TY  - JOUR
AB  - Enzymatic synthesis of δ-lactones using Baeyer-Villiger monooxygenases (BVMOs) has potential in the fragrance and flavor industries but is constrained by poor activity toward ortho-alkyl-substituted cyclopentanones, key δ-lactone precursors. We determined the crystal structure of a BVMO derived from Oceanicola granulosus (OgBVMO), uncovering a unique loop adjacent to key catalytic residue R335. Site-saturation mutagenesis of loop residues A338 and A339 identified the A339E variant, obtaining a 2.4- to 3-fold increase in catalytic activity toward ortho-alkyl-substituted cyclopentanones (2-methyl-, 2-ethyl-, 2-hexyl-, and 2-heptylcyclopentanone). Further engineering the substrate-binding pocket yielded the Q442N variant, improving activity by 2.7-3.8-fold. Remarkably, the combinatorial mutant A339E/Q442N achieved 3.3-5.2-fold higher activity than the wild-type. Molecular dynamics simulations indicated that these improvements were driven by more favorable nucleophilic attack distances, underscoring the synergistic effects of distal and active-site mutations. These findings offer valuable insights into enhancing the catalytic activity of BVMOs, supporting the green manufacturing of high-value flavor compounds.
AU  - Du, Y.*
AU  - Lv, X.*
AU  - Siebenmorgen, T.
AU  - Popowicz, G.M.
AU  - Feng, C.*
AU  - Ma, Y.*
AU  - Wang, Y.*
C1  - 74851
C2  - 57635
CY  - 1155 16th St, Nw, Washington, Dc 20036 Usa
SP  - 14453-14466
TI  - Enhancing catalytic activity of a Baeyer-Villiger monooxygenase from Oceanicola granulosus: Simultaneous engineering of the distal site and active site.
JO  - J. Agric. Food Chem.
VL  - 73
IS  - 23
PB  - Amer Chemical Soc
PY  - 2025
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Iron (Fe) is present in foods and food supplements in a wide variety of Fe species. Caution needs to be paid in the case of overdosing on this essential trace element as adverse effects like neurodegenerative diseases are associated with increased iron levels in the brain. However, knowledge regarding the species-specific effects of nutritionally relevant Fe species is limited. Therefore, we treated the nematode Caenorhabditis elegans (C. elegans) with an overdose of the Fe species iron(III) ammonium citrate (FAC), iron(II) gluconate (FeGlu), and iron(II) chloride (FeCl2) for 5 and 24 h. While the bioavailability of Fe was highest with FeCl2 and lowest with FAC, the effects on tested endpoints, such as superoxide dismutase activity, translocation of the transcription factor daf-16 (human FOXO3), mitochondrial reactive oxygen and nitrogen species, and apoptotic cells were similar. This study provides further insights into Fe-species-specific effects on genes related to Fe homeostasis of C. elegans by studying gene expression and investigating C. elegans mutants lacking smf-3, ftn-1, ftn-2, dcytb (f55h2.5), and cp (f21d5.3). Thus, these findings underline the significance of the oxidation state and ligand of Fe species with respect to bioavailability while also identifying the key genes involved in Fe homeostasis in C. elegans.
AU  - Gremme, A.*
AU  - Safa Flaih, Z.A.*
AU  - Scholz, J.*
AU  - Gerisch, E.*
AU  - Thiel, A.*
AU  - McColl, G.*
AU  - Hayen, H.*
AU  - Michalke, B.
AU  - Bornhorst, J.*
C1  - 73254
C2  - 56973
CY  - 1155 16th St, Nw, Washington, Dc 20036 Usa
TI  - Is ferric the same as ferrous? Effect of nutritionally relevant iron species in C. elegans: Bioavailability, iron homeostasis, oxidative stress, and cell death.
JO  - J. Agric. Food Chem.
VL  - 73
IS  - 6
PB  - Amer Chemical Soc
PY  - 2025
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Spot blotch of barley (Hordeum vulgare L.), caused by Bipolaris sorokiniana, is responsible for major losses in crop yield. Breeding-resistant barley varieties have proven to be an effective countermeasure for protecting agricultural production. Plants react to pathogen attacks by up-regulating secondary metabolites. Marker compounds for a B. sorokiniana infection are examined by untargeted UPLC-TOF-MS metabolomics and lipidomics techniques. Through the analysis of nine quantitatively resistant and susceptible barley genotypes, derived from the nested association mapping population HEB-25, followed by structure identification experiments and spore germination assays, 57 metabolites are identified. In addition to previously known metabolites, the unknown compounds 5-carboxydidehydroblumenol C-9-O-ß-d-glucoside (46) and grasshopper ketone 3-sulfate (47) were elucidated. 5-Carboxyblumenol C-9-O-ß-d-glucoside (45) was described for the first time in barley leaves. Pheophytin derivatives, oxylipins, linolenate-conjugated lipids, and flavone glycosides were described for the first time in connection with infections by phytopathogenic fungi or resistance in barley.
AU  - Kurzweil, L.*
AU  - Stark, T.D.*
AU  - Hille, K.*
AU  - Hoheneder, F.*
AU  - Mrtva, J.*
AU  - Hausladen, J.*
AU  - Lenk, M.
AU  - Motawia, M.S.*
AU  - Strittmatter, N.*
AU  - Vlot, A.C.
AU  - Pillen, K.*
AU  - So̷rensen, M.*
AU  - Mo̷ller, B.L.*
AU  - Hückelhoven, R.*
AU  - Dawid, C.*
C1  - 75581
C2  - 58226
CY  - 1155 16th St, Nw, Washington, Dc 20036 Usa
SP  - 24662–24687
TI  - UPLC-ESI-TOF-MS profiling of metabolome alterations in barley (Hordeum vulgare L.) leaves induced by Bipolaris sorokiniana.
JO  - J. Agric. Food Chem.
VL  - 73
IS  - 39
PB  - Amer Chemical Soc
PY  - 2025
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The removal of husks before the mashing process, also known as the Kubessa method, is an established brewing practice often positively associated with smoothness and better flavor-stability of beer. Empirical evidence on the effect of the Kubessa method on beer, however, has been lacking. Similarly, our study's comprehensive analysis of established brewing attributes revealed that traditional methods do not fully capture the impact of husk separation in beer brewing. Conclusive evidence of the Kubessa method's impact on beer aging chemistry was obtained through ultrahigh resolution mass spectrometry (FT-ICR-MS), revealing intricate molecular details inaccessible to conventional analytical techniques. The compositional information on thousands of molecules in Kubessa beer was resolved and compared to whole malt mashing. Machine learning algorithms applied to aging experiments identified over 500 aging-related compounds inhibited by husk separation. Complementary Time of flight mass spectrometry (ToF-MS) coupled with chromatography further confirmed that the mashing of husks introduces sulfur-containing lipid compounds. These significant differences in the beer composition provide valuable insights for further investigation into the staling protective effect of husk-separation (Kubessa process) during beer production, as empirically demonstrated in this work.
AU  - Pieczonka, S.
AU  - Brass, L.*
AU  - Lehnhardt, F.*
AU  - Eiken, J.*
AU  - Wachtler, A.
AU  - Weidner, L.
AU  - Brauer, J.*
AU  - Rychlik, M.*
AU  - Gastl, M.*
AU  - Schmitt-Kopplin, P.
AU  - Zarnkow, M.*
C1  - 71613
C2  - 56309
CY  - 1155 16th St, Nw, Washington, Dc 20036 Usa
SP  - 20048-20055
TI  - Husk separation (Kubessa Method) impacts the aging chemistry of beer.
