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Manitchotpisit P, Watanapokasin R, Price NP, Bischoff KM, Tayeh M, Teeraworawit S, Kriwong S, Leathers TD
Aureobasidium pullulans as a source of liamocins (heavy oils) with anticancer activity
World Journal of Microbiology and Biotechnology 30(8) (2014)
2199-2204
|
D-Man-ol-(1-1)-+
|
Subst-(1-5)-Subst-(1-5)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)CC(O)C{1}C(O)=O |
Show graphically |
Aureobasidium pullulans NRRL 62041
(previously named: Dematium pullulans NRRL 62041)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 50382
(previously named: Dematium pullulans NRRL 50382)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62034
(previously named: Dematium pullulans NRRL 62034)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62038
(previously named: Dematium pullulans NRRL 62038)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62039
(previously named: Dematium pullulans NRRL 62039)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62040
(previously named: Dematium pullulans NRRL 62040)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62031
(previously named: Dematium pullulans NRRL 62031)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62042
(previously named: Dematium pullulans NRRL 62042)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 50384
(previously named: Dematium pullulans NRRL 50384)
(Ancestor NCBI TaxID 5580,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
NCBI PubMed ID: 24659335Publication DOI: 10.1007/s11274-014-1639-7Journal NLM ID: 9012472Correspondence: Leathers TD <tim.leathers
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, Department of Medical Sciences, Faculty of Science, Rangsit University, Pathumthani, Thailand, Department of Biochemistry, Faculty of Medicine, Srinakharinwirot University, Bangkok, Thailand
Liamocins are structurally unique, heavier-than-water “oils” produced by certain strains of Aureobasidium pullulans. The aim of the current study is to identify new sources of liamocins and evaluate their potential as anticancer agents. Nine strains of A. pullulans from phylogenetic clades 8, 9, and 11 were examined for the first time for production of liamocins. Strains in these clades have only been isolated from tropical environments, and all strains tested here were from various locations in Thailand. Strains RSU 9, RSU 21, and RSU 29, all from clade 11, produced from 7.0 to 8.6 g liamocins/l from medium containing 5 % sucrose. These are the highest yields of liamocins that we have found thus far. These strains also produced from 9.4 to 17 g pullulan/l. The structural identity of liamocins was confirmed by matrix-assisted laser desorption/ionization mass spectrometry; differential spectra were obtained in which the dominant ion was either at about m/z 805.5 or m/z 949.6, consistent with the structure of liamocins. Liamocins from A. pullulans strains RSU 9 and RSU 21 inhibited two human breast cancer cell lines and a human cervical cancer cell line (IC50 values of 32.2 ± 1.4 to 63.1 ± 2.4 μg liamocins/ml) but were not toxic to a normal cell line. Liamocins weakly inhibited a strain of Enterococcus faecalis, but did not inhibit strains of Lactobacillus fermentum, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. Thus, A. pullulans phylogenetic clade 11 is a promising source of liamocins, and these compounds merit further examination as potential anticancer agents.
phylogeny, pullulan, Aureobasidium pullulans, liamocins, anticancer agents
Structure type: monomer ; 764.92 (NRRL 50382), 764.93 (NRRL 62034), 764.70 (NRRL 62038), 765.34 (NRRL 62039), 764.66 (NRRL 62040), 764.32 (NRRL 62031), 766.13 (NRRL 50384)
C
36H
68O
15Location inside paper: fig. 1 (liamocin A1), fig. 2
Trivial name: liamocin A1
Compound class: glycolipid
Contained glycoepitopes: IEDB_114705
Methods: extraction, antibacterial assay, anticancer activity assay, MALDI–TOF MS
Biological activity: Liamocins from A. pullulans strains NRRL 62031 and NRRL 62042 inhibited two human breast cancer cell lines (SK-BR-3 and T47D) and a human cervical cancer cell line (HeLa) (IC50 values of 32.2±1.4 to 63.1±2.4 μg liamocins/ml) but were not toxic to a normal cell line; liamocins obtained from the other strains appeared to be less active. Liamocins weakly inhibited a strain of Enterococcus faecalis with MIC values of 156-615 μg liamocin/ml.
