Contact dermatitis to alpha-lipoic acid in an anti-wrinkle cream.
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Biomedical subjects
Publications and source records attributed to O Bergendorff.
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Allergic contact dermatitis is often caused by solid products such as rubber gloves. Patch testing with the product as is often gives negative results. Extraction of the haptens into an organic solvent is commonly performed to achieve a more correct investigation. The technique used for extraction of haptens from solid materials is only sporadically described. In this study, we investigated and optimized the yields of dithiocarbamates obtained by extraction from rubber gloves. The influence of solvent, extraction time and the procedures for extraction are evaluated. The delivery of zinc dibutyldithiocarbamate from the patch test preparation to the skin is determined.
The thiuram mix used in patch testing originally contains 4 compounds. However, chemical analysis of the test preparation revealed that several new compounds are spontaneously formed during storage. The structures of these compounds have been determined and the rate of their formation has been studied in buffer solution at pH 7.4. After a few hours, a large amount of mixed disulfides are formed in solutions originally containing only symmetric disulfides. The impact on the test result of the formation of asymmetric disulfides has been investigated by testing on thiuram-sensitive volunteers with different preparations of mixed thiuram disulfides. In our study, the formation of new asymmetric thiuram disulfides from the original symmetric thiuram disulfides in the test preparation had no influence on the result of the patch testing. However, as the chemical analysis showed that the mix composition changes during the period when the preparations are used, and differs between suppliers, the question is raised as to whether it is acceptable to use test preparations with a composition that is different from that labelled on the protocol.
N,N'-disalicylidene-1,2-diaminopropane is a copper inhibitor present in some adhesive plasters, rubber products and gasoline. Upon contact with water it is hydrolyzed to salicylaldehyde and 1,2-diaminopropane. All patients in this study showed positive patch-test reactions to N,N'-disalicylidene-1,2-diaminopropane, and also to 1,2-diaminopropane and ethylenediamine. None reacted to salicylaldehyde. Patch testing with different N,N'-disalicylidene-derivatives showed localization of the amino groups in positions 1 and 2 to be a prerequisite of cross-reactivity to 1,2-diaminopropane and ethylenediamine. An extraction procedure and a high-performance liquid chromatography (HPLC) method for the analysis of adhesive plasters is described. Studies of the hydrolysis of the copper inhibitor at physiological pH showed rapid formation of 1,2-diaminopropane under biomimetic conditions.
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Eight furanocoumarins were isolated from a methanol extract of dried roots of Angelica dahurica. One of these, phellopterin, strongly (IC50 = 0.36 microM) inhibits the binding of [3H]diazepam to central nervous system benzodiazepine receptors in vitro, while the others, despite their structural similarities with phellopterin, are considerably less active.
All sesquiterpenes present in a sample of scented myrrh were isolated and characterised. Seven compounds, with cadinane, guaiane, oplopane, and eudesmane skeletons, were obtained, of which two are new and two are reported from a natural source for the first time. The major component, T-cadinol, has previously been shown to possess smooth muscle-relaxing properties, and the major purpose of the investigation was to compare the effects of the minor and more polar sesquiterpenes with that of T-cadinol in the rat aorta. Like T-cadinol, the minor sesquiterpenes are more efficient in reducing K(+)-induced contractions than those induced by the alpha-adrenoceptor agonist phenylephrine, however, they were all less potent than T-cadinol.
At evaluation of contact dermatitis caused by solid material, patch testing is usually performed with the material as such and with extracts of it. In this study, optimization of the extraction technique monitored by quantitative HPLC analysis of the extracted haptens is described for mercaptobenzothiazole derivatives. Several solvents with different properties are included. Acetone has traditionally been a solvent widely used for the extraction of organic haptens from solid products. However, acetone and other ketones are not inert solvents. The rubber accelerators 2-(4-morpholinyl mercapto) benzothiazole (MMBT) and N-cyclohexyl-2-benzothiazyl sulfenamide (CBS) react with acetone, yielding 2 new compounds, which were isolated and characterised by NMR and MS. For the extraction of solid rubber products, methyl tert-butyl ether (MTBE) was found to be a more suitable solvent which is unreactive to most common haptens.
