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PubMed1986

Two modes of analgesic action of aspirin, and the site of analgesic action of salicylic acid.

The analgesic activities of aspirin and salicylic acid were investigated by means of the lame-walking test in adjuvant-induced hind-paw-oedematous rats. Aspirin showed ca. 4 times more potent analgesic activity than did salicylic acid in the lame-walking test. The analgesic activity of aspirin was decreased to the level of that of salicylic acid by injection of prostaglandin E2 into the inflamed tissue. The analgesic activity of salicylic acid was not decreased by the same treatment. Salicylic acid inhibited the lame-walking reaction when given intracerebroventricularly. On the other hand, salicylic acid did not inhibit the lame-walking reaction by topical administration on the inflamed hind paw. However, with topical administration, salicylic acid inhibited the carrageenin-induced hind-paw oedema. These results suggest that aspirin has two analgesic effects on the inflammatory pain; one may be the inhibition of prostaglandin biosynthesis by acetylation of cyclo-oxygenase, and the other may be an action due to salicylic acid. Salicylic acid may produce its analgesic action mainly via a central mechanism.

Analgesia↗
PubMed1991

Topical salicylic acid interferes with UVB therapy for psoriasis.

Salicylic acid has been widely used in the topical treatment of psoriasis. Chemically it is closely related to paraaminobenzoic acid. Following in vitro studies indicating that salicylic acid might exhibit relevant UVB absorption, we found that salicylic acid had a clinically pronounced filter effect when applied prior to UVB exposure. The duration of photoprotection after application was more than 12 h, sometimes exceeding 24 h. In a prospective, randomized, double-blind, left-right comparison study in patients with psoriasis between emollients with and without salicylic acid, salicylic acid was shown to decrease the clearing rate significantly.

Administration, Cutaneous↗
PubMed1994

Pharmacokinetic analysis of in vivo metabolism of amino acid or dipeptide conjugates of salicylic acid in rabbit intestinal microorganisms.

We analyzed the pharmacokinetics of salicylic acid (SA)-amino acid (alanine, glutamic acid, methionine, and tyrosine) or SA-dipeptide (glycylglycine) conjugates in rabbits, by using a model that takes into account the metabolism of prodrug to SA by intestinal microorganisms and, also, by model-independent analysis. The blood concentration profiles of these prodrugs and released SA following intracecal and oral administration to rabbits were obtained previously (Nakamura et al., J. Pharm. Pharmacol., 44, 295-299, 1992; Chem. Pharm. Bull., 40, 2164-2168, 1992; Int. J. Pharm., 87, 59-66, 1992; J. Pharm. Pharmacol., 44, 713-716, 1992). First, the overall in vivo behavior was evaluated by statistical moment analysis. Next, the blood concentration profiles of prodrug and SA following intracecal and oral administration were simultaneously fitted to the above model. In general, good agreement was observed between fitted lines and experimental data for every prodrug, suggesting the validity of this model. The obtained parameters characterized the difference in the rate of metabolism and absorption among the prodrugs. Lower absorbability and enhanced hydrolysis rate of the prodrug lead to prolonged blood concentration of SA.

Administration, Oral↗
PubMed2001

A nuclear casein kinase 2 activity is involved in early events of transcriptional activation induced by salicylic acid in tobacco.

Salicylic acid (SA) activates immediate early transcription of genes controlled by a family of DNA promoter elements named as-1-like elements. These elements are functional in the promoter of glutathione S-transferase genes. We have previously shown that SA increases the binding of tobacco (Nicotiana tabacum cv Xanthi nc) nuclear factors to the as-1 sequence in a process mediated by protein phosphorylation. In this study we give evidence for the participation of a nuclear protein kinase CK2 (casein kinase 2) in the pathway activated by SA in tobacco. The first line of evidence comes from the evaluation of the CK2 activity in nuclear extracts prepared from tobacco plants treated with SA or water as a control. Results from these experiments indicate that SA increases the nuclear CK2 activity. The second line of evidence derives from the evaluation of the in vivo effect of 5,6-dichloro-1-(beta-D-ribofuranosyl) benzimidazole (DRB), a cell-permeable CK2 inhibitor, on the responsiveness of the as-1 sequence to SA. Results from these experiments indicate that DRB impairs the activating effect of SA on the transcription of both, the GUS reporter gene controlled by a tetramer of the as-1 element, and the endogenous gnt35 gene encoding a glutathione S-transferase, in transgenic tobacco plants. DRB also impaired the increasing effect of SA on the binding of nuclear factors to the as-1 element. Furthermore, transcription of the as-1/GUS reporter gene activated by the synthetic auxin 2,4-dichlorophenoxyacetic acid and by methyl jasmonate was also inhibited by DRB. To our knowledge, this is the first report in which activation of a CK2 enzyme by a plant hormone is reported.