Synthetic data: biosynthesis
Related record ID(s): 47469, 47470, 47471
NCBI Taxonomy refs (TaxIDs): 5580
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
Collapse this record
Manitchotpisit P, Watanapokasin R, Price NP, Bischoff KM, Tayeh M, Teeraworawit S, Kriwong S, Leathers TD
Aureobasidium pullulans as a source of liamocins (heavy oils) with anticancer activity
World Journal of Microbiology and Biotechnology 30(8) (2014)
2199-2204
|
D-Man-ol-(1-1)-+
|
Subst-(1-5)-Subst-(1-5)-Subst3Ac
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)C{3}C(O)C{1}C(O)=O |
Show graphically |
Aureobasidium pullulans NRRL 62041
(previously named: Dematium pullulans NRRL 62041)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 50382
(previously named: Dematium pullulans NRRL 50382)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62034
(previously named: Dematium pullulans NRRL 62034)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62038
(previously named: Dematium pullulans NRRL 62038)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62039
(previously named: Dematium pullulans NRRL 62039)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62040
(previously named: Dematium pullulans NRRL 62040)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62031
(previously named: Dematium pullulans NRRL 62031)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62042
(previously named: Dematium pullulans NRRL 62042)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 50384
(previously named: Dematium pullulans NRRL 50384)
(Ancestor NCBI TaxID 5580,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
NCBI PubMed ID: 24659335Publication DOI: 10.1007/s11274-014-1639-7Journal NLM ID: 9012472Correspondence: Leathers TD <tim.leathers
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, Department of Medical Sciences, Faculty of Science, Rangsit University, Pathumthani, Thailand, Department of Biochemistry, Faculty of Medicine, Srinakharinwirot University, Bangkok, Thailand
Liamocins are structurally unique, heavier-than-water “oils” produced by certain strains of Aureobasidium pullulans. The aim of the current study is to identify new sources of liamocins and evaluate their potential as anticancer agents. Nine strains of A. pullulans from phylogenetic clades 8, 9, and 11 were examined for the first time for production of liamocins. Strains in these clades have only been isolated from tropical environments, and all strains tested here were from various locations in Thailand. Strains RSU 9, RSU 21, and RSU 29, all from clade 11, produced from 7.0 to 8.6 g liamocins/l from medium containing 5 % sucrose. These are the highest yields of liamocins that we have found thus far. These strains also produced from 9.4 to 17 g pullulan/l. The structural identity of liamocins was confirmed by matrix-assisted laser desorption/ionization mass spectrometry; differential spectra were obtained in which the dominant ion was either at about m/z 805.5 or m/z 949.6, consistent with the structure of liamocins. Liamocins from A. pullulans strains RSU 9 and RSU 21 inhibited two human breast cancer cell lines and a human cervical cancer cell line (IC50 values of 32.2 ± 1.4 to 63.1 ± 2.4 μg liamocins/ml) but were not toxic to a normal cell line. Liamocins weakly inhibited a strain of Enterococcus faecalis, but did not inhibit strains of Lactobacillus fermentum, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. Thus, A. pullulans phylogenetic clade 11 is a promising source of liamocins, and these compounds merit further examination as potential anticancer agents.
phylogeny, pullulan, Aureobasidium pullulans, liamocins, anticancer agents
Structure type: monomer ; 807.47 (NRRL 62041), 806.87 (NRRL 50382), 806.49 (NRRL 62034), 806.99 (NRRL 62038), 807.13 (NRRL 62039), 806.58 (NRRL 62040), 806.38 (NRRL 62031), 805.92 (NRRL 62042), 808.09 (NRRL 50384)
C
36H
68O
15Location inside paper: fig. 1 (liamocin A2), fig. 2
Trivial name: liamocin A2
Compound class: glycolipid
Contained glycoepitopes: IEDB_114705
Methods: extraction, antibacterial assay, anticancer activity assay, MALDI–TOF MS
Biological activity: Liamocins from A. pullulans strains NRRL 62031 and NRRL 62042 inhibited two human breast cancer cell lines (SK-BR-3 and T47D) and a human cervical cancer cell line (HeLa) (IC50 values of 32.2±1.4 to 63.1±2.4 μg liamocins/ml) but were not toxic to a normal cell line; liamocins obtained from the other strains appeared to be less active. Liamocins weakly inhibited a strain of Enterococcus faecalis with MIC values of 156-615 μg liamocin/ml.
