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PubMed1990

Immunochemical detection of glycosphingolipids on thin-layer chromatograms.

A sensitive immunochemical method was developed for the detection of glycosphingolipids on thin-layer chromatograms. The procedure involves oxidation of diol groups of glycosphingolipids with sodium periodate, derivatization of the formed aldehyde groups with digoxigenin-hydrazide, and reaction of the bound digoxigenin with an alkaline phosphatase-labeled polyclonal anti-digoxigenin antibody. The latter is detected by an insoluble indigo-like dye as a result of dephosphorylation of 5-bromo-4-chloro-3-indolyl phosphate. The detectability of all glycosphingolipid species was improved over that of the orcinol and resorcinol staining methods. Two nanograms of the standard gangliosides GM1, GD1A, and GT1 was detected, whereas the detection limit for short-chain neutral glycosphingolipids was in the range of 20-50 ng. Long-chain glycosphingolipids were detectable with a particularly high sensitivity. Selective staining of the gangliosides could be achieved by the use of low periodate concentrations.

Antibodies↗
PubMed1994

Formaldehyde-free collagen glue in experimental lung gluing.

Because of the well-known limitations of the adhesive strength of fibrin glue, it is imperative to develop a stronger glue with acceptable biocompatibility. This was accomplished by removing the formaldehyde component from gelatin-resorcinol-formaldehyde glue and replacing it by two less toxic aldehydes--pentanedial and ethanedial. To evaluate the adhesive strength of this new glue, GR-DIAL, lung incisions in rabbit hybrids were glued together. Each group (n = 5) was examined histologically after 2 days and 1, 2, and 4 weeks. The glue disintegrated gradually with good bioresorption when the incision was closed with a thin layer of glue. The healing process was favorable, indicating good biocompatibility. Therefore, GR-DIAL glue is capable of enhancing the use of surgical glues in the field of thoracic surgery by enabling surgeons to close larger parenchymal lesions than with fibrin glue.

Animals↗
PubMed1995

Comparative study of biological glues: cryoprecipitate glue, two-component fibrin sealant, and "French" glue.

BACKGROUND: Although biological glues have been used clinically in cardiovascular operations, there are no comprehensive comparative studies to help clinicians select one glue over another. In this study we determined the efficacy in controlling suture line and surface bleeding and the biophysical properties of cryoprecipitate glue, two-component fibrin sealant, and "French" glue containing gelatin-resorcinol-formaldehyde-glutaraldehyde (GRFG). METHODS: Twenty-four dogs underwent a standardized atriotomy and aortotomy; the incisions were closed with interrupted 3-0 polypropylene sutures placed 3 mm apart. All dogs had a 3- by 3-cm area of the anterior wall of the right ventricle abraded until bleeding occurred. The animals were randomly allocated into four groups: in group 1 (n = 6) bleeding from the suture lines and from the epicardium was treated with cryoprecipitate glue; in group 2 (n = 6) bleeding was treated with two-component fibrin sealant; group 3 (n = 6) was treated with GRFG glue; group 4 (n = 6) was the untreated control group. The glues were also evaluated with regard to histomorphology, tensile strength, and virology. RESULTS: The cryoprecipitate glue and the two-component fibrin sealant glue were equally effective in controlling bleeding from the aortic and atrial suture lines. Although the GRFG glue slowed bleeding significantly at both sites compared to baseline, it did not provide total control. The control group required additional sutures to control bleeding. The cryoprecipitate glue and the two-component fibrin sealant provided a satisfactory clot in 3 to 4 seconds on the epicardium, whereas the GRFG glue generated a poor clot. There were minimal adhesions in the subpericardial space in the cryoprecipitate and the two-component fibrin sealant groups, whereas moderate-to-dense adhesions were present in the GRFG glue group at 6 weeks. The two-component fibrin sealant was completely reabsorbed by 10 days, but cryoprecipitate and GRFG glues were still present. On histologic examination, both fibrin glues exhibited minimal tissue reaction; in contrast, extensive fibroblastic proliferation was caused by the GRFG glue. The two-component and GRFG glues had outstanding adhesive property; in contrast, the cryoprecipitate glue did not show any adhesive power. The GRFG glue had a significantly greater tensile strength than the two-component fibrin sealant. Random samples from both cryoprecipitate and the two-component fibrin glue were free of hepatitis and retrovirus. CONCLUSIONS: The GRFG glue should be used as a tissue reinforcer; the two-component fibrin sealer is preferable when hemostatic action must be accompanied with mechanical barrier; and finally, the cryoprecipitate glue can be used when hemostatic action is the only requirement.

