Microorganisms phenol toxicity

Soil microorganisms produce many compounds that are potentially toxic to higher plants. Examples include members of the following antibiotics (1-6), fatty and phenolic acids (7-12), amino compounds (13-15), and trichothecenes (16, 17). "Soil sickness" and "replant problems" have been reported where certain crops or their residues interfere with establishment of a subsequent crop (18, 19). Toxins resulting from microbial activity sometimes are involved, but it is often unclear whether these are synthesized de novo in microbial metabolism or are breakdown products of the litter itself (20). 

The contaminants that can be removed by flotation include conventional pollutants such as BOD, COD, total suspended solids (TSS), phosphorus, phenols, oil and grease, as well as toxic pollutants including heavy metals, toxic organics, pathogenic microorganisms, and radioactive radon 22.28,33,54,64,100-102... 

Phenolic acids can be allelopathic but their presence in soil is ephemeral due to rapid degradation and/or sorption by soil particles (Inderjit 2004). Sorption of benzoic acid onto soil particles increased with concentration and it may explain the reason for the limited allelopathic effect of benzoic acid at concentrations often recorded in natural soil (Inderjit 2004). Microorganisms help to generate allelochemicals, but they may also modify toxic compounds into nontoxic compounds (Khanh et al. 2005). Allelochemicals are changed in composition and quantity during the residue decomposition. Allelopathy plays an important function in nutrient recycling (Rice 1984). 

Many allelochemicals are decomposed in soil, either abiotically (37) or by microorganisms (95-100). Obviously, the attainment of active concentrations of allelochemicals in soil depends on the relative rates of addition and inactivation. It is important to understand also that microbial decomposition of allelochemicals does not necessarily result in a decrease in allelopathic activity. In fact, the reverse may be true. Hydrojuglone is oxidized in soil to juglone, a quinone that is inhibitory to some species at a 10 ° M concentration (101). Isoflavonoids produced by red clover are decomposed to even more toxic phenolic compounds (95) and to repeat, amygdalin from peach roots is changed to hydrogen cyanide and benzaldehyde which cause the peach replant problem (88), and phlorizin from apple roots is decomposed to several phenolic compounds that appear to be responsible for the apple replant problem (100). 

The biochemical mechanisms through which allelochemicals exert deleterious or toxic effects on plants are, for the most part, unknown (1). Some phenolic acids, cinnamic acids, coumarins, and flavonoids have been reported to inhibit photosynthesis and respiration of intact plants and microorganisms. However, the mechanisms, at the molecular level, through which the compounds interfere, remain to be ascertained. Some phenolic acids, coumarins, and flavonoids were reported to Inhibit C02-dependent 0 ... 

Oxidation of phenols is one of the most important aspects of these compounds to the biologist. Oxidation of phenolic compounds can result in the browning of tissues. Well-known examples are the browning of lfuits after they have been cut. Oxidation can also result in the formation of metabolites that are toxic to animals and plants, and that can account for spoilage of foods in processing. On the other hand, toxic compounds formed from the oxidation of phenolics can inhibit pathogenic microorganisms. Certain phenols are used as retardants or antioxidants to prevent the oxidation of fatty acids. 

Because of their extensive use in industrial activities, phenolic compounds are abundant in many wastewaters. They are present in oil refining, petrochemical, plastic, pesticide, carbon liquefaction, and food processing industrial wastewaters. In addition, phenol-like structures are part of the macromolecular natural humic substances present in water humics are known precursors of trihalomethane compounds in drinking water chlorination [176,177], These compounds are refractory to conventional processes such as biological oxidation because of their toxicity for microorganisms [178]. 

Chemotherapy based on selective toxicity was first conceived by Paul Ehrlich. It relied on the principle that the drug should be more toxic and harmful for the invading microorganism than for the host. This understanding rendered the phenolic compounds and alcohols unsatisfactory as chemotherapeutic agents, since they caused considerable damage to the eukaryotic cells and their natural defense mechanisms. 

The majority of phenols, especially those containing chlorine, are toxic to microorganisms. However, the majority of phenols are too phytotoxic to permit their use as agricultural fungicides. They are widely used as industrial fungicides. Dinocap, a mixture of several compounds, was first introduced in 1946 as a non-systemic aphidde and contact fungicide. Dinocap is used to control powdery mildew on major horticultural crops. Unlike the herbicide DNOC and other chlorinated phenols, dinocap has relatively low mammalian toxicity. 

As said above, plant root chemistry may also influence deeply alpine soil microorganism s biomass. It turns out that the particular chemical composition of exudates is a strong selective force in favour of bacteria that can catabolize particular compounds. Plants support heterotrophic microorganisms by way of rhizodeposition of root exudates and litter from dead tissue that include phenolic acids, flavonoids, terpenoids, carbohydrates, hydroxamic acids, aminoacids, denatured protein from dying root cells, CO2, and ethylene (Wardle, 1992). In certain plants, as much as 20-30% of fixed carbon may be lost as rhizodeposition (Lynch and Whipps, 1990). Most of these compounds enter the soil nutrient cycle by way of the soil microbiota, giving rise to competition between the myriad species living there, from microarthropods and nematodes to mycorrhiza and bacteria, for these resources (e.g. Hoover and Crossley, 1995). There is evidence that root phenolic exudates are metabolized preferentially by some soil microbes, while the same compounds are toxic to others. Phenolic acids usually occur in small concentration in soil chiefly because of soil metabolism while adsorption in clay and other soil particles plays a minor role (Bliun et al., 1999). However, their phytotoxicity is compounded by synergism between particular mixtures (Blum, 1996). 

Although the biodegradation of phenols and anilines is well established, these are relatively toxic compounds and some microorganisms detoxify them by acylation as an alternative to biodegradation. For example, acetylation of pentachlorophenol has been observed (Rottt et al. 1979), and acetylation of substituted anilines has been established 4-chloroaniline is converted into 4-chloroacetanilide by Fusarium oxysporum (Kaufman et al. 1973) and 2-nitro-4-aminotol-uene that is produced from 2,4-dinitrotoluene by a species of Mucrosporium sp. (McCormick et al. 1978) is converted into 3-nitro-4-methylacetanilide. All these neutral compounds may plausibly be assumed to be less toxic than their precursors. 

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