Misincorporation of free <i>m</i>-tyrosine into cellular proteins: a potential cytotoxic mechanism for oxidized amino acids

Gürer-Orhan, Hande; Erçal, Nuran; Mare, Suneetha; Pennathur, Subramaniam; Orhan, Hilmi; Heinecke, Jay W.

doi:10.1042/bj20051964

Cited by 74 publications

(81 citation statements)

References 33 publications

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“…However, because significant growth inhibition is observed at Ͼ100-fold lower concentrations in Arabidopsis than in B. subtilis (23) or Chinese hamster ovary cells (24), plant proteins would have to be uniquely sensitive to m-tyrosine incorporation.…”

Section: Resultsmentioning

confidence: 99%

“…m-Tyrosine is incorporated into proteins in place of phenylalanine in bacteria (23) and mammalian cells (24), where it is associated with increased protein turnover (25). Vigna radiata (mung bean) phenylalanine tRNA synthase accepts m-tyrosine with 25% of the efficiency of phenylalanine (26), suggesting that m-tyrosine might also be misincorporated into plant proteins.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Grass roots chemistry: meta -Tyrosine, an herbicidal nonprotein amino acid

Bertin

Weston²,

Huang

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

172

185

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Fine fescue grasses displace neighboring plants by depositing large quantities of an aqueous phytotoxic root exudate in the soil rhizosphere. Via activity-guided fractionation, we have isolated and identified the nonprotein amino acid m-tyrosine as the major active component. m-Tyrosine is significantly more phytotoxic than its structural isomers o-and p-tyrosine. We show that mtyrosine exposure results in growth inhibition for a wide range of plant species and propose that the release of this nonprotein amino acid interferes with root development of competing plants. Acid hydrolysis of total root protein from Arabidopsis thaliana showed incorporation of m-tyrosine, suggesting this as a possible mechanism of phytotoxicity. m-Tyrosine inhibition of A. thaliana root growth is counteracted by exogenous addition of protein amino acids, with phenylalanine having the most significant effect. The discovery of m-tyrosine, as well as a further understanding of its mode(s) of action, could lead to the development of biorational approaches to weed control.allelopathy ͉ festuca ͉ rhizosphere ͉ root ecology ͉ Arabidopsis R oot exudation of small molecules plays a major role in plant ecosystems and is often associated with the development of competitive advantage through allelopathy (1, 2). Juglone, a highly phytotoxic naphthoquinone produced by black walnut (Juglans nigra L.), and sorgoleone, a substituted quinone from sorghum (Sorghum spp.), are two classic examples of potently active allelochemicals deposited via the plant's living root system ( Fig. 1) (3). Elucidation of the structures and mode of action of previously unknown root-derived phytotoxins could lead to new biorational approaches to weed control.Because of their stress tolerance and disease resistance, fescue (Festuca spp.) grasses are commonly used in landscape, roadside, and pasture settings, as well as for conservation purposes (4, 5). The unusual ability of many fine leaf fescue species to outcompete other plants is well known, and previous investigations suggested that fescue root exudates have phytotoxic properties (4). Here, we report the isolation, identification, and biological activity of m-tyrosine, a potent, structurally unusual broadspectrum phytotoxin exuded by the roots of some fine leaf fescue grasses. Results and DiscussionIn an initial field evaluation of 80 fine fescue cultivars, 8 cultivars with strong weed suppressive potential were identified and their allelopathic potential in laboratory settings was confirmed (4). Based on both field and laboratory results, we selected ''Intrigue,'' a common Chewing's fescue cultivar (Festuca rubra L. ssp. commutata), for further studies.To identify the allelopathic compound(s) contained in Intrigue root exudates, we developed an activity-guided separation scheme based on the inhibition of lettuce (Lactuca sativa L.) radicle elongation in a filter paper-based assay. By using this assay, we compared the phytotoxicity of root surface washes (hexanes, dichloromethane, methanol, and water) prepared from 2-w...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Grass roots chemistry: meta -Tyrosine, an herbicidal nonprotein amino acid

Bertin

Weston²,

Huang

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

172

185

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“…As a mechanism of cytotoxicity, misincorporation of m-tyrosine in place of phenylalanine into cellular protein was suggested in bacteria 37) and cultured Chinese-hamster ovary cells. 38) Plant amino acids having anti-microbial and insecticidal activities revealed that one mechanism of toxicity was the incorporation of non-protein amino acids into the cellular protein of predators; however, the biosynthetic incorporation of m-tyrosine into plant systems has not been well studied. Mung bean phenylalanine tRNA synthase accepts m-tyrosine with 25% efficiency of phenylalanine, suggesting that m-tyrosine might also be misincorporated into plant proteins; a small amount of m-tyrosine was detected from the root protein of m-tyrosine-treated Arabidopsis seedlings.…”

