Development of a Cradle-to-Grave Approach for Acetylated Acidic Sophorolipid Biosurfactants

International audienceMicrobial production of biosurfactants represents one of the most interesting alternatives to classical petrol-based compounds due to their low toxicity, high biodegradability, and biological production processes from renewable bioresources. However, some of the main drawbacks generally encountered are the low productivities and the small number of chemical structures available, which limit widespread application of biosurfactants. Although chemical derivatization of (microbial) biosurfactants offers opportunities to broaden the panel of available molecules, direct microbial synthesis is still the preferred option and the use of engineered strains is becoming a valid alternative. In this multidisciplinary work we show the entire process of conception, upscaling of fermentation (150 L) and sustainable purification (filtration), application (foaming, solubilization, antibacterial), and life cycle analysis of acetylated acidic sophorolipids, directly produced by the Starmerella bombicola esterase knock out yeast strain, rather than purified using chromatography from the classical, but complex, mixture of acidic and lactonic sophorolipids

Extraction-free analysis in cosmetics by digital image colorimetry, illustrated by the quantification of urea

An extraction-free methodology is proposed for quantifying urea in cosmetics, which relies on urea-mediated decrease of methyl red decoloration by sodium hypochlorite. The method is applied directly to the cosmetic formulation and the resulting color intensity is captured by a smartphone camera. We demonstrate a linear relationship between color intensity and urea concentration in O/W emulsions and a shampoo. This quantification methodology is fully validated by determining its technical characteristics in an O/W cosmetic emulsion: The standard curve is linear over 2.5–30.0 % w/w urea (R2 ≥ 0.985). The coefficient of variation (CV %) on all quality control levels is ≤ 12.54 % for intermediate precision, indicating acceptable precision. Bias is up to ±4.93 % in the emulsion, indicating acceptable accuracy and a countable matrix effect. The proposed analysis setup in combination with a standard addition methodology is applied to verify urea content in purpose-made emulsions: bias is ≤±10.9 %, even in the presence of interfering ammonia. We finally demonstrate that the camera-captured color intensity of an O/W emulsion is proportional to different colorant concentrations in the formulation. This opens the route for further applications of the proposed setup to other ingredients capable of generating a colored product upon suitable reaction inside the formulation matrix

Carbon Nanotubes Decorated with Palladium Nanoparticles: Synthesis, Characterization, and Catalytic Activity

In this article, the in situ preparation of palladium nanoparticles, as mediated by the self-regulated reduction of palladium acetate with the aid of sodium dodecyl sulfate (SDS), followed by subsequent deposition onto single-walled carbon nanotubes and multiwalled carbon nanotubes (MWCNTs), is reported. The surfactant SDS plays a dual role, namely, aids the solubilization of carbon nanotubes (CNTs) and reduces palladium acetate to palladium nanoparticles. The so-formed nanoPd-CNTs hybrid material is soluble in polar solvents, such as methanol and N,N-dimethylformamide. In this work, the nanoPd-CNTs hybrid material is characterized by electronic absorption spectroscopy, Raman and X-ray photoelectron spectroscopy, thermogravimetric analysis, and transmission electron microscopy. Moreover, the catalytic activity of the nanoPd-MWCNTs hybrid material is evaluated toward the reduction of carbon-carbon olefinic bonds as well as the formation of carbon-carbon bonds in the frame of Suzuki and Stille coupling reactions. We conclude that the synthesized nanoPd-MWCNTs hybrid material shows significant catalytic activity, higher than when conventional catalyst is used, in the hydrogenation of olefinic substrates as demonstrated after evaluation of the measured number of turnovers and turnover frequency parameters.

Synthesis, Bioactivity, Pharmacokinetic and Biomimetic Properties of Multi-Substituted Coumarin Derivatives

A series of novel multi-substituted coumarin derivatives were synthesized, spectroscopically characterized, and evaluated for their antioxidant activity, soybean lipoxygenase (LOX) inhibitory ability, their influence on cell viability in immortalized human keratinocytes (HaCaT), and cytotoxicity in adenocarcinomic human alveolar basal epithelial cells (A549) and human melanoma (A375) cells, in vitro. Coumarin analogues 4a–4f, bearing a hydroxyl group at position 5 of the coumarin scaffold and halogen substituents at the 3-phenyl ring, were the most promising ABTS•+ scavengers. 6,8-Dibromo-3-(4-hydroxyphenyl)-4-methyl-chromen-2-one (4k) and 6-bromo-3-(4,5-diacetyloxyphenyl)-4-methyl-chromen-2-one (3m) exhibited significant lipid peroxidation inhibitory activity (IC50 36.9 and 37.1 μM). In the DCF-DA assay, the 4′-fluoro-substituted compound 3f (100%), and the 6-bromo substituted compounds 3i (80.9%) and 4i (100%) presented the highest activity. The 3′-fluoro-substituted coumarins 3e and 4e, along with 3-(4-acetyloxyphenyl)-6,8-dibromo-4-methyl-chromen-2-one (3k), were the most potent lipoxygenase (LOX) inhibitors (IC50 11.4, 4.1, and 8.7 μM, respectively) while displaying remarkable hydroxyl radical scavenging ability, 85.2%, 100%, and 92.9%, respectively. In silico docking studies of compounds 4e and 3k, revealed that they present allosteric interactions with the enzyme. The majority of the analogues (100 μΜ) did not affect the cell viability of HaCaT cells, though several compounds presented over 60% cytotoxicity in A549 or A375 cells. Finally, the human oral absorption (%HOA) and plasma protein binding (%PPB) properties of the synthesized coumarins were also estimated using biomimetic chromatography, and all compounds presented high %HOA (>99%) and %PPB (60–97%) values