Fate of bisphenol A during treatment with the litter-decomposing fungi Stropharia rugosoannulata and Stropharia coronilla

Kabiersch, Grit; Rajasärkkä, Johanna; Ullrich, René; Tuomela, Marja; Hofrichter, Martin; Virta, Marko; Hatakka, Annele; Steffen, Kari

doi:10.1016/j.chemosphere.2010.12.094

Cited by 33 publications

(16 citation statements)

References 45 publications

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“…was already previously shown to act on BPA as well as on other prominent micropollutants present in water (Hofmann and Schlosser, 2016). Moreover, S. rugosoannulata has been reported to metabolize BPA in addition to other organic environmental pollutants before (Kabiersch et al, 2011;Pozdnyakova et al, 2018).…”

Section: Discussionmentioning

confidence: 90%

Biotransformation of Phthalate Plasticizers and Bisphenol A by Marine-Derived, Freshwater, and Terrestrial Fungi

et al. 2020

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Phthalate esters (PEs, Phthalates) are environmentally ubiquitous as a result of their extensive use as plasticizers and additives in diverse consumer products. Considerable concern relates to their reported xenoestrogenicity and consequently, microbial-based attenuation of environmental PE concentrations is of interest to combat harmful downstream effects. Fungal PE catabolism has received less attention than that by bacteria, and particularly fungi dwelling within aquatic environments remain largely overlooked in this respect. We have compared the biocatalytic and biosorptive removal rates of din -butyl phthalate (DBP) and diethyl phthalate (DEP), chosen to represent two environmentally prominent PEs of differing structure and hydrophobicity, by marine-, freshwater-, and terrestrial-derived fungal strains. Bisphenol A, both an extensively used plastic additive and prominent environmental xenoestrogen, was included as a reference compound due to its well-documented fungal degradation. Partial pathways of DBP metabolization by the ecophysiologically diverse asco-and basidiomycete strains tested were proposed with the help of UPLC-QTOF-MS analysis. Species specific biochemical reaction steps contributing to DBP metabolism were also observed. The involved reactions include initial cytochrome P450-dependent monohydroxylations of DBP with subsequent further oxidation of related metabolites, de-esterification via either hydrolytic cleavage or cytochrome P450-dependent oxidative O-dealkylation, transesterification, and demethylation steps-finally yielding phthalic acid as a central intermediate in all pathways. Due to the involvement of ecophysiologically and phylogenetically diverse filamentous and yeast-like fungi native to marine, freshwater, and terrestrial habitats the results of this study outline an environmentally ubiquitous pathway for the biocatalytic breakdown of plastic additives. Beyond previous research into fungal PE metabolism which emphasizes hydrolytic de-esterification as the primary catabolic step, a prominent role of cytochrome P450 monooxygenase-catalyzed reactions is established.

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Section: Discussionmentioning

confidence: 90%

Biotransformation of Phthalate Plasticizers and Bisphenol A by Marine-Derived, Freshwater, and Terrestrial Fungi

et al. 2020

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“…The organisms such as fungi (Kabiersch et al, 2011), plant-cultured cells (Saiyood et al, 2010) as well as bacteria (Kang and Kondo, 2002a,b;Lobos et al, 1992;Yamanaka et al, 2007) can all be used as biocatalysts for BPA biodegradation. However, all the biodegradations above were carried out under aerobic condition, and no reference reported the capability of both aerobic and anaerobic degradation of BPA by one facultative anaerobe.…”

Section: Introductionmentioning

confidence: 99%

Biodegradation and detoxification of bisphenol A with one newly-isolated strain Bacillus sp. GZB: Kinetics, mechanism and estrogenic transition

Wong

et al. 2012

Bioresource Technology

103

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“…4). The mechanism is described as follows: 1) BPA is oxidized to form hydroquinone and the isopropylphenol carbocation (Kolvenbach et al, 2007); 2) 4-isopropenylphenol (MW ¼134) and 4-isopropylphenol (MW¼136) are formed from isopropylphenol carbocations by the loss of H þ or through the addition of H À ; isopropenylphenol is further transformed to hydroacetophenone (MW ¼ 136) and phydroxybenzaldehyde (MW ¼ 122) (Li et al, 2012); 3) the isopropylphenol carbocation can also react with water to form 4-(2-hydroxylpropan-2-yl)phenol (MW ¼ 152) (Huang and Weber, 2005); 4) products with masses of 244, 260 and 268 may arise from radical coupling reactions involving the isopropylphenol carbocation and other intermediates (Kabiersch et al, 2011). Notably, Suzuki et al (2004) reported a significantly reduced estrogenic activity because of metabolite formation (e.g., hydroxyacetophenone and p-hydroxybenzaldehyde) during BPA biodegradation.…”

Section: Identification Of the Main Degradation Enzyme Metabolites Amentioning

confidence: 99%

Edible fungus degrade bisphenol A with no harmful effect on its fatty acid composition

Zhang

Chen

et al. 2015

Ecotoxicology and Environmental Safety

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Fate of bisphenol A during treatment with the litter-decomposing fungi Stropharia rugosoannulata and Stropharia coronilla

Cited by 33 publications

References 45 publications

Biotransformation of Phthalate Plasticizers and Bisphenol A by Marine-Derived, Freshwater, and Terrestrial Fungi

Biotransformation of Phthalate Plasticizers and Bisphenol A by Marine-Derived, Freshwater, and Terrestrial Fungi

Biodegradation and detoxification of bisphenol A with one newly-isolated strain Bacillus sp. GZB: Kinetics, mechanism and estrogenic transition

Edible fungus degrade bisphenol A with no harmful effect on its fatty acid composition

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