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Fig. 7 in Metabolite profiling reveals a role for intercellular dihydrocamalexic acid in the response of mature Arabidopsis thaliana to Pseudomonas syringae

Fig. 7. Exogenous infiltration of dihydrocamalexic acid (DHCA) and bacterial quantification of Pseudomonas syringae in rosette leaves of 7-week old Col-0 and cyp71a12/cyp71a13. DHCA (0.07 μg/mL or 0.25 μg/mL) was applied via pressure infiltration to 7-week-old plants at 24 h postinoculation with P. syringae or mock solution (0.06% DMSO in 10 mM MgCl2). Bacterial levels were quantified at 3 days postinoculation with Pst. Values represent the mean ± standard deviation of three sample replicates (n = 3) consisting of 8 plants each. Different letters indicate statistically significant differences (ANOVA, Tukey's honestly significant difference [HSD], P <0.05).

Fig. 6 in Metabolite profiling reveals a role for intercellular dihydrocamalexic acid in the response of mature Arabidopsis thaliana to Pseudomonas syringae

Fig. 6. Effect of dihydrocamalexic acid (DHCA) and salicylic acid (SA) on biofilm formation of Pseudomonas syringae (Pst) in vitro. Dose-dependent effect of (A) SA and (B) DHCA on Pst biofilm formation in Hrp-inducing minimal medium as measured by crystal violet staining of surface-adherent cells and de-staining with acetic acid (OD570) after stationary incubation for 24, 32, 48, or 60 h. Each data point is the mean ± SD of five wells per concentration from a 96-well non-tissueculture-treated plate. Different letters indicate statistically significant differences (one-way ANOVA, Tukey's honestly significant difference [HSD], P <0.05). Ns indicates not significant. Bars (from left to right) within each timepoint are: 18 μg/mL, 4.5 μg/mL, 1.2 μg/mL, 0.3 μg/mL, and 0 μg/mL. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 5 in Metabolite profiling reveals a role for intercellular dihydrocamalexic acid in the response of mature Arabidopsis thaliana to Pseudomonas syringae

Fig. 5. Growth of Pseudomonas syringae (Pst) in the presence of dihydrocamalexic acid (DHCA), camalexin, or DHCA analogs in vitro. Dose-dependent effect of (S)-dihydrocamalexic acid (A), camalexin (B), (1) (R)-2-(phenyl)-4,5-dihydrothiazole-4-carboxylic acid (C), (2) (S)-2-(phenyl)-4,5-dihydrothiazole-4-carboxylic acid (D), (3) (R)-2-(4-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid (E), and (4) (S)-2-(4-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid (F) on the growth of Pst in Hrp-inducing minimal medium as measured by turbidity (OD) after incubation for 68 h at room temperature (approximately 25 ◦ C). Each data 600 point is the mean ± SD of three wells per concentration from a 96-well non-tissue-culture-treated plate.

Fig. 4 in Metabolite profiling reveals a role for intercellular dihydrocamalexic acid in the response of mature Arabidopsis thaliana to Pseudomonas syringae

Fig. 4. Quantification of dihydrocamalexic acid (DHCA) (m/z 247.0541, [C12H10N2O2S þ H]) in intercellular washing fluids (IWFs). DHCA levels measured in IWFs from Col-0, cyp71a12/cyp71a13, and cyp71b15 (all 7-weeks post-germination) 24 h after inoculation with P. syringae (Pst) or 10 mM MgCl2 (mock-inoculation) measured by UPLC-MS electrospray ionization in positive mode (ESI+). Values represent the mean ± standard deviation of three sample replicates (n = 3). Different letters indicate statistically significant differences (one-way ANOVA, Tukey's honestly significant difference [HSD], P <0.05). Standard curves were prepared using synthetic DHCA (2 pg–6 μg on column).

Fig. 3 in Metabolite profiling reveals a role for intercellular dihydrocamalexic acid in the response of mature Arabidopsis thaliana to Pseudomonas syringae

Fig. 3. Identification of dihydrocamalexic acid (DHCA) in intercellular washing fluids. Extracted ion chromatograms and mass spectra for DHCA (m/z 247.0541, [C12H10N2O2S + H] in intercellular washing fluids from Pseudomonas syringae-inoculated leaves compared to a synthetic standard. (A) Extracted ion chromatograms and (B) MSMS (25 eV). n. d. Indicates compound not detected. Samples were run in positive electrospray ionization mode.

