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Casillo A, Fabozzi A, Russo Krauss I, Parrilli E, Biggs CI, Gibson MI, Lanzetta R, Arato V, Appavou MS, Radulescu A, Tutino ML, Paduano L, Corsaro MM
Physicochemical Approach to Understanding the Structure, Conformation, and Activity of Mannan Polysaccharides
Biomacromolecules 22(4) (2021)
1445-1457
|
a-D-Manp-(1-2)-+
|
a-D-Manp-(1-3)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-+ |
| |
/Variants 0/-a-D-Manp-(1-2)-+ | |
| | |
-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-
/Variants 0/ is:
a-D-Manp-(1-2)-
OR (exclusively)
12%a-D-Glcp-(1-2)- |
Show graphically |
Psychrobacter arcticus 273-4
(NCBI TaxID 259536,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 33729771Publication DOI: 10.1021/acs.biomac.0c01659Journal NLM ID: 100892849Publisher: Washington, DC: American Chemical Society
Correspondence: Luigi Paduano <lpaduano
unina.it>; Maria M. Corsaro <corsaro
unina.it>
Institutions: Department of Chemical Sciences, University of Naples 'Federico II', Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Naples, Italy, CSGI - Consorzio per lo Sviluppo dei Sistemi a Grande Interfase, Florence, Italy, Department of Chemistry, University of Warwick, Coventry CV4 7AL, U.K, Jülich Centre for Neutron Science, Garching Forschungszentrum, Lichtenbergstrasse 1, D-857478 Garching bei Munchen, Germany
Extracellular polysaccharides are widely produced by bacteria, yeasts, and algae. These polymers are involved in several biological functions, such as bacteria adhesion to surface and biofilm formation, ion sequestering, protection from desiccation, and cryoprotection. The chemical characterization of these polymers is the starting point for obtaining relationships between their structures and their various functions. While this fundamental correlation is well reported and studied for the proteins, for the polysaccharides, this relationship is less intuitive. In this paper, we elucidate the chemical structure and conformational studies of a mannan exopolysaccharide from the permafrost isolated bacterium Psychrobacter arcticus strain 273-4. The mannan from the cold-adapted bacterium was compared with its dephosphorylated derivative and the commercial product from Saccharomyces cerevisiae. Starting from the chemical structure, we explored a new approach to deepen the study of the structure/activity relationship. A pool of physicochemical techniques, ranging from small-angle neutron scattering (SANS) and dynamic and static light scattering (DLS and SLS, respectively) to circular dichroism (CD) and cryo-transmission electron microscopy (cryo-TEM), have been used. Finally, the ice recrystallization inhibition activity of the polysaccharides was explored. The experimental evidence suggests that the mannan exopolysaccharide from P. arcticus bacterium has an efficient interaction with the water molecules, and it is structurally characterized by rigid-rod regions assuming a 14-helix-type conformation.
conformation, structure, extracellular polysaccharide, biological activity, biofilm formation, Psychrobacter arcticus, Saccharomyces cerevisiae
Structure type: polymer chemical repeating unit
Location inside paper: scheme 1, table S1, mannanP.arc_HF
Trivial name: mannan
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141111,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_174840,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, methylation, gel filtration, NMR-2D, GC-MS, sugar analysis, CD, HF hydrolysis, IRI, DLS, surface tension titration, SANS, SLS, cryo-TEM
Comments, role: HF hydrolysis of the EPS
Related record ID(s): 10833
NCBI Taxonomy refs (TaxIDs): 259536
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6,6,6,6 aDManp 100.6 71.3 71.7 68.1 72.1 66.7
6,6,6,2 aDManp 101.8 79.7 71.6 68.1 74.5 62.3
