Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: cell wallAssociated disease: infection due to Candida [ICD11:
XN3CL 
]
The structure was elucidated in this paperNCBI PubMed ID: 10570818Journal NLM ID: 8406612Publisher: Springer
Correspondence: bdyoon
kribb4680.kribb.re.kr
Institutions: Environmental Microbiology, Korea Research Institute of Bioscience and Biotechnology, Taejeon, South Korea, Laboratory of Cell Biotechnology, Graduate School of Biological Sciences, Nara Institute of Science and Technology, Nara, Japan
One yeast strain, SY16, was selected as a potential producer of a biosurfactant, and identified as a Candida species. A biosurfactant produced from Candida sp. SY16 was purified and confirmed to be a glycolipid. This glycolipid-type biosurfactant lowered the surface tension of water to 29 dyne/cm at critical micelle concentration of 10 mg/l (1.5 x 10(-5) M), and the minimum interfacial tension was 0.1 dyne/cm against kerosene. Thin-layer and high-pressure liquid chromatography studies demonstrated that the glycolipid contained mannosylerythritol as a hydrophilic moiety. The hydrophilic sugar moiety of the biosurfactant was determined to be β-D-mannopyranosyl-(1→4)-O-meso-erythritol by nuclear magnetic resonance (NMR) and fast atom bombardment mass-spectroscopy analyses. The hydrophobic moiety, fatty acids, of the biosurfactant was determined to be hexanoic, dodecanoic, tetradecanoic, and tetradecenoic acid by gas chromatography-mass spectroscopy. The structure of the native biosurfactant was determined to be 6-O-acetyl-2,3-di-O-alkanoyl-β-D-mannopyranosyl-(1→4)-O-meso- erythritol by NMR analyses. We newly determined that an acetyl group was linked to the C-6 position of the D-mannose unit in the hydrophilic sugar moiety.
mannosylerythritol
Structure type: oligomer
Location inside paper: p.720, fig.5, MEL-SY16, table 2,fig.2,fig.3ab,table 3, table 4, fig.4
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, methylation, NMR-2D, FAB-MS, GC-MS, TLC, NMR-1D, HPLC, extraction, CC, determination of surface tension
Comments, role: NMR data in CD3OD are also published; LIP is saturated or unsaturated fatty acids with a chain length of C6, C12, or C14
Related record ID(s): 40404, 40568, 40569, 41261, 41747, 41759, 41792, 41803, 41838, 41962, 41963, 41967, 42021, 42022, 42095, 42096, 42097, 42192, 42193, 42194, 42277, 42283, 42284, 42299, 43338, 43339, 43340, 43341, 43342, 43404, 43412, 43413, 43414, 43415, 43416
NCBI Taxonomy refs (TaxIDs): 304695
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,2 LIP
4,3 LIP
4,6 Ac
4 bDManp 102.7 73.5 75.6 69.6 78.9 63.7
xDEry-ol 65.2 72.9 74.2 72.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,2 LIP
4,3 LIP
4,6 Ac
4 bDManp 4.67 4.00 3.62 3.53 3.35 3.72-3.88
xDEry-ol 3.62-3.73 3.77 3.72 3.83-3.94
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,2 LIP
4,3 LIP
4,6 Ac
4 bDManp 102.7/4.67 73.5/4.00 75.6/3.62 69.6/3.53 78.9/3.35 63.7/3.72-3.88
xDEry-ol 65.2/3.62-3.73 72.9/3.77 74.2/3.72 72.9/3.83-3.94
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,2 | LIP | |
| 4,3 | LIP | |
| 4,6 | Ac | |
| 4 | bDManp | 4.67 | 4.00 | 3.62 | 3.53 | 3.35 | 3.72
3.88 |
| | xDEry-ol | 3.62
3.73 | 3.77 | 3.72 | 3.83
3.94 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,2 | LIP | |
| 4,3 | LIP | |
| 4,6 | Ac | |
| 4 | bDManp | 102.7 | 73.5 | 75.6 | 69.6 | 78.9 | 63.7 |
| | xDEry-ol | 65.2 | 72.9 | 74.2 | 72.9 | |
|
There is only one chemically distinct structure:
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