2. Academic Validation
  3. Azoxystrobin amine: A novel azoxystrobin degradation product from Bacillus licheniformis strain TAB7

Azoxystrobin amine: A novel azoxystrobin degradation product from Bacillus licheniformis strain TAB7

  • Chemosphere. 2021 Jun;273:129663. doi: 10.1016/j.chemosphere.2021.129663.
Enock Mpofu 1,  Amirah Alias 2,  Keisuke Tomita 1,  Chiho Suzuki-Minakuchi 3,  Kenji Tomita 4,  Joydeep Chakraborty 1,  Michal Malon 5,  Yusuke Ogura 6,  Hirosato Takikawa 6,  Kazunori Okada 1,  Toshiaki Kimura 7,  Hideaki Nojiri 8
Affiliations

Affiliations

  • 1 Biotechnology Research Center, The University of Tokyo, Tokyo, 113-8657, Japan.
  • 2 Biotechnology Research Center, The University of Tokyo, Tokyo, 113-8657, Japan; Faculty of Science and Marine Environment, Universiti Malaysia Terengganu, 21030, Kuala Nerus, Terengganu, Malaysia.
  • 3 Biotechnology Research Center, The University of Tokyo, Tokyo, 113-8657, Japan; Collaborative Research Institute for Innovative Microbiology, The University of Tokyo, Tokyo, 113-8657, Japan.
  • 4 Department of Applied Biological Chemistry, The University of Tokyo, Tokyo, 113-8657, Japan.
  • 5 JEOL Ltd., 3-1-2 Musashino, Akishima, Tokyo, 196-8558, Japan.
  • 6 Department of Applied Biochemistry, The University of Tokyo, Tokyo, 113-8657, Japan.
  • 7 Agriculture and Biotechnology Business Division, Toyota Motor Corporation, 1099 Marune, Kurozasa-cho, Miyoshi-shi, Aichi, 470-0201, Japan.
  • 8 Biotechnology Research Center, The University of Tokyo, Tokyo, 113-8657, Japan; Collaborative Research Institute for Innovative Microbiology, The University of Tokyo, Tokyo, 113-8657, Japan. Electronic address: anojiri@g.ecc.u-tokyo.ac.jp.
PMID: 33515965 DOI: 10.1016/j.chemosphere.2021.129663
Abstract

Azoxystrobin (AZ) is a broad-spectrum synthetic fungicide widely used in agriculture globally. However, there are concerns about its fate and effects in the environment. It is reportedly transformed into azoxystrobin acid as a major metabolite by environmental Microorganisms. Bacillus licheniformis strain TAB7 is used as a compost deodorant in commercial compost and has been found to degrade some phenolic and agrochemicals compounds. In this article, we report its ability to degrade azoxystrobin by novel degradation pathway. Biotransformation analysis followed by identification by electrospray ionization-mass spectrometry (MS), high-resolution MS, and nuclear magnetic resonance spectroscopy identified methyl (E)-3-amino-2-(2-((6-(2-cyanophenoxy)pyrimidin-4-yl)oxy)phenyl)acrylate, or (E)-azoxystrobin amine in short, and (Z) isomers of AZ and azoxystrobin amine as the metabolites of (E)-AZ by TAB7. Bioassay testing using Magnaporthe oryzae showed that although 40 μg/mL of (E)-AZ inhibited 59.5 ± 3.5% of the electron transfer activity between mitochondrial Complexes I and III in M. oryzae, the same concentration of (E)-azoxystrobin amine inhibited only 36.7 ± 15.1% of the activity, and a concentration of 80 μg/mL was needed for an inhibition rate of 56.8 ± 7.4%, suggesting that (E)-azoxystrobin amine is less toxic than the parent compound. To our knowledge, this is the first study identifying azoxystrobin amine as a less-toxic metabolite from Bacterial AZ degradation and reporting on the enzymatic isomerization of (E)-AZ to (Z)-AZ, to some extent, by TAB7. Although the fate of AZ in the soil microcosm supplemented with TAB7 will be needed, our findings broaden our knowledge of possible AZ biotransformation products.

Keywords

Azoxystrobin; Azoxystrobin amine; Biotransformation; Fungicide; NMR; Strobilurins.

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