Found 13 structures.
Displayed structures from 1 to 13
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1. Compound ID: 18452
| Cyclic
?%Ac-6)-+
|
-2)-/Variants 0/-b-D-Glcp6(%)Ac-(1-
/Variants 0/ is:
b-D-Glcp-(1-16)-16HOPam-(1-4)-
OR (exclusively)
b-D-Glcp-(1-15)-15HOPam-(1-4)- |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=1
Trivial name: lactone sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7246
Hommel RK, Weber L, Weiss A, Himmelreich U, Rilke O, Kleber H-P "Production of sophorose lipid by Candida (Torulopsis) apicola grown on glucose" -
Journal of Biotechnology 33(2) (1994) 147-155
The production of extracellular sophorose lipid by Candida apicola IMET 43747 was studied after growth on glucose as sole carbon source. In the presence of citrate and after 120 h of cultivation, the microcrystalline lactonic sophorose lipid started to appear in the medium. The lipid was shown to accumulate in the cell wall and only a minor part was liberated into the medium. By means of NMR studies it was shown that the cell wall-bound and the liberated lactonic sophorose lipid were identical and had a hydroxy Δ8-hexadecenoic acid backbone. Biotransformation of d-[1-13C]glucose revealed that in glucose-grown cells glucose was degraded to trioses which were rearranged and flow backward via the gluconeogenic pathway into the glycolipid as documented by scrambling of the 13C label from the C-1 position into the d-[6-13C]glucose of sophorose. A further part of the trioses was used for de novo synthesis of the glycolipid fatty acid moiety via acetyl-CoA. By use of a mixed substrate, i.e., glucose and hexadecane, part of the glucose added was directly incorporated into the carbohydrate moiety of the lipid. These results are discussed in terms of the physiological significance of the sophorose lipid to act as extracellular carbon storage material.
NMR spectroscopy, electron microscopy, Candida (Torulopsis) apicola, Candida (Torulopsis) bombicola, sophorose lipid, biosurfactant formation, biotransformation, glycolysis, gluconeogenesis
Publication DOI: 10.1016/0168-1656(94)90107-4Journal NLM ID: 8411927Publisher: Amsterdam: Elsevier
Institutions: Cell Technologie Leipzig, Leipzig, Germany, Hoffmann-La Roche, Basel, Switzerland, Anatomisches Institut, Leipzig, Germany, FB Chemie, Leipzig, Germany, Medizinische Akademie, Dresden, Germany, FB Biowissenschaften Biochemie, Leipzig, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, NMR-1D, extraction, HPTLC
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2. Compound ID: 18649
Structure type: oligomer
; 638, 680
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7320
Ma XJ, Li H, Shao LJ, Shen J, Song X "Effects of nitrogen sources on production and composition of sophorolipids by Wickerhamiella domercqiae var. sophorolipid CGMCC 1576." -
Applied Microbiology and Biotechnology 91(6) (2011) 1623-1632
The effects of nitrogen sources on growth of sophorolipid-producing yeast, Wickerhamiella domercqiae var. sophorolipid CGMCC 1576 and on production and composition of sophorolipids were studied. Organic nitrogen sources are more favorable for accumulation of biomass than inorganic ones. Presence of ammonium ion from different inorganic nitrogen sources (except NH(4)HCO(3)) greatly inhibited the production of lactonic sophorolipids. However, when organic nitrogen sources were used, lactonic sophorolipid production was strongly increased. Production of crystalline lactonic sophorolipids from organic/inorganic nitrogen sources was enhanced with the increase of pH value adjusted by sodium hydroxide or sodium citrate solution. Fourier-transform infrared (FT-IR), gas chromatography mass spectrometry (GC-MS), high-performance liquid chromatography (HPLC), and mass spectra (MS) were employed to compare the composition of sophorolipid mixture obtained from different nitrogen sources. More than 15 acidic sophorolipid molecules and only 4 lactonic sophorolipid molecules were produced by using 1.27 g/l ammonium sulfate as nitrogen source; they were separated by preparative HPLC and their structures were elucidated by MS. These results suggest extraordinary regulatory effects of nitrogen source on growth and sophorolipid synthesis of W. domercqiae var. sophorolipid.
