Interaction between selenium and essential micronutrient elements in plants: A systematic review.

Nutrient imbalance (i.e., deficiency and toxicity) of microelements is an outstanding environmental issue that influences each aspect of ecosystems. Although the crucial roles of microelements in entire lifecycle of plants have been widely acknowledged, the effective control of microelements is still neglected due to the narrow safe margins. Selenium (Se) is an essential element for humans and animals. Although it is not believed to be indispensable for plants, many literatures have reported the significance of Se in terms of the uptake, accumulation, and detoxification of essential microelements in plants. However, most papers only concerned on the antagonistic effect of Se on metal elements in plants and ignored the underlying mechanisms. There is still a lack of systematic review articles to summarize the comprehensive knowledge on the connections between Se and microelements in plants. In this review, we conclude the bidirectional effects of Se on micronutrients in plants, including iron, zinc, copper, manganese, nickel, molybdenum, sodium, chlorine, and boron. The regulatory mechanisms of Se on these micronutrients are also analyzed. Moreover, we further emphasize the role of Se in alleviating element toxicity and adjusting the concentration of micronutrients in plants by altering the soil conditions (e.g., adsorption, pH, and organic matter), promoting microbial activity, participating in vital physiological and metabolic processes, generating element competition, stimulating metal chelation, organelle compartmentalization, and sequestration, improving the antioxidant defense system, and controlling related genes involved in transportation and tolerance. Based on the current understanding of the interaction between Se and these essential elements, future directions for research are suggested.

Assessment of Biodegradation Efficiency of Polychlorinated Biphenyls (PCBs) and Petroleum Hydrocarbons (TPH) in Soil Using Three Individual Bacterial Strains and Their Mixed Culture.

Biodegradation is one of the most effective and profitable methods for the elimination of toxic polychlorinated biphenyls (PCBs) and total petroleum hydrocarbons (TPH) from the environment. In this study, aerobic degradation of the mentioned pollutants by bacterial strains Mycolicibacterium frederiksbergense IN53, Rhodococcus erythropolis IN129, and Rhodococcus sp. IN306 and mixed culture M1 developed based on those strains at 1:1:1 ratio was analyzed. The effectiveness of individual strains and of the mixed culture was assessed based on carried out respirometric tests and chromatographic analyses. The Rhodococcus sp. IN306 turned out most effective in terms of 18 PCB congeners biodegradation (54.4%). The biodegradation index was decreasing with an increasing number of chlorine atoms in a molecule. Instead, the Mycolicobacterium frederiksbergense IN53 was the best TPH degrader (37.2%). In a sterile soil, contaminated with PCBs and TPH, the highest biodegradation effectiveness was obtained using inoculation with mixed culture M1, which allowed to reduce both the PCBs (51.8%) and TPH (34.6%) content. The PCBs and TPH biodegradation capacity of the defined mixed culture M1 was verified ex-situ with prism method in a non-sterile soil polluted with aged petroleum hydrocarbons (TPH) and spent transformer oil (PCBs). After inoculation with mixed culture M1, the PCBs were reduced during 6 months by 84.5% and TPH by 70.8% as well as soil toxicity was decreased.

Long-term ionic plasticity of GABAergic signalling in the hypothalamus.

The hypothalamus contains a number of nuclei that subserve a variety of functions, including generation of circadian rhythms, regulation of hormone secretion and maintenance of homeostatic levels for a variety of physiological parameters. Within the hypothalamus, γ-amino-butyric acid (GABA) is one of the major neurotransmitters responsible for cellular communication. Although GABA most commonly serves as an inhibitory neurotransmitter, a growing body of evidence indicates that it can evoke post-synaptic excitation as a result of the active regulation of intracellular chloride concentration. In this review, we consider the evidence for this ionic plasticity of GABAergic synaptic transmission in five distinct cases in hypothalamic cell populations. We argue that this plasticity serves as part of the functional response to or is at least associated with dehydration, lactation, hypertension and stress. As such, GABA excitation should be considered as part of the core homeostatic mechanisms of the hypothalamus.

Review on the significance of chlorine for crop yield and quality.

