Degradation of an endocrine disrupting chemical, DEHP [di-(2-ethylhexyl)-phthalate], by Fusarium oxysporum f. sp. pisi cutinase

Appl Microbiol Biotechnol. 2003 Nov;63(1):75-80. doi: 10.1007/s00253-003-1332-5. Epub 2003 May 15.

Abstract

The efficiency of two lypolytic enzymes (fungal cutinase, yeast esterase) in the degradation of di-(2-ethylhexyl)-phthalate (DEHP) was investigated. The DEHP-degradation rate of fungal cutinase was surprisingly high, i.e. almost 70% of the initial DEHP (500 mg/l) was decomposed within 2.5 h and nearly 50% of the degraded DEHP disappeared within the initial 15 min. With the yeast esterase, despite the same concentration, more than 85% of the DEHP remained even after 3 days of treatment. During the enzymatic degradation of DEHP, several DEHP-derived compounds were detected and time-course changes in composition were also monitored. During degradation with fungal cutinase, most DEHP was converted into 1,3-isobenzofurandione (IBF) by diester hydrolysis. In the degradation by yeast esterase, two organic chemicals were produced from DEHP: IBF and an unidentified compound (X). The final chemical composition after 3 days was significantly dependent on the enzyme used. Fungal cutinase produced IBF as a major degradation compound. However, in the DEHP degradation by yeast esterase, compound X was produced in abundance in addition to IBF. The toxic effects of the final degradation products were investigated, using various recombinant bioluminescent bacteria and, as a result, the degradation products from yeast esterase were shown to contain a toxic hazard, causing oxidative stress and damage to protein synthesis.

MeSH terms

  • Candida / enzymology
  • Candida / metabolism
  • Carboxylic Ester Hydrolases / metabolism*
  • Diethylhexyl Phthalate / metabolism*
  • Esterases / metabolism
  • Estrogen Antagonists / metabolism*
  • Furans / metabolism
  • Fusarium / enzymology*
  • Fusarium / metabolism

Substances

  • Estrogen Antagonists
  • Furans
  • Diethylhexyl Phthalate
  • Esterases
  • Carboxylic Ester Hydrolases
  • cutinase