Section: Phytotoxic Activity and Action Mechanism Of M-tyrosinementioning

confidence: 99%

The mechanisms of phytotoxic action and selectivity of non-protein aromatic amino acids L-DOPA and m-tyrosine

Matsumoto

2011

J. Pestic. Sci.

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Many non-protein aromatic amino acids have been found in plants. Among the amino acids, L-DOPA (L-3, 4-dihydroxyphenylalanine) and m-tyrosine (L-3-hydroxyphenylalanine) show unique phytotoxic activity. In this review, the action mechanisms of L-DOPA and m-tyrosine as allelochemicals are discussed. The phytotoxicity of L-DOPA is considered to be due to oxidative damage caused by reactive oxygen species generated from the melanin synthesis pathway. Selectivity among species might be achieved by the differential activity of an enzyme, polyphenol oxidase (PPO), catalyzing the conversion of L-DOPA to DOPA quinone in melanin synthesis pathway. Plant species with high PPO activity introduce more L-DOPA in melanogenesis and generate a greater amount of toxic reactive oxygen species. An antioxidant, ascorbic acid, reduced melanin formation by suppressing PPO activity and recovered from L-DOPA toxicity. We found that m-tyrosine had strong phytotoxic activity in lettuce. Interestingly, m-tyrosine also suppressed the growth of barnyardgrass, which is tolerant to L-DOPA. Like L-DOPA, m-tyrosine induced lipid peroxide formation in lettuce; however, this oxidative damage was not rescued by ascorbic acid but by phenylalanine. It is known that certain structural analogues of protein amino acids can be misincorporated into proteins; however, our recent results suggested that m-tyrosine is not incorporated into the proteins of rice root, which is sensitive to m-tyrosine. The mechanism of the phytotoxicity of m-tyrosine is still under investigation. © Pesticide Science Society of Japan

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“…There is evidence that in protein synthesis, mtyrosine is incorporated in bacteria instead of phenylalanine (Aronson e Wermus, 1965), in mammalian cells (Gurer-Orhan, 2006;Matayatsuk et al, 2007) and vegetables (Rodgers et al, 2002). For example, in Vigna radiata phenylalanine tRNA synthetase catalyzes also up to 25% of m-tyrosine instead of phenylalanine (Rodgers et al, 2002).…”

Section: Meta-tyrosinementioning

confidence: 99%

Uso potencial de aminoácidos não-proteinogênicos como aleloquímicos

Fipke

Vidal

2015

RBHerbicidas

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-From existing amino acids, twenty are directly involved in the formation of proteins.The others are known as non-proteinogenic amino acids (NPAA). The NPAA have different functions, including anti-herbivory activity, antimicrobial, protection from stress, cell signaling, nitrogen storage, as toxins against invertebrates and vertebrates and as allelochemicals. Plants are able to release these metabolites in the soil, which may influence the growth and development of neighboring plants, both positively and negatively. The objective of this review is to describe the chemical characteristics, the allelopathic potential and selectivity for crops of non-proteinogenic amino acids m-tyrosine, L-DOPA, methionine sulfoximine and azetidine. Keywords: m-tyrosine; L-3,4-dihydroxyphenylalanine; MSO; azetidine-2-carboxylic acid Resumo -Dos aminoácidos existentes, vinte estão envolvidos diretamente na formação de proteínas. Os demais são conhecidos como aminoácidos não-proteinogênicos (AANP). Os AANP possuem diferentes funções, incluindo atividade anti-herbivoria, antimicrobiana, proteção contra o estresse, sinalização celular, armazenamento de nitrogênio, como toxinas contra invertebrados e vertebrados e, também, como aleloquímicos. As plantas são capazes de liberar esses metabólitos no solo, os quais podem influenciar o crescimento e desenvolvimento de plantas vizinhas, tanto positiva como negativamente. O objetivo dessa revisão é descrever as características químicas, o potencial alelopático e a seletividade para culturas dos aminoácidos não-proteinogênicos mtirosina, L-DOPA, metionina sulfoximina e azetidino.

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Misincorporation of free m-tyrosine into cellular proteins: a potential cytotoxic mechanism for oxidized amino acids

Cited by 74 publications

References 33 publications

Grass roots chemistry: meta -Tyrosine, an herbicidal nonprotein amino acid

Grass roots chemistry: meta -Tyrosine, an herbicidal nonprotein amino acid

The mechanisms of phytotoxic action and selectivity of non-protein aromatic amino acids L-DOPA and m-tyrosine

Uso potencial de aminoácidos não-proteinogênicos como aleloquímicos

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