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1. (Article ID: 39)
Cedzynski M, Knirel YA, Rozalski A, Shashkov AS, Vinogradov EV, Kaca W
The structure and serological specificity of Proteus mirabilis O43 O-antigen
European Journal of Biochemistry 232 (1995)
558-562
On the basis of sugar analysis and NMR spectroscopy, including selective spin-decoupling, one-dimensional NOE, two-dimensional homonuclear and 13C,1H-heteronuclear correlation spectroscopy, the following structure of the acidic O-specific polysaccharide of Proteus mirabilis O43 was established: →4)-α-D-GalpA-(1→3)-α-D-GalpA-(1→3)-α-D-GlcpNAc-(1→4)-α - D-Glcp-(1→, where GalA is galacturonic acid and Galp is galactopyranose. No serological cross-reactivity was observed between lipopolysaccharides of P. mirabilis O43 and other studied Proteus strains, except for P. mirabilis O10. The O-specific polysaccharide of P. mirabilis O43 was serologically active in precipitation and inhibition tests but the activity was lost after periodate oxidation. These data suggest that the O43 specificity is determined by a wide epitope with the immunodominant role of 4-substituted D-Glc or/and D-GalA, which are destroyed by periodate oxidation
Lipopolysaccharide, LPS, structure, polysaccharide, O-antigen, O antigen, Proteus, Proteus mirabilis, serological, serology, specificity
NCBI PubMed ID: 7556207Publication DOI: 10.1111/j.1432-1033.1995.558zz.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Center of Microbiology and Virology, Polish Academy of Sciences, Lodz
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis
The publication contains the following compound(s):
- Compound ID: 184
|
-4)-a-D-GalpA-(1-3)-a-D-GalpA-(1-3)-a-D-GlcpNAc-(1-4)-a-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G14227DY, GlycomeDB:
3403
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2. (Article ID: 119)
Trent MS, Ribeiro AA, Doerrler WT, Lin S, Cotter RJ, Raetz CRH
Accumulation of a polyisoprene-linked amino sugar in polymyxin resistant Salmonella typhimurium and Escherichia coli. Structural characterization and transfer to lipid A in the periplasm
Journal of Biological Chemistry 276(46) (2001)
43132-43144
Polymyxin-resistant mutants of Escherichia coli and Salmonella typhimurium accumulate a novel minor lipid that can donate 4-amino-4-deoxy-l-arabinose units (l-Ara4N) to lipid A. We now report the purification of this lipid from a pss(-) pmrA(C) mutant of E. coli and assign its structure as undecaprenyl phosphate-α-L-Ara4N. Approximately 0.2 mg of homogeneous material was isolated from an 8-liter culture by solvent extraction, followed by chromatography on DEAE-cellulose, C18 reverse phase resin, and silicic acid. Matrix-assisted laser desorption ionization/time of flight mass spectrometry in the negative mode yielded a single species [M - H](-) at m/z 977.5, consistent with undecaprenyl phosphate-α-L-Ara4N (M(r) = 978.41). (31)P NMR spectroscopy showed a single phosphorus atom at -0.44 ppm characteristic of a phosphodiester linkage. Selective inverse decoupling difference spectroscopy demonstrated that the undecaprenyl phosphate group is attached to the anomeric carbon of the l-Ara4N unit. One- and two-dimensional (1)H NMR studies confirmed the presence of a polyisoprene chain and a sugar moiety with chemical shifts and coupling constants expected for an equatorially substituted arabinopyranoside. Heteronuclear multiple-quantum coherence spectroscopy analysis demonstrated that a nitrogen atom is attached to C-4 of the sugar residue. The purified donor supports in vitro conversion of lipid IV(A) to lipid II(A), which is substituted with a single l-Ara4N moiety. The identification of undecaprenyl phosphate-α-L-Ara4N implies that l-Ara4N transfer to lipid A occurs in the periplasm of polymyxin-resistant strains, and establishes a new enzymatic pathway by which Gram-negative bacteria acquire antibiotic resistance.
Escherichia coli, lipid A, polymyxin-resistant mutants, Salmonella typhimurium
NCBI PubMed ID: 11535605Publication DOI: 10.1074/jbc.M106962200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: raetz

biochem.duke.edu
Institutions: Department of Biochemistry and the Duke NMR Spectroscopy Center and Department of Radiology, Duke University Medical Center, Durham, North Carolina 27710, Middle Atlantic Mass Spectrometry Laboratory, Department of Pharmacology and Molecular Sciences, The Johns Hopkins University School of Medicine, Baltimore, Maryland 21205-2185, USA
Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, TLC, 31P NMR, MALDI-TOF MS, radiolabeling, NMR-1D, genetic methods, biochemical methods, radioactivity measurement
The publication contains the following compound(s):
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3. (Article ID: 7322)
Shiono Y, Kikuchi M, Koseki T, Murayama T, Kwon E, Aburai N, Kimura K
Isopimarane diterpene glycosides, isolated from endophytic fungus Paraconiothyrium sp. MY-42
Phytochemistry 72(11-12) (2011)
1400-1405
Six isopimarane diterpenes, compounds 1-6, were isolated from the endophytic fungus Paraconiothyrium sp. MY-42. Compound 1 possesses a 19-glucopyranosyloxy group. Its structure was first elucidated by spectroscopic data analysis and finally confirmed by X-ray crystallography, whereas structures 2-6 were mainly elucidated based on the analysis of spectroscopic evidence. Compounds 2 and 3 showed moderate cytotoxicities against the human promyelocytic leukemia cell line HL60 (IC50 6.7 μM value for 2 and 9.8 μM for 3).