Animals↗
PubMed1991

Hypochlorous acid-induced mobilization of zinc from metalloproteins.

Hypochlorous acid (HOCl), a neutrophil oxidant, can contribute to tissue injury at sites of inflammation by its reactivity with protein sulfhydryls. The present study shows that physiological concentrations (50-200 microM) of HOCl can displace Zn2+ from metalloproteins, such as metallothionein and alcohol dehydrogenase, in which the metal is bound to sulfhydryls by means of thiolate (S-Zn) bonds. No mobilization of Zn2+ was observed from superoxide dismutase in which the metal is not bound to cysteine, suggesting that HOCl reacts selectively with thiolate bonds. Zn2+ mobilization, measured spectrophotometrically with the metallochromic indicator 4-(2-pyridylazo)resorcinol, was also observed from complexes of this metal with other thiol-containing compounds such as 2,3-dimercaptopropanol and metallothionein fragment 56-61. HOCl cleavage of the thiolate bonds was confirmed by the decrease in absorbance at 250 nm. This study shows for the first time that HOCl can mobilize protein-bound Zn2+ and suggests that neutrophil oxidant injury may be partially mediated by the mobilization of cellular Zn2+.

Amino Acid Sequence↗
PubMed1988

The effect of nonadec(en)ylresorcinol on the fluidity of liposome and erythrocyte membranes.

The effect of alk(en)ylresorcinol homologs (5-(n-nonadecyl)- and 5-(n-nonadecenyl)resorcinol) on the mobility of 5-doxyl- and 12-doxylstearate spin probes incorporated into DMPC, DMPC-cholesterol and erythrocyte membranes was studied. It was found that both homologs affect the properties of hydrophobic environment of the membranes: (1) In DMPC vesicles both homologs induce an increase in the order parameter of 5-doxylstearate at temperatures of Tc and above. (2) At higher concentrations of both homologs a decrease in mobility of the 12-doxylstearate was also observed. (3) In the presence of cholesterol in the liposome membrane the influence of alk(en)ylresorcinols on the mobility of spin probes was much greater, depending on the cholesterol content and the position of the probe in the bilayer. (4) In natural membranes (erythrocyte ghosts) both alkyl- and alkenylresorcinols induced a decrease of mobility in the region of 12-doxylstearate as well as in the region closer to the polar head groups of lipids (5-doxylstearate).

Cholesterol↗
PubMed1987

Mechanism of antitumoral activity of catechols in culture.

Cell lines Raji and K 562, lacking tyrosinase, and two melanotic human melanoma cell lines (IRE 1 and IRE 2), were exposed to concentrations from 5 X 10(-3) M to 10(-5) M of different phenols which are substrates of tyrosinase, i.e. l-dopa, dopamine, hydroquinone, terbutylcatechol, and of phenols which are not substrates of the tyrosinase, i.e. resorcinol, butylated hydroxyanisole and hydroquinone dimethyl ether. Cultures were carried out in the presence or in the absence of oxygen radical scavenger enzymes superoxide dismutase, catalase and peroxidase. The stability of each substance in culture medium was assayed by high performance liquid chromatography (HPLC). Results showed that: catechols which are substrates of tyrosinase decompose fully after 24 hr in medium; they are equally toxic for melanoma and non-melanoma cell lines; their toxicity increases when they are preincubated in medium for 24 hr and 48 hr before addition of cells; their toxicity is significantly reduced by addition of scavenger enzymes; on the contrary, phenols not substrates of tyrosinase are stable in medium and their toxicity is not reduced by scavenger enzymes. It is concluded that tyrosinase does not play a major role in catechol toxicity in vitro, which is probably due to some products of catechol decomposition, especially oxygen radicals, acting outside the cells.

Anisoles↗
PubMed1977

Aspects of the spasmogenic effects of acetate esters on ileal smooth muscle.

