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Structure type: oligomer ; 706
Trivial name: sophorolipid anionic acid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192

• Article ID: 6851
  De Koster CG, Heerma W, Pepermans HA, Groenewegen A, Peters H, Haverkamp J "Tandem mass spectrometry and nuclear magnetic resonance spectroscopy studies of Candida bombicola sophorolipids and product formed on hydrolysis by cutinase" - Analytical Biochemistry 230(1) (1995) 135-148
  

  Natural mixtures of sophorolipids produced by the yeast Candida bombicola have been analyzed by fast atom bombardment (FAB)-MS and collision-induced dissociation (CID)-MS. Some pure components have been analysed by two-dimensional NMR spectroscopy. The presence of acidic, lactonic, and O-acetylated forms and the position of double bonds in the fatty acid part of these glycolipids can be easily inferred from positive and negative ion FAB-mass spectra. Details about position of O-acetylation can be obtained from CID mass spectra of [M+H]+ and [M-H]- ions and from the NMR spectra. Differences in CID fragmentation between protonated and sodiated molecular ions are discussed in detail. Enzymatic hydrolysis of 6',6'-di-O-acetyl sophorolipid lactone by cutinase from Fusarium solani results specifically in the removal of the 6'-O-acetyl group, whereas the 6'-O-acetyl and lactone group are resistant. This specificity is explained from a three-dimensional model of the sophorolipid generated on the basis of the short 1H,1H distances as inferred from the NMR (ROESY) spectra

  biosynthesis, chemistry, metabolism, Non-U.S.Gov't, molecular, Molecular Structure, Carbohydrate Sequence, Molecular Sequence Data, hydrolysis, spectrometry, Magnetic Resonance Spectroscopy, methods, glycolipids, models, isolation & purification, Spectrum Analysis, Mass, Fast Atom Bombardment, Research Support, Candida, Surface-Active Agents, Anions, Ions, Carboxylic Ester Hydrolases, Detergents, Hydrolases

  NCBI PubMed ID: 8585609
  Journal NLM ID: 0370535
  Publisher: Academic Press
  Institutions: Bijvoet Center for Biomolecular Research, Mass Spectrometry Group, University of Utrecht, Utrecht, The Netherlands
  Methods: NMR-2D, FAB-MS, CID-MS, enzymatic deacetylation
  
   
  
  Candida bombicola
  CSDB ID 11403 (all data & tools)

Show legend Show as text

Structure type: cyclic polymer repeating unit ; 688; n=1
Trivial name: sophorolipid neutral lactone
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192

• Article ID: 6851
  De Koster CG, Heerma W, Pepermans HA, Groenewegen A, Peters H, Haverkamp J "Tandem mass spectrometry and nuclear magnetic resonance spectroscopy studies of Candida bombicola sophorolipids and product formed on hydrolysis by cutinase" - Analytical Biochemistry 230(1) (1995) 135-148
  

  Natural mixtures of sophorolipids produced by the yeast Candida bombicola have been analyzed by fast atom bombardment (FAB)-MS and collision-induced dissociation (CID)-MS. Some pure components have been analysed by two-dimensional NMR spectroscopy. The presence of acidic, lactonic, and O-acetylated forms and the position of double bonds in the fatty acid part of these glycolipids can be easily inferred from positive and negative ion FAB-mass spectra. Details about position of O-acetylation can be obtained from CID mass spectra of [M+H]+ and [M-H]- ions and from the NMR spectra. Differences in CID fragmentation between protonated and sodiated molecular ions are discussed in detail. Enzymatic hydrolysis of 6',6'-di-O-acetyl sophorolipid lactone by cutinase from Fusarium solani results specifically in the removal of the 6'-O-acetyl group, whereas the 6'-O-acetyl and lactone group are resistant. This specificity is explained from a three-dimensional model of the sophorolipid generated on the basis of the short 1H,1H distances as inferred from the NMR (ROESY) spectra

  biosynthesis, chemistry, metabolism, Non-U.S.Gov't, molecular, Molecular Structure, Carbohydrate Sequence, Molecular Sequence Data, hydrolysis, spectrometry, Magnetic Resonance Spectroscopy, methods, glycolipids, models, isolation & purification, Spectrum Analysis, Mass, Fast Atom Bombardment, Research Support, Candida, Surface-Active Agents, Anions, Ions, Carboxylic Ester Hydrolases, Detergents, Hydrolases

  NCBI PubMed ID: 8585609
  Journal NLM ID: 0370535
  Publisher: Academic Press
  Institutions: Bijvoet Center for Biomolecular Research, Mass Spectrometry Group, University of Utrecht, Utrecht, The Netherlands
  Methods: NMR-2D, FAB-MS, CID-MS, enzymatic deacetylation
  
   
  
  Candida bombicola
  CSDB ID 14403 (all data & tools)

Show legend Show as text

Structure type: cyclic polymer repeating unit ; n=1
C₁₇H₂₄O₁₄
Trivial name: lactone sophorolipid, sophorolipid
Compound class: glycolipid, sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 4255
  Lang S "Biological amphiphiles (microbial biosurfactants)" - Current Opinion in Colloid and Interface Science 7(1-2) (2002) 12-20
  

  Low- and high-molecular-weight biosurfactants are of great interest because of their physicochemical and biological properties, which can be exploited in oil, food, cosmetic and pharmaceutical industries. As for the general types of microbial amphiphiles, the data accumulated over recent years are adding new interesting molecular structures to well-known compounds. Using new strains and cultivation conditions, positive results were found in basic studies of lowering the surface tension of water (72 mN/m ? 27 mN/m, cmc: 150 mg/l; rhamnose lipids from Pseudomonas aeruginosa), of size determinations of micelles and vesicles (iturin A, a lipopeptide from Bacillus subtilis), of emulsifying properties, biological activities, as well as of application tests in soil remediation.

  biosynthesis, review, rhamnose, glycolipid, preparation, lipids, surfactant, surface properties, physicochemical properties, surface tension, emulsifying power, microorganism, lipopeptide, biological properties

  Publication DOI: 10.1016/S1359-0294(02)00007-9
  Journal NLM ID: 9614964
  Publisher: Current Science
  Correspondence: s.lang@tu-bs.de
  Institutions: Technical University of Braunschweig, Institute of Biochemistry and Biotechnology, Biotechnology Group, Spielmannstr. 7, D-38106 Braunschweig, Germany, Technical University of Braunschweig, Institute of Biochemistry and Biotechnology, Biotechnology Group, Spielmannstr. 7, 38106 Braunschweig, ALLEMAGNE
  
   
  
  Candida bombicola ATCC22214
  CSDB ID 15008 (all data & tools)
• Article ID: 7216
  Chen J, Song X, Zhang H, Qu Y "Production, structure elucidation and anticancer properties of sophorolipid from Wickerhamiella domercqiae" - Enzyme and Microbial Technology 39(3) (2006) 501-506
  

  A yeast strain Y2A producing a large amount of biosurfactants was isolated from oil-containing wastewater and identified as Wickerhamiella domercqiae by BIOLOG analysis and routine yeast identification method. The crude biosurfactants produced from Y2A were obtained by extract with ethyl acetate and proved to be a mixture of glycolipids by thin layer chromatography (TLC). The main product was separated and purified by HPLC and then characterized as sophorolipid by nuclear magnetic resonance (NMR) and mass spectroscopy (MS). This is the first report on sophorolipids produced from W. domercqiae. Subsequently, the cytotoxic effects of the sophorolipid on cancer cells of H7402, A549, HL60 and K562 were investigated by MTT assay. The results showed a dose-dependent inhibition ratio on cell viability according to the drug concentration ≤62.5 μg/ml. These findings suggested that the sophorolipid produced by W. domercqiae have anticancer activity.

  anticancer activity, sophorolipid, Wickerhamiella domercqiae, human cancer cell

  Publication DOI: 10.1016/j.enzmictec.2005.12.022
  Journal NLM ID: 8003761
  Correspondence: Song X ; Qu Y
  Institutions: State Key Lab of Microbial Technology, Shandong University, Jinan, China, State Key Lab of Microbial Technology, Shandong University, Jinan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, NMR-1D, HPLC, extraction, cell growth, cell viability assay, evaporation, determination of surface tension, MTT
  
   
  
  Wickerhamiella domercqiae Y2A
  CSDB ID 43408 (all data & tools)
• 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: 21502725
  Publication DOI: 10.5650/jos.60.267
  Journal NLM ID: 101175339
  Publisher: 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
  
   
  
  Starmerella bombicola NBRC 10243
  CSDB ID 43571 (all data & tools)
• Article ID: 7644
  Konishi M, Morita T, Fukuoka T, Imura T, Uemura S, Iwabuchi H, Kitamoto D "Selective production of acid-form sophorolipids from glycerol by Candida floricola" - Journal of Oleo Science 66(12) (2017) 1365-1373
  

  Biosurfactants (BSs) are produced in abundance from various feedstocks by diverse microorganisms, and are used in various applications. In this paper, we describe a new yeast isolate that produces glycolipid-BSs from glycerol, with the aim of enhancing the utilization of the surplus glycerol produced by the oleo-chemical industry. As a result of the screening, strain ZM1502 was obtained as a potential producer of BS from glycerol. Based on TLC analysis, the strain produced glycolipid BSs. According to structural analyses (NMR, MALDI-TOF MS, and GC-MS), the main component of the glycolipids was 6’,6”-di-O-acetylated acid-form sophorolipid (SL). Interestingly, the strain produced only acid-form SL, without lactone-form SLs, although the conventional SL-producing yeast, Starmerella bombicola, produces lactone-form SLs with small amounts of the acid-form. Based on taxonomy, the strain was identified as Candida floricola. It produced 3.5 g/L of acid-form SLs in 20% (w/v) glycerol. In addition, C. floricola CBS7290 and NBRC10700T also produced only acid-form SLs from glycerol. These results suggest that C. floricola would enhance the utilization of waste glycerol as a fermentation feedstock and facilitate a broad range of applications for SLs.

  glycerol, sophorolipid, acid-form sophorolipid, Candida floricola

  NCBI PubMed ID: 29129899
  Publication DOI: 10.5650/jos.ess17116
  Journal NLM ID: 101175339
  Publisher: Tokyo: Japan Oil Chemists Society
  Correspondence: Dai Kitamoto
  Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan, Chemicals Division, Lion Corporation, Tokyo, Japan, Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, Kitami, Japan, Research Institute for Chemical Process Technology, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan, Lion Specialty Chemicals Co., Ltd., Tokyo, Japan, Lion Corporation, Tokyo, Japan
  Methods: 13C NMR, 1H NMR, TLC, HPLC, GS-MS, HMBC, MALDI-TOF-MS
  
   
  
  Starmerella bombicola NBRC10243
  CSDB ID 43002 (all data & tools)
• Article ID: 7856
  Wadekar S, Kale S, Lali A, Bhowmick D, Pratap A "Sophorolipid production by Starmerella bombicola (ATCC 22214) from virgin and waste frying oils, and the effects of activated earth treatment of the waste oils" - Journal of the American Oil Chemists' Society 89(6) (2012) 1029-1039
  

  Frying is one of the most common processes in households, restaurants and food industries. During frying, oil undergoes degradation and hence has to be replaced time to time. This creates large amounts of waste causing disposal and environmental problems. Sophorolipids are produced by microbial bioconversion of refined vegetable oils along with glucose. The raw material cost accounts for 10-30% of the overall cost of biosurfactant production that can be reduced by using a low cost substrate like waste frying oil. In the present work, waste frying oils were used in the production of sophorolipids at the shake flask level. It gave mainly (70-80%) the acidic form of sophorolipids. It was observed that the linoleic acid was preferentially consumed over other fatty acids by the organism (Starmerella bombicola). The activated earth treatment was found to improve the yield of sophorolipids and hence the treatment can be used to convert waste frying oil as a low cost substrate into a cost effective carbon source.