Amino Acid Sequence↗
PubMed2006

Salicylic acid determination in cow urine and drugs using a bienzymatic sensor.

An enzymatic biosensor was developed for salicylic acid (salicylate ion) determined using a Clark type gas diffusion electrode and two enzymes (tyrosinase and salicylate hydroxylase) entrapped in a cellulose triacetate membrane. After optimization, the method was applied to the determination of salicylic acid in cow urine. Relatively good recoveries were achieved, between about 83% and 109%, using the calibration curve, and acceptable precision (R.S.D. about 8%). The method is now being tested for the determination of salicylic acid contained in commercially available drug specialities or galenic products. So far agreement with nominal values has been found to be between 75% and 110% with a R.S.D. of less than 8%.

Animals↗
PubMedDate not supplied

[Response of corn plants to the effect of salicylic acid and Fusarium moniliforme].

Effect of salicylic acid and Fusarium moniliforme on trypsin inhibitor activity, lectine activity, lectine carbohydrate specificity, and salicylic acid content in sprouted maize was studied. Changes in trypsin inhibitor activity, lectine activity, and content of endogenous salicylic acid during action of exogenous salicylic acid or pathogen were shown to depend on resistance of maize lines to fusariosis pathogen. Salicylic acid was proposed to take part in induction of trypsin and lectine inhibitors. Trypsin and lectine inhibitors are important in formation of sprouted maize resistance to abiotic and biotic factors.

Carbohydrate Metabolism↗
PubMed2006

Removal of salicylic acid on perovskite-type oxide LaFeO3 catalyst in catalytic wet air oxidation process.

It has been found that salicylic acid can be removal effectively at the lower temperature of 140 degrees C on perovskite-type oxide LaFeO3 catalyst in the catalytic wet air oxidation (CWAO) process. Under the same condition, the activities for the CWAO of phenol, benzoic acid and sulfonic salicylic acid have been also investigated. The results indicated that, with compared to the very poor activities for phenol and benzoic acid, the activities for salicylic acid and sulfonic salicylic acid were very high, which are attributed to their same intramolecular H-bonding structures. With the role of hard acidity of intramolecular H-bonding, salicylic acid and sulfonic salicylic acid can be adsorbed effectively on the basic center of LaFeO3 catalyst and are easy to take place the total oxidation reaction. However, at temperatures higher than 140 degrees C, the intramolecular H-bonding structure of salicylic acid was destroyed and the activities at 160 and 180 degrees C decreased greatly, which confirms further the key role of intramolecular H-bonding in the CWAO. Moreover, the LaFeO3 catalyst also indicated a superior stability of activity and structure in CWAO of salicylic acid.

Air↗
PubMed1999

Purification, cloning, and expression of a pathogen inducible UDP-glucose:Salicylic acid glucosyltransferase from tobacco.

Salicylic acid (SA) plays an important role in plant disease resistance. Inoculation of tobacco leaves with incompatible pathogens triggers the biosynthesis of SA which accumulates primarily as the SA 2-O-beta-D-glucoside (SAG) and glucosyl salicylate (GS). The tobacco UDP-glucose:salicylic acid glucosyltransferase (SA GTase) capable of forming both SAG and GS was purified, characterized, and partially sequenced. It has an apparent molecular mass of 48 kDa, a pH optimum of 7.0, and an isoelectric point at pH 4.4. UDP-glucose was the sole sugar donor for the enzyme. However, SA and several phenolics served as glucose acceptors. The apparent K(m) values for UDP-glucose and SA were 0.27 and 1-2 mM, respectively. Zn(2+) and UDP inhibited its activity. The corresponding cDNA clone which encoded a protein of 459 amino acids was isolated from an SA-induced tobacco cDNA library and overexpressed in Escherichia coli. The recombinant protein catalyzed the formation of SAG and GS, and exhibited a broad specificity to simple phenolics, similar to that of the purified enzyme. Northern blot analysis showed that the SA GTase mRNA was induced both by SA and incompatible pathogens. The rapid induction timing of the mRNA by SA indicates that it belongs to the early SA response genes.

