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PubMed1989

Regulation of heat production in the inflorescences of an Arum lily by endogenous salicylic acid.

We have recently purified calorigen, the natural trigger for heat production in the inflorescences of Sauromatum guttatum Schott (voodoo lily), a thermogenic plant, and identified it as salicylic acid. Since then an analytical assay was developed that allows the quantitation of salicylic acid in plant tissues. This assay was used to demonstrate that on the day preceding the day of blooming the levels of salicylic acid in the thermogenic organs (appendix and lower spadix) of the voodoo lily increased almost 100-fold, reaching a level of 1 mug/g of fresh weight. The level of salicylic acid in the appendix started to rise in the afternoon and reached its maximum in the late evening, whereas the maximum accumulation of salicylic acid in the lower spadix occurred late at night. The increase in salicylic acid level in the appendix was followed the next morning by a spectacular metabolic burst that lasted for about 7 hr and at its peak increased the appendix temperature by over 12 degrees C. The second, 14-hr-long, thermogenic episode in the lower spadix started late at night and ended on the following morning, after maximum temperature increases of more than 10 degrees C. The concentration of salicylic acid in both thermogenic tissues promptly returned to basal, preblooming levels at the end of the thermogenic periods. The thermogenic response was under strong photoperiodic and developmental control, with salicylic acid eliciting much stronger thermogenic responses in light than in darkness. Similar surges in salicylic acid occurred in nonthermogenic male and female flowers, while the concentration of salicylic acid in the spathe remained consistently below 20 ng/g of fresh weight. Of 33 analogs of salicylic acid tested, only 2,6-dihydroxybenzoic acid and acetylsalicylic acid (aspirin) were thermogenic. The activity of 2,6-dihydroxybenzoic acid exceeded that of salicylic acid.

Journal Article↗
PubMed1989

Detection and determination of salicylic acid impurity in aspirin tablet formulations' by high performance liquid chromatography.

Salicylic acid is a major hydrolytic degradation product of aspirin, responsible especially for gastric irritation during oral aspirin administration. This impurity was investigated in 12 different brands of aspirin formulation readily available in our locality. A simple, rapid and sensitive high performance liquid chromatographic method was adopted for this investigation. The mobile phase was methanol/water (20/80, v/v) adjusted to pH 2.5 with phosphoric acid and was run on a 50 mm reversed-phase column monitored at 240 nm. The limit of detection for salicylic acid was 5 ng. Only three of these formulations showed the presence of salicylic acid impurity and all these contained salicylic acid in excess of the USP 1980 limit of 0.3% salicylic acid per tablet.

Aspirin↗
PubMed1998

Salicylic acid peels for the treatment of photoaging.

Several chemical agents are currently used to perform superficial chemical peels of the face. These include trichloracetic acid (15-30%), alpha-hydroxy acids (e.g., glycolic acid, 40-70%), and Jessner's solution (14% lactic acid, 14% resorcinol, and 14% salicylic acid). We have developed salicylic acid, a beta-hydroxy acid, at a higher strength (30% in a hydro-ethanolic vehicle) as an alternative peel. This peel has distinct advantages for resurfacing moderately photodamaged facial skin. We have peeled patients singly and multiply at 4-week intervals. The benefits are fading of pigment spots, decreased surface roughness, and reduction of fine lines.

Adult↗
PubMed1984

Drug absorption from the gastrointestinal tract and immunity: the mechanism of the decreased absorption of salicylic acid during systemic anaphylaxis. I.

Previous studies have demonstrated the decrease of intestinal salicylic acid absorption in ovalbumin-immunized rats during systemic anaphylaxis. In the present study, the mechanism whereby systemic anaphylaxis interferes with the intestinal absorption of salicylic acid was studied. The pH of the luminal solution was not affected by the intravenous challenge with ovalbumin. A significant increase of the intraluminal protein was observed in rats under systemic anaphylaxis. However, there was no significant difference between ovalbumin-treated rats and saline-treated ones on the binding of salicylic acid with intraluminal macromolecular substances. Enhanced mucus release in the perfusate was also observed in sensitized rats but the extent of decrease in absorption of salicylic acid did not correlate with the increase in amount of the intraluminal mucus in the same animals. In addition, no significant effect was observed on the uptake by the intestinal everted sac of rats with systemic anaphylaxis. These findings suggested that mucus as well as protein is not responsible for the decrease of absorption of salicylic acid induced by systemic anaphylaxis. From these observations, it would appear that the circulatory changes in the gastrointestinal tract may play an important role in the decreased absorption of salicylic acid during systemic anaphylaxis.

