Found 15 structures.
Displayed structures from 1 to 15
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1. Compound ID: 6761
|
S-6)-+
|
/Variants 0/-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcNAc
/Variants 0/ is:
C16={?,?}-(1-2)-
OR (exclusively)
C16={?,?,?}-(1-2)- |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 3065
Spaink HP "The molecular basis of the host specificity of the Rhizobium bacteria" -
Antonie van Leeuwenhoek 65 (1994) 81-98
The interaction between soil bacteria belonging to the genera Rhizobium, Bradyrhizobium and Azorhizobium and leguminous plants results in the induction of a new plant organ, the root nodule. After invading these root nodules via infection threads the bacteria start to fix atmospheric nitrogen into ammonia which is beneficial for the host plant. This symbiotic interaction is highly host-specific in that each rhizobial strain is able to associate with only a limited number of host plant species. The subject of this presentation is the molecular mechanism by which the bacterium determines its host-specific characteristics. This mechanism appears to be based on at least two stages of molecular signaling between the bacterium and the plant host. In the first stage, flavonoids secreted by the plant root induce, in a host specific way, the transcription of bacterial genes which are involved in nodulation, the so-called nod genes. This leads to the second step of the signaling system: the production and secretion of lipo-oligosaccharide molecules by the Rhizobium bacteria. These signal molecules, which are acylated forms of small fragments of chitin, have various discernable effects on the roots of the host plants. One of these effects is the dedifferentiation of groups of cells located in the cortex which leads to the formation of nodule meristems. In their mitogenic activity the bacterial signals resemble several well-known plant hormones like auxins and cytokinins. However, there are two major differences: (i) the bacterial signals lead to the induction of a specific organ and (ii) they are host-specific in that only the signals produced by compatible bacteria are able to induce meristems. The nod genes determine this stage of host specificity by their essential role in the biosynthesis of the signal molecules. They appear to encode enzymes which are involved in the processes of fatty acid biosynthesis, fatty acid transfer, chitin synthesis and chitin modification. I will illustrate the statement that the nod gene products are ideal model enzymes for the study of these important processes because they are not needed in the free-living state of the bacteria.
symbiosis, plant-microbe interaction, nodulation genes, signal molecules
NCBI PubMed ID: 7718036Publication DOI: 10.1007/BF00871750Journal NLM ID: 0372625Publisher: Dordrecht: Kluwer Academic
Institutions: Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University, Leiden, The Netherlands
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2. Compound ID: 6762
|
S-6)-+
|
C16={?,?}-(1-2)-b-D-GlcpN6(%)Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcNAc |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 3065
Spaink HP "The molecular basis of the host specificity of the Rhizobium bacteria" -
Antonie van Leeuwenhoek 65 (1994) 81-98
The interaction between soil bacteria belonging to the genera Rhizobium, Bradyrhizobium and Azorhizobium and leguminous plants results in the induction of a new plant organ, the root nodule. After invading these root nodules via infection threads the bacteria start to fix atmospheric nitrogen into ammonia which is beneficial for the host plant. This symbiotic interaction is highly host-specific in that each rhizobial strain is able to associate with only a limited number of host plant species. The subject of this presentation is the molecular mechanism by which the bacterium determines its host-specific characteristics. This mechanism appears to be based on at least two stages of molecular signaling between the bacterium and the plant host. In the first stage, flavonoids secreted by the plant root induce, in a host specific way, the transcription of bacterial genes which are involved in nodulation, the so-called nod genes. This leads to the second step of the signaling system: the production and secretion of lipo-oligosaccharide molecules by the Rhizobium bacteria. These signal molecules, which are acylated forms of small fragments of chitin, have various discernable effects on the roots of the host plants. One of these effects is the dedifferentiation of groups of cells located in the cortex which leads to the formation of nodule meristems. In their mitogenic activity the bacterial signals resemble several well-known plant hormones like auxins and cytokinins. However, there are two major differences: (i) the bacterial signals lead to the induction of a specific organ and (ii) they are host-specific in that only the signals produced by compatible bacteria are able to induce meristems. The nod genes determine this stage of host specificity by their essential role in the biosynthesis of the signal molecules. They appear to encode enzymes which are involved in the processes of fatty acid biosynthesis, fatty acid transfer, chitin synthesis and chitin modification. I will illustrate the statement that the nod gene products are ideal model enzymes for the study of these important processes because they are not needed in the free-living state of the bacteria.