Fig. 1 in Metabolite profiling reveals a role for intercellular dihydrocamalexic acid in the response of mature Arabidopsis thaliana to Pseudomonas syringae

Fig. 1. Biosynthesis pathway of tryptophan-derived specialised metabolism in Arabidopsis thaliana (simplified). Dashed arrows indicate potential nonenzymatic reactions. Multiple arrows indicate multiple reaction steps simplified for presentation. IAOx: indole-3-acetaldoxime, I3M: indole-3- methylglucosinolate, IAN: indole-3-acetonitrile, ICHO: indole-3-carbaldehyde, ICOOH: indole-3-carboxylic acid, ICN: indole-3-carbonyl nitrile, 4-OH-ICN: 4- hydroxyindole-3-carbonyl nitrile, NSP: nitrile-specifier protein, FOX1: flavin-dependent oxidoreductase, AAO1: Arabidopsis aldehyde oxidase I, GGP: gammaglutamyl peptidase, GGT: gamma-glutamyl transpeptidase DHCA: dihydrocamalexic acid. Modified from Rajniak et al. (2015); Müller et al. (2019).

Fig. 5. Total ubiquinone-9 in 3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Fig. 5. Total ubiquinone-9 content in the rosette leaves of wild-type, ugt78d2, f3′h, and f3′h/ugt78d2 plants. Plants were grown on soil in 16-h days (110 μE m 2 s 1) at 22 ◦C for 3 weeks. Data represent the means of 7–8 biological replicates ±SE. P values from an analysis of variance between each mutant and the wild-type reference are indicated above the bars. The asterisk indicates significant differences from the wild type as determined by variance analysis (P <α = 0.1).

Fig. 4. 4 in 3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Fig. 4. 4-hydroxybenzoate content in A. thaliana roots and rosette leaves. Roots were harvested from 17-day-old axenic cultures, while rosette leaves were harvested from 3-week-old plants grown on soil. Samples were processed with and without acidic hydrolysis, and 4-hydroxybenzoate was quantified by HPLCspectrophotometry. Data represent the means of 3–4 biological replicates ± SE. P values from an analysis of variance between the ugt78d1/ugt78d2 knockout and the wild-type reference are indicated above the bars. Threshold for statistically significant differences between ugt78d1/ugt78d2 and wild-type data as determined by variance analysis was P <α = 0.1. n.d.: not detected.

Fig. 1 in 3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Fig. 1. Metabolic origins of 4-hydroxybenzoate for ubiquinone biosynthesis in plant cells. Note that chemical modeling of the peroxidative cleavage of kaempferol predicts that peroxidases do not act on kaempferol itself, but on its α-diketone tautomer. The formation of the latter is contingent on the presence of a double bond between C-2 and C-3 and a free C-3- OH on the C-ring. Dashed arrows indicate unknown and/or multiple steps. Ara, arabinosyl; Glu, glucosyl; Rha, Rhamnosyl; UGT78D1, flavonol 3-O-rhamnosyltransferase; UGT78D2, flavonol 3-O-glucosyltransferase; UGT78D3, flavonol 3-O- arabinosyltransferase.

Fig. 3 in 3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Fig. 3. Total ubiquinone content and rate of de novo ubiquinone biosynthesis in A. thaliana. A) Total ubiquinone-9 content in the rosette leaves of 3-week-old wild-type, ugt78d1, ugt78d2, ugt78d3 and ugt78d1/ugt78d2 plants grown on soil. B) Relative ubiquinone-9- [Ring-13C] labeling in the leaves of axenically 6 grown wild-type, ugt78d1, ugt78d2, ugt78d3 and ugt78d1/ugt78d2 plants fed for 3h with 250 μM of phenylalanine-[Ring- 13C]. Data represent the means of 4–6 6 biological replicates ± SE. P values from an analysis of variance between each mutant and the wild-type reference are indicated above the bars. Asterisks indicate significant differences from the wild type as determined by variance analysis (P <α = 0.1).

Fig. 47 in The scope of flavin-dependent reactions and processes in the model plant Arabidopsis thaliana

Fig. 47. Reaction catalyzed by D-amino acid oxidase. Regeneration of the reduced FAD occurs by dioxygen leading to the production of hydrogen peroxide (top). Note that the direct product of the oxidation, the corresponding imino acid, is non-enzymatically hydrolyzed to yield the α-keto acid and ammonia.

Fig. 33 in The scope of flavin-dependent reactions and processes in the model plant Arabidopsis thaliana

Fig. 33. Reaction of flavin-dependent monooxygenases involved in auxin biosynthesis. All enzymes forming clade 2 were shown to play an important role in auxin biosynthesis, as they were identified to mediate the conversion of indole-3-pyruvic acid to indole-3-acetic acid (Dai et al., 2013; Mashiguchi et al., 2011).

