Self-assembling properties of glycolipid biosurfactants and their potential applications

Kitamoto, Daï; Morita, Tomotake; Fukuoka, Tokuma; Konishi, Masaaki; Imura, Tomohiro

doi:10.1016/j.cocis.2009.05.009

Cited by 259 publications

(208 citation statements)

References 75 publications

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“…Furthermore, most glycolipids have additional chemical functions like acetylenic, carboxylic, 4,5 hydroxy 4 in their aliphatic moiety, thus increasing the level of complexity and functionality of these compounds and making them promising precursors for application in advanced material science. 10,11 However, even their simplest structural form hides an underlying complexity in terms of collective supramolecular behaviour.…”

Section: Introductionmentioning

confidence: 99%

pH-Driven Self-Assembly of Acidic Microbial Glycolipids

et al. 2016

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Microbial glycolipids are a class of well-known compounds, but their self-assembly behavior is still not well understood. While the free carboxylic acid end group makes some of them interesting stimuli-responsive compounds, the sugar hydrophilic group and the nature of the fatty acid chain make the understanding of their self-assembly behavior in water not easy and highly unpredictable. Using cryo-transmission electron microscopy (cryo-TEM) and both pH-dependent in situ and ex situ small angle X-ray scattering (SAXS), we demonstrate that the aqueous self-assembly at room temperature (RT) of a family of β-d-glucose microbial glycolipids bearing a saturated and monounsaturated C18 fatty acid chain cannot be explained on the simple basis of the well-known packing parameter. Using the “pH-jump” process, we find that the molecules bearing a monosaturated fatty acid forms vesicles below pH 6.2, as expected, but the derivative with a saturated fatty acid forms infinite bilayer sheets below pH 7.8, instead of vesicles. We show that this behavior can be explained on the different bilayer membrane elasticity as a function of temperature. Membranes are either flexible or stiff for experiments performed at a temperature respectively above or below the typical melting point, T M, of the lipidic part of each compound. Finally, we also show that the disaccharide-containing acidic cellobioselipid forms a majority of chiral fibers, instead of the expected micelles.

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Section: Introductionmentioning

confidence: 99%

pH-Driven Self-Assembly of Acidic Microbial Glycolipids

et al. 2016

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“…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%

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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“…They have attracted considerable interest in recent years due to their unique properties (e.g., biodegradability, biocompatibility, mild production conditions, and various functions) [1][2][3] as compared to chemically synthesized surfactants. Despite the many advantages of using BSs in various technology areas, commercial applications of them have been limited.…”

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confidence: 99%

“…1) are representative glycolipid BSs, abundantly produced by various yeast strains belonging to the genera Starmerella and Pseudozyma at yields of 100 g/L or more. [1][2][3][4] These BSs show not only excellent interfacial and self-assembling properties [8][9][10] but also versatile biological actions, including antitumor and anti-inflammatory effects. 11,12) Many yeast strains are known to be present in various food materials.…”

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confidence: 99%

Biosurfactant-producing yeasts widely inhabit various vegetables and fruits

Konishi

Maruoka

Furuta

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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The isolation of biosurfactant-producing yeasts from food materials was accomplished. By a combination of a new drop collapse method and thin-layer chromatography, 48 strains were selected as glycolipid biosurfactant producers from 347 strains, which were randomly isolated from various vegetables and fruits. Of the producers, 69% were obtained from vegetables of the Brassica family. Of the 48 producers, 15 strains gave relatively high yields of mannosylerythritol lipids (MELs), and were identified as Pseudozyma yeasts. These strains produced MELs from olive oil at yields ranging from 8.5 to 24.3 g/L. The best yield coefficient reached 0.49 g/g as to the carbon sources added. Accordingly, MEL producers were isolated at high efficiency from various vegetables and fruits, indicating that biosurfactant producers are widely present in foods. The present results should facilitate their application in the food and related industries.

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Self-assembling properties of glycolipid biosurfactants and their potential applications

Cited by 259 publications

References 75 publications

pH-Driven Self-Assembly of Acidic Microbial Glycolipids

pH-Driven Self-Assembly of Acidic Microbial Glycolipids

Surface-induced assembly of sophorolipids

Biosurfactant-producing yeasts widely inhabit various vegetables and fruits

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