The synthesis and antitumour and antibacterial activity of coumarin and chromone phosphorohydrazones have been reported. This study describes influence of phosphorohydrazones derivatives of coumarin and chromone on the polymerization and viscosity of fibrin. The fibrin polymerization assay was performed by the Shen and Lorand method and the clot viscosity was measured on the basis of Shen and Lorand and Marchi and coworkers methods. Among the eight compounds tested, one coumarin derivative and two chromone derivatives showed significant activity
Field bindweed (Convolvulus arvensis L.) has an impressive array of survival techniques, due to which it has become one of the worst weeds. This persistent field darnel is native to Eurasia but has spread to many parts of the world. TLC and HPLC were applied to carry out qualitative and quantitative determination of polyphenols compounds in bindweed, such as coumarins and phenolic acids: free and liberated by acid and alkaline hydrolysis. We identified and confirmed umbelliferone and scopoletin in the coumaries fraction. In the fraction of phenolic acids we noticed the occurrence of protocatechuic, caffeic, chlorogenic, gentisic, p-coumaric, p-hydroxybenzoic, p-hydroxyphenylo- acetic, ferulic, vanillic and salicylic. The caffeic (31.24 mg%), vanillic (5.8 mg%) and protocatechuic (4.62 mg%) acids were found to be the dominant compounds in the analysed plant.
Coumarins are very common biologically active compounds that have been found in numerous species of the family Apiaceae. The biological and pharmacological activity of these substances has very interesting properties. Coumarins also play a major role in the plant defence system. The quality and quantity of furano- and piranocoumarins is important for a defensive role in a plant as these compounds form a barier between the environment and plant organs. In order to study the plant defence mechanism it is necessary to carry out a qualitative and quantitative analysis of both furano- and pyranocoumarins. In this paper the studies on the optimum extraction and their influence on the yield of furano- and pyranocoumarins from fruits of the species Peucedanum verticillare are reported. The coumarins were analysed quantitatively by a combined method of SPE and RP-HPLC.
Typical chromatographic methods were successfully applied to isolate nine flavonoid compounds and two coumarin glycosides from the inflorescences and the herb of Hieracium pilosella L. Repeated column chromatography, occasionally paper chromatography and recrystallization made the separation of three flavonoid aglycones and six glycosides - possible. Coumarin glycosides were isolated by preparative thin layer chromatography. Subsequent UV, NMR and MS analyses have led to identification of the following flavonoid derivatives: known for the species - apigenin, luteolin, luteolin 7-O- ß-glucopyranoside, luteolin 4’-O-ß-glucopyranoside, isoetin 7-O-ß- -glucopyranoside, isoetin 4’-O-ß-glucuronide and new for the species – kaempferol 3-methyl ether and apigenin 7-O-ß-glucopyranoside. Third isoetin glycoside contained two different sugar moieties: xylose and glucose, probably attached to the hydroxyl groups at C-4’ or C-4’ and C-2’(or 5’) of an aglycone. Umbelliferone 7-O-ß-glucopyranoside (skimmin) and new for the genus Hieracium esculetin 7-O-ß-glucopyranoside (cichoriin) were determined by NMR and MS methods.
Our studies show the influence of coumarins: xanthotoxin and o,o-dimethyl-fraxetin on apoptosis in human peripheral blood lymphocytes in vitro. Lymphocytes (derived by ethical protocol) were cultured for 72 h in vivo. The cell cultures were stimulated with xanthotoxin or o,o-dimethyl-fraxetin in various concentrations. Apoptotic cells (compaction and margination of nuclear chromatin, cytoplasmic condensation, membrane blebbing and cell shrinkage) were observed in BX41 fluorescent Olympus microscope and recorded by MultiScan software. We observed the highest induction of apoptosis in cells stimulated with xanthotoxin in doses ≥50 μM in 48-hrs-cultures.
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Using the whole-cell patch-clamp technique, the influence of selected multidrug resistance modulators, both plant-derived compounds and derivatives on the activity of voltage-gated potassium channels Kv1.3 was investigated. Twelve compounds with phenolic and terpenic structures were tested: the stilbenes piceatannol (1) and its tetramethoxy (2) and tetracetoxy (3) derivatives, the flavonoids naringenin (4) and its methylated derivatives: naringenin-4',7-dimethylether (5) and naringenin-7-methylether (6), and aromadendrin (7), the coumarins esculetin (8) and scopoletin (9) and ent-abietane diterpenes, helioscopinolide B (10) and its 3ß-acetoxy derivative (11) and helioscopinolide E (12). The studies were performed on a model system with Kv1.3 channels endogenously expressed in human T lymphocytes. Obtained data provide evidence that compounds 2, 5 and 6 applied at 30 µM inhibited the amplitude of recorded currents to 31%, 4% and 29% of its control value, respectively. On the other hand, compounds 3, 4, 7-12 (at 30 µM) and compound 1 (at 40 µM) did not affect significantly the channel activity. These results indicate that some methoxy-derivatives of the tested compounds are effective inhibitors of Kv1.3 channels. Since the inhibition of Kv1.3 channels may inhibit the proliferation of prostate, breast and colon cancer cells expressing these channels, the channel inhibitors may exert an antiproliferative action. This action combined with a simultaneous modulation of the multidrug resistance may be significant for a potential application of these compounds in cancer chemotherapy.