JO  - J. Agric. Food Chem.
VL  - 72
IS  - 36
PB  - Amer Chemical Soc
PY  - 2024
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Thermal processing of food plays a fundamental role in everyday life. Whereas most researchers study thermal processes directly in the matrix, molecular information in the form of non- and semivolatile compounds conveyed by vaporous emissions is often neglected. We performed a metabolomics study of processing emissions from 96 different food items to define the interaction between the processed matrix and released metabolites. Untargeted profiling of vapor samples revealed matrix-dependent molecular spaces that were characterized by Fourier-transform ion cyclotron resonance-mass spectrometry and ultra-performance liquid chromatography-mass spectrometry. Thermal degradation products of peptides and amino acids can be used for the differentiation of animal-based food from plant-based food, which generally is characterized by secondary plant metabolites or carbohydrates. Further, heat-sensitive processing indicators were characterized and discussed in the background of the Maillard reaction. These reveal that processing emissions contain a dense layer of information suitable for deep insights into food composition and control of cooking processes based on processing emissions.
AU  - Weidner, L.
AU  - Cannas, J.V.*
AU  - Rychlik, M.*
AU  - Schmitt-Kopplin, P.
C1  - 68733
C2  - 54942
CY  - 1155 16th St, Nw, Washington, Dc 20036 Usa
SP  - 17442-17454
TI  - Molecular characterization of cooking processes: A metabolomics decoding of vaporous emissions for food markers and thermal reaction indicators.
JO  - J. Agric. Food Chem.
VL  - 71
IS  - 45
PB  - Amer Chemical Soc
PY  - 2023
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Precise controlling and monitoring the status of the coffee roasting process is essential for consistent product quality and optimization toward targeted coffee properties. In small-scale roasting experiments, the chemical composition of the roasting offgas was analyzed by online single-photon ionization time-of-flight mass spectrometry (SPI-TOFMS) at 118 nm with 5 s time resolution. Subsequently, mass spectra at the drop of the coffee beans were combined with off-line measurements of roast degree, described by color value "Colorette", and the antioxidant capacity, obtained from the Folin-Ciocalteu (FC) assay, in an explanatory projection on latent structure regression model. While the roast degree gives an indication of the coffee flavor, antioxidants in brewed coffee are regarded as beneficial for human health. Colorette and FC values could be derived from the SPI mass spectra with root-mean-square errors from Monte Carlo cross-validation of 6.0 and 139 mg of gallic acid equiv L-1, respectively, and explained covariance (R-2(CV)) better than 89%. Finally, the regression models were applied to the SPI mass spectra over the entire roast to demonstrate the predictive ability for online process control in real time.
AU  - Heide, J.*
AU  - Czech, H.
AU  - Ehlert, S.*
AU  - Koziorowski, T.*
AU  - Zimmermann, R.
C1  - 57895
C2  - 48167
CY  - 1155 16th St, Nw, Washington, Dc 20036 Usa
SP  - 4752-4759
TI  - Towards smart online coffee roasting process control: Feasibility of real-time. prediction of coffee roast degree and brew antioxidant capacity by single-photon ionization mass spectrometric monitoring of roast gases.
JO  - J. Agric. Food Chem.
VL  - 68
IS  - 17
PB  - Amer Chemical Soc
PY  - 2020
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Wines aged in oak wood barrels with various uniform tannin contents (which were classified according to their total ellagitannins contents as predicted by Near Infrared Spectroscopy on the untoasted wood) and different toasting levels (high precision toasting by radiation) were distinguished according to their overall abilities to resist against oxidation. Wine trials were carried out on two different vintages (2015, 2016) and three grape varieties (Sauvignon blanc, Semillon, Chardonnay). Regardless of the vintage and the wine matrix, a relationship was established between wine oxidative stability (based on EPR spin trapping methodology) and oak barrel tannin potential. The extraction kinetic of ellagitannins by wines appeared linear during barrel aging and achieved its maximum at six or eight months, in a grape variety dependent manner. Oak wood barrel tannin potentials and toastings had no effect on wine glutathione and polyphenols contents. However, wines aged in new barrels with both low and medium tannin potentials, preserved at the end of aging and important number of S-N containing compounds, which was in addition to the known ellagitanins, revealed wines better antioxidant stability.
AU  - Nikolantonaki, M.*
AU  - Daoud, S.*
AU  - Noret, L.*
AU  - Coelho, C.*
AU  - Badet-Murat, M.L.*
AU  - Schmitt-Kopplin, P.
AU  - Gougeon, R.D.*
C1  - 56582
C2  - 47159
CY  - 1155 16th St, Nw, Washington, Dc 20036 Usa
SP  - 8402-8410
TI  - Impact of oak wood barrel tannin potential and toasting on white wine antioxidant stability.
JO  - J. Agric. Food Chem.
VL  - 67
IS  - 30
PB  - Amer Chemical Soc
PY  - 2019
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Food processing of infant formula alters chemical structures, including the formation of Maillard reaction products between proteins and sugars. We detected early Maillard reaction products, so-called Amadori products, in stool samples of formula-fed infants. In total, four Amadori products (N-deoxylactulosyllysine, N-deoxyfructosyllysine, N-deoxylactulosylleucylisoleucine, N-deoxyfructosylleucylisoleucine) were identified by a combination of complementary nontargeted and targeted metabolomics approaches. Chemical structures were confirmed by preparation and isolation of reference compounds, LC-MS/MS, and NMR. The leucylisoleucine Amadori compounds, which most likely originate from beta-lactoglobulin, were excreted throughout the first year of life in feces of formula-fed infants but were absent in feces of breastfed infants. Despite high inter- and intraindividual differences of Amadori products in the infants' stool, solid food introduction resulted in a continuous decrease, proving infant formula as the major source of the excreted Amadori products.
AU  - Sillner, N.
AU  - Walker, A.
AU  - Hemmler, D.
AU  - Bazanella, M.*
AU  - Heinzmann, S.S.
AU  - Haller, D.*
AU  - Schmitt-Kopplin, P.
C1  - 56561
C2  - 47140
CY  - 1155 16th St, Nw, Washington, Dc 20036 Usa
SP  - 8061-8069
TI  - Milk-derived amadori products in feces of formula-fed infants.
JO  - J. Agric. Food Chem.
VL  - 67
IS  - 28
PB  - Amer Chemical Soc
PY  - 2019
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Coffee beans of two cultivars, Arabica (Mexico) and Robusta (Vietnam), were roasted in a small-scale drum roaster at different temperature profiles. Evolving volatile compounds out of the roasting off-gas were analyzed by photoionization mass spectrometry at four different wavelengths, either with single-photon ionization (SPI) or resonance-enhanced multiphoton ionization (REMPI). The different analyte selectivities at the four wavelengths and their relevance for the examination of the roasting process were discussed. Furthermore, intensities of observed m/z were grouped by non-negative matrix factorization (NMF) to reveal the temporal evolutions of four roasting phases ("evaporation", "early roast", "late roast", and "overroast") from NMF scores and the corresponding molecular composition from the NMF factor loadings, giving chemically sound results concerning the roasting phases. Finally, linear classifiers were constructed from real mass spectra at maximum NMF scores by linear discriminant analysis to obtain quantities which are simple to measure for real-time analysis of the roasting process.
AU  - Czech, H.*
AU  - Schepler, C.*
AU  - Klingbeil, S.*
AU  - Ehlert, S.*
AU  - Howell, J.*
AU  - Zimmermann, R.
