Sophorolipids

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Wim Soetaert - One of the best experts on this subject based on the ideXlab platform.

  • asymmetrical symmetrical divalent and y shaped bola amphiphiles the relationship between the molecular structure and self assembly in amino derivatives of sophorolipid biosurfactants
    Journal of Physical Chemistry B, 2019
    Co-Authors: Niki Baccile, Wim Soetaert, Sophie Roelants, Inge N. A. Van Bogaert, K. M. Van Geem, Jonas Everaert, Martha Brennich, Elisabeth Delbeke, Chloe Seyrig, Christian V. Stevens
    Abstract:

    Conventional head-chain but also more exotic divalent, Gemini, or bolaform amphiphiles have in common well-defined hydrophilic and hydrophobic blocks with often a predictable self-assembly behavior. However, new categories of amphiphiles, such as microbial biosurfactants, challenge such conventional understanding because of the poorly defined boundaries between the hydrophilic and hydrophobic portions. Microbial glycolipids, such as Sophorolipids, rhamnolipids, or cellobioselipids, interesting biodegradable, nontoxic, alternatives to synthetic surfactants, all represent interesting examples of atypical amphiphiles with partially predictable self-assembly properties. However, their limited molecular diversity strongly limits their application potential. For this reason, we used them as ready-made platform to prepare a whole class of new derivatives. In particular, a broad range of amino derivatives of sophorolipid biosurfactant was recently prepared with the goal of producing biobased antimicrobial and tra...

  • MINI-REVIEW Microbial production and application of Sophorolipids
    2016
    Co-Authors: Inge N. A. Van Bogaert, Wim Soetaert, Dirk Develter, Karen Saerens, Ra De Muynck, Erick Vandamme
    Abstract:

    Abstract Sophorolipids are surface-active compounds syn-thesized 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 ecotox-icity, and production based on renewable resources. In this paper, an overview is given of the producing yeast strains and various aspects of fermentative sophorolipid produc-tion. 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

  • characterization of a novel enzyme starmerella bombicola lactone esterase sble responsible for sophorolipid lactonization
    Applied Microbiology and Biotechnology, 2016
    Co-Authors: Katarzyna Ciesielska, Wim Soetaert, Sophie Roelants, Inge N. A. Van Bogaert, Sara Groeneboer, Stijn De Waele, Isabel Vandenberghe, Bart Devreese
    Abstract:

    We recently discovered a novel enzyme in the exoproteome of Starmerella bombicola, which is structurally related to Candida antarctica lipase A. A knockout strain for this enzyme does no longer produce lactonic Sophorolipids, prompting us to believe that this protein is the missing S. bombicola lactone esterase (SBLE). SBLE catalyzes a rather unusual reaction, i.e., an intramolecular esterification (lactonization) of acidic Sophorolipids in an aqueous environment, which raised questions about its activity and mode of action. Here, we report the heterologous production of this enzyme in Pichia pastoris and its purification in a two-step strategy. Purified recombinant SBLE (rSBLE) was used to perform HPLC and liquid chromatography mass spectrometry (LCMS)-based assays with different sophorolipid mixtures. We experimentally confirmed that SBLE is able to perform ring closure of acetylated acidic Sophorolipids. This substrate was selected for rSBLE kinetic studies to estimate the apparent values of K m . We established that rSBLE displays optimal activity in the pH range of 3.5 to 6 and has an optimal temperature in the range of 20 to 50 °C. Additionally, we generated a rSBLE mutant through site-directed mutagenesis of Ser194 in the predicted active site pocket and show that this mutant is lacking the ability to lactonize Sophorolipids. We therefore propose that SBLE operates via the common serine hydrolase mechanism in which the catalytic serine residue is assisted by a His/Asp pair.

  • Petroselinic acid purification and its use for the fermentation of new Sophorolipids.
    AMB Express, 2016
    Co-Authors: Elisabeth Delbeke, Evelien Uitterhaegen, Thierry Talou, Wim Soetaert, Inge N. A. Van Bogaert, Jonas Everaert, Stijn Verweire, Arno Verlee, Christian V. Stevens
    Abstract:

    Petroselinic acid, a positional isomer of oleic acid, was isolated from the vegetable oil of Coriandrum sativum fruits. This uncommon fatty acid was subsequently used as substrate for sophorolipid fermentation with a Starmerella bombicola lactone esterase overexpression (oe sble) strain. A petroselinic acid based diacetylated sophorolipid lactone was obtained in high purity without incorporation of de novo synthesized fatty acids such as oleic acid. A total production of 40 g/L was obtained. The petroselinic acid based sophorolipid lactone was subsequently hydrolyzed towards the petroselinic acid based sophorolipid acid. For both compounds, their critical micelle concentration (CMC) and corresponding surface tension were compared to their oleic acid based counterparts. Both petroselinic acid based Sophorolipids displayed a much lower CMC value than their oleic acid based counterparts, although their minimal surface tension was the same. Besides, the sophorolipid fermentation product was chemically modified towards a novel C12 sophorolipid aldehyde. This derivative constitutes an interesting building block for further modification towards new-to-nature Sophorolipids with high potential for self-assembly applications.

