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PubMedDate not supplied

Structural studies on polymer whiskers by transmission electron microscopy: I. Morphological and high-resolution observations.

The structures of poly(p-hydroxybenzoic acid) (PHBA) whisker crystals and crystalline fine fibrils of copolymer prepared from p-hydroxybenzoic acid (HBA) and 2-hydroxy-6-naphthoic acid (HNA), namely poly(HBA/HNA) (monomer molar ratio: 97/3), were investigated by transmission electron microscopy (TEM). As for a PHBA whisker, microfibril-like bright regions were recognized in the 210 dark-field image. In the high-resolution TEM image of another PHBA whisker, however, lattice fringes were continuous through the whisker, showing that the whisker is highly crystalline and almost perfect. On the other hand, in the high-resolution images of poly(HBA/HNA) fine fibrils, granular crystallites (20-40 nm in lateral dimension) were observed. The lattice fringes in the crystallites were not successfully indexed with the orthorhombic unit cells of the homopolymer crystal, suggesting the coexistence of another different structure as a minor component.

Crystallization↗
PubMed1998

Catechin metabolites after intake of green tea infusions.

Green tea contains relatively large amounts of catechins, that have been recognized to be efficient free-radical scavengers. In spite of a largely described antioxidant effect, the metabolic fate of catechins in humans has been scarcely studied. An infusion of green tea (about 400 mg of catechins) was given to healthy volunteers; plasma and urine samples were collected for 5 h and 2 days, respectively. Epigallocatechin gallate and epicatechin gallate were detected in plasma samples, reaching the maximum concentration (2 microM) at 2 h. Urine samples collected at 6-48 h contained detectable amounts of final catechin metabolites, including 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3-methoxy-4-hydroxy-hippuric acid and 3-methoxy-4-hydroxybenzoic acid (vanillic acid). The total content of these metabolites averaged 60 mg. The levels of free plasma catechins account only partly for the increased (approximately +20%) total radical-trapping antioxidant parameter (TRAP) detected after green tea intake. Catechin conjugates (glucuronide and sulphate) and metabolites may add further contribution and explain the measured TRAP increase.

Antioxidants↗
PubMed2005

Positional and geometrical anionic isomer separations by capillary electrophoresis-electrospray ionization-mass spectrometry.

Capillary electrophoresis-electrospray ionization-mass spectrometry (CE-ESI-MS) was applied to the analysis of polar positional and geometrical anionic isomers. Since the investigated positional and geometrical anionic isomers have different pK(a) values, they could be separated by CE-ESI-MS under simple analytical conditions using a bare fused-silica capillary and volatile ammonium acetate buffer after optimizing buffer pH. Ortho-, meta-, para-hydroxybenzoate positional isomers were completely separated on a fused-silica capillary with 20 mM ammonium acetate buffer at pH 10.0, and cis-, trans-cyclohexane dicarboxylate geometrical isomers could be also separated with 20 mM ammonium acetate buffer at pH 4.0. Several analytical parameters affecting ESI-MS sensitivity were also investigated. It was found that both running buffer pH and sheath liquid pH had significant effects on the selectivity and the sensitivity on CE-ESI-MS analysis while sheath flow rate and other parameters had little influence. Under optimized conditions, linearity, detection limit, and repeatability of the analysis of hydroxybenzoate isomers were examined, and good results were obtained. It was found that the method presented in this paper is a simple, robust, and cost-effective method for simultaneous analysis of positional and geometrical anionic isomers as well as of other small anionic compounds.

Anions↗
PubMed1976

The involvement of a diol-epoxide in the metabolic activation of benzo(a)pyrene in human bronchial mucosa and in mouse skin.

DNA has been isolated from human bronchial segments that have been treated in short-term organ culture with 3H-labelled benzo (a) pyrene. DNA has also been isolated from mouse skin treated with 3H-labelled samples of benzo (a) pyrene, with the related radioactive 4,5-, 7,8- and 9,10-dihydrodiols and with 3H-3-hydroxybenzo (a) pyrene. Sephadex LH20 column chromatography of hydrolysates of these DNA samples showed that the hydrocarbondeoxyribonucleoside products formed in benzo (a)-pyrene-treated human bronchial mucosa and mouse skin are indistinguishable from those that are formed when 7,8-dihydro-7,8-dihydroxybenzo (a) pyrene 9,10-oxide reacts with DNA in solution. These same hydrocarbon-deoxyribonucleoside products were also found in hydrolysates of DNA from mouse skin treated with 7,8-dihydro-7,8-dihydroxybenzo (a)-pyrene but products of this type were not detected in hydrolysates of DNA following treatment of mouse skin either with the 4,5- or 9,10-dihydrodiols or with 3-hydroxybenzo (a) pyrene. This results show that the metabolic activation of benzo (a) pyrene to a diolepoxide, 7,8-dihydro-7,8-dihydroxybenzo (a) pyrene 9,10-oxide, which reacts with DNA, is the same in human bronchial mucosa, a tissue in which this hydrocarbon is suspected of being carcinogenic, as it is in mouse skin and in hamster embryo cells, two situations in which benzo(a)pyrene is known to induce malignancy.