Synthetic data: biosynthesis
Related record ID(s): 47468, 47470, 47471
NCBI Taxonomy refs (TaxIDs): 5580
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
Collapse this record
Manitchotpisit P, Watanapokasin R, Price NP, Bischoff KM, Tayeh M, Teeraworawit S, Kriwong S, Leathers TD
Aureobasidium pullulans as a source of liamocins (heavy oils) with anticancer activity
World Journal of Microbiology and Biotechnology 30(8) (2014)
2199-2204
|
D-Man-ol-(1-1)-+
|
Subst-(1-5)-Subst-(1-5)-Subst-(1-5)-Subst
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)CC(O)C{1}C(O)=O |
Show graphically |
Aureobasidium pullulans NRRL 62041
(previously named: Dematium pullulans NRRL 62041)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 50382
(previously named: Dematium pullulans NRRL 50382)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62034
(previously named: Dematium pullulans NRRL 62034)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62038
(previously named: Dematium pullulans NRRL 62038)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62039
(previously named: Dematium pullulans NRRL 62039)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62040
(previously named: Dematium pullulans NRRL 62040)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62031
(previously named: Dematium pullulans NRRL 62031)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62042
(previously named: Dematium pullulans NRRL 62042)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 50384
(previously named: Dematium pullulans NRRL 50384)
(Ancestor NCBI TaxID 5580,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
NCBI PubMed ID: 24659335Publication DOI: 10.1007/s11274-014-1639-7Journal NLM ID: 9012472Correspondence: Leathers TD <tim.leathers
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, Department of Medical Sciences, Faculty of Science, Rangsit University, Pathumthani, Thailand, Department of Biochemistry, Faculty of Medicine, Srinakharinwirot University, Bangkok, Thailand
Liamocins are structurally unique, heavier-than-water “oils” produced by certain strains of Aureobasidium pullulans. The aim of the current study is to identify new sources of liamocins and evaluate their potential as anticancer agents. Nine strains of A. pullulans from phylogenetic clades 8, 9, and 11 were examined for the first time for production of liamocins. Strains in these clades have only been isolated from tropical environments, and all strains tested here were from various locations in Thailand. Strains RSU 9, RSU 21, and RSU 29, all from clade 11, produced from 7.0 to 8.6 g liamocins/l from medium containing 5 % sucrose. These are the highest yields of liamocins that we have found thus far. These strains also produced from 9.4 to 17 g pullulan/l. The structural identity of liamocins was confirmed by matrix-assisted laser desorption/ionization mass spectrometry; differential spectra were obtained in which the dominant ion was either at about m/z 805.5 or m/z 949.6, consistent with the structure of liamocins. Liamocins from A. pullulans strains RSU 9 and RSU 21 inhibited two human breast cancer cell lines and a human cervical cancer cell line (IC50 values of 32.2 ± 1.4 to 63.1 ± 2.4 μg liamocins/ml) but were not toxic to a normal cell line. Liamocins weakly inhibited a strain of Enterococcus faecalis, but did not inhibit strains of Lactobacillus fermentum, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. Thus, A. pullulans phylogenetic clade 11 is a promising source of liamocins, and these compounds merit further examination as potential anticancer agents.
phylogeny, pullulan, Aureobasidium pullulans, liamocins, anticancer agents
Structure type: monomer ; 951.56 (NRRL 62041), 951.56 (NRRL 50382), 950.61 (NRRL 62034), 951.26 (NRRL 62038), 951.32 (NRRL 62039), 951.40 (NRRL 62040), 950.42 (NRRL 62031), 950.00 (NRRL 62042), 952.43 (NRRL 50384)
C
36H
68O
15Location inside paper: fig. 1 (liamocin B1), fig. 2
Trivial name: liamocin B1
Compound class: glycolipid
Contained glycoepitopes: IEDB_114705
Methods: extraction, antibacterial assay, anticancer activity assay, MALDI–TOF MS
Biological activity: Liamocins from A. pullulans strains NRRL 62031 and NRRL 62042 inhibited two human breast cancer cell lines (SK-BR-3 and T47D) and a human cervical cancer cell line (HeLa) (IC50 values of 32.2±1.4 to 63.1±2.4 μg liamocins/ml) but were not toxic to a normal cell line; liamocins obtained from the other strains appeared to be less active. Liamocins weakly inhibited a strain of Enterococcus faecalis with MIC values of 156-615 μg liamocin/ml.
