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A new coumarin glucoside, 3'(S)-hydroxy-2',2'-dimethyl-dihydropyranocoumarin-8-beta-d-glucopyranosyl, one coumarin, five furanocoumarins, three bicoumarins, three quinoline alkaloids and one sinapoyl sucrose derivative have been isolated from the roots of Ruta corsica.
Heparin and coumarin (Marcumar) as well as coumarin combined with a diphosphonate (EHDP) were examined histologically and histochemically with regard to their effect on the structure of the epiphyseal cartilage in rats. Topo-optical reactions were used to assess the submicroscopic structural changes in the developing trabeculae of metaphysis. The zone of resting cartilage and the zone of young proliferation cartilage in epiphyseal plates revealed a reduced cell count due to the influence of anticoagulants. With regard to the matrix of the epiphyseal plate, it may be stated that its ultrastructure appeared partly regular and that, on the other hand, large areas of degeneration were detected in the connective-tissue. The negative effect of anticoagulants on the ground substance could not be reduced definitely by means of a diphosphonate (EHDP) in conjunction with Marcumar which was administered simultaneously.
It is well known that toddalolactone (1) is a main component of Toddalia asiatica (L.) Lam. (T. aculeata Pers.) (Rutaceae). However, supercritical fluid (SCF) extraction of the plant by using CO2 showed that a main component of the extract was not 1, but aculeatin (2), a coumarin having an epoxy ring on the side chain. The same result was obtained from Soxhlet extraction by using aprotic solvents. On the other hand, Soxhlet extraction by using methanol yielded 13, corresponding to a methanol adduct of 2, as an additional component, which was able to be also produced in 50.2% yield only by heating pure 2 in methanol, indicating that the epoxy ring in 2 can be easily attacked by a weak nucleophile like methanol. These facts strongly suggested that 1, corresponding to the hydrate of 2, was an artefact derived from 2 during extraction. SCF extraction under various conditions was examined in detail by quantitative analyses of 1 and 2 by high performance liquid chromatography and the optimum condition extracting the both components was found to be at 40 degrees C and at 300 kg/cm2. The condition was applied to the plant treated with aqueous sodium hydrogen carbonate in order to remove any acidic substances and 1 was still detected in the extract. Thus, it is conclude that 1 should be a genuine natural coumarin but that previous isolation of 1 as a main component resulted in an isolation of an artefact derived from 2. SCF extraction was suggested to be a useful extraction method.
Blood concentration-time data of coumarin (C), 7-hydroxycoumarin (7-HC) and 7-hydroxycoumarin glucuronide (7-HCG) were obtained in rats receiving intraperitoneal doses of C ranging from 2.5 to 60 mg/kg and of 7-HC ranging from 2.5 to 20 mg/kg. Coumarin blood levels were fit to pharmacokinetic models using computer programs including NONLIN, modified ESTRIP, RESID and AUCRPP. The other molecular species were treated pharmacokinetically by linear least squares regression analysis. C blood concentrations were indicated to be dose-dependent at doses greater than 10 mg/kg. Only trace amounts of 7-HC were found upon C administration, however, 7-HCG was found in measurable quantities at all dose levels. The blood concentration-time data of 7-HC and 7-HCG were very erratic with considerable intersubject variation. 7-HC levels upon 7-HC dosing were found to have extremely short half-lives of elimination for all animals tested. Deviation from linearity was apparent at the 20 mg/kg dose for 7-HC. The 7-HCG metabolite upon 7-HC dosing also showed dose-dependent kinetics at the 20 mg/kg dose. 7-HCG was found to appear at variable rates in the blood with peak times ranging from about 2 to 50 min.
The interaction of ionic liquid with water in 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6])/Triton X-100 (TX-100)/H2O ternary microemulsions, i.e., "[bmim][PF6]-in-water" microregions of the microemulsions, has been studied by the dynamics of solvent and rotational relaxation of coumarin 153 (C-153) and coumarin 151 (C-151). The variation of the time constants of solvent relaxation of C-153 is very small with an increase in the [bmim][PF6]/TX-100 ratio (R). The rotational relaxation time of C-153 also remains unchanged in all micremulsions of different R values. The invariance of solvation and rotational relaxation times of C-153 indicates that the position of C-153 remains unaltered with an increase in R and probably the probe is located at the interfacial region of [bmim][PF6] and TX-100 in the microemulsions. On the other hand, in the case of C-151, with an increase in R the fast component of the solvation time gradually increases and the slow component gradually decreases, although the change in solvation time is small in comparison to that of microemulsions containing common polar solvents such as water, methanol, acetonitrile, etc. The rotational relaxation time of C-151 increases with an increase in R. This indicates that with an increase in the [bmim][PF6] content the number of C-151 molecules in the core of the microemulsions gradually increases. In general, the solvent relaxation time is retarded in this room temperature ionic liquid/water-containing microemulsion compared to that of a neat solvent, although retardation is very small compared to that of the solvent relaxation time of the conventional solvent in the core of the microemulsions.
The sensory capabilities of two novel di(2-picolyl)amine (DPA)-substituted coumarins are described and it is shown that the variation of the point of attachment of the DPA group to the coumarin framework controls their sensing behavior: the 4-substituted system is a CHEF-type sensor that shows a significant increase in fluorescence intensity upon Zn(2+) binding, whereas the 3-substituted system is a ratiometric sensor.
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