C1  - 48927
C2  - 41515
CY  - Washington
SP  - 5223-5231
TI  - Resolving coffee roasting-degree phases based on the analysis of volatile compounds in the roasting off-gas by Photoionization Time-of-Flight Mass Spectrometry (PI-TOFMS) and statistical data analysis: Toward a PI-TOFMS roasting model.
JO  - J. Agric. Food Chem.
VL  - 64
IS  - 25
PB  - Amer Chemical Soc
PY  - 2016
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Specific and sensitive food biomarkers are necessary to support dietary intake assessment and link nutritional habits to potential impact on human health. A multistep nutritional intervention study was conducted to suggest novel biomarkers for coffee consumption. (1)H NMR metabolic profiling combined with multivariate data analysis resolved 2-furoylglycine (2-FG) as a novel putative biomarker for coffee consumption. We relatively quantified 2-FG in the urine of coffee drinkers and investigated its origin, metabolism, and excretion kinetics. When searching for its potential precursors, we found different furan derivatives in coffee products, which are known to get metabolized to 2-FG. Maximal urinary excretion of 2-FG occurred 2 h after consumption (p = 0.0002) and returned to baseline after 24 h (p = 0.74). The biomarker was not excreted after consumption of coffee substitutes such as tea and chicory coffee and might therefore be a promising acute biomarker for the detection of coffee consumption in human urine.
AU  - Heinzmann, S.S.
AU  - Holmes, E.*
AU  - Kochhar, S.*
AU  - Nicholson, J.K.*
AU  - Schmitt-Kopplin, P.
C1  - 46934
C2  - 39066
SP  - 8615-8621
TI  - 2-Furoylglycine as a candidate biomarker of coffee consumption.
JO  - J. Agric. Food Chem.
VL  - 63
IS  - 38
PY  - 2015
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Plants can extensively transform contaminants after uptake through phase I and phase II metabolism to a large diversity of products. UPLC-QToF-MS was used to detect and identify metabolites of the bacteriostatic agent triclosan in a horseradish hairy root culture. Thirty-three metabolites of triclosan were recognized by a stepwise approach of mass defect filtering, multivariate data analysis, and isotope pattern filtering from a data set of several thousands of signals in the exposed culture. Structure proposals were elaborated for 23 triclosan metabolites on the basis of their MS data. The majority were identified as conjugates (phase II metabolites) such as saccharides or sulfosaccharides. Additionally, a disulfosaccharide was identified as a plant metabolite for the first time. Besides that, also conjugates of a phase I metabolite, hydroxytriclosan, were determined in horseradish tissue extracts. Dehalogenation products of triclosan were not observed. The large number of metabolites detected and identified in this study emphasizes the importance of a comprehensive analytical approach in studies on the uptake and fate of organic contaminants in plants.
AU  - Macherius, A.*
AU  - Seiwert, B.*
AU  - Schröder, P.
AU  - Huber, C.
AU  - Lorenz, W.*
AU  - Reemtsma, T.*
C1  - 30616
C2  - 33774
CY  - Washington
SP  - 1001-1009
TI  - Identification of plant metabolites of environmental contaminants by UPLC-QToF-MS: The in vitro metabolism of triclosan in horseradish.
JO  - J. Agric. Food Chem.
VL  - 62
IS  - 5
PB  - Amer Chemical Soc
PY  - 2014
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Simulated sunlight irradiation causing degradation of amidosulfuron, a pyrimidinylsulfonylurea herbicide, has been investigated in aqueous solution. The main degradation products were followed up by ultrahigh-pressure liquid chromatography with a UV detector (UHPLC-UV) and identified by combining ultrahight-pressure liquid chromatography-mass spectrometry (UHPLC-MS) and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS). On the basis of the retrosynthetic analysis, the most identified degradation products were mainly due to the losses of methylsulfamic acid (CH5NO3S), sulfocarbamic acid (CH3NO5S), carbamic acid (CH3NO2), methyl(methylsulfonyl)sulfamic acid (C2H7NO5S2), N-methylmethanesulfonamide (C2H7NO2S), and sulfonic acid (H2SO4) molecules. Accordingly, O and S-demethylation as well as hydroxylation processes were also observed. Sum formulas of the main degradation products were assigned, and a mechanical pathway is proposed.
AU  - Harir, M.
AU  - Chnirheb, A.
AU  - Kanawati, B.
AU  - El Azzouzi, M.*
AU  - Schmitt-Kopplin, P.
C1  - 25733
C2  - 31921
SP  - 5271-5278
TI  - Chromatography and high-resolution mass spectrometry for the characterization of the degradation products of the photodegradation of amidosulfuron: An analytical approach.
JO  - J. Agric. Food Chem.
VL  - 61
IS  - 22
PB  - Amer. Chemical Soc.
PY  - 2013
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Botrytis cinerea infection of grape berries leads to changes in the chemical composition of grape and the corresponding wine and, thus, affects wine quality. The metabolic effect of Botrytis infection in Champagne base wine was investigated through a (1)H NMR-based metabolomic approach. Isoleucine, leucine, threonine, valine, arginine, proline, glutamine, γ-aminobutyric acid (GABA), succinate, malate, citrate, tartarate, fructose, glucose, oligosaccharides, amino acid derivatives, 2,3-butanediol, acetate, glycerol, tyrosine, 2-phenylethanol, trigonelline, and phenylpropanoids in a grape must and wine were identified by (1)H NMR spectroscopy and contributed to metabolic differentiations between healthy and botrytized wines by using multivariate statistical analysis such as principal component analysis (PCA). Lowered levels of glycerol, 2,3-butanediol, succinate, tyrosine, valine derivative, and phenylpropanoids but higher levels of oligosaccharides in the botrytized wines were main discriminant metabolites, demonstrating that Botrytis infection of grape caused the fermentative retardation during alcoholic fermentation because the main metabolites responsible for the differentiation are fermentative products. Moreover, higher levels of several oligosaccharides in the botrytized wines also indicated the less fermentative behavior of yeast in the botrytized wines. This study highlights a metabolomic approach for better understanding of the comprehensive metabolic influences of Botrytis infection of grape berries in Champagne wines.
AU  - Hong, Y.S.*
AU  - Cilindre, C.*
AU  - Liger-Belair, G.*
AU  - Jeandet, P.*
AU  - Hertkorn, N.
AU  - Schmitt-Kopplin, P.
C1  - 6578
C2  - 28932
SP  - 7237-7245
TI  - Metabolic influence of Botrytis cinerea infection in champagne base wine.
JO  - J. Agric. Food Chem.
VL  - 59
IS  - 13
PB  - American Chemical Society
PY  - 2011
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Xanthohumol (XN) is the major prenylated chalcone of hops and hence an ingredient of beer. Despite many advances in understanding of the pharmacology of XN, one largely unresolved issue is its low bioavailability in the human organism. Also, not much is known about its actual concentrations and pharmacokinetics in liver and intestinal cells. Therefore, the uptake, intracellular distribution, and kinetics of XN were studied in various cell types, namely, hepatocellular carcinoma cells (HuH-7), hepatic stellate cells (HSC), primary cultured hepatocytes, and colorectal adenocarcinoma cells (Caco-2). Fluorescent microscopy allowed for the first time visualization and tracing of the uptake and intracellular distribution of XN. A rapid accumulation of XN concentrations that were up to >60-fold higher than the concentration present in the ambient culture medium was observed. Fluorescence recovery after photobleaching experiments revealed that most XN molecules are bound to cellular proteins, which may alter properties of cellular factors.
