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PubMed2002

Recent breakthroughs in the study of salicylic acid biosynthesis.

Salicylic acid is an important regulator of induced plant resistance to pathogens. Consequently, the biosynthesis of salicylic acid and its regulation has received a lot of attention. Salicylic acid can be made from phenylalanine via cinnamic and benzoic acid. Recently, genetic studies in Arabidopsis have shown that salicylic acid is made in the chloroplast from isochorismate, a pathway that is known to operate in prokaryotes.

Arabidopsis↗
PubMed2002

New formulation of chemical peeling agent: 30% salicylic acid in polyethylene glycol. Absorption and distribution of 14C-salicylic acid in polyethylene glycol applied topically to skin of hairless mice.

Salicylic acid is used in chemical peeling procedures. However, they have caused many side effects, even salicylism. To achieve a salicylic acid peeling that would be safer for topical use, we recently developed a new formulation consisting of 30% salicylic acid in polyethylene glycol (PEG) vehicle. In an extension of our previous research, we studied the absorption of 30% salicylic acid labeled with 14C in PEG vehicle applied topically to the intact and damaged skin of male hairless mice. An ointment containing 3 mg salicylic acid in 10 mg vehicle was applied to both groups. In animals with intact skin, 1 h after application the plasma concentration of radioactivity was 1665.1 ng eq/ml, significantly lower than the 21437.6 ng eq/ml observed in mice with damaged skin. Microautoradiograms of intact skin showed that the level of radioactivity in the cornified cell layer was similar at 6 h after application. However, in damaged skin, the overall level of radioactivity showed a decrease by 3 h after application. In the carcasses remaining after the treated intact and damaged skin had been removed, 0.09 and 11.38% of the applied radioactivity remained, respectively. These findings confirm that 30% salicylic acid in PEG vehicle is little absorbed through the intact skin of hairless mice, and suggest that salicylism related to absorption through the skin of quantities of topically applied salicylic acid is not likely to occur in humans with intact skin during chemical peeling with this preparation. This new preparation of 30% salicylic acid in PEG vehicle is believed to be safe for application as a chemical peeling agent.

Absorption↗
PubMedDate not supplied

[Serum levels of salicylic acid in patients with psoriasis treated with 10% salicylic acid ointment].

Ten patients with psoriasis were treated for three days with salicylic acid ointment with vaseline vehicle. In all patients the serum concentration of salicylic acid increased systematically and the concentration depended on the amount of ointment used and on psoriasis form. Only in one case of exudative psoriasis the level of salicylic acid reached the value causing intoxication, and produced a diffuse inflammatory erythema with itching. The treatment caused no changes of biochemical indices.

Administration, Cutaneous↗
PubMed2001

Salicylic acid in the serum of subjects not taking aspirin. Comparison of salicylic acid concentrations in the serum of vegetarians, non-vegetarians, and patients taking low dose aspirin.

AIMS: To determine serum salicylic acid concentrations in non-vegetarians and vegetarians not taking salicylate drugs, and to compare these concentrations with those found in patients taking aspirin, 75 mg daily. METHODS: Serum samples were obtained from vegetarians (n = 37) and non-vegetarians (n = 39) not taking salicylate drugs. Non-vegetarians and vegetarians were recruited from the community and from a Buddhist monastery, respectively, in Dumfries and Galloway, Scotland. Patients (n = 14) taking aspirin (75 mg daily) were recruited from the Dumfries diabetic clinic. Serum salicylic acid concentrations were determined using a high performance liquid chromatography method with electrochemical detection. RESULTS: Salicylic acid was detected in every serum sample analysed. Higher serum concentrations of salicylic acid were found in vegetarians than non-vegetarians: median concentrations of 0.11 (range, 0.04-2.47) micromol/litre and 0.07 (range, 0.02-0.20) micromol/litre, respectively; the median of the difference was 0.05 micromol/litre (95% confidence interval for difference, 0.03 to 0.08; p < 0.0001). The median serum concentration of salicylic acid in patients taking aspirin (75 mg daily) was 10.03 (range, 0.23-25.40) micromol/litre, which was significantly higher than that found in non-vegetarians and vegetarians. There was overlap in serum salicylic acid concentrations between the vegetarians and patients taking aspirin. CONCLUSIONS: Salicylic acid, a non-steroidal anti-inflammatory drug, is present in fruits and vegetables and is found in higher concentrations in vegetarians than non-vegetarians. This suggests that a diet rich in fruits and vegetables contributes to the presence of salicylic acid in vivo. There is overlap between the serum concentrations of salicylic acid in vegetarians and patients taking aspirin, 75 mg daily. These findings may explain, in part, the health promoting effects of dietary fruits and vegetables.

Adult↗
PubMed2002

Protection against heat stress-induced oxidative damage in Arabidopsis involves calcium, abscisic acid, ethylene, and salicylic acid.