6,6,6 aDManp 99.4 80.0 71.4-71.5 67.8 72.1 66.9
6,6,2,2,3 aDManp 103.5 71.3 71.6 68.2 74.5 62.4
6,6,2,2 aDManp 103.5 70.9 79.2 67.6 72.5 62.4
6,6,2 aDManp 101.8 79.7 71.6 68.1 74.5 62.3
6,6 aDManp 99.4 80.0 71.4-71.5 67.8 72.1 66.9
6,2 aDManp 103.4 71.3 71.7 68.1 74.4 62.4
6 aDManp 99.4 80.0 71.4-71.5 67.8 72.1 66.9
aDManp 99.0 72.7 74.6 68.0 70.8 66.7
6,6,6,2,2 12%aDGlcp 104.3 74.4 76.7 70.9 76.1 62.4
6,6,6,2,2 aDManp 103.4 71.3 71.7 68.1 74.4 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6,6,6,6 aDManp 4.79 3.88 3.73 3.59 ? 3.64-3.79
6,6,6,2 aDManp 5.19 4.01 3.81 3.63 3.66 3.64-3.79
6,6,6 aDManp 4.99-5.01 3.91-3.93 3.81-3.83 3.73 3.70 3.58-3.89
6,6,2,2,3 aDManp 5.04 3.96 3.75 3.53 3.66 3.64-3.78
6,6,2,2 aDManp 4.93 4.11 3.84 3.72 3.69 3.64-3.79
6,6,2 aDManp 5.19 4.01 3.81 3.63 3.66 3.64-3.79
6,6 aDManp 4.99-5.01 3.91-3.93 3.81-3.83 3.73 3.70 3.58-3.89
6,2 aDManp 4.94 3.96 3.70 3.53 3.66 3.64-3.79
6 aDManp 4.99-5.01 3.91-3.93 3.81-3.83 3.73 3.70 3.58-3.89
aDManp 4.86 3.46 3.60 3.60 3.41 3.65-3.87
6,6,6,2,2 12%aDGlcp 4.42 3.22 3.38 3.32 3.53 3.64-3.79
6,6,6,2,2 aDManp 4.94 3.96 3.70 3.53 3.66 3.64-3.79
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6,6,6,6 aDManp 100.6/4.79 71.3/3.88 71.7/3.73 68.1/3.59 72.1/? 66.7/3.64-3.79
6,6,6,2 aDManp 101.8/5.19 79.7/4.01 71.6/3.81 68.1/3.63 74.5/3.66 62.3/3.64-3.79
6,6,6 aDManp 99.4/4.99-5.01 80.0/3.91-3.93 71.4-71.5/3.81-3.83 67.8/3.73 72.1/3.70 66.9/3.58-3.89
6,6,2,2,3 aDManp 103.5/5.04 71.3/3.96 71.6/3.75 68.2/3.53 74.5/3.66 62.4/3.64-3.78
6,6,2,2 aDManp 103.5/4.93 70.9/4.11 79.2/3.84 67.6/3.72 72.5/3.69 62.4/3.64-3.79
6,6,2 aDManp 101.8/5.19 79.7/4.01 71.6/3.81 68.1/3.63 74.5/3.66 62.3/3.64-3.79
6,6 aDManp 99.4/4.99-5.01 80.0/3.91-3.93 71.4-71.5/3.81-3.83 67.8/3.73 72.1/3.70 66.9/3.58-3.89
6,2 aDManp 103.4/4.94 71.3/3.96 71.7/3.70 68.1/3.53 74.4/3.66 62.4/3.64-3.79
6 aDManp 99.4/4.99-5.01 80.0/3.91-3.93 71.4-71.5/3.81-3.83 67.8/3.73 72.1/3.70 66.9/3.58-3.89
aDManp 99.0/4.86 72.7/3.46 74.6/3.60 68.0/3.60 70.8/3.41 66.7/3.65-3.87
6,6,6,2,2 12%aDGlcp 104.3/4.42 74.4/3.22 76.7/3.38 70.9/3.32 76.1/3.53 62.4/3.64-3.79
6,6,6,2,2 aDManp 103.4/4.94 71.3/3.96 71.7/3.70 68.1/3.53 74.4/3.66 62.4/3.64-3.79
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6,6,6,6 | aDManp | 4.79 | 3.88 | 3.73 | 3.59 | ? | 3.64
3.79 |
| 6,6,6,2 | aDManp | 5.19 | 4.01 | 3.81 | 3.63 | 3.66 | 3.64
3.79 |
| 6,6,6 | aDManp | 4.99
5.01 | 3.91
3.93 | 3.81
3.83 | 3.73 | 3.70 | 3.58
3.89 |
| 6,6,2,2,3 | aDManp | 5.04 | 3.96 | 3.75 | 3.53 | 3.66 | 3.64
3.78 |
| 6,6,2,2 | aDManp | 4.93 | 4.11 | 3.84 | 3.72 | 3.69 | 3.64
3.79 |
| 6,6,2 | aDManp | 5.19 | 4.01 | 3.81 | 3.63 | 3.66 | 3.64
3.79 |
| 6,6 | aDManp | 4.99
5.01 | 3.91
3.93 | 3.81
3.83 | 3.73 | 3.70 | 3.58
3.89 |
| 6,2 | aDManp | 4.94 | 3.96 | 3.70 | 3.53 | 3.66 | 3.64
3.79 |
| 6 | aDManp | 4.99
5.01 | 3.91
3.93 | 3.81
3.83 | 3.73 | 3.70 | 3.58
3.89 |
| | aDManp | 4.86 | 3.46 | 3.60 | 3.60 | 3.41 | 3.65
3.87 |
| 6,6,6,2,2 | 12%aDGlcp | 4.42 | 3.22 | 3.38 | 3.32 | 3.53 | 3.64
3.79 |
| 6,6,6,2,2 | aDManp | 4.94 | 3.96 | 3.70 | 3.53 | 3.66 | 3.64
3.79 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6,6,6,6 | aDManp | 100.6 | 71.3 | 71.7 | 68.1 | 72.1 | 66.7 |
| 6,6,6,2 | aDManp | 101.8 | 79.7 | 71.6 | 68.1 | 74.5 | 62.3 |
| 6,6,6 | aDManp | 99.4 | 80.0 | 71.4
71.5 | 67.8 | 72.1 | 66.9 |
| 6,6,2,2,3 | aDManp | 103.5 | 71.3 | 71.6 | 68.2 | 74.5 | 62.4 |
| 6,6,2,2 | aDManp | 103.5 | 70.9 | 79.2 | 67.6 | 72.5 | 62.4 |
| 6,6,2 | aDManp | 101.8 | 79.7 | 71.6 | 68.1 | 74.5 | 62.3 |
| 6,6 | aDManp | 99.4 | 80.0 | 71.4
71.5 | 67.8 | 72.1 | 66.9 |
| 6,2 | aDManp | 103.4 | 71.3 | 71.7 | 68.1 | 74.4 | 62.4 |
| 6 | aDManp | 99.4 | 80.0 | 71.4
71.5 | 67.8 | 72.1 | 66.9 |
| | aDManp | 99.0 | 72.7 | 74.6 | 68.0 | 70.8 | 66.7 |
| 6,6,6,2,2 | 12%aDGlcp | 104.3 | 74.4 | 76.7 | 70.9 | 76.1 | 62.4 |