symbiosis, plant-microbe interaction, nodulation genes, signal molecules
NCBI PubMed ID: 7718036Publication DOI: 10.1007/BF00871750Journal NLM ID: 0372625Publisher: Dordrecht: Kluwer Academic
Institutions: Institute of Molecular Plant Sciences, Clusius Laboratory, Leiden University, Leiden, The Netherlands
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3. Compound ID: 6822
|
S-6)-+
|
/Variants 0/-b-D-GlcpN6Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcpNAc
/Variants 0/ is:
C16={?,?}-(1-2)-
OR (exclusively)
C16={?,?,?}-(1-2)- |
Show graphically |
Structure type: oligomer
Trivial name: NodRm-IV(C16:2,S), NodRm-V(C16:2,S)
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 3111
Dénarié J, Cullimore J "Lipo-oligosaccharide nodulation factors: A new class of signaling molecules mediating recognition and morphogenesis" -
Cell 74 (1993) 951-954
The legume-rhizobia symbiosis is estimated to fix per annum as much nitrogen as the fertilizer industry and is of great agronomic and ecological importance. This efficient nitrogen-fixing association occurs as a result of the formation of a new specialized organ, the root nodule, which is induced by the prokaryotic symbiont on its specific plant partner (see Nap and Bisseling, 1990). The rhizobial genes that determine the host recognition and nodulation have recently been found to specify the synthesis of excreted lipo-oligosaccharide signals (Figure 1) which are capable of eliciting, at extremely low concentrations, many of the plant responses characteristic of the bacteria themselves. These responses include the initiation of cell division, induction of specific changes in cell morphology, and triggering of a plant organogenic program leading to the formation of the nodule. This review focuses on the role of this new class of signaling molecules in host-partner recognition and nodule development in the legume-rhizobia symbiosis.
NCBI PubMed ID: 8402884Publication DOI: 10.1016/0092-8674(93)90717-5Journal NLM ID: 0413066Publisher: Cambridge, MA: Cell Press
Institutions: Laboratoire de Biologie Moléculaire, des Relations Plantes-Microorganismes CNRS-INRA, Castanet-Tolosan, France
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4. Compound ID: 10134
|
S-6)-+
|
C16={?,?}-(1-2)-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Trivial name: NodRm-IV(C16:2,S), NodRm-V(C16:2,S)
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 4216
Felle HH, Kondorosi E, Kondorosi A, Schultze M "Nod signal-induced plasma membrane potential changes in alfalfa root hairs are differentially sensitive to structural modifications of the lipochitooligosaccharide" -
Plant Journal: for Cell and Molecular Biology 7 (1995) 939-947
Lipochitooligosaccharide Nod signals are important determinants of host specificity in the Rhizobium-legume symbiosis. The most rapid response of plant cells to the R. meliloti Nod signal NodRm-IV(C16:2,S) reported so far is the depolarization of the plasma membrane potential in alfalfa root hairs. In order to investigate whether this response may be part of a specific signal transduction cascade involved in the nodulation process, its specificity was studied with respect to host-specific modifications of the lipochitooligosaccharide. Five different Nod factors displaying different degrees of activity in inducing root hair deformation or cortical cell divisions on alfalfa were tested. The ability of the Nod factors to elicit plasma membrane depolarization correlated well with their activity in the bioassays. Removal of the sulfate group (NodRm-IV(C16:2)) led to inactivation of the Nod factor. An increase in the length of the chitooligosaccharide backbone (NodRm-V(C16:2,S)) or saturation of the acyl chain (NodRm-IV(C16:0,S)) resulted in severely reduced activity. In contrast, the O-acetyl group at the non-reducing terminus in NodRm-IV(Ac,C16:2,S), which confers substantially higher activity in long-term bioassays, did not enhance plasma membrane depolarization significantly in comparison with the non-O-acetylated factor. Thus, the rapid plasma membrane response is differentially sensitive to various structural motifs of the lipochitooligosaccharide. These data suggest that the different substituents modifying the basic Nod factor structure may have distinct functions, not all of them contributing to the interaction with a putative receptor in root hair cells. However, the overall specificity of the membrane depolarization for the cognate Nod factors raises the possibility that it is involved in a Nod signal transduction pathway.
