Transformation of Azo Dye Isomers by Streptomyces chromofuscus A11.

Fourteen mono-azo dyes were used to study the effects of substitution patterns on the biodegradability of dimethyl-hydroxy-azobenzene 4(prm1)-sulfonic acids by Streptomyces chromofuscus A11. Two substitution patterns were analyzed: (i) all possible substitution patterns of the two methyl and hydroxy substitution groups, 2-hydroxy (3,5; 4,5; 5,6) dimethyl and 4-hydroxy (2,3; 2,5; 2,6; 3,5) dimethyl isomers of azobenzene 4(prm1)-sulfonic acid; and (ii) replacement of the sulfonic group with a carboxylic group in these sulfonated azo dyes. The structural pattern of the hydroxy group in para position relative to the azo linkage and of two methyl substitution groups in ortho position relative to the hydroxy group was the most susceptible to degradation. Replacement of the sulfonic group with a carboxylic group enhanced overall dye degradability by S. chromofuscus A11.

Transformation of 2,4,6-trinitrotoluene (TNT) by actinomycetes isolated from TNT-contaminated and uncontaminated environments.

Actinomycete strains isolated from 2,4,6-trinitrotoluene (TNT)-contaminated and uncontaminated environments were compared for TNT tolerance and abilities to transform TNT. Regardless of previous TNT exposure history, no significant differences in TNT tolerance were seen among strains. Selected strains did not significantly mineralize [14C]TNT. The actinomycetes did, however, transform TNT into reduced intermediates. The data indicate that, in actinomycete-rich aerobic environments like composts, actinomycetes will transform TNT into intermediates which are known to form recalcitrant polymers.

New pathway for degradation of sulfonated azo dyes by microbial peroxidases of Phanerochaete chrysosporium and Streptomyces chromofuscus.

Pathways for the degradation of 3,5-dimethyl-4-hydroxy-azobenzene-4'-sulfonic acid (I) and 3-methoxy-4-hydroxyazobenzene-4'-sulfonamide (II) by the manganese peroxidase and ligninase of Phanerochaete chrysosporium and by the peroxidase of Streptomyces chromofuscus have been proposed. Twelve metabolic products were found, and their mechanisms of formation were explained. Preliminary oxidative activation of the dyes resulted in the formation of cationic species, making the molecules vulnerable to the nucleophilic attack of water. Two types of hydrolytic cleavage were observed. Asymmetric splitting gave rise to quinone and diazene derivatives, while symmetric splitting resulted in the formation of quinone monoimine and nitroso derivatives. These unstable intermediates underwent further redox, oxidation, and hydrolytic transformation, eventually furnishing 11 organic products and ammonia.

Mineralization of sulfonated azo dyes and sulfanilic acid by Phanerochaete chrysosporium and Streptomyces chromofuscus.

Five 14C-radiolabeled azo dyes and sulfanilic acid were synthesized and used to examine the relationship between dye substitution patterns and biodegradability (mineralization to CO2) by a white-rot fungus and an actinomycete. 4-Amino-[U-14C]benzenesulfonic acid and 4-(3-sulfo-4-aminophenylazo)-[U-14C]benzenesulfonic acid were used as representative compounds having sulfo groups or both sulfo and azo groups. Such compounds are not known to be present in the biosphere as natural products. The introduction of lignin-like fragments into the molecules of 4-amino-[U-14C]benzenesulfonic acid and 4-(3-sulfo-4-aminophenylazo)-[U-14C]benzenesulfonic acid by coupling reactions with guaiacol (2-methoxyphenol) resulted in the formation of the dyes 4-(3-methoxy-4-hydroxyphenylazo)-[U-14C]benzenesulfonic acid and 4-(2-sulfo-3'-methoxy-4'-hydroxy-azobenzene-4-azo)-[U-14C]benzenesulf oni c acid, respectively. The synthesis of acid azo dyes 4-(2-hydroxy-1-naphthylazo)-[U-14C]benzenesulfonic acid and 4-(4-hydroxy-1-naphthylazo)-[U-14C]benzenesulfonic acid also allowed the abilities of these microorganisms to mineralize these commercially important compounds to be evaluated. Phanerochaete chrysosporium mineralized all of the sulfonated azo dyes, and the substitution pattern did not significantly influence the susceptibility of the dyes to degradation. In contrast, Streptomyces chromofuscus was unable to mineralize aromatics with sulfo groups and both sulfo and azo groups. However, it mediated the mineralization of modified dyes containing lignin-like substitution patterns. This work showed that lignocellulolytic fungi and bacteria can be used for the biodegradation of anionic azo dyes, which thus far have been considered among the xenobiotic compounds most resistant to biodegradation.(ABSTRACT TRUNCATED AT 250 WORDS)

Influence of aromatic substitution patterns on azo dye degradability by Streptomyces spp. and Phanerochaete chrysosporium.

Twenty-two azo dyes were used to study the influence of substituents on azo dye biodegradability and to explore the possibility of enhancing the biodegradabilities of azo dyes without affecting their properties as dyes by changing their chemical structures. Streptomyces spp. and Phanerochaete chrysosporium were used in the study. None of the actinomycetes (Streptomyces rochei A10, Streptomyces chromofuscus A11, Streptomyces diastaticus A12, S. diastaticus A13, and S. rochei A14) degraded the commercially available Acid Yellow 9. Decolorization of monosulfonated mono azo dye derivatives of azobenzene by the Streptomyces spp. was observed with five azo dyes having the common structural pattern of a hydroxy group in the para position relative to the azo linkage and at least one methoxy and/or one alkyl group in an ortho position relative to the hydroxy group. The fungus P. chrysosporium attacked Acid Yellow 9 to some extent and extensively decolorized several azo dyes. A different pattern was seen for three mono azo dye derivatives of naphthol. Streptomyces spp. decolorized Orange I but not Acid Orange 12 or Orange II. P. chrysosporium, though able to transform these three azo dyes, decolorized Acid Orange 12 and Orange II more effectively than Orange I. A correlation was observed between the rate of decolorization of dyes by Streptomyces spp. and the rate of oxidative decolorization of dyes by a commercial preparation of horseradish peroxidase type II, extracellular peroxidase preparations of S. chromofuscus A11, or Mn(II) peroxidase from P. chrysosporium. Ligninase of P. chrysosporium showed a dye specificity different from that of the other oxidative enzymes.(ABSTRACT TRUNCATED AT 250 WORDS)