Biodegradation of juvenoid diastereoisomers: radio-HPLC and MS analysis

Chemosphere. 2005 Sep;60(9):1197-202. doi: 10.1016/j.chemosphere.2005.02.012. Epub 2005 Apr 1.

Abstract

Microbial degradation of two diastereoisomeric forms 2 and 3 of a selected juvenoid (insect juvenile hormone bioanalog), ethyl N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate was studied and the degradation products analyzed. Degradation experiments were performed using simple modeling under laboratory conditions. A Candida sp. strain T1, isolated from soil, was chosen as a biodegradation species. Radiolabeling of the studied compounds 2 and 3 was used in combination with radio-HPLC and MS analysis to increase the limits of detection, monitoring and isolation of trace quantities of the products of degradation and/or transformation. Resulting from the microbial processes using 2 or 3 as source compounds, three identical products (4-6) of their biodegradation were produced. Compound 2 also afforded two additional products (7, 8). Radio-HPLC analysis and separation, and subsequent MS analysis of the degradation mixtures resulted in identification of the degradation products. The degree and the rate of biodegradation of 2 and 3 were analyzed after 1, 3 and 7 days from the beginning of the experiment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biodegradation, Environmental
  • Biotransformation
  • Carbamates / chemistry
  • Carbamates / metabolism*
  • Carbamates / toxicity
  • Chromatography, High Pressure Liquid / methods
  • Daphnia / metabolism*
  • Insecta
  • Isotope Labeling
  • Juvenile Hormones / chemistry
  • Juvenile Hormones / metabolism*
  • Juvenile Hormones / toxicity
  • Mass Spectrometry / methods
  • Soil Microbiology*
  • Stereoisomerism
  • Time Factors

Substances

  • Carbamates
  • Juvenile Hormones
  • ethyl N-(2-(4-((2,2-(ethylenedioxy)cyclohexyl)methyl)phenoxy)ethyl)carbamate