Amino Acid Sequence↗
PubMed1989

Does the acetyl group of aspirin contribute to the antiinflammatory efficacy of salicylic acid in the treatment of rheumatoid arthritis? The Multicenter Salsalate/Aspirin Comparison Study Group.

In a multicenter, double blind, parallel group study, 233 patients with classical or definite rheumatoid arthritis (RA) were randomized to 12 weeks of either salsalate (salicylsalicylic acid, nonacetylated salicylate) or aspirin following disease flare. One hundred-fifty patients completed, 83 taking salsalate and 67 taking aspirin. Patients received initial doses of 3 g/day of salsalate or 3.6 g/day of aspirin. Doses were adjusted during the first 5 weeks for efficacy and tolerance. Both treatments were equally effective as measured by all the usual variables, but there was a higher incidence of severe gastrointestinal problems among patients taking aspirin. Thus, this study demonstrated that the acetyl group of aspirin does not enhance the antiinflammatory efficacy of salicylic acid in RA.

Acetylation↗
PubMed2000

[Study on the effects of salicylic acid on taxol biosynthesis].

The influence of salicylic acid on the production of taxanes in plant cell culture was studied. Experimental results showed that addition of salicylic acid at concentration of 0.1 mg/L could enhance the production of taxol to three-fold. The concentration of 10-DAB and baccatin III was also increasing while taxol concentration increases under salicylic acid elicitation. On the basis of the kinetic analysis about the simplified taxol biosynthesis pathway, a probable reason that salicylic acid improves the rate of 10-DAB producing reaction was introduced. The results above can direct its inducing mechanic research and provide the basis of multiple-elicitors synergism. The concentration of taxol arrives at 39 mg.L-1 induced by salicylic acid with silver nitrate, being 150 percent of the sum of taxol obtained under elicitation of salicylic acid and silver nitrate respectively.

Antineoplastic Agents, Phytogenic↗
PubMed2005

Glucuronidation of the aspirin metabolite salicylic acid by expressed UDP-glucuronosyltransferases and human liver microsomes.

Acetylsalicylic acid (aspirin) is a common nonsteroidal anti-inflammatory drug used for treatment of pain and arthritis. In the body, acetylsalicylic acid is rapidly deacetylated to form salicylic acid. Both compounds have been proposed as anti-inflammatory agents. Major metabolites of salicylic acid are its acyl and phenolic glucuronide conjugates. Formation of these conjugates, catalyzed by UDP-glucuronosyltransferases (UGTs), decreases the amount of pharmacologically active salicylic acid present. We aimed to identify the UGTs catalyzing the glucuronidation of salicylic acid using both heterologously expressed enzymes and pooled human liver microsomes (HLMs) and to develop a liquid chromatography-tandem mass spectrometry method to quantify glucuronidation activity of UGTs 1A1, 1A3, 1A4, 1A6, 1A7, 1A8, 1A9, 1A10, 2B4, 2B7, 2B15, and 2B17 Supersomes. All UGTs tested, except 1A4, 2B15, and 2B17, catalyzed salicylic acid phenolic and acyl glucuronidation. Ratios of salicylic acid phenolic to acyl glucuronide formation varied more than 12-fold from 0.5 for UGT1A6 to 6.1 for UGT1A1. These results suggest that all UGTs except 1A4, 2B15, and 2B17 might be involved in the glucuronidation of salicylic acid in vivo. From comparisons of apparent Km values determined in pooled HLMs and in expressed UGTs, UGT2B7 was suggested as a likely catalyst of salicylic acid acyl glucuronidation, whereas multiple UGTs were suggested as catalysts of phenolic glucuronidation. The results of this UGT screening may help target future evaluation of the effects of UGT polymorphisms on response to aspirin in clinical and population-based studies.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed1995

Biosynthesis and metabolism of salicylic acid.