Wickerhamiella domercqiae var. sophorolipid CGMCC 1576, Lactonic sophorolipid, Acidic sophorolipid, Organic nitrogen source, Inorganic nitrogen source
NCBI PubMed ID: 21590287Publication DOI: 10.1007/s00253-011-3327-yJournal NLM ID: 8406612Publisher: Springer
Correspondence: Ma XJ
Institutions: State Key Laboratory of Microbial Technology and National Glycoengineering Research Centre, Shandong University, Jinan, China
Methods: GC-MS, MS, FTIR, HPLC
- Article ID: 7870
Yang X, Zhu L, Xue C, Chen Y, Qu L, Lu W "Recovery of purified lactonic sophorolipids by spontaneous crystallization during the fermentation of sugarcane molasses with Candida albicans O-13-1" -
Enzyme and Microbial Technology 51(6-7) (2012) 348-353
Numerous studies have focused on how to obtain high yield of sophorolipids using low-cost materials as substrates, and there has been various work on the experimental methods for purifying lactonic sophorolipids. These studies have not yet obtained satisfied results in combining a low-cost fermentation process and the purification of lactonic sophorolipids. This study establishes a fed-batch fermentation process of purifying sophorolipids from Candida albicans O-13-1 using low-cost sugarcane molasses as the substrate. In the optimized conditions of this research, using sugarcane molasses as a substrate and product synthesis based on the temperature stage-controlled fermentation, our result indicates that sophorolipids production could reach 108.7 g/L. More importantly, lactonic sophorolipids can crystallize and precipitate during our established fermentation process. The structures and content of sophorolipids separated from the fermentation broth and sophorolipids crystallized in the fermentation broth were analyzed by a scanning electron microscope (SEM) and liquid chromatography-mass spectrometry (LC-MS). The fermentation process produced 90.5 g/L crystallized lactonic sophorolipids with 90.51% purity. This is an energy-saving and low-cost method to obtain such pure lactonic sophorolipids.
Candida albicans, Crystallization, Lactonic sophorolipid, molasses, soybean oil, temperature stage-control
NCBI PubMed ID: 23040390Publication DOI: 10.1016/j.enzmictec.2012.08.002Journal NLM ID: 8003761Correspondence: Lu W
Institutions: Department of Biological Engineering and Key Laboratory of Systems, Bioengineering of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin, China, China Offshore Environmental Service Ltd., Tianjin, China
Methods: HPLC, extraction, microscopy, LC-MS, cell growth, SEM
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3. Compound ID: 18651
Structure type: cyclic polymer repeating unit
; n=1
Compound class: glycolipid, sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7321
Takahashi M, Morita T, Wada K, Hirose N, Fukuoka T, Imura T, Kitamoto D "Production of sophorolipid glycolipid biosurfactants from sugarcane molasses using Starmerella bombicola NBRC 10243" -
Journal of Oleo Science 60(5) (2011) 267-273
Biosurfactants (BS) are produced by a variety of microorganisms from renewable resources, and have unique properties compared to chemical surfactants. In order to attain efficient production of BS from low-cost materials, we focused our attention on the use of sugarcane molasses. Fifteen yeast strains that are known as BS producers were examined for BS productivity from a culture medium consisting of only molasses and water. Among the strains tested, only Starmerella bombicola NBRC 10243 produced sophorolipids (SL), which are glycolipid BS. The culture conditions for the yeast were then investigated in a shake-flask culture. SL production was significantly affected by the pH of the medium and was highly accelerated at pH 6. Under the optimum conditions, the amount of SL reached 14.4 g/L after 120 h from a medium containing 150 g/L of total sugars. We tried to improve the production of SL further by feeding the molasses using a jar fermentor. Interestingly, the amount of SL increased up to 22.8 g/L after 120 h; the production rate was 1.6-fold higher than that in the shake-flask culture. These results suggest that the present yeast should have great potential for the low-cost production of SL, and facilitate the application of BS in various fields.
sophorolipids, yeast, glycolipid biosurfactant, sugarcane molasses, Starmerella bombicola
NCBI PubMed ID: 21502725Publication DOI: 10.5650/jos.60.267Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Kitamoto D
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central, Tsukuba, Japan, Okinawa Prefectural Agricultural Research Center, Okinawa, Japan, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology AIST, AIST Tsukuba Central, Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, TLC, MALDI-TOF MS, HPLC, extraction, GS-MS, COSY, HPLC-ELSD
- Article ID: 9107
Weber L, Stach J, Haufe G, Hommel R, Kleber HP "Elucidation of the structure of an unusual cyclic glycolipid from Torulopsis apicola" -
Carbohydrate Research 206(1) (1990) 13-19
The yeast Torulopsis apicola produces a microcrystalline mixture of glycolipids, the major component of which has been identified as the novel 16-(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)hexadecanoic acid l',4''-lactone 6',6''-diacetate (2) by spectroscopic methods.