Anaphylaxis↗
PubMed2002

Zeta-crystallin displays strong selectivity for salicylic acid over aspirin.

Interaction of camel lens zeta-crystallin with aspirin was investigated by activity and fluorescence measurements. Aspirin minimally inhibited the oxidoreductase activity of the enzyme and weakly quenched its fluorescence. However, significant fluorescence quenching of zeta-crystallin coincided with the appearance of a fluorescence signal characteristic of salicylic acid thereby raising the possibility that salicylic acid might have been the moiety responsible for inhibition and fluorescence quenching. Direct fluorescence measurements showed that zeta-crystallin had a much higher affinity for salicylic acid than aspirin (K(i) of about 24 microM for salicylic acid versus 630 microM for aspirin). Salicylic acid was also far more effective in inhibiting zeta-crystallin than aspirin (K(i) values were 23 microM versus 820 microM, respectively). Inhibition kinetics suggested that salicylic acid interacted with zeta-crystallin via a binding site that was distinct from that of NADPH. Salicylic acid also interacted with and quenched the fluorescence of camel lens alpha-crystallin suggesting a general mode of interaction with lens proteins. Within the normal therapeutic concentrations of salicylic acid or aspirin, only crystallin-salicylic acid interactions might be significant. These results showed that camel lens zeta- and alpha-crystallin exhibited remarkable selectivity for salicylic acid over aspirin, and thus, could be considered as salicylate-binding proteins.

Animals↗
PubMed2005

Humic substances can modulate the allelopathic potential of caffeic, ferulic, and salicylic acids for seedlings of lettuce (Lactuca sativa L.) and tomato (Lycopersicon esculentum Mill.).

The capacity of a leonardite humic acid (LHA), a soil humic acid (SHA), and a soil fulvic acid (SFA) in modulating the allelopathic potential of caffeic acid (CA), ferulic acid (FA), and salicylic acid (SA) on seedlings of lettuce (Lactuca sativa L.) and tomato (Lycopersicon esculentum Mill.) was investigated. Lettuce showed a sensitivity greater than that of tomato to CA, FA, and SA phytotoxicity, which was significantly reduced or even suppressed in the presence of SHA or SFA, especially at the highest dose, but not LHA. In general, SFA was slightly more active than SHA, and the efficiency of the action depended on their concentration, the plant species and the organ examined, and the allelochemical. The daily measured residual concentration of CA and FA decreased drastically and that of SA slightly in the presence of germinating seeds of lettuce, which were thus able to absorb and/or enhance the degradation of CA and FA. The adsorption capacity of SHA for the three allelochemicals was small and decreased in the order FA > CA > SA, thus suggesting that adsorption could be a relevant mechanism, but not the only one, involved in the "antiallelopathic" action.

Adsorption↗
PubMed1998

Effect of ointment bases on topical and transdermal delivery of salicylic acid in rats: evaluation by skin microdialysis.