  HPLC, sophorolipids, waste frying oil, activated earth treatment, linoleic acid

  Publication DOI: 10.1007/s11746-011-1986-6
  Journal NLM ID: 7505574
  Publisher: Champaign, IL: American Oil Chemists Society
  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, IR, TLC, HPLC, UV, extraction, LC-MS, CC, cell growth, evaporation, centrifugation, determination of surface tension
  
   
  
  Starmerella bombicola ATCC 22214 MTCC 1910
  CSDB ID 45919 (all data & tools)
• 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: 22394062
  Publication DOI: 10.1080/10826068.2011.577883
  Journal NLM ID: 9607037
  Publisher: 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
  
   
  
  Starmerella bombicola ATCC 22214 MTCC 1910
  CSDB ID 45924 (all data & tools)
• Article ID: 7908
  Cortés-Sánchez AJ, Hernández-Sánchez H, Jaramillo-Flores ME "Biological activity of glycolipids produced by microorganisms: New trends and possible therapeutic alternatives" - Microbiological Research 168(1) (2013) 22-32
  

  Several biological processes in prokaryotic and eukaryotic organisms require the presence of glycolipids (biosurfactants), compounds with both hydrophilic and hydrophobic groups in their structure. They constitute the backbone of different metabolic functions and biological structures such as cell membranes. Besides being structural components, glycolipids show surface activity in the interfaces and are mainly produced by microorganisms. Interest in biosurfactants has increased considerably in recent times due to their applications in the environmental, oil, food, and pharmaceutical industries, since they have unique properties such as low toxicity, high biodegradability, environmentally friendly, foaming capacity, high selectivity and specificity at extreme temperatures, pH and salinity, as well as biological activity. All of these properties are considered advantages over other chemical surfactants, and therefore glycolipids are considered a good alternative, given the current interest on sustainable development. The present work shows a general view of bio-surfactants of microbial origin, particularly of glycolipids, referring to several studies on their biological activity that have revealed their great potential in the medical–biological field, discovering interesting possibilities for their therapeutic application in the near future.

  biological activity, glycolipids, metabolite, biosurfactants, antimicrobials

  NCBI PubMed ID: 22959834
  Publication DOI: 10.1016/j.micres.2012.07.002
  Journal NLM ID: 9437794
  Publisher: G. Fischer
  Correspondence: jaramillo_flores@hotmail.com
  Institutions: Departamento de Graduados e Investigación en Alimentos, Escuela Nacional de Ciencias Biológicas-IPN, Carpio y Plan de Ayala, México, Mexico
  
   
  
  Wickerhamiella domercqiae
  CSDB ID 44878 (all data & tools)
• Article ID: 8173
  Kotland A, Hadef I, Renault JH, Hamzaoui M, Martinez A, Borie N, Guilleret A, Reynaud R, Hubert J "Gradient elution method in centrifugal partition chromatography for the separation of a complex sophorolipid mixture obtained from Candida bombicola yeasts" - Journal of Separation Science 36(8) (2013) 1362-1369
  

  Sophorolipids represent an important class of natural surfactants with a variety of environmental, cosmetic, and pharmaceutical applications. Despite their promising physicochemical and biological properties, the use of sophorolipids is hampered by the lack of information regarding their individual structure-activity relationships. The major difficulty in isolating pure sophorolipids arises from the high complexity of crude fermentation media composition and from their strong structural similarities. In this work, a centrifugal partition chromatography method was developed in an original gradient elution mode for the separation of sophorolipids produced by the yeast Candida bombicola. Experiments were realized by using three sets of solvent systems composed of n-heptane, ethyl acetate, n-butanol, methanol, and water in different proportions. The separation was performed at 5 mL/min in the ascending mode by increasing progressively the polarity of the organic mobile phase. In these conditions, more than 80% of the sophorolipids present in the initial crude fermentation extract were eluted successively from the most hydrophobic lactone forms to the most hydrophilic acid forms. The structures of the isolated sophorolipids were further elucidated by HPLC and NMR analyses.Sophorolipids represent an important class of natural surfactants with a variety of environmental, cosmetic, and pharmaceutical applications. Despite their promising physicochemical and biological properties, the use of sophorolipids is hampered by the lack of information regarding their individual structure-activity relationships. The major difficulty in isolating pure sophorolipids arises from the high complexity of crude fermentation media composition and from their strong structural similarities. In this work, a centrifugal partition chromatography method was developed in an original gradient elution mode for the separation of sophorolipids produced by the yeast Candida bombicola. Experiments were realized by using three sets of solvent systems composed of n-heptane, ethyl acetate, n-butanol, methanol, and water in different proportions. The separation was performed at 5 mL/min in the ascending mode by increasing progressively the polarity of the organic mobile phase. In these conditions, more than 80% of the sophorolipids present in the initial crude fermentation extract were eluted successively from the most hydrophobic lactone forms to the most hydrophilic acid forms. The structures of the isolated sophorolipids were further elucidated by HPLC and NMR analyses.

  sophorolipids, Candida bombicola, centrifugal partition chromatography

  NCBI PubMed ID: 23520018
  Publication DOI: 10.1002/jssc.201201033
  Journal NLM ID: 101088554
  Publisher: Weinheim: Wiley-VCH
  Correspondence: Hubert J
  Institutions: Université de Reims Champagne-Ardenne, Reims, France, Soliance, Pomacle, France
  Methods: 13C NMR, 1H NMR, HPLC, HMBC, COSY, HSQC
  
   
  
  Candida bombicola
  CSDB ID 45084 (all data & tools)
• Article ID: 8385
  Konishi M, Yoshida Y, Horiuchi J "Efficient production of sophorolipids by Starmerella bombicola using a corncob hydrolysate medium" - Journal of Bioscience and Bioengineering 119(3) (2015) 317-322
  

  Sophorolipids (SLs) are amphiphilic compounds produced from a variety of saccharides and vegetable oils by the yeast Starmerella bombicola and related strains, and they have commercial uses as detergents. In the present study, SL production was investigated using a corncob hydrolysate (CCH) medium derived from lignocellulosic feedstocks as a source of hydrophilic carbon substrates. Excess sulfuric acid concentrations during pretreatment of the corncobs increased the furfural concentrations and turned the CCH dark brown. The optimal sulfuric acid concentration was 1% (w/v), and the treated CCH, containing 45 g/l glucose, allowed the production of 33.7 g/l of SLs following 4 days of cultivation. Additional autoclaving (121°C, 20 min) inhibited SL production and cell growth by 36% and 40%, respectively. Ammonium nitrate (0.1 g-N/l) restored SL production to the autoclaved CCH. Finally, a cost-effective SL production of 49.2 g/l, with a volumetric productivity of 12.3 g/l/day, was achieved using CCH medium during batch cultivation in a jar fermentor

  biosurfactant, sophorolipids, Starmerella bombicola, lignocellulosic biomass, corncob hydrolysate, surface-active glycolipid

  NCBI PubMed ID: 25240400
  Publication DOI: 10.1016/j.jbiosc.2014.08.007
  Journal NLM ID: 100888800
  Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
  Correspondence: Konishi M ; Konishi M
  Institutions: Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, Kitami, Japan
  Methods: 13C NMR, 1H NMR, TLC, MALDI-TOF MS, HPLC, UV, extraction, CC, cell growth, evaporation
  
   
  
  Starmerella bombicola NBRC 10243
  CSDB ID 48237 (all data & tools)
• Article ID: 8390
  Solaiman DKY, Ashby RD, Zerkowski JA, Krishnama A, Vasanthan N "Control-release of antimicrobial sophorolipid employing different biopolymer matrices" - Biocatalysis and Agricultural Biotechnology 4(3) (2015) 342-348
  

  Sophorolipid (SL) purified from fermentation broth of Candida bombicola grown on oleic acid and glucose substrates was embedded at 0%, 9%, 17%, and 29% (%-total weight of final product) in solvent-cast films of poly(L-lactic acid) (PLLA), poly(ε-caprolactone), and poly(hydroxybutyrate) (PHB). Growth-inhibition activity of the SL-biopolymers against Propionibacterium acnes, a causative agent of acne vulgaris skin condition, is dependent on the SL contents of the films; the degree of inhibition as determined from the width of the zone of inhibition in agar-plate assays follows the order of SL-PCL>SL-PLLA>SL-PHB. The release of SL from the films into aqueous medium after a 4-d shaking at 25 °C showed that SL-PLLA (30.1±1.7 wt% SL released) most readily released the embedded SL, followed by SL-PHB (11.4±4.3 wt%) and SL-PCL (4.3±1.4 wt%). Thermal properties as determined by differential scanning calorimetry showed that SL decreases the heat of fusion (ΔH) and the melting temperature (Tm) of the biopolymers, indicating for the first time its usefulness as a plasticizer to prevent crystallization. In summary, the study shows the feasibility of controlling the release of antimicrobial SL by varying the type of biopolymer used, with the added advantage of SL functioning as a plasticizer to improve the physical properties of the film in term of lower crystallinity. Future research could benefit the agricultural sector via new developments as varied as antimicrobial food packaging and algal bloom mitigation

  glycolipid, antibacterial, biosurfactant, algicidal, biopolymer film

  Publication DOI: 10.1016/j.bcab.2015.06.006
  Journal NLM ID: 101589270
  Publisher: Atlanta, GA: Elsevier
  Correspondence: Solaiman DKY ; Vasanthan N
  Institutions: Eastern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Wyndmoor, USA, Department of Chemistry and Biochemistry, Long Island University Brooklyn Campus, Brooklyn, USA
  Methods: HPLC, extraction, cell growth, precipitation, evaporation, antimicrobial assay, ELSD
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 48257 (all data & tools)
• Article ID: 8523
  Abdel-Mawgoud AM, Stephanopoulos G "Simple glycolipids of microbes: Chemistry, biological activity and metabolic engineering" - Synthetic and Systems Biotechnology 3(1) (2018) 3-19
  

  Glycosylated lipids (GLs) are added-value lipid derivatives of great potential. Besides their interesting surface activities that qualify many of them to act as excellent ecological detergents, they have diverse biological activities with promising biomedical and cosmeceutical applications. Glycolipids, especially those of microbial origin, have interesting antimicrobial, anticancer, antiparasitic as well as immunomodulatory activities. Nonetheless, GLs are hardly accessing the market because of their high cost of production. We believe that experience of metabolic engineering (ME) of microbial lipids for biofuel production can now be harnessed towards a successful synthesis of microbial GLs for biomedical and other applications. This review presents chemical groups of bacterial and fungal GLs, their biological activities, their general biosynthetic pathways and an insight on ME strategies for their production.

  glycosides, biosurfactant, glycolipids biosynthesis, glycosyl/acyl transferases, lipid biotechnology, physiological roles

  NCBI PubMed ID: 29911195
  Publication DOI: 10.1016/j.synbio.2017.12.001
  Journal NLM ID: 101694371
  Publisher: Beijing, China: KeAi Communications Co.
  Correspondence: Stephanopoulos G
  Institutions: Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, USA
  
   
  
  Candida bombicola, Candida apicola, Wickerhamiella domercqiae
  CSDB ID 48566 (all data & tools)
• Article ID: 8568
  Kanwar R, Gradzielski M, Mehta SK "Biomimetic solid lipid nanoparticles of sophorolipids designed for antileprosy drugs" - Journal of Physical Chemistry B 122(26) (2018) 6837-6845
  

  The objective of the present work was to develop solid lipid nanoparticles (SLNs) as drug-encapsulating structures by the solvent injection method. In this report, for the first time the inherent potential of lactonic sophorolipid (glycolipid) was exploited to formulate SLNs. A range of different Pluronic copolymers were screened by dynamic and static light scattering with the aim of obtaining most stable SLNs. To comprehend the structure of the SLNs, techniques such as transmission electron microscopy, differential scanning calorimetry, Fourier transform infrared spectroscopy, and X-ray diffraction were employed. A clear correlation between the type of Pluronic and size and stability of the SLNs could be drawn. The vector properties of the formed SLNs were assessed for both the encapsulated hydrophobic drugs-rifampicin and dapsone. To elucidate the transport mechanism of drug release, kinetic modeling was carried out on the drug release profiles. The promising results of sophorolipid-based SLNs have actually established a new arena beneath the significantly developed field of SLNs.