  • Characterization of sophorolipid biosynthetic enzymes from Starmerella bombicola.
    FEMS Yeast Research, 2015
    Co-Authors: Karen Saerens, Inge N. A. Van Bogaert, Wim Soetaert
    Abstract:

    Altering glycolipid structure by genetic engineering of Starmerella bombicola is a recently started research topic and worthy alternative to the unsuccessful selective feeding strategies conventionally applied to reach this goal. One question to be addressed when expressing heterologous proteins in S. bombicola is the activity of the subsequent biosynthetic enzymes toward such modified substrates. In this scope, we studied the substrate specificity of the UDP-glucosyltransferases UgtA1 and UgtB1, responsible for the stepwise synthesis of Sophorolipids from a hydroxylated fatty acid, and that of the acetyltransferase, responsible for acetylation of the sophorolipid molecule. All enzymes showed specificity toward a C18:1 chained acceptor and both glucosyltransferases were highly selective toward the UDP-glucose donor. Severe product inhibition of the glucosyltransferases explains the limited accumulation of sophorolipid intermediates by earlier created single deletion mutants of S. bombicola. Finally, a more detailed study of the acetylation of sophorolipid intermediates sheds light on the enzymatic cascade during synthesis.

Xin Song - One of the best experts on this subject based on the ideXlab platform.

  • In Vitro and in Vivo Anticancer Activity of Sophorolipids to Human Cervical Cancer
    Applied Biochemistry and Biotechnology, 2016
    Co-Authors: Wei Guo, Xin Song
    Abstract:

    Six characteristic di-acetylated lactonic Sophorolipids with C16:1, C16:0, C18:0, C18:1, C18:2, and C18:3 fatty acid were obtained from Starmerella bombicola CGMCC 1576. In order to confirm their anticancer activity against human cervical cancer cells and reveal the structure-activity relationships, their anti-proliferation effects on HeLa and CaSki cells were estimated. The cytotoxicity of sophorolipid molecules with different degrees of unsaturation was proved to be influenced by carbon chain length of Sophorolipids. The longer the carbon chain length, the stronger the cytotoxicity of Sophorolipids. The inhibitory mechanism of a di-acetylated lactonic C18:1 sophorolipid on HeLa cells was investigated. The cells developed many features of apoptosis and cell cycle was blocked at G0 phase and partly at G2 phase. The expression of CHOP and Bip/GRP78 was induced. Caspase-12 and caspase-3 were both activated. However, mitochondrial membrane potential and concentration of cytosolic cytochrome C did not change. The induced apoptosis of HeLa cells was probably triggered through endoplasmic reticulum signaling pathway without involvement of mitochondria. In vivo, 5, 50, and 500 mg/kg lactonic Sophorolipids showed 29.90, 41.24, and 52.06 % of inhibition without significant toxicity to tumor-bearing mice, respectively. Our findings may suggest a potential use of Sophorolipids in human cervical cancer treatment.

  • identification and characterization of a flavin containing monooxygenase moa and its function in a specific sophorolipid molecule metabolism in starmerella bombicola
    Applied Microbiology and Biotechnology, 2016
    Co-Authors: Chengqiang Xia, Xin Song
    Abstract:

    The yeast Starmerella bombicola CGMCC 1576 can produce abundant Sophorolipids (SLs) including almost equal proportion of acidic and lactonic SLs. In this study, a monooxygenase MoA responsible for the metabolism of a sophorolipid molecule, C18:2 diacetylated acidic sophorolipid (C18:2 DASL), was identified, through genomic analysis, protein modeling, and gene knocking out strategy. The yield and compositions of SLs produced by the deletion mutant ∆moA changed dramatically. In HPLC chromatogram, the UV absorption area of C18:2 DASL (one major acidic sophorolipid component) increased from 9.84 × 10(6) mAU × s to 34.26 × 10(6) mAU × s by an increase of 248.17 % when oleic acid was used as hydrophobic carbon source. Moreover, when linoleic acid was used as hydrophobic carbon source, the content of C18:2 DASL component produced by the overexpressed strain Peno::moA decreased significantly compared with that of wild type and △moA. Furthermore, the MoA enzyme was heterologously expressed in Escherichia coli JM109 (DE3) with a recombinant plasmid named pMAL-c2x-moA, and the purified enzyme was obtained through a maltose-binding protein (MBP) affinity chromatography column. The purified C18:2 DASL and C18:1 DASL were applied to be catalyzed by MoA enzyme, respectively; it turned to be that C18:1 DASL still remained in the MoA reaction system, but C18:2 DASL disappeared.

  • production of Sophorolipids with eicosapentaenoic acid and docosahexaenoic acid from wickerhamiella domercqiae var sophorolipid using fish oil as a hydrophobic carbon source
    Biotechnology Letters, 2013
    Co-Authors: Shuang Wang, Xin Song
    Abstract:

    Sophorolipids (SLs) were synthesized by Wickerhamiella domercqiae var. sophorolipid CGMCC 1576 grown on fish oil and glucose. They were purified using preparative HPLC and their structures were identified by MS/MS. The yields of total and lactonic SLs were 47 and 19 g l−1 in shake-flasks when fish oil 4 % (v/v) was used with glucose in the medium. The composition of SL mixture contained more than 20 SL molecules. Several unconventional SL molecules with eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA) including zero-, mono- and di-acetylated acidic SLs with EPA and a di-acetylated acidic SL with DHA were obtained. Two unconventional lactonic SL molecules, non-acetylated lactonic SL with 22:3 and non-acetylated lactonic SL with 20:0, were also obtained.

  • Bioactivities of Sophorolipid with Different Structures Against Human Esophageal Cancer Cells
    Journal of Surgical Research, 2012
    Co-Authors: Lingjian Shao, Xin Song
    Abstract:

    Background Sophorolipids (SLs) obtained from yeast broth are mixtures of many sophorolipid molecules with different structures, and have attracted more attention since they were found to have good antimicrobial, anticancer, anti-inflammatory, and anti-HIV activities. We investigated the effects of sophorolipid molecules with different structures on human esophageal cancer cells in the present work. Materials and Methods Ten sophorolipid (SL) molecules were separated and purified from the Sophorolipids mixture using preparative HPLC, and their structures were identified by MS analyses. The effects of sophorolipid molecules with different structures on two human esophageal cancer cell lines, KYSE 109 and KYSE 450, were investigated by MTT assay. Results The structures of the 10 sophorolipid molecules differ in acetylation degree of sophorose, unsaturation degree of hydroxyl fatty acid, and lactonization or ring opening. The results demonstrated that the inhibition of diacetylated lactonic sophorolipid on two esophageal cancer cells (total inhibition at 30 μg/mL concentration) was stronger than that of monoacetylated lactonic sophorolipid (totally inhibition at 60 μg/mL concentration). Difference of unsaturation degree of hydroxyl fatty acid in SL molecules also had obvious influence on their cytotoxicity to esophageal cancer cells. The sophorolipid with one double bond in fatty acid part had the strongest cytotoxic effect on two esophageal cancer cells (total inhibition at 30 μg/mL concentration). Acidic sophorolipid showed hardly any anticancer activity against esophageal cancer cells. Conclusions In this study, the relationship of anticancer activities of natural sophorolipid molecules and the differences in their structures was revealed, which probably further reveals the mechanism of SL bioactivities and will be helpful in the modification of SL structures to obtain more novel SLs with excellent bioactivities.

  • Effects of nitrogen sources on production and composition of Sophorolipids by Wickerhamiella domercqiae var. sophorolipid CGMCC 1576
    Applied Microbiology and Biotechnology, 2011
    Co-Authors: Lingjian Shao, Jing Shen, Xin Song
    Abstract:

    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 NH4HCO3) 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.

Bart Devreese - One of the best experts on this subject based on the ideXlab platform.