cytotoxicity, endophytic fungus, Isopimarane diterpenes, Paraconiothyrium sp.
NCBI PubMed ID: 21612804Publication DOI: 10.1016/j.phytochem.2011.04.016Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Shiono Y
tds1.tr.yamagata-u.ac.jp>
Institutions: Department of Bioresource Engineering, Faculty of Agriculture, Yamagata University, Yamagata, Japan, Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Miyagi, Japan, Laboratory of Chemical Biology, Faculty of Agriculture, Iwate University, Iwate, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, MS, HPLC, crystallography, UV, extraction, optical rotation measurement, CC, HR-FAB-MS
The publication contains the following compound(s):
- Compound ID: 18665
|
a-D-Glcp-(1-19)-Subst
Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO |
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Structure type: monomer
; 465.2860 [M-H]-
C26H42O7
Compound class: diterpene glycoside
- Compound ID: 18666
|
a-D-GlcpNAc-(1-19)-Subst
Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO |
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Structure type: monomer
; 506.3122 [M-H]-
C28H44NO7
Compound class: diterpene glycoside
- Compound ID: 18667
|
a-D-Glcp-(1-19)-Subst
Subst = 19-hydroxyisopimara-7,15-dien-3-one = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\CC2[C@@](C)({19}CO)C(=O)CC[C@]12C)C3 |
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Structure type: monomer
; 463.2699 [M-H]-
C26H40O7
Compound class: diterpene glycoside
- Compound ID: 18668
|
a-D-GlcpNAc-(1-19)-Subst
Subst = 19-hydroxyisopimara-7,15-dien-3-one = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\CC2[C@@](C)({19}CO)C(=O)CC[C@]12C)C3 |
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Structure type: monomer
; 504.2969 [M-H]-
C28H42NO7
Compound class: diterpene glycoside
- Compound ID: 18669
|
a-D-Glcp-(1-19)-Subst
Subst = 7-oxoisopimara-8(9),15-diene-3β,19β-diol = SMILES C[C@](C1)(C=C)CCC([C@@](C2C3)(C)CC{3}C(O)[C@]2(C){19}CO)=C1C3=O |
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Structure type: monomer
; 479.2643 [M-H]-
C26H40O8
Compound class: diterpene glycoside
- Compound ID: 18670
|
a-D-GlcpNAc-(1-19)-Subst
Subst = 7-oxoisopimara-8(9),15-diene-3β,19β-diol = SMILES C[C@](C1)(C=C)CCC([C@@](C2C3)(C)CC{3}C(O)[C@]2(C){19}CO)=C1C3=O |
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Structure type: monomer
; 520.2915 [M-H]-
C28H42NO8
Compound class: diterpene glycoside
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4. (Article ID: 8154)
Herath W, Khan SI, Khan IA
Microbial metabolism. Part 14. Isolation and bioactivity evaluation of microbial metabolites of resveratrol
Natural Product Research 27(16) (2013)
1437-1444
The fungi, Beauveria bassiana (ATCC 13144) and Penicillium chrysogenium (ATCC 9480) transformed resveratrol to resveratrol-3-O-sulphate. The former, in addition, gave 5-methoxyresveratrol-3-O-β-glucoside with the latter yielding 5-methoxyresveratrol-3-O-sulphate. The structures were established by spectroscopic methods. Evaluation of biological activity of metabolites through a series of mammalian cell based assays indicated that resveratrol tends to lose its anti-inflammatory, cytotoxic and anti-oxidant activities with the substitution of its hydroxyl groups.
resveratrol, microbial metabolism, Beauveria bassiana, Penicillium chrysogenium
NCBI PubMed ID: 22950854Publication DOI: 10.1080/14786419.2012.722089Journal NLM ID: 101167924Publisher: Milton Park, UK : Taylor & Francis Health Sciences
Correspondence: Khan IA
olemiss.edu>
Institutions: National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, MS, USA, Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, MS, USA
Methods: 13C NMR, 1H NMR, IR, TLC, UV, HR-ESI-MS, HMBC
The publication contains the following compound(s):
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