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Yamamoto S, Fukuoka T, Imura T, Morita T, Yanagidani S, Kitamoto D, Kitagawa M
Production of a novel mannosylerythritol lipid containing a hydroxy fatty acid from castor oil by Pseudozyma tsukubaensis
Journal of Oleo Science 62(6) (2013)
381-389
Pseudozyma antarctica JCM 10317T
(later renamed to: Moesziomyces antarcticus JCM 10317T)
(Ancestor NCBI TaxID 84753,
species name lookup)
Pseudozyma hubeiensis KM-59
(Ancestor NCBI TaxID 327079,
species name lookup)
Pseudozyma graminicola CBS 10092
(later renamed to: Sporisorium graminicola)
(Ancestor NCBI TaxID 280036,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 23728329Publication DOI: 10.5650/jos.62.381Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Masaru_Kitagawa
toyobo.jp
Institutions: Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan, Toyobo Co., Ltd. Tsuruga Institute of Biotechnology, Tsuruga Fukui, Japan, Toyobo Co., Ltd. Biochemical Dept., Osaka, Japan
Mannosylerythritol lipids (MELs) are glycolipid biosurfactants produced by various yeasts belonging to the genus Pseudozyma, which exhibit excellent surface activities as well as versatile biochemical activities. A study on P. tsukubaensis NBRC1940 as a mono-acetylated MEL (MEL-B) producer revealed that the yeast accumulated a novel glycolipid from castor oil at a yield of 22 g/L. Its main chemical structure was identified as 1-O-β-(2'-O-alka(e)noyl-3'-O-hydroxyalka(e)noyl-6'-O-acetyl-D-mannopyranosyl)-D-erythritol designated as "new MEL-B." The new MEL-B, comprising a hydroxy fatty acid had a reduced surface tension of 28.5 mN/m at a critical micelle concentration (CMC) of 2.2×10^-5 M in water. The observed CMC was 5-fold higher than that of conventional MEL-B. When conventional MEL-B was dispersed in water, it self-assembled to form the lamellar (L(α)) phase at a wide range of concentrations. In contrast, new MEL-B formed spherical oily droplets similar to the sponge (L3) phase, which is observed in aqueous solutions of di-acetylated MEL (MEL-A). The data suggest that the newly identified MEL-B is likely to have a different structure and interfacial properties compared to the conventional MELs, and could facilitate an increase in the application of glycolipid biosurfactants.
glycolipid, biosurfactant, mannosylerythritol lipid, Pseudozyma yeast, Hydroxy fatty acid
Structure type: oligomer
Location inside paper: MEL, fig.1
Trivial name: mannosylerythritol, MEL, mannosylerythritol, mannosylerythritol lipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, TLC, MALDI-TOF MS, HPLC, extraction, CC, determination of surface tension, self-assembling assay
Comments, role: LIP = C8-C16
Related record ID(s): 47169, 47170
NCBI Taxonomy refs (TaxIDs): 84753,
327079,
280036Reference(s) to other database(s): GenDB:AF038826
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There is only one chemically distinct structure:
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Yamamoto S, Fukuoka T, Imura T, Morita T, Yanagidani S, Kitamoto D, Kitagawa M
Production of a novel mannosylerythritol lipid containing a hydroxy fatty acid from castor oil by Pseudozyma tsukubaensis
Journal of Oleo Science 62(6) (2013)
381-389
Pseudozyma tsukubaensis NBRC 1940
(Ancestor NCBI TaxID 5483,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 23728329Publication DOI: 10.5650/jos.62.381Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Masaru_Kitagawa
toyobo.jp
Institutions: Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan, Toyobo Co., Ltd. Tsuruga Institute of Biotechnology, Tsuruga Fukui, Japan, Toyobo Co., Ltd. Biochemical Dept., Osaka, Japan
Mannosylerythritol lipids (MELs) are glycolipid biosurfactants produced by various yeasts belonging to the genus Pseudozyma, which exhibit excellent surface activities as well as versatile biochemical activities. A study on P. tsukubaensis NBRC1940 as a mono-acetylated MEL (MEL-B) producer revealed that the yeast accumulated a novel glycolipid from castor oil at a yield of 22 g/L. Its main chemical structure was identified as 1-O-β-(2'-O-alka(e)noyl-3'-O-hydroxyalka(e)noyl-6'-O-acetyl-D-mannopyranosyl)-D-erythritol designated as "new MEL-B." The new MEL-B, comprising a hydroxy fatty acid had a reduced surface tension of 28.5 mN/m at a critical micelle concentration (CMC) of 2.2×10^-5 M in water. The observed CMC was 5-fold higher than that of conventional MEL-B. When conventional MEL-B was dispersed in water, it self-assembled to form the lamellar (L(α)) phase at a wide range of concentrations. In contrast, new MEL-B formed spherical oily droplets similar to the sponge (L3) phase, which is observed in aqueous solutions of di-acetylated MEL (MEL-A). The data suggest that the newly identified MEL-B is likely to have a different structure and interfacial properties compared to the conventional MELs, and could facilitate an increase in the application of glycolipid biosurfactants.
