Chemical and biologically active constituents of Salsola collina

Jin, Yingxue; Du, Jing-Ling; Yang, Yan; Li, Jin; Song, Yan; Zhang, Wei; Chen, Haisheng

doi:10.1007/s10600-011-9896-2

Cited by 19 publications

(37 citation statements)

References 13 publications

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“…In this study, we discovered that transgenic expression of the herbicide-resistance enzyme BAR of bacterial origin indeed acetylate two endogenous amino acids, resulting in the ectopic accumulation of acetyl-aminoadipate and acetyl-tryptophan. While acetyl-tryptophan is a naturally occurring metabolite found in numerous plant species, including Arabidopsis, Salsola collina , Glycine max , Solanum lycopersicum , Cocos nucifera , and Ginkgo biloba 24,25 , to the best of our knowledge, acetyl-aminoadipate has never been reported as an endogenous plant metabolite. Interestingly, in line with our findings, a recent study reported the ectopic accumulation of acetyl-aminoadipate in the flower tissue of a BAR-containing T-DNA mutant of Arabidopsis, which could not be rationalized by the mutated gene 26 .…”

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confidence: 93%

Non-specific activities of the major herbicide-resistance gene BAR

et al. 2017

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Bialaphos resistance (BAR) and phosphinothricin acetyltransferase (PAT) genes, which convey resistance to the broad-spectrum herbicide phosphinothricin (also known as glufosinate) via N-acetylation, have been globally used in basic plant research and genetically engineered crops . Although early in vitro enzyme assays showed that recombinant BAR and PAT exhibit substrate preference toward phosphinothricin over the 20 proteinogenic amino acids , indirect effects of BAR-containing transgenes in planta, including modified amino acid levels, have been seen but without the identification of their direct causes . Combining metabolomics, plant genetics and biochemical approaches, we show that transgenic BAR indeed converts two plant endogenous amino acids, aminoadipate and tryptophan, to their respective N-acetylated products in several plant species. We report the crystal structures of BAR, and further delineate structural basis for its substrate selectivity and catalytic mechanism. Through structure-guided protein engineering, we generated several BAR variants that display significantly reduced non-specific activities compared with its wild-type counterpart in vivo. The transgenic expression of enzymes can result in unintended off-target metabolism arising from enzyme promiscuity. Understanding such phenomena at the mechanistic level can facilitate the design of maximally insulated systems featuring heterologously expressed enzymes.

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confidence: 93%

Non-specific activities of the major herbicide-resistance gene BAR

et al. 2017

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“…Only about 60 biological active ingredients have been detected from S. collina, including flavonoids, alkaloids, phenolic acids, organic acids, sterols, etc. [ 6 , 8 , 9 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. The main compounds are flavonoids and phenolic acids.…”

Section: Introductionmentioning

confidence: 99%

“…The main compounds are flavonoids and phenolic acids. The 18 reported flavonoids mainly involve flavones, flavonols and isoflavones [ 6 , 14 , 17 , 18 , 19 , 20 ]. Twelve phenolic acids have been identified from S. collina , such as vanillic acid, ferulic acid, salicylic acid, etc.…”

Section: Introductionmentioning

confidence: 99%

Widely Targeted Metabolomics Analysis of Different Parts of Salsola collina Pall

Chen

Duan

et al. 2021

Molecules

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Salsola collina Pall has a long history of being used as a traditional medicine to treat hypertension, headache, insomnia, constipation and vertigo. However, only a few biologically active substances have been identified from S. collina. Here, the shoots and roots of S. collina, namely L-Sc and R-Sc, were studied. The primary and secondary metabolites were investigated using ultrahigh-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (UPLC-ESI-MS/MS). A total of 637 putative metabolites were identified and these metabolites were mainly classified into ten different categories. Correlation analysis, hierarchical clustering analysis, principal component analysis and orthogonal partial least squares discriminant analysis of metabolites showed that the L-Sc samples could be clearly separated from the R-Sc samples. Differential accumulated metabolite analysis revealed that most of differential primary metabolites were significantly lower in the L-Sc than in the R-Sc. Conversely, the major differential secondary metabolites had higher levels in the L-Sc than in the R-Sc. Further analysis indicated that the flavonoids were the major putative antioxidant components and most of putative antioxidant components exhibited higher relative concentrations in the L-Sc than the R-Sc. These results improve our understanding of metabolite accumulation and provide a reference for the study of medicinal value in S. collina.

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“…Our findings therefore suggest a revised procedure incorporating metabolomics analysis for future assessment of GM crops in order to establish substantial equivalence, a central aspect of the risk assessment process 27 . While acetyl-tryptophan is a naturally occurring metabolite found in numerous plant species, including Arabidopsis, Salsola collina, Glycine max, Solanum lycopersicum, Cocos nucifera, and Ginkgo biloba 28,29 , to the best of our knowledge, acetyl-aminoadipate has never been reported as an endogenous plant metabolite in non-transgenic plants. However, in line with our findings, a recent study showed that acetyl-aminoadipate accumulates in flowers of a BAR-containing mutant of Arabidopsis 30 .…”

Section: Transgenic Expression Of Enzymes Catalyzing a Variety Of Desmentioning

confidence: 92%

Discovery and reduction of nonspecific activities of the major herbicide-resistance gene BAR

Christ

Hochstrasser

Guyer

et al. 2017

Preprint

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Herbicide resistance is a major trait of genetically modified (GM) crops. Currently, resistance to phosphinothricin (also known as glufosinate) is the second most widespread genetically engineered herbicide-resistance trait in crops after glyphosate resistance 1,2 . Resistance to phosphinothricin in plants isachieved by transgenic expression of the bialaphos resistance (BAR) or phosphinothricin acetyltransferase (PAT) genes, which were initially isolated from the natural herbicide bialaphos-producing soil bacteria Streptomyces hygroscopicus and S. viridochromogenes, respectively 3,4 . Mechanistically, BAR and PAT encode phosphinothricin acetyltransferase, which transfers an acetyl group from acetyl coenzyme A (acetyl-CoA) to the α-NH 2 group of phosphinothricin, resulting in herbicide inactivation 1 . Although early in vitro enzyme assays showed that recombinant BAR and PAT exhibit substrate preference toward phosphinothricin over the 20 proteinogenic amino acids 1 , whether transgenic expression of BAR and PAT affects plant endogenous metabolism in vivo was not known. Combining metabolomics, plant genetics, and biochemical approaches, we show that transgenic BAR indeed converts two plant endogenous amino acids, aminoadipate and tryptophan, to their respective N-acetylated products in several plant species examined. We report the crystal structures of BAR, and further delineate structural basis for its substrate selectivity and catalytic mechanism.Through structure-guided protein engineering, we generated several BAR variants that display significantly reduced nonspecific activities compared to its wild-type counterpart.Our results demonstrate that transgenic expression of enzymes as a common strategy in modern biotechnology may render unintended metabolic consequences arisen from enzyme promiscuity. Understanding of such phenomena at the mechanistic level will facilitate better design of maximally insulated systems featuring heterologously expressed enzymes. Peak area (a.u.) Peak area (a.u.) Acetyl-aminoadipate Acetyl-tryptophan K M = 132 ± 19 µM Vmax = 4.57 ± 0.23 nkat/mg Peak area (a.u.) Peak area (a.u.) Acetyl-aminoadipate Acetyl-tryptophan

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Chemical and biologically active constituents of Salsola collina

Cited by 19 publications

References 13 publications

Non-specific activities of the major herbicide-resistance gene BAR

Non-specific activities of the major herbicide-resistance gene BAR

Widely Targeted Metabolomics Analysis of Different Parts of Salsola collina Pall

Discovery and reduction of nonspecific activities of the major herbicide-resistance gene BAR

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