glycolipid, Candida apicola, lactone, Torulopsis apicola
NCBI PubMed ID: 2081340Publication DOI: 10.1016/0008-6215(90)84002-cJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Karl-Marx-University, Leipzig, Germany, Department of Biosciences-Biochemistry, Karl-Marx-University, Leipzig, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, cell growth
- Article ID: 9344
da Fontoura ICC, Saikawa GIA, Silveira VAI, Pan NC, Amador IR, Baldo C, da Rocha SPD, Celligoi MAPC "Antibacterial activity of sophorolipids from Candida bombicola against human pathogens" -
Brazilian Archives of Biology and Technology 63 (2020) ID e20180568
Sophorolipids are glycolipids that have natural antimicrobial properties and present great potential in the pharmaceutical field. The present study aimed to produce sophorolipids from Candida bombicola using a chicken fat-based medium and evaluate the antimicrobial activity against Gram-negative (Proteus mirabilis, Escherichia coli, Salmonella enterica subsp. enterica) and Gram-positive bacteria (Enterococcus faecium, Staphylococcus aureus and Streptococcus mutans). The production of sophorolipids reached 27.86 g/L. Based on the structural characterization, 73.55% of the sophorolipids present a mixture of acidic monoacetylated C18:2 and lactonic diacetylated C16:0, and 26.45% were present in the diacetylated C18:1 lactonic form. Bacteria submitted to sophorolipid exposure showed a reduction in viability at doses of 500 μg/mL and 2,000 μg/mL against Gram-positive and Gram-negative bacteria, respectively. These results suggest that sophorolipids produced in chicken fat medium may be used as antimicrobial agents to prevent or eliminate contamination by different pathogens.
biosurfactant, sophorolipids, Candida bombicola, lipid residue, antibacterial properties
Publication DOI: 10.1590/1678-4324-2020180568Journal NLM ID: 9815356Publisher: Curitiba, Paraná: Instituto de Tecnologia do Paraná
Correspondence: macelligoi@uel.br
Institutions: Department of Biochemistry and Biotechnology, State University of Londrina, Londrina, Brazil, Department of Microbiology, State University of Londrina, Londrina, Brazil
Methods: TLC, ESI-MS, HPLC, extraction, cell growth, antibacterial assay, phenol-sulfuric acid assay, centrifugation
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4. Compound ID: 18652
Structure type: cyclic polymer repeating unit
; n=1
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7321
Takahashi M, Morita T, Wada K, Hirose N, Fukuoka T, Imura T, Kitamoto D "Production of sophorolipid glycolipid biosurfactants from sugarcane molasses using Starmerella bombicola NBRC 10243" -
Journal of Oleo Science 60(5) (2011) 267-273
Biosurfactants (BS) are produced by a variety of microorganisms from renewable resources, and have unique properties compared to chemical surfactants. In order to attain efficient production of BS from low-cost materials, we focused our attention on the use of sugarcane molasses. Fifteen yeast strains that are known as BS producers were examined for BS productivity from a culture medium consisting of only molasses and water. Among the strains tested, only Starmerella bombicola NBRC 10243 produced sophorolipids (SL), which are glycolipid BS. The culture conditions for the yeast were then investigated in a shake-flask culture. SL production was significantly affected by the pH of the medium and was highly accelerated at pH 6. Under the optimum conditions, the amount of SL reached 14.4 g/L after 120 h from a medium containing 150 g/L of total sugars. We tried to improve the production of SL further by feeding the molasses using a jar fermentor. Interestingly, the amount of SL increased up to 22.8 g/L after 120 h; the production rate was 1.6-fold higher than that in the shake-flask culture. These results suggest that the present yeast should have great potential for the low-cost production of SL, and facilitate the application of BS in various fields.
