Abstract
Agmenellum quadruplicatum strain PR-6 and Oscillatoria sp. strain JCM grown photoautotrophically in the presence of aniline metabolized the aromatic amine to formanilide, acetanilide and p-aminophenol. The metabolites were isolated by either thin-layer, gas-liquid or high pressure liquid chromatography and identified by comparison of their chromatographic, ultraviolet absorbance and mass spectral properties with those of authentic compounds. The toxicity of aniline derivatives towards Agmenellum quadruplicatum strain PR-6 indicated that the cyanobacterium was extremely sensitive to o-, m- and p-aminophenols, and phenylhydroxylamine.
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Abbreviations
- TLC:
-
thin layer chromatography
- HPLC:
-
high pressure liquid chromatography
- GC/MS:
-
gas chromatography/mass spectrometry
- m/e:
-
mass to charge ratio
References
Alexander M (1981) Biodegradation of chemicals of environmental concern. Science 211:132–138
Batterton J, Winters K, Van Baalen C (1978) Anilines: Selective toxicity to blue green algae. Science 199:1068–1070
Booth J, Boyland E (1964) The biochemistry of aromatic amines. Enzymatic N-hydroxylation of arylamines and conversion of arylhydroxylamines, into o-aminophenols. Biochem J 91:362–369
Cerniglia CE, Gibson DT, Van Baalen C (1979) Algal oxidation of aromatic hydrocarbons: Formation of 1-naphthol from naphthalene by Agmenellum quadruplicatum, strain PR-6. Biochem Biophys Res Commun 88:50–58
Cerniglia CE, Gibson DT, Van Baalen C (1980a) Oxidation of naphthalene by the cyanobacterium Oscillatoria sp. strain JCM. J Gen Microbiol 125:485–494
Cerniglia CE, Gibson DT, Van Baalen C (1980b) Oxidation of naphthalene by cyanobacteria and microalgae. J Gen Microbiol 116:495–500
Cerniglia CE, Van Baalen C, Gibson DT (1980c) Oxidation of biphenyl by the cyanobacterium Oscillatoria sp. strain JCM. Arch Microbiol 125:203–207
Daly JW, Jerina DM, Witkop B (1972) Arene oxides and the NIH shift: The metabolism toxicity and carcinogenicity of aromatic compounds. Experientia 28:1129–1149
Ferris JP, Fasco MJ, Stylianopoulou FL, Jerina DM, Daly JW, Jeffrey AM (1973) Mono-oxygenase activity in Cunninghamella bainieri. Evidence for a fungal system similar to liver microsomes. Arch Biochem Biophys 156:97–103
Games LM, Hites RA (1977) Composition, treatment efficiency and environmental significance of dye manufacturing plant effluents. Ann Chem 49:1433–1440
Gothoskar SV, Benjamin T, Roller PP, Weisburger EK (1979) N-Formylation of an aromatic amine as a metabolic pathway. Xenobiotica 9:533–537
Kiese M (1974) Methemoglobinemia: A comprehensive treatise: Causes, consequences and correction of increased contents of ferrihemoglobin in blood. CRS Press, Cleveland, Ohio, pp 259
Miller EC, Miller JA (1976) The metabolism of chemical carcinogens to reactive electrophiles and their possible mechanisms of action in carcinogenesis. In: CE Searle (ed) Chemical carcinogens, ACS Monograph 173. Washington, DC: American Chemical Society, pp 737–762
Myers J (1950) The culturing of algae for physiological research. In: J Brunel, GW Prescott, LH Tiffany (eds) The culturing of algae. Charles F. Kettering Foundation, Yellow Springs, Ohio, USA, pp 45–51
Smith RV, Rosazza JP (1974) Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch Biochem Biophys 161:551–558
Van Baalen C (1962) Studies on marine blue-green algae. Bot Mar 4:129–139
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Cerniglia, C.E., Freeman, J.P. & Van Baalen, C. Biotransformation and toxicity of aniline and aniline derivatives in cyanobacteria. Arch. Microbiol. 130, 272–275 (1981). https://doi.org/10.1007/BF00425939
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DOI: https://doi.org/10.1007/BF00425939