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1. (CSDB ID: 8455) | report error |
| Cyclic a-D-Xylp-(1-7)-+ | -2)-D-Gln-(1-2)-Gly-(1-2)-L-Pro-(1-2)-L-Val-(1-2)-D-Tyr-(1-2)-L-Ser-(1-2)-D-Leu-(1-2)-L-Thr-(1-2)-D-Leu-(1-2)-L-Pro-(1-3)-Subst-(1- Subst = 3,5-dihydroxy-2-methyldecanoic acid (desmamide C) = SMILES CCCCC{5}C(O)C{3}C(O)C(C){1}C(O)=O | Show graphically |
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Desmonostoc muscorum LEGE 12446
(Ancestor NCBI TaxID 1179,
species name lookup)
ciimar.up.pt>Certain cyanobacteria of the secondary metabolite-rich order Nostocales can establish permanent symbioses with a large number of cycads, by accumulating in their coralloid roots and shifting their metabolism to dinitrogen fixation. Here, we report the discovery of two new lipoglycopeptides, desmamides A (1) and B (2), together with their aglycone desmamide C (3), from the nostocalean cyanobacterium Desmonostoc muscorum LEGE 12446 isolated from a cycad (Cycas revoluta) coralloid root. The chemical structures of the compounds were elucidated using a combination of 1D and 2D NMR spectroscopy and mass spectrometry. The desmamides are decapeptides featuring O-glycosylation of tyrosine (in 1 and 2) and an unusual 3,5-dihydroxy-2-methyldecanoic acid residue. The biosynthesis of the desmamides was studied by substrate incubation experiments and bioinformatics. We describe herein the dsm biosynthetic gene cluster and propose it to be associated with desmamide production. The discovery of this class of very abundant (>1.5% d.w.) bacterial lipoglycopeptides paves the way for exploration of their potential role in root endosymbiosis.
structure, NMR spectroscopy, mass spectrometry, cyanobacteria, marine, lipoglycopeptides, Desmonostoc muscorum
Structure type: cyclic polymer repeating unit ; 1388.7577 [M+H]+13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 3,2,2,2,2,2,2,2,2,2 xDGln 171.7 53.1 27.7 31.7 171.7 3,2,2,2,2,2,2,2,2 xXGly 167.1 41.3 3,2,2,2,2,2,2,2 xLPro 172.4 59.2 28.9 24.4 46.6 3,2,2,2,2,2,2 xLVal 170.4 59.8 29.5 18.6 18.7 3,2,2,2,2,2,7 aDXylp 97.6 71.6 73.2 69.7 62.5 3,2,2,2,2,2 xDTyr 171.5 54.1 36.6 131.2 129.9 116.5 155.4 116.5 129.9 3,2,2,2,2 xLSer 169.8 56.5 61.5 3,2,2,2 xDLeu 172.1 48.8 40.3 24.0 23.2 23.2 3,2,2 xLThr 169.5 58.3 66.8 19.4 3,2 xDLeu 170.6 48.8 41.1 24.0 21.4 21.4 3 xLPro 171.4 59.0 28.5 24.7 45.9 Subst 172.5 43.7 72.9 38.4 66.3 37.7 24.8 24.8 22.1 14.0 13.6 1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 3,2,2,2,2,2,2,2,2,2 xDGln - 4.15 1.74-1.86 1.88-2.12 - 3,2,2,2,2,2,2,2,2 xXGly - 3.80-3.96 3,2,2,2,2,2,2,2 xLPro - 4.38 2.00 1.97 3.51-3.75 3,2,2,2,2,2,2 xLVal - 3.76 1.72 0.46 0.66 3,2,2,2,2,2,7 aDXylp 5.31 3.36 3.55 3.34 3.33-3.45 3,2,2,2,2,2 xDTyr - 4.53 2.64-3.13 - 7.13 6.91 - 6.91 7.13 3,2,2,2,2 xLSer - 4.16 3.65-3.75 3,2,2,2 xDLeu - 4.32 1.42-1.50 1.64 0.87 0.87 3,2,2 xLThr - 4.19 3.91 1.00 3,2 xDLeu - 4.65 1.48 1.64 0.83 0.83 3 xLPro - 4.27 2.13 1.85 3.46 Subst - 2.55 5.06 1.46 3.33 1.28 1.28 1.28 1.25 0.86 0.98 1H/13C HSQC data: Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 3,2,2,2,2,2,2,2,2,2 xDGln 53.1/4.15 27.7/1.74-1.86 31.7/1.88-2.12 3,2,2,2,2,2,2,2,2 xXGly 41.3/3.80-3.96 3,2,2,2,2,2,2,2 xLPro 59.2/4.38 28.9/2.00 24.4/1.97 46.6/3.51-3.75 3,2,2,2,2,2,2 xLVal 59.8/3.76 29.5/1.72 18.6/0.46 18.7/0.66 3,2,2,2,2,2,7 aDXylp 97.6/5.31 71.6/3.36 73.2/3.55 69.7/3.34 62.5/3.33-3.45 3,2,2,2,2,2 xDTyr 54.1/4.53 36.6/2.64-3.13 129.9/7.13 116.5/6.91 116.5/6.91 129.9/7.13 3,2,2,2,2 xLSer 56.5/4.16 61.5/3.65-3.75 3,2,2,2 xDLeu 48.8/4.32 40.3/1.42-1.50 24.0/1.64 23.2/0.87 23.2/0.87 3,2,2 xLThr 58.3/4.19 66.8/3.91 19.4/1.00 3,2 xDLeu 48.8/4.65 41.1/1.48 24.0/1.64 21.4/0.83 21.4/0.83 3 xLPro 59.0/4.27 28.5/2.13 24.7/1.85 45.9/3.46 Subst 43.7/2.55 72.9/5.06 38.4/1.46 66.3/3.33 37.7/1.28 24.8/1.28 24.8/1.28 22.1/1.25 14.0/0.86 13.6/0.98