sophorolipids, yeast, glycolipid biosurfactant, sugarcane molasses, Starmerella bombicola
NCBI PubMed ID: 21502725Publication DOI: 10.5650/jos.60.267Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Kitamoto D
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central, Tsukuba, Japan, Okinawa Prefectural Agricultural Research Center, Okinawa, Japan, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology AIST, AIST Tsukuba Central, Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, TLC, MALDI-TOF MS, HPLC, extraction, GS-MS, COSY, HPLC-ELSD
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5. Compound ID: 18653
Structure type: cyclic polymer repeating unit
; n=1
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7321
Takahashi M, Morita T, Wada K, Hirose N, Fukuoka T, Imura T, Kitamoto D "Production of sophorolipid glycolipid biosurfactants from sugarcane molasses using Starmerella bombicola NBRC 10243" -
Journal of Oleo Science 60(5) (2011) 267-273
Biosurfactants (BS) are produced by a variety of microorganisms from renewable resources, and have unique properties compared to chemical surfactants. In order to attain efficient production of BS from low-cost materials, we focused our attention on the use of sugarcane molasses. Fifteen yeast strains that are known as BS producers were examined for BS productivity from a culture medium consisting of only molasses and water. Among the strains tested, only Starmerella bombicola NBRC 10243 produced sophorolipids (SL), which are glycolipid BS. The culture conditions for the yeast were then investigated in a shake-flask culture. SL production was significantly affected by the pH of the medium and was highly accelerated at pH 6. Under the optimum conditions, the amount of SL reached 14.4 g/L after 120 h from a medium containing 150 g/L of total sugars. We tried to improve the production of SL further by feeding the molasses using a jar fermentor. Interestingly, the amount of SL increased up to 22.8 g/L after 120 h; the production rate was 1.6-fold higher than that in the shake-flask culture. These results suggest that the present yeast should have great potential for the low-cost production of SL, and facilitate the application of BS in various fields.
sophorolipids, yeast, glycolipid biosurfactant, sugarcane molasses, Starmerella bombicola
NCBI PubMed ID: 21502725Publication DOI: 10.5650/jos.60.267Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Kitamoto D
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central, Tsukuba, Japan, Okinawa Prefectural Agricultural Research Center, Okinawa, Japan, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology AIST, AIST Tsukuba Central, Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, TLC, MALDI-TOF MS, HPLC, extraction, GS-MS, COSY, HPLC-ELSD
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6. Compound ID: 18654
Structure type: cyclic polymer repeating unit
; n=1
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7321
Takahashi M, Morita T, Wada K, Hirose N, Fukuoka T, Imura T, Kitamoto D "Production of sophorolipid glycolipid biosurfactants from sugarcane molasses using Starmerella bombicola NBRC 10243" -
Journal of Oleo Science 60(5) (2011) 267-273
Biosurfactants (BS) are produced by a variety of microorganisms from renewable resources, and have unique properties compared to chemical surfactants. In order to attain efficient production of BS from low-cost materials, we focused our attention on the use of sugarcane molasses. Fifteen yeast strains that are known as BS producers were examined for BS productivity from a culture medium consisting of only molasses and water. Among the strains tested, only Starmerella bombicola NBRC 10243 produced sophorolipids (SL), which are glycolipid BS. The culture conditions for the yeast were then investigated in a shake-flask culture. SL production was significantly affected by the pH of the medium and was highly accelerated at pH 6. Under the optimum conditions, the amount of SL reached 14.4 g/L after 120 h from a medium containing 150 g/L of total sugars. We tried to improve the production of SL further by feeding the molasses using a jar fermentor. Interestingly, the amount of SL increased up to 22.8 g/L after 120 h; the production rate was 1.6-fold higher than that in the shake-flask culture. These results suggest that the present yeast should have great potential for the low-cost production of SL, and facilitate the application of BS in various fields.
