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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Associated disease: infection due to Candida [ICD11: XN3CL

]

The structure was elucidated in this paper
NCBI PubMed ID: 22197069
Publication DOI: 10.1016/j.carres.2011.07.016
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: 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
Location inside paper: Table 1, C, p.38, right column, paragraph 2
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, acid hydrolysis, MALDI-TOF MS, extraction, cell growth, evaporation, determination of surface tension
Comments, role: NMR solvent was not specified

Related record ID(s): 45989, 45990, 45991, 45992, 45993, 45994
NCBI Taxonomy refs (TaxIDs): 1008382
Show glycosyltransferases

NMR conditions: at 300 K [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	171.2	19.3
18,2	bDGlcp	101.6	82.4	76.1	70.0	74.2	63.4
18,6	%Ac	171.3	19.5
18	bDGlcp	104.0	74.5	76.1	70.0	73.6	63.3
	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	-	2.07
18,2	bDGlcp	4.41	3.40	3.56	3.32	3.46	4.21-4.39
18,6	%Ac	-	2.06
18	bDGlcp	4.57	3.26	3.39	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		19.3/2.07
18,2	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
18,6	%Ac		19.5/2.06
18	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
	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		2.07
18,2	bDGlcp	4.41	3.40	3.56	3.32	3.46	4.21 4.39
18,6	%Ac		2.06
18	bDGlcp	4.57	3.26	3.39	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	171.2	19.3
18,2	bDGlcp	101.6	82.4	76.1	70.0	74.2	63.4
18,6	%Ac	171.3	19.5
18	bDGlcp	104.0	74.5	76.1	70.0	73.6	63.3
	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:

$CC(=O)OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](COC(C)=O)O[C@H]2OCCCCCCCC/C=C\CCCCCCCC(=O)O)[C@H](O)[C@@H](O)[C@@H]1O$

SVG MW SMILES 3D mol Ionize