Acetate esters, such as aspirin methylester, aspirin and resorcinol monoacetate, induced contractions of guinea-pig ileum. Their actions were selectively antagonized by atropine, but were not affected by ganglion blocking agents, conduction blockers, aging with cooling, anoxia or antihistaminics. On the other hand, N-acetates, such as acetanilide and p-acetaminophenol, and no contractile action on the ileum. These acetate esters thus seemed to have a cholinergic action, and not a direct action on muscle or other known specific receptors for endogenous active substances. The contractions induced by the acetate esters were selectively potentiated by low concentrations of choline, whereas those induced by acetylcholine, nicotine, 5-hydroxytryptamine and histamine were not. However, N-acetates did not induce the contractions even in the presence of choline. Organophosphorus cholinesterase inhibitors, such as diisopropyl fluorophosphate and paraoxon, selectively and irreversibly inhibited the actions of aspirin and N,O-diacetyl-p-aminophenol with or without choline. From these results, it is concluded that the acetate esters with or without choline act through the cholinergic system. However, their actions cannot be explained in terms of known mechanisms, such as acetylcholine release, cholinesterase inhibition or a direct muscarinic action. Therefore, the acetate esters, including phenyl acetate which was supposed to be a releaser of acetylcholine, seem to have a hitherto undescribed type of cholinergic action whose mechanism is unknown. It seems that organophosphate-sensitive esterase(s) in the preparation may be essential for initiation of the actions of the acetate esters with or without choline, but the mechanism of the effect of choline is unknown.

Acetates↗
PubMed1995

Easy and inexpensive diffusion tests for detecting the assimilation of aromatic compounds by yeast-like fungi. Part I. Assimilation of dihydroxyphenols.

A number of easy and inexpensive diffusion tests have been proposed to find microorganisms that are able to decompose aromatic compounds. These tests made it possible to show the assimilation of catechol, resorcinol and hydroquinone by selected yeast-like fungi. The tests may be used to choose highly active strains from culture collections.

Candida↗
PubMed1992

Humic acid: inhibitor of plasmin.

Synthetic humic acid, well water humic acid and commercial humic acid (Aldrich) all have the ability to inhibit human plasmin activity. At a concentration of 20 micrograms/ml, all three species will result in 93%, 70% and 40% of residual plasmin activity, respectively. The components of humic acid, such as protocatechuic acid, resorcinol, vanillic acid and ferulic acid do not have such inhibitory activities. The ability of humic acid to inhibit human plasmin has not been reported. It is, therefore, a new plasmin inhibitor.

Coumaric Acids↗
PubMed1996

Transcriptional regulation of the human NAD(P)H:quinone oxidoreductase (NQO1) gene by monofunctional inducers.

The upstream region of the human NAD(P)H:quinone oxidoreductase (NQO1) gene contains a functional antioxidant responsive element (ARE) and an overlapping 12-O-tetradecanoyl-phorbol-13-acetate responsive element (TRE), with the sequence TGACTCAGCA. We show that the ARE (TGACNNNGCA) is required for induction by redox cycling phenolics (p-benzoquinone, catechol and hydroquinone), which are monofunctional inducers and induce NQO1 without the requirement for activation by cytochrome P-450. The TRE (TGACTCA) is involved only in basal expression. A plasmid containing overlapping ARE-TRE (TGACTCAGCA) sequences (-587 to -379) from the NAD(P)H:quinone oxidoreductase gene was transiently transfected into Hep G2 cells. In the absence of inducers, basal expression was 4-fold higher than in F9 cells (which lack AP-1 activity). Using subcloned oligonucleotides containing the ARE-TRE sequence (-473 to -440), the ARE sequence alone (TCA changed to GAC) and the TRE sequence alone (GC changed to TA), the basal level of expression was in the order: TRE > TRE-ARE > ARE in Hep G2 cells. Using F9 cells, basal expression was detected using the combination ARE-TRE sequence or the ARE, but not the TRE alone, p-Benzoquinone, catechol and hydroquinone, but not resorcinol, induced gene expression in both Hep G2 and F9 cells via the ARE-TRE and ARE sequences, but the TRE sequence did not contribute to this induction. We therefore conclude that induction of human NAD(P)H:quinone oxidoreductase by monofunctional inducers is via the ARE and not the TRE, and that the induction is mediated by proteins other than Fos and Jun.