Publication DOI: 10.1046/j.1365-313X.1995.07060939.xJournal NLM ID: 9207397Publisher: Oxford: Blackwell Scientific Publishers and BIOS Scientific Publishers for the Society for Experimental Biology
Institutions: Institut des Sciences Végétales, CNRS, Gif-sur-Yvette, France, Institute of Genetics, Biological Research Center, Hungarian Academy of Sciences, Szeged, Hungary, Botanisches Institut I, Universität Giessen, Giessen, Germany
Methods: plant assays, plasma membrane potential, conductance measurment
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5. Compound ID: 10136
|
S-6)-+
|
C16={?,?}-(1-2)-b-D-GlcpN6Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Trivial name: NodRm-IV(Ac,C16:2,S)
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 4216
Felle HH, Kondorosi E, Kondorosi A, Schultze M "Nod signal-induced plasma membrane potential changes in alfalfa root hairs are differentially sensitive to structural modifications of the lipochitooligosaccharide" -
Plant Journal: for Cell and Molecular Biology 7 (1995) 939-947
Lipochitooligosaccharide Nod signals are important determinants of host specificity in the Rhizobium-legume symbiosis. The most rapid response of plant cells to the R. meliloti Nod signal NodRm-IV(C16:2,S) reported so far is the depolarization of the plasma membrane potential in alfalfa root hairs. In order to investigate whether this response may be part of a specific signal transduction cascade involved in the nodulation process, its specificity was studied with respect to host-specific modifications of the lipochitooligosaccharide. Five different Nod factors displaying different degrees of activity in inducing root hair deformation or cortical cell divisions on alfalfa were tested. The ability of the Nod factors to elicit plasma membrane depolarization correlated well with their activity in the bioassays. Removal of the sulfate group (NodRm-IV(C16:2)) led to inactivation of the Nod factor. An increase in the length of the chitooligosaccharide backbone (NodRm-V(C16:2,S)) or saturation of the acyl chain (NodRm-IV(C16:0,S)) resulted in severely reduced activity. In contrast, the O-acetyl group at the non-reducing terminus in NodRm-IV(Ac,C16:2,S), which confers substantially higher activity in long-term bioassays, did not enhance plasma membrane depolarization significantly in comparison with the non-O-acetylated factor. Thus, the rapid plasma membrane response is differentially sensitive to various structural motifs of the lipochitooligosaccharide. These data suggest that the different substituents modifying the basic Nod factor structure may have distinct functions, not all of them contributing to the interaction with a putative receptor in root hair cells. However, the overall specificity of the membrane depolarization for the cognate Nod factors raises the possibility that it is involved in a Nod signal transduction pathway.
Publication DOI: 10.1046/j.1365-313X.1995.07060939.xJournal NLM ID: 9207397Publisher: Oxford: Blackwell Scientific Publishers and BIOS Scientific Publishers for the Society for Experimental Biology
Institutions: Institut des Sciences Végétales, CNRS, Gif-sur-Yvette, France, Institute of Genetics, Biological Research Center, Hungarian Academy of Sciences, Szeged, Hungary, Botanisches Institut I, Universität Giessen, Giessen, Germany
Methods: plant assays, plasma membrane potential, conductance measurment
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6. Compound ID: 10140
|
S-6)-+
|
C16={?,?}-(1-2)-b-D-GlcpN6(%)Ac-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Trivial name: NodRm-IV(C16:2,Ac,S), NodRm-V(C16:2,Ac,S)
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 4217
Spaink HP, Lugtenberg BJJ "Role of rhizobial lipo-chitin oligosaccharide signal molecules in root nodule organogenesis" -
Plant Molecular Biology 26 (1994) 1413-1422
The role of oligosaccharide molecules in plant development is discussed. In particular the role of the rhizobial lipo-chitin oligosaccharide (LCO) signal molecules in the development of the root nodule indicates that oligosaccharides play an important role in organogenesis in plants. Recent results of the analyses of structures and of the biosynthesis of the LCO molecules are summarized in this paper. The knowledge and technologies that resulted from these studies will be important tools for further studying the function of LCO signals in the plant and in the search for analogous signal molecules produced by plants.
NCBI PubMed ID: 7858197Publication DOI: 10.1007/BF00016482Journal NLM ID: 9106343Publisher: Dordrecht: Kluwer Academic
Institutions: Institute of Molecular Plant Sciences, Leiden University, The Netherlands
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7. Compound ID: 10141
|
S-6)-+
|
/Variants 0/-b-D-GlcpN-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc
/Variants 0/ is:
C16={?,?}-(1-2)-
OR (exclusively)
C16={?,?,?}-(1-2)- |
Show graphically |
Structure type: oligomer
Trivial name: NodRm-IV(C16:2,S), NodRm-V(C16:2,S)
Compound class: LOS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_153212,IEDB_1635956,IEDB_241099,IEDB_241119,IEDB_241120,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 4217
Spaink HP, Lugtenberg BJJ "Role of rhizobial lipo-chitin oligosaccharide signal molecules in root nodule organogenesis" -
Plant Molecular Biology 26 (1994) 1413-1422
The role of oligosaccharide molecules in plant development is discussed. In particular the role of the rhizobial lipo-chitin oligosaccharide (LCO) signal molecules in the development of the root nodule indicates that oligosaccharides play an important role in organogenesis in plants. Recent results of the analyses of structures and of the biosynthesis of the LCO molecules are summarized in this paper. The knowledge and technologies that resulted from these studies will be important tools for further studying the function of LCO signals in the plant and in the search for analogous signal molecules produced by plants.
