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Cited by 37Per- and polyfluoroalkyl substances researchToxic Organic Pollutants ImpactEnvironmental Toxicology and Ecotoxicology

Mechanisms for tissue-specific accumulation and phase I/II transformation of 6:2 fluorotelomer phosphate diester in earthworm (M. guillelmi)

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Zhu, Yumin, Jia, Yibo, Liu, Menglin, Yang, Liping, Yi, Shujun, Feng, Xuemin, Zhu, Lingyan·2021·Environment International
DOI 10.1016/j.envint.2021.106451
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Abstract

Polyfluoroalkyl phosphate esters (PAPs) are high production volume surfactants used in the food contact paper and packaging industries. They are prone to partition to soil due to their strong hydrophobicity and may biotransform into recalcitrant perfluoroalkyl carboxylic acids (PFCAs); little is known about their fate and behaviors in terrestrial organisms. Here, geophagous earthworms (M. guillelmi) were exposed to 6:2 fluorotelomer phosphate diester (6:2 diPAP)-contaminated soil to examine tissue-specific accumulation and biotransformation. 6:2 diPAP quickly accumulated in M. guillelmi with the highest biota-soil-accumulation factor (BSAF) in the gut, followed by the organs, skin, and body fluid. The total amount of 6:2 diPAP accumulated in the skin was the highest due to its high mass content. These results indicated that skin absorption and gut processes were two major pathways for earthworms to accumulate 6:2 diPAP from soil. In vitro desorption experiments indicated that the gut digestion fluid greatly promoted the desorption of 6:2 diPAP from the soil and enhanced its bioavailability. Degradation of 6:2 diPAP in the soil was stimulated when the earthworm appeared. In contrast to the soil, a more extensive transformation occurred in the earthworm. Perfluorohexanoic acid (PFHxA) was the primary phase Ⅰ product, followed by perfluoropentyl propanoic acid (FPePA), perfluoropentanoic acid (PFPeA), 2-perfluorohexyl ethanoic acid (FHEA), and perfluoroheptanoic acid (PFHpA), which confirmed the occurrence of α- and β-oxidation in earthworms. For the first time, a new phase II product, namely, a 6:2 fluorotelomer alcohol sulfate conjugate, was identified in earthworms at unexpectedly high levels, which might be the primary way earthworms eliminate 6:2 diPAP. Both in vivo and in vitro experiments suggested that 6:2 diPAP experienced faster and more extensive biotransformation in the gut than in the organs. This work sheds light on the bioaccumulation and biotransformation of 6:2 diPAP in terrestrial invertebrates, providing strong evidence of indirect sources of PFCAs in the environment.

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  • 6:2 diPAP was transformed in vivo in the geophagous earthworm (Metaphire guillelmi) to known PAP-biodegradation products such as PFHxA, PFHpA and PFPeA.

    “Besides bacteria, it is also important to note that 6:2 diPAP was transformed in vivo in the geophagous earthworm (Metaphire guillelmi) to known PAP-biodegradation products such as PFHxA, PFHpA and PFPeA (B. Zhu et al., 2021; Y. Zhu et al., 2021).”

    From A review of microbial degradation of per- and polyfluoroalkyl substances (PFAS): Biotransformation routes and enzymes (2023) · cites this paper as Y. Zhu et al., 2021

  • 6:2 diPAP was transformed in vivo in the geophagous earthworm (Metaphire guillelmi) to known PAP-biodegradation products such as PFHxA, PFHpA and PFPeA.

    “Besides bacteria, it is also important to note that 6:2 diPAP was transformed in vivo in the geophagous earthworm (Metaphire guillelmi) to known PAP-biodegradation products such as PFHxA, PFHpA and PFPeA (B. Zhu et al., 2021; Y. Zhu et al., 2021).”

    From A review of microbial degradation of per- and polyfluoroalkyl substances (PFAS): Biotransformation routes and enzymes (2023) · cites this paper as B. Zhu et al., 2021

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Cited by

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Authors
Zhu, Y., Jia, Y., Liu, M., Yang, L., Yi, S., Feng, X., & Zhu, L.
Affiliations
Nankai University (CN)
Corresponding author
Zhu, Lingyan
ORCID
Venue
Environment International
Publisher
Elsevier BV
Published
2021-06
Volume
151
Pages
106451
ISSN
0160-4120 (ISSN-L)
DOI
10.1016/j.envint.2021.106451
OpenAlex
W3135498999
Cited by
37
References
2
Citations by year
2026: 4 · 2025: 8 · 2024: 8 · 2023: 7 · 2022: 9 · 2021: 1
FWCI
2.32
Type
journal article
Language
en
Open access
Licence
Locations
  • Environment International (publishedVersion, cc-by-nc-nd)
  • PubMed (publishedVersion)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
Funders
  • National Natural Science Foundation of China
  • Ministry of Education of the Peoples Republic of China Yangtze River Scholar
  • Ministry of Science and Technology of the People's Republic of China
Topics
  • Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
  • Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
  • Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Environmental Toxicology and Ecotoxicology
Keywords
earthworms, tissue-specific accumulation, biotransformation, phase I and phase II metabolism, perfluorohexanoic acid, soil desorption, bioavailability, earthworms as bioindicators, terrestrial invertebrates, perfluorinated carboxylic acids, food contact paper
MeSH terms
Animals, Biotransformation, Oligochaeta, Phosphates, Organophosphates, Soil, Soil Pollutants

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