| 6,6,6,2,2 | aDManp | 103.4 | 71.3 | 71.7 | 68.1 | 74.4 | 62.4 |
|
There is only one chemically distinct structure:
Expand this record
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Guo H, Rischer M, Westermann M, Beemelmanns C
Two Distinct Bacterial Biofilm Components Trigger Metamorphosis in the Colonial Hydrozoan Hydractinia echinata
mBio 12(3) (2021)
e0040121
Alcaligenes faecalis
(NCBI TaxID 511,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
NCBI PubMed ID: 34154406Publication DOI: 10.1128/mBio.00401-21Journal NLM ID: 101519231Publisher: Washington, DC: American Society for Microbiology
Correspondence: Christine.Beemelmanns
hki-jena.de
Institutions: Leibniz Institute for Natural Product Research and Infection Biology-Hans Knoll Institute, Jena, Germany, Electron Microscopy Centre, Friedrich Schiller University Jena, Jena, Germany
In marine environments, the bacterially induced metamorphosis of larvae is a widespread cross-kingdom communication phenomenon that is critical for the persistence of many marine invertebrates. However, the majority of inducing bacterial signals and underlying cellular mechanisms remain enigmatic. The marine hydroid Hydractinia echinata is a well-known model system for investigating bacterially stimulated larval metamorphosis, as larvae transform into the colonial adult stage within 24 h of signal detection. Although H. echinata has served as a cell biological model system for decades, the identity and influence of bacterial signals on the morphogenic transition remained largely unexplored. Using a bioassay-guided analysis, we first determined that specific bacterial (lyso)phospholipids, naturally present in bacterial membranes and vesicles, elicit metamorphosis in Hydractinia larvae in a dose-response manner. Lysophospholipids, as single compounds or in combination (50 μM), induced metamorphosis in up to 50% of all larvae within 48 h. Using fluorescence-labeled bacterial phospholipids, we demonstrated that phospholipids are incorporated into the larval membranes, where interactions with internal signaling cascades are proposed to occur. Second, we identified two structurally distinct exopolysaccharides of bacterial biofilms, the new Rha-Man polysaccharide from Pseudoalteromonas sp. strain P1-9 and curdlan from Alcaligenes faecalis, to induce metamorphosis in up to 75% of tested larvae. We also found that combinations of (lyso)phospholipids and curdlan induced transformation within 24 h, thereby exceeding the morphogenic activity observed for single compounds and bacterial biofilms. Our results demonstrate that two structurally distinct, bacterium-derived metabolites converge to induce high transformation rates of Hydractinia larvae and thus may help ensure optimal habitat selection. IMPORTANCE Bacterial biofilms profoundly influence the recruitment and settlement of marine invertebrates, critical steps for diverse marine processes such as the formation of coral reefs, the maintenance of marine fisheries, and the fouling of submerged surfaces. However, the complex composition of biofilms often makes the characterization of individual signals and regulatory mechanisms challenging. Developing tractable model systems to characterize these coevolved interactions is the key to understanding fundamental processes in evolutionary biology. Here, we characterized two types of bacterial signaling molecules, phospholipids and polysaccharides, that induce the morphogenic transition. We then analyzed their abundance and combinatorial activity. This study highlights the general importance of multiple bacterial signal converging activity in development-related cross-kingdom signaling and poses the question of whether complex lipids and polysaccharides are general metamorphic cues for cnidarian larvae.
