Novel phosphorylation of aldrin-trans-diol by dieldrin-degrading fungus Mucor racemosus strain DDF

Ken ichi Yamazaki, Kazuhiro Takagi, Ryota Kataoka, Masaaki Kotake, Teiko Yamada, Hiromasa Kiyota

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Dieldrin is one of the most persistent organic pollutants, and its oxidative degradation pathways by aerobic microorganisms to 6,7 trans-dihydroxydihydroaldrin (otherwise known as aldrin trans-diol) and 9-hydroxydieldrin are well documented. The dieldrin-degrading fungus, Mucor racemosus strain DDF, can decrease dieldrin levels with simultaneous production of a small amount of aldrin trans-diol. A reduction in the levels of aldrin trans-diol by strain DDF has also been observed. Based on these results, it has been suggested that strain DDF transforms dieldrin to more polar compounds via aldrin trans-diol. We have conducted a study to identify the metabolites arising from aldrin trans-diol. The results showed that strain DDF gave reduced levels of aldrin trans-diol and also produced unknown metabolites. Ultra performance liquid chromatography-electrospray ionization-mass spectroscopy (UPLC-ESI-MS) analysis indicated the metabolites to be either sulfated- or phosphorylated- derivatives of aldrin trans-diol, but with the metabolites retaining six chlorine atoms. Therefore, the candidate derivatives were synthesized and the retention times of the natural metabolite and the synthetic phosphate were compared. As a result of a co-injection experiment, the metabolites were determined to be aldrin trans-diol exo- and endo-phosphates. These results were also supported by high-resolution-fast atom bombardment-mass spectrometry (HR-FAB-MS) of the natural metabolite (δ=0.63ppm). Phosphorylation of aldrin trans-diol is the first reported example of phosphate conjugation in microorganisms.

Original languageEnglish
Pages (from-to)36-40
Number of pages5
JournalInternational Biodeterioration and Biodegradation
Volume92
DOIs
Publication statusPublished - 2014

Fingerprint

Aldrin
Dieldrin
Mucor
Phosphorylation
dieldrin
Metabolites
Fungi
metabolite
fungus
Phosphates
phosphate
Microorganisms
microorganism
Derivatives
Electrospray ionization
Atoms
Organic pollutants
Liquid chromatography
Fast Atom Bombardment Mass Spectrometry
Chlorine

Keywords

  • Bioremediation
  • Dieldrin
  • Fungus
  • HR-FAB-MS
  • LC-ESI-MS
  • Phosphate conjugation

ASJC Scopus subject areas

  • Waste Management and Disposal
  • Microbiology
  • Biomaterials

Cite this

Novel phosphorylation of aldrin-trans-diol by dieldrin-degrading fungus Mucor racemosus strain DDF. / Yamazaki, Ken ichi; Takagi, Kazuhiro; Kataoka, Ryota; Kotake, Masaaki; Yamada, Teiko; Kiyota, Hiromasa.

In: International Biodeterioration and Biodegradation, Vol. 92, 2014, p. 36-40.

Research output: Contribution to journalArticle

Yamazaki, Ken ichi ; Takagi, Kazuhiro ; Kataoka, Ryota ; Kotake, Masaaki ; Yamada, Teiko ; Kiyota, Hiromasa. / Novel phosphorylation of aldrin-trans-diol by dieldrin-degrading fungus Mucor racemosus strain DDF. In: International Biodeterioration and Biodegradation. 2014 ; Vol. 92. pp. 36-40.
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AU - Kotake, Masaaki

AU - Yamada, Teiko

AU - Kiyota, Hiromasa

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N2 - Dieldrin is one of the most persistent organic pollutants, and its oxidative degradation pathways by aerobic microorganisms to 6,7 trans-dihydroxydihydroaldrin (otherwise known as aldrin trans-diol) and 9-hydroxydieldrin are well documented. The dieldrin-degrading fungus, Mucor racemosus strain DDF, can decrease dieldrin levels with simultaneous production of a small amount of aldrin trans-diol. A reduction in the levels of aldrin trans-diol by strain DDF has also been observed. Based on these results, it has been suggested that strain DDF transforms dieldrin to more polar compounds via aldrin trans-diol. We have conducted a study to identify the metabolites arising from aldrin trans-diol. The results showed that strain DDF gave reduced levels of aldrin trans-diol and also produced unknown metabolites. Ultra performance liquid chromatography-electrospray ionization-mass spectroscopy (UPLC-ESI-MS) analysis indicated the metabolites to be either sulfated- or phosphorylated- derivatives of aldrin trans-diol, but with the metabolites retaining six chlorine atoms. Therefore, the candidate derivatives were synthesized and the retention times of the natural metabolite and the synthetic phosphate were compared. As a result of a co-injection experiment, the metabolites were determined to be aldrin trans-diol exo- and endo-phosphates. These results were also supported by high-resolution-fast atom bombardment-mass spectrometry (HR-FAB-MS) of the natural metabolite (δ=0.63ppm). Phosphorylation of aldrin trans-diol is the first reported example of phosphate conjugation in microorganisms.

AB - Dieldrin is one of the most persistent organic pollutants, and its oxidative degradation pathways by aerobic microorganisms to 6,7 trans-dihydroxydihydroaldrin (otherwise known as aldrin trans-diol) and 9-hydroxydieldrin are well documented. The dieldrin-degrading fungus, Mucor racemosus strain DDF, can decrease dieldrin levels with simultaneous production of a small amount of aldrin trans-diol. A reduction in the levels of aldrin trans-diol by strain DDF has also been observed. Based on these results, it has been suggested that strain DDF transforms dieldrin to more polar compounds via aldrin trans-diol. We have conducted a study to identify the metabolites arising from aldrin trans-diol. The results showed that strain DDF gave reduced levels of aldrin trans-diol and also produced unknown metabolites. Ultra performance liquid chromatography-electrospray ionization-mass spectroscopy (UPLC-ESI-MS) analysis indicated the metabolites to be either sulfated- or phosphorylated- derivatives of aldrin trans-diol, but with the metabolites retaining six chlorine atoms. Therefore, the candidate derivatives were synthesized and the retention times of the natural metabolite and the synthetic phosphate were compared. As a result of a co-injection experiment, the metabolites were determined to be aldrin trans-diol exo- and endo-phosphates. These results were also supported by high-resolution-fast atom bombardment-mass spectrometry (HR-FAB-MS) of the natural metabolite (δ=0.63ppm). Phosphorylation of aldrin trans-diol is the first reported example of phosphate conjugation in microorganisms.

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