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Vasorelaxant effect of stilbenes from rhizome extract of rhubarb (Rheum undulatum) on the contractility of rat aorta.

The vascular relaxant effect of the rhizome extract of Rheum undulatum was evaluated with isolated rat thoracic aorta preparations. The methanol extract of the rhizome induced a concentration-dependent relaxation of aortic preparations precontracted with 0.3 microm phenylephrine (EC50 value: 5.8 microg/mL). The activity-guided fractionation of the extract led to the isolation of seven hydroxystilbene components as active principles, i.e. piceatannol, resveratrol, desoxyrhapontigenin, rhapontigenin, piceid, rhaponticin and epsilon-viniferin. Of these, piceatannol, a tetrahydroxystilbene, exhibited the most potent vascular relaxant effect in rat aortic preparations (EC50 value 2.4 microm). The vasorelaxant effect of piceatannol on endothelium-intact aorta rings was diminished completely by the removal of functional endothelium or by pretreatment of the aortic tissues with N(G)-nitro-l-arginine methyl ester. These results suggest that piceatannol may be the major mediator responsible for the vasorelaxing properties of the rhizome extract of Rheum undulatum and the vasorelaxant effects of the piceatannol may be mediated via endothelium-dependent nitric oxide signaling pathway.

Animals↗

Small-conductance chloride channels induced by cAMP, Ca2+, and hypotonicity in HT29 cells: ion selectivity, additivity and stilbene sensitivity.

Previous studies in HT29 cells utilizing the cell-attached nystatin (CAN) method [Greger R, Kunzelmann K (1991) Pflügers Arch 419:209-211] have revealed that the Cl- channels induced by cAMP or by increasing cytosolic Ca2+, e.g. by addition of ATP, and by hypotonic cell swelling share in common their conductance, which was so small in our studies [Kunzelmann et al. (1992) Pflügers Arch (in press)] that we could not resolve it at the single-channel level. This prompted the question whether these Cl- conductances can be distinguished in terms of their ion selectivity and sensitivity towards inhibitors. Whether these pathways are additive or not was also examined. The present study utilized the whole-cell patch-clamp and the CAN methods. A total of 160 patches were studied. In whole-cell patches 8-(4-chlorophenylthio)-cAMP (cAMP, 0.1 +/- 1 mmol/l) induced a significant depolarization by 5 mV and a twofold increase in conductance (G) from 6.2 +/- 1.5 nS to 11.7 +/- 3.2 nS (n = 15). Total replacement of Cl- by Br- and I- in cAMP-treated cells hyperpolarized the membrane voltage (V) significantly from -35 +/- 2.8 to -39 +/- 3.4 and -45 +/- 3.3 mV respectively, but had no detectable effect on G, which was 11.9 +/- 3.3 nS in the case of Br- and 11.8 +/- 3.3 nS in the case of I-. Hence, the permselectivity of the cAMP pathway was I- > Br- > Cl-, but the conductances for these anions were all indistinguishable.(ABSTRACT TRUNCATED AT 250 WORDS)

4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid↗

The mechanism of alloxan toxicity: an indication for alloxan complexes in tissues and alloxan inhibition of 4-acetamido-4'-isothiocyanato-stilbene-2,2'-disulphonic acid (SITS) binding for the liver cell membrane.

It is shown that alloxan inhibits binding of SITS to liver cells. This indicates the cell membrane as a site of alloxan action. Alloxan is found to react with tissues to form complexes that are detectable up to 3 hrs after alloxan treatment. On the basis of the present findings, an assumption is made that alloxan inhibits a cell membrane processes by blockade of functionally importnat groups.

Alloxan↗

Synthesis of tritiated 4,4'-diisothiocyano-2,2'-stilbene disulfonic acid ([3H]DIDS) and its covalent reaction with sites related to anion transport in human red blood cells.

The potent and specific inhibitor of anion permeability, 4,4'-diisothicyanostilbene-2,2'-disulfonic acid (DIDS) was synthesized in tritiated form ([3H]DIDS) from tritiated 5-nitrotoluene-o-sulfonic acid. Its reactions with and effects on red blood cells were compared with those of a reduced form ([3H]H2DIDS), previously used as a tracer for DIDS. The rate of covalent reaction of [3H]DIDS was substantially faster than that of [3H]H2DIDS at all temperatures tested. With both agents, the rate of reaction was increased in alkaline media, although the response occurred at a lower pH with [3H]DIDS. On the other hand, the relationship of irreversible membrane binding to the degree of inhibition of sulfate fluxes was linear and virtually the same for both agents, with 100% inhibition associated with the binding of approximately 1.2 X 10(6) molecules per cell. About 90% of the binding for each probe was to a particular membrane protein, known as band 3, equivalent to about 1 mole of agent per mole of protein.

Anions↗

Stilbene-like molecules as fluorescent probes applied for monitoring of polymerization process.

2-(p-N,N-dimethylaminostyryl)benzoxazole (OS), 2-(p-N,N-dimethylaminostyryl)-benzothiazole (SS) and 2-(p-N,N-dimethylaminostyryl)naphtiazole (PS) were prepared and their absorption and fluorescence spectra were measured in various solvents at room temperature. On the basis of the solvatochromic behavior the ground state (mu(g)) and excited state (mu(e)) dipole moments of these pN,N-dimethylaminostyryl derivatives were evaluated. The dipole moments (mu(g) and mu(e)) were estimated from solvatochromic shifts of absorption and fluorescence spectra as function of the dielectric constant (epsilon) and refractive index (n) of applied solvents. The absorption spectra only slightly are affected by the solvent polarity in contrast to the fluorescence spectra that are highly solvatochromic and display a large Stokes shift. The analysis of the solvatochromic behavior of the fluorescence spectra as function of Deltaf (epsilon, n) revealed that the emission occurs from a high polarity excited state. The large dipole moment change along with the strongly red-shifted fluorescence, as the solvent polarity is increased, demonstrate the formation of an intramolecular charge transfer state (ICT). Compounds under the study were used as fluorescence probes for monitoring the kinetics of polymerization. The study on the changes in fluorescence intensity and spectroscopic shifts of studied compounds were carried out during thermally initiated polymerization of methyl methacrylate (MMA) and during photoinitiated polymerization of 2-ethyl-2-(hydroxymethyl)propane-1,3-diol triacrylate (TMPTA).

Acrylates↗