AI Article Synopsis
- Synthetic monorhamnolipids, specifically Rha-C10-C10, are produced as distinct diastereomers (four possible types) based on the type of β-hydroxyalkanoic acid used, differing from natural rhamnolipids.
- Biodegradability tests showed that both synthetic and biosynthesized forms are highly biodegradable, with mineralization rates between 34% and 92%.
- Toxicity assessments indicated slight ecological toxicity in both synthetic and natural forms, with significant mortality in zebrafish at high concentrations, though one synthetic variant (Rha-C10-C10 (R,R)) showed no developmental effects.
Article Abstract
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 respirometry), acute toxicity (Microtox assay), embryo toxicity (Zebrafish assay), and cytotoxicity (xCELLigence and MTS assays) of synthetic rhamnosyl-β-hydroxydecanoyl-β-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 EC values ranging from 39.6 to 87.5 μM. 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 μM, except the Rha-C10-C10 (R,R) which showed no developmental effects. xCELLigence and MTS showed IC values ranging from 103.4 to 191.1 μM 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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6289288 | PMC |
| http://dx.doi.org/10.1016/j.jhazmat.2018.10.050 | DOI Listing |
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Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers.
J Hazard Mater
February 2019
Department of Soil, Water and Environmental Science, The University of Arizona, Tucson, AZ, 85721, USA. Electronic address:
Article Synopsis
- Synthetic monorhamnolipids, specifically Rha-C10-C10, are produced as distinct diastereomers (four possible types) based on the type of β-hydroxyalkanoic acid used, differing from natural rhamnolipids.
- Biodegradability tests showed that both synthetic and biosynthesized forms are highly biodegradable, with mineralization rates between 34% and 92%.
- Toxicity assessments indicated slight ecological toxicity in both synthetic and natural forms, with significant mortality in zebrafish at high concentrations, though one synthetic variant (Rha-C10-C10 (R,R)) showed no developmental effects.
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