exopolysaccharide, polysaccharides, natural products, Pseudoalteromonas, phospholipids, biofouling, Hydractinia, marine microbiology, metamorphosis, microbial ecology, phospholipid-mediated signaling
Structure type: homopolymer ; 50000-200000
Location inside paper: Fig. 9C, curdlan
Trivial name: curdlan
Compound class: EPS
Contained glycoepitopes: IEDB_1397514,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_161166,IEDB_2278476,IEDB_2278477,IEDB_558869,IEDB_857743,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, GC-MS, chemical analysis, TLC, biological assays, HPLC, enzymatic digestion, alkaline treatment, SEM, cryo-TEM, metamorphosis assay, HR-MS/MS
Related record ID(s): 10858
NCBI Taxonomy refs (TaxIDs): 511
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
Collapse this record
Casillo A, Fabozzi A, Russo Krauss I, Parrilli E, Biggs CI, Gibson MI, Lanzetta R, Arato V, Appavou MS, Radulescu A, Tutino ML, Paduano L, Corsaro MM
Physicochemical Approach to Understanding the Structure, Conformation, and Activity of Mannan Polysaccharides
Biomacromolecules 22(4) (2021)
1445-1457
|
a-D-Manp-(1--P--2)--a-D-Manp-(1-2)-+
|
a-D-Manp-(1-3)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-+ |
| |
/Variants 0/-a-D-Manp-(1-2)-+ | |
| | |
-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-
/Variants 0/ is:
a-D-Manp-(1-2)-
OR (exclusively)
12%a-D-Glcp-(1-2)- |
Show graphically |
Psychrobacter arcticus 273-4
(NCBI TaxID 259536,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 33729771Publication DOI: 10.1021/acs.biomac.0c01659Journal NLM ID: 100892849Publisher: Washington, DC: American Chemical Society
Correspondence: Luigi Paduano <lpaduano
unina.it>; Maria M. Corsaro <corsaro
unina.it>
Institutions: Department of Chemical Sciences, University of Naples 'Federico II', Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Naples, Italy, CSGI - Consorzio per lo Sviluppo dei Sistemi a Grande Interfase, Florence, Italy, Department of Chemistry, University of Warwick, Coventry CV4 7AL, U.K, Jülich Centre for Neutron Science, Garching Forschungszentrum, Lichtenbergstrasse 1, D-857478 Garching bei Munchen, Germany
Extracellular polysaccharides are widely produced by bacteria, yeasts, and algae. These polymers are involved in several biological functions, such as bacteria adhesion to surface and biofilm formation, ion sequestering, protection from desiccation, and cryoprotection. The chemical characterization of these polymers is the starting point for obtaining relationships between their structures and their various functions. While this fundamental correlation is well reported and studied for the proteins, for the polysaccharides, this relationship is less intuitive. In this paper, we elucidate the chemical structure and conformational studies of a mannan exopolysaccharide from the permafrost isolated bacterium Psychrobacter arcticus strain 273-4. The mannan from the cold-adapted bacterium was compared with its dephosphorylated derivative and the commercial product from Saccharomyces cerevisiae. Starting from the chemical structure, we explored a new approach to deepen the study of the structure/activity relationship. A pool of physicochemical techniques, ranging from small-angle neutron scattering (SANS) and dynamic and static light scattering (DLS and SLS, respectively) to circular dichroism (CD) and cryo-transmission electron microscopy (cryo-TEM), have been used. Finally, the ice recrystallization inhibition activity of the polysaccharides was explored. The experimental evidence suggests that the mannan exopolysaccharide from P. arcticus bacterium has an efficient interaction with the water molecules, and it is structurally characterized by rigid-rod regions assuming a 14-helix-type conformation.