Animals↗
PubMed1981

In vivo formation of benzo(alpha)pyrene diol epoxide-deoxyadenosine adducts in the skin of mice susceptible to benzo(alpha)pyrene-induced carcinogenesis.

The hydrocarbon-deoxyribonucleoside adducts formed in mouse skin DNA have been determined following topical application of an initiating dose of benzo(a)pyrene to Swiss mice, a strain shown to be susceptible to benzo(a)pyrene-induced skin carcinogenesis. Several DNA-bound products were formed, of which the major one (60% of total adducts), in agreement with other workers' findings, was derived from reaction of (+/-) 7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9,10-tetrahydrobenzo(alpha)pyrene (BDE) with the exocyclic aminogroup of deoxyguanosine. A further product (9-10% of total adducts), previously observed only after microsomal activation of benzo(a)pyrene, was observed and co-chromatographed with a further metabolite of 9-hydroxybenzo(alpha)pyrene bound to an uncharacterized base in the DNA. Two otherr products (2-3% of total adducts) were also found in the in vivo studies which co-chromatographed with BPDE-deoxyadenosine adducts and arose from cis and trans addition of the exocyclic amino group of deoxyadenosine to the 7R form, but not the 7S form, of BPDE. In contrast to this, the major in vitro deoxyadenosine-bound products, formed following reaction of BPDE with calf-thymus DNA, were derived from the 7S form of BPDE, suggesting either stereoselective formation or reaction of the 7R form of BPDE in mouse skin in vivo. Similar amounts of BPDE-deoxyguanosine and BPDE-deoxyadenosine adducts, as well as those derived from further metabolism of 9-hydroxybenzo(alpha)pyrene were formed in three strains of mice reported to have widely differing susceptibilities to polycyclic hydrocarbon-induced skin carcinogenesis. The relevance of these different hydrocarbon-DNA adducts to carcinogenesis requires further investigation.

Animals↗
PubMed1989

Glucose and sulfate conjugation of phenolic compounds by the spiny lobster (Panulirus argus).

Previous work has shown that the hepatopancreas of the spiny lobster (Panulirus argus) contains a mixed-function oxidase system capable of catalyzing the monooxygenation of polycyclic aromatic hydrocarbons to highly toxic products similar to those formed by mammalian tissues. Studies were designed to determine the ability of the spiny lobster to conjugate the phenolic compounds 4-methylumbelliferone, p-nitrophenol, beta-naphthol, and 3-hydroxybenzo[a]pyrene with endogenous molecules. The hepatopancreas contained UDP-glucose (UDPG) dependent glucosyltransferase, while no activity was detected when UDP-glucuronic acid was used as the cosubstrate. Atypical Michaelis-Menten kinetics result with varying concentrations of UDPG, indicating that multiple forms of glucosyltransferase may exist in this organ. The activity was localized in the microsomal fraction, exhibited a pH optimum at 8.0-8.5, and a temperature optimum of 30 degrees C. Sulfate conjugation was found only in the cytosolic fraction of the antennal gland and used adenosine 3'-phosphate 5'-phosphosulfate (PAPS) as the sulfate donor (Km(apparent) = 9.0 +/- 4.9 microM). Hepatopancreas cytosol inhibited sulfotransferase activity. The pH optimum of antennal gland sulfotransferase was a function of the substrate and ranged from 5.5 to 7.4. Analysis of spiny lobster urine 24 hr following exposure to 3-hydroxybenzo[a]pyrene demonstrated the ability of the lobster to form both the sulfate and glucoside conjugate in vivo.

Animals↗
PubMed1984

Expanded solubility parameter approach. I: Naphthalene and benzoic acid in individual solvents.