  X-ray, TEM, nanoparticles, drug delivery systems

  NCBI PubMed ID: 29874078
  Publication DOI: 10.1021/acs.jpcb.8b03081
  Journal NLM ID: 101157530
  Publisher: Washington, DC: American Chemical Society
  Correspondence: Mehta SK ; Gradzielski M
  Institutions: Department of Chemistry and Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, India, Stranski Laboratorium für Physikalische und Theoretische Chemie, Institut für Chemie, Technische Universität Berlin, Berlin, Germany
  Methods: X-ray, FTIR, dialysis, dynamic light scattering, TEM, static light scattering, differential scanning calorimetry
  
   
  
  Starmerella bombicola
  CSDB ID 48748 (all data & tools)
• Article ID: 8586
  Maeng Y, Kim KT, Zhou X, Jin L, Kim KS, Kim YH, Lee S, Park JH, Chen X, Kong M, Cai L, Li X "A novel microbial technique for producing high-quality sophorolipids from horse oil suitable for cosmetic applications" - Microbial Biotechnology 11(5) (2018) 917-929
  

  Horse oil contains linoleic, palmitoleic and unsaturated fatty acids that are similar to those in human skin, and may therefore be an ideal substance from which to isolate biosurfactants for cosmetic products to improve human skin quality. Herein, an innovative approach was developed to synthesise sophorolipids from horse oil by hydrolysis, followed by fermentation using the yeast Candida bombicola. The yield of sophorolipids from direct fermentation of horse oil and hydrolysed horse oil was 40.6 ± 1.3 g l-1 and 58.4 ± 1.8 g l-1 respectively. To further increase the yield, 30-40 g l-1 glucose was added in a fed-batch fermentation process to maintain the pH between 4.0 and 4.5, resulting in a conversion yield of 71.7 ± 0.8 g l-1 . The purity and structure of the synthesised sophorolipids were analysed by ultra-performance liquid chromatography-mass spectrometry and nuclear magnetic resonance. An in vitro human dermal fibroblast model was used as a surrogate for human skin to measure elastase inhibition activity. Antiwrinkle properties of isolated sophorolipids were better than those of horse oil or hydrolysed horse oil in several in vitro assays. Furthermore, no cytotoxicity was observed at a concentration of 50 μg ml-1 , and wound-healing capacity was evident in a cell culture model. Additionally, the synthesised sophorolipids attenuated lipopolysaccharide-induced expression of inflammatory cytokines in macrophages, and efficiently inhibited several strains of bacteria and yeast. In conclusion, fed-batch fermentation of hydrolysed horse oil is a novel and efficient approach for producing high-quality and high-yield sophorolipids that exhibit great potential as cosmetic ingredients.

  structure, Candida bombicola, sophorolipid production, horse oil

  NCBI PubMed ID: 30022625
  Publication DOI: 10.1111/1751-7915.13297
  Journal NLM ID: 101316335
  Publisher: Hoboken, NJ: Wiley-Blackwell
  Correspondence: Li X ; Cai L
  Institutions: School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China, Collaborative Innovation Center of Biomedicine, Wenzhou Medical University-Wenzhou University, Wenzhou, China, Ningbo First Hospital, Ningbo, China, BiolandBiotec. Co., Ltd., Zhangjiang Modern Medical Device Park, Pudong, Shanghai, China, SK Bioland, Cheonan, Korea, SK Bioland, Cheongju, Korea, Departments of Pediatrics, Radiation Oncology, Pharmacology and Toxicology, Pediatric Research Institute, University of Louisville, Louisville, USA
  Methods: 13C NMR, 1H NMR, biological assays, extraction, chromatography, statistical analysis, cytokines assay, antibacterial assay, UPLC-MS/MS, cytotoxicity assay, HMBC, DEPT, COSY, antifungal activity test
  
   
  
  Candida bombicola ATCC22214
  CSDB ID 48797 (all data & tools)
• Article ID: 8700
  Dubey P, Kumar S, Aswal VK, Ravindranathan S, Rajamohanan PR, Prabhune A, Nisal A "Silk fibroin-sophorolipid gelation: deciphering the underlying mechanism" - Biomacromolecules 17(10) (2016) 3318-3327
  

  Silk fibroin (SF) protein, produced by silkworm Bombyx mori, is a promising biomaterial, while sophorolipid (SL) is an amphiphilic functional biosurfactant synthesized by nonpathogenic yeast Candida bombicola. SL is a mixture of two forms, acidic (ASL) and lactonic (LSL), which when added to SF results in accelerated gelation of silk fibroin. LSL is known to have multiple biological functionalities and hence hydrogels of these green molecules have promising applications in the biomedical sector. In this work, SANS, NMR, and rheology are employed to examine the assembling properties of individual and mixed SLs and their interactions with SF to understand the mechanism that leads to rapid gelation. SANS and NMR studies show that ASL assembles to form charged micelles, while LSL forms micellar assemblies and aggregates of a mass fractal nature. ASL and LSL together form larger mixed micelles, all of which interact differently with SF. It is shown that preferential binding of LSL to SF causes rapid unfolding of the SF chain leading to the formation of intermolecular beta sheets, which trigger fast gelation. Based on the observations, a mechanism for gelation of SF in the presence of different sophorolipids is proposed.

  biosurfactant, yeast, sophorolipid, Candida bombicola

  NCBI PubMed ID: 27643890
  Publication DOI: 10.1021/acs.biomac.6b01069
  Journal NLM ID: 100892849
  Publisher: Washington, DC: American Chemical Society
  Correspondence: Prabhune A ; Nisal A
  Institutions: Biochemical Sciences Division, Central NMR Facility, National Chemical Laboratory, Pune, India, Polymer Science and Engineering, National Chemical Laboratory, Pune, India, Solid State Physics Division, Bhabha Atomic Research Centre, Mumbai, India
  Methods: 13C NMR, 1H NMR, ROESY, TOCSY, small-angle neutron scattering (SANS), HMBC, COSY, HSQC
  
   
  
  Starmerella bombicola ATCC 22214
  CSDB ID 42717 (all data & tools)
• Article ID: 8810
  Van Renterghem L, Roelants SLKW, Baccile N, Uyttersprot K, Taelman MC, Everaert B, Mincke S, Ledegen S, Debrouwer S, Scholtens K, Stevens C, Soetaert W "From lab to market: An integrated bioprocess design approach for new-to-nature biosurfactants produced by Starmerella bombicola" - Journal of Microbiology 115(5) (2018) 1195-1206
  

  Glycolipid microbial biosurfactants, such as sophorolipids (SLs), generate high industrial interest as 100% biobased alternatives for traditional surfactants. A well-known success story is the efficient SL producer Starmerella bombicola, which reaches titers well above 200 g/L. Recent engineering attempts have enabled the production of completely new types of molecules by S. bombicola, e.g. the bolaform SLs. Scale-up of bolaform SL production was performed at 150 L scale. The purified product was evaluated in detergent applications, as classic SLs are mostly applied in eco-friendly detergents. In this paper, we show that they can be used as green and non-irritant surfactants in for example (automatic) dishwashing applications. However, due to the presence of an ester function in the biosurfactant molecule a limited chemical stability at higher pH values (>6.5) was noticed, (therefore called 'non-symmetrical' (nsBola)) which, is a major drawback that will most likely inhibit market introduction. An integrated bioprocess design (IBPD) strategy was thus applied to resolve this issue. The strategy was to replace the fed fatty acids with fatty alcohols, to generate so-called "symmetrical bolaform (sBola) sophorosides (SSs)," containing two instead of one glycosidic bond. Next to a change in feeding strategy, the blocking of the fatty alcohols from metabolizing/oxidizing through the suggested ω-oxidation pathway was necessary. For the latter, two putative fatty alcohol oxidase genes (fao1 and fao2) were identified in the S. bombicola genome and deleted in the bolaform SL producing strain (ΔatΔsble). Shake flask experiments for these new strains (ΔatΔsbleΔfao1 and ΔatΔsbleΔfao2) were performed to evaluate if the fed fatty alcohols were directly implemented into the SL biosynthesis pathway. Indeed, sBola sophorosides (SSs) production up to 20 g/L was observed for the ΔatΔsbleΔfao1 strain. Unexpectedly, the ΔatΔsbleΔfao2 strain only produced minor amounts of sBola sophorosides (SSs), and mainly nsBola SLs (alike the parental ΔatΔsble strain). The sBola sophorosides (SSs) were purified and their symmetrical structure was confirmed by NMR. They were found to be significantly more stable at higher pH, opening up the application potential of the biosurfactant by enhancing its stability properties.

  biosurfactant, sophorolipid, starmerella, strain engineering, application testing, fermentation and purification

  NCBI PubMed ID: 29288587
  Publication DOI: 10.1002/bit.26539
  Journal NLM ID: 9703165
  Publisher: Seoul: Microbiological Society of Korea
  Correspondence: Roelants SLKW
  Institutions: Ghent University, Centre for Industrial Biotechnology and Biocatalysis (InBio.be), Ghent, Belgium, Bio Base Europe Pilot Plant, Ghent, Belgium, Sorbonne Universités, UPMC Univ Paris 06, CNRS, Collège de France, Chimie de la Matière Condensée de Paris (UMR 7574), Paris, France, EOC Group, Oudenaarde, Belgium, Ghent University, Sustainable Organic Chemistry and Technology, Gent, Belgium
  Methods: 13C NMR, 1H NMR, TLC, alkaline hydrolysis, PLC, LC-MS, TOCSY, GC-FID, HMBC, centrifugation, COSY, HSQC, ultrafiltration, HPLC-ELSD, UPLC, small-angle X-ray scattering (SAXS), surface tension determination, H2BC
  
