Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1534/genetics.114.168690Journal NLM ID: 0374636Publisher: Baltimore, MD: Genetics Society of America
Correspondence: chapple
purdue.edu, bdilkes
purdue.edu
Institutions: Department of Biochemistry, Purdue University, West Lafayette, Indiana 47907, Department of Horticulture and Landscape Architecture, Purdue University, West Lafayette, Indiana 47907, Purdue Interdepartmental NMR Facility, Purdue University, West Lafayette, Indiana 47907, Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, Department of Plant Sciences, University of California, Davis, California 95616
Plant secondary metabolism is an active research area because of the unique and important roles the specialized metabolites have in the interaction of plants with their biotic and abiotic environment, the diversity and complexity of the compounds and their importance to human medicine. Thousands of natural accessions of Arabidopsis thaliana characterized with increasing genomic precision are available, providing new opportunities to explore the biochemical and genetic mechanisms affecting variation in secondary metabolism within this model species. In this study, we focused on four aromatic metabolites that were differentially accumulated among 96 Arabidopsis natural accessions as revealed by leaf metabolic profiling. Using UV, mass spectrometry, and NMR data, we identified these four compounds as different dihydroxybenzoic acid (DHBA) glycosides, namely 2,5-dihydroxybenzoic acid (gentisic acid) 5-O-β-D-glucoside, 2,3-dihydroxybenzoic acid 3-O-β-D-glucoside, 2,5-dihydroxybenzoic acid 5-O-β-D-xyloside, and 2,3-dihydroxybenzoic acid 3-O-β-D-xyloside. Quantitative trait locus (QTL) mapping using recombinant inbred lines generated from C24 and Col-0 revealed a major-effect QTL controlling the relative proportion of xylosides vs. glucosides. Association mapping identified markers linked to a gene encoding a UDP glycosyltransferase gene. Analysis of Transfer DNA (T-DNA) knockout lines verified that this gene is required for DHBA xylosylation in planta and recombinant protein was able to xylosylate DHBA in vitro. This study demonstrates that exploiting natural variation of secondary metabolism is a powerful approach for gene function discovery.
glycosides, Arabidopsis, Secondary metabolism, Natural variation, dihydrozybenzoic acid, UDP glycosyltransferase (UGT)
Structure type: monomer
Location inside paper: Figure 3C
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332
Methods: 13C NMR, 1H NMR, HPLC, LC-MS, enzymatic assay, genetic manipulations
Enzymes that release or process the structure: UGT89A2
Related record ID(s): 60948, 60950, 60951
NCBI Taxonomy refs (TaxIDs): 3702
Show glycosyltransferases
NMR conditions: in CD3OD at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7
5 bDXylp 101.9 72.7 75.4 69 65.1
xXGent 116.9 155.6 117.4 124.0 148.9 117.9 173.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7
5 bDXylp 4.88 3.46 3.47 3.63 3.37-3.94
xXGent - - 6.83 7.14 - 7.45 -
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7
5 bDXylp 101.9/4.88 72.7/3.46 75.4/3.47 69/3.63 65.1/3.37-3.94
xXGent 117.4/6.83 124.0/7.14 117.9/7.45
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 |
|---|
| 5 | bDXylp | 4.88 | 3.46 | 3.47 | 3.63 | 3.37
3.94 | |
| | xXGent |
|
| 6.83 | 7.14 |
| 7.45 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 |
|---|
| 5 | bDXylp | 101.9 | 72.7 | 75.4 | 69 | 65.1 | |
| | xXGent | 116.9 | 155.6 | 117.4 | 124.0 | 148.9 | 117.9 | 173.8 |
|
There is only one chemically distinct structure:
Found 
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