conformation, structure, extracellular polysaccharide, biological activity, biofilm formation, Psychrobacter arcticus, Saccharomyces cerevisiae
Structure type: polymer chemical repeating unit
Location inside paper: abstract, scheme 1, table 1, mannanP.arc
Trivial name: mannan
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141111,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144996,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_174840,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, methylation, gel filtration, NMR-2D, GC-MS, sugar analysis, CD, HF hydrolysis, IRI, DLS, surface tension titration, SANS, SLS, cryo-TEM
Related record ID(s): 7897
NCBI Taxonomy refs (TaxIDs): 259536
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6,6,6,6 aDManp 100.6 71.3 72.1 68.1 72.1 66.7
6,6,6,2 aDManp 101.8 79.8 71.5 68.1 74.4 62.3
6,6,6 aDManp 99.4 80.0 71.4-71.5 67.8 72.1 66.9
6,6,2,2,3 aDManp 103.5 71.3 71.6 68.2 74.5 62.4
6,6,2,2 aDManp 103.5 70.9 79.2 67.6 72.5 62.4
6,6,2 aDManp 101.8 79.8 71.5 68.1 74.4 62.3
6,6 aDManp 99.4 80.0 71.4-71.5 67.8 72.1 66.9
6,2,2,0 aDManp 97.5 71.8 71.3 67.6 ? ?
6,2,2 P
6,2 aDManp 101.8 79.8 71.5 68.1 74.4 62.3
6 aDManp 99.4 80.0 71.4-71.5 67.8 72.1 66.9
aDManp 100.6 71.3 72.1 68.1 72.1 66.7
6,6,6,2,2 12%aDGlcp 102.9 74.0 74.9 71.8 77.5 62.4
6,6,6,2,2 aDManp 103.4 71.3 71.7 68.1 74.4 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6,6,6,6 aDManp 4.79 3.88 3.72 3.59 3.63 3.67-3.84
6,6,6,2 aDManp 5.19 4.01 3.80 3.62 3.66 3.64-3.80
6,6,6 aDManp 4.99-5.01 3.91-3.93 3.81-3.83 3.73 3.72 3.57-3.91
6,6,2,2,3 aDManp 5.04 3.96 3.75 3.53 3.66 3.64-3.78
6,6,2,2 aDManp 4.93 4.11 3.85 3.64 3.70 3.64-3.78
6,6,2 aDManp 5.19 4.01 3.80 3.62 3.66 3.64-3.80
6,6 aDManp 4.99-5.01 3.91-3.93 3.81-3.83 3.73 3.72 3.57-3.91
6,2,2,0 aDManp 5.34 3.91 3.88 3.68 ? ?
6,2,2 P
6,2 aDManp 5.19 4.01 3.80 3.62 3.66 3.64-3.80
6 aDManp 4.99-5.01 3.91-3.93 3.81-3.83 3.73 3.72 3.57-3.91
aDManp 4.79 3.88 3.72 3.59 3.63 3.67-3.84
6,6,6,2,2 12%aDGlcp 4.36 3.17 3.45 3.69 3.67 3.64-3.78
6,6,6,2,2 aDManp 4.94 3.96 3.70 3.53 3.66 3.64-3.78
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6,6,6,6 aDManp 100.6/4.79 71.3/3.88 72.1/3.72 68.1/3.59 72.1/3.63 66.7/3.67-3.84
6,6,6,2 aDManp 101.8/5.19 79.8/4.01 71.5/3.80 68.1/3.62 74.4/3.66 62.3/3.64-3.80
6,6,6 aDManp 99.4/4.99-5.01 80.0/3.91-3.93 71.4-71.5/3.81-3.83 67.8/3.73 72.1/3.72 66.9/3.57-3.91
6,6,2,2,3 aDManp 103.5/5.04 71.3/3.96 71.6/3.75 68.2/3.53 74.5/3.66 62.4/3.64-3.78
6,6,2,2 aDManp 103.5/4.93 70.9/4.11 79.2/3.85 67.6/3.64 72.5/3.70 62.4/3.64-3.78
6,6,2 aDManp 101.8/5.19 79.8/4.01 71.5/3.80 68.1/3.62 74.4/3.66 62.3/3.64-3.80
6,6 aDManp 99.4/4.99-5.01 80.0/3.91-3.93 71.4-71.5/3.81-3.83 67.8/3.73 72.1/3.72 66.9/3.57-3.91
6,2,2,0 aDManp 97.5/5.34 71.8/3.91 71.3/3.88 67.6/3.68 ?/? ?/?