NCBI PubMed ID: 7858197Publication DOI: 10.1007/BF00016482Journal NLM ID: 9106343Publisher: Dordrecht: Kluwer Academic
Institutions: Institute of Molecular Plant Sciences, Leiden University, The Netherlands
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8. Compound ID: 18110
|
56%But-(1-2)-+
|
/Variants 0/-b-D-Manp4Ac-(1-4)-D-Ery-ol
/Variants 0/ is:
Pam-(1-3)-
OR (exclusively)
Myr-(1-3)-
OR (exclusively)
C16={?,?}-(1-3)-
OR (exclusively)
LIP-(1-3)- |
Show graphically |
Structure type: oligomer
; 655.9 (C16:1 and C4:0), 657.9 (C16:0 and C4:0) [M+Na]+
Trivial name: 4-O-[(4'-O-acetyl-3'-O-alka(e)noyl-2'-O-butanoyl)-β-D-mannopyranosyl]-D-erythritol
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_141181,IEDB_144983,IEDB_152206,IEDB_176772,IEDB_983930,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 7087
Morita T, Konishi M, Fukuoka T, Imura T, Kitamoto D "Identification of Ustilago cynodontis as a New Producer of Glycolipid Biosurfactants, Mannosylerythritol Lipids, Based on Ribosomal DNA Sequences" -
Journal of Oleo Science 57(10) (2008) 549-556
Mannosylerythritol lipids (MELs) are one of the most promising glycolipid biosurfactants known because of their multifunctionality and biocompatibility. The search for novel producers of MELs was undertaken based on the analysis of ribosomal DNA sequences on basidiomycetous yeasts. The bermuda grass smut fungus Ustilago cynodontis NBRC 7530, which taxonomically relates to Pseudozyma shanxiensis known as a MEL-C producer, was found to accumulate glycolipids in the cultured medium. Under a shake flask culture with soybean oil, the amount of the glycolipids was 1.4 g/L for 7 days at 25 degrees C. As a result of the structural characterization, the main glycolipids was identified as 4-O-[(4'-O-acetyl-3'-O-alka(e)noyl-2'-O-butanoyl)-β-D-mannopyranosyl]-D-erythritol, and the major fatty acids were C(14) and C(16) ones. The glycolipid was highly hydrophilic MEL-C, and very similar to those produced by P. shanxiensis. The fungi of the genus Ustilago are thus likely to be potential producers of MELs as well as the yeasts of the genus Pseudozyma.
glycolipid, biosurfactant, yeast, Ustilago, mannosylerythritol lipid, Pseudozyma, smut fungi
NCBI PubMed ID: 18781055Publication DOI: 10.5650/jos.57.549Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Dai Kitamoto
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, TLC, MALDI-TOF MS, composition analysis, HPLC, extraction, CC, phylogenetic analysis
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9. Compound ID: 18111
|
/Variants 0/-b-D-Manp2Ac4Ac-(1-4)-D-Ery-ol
/Variants 0/ is:
Pam-(1-3)-
OR (exclusively)
Myr-(1-3)-
OR (exclusively)
C16={?,?}-(1-3)-
OR (exclusively)
LIP-(1-3)- |
Show graphically |
Structure type: oligomer
Trivial name: 4-O-[(4'-O-acetyl-3'-O-alka(e)noyl-2'-O-acetyl)-β-D-mannopyranosyl]-D-erythritol
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_141181,IEDB_144983,IEDB_152206,IEDB_176772,IEDB_983930,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 7087
Morita T, Konishi M, Fukuoka T, Imura T, Kitamoto D "Identification of Ustilago cynodontis as a New Producer of Glycolipid Biosurfactants, Mannosylerythritol Lipids, Based on Ribosomal DNA Sequences" -
Journal of Oleo Science 57(10) (2008) 549-556
Mannosylerythritol lipids (MELs) are one of the most promising glycolipid biosurfactants known because of their multifunctionality and biocompatibility. The search for novel producers of MELs was undertaken based on the analysis of ribosomal DNA sequences on basidiomycetous yeasts. The bermuda grass smut fungus Ustilago cynodontis NBRC 7530, which taxonomically relates to Pseudozyma shanxiensis known as a MEL-C producer, was found to accumulate glycolipids in the cultured medium. Under a shake flask culture with soybean oil, the amount of the glycolipids was 1.4 g/L for 7 days at 25 degrees C. As a result of the structural characterization, the main glycolipids was identified as 4-O-[(4'-O-acetyl-3'-O-alka(e)noyl-2'-O-butanoyl)-β-D-mannopyranosyl]-D-erythritol, and the major fatty acids were C(14) and C(16) ones. The glycolipid was highly hydrophilic MEL-C, and very similar to those produced by P. shanxiensis. The fungi of the genus Ustilago are thus likely to be potential producers of MELs as well as the yeasts of the genus Pseudozyma.