Plants, in common with all organisms, have evolved mechanisms to cope with the problems caused by high temperatures. We examined specifically the involvement of calcium, abscisic acid (ABA), ethylene, and salicylic acid (SA) in the protection against heat-induced oxidative damage in Arabidopsis. Heat caused increased thiobarbituric acid reactive substance levels (an indicator of oxidative damage to membranes) and reduced survival. Both effects required light and were reduced in plants that had acquired thermotolerance through a mild heat pretreatment. Calcium channel blockers and calmodulin inhibitors increased these effects of heating and added calcium reversed them, implying that protection against heat-induced oxidative damage in Arabidopsis requires calcium and calmodulin. Similar to calcium, SA, 1-aminocyclopropane-1-carboxylic acid (a precursor to ethylene), and ABA added to plants protected them from heat-induced oxidative damage. In addition, the ethylene-insensitive mutant etr-1, the ABA-insensitive mutant abi-1, and a transgenic line expressing nahG (consequently inhibited in SA production) showed increased susceptibility to heat. These data suggest that protection against heat-induced oxidative damage in Arabidopsis also involves ethylene, ABA, and SA. Real time measurements of cytosolic calcium levels during heating in Arabidopsis detected no increases in response to heat per se, but showed transient elevations in response to recovery from heating. The magnitude of these calcium peaks was greater in thermotolerant plants, implying that these calcium signals might play a role in mediating the effects of acquired thermotolerance. Calcium channel blockers and calmodulin inhibitors added solely during the recovery phase suggest that this role for calcium is in protecting against oxidative damage specifically during/after recovery.

Abscisic Acid↗
PubMed1988

Monochloroacetic acid and 60% salicylic acid as a treatment for simple plantar warts: effectiveness and mode of action.

Monochloroacetic acid crystals and 60% salicylic acid ointment was found to be more effective than placebo as a treatment for simple plantar warts in a double blind study on 57 patients. Nineteen (66%) patients in the active treatment group compared with five (18%) patients in the placebo group were cured after 6 weeks (P = 0.002). The active treatment was associated with a significantly higher cure rate 6 months after entry (P = 0.04). Treatments were well tolerated. IgG or IgM antibodies or both to human papilloma virus (HPV) types 1 or 2 or both were detected significantly more frequently in the actively treated group 6 weeks after entry (P = 0.0005). Twelve (50%) patients considered to be cured had no detectable secondary immune response. Our results suggest that cure does not depend primarily on the humoral system but rather on mechanical destruction of wart tissue, or occurs as a result of cell mediated immunity.

Acetates↗
PubMedDate not supplied

The second acidic constant of salicylic acid.

The second dissociation constant of salicylic acid (H2L) has been determined, at 25 degrees C, in NaCl ionic media by UV spectrophotometric measurements. The investigated ionic strength values were 0.16, 0.25, 0.50, 1.0, 2.0 and 3.0 M. The protolysis constants calculated at the different ionic strengths yielded, with the Specific Interaction Theory, the infinite dilution constant, log beta1(0) = 13.62 +/- 0.03, for the equilibrium L2- + H+ <==> HL-. The interaction coefficient between Na+ and L2-, b(Na+, L2-) = 0.02 +/- 0.07, has been also calculated.

Hydrogen-Ion Concentration↗
PubMedDate not supplied

Salicylic acid and PEG-contained polyanhydrides: synthesis, characterization, and in vitro salicylic acid release.

Poly [bi(o-carboxyphenyl)adipate-polyethylene glycol] anhydrides--P(BOCA-PEG)--polymeric drugs were synthesized and characterized by Fourier transformed infrared spectroscopy, NMR, DSC, gel permeation chromatography, etc. Salicylic acid loading efficiency of these polymers ranged from 43.5% to 71.3%, which was much higher than that of other polymeric drugs with salicylic acid. The in vitro release of salicylic acid from the polymers was carried out in buffer conditions with different pH values and and rat gastrointestinal contents. The results showed the release rate of salicylic acid increased with the increase of PEG content in the polymers and the increase of pH value of degradation buffer solution. The rat cecal contents also greatly promoted the release of salicylic acid. In 0.1M phosphate buffer solution at pH8.0, 37 degrees C containing 5% rat cecal contents, P(BOCA-PEG200)(80:20) had 15% salicylic acid released in 21 hr, indicating its potential use in colon-specific salicylic acid delivery.

Animals↗
PubMed2001

Salicylic acid response in rice: influence of salicylic acid on H(2)O(2) accumulation and oxidative stress.

We have studied the accumulation of hydrogen peroxide in rice leaves in response to salicylic acid (SA) treatment. H(2)O(2) accumulation was localized in the veins. While the activity of the H(2)O(2) degrading enzyme peroxidase was inhibited in response to SA, superoxide dismutase activity, which generates H(2)O(2), did not show any change. An increase in the activity of glutathione reductase, a peroxide degrading enzyme, was observed upon SA treatment, similar to the response reported by accumulation of active oxygen species. In rice leaves transformed with CaMV-GUS fusions, we found that SA treatment induced transcriptional activation through as-1 element. As-1 has been implicated in protective mechanisms that operate during some types of oxidative stress and the hypersensitive response (HR). Expression of rice pathogenesis-related protein 5 (PR5), one of the PR genes associated with systemic acquired resistance, was induced by SA. This induction seems to be independent of the H(2)O(2) accumulation induced by SA. Inoculation of rice leaves with the rice blast fungus, Magneporthe grisea, also led to the accumulation of H(2)O(2) in the veins, suggesting the presence of common signals between SA and pathogen responses. Thus SA application seems to induce oxidative stress in rice through H(2)O(2); a signal molecule implicated in biotic and abiotic stress responses.