Microdialysis has been used to determine the concentration of salicylic acid in skin tissue and plasma periodically for 4 h to evaluate the effect of ointment bases on topical and transdermal delivery of salicylic acid. The ointment bases examined were solbase (water-soluble), poloid and white petrolatum (oleaginous), hydrophilic poloid (water in oil (w/o) type emulsion lacking water) and absorptive ointment (w/o-type emulsion containing water). The ointments (0.1 g) containing 25 micromol salicylic acid were applied for 2 h to the surface of rat skin (1 cm2) with (intact) or without the stratum corneum. For intact skin, the extent of topical delivery from different ointments, evaluated by the area under the concentration-time curve (AUC) of salicylic acid in the skin tissue (AUCskin), increased in the order solbase << white petrolatum, poloid, hydrophilic poloid << absorptive ointment. The ratio of AUCskin (topical delivery) to the AUC of salicylic acid in plasma (AUCplasma, transdermal delivery) varied remarkably among the different bases, the greatest ratio being observed for absorptive ointment. When the ointments were applied to skin surface without stratum corneum, AUCskin for solbase was much higher (about 45 times that for intact skin), whereas only a small (two-fold) increase was observed for poloid and hydrophilic poloid and the increase was negligible for white petrolatum and absorptive ointment. For skin without the stratum corneum, the ratio AUCskin/AUCplasma for the different ointments was comparable, although the magnitudes of AUCskin and AUCplasma still varied substantially. The variance of AUC values arises as a result of the different rates of release of salicylic acid from the bases. These results indicate that: the topical and transdermal delivery of salicylic acid in intact skin varies substantially among different ointment bases, and the greatest topical delivery is observed for absorptive ointment; use of absorptive ointment increases the retention of salicylic acid in the stratum corneum; and the stratum corneum functions strongly as a penetration barrier for solbase, moderately for poloid and hydrophilic poloid, and less for absorptive ointment and white petrolatum.

Animals↗
PubMed1994

The ocs element in the soybean GH2/4 promoter is activated by both active and inactive auxin and salicylic acid analogues.

The octopine synthase (ocs or ocs-like) element has been previously reported to be responsive to the plant hormones, auxin, salicylic acid, and methyl jasmonate. Using transient assays with carrot protoplasts, we have demonstrated that an ocs element from the soybean auxin-inducible GH2/4 promoter is not only activated by strong auxins (i.e., 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid, alpha-naphthalene acetic acid) and salicylic acid, but also by weak auxin analogues (beta-naphthalene acetic acid), inactive auxin analogs (i.e., 2,3-dichlorophenoxyacetic acid, 2,4,6-trichlorophenoxyacetic acid), and inactive salicylic acid analogs (3-hydroxybenzoic acid and 4-hydroxybenzoic acid). Our results indicate that the ocs element in the GH2/4 promoter is not selectively induced by plant hormones and might function similarly to tandem AP-1 sites in some animal glutathione S-transferase (GST) genes. The ocs element, like the AP-1 sites in animal GST promoters, may be induced not only by certain hormones but also by some non-hormonal stress-inducing or electrophilic agents.

Amino Acid Oxidoreductases↗
PubMed2001

Responses of transformed root culture of Atropa belladonna to salicylic acid stress.

The effect of salicylic acid (SA) on tropane alkaloid production and the responses to SA stress of transformed root cultures of Atropa belladonna (belladonna) were investigated. Treatment of A. belladonna transformed roots with 0.2 mM SA did not have any effect on tropane alkaloid production, but two compounds were produced in the medium. These were identified as the SA derivatives methylsalicylate and methyl-o-methoxybenzoate by high-resolution mass spectrometry and UV spectrometry. In contrast, treatment with 2 mM salicylic acid stimulated tropane alkaloid release from the transformed roots into the medium by up to 35% of the total alkaloids after 24 h, and the SA derivatives were not observed in the medium. These results revealed that transformed root of A. belladonna exhibits distinct by different responses to SA stress depending on the SA concentration.

Journal Article↗
PubMed2000

Efficacy of hydroquinone cream (USP 4%) used alone or in combination with salicylic acid peels in improving photodamage on the neck and upper chest.

BACKGROUND: Salicylic acid, hydroquinone, and glycolic acid have been proved effective in the treatment of photodamaged facial skin. Few reports are available on the treatment of photodamage on the neck and upper chest. OBJECTIVE: This study's purpose was to evaluate the efficacy of a cream containing 4% hydroquinone and 2% glycolic acid (LUSTRA) used alone or with salicylic acid peels in reversing actinic damage on the neck and upper chest. METHODS: Nineteen women with moderate to advanced photodamage on the neck and upper chest applied a cream containing 4% hydroquinone and 2% glycolic acid twice daily on photodamaged areas for 12 weeks. Nine of these subjects had salicylic acid peels every 3 weeks. Improvements were assessed by the investigator, the subjects, and Mexameter readings measuring melanin and erythema levels. RESULTS: The result shows that there was a 33-71% improvement in photodamage, hyperpigmentation, texture, fine lines, dryness, tone, and clarity in both groups. There were no significant differences between the two treatments. CONCLUSION: Hydroquinone 4% cream with 2% glycolic acid is safe and effective in improving photodamage on the neck and upper chest when used alone or in combination with salicylic acid peels.