The chloride concentration in the plant determines yield and quality formation for two reasons. First, chlorine is a mineral nutrient and deficiencies thereof induce metabolic problems that interfere with growth. However, due to low requirement of most crops, deficiency of chloride hardly appears in the field. Second, excess of chloride, an event that occurs under chloride-salinity, results in severe physiological dysfunctions impairing both quality and yield formation. The chloride ion can effect quality of plant-based products by conferring a salty taste that decreases market appeal of e.g. fruit juices and beverages. However, most of the quality impairments are based on physiological dysfunctions that arise under conditions of chloride-toxicity: Shelf life of persimmon is shortened due to an autocatalytic ethylene production in fruit tissues. High concentrations of chloride in the soil can increase phyto-availability of the heavy metal cadmium, accumulating in wheat grains above dietary intake thresholds. When crops are cultivated on soils that are moderately salinized by chloride, nitrate fertilization might be a strategy to suppress uptake of chloride by means of an antagonistic anion-anion uptake competition. Overall, knowledge about proteins that catalyse chloride-efflux out of the roots or that restrict xylem loading is needed to engineer more resistant crops.

Changes in the element concentration of the dorsal hippocampus CA1 region during memory consolidation and reconsolidation.

The concentration and distribution of Mg, P, Cl, K, Cu and Zn in the dorsal hippocampus CA1 region of rat brains were studied during memory consolidation and reconsolidation processes stimulated with inhibitory avoidance (IA) tests. Experimental rats were divided into four groups: i) group not submitted to inhibitory avoidance task (IA-N); ii) group submitted to inhibitory avoidance training session (IA-Y); iii) group submitted to inhibitory avoidance reactivation session but did not step down from the platform (IAR-N); and iv) group submitted to avoidance reactivation session and stepped down from the platform (IAR-Y). Elemental concentration and distribution in the CA1 hippocampus region were obtained through the Particle-Induced X-ray Emission (PIXE) technique. The results indicate that the concentration of Mg, P, Cl, K and Cu increased during memory consolidation. During the memory reconsolidation process, the concentrations of Mg, P, Cl and K increased, while Cu and Zn had no significant changes with respect to their basal condition. These results show that the major part of these elements may be engaged in memory consolidation could be also participating in memory reconsolidation. For all elements, the general trend related to their concentration did not change during reconsolidation regardless the presence of a novelty event, i.e. stepping down from the platform.

Ammonium reduces chromium toxicity in the freshwater alga Chlorella vulgaris.

The aim of the present study was to investigate the protective effect of ammonium (NH4 (+)) on Cr toxicity to the freshwater alga Chlorella vulgaris. We followed an array of cellular functions and biomolecules in C. vulgaris cells exposed to 50 or 100 µM Cr at three different initial NH4 (+) concentrations (0.5, 3, and 10 mM). The results showed that Cr strongly inhibited cell yield of C. vulgaris, but 10 mM NH4 (+) could decrease by more than two-fold Cr toxicity on cell yield compared to exposure to 0.5 mM NH4 (+). Cr toxicity on gene transcripts and cellular substructure was also much lower at high than at low NH4 (+). Our results suggest that this protecting effect of NH4 (+) on intracellular Cr toxicity could be due to several factors, such as enhance uptake of phosphorus, increase in C and N assimilation efficiency, and increase transcription of photosynthesis-related genes.

NAA-SLR and ICP-AES application in the assessment of mass fraction of 19 chemical elements in pediatric and young adult prostate glands.

The effect of age on the mass fraction of 19 chemical elements in the intact prostate of 50 apparently healthy 0-30-year-old males was investigated by neutron activation analysis with high-resolution spectrometry of short-lived radionuclides and inductively coupled plasma atomic emission spectrometry. Mean values (M ± standard error of the mean) for mass fraction (in milligrams per kilogram, on dry weight basis) of chemical elements were as follows: Al, 77 ± 17; B, 1.31 ± 0.29; Ba, 4.0 ± 1.2; Br, 37.7 ± 4.3; Ca, 1,536 ± 189; Cl, 13,414 ± 949; Cu, 12.3 ± 2.1; Fe, 132 ± 11; K, 11,547 ± 468; Li, 0.064 ± 0.009; Mg, 922 ± 89; Mn, 1.88 ± 0.16; Na, 9,834 ± 411; P, 6,741 ± 335; S, 8,034 ± 251; Si, 199 ± 34; Sr, 1.40 ± 0.19; and Zn, 277 ± 33. The upper limit of mean mass fraction of V was ≤0.24. This work revealed that there is significant tendency for the mass fractions of Ca, K, Mg, and Zn in the prostate tissue of healthy individuals to increase with age from the time of birth up to 30 years. It means that Ca, K, Mg, and Zn mass fractions in prostate tissue are the androgen-dependent parameters. Our finding of a positive correlation between the prostatic Zn and Ca, K, Mg, P, and S mass fractions indicates that there is a special relationship of Zn with some main electrolytes (Ca, K, and Mg) and with P- and S-containing compounds in the prostate. It was shown also that high levels of Al, B, Ba, Br, Cl, Li, Na, and Sr mass fraction in prostate tissue do not indicate a direct involvement of these elements in the reproductive function of the prostate.