sophorolipids, yeast, glycolipid biosurfactant, sugarcane molasses, Starmerella bombicola
NCBI PubMed ID: 21502725Publication DOI: 10.5650/jos.60.267Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Kitamoto D
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central, Tsukuba, Japan, Okinawa Prefectural Agricultural Research Center, Okinawa, Japan, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology AIST, AIST Tsukuba Central, Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, TLC, MALDI-TOF MS, HPLC, extraction, GS-MS, COSY, HPLC-ELSD
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7. Compound ID: 18655
Structure type: oligomer
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7321
Takahashi M, Morita T, Wada K, Hirose N, Fukuoka T, Imura T, Kitamoto D "Production of sophorolipid glycolipid biosurfactants from sugarcane molasses using Starmerella bombicola NBRC 10243" -
Journal of Oleo Science 60(5) (2011) 267-273
Biosurfactants (BS) are produced by a variety of microorganisms from renewable resources, and have unique properties compared to chemical surfactants. In order to attain efficient production of BS from low-cost materials, we focused our attention on the use of sugarcane molasses. Fifteen yeast strains that are known as BS producers were examined for BS productivity from a culture medium consisting of only molasses and water. Among the strains tested, only Starmerella bombicola NBRC 10243 produced sophorolipids (SL), which are glycolipid BS. The culture conditions for the yeast were then investigated in a shake-flask culture. SL production was significantly affected by the pH of the medium and was highly accelerated at pH 6. Under the optimum conditions, the amount of SL reached 14.4 g/L after 120 h from a medium containing 150 g/L of total sugars. We tried to improve the production of SL further by feeding the molasses using a jar fermentor. Interestingly, the amount of SL increased up to 22.8 g/L after 120 h; the production rate was 1.6-fold higher than that in the shake-flask culture. These results suggest that the present yeast should have great potential for the low-cost production of SL, and facilitate the application of BS in various fields.
sophorolipids, yeast, glycolipid biosurfactant, sugarcane molasses, Starmerella bombicola
NCBI PubMed ID: 21502725Publication DOI: 10.5650/jos.60.267Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Kitamoto D
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central, Tsukuba, Japan, Okinawa Prefectural Agricultural Research Center, Okinawa, Japan, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology AIST, AIST Tsukuba Central, Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, TLC, MALDI-TOF MS, HPLC, extraction, GS-MS, COSY, HPLC-ELSD
- Article ID: 7857
Wadekar SD, Kale SB, Lali AM, Bhowmick DN, Pratap AP "Utilization of sweetwater as a cost-effective carbon source for sophorolipids production by Starmerella bombicola (ATCC 22214)" -
Preparative Biochemistry and Biotechnology 42(2) (2012) 125-142
Biosurfactants are microbially synthesized surfactants that are environmental friendly due to low toxicity. Sophorolipid is one of the simplest biosurfactants with well-defined structure produced by Starmerella bombicola(ATCC 22214) on glucose and vegetable oil as the carbon source. The raw material cost accounts for 10-30% of the overall cost. Glycerol is readily available from a commercial fat-splitting process as sweetwater at a very low cost. Sophorolipids was synthesized using glycerol and sweetwater as a cost-effective carbon source. The glycerol was further replaced with sweetwater as a source of glycerol. Optimum glycerol concentration was 15% w/v with 10% w/v sunflower oil, giving 6.6 g/L of sophorolipids. The crude sophorolipid contains two major components; both of them were lactonic sophorolipids as analyzed by reverse-phase high-performance liquid chromatography (RP-HPLC), liquid chromatography-mass spectroscopy (LC-MS), and nuclear magnetic resonance ((1)H-NMR).
glycerol, optimization, sophorolipids, LC-MS, 1H-NMR, sweetwater
NCBI PubMed ID: 22394062Publication DOI: 10.1080/10826068.2011.577883Journal NLM ID: 9607037Publisher: New York, NY: Marcel Dekker
Correspondence: Pratap AP
; Pratap AP
Institutions: Department of Oils, Oleochemicals and Surfactants Technology, Institute of Chemical Technology, Mumbai, India, Department of Chemical Engineering, DBT-ICT Centre for Energy Biosciences, Institute of Chemical Technology, Mumbai, India
Methods: 1H NMR, TLC, ESI-MS, HPLC, UV, extraction, LC-MS, CC, cell growth, evaporation, centrifugation, determination of surface tension
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8. Compound ID: 18656
Structure type: oligomer
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7321
Takahashi M, Morita T, Wada K, Hirose N, Fukuoka T, Imura T, Kitamoto D "Production of sophorolipid glycolipid biosurfactants from sugarcane molasses using Starmerella bombicola NBRC 10243" -
Journal of Oleo Science 60(5) (2011) 267-273
Biosurfactants (BS) are produced by a variety of microorganisms from renewable resources, and have unique properties compared to chemical surfactants. In order to attain efficient production of BS from low-cost materials, we focused our attention on the use of sugarcane molasses. Fifteen yeast strains that are known as BS producers were examined for BS productivity from a culture medium consisting of only molasses and water. Among the strains tested, only Starmerella bombicola NBRC 10243 produced sophorolipids (SL), which are glycolipid BS. The culture conditions for the yeast were then investigated in a shake-flask culture. SL production was significantly affected by the pH of the medium and was highly accelerated at pH 6. Under the optimum conditions, the amount of SL reached 14.4 g/L after 120 h from a medium containing 150 g/L of total sugars. We tried to improve the production of SL further by feeding the molasses using a jar fermentor. Interestingly, the amount of SL increased up to 22.8 g/L after 120 h; the production rate was 1.6-fold higher than that in the shake-flask culture. These results suggest that the present yeast should have great potential for the low-cost production of SL, and facilitate the application of BS in various fields.