Chemexfoliation↗
PubMed1966

Biosynthesis and utilization of aromatic compounds by Mycobacterium smegmatis with particular reference to the origin of salicylic acid.

1. Although Mycobacterium smegmatis could utilize a number of aromatic compounds as sole sources of carbon for growth, it did not appear to be able to use salicylic acid for growth or to metabolize it to any great extent. 2. When M. smegmatis was grown on shikimic acid as sole source of carbon, salicylic acid, anthranilic acid and 3,4-dihydroxybenzoic acid were released into the medium. When it was grown on quinic acid these compounds, together with p-hydroxybenzoic acid, p-hydroxyphenylacetic acid and a number of unidentified compounds, were formed. When it was grown on glucose only small amounts of salicylic acid could be detected. 3. When a washed suspension of cells with a normal iron content was incubated with shikimic acid, only small amounts of aromatic compounds were formed in the medium. When the cells were iron-deficient, substantial amounts of salicylic acid, 3,4-dihydroxybenzoic acid and catechol were formed, together with several other compounds not definitely identified. 4. When washed suspensions of cells, whether iron-sufficient or iron-deficient, were incubated with tryptophan no evidence of formation of salicylic acid, anthranilic acid or phenolic compounds was obtained. Washed suspensions did not convert anthranilic acid into salicylic acid. 5. When cell-free extracts of M. smegmatis were incubated with shikimic acid, or shikimic acid 5-phosphate, traces of anthranilic acid were formed under certain conditions. No formation of salicylic acid or other phenolic compound was observed even when a number of combinations of cofactors and coenzymes were tried.

Benzoates↗
PubMed2003

The metabolic pathway of salicylic acid rather than of chlorogenic acid is involved in the stress-induced flowering of Pharbitis nil.

We examined the involvement of chlorogenic acid (CGA) and salicylic acid (SA) in the stress-induced flowering of Pharbitis nil (synonym Ipomoea nil). The incorporation efficiency of exogenously applied CGA and the deactivation rate of incorporated CGA were determined in cotyledons by high-performance liquid chromatography. The assay plants could not incorporate a sufficient amount of CGA via roots. The perfusion technique by which the assay solution was forced into the plant from the cut end of the hypocotyl improved the efficiency of CGA incorporation. However, no flower-inducing activity was detected, indicating that CGA was not involved in flowering. It was concluded that the close correlation between CGA content and flowering response is merely coincidence or a parallelism. Flowering under long-day conditions induced by low-temperature stress was completely inhibited by aminooxyacetic acid (AOA), an inhibitor of phenylalanine ammonialyase. The flower-inhibiting effect of AOA was nullified by co-applied t-cinnamic acid and by benzoic acid. This indicates that the metabolic pathway from t-cinnamic acid to SA via benzoic acid is involved in the stress-induced flowering. The results indicate that the metabolic pathway of SA is involved in the stress-induced flowering of P. nil not the metabolic pathway of CGA.

Aminooxyacetic Acid↗
PubMed2004

FT-IR and NMR spectroscopic studies of salicylic acid derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy derivatives.

The 2,4- and 2,5-dihydroxybenzamides (8, 9) were synthesized from their corresponding methyl esters. The structures and the spectral properties of investigated salicylic acid (1), 2,4- and 2,5-dihydroxy benzoic acids (2, 3), their methyl esters (4-6) and amides (7-9) were analyzed by means of FT-IR and one- and two-dimensional homo- and heteronuclear 1H and 13C NMR spectroscopies. Comparison of FT-IR and NMR spectral data of investigated compounds showed that the spectral characteristics of 2,4-dihydroxy benzoic acid derivatives are more similar to those of 2-hydroxy benzoic acid (salicylic acid) derivatives than to those of 2,5-dihydroxy benzoic acid derivatives. The results suggest that the spatial orientation of amide protons in 2,4-dihydroxy benzamide resembles more that in salicylamide than that in 2,5-dihydroxy benzamide.