1H NMR data:
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13C NMR data:
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2. (CSDB ID: 20935) | report error |
| Cyclic a-D-Xylp4Ac-(1-7)-+ | -2)-D-Gln-(1-2)-Gly-(1-2)-L-Pro-(1-2)-L-Val-(1-2)-D-Tyr-(1-2)-L-Ser-(1-2)-D-Leu-(1-2)-L-Thr-(1-2)-D-Leu-(1-2)-L-Pro-(1-3)-Subst-(1- Subst = 3,5-dihydroxy-2-methyldecanoic acid (desmamide C) = SMILES CCCCC{5}C(O)C{3}C(O)C(C){1}C(O)=O | Show graphically |
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Desmonostoc muscorum LEGE 12446
(Ancestor NCBI TaxID 1179,
species name lookup)
ciimar.up.pt>Certain cyanobacteria of the secondary metabolite-rich order Nostocales can establish permanent symbioses with a large number of cycads, by accumulating in their coralloid roots and shifting their metabolism to dinitrogen fixation. Here, we report the discovery of two new lipoglycopeptides, desmamides A (1) and B (2), together with their aglycone desmamide C (3), from the nostocalean cyanobacterium Desmonostoc muscorum LEGE 12446 isolated from a cycad (Cycas revoluta) coralloid root. The chemical structures of the compounds were elucidated using a combination of 1D and 2D NMR spectroscopy and mass spectrometry. The desmamides are decapeptides featuring O-glycosylation of tyrosine (in 1 and 2) and an unusual 3,5-dihydroxy-2-methyldecanoic acid residue. The biosynthesis of the desmamides was studied by substrate incubation experiments and bioinformatics. We describe herein the dsm biosynthetic gene cluster and propose it to be associated with desmamide production. The discovery of this class of very abundant (>1.5% d.w.) bacterial lipoglycopeptides paves the way for exploration of their potential role in root endosymbiosis.
structure, NMR spectroscopy, mass spectrometry, cyanobacteria, marine, lipoglycopeptides, Desmonostoc muscorum
Structure type: cyclic polymer repeating unit ; 1430.7666 [M+H]+13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 3,2,2,2,2,2,2,2,2,2 xDGln 173.7 53.2 27.7 31.7 171.7 3,2,2,2,2,2,2,2,2 xXGly 167.1 41.3 3,2,2,2,2,2,2,2 xLPro 172.3 59.2 28.9 24.4 46.6 3,2,2,2,2,2,2 xLVal 170.4 59.7 29.5 18.6 18.7 3,2,2,2,2,2,7,4 Ac 170.0 21.2 3,2,2,2,2,2,7 aDXylp 97.3 71.5 69.9 71.4 58.8 3,2,2,2,2,2 xDTyr 171.5 54.2 36.7 131.5 130.0-130.2 116.5 155.4 116.5 130.0-130.2 3,2,2,2,2 xLSer 169.8 56.6 61.4 3,2,2,2 xDLeu 172.2 48.9 40.0 24.0 23.2 23.2 3,2,2 xLThr 169.5 58.3 66.8 19.6 3,2 xDLeu 170.6 48.9 41.0 24.0 21.7 21.7 3 xLPro 171.4 59.0 28.5 24.4 45.9 Subst 172.5 43.7 72.9 38.4 65.9 37.8 31.4 24.8 22.1 14.0 13.6 1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 3,2,2,2,2,2,2,2,2,2 xDGln - 4.14 1.75-1.88 1.89-2.12 - 3,2,2,2,2,2,2,2,2 xXGly - 3.80-3.96 3,2,2,2,2,2,2,2 xLPro - 4.38 2.00 1.98 3.51-3.76 3,2,2,2,2,2,2 xLVal - 3.75 1.72 0.46 0.66 3,2,2,2,2,2,7,4 Ac - 2.02 3,2,2,2,2,2,7 aDXylp 5.40 3.48 3.78 4.62 3.37-3.58 3,2,2,2,2,2 