   
  
  Starmerella bombicola
  CSDB ID 49089 (all data & tools)
• Article ID: 8922
  Kaur G, Wang H, To MH, Roelants SLKW, Soetaert W, Lin CSK "Efficient sophorolipids production using food waste" - Journal of Cleaner Production 232 (2019) 1-11
  

  Recent sustainable development goals of food security, environmental protection, material and energy efficiency are the key drivers of the valorization of food waste. In the present work, the production of biosurfactant sophorolipids from several (food) waste streams was investigated, using the non-pathogenic yeast Starmerella bombicola. From a preliminary screening, restaurant food waste emerged as the most suitable feedstock compared to bakery waste, textile waste, used corn oil, animal fat and lipid fraction of hydrolyzed food waste. Restaurant food waste was subsequently used for sophorolipids production in a laboratory-scale bioreactor. Food waste obtained from a local restaurant was subjected to enzymatic hydrolysis for 16 h, yielding a hydrolysate containing about 100 g/L glucose and 2.4 g/L free amino nitrogen. High SL process efficiency was achieved by fed-batch fermentation using the restaurant food waste hydrolysate as the complete batch medium, i.e. without any supplementation of additional medium components such as vitamins, salts, nitrogen or phosphate. Controlled feeding of glucose and oleic acid to the culture was performed after the batch phase. A sophorolipids titer of 115.2 g/L was obtained in a fermentation time of 92 h resulting in an overall volumetric productivity of 1.25 g/L.h. These results achieved for sophorolipids productivity using hydrolyzed food waste are in the same order of magnitude as the reported values using traditional (complex) fermentation media. This indicates the suitability of the developed process using food waste for the advancement of waste-based bio-processes for the production of sophorolipids.

  fermentation, biosurfactant, Starmerella bombicola, restaurant food waste, second generation substrate, valorization

  Publication DOI: 10.1016/j.jclepro.2019.05.326
  Journal NLM ID: 101538287
  Publisher: Amsterdam: Elsevier Science
  Correspondence: Lin CSK
  Institutions: Bio Base Europe Pilot Plant, Ghent, Belgium, Department of Biology, Hong Kong Baptist University, Hong Kong, China, School of Energy and Environment, City University of Hong Kong, Hong Kong, China, Centre for Industrial Biotechnology and Biocatalysis (InBio.be), Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium
  Methods: 1H NMR, IR, HPLC, enzymatic digestion, colorimetry, cell growth, spectrophotometry, optical density measurement, HPLC-ELSD, vacuum filtration, anthrone assay
  
   
  
  Starmerella bombicola ATCC 22214
  CSDB ID 49772 (all data & tools)
• Article ID: 8926
  Ozdener MH, Ashby RD, Jyotaki M, Elkaddi N, Spielman AI, Bachmanov AA, Solaiman DKY "Sophorolipid biosurfactants activate taste receptor type 1 member 3-mediated taste responses and block responses to bitter taste In vitro and In vivo" - Journal of Surfactants and Detergents 22(3) (2019) 441-449
  

  Sophorolipids (SL) are typically produced and secreted by select nonpathogenic yeast species (i.e., Candida) from renewable substrates. They are currently being used by industry on a limited basis in formulations for cleaning solutions as well as laundry and dishwashing detergents. Due to the nature of their chemical structure, it was hypothesized that SL would demonstrate taste-sensory properties. In this study, SL were produced via fermentation on a mixed substrate platform with glucose and either palmitic acid, stearic acid, or oleic acid using Candida (currently reclassified as Starmerella) bombicola ATCC 22214. The taste properties of SL were determined using a single-cell manual calcium imaging technique on cultured human fungiform taste papillae (HBO) cells. The results of those studies demonstrated that sweetener-responsive HBO cells also respond to SL, and these responses are mediated by the type 1 taste receptors 3 (T1R3), because they were blocked by lactisole (a T1R3 receptor-specific blocker). The involvement of the T1R3 receptor in SL recognition was confirmed via the chorda tympani nerve recording (CTNR) study in a (−/−) T1R3 knockout (KO) mouse model. We further demonstrated that SL are capable of blocking the bitter stimuli-elicited responses both in HBO cells and in the CTNR study. This is the first report demonstrating that SL have taste-sensory properties, which opens up numerous possibilities for practical applications of SL to ameliorate bitter tastes in foods and drugs and understand the potential source of dysgeusia in some patients.

  sophorolipids, taste cell, sensory, HBO cells, bitter, sweet, T1R3

  Publication DOI: 10.1002/jsde.12246
  Journal NLM ID: 101527053
  Publisher: Champaign, IL : AOCS Press
  Correspondence: Ozdener MH ; Solaiman DKY
  Institutions: Eastern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Wyndmoor, USA, Monell Chemical Senses Center, Philadelphia, USA, New York University College of Dentistry, New York, USA
  Methods: biological assays, RT-PCR, LC-MS, cell growth, optical microscopy, TIC, immunocytochemical analyses
  
   
  
  Starmerella bombicola ATCC 22214
  CSDB ID 49778 (all data & tools)
• Article ID: 8932
  Wang H, Roelants SLKW, To MH, Patria RD, Kaur G, Lau NZ, Lau CY, Van Bogaert INA, Soetaert W, Lin CSK "Starmerella bombicola: recent advances on sophorolipids production and prospects of waste stream utilization" - Journal of Chemical Technology and Biotechnology 94(4) (2019) 999-1007
  

  Sophorolipids is one of the most extensively studied microbial biosurfactants. Starmerella bombicola is the most productive strain known for sophorolipid production with volumetric productivity of up to 3.7g/(L∙h). This review focuses on the two most important aspects that have an influence on sophorolipid commercialization. Firstly, the metabolic engineering achievements of S. bombicola in the last decade were summarized. Secondly, three improvements of bioprocess were described including alternative feedstock, fermentation strategy and special designed bioreactor. Discussion has been made on the waste source that have been used as feedstock for sophorolipids production, and this review also emphasized the potential of food waste as nutrient source. Fermentation strategies that correlated with the special designed bioreactors for commercialization were also discussed in detail.

  sophorolipids, Starmerella bombicola, food waste, genetic modification, special designed bioreactor

  Publication DOI: 10.1002/jctb.5847
  Journal NLM ID: 8711102
  Publisher: Chichester Sussex: Published For The Society Of Chemical Industry By Wiley And Sons Ltd
  Correspondence: carollin@cityu.edu.hk
  Institutions: BioPort Group, Centre for Synthetic Biology, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium, Bio Base Europe Pilot Plant, Ghent, Belgium, Centre for Industrial Biotechnology and Biocatalysis (InBio.be), Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium, School of Energy and Environment, City University of Hong Kong, Kowloon, Hong Kong, China, Sino-Forest Applied Research Centre for Pearl River Delta Environment and Department of Biology, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
  
   
  
  Starmerella bombicola
  CSDB ID 49806 (all data & tools)
• Article ID: 8934
  Yang L, Li Y, Zhang X, Liu T, Chen J, Wei L, Hua Q "Metabolic profiling and flux distributions reveal a key role of acetyl-CoA in sophorolipid synthesis by Candida bombicola" - Biochemical Engineering Journal 145 (2019) 74-82
  

  Sophorolipids are important biosurfactants produced by the wild-type strain of Candida bombicola ATCC 22214, with antimicrobial, antiviral, and anticancer activities. Our previous study showed that a mutant strain lacking multifunctional enzyme type 2 displayed extremely low sophorolipid production capacity compared to the wild-type strain. In the present study, we aimed to reveal the possible reasons for this deficiency through a series of analytical methods. First, comparative metabolic profiling analysis between the wild-type and mutant strains was performed. Multivariate statistical analysis, including principal component analysis and orthogonal partial least squares discriminant analysis, showed that nine potential metabolites were closely associated with the metabolic differences between strains. Second, metabolic flux analysis revealed that an inadequate supply of intracellular acetyl-CoA in the mutant strain could significantly affect the biosynthesis of sophorolipids. In addition, supplementation of citric acid recovered the sophorolipid production in the mutant strain by approximately 83%, suggesting that citrate metabolism plays an important role in sophorolipid biosynthesis. These findings provide novel theoretical insights for further improving the production of sophorolipids in C. bombicola.

  biosurfactant, acetyl-CoA, sophorolipid, Candida bombicola, metabolic flux, metabolic profile

  Publication DOI: 10.1016/j.bej.2019.02.013
  Journal NLM ID: 9891831
  Publisher: Amsterdam; New York, NY: Elsevier
  Correspondence: Li Y ; Hua Q
  Institutions: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, China, Shanghai Collaborative Innovation Center for Biomanufacturing Technology, Shanghai, China
  Methods: methylation, GC-MS, alkaline hydrolysis, extraction, cell growth, derivatization, LC, centrifugation, UHPLC-MS, HPLC-UV
  
   
  
  Candida bombicola ATCC22214
  CSDB ID 49811 (all data & tools)
• Article ID: 9105
  Bisht KS, Gross RA, Kaplan DL "Enzyme-mediated regioselective acylations of sophorolipids" - Journal of Organic Chemistry 64(3) (1999) 780-789
  

  Enzymatic synthesis of well-defined sophorolipid analogues for evaluation of their bioactivities and as new building blocks for the preparation of glycolipid-based amphiphilic polymers is described. Lipase Novozym 435 from Candida antarctica has been shown to be an efficient catalyst for acylation of sophorolipids esters. A mixture of sophorolipids produced by Torulopsis bombicola was esterified by reaction with sodium alcoxide. The alkyl esters of sophorose lipids were subjected to Novozym 435 catalyzed acylation in dry tetrahydrofuran (THF) with vinyl acrylate and vinyl acetate to diacyl derivatives. The reactions were highly regioselective, and exclusive acylation of the hydroxyl groups on C-6' and C-6'' took place. Methyl ester in the absence of the acylating agent, or with the agent at a concentration less than equimolar, gave sophorolactone (9). Careful analysis of the spectral data revealed it to be a synthetic analogue of microbially produced macrolactone. Sophorolactone (9) differs in the site at which the sophorose ring is attached to the fatty acid. Specifically, in 9, unlike the natural sophorolipids, the fatty acid carboxyl carbon is linked to the C-6'' hydroxyl, not to the C-4'' hydroxyl. Subsequent acrylation of 9 catalyzed by Novozym 435 led to the formation of the C-6' monoacryl derivative linked only to the primary site.

  acylation, sophorolipids, Candida bombicola, Torulopsis bombicola, Novozym 435, Candida antarctica

  NCBI PubMed ID: 11674146
  Publication DOI: 10.1021/jo981497m
  Journal NLM ID: 2985193R
  Publisher: Columbus, OH: American Chemical Society
  Institutions: Polytechnic University, Six Metrotech Center, Brooklyn, USA, Department of Chemical Engineering, Tufts University, Medford, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, MALDI-TOF MS, enzymatic digestion, extraction, optical rotation measurement, CC, enzymatic synthesis, cell growth, centrifugation
  
   
  
  Torulopsis bombicola
  CSDB ID 50184 (all data & tools)
• Article ID: 9106
  Bisht KS, Gao W, Gross RA "Glycolipids from Candida bombicola: Polymerization of a 6-O-acryloyl sophorolipid derivative" - Macromolecules 33(17) (2000) 6208-6210
  