glycolipid, biosurfactant, yeast, Ustilago, mannosylerythritol lipid, Pseudozyma, smut fungi
NCBI PubMed ID: 18781055Publication DOI: 10.5650/jos.57.549Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Dai Kitamoto
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, TLC, MALDI-TOF MS, composition analysis, HPLC, extraction, CC, phylogenetic analysis
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10. Compound ID: 18112
|
/Variants 1/-+
|
/Variants 0/-b-D-Manp4Ac-(1-4)-D-Ery-ol
/Variants 0/ is:
Pam-(1-3)-
OR (exclusively)
C16={?,?}-(1-3)-
OR (exclusively)
LIP-(1-3)-
/Variants 1/ is:
Pam-(1-2)-
OR (exclusively)
C16={?,?}-(1-2)-
OR (exclusively)
LIP-(1-2)- |
Show graphically |
Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_141181,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 7087
Morita T, Konishi M, Fukuoka T, Imura T, Kitamoto D "Identification of Ustilago cynodontis as a New Producer of Glycolipid Biosurfactants, Mannosylerythritol Lipids, Based on Ribosomal DNA Sequences" -
Journal of Oleo Science 57(10) (2008) 549-556
Mannosylerythritol lipids (MELs) are one of the most promising glycolipid biosurfactants known because of their multifunctionality and biocompatibility. The search for novel producers of MELs was undertaken based on the analysis of ribosomal DNA sequences on basidiomycetous yeasts. The bermuda grass smut fungus Ustilago cynodontis NBRC 7530, which taxonomically relates to Pseudozyma shanxiensis known as a MEL-C producer, was found to accumulate glycolipids in the cultured medium. Under a shake flask culture with soybean oil, the amount of the glycolipids was 1.4 g/L for 7 days at 25 degrees C. As a result of the structural characterization, the main glycolipids was identified as 4-O-[(4'-O-acetyl-3'-O-alka(e)noyl-2'-O-butanoyl)-β-D-mannopyranosyl]-D-erythritol, and the major fatty acids were C(14) and C(16) ones. The glycolipid was highly hydrophilic MEL-C, and very similar to those produced by P. shanxiensis. The fungi of the genus Ustilago are thus likely to be potential producers of MELs as well as the yeasts of the genus Pseudozyma.
