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Identification, Characteristics and Mechanism of 1-Deoxy-N-acetylglucosamine from Deep-Sea Virgibacillus dokdonensis MCCC 1A00493

1
State Key Laboratory of Agricultural Microbiology, National Engineering Research Center of Microbe Pesticides, College of Life Science and Technology, Huazhong Agricultural University, Wuhan 430070, China
2
Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China
3
School of Pharmaceutical Sciences, Wuhan University, Wuhan 430070, China
4
Key Laboratory of Magnetic Resonance in Biological Systems, State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Centre for Magnetic Resonance, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences, Wuhan 430071, China
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2018, 16(2), 52; https://doi.org/10.3390/md16020052
Received: 2 December 2017 / Revised: 1 February 2018 / Accepted: 2 February 2018 / Published: 7 February 2018
(This article belongs to the Special Issue Isolation and Structure Elucidation of Marine Secondary Metabolites)
Xanthomonas oryzae pv. oryzae, which causes rice bacterial blight, is one of the most destructive pathogenic bacteria. Biological control against plant pathogens has recently received increasing interest. 1-Deoxy-N-acetylglucosamine (1-DGlcNAc) was extracted from the supernatant of Virgibacillus dokdonensis MCCC 1A00493 fermentation through antibacterial bioassay-guided isolation. Its structure was elucidated by LC/MS, NMR, chemical synthesis and time-dependent density functional theory (TD-DFT) calculations. 1-DGlcNAc specifically suppressed X. oryzae pv. oryzae PXO99A (MIC was 23.90 μg/mL), but not other common pathogens including Xanthomonas campestris pv. campestris str.8004 and Xanthomonas oryzae pv. oryzicola RS105. However, its diastereomer (2-acetamido-1,5-anhydro-2-deoxy-d-mannitol) also has no activity to X. oryzae pv. oryzae. This result suggested that activity of 1-DGlcNAc was related to the difference in the spatial conformation of the 2-acetamido moiety, which might be attributed to their different interactions with a receptor. Eighty-four unique proteins were found in X. oryzae pv. oryzae PXO99A compared with the genome of strains8004 and RS105 by blastp. There may be unique interactions between 1-DGlcNAc and one or more of these unique proteins in X. oryzae pv. oryzae. Quantitative real-time PCR and the pharmMapper server indicated that proteins involved in cell division could be the targets in PXO99A. This research suggested that specificity of active substance was based on the active group and spatial conformation selection, and these unique proteins could help to reveal the specific mechanism of action of 1-DGlcNAc against PXO99A. View Full-Text
Keywords: Virgibacillus dokdonensis; Xanthomonas oryzae pv. oryzae; 1-Deoxy-N-acetylglucosamine; antibacterial characteristics; mechanism Virgibacillus dokdonensis; Xanthomonas oryzae pv. oryzae; 1-Deoxy-N-acetylglucosamine; antibacterial characteristics; mechanism
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Huang, D.; Shao, Z.-Z.; Yu, Y.; Cai, M.-M.; Zheng, L.-Y.; Li, G.-Y.; Yu, Z.-N.; Yi, X.-F.; Zhang, J.-B.; Hao, F.-H. Identification, Characteristics and Mechanism of 1-Deoxy-N-acetylglucosamine from Deep-Sea Virgibacillus dokdonensis MCCC 1A00493. Mar. Drugs 2018, 16, 52.

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