  The strategy was developed for the site-selective incorporation of an acryl group in the sophorolipid molecule. The acryoyl sophorolipid derivative copolymer structures generated have controlled quantities of a unique amphiphilic structure that will be of interest in solution studies that will follow. It is also noteworthy to point out that this work made use of a chemoenzymatic approach, exploiting the best of enzyme and chemical methods.

  carbohydrates, Polymers, hydroxyls, organic compounds, copolymers

  Publication DOI: 10.1021/ma0001537
  Journal NLM ID: 0365316
  Publisher: ACS
  Institutions: Polytechnic University, NSF Center for Biocatalysis and Bioengineering, Six Metrotech Center, Brooklyn, USA
  Methods: 13C NMR, 1H NMR, MS, GPC, optical rotation measurement, CC, enzymatic assay, derivatization
  
   
  
  Candida bombicola
  CSDB ID 50186 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 729.8 [M+Na]+
Compound class: glycolipid, sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7218
  Konishi M, Fukuoka T, Morita T, Imura T, Kitamoto D "Production of new types of sophorolipids by Candida batistae" - Journal of Oleo Science 57(6) (2008) 359-369
  

  Sophorolipids (SLs) are glycolipid biosurfactants abundantly produced from different feedstocks by yeasts, and have been widely developed for various applications. In this study, we searched for novel SLs, aiming to broaden the functions and application range. As a result of screening based on the phylogenetic information of a known SL producer, we found that Candida batistae CBS 8550 produces new types of SLs. Interestingly, the present product mainly constituted acid-form SLs (more than 60% of the total SLs), considerably different from conventional SLs that mainly constitute lactone-form ones. In the shake-flask culture with glucose and olive oil as the carbon sources, the yeast produced 6 g/L of SLs after 3 days cultivation. The critical micelle concentrations of the present SL product and isolated acid-form SL (GL-A) were 366 and 138 mg/L, respectively, while those of conventional SLs and isolated acid-form SL were 17 and 95 mg/L, respectively. From these results, the phylogenetic approach should lead to the discovery of new biosurfactant producers, and the yeast product possessing high hydrophilicity may facilitate a broad range of applications for SLs.

  glycolipid, biosurfactant, sophorolipids, Candida batistae

  NCBI PubMed ID: 18469499
  Publication DOI: 10.5650/jos.57.359
  Journal NLM ID: 101175339
  Publisher: Tokyo: Japan Oil Chemists Society
  Correspondence: Dai Kitamoto
  Institutions: Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology, Ibaraki, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, MALDI-TOF MS, NMR-1D, extraction, methylation analysis, CC, determination of surface tension
  
   
  
  Starmerella bombicola NBRC 10243
  CSDB ID 43411 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: acidic sophorolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7264
  Joshi-Navare K, Shiras A, Prabhune A "Differentiation-inducing ability of sophorolipids of oleic and linoleic acids using a glioma cell line" - Biotechnology Journal 6(5) (2011) 509-512
  

  Sophorolipids are biosurfactants produced by non-pathogenic yeasts. They show structural similarity with the membrane components of mammalian cells, i.e., glycosphingolipids and gangliosides, which are involved in processes such as signaling, oncogenesis, and differentiation. Sophorolipids have been reported to induce differentiation in several leukemic cell lines, cell death via apoptosis in a human liver cancer cell line, and necrosis in a pancreatic adenocarcinoma cell line. Here we report, for the first time, the effects of precursor fatty acids and sophorolipids of oleic and linoleic acids in pure acidic and crude forms on LN-229, a glioma cell line. In response to different sophorolipid forms, various morphological changes were observed, such as formation of long thread-like extensions arising from the ends of the cells, cell alignment, cell elongation and bundle formation in a dose-dependent manner. In this study we present the morphological evidence of the potential of sophorolipids as differentiation inducers.

  differentiation, sophorolipid, glioma, LN-229

  NCBI PubMed ID: 21381203
  Publication DOI: 10.1002/biot.201000345
  Journal NLM ID: 101265833
  Publisher: Weinheim: Wiley-VCH Verlag
  Correspondence: aa.prabhune@ncl.res.in
  Institutions: Biochemical Sciences Division, National Chemical Laboratory, Pune, India, National Centre for Cell Sciences, University of Pune, Pune, India
  Methods: NMR, extraction, antitumor activity assay, MTT
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 43447 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₃₀H₅₄O₁₂
Compound class: glycolipid, sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7303
  Saerens KM, Zhang J, Saey L, Van Bogaert IN, Soetaert W "Cloning and functional characterization of the UDP-glucosyltransferase UgtB1 involved in sophorolipid production by Candida bombicola and creation of a glucolipid-producing yeast strain" - Yeast 28(4) (2011) 279–292
  

  Sophorolipids produced by the non-pathogenic yeast Candida bombicola ATCC 22214 are glycolipid biosurfactants applied commercially as biodegradable and eco-friendly detergents. Their low cell toxicity, excellent wetting capability and antimicrobial activity attract the attention of high-value markets, such as the cosmetic and pharmaceutical industries. Although sophorolipid production yields have been increased by the optimization of fermentation parameters and feed sources, the biosynthetic pathway and genetic mechanism behind sophorolipid production still remains unclear. Here we identify a UDP-glucosyltransferase gene, UGTB1, with a key function in this economically important pathway. The protein shows sequence and structural homology to several bacterial glycosyltransferases involved in macrolide antibiotic synthesis. Deletion of UGTB1 in C. bombicola did not affect cell growth and resulted in a yeast producing glucolipids, thereby opening the route for in vivo production of these glycolipid intermediates. Activity assays on cell lysates confirmed that the identified gene is responsible for the second glucosylation step during sophorolipid production and illustrated that sophorolipid production in C. bombicola involves the stepwise action of two independent glucosyltransferases. The complete UGTB1 sequence data have been submitted to the GenBank database (http://www.ncbi.nlm.nih.gov) under Accession No. HM440974.

  glucosyltransferase, biosurfactant, sophorolipid, Candida bombicola, glucolipid

  NCBI PubMed ID: 21456054
  Publication DOI: 10.1002/yea.1838
  Journal NLM ID: 8607637
  Publisher: Chichester, Wiley
  Correspondence: Saerens KM
  Institutions: Laboratory of Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Ghent,Belgium
  Methods: DNA techniques, MS, HPLC, extraction, GC–MS
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 43557 (all data & tools)
• Article ID: 7315
  Saerens KMJ, Roelants SLKW, Van Bogaert INA, Soetaert W "Identification of the UDP-glucosyltransferase gene UGTA1, responsible for the first glucosylation step in the sophorolipid biosynthetic pathway of Candida bombicola ATCC 22214" - FEMS Yeast Research 11(1) (2011) 123–132
  

  Candida bombicola ATCC 22214 is applied commercially for the production of sophorolipids from renewable resources such as vegetable oils or waste streams. Although much research has been performed on optimization of fermentation conditions and on the influence of feed source and process parameters on sophorolipid structures and yields, the metabolic pathway of these important bioproducts remains unclear. Here, we identify a glucosyltransferase gene UGTA1 and show that the gene product is responsible for the first glucosylation step in the biosynthetic pathway of sophorolipids. Moreover, we provide evidence that the second glucosylation step is catalysed by a different glucosyltransferase that acts independently from the first. Therefore, the biosynthesis of sophorolipids by C. bombicola involves two glucosyltransferases that act in a stepwise manner. The UGTA1 gene described here is the first identified gene with a clear function in sophorolipid production by this economically important yeast.

  glucosyltransferase, biosurfactant, sophorolipid, Candida bombicola

  Publication DOI: 10.1111/j.1567-1364.2010.00695.x
  Journal NLM ID: 101085384
  Publisher: Oxford University Press
  Correspondence: Saerens KMJ
  Institutions: Laboratory of Industrial Biotechnology and Biocatalysis (InBio.be), Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium
  Methods: HPLC-ELSD, enzyme assays
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 43617 (all data & tools)
• 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: 21502725
  Publication DOI: 10.5650/jos.60.267
  Journal NLM ID: 101175339
  Publisher: 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
  
   
  
  Starmerella bombicola NBRC 10243
  CSDB ID 43580 (all data & tools)
• Article ID: 7369
  Baccile N, Babonneau F, Jestin J, Pehau-Arnaudet G, Van Bogaert I "Unusual, pH-induced, self-assembly of sophorolipid biosurfactants" - ACS Nano 6(6) (2012) 4763-4776
  

  An increasing need exists for simple, bioderived, nontoxic, and up-scalable compounds with stimuliresponsive properties. Acidic sophorolipids (SL) are glucose-based biosurfactants derived from the yeast broth of Candida bombicola (teleomorph: Starmerella bombicola). The specific design of this molecule, a sophorose head with a free end-COOH group at the end of the alkyl chain, makes it a potentially interesting pH-responsive compound. We have specifically investigated this assumption using a combination of small angle neutron scattering (SANS), transmission electron microscopy under cryogenic conditions (Cryo-TEM), and nuclear magnetic resonance (NMR) techniques and found a strong dependence of SL self-assembly on the degree of ionization, R, of the COOH group at concentration values as low as 5 and 0.5 wt %. At least three regimes can be identified where the supramolecular behavior of SL is unexpectedly different: (1) at low R values, self-assembly is driven by concentration, C, and micelles are mainly identified as nonionic objects whose curvature decreases (sphere-to-rod) with C; (2) at mid R values, the formation of COO- groups introduces negative charges at themicellar surface inducing an increase in curvature (rod-to-sphere transition). Repulsive electrostatic long-range interactions appear at this stage. In both regimes 1 and 2, the cross-section radius of the micelles is below 25 Å. This behavior is concentration independent. (3) At R = 1, individual micelles seem to favor the formation of large netlike tubular aggregates whose size is above 100 nm. Such a complex behavior is very unique as it is generally not observed for common alkyl-based surfactants in concentration ranges below 5-10 wt %.