6,2,2 P
6,2 aDManp 101.8/5.19 79.8/4.01 71.5/3.80 68.1/3.62 74.4/3.66 62.3/3.64-3.80
6 aDManp 99.4/4.99-5.01 80.0/3.91-3.93 71.4-71.5/3.81-3.83 67.8/3.73 72.1/3.72 66.9/3.57-3.91
aDManp 100.6/4.79 71.3/3.88 72.1/3.72 68.1/3.59 72.1/3.63 66.7/3.67-3.84
6,6,6,2,2 12%aDGlcp 102.9/4.36 74.0/3.17 74.9/3.45 71.8/3.69 77.5/3.67 62.4/3.64-3.78
6,6,6,2,2 aDManp 103.4/4.94 71.3/3.96 71.7/3.70 68.1/3.53 74.4/3.66 62.4/3.64-3.78
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6,6,6,6 | aDManp | 4.79 | 3.88 | 3.72 | 3.59 | 3.63 | 3.67
3.84 |
| 6,6,6,2 | aDManp | 5.19 | 4.01 | 3.80 | 3.62 | 3.66 | 3.64
3.80 |
| 6,6,6 | aDManp | 4.99
5.01 | 3.91
3.93 | 3.81
3.83 | 3.73 | 3.72 | 3.57
3.91 |
| 6,6,2,2,3 | aDManp | 5.04 | 3.96 | 3.75 | 3.53 | 3.66 | 3.64
3.78 |
| 6,6,2,2 | aDManp | 4.93 | 4.11 | 3.85 | 3.64 | 3.70 | 3.64
3.78 |
| 6,6,2 | aDManp | 5.19 | 4.01 | 3.80 | 3.62 | 3.66 | 3.64
3.80 |
| 6,6 | aDManp | 4.99
5.01 | 3.91
3.93 | 3.81
3.83 | 3.73 | 3.72 | 3.57
3.91 |
| 6,2,2,0 | aDManp | 5.34 | 3.91 | 3.88 | 3.68 | ? | ? |
| 6,2,2 | P | |
| 6,2 | aDManp | 5.19 | 4.01 | 3.80 | 3.62 | 3.66 | 3.64
3.80 |
| 6 | aDManp | 4.99
5.01 | 3.91
3.93 | 3.81
3.83 | 3.73 | 3.72 | 3.57
3.91 |
| | aDManp | 4.79 | 3.88 | 3.72 | 3.59 | 3.63 | 3.67
3.84 |
| 6,6,6,2,2 | 12%aDGlcp | 4.36 | 3.17 | 3.45 | 3.69 | 3.67 | 3.64
3.78 |
| 6,6,6,2,2 | aDManp | 4.94 | 3.96 | 3.70 | 3.53 | 3.66 | 3.64
3.78 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6,6,6,6 | aDManp | 100.6 | 71.3 | 72.1 | 68.1 | 72.1 | 66.7 |
| 6,6,6,2 | aDManp | 101.8 | 79.8 | 71.5 | 68.1 | 74.4 | 62.3 |
| 6,6,6 | aDManp | 99.4 | 80.0 | 71.4
71.5 | 67.8 | 72.1 | 66.9 |
| 6,6,2,2,3 | aDManp | 103.5 | 71.3 | 71.6 | 68.2 | 74.5 | 62.4 |
| 6,6,2,2 | aDManp | 103.5 | 70.9 | 79.2 | 67.6 | 72.5 | 62.4 |
| 6,6,2 | aDManp | 101.8 | 79.8 | 71.5 | 68.1 | 74.4 | 62.3 |
| 6,6 | aDManp | 99.4 | 80.0 | 71.4
71.5 | 67.8 | 72.1 | 66.9 |
| 6,2,2,0 | aDManp | 97.5 | 71.8 | 71.3 | 67.6 | ? | ? |
| 6,2,2 | P | |
| 6,2 | aDManp | 101.8 | 79.8 | 71.5 | 68.1 | 74.4 | 62.3 |
| 6 | aDManp | 99.4 | 80.0 | 71.4
71.5 | 67.8 | 72.1 | 66.9 |
| | aDManp | 100.6 | 71.3 | 72.1 | 68.1 | 72.1 | 66.7 |
| 6,6,6,2,2 | 12%aDGlcp | 102.9 | 74.0 | 74.9 | 71.8 | 77.5 | 62.4 |
| 6,6,6,2,2 | aDManp | 103.4 | 71.3 | 71.7 | 68.1 | 74.4 | 62.4 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":100.6,"l":"1","c":[0,0,225]},{"s":71.3,"l":"2","c":[0,0,225]},{"s":72.1,"l":"3","c":[0,0,225]},{"s":68.1,"l":"4","c":[0,0,225]},{"s":72.1,"l":"5","c":[0,0,225]},{"s":66.7,"l":"6","c":[0,0,225]},{"s":101.8,"l":"1","c":[230,0,30]},{"s":79.8,"l":"2","c":[230,0,30]},{"s":71.5,"l":"3","c":[230,0,30]},{"s":68.1,"l":"4","c":[230,0,30]},{"s":74.4,"l":"5","c":[230,0,30]},{"s":62.3,"l":"6","c":[230,0,30]},{"s":99.4,"l":"1","c":[0,165,0]},{"s":80,"l":"2","c":[0,165,0]},{"s":71.45,"l":"3","c":[0,165,0]},{"s":67.8,"l":"4","c":[0,165,0]},{"s":72.1,"l":"5","c":[0,165,0]},{"s":66.9,"l":"6","c":[0,165,0]},{"s":103.5,"l":"1","c":[120,0,225]},{"s":71.3,"l":"2","c":[120,0,225]},{"s":71.6,"l":"3","c":[120,0,225]},{"s":68.2,"l":"4","c":[120,0,225]},{"s":74.5,"l":"5","c":[120,0,225]},{"s":62.4,"l":"6","c":[120,0,225]},{"s":103.5,"l":"1","c":[0,192,255]},{"s":70.9,"l":"2","c":[0,192,255]},{"s":79.2,"l":"3","c":[0,192,255]},{"s":67.6,"l":"4","c":[0,192,255]},{"s":72.5,"l":"5","c":[0,192,255]},{"s":62.4,"l":"6","c":[0,192,255]},{"s":101.8,"l":"1","c":[220,0,180]},{"s":79.8,"l":