system. Materials and methods A hairy root culture of A. rusticana was treated with acetaminophen in a liquid culture. The formation and identification of metabolites over time were analyzed using HPLC-DAD and LC-MS n techniques. Results With LC-MS technique, we were able to detect paracetamol and identify three of its metabolites in root cells of A. rusticana. Six hours after incubation with 1 mM of acetaminophen, the distribution of acetaminophen and related metabolites in the cells resulted in 18% paracetamol, 64% paracetamol-glucoside, 17% paracetamol glutathione, and 1% of the corresponding cysteine conjugate. Discussion The formation of two independently formed metabolites in plant root cells again revealed strong similarities between plant and mammalian detoxification systems. The detoxification mechanism of glucuronization in mammals is mirrored by glucosidation of xenobiotics in plants. Furthermore, in both systems, a glutathione conjugate is formed. Due to the existence of P450 enzymes in plants, the formation of the highly reactive NAPQI intermediate is possible. Conclusions In this study, we introduce the hairy root cell culture of A. rusticana L. as a suitable model system to study the fate of acetaminophen in plant tissues. Our first results point to the direction of plants being able to take up and detoxify the model substrate paracetamol. These first findings underline the great potential of using plants for waste water treatments in constructed wetlands. Recommendations and perspectives This very first study on the detoxification of a widely used antipyretic agent in plant tissues again shows the flexibility of plant detoxification systems and their potential in waste water treatment facilities. This study covers only the very first steps of acetaminophen detoxification in plants; s...

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

Metabolism of acetaminophen (paracetamol) in plants—two independent pathways result in the formation of a glutathione and a glucose conjugate

Huber¹,

Bartha²,

Harpaintner³

et al. 2009

Environ Sci Pollut Res

120

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“…Up regulation of both the putative sucrose synthase transcripts identified in this study during early maturation (JC1 stage) suggests the importance of sucrose synthase (King et al 1997;Li et al 2006) in providing carbon for oil biosynthesis. Higher transcript level for the putative UDP-glycosyl transferase only in JC1 also indicates a key role for the corresponding enzyme in transferring (Bowles et al 2005) sugar moieties from activated sugars to acceptor molecules like proteins, lipids and secondary metabolites, particularly during early seed maturation stages. Expression of seven out of twelve genes putatively involved in central carbon metabolism was up regulated in mid-to-late maturation stage (JC3).…”

Section: Transcripts Related To Central Carbon Metabolismmentioning

confidence: 96%

Differential expression analysis of transcripts related to oil metabolism in maturing seeds of Jatropha curcas L.

Chandran

Sankararamasubramanian

Kumar

et al. 2014

Physiol Mol Biol Plants

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Jatropha curcas has been widely studied at the molecular level due to its potential as an alternative source of fuel. Many of the reports till date on this plant have focussed mainly on genes contributing to the accumulation of oil in its seeds. A suppression subtractive hybridization strategy was employed to identify genes which are differentially expressed in the mid maturation stage of J. curcas seeds. Random expressed sequence tag sequencing of the cDNA subtraction library resulted in 385 contigs and 1,428 singletons, with 591 expressed sequence tags mapping for enzymes having catalytic roles in various metabolic pathways. Differences in transcript levels in early and mid-to-late maturation stages of seeds were also investigated using sequence information obtained from the cDNA subtraction library. Seven out of 12 transcripts having putative roles in central carbon metabolism were up regulated in early seed maturation stage while lipid metabolism related transcripts were detected at higher levels in the later stage of seed maturation. Interestingly, 4 of the transcripts revealed putative alternative splice variants that were specifically present or up regulated in the early or late maturation stage of the seeds. Transcript expression patterns from the current study using maturing seeds of J. curcas reveal a subtle balancing of oil accumulation and utilization, which may be influenced by their energy requirements.

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“…Plant UGTs possess an adjusted version of the conserved amino acid region named PSPG motif (plant secondary product glycosyltransferase) (Hughes and Hughes 1994;Paquette et al 2003), and acceptors include metabolites like plant hormones, phenylpropanoids, Xavonoids, coumarins, terpenoids, cyanohydrins, thiohydroxamates, and alkaloids (Vogt and Jones 2000;Bowles et al 2006). The broad spectrum of acceptors and the altered chemical features of glycosides suggest that UGTs play major roles in stabilization and colour determination of pigments, the adjustment of plant growth regulators, and plant defences against microbial and viral infections Gachon et al 2005;Bowles et al 2005Bowles et al , 2006. This is also mirrored in the number of PSPG genes reported.…”

Section: Introductionmentioning

confidence: 99%

Recombinant expression and functional characterisation of regiospecific flavonoid glucosyltransferases from Hieracium pilosella L.

Witte

Moco

Vervoort

et al. 2009

Planta

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Five glucosyltransferases were cloned by RT-PCR ampliWcation using total RNA from Hieracium pilosella L. (Asteraceae) inXorescences as template. Expression was accomplished in Escherichia coli, and three of the HIS-tagged enzymes, UGT90A7, UGT95A1, and UGT72B11 were partially puriWed and functionally characterised as UDP-glucose:Xavonoid O-glucosyltransferases. Both UGT90A7 and UGT95A1 preferred luteolin as substrate, but possessed diVerent regiospeciWcity proWles. UGT95A1 established a new subgroup within the UGT family showing high regiospeciWcity towards the C-3Ј hydroxyl group of luteolin, while UGT90A7 primarily yielded the 4Ј-O-glucoside, but concomitantly catalysed also the formation of the 7-O-glucoside, which could account for this Xavones glucoside in H. pilosella Xower heads. Semi quantitative expression proWles revealed that UGT95A1 was expressed at all stages of inXorescence development as well as in leaf and stem tissue, whereas UGT90A7 transcript abundance was nearly limited to Xower tissue and started to develop with the pigmentation of closed buds. Other than these enzymes, UGT72B11 showed rather broad substrate acceptance, with highest activity towards Xavones and Xavonols which have not been reported from H. pilosella. As umbelliferone was also readily accepted, this enzyme could be involved in the glucosylation of coumarins and other metabolites.

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Glycosyltransferases: managers of small molecules

Cited by 442 publications

References 55 publications

Metabolism of acetaminophen (paracetamol) in plants—two independent pathways result in the formation of a glutathione and a glucose conjugate

Metabolism of acetaminophen (paracetamol) in plants—two independent pathways result in the formation of a glutathione and a glucose conjugate

Differential expression analysis of transcripts related to oil metabolism in maturing seeds of Jatropha curcas L.

Recombinant expression and functional characterisation of regiospecific flavonoid glucosyltransferases from Hieracium pilosella L.

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