Synthetic data: biosynthesis
Related record ID(s): 47468, 47469, 47471
NCBI Taxonomy refs (TaxIDs): 5580
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
Collapse this record
Manitchotpisit P, Watanapokasin R, Price NP, Bischoff KM, Tayeh M, Teeraworawit S, Kriwong S, Leathers TD
Aureobasidium pullulans as a source of liamocins (heavy oils) with anticancer activity
World Journal of Microbiology and Biotechnology 30(8) (2014)
2199-2204
|
D-Man-ol-(1-1)-+
|
Subst-(1-5)-Subst-(1-5)-Subst-(1-5)-Subst3Ac
Subst = 3,5-dihydroxydecanoic acid = SMILES CCCCC{5}C(O)C{3}C(O)C{1}C(O)=O |
Show graphically |
Aureobasidium pullulans NRRL 62041
(previously named: Dematium pullulans NRRL 62041)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 50382
(previously named: Dematium pullulans NRRL 50382)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62034
(previously named: Dematium pullulans NRRL 62034)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62038
(previously named: Dematium pullulans NRRL 62038)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62039
(previously named: Dematium pullulans NRRL 62039)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62040
(previously named: Dematium pullulans NRRL 62040)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62031
(previously named: Dematium pullulans NRRL 62031)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 62042
(previously named: Dematium pullulans NRRL 62042)
(Ancestor NCBI TaxID 5580,
species name lookup)
Aureobasidium pullulans NRRL 50384
(previously named: Dematium pullulans NRRL 50384)
(Ancestor NCBI TaxID 5580,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
NCBI PubMed ID: 24659335Publication DOI: 10.1007/s11274-014-1639-7Journal NLM ID: 9012472Correspondence: Leathers TD <tim.leathers
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, Department of Medical Sciences, Faculty of Science, Rangsit University, Pathumthani, Thailand, Department of Biochemistry, Faculty of Medicine, Srinakharinwirot University, Bangkok, Thailand
Liamocins are structurally unique, heavier-than-water “oils” produced by certain strains of Aureobasidium pullulans. The aim of the current study is to identify new sources of liamocins and evaluate their potential as anticancer agents. Nine strains of A. pullulans from phylogenetic clades 8, 9, and 11 were examined for the first time for production of liamocins. Strains in these clades have only been isolated from tropical environments, and all strains tested here were from various locations in Thailand. Strains RSU 9, RSU 21, and RSU 29, all from clade 11, produced from 7.0 to 8.6 g liamocins/l from medium containing 5 % sucrose. These are the highest yields of liamocins that we have found thus far. These strains also produced from 9.4 to 17 g pullulan/l. The structural identity of liamocins was confirmed by matrix-assisted laser desorption/ionization mass spectrometry; differential spectra were obtained in which the dominant ion was either at about m/z 805.5 or m/z 949.6, consistent with the structure of liamocins. Liamocins from A. pullulans strains RSU 9 and RSU 21 inhibited two human breast cancer cell lines and a human cervical cancer cell line (IC50 values of 32.2 ± 1.4 to 63.1 ± 2.4 μg liamocins/ml) but were not toxic to a normal cell line. Liamocins weakly inhibited a strain of Enterococcus faecalis, but did not inhibit strains of Lactobacillus fermentum, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. Thus, A. pullulans phylogenetic clade 11 is a promising source of liamocins, and these compounds merit further examination as potential anticancer agents.
phylogeny, pullulan, Aureobasidium pullulans, liamocins, anticancer agents
Structure type: monomer ; 967.45 (NRRL 62041), 967.58 (NRRL 50382), 966.43 (NRRL 62034), 967.20 (NRRL 62038), 967.38 (NRRL 62039), 967.33 (NRRL 62040), 966.37 (NRRL 62031), 965.98 (NRRL 62042), 968.28 (NRRL 50384)
C
36H
68O
15Location inside paper: fig. 1 (liamocin B2), fig. 2
Trivial name: liamocin B2
Compound class: glycolipid
Contained glycoepitopes: IEDB_114705
Methods: extraction, antibacterial assay, anticancer activity assay, MALDI–TOF MS
Biological activity: Liamocins from A. pullulans strains NRRL 62031 and NRRL 62042 inhibited two human breast cancer cell lines (SK-BR-3 and T47D) and a human cervical cancer cell line (HeLa) (IC50 values of 32.2±1.4 to 63.1±2.4 μg liamocins/ml) but were not toxic to a normal cell line; liamocins obtained from the other strains appeared to be less active. Liamocins weakly inhibited a strain of Enterococcus faecalis with MIC values of 156-615 μg liamocin/ml.
Synthetic data: biosynthesis
Related record ID(s): 47468, 47469, 47470
NCBI Taxonomy refs (TaxIDs): 5580
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
Collapse this record
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