Microbial synthesis of sophorolipids

Bogaert, Inge Van; Zhang, Jinxin; Soetaert, Wim

doi:10.1016/j.procbio.2011.01.010

Cited by 217 publications

(153 citation statements)

References 103 publications

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“…98 In literature, it has been reported that the sophorolipids could lower the surface tension of water from 72.8 mJ m À2 to 40-30 mJ m À2 . 44 In the present systems, for all samples, we found that S o 0 for each sample, in principle, a dewetting phenomenon occurred during the drying of the sophorolipids film. 99 In addition, Lee et al 100 have demonstrated that dispersive forces would stabilize the film while polar ones would induce dewetting.…”

Section: Discussionsupporting

confidence: 53%

“…The experiments have been performed using sophorolipids, 39,40 a class of microbial glycolipids obtained from yeasts. [41][42][43][44][45] They have been studied for the last 20 years because of their low carbon footprint and their extensive applications as antibacterial and antifungal agents, 46,47 activity against cancer cells, 48,49 cosmetic products 50,51 and biosurfactants. [52][53][54] The solution properties of non-acetylated, monounsaturated, acidic sophorolipids (SL, see Fig.…”

Section: Introductionmentioning

confidence: 99%

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Surface-induced assembly of sophorolipids

Peyre

Hamraoui

Faustini

et al. 2017

Phys. Chem. Chem. Phys.

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The surface self-assembly properties of acidic sophorolipids, a bolaform microbial glycolipids with pHresponsive properties in solution, were studied based on the chemical nature of the support and pH of the solution. Sophorolipids generally form micelles in water but formation of morphologies like platelets and twisted fibers depending on pH have also been reported. The surface self-assembly was achieved using dip-coating on three different substrates namely gold, silicon(111) and TiO 2 anatase. Deposition conditions (dip-coating withdrawal speed, relative humidity, temperature) were tested, and it was found that optimum self-assembly occurred at a withdrawal speed of 1 mm s À1 , T of 25 1C and relative humidity of 25%. The local structure of the sophorolipid films was characterized by Atomic Force Microscopy, while Scanning Electron Microscopy was used to characterize the spatial homogeneity. We also attempted to correlate dispersive, electron donor and electron attractor surface energy components, using Good-Van Oss's approach, and the behavior of sophorolipids. We found that when the surface energy is dominated by dispersive components, sophorolipids spontaneously assemble into entangled needles at all pH values (4, 6 and 11). However, when the surface energy is dominated by electronic components, pH has a strong influence on the surface self-assembly. We could discriminate three major organizations: homogeneous layer, isolated aggregates and a two-dimensional network similar to block copolymer surface self-assembly.

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Section: Discussionsupporting

confidence: 53%

Section: Introductionmentioning

confidence: 99%

Surface-induced assembly of sophorolipids

Peyre

Hamraoui

Faustini

et al. 2017

Phys. Chem. Chem. Phys.

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“…I). The formed sophorolipids are secreted into the fermentation medium, making them easy to recover from the yeast culture with a yield up to 400 g/l ( 12 ). A recent study has shown that S. bombicola can convert the unnatural substrate ARA to 20-HETE (scheme shown in Fig.…”

Section: Lc-ms/ms Analysismentioning

confidence: 99%

Preparation of 20-HETE using multifunctional enzyme type 2-negative Starmerella bombicola

Bogaert

Zhang

Yang

et al. 2013

Journal of Lipid Research

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(19-HETE) and 20-HETE ( 2 ). 20-HETE has been shown to have an array of largely detrimental effects, inducing hypertension, endothelial dysfunction, infl ammation, cardiovascular diseases, angiogenesis, and tumor growth ( 3-8 ). Our recent research has shown that long-term administration of COX inhibitor rofecoxib caused a greater than 100-fold increase of circulating 20-HETE in a murine model, which suggests that the 20-HETE pathway contributes to the cardiovascular risks of COX inhibitors ( 9 ). More studies are needed to investigate the biological activities and mechanisms of 20-HETE.Development of a scalable method to prepare 20-HETE would greatly facilitate the evaluation of its biological activities and potential therapeutic applications, particularly in animal experiments that require relatively large amount of materials. 20-HETE is commercially available but prohibitively expensive ($4,000 per mg from Caymen Chemicals, Ann Arbor, MI). Chemical synthesis of 20-HETE has been reported ( 10 ); however, the multistep synthesis was challenging to carry out. Enzymatic conversion of ARA to 20-HETE using CYP enzyme(s) is attractive; however, the reaction is low-yield, is diffi cult to scale up, and requires the expensive cofactor NADPH or enzyme systems that generate NADPH. Biotransformation utilizing the nonpathogenic yeast Starmerella bombicola , which expresses CYP / -1-hydroxylases such as CYP52M1, is a promising alternative strategy ( 11 ). This yeast is known for its ability to produce sophorolipids, whose biosynthesis involves hydroxylation of fatty acids at the terminal or subterminal positions by the action of CYP / -1-hydroxylases in order to govern glycosidical coupling to the di-glucoside sophorose. The obtained sophorolipids can undergo further The lipid mediators derived from the arachidonic acid (ARA) cascade are important because these signaling lipids regulate many critical biological processes from infl ammation to tumorigenesis ( 1 ). Therefore, they are important therapeutic targets for many human diseases, and a significant proportion of drugs on the market targets lipid signaling of the ARA cascade. These lipid mediators are best known as prostaglandins and leukotrienes derived from the cyclooxygenase (COX) and lipoxygenase (LOX) pathways, respectively ( 1 ). Besides the intensively studied COX and LOX pathways, ARA is also a substrate of cytochrome P450 (CYP) / -1-hydroxylases (mainly CYP4A and CYP4F), which metabolize it to 19-hydroxyeicosatetraenoic acid This work was supported by National Institutes of Health Grants U24 DK097154, R01 ES-02710 (to B.D.H.), and P42 ES04699 (to B.D.H.

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“…3. This pathway is based on biosynthesis schemes of Fleurackers (2006) and Van Bogaert et al (2011) for classical sophorolipids (fatty acids as co-substrate), and now adapted to the uncommon ketone cosubstrate.…”

Section: A Proposal For the Biosynthetic Pathway For The Formation Ofmentioning

confidence: 99%

“…Further minor differences are associated with the hydroxy fatty acid chain (16 or 18 carbon atoms, saturated or unsaturated chain). Van Bogaert et al (2011) suggested a biosynthetic pathway for this kind of glycolipids. Enzyme-mediated, regioselective modifi cations of the native sophorolipids have been reported (Bisht et al, 1999;Singh et al, 2003).…”

Section: Introductionmentioning

confidence: 99%