AU  - Wolff, H.
AU  - Motyl, M.*
AU  - Hellerbrand, C.*
AU  - Heilmann, J.*
AU  - Kraus, B.*
C1  - 6909
C2  - 29268
CY  - Washington, DC, USA
SP  - 12893-12901
TI  - Xanthohumol uptake and intracellular kinetics in hepatocytes, hepatic stellate cells, and intestinal cells.
JO  - J. Agric. Food Chem.
VL  - 59
IS  - 24
PB  - American Chemical Society
PY  - 2011
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Solar radiation is a key environmental signal in regulation of plant secondary metabolism. Since metabolic responses to light and ultraviolet (UV) radiation exposure are known to depend on the ratio of spectral ranges (e.g., UV-B/PAR), we examined effects of different UV-B radiation (280-315 nm) and photosynthetically active radiation (PAR, 400-700 nm) levels and ratios on yield and pattern of monoterpenoid essential oil of peppermint. Experiments were performed in exposure chambers, technically equipped for realistic simulation of natural climate and radiation. The experimental design comprised four irradiation regimes created by the combination of two PAR levels including or excluding UV-B radiation. During flowering, the highest essential oil yield was achieved at high PAR (1150 micromol m(-2) s(-1)) and approximate ambient UV-B radiation (0.6 W m(-2)). Regarding the monoterpene pattern, low PAR (550 micromol m(-2) s(-1)) and the absence of UV-B radiation led to reduced menthol and increased menthone contents and thereby to a substantial decrease in oil quality. Essential oil yield could not be correlated with density or diameter of peltate glandular trichomes, the epidermal structures specialized on biosynthesis, and the accumulation of monoterpenes. The present results lead to the conclusion that production of high quality oils (fulfilling the requirements of the Pharmacopoeia Europaea) requires high levels of natural sunlight. In protected cultivation, the use of UV-B transmitting covering materials is therefore highly recommended.
AU  - Behn, H.*
AU  - Albert, A.
AU  - Marx, F.*
AU  - Noga, G.*
AU  - Ulbrich, A.*
C1  - 4177
C2  - 27696
SP  - 7361-7367
TI  - Ultraviolet-B and photosynthetically active radiation interactively affect yield and pattern of monoterpenes in leaves of peppermint (Mentha x piperita L.).
JO  - J. Agric. Food Chem.
VL  - 58
IS  - 12
PB  - American Chemical Society
PY  - 2010
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Domoic acid (DA), a neurotoxic amino acid produced by some strains of phytoplankton, is responsible for the human toxic syndrome amnesic shellfish poisoning. This exocitotoxin results in neuronal degeneration and necrosis in specific regions of the hippocampus. Because DA accumulates mostly in shellfish, causing outbreaks in different countries, screening for DA has been carried out with various assays. Although bioassays and immunoassays have been developed, several liquid chromatographic methods for the determination of DA in different matrices such as shellfish, algae, or seawater have been reported. Additionally, other alternative methods such as capillary electrophoresis and capillary electrochromatography have been described. This paper summaries the toxicology, the chemistry, and the developed determination methods of DA.
AU  - He, Y.
AU  - Fekete, A.
AU  - Chen, G.N.*
AU  - Harir, M.
AU  - Zhang, L.*
AU  - Tong, P.*
AU  - Schmitt-Kopplin, P.
C1  - 2742
C2  - 28187
CY  - Washington, DC
SP  - 11525-11533
TI  - Analytical approaches for an important shellfish poisoning agent: Domoic acid.
JO  - J. Agric. Food Chem.
VL  - 58
IS  - 22
PB  - AMERICAN CHEMICAL SOCIETY
PY  - 2010
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Soft single photon ionization-time-of-flight mass spectrometry (SPI-TOFMS) and principal component analysis (PCA) were applied for the characterization and discrimination of the chemical patterns of all individual cigarette puffs from the 2R4F University of Kentucky research reference cigarette. The SPI-TOFMS was connected to a smoking machine, and 10 cigarettes were smoked under defined smoking conditions. A total of 41 detected mass signals could be clearly assigned to smoke constituents (e.g., unsaturated hydrocarbons, aromatic species, sulfurous compounds, and nitrogen-containing substances). For further analysis, the on-line recorded mass signals were added up for each cigarette puff resulting in a single summed mass spectrum for each puff. The so-achieved puff-by-puff resolved yields were additionally normalized by the corresponding total ion signal, which eliminated the influences of varying amounts of burnt tobacco. These values were incorporated into a PCA to find differences and similarities in the chemical patterns of the individual cigarette puffs. In addition, absolute (without normalization) and normalized puff resolved yields were used to clarify occurring trends. Thereby, it was shown that the chemical pattern of the first cigarette puff was very unique, whereby extraordinary high yields of unsaturated hydrocarbons are mainly responsible for this. Depending on the smoking procedure, the chemical pattern of the second puff can also be separated from the first and the third puff. In this case, nitrogen-containing substances play an important role. Puffs three to eight show only small but observable differences. These changes are greater influenced by oxygen-containing and sulfurous smoke constituents. The findings reveal that the overall chemical patterns of machine-smoked cigarette puffs vary quite a lot during the smoking process. This lets us assume that the burden of hazardous compounds for the human smoker also differs from puff to puff.
AU  - Adam, T.*
AU  - Baker, R.R.*
AU  - Zimmermann, R.
C1  - 5007
C2  - 24324
SP  - 2055-2061
TI  - Characterization of puff-by-puff resolved cigarette mainstream smoke by single photon ionization-time-of-flight mass spectrometry and principal component analysis.
JO  - J. Agric. Food Chem.
VL  - 55
IS  - 6
PB  - American Chemical Soc.
PY  - 2007
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Direct degradation of imazapic, an herbicide of the imidazoline family, has been investigated in aqueous solution at different concentrations, pH values, and temperatures. The efficiency of the photodegradation process has been evaluated through degradation rate constants that could be fitted best with pseudo-first-order kinetics (Ct = C0 e–kt). Ultrahigh resolution mass spectrometry (FTICR/MS) was used in electrospray ionization mode as a tool to study the photolysis process on a molecular level, whereas UV–vis and high-performance liquid chromatography/mass spectrometry analysis were used to follow, by time, the evolution of the intermediates. Taking advantage of the high resolving power of FTICR/MS to perform precise formula assignments taking account of the natural abundance of isotopes, we herein propose and demonstrate an approach using 2D-derived van Krevelen visualization (O/C, H/C, m/z) to confirm the formation of imazapic intermediates. Such an approach allows a qualitative analysis of intermediates and elucidates the plausible reaction pathways of the photolysis process. More than eight photoproducts were separated and identified as a phototransformation of the imidazole ring. A mechanistical pathway was proposed.
AU  - Harir, M.
AU  - Gáspár, A.
AU  - Frommberger, M.
AU  - Lucio, M.
AU  - El Azzouzi, M.*
AU  - Martens, D.*
AU  - Kettrup, A.*
AU  - Schmitt-Kopplin, P.
C1  - 54221
C2  - 45281
SP  - 9936-9943
TI  - Photolysis pathway of imazapic in aqueous solution: ultrahigh resolution mass spectrometry analysis of intermediates.
JO  - J. Agric. Food Chem.
