TY - JOUR
T1 - Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers
AU - Hogan, David E.
AU - Tian, Fei
AU - Malm, Scott W.
AU - Olivares, Christopher
AU - Palos Pacheco, Ricardo
AU - Simonich, Michael T.
AU - Hunjan, Anoop S.
AU - Tanguay, Robert L.
AU - Klimecki, Walter T.
AU - Polt, Robin
AU - Pemberton, Jeanne E.
AU - Curry, Joan E.
AU - Maier, Raina M.
N1 - Funding Information:
This work was supported by a National Science Foundation (NSF) Graduate Research Fellowship Grant ( DGE-1143953 , 7/15/2011-6/30/2016 ) to DEH and a NSF Networks for Sustainable Molecular Design and Synthesis Grant ( CHE-1339597 ) co-funded with the Environmental Protection Agency . Zebrafish toxicity tests were supported by the 2014 NIEHS KC Donnelly Externship to CIO and the University of Arizona Superfund Program Training Core (NIEHS grant P42 ES0940 ). SWM was supported as a NIEHS Trainee in Toxicology of Human Diseases (NIEHS grant T32 ES007091 ). RPP was supported by fellowships from Consejo Nacional de Ciencia y Tecnología and Secretaría de Educación Pública of México.
Funding Information:
This work was supported by a National Science Foundation (NSF) Graduate Research Fellowship Grant (DGE-1143953, 7/15/2011-6/30/2016) to DEH and a NSF Networks for Sustainable Molecular Design and Synthesis Grant (CHE-1339597) co-funded with the Environmental Protection Agency. Zebrafish toxicity tests were supported by the 2014 NIEHS KC Donnelly Externship to CIO and the University of Arizona Superfund Program Training Core (NIEHS grant P42 ES0940). SWM was supported as a NIEHS Trainee in Toxicology of Human Diseases (NIEHS grant T32 ES007091). RPP was supported by fellowships from Consejo Nacional de Ciencia y Tecnología and Secretaría de Educación Pública of México.
Publisher Copyright:
© 2018 Elsevier B.V.
PY - 2019/2/15
Y1 - 2019/2/15
N2 - 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 (CO2 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 EC50 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 IC50 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.
AB - 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 (CO2 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 EC50 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 IC50 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.
KW - Biodegradation
KW - Biosurfactant
KW - Rhamnolipid
KW - Stereochemistry
KW - Toxicity
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U2 - 10.1016/j.jhazmat.2018.10.050
DO - 10.1016/j.jhazmat.2018.10.050
M3 - Article
C2 - 30390580
AN - SCOPUS:85055730562
VL - 364
SP - 600
EP - 607
JO - Journal of Hazardous Materials
JF - Journal of Hazardous Materials
SN - 0304-3894
ER -