Translocation of (125)I, (75)Se and (36)Cl to edible parts of radish, potato and green bean following wet foliar contamination under field conditions.

Specific translocation factor values (ftr) for (129)I, (79)Se and (36)Cl following foliar transfer are still missing from the IAEA reference databases. The translocation of the short-lived isotopes, (125)I, (75)Se, and (36)Cl, to radish, potato and green bean edible parts was measured under field conditions following acute and chronic wet foliar contamination at various plant growth stages in the absence of leaching caused by rain. The translocation factors obtained for (125)I ranged from 0.8 to 2.6% for radish, from 0.1 to 2.3% for potato and from 0.1 to 2.6% for bean. The translocation factors obtained for (75)Se ranged from 6.3 to 21% for radish, from 1.6 to 32.6% for potato and from 7.7 to 22.8% for bean (values similar to Cs or even higher). The translocation factors obtained for (36)Cl were close to those for (75)Se and ranged from 4.3 to 28.8% for radish, from 0.5 to 31.5% for potato and from 4.3 to 16.3% for bean. Iodide showed the lowest apparent mobility because of its preferential fixation in or on the leaves and a significant amount was probably volatilized. Selenite internal transfer was significant and possibly followed the sulfur metabolic pathway. Chloride was very mobile and quickly diffused throughout the plant. The translocation factors varied with the growth stage and depended on the development state of the edible tissue and its associated sink strength for nutrients and assimilates. For radish, translocation was high during the early vegetative stages. For potato, wheat and bean, a major peak in translocation was seen during the flowering growth stage and the concomitant growth of potato tubers. An additive effect of successive contamination events on translocated elements was shown in radish but not in bean and potato. The highest translocation value obtained for an acute contamination event was shown to be an adequate, conservative indicator of chronic contamination in absence of specific values. Due to the absence of rain leaching during the experiment this study probably provides translocation values among the highest that could be recorded.

Integrating carbon-halogen bond formation into medicinal plant metabolism.

Halogenation, which was once considered a rare occurrence in nature, has now been observed in many natural product biosynthetic pathways. However, only a small fraction of halogenated compounds have been isolated from terrestrial plants. Given the impact that halogenation can have on the biological activity of natural products, we reasoned that the introduction of halides into medicinal plant metabolism would provide the opportunity to rationally bioengineer a broad variety of novel plant products with altered, and perhaps improved, pharmacological properties. Here we report that chlorination biosynthetic machinery from soil bacteria can be successfully introduced into the medicinal plant Catharanthus roseus (Madagascar periwinkle). These prokaryotic halogenases function within the context of the plant cell to generate chlorinated tryptophan, which is then shuttled into monoterpene indole alkaloid metabolism to yield chlorinated alkaloids. A new functional group-a halide-is thereby introduced into the complex metabolism of C. roseus, and is incorporated in a predictable and regioselective manner onto the plant alkaloid products. Medicinal plants, despite their genetic and developmental complexity, therefore seem to be a viable platform for synthetic biology efforts.

The effects of fixed orthodontic appliances on saliva flow rate and saliva electrolyte concentrations.

Fixed appliance orthodontic treatment may affect local saliva secretion; however, there is limited information available about this respect in the literature. Understanding how fixed appliance orthodontic treatment affects local saliva secretion could provide insight on possible contributions of salivary changes towards decalcification. In this study, we found that during the first month of fixed orthodontic treatment, the whole saliva flow rate, upper labial saliva flow rate and concentrations of whole saliva sodium and chlorine increased significantly, while the concentrations of calcium, phosphorous and potassium in whole saliva decreased. However, all these were in normal levels after 3 months. This study demonstrated that saliva flow rate was increased and saliva electrolytes were changed at early stage when placing fixed orthodontic appliances, which was considered due to increased mechanosensation.