VL  - 55
IS  - 24
PY  - 2007
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The antibacterial drug furazolidone belonging to the group of nitrofuran antibacterial agents has been widely used as an antibacterial and antiprotozoal feed additive for poultry, cattle, and farmed fish in China. During application a large proportion of the administered drug may reach the environment directly or via feces. Although the use of furazolidone is prohibited in numerous countries, there are indications of its illegal use. It is known that furazolidone can be rapidly metabolized to 3-amino-2-oxazolidinone (AOZ) in the body of the target organism. In this study, a total of 21 fish feed samples, including 17 commercial fish feeds from local markets in China (representing 15 different formulations) and 4 fish feeds obtained from Germany and Turkey, respectively, are analyzed to determine whether the drug is still illegally used or commercially available feeds are contaminated by this drug. High-performance liquid chromatography (HPLC) and liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) methods have been implemented to determine furazolidone and its metabolite AOZ in fish feeds containing animal protein, respectively. An efficient and convenient cleanup method for the determination of furazolidone in fish feeds is developed, and a simple cleanup method for the determination of AOZ is used. Method recoveries for samples used were determined as 87.7-98.3% for furazolidone at two spike levels of 2.0 and 5.0 ng g-1 and as 95.6-102.8% for AOZ at spike levels of 0.4 and 0.8 ng g-1. Limits of detections were 0.4 ng g-1 for furazolidone and 0.05 ng g-1 for AOZ. The established methods are therefore suitable for the determination of furazolidone and its metabolite AOZ in fish feeds at trace contamination levels. Using the established methods, all fish feed samples have been proved to be furazolidone negative; however, AOZ is tested in 16 of 17 fish feeds obtained from local markets in the Hubei province of China, with a positive rate as high as 94.1%.
AU  - Hu, X.-Z.*
AU  - Xu, Y.*
AU  - Yediler, A.
C1  - 837
C2  - 24429
SP  - 1144-1149
TI  - Determinations of Residual Furazolidone and Its Metabolite, 3-Amino-2-oxazolidinone (AOZ), in Fish Feeds by HPLC-UV and LC-MS/MS, Respectively.
JO  - J. Agric. Food Chem.
VL  - 55
IS  - 4
PB  - Amer. Chemical Soc.
PY  - 2007
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Butkovic, V.*
AU  - Klasinc, L.*
AU  - Bors, W.
C1  - 3347
C2  - 21833
SP  - 2816-2820
TI  - Kinetic study of flavonoid reactions with stable radicals.
JO  - J. Agric. Food Chem.
VL  - 52
PY  - 2004
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Cox, L.*
AU  - Fernandes, M.C.*
AU  - Zsolnay, A.
AU  - Hermosin, M.C.*
AU  - Cornejo, J.*
C1  - 4954
C2  - 21982
SP  - 5635-5642
TI  - Changes in dissolved organic carbon of soil amendments with aging: Effect on pesticide adsorbtion behavior.
JO  - J. Agric. Food Chem.
VL  - 52
PY  - 2004
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Krämer, P.M.
AU  - Goodrow, M.H.*
AU  - Kremmer, E.
C1  - 3615
C2  - 21782
SP  - 2462-2471
TI  - Enzyme-linked immunosorbent assays based on rabbit polyclonal and rat monoclonal antibodies against isoproturon.
JO  - J. Agric. Food Chem.
VL  - 52
PY  - 2004
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Krämer, P.M.
AU  - Kremmer, E.
AU  - Forster, S.
AU  - Goodrow, M.H.*
C1  - 3707
C2  - 22045
SP  - 6394-6401
TI  - Extending the working range of immunoanalysis by exploitation of two monoclonal antibodies.
JO  - J. Agric. Food Chem.
VL  - 52
PY  - 2004
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Dorfner, R.
AU  - Ferge, T.
AU  - Kettrup, A.
AU  - Zimmermann, R.
AU  - Yeretzian, C.*
C1  - 10117
C2  - 21231
SP  - 5768-5773
TI  - Real-Time Monitoring of 4-Vinylguaiacol, Guaiacol and Phenol during Coffee Roasting by Resonant Laser Ionization Time-of-Flight Mass Spectrometry.
JO  - J. Agric. Food Chem.
VL  - 51
PY  - 2003
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Hofmann, T.*
AU  - Bors, W.
AU  - Stettmaier, K.
C1  - 20879
C2  - 18936
SP  - 379-390
TI  - Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids.
JO  - J. Agric. Food Chem.
VL  - 47
PY  - 1999
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Hofmann, T.*
AU  - Bors, W.
AU  - Stettmaier, K.
C1  - 20880
C2  - 18937
SP  - 391-396
TI  - Radical-assisted melanoidin formation during thermal processing of foods as well as under physiological conditions.
JO  - J. Agric. Food Chem.
VL  - 47
PY  - 1999
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Sandermann, H.
AU  - Musick, T.J.
AU  - Aschbacher, P.W.
C1  - 19746
C2  - 12889
SP  - 2001-2007
TI  - Animal Bioavailability of a 3,4-Dichloroaniline-Lignin Metabolite Fraction from Wheat.
JO  - J. Agric. Food Chem.
VL  - 40
PY  - 1992
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The photolysis of the fungicide metalaxyl in aqueous solution has been examined, Irradiation at 254 and 290 nm resulted, respectively, in 53 and 10% substrate transformation in 3 h. Long-time (65 h) irradiation under artificial sunlight in the presence of commercially available humic acid resulted in 65% degradation of the chemical. The photolysis leads not only to rearrangement of the N-acyl group to the aromatic ring but also to demethoxyiation, N-deacylation, and elimination of the methoxycarbonyl group from the molecule.
AU  - Sukul, P.
AU  - Moza, P.N.
AU  - Hustert, K.
AU  - Kettrup, A.
C1  - 40566
C2  - 38772
SP  - 2488-2492
TI  - Photochemistry of metalaxyl.
JO  - J. Agric. Food Chem.
VL  - 40
IS  - 12
PY  - 1992
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Winkler, R.
AU  - Sandermann, H.
C1  - 19745
C2  - 12888
SP  - 2008-2012
TI  - N-Glucosyl Conjugates of Chlorinated Anilines: Spontaneous Formation and Cleavage.
JO  - J. Agric. Food Chem.
VL  - 40
PY  - 1992
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Pendimethalin decomposed readily when irradiated in methanol at wavelengths λ ≥ 250 nm to form a number of products. In addition to the N-dealkylated intermediates, the principal products were 2-methyl-4,6-dinitro-5-[(l-ethylpropyl)amino]benzaldehydeand2-methyl-4,6- dinitro-5-[(l-ethylpropyl)amino]benz;yl alcohol. The decomposition at sunlight wavelengths (λ ≥ 290 nm) in methanol is relatively slower and also leads to N-dealkylation and arylmethyl oxidation. Neither acid nor alkali has an effect on the rate of disappearance of pendimethalin. At acidic pH N-dealkylation takes place, whereas at alkaline pH one of the NO2 groups is replaced by an OH group.
AU  - Pal, S.K.
AU  - Moza, P.N.
AU  - Kettrup, A.
C1  - 40829
C2  - 11811
SP  - 797-800
TI  - Photochemistry of pendimethalin.
JO  - J. Agric. Food Chem.
VL  - 39
IS  - 4
PY  - 1991
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Sandermann, H.
AU  - Arjmand, M.
AU  - Gennity, I.
AU  - Winkler, R.
AU  - Struble, C.B.
AU  - Aschbacher, P.W.
C1  - 18361
C2  - 11552
SP  - 1877-1880
TI  - Animal Bioavailability of Defined Xenobiotic Lignin Metabolites.
JO  - J. Agric. Food Chem.
VL  - 38
PY  - 1990
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Lignin has been recognized as a major component of bound pesticide residues in plants and is thought to be undigestible in animals. Two defined ring-U-14C-labeled chloroaniline/lignin metabolites have now been fed to rats, where a release of ∼66% of the bound xenobiotic occurred in the form of simple chloroaniline derivatives. The observed high degree of bioavailability indicates that bound pesticidal residues may possess ecotoxicological significance. In parallel studies, the white-rot fungus Phanerochaete chrysosporium was more efficient, and a soil system was much less efficient, in the degradation of the [ring-U-14C]chloroaniline/lignin metabolites.
AU  - Sandermann, H.J.
AU  - Arjmand, M.
AU  - Gennity, I.
AU  - Winkler, R.
AU  - Struble, C.B.*
AU  - Aschbacher, P.W.*
C1  - 42101
C2  - 40270
SP  - 1877-1880
TI  - Animal bioavailability of defined xenobiotic lignin metabolites.
JO  - J. Agric. Food Chem.
VL  - 38
IS  - 9
PY  - 1990
SN  - 0021-8561
ER  - 

TY  - JOUR
AU  - Reiml, D.
AU  - Scheunert, I.
AU  - Korte, F.
C1  - 17820
C2  - 9456
SP  - 244-248
TI  - Leaching of Conversion Products of (14C)Buturon from Soil during 12 Years after Application.
JO  - J. Agric. Food Chem.
VL  - 37
IS  - 1
PY  - 1989
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Buturon (ring 14C) was applied to wheat and soil in two successive years (3 kg/ha each year) at outdoor conditions. Residual radioactive substances in the upper soil layer (0-10-cm depth) were measured 1.5, 2.5, 3.5, 6.0, and 6.5 years after the first treatment. The decline of total radiocarbon was a two-stage process. Mass balance studies were conducted 1.5, 2.5, and 6.5 years after the first treatment; total recoveries were 83, 47, and 27%, respectively, of the applied radioactivity. Extractability of residues with cold chloroform was 20-30% of total residues. Whereas the chloroform-soluble conversion products identified after the first growing period mostly resulted from alterations within the side chain of buturon, after seven seasons only hydroxylated and/or methoxylated derivatives of 4-chloroaniline could be detected.
AU  - Constenla, M.A.
AU  - Moza, P.N.
AU  - Scheunert, I.
AU  - Haque, A.U.
AU  - Klein, W.
C1  - 34188
C2  - 38252
SP  - 208-211
TI  - Fate of buturon-14C in soil during seven seasons of exposure under outdoor conditions.
JO  - J. Agric. Food Chem.
VL  - 32
IS  - 2
PY  - 1984
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - 4-Chloroaniline-14C was applied to soil in a lysimeter, corresponding to about 1.25 ppm to a depth of 10 cm, and barley was sown. After 20 weeks, a total of 32.8% of the radiocarbon applied was recovered, in soil 32.4%, in plants 0.3%, and in leaching water 0.1%. The radioactivity in soil consisted of 30.8% unextractable residues and 1.6% soluble conversion products; that in plants consisted of 0.24% unextractable residues and 0.03% soluble metabolites (percent of applied 14C). In the second and third year after the application, potatoes and carrots, respectively, were grown; total recoveries were 32.0% and 31.2%, respectively. The soluble radioactive fractions in soil and plants of the two first years contained 4-chloroformanilide (I), 4-chloroacetanilide (II), 4-chloronitrobenzene (III), 4-chloronitrosobenzene (IV), 4,4′-dichloroazoxybenzene (V), and 4,4′-dichloroazobenzene (VI). The radioactive substances unextractable in soil and those in leaching water were partially hydrolyzable and gave 4-chloroaniline.
AU  - Freitag, D.
AU  - Scheunert, I.
AU  - Klein, W.
AU  - Korte, F.
C1  - 42126
C2  - 38337
SP  - 203-207
TI  - Long-term fate of 4-chloroaniline-14C in soil and plants under outdoor conditions. A contribution to terrestrial ecotoxicology of chemicals.
JO  - J. Agric. Food Chem.
VL  - 32
IS  - 2
PY  - 1984
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Sheep were contaminated with hexachlorobenzene and then fed a conventional diet with or without 5% mineral oil or hexadecane. Similar to nonruminant species, both treatments enhanced fecal excretion of hexachlorobenzene about 3-fold and reduced levels of hexachlorobenzene stored in adipose tissue. Normal digestive functions of the animals, including fiber digestion by rumen microbes, were not affected by the administration of the aliphatic hydrocarbons. Dietary administration of mineral oil could be an inexpensive way to save livestock contaminated with toxic lipophilic compounds, such as many pesticides and industrial chemicals.
AU  - Rozman, K.K.
AU  - Rozman, T.A.
AU  - Greim, H.A.
AU  - Nieman, I.J.*
AU  - Smith, G.S.*
C1  - 42327
C2  - 38504
SP  - 98-100
TI  - Use of aliphatic hydrocarbons in feed to decrease body burdens of lipophilic toxicants in livestock.
JO  - J. Agric. Food Chem.
VL  - 30
IS  - 1
PY  - 1982
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - After application of pentachlorophenol-14C at 23 kg/ha to flooded rice soil in a plant growth chamber, 36.5% was recovered in soil after one growing period and 30.1% after two periods. After one growing period, the residues were 28.61% unidentified unextractable substances, 0.51% unchanged free pentachlorophenol, 0.61% conjugated pentachlorophenol, 1.67% free tetra- and trichlorophenols, <0.01% conjugated trichlorophenols, 0.33% anisoles, and 4.74% highly polar, mostly nonhydrolyzable compounds (percent of applied radioactivity). In the second growing period, the portion of unextractable residues in soil increased; the composition of the extractable radioactivity was similar to that of the first vegetation period.
AU  - Weiss, U.M.
AU  - Scheunert, I.
AU  - Klein, W.
AU  - Korte, F.
C1  - 33055
C2  - 38597
SP  - 1191-1194
TI  - Fate of pentachlorophenol-14C in soil under controlled conditions.
JO  - J. Agric. Food Chem.
VL  - 30
IS  - 6
PY  - 1982
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Pentachlorophenol-14C was applied to soil (23 kg/ha), and rice plants were grown over two vegetation periods under flooded conditions. The uptake of radioactivity by plants was 12.9% in the first and 2.5% in the second year. Rice roots (first year) contained 0.14% of the applied radioactivity as free pentachlorophenol; 0.06% was conjugated pentachlorophenol, 0.43% free and conjugated lower chlorinated phenols, 0.07% anisoles, 0.01% dimethoxytetrachlorobenzenes, 0.03% 1,2-dihydroxy- and/or monohydroxymonomethoxytetrachlorobenzene, 0.48% polar nonhydrolyzable substances, and 3.95% unextractable residues. In the straw (first year), neither pentachlorophenol nor lower chlorinated phenols or anisoles were detected; the main metabolite (0.63%) was probably tetrachlorobenzoquinone. In the grains, low radioactive residues (0.12% of applied radioactivity or 4 ppm equivalent to pentachlorophenol) could not be identified. In the second year (pentachlorophenol residues in soil corresponding to ∼8.4 kg/ha), the portion of unextractable residues in the plants increased, and lower chlorinated conjugated phenols were identified.
AU  - Weiss, U.M.
AU  - Moza, P.N.
AU  - Scheunert, I.
AU  - Haque, A.U.
AU  - Korte, F.
C1  - 40917
C2  - 38863
SP  - 1186-1190
TI  - Fate of pentachlorophenol-14C in rice plants under controlled conditions.
JO  - J. Agric. Food Chem.