Benzamides↗
PubMed2005

Laser spectroscopic investigation of salicylic acids hydrogen bonded with water in supersonic jets: Microsolvation effects for excited state proton dislocation.

Geometric structures and excited-state proton dislocation of size-selected salicylic acid clusters (salicylic acid and 5-methoxysalicylic acid) with water were studied by using laser spectroscopic techniques. Fluorescence excitation, dispersed fluorescence, and infrared (IR) spectra of those clusters in supersonic jets were examined for both the electronic ground (S0) and first excited (S1) states. The geometric structures of the clusters were determined on the basis of the IR spectra of the OH stretch region with the help of quantum chemical calculations. The hydroxyl group of the water moiety in the clusters forms a ring involving the carboxylic group of the salicylic acid moiety. The IR spectra in S0 show that the intramolecular hydrogen bond in the salicylic acid moiety is still held upon cluster formation, but the phenolic OH stretch band intensity is remarkably weaken in the clusters. The IR spectra in the S1 state and dispersed fluorescence spectra indicated that the intramolecular excited state proton dislocation is hardly affected by the microsolvation with water, in contrast with the strong suppression of the dislocation in the self-solvation.

Journal Article↗
PubMed2006

Salicylic acid content of spices and its implications.

This work was done to determine the salicylate content of a variety of commonly used spices and to assess whether this potential dietary source of salicylate was bioavailable. Spices, Indian cooked dishes, and blood and urine samples taken after ingestion of a test meal were investigated for their salicylate content using high-performance liquid chromatography with electrochemical detection. The serum salicylic acid concentrations in samples from villagers in southern India were also measured and have been compared with typical European values. Salicylic acid was determined in all spices (up to 1.5 wt %) and cooked dishes. The salicylate content of blood and urine was shown to increase following consumption of the meal, indicating that this dietary source of salicylic acid was bioavailable. Salicylic acid levels in the serum from rural Indians were significantly (median almost 3-fold) higher than values previously measured in Western vegetarians. Chemoprotective aspirin is rapidly hydrolyzed to salicylic acid, and this phytochemical may contribute to the low cancer incidence in rural India.

Adult↗
PubMed1958

The relative potencies of some substituted salicylic acids as metabolic stimulants in the intact rat.

The effects of eighteen substituted benzoic acids on the rate of oxygen consumption have been studied in rats. 2:3-Dihydroxybenzoic acid, phthalic acid and 6-methylsalicylic acid were, at the doses used, inactive; m- and p-hydroxybenzoic acid, 2:4-, 2:5-, 2:6-, 3:4-, and 3:5-dihydroxybenzoic acid, o-aminobenzoic acid, salicyluric acid, salicylamide and 5-aminosalicylic acid decreased the rate of oxygen consumption. Only salicylic acid and o-, m- and p-cresotic acid (3-, 4- and 5-methylsalicylic acid respectively) increased the rate of oxygen consumption. Molar potency ratios of the cresotic acids as metabolic stimulants relative to salicylic acid were determined; o-cresotic acid was the most powerful with a ratio of 2.61, m- and pcresotic acid had values of 1.78 and 1.89 respectively. Two possible explanations of the higher potencies of the cresotic acids were considered. No difference in the primary action of the drug was established by determining the effect on rate of oxygen consumption of a mixture of o-cresotic and salicylic acids. An alternative possibility was that the rates of detoxication and excretion of the cresotic acids differed among themselves and from salicylic acid. No such differences were found.

Animals↗
PubMed2004

[Development of salicylic acid detector tube].

A detector tube was successfully devised for the screening of salicylic acid in urine. It, named "salicylic acid detector tube", consists of glass tube in which silica gel coated with 5% (w/w) of ferric chloride is enclosed. A pipette rubber cap was attached to an end of the tube, and another end was inserted into urine sample. The sample was then introduced into the tube, the color of the reagent immediately turned purple under the condition of more than 50 microg/ml of salicylic acid in urine. This device was useful for the emergency screening of salicylic acid in acute poisoning cases with aspirin.

Acute Disease↗