The present investigation was conducted during two successive seasons of 2004/2005 and 2005/2006 in order to study the effect of two different sowing times and two macro- and microfoliar fertilizers on yield and chemical composition of Ruta graveolens plants. Delay in sowing from 20 October to 20 November resulted in significant promotion for herb dry weight (g/m2) as well as percentage and yield of essential oil of herb. In contrast, the accumulation of rutin and coumarin contents was higher at the first sowing time than the second one. The main constituent of essential oil in herb was identified as 2-undecanone. It represented 60.74% of identified herb essential oil at first sowing date and decreased to 55.88% at second date. Both foliar fertilizers, Crestalon and Leaf drip, promoted herb dry weight. Leaf drip was more favorable to improve these criteria than Crestalon. In general, the highest content of essential oil, rutin and coumarin were recorded with application of 1000 or 2000 ppm of Leaf drip. The maximum yield of herb and essential oil resulted in plants of the second date of sowing and fertilized with Leaf drip at 2000 ppm.
Southern sweet-grass is a perennial grass distributed through north-eastern Europe. In Poland, this rare, partially protected plant grows wild in well-lit coniferous or mixed forests. Its leaves, rich in coumarin compounds, are used for aromatization of alcohols. Taking into account high demand on this raw material and decrease in the number of southern sweetgrass populations it is recommended to introduce the plant into cultivation systems. In this study 12 populations of southern sweet-grass were selected and assessed in terms of their cultivation usefulness. The presence of associated plant species growing on its natural sites was investigated as well as light irradiance on those stands. The species was found in 3 types of forest communities. Air dry mass of leaves per plant varied in analyzed populations from 1.73 to 11.07 g. They were significantly diversified in the total content of coumarins (0.36–0.96%), flavonoids (0.09–0.26%) and polyphenolic acids (0.13–0.29%). The diversity concerning the content of coumarin, a quality indicator of leaves, was even higher. The content of this compound varied from 52.03 to 275.74 mg/100 g d. m. Among the analyzed populations, the most interesting seem to be population No. 12 (Jedwabno) and population No. 10 (Ruciane) characterized with relatively high mass of leaves and the highest content of the identified active compounds, including coumarin.
Acute pancreatitis (AP) is the most common gastrointestinal disease leading to hospitalizations and unexpected deaths. The development of AP leads to damage of the pancreatic microcirculation with a cascade of subsequent events resulting, among others, in coagulopathy. Previous research showed that anticoagulants can be important therapeutic agents. Heparin and acenocoumarol can alleviate the course of AP, as well as accelerate healing and post-inflammatory regeneration of the pancreas. The aim of this study was to determine whether warfarin, a drug with more stable effects than acenocoumarol, affects the healing and regeneration of the pancreas in the cerulein-induced AP. AP was evoked in Wistar male rats by intraperitoneal administration of cerulein. The first dose of warfarin (45, 90 or 180 µg/kg) was administered 24 hours after the first dose of cerulein and the doses of warfarin were repeated once a day in subsequent 10 days. The severity of AP was assessed immediately after the last dose of cerulein, as well as at days 1, 2, 3, 5, and 10 after AP induction. Treatment with warfarin dose-dependently increased international normalized ratio (INR) and attenuated the severity of pancreatitis in histological examination and accelerated pancreatic recovery. These effects were accompanied with a faster reduction in the AP-evoked increase in serum activity of amylase and lipase, the serum concentration of pro-inflammatory interleukin-1β, and the plasma level of D-Dimer. In addition, treatment with warfarin decreased pancreatic weight (an index of pancreatic edema) and improved pancreatic blood flow in rats with AP. The therapeutic effect was particularly pronounced after the administration of warfarin at a dose of 90 µg/kg. We conclude that treatment with warfarin accelerated regeneration of the pancreas and recovery in the course of cerulein-induced mild-edematous acute pancreatitis.