VL  - 30
IS  - 6
PY  - 1982
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - 2,4′,5-Trichlorobiphenyl-14C (1.28 kg/ha) and 2,2′,4,4′,6-pentachlorobiphenyl-14C (1.12 kg/ha) were applied each to soil in a lysimeter-type box under outdoor conditions, and carrots were grown. In the following year, sugar beets were grown without retreatment. For the trichlorobiphenyl, only 32.5% of the applied radioactivity was recovered in soil and plants after the first season; 67.5% was lost due to volatilization, uptake by carrot plants was 3.1% of the applied radioactivity. The radioactivity remaining in the soil was partly dispersed to a depth of 40 cm and consisted of 78.7% trichlorobiphenyl, 1.6% soluble conversion products, and 19.7% unextractable residues; in the second year, total recovery as well as the portion of unchanged parent compound decreased. Uptake by sugar beets was only 0.2%. The soluble conversion products in plants and soil were identified as oxygenated metabolites. For the pentachlorobiphenyl, total recovery was 58.5%, and loss due to volatilization 41.5%, uptake by crops 1.4% (after first season), and conversion below 1%; no metabolites were identified.
AU  - Moza, P.N.
AU  - Scheunert, I.
AU  - Klein, W.
AU  - Korte, F.
C1  - 41506
C2  - 35779
SP  - 1120-1124
TI  - Studies with 2,4′,5-trichlorobiphenyl-14C and 2,2′,4,4′,6-pentachlorobiphenyl-14C in carrots, sugar beets, and soil.
JO  - J. Agric. Food Chem.
VL  - 27
IS  - 5
PY  - 1979
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - With the help of column chromatography, 3 new substances, 1-exo,4,5,7,8,8- hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoindene 1-exo,2-exo,4,5,7,8,8- heptachloro-3a,4,7,7a-tetrahydro-4,7-methanoindane, and 1-exo,2-exo,4,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methanoindane, were isolated from technical chlordane and were identified by spectroscopic methods (mass spectrometry, infrared, and 1H NMR). These compounds could be synthesized by photochemical dechlorination of heptachlor and of α- (or cis-) chlordane in methanol. In addition, the mixture was investigated by capillary gas chromatography and by combined gas chromatography and mass spectrometry. The data obtained were used to characterize the composition of technical chlordane.
AU  - Parlar, H.A.
AU  - Hustert, K.
AU  - Gaeb, S.
AU  - Korte, F.
C1  - 41594
C2  - 35781
SP  - 278-283
TI  - Isolation, identification, and chromatographic characterization of some chlorinated C10 hydrocarbons in technical chlordane.
JO  - J. Agric. Food Chem.
VL  - 27
IS  - 2
PY  - 1979
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Twelve male rats were fed a diet containing 3.3 ppm Kepone-14C for 3 days. After 1 day on the control diet, six animals received a ration containing 8% light liquid paraffin for 24 days. The remaining six animals served as control. Paraffin-treated rats excreted significantly more radioactivity with feces (61%) compared to controls (52%) and had significantly lower concentrations of radioactivity in 14 of 18 tissues analyzed. Excretion of radioactivity with urine was of minor importance (0.5-0.6%) in both groups.
AU  - Richter, E.*
AU  - Lay, J.P.
AU  - Klein, W.
AU  - Korte, F.
C1  - 41833
C2  - 35748
SP  - 187-189
TI  - Enhanced elimination of Kepone-14C in rats fed liquid paraffin.
JO  - J. Agric. Food Chem.
VL  - 27
IS  - 1
PY  - 1979
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - During the decomposition of sodium pentachlorophenolate by Alcaligenes eutrophus, Aeromonas hydrophila var. hydrophila and var. anaerogenes, Azotobacter chroococcum, Azotobacter vinelandii, Flavobacterium aquatile, Pseudomonas fluorescens, Cytophaga johnsonae, Corynebacterium aquaticum, Brevibacterium testaceum, and Arthrobacter globiformis the following were identified as metabolites: pentachlorophenol acetate, pentachloroanisole, 2,3,4,5-tetrachloroanisole, 2,3,4,6-tetrachloroanisole, 2,3,5,6-tetrachloroanisole, 2,3,4,5-tetrachlorophenol, 2,3,5,6- tetrachlorophenol, tetrachlororesorcinol, tetrachlorohydroquinone, and tetrachlorocatechol diacetate, the principal metabolite being pentachlorophenol acetate. Up to 6.2% of the sodium pentachlorophenolate used was recovered as pentachlorophenol acetate, while all other metabolites were found in amounts less than 1% of the starting compound.
AU  - Rott, B.
AU  - Nitz, S.
AU  - Korte, F.
C1  - 41643
C2  - 35778
SP  - 306-310
TI  - Microbial decomposition of sodium pentachlorophenolate.
JO  - J. Agric. Food Chem.
VL  - 27
IS  - 2
PY  - 1979
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Of a series of microorganisms isolated from the soil, Hypocrea pilulifera, a fungus of the Ascomycetes class, is the only one able to metabolize the herbicide methabenzthiazuron. In cultures of this fungus the distribution of radioactivity between the individual extract fractions was found to be the following: chloroform extract fraction 73.6-79.4%, water extract fraction 6.2-11.8%, and mycelium extract fraction 3.7-12.1%. As the incubation period is lengthened, the water-soluble metabolites increase while the chloroform-soluble ones decrease. The degradation rate of [14C]methabenzthiazuron is 16% of the [14C]methabenzthiazuron recovered in 7 weeks. Six transformation products of [14C]methabenzthiazuron were isolated with the aid of thin-layer and column chromatography and characterized with the aid of spectroscopic and chromatographic methods.
AU  - Goettfert, J.
AU  - Parlar, H.A.
AU  - Korte, F.*
C1  - 42089
C2  - 35824
SP  - 628-632
TI  - Microbial transformation of [14C]methabenzthiazuron by the soil fungus Hypocrea Cf. pilulifera Webster St. Con: Isolation, identification, and characterization of some metabolites from the chloroform extract.
JO  - J. Agric. Food Chem.
VL  - 26
IS  - 3
PY  - 1978
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The gas chromatographic determination of cyclodiene insecticides and their conversion products is often rendered difficult by the presence of PCB residues in environmental samples. This problem can be satisfactorily overcome by inducing photoisomerization reactions (λ > 290 nm) of some cyclodiene insecticides, thus producing the corresponding photoisomers in high yields. The photoisomers have longer retention times than their parent compounds and can therefore be identified and quantitatively determined by gas chromatography. The method can be improved by a subsequent UV irradiation of the samples with wavelengths above 230 nm in methanol. This procedure yields photodechlorinated products of the PCBs with shorter retention times but leaves the photoisomerization products of cyclodiene insecticides unaffected.
AU  - Mansour, M.
AU  - Parlar, H.A.
C1  - 33192
C2  - 35631
SP  - 483-485
TI  - Gas chromatographic determination of several cyclodiene insecticides in the presence of polychlorinated biphenyls by photoisomerization reactions.
JO  - J. Agric. Food Chem.
VL  - 26
IS  - 2
PY  - 1978
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The photoreactions of the heptachlor transformation product 1-exo-hydroxychlordene (exo-4,5,6,7,-8,8-hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoinden-1-ol) (2) dissolved in organic solvents, as a solid on glass, and dispersed on plant leaf surfaces have been investigated. In addition to the (2 + 2) cycloaddition typical for this substance class, an entirely novel intramolecular photoisomerization reaction was found. This reaction leads to cyclic ketone, 1,1a,2,2,3,exo-6-hexachloro-1a,2,3,3a,5a,5b-hexahydro-1,3-methano-1H- cyclobuta[cd]pentalen-4-one (8), whose structure was established by spectral data obtained by mass spectrometry, infrared spectrometry, and 1H and 13C nuclear magnetic resonance measurements.