glycolipid, biosurfactant, yeast, Ustilago, mannosylerythritol lipid, Pseudozyma, smut fungi
NCBI PubMed ID: 18781055Publication DOI: 10.5650/jos.57.549Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Dai Kitamoto
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, TLC, MALDI-TOF MS, composition analysis, HPLC, extraction, CC, phylogenetic analysis
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11. Compound ID: 18202
|
/Variants 1/-+
|
/Variants 0/-b-D-Manp4Ac-(1-4)-Ery-ol
/Variants 0/ is:
Lau-(1-3)-
OR (exclusively)
Hxo-(1-3)-
OR (exclusively)
C16={?,?}-(1-3)-
/Variants 1/ is:
Lau-(1-2)-
OR (exclusively)
Hxo-(1-2)-
OR (exclusively)
C16={?,?}-(1-2)- |
Show graphically |
Structure type: oligomer
Trivial name: mannosylerythritol lipid (MEL-C)
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_534864,IEDB_983930,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 7130
Konishi M, Morita T, Fukuoka T, Imura T, Kakugawa K, Kitamoto D "Production of different types of mannosylerythritol lipids as biosurfactants by the newly isolated yeast strains belonging to the genus Pseudozyma" -
Applied Microbiology and Biotechnology 75(3) (2007) 521-531
Mannosylerythritol lipids (MEL), which are abundantly secreted by yeasts, are one of the most promising biosurfactants known. To obtain various types of MEL and to attain a broad range of applications for them, screening of novel producers was undertaken. Thirteen strains of yeasts were successfully isolated as potential MEL producers; they showed high production yields of MEL of around 20 g l−1 from 40 g l−1 of soybean oil. Based on the taxonomical study, all the strains were classified to be the genus Pseudozyma. It is interesting to note that they were categorized into three groups according to their production patterns of MEL. The first group, which included 11 strains taxonomically closely related to high-level MEL producers such as Pseudozyma antarctica and Pseudozyma aphidis, mainly produced 4-O-[(4′,6′-di-O-acetyl-2′,3′-di-O-alkanoyl)-β-D-mannopyranosyl]-meso-erythritol (MEL-A) together with 4-O-[(6′-mono-O-acetyl-2′,3′-di-O-alkanoyl)-β-D-mannopyranosyl]-meso-erythritol (MEL-B) and 4-O-[(4′-mono-O-acetyl-2′,3′-di-O-alkanoyl)-β-D-mannopyranosyl]-meso-erythritol (MEL-C) as the minor components. The second group of one strain, which was related to Pseudozyma tsukubaensis, predominantly produced MEL-B. The third group of one strain, which was closely related to Pseudozyma hubeiensis, mainly produced MEL-C; this is the first observation of the efficient production of MEL-C from soybean oil. Moreover, the major fatty acids of the obtained MEL-C were C6, C12, and C16 acids, and were considerably different from those of the other MEL hitherto reported. The biosynthetic manner for MEL is thus likely to significantly vary among the Pseudozyma strains; the newly isolated strains would enable us to attain a large-scale production of MEL and to obtain various types of MEL with different hydrophobic structures.
glycolipid, biosurfactant, mannosylerythritol lipid, Pseudozyma
NCBI PubMed ID: 17505770Publication DOI: 10.1007/s00253-007-0853-8Journal NLM ID: 8406612Publisher: Springer
Correspondence: Dai Kitamoto
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Ibaraki, Japan, Faculty of Applied Information Science, Hiroshima Institute of Technology, Hiroshima, Japan
Methods: 13C NMR, 1H NMR, methylation, GC-MS, TLC, composition analysis, HPLC, extraction, phylogenetic analysis
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12. Compound ID: 18334
|
But-(1-2)-+
|
/Variants 0/-b-D-Manp4Ac-(1-4)-D-Ery-ol
/Variants 0/ is:
Pam-(1-3)-
OR (exclusively)
C16={?,?}-(1-3)-
OR (exclusively)
LIP-(1-3)- |
Show graphically |
Structure type: oligomer
Trivial name: MEL-C (4-O-[(4'-O-acetyl-3'-O-alka(e)noyl-2'-O-butanoyl)-β-D-mannopyranosyl]-D-erythritol)
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_141181,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 7166
Morita T, Konishi M, Fukuoka T, Imura T, Kitamoto D "Production of glycolipid biosurfactants, mannosylerythritol lipids, by Pseudozyma siamensis CBS 9960 and their interfacial properties" -
Journal of Bioscience and Bioengineering 105(5) (2008) 493-502
The search for a novel producer of glycolipid biosurfactants, mannosylerythritol lipids (MELs), was undertaken on the basis of the analysis of ribosomal DNA sequences of yeast strains of the genus Pseudozyma. In the course of the investigation, Pseudozyma siamensis CBS 9960, which is closely related to Pseudozyma shanxiensis, a known MEL-C producer but with a different morphology, was found to accumulate a large amount of glycolipids. On thin layer chromatography, the extracellular glycolipids showed nearly the same spots as those of the MELs produced by P. shanxiensis. However, the result of high-performance liquid chromatography analysis revealed that the present strain has a much higher glycolipid production yield than P. shanxiensis. From the structural characterization by (1)H and (13)C NMR, the major glycolipid (more than 84% of the total) was identified as a mixture of 4-O-[(2',4'-di-O-acetyl-3'-O-alka(e)noyl)-β-D-mannopyranosyl]-D-erythritol and 4-O-[(4'-O-acetyl-3'-O-alka(e)noyl-2'-O-butanoyl)-β-D-mannopyranosyl]-D-erythritol, both of which are types of MEL-C. The present MEL-C possessed a short-chain acid (C(2) or C(4)) at the C-2' position and a long-chain acid (C(16)) at the C-3' position of the mannose moiety, and thus, the hydrophobic part was considerably different from that of conventional MELs, which mainly possess two medium-chain acids (C(10)) at the C-2' and C-3' positions. Under optimal growth conditions with safflower oil in a shake culture, the total amount of MELs reached approximately 19 g/l after 9 d at 25 degrees C. We further investigated the interfacial properties of the present MEL-C, considering its unique hydrophobic structure. The observed critical micelle concentration (CMC) and the surface tension at the CMC of the MEL were 4.5 x 10(-6) M and 30.7 mN/m, respectively. In addition, on a water penetration scan, the MEL efficiently formed the liquid crystal phases such as hexagonal (H) and lamella (L(a)) at a wide range of concentrations. These results demonstrated that the newly identified MEL-C produced by P. siamensis exhibits not only high surface activity but also excellent self-assembling properties, and should facilitate the development of promising yeast biosurfactants.