Fig. 28 in The scope of flavin-dependent reactions and processes in the model plant Arabidopsis thaliana

Fig. 28. Reaction of phytoene dehydrogenase/desaturase. The enzyme introduces two double bonds at position 11 and 11′ and mediates the concomitant trans-to-cis isomerization at position 9 and 9'. Reoxidation of the reduced cofactor is achieved by electron transfer to plastoquinone in the plastid membrane.

Fig. 7 in The scope of flavin-dependent reactions and processes in the model plant Arabidopsis thaliana

Fig. 7. Reactions catalyzed by isovaleryl-CoA dehydrogenase in valine and isoleucine degradation. Reoxidation of reduced FAD occurs by electron donation to ETF, which in turn feeds the electrons into the mETC via ETF-QO.

Fig. 5 in In silico characterization of class II plant defensins from Arabidopsis thaliana

Fig. 5. Secondary structure evolution during the simulations. The overall secondary structures of (A) A7REG2 and (B) A7REG4 are maintained during the simulations, with the exception of the first β-strand, which could transit to β-bridge and/or coils. The final three-dimensional structures at 300 ns of simulation are displayed on the right side of DSSP. Disulfide bridges are represented in ball and sticks.

Fig. 2 in In silico characterization of class II plant defensins from Arabidopsis thaliana

Fig. 2. Alignment between sequences obtained at the end of semi-automatic search and known class II plant defensins. Signal peptide, mature defensin and Cterminal prodomain regions are indicated by the bottom ruler. The "GXC" γ-core motif is highlighted by a magenta box; none of A. thaliana sequences have the characteristic γ-core GXCX3-9C motif between the IV and VI cysteine residues. Cysteine residues are highlighted in yellow and the lines above the sequences indicate the bond pattern between them. Cis-proline motifs are marked in grey. Predicted C-terminal prodomain recognition site is highlighted by a green box, comprising a pair of charged residues, of which the first is always a negative one. Based on this signature, we propose the RegEx "CX8-10CX2-18CX3CX2-10[GAPSIDERYW]XCX4- 17CXCX3CX2[DE][DERK]" for future studies regarding the identification of class II defensins. Charged residues of C-Terminal prodomain are highlighted in blue (positively charged) or red (negatively charged). ZmERS6, NaD1, PhD1, PhD2 presented a negatively charged C-terminal prodomain, in contrast to A7REG2 (positively charged) and A7REG4 (neutral). Sd5 is a partial sequence, and despite the known terminal residues indicated a positively charged C-terminal prodomain, its actual charge is unknown. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 4 in In silico characterization of class II plant defensins from Arabidopsis thaliana

Fig. 4. Tridimensional molecular models of the sequences. (A) After removal of signal peptide and C-terminal prodomain, both sequences resulted in a 43 amino acid residue mature chain with 72% of identity. The α-core region is highlighted by a green box, showing the accumulated mutations between both sequences. The "AXC" motif from γ-core is highlighted by a red box. (B) A7REG2 and (C) A7REG4 structures. Disulfide bonds are represented in ball and sticks. Both models were generated using the sugar cane (Saccharum officinarum) defensin 5 (SD5, PDB ID: 2KSK) (de Paula et al., 2011). On the Ramachandran plot, A7REG2 model presented 83.3% of residues in favored regions, 13.9% in allowed regions and 2.8% in generously allowed regions; while A7REG4 model presented model presented 77.8% of residues in favored regions, 13.9% in allowed regions and 8.3% in generously allowed regions. In addition, models also presented a Z-Score on ProSa II of 4.47 and 5.74, respectively. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 1 in In silico characterization of class II plant defensins from Arabidopsis thaliana

Fig. 1. Flowchart of identification of class II defensins. The indigo boxes indicated steps performed by Perl scripts and the red boxes, steps curated by hand. The white boxes indicated the number of sequences for each respective step. The sequences from A. thaliana were retrieved from UniProt database; the defensin RegEx "CX2-18CX3CX2-10[GAPSIDERYW]XCX4-17CXC" was determined by Zhu (Zhu, 2008). The complete sequences were retrieved according the UniProt annotations; and the sequences predicted to be secreted were selected according to the Phobius prediction, presenting signal peptide and no transmembrane domains. The selected sequences at the end of the process represented less than 1% of all defensin sequences from A. thaliana. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)

Fig. 3 in In silico characterization of class II plant defensins from Arabidopsis thaliana

Fig. 3. Expression profile of coding genes for A7REG2 and A7REG4 (AGI AT1G73603 and AT1G73607, respectively). (A) Expression in flowers. Y axis represents the number of flowers in the inflorescence, at the moment of the anthesis of the first flower (B) Expression in ovules. Y axis represents the number of the silique from which ovules were taken, at the moment when the first silique is 1 cm long (C) Expression in seeds. Y axis represents the number of the silique from which seeds were taken at the moment of the abscission of the first flower.