Amino Acid Sequence↗
PubMed1991

Lack of modification by naturally occurring antioxidants of 3,2'-dimethyl-4-aminobiphenyl-initiated rat prostate carcinogenesis.

The modifying effects of 6 naturally occurring antioxidants on 3,2'-dimethyl-4-aminobiphenyl (DMAB)-initiated rat prostate carcinogenesis were investigated in male F344 rats. Animals were pretreated with DMAB in a 20-week initiation protocol and then administered basal diet containing 0.8% catechol, 0.8% resorcinol, 0.8% hydroquinone, 2 ppm selenium, 2% gamma-orysanol or 1% alpha-tocopherol for 40 weeks. The experiment was terminated at week 60 for histopathological assessment of lesion development. Atypical hyperplasias and carcinomas of the prostate were observed in the ventral lobe in all groups treated with DMAB. However, the incidences of these lesions were not significantly different between carcinogen control and antioxidant-treated groups. There were also no significant increases or decreases in the incidences of tumors in any other organs.

Aminobiphenyl Compounds↗
PubMed1992

Mechanisms of DNA damage induced in rat hepatocytes by quinones.

Hydroquinone (HQ), catechol (CAT), duroquinone (DQ) and resorcinol (RES) have been shown to induce single-strand breaks (SSB) in DNA in isolated hepatocytes using the alkaline elution assay. The relative capacities of these agents to induce SSB were shown to be: DQ = HQ much greater than CAT greater than RES. Preincubation of hepatocytes with the Ca(2+)-chelator Quin-2 AM reduced the level of DNA damage to a great extent, as did treatment with DQ and RES, and, to a lesser extent, treatment with HQ and CAT. Preincubation with an inhibitor of poly(ADP-ribose) polymerase, 3-amino-benzamide, did not influence the extent of DNA damage caused by DQ and RES, but increased the damage caused by HQ and CAT. The conclusion of the present investigation was that the dominating reaction of HQ and CAT, with DNA is an arylation, whereas DQ and RES induce DNA damage by oxidative stress.

Animals↗
PubMed1994

Efficient tissue gluing in aortic dissection.

The authors' method for uniting the dissected aortic wall layers with the help of gelatine-resorcinol adhesive is described focusing on special instruments used in this conjunction.

Aortic Dissection↗
PubMed2004

A high-performance liquid chromatography method for determining transition metal content in proteins.

Transition metals are common components of cellular proteins and the detailed study of metalloproteins necessitates the identification and quantification of bound metal ions. Screening for metals is also an informative step in the initial characterization of the numerous unknown and unclassified proteins now coming through the proteomic pipeline. We have developed a high-performance liquid chromatography method for the quantitative determination of the most prevalent biological transition metals: manganese, iron, cobalt, nickel, copper, and zinc. The method is accurate and simple and can be adapted for automated high-throughput studies. The metal analysis involves acid hydrolysis to release the metal ions into solution, followed by ion separation on a mixed-bead ion-exchange column and absorbance detection after postcolumn derivatization with the metallochromic indicator 4-(2-pyridylazo)resorcinol. The potential interferences by common components of protein solutions were investigated. The metal content of a variety of metalloproteins was analyzed and the data were compared to data obtained from inductively coupled plasma-atomic emission spectroscopy. The sensitivity of the assay allows for the detection of 0.1-0.8 nmol, depending on the metal. The amount of protein required is governed by the size of the protein and the fraction of protein with metal bound. For routine analysis 50 microg was used but for many proteins 10 microg would be sufficient. The advantages, disadvantages, and possible applications of this method are discussed.

Animals↗
PubMed2003

Biosynthesis of 5-alkylresorcinol in rice: incorporation of a putative fatty acid unit in the 5-alkylresorcinol carbon chain.