  Self-assembly, sophorolipids, biosurfactants, ionization degree, pH-responsive, microbial-derived surfactants, small angle neutron scattering, cryo-TEM

  NCBI PubMed ID: 22642974
  Publication DOI: 10.1021/nn204911k
  Journal NLM ID: 101313589
  Publisher: American Chemical Society
  Correspondence: niki.baccile@upmc.fr
  Institutions: UPMC Université Paris 06, UMR 7574, Chimie de la Matière Condensée de Paris, Paris, France, CNRS and §Collège de France, UMR 7574, Chimie de la Matière Condensée de Paris, Paris, France, Laboratoire Léon Brillouin, LLB, CEA Saclay, Gif-sur-Yvette, France, Plate-Forme de Cryomicroscopie Moléculaire, URA 2185, Institut Pasteur, Paris, France, InBio, Department of Biochemical and Microbial Technology, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium
  Methods: 1H NMR, small-angle neutron scattering (SANS), TEM, NOESY
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 43784 (all data & tools)
• Article ID: 7425
  Van Bogaert IN, Saerens K, De Muynck C, Develter D, Soetaert W, Vandamme EJ "Microbial production and application of sophorolipids" - Applied Microbiology and Biotechnology 76(1) (2007) 23-24
  

  Sophorolipids are surface-active compounds synthesized by a selected number of yeast species. They have been known for over 40 years, but because of growing environmental awareness, they recently regained attention as biosurfactants due to their biodegradability, low ecotoxicity, and production based on renewable resources. In this paper, an overview is given of the producing yeast strains and various aspects of fermentative sophorolipid production. Also, the biochemical pathways and regulatory mechanisms involved in sophorolipid biosynthesis are outlined. To conclude, a summary is given on possible applications of sophorolipids, either as native or modified molecules.

  biosurfactant, sophorolipids, yeast, Candida bombicola, Candida apicola

  NCBI PubMed ID: 17476500
  Publication DOI: 10.1007/s00253-007-0988-7
  Journal NLM ID: 8406612
  Publisher: Springer
  Correspondence: Inge.VanBogaert@UGent.be
  Institutions: Department of Biochemical and Microbial Technology, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium, Ecover Belgium NV, Belgium, Ecover Belgium NV, Belgium
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 43929 (all data & tools)
• Article ID: 7565
  Gorin PA, Spencer JF, Tulloch AP "Hydroxy fatty acid glycosides of sophorose from Torulopsis magnoliae" - Canadian Journal of Chemistry 39(4) (1961) 846-855
  

  The oil formed during fermentation by a strain of Torulopsis magnoliae consisted mainly of partly acetylated 2-O-β-D-glucopyranosyl-D-glucopyranose units attached β-glycosidically to 17-L-hydroxyoctadecanoic and 17-L-hydroxy-9-octadecenoic acids.

  biosurfactant, sophorolipid, Torulopsis magnoliae, Starmerella magnoliae, Candida magnoliae

  Publication DOI: 10.1139/v61-104
  Journal NLM ID: 0372705
  Publisher: National Research Council of Canada Canada
  Institutions: National Research Council of Canada, Prairie Regional Laboratory, Saskatoon, SK, Canada
  Methods: methylation, deacetylation, acid hydrolysis, GLC, extraction, optical rotation measurement, oxidation, cell growth, evaporation
  
   
  
  Torulopsis magnoliae
  CSDB ID 44335 (all data & tools)
• Article ID: 7637
  Solaiman DKY, Ashby RD, Uknalis J "Characterization of growth inhibition of oral bacteria by sophorolipid using a microplate-format assay" - Journal of Microbiological Methods 136 (2017) 21-29
  

  Sophorolipid (SL) is a class of glycolipid biosurfactant produced by yeast and has potent antimicrobial activity against many microorganisms. In this paper, a microplate-based method was developed to characterize the growth inhibition by SL on five representative species of caries-causing oral bacteria. Bacterial growth on microplate in the absence and presence of varying concentrations of SL was continuously monitored by recording the absorbance at 600nm of the cultures using a microplate reader. The results showed that SL completely inhibited the growth of the Lactobacilli at ≥1mg/ml and the Streptococci at much lower concentrations of ≥50μg/ml. More importantly, we further defined the mechanism of antimicrobial activity of SL by analyzing the pattern of the cell growth curves. SL at sublethal concentrations (<1mg/ml) is bactericidal towards the Lactobacilli; it lengthens the apparent cell-doubling time (Td) and decreases the final cell density (as indicated by A600nm) in a concentration-dependent manner. Against the oral Streptococci, on the other hand, SL at sublethal concentrations (<50μg/ml) is bacteriostatic; it delays the onset of cell growth in a concentration-dependent fashion, but once the cell growth is commenced there is no noticeable adverse effect on Td and the final A600nm. Scanning electron microscopic (SEM) study of L. acidophilus grown in sublethal concentration of SL reveals extensive structural damage to the cells. S. mutans grown in sublethal level of SL did not show morphological damage to the cells, but numerous protruding structures could be seen on the cell surface. At the respective lethal levels of SL, L. acidophilus cells were lysed (at 1mg/ml SL) and the cell surface structure of S. mutans (at 130μg/ml SL) was extensively deformed. In summary, this paper presents the first report on a detailed analysis of the effects of SL on Lactobacilli and Streptococci important to oral health and hygiene.

  biosurfactant, antimicrobial agent, growth-inhibition mechanism, injured cells, microplate assay, tooth decay

  NCBI PubMed ID: 28268111
  Publication DOI: 10.1016/j.mimet.2017.02.012
  Journal NLM ID: 8306883
  Correspondence: dan.solaiman@ars.usda.gov
  Institutions: U.S. Department of Agriculture, Agricultural Research Service, Eastern Regional Research Center, Wyndmoor, USA
  
   
  
  Starmerella bombicola
  CSDB ID 42930 (all data & tools)
• Article ID: 7903
  Baccile N, Noiville R, Stievanod L, Van Bogaerte I "Sophorolipids-functionalized iron oxide nanoparticles" - Physical Chemistry Chemical Physics 15(5) (2013) 1606-1620
  

  Functional iron oxide nanoparticles (NP) have been synthesized in a one and a two-step method using a natural functional glycolipid belonging to the family of sophorolipids (SL). These compounds, whose open acidic form is highly suitable for nanoparticle stabilization, are readily obtained by a fermentation process of the yeast Candida bombicola (polymorph Starmerella bombicola) in large amounts. The final carbohydrate coated iron oxide nanoparticles represent interesting potentially biocompatible materials for biomedical applications. According to the synthesis strategy, magnetic properties can eventually be tuned, thus putting in evidence the direct effect of the glycolipid on the final material’s structure (maghemite and ferrihydrite have been obtained here). A combination of FT-IR, Dynamic Light Scattering (DLS) and UV-Vis experiments shows that SL complex the nanoparticle surface via their accessible COOH group thus forming stable colloids, whose hydrodynamic diameter mostly varies between 10 nm and 30 nm, both in water and in KCl-containing (0.01 M and 2 M) solutions. The materials can stand multiple filtration steps (up to 10) at different extents, where the largest recorded average aggregate size is 100 nm. In general, materials synthesized at T = 80 1C display better stability and smaller size distribution than those obtained at room temperature.

  sophorolipid

  NCBI PubMed ID: 23247504
  Publication DOI: 10.1039/c2cp41977g
  Journal NLM ID: 100888160
  Publisher: Royal Society of Chemistry
  Correspondence: niki.baccile@upmc.fr
  Institutions: InBio, Department of Biochemical and Microbial Technology, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium, UPMC Univ Paris, Chimie de la Matière Condensée de Paris, Paris, France, CNRS, Chimie de la Matière Condensée de Paris, Paris, France, Collège de France, Chimie de la Matière Condensée de Paris, Paris, France, Institut Charles Gerhardt Montpellier - AIME, Université Montpellier II, Montpellier, France
  Methods: 13C NMR, 1H NMR, X-ray, FTIR, extraction, TEM, UV-VIS
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 44867 (all data & tools)
• Article ID: 7914
  Baccile N, Fontecave T, Boissiere C, Van Bogaert INA "Hierarchical porosity in silica thin films by a one-step templating strategy using a stimuli-responsive bioderived glycolipid" - Journal of Physical Chemistry C 117(45) (2013) 23899-23907
  

  Hierarchical porosity in thin films obtained with the evaporation induced self-assembly method is a major challenge that is generally accomplished by combining different templating compounds or strategies, each one typical for a given size range. For instance, for small−medium-sized pores (below 20 nm) a library of surfactants exists, while colloids and polymers, as well as phase separation and water condensation strategies, are used for large mesopores to macropores (up to several micrometers). Here, we report the pH-dependent templating effect using a class of entirely bioderived, functional glycolipids obtained from the culture broth of the yeast Starmerella bombicola. We show that these compounds can be used to achieve a micro-to-macro hierarchical porosity in a one-step process by simply tuning the solution pH and without using any additional cosurfactant, cosolvent, or pore-swelling agent. Small-angle X-ray scattering, transmission electron microscopy, scanning electron microscopy, and ellipsoporosimetry data show the multiscale porous texture of silica thin films.

  Publication DOI: 10.1021/jp409529j
  Journal NLM ID: 101299949
  Publisher: Washington, DC: American Chemical Society
  Correspondence: niki.baccile@upmc.fr
  Institutions: InBio, Department of Biochemical and Microbial Technology, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium, Chimie de la Matière Condensée de Paris, Paris, France, Chimie de la Matière Condensée de Paris, Collège de France, Paris, France
  Methods: X-ray, GC, extraction, hydrolysis, dynamic light scattering, SEM, TEM
  
   
  
  Starmerella bombicola
  CSDB ID 44895 (all data & tools)
• Article ID: 8105
  Cuvier AS, Babonneau F, Berton J, Stevens CV, Fadda GC, Pehau-Arnaudet G, Le Griel P, Prévost S, Perez J, Baccile N "Nanoscale platelet formation by monounsaturated and saturated sophorolipids under basic pH conditions" - Chemistry: a European Journal 21(52) (2015) 19265-19277
  

  The self-assembly behavior of the yeast-derived bolaamphiphile sophorolipid (SL) is generally studied under acidic/neutral pH conditions, at which micellar and fibrillar aggregates are commonly found, according to the (un)saturation of the aliphatic chain: the cis form, which corresponds to the oleic acid form of SL, spontaneously forms micelles, whereas the saturated form, which corresponds to the stearic acid form of SL, preferentially forms chiral fibers. By using small-angle light and X-ray scattering (SLS, SAXS) combined with high-sensitivity transmission electron microscopy imaging under cryogenic conditions (cryo-TEM), the nature of the self-assembled structures formed by these two compounds above pH 10, which is the pH at which they are negatively charged due to the presence of a carboxylate group, has been explored. Under these conditions, these compounds self-assemble into nanoscale platelets, despite the different molecular structures. This work shows that the electrostatic repulsion forces generated by COO(-) mainly drive the self-assembly process at basic pH, in contrast with that found at pH below neutrality, at which self-assembly is driven by van der Waals forces and hydrogen bonding, and thus, is in agreement with previous findings on carbohydrate-based gemini surfactants.