glycolipid, biosurfactant, mannosylerythritol lipid, Pseudozyma, surface activity, lyotropic liquid crystal
NCBI PubMed ID: 18558340Publication DOI: 10.1263/jbb.105.493Journal NLM ID: 100888800Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
Correspondence: Dai Kitamoto
Institutions: Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, GC-MS, TLC, MALDI-TOF MS, composition analysis, HPLC, enzyme assay, extraction, microscopy, phylogenetic analysis, determination of surface tension, water penetration scan technique
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13. Compound ID: 18335
|
/Variants 0/-b-D-Manp2Ac4Ac-(1-4)-D-Ery-ol
/Variants 0/ is:
Pam-(1-3)-
OR (exclusively)
C16={?,?}-(1-3)-
OR (exclusively)
LIP-(1-3)- |
Show graphically |
Structure type: oligomer
Trivial name: MEL-C (4-O-[(2',4'-di-O-acetyl-3'-O-alka(e)noyl)-β-D-mannopyranosyl]-D-erythritol)
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_141181,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 7166
Morita T, Konishi M, Fukuoka T, Imura T, Kitamoto D "Production of glycolipid biosurfactants, mannosylerythritol lipids, by Pseudozyma siamensis CBS 9960 and their interfacial properties" -
Journal of Bioscience and Bioengineering 105(5) (2008) 493-502
The search for a novel producer of glycolipid biosurfactants, mannosylerythritol lipids (MELs), was undertaken on the basis of the analysis of ribosomal DNA sequences of yeast strains of the genus Pseudozyma. In the course of the investigation, Pseudozyma siamensis CBS 9960, which is closely related to Pseudozyma shanxiensis, a known MEL-C producer but with a different morphology, was found to accumulate a large amount of glycolipids. On thin layer chromatography, the extracellular glycolipids showed nearly the same spots as those of the MELs produced by P. shanxiensis. However, the result of high-performance liquid chromatography analysis revealed that the present strain has a much higher glycolipid production yield than P. shanxiensis. From the structural characterization by (1)H and (13)C NMR, the major glycolipid (more than 84% of the total) was identified as a mixture of 4-O-[(2',4'-di-O-acetyl-3'-O-alka(e)noyl)-β-D-mannopyranosyl]-D-erythritol and 4-O-[(4'-O-acetyl-3'-O-alka(e)noyl-2'-O-butanoyl)-β-D-mannopyranosyl]-D-erythritol, both of which are types of MEL-C. The present MEL-C possessed a short-chain acid (C(2) or C(4)) at the C-2' position and a long-chain acid (C(16)) at the C-3' position of the mannose moiety, and thus, the hydrophobic part was considerably different from that of conventional MELs, which mainly possess two medium-chain acids (C(10)) at the C-2' and C-3' positions. Under optimal growth conditions with safflower oil in a shake culture, the total amount of MELs reached approximately 19 g/l after 9 d at 25 degrees C. We further investigated the interfacial properties of the present MEL-C, considering its unique hydrophobic structure. The observed critical micelle concentration (CMC) and the surface tension at the CMC of the MEL were 4.5 x 10(-6) M and 30.7 mN/m, respectively. In addition, on a water penetration scan, the MEL efficiently formed the liquid crystal phases such as hexagonal (H) and lamella (L(a)) at a wide range of concentrations. These results demonstrated that the newly identified MEL-C produced by P. siamensis exhibits not only high surface activity but also excellent self-assembling properties, and should facilitate the development of promising yeast biosurfactants.