An expanded solubility parameter system was tested in conjunction with the extended Hansen solubility approach and the UNIFAC method to calculate the solubilities of naphthalene and benzoic acid in polar and nonpolar solvents. The expanded parameter system is characterized by delta d for the dispersion force, delta p for dipolar forces, a basic or electron-donor parameter, delta b, and an acidic or electron-acceptor parameter delta a. The correlation between the calculated and observed solubilities of benzoic acid was increased by use of the four-parameter system. An indicator variable was required to bring the solubilities into line in strongly dipolar solvents such as N,N-dimethylformamide. For naphthalene, use of the four-parameter approach proved not to be an improvement over the three-parameter extended Hansen solubility approach. The UNIFAC method was not successful in calculating solubilities of benzoic acid in the 40 polar and nonpolar solvents. A triangular plot of the three Hansen parameters for benzoic acid, p-hydroxybenzoic acid, and methyl p-hydroxybenzoate illustrated the contributions of dispersion, dipolar, and Lewis acid-base (hydrogen bonding) interaction forces among the three benzoic acid compounds and the various classes of solvents. A multiple regression procedure for calculating the four partial solubility parameters of drug solutes was developed.

Benzoates↗
PubMed2005

Determination of preservatives in cosmetics and food samples by micellar liquid chromatography.

An analytical procedure has been developed for the analysis of benzoic acid, p-hydroxybenzoic acid, methyl-, ethyl-, propyl-, isopropyl-, and butyl esters of p-hydroxybenzoic acid by micellar liquid chromatography. After dilution in n-propanol the sample was directly injected onto a Lichrosorb ODS, 5 microm (250 x 4.6 mm ID) column and eluted with aqueous 2% Brij-35 adjusted to pH 3.0 with phosphoric acid:propanol (80:20 v/v) at a flow rate of 1 mL min(-1) and UV detection at 254 nm. A linear calibration curve was obtained simultaneously for each component in the range of 50-500 microg mL(-1) for benzoic acid and 5-150 microg mL(-1) for the other components; detection limits were within 25-250 ng mL(-1) corresponding to 125-1250 pg per injection (5 microL). The reproducibility in terms of average peak area and average retention time was obtained with coefficients of variation (CV) of 1.2% and 0.5%. The method was applied to analysis of these compounds in cosmetics (shampoos, hand lotions, creams, and bath foam) and food samples.

Animals↗
PubMed2003

Isolation, characterization and biological activity of betulinic acid and ursolic acid from Vitex negundo L.

Two pentacyclic triterpenoids, betulinic acid (3beta-hydroxylup-20-(29)-en-28-oic acid) (3), and ursolic acid (2beta-hydroxyurs-12-en-28-oic acid) (4), were isolated for the first time from leaves of Vitex negundo L. along with three other compounds; an aliphatic alcohol n-hentriacontanol (1), beta-sitosterol (2) and p-hydroxybenzoic acid (5). Their antifeedant activity against the larvae of an agricultural pest, the castor semilooper (Achoea janata), in a no-choice laboratory assay and their antibacterial activity against Bacillus subtilis and Escherichia coli, by the paper disc method, were tested. Ursolic acid (4) showed more effective antifeedant activity than the betulinic acid (3). However, both these compounds have shown a very mild antibacterial activity. The other three compounds; n-hentriacontanol (1), beta-sitosterol (2) and p-hydroxybenzoic acid (5) have shown a little antifeedant activity against the larvae and did not show any antibacterial activity.

Animals↗
PubMed2003

Anti-sickling potential of a Nigerian herbal formula (ajawaron HF) and the major plant component (Cissus populnea L. CPK).

The anti-sickling activities of the extracts of the roots of a plant Cissus populnea L. (CPK) (a major constituent of a herbal formula Ajawaron HF used in the management of sickle cell disease in south-west Nigeria) has been examined. Phytochemical examination of the extract showed the presence of anthraquinone derivatives, steroidal glycosides and cardiac glycosides. Alkaloids and tannins were completely absent in the CPK extracts. Evaluation of the anti-sickling activity involved the use of both positive (p-hydroxybenzoic acid, 5 microg/mL) and negative control (normal saline) for each set of experiments aimed at the inhibition of sodium metabisulphite-induced sickling of the HbSS red blood cells obtained from confirmed non-crisis state sickle-cell patients. The chloroform and water partitioned fractions of the cold methanol extracts of CPK exhibited a 62.2% and 52.9% inhibition of sickling, respectively, at 180 min. The herbal formula (HF) aqueous extract showed the highest anti-sickling activity on a weight by weight basis of all the extracts and fractions tested, giving a 71.4% inhibition of sickling at the end of 180 min incubation when compared with the normal saline control. The maximum percentage inhibition of sickling exhibited by the p-hydroxybenzoic acid control was 46.0% at 90 min incubation.

Anemia, Sickle Cell↗
PubMed1993

Quantitative aspects of the matrix-assisted laser desorption mass spectrometry of complex oligosaccharides.