  Self-assembly, Nanostructures, amphiphiles, basicity, micelles

  NCBI PubMed ID: 26592728
  Publication DOI: 10.1002/chem.201502933
  Journal NLM ID: 9513783
  Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
  Correspondence: Cuvier AS
  Institutions: Institut Pasteur, Paris, France, Laboratoire Léon Brillouin, LLB, CEA Saclay, Gif-sur-Yvette, France, Sorbonne Universités, UPMC Univ Paris, CNRS, Collége de France, Chimie de la Matiére Condensee de Paris, Paris, France, SynBioC, Department of Sustainable Organic Chemistry and Technology Ghent University, Ghent, Belgium, ESRF - The European Synchrotron, Grenoble, France, SWING, Synchrotron Soleil, Gif-sur-Yvette, France
  Methods: 1H NMR, alkaline hydrolysis, TEM, SANS, SLS, SAXS, hydrogenation
  
   
  
  Candida bombicola
  CSDB ID 42346 (all data & tools)
• Article ID: 8173
  Kotland A, Hadef I, Renault JH, Hamzaoui M, Martinez A, Borie N, Guilleret A, Reynaud R, Hubert J "Gradient elution method in centrifugal partition chromatography for the separation of a complex sophorolipid mixture obtained from Candida bombicola yeasts" - Journal of Separation Science 36(8) (2013) 1362-1369
  

  Sophorolipids represent an important class of natural surfactants with a variety of environmental, cosmetic, and pharmaceutical applications. Despite their promising physicochemical and biological properties, the use of sophorolipids is hampered by the lack of information regarding their individual structure-activity relationships. The major difficulty in isolating pure sophorolipids arises from the high complexity of crude fermentation media composition and from their strong structural similarities. In this work, a centrifugal partition chromatography method was developed in an original gradient elution mode for the separation of sophorolipids produced by the yeast Candida bombicola. Experiments were realized by using three sets of solvent systems composed of n-heptane, ethyl acetate, n-butanol, methanol, and water in different proportions. The separation was performed at 5 mL/min in the ascending mode by increasing progressively the polarity of the organic mobile phase. In these conditions, more than 80% of the sophorolipids present in the initial crude fermentation extract were eluted successively from the most hydrophobic lactone forms to the most hydrophilic acid forms. The structures of the isolated sophorolipids were further elucidated by HPLC and NMR analyses.Sophorolipids represent an important class of natural surfactants with a variety of environmental, cosmetic, and pharmaceutical applications. Despite their promising physicochemical and biological properties, the use of sophorolipids is hampered by the lack of information regarding their individual structure-activity relationships. The major difficulty in isolating pure sophorolipids arises from the high complexity of crude fermentation media composition and from their strong structural similarities. In this work, a centrifugal partition chromatography method was developed in an original gradient elution mode for the separation of sophorolipids produced by the yeast Candida bombicola. Experiments were realized by using three sets of solvent systems composed of n-heptane, ethyl acetate, n-butanol, methanol, and water in different proportions. The separation was performed at 5 mL/min in the ascending mode by increasing progressively the polarity of the organic mobile phase. In these conditions, more than 80% of the sophorolipids present in the initial crude fermentation extract were eluted successively from the most hydrophobic lactone forms to the most hydrophilic acid forms. The structures of the isolated sophorolipids were further elucidated by HPLC and NMR analyses.

  sophorolipids, Candida bombicola, centrifugal partition chromatography

  NCBI PubMed ID: 23520018
  Publication DOI: 10.1002/jssc.201201033
  Journal NLM ID: 101088554
  Publisher: Weinheim: Wiley-VCH
  Correspondence: Hubert J
  Institutions: Université de Reims Champagne-Ardenne, Reims, France, Soliance, Pomacle, France
  Methods: 13C NMR, 1H NMR, HPLC, HMBC, COSY, HSQC
  
   
  
  Candida bombicola
  CSDB ID 45090 (all data & tools)
• Article ID: 8700
  Dubey P, Kumar S, Aswal VK, Ravindranathan S, Rajamohanan PR, Prabhune A, Nisal A "Silk fibroin-sophorolipid gelation: deciphering the underlying mechanism" - Biomacromolecules 17(10) (2016) 3318-3327
  

  Silk fibroin (SF) protein, produced by silkworm Bombyx mori, is a promising biomaterial, while sophorolipid (SL) is an amphiphilic functional biosurfactant synthesized by nonpathogenic yeast Candida bombicola. SL is a mixture of two forms, acidic (ASL) and lactonic (LSL), which when added to SF results in accelerated gelation of silk fibroin. LSL is known to have multiple biological functionalities and hence hydrogels of these green molecules have promising applications in the biomedical sector. In this work, SANS, NMR, and rheology are employed to examine the assembling properties of individual and mixed SLs and their interactions with SF to understand the mechanism that leads to rapid gelation. SANS and NMR studies show that ASL assembles to form charged micelles, while LSL forms micellar assemblies and aggregates of a mass fractal nature. ASL and LSL together form larger mixed micelles, all of which interact differently with SF. It is shown that preferential binding of LSL to SF causes rapid unfolding of the SF chain leading to the formation of intermolecular beta sheets, which trigger fast gelation. Based on the observations, a mechanism for gelation of SF in the presence of different sophorolipids is proposed.

  biosurfactant, yeast, sophorolipid, Candida bombicola

  NCBI PubMed ID: 27643890
  Publication DOI: 10.1021/acs.biomac.6b01069
  Journal NLM ID: 100892849
  Publisher: Washington, DC: American Chemical Society
  Correspondence: Prabhune A ; Nisal A
  Institutions: Biochemical Sciences Division, Central NMR Facility, National Chemical Laboratory, Pune, India, Polymer Science and Engineering, National Chemical Laboratory, Pune, India, Solid State Physics Division, Bhabha Atomic Research Centre, Mumbai, India
  Methods: 13C NMR, 1H NMR, ROESY, TOCSY, small-angle neutron scattering (SANS), HMBC, COSY, HSQC
  
   
  
  Starmerella bombicola ATCC 22214
  CSDB ID 42716 (all data & tools)
• Article ID: 8931
  Van Renterghem L, Clicque H, Huyst A, Roelants SLKW, Soetaert W "Miniaturization of Starmerella bombicola fermentation for evaluation and increasing (novel) glycolipid production" - Applied Microbiology and Biotechnology 103(11) (2019) 4347-4362
  

  Both strain engineering and process optimization are intensively studied in microbial biosurfactant literature. However, screening of multiple strains and/or medium components in parallel is a very labor-intensive and timely process, considering the only applied technique nowadays is evaluation through shake flask and/or bioreactor experiments. Therefore, in this work, the development, optimization, and application of a more throughput technique-based on 24-deep well plates-are described for a new Starmerella bombicola strain producing bolaform sophorolipids. To develop an optimal setup, the influence of plate position and culture volume and the type of sandwich cover was investigated. Optimal parameters, which did not result in significant differences compared with shake flask experiments concerning growth, glucose consumption, and production of novel sophorolipids, were defined and validated. Next, the new method was applied to evaluate the influence of the use of alternative (commercial) nitrogen sources in comparison with the yeast extract currently applied in the production medium, aiming to increase production efficiency. Self-made yeast extracts from S. bombicola cells were also included to evaluate possible recycling of cells after fermentation. In conclusion, the designed method enabled the efficient and successful comparison of ten different nitrogen sources in varying concentrations (1, 4, and 10 g/L) on bola sophorolipid production, which can now also be performed for other parameters important for growth and/or glycolipid production.

  glycolipid, biosurfactant, Starmerella bombicola, medium optimization, nitrogen source, throughput screening

  NCBI PubMed ID: 30949810
  Publication DOI: 10.1007/s00253-019-09766-3
  Journal NLM ID: 8406612
  Publisher: Springer
  Correspondence: sophie.roelants@ugent.be
  Institutions: Centre for Industrial Biotechnology and Biocatalysis (InBio.be), Ghent University, Ghent, Belgium
  Methods: TLC, enzymatic digestion, cell growth, evaporation, centrifugation, optical density measurement, UPLC-ELSD
  
   
  
  Starmerella bombicola ATCC 22214 (ΔatΔsble mutant)
  CSDB ID 49801 (all data & tools)

Show legend Show as text

Structure type: monomer ; 460 [M+H]+
Compound class: glucolipid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7303
  Saerens KM, Zhang J, Saey L, Van Bogaert IN, Soetaert W "Cloning and functional characterization of the UDP-glucosyltransferase UgtB1 involved in sophorolipid production by Candida bombicola and creation of a glucolipid-producing yeast strain" - Yeast 28(4) (2011) 279–292
  

  Sophorolipids produced by the non-pathogenic yeast Candida bombicola ATCC 22214 are glycolipid biosurfactants applied commercially as biodegradable and eco-friendly detergents. Their low cell toxicity, excellent wetting capability and antimicrobial activity attract the attention of high-value markets, such as the cosmetic and pharmaceutical industries. Although sophorolipid production yields have been increased by the optimization of fermentation parameters and feed sources, the biosynthetic pathway and genetic mechanism behind sophorolipid production still remains unclear. Here we identify a UDP-glucosyltransferase gene, UGTB1, with a key function in this economically important pathway. The protein shows sequence and structural homology to several bacterial glycosyltransferases involved in macrolide antibiotic synthesis. Deletion of UGTB1 in C. bombicola did not affect cell growth and resulted in a yeast producing glucolipids, thereby opening the route for in vivo production of these glycolipid intermediates. Activity assays on cell lysates confirmed that the identified gene is responsible for the second glucosylation step during sophorolipid production and illustrated that sophorolipid production in C. bombicola involves the stepwise action of two independent glucosyltransferases. The complete UGTB1 sequence data have been submitted to the GenBank database (http://www.ncbi.nlm.nih.gov) under Accession No. HM440974.

  glucosyltransferase, biosurfactant, sophorolipid, Candida bombicola, glucolipid

  NCBI PubMed ID: 21456054
  Publication DOI: 10.1002/yea.1838
  Journal NLM ID: 8607637
  Publisher: Chichester, Wiley
  Correspondence: Saerens KM
  Institutions: Laboratory of Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Ghent,Belgium
  Methods: DNA techniques, MS, HPLC, extraction, GC–MS
  
   
  
  Candida bombicola B11
  CSDB ID 43591 (all data & tools)

Show legend Show as text

Structure type: monomer ; 502 [M+H]+
Compound class: glucolipid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7303
  Saerens KM, Zhang J, Saey L, Van Bogaert IN, Soetaert W "Cloning and functional characterization of the UDP-glucosyltransferase UgtB1 involved in sophorolipid production by Candida bombicola and creation of a glucolipid-producing yeast strain" - Yeast 28(4) (2011) 279–292
  

  Sophorolipids produced by the non-pathogenic yeast Candida bombicola ATCC 22214 are glycolipid biosurfactants applied commercially as biodegradable and eco-friendly detergents. Their low cell toxicity, excellent wetting capability and antimicrobial activity attract the attention of high-value markets, such as the cosmetic and pharmaceutical industries. Although sophorolipid production yields have been increased by the optimization of fermentation parameters and feed sources, the biosynthetic pathway and genetic mechanism behind sophorolipid production still remains unclear. Here we identify a UDP-glucosyltransferase gene, UGTB1, with a key function in this economically important pathway. The protein shows sequence and structural homology to several bacterial glycosyltransferases involved in macrolide antibiotic synthesis. Deletion of UGTB1 in C. bombicola did not affect cell growth and resulted in a yeast producing glucolipids, thereby opening the route for in vivo production of these glycolipid intermediates. Activity assays on cell lysates confirmed that the identified gene is responsible for the second glucosylation step during sophorolipid production and illustrated that sophorolipid production in C. bombicola involves the stepwise action of two independent glucosyltransferases. The complete UGTB1 sequence data have been submitted to the GenBank database (http://www.ncbi.nlm.nih.gov) under Accession No. HM440974.

  glucosyltransferase, biosurfactant, sophorolipid, Candida bombicola, glucolipid

  NCBI PubMed ID: 21456054
  Publication DOI: 10.1002/yea.1838
  Journal NLM ID: 8607637
  Publisher: Chichester, Wiley
  Correspondence: Saerens KM
  Institutions: Laboratory of Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Ghent,Belgium
  Methods: DNA techniques, MS, HPLC, extraction, GC–MS
  
   
  
  Candida bombicola B11
  CSDB ID 43592 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 729 [M+Na]+
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7305
  Price NP, Ray KJ, Vermillion KE, Dunlap CA, Kurtzman CP "Structural characterization of novel sophorolipid biosurfactants from a newly identified species of Candida yeast" - Carbohydrate Research 348 (2011) 33-41
  

