Ralstonia solanacearum, one of the most destructive crop pathogens worldwide, causes bacterial wilt disease in a wide range of host plants. The major component of the outer membrane of Gram-negative bacteria, lipopolysaccharides (LPS), has been shown to function as elicitors of plant defense leading to the activation of signaling and defense pathways in several plant species. LPS from a R. solanacearum strain virulent on tomato (LPSR. sol.), were purified, chemically characterized, and structurally elucidated. The lipid A moiety consisted of tetra- to hexa-acylated bis-phosphorylated disaccharide backbone, also decorated by aminoarabinose residues in minor species, while the O-polysaccharide chain consisted of either linear tetrasaccharide or branched pentasaccharide repeating units containing α-L-rhamnose, N-acetyl-β-D-glucosamine, and β-L-xylose. These properties might be associated with the evasion of host surveillance, aiding the establishment of the infection. Using untargeted metabolomics, the effect of LPSR. sol. elicitation on the metabolome of Solanum lycopersicum leaves was investigated across three incubation time intervals with the application of UHPLC-MS for metabolic profiling. The results revealed the production of oxylipins, e.g., trihydroxy octadecenoic acid and trihydroxy octadecadienoic acid, as well as several hydroxycinnamic acid amide derivatives, e.g., coumaroyl tyramine and feruloyl tyramine, as phytochemicals that exhibit a positive correlation to LPSR. sol. treatment. Although the chemical properties of these metabolite classes have been studied, the functional roles of these compounds have not been fully elucidated. Overall, the results suggest that the features of the LPSR. sol. chemotype aid in limiting or attenuating the full deployment of small molecular host defenses and contribute to the understanding of the perturbation and reprogramming of host metabolism during biotic immune responses

lipopolysaccharides, metabolomics, Plant immunity, phenylpropanoids, Solanum lycopersicum, hydroxycinnamic acid amides, oxylipins

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,2,4	%bLXylp	103.5	73.2	76.1	69.3	65.0
3,3,2	aLRhap	101.7	69.8	?	79.4	69.3	16.7
3,3	aLRhap	100.9	77.8	70.1	71.2	69.3	16.7
3	aLRhap	101.1	70.7	77.4	71.5	69.1	16.7
2	Ac	?	22.3
	bDGlcpN	102.0	55.8	81.6	68.3	75.8	60.6


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,2,4	%bLXylp	4.34	3.41	3.33	3.50	3.19-3.90
3,3,2	aLRhap	4.91	4.18	3.78	3.63	3.63	1.18
3,3	aLRhap	5.07	3.99	3.85	3.40	3.66	1.25
3	aLRhap	4.77	3.75	3.72	3.46	3.95	1.16
2	Ac	-	1.96
	bDGlcpN	4.66	3.80	3.53	3.48	3.40	3.70-3.85


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,3,2,4	%bLXylp	103.5/4.34	73.2/3.41	76.1/3.33	69.3/3.50	65.0/3.19-3.90
3,3,2	aLRhap	101.7/4.91	69.8/4.18	?/3.78	79.4/3.63	69.3/3.63	16.7/1.18
3,3	aLRhap	100.9/5.07	77.8/3.99	70.1/3.85	71.2/3.40	69.3/3.66	16.7/1.25
3	aLRhap	101.1/4.77	70.7/3.75	77.4/3.72	71.5/3.46	69.1/3.95	16.7/1.16
2	Ac		22.3/1.96
	bDGlcpN	102.0/4.66	55.8/3.80	81.6/3.53	68.3/3.48	75.8/3.40	60.6/3.70-3.85

The spectrum also has 2 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

[*]O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](C)O[C@@H](O[C@@H]4[C@@H](NC(C)=O)[C@H]([*])O[C@H](CO)[C@H]4O)[C@@H]3O)O[C@@H](C)[C@H](O)[C@H]2O)O[C@@H](C)[C@@H]1O[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O

773.735 g/mol (C₃₁H₅₁R₂NO₂₁, R = next and previous repeats, not counted in mol weight)

Ralstonia solanacearum, one of the most destructive crop pathogens worldwide, causes bacterial wilt disease in a wide range of host plants. The major component of the outer membrane of Gram-negative bacteria, lipopolysaccharides (LPS), has been shown to function as elicitors of plant defense leading to the activation of signaling and defense pathways in several plant species. LPS from a R. solanacearum strain virulent on tomato (LPSR. sol.), were purified, chemically characterized, and structurally elucidated. The lipid A moiety consisted of tetra- to hexa-acylated bis-phosphorylated disaccharide backbone, also decorated by aminoarabinose residues in minor species, while the O-polysaccharide chain consisted of either linear tetrasaccharide or branched pentasaccharide repeating units containing α-L-rhamnose, N-acetyl-β-D-glucosamine, and β-L-xylose. These properties might be associated with the evasion of host surveillance, aiding the establishment of the infection. Using untargeted metabolomics, the effect of LPSR. sol. elicitation on the metabolome of Solanum lycopersicum leaves was investigated across three incubation time intervals with the application of UHPLC-MS for metabolic profiling. The results revealed the production of oxylipins, e.g., trihydroxy octadecenoic acid and trihydroxy octadecadienoic acid, as well as several hydroxycinnamic acid amide derivatives, e.g., coumaroyl tyramine and feruloyl tyramine, as phytochemicals that exhibit a positive correlation to LPSR. sol. treatment. Although the chemical properties of these metabolite classes have been studied, the functional roles of these compounds have not been fully elucidated. Overall, the results suggest that the features of the LPSR. sol. chemotype aid in limiting or attenuating the full deployment of small molecular host defenses and contribute to the understanding of the perturbation and reprogramming of host metabolism during biotic immune responses

lipopolysaccharides, metabolomics, Plant immunity, phenylpropanoids, Solanum lycopersicum, hydroxycinnamic acid amides, oxylipins

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CCCCCCCCCCCC[C@H](O)C(=O)O[C@H](CCCCCCCCCCC)CC(=O)N[C@H]1[C@@H](OP(=O)(O)O)O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@H]2NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H](O)[C@@H]1O

1588.034 g/mol (C₈₀H₁₅₂N₂O₂₄P₂)