A previously unspecified "starter" unit in the predicted biosynthesis pathway of 5-alkylresorcinols has now identified as a fatty acid or its equivalent, using an efficient 5-alkylresorcinol production system of etiolated rice seedlings. Feeding saturated, odd-carbon fatty acid ester substrates from C11 to C19 specifically and markedly increased the amount of the corresponding 5-alkylresorcinol homologs with even-carbon chains that are shorter by one carbon than those of the supplied fatty acids. The amount of these homologs depended on substrate concentration. Some of the homologs whose amounts increased had linear carbon chains and the dodecyl homolog was shown to be 5-n-dodecylresorcinol. Moreover, the 13C label in the dodecyl homolog that was biosynthesized from the [1-13C]tridecanoate substrate was localized on the C-5 carbon of the resorcinol ring. These results obviously show that the fatty acid unit acts as a direct precursor and forms the side-chain moiety of 5-n-alkylresorcinol via the predicted biosynthesis pathway.

Alkylation↗
PubMed2004

A mechanistic study on the nuclease activities of some hydroxystilbenes.

The nuclease activities of a series of hydroxystilbeneoids have been studied so as to establish a structure-activity correlation and deduce the mechanistic pathway of the process. Although the test compounds could nick plasmid DNA, only three of these including resveratrol produced double strand breaks in DNA. Amongst these new stilbenes, compound 2e containing a partially methylated catechol and a C-4 hydroxy moieties was equally potent as resveratrol. The activities of the unprotected catechol-derivatives were less than those of the resorcinol-derivatives, which were, however, compensated by partial methylation of the former. The presence of Cu(2+) and O(2) and the participation of a Cu(+)-oxo intermediate were obligatory in the process which did not require addition of any external reducing agent. Overall, the differential nuclease activities of the compounds could be explained primarily with their superoxide anion generation abilities, and to a lesser extent with their DNA binding and Cu(2+) reducing capacities. The amount of superoxide anion produced by the compounds depended strongly on their Cu(+)-complexation abilities, which again, was decided by the pattern and nature of the oxygenated substituents in the aromatic rings.

Catechols↗
PubMed2005

Rapid separation of antimicrobial metabolites by microchip electrophoresis with UV linear imaging detection.

This research examines microchip electrophoresis with linear imaging UV detection for the analysis of antimicrobial metabolites, monoacetylphloroglucinol (MAPG) and 2,4-diacetylphloroglucinol (2,4-DAPG) from Pseudomonas fluorescens F113. Initial results show the separation of MAPG, 2,4-DAPG and resorcinol in less than 20 s. This was achieved using a quartz microchip with a separation channel length of 25 mm. In order to quantitate the amount of MAPG and 2,4-DAPG in a microbial cultured supernatant sample, on-chip sample introduction in a methanol/buffer matrix was investigated. Sample introduction/injection parameters were optimized to improve sensitivity and thus decrease the limit of detection (LOD). The amount of antimicrobial metabolites present was quantitated with a separation time of 15 s. A previously developed capillary electrophoretic method was compared to the microchip method in relation to speed, efficiency, precision, linear range and limit of detection. This investigation shows the fastest separation so far of these antimicrobial metabolites with high efficiency.

Electrophoresis, Microchip↗
PubMed2006

Homolog separation, a necessity for the proper identification of fungal metabolites.

Monitoring of fungal extracts for the production of novel metabolites, using a modular analytical system combining HPLC with UV-MS-ELS detection, identified culture LL-W1278 as a fungus producing new biopolymers. Only a non-routine HPLC analysis of a culture extract revealed that the standard water-acetonitrile elution method did not separate all members of the metabolite complex. Fine-tuning the eluting solvents established that it was essential to include acid with the water-methanol system to separate the new materials. The routinely used water-acetonitrile system, with or without acid, was incapable of separating all homologues. With the modified method the new homologues W1278-Ax, Bx, and Cx were separated. LC/MS analysis indicated that these compounds had molecular weights of 706, 900, and 1094, respectively, 44 mass units lower than their three major homologues, W1278-A, B, and C, identified previously. UV and NMR data as well as mass fragmentation patterns established unambiguously that the new compounds lacked a carboxyl group at the terminal resorcinol unit of the biopolymer, consisting of several catenated hydroxymellein residues. A time study concerning the stability of these fungal metabolites showed a slow, but complete degradation of the primary metabolites over several months when kept as a DMSO solution.

Ascomycota↗