AU  - Parlar, H.A.
AU  - Mansour, M.
AU  - Baumann, R.
C1  - 41774
C2  - 38177
SP  - 1321-1324
TI  - Photoreactions of hydroxychlordene in solution, as solids, and on the surface of leaves.
JO  - J. Agric. Food Chem.
VL  - 26
IS  - 6
PY  - 1978
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The constituent of technical chlordane designated compound C is an isomer of chlordene (C10H6Cl6). This isomer is formed via the rearrangement of isochlordene by the action of chlorine or free-radical initiating agents, such as Bz2O2/CCl4. By means of spectroscopic data (MS, IR, 1H NMR, and 13C NMR), it was shown that compound C does not possess the cyclodiene-type structure but corresponds to 3a,4,5,5a,5b,6-hexachloro-1a,2,3,3a,5a,5b-hexahydro-1,3-methano-1H-cyclobuta[gh] pentalene (III).
AU  - Gäb, S.
AU  - Parlar, H.A.
AU  - Korte, F.*
C1  - 41855
C2  - 35691
SP  - 1224-1226
TI  - Structural elucidation of compound C. A chlordene isomer constituent of technical chlordane.
JO  - J. Agric. Food Chem.
VL  - 25
IS  - 5
PY  - 1977
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The technical chlordane constituent designated compound K is a formal isomer of chlordane (C10H6Cl8) which is formed by chlorination of α-chlordene (1) (C10H6Cl6) via a Wagner-Meerwein rearrangement. Structural elucidation of K involves dechlorination reactions, especially spectroscopic studies (MS, 1H NMR, and 13C NMR) of various photodechlorination products (3-7). From these data a structure for compound K is proposed. Confirmation of this structure is obtained by single-crystal x-ray diffraction. According to the results, compound K corresponds to 2,4,4,5,6,6,7,8-octachlorooctahydro-1,5-ethenopentalene (2).
AU  - Gäb, S.
AU  - Born, L.*
AU  - Parlar, H.A.
AU  - Korte, F.*
C1  - 42370
C2  - 0
SP  - 1365-1371
TI  - Structural elucidation of an octachloro component of technical chlordane (compound K) by spectroscopic and X-ray methods.
JO  - J. Agric. Food Chem.
VL  - 25
IS  - 6
PY  - 1977
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The ir, MS, 1H NMR, and 13C NMR spectroscopic behavior of the synthetically produced low chlorinated bornane derivatives was studied. The obtained data were used for the spectral analysis of compound I, a substance isolated from technical toxaphene. It was further attempted to characterize the composition of technical toxaphene on the basis of spectroscopic data from defined toxaphene fractions.
AU  - Parlar, H.A.
AU  - Nitz, S.*
AU  - Gäb, S.*
AU  - Korte, F.*
C1  - 42097
C2  - 35674
SP  - 68-72
TI  - A contribution to the structure of the toxaphene components. Spectroscopic studies on chlorinated bornane derivatives.
JO  - J. Agric. Food Chem.
VL  - 25
IS  - 1
PY  - 1977
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - The technical chlordane constituents designated α-, β-, and γ-chlordene are isomers of chlordene (C10H6Cl6). These isomers are formed via the rearrangement of chlordene by the action of Cl2 or free-radical initiating agents, and they no longer possess the cyclodiene-type structure. Elucidation of these isomeric structures involved various chemical derivitization reactions. Oxidation with chromic oxide yielded ketones and epoxides while reduction with Zn-HOAc or CrCl2 produced mono- and didechlorinated homologs. Photoisom-ers, in which the two original ClC=CCl bonds had been cross-linked, resulted from their unsensitized uv irradiation. Spectral confirmation of structure was obtained by 1H NMR and gas chromatography-mass spectrometry (GC-MS) studies. It is postulated that α-chlordene is 1,2,3,5,7,8-hexa-chloro-1,3a,4,5,6,6a - hexahydro-1,4-ethenopentalene (III) and β-chlordene is 2,3,3a,4,5,7-hexa-chloro-3a,6,7,7a-tetrahydro-1,6-methano-1H-indene (XIII), with γ-chlordene (XI) being the 2,3,3a,4,5,8-hexachloro isomer of β-chlordene.
AU  - Cochrane, W.P.*
AU  - Parlar, H.A.
AU  - Gäb, S.
AU  - Korte, F.
C1  - 42534
C2  - 0
SP  - 882-886
TI  - Structural elucidation of the chlordene isomer constituents of technical chlordane.
JO  - J. Agric. Food Chem.
VL  - 23
IS  - 5
PY  - 1975
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Fifteen months after application of photodieldrin14C to soil (5 ppm of dry weight) in the open air, the following conversion products were identified by TLC, GLC, and mass spectrometry: the bridged isomer of dihydrochlordene dicarboxylic acid (1,7,8,exo-9,10,10-hexachlorotetracyclo[5.2.1.02,6.0 4,8]decane-3,5-exo,exo-dicarboxylic acid), amounting to about 0.5% of recovered radio-activity, a methoxylated derivative of this acid, amounting to about 0.5% of recovered radioactivity, and a bridged isomer of trans-4,5-dihydroxy-4,5-dihydroaldrin (3,exo-4,5,6,6,7-hexachloro-11,12-trans-dihydroxypentacyclo[6.4.0.0 2,10.03,7.05,9]dodecane), amounting to about 1% of recovered radioactivity.
AU  - Weisgerber, I.
AU  - Bieniek, D.
AU  - Kohli, J.
AU  - Klein, W.
C1  - 41931
C2  - 35849
SP  - 873-876
TI  - Isolation and identification of three unreported photodieldrin-14C metabolites in soil.
JO  - J. Agric. Food Chem.
VL  - 23
IS  - 5
PY  - 1975
SN  - 0021-8561
ER  - 

TY  - JOUR
AB  - Aldrin-14C has been applied to soils under outdoor conditions in Germany (2.9 kg/ha) and England (3.2 kg/ha) and potatoes have been sown. At harvest, more than 60% of the total radioactivity recovered from the soil and plants was due to metabolites, mainly dieldrin and a group of hydrophilic products, of which the main compound was identified as dihydrochlordene-14C dicarboxylic acid (1,2,3,4,8,8-hexachloro-1,4,4a,6,7,7a - hexahydro-1,4-endo-methylene-indene - 5,7-dicarboxylic acid). Photodieldrin-14C was also detected in small amounts in the potato haulm from England, as were traces of photoaldrin-14C in both soils. The conversion of aldrin-14C was least in the upper soil layer and greatest in deeper soil layers (10-60 cm from surface) and in the plants. Only very low residues were detected in the deeper soil layers in England, whereas more radioactivity was found in the deeper soil samples in Germany. The leaching water of the experiment in Germany contained only dihydrochlordene-14C dicarboxylic acid (0.02 ppm).
AU  - Klein, W.
AU  - Kohli, J.
AU  - Weisgerber, I.
AU  - Korte, F.
C1  - 42301
C2  - 35381
SP  - 152-156
TI  - Fate of aldrin-14C in potatoes and soil under outdoor conditions.
JO  - J. Agric. Food Chem.
VL  - 21
IS  - 2
PY  - 1973
SN  - 0021-8561
ER  -