  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

  NCBI PubMed ID: 22197069
  Publication DOI: 10.1016/j.carres.2011.07.016
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: Price NP
  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
  Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, MALDI-TOF MS, HPLC, extraction, determination of surface tension, GC–MS
  
   
  
  Starmerella bombicola NRRL Y-17069
  CSDB ID 43568 (all data & tools)

Show legend Show as text

Structure type: cyclic polymer repeating unit ; n=1, 729 [M+Na]+
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7305
  Price NP, Ray KJ, Vermillion KE, Dunlap CA, Kurtzman CP "Structural characterization of novel sophorolipid biosurfactants from a newly identified species of Candida yeast" - Carbohydrate Research 348 (2011) 33-41
  

  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

  NCBI PubMed ID: 22197069
  Publication DOI: 10.1016/j.carres.2011.07.016
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: Price NP
  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
  Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, MALDI-TOF MS, HPLC, extraction, determination of surface tension, GC–MS
  
   
  
  Starmerella bombicola NRRL Y-17069
  CSDB ID 43594 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 622 [M]+
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7308
  Saerens KM, Saey L, Soetaert W "One-step production of unacetylated sophorolipids by an acetyltransferase negative Candida bombicola" - Biotechnology and Bioengineering 108(12) (2011) 2923-2931
  

  Sophorolipids from the non-pathogenic yeast Candida bombicola are applied commercially as biodegradable, eco-friendly surface active agents. These sophorolipids are produced by cultivation in presence of a hydrophobic carbon source and are always constituted of a mixture of structurally related molecules. For some applications however, certain structural variants perform better than others. Acetylation of the sophorolipid molecule is such a parameter that gains interest because of its influence on water solubility, foaming properties, and biological activity. Fully unacetylated sophorolipids therefore are interesting metabolites but cannot be produced in a pure way by conventional cultivation. Here we report the identification of the acetyltransferase gene AT, responsible for acetylation of de novo synthesized sophorolipids in Candida bombicola. By the creation of a Δat deletion mutant, we could create a yeast strain producing purely unacetylated sophorolipids with a yield of 5 ± 0.7 g/L using rapeseed oil as hydrophobic carbon source. In contrast to the chemical production of unacetylated sophorolipids used nowadays, the microbial production leads to mainly lactonic sophorolipids, in addition to minor amounts of acidic sophorolipids.

  acetyltransferase, sophorolipids, biosurfactants, Candida bombicola

  NCBI PubMed ID: 21702032
  Publication DOI: 10.1002/bit.23248
  Journal NLM ID: 7502021
  Publisher: New York: Wiley-VCH
  Correspondence: Saerens KM
  Institutions: Laboratory of Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium
  Methods: DNA techniques, ESI-MS, extraction, HPLC-ELSD, HPLC-RI
  
   
  
  Candida bombicola ATCC 22214 Δat3 mutant
  CSDB ID 43597 (all data & tools)

Show legend Show as text

Structure type: cyclic polymer repeating unit ; 604 [M]+, n=1
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7308
  Saerens KM, Saey L, Soetaert W "One-step production of unacetylated sophorolipids by an acetyltransferase negative Candida bombicola" - Biotechnology and Bioengineering 108(12) (2011) 2923-2931
  

  Sophorolipids from the non-pathogenic yeast Candida bombicola are applied commercially as biodegradable, eco-friendly surface active agents. These sophorolipids are produced by cultivation in presence of a hydrophobic carbon source and are always constituted of a mixture of structurally related molecules. For some applications however, certain structural variants perform better than others. Acetylation of the sophorolipid molecule is such a parameter that gains interest because of its influence on water solubility, foaming properties, and biological activity. Fully unacetylated sophorolipids therefore are interesting metabolites but cannot be produced in a pure way by conventional cultivation. Here we report the identification of the acetyltransferase gene AT, responsible for acetylation of de novo synthesized sophorolipids in Candida bombicola. By the creation of a Δat deletion mutant, we could create a yeast strain producing purely unacetylated sophorolipids with a yield of 5 ± 0.7 g/L using rapeseed oil as hydrophobic carbon source. In contrast to the chemical production of unacetylated sophorolipids used nowadays, the microbial production leads to mainly lactonic sophorolipids, in addition to minor amounts of acidic sophorolipids.

  acetyltransferase, sophorolipids, biosurfactants, Candida bombicola

  NCBI PubMed ID: 21702032
  Publication DOI: 10.1002/bit.23248
  Journal NLM ID: 7502021
  Publisher: New York: Wiley-VCH
  Correspondence: Saerens KM
  Institutions: Laboratory of Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium
  Methods: DNA techniques, ESI-MS, extraction, HPLC-ELSD, HPLC-RI
  
   
  
  Candida bombicola ATCC 22214 Δat3 mutant
  CSDB ID 43598 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: bolaform
Compound class: glycolipid, sophorolipid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7314
  Saerens KMJ, Roelants SLKW, Van Bogaert INA, Soetaert W "Identification of the UDP-glucosyltransferase gene UGTA1, responsible for the first glucosylation step in the sophorolipid biosynthetic pathway of Candida bombicola ATCC 22214" - FEMS Yeast Research 11(1) (2011) 123-132
  

  Candida bombicola ATCC 22214 is applied commercially for the production of sophorolipids from renewable resources such as vegetable oils or waste streams. Although much research has been performed on optimization of fermentation conditions and on the influence of feed source and process parameters on sophorolipid structures and yields, the metabolic pathway of these important bioproducts remains unclear. Here, we identify a glucosyltransferase gene UGTA1 and show that the gene product is responsible for the first glucosylation step in the biosynthetic pathway of sophorolipids. Moreover, we provide evidence that the second glucosylation step is catalysed by a different glucosyltransferase that acts independently from the first. Therefore, the biosynthesis of sophorolipids by C. bombicola involves two glucosyltransferases that act in a stepwise manner. The UGTA1 gene described here is the first identified gene with a clear function in sophorolipid production by this economically important yeast.

  glucosyltransferase, biosurfactant, sophorolipid, Candida bombicola

  Publication DOI: 10.1111/j.1567-1364.2010.00695.x
  Journal NLM ID: 101085384
  Publisher: Oxford University Press
  Correspondence: Saerens KMJ
  Institutions: Laboratory of Industrial Biotechnology and Biocatalysis (InBio.be), Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium
  Methods: enzyme assays
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 43630 (all data & tools)
• Article ID: 7425
  Van Bogaert IN, Saerens K, De Muynck C, Develter D, Soetaert W, Vandamme EJ "Microbial production and application of sophorolipids" - Applied Microbiology and Biotechnology 76(1) (2007) 23-24
  

  Sophorolipids are surface-active compounds synthesized by a selected number of yeast species. They have been known for over 40 years, but because of growing environmental awareness, they recently regained attention as biosurfactants due to their biodegradability, low ecotoxicity, and production based on renewable resources. In this paper, an overview is given of the producing yeast strains and various aspects of fermentative sophorolipid production. Also, the biochemical pathways and regulatory mechanisms involved in sophorolipid biosynthesis are outlined. To conclude, a summary is given on possible applications of sophorolipids, either as native or modified molecules.

  biosurfactant, sophorolipids, yeast, Candida bombicola, Candida apicola

  NCBI PubMed ID: 17476500
  Publication DOI: 10.1007/s00253-007-0988-7
  Journal NLM ID: 8406612
  Publisher: Springer
  Correspondence: Inge.VanBogaert@UGent.be
  Institutions: Department of Biochemical and Microbial Technology, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium, Ecover Belgium NV, Belgium, Ecover Belgium NV, Belgium
  
   
  
  Candida bombicola ATCC 22214
  CSDB ID 43928 (all data & tools)
• Article ID: 9353
  Ben Messaoud G, Le Griel P, Prévost S, Hermida-Merino D, Soetaert W, Roelants SLKW, Stevens CV, Baccile N "Single-molecule lamellar hydrogels from bolaform microbial glucolipids" - Soft Matter 16(10) (2020) 2528-2539
  

  Lipid lamellar hydrogels are rare soft fluids composed of a phospholipid lamellar phase instead of fibrillar networks. The mechanical properties of these materials are controlled by defects, induced by local accumulation of a polymer or surfactant in a classical lipid bilayer. Herein we report a new class of lipid lamellar hydrogels composed of one single bolaform glycosylated lipid obtained by fermentation. The lipid is self-organized into flat interdigitated membranes, stabilized by electrostatic repulsive forces and stacked in micrometer-sized lamellar domains. The defects in the membranes and the interconnection of the lamellar domains are responsible, from the nano- to the micrometer scales, for the elastic properties of the hydrogels. The lamellar structure is probed by combining small angle X-ray and neutron scattering (SAXS, SANS), the defect-rich lamellar domains are visualized by polarized light microscopy while the elastic properties are studied by oscillatory rheology. The latter show that both storage G' and loss G'' moduli scale as a weak power-law of the frequency, that can be fitted with fractional rheology models. The hydrogels possess rheo-thinning properties with second-scale recovery. We also show that ionic strength is not only necessary, as one could expect, to control the interactions in the lamellar phase but, most importantly, it directly controls the elastic properties of the lamellar gels.

  hydrogels, Starmerella bombicola, bolaform, lamellar structure

  NCBI PubMed ID: 32076696
  Publication DOI: 10.1039/c9sm02158b
  Journal NLM ID: 101295070
  Publisher: Cambridge, UK: Royal Society of Chemistry
  Correspondence: niki.baccile@sorbonne-universite.fr
  Institutions: Institut Laue-Langevin, Grenoble, France, Ghent University, Centre for Industrial Biotechnology and Biocatalysis (InBio.be), Ghent, Belgium, Bio Base Europe Pilot Plant, Ghent, Belgium, Sorbonne Université, Centre National de la Recherche Scientifique, Laboratoire de Chimie de la Matière Condensée de Paris, LCMCP, Paris, France, Netherlands Organisation for Scientific Research (NWO), Grenoble, France, SynBioC, Department of Green Chemistry and Technology, Ghent University, Ghent, Belgium
  Methods: NMR, HPLC, differential scanning calorimetry (DSC), microscopy, LC-MS, cell growth, confocal scanning laser microscopy, rheological study, SANS, SAXS
  
   
  
  Starmerella bombicola (ΔugtB1 mutant)
  CSDB ID 50971 (all data & tools)

Show legend Show as text

Structure type: cyclic polymer repeating unit ; 688, n=1, 646
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• 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: 21590287
  Publication DOI: 10.1007/s00253-011-3327-y
  Journal NLM ID: 8406612
  Publisher: 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
  
   
  
  Wickerhamiella domercqiae var. sophorolipid CGMCC 1576
  CSDB ID 43639 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 622, 664, 706
Compound class: sophorolipid
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• 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: 21590287
  Publication DOI: 10.1007/s00253-011-3327-y
  Journal NLM ID: 8406612
  Publisher: 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
  
   
  
  Wickerhamiella domercqiae var. sophorolipid CGMCC 1576
  CSDB ID 43641 (all data & tools)
• 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: 23040390
  Publication DOI: 10.1016/j.enzmictec.2012.08.002
  Journal NLM ID: 8003761
  Correspondence: 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
  
   
  
  Candida albicans O-13-1
  CSDB ID 45945 (all data & tools)