sophorolipids, yeast, glycolipid biosurfactant, sugarcane molasses, Starmerella bombicola
NCBI PubMed ID: 21502725Publication DOI: 10.5650/jos.60.267Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Kitamoto D
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central, Tsukuba, Japan, Okinawa Prefectural Agricultural Research Center, Okinawa, Japan, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology AIST, AIST Tsukuba Central, Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, TLC, MALDI-TOF MS, HPLC, extraction, GS-MS, COSY, HPLC-ELSD
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9. Compound ID: 18657
Structure type: oligomer
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7321
Takahashi M, Morita T, Wada K, Hirose N, Fukuoka T, Imura T, Kitamoto D "Production of sophorolipid glycolipid biosurfactants from sugarcane molasses using Starmerella bombicola NBRC 10243" -
Journal of Oleo Science 60(5) (2011) 267-273
Biosurfactants (BS) are produced by a variety of microorganisms from renewable resources, and have unique properties compared to chemical surfactants. In order to attain efficient production of BS from low-cost materials, we focused our attention on the use of sugarcane molasses. Fifteen yeast strains that are known as BS producers were examined for BS productivity from a culture medium consisting of only molasses and water. Among the strains tested, only Starmerella bombicola NBRC 10243 produced sophorolipids (SL), which are glycolipid BS. The culture conditions for the yeast were then investigated in a shake-flask culture. SL production was significantly affected by the pH of the medium and was highly accelerated at pH 6. Under the optimum conditions, the amount of SL reached 14.4 g/L after 120 h from a medium containing 150 g/L of total sugars. We tried to improve the production of SL further by feeding the molasses using a jar fermentor. Interestingly, the amount of SL increased up to 22.8 g/L after 120 h; the production rate was 1.6-fold higher than that in the shake-flask culture. These results suggest that the present yeast should have great potential for the low-cost production of SL, and facilitate the application of BS in various fields.
sophorolipids, yeast, glycolipid biosurfactant, sugarcane molasses, Starmerella bombicola
NCBI PubMed ID: 21502725Publication DOI: 10.5650/jos.60.267Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Kitamoto D
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central, Tsukuba, Japan, Okinawa Prefectural Agricultural Research Center, Okinawa, Japan, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology AIST, AIST Tsukuba Central, Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, TLC, MALDI-TOF MS, HPLC, extraction, GS-MS, COSY, HPLC-ELSD
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10. Compound ID: 18658
Structure type: oligomer
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7321
Takahashi M, Morita T, Wada K, Hirose N, Fukuoka T, Imura T, Kitamoto D "Production of sophorolipid glycolipid biosurfactants from sugarcane molasses using Starmerella bombicola NBRC 10243" -
Journal of Oleo Science 60(5) (2011) 267-273
Biosurfactants (BS) are produced by a variety of microorganisms from renewable resources, and have unique properties compared to chemical surfactants. In order to attain efficient production of BS from low-cost materials, we focused our attention on the use of sugarcane molasses. Fifteen yeast strains that are known as BS producers were examined for BS productivity from a culture medium consisting of only molasses and water. Among the strains tested, only Starmerella bombicola NBRC 10243 produced sophorolipids (SL), which are glycolipid BS. The culture conditions for the yeast were then investigated in a shake-flask culture. SL production was significantly affected by the pH of the medium and was highly accelerated at pH 6. Under the optimum conditions, the amount of SL reached 14.4 g/L after 120 h from a medium containing 150 g/L of total sugars. We tried to improve the production of SL further by feeding the molasses using a jar fermentor. Interestingly, the amount of SL increased up to 22.8 g/L after 120 h; the production rate was 1.6-fold higher than that in the shake-flask culture. These results suggest that the present yeast should have great potential for the low-cost production of SL, and facilitate the application of BS in various fields.
