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 ; 1980.10 [M+Na]+, 2022.10 [M+Na]+, 2064.11 [M+Na]+, 2106.11 [M+Na]+
Location inside paper: fig. 4, structure N, structure O, structure P, structure Q
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
Comments, role: Structure N is tri-O-acetyl trimer with ion mass 1980.10 [M+Na]+; structure O is tetra-O-acetyl trimer with ion mass 2022.10 [M+Na]+; structure P is penta-O-acetyl trimer with ion mass 2064.11 [M+Na]+; structure Q is hexa-O-acetyl trimer with ion mass 2106.11 [M+Na]+.
Related record ID(s): 43568, 43569, 43570, 43575, 43578, 43594, 43595, 43616, 48567
NCBI Taxonomy refs (TaxIDs): 1008382
Show glycosyltransferases
There is only one chemically distinct structure:
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(previously named: Candida kuoi; later renamed to: Starmerella kuoi)