Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Associated disease: infection due to Candida [ICD11:
XN3CL 
]
The structure was elucidated in this paperNCBI PubMed ID: 22197069Publication DOI: 10.1016/j.carres.2011.07.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Price NP <neil.price
ars.usda.gov>
Institutions: USDA-ARS-NCAUR, Renewable Product Technology, Peoria, IL, USA, USDA-ARS-NCAUR, Functional Foods, Peoria, IL, USA, USDA-ARS-NCAUR, Crop Bioprotection, Peoria, IL, USA, USDA-ARS-NCAUR, Bacterial Foodbourne Pathogens & Mycology Research Units, Peoria, IL, USA
Sophorolipids are a group of O-acylsophorose-based biosurfactants produced by several yeasts of the Starmerella clade. The known sophorolipids are typically partially acetylated 2-O-β-D-glucopyranosyl-D-glucopyranose (sophorose) O-β-glycosidically linked to 17-L-hydroxy-Δ9-octadecenoic acid, where the acyl carboxyl group often forms a 4″-lactone to the terminal glucosyl residue. In a recent MALDI-TOFMS-based screen for sophorolipid-producing yeasts we identified a new species, Candida sp. NRRL Y-27208, that produces significant amounts of novel sophorolipids. This paper describes the structural characterization of these new compounds, using carbohydrate and lipid analysis, mass spectrometry, and NMR spectroscopy. Unlike those reported previously, the NRRL Y-27208 sophorolipids contain an ω-hydroxy-linked acyl group (typically 18-hydroxy-Δ9-octadecenoate), and occur predominantly in a non-lactone, anionic form. In addition, 17 dimeric and trimeric sophoroses were identified by MALDI-TOFMS from this strain. The surfactant-like properties of these sophorolipids have value as potential replacements for petroleum-based detergents and emulsifiers.
NMR, mass spectrometry, sophorolipids, biosurfactants, MALDI-TOFMS, starmerella
Structure type: oligomer ; 729 [M+Na]+
Location inside paper: fig. 1, p. 34, Table I (column C), fig.8
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, MALDI-TOF MS, HPLC, extraction, determination of surface tension, GC–MS
Related record ID(s): 43568, 43570, 43575, 43578, 43583, 43594, 43595, 43616
NCBI Taxonomy refs (TaxIDs): 1008382
Show glycosyltransferases
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18
18,2,6 Ac 171.3 19.5
18,2 bDGlcp 104.0 74.5 76.1 70.0 73.6 63.3
18,6 Ac 171.2 19.3
18 bDGlcp 101.6 82.4 76.1 70.0 74.2 63.4
lX18HOOle 176.3 33.6 24.7 28-30 28-30 28-30 28-30 26.7 129.4 129.4 26.7 28-30 28-30 28-30 28-30 28-30 29.3 69.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18
18,2,6 Ac - 2.06
18,2 bDGlcp 4.57 3.26 3.39 3.32 3.46 4.21-4.39
18,6 Ac - 2.07
18 bDGlcp 4.41 3.40 3.56 3.32 3.46 4.21-4.39
lX18HOOle - 2.29 1.61 1.3-1.4 1.3-1.4 1.3-1.4 1.3-1.4 2.04 5.36 5.36 2.04 1.3-1.4 1.3-1.4 1.3-1.4 1.3-1.4 1.3-1.4 1.61 3.58-3.82
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 C15/H15 C16/H16 C17/H17 C18/H18
18,2,6 Ac 19.5/2.06
18,2 bDGlcp 104.0/4.57 74.5/3.26 76.1/3.39 70.0/3.32 73.6/3.46 63.3/4.21-4.39
18,6 Ac 19.3/2.07
18 bDGlcp 101.6/4.41 82.4/3.40 76.1/3.56 70.0/3.32 74.2/3.46 63.4/4.21-4.39
lX18HOOle 33.6/2.29 24.7/1.61 28-30/1.3-1.4 28-30/1.3-1.4 28-30/1.3-1.4 28-30/1.3-1.4 26.7/2.04 129.4/5.36 129.4/5.36 26.7/2.04 28-30/1.3-1.4 28-30/1.3-1.4 28-30/1.3-1.4 28-30/1.3-1.4 28-30/1.3-1.4 29.3/1.61 69.5/3.58-3.82
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 |
|---|
| 18,2,6 | Ac |
| 2.06 | |
| 18,2 | bDGlcp | 4.57 | 3.26 | 3.39 | 3.32 | 3.46 | 4.21
4.39 | |
| 18,6 | Ac |
| 2.07 | |
| 18 | bDGlcp | 4.41 | 3.40 | 3.56 | 3.32 | 3.46 | 4.21
4.39 | |
| | lX18HOOle |
| 2.29 | 1.61 | 1.3
1.4 | 1.3
1.4 | 1.3
1.4 | 1.3
1.4 | 2.04 | 5.36 | 5.36 | 2.04 | 1.3
1.4 | 1.3
1.4 | 1.3
1.4 | 1.3
1.4 | 1.3
1.4 | 1.61 | 3.58
3.82 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 |
|---|
| 18,2,6 | Ac | 171.3 | 19.5 | |
| 18,2 | bDGlcp | 104.0 | 74.5 | 76.1 | 70.0 | 73.6 | 63.3 | |
| 18,6 | Ac | 171.2 | 19.3 | |
| 18 | bDGlcp | 101.6 | 82.4 | 76.1 | 70.0 | 74.2 | 63.4 | |
| | lX18HOOle | 176.3 | 33.6 | 24.7 | 28
30 | 28
30 | 28
30 | 28
30 | 26.7 | 129.4 | 129.4 | 26.7 | 28
30 | 28
30 | 28
30 | 28
30 | 28
30 | 29.3 | 69.5 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
(previously named: Candida kuoi; later renamed to: Starmerella kuoi)