  • characterization of a novel enzyme starmerella bombicola lactone esterase sble responsible for sophorolipid lactonization
    Applied Microbiology and Biotechnology, 2016
    Co-Authors: Katarzyna Ciesielska, Wim Soetaert, Sophie Roelants, Inge N. A. Van Bogaert, Sara Groeneboer, Stijn De Waele, Isabel Vandenberghe, Bart Devreese
    Abstract:

    We recently discovered a novel enzyme in the exoproteome of Starmerella bombicola, which is structurally related to Candida antarctica lipase A. A knockout strain for this enzyme does no longer produce lactonic Sophorolipids, prompting us to believe that this protein is the missing S. bombicola lactone esterase (SBLE). SBLE catalyzes a rather unusual reaction, i.e., an intramolecular esterification (lactonization) of acidic Sophorolipids in an aqueous environment, which raised questions about its activity and mode of action. Here, we report the heterologous production of this enzyme in Pichia pastoris and its purification in a two-step strategy. Purified recombinant SBLE (rSBLE) was used to perform HPLC and liquid chromatography mass spectrometry (LCMS)-based assays with different sophorolipid mixtures. We experimentally confirmed that SBLE is able to perform ring closure of acetylated acidic Sophorolipids. This substrate was selected for rSBLE kinetic studies to estimate the apparent values of K m . We established that rSBLE displays optimal activity in the pH range of 3.5 to 6 and has an optimal temperature in the range of 20 to 50 °C. Additionally, we generated a rSBLE mutant through site-directed mutagenesis of Ser194 in the predicted active site pocket and show that this mutant is lacking the ability to lactonize Sophorolipids. We therefore propose that SBLE operates via the common serine hydrolase mechanism in which the catalytic serine residue is assisted by a His/Asp pair.

  • SILAC-based proteome analysis of Starmerella bombicola sophorolipid production.
    Journal of Proteome Research, 2013
    Co-Authors: Katarzyna Ciesielska, Inge Van Bogaert, Wim Soetaert, Sara Groeneboer, Yao-cheng Lin, Yves Van De Peer, Bart Devreese
    Abstract:

    Starmerella (Candida) bombicola is the biosurfactant-producing species that caught the greatest deal of attention in the academic and industrial world due to its ability of producing large amounts of Sophorolipids. Despite its high economic potential, the biochemistry behind the sophorolipid biosynthesis is still poorly understood. Here we present the first proteomic characterization of S. bombicola for which we created a lys1Δ mutant to allow the use of SILAC for quantitative analysis. To characterize the processes behind the production of these biosurfactants, we compared the proteome of sophorolipid producing (early stationary phase) and nonproducing cells (exponential phase). We report the simultaneous production of all known enzymes involved in sophorolipid biosynthesis including a predicted sophorolipid transporter. In addition, we identified the heme binding protein Dap1 as a possible regulator for Cyp52M1. Our results further indicate that ammonium and phosphate limitation are not the sole limitin...

  • SILAC-Based Proteome Analysis of Starmerella bombicola Sophorolipid Production
    2013
    Co-Authors: Katarzyna Ciesielska, Inge Van Bogaert, Wim Soetaert, Sara Groeneboer, Yves Van De Peer, Yao-chen Lin, Bart Devreese
    Abstract:

    Starmerella (Candida) bombicola is the biosurfactant-producing species that caught the greatest deal of attention in the academic and industrial world due to its ability of producing large amounts of Sophorolipids. Despite its high economic potential, the biochemistry behind the sophorolipid biosynthesis is still poorly understood. Here we present the first proteomic characterization of S. bombicola for which we created a lys1Δ mutant to allow the use of SILAC for quantitative analysis. To characterize the processes behind the production of these biosurfactants, we compared the proteome of sophorolipid producing (early stationary phase) and nonproducing cells (exponential phase). We report the simultaneous production of all known enzymes involved in sophorolipid biosynthesis including a predicted sophorolipid transporter. In addition, we identified the heme binding protein Dap1 as a possible regulator for Cyp52M1. Our results further indicate that ammonium and phosphate limitation are not the sole limiting factors inducing sophorolipid biosynthesis

Christoph Syldatk - One of the best experts on this subject based on the ideXlab platform.

  • Production of Sophorolipids from whey
    Applied Microbiology and Biotechnology, 1999
    Co-Authors: Ralf T Otto, Hansjoachim Daniel, Matthias Reuss, G. Pekin, K. Müller-decker, G. Fürstenberger, Christoph Syldatk
    Abstract:

    Sophorolipids, obtained by a two-stage process starting from deproteinized whey concentrate using Cryptococcus curvatus ATCC 20509 and Candida bombicola ATCC 22214, were compared to products from one-stage processes, using different lipidic compounds as substrates. Results showed that above all carbon source and not cultivation conditions had a distinct influence on the composition of the crude product mixture and therefore on the physicochemical and biological properties of the Sophorolipids, such as, for example, surface activity, cytotoxicity and stability against hydrolases. The results were completed by corresponding data for purified mono- and diacetylated (17-hydroxyoctadecenoic)-1′,4′′-lactonized Sophorolipids. Crude sophorolipid mixtures showed moderate to good surface active properties (SFTmin 39 mN m−1, CMC 130 mg l−1), water solubilities (2–3 g l−1) and low cytotoxicities (LC50 300–700 mg l−1). In contrast, purified Sophorolipids were more surface active (SFTmin 36 mN m−1, CMC 10 mg l−1), less water soluble (max. 70 mg l−1) and showed stronger cytotoxic effects (LC50 15 mg l−1). Incubation of crude sophorolipid mixtures with different hydrolases demonstrated that treatment with commercially available lipases such as from Candida rugosa and Mucor miehei distinctly reduced the surface active properties of the Sophorolipids, while treatment with porcine liver esterase and glycosidases had no effect.

  • production of Sophorolipids from whey development of a two stage process with cryptococcus curvatus atcc 20509 and candida bombicola atcc 22214 using deproteinized whey concentrates as substrates
    Applied Microbiology and Biotechnology, 1999
    Co-Authors: Hansjoachim Daniel, Ralf T Otto, Matthias Reuss, Michael Binder, Christoph Syldatk
    Abstract:

    In order to produce Sophorolipids from whey, thereby lowering the lactose content and biological oxygen demand, a two-step batch cultivation process was developed including medium sterilization by filtration. In the first step, whey was sterilized by a combination of crossflow and sterile filtration. Because the sophorolipid-producing yeast Candida bombicola ATCC 22214 was not able to use lactose as a carbon source directly, the oleaginous yeast Cryptococcus curvatus ATCC 20509 was grown on deproteinized whey concentrates (DWC). With 1: 1 diluted DWC-20, lactose was consumed as the carbon source and biomass (24 g/l dry weight content) as well as single-cell oil (SCO, 10 g/l) were produced. The cultivation broth was disrupted with a glass bead mill and it served as medium for growth (29 g cell dry mass/l) and sophorolipid production (12 g/l) of the yeast C. bombicola.

Inge N. A. Van Bogaert - One of the best experts on this subject based on the ideXlab platform.

  • asymmetrical symmetrical divalent and y shaped bola amphiphiles the relationship between the molecular structure and self assembly in amino derivatives of sophorolipid biosurfactants
    Journal of Physical Chemistry B, 2019
    Co-Authors: Niki Baccile, Wim Soetaert, Sophie Roelants, Inge N. A. Van Bogaert, K. M. Van Geem, Jonas Everaert, Martha Brennich, Elisabeth Delbeke, Chloe Seyrig, Christian V. Stevens
    Abstract:

    Conventional head-chain but also more exotic divalent, Gemini, or bolaform amphiphiles have in common well-defined hydrophilic and hydrophobic blocks with often a predictable self-assembly behavior. However, new categories of amphiphiles, such as microbial biosurfactants, challenge such conventional understanding because of the poorly defined boundaries between the hydrophilic and hydrophobic portions. Microbial glycolipids, such as Sophorolipids, rhamnolipids, or cellobioselipids, interesting biodegradable, nontoxic, alternatives to synthetic surfactants, all represent interesting examples of atypical amphiphiles with partially predictable self-assembly properties. However, their limited molecular diversity strongly limits their application potential. For this reason, we used them as ready-made platform to prepare a whole class of new derivatives. In particular, a broad range of amino derivatives of sophorolipid biosurfactant was recently prepared with the goal of producing biobased antimicrobial and tra...

  • Increasing Uniformity of Biosurfactant Production in Starmerella bombicola via the Expression of Chimeric Cytochrome P450s
    MDPI AG, 2018
    Co-Authors: Robin Geys, Inge N. A. Van Bogaert, Marilyn De Graeve, Christian Stevens, Sofie Lodens, Jeroen Van Malderen, Christophe Lemmens, Margaux De Smet, Stein Mincke, Sofie L. De Maeseneire
    Abstract:

    Sophorolipids are one of the best known microbial biosurfactants and are produced by several yeast species. The best studied producer is Starmerella bombicola, a non-pathogenic yeast associated in nature with bumblebees. Sophorolipids are built up of the rare disaccharide sophorose, which is attached to a fatty acid through a glyosidic bound. Sophorolipids produced by S. bombicola mainly contain oleic acid as the incorporated hydrophobic group. Other chain lengths can, to a certain content, be incorporated by feeding the yeast with substrates of alternative chain lengths. However, the efficiency for such substrates is low as compared to the preferred C18 chain length and defined by the substrate specificity of the first enzymatic step in sophorolipid biosynthesis, i.e., the cytochrome P450 enzyme CYP52M1. To increase product uniformity and diversity at the same time, a new strain of S. bombicola was developed that produces Sophorolipids with a palmitic acid acyl chain. This was achieved by heterologous expression of the cytochrome P450 cyp1 gene of Ustilago maydis and feeding with palmitic acid. Optimization of the production was done by protein and process engineering

  • MINI-REVIEW Microbial production and application of Sophorolipids
    2016
    Co-Authors: Inge N. A. Van Bogaert, Wim Soetaert, Dirk Develter, Karen Saerens, Ra De Muynck, Erick Vandamme
    Abstract:

    Abstract Sophorolipids are surface-active compounds syn-thesized 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 ecotox-icity, and production based on renewable resources. In this paper, an overview is given of the producing yeast strains and various aspects of fermentative sophorolipid produc-tion. 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

  • Lactonic Sophorolipids Increase Tumor Burden in Apcmin+/- Mice.
    PLOS ONE, 2016
    Co-Authors: Breedge Callaghan, Sophie Roelants, Inge N. A. Van Bogaert, Helen L. Lydon, Roger Marchant, Ibrahim M. Banat, Christopher A. Mitchell
    Abstract:

    Sophorolipids (SL) are amphiphilic biosurfactant molecules consisting of a disaccharide sophorose with one fatty acid at the C1 position and optional acetylation at the C6'and C6" positions. They exist in a closed ring lactonic (LSL) or open acidic (ASL) structure Sophorolipids are produced in crude mixtures in economically viable amounts by the yeast Starmerella bombicola and used in a variety of consumer products. Varying levels of anti- proliferative and anti-cancer activity of crude sophorolipid mixtures are described in a number of tumor cell lines in vitro. However, significant inter-study variation exists in the composition of sophorolipid species as well as other biologically active compounds in these mixtures, which makes interpretation of in vitro and in vivo studies difficult. We produced a 96% pure C18:1 lactonic sophorolipid that dose-dependently reduces the viability of colorectal cancer, as well as normal human colonic and lung cell lines in vitro. Oral administration of vehicle-only; or lactonic Sophorolipids (50 mg/kg for 70 days), to Apcmin+/- mice resulted in an increase in the number (55.5 ± 3.3 vs 70.50 ± 7.8: p < 0.05) and size (modal size 2mm vs 4mm) of intestinal polyps. Lactonic administration resulted in a systematic effect via reduced hematocrit (49.5 ± 1.0 vs 28.2 ± 2.0 vs: p

  • lactonic Sophorolipids increase tumor burden in apcmin mice
    PLOS ONE, 2016
    Co-Authors: Breedge Callaghan, Sophie Roelants, Inge N. A. Van Bogaert, Helen L. Lydon, Roger Marchant, Ibrahim M. Banat, Christopher A. Mitchell
    Abstract:

    Sophorolipids (SL) are amphiphilic biosurfactant molecules consisting of a disaccharide sophorose with one fatty acid at the C1 position and optional acetylation at the C6'and C6" positions. They exist in a closed ring lactonic (LSL) or open acidic (ASL) structure Sophorolipids are produced in crude mixtures in economically viable amounts by the yeast Starmerella bombicola and used in a variety of consumer products. Varying levels of anti- proliferative and anti-cancer activity of crude sophorolipid mixtures are described in a number of tumor cell lines in vitro. However, significant inter-study variation exists in the composition of sophorolipid species as well as other biologically active compounds in these mixtures, which makes interpretation of in vitro and in vivo studies difficult. We produced a 96% pure C18:1 lactonic sophorolipid that dose-dependently reduces the viability of colorectal cancer, as well as normal human colonic and lung cell lines in vitro. Oral administration of vehicle-only; or lactonic Sophorolipids (50 mg/kg for 70 days), to Apcmin+/- mice resulted in an increase in the number (55.5 ± 3.3 vs 70.50 ± 7.8: p < 0.05) and size (modal size 2mm vs 4mm) of intestinal polyps. Lactonic administration resulted in a systematic effect via reduced hematocrit (49.5 ± 1.0 vs 28.2 ± 2.0 vs: p<0.03) and splenomegaly (0.56 ± 0.03g vs 0.71 ± 0.04g; p<0.01) confirming exacerbation of disease progression in this model.