Comparative studies of the matrix-assisted laser desorption ionization of complex oligosaccharides were made using a range of mono, di- and tri-substituted benzoic acids, substituted coumarins and cinnamic acids. The best results were obtained with 2,5-dihydroxybenzoic acid (2,5-DHB). Detection limits using this matrix were in the range of 100 fmol for complex and high mannose sugars, some 2-fold better than those obtained with alpha-cyano-4-hydroxycinnamic acid and 10-fold better than with an earlier oligosaccharide matrix, 3-amino-4-hydroxybenzoic acid. The strongest signals were achieved with a matrix-to-sample ratio of about 5000:1. Little correlation was found between the measured peak height and sample loading when 3-amino-4-hydroxybenzoic acid was used as the matrix and the signal appeared to saturate at a sample level of around 30 pmol. However, good correlation was found between the amount of sample loaded onto the target and the response when an analogous compound was used as an internal standard and peak ratios were measured. In contrast to this, the use of 2,5-dihydroxybenzoic acid as the matrix enabled the oligosaccharide to be measured over the range 100 fmol to at least 100 pmol with an excellent linear correlation between sample quantity and response and without the need of a standard. No evidence of saturation was found with this matrix. With 2,5-DHB (other matrices were not tested), the oligosaccharide signal strength was found to fall with increasing molecular weight in a linear manner and similar to that found previously with proteins.(ABSTRACT TRUNCATED AT 250 WORDS)

Mass Spectrometry↗
PubMed2000

The effects of aliphatic (n-nonane), naphtenic (1,2, 4-trimethylcyclohexane), and aromatic (1,2,4-trimethylbenzene) hydrocarbons on respiratory burst in human neutrophil granulocytes.

This study investigates the effects of aliphatic (n-heptane, n-nonane), naphtenic (methylcyclohexane, 1,2,4-trimethylcyclohexane (TMCH)), and aromatic (methylbenzene, 1,2,4-trimethylbenzene (TMB)) hydrocarbons on respiratory burst in human granulocytes. The free radical formation was measured as 2,7-dichlorofluorescein diacetate-amplified (DCF) fluorescence, by electron paramagnetic resonance (EPR) spectroscopy and by hydroxylation of 4-hydroxybenzoate. The chemotactic peptide N-formyl-met-leu-phe (fMLP) and phorbol 12-myristate 13-acetate (PMA), a diacylglycerol analogue, were included as positive controls. DCF fluorescence was elevated in a concentration-dependent manner by C9 hydrocarbons. The C7 hydrocarbons did not stimulate respiratory burst in the concentration range examined. The naphtenic hydrocarbon TMCH showed the strongest effect on respiratory burst and was therefore selected for mechanistic studies of this free radical formation. In the absence of extracellular Ca(2+), fluorescence in response to TMCH and fMLP was reduced by 77 and 90%, respectively. Preincubation of the granulocytes with the protein kinase C inhibitor bisindolylmaleimide reduced the DCF fluorescence stimulated with TMCH, fMLP, and PMA by 82, 56, and 90%, respectively. The phospholipase C inhibitor U73122 lowered the TMCH- and fMLP-activated DCF fluorescence by 87 and 76%. In addition, the TMCH- and fMLP-induced DCF fluorescence, after the preincubation with the phospholipase D modulator n-butanol, was lowered by 83 and 52%, respectively. The importance of protein kinase C, phospholipase C, and phospholipase D for elevation of respiratory burst was also demonstrated by the EPR experiments using the spin trap 5-diethoxyphosphoryl-5-methyl-1-pyrroline-N-oxide (DEPMPO). Preincubation with the NADPH oxidase inhibitor diphenyleneiodonium and diethyldithiocarbamate, which inhibits superoxide dismutase, led to an almost complete reduction of DCF fluorescence in response to TMCH, fMLP, and PMA. Preincubation with diethyldithiocarbamate led to the elevation of superoxide adducts of DEPMPO. The hydrocarbons stimulated formation of mainly the superoxide (O(*-)(2)) adduct of DEPMPO (DEPMPO-OOH) but also small amounts of the hydroxyl adduct ((*)OH) (DEPMPO-OH). Using 4-hydroxybenzoate as a hydroxyl radical trap confirmed formation of (*)OH after stimulation with the hydrocarbons. In conclusion, our findings indicate that TMCH-activated respiratory burst is dependent on the Ca(2+)-dependent phospholipase C, phospholipase D, and protein kinase C prior to activation of the NADPH oxidase.

1-Butanol↗
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↗
PubMed1994

Evidence that phenol phosphorylation to phenylphosphate is the first step in anaerobