MetaboLightsapplication/xmlftp://ftp.ebi.ac.uk/pub/databases/metabolights/studies/public/MTBLS1847/m_MTBLS1847_GC-MS_positive__metabolite_profiling_v2_maf.tsvftp://ftp.ebi.ac.uk/pub/databases/metabolights/studies/public/MTBLS1847/s_MTBLS1847.txtftp://ftp.ebi.ac.uk/pub/databases/metabolights/studies/public/MTBLS1847/i_Investigation.txtftp://ftp.ebi.ac.uk/pub/databases/metabolights/studies/public/MTBLS1847/a_MTBLS1847_GC-MS_positive__metabolite_profiling.txtftp://ftp.ebi.ac.uk/pub/databases/metabolights/studies/public/MTBLS1847/RAW_FILESftp://ftp.ebi.ac.uk/pub/databases/metabolights/studies/public/MTBLS1847/files-all.jsonftp://ftp.ebi.ac.uk/pub/databases/metabolights/studies/public/MTBLS1847/DERIVED_FILESftp://ftp.ebi.ac.uk/pub/databases/metabolights/studies/public/MTBLS1847primaryOK200Lukasz MarczakMetaboLightsPublicGas Chromatography MS - positive<p>The transfer line and ion source temperatures in MS system were maintained at 250 °C. EI ionization was performed with 70 eV energy. Mass spectra were recorded in the mass range of 50–850 m/z.</p><p>The extracts were analyzed using TRACE 1310 GC oven with TSQ8000 triplequad MS from Thermo Scientific equipped with a DB-5 ms bonded-phase fused-silica capillary column (30 m length, 0.25 mm inner diameter, 0.25 µm film thickness) (J&W Scientific Co., USA). The mixture components were separated on a GC column using the following temperature gradient: 2 min at 70 °C and then 10 °C/min to 300 °C with a hold for 10 min at 300 °C (36 min in total). As a carrier gas, helium was used at a flow rate of 1 ml/min. 1 µl of each sample was injected in splitless mode. For sample introduction, a PTV injector was used starting at 40 °C for 0.1 min, and after that, the temperature was raised at 6 °C/s to 350 °C.</p>Pb Stress and Ectomycorrhizas: Strong Protective Proteomic Responses in Poplar Roots Inoculated with <i>Paxillus involutus</i> Isolate and Characterized by Low Root Colonization Intensity. 10.3390/ijms22094300. PMID:33919023Institute of Bioorganic Chemistry Polish Academy of SciencesPopulusmass spectrometry<p>The root metabolites for GC MS/MS were isolated from 5 mg of root and P. i. mycelium by methanol extraction and were further derivatized in a standard manner with N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA)<strong>[1].</strong></p><p><br></p><p><strong>Ref:</strong></p><p><strong>[1] </strong>Swarcewicz, B.; Sawikowska, A.; Marczak, Ł.; Łuczak, M.; Ciesiołka, D.; Krystkowiak, K.; Kuczy ´nska, A.; Pi´slewska-Bednarek, M.; Krajewski, P.; Stobliecki, M. Effect of drought stress on metabolite contents in barley recombinant inbred line population revealed by untargeted GC–MS profiling. Acta Physiol. Plant 2017, 39, 158</p>https://www.ebi.ac.uk/metabolights/MTBLS1847Agnieszka Szuba.Rafał Kozłowski.Łukasz Marczak. Institute of Bioorganic Chemistry Polish Academy of Sciences. lukasmar@ibch.poznan.pl.<p>Raw files were converted to net <strong>cdf </strong>format using <strong>Thermo file converter.</strong> </p>Treatment<p><strong>Poplar Trees and Fungal Cultures </strong></p><p>In our experiment, we compared 3 variants: <strong>nonmycorrhized (NM) </strong>plants grown in <strong>control </strong>conditions (<strong>NM-Control</strong>), <strong>nonmycorrhized </strong>plants exposed to <strong>Pb </strong>(<strong>NM-Pb</strong>) and <strong>inoculated </strong>poplars exposed to <strong>Pb </strong>(<strong>M-Pb</strong>). <strong>Populus × canescens</strong> microcuttings were cultivated in vitro in agar (0.8%) containing full-strength Murashige and Skoog medium (MS) supplemented with 1.5% sucrose covered with 3 mm of modified Melin–Norkrans medium (MNM) containing 1% glucose and 0.5% maltose. For the<strong> NM-Pb</strong> and <strong>M-Pb </strong>treatments, the agar medium was supplemented with 0.75 mM Pb(NO3)2. For the control treatment, nitrogen was compensated for with 0.75 mM NH4NO3. The final pH was adjusted to 5.5. </p><p><br></p><p>In the present study, we used <strong>Paxillus involutus</strong>, which increased in vitro poplar microcutting growth despite the low colonization ratio (Szuba, unpublished results). Fragments of barcoded (data not shown)<strong> P. involutus</strong> mycelium were placed near the freshly transferred poplar microcuttings growing in the 2-layer agar medium. Poplar cultures were grown in a growth chamber at 21 °C in 60% relative humidity with a 16 h/8 h day/night photoperiod using cool white fluorescent light (150 µmol m−2 s −1). Additionally, for the metabolomic study, pure cultures of<strong> P. involutus</strong> were cultivated in darkness in MNM medium on Petri dishes <strong>[1]</strong>.</p><p><br></p><p><strong>Harvesting and Biometrical, Biochemical and Root Colonization Analyses</strong></p><p>6 wks after inoculation, the leaves, stems and <strong>roots </strong>were weighed. Pooled samples of <strong>roots </strong>and agar medium as well as P. involutus hyphae (from the pure culture) were immediately frozen in liquid nitrogen and stored at –80 ◦C until analysis. For the <strong>M-Pb</strong> treatment, the <strong>root </strong>colonization level was assessed. The <strong>root </strong>tip morpho-type percentage was determined using ImageJ 1.48 v Software (Wayne Rasband, Bethesda, MD, USA) from high-resolution images captured during harvest. Categorization was performed on the basis of the anatomical structure of representative root tip morphotypes (selected during harvest and immediately analyzed under a microscope exactly according to <strong>[1]</strong>). <strong>Root </strong>tips were divided into three categories established during our previous study<strong>[1],[2]</strong>: ‘<strong>nonmycorrhized</strong>’ root tips and 2 stages of <strong>root </strong>tip colonization, ‘changed’ <strong>root </strong>tips (root tips devoid of root hairs and covered with fungi—such root tips do not have the fully developed Hartig net) and ‘fully mycorrhized’ root tips (swollen, shortened root tips with a very well-developed mantle —such phenotypes have a well-developed mantle and Hartig net). Pooled dried leaf (50 µg; we also analyzed the foliar P level; see <strong>Figure S1 </strong>in the paper associated with this study), stem and root (10 µg) samples were used to measure the Pb level in terms of both the concentration (µg/DWg) and content (mg per plant). The Pb translocation factor was calculated according to formula: Sum of Pb contents in stem and leaves (per plant) Root Pb content (per plant) . Mineral analyses were completed with 6 replicates using an inductively coupled plasma time-of-flight mass spectrometer (GBC Scientific Equipment, Hampshire, Braeside, Australia) as described in the previous published paper<strong>[1]</strong>. Agar medium was agitated for 10 min at 4 °C and then filtered through Miracloth (Millipore). The obtained supernatants were analyzed with an Elmetron CX-551 pH meter (n = 4).</p><p><br></p><p><strong>Refs:</strong></p><p><strong>[1] </strong>Szuba, A.; Karli ´nski, L.; Krzesłowska, M.; Hazubska–Przybył, T. Inoculation with a Pb–tolerant strain of Paxillus involutus improves growth and Pb tolerance of Populus × canescens under in vitro conditions. Plant Soil 2017, 412, 253–266.</p><p><strong>[2]</strong> Szuba A, Marczak Ł, Karliński L, Mucha J, Tomaszewski D. Regulation of the leaf proteome by inoculation of Populus × canescens with two Paxillus involutus isolates differing in root colonization rates. Mycorrhiza. 2019 Oct;29(5):503-517. doi: 10.1007/s00572-019-00910-5. Epub 2019 Aug 27. PMID: 31456074</p>Metabolomicsectomycorrhizaheavy metalsProteomicsCitrateuntargeted metabolitesDilution effectectomycorrhizaheavy metalsProteomicsCitrateuntargeted metabolitesDilution effectroot<p><strong>LECO ChromaTOF</strong> software was used for data acquisition, automatic peak detection, mass spectrum deconvolution, retention index calculation and <strong>NIST</strong> library searches. Retention indexes (RI) for each compound were calculated based on the alkane series mixture (C-10 to C-36) analysis. Metabolites were identified by library searches (<strong>NIST </strong>and Fiehn libraries); the analyte was considered identified when the quality threshold was passed, i.e., at a similarity index (SI) above 700 and a matching retention index ± 10. Artifacts (alkanes, column bleed, plasticizers, MSTFA and reagents) were identified analogously and then excluded from further analyses. The obtained data were normalized against the sum of the chromatographic peak areas (using the TIC approach), and the resulting tables were transferred into <strong>Perseus </strong>software (Max Planck). The ion intensities were transformed to log values and filtered for blanks in samples. The missing values in the Perseus data table were replaced (by constant value (0) imputation), and such prepared matrixes were used for the statistical calculations (see below).</p><p><br></p><p><strong>Statistical and Bioinformatics Analyses </strong></p><p>Statistical analyses of the biometric features of poplars and Pb levels (as well as leaf pigments and foliar mineral composition; see <strong>Figure S1 </strong>in the paper associated with this study) were performed using <strong>JMP Pro 13.0.0 </strong>software (SAS Institute Inc.). Values were considered significant according to T tests or ANOVA/post hoc HSD tests (α = 0.05). Statistical calculations for the molecular data (proteomic and metabolomic analyses) were performed in <strong>Perseus </strong>software. The log values (for information on data matrix preparation, see above) were analyzed using two-sample T tests and/or multisample ANOVA (α = 0.05; FDR = 0.05). Only the significantly differentially abundant compounds were subjected to a hierarchical analysis. For clustering analysis, data were normalized using the Z-score algorithm.</p>Benzoic acidEthyl ?-D-glucopyranosideMannoseMannobioseL-Proline, 5-oxoerythro-Tetrodialdose2-Hydroxyadipic acidGlycerol4,6-Dihydroxypyrimidine4-Hydroxybenzoic acidGalacto-HexodialdoseD-(+)-TrehaloseNonanoic acidL-(-)-Arabitoll-Aspartic acidl-Isoleucine, trimethylsilyl esterRibitolRibonic acidN-Ethyl-hexahydro-1H-azepinePhosphorylethanolaminecitric acid2-Pyrrolidone-5-carboxylic acid2-Oxoglutaric acidl-GlutamineD-(-)-Lyxofuranose2-Butenedioic acidGlutamic acidD-(-)-Fructose3-Pyridinecarboxylic acidArabinaric acidAucubinHexadecanoic acidLactuloseCinnamic acidPyruvic acidL-Threonic acidGlycineL-AsparagineD-MannitolSitosterolhydroquinone O-beta-D-glucopyranosideGlycerol-3-phosphateGlycolic acid3-Hydroxyphenylpropionic acidD-(+)-TalofuranoseNiacinamideMyo-InositolTetradecaneL-threonineD-(+)-CellobiosehydroxylamineTryptophanGalactinol1-MonopalmitinPropanedioic acidl-AlanineMannose-6-phosphateL-Threitol1-Cyclohexene-1-carboxylic acidL-ValineEthanedioic acidEthanimidic acid1,2-BenzenediolOctadecanoic acidMyo-Inositol phosphateD-(-)-Erythrose1,5-Anhydro-D-sorbitol9,12-Octadecadienoic acidTalopyranoseGlyceric acidGlycine, N-formyl-L-(+)-ThreoseD-(+)-TuranoseGalactaric acidMaltose?-Linolenic acid(+)-?-TocopherolSuccinic acidD-LactoseD-Gluconic acid1,3-DioxolaneD-(-)-RibofuranoseGlyceryl-glycosideD-GlucoseSerineDodecanoic acidD-Allose4-Hydroxybutyric acidN-?-Acetyl-L-LysineGalactitolPyridine, 1-oxided-Galactose2-Deoxy-1,3,4,5-tetrakis-pentitolGuloseGlyceric acid-3-phosphatel-Leucine, trimethylsilyl esterD-(+)-Xylosed-Ribosel-Methionine, trimethylsilyl esterL-(+)-Tartaric acidAconitic acid3-Hydroxy-3-methylglutaric acidD-(-)-Lyxose1,2,3-Propanetricarboxylic acidThe commonly observed increased heavy metal tolerance of ectomycorrhized plants is usually linked with the protective role of the fungal hyphae covering colonized plant root tips. However, the molecular tolerance mechanisms in heavy metal stressed low-colonized ectormyocrrhizal plants characterized by an ectomycorrhiza-triggered increases in growth are unknown. Here, we examined Populus × canescens microcuttings inoculated with the Paxillus involutus isolate, which triggered an increase in poplar growth despite successful colonization of only 1.9% ± 0.8 of root tips. The analyzed plants, lacking a mantle-a protective fungal biofilter-were grown for 6 weeks in agar medium enriched with 0.75 mM Pb(NO3)2. In minimally colonized 'bare' roots, the proteome response to Pb was similar to that in noninoculated plants (e.g., higher abundances of PM- and V-type H+ ATPases and lower abundance of ribosomal proteins). However, the more intensive activation of molecular processes leading to Pb sequestration or redirection of the root metabolic flux into amino acid and Pb chelate (phenolics and citrate) biosynthesis coexisted with lower Pb uptake compared to that in controls. The molecular Pb response of inoculated roots was more intense and effective than that of noninoculated roots in poplars.The commonly observed increased heavy metal tolerance of ectomycorrhized plants is usually linked with the protective role of the fungal hyphae covering colonized plant root tips. However, the molecular tolerance mechanisms in heavy metal stressed low-colonized ectormyocrrhizal plants characterized by an ectomycorrhiza-triggered increases in growth are unknown. Here, we examined <i>Populus × canescens</i> microcuttings inoculated with the <i>Paxillus involutus</i> isolate, which triggered an increase in poplar growth despite successful colonization of only 1.9% ± 0.8 of root tips. The analyzed plants, lacking a mantle-a protective fungal biofilter-were grown for 6 weeks in agar medium enriched with 0.75 mM Pb(NO<sub>3</sub>)<sub>2</sub>. In minimally colonized 'bare' roots, the proteome response to Pb was similar to that in noninoculated plants (e.g., higher abundances of PM- and V-type H<sup>+</sup> ATPases and lower abundance of ribosomal proteins). However, the more intensive activation of molecular processes leading to Pb sequestration or redirection of the root metabolic flux into amino acid and Pb chelate (phenolics and citrate) biosynthesis coexisted with lower Pb uptake compared to that in controls. The molecular Pb response of inoculated roots was more intense and effective than that of noninoculated roots in poplars.Pb Stress and Ectomycorrhizas: Strong Protective Proteomic Responses in Poplar Roots Inoculated with Paxillus involutus Isolate and Characterized by Low Root Colonization Intensity.Pb Stress and Ectomycorrhizas: Strong Protective Proteomic Responses in Poplar Roots Inoculated with <i>Paxillus involutus</i> Isolate and Characterized by Low Root Colonization Intensity.Szuba Agnieszka A, Marczak Łukasz Ł, Kozłowski Rafał Rprojections, AT1G11140, True Poplar, bioformation, Black, lamellae, FON1, Pflanze, postnatal development, Aminosaeure, Aminocarbonsaeure, A4, Amino acid, high weight, Ribosomal Protein, growth and development, SUPERMAN, biosynthesis, Poplar, alpha-amino acid, FLORAL ORGAN NUMBER 1, GRO:0005338, supernumerary, process of organ, TYPE, viridiplantae, CG12298, Balsam Poplar, protrusion, SUB, DAGA4, lamella, Root, True Poplars, Populus fremontii, exact), Roles, DmelCG12298, responsivity, heavy, SUP, Concepts, SCRAMBLED, Low, nigras, MAM, SCG3, KIF20A, multicellular organismal biosynthetic process, plantae, mantle tissue, reactivity, increased, Ribosomal, single-organism biosynthetic process, me75, amino acids, formation, anabolism, mei-1794, Bdr, plants, ridges, Super protein, Populus balsamiferas, D17Mit170, Cottonwoods, T1, sp, SNAP-25, synthesis, Hyphas, Black Poplar, Mif1, radix (exact), Populus nigra, climbing root (narrow), papilla, Role Concepts, SRF9, laminae, Tip, Agaricus involutus, Tips, radices (exact, anatomical protrusion, Root Tips, cou, True, Metal, raíz (Spanish, Root Tip, Balsam Poplars, anatomical process, plural), Aminokarbonsaeure, land plants, Proteins, Meristems, STRUBBELIG, lamina, Populus balsamifera., total expressed protein, flanges, aerial root (narrow), Populus fremontius, Synaptosomal-associated 25 kDa protein, alpha-amino acids, Tl3, Tl2, Populus, alpha-amino carboxylic acids, Poplars, LGMD2C, Concept, all, STRUBBELIG-RECEPTOR FAMILY 9, development, uptake, Lr, Role Concept, Black Poplars, Protein, shelf, Role, GENA70, 根 (Japanese, Hypha, activation, flange, organ process, Populus balsamifera, Amino Acid, Acid, poplar, poplars, DMDA1, Amino acids, growth pattern, poplar trees, increased number, non-developmental growth, shelves, Dub, postnatal growth, Populus L., Plant, FLO10, root, Amino, HERP, balsamiferas, projection, ridge, present in greater numbers in organism, processes, process, higher plants, DMDA, Populus nigras, spine, fremontius, SCARMD2, Bra, processus, Acids, response, Cottonwood, growth, T19D16.8, Balsam, Proteomes, SCM, accessory, FLORAL DEFECTIVE 10strong, poplar, radices (exact, me75, poplars, cou, raíz (Spanish, poplar trees, plural), Populus L., aerial root (narrow), root, Tl3, GRO:0005338, Tl2, D17Mit170, T1, climbing root (narrow)., all, radix (exact), Lr, exact), resilient, tough, Bra, 根 (Japanese, Low, Agaricus involutusprojections, True Poplar, bioformation, Black, lamellae, Pflanze, postnatal development, Aminosaeure, Aminocarbonsaeure, A4, Amino acid, high weight, Ribosomal Protein, growth and development, biosynthesis, Poplar, D4H1S1733E, alpha-amino acid, GRO:0005338, supernumerary, process of organ, TYPE, viridiplantae, Balsam Poplar, protrusion, DAGA4, lamella, nitrate(1-), Root, True Poplars, Populus fremontii, exact), Roles, responsivity, heavy, Dana, Concepts, Low, nigras, MAM, SCG3, multicellular organismal biosynthetic process, plantae, mantle tissue, DAND1, reactivity, increased, Ribosomal, single-organism biosynthetic process, me75, amino acids, formation, anabolism, plants, ridges, Populus balsamiferas, D17Mit170, Cottonwoods, T1, synthesis, Hyphas, Black Poplar, trioxidonitrate(1-), radix (exact), Populus nigra, trioxonitrate(1-), climbing root (narrow), papilla, Role Concepts, DAN, D1S1733E, NO3(-), laminae, Tip, Agaricus involutus, NITRATE ION, Tips, radices (exact, anatomical protrusion, Root Tips, cou, True, Metal, raíz (Spanish, Root Tip, Balsam Poplars, anatomical process, plural), Aminokarbonsaeure, land plants, Proteins, Meristems, lamina, Populus balsamifera., NO3, total expressed protein, flanges, aerial root (narrow), Populus fremontius, alpha-amino acids, Tl3, Tl2, Populus, alpha-amino carboxylic acids, Poplars, LGMD2C, Concept, all, development, uptake, Lr, Role Concept, Black Poplars, Protein, shelf, Role, NB, 根 (Japanese, Hypha, trioxonitrate(V), activation, flange, organ process, Populus balsamifera, Amino Acid, Acid, poplar, poplars, DMDA1, Amino acids, growth pattern, nitrate, poplar trees, increased number, non-developmental growth, shelves, postnatal growth, Populus L., Plant, root, Amino, balsamiferas, projection, ridge, present in greater numbers in organism, processes, process, higher plants, DMDA, [NO3](-), Populus nigras, spine, fremontius, SCARMD2, Bra, processus, Acids, response, Cottonwood, growth, Balsam, Proteomes, accessorystrong, poplar, radices (exact, me75, poplars, cou, raíz (Spanish, poplar trees, plural), Populus L., aerial root (narrow), root, Tl3, GRO:0005338, Tl2, D17Mit170, T1, climbing root (narrow)., all, radix (exact), Lr, exact), resilient, tough, Bra, 根 (Japanese, Low, Agaricus involutus0.00.00.00.00.0falsePb Stress and Ectomycorrhizas: Strong Protective Proteomic Responses in Poplar Roots Inoculated with Paxillus involutus Isolate and Characterized by Low Root Colonization IntensityThe commonly observed increased heavy metal tolerance of ectomycorrhized plants is usually linked with the protective role of the fungal hyphae covering colonized plant root tips. However, the molecular tolerance mechanisms in heavy metal stressed low-colonized ectormyocrrhizal plants characterized by an ectomycorrhiza-triggered increases in growth are unknown. Here, we examined <i>Populus × canescens</i> microcuttings inoculated with the <i>Paxillus involutus</i> isolate, which triggered an increase in poplar growth despite successful colonization of only 1.9% ± 0.8 of root tips. The analyzed plants, lacking a mantle-a protective fungal biofilter-were grown for 6 weeks in agar medium enriched with 0.75 mM Pb(NO<sub>3</sub>)<sub>2</sub>. In minimally colonized 'bare' roots, the proteome response to Pb was similar to that in noninoculated plants (e.g., higher abundances of PM- and V-type H<sup>+</sup> ATPases and lower abundance of ribosomal proteins). However, the more intensive activation of molecular processes leading to Pb sequestration or redirection of the root metabolic flux into amino acid and Pb chelate (phenolics and citrate) biosynthesis coexisted with lower Pb uptake compared to that in controls. The molecular Pb response of inoculated roots was more intense and effective than that of noninoculated roots in poplars.2022-01-112020-06-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:42090CHEBI:27897CHEBI:15429CHEBI:15824CHEBI:15428CHEBI:18305CHEBI:15671CHEBI:18145CHEBI:17057CHEBI:17053CHEBI:22592CHEBI:30830CHEBI:1427CHEBI:30794CHEBI:16988CHEBI:149529CHEBI:17716CHEBI:16995CHEBI:15940CHEBI:18135CHEBI:16070CHEBI:24406CHEBI:177827CHEBI:28842CHEBI:29019CHEBI:12936CHEBI:29136CHEBI:16977CHEBI:17306CHEBI:16857CHEBI:18403CHEBI:184008CHEBI:17553CHEBI:132960CHEBI:62318CHEBI:27904CHEBI:17154CHEBI:25448CHEBI:17393CHEBI:21405CHEBI:30852CHEBI:25164CHEBI:149542CHEBI:22211CHEBI:25048CHEBI:15756CHEBI:17822CHEBI:18237CHEBI:17268CHEBI:17023CHEBI:188950CHEBI:32528CHEBI:27693CHEBI:15908CHEBI:188939CHEBI:30746CHEBI:87597CHEBI:188945CHEBI:188947CHEBI:22958CHEBI:6359CHEBI:188942CHEBI:17497CHEBI:18183CHEBI:33508CHEBI:32816CHEBI:69081CHEBI:53455CHEBI:30915CHEBI:15978CHEBI:15741CHEBI:16831CHEBI:16551CHEBI:33198CHEBI:61512CHEBI:45969CHEBI:18050CHEBI:616988CHEBI:30763CHEBI:49028CHEBI:30805CHEBI:33511CHEBI:69796CHEBI:16899CHEBI:30769CHEBI:68462CHEBI:17505CHEBI:16813CHEBI:17634CHEBI:37684CHEBI:17754CHEBI:41253CHEBI:17351CHEBI:17196CHEBI:47013CHEBI:27386CHEBI:29565CHEBI:166508CHEBI:16414CHEBI:15963CHEBI:21717CHEBI:37691