Pathways of salicylic acid (SA) biosynthesis and metabolism in tobacco have been recently identified. SA, an endogenous regulator of disease resistance, is a product of phenylpropanoid metabolism formed via decarboxylation of trans-cinnamic acid to benzoic acid and its subsequent 2-hydroxylation to SA. In tobacco mosaic virus-inoculated tobacco leaves, newly synthesized SA is rapidly metabolized to SA O-beta-D-glucoside and methyl salicylate. Two key enzymes involved in SA biosynthesis and metabolism: benzoic acid 2-hydroxylase, which converts benzoic acid to SA, and UDPglucose:SA glucosyltransferase (EC 2.4.1.35), which catalyzes conversion of SA to SA glucoside have been partially purified and characterized. Progress in enzymology and molecular biology of SA biosynthesis and metabolism will provide a better understanding of signal transduction pathway involved in plant disease resistance.

Journal Article↗
PubMed2002

H(+)-linked transport of salicylic acid, an NSAID, in the human trophoblast cell line BeWo.

We investigated the transport of salicylic acid and L-lactic acid across the placenta using the human trophoblast cell line BeWo. We performed uptake experiments and measured the change in intracellular pH (pH(i)). The uptakes of [(14)C]salicylic acid and L-[(14)C]lactic acid were temperature- and extracellular pH-dependent and saturable at higher concentrations. Both uptakes were also reduced by FCCP, nigericin, and NaN(3). Various nonsteroidal anti-inflammatory drugs (NSAIDs) strongly inhibited the uptake of L-[(14)C]lactic acid. Salicylic acid and ibuprofen noncompetitively inhibited the uptake of L-[(14)C]lactic acid. alpha-Cyano-4-hydroxycinnamate (CHC), a monocarboxylate transporter inhibitor, suppressed the uptake of L-[(14)C]lactic acid but not that of [(14)C]salicylic acid. CHC also suppressed the decrease of pH(i) induced by L-lactic acid but had little effect on that induced by salicylic acid or diclofenac. These results suggest that NSAIDs are potent inhibitors of lactate transporters, although they are transported mainly by a transport system distinct from that for L-lactic acid.

Acids↗
PubMed1999

Carrier-mediated absorption of salicylic acid from hamster cheek pouch mucosa.

Previously, we found that monocarboxylic acids undergo carrier-mediated transport in primary cultures of oral mucosal epithelial cells.1 In this study, we investigated whether carrier-mediated absorption of a monocarboxylic acid from the oral mucosa occurs in vivo. Salicylic acid was administered to hamster cheek pouch. At predetermined intervals, the concentration of salicylic acid in the fluid remaining in the cheek pouch lumen and the blood salicylic acid concentration were determined. The absorption of salicylic acid was saturable at high salicylic acid concentrations. Sodium azide, a metabolic inhibitor, and carbonylcyanide p-trifluoromethoxyphenylhydrazone (FCCP), a protonophore, significantly inhibited the absorption of salicylic acid but not the absorption of salicylamide from the oral mucosa. Various monocarboxylic acids inhibited the absorption of salicylic acid, whereas dicarboxylic acids had no such effect. Transfer of [14C]salicylic acid from the cheek pouch mucosa to the systemic circulation was observed, and the blood [14C]salicylic acid concentration in the case of coadministration with propionic acid was significantly lower than that in the case of no propionic acid coadministration. These results show that monocarboxylic acids undergo carrier-mediated absorption from the hamster cheek pouch mucosa.

Absorption↗
PubMed1984

Direct preparation of spherically agglomerated salicylic acid crystals during crystallization.

Needle-like salicylic acid crystals were transformed into a spherically shaped dense form during crystallization by the spherical crystallization technique. Agitation of a mixture of ethanol-water-chloroform containing salicylic acid yielded spherically agglomerated salicylic acid crystals. The crystallinity of the agglomerated salicylic acid the amount of ethanol in the solvent mixture was decreased. The wettability of the agglomerated crystals increased when the amount of ethanol in the solvent mixture was decreased, and this enhanced the dissolution rate of the crystals. The remarkable improvements in the flow and packing of the agglomerated crystals enabled the direct compression of the crystals.

Chemical Phenomena↗