glycolipid, biosurfactant, mannosylerythritol lipid, Pseudozyma yeast, Hydroxy fatty acid
Structure type: oligomer
Location inside paper: MEL-B, fig.1, fig.3(a), fig.6(a)
Trivial name: MEL-B (mannosylerythritol lipid), mannosylerythritol-B, MEL-B, mannosylerythritol-B, mannosylerythritol, S-mannosylerythritol-B, MEL-B
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, TLC, MALDI-TOF MS, HPLC, extraction, CC, determination of surface tension, self-assembling assay
Comments, role: substrate is olive oil; LIP = C8:0 (38.3%), C12:0 (20.1%), C14:0 (33.8%)
Related record ID(s): 47168, 47170, 49745, 49762
NCBI Taxonomy refs (TaxIDs): 5483
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There is only one chemically distinct structure:
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Yamamoto S, Fukuoka T, Imura T, Morita T, Yanagidani S, Kitamoto D, Kitagawa M
Production of a novel mannosylerythritol lipid containing a hydroxy fatty acid from castor oil by Pseudozyma tsukubaensis
Journal of Oleo Science 62(6) (2013)
381-389
|
Oco-(1-2)-+
|
Subst-(1-3)-b-D-Manp6Ac-(1-4)-D-Ery-ol
Subst = 8-hydroxytetradec-5E-enoic acid = SMILES CCCCCC{8}C(O)C/C=C/CCC{1}C(=O)O |
Show graphically |
Pseudozyma tsukubaensis NBRC 1940
(Ancestor NCBI TaxID 5483,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperNCBI PubMed ID: 23728329Publication DOI: 10.5650/jos.62.381Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Masaru_Kitagawa
toyobo.jp
Institutions: Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan, Toyobo Co., Ltd. Tsuruga Institute of Biotechnology, Tsuruga Fukui, Japan, Toyobo Co., Ltd. Biochemical Dept., Osaka, Japan
Mannosylerythritol lipids (MELs) are glycolipid biosurfactants produced by various yeasts belonging to the genus Pseudozyma, which exhibit excellent surface activities as well as versatile biochemical activities. A study on P. tsukubaensis NBRC1940 as a mono-acetylated MEL (MEL-B) producer revealed that the yeast accumulated a novel glycolipid from castor oil at a yield of 22 g/L. Its main chemical structure was identified as 1-O-β-(2'-O-alka(e)noyl-3'-O-hydroxyalka(e)noyl-6'-O-acetyl-D-mannopyranosyl)-D-erythritol designated as "new MEL-B." The new MEL-B, comprising a hydroxy fatty acid had a reduced surface tension of 28.5 mN/m at a critical micelle concentration (CMC) of 2.2×10^-5 M in water. The observed CMC was 5-fold higher than that of conventional MEL-B. When conventional MEL-B was dispersed in water, it self-assembled to form the lamellar (L(α)) phase at a wide range of concentrations. In contrast, new MEL-B formed spherical oily droplets similar to the sponge (L3) phase, which is observed in aqueous solutions of di-acetylated MEL (MEL-A). The data suggest that the newly identified MEL-B is likely to have a different structure and interfacial properties compared to the conventional MELs, and could facilitate an increase in the application of glycolipid biosurfactants.
glycolipid, biosurfactant, mannosylerythritol lipid, Pseudozyma yeast, Hydroxy fatty acid
Structure type: oligomer
Location inside paper: MEL-B, fig.1, fig.3(b), table 2, fig.6(b)
Trivial name: mannosylerythritol
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, TLC, MALDI-TOF MS, HPLC, extraction, CC, determination of surface tension, self-assembling assay
Comments, role: substrate is castor oil; LIP = C8:0 (36.5%), C14:1 (60.8%)
Related record ID(s): 47168, 47169
NCBI Taxonomy refs (TaxIDs): 5483
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14
4,2 lXOco 173.6 33.9 24.5-25.6 22.5-32.0 22.5-32.0 22.5-32.0 22.5-32.0 13.3
4,3 Subst 173.1 33.3 24.5-25.6 26.5 126.9-130.5 126.9-130.5 35.1 71.3 22.5-32.0 22.5-32.0 22.5-32.0 22.5-32.0 22.5-32.0 13.3
4,6 Ac 171.4 19.5
4 bDManp 98.8 69.4 73.8 65.0 74.5 63.4
xDEry-ol 63.4 72.3 70.9 71.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14
4,2 lXOco - 2.40 1.60-1.71 1.23-1.51 1.23-1.51 1.23-1.51 1.23-1.51 0.85-0.95
4,3 Subst - 2.29 1.60-1.71 2.02-2.14 5.30-5.43 5.30-5.43 2.20 3.56 1.23-1.51 1.23-1.51 1.23-1.51 1.23-1.51 1.23-1.51 0.85-0.95
4,6 Ac - 2.08
4 bDManp 4.85 5.45 4.93 3.75 3.62 4.27-4.45
xDEry-ol 3.56-3.70 3.57 3.68 3.85
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 C12/H12 C13/H13 C14/H14
4,2 lXOco 33.9/2.40 24.5-25.6/1.60-1.71 22.5-32.0/1.23-1.51 22.5-32.0/1.23-1.51 22.5-32.0/1.23-1.51 22.5-32.0/1.23-1.51 13.3/0.85-0.95
4,3 Subst 33.3/2.29 24.5-25.6/1.60-1.71 26.5/2.02-2.14 126.9-130.5/5.30-5.43 126.9-130.5/5.30-5.43 35.1/2.20 71.3/3.56 22.5-32.0/1.23-1.51 22.5-32.0/1.23-1.51 22.5-32.0/1.23-1.51 22.5-32.0/1.23-1.51 22.5-32.0/1.23-1.51 13.3/0.85-0.95
4,6 Ac 19.5/2.08
4 bDManp 98.8/4.85 69.4/5.45 73.8/4.93 65.0/3.75 74.5/3.62 63.4/4.27-4.45
xDEry-ol 63.4/3.56-3.70 72.3/3.57 70.9/3.68 71.5/3.85
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 |
|---|
| 4,2 | lXOco |
| 2.40 | 1.60
1.71 | 1.23
1.51 | 1.23
1.51 | 1.23
1.51 | 1.23
1.51 | 0.85
0.95 | |
| 4,3 | Subst |
| 2.29 | 1.60
1.71 | 2.02
2.14 | 5.30
5.43 | 5.30
5.43 | 2.20 | 3.56 | 1.23
1.51 | 1.23
1.51 | 1.23
1.51 | 1.23
1.51 | 1.23
1.51 | 0.85
0.95 |
| 4,6 | Ac |
| 2.08 | |
| 4 | bDManp | 4.85 | 5.45 | 4.93 | 3.75 | 3.62 | 4.27
4.45 | |
| | xDEry-ol | 3.56
3.70 | 3.57 | 3.68 | 3.85 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 |
|---|
| 4,2 | lXOco | 173.6 | 33.9 | 24.5
25.6 | 22.5
32.0 | 22.5
32.0 | 22.5
32.0 | 22.5
32.0 | 13.3 | |
| 4,3 | Subst | 173.1 | 33.3 | 24.5
25.6 | 26.5 | 126.9
130.5 | 126.9
130.5 | 35.1 | 71.3 | 22.5
32.0 | 22.5
32.0 | 22.5
32.0 | 22.5
32.0 | 22.5
32.0 | 13.3 |
| 4,6 | Ac | 171.4 | 19.5 | |
| 4 | bDManp | 98.8 | 69.4 | 73.8 | 65.0 | 74.5 | 63.4 | |
| | xDEry-ol | 63.4 | 72.3 | 70.9 | 71.5 | |
|
There is only one chemically distinct structure:
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