sophorolipids, yeast, glycolipid biosurfactant, sugarcane molasses, Starmerella bombicola
NCBI PubMed ID: 21502725Publication DOI: 10.5650/jos.60.267Journal NLM ID: 101175339Publisher: Tokyo: Japan Oil Chemists Society
Correspondence: Kitamoto D
Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central, Tsukuba, Japan, Okinawa Prefectural Agricultural Research Center, Okinawa, Japan, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology AIST, AIST Tsukuba Central, Tsukuba, Japan
Methods: 13C NMR, 1H NMR, methylation, TLC, MALDI-TOF MS, HPLC, extraction, GS-MS, COSY, HPLC-ELSD
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11. Compound ID: 19685
Structure type: cyclic polymer repeating unit
; 578.69, n=1
C28H50O12
Compound class: glycolipid, sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7763
Sen S, Borah SN, Bora A, Deka S "Production, characterization, and antifungal activity of a biosurfactant produced by Rhodotorula babjevae YS3" -
Microbial Cell Factories 16(1) (2017) 95
Sophorolipids are one of the most promising glycolipid biosurfactants and have been successfully employed in bioremediation and various other industrial sectors. They have also been described to exhibit antimicrobial activity against different bacterial species. Nevertheless, previous literature pertaining to the antifungal activity of sophorolipids are limited indicating the need for further research to explore novel strains with wide antimicrobial activity. A novel yeast strain, Rhodotorula babjevae YS3, was recently isolated from an agricultural field in Assam, Northeast India. This study was primarily emphasized at the characterization and subsequent evaluation of antifungal activity of the sophorolipid biosurfactant produced by R. babjevae YS3. The growth kinetics and biosurfactant production by R. babjevae YS3 was evaluated by cultivation in Bushnell-Haas medium containing glucose (10% w/v) as the sole carbon source. A reduction in the surface tension of the culture medium from 70 to 32.6 mN/m was observed after 24 h. The yield of crude biosurfactant was recorded to be 19.0 g/l which might further increase after optimization of the growth parameters. The biosurfactant was characterized to be a heterogeneous sophorolipid (SL) with both lactonic and acidic forms after TLC, FTIR and LC-MS analyses. The SL exhibited excellent oil spreading and emulsifying activity against crude oil at 38.46 mm2 and 100% respectively. The CMC was observed to be 130 mg/l. The stability of the SL was evaluated over a wide range of pH (2-10), salinity (2-10% NaCl) and temperature (at 120 °C for time intervals of 30 up to 120 min). The SL was found to retain surface-active properties under the extreme conditions. Additionally, the SL exhibited promising antifungal activity against a considerably broad group of pathogenic fungi viz. Colletotrichum gloeosporioides, Fusarium verticilliodes, Fusarium oxysporum f. sp. pisi, Corynespora cassiicola, and Trichophyton rubrum. The study reports, for the first time, the biosurfactant producing ability of R. babjevae, a relatively lesser studied yeast. The persistent surface active properties of the sophorolipid in extreme conditions advocates its applicability in diverse environmental and industrial sectors. Further, antifungal activities against plant and human pathogens opens up possibilities for development of efficient and eco-friendly antifungal agents with agricultural and biomedical applications.
biosurfactant, antifungal activity, sophorolipid, LC-MS, Rhodotorula babjevae
NCBI PubMed ID: 28558761Publication DOI: 10.1186/s12934-017-0711-zJournal NLM ID: 101139812Publisher: London: BioMed Central
Correspondence: sureshdeka@gmail.com
Institutions: Environmental Biotechnology Laboratory, Life Sciences Division, Institute of Advanced Study in Science and Technology(IASST), Guwahati, India, Department of Bioengineering and Technology, Institute of Science and Technology, Gauhati University, Guwahati, India
Methods: DNA sequencing, TLC, biological assays, extraction, LC-MS, CC, LC-ESI-MS, cell growth, centrifugation, determination of surface tension, FT-IR
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12. Compound ID: 19900
| Cyclic
-4)-b-D-Glcp6(%)Ac-(1-2)-b-D-Glcp6(%)Ac-(1-15)-15HOPam-(1- |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=1, 620, 662
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7870
Yang X, Zhu L, Xue C, Chen Y, Qu L, Lu W "Recovery of purified lactonic sophorolipids by spontaneous crystallization during the fermentation of sugarcane molasses with Candida albicans O-13-1" -
Enzyme and Microbial Technology 51(6-7) (2012) 348-353
Numerous studies have focused on how to obtain high yield of sophorolipids using low-cost materials as substrates, and there has been various work on the experimental methods for purifying lactonic sophorolipids. These studies have not yet obtained satisfied results in combining a low-cost fermentation process and the purification of lactonic sophorolipids. This study establishes a fed-batch fermentation process of purifying sophorolipids from Candida albicans O-13-1 using low-cost sugarcane molasses as the substrate. In the optimized conditions of this research, using sugarcane molasses as a substrate and product synthesis based on the temperature stage-controlled fermentation, our result indicates that sophorolipids production could reach 108.7 g/L. More importantly, lactonic sophorolipids can crystallize and precipitate during our established fermentation process. The structures and content of sophorolipids separated from the fermentation broth and sophorolipids crystallized in the fermentation broth were analyzed by a scanning electron microscope (SEM) and liquid chromatography-mass spectrometry (LC-MS). The fermentation process produced 90.5 g/L crystallized lactonic sophorolipids with 90.51% purity. This is an energy-saving and low-cost method to obtain such pure lactonic sophorolipids.