glycolipid, biosurfactant, mannosylerythritol lipid, Pseudozyma, surface activity, lyotropic liquid crystal
NCBI PubMed ID: 18558340Publication DOI: 10.1263/jbb.105.493Journal NLM ID: 100888800Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
Correspondence: Dai Kitamoto
Institutions: Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, GC-MS, TLC, MALDI-TOF MS, composition analysis, HPLC, enzyme assay, extraction, microscopy, phylogenetic analysis, determination of surface tension, water penetration scan technique
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14. Compound ID: 22664
|
/Variants 0/-a-D-Manp-(1-3)-Subst
/Variants 0/ is:
Ste-(1-6)-
OR (exclusively)
Pam-(1-6)-
OR (exclusively)
Myr-(1-6)-
OR (exclusively)
Lau-(1-6)-
OR (exclusively)
C18={?}-(1-6)-
OR (exclusively)
C16={?,?}-(1-6)-
OR (exclusively)
LIP-(1-6)-
Subst = cholesterol = SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC{3}[C@@H](C4)O)C)C |
Show graphically |
Structure type: monomer
Compound class: glycoside, steroid glycoside
Contained glycoepitopes: IEDB_130701,IEDB_141181,IEDB_144983,IEDB_152206,IEDB_176772,IEDB_534864,IEDB_534865,IEDB_983930,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 5704
Nguyen T, Hosono Y, Shimizu T, Yamasaki S, Williams SJ "Candida albicans steryl 6-O-acyl-α-D-mannosides agonize signalling through Mincle" -
Chemical Communications 56(95) (2020) 15060-15063
The C-type lectin receptor Mincle binds Candida albicans and has been implicated in its pathobiology, but the molecular effectors responsible have not been identified. We report the synthesis of cholesteryl and ergosteryl 6-O-acyl-α-D-mannosides, produced by C. albicans mycelium, and demonstrate their ability to signal through human and mouse Mincle.
Candida albicans, Mincle receptor, acylmannosides, tumour necrosis factor
NCBI PubMed ID: 33196722Publication DOI: 10.1039/d0cc06263dJournal NLM ID: 9610838Publisher: Cambridge: Royal Society of Chemistry
Correspondence: sjwill@unimelb.edu.au
Institutions: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Australia, Department of Molecular Immunology, Immunology Frontier Research Center, Osaka University, Suita, Japan, Department of Molecular Immunology, Research Institute for Microbial Diseases, Osaka University, Suita, Japan
Methods: ELISA, biological assays
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15. Compound ID: 22666
|
/Variants 0/-a-D-Manp-(1-3)-Subst
/Variants 0/ is:
Ste-(1-6)-
OR (exclusively)
Pam-(1-6)-
OR (exclusively)
Myr-(1-6)-
OR (exclusively)
Lau-(1-6)-
OR (exclusively)
C18={?}-(1-6)-
OR (exclusively)
C16={?,?}-(1-6)-
OR (exclusively)
LIP-(1-6)-
Subst = ergosterol = SMILES O{3}[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@@]3(C)CC4 |
Show graphically |
Structure type: monomer
Compound class: glycoside, steroid glycoside
Contained glycoepitopes: IEDB_130701,IEDB_141181,IEDB_144983,IEDB_152206,IEDB_176772,IEDB_534864,IEDB_534865,IEDB_983930,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 5704
Nguyen T, Hosono Y, Shimizu T, Yamasaki S, Williams SJ "Candida albicans steryl 6-O-acyl-α-D-mannosides agonize signalling through Mincle" -
Chemical Communications 56(95) (2020) 15060-15063
The C-type lectin receptor Mincle binds Candida albicans and has been implicated in its pathobiology, but the molecular effectors responsible have not been identified. We report the synthesis of cholesteryl and ergosteryl 6-O-acyl-α-D-mannosides, produced by C. albicans mycelium, and demonstrate their ability to signal through human and mouse Mincle.
Candida albicans, Mincle receptor, acylmannosides, tumour necrosis factor
NCBI PubMed ID: 33196722Publication DOI: 10.1039/d0cc06263dJournal NLM ID: 9610838Publisher: Cambridge: Royal Society of Chemistry
Correspondence: sjwill@unimelb.edu.au
Institutions: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Australia, Department of Molecular Immunology, Immunology Frontier Research Center, Osaka University, Suita, Japan, Department of Molecular Immunology, Research Institute for Microbial Diseases, Osaka University, Suita, Japan
Methods: ELISA, biological assays
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Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
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