"2","c":[220,0,180]},{"s":71.5,"l":"3","c":[220,0,180]},{"s":68.1,"l":"4","c":[220,0,180]},{"s":74.4,"l":"5","c":[220,0,180]},{"s":62.3,"l":"6","c":[220,0,180]},{"s":99.4,"l":"1","c":[100,160,0]},{"s":80,"l":"2","c":[100,160,0]},{"s":71.45,"l":"3","c":[100,160,0]},{"s":67.8,"l":"4","c":[100,160,0]},{"s":72.1,"l":"5","c":[100,160,0]},{"s":66.9,"l":"6","c":[100,160,0]},{"s":97.5,"l":"1","c":[210,210,0]},{"s":71.8,"l":"2","c":[210,210,0]},{"s":71.3,"l":"3","c":[210,210,0]},{"s":67.6,"l":"4","c":[210,210,0]},{"s":101.8,"l":"1","c":[210,110,0]},{"s":79.8,"l":"2","c":[210,110,0]},{"s":71.5,"l":"3","c":[210,110,0]},{"s":68.1,"l":"4","c":[210,110,0]},{"s":74.4,"l":"5","c":[210,110,0]},{"s":62.3,"l":"6","c":[210,110,0]},{"s":99.4,"l":"1","c":[90,45,15]},{"s":80,"l":"2","c":[90,45,15]},{"s":71.45,"l":"3","c":[90,45,15]},{"s":67.8,"l":"4","c":[90,45,15]},{"s":72.1,"l":"5","c":[90,45,15]},{"s":66.9,"l":"6","c":[90,45,15]},{"s":100.6,"l":"1","c":[0,240,192]},{"s":71.3,"l":"2","c":[0,240,192]},{"s":72.1,"l":"3","c":[0,240,192]},{"s":68.1,"l":"4","c":[0,240,192]},{"s":72.1,"l":"5","c":[0,240,192]},{"s":66.7,"l":"6","c":[0,240,192]},{"s":102.9,"l":"1","c":[140,0,50]},{"s":74,"l":"2","c":[140,0,50]},{"s":74.9,"l":"3","c":[140,0,50]},{"s":71.8,"l":"4","c":[140,0,50]},{"s":77.5,"l":"5","c":[140,0,50]},{"s":62.4,"l":"6","c":[140,0,50]},{"s":103.4,"l":"1","c":[0,0,110]},{"s":71.3,"l":"2","c":[0,0,110]},{"s":71.7,"l":"3","c":[0,0,110]},{"s":68.1,"l":"4","c":[0,0,110]},{"s":74.4,"l":"5","c":[0,0,110]},{"s":62.4,"l":"6","c":[0,0,110]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Guo H, Rischer M, Westermann M, Beemelmanns C
Two Distinct Bacterial Biofilm Components Trigger Metamorphosis in the Colonial Hydrozoan Hydractinia echinata
mBio 12(3) (2021)
e0040121
Pseudoalteromonas sp. P1-9
(Ancestor NCBI TaxID 53246,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 34154406Publication DOI: 10.1128/mBio.00401-21Journal NLM ID: 101519231Publisher: Washington, DC: American Society for Microbiology
Correspondence: Christine.Beemelmanns
hki-jena.de
Institutions: Leibniz Institute for Natural Product Research and Infection Biology-Hans Knoll Institute, Jena, Germany, Electron Microscopy Centre, Friedrich Schiller University Jena, Jena, Germany
In marine environments, the bacterially induced metamorphosis of larvae is a widespread cross-kingdom communication phenomenon that is critical for the persistence of many marine invertebrates. However, the majority of inducing bacterial signals and underlying cellular mechanisms remain enigmatic. The marine hydroid Hydractinia echinata is a well-known model system for investigating bacterially stimulated larval metamorphosis, as larvae transform into the colonial adult stage within 24 h of signal detection. Although H. echinata has served as a cell biological model system for decades, the identity and influence of bacterial signals on the morphogenic transition remained largely unexplored. Using a bioassay-guided analysis, we first determined that specific bacterial (lyso)phospholipids, naturally present in bacterial membranes and vesicles, elicit metamorphosis in Hydractinia larvae in a dose-response manner. Lysophospholipids, as single compounds or in combination (50 μM), induced metamorphosis in up to 50% of all larvae within 48 h. Using fluorescence-labeled bacterial phospholipids, we demonstrated that phospholipids