TY - JOUR
T1 - DEGRADATION PATHWAYS AND MECHANISMS OF SUBSTITUTED INDOLES UNDER METHANOGENIC CONDITION
AU - Wang, Yingying
AU - Qiu, Wanfei
AU - Fan, Yanzhen
AU - Gu, Ji-Dong
PY - 2002
Y1 - 2002
N2 - Degradation of indole by an indoledegrading methanogenic consortium enriched from sewage sludge proceeded through a twostep hydroxylation pathway yielding oxindole and isatin. The ability of this consortium to hydroxylate and subsequently degrade substituted indoles was investigated. Of the substituted indoles tested, the consortium was able to transform or degrade 3 methylindole and 3indolyl acetate. Oxindole, 3methyloxindole, and indoxyl were identified as degradation metabolites of indole, 3methylindole, and 3indolyl acetate, respectively. Isatin (indole2, 3dione) was produced as an intermediate when the consortium was amended with oxindole, which provided the evidence that degradation of indole proceeded through successive hydroxylation of the 2 and 3positions prior to ring cleavage between the C2 and C3 atoms on the pyrrole ring of indole. The presence of a methyl group ( CH3) at either the 1 or 2position of indole inhibited the initial hydroxylation reaction. The substituted indole, 3methylindole, was hydroxylated at the 2position but not at the 3position and could not be further metabolized through the oxindoleisatin pathway. Indoxyl (indole3one), the deacetylated product of 3 indolyl acetate, was not hydroxylated at the 2position and thus was not further metabolized by the consortium. When an H atom or electrondonating group (i.e., CH3) was present at the 3 position, hydroxylation proceeded at the 2position, but the presence of electronwithdrawing substituent groups (i.e.,OH orCOOH) at the 3position inhibited hydroxylation. Tab 1, Fig 4, Ref 25
AB - Degradation of indole by an indoledegrading methanogenic consortium enriched from sewage sludge proceeded through a twostep hydroxylation pathway yielding oxindole and isatin. The ability of this consortium to hydroxylate and subsequently degrade substituted indoles was investigated. Of the substituted indoles tested, the consortium was able to transform or degrade 3 methylindole and 3indolyl acetate. Oxindole, 3methyloxindole, and indoxyl were identified as degradation metabolites of indole, 3methylindole, and 3indolyl acetate, respectively. Isatin (indole2, 3dione) was produced as an intermediate when the consortium was amended with oxindole, which provided the evidence that degradation of indole proceeded through successive hydroxylation of the 2 and 3positions prior to ring cleavage between the C2 and C3 atoms on the pyrrole ring of indole. The presence of a methyl group ( CH3) at either the 1 or 2position of indole inhibited the initial hydroxylation reaction. The substituted indole, 3methylindole, was hydroxylated at the 2position but not at the 3position and could not be further metabolized through the oxindoleisatin pathway. Indoxyl (indole3one), the deacetylated product of 3 indolyl acetate, was not hydroxylated at the 2position and thus was not further metabolized by the consortium. When an H atom or electrondonating group (i.e., CH3) was present at the 3 position, hydroxylation proceeded at the 2position, but the presence of electronwithdrawing substituent groups (i.e.,OH orCOOH) at the 3position inhibited hydroxylation. Tab 1, Fig 4, Ref 25
KW - indoles
KW - pathway
KW - methanogenic condition
UR - http://www.cibj.com/Upload/PaperUpLoad/ebook/2002/05/14.pdf
M3 - 文章
JO - Chinese Journal of Appplied Environmental Biology
JF - Chinese Journal of Appplied Environmental Biology
ER -