Ocean to continent transfer of atmospheric Se as revealed by epiphytic lichens.

There is still a long-term debate concerning the relative contributions of naturally emitted and anthropogenic Se at the regional and local scales. Here, Se and heavy metal concentrations are reported for epiphytic lichens collected in coastal and inland areas from the USA, Canada and France for assessing atmospheric Se source. Correlations found between Se and Cl in lichens confirmed the major marine biogenic source for atmospheric Se. Continental samples do not show systematic relationships between Se and other metal (Pb, Cu, In ...) contents, even for lichens collected in the vicinity of smelters or close to urban areas. Our results suggest that, although anthropogenic Se may be present, the marine biogenic Se source is a major contributor to atmospheric Se for our sampling locations. The contribution of naturally emitted atmospheric Se may be significant in urban and industrial areas and should be taken into account for further studies.

Methanol extract of Longanae Arillus augments pentobarbital-induced sleep behaviors through the modification of GABAergic systems.

This experiment was performed to investigate whether methanol extract of Longanae Arillus (MELA) has hypnotic effects and/or enhances pentobarbital-induced sleep behaviors through the GABAergic systems. MELA prolonged sleep time and reduced sleep latency induced by pentobarbital similar to muscimol, a GABAA receptors agonist. MELA also increased sleep rate and sleep time in the combined administration with pentobarbital at the sub-hypnotic dosage and showed synergic effects with muscimol in potentiating sleep onset and enhancing sleep time induced by pentobarbital. However, MELA itself did not induce sleep at higher dose which was used in this experiment. In addition, both of MELA and pentobarbital increased chloride influx in primary cultured cerebellar granule cells. MELA increased GABAA receptors gamma-subunit expression and had no effect on the expression of alpha- and beta-subunits, and glutamic acid decarboxylase (GAD) in primary cultured cerebellar granule cells, showing different expression of subunits from pentobarbital. In conclusion, MELA itself does not induce sleep, but it augments pentobarbital-induced sleep behaviors through the modification of GABAergic systems.

Abiotic methyl bromide formation from vegetation, and its strong dependence on temperature.

Methyl bromide (CH3Br) is the most abundant brominated organic compound in the atmosphere. It is known to originate from natural and anthropogenic sources, although many uncertainties remain regarding strengths of both sources and sinks and the processes leading to its formation. In this study a potential new CH3Br source from vegetation has been examined, analogous to the recently discovered abiotic formation of methyl chloride from plant pectin. Several plant samples with known bromine content, including ash (Fraxinus excelsior), saltwort (Batis maritima), tomato reference material (NIST-1573a), hay reference material (IAEA V-10), and also bromine enriched pectin, were incubated in the temperature range of 25-50 degrees C and analyzed for CH3Br emission using gas chromatography/mass spectrometry. All plant samples inspected showed an exponential increase in CH3Br emission as a function of temperature increase, i.e., emissions were observed to approximately double with every 5 degrees C rise in temperature. Next to temperature, it was found that emissions of CH3Br were also dependent on the bromine content of the plants. The highest CH3Br release rates were found for the saltwort which contained the highest bromine concentration. Arrhenius plots confirmed that the observed emissions were from an abiotic origin. The contribution of abiotic CH3Br formation from vegetation to the global budget will vary geographically as a result of regional differences in both temperature and bromide content of terrestrial plants.

Cell viability and prostacyclin release in cultured human umbilical vein endothelial cells.

Construction of efficient substitutes of human blood vessels is strongly dependent on the use of viable and fully functional cultured endothelial cells (ECs). However, very few reports have been published to date focused on the evaluation of cell viability of cultured ECs. In this work, we have determined cell viability, von Willebrand factor, and prostacyclin (PGI(2)) activity in primary cell cultures of human umbilical vein ECs, to identify the specific cell passage that is more appropriate for the development of artificial organs by tissue engineering. Cell viability was determined by quantification of the intracellular concentration of several ions by highly sensitive electron probe X-ray microanalysis, whereas von Willebrand was assayed by immunohistochemistry and PGI(2) release was quantified by radioimmunoassay. The results of our analyses demonstrate that the K/Na ratio was different for each cell passage (4.72 for the first passage, 4.55 for the second passage, and 7.82 for the third passage), suggesting that the highest cell viability corresponds to the third passage. In contrast, PGI(2) production was higher at the first two cell passages, with a significant decrease at the third passage (6.46 +/- 0.10, 5.98 +/- 0.08, and 1.62 +/- 0.05 ng/mL of supernatant for the first, second, and third passages, respectively), whereas von Willebrand expression was similar among the three cell passages analyzed in this work (64.12%, 66.66%, 65.93% of positive cells, respectively). These data suggest that cells corresponding to the second cell passage show the best ratio of viability to functionality and should therefore be used for tissue engineering protocols.