are incorporated into the larval membranes, where interactions with internal signaling cascades are proposed to occur. Second, we identified two structurally distinct exopolysaccharides of bacterial biofilms, the new Rha-Man polysaccharide from Pseudoalteromonas sp. strain P1-9 and curdlan from Alcaligenes faecalis, to induce metamorphosis in up to 75% of tested larvae. We also found that combinations of (lyso)phospholipids and curdlan induced transformation within 24 h, thereby exceeding the morphogenic activity observed for single compounds and bacterial biofilms. Our results demonstrate that two structurally distinct, bacterium-derived metabolites converge to induce high transformation rates of Hydractinia larvae and thus may help ensure optimal habitat selection. IMPORTANCE Bacterial biofilms profoundly influence the recruitment and settlement of marine invertebrates, critical steps for diverse marine processes such as the formation of coral reefs, the maintenance of marine fisheries, and the fouling of submerged surfaces. However, the complex composition of biofilms often makes the characterization of individual signals and regulatory mechanisms challenging. Developing tractable model systems to characterize these coevolved interactions is the key to understanding fundamental processes in evolutionary biology. Here, we characterized two types of bacterial signaling molecules, phospholipids and polysaccharides, that induce the morphogenic transition. We then analyzed their abundance and combinatorial activity. This study highlights the general importance of multiple bacterial signal converging activity in development-related cross-kingdom signaling and poses the question of whether complex lipids and polysaccharides are general metamorphic cues for cnidarian larvae.
exopolysaccharide, polysaccharides, natural products, Pseudoalteromonas, phospholipids, biofouling, Hydractinia, marine microbiology, metamorphosis, microbial ecology, phospholipid-mediated signaling
Structure type: polymer chemical repeating unit
Location inside paper: Fig. 9C, Fig. S21, table S2
Trivial name: a morphogenic polysaccharide
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_136105,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, GC-MS, chemical analysis, TLC, biological assays, HPLC, enzymatic digestion, alkaline treatment, SEM, cryo-TEM, metamorphosis assay, HR-MS/MS
Related record ID(s): 7995
NCBI Taxonomy refs (TaxIDs): 53246
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3 aLRhap 96.15 68.83 76.67 77.30 68.41 16.82
?DManp 101.15 66.49 75.05 64.48 72.65 60.61
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3 aLRhap 4.96 4.42 4.59 3.75 4.13 1.32
?DManp 4.99 4.21 3.86 3.83 4.11 3.81-3.90
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3 aLRhap 96.15/4.96 68.83/4.42 76.67/4.59 77.30/3.75 68.41/4.13 16.82/1.32
?DManp 101.15/4.99 66.49/4.21 75.05/3.86 64.48/3.83 72.65/4.11 60.61/3.81-3.90
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3 | aLRhap | 4.96 | 4.42 | 4.59 | 3.75 | 4.13 | 1.32 |
| | ?DManp | 4.99 | 4.21 | 3.86 | 3.83 | 4.11 | 3.81
3.90 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3 | aLRhap | 96.15 | 68.83 | 76.67 | 77.30 | 68.41 | 16.82 |
| | ?DManp | 101.15 | 66.49 | 75.05 | 64.48 | 72.65 | 60.61 |
|
There is only one chemically distinct structure:
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