Journal Article↗
PubMed2003

Plastidial fatty acid signaling modulates salicylic acid- and jasmonic acid-mediated defense pathways in the Arabidopsis ssi2 mutant.

A mutation in the Arabidopsis gene ssi2/fab2, which encodes stearoyl-acyl carrier protein desaturase (S-ACP-DES), results in the reduction of oleic acid (18:1) levels in the mutant plants and also leads to the constitutive activation of NPR1-dependent and -independent defense responses. By contrast, ssi2 plants are compromised in the induction of the jasmonic acid (JA)-responsive gene PDF1.2 and in resistance to the necrotrophic pathogen Botrytis cinerea. Although S-ACP-DES catalyzes the initial desaturation step required for JA biosynthesis, a mutation in ssi2 does not alter the levels of the JA precursor linolenic acid (18:3), the perception of JA or ethylene, or the induced endogenous levels of JA. This finding led us to postulate that the S-ACP-DES-derived fatty acid (FA) 18:1 or its derivative is required for the activation of certain JA-mediated responses and the repression of the salicylic acid (SA) signaling pathway. Here, we report that alteration of the prokaryotic FA signaling pathway in plastids, leading to increased levels of 18:1, is required for the rescue of ssi2-triggered phenotypes. 18:1 levels in ssi2 plants were increased by performing epistatic analyses between ssi2 and several mutants in FA pathways that cause an increase in the levels of 18:1 in specific compartments of the cell. A loss-of-function mutation in the soluble chloroplastic enzyme glycerol-3-phosphate acyltransferase (ACT1) completely reverses SA- and JA-mediated phenotypes in ssi2. In contrast to the act1 mutation, a loss-of-function mutation in the endoplasmic reticulum-localized omega6 oleate desaturase (FAD2) does not alter SA- or JA-related phenotypes of ssi2. However, a mutation in the plastidial membrane-localized omega6 desaturase (FAD6) mediates a partial rescue of ssi2-mediated phenotypes. Although ssi2 fad6 plants are rescued in their morphological phenotypes, including larger size, absence of visible lesions, and straight leaves, these plants continue to exhibit microscopic cell death and express the PR-1 gene constitutively. In addition, these plants are unable to induce the expression of PDF1.2 in response to the exogenous application of JA. Because the act1 mutation rescues all of these phenotypes in ssi2 fad6 act1 triple-mutant plants, act1-mediated reversion may be mediated largely by an increase in the free 18:1 content within the chloroplasts. The reversion of JA responsiveness in ssi2 act1 plants is abolished in the ssi2 act1 coi1 triple-mutant background, suggesting that both JA- and act1-generated signals are required for the expression of the JA-inducible PDF1.2 gene. Our conclusion that FA signaling in plastids plays an essential role in the regulation of SSI2-mediated defense signaling is further substantiated by the fact that overexpression of the N-terminal-deleted SSI2, which lacks the putative plastid-localizing transit peptide, is unable to rescue ssi2-triggered phenotypes, as opposed to overexpression of the full-length protein.

Arabidopsis↗
PubMed1989

[Salicylic acid and urea--possible modification of the keratolytic effect of salicylic acid by urea].

The keratolytic effect of salicylic acid was measured with a colorimeter after staining the outer layers of the stratum corneum with silver nitrate. Salicylic acid was used in a concentration of 5% or 10% in vaseline or of 5% in an improved vehicle. The results of two experiments showed that improvement of the vehicle increased the keratolytic effect of salicylic acid and that urea played a major role in this improvement.

Dermatologic Agents↗
PubMed2001

Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid.

11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the aldehyde and triphenylphosphonium iodides in the presence of BuLi gave the methoxybenzoates, and then treatments of these methoxybenzoates with BBr3 in CH2Cl2 and 10% NaOH in ethanol gave 6-18(Z),11(Z)-pentadecadienyllsalicylic acid (anacardic acid 3) and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid (anacardic acid 4) which were isolated from plants of the anacardiaceae.

Alkenes↗
PubMed1976

Dermatopharmacology of salicylic acid. III. Topical contra-inflammatory effect of salicylic acid and other drugs in animal experiments.

The acute contra-inflammatory effects of salicylic acid, three standard dermatocorticoids and four contact antiphlogistics have been investigated by means of a UV dermatitis inhibition test in the guinea pig. The substances tested had a distinct inhibitory effect on the development of erythema and can be ranked in the following ascending order of activity (percent of maximum possible score): bufexamac = 36%, salicylic acid = 37%, hydrocortisone = 44%, acetylsalicylic acid = 48%, flumethasone pivalate = 51%, fluocinolone acetonide = 51%, phenylbutazone = 56%, and indomethacin = 58%.

Administration, Topical↗