p-phenylenediamine derivatives are widely used in industry and in cosmetics, and several of them are well-known sensitizers. One group of allergenic p-phenylenediamine derivatives are used as colour film developers. Cross-reactivity between the colour film developers has been reported. In this paper, an occupational facial dermatitis due to colour film developers is described. The patient reacted to colour film developers (CD-1, CD-2, CD-3, and CD-4), but not to other p-phenylenediamine derivatives tested. He also showed allergic reactions to Disperse Blue 106 and Disperse Blue 124 and to Disperse Red 17, but not to Disperse Orange 3. The activation of the colour film developers by oxidation at physiological pH was analysed with chemical methods, and the mechanism responsible for the concomitant reactivities to the colour film developers and the disperse dyes at a molecular level is discussed.
S-(4-hydroxybenzyl)glutathione was isolated as the major principle responsible for the inhibition of the in vitro binding of kainic acid to brain glutamate receptors by water extracts of the plant Gastrodia elata. The affinity (IC50 value) of the compound is slightly lower compared to glutamate and glutathione.
Four flavonols with spasmolytic activity have been isolated from a methanol extract of Artemisia abrotanum L. (Asteraceae), as the principles primarily responsible for the smooth muscle relaxing activity of this plant. The flavonols show a dose-dependent relaxing effect on the carbacholine-induced contraction of guinea-pig trachea, the EC50 values for compounds 1-3 are 20-30 mumol/l while compound 4 is less active.
A novel prenylated isoflavanone, sigmoidin I, has been isolated from the roots of Erythrina sigmoidea, in addition to the known isoflavones, corylin and neobavaisoflavone and the known pterocarpan, phaseollidin. Its structure was established as 7,4'-dihydroxy-3'-methoxy-5'-(3-methylbut-2-enyl) isoflavanone by means of spectroscopic analyses and chemical transformations. Neobavaisoflavone displayed antifungal potency in vitro with minimum inhibitory concentrations against Aspergillus fumigatus and Cryptococcus neoformans, of 50 mg ml-1.
In addition to the two known compounds neotautenol [2] and erythrinassinate B [4], two new compounds, an isoflavanone named sigmoidin J [1] and a coumestan derivative named sigmoidin K [3], have been isolated and characterized from the root bark of the Cameroonian medicinal plant Erythrina sigmoidea. Their structures have been established as 7, 4'-dihydroxy-2',5'-dimethoxy-6'(gamma, gamma-dimethylally)isoflavanone [1] and 3,9-dihydroxy-2,10-(gamma, gamma dimethylallyl) coumestan [3], respectively, by spectroscopic techniques and from chemical evidence.
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Two flavones, 4',5,7-trihydroxy-6-methoxy flavone (dinatin) and 4',5-dihydroxy-6, 7-dimethoxy flavone (skrofulein), were extracted from Artemisia herba alba L. Dinatin and skrofulein inhibited the binding of [methyl-3H]diazepam to rat brain membranes in vitro with IC50 of 1.3 and 23 mumol.L-1, respectively. The GABA-ratios (the ratio of IC50 values in the absence/presence of GABA in the binding assay) were 1.1 and 1.2 for dinatin and skrofulein, respectively. Both flavones induced a slight increase in [35S] TBPS binding. The data suggest that the flavones are antagonists or partial agonists of benzodiazepine receptors.
Ethanolic extracts from dried leaves of sage (Salvia officinalis) showed inhibition of [35S]tertiary-butylbicyclophosphorothionate ([35S]TBPS) binding to rat brain membranes in vitro. This ligand is considered to bind to the chloride channel of the GABA/benzodiazepine receptor complex in brain tissue. Substances having inhibitory activity were purified and their chemical structure identified as the diterpenes carnosic acid and carnosol (IC50 values of 33 +/- 3 microM and 57 +/- 4 microM, respectively). The two compounds did not affect binding of the ligands [3H]muscimol and [3H]diazepam to the GABA/benzodiazepine complex in vitro. Saturation experiments of [35S]TBPS binding indicated that carnosic acid decreases the binding affinity.