Liamocins are polyol lipids produced by the fungus Aureobasidium pullulans, and have selective antibacterial activity against Streptococcus species. Liamocins produced by A. pullulans strain NRRL 50380 on sucrose medium have a d-mannitol head group ester-linked to 3,5-dihydroxydecanoate acyl chains, three or four of which are joined together by 1,5-polyester bonds (liamocins Man-A1 and Man-B1), and similar 3'-O-acetylated analogs (Man-A2 and Man-B2). However, other types of liamocins are produced depending on the choice of strain and growth conditions. In the current study, growth on different polyols, but not sugars, resulted in considerable structural variation, including liamocins with d-galactitol (dulcitol), d-sorbitol (glucitol), d- and l-arabitol, d-xylitol, l-threitol and glycerol head groups. The head groups of liamocins produced on arabitol were shown to be entirely composed of d-arabitol. These liamocin variants were structurally characterized by NMR and MS, and tested for antibacterial activity. The new liamocin variants also had selective activity against Streptococcus. Liamocin structural variants are novel antibacterials against Streptococcus sp. that merit further investigation.
NCBI PubMed ID: 27436607Publication DOI: 10.1038/ja.2016.92Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Correspondence: neil.price

ars.usda.gov
Institutions: Renewable Product Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, US Department of Agriculture, Peoria, IL, USA, Crop Bioprotection Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, US Department of Agriculture, Peoria, IL, USA, School of Biological Sciences, Illinois State University, Normal, USA
Methods: 13C NMR, 1H NMR, GC-MS, MALDI-TOF MS, HMBC, COSY
- Compound ID: 19299
|
b-D-Manp-(1-5)-+
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Subst-(5-1)-Subst3Ac-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)C{3}C(O)C{1}C(O)=O |
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Structure type: monomer
Compound class: glycolipid
- Compound ID: 19289
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D-Man-ol-(1-1)-Subst-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)CC(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 763.722 [M+Na]+
C36H68O15
Compound class: glycolipid
- Compound ID: 19290
|
D-Man-ol-(1-1)-Subst3Ac-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)C{3}C(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 805.711 [M+Na]+
C38H70O16
Compound class: glycolipid
- Compound ID: 19291
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D-Man-ol-(1-1)-Subst-(5-1)-Subst-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)CC(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 949.721 [M+Na]+
C46H86O18
Compound class: glycolipid
- Compound ID: 19292
|
D-Man-ol-(1-1)-Subst3Ac-(5-1)-Subst-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)C{3}C(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 991.695 [M+Na]+
C48H88O19
Compound class: glycolipid
- Compound ID: 19293
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D-Ara-ol-(1-1)-Subst-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)CC(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 733.756 [M+Na]+
C35H66O14
Compound class: glycolipid
- Compound ID: 19294
|
D-Ara-ol-(1-1)-Subst3Ac-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)C{3}C(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 775.758 [M+Na]+
C37H68O15
Compound class: glycolipid
- Compound ID: 19295
|
D-Ara-ol-(1-1)-Subst-(5-1)-Subst-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)CC(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 919.780 [M+Na]+
C47H86O18
Compound class: glycolipid
- Compound ID: 19296
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L-Thre-ol-(1-1)-Subst-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)CC(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 703.726 [M+Na]+
C34H64O13
Compound class: glycolipid
- Compound ID: 19297
|
L-Thre-ol-(1-1)-Subst3Ac-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)C{3}C(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 745.734 [M+Na]+
C36H66O14
Compound class: glycolipid
- Compound ID: 19298
|
L-Thre-ol-(1-1)-Subst-(5-1)-Subst-(5-1)-Subst-(5-1)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)CC(O)C{1}C(O)=O |
Show graphically |
Structure type: monomer
; 889.845 [M+Na]+
C44H82O16
Compound class: glycolipid