Theobromine

About: Theobromine is a research topic. Over the lifetime, 1137 publications have been published within this topic receiving 29723 citations. The topic is also known as: 3,7-Dimethylxanthine & Theobromin.

Synthesis and anticancer activity of silver(I)-N-heterocyclic carbene complexes derived from the natural xanthine products caffeine, theophylline and theobromine.

Abstract: A new library of silver(I)-N-heterocyclic carbene complexes prepared from the natural products caffeine, theophylline and theobromine is reported. The complexes have been fully characterised using a combination of NMR spectroscopy, mass spectrometry, elemental analysis and X-ray diffraction analysis. Furthermore, the hydrophobicity of the complexes has been measured. The silver(I)-N-heterocyclic carbenes have been evaluated for their antiproliferative properties against a range of cancer cell lines of different histological types, and compared to cisplatin. The data shows different profiles of response when compared to cisplatin in the same panel of cells, indicating a different mechanism of action. Furthermore, it appears that the steric effect of the ligand and the hydrophobicity of the complex both play a role in the chemosensitivity of these compounds, with greater steric bulk and greater hydrophilicity delivering higher cytotoxicity.

Long‐term Treatment with some Methylxanthines Decreases the Susceptibility to Bicuculline‐ and Pentylenetetrazol‐induced Seizures in Mice. Relationship to c‐ios Expression and Receptor Binding

Abstract: The effects of long-term oral administration of low doses of caffeine (0.3 g/l) and its metabolites theophylline, theobromine and paraxanthine (each at 0.5 g/l in drinking water) on bicuculline- and pentylenetetrazol (PTZ) -induced seizures and c-fos expression were studied in mice. In addition, adenosine and benzodiazepine receptor density was examined. The plasma levels of the methylxanthines were much higher during the active period at night than during the day. The maximal level of caffeine was 14 μM. Brain theophylline levels (8-13 nmol/g) tended to be higher and more constant than brain caffeine levels in caffeine-consuming mice. Clonic seizures induced by bicuculline (4 mg/kg i.p.) were significantly reduced in severity by 14 day caffeine treatment and mortality was also reduced. Long-term treatment with caffeine metabolites was less effective. The seizures induced by PTZ (60 mg/kg i.p.) were also significantly reduced by long-term caffeine treatment. After bicuculline or PTZ treatment, c-fos mRNA expression was weaker in the cerebral cortex in animals receiving caffeine, irrespective of whether the animals had seizures or not. No significant changes in the binding of adenosine receptor ligands or benzodiazepines were seen after long-term caffeine treatment. These results show that long-term treatment with caffeine in a dose that is commonly seen in humans decreases the seizures induced by bicuculline, and to a lesser extent, those induced by PTZ. This may be related to a decreased neuronal excitability. The effect is due to the combined effects of theophylline, to which caffeine is metabolized in brain, and of caffeine itself, but could not be ascribed to changes in A1 and A2A adenosine or benzodiazepine receptors.

Degradation of caffeine and related methylxanthines by Serratia marcescens isolated from soil under coffee cultivation

Abstract: A strain of Serratia marcescens showing the ability to degrade caffeine and other methylxanthines was isolated from soil under coffee cultivation. Growth was observed only with xanthines methylated at the 7 position (caffeine, 1,3,7-dimethylxanthine; paraxanthine, 1,7-dimethylxanthine; theobromine, 3,7-dimethylxanthine and 7-methylxanthine). Paraxanthine and theobromine were released in liquid medium when caffeine was used as the sole source of carbon and nitrogen. When paraxanthine or theobromine were used, 3-methylxanthine, 7-methylxanthine, and xanthine were detected in the liquid medium. Serratia marcescens did not grow with theophylline (1,3-dimethylxanthine), 1-methylxanthine, and 3-methylxanthine, and poor growth was observed with xanthine. Methyluric acid formation from methylxanthines was tested in cell-free extracts by measuring dehydrogenase reduction of tetrazolium salt in native-polyacrylamide gel electrophoresis gel. Activity was observed for all methylxanthines, even those with which no bacterial growth was observed. Our results suggest that in this strain of S. marcescens caffeine is degraded to theobromine (3,7-dimethylxanthine) and/or paraxanthine (1,7-dimethylxanthine), and subsequently to 7-methylxanthine and xanthine. Methyluric acid formation could not be confirmed.