xDTyr - 4.53 2.65-3.13 - 7.15 6.93 - 6.93 7.15 3,2,2,2,2 xLSer - 4.16 3.57-3.64 3,2,2,2 xDLeu - 4.32 1.50-1.55 1.65 0.87 0.87 3,2,2 xLThr - 4.19 3.91 1.00 3,2 xDLeu - 4.65 1.40-1.50 1.65 0.83 0.83 3 xLPro - 4.27 2.13 1.87 3.46 Subst - 2.55 5.06 1.46 3.33 1.28 1.24 1.29 1.26 0.85 0.97 1H/13C HSQC data: Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 3,2,2,2,2,2,2,2,2,2 xDGln 53.2/4.14 27.7/1.75-1.88 31.7/1.89-2.12 3,2,2,2,2,2,2,2,2 xXGly 41.3/3.80-3.96 3,2,2,2,2,2,2,2 xLPro 59.2/4.38 28.9/2.00 24.4/1.98 46.6/3.51-3.76 3,2,2,2,2,2,2 xLVal 59.7/3.75 29.5/1.72 18.6/0.46 18.7/0.66 3,2,2,2,2,2,7,4 Ac 21.2/2.02 3,2,2,2,2,2,7 aDXylp 97.3/5.40 71.5/3.48 69.9/3.78 71.4/4.62 58.8/3.37-3.58 3,2,2,2,2,2 xDTyr 54.2/4.53 36.7/2.65-3.13 130.0-130.2/7.15 116.5/6.93 116.5/6.93 130.0-130.2/7.15 3,2,2,2,2 xLSer 56.6/4.16 61.4/3.57-3.64 3,2,2,2 xDLeu 48.9/4.32 40.0/1.50-1.55 24.0/1.65 23.2/0.87 23.2/0.87 3,2,2 xLThr 58.3/4.19 66.8/3.91 19.6/1.00 3,2 xDLeu 48.9/4.65 41.0/1.40-1.50 24.0/1.65 21.7/0.83 21.7/0.83 3 xLPro 59.0/4.27 28.5/2.13 24.4/1.87 45.9/3.46 Subst 43.7/2.55 72.9/5.06 38.4/1.46 65.9/3.33 37.8/1.28 31.4/1.24 24.8/1.29 22.1/1.26 14.0/0.85 13.6/0.97
1H NMR data:
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13C NMR data:
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3. (CSDB ID: 50370) | report error |
| b-D-Glcp-(1-4)-Subst Subst = zearalenone = SMILES C[C@H]1CCCC(CCC/C=C/C2=C{4}C(O)=C{2}C(O)=C2C(O1)=O)=O | Show graphically |
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Fusarium
(NCBI TaxID 5506,
species name lookup)
UGent.beJuveniles are considered as one of the most vulnerable population groups concerning mycotoxins and their modified forms. The weaning stage is a particularly vulnerable period in the life of mammals, reflected in intestinal and immune dysfunction. The current study investigated the toxicokinetic (TK) characteristics of zearalenone (ZEN), zearalenone-14-glucoside (ZEN14G), and zearalenone-14-sulfate (ZEN14S) in weaned (4-week-old) piglets, by means of oral and intravenous administration of equimolar doses, i.e., 331, 500, and 415 μg/kg bodyweight, respectively. Plasma and urine were sampled pre- and post-administration and were quantitatively analyzed for ZEN, ZEN14G, ZEN14S, and in vivo metabolites by liquid chromatography-high-resolution mass spectrometry. Tailor-made TK models were elaborated to process data. A statistical comparison of the results was performed with TK data obtained in a previously reported study in pigs of 8 weeks of age. Additionally, porcine plasma protein binding was determined to support TK findings. The TK results for ZEN, ZEN14G, and ZEN14S, obtained in 4- and 8-week-old pigs, revealed significant age-related differences, based on differences in intestinal permeability, body fat content, gastrointestinal transit time, and biotransformation, with a special emphasis on an increased absorbed fraction of ZEN14G, i.e., 94 vs 61% in 4- compared to 8-week-old pigs. Since the growing pig has been reported to be a suitable pediatric animal model for humans concerning TK processes, these results may contribute to refine the risk assessment concerning modified ZEN forms in juvenile animals and humans.
pig, zearalenone, toxicokinetics, weaning, zearalenone-14-glucoside, zearalenone-14-sulfate
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