Candida albicans, Crystallization, Lactonic sophorolipid, molasses, soybean oil, temperature stage-control
NCBI PubMed ID: 23040390Publication DOI: 10.1016/j.enzmictec.2012.08.002Journal NLM ID: 8003761Correspondence: Lu W
Institutions: Department of Biological Engineering and Key Laboratory of Systems, Bioengineering of the Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin, China, China Offshore Environmental Service Ltd., Tianjin, China
Methods: HPLC, extraction, microscopy, LC-MS, cell growth, SEM
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13. Compound ID: 22646
Structure type: cyclic polymer repeating unit
; 661
Compound class: glycolipid, sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9341
Ceresa C, Fracchia L, Williams M, Banat IM, Díaz De Rienzo MA "The effect of sophorolipids against microbial biofilms on medical-grade silicone" -
Journal of Biotechnology 309 (2020) 34-43
Recent medical strategies rely on the search for effective antimicrobials as surface coatings to prevent and treat infections in humans and animals. Biosurfactants have recently been shown to have properties as antiadhesive and antibiofilm agents. Sophorolipids in particular are biosurfactant molecules known to act as therapeutic agents. This study aimed to evaluate antimicrobial properties of sophorolipids in medical-grade silicone discs using strains of clinical relevance. Sophorolipids were produced under fed batch conditions, ESI-MS analyses were carried out to confirm the congeners present in each formulation. Three different products were obtained SLA (acidic congeners), SL18 (lactonic congeners) and SLV (mixture of acidic and lactonic congeners) and were tested against Staphylococcus aureus ATCC 6538, Pseudomonas aeruginosa ATCC 10145 and Candida albicans IHEM 2894. All three congener mixtures showed a biofilms disruption effect (> 0.1 % w/v) of 70 %, 75 % and 80 % for S. aureus, P. aeruginosa and C. albicans, respectively. On pre-coated silicone discs, biofilm formation of S. aureus was reduced by 75 % using SLA 0.8 % w/v. After 1.5 h the inhibition of C. albicans attachment was between 45-56 % whilst after 24 h incubation the percentage of inhibition for the cell attachment increased to 68-70 % when using SLA 0.8 % w/v. Finally, in co-incubation experiments SLA 0.05 % w/v significantly reduced the ability of S. aureus and C. albicans to form biofilms and to adhere to surfaces by 90-95 % at concentrations between 0.025-0.1 % w/v. In conclusion sophorolipids significantly reduced the cell attachment of both tested strains which suggests that these molecules could have a potential role as coating agents on medical grade silicone devices for the preventions of Gram positive bacteria and yeast infections.
Pseudomonas aeruginosa, Staphylococcus aureus, biofilms, Candida albicans, sophorolipids, medical-grade silicone
NCBI PubMed ID: 31887325Publication DOI: 10.1016/j.jbiotec.2019.12.019Journal NLM ID: 8411927Publisher: Amsterdam: Elsevier
Correspondence: m.a.diaz@ljmu.ac.uk
Institutions: School of Biomedical Sciences, University of Ulster, Coleraine, UK, Department of Pharmaceutical Sciences, Università del Piemonte Orientale ''A. Avogadro'', Novara, Italy, School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Liverpool, UK
Methods: ESI-MS, colorimetry, extraction, cell growth, SEM, antimicrobial assay, MTT
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