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Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers.

ABSTRACT: Synthetic monorhamnolipids differ from biologically produced material because they are produced as single congeners, depending on the ?-hydroxyalkanoic acid used during synthesis. Each congener is produced as one of four possible diastereomers resulting from two chiral centers at the carbinols of the lipid tails [(R,R), (R,S), (S,R) and (S,S)]. We compare the biodegradability (CO2 respirometry), acute toxicity (Microtox assay), embryo toxicity (Zebrafish assay), and cytotoxicity (xCELLigence and MTS assays) of synthetic rhamnosyl-?-hydroxydecanoyl-?-hydroxydecanoate (Rha-C10-C10) monorhamnolipids against biosynthesized monorhamnolipid mixtures (bio-mRL). All Rha-C10-C10 diastereomers and bio-mRL were inherently biodegradable ranging from 34 to 92% mineralized. The Microtox assay showed all Rha-C10-C10 diastereomers and bio-mRL are slightly toxic according to the US EPA ecotoxicity categories with 5?min EC50 values ranging from 39.6 to 87.5??M. The zebrafish assay showed that of 22 developmental endpoints tested, only mortality was observed at 120?h post fertilization; all Rha-C10-C10 diastereomers and bio-mRL caused significant mortality at 640??M, except the Rha-C10-C10 (R,R) which showed no developmental effects. xCELLigence and MTS showed IC50 values ranging from 103.4 to 191.1??M for human lung cell line H1299 after 72?h exposure. These data provide key information regarding Rha-C10-C10 diastereomers that is pertinent when considering potential applications.

SUBMITTER: Hogan DE

PROVIDER: S-EPMC6289288 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers.

Hogan David E DE Tian Fei F Malm Scott W SW Olivares Christopher C Palos Pacheco Ricardo R Simonich Michael T MT Hunjan Anoop S AS Tanguay Robert L RL Klimecki Walter T WT Polt Robin R Pemberton Jeanne E JE Curry Joan E JE Maier Raina M RM

Journal of hazardous materials 20181101

Synthetic monorhamnolipids differ from biologically produced material because they are produced as single congeners, depending on the β-hydroxyalkanoic acid used during synthesis. Each congener is produced as one of four possible diastereomers resulting from two chiral centers at the carbinols of the lipid tails [(R,R), (R,S), (S,R) and (S,S)]. We compare the biodegradability (CO<sub>2</sub> respirometry), acute toxicity (Microtox assay), embryo toxicity (Zebrafish assay), and cytotoxicity (xCEL ...[more]

PMID: 30390580

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Project description:Parabens (esters of p-hydroxybenzoic acid) are xenobiosis belonging to endocrine disruptors and commonly used as a preservative in cosmetics, food, pharmaceutical, and personal care products. Their wide use is leading to their appearance in water and wastewater in the range from ng/L to mg/L. In fact, the toxicity of benzylparaben is comparable to bisphenol A. Therefore, it is important to find not only effective but also ecofriendly methods for their removal from aqueous environment since the traditional wastewater treatment approaches are ineffective. Herein, for the first time, such extended comparison of several radical-driven technologies for paraben mixture degradation is presented. The detailed evaluation included (1) comparison of ozone and hydroxyl peroxide processes; (2) comparison of catalytic and photocatalytic processes (including photocatalytic ozonation); (3) characterisation of catalysts using SEM, XRD, DRS, XPS techniques and BET isotherm; (4) mineralisation, biodegradability and toxicity assessment; and (5) cost assessment. O3, H2O2/Fe2+, H2O2/UVC, O3/H2O2, O3/UVA, O3/H2O2/UVA, UVA/catalyst, O3/catalyst and O3/UVA/catalyst were selected from advanced oxidation processes to degrade parabens as well as to decrease its toxicity towards Aliivibrio fischeri, Corbicula fluminea and Lepidium sativum. Research was focused on the photocatalytic process involving visible light (UVA and natural sunlight) and TiO2 catalysts modified by different metals (Ag, Pt, Pd, Au). Photocatalytic oxidation showed the lowest efficiency, while in combining ozone with catalysis and photocatalysis process, degradation efficiency and toxicity removal were improved. Photocatalytic ozonation slightly improved degradation efficiency but appreciably decreased transferred ozone dose (TOD). Results indicate that the degradation pathway is different, or different transformation products (TPs) could be formed, despite that the hydroxyl radicals are the main oxidant. Graphical abstract.

Dataset Information

Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers.

Publications

Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers.

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