Revision and meta-analysis of selected biosphere parameter values for chlorine, iodine, neptunium, radium, radon and uranium.

There is a continual supply of new experimental data that are relevant to the assessment of the potential impacts of nuclear fuel waste disposal. In the biosphere, the traditional assessment models are data intensive, and values are needed for several thousand parameters. This is augmented further when measures of central tendency, statistical dispersion, correlations and truncations are required for each parameter to allow probabilistic risk assessment. Recent reviews proposed values for 10-15 key element-specific parameters relevant to (36)Cl, (129)I, (222)Rn, (226)Ra, (237)Np and (238)U, and some highlights from this data update are summarized here. Several parameters for Np are revised downward by more than 10-fold, as is the fish/water concentration ratio for U. Soil solid/liquid partition coefficients, Kd, are revised downward by 10-770-fold for Ra. Specific parameters are discussed in detail, including degassing of I from soil; sorption of Cl in soil; categorization of plant/soil concentration ratios for U, Ra and Np; Rn transfer from soil to indoor air; Rn degassing from surface water; and the Ca dependence of Ra transfers.

Geobacter lovleyi sp. nov. strain SZ, a novel metal-reducing and tetrachloroethene-dechlorinating bacterium.

A bacterial isolate, designated strain SZ, was obtained from noncontaminated creek sediment microcosms based on its ability to derive energy from acetate oxidation coupled to tetrachloroethene (PCE)-to-cis-1,2-dichloroethene (cis-DCE) dechlorination (i.e., chlororespiration). Hydrogen and pyruvate served as alternate electron donors for strain SZ, and the range of electron acceptors included (reduced products are given in brackets) PCE and trichloroethene [cis-DCE], nitrate [ammonium], fumarate [succinate], Fe(III) [Fe(II)], malate [succinate], Mn(IV) [Mn(II)], U(VI) [U(IV)], and elemental sulfur [sulfide]. PCE and soluble Fe(III) (as ferric citrate) were reduced at rates of 56.5 and 164 nmol min(-1) mg of protein(-1), respectively, with acetate as the electron donor. Alternate electron acceptors, such as U(VI) and nitrate, did not inhibit PCE dechlorination and were consumed concomitantly. With PCE, Fe(III) (as ferric citrate), and nitrate as electron acceptors, H(2) was consumed to threshold concentrations of 0.08 +/- 0.03 nM, 0.16 +/- 0.07 nM, and 0.5 +/- 0.06 nM, respectively, and acetate was consumed to 3.0 +/- 2.1 nM, 1.2 +/- 0.5 nM, and 3.6 +/- 0.25 nM, respectively. Apparently, electron acceptor-specific acetate consumption threshold concentrations exist, suggesting that similar to the hydrogen threshold model, the measurement of acetate threshold concentrations offers an additional diagnostic tool to delineate terminal electron-accepting processes in anaerobic subsurface environments. Genetic and phenotypic analyses classify strain SZ as the type strain of the new species, Geobacter lovleyi sp. nov., with Geobacter (formerly Trichlorobacter) thiogenes as the closest relative. Furthermore, the analysis of 16S rRNA gene sequences recovered from PCE-dechlorinating consortia and chloroethene-contaminated subsurface environments suggests that Geobacter lovleyi belongs to a distinct, dechlorinating clade within the metal-reducing Geobacter group. Substrate versatility, consumption of electron donors to low threshold concentrations, and simultaneous reduction of electron acceptors suggest that strain SZ-type organisms have desirable characteristics for bioremediation applications.

Changes in intracellular electrolyte concentrations during apoptosis induced by UV irradiation of human myeloblastic cells.

Decreases in the intracellular concentrations of both K(+) and Cl(-) have been implicated in playing a major role in the progression of apoptosis, but little is known about the temporal relationship between decreases in electrolyte concentration and the key events in apoptosis, and there is no information about how such decreases affect different intracellular compartments. Electron probe X-ray microanalysis was used to determine changes in element concentrations (Na, P, Cl, and K) in nucleus, cytoplasm, and mitochondria in U937 cells undergoing UV-induced apoptosis. In all compartments, the initial stages of apoptosis were characterized by decreases in [K] and [Cl]. The largest decreases in these elements were in the mitochondria and occurred before the release of cytochrome c. Initial decreases in [K] and [Cl] also preceded apoptotic changes in the nucleus. In the later stages of apoptosis, the [K] continued to decrease, whereas that of Cl began to increase toward control levels and was accompanied by an increase in [Na]. In the nucleus, these increases coincided with poly(ADP-ribose) polymerase cleavage, chromatin condensation, and DNA laddering. The cytoplasm was the compartment least affected and the pattern of change of Cl was similar to those in other compartments, but the decrease in [K] was not significant until after active caspase-3 was detected. Our results support the concept that normotonic cell shrinkage occurs early in apoptosis, and demonstrate that changes in the intracellular concentrations of K and Cl precede apoptotic changes in the cell compartments studied.

Elemental changes in the brain, muscle, and gut cells of the housefly, Musca domestica, exposed to heavy metals.

The toxic effects of heavy metals on organisms are well established. However, their specific action at the cellular level in different tissues is mostly unknown. We have used the housefly, Musca domestica, as a model organism to study the toxicity of four heavy metals: copper (Cu), zinc (Zn), cadmium (Cd), and lead (Pb). These have been fed to larvae at low and high, semi-lethal concentrations, and their accumulation in the head, thorax, and abdomen was subsequently measured in adult flies. In addition, their impact on the cellular concentration of several elements important for cell metabolism-sodium (Na+), magnesium (Mg++), phosphorous (P), sulphur (S), chloride (Cl-) and potassium (K+)-were measured in neural cells, muscle fibers, and midgut epithelial cells. Our study showed that the heavy metals accumulate mainly in the abdomen, in which the concentrations of two of the xenobiotic metals, Cd and Pb, were 213 and 23 times more concentrated, respectively, than in controls. All the heavy metals affected the cellular concentration of light elements in all cell types, but the changes observed were dependent on tissue type and were specific for each heavy metal, and its concentration.

Leishmania donovani amastigotes mobilize organic and inorganic osmolytes during regulatory volume decrease.

The protozoan parasite Leishmania donovani encounters large fluctuations in osmolality as it cycles between its insect vector and human host. The flagellated promastigote exhibits regulatory volume responses involving organic and inorganic osmolytes, but little is known about volume regulation in the clinically relevant amastigote that multiplies within the parasitophorous vacuoles of mammalian host cells. Using a combination of morphological, X-ray microanalytical, and biochemical approaches we determined that non-motile amastigotes respond to hypotonic stress with (1) an amino acid and l-alanine-mediated regulatory volume decrease, and (2) a parallel release of Na+, K+, P (presumably as negatively charged phosphates), and subsequently Cl- from cytoplasm and the cell as a whole. In addition P, Zn2+, and subsequently Ca2+ increase in acidocalcisomes as Cl- content declines in this compartment. This evidence is the first to document subcellular translocation of, and thus a potential role for, zinc in volume regulatory responses. These coordinated changes in organic and inorganic osmolytes demonstrate that amastigote subcellular compartments, particularly acidocalcisomes, function in maintaining ionic homeostasis in the response of Leishmania amastigotes to hypo-osmotic stress.

Structural characterization of 5,6-dichlorotetradecanoic acid, an isolated metabolite of 9,10-dichlorooctadecanoic acid, by studying picolinyl esters, pyrrolidides and methyl esters with electron ionization mass spectrometry.

A method is presented for identification of positional isomers of dichlorinated fatty acids, based on derivatization to picolinyl esters prior to gas chromatographic/mass spectrometric analysis in the electron ionization mode. The mass spectra of the picolinyl esters showed structure-specific fragmentation patterns. By using the picolinyl ester, 5,6-dichlorotetradecanoic acid was identified as a metabolite from a cell-culture medium obtained by culturing human cell lines in media supplemented with threo-9,10-dichlorooctadecanoic acid. This indicates that dichlorinated fatty acids are degraded by beta-oxidation. It is also possible to locate tentatively the position of chlorine atoms in 5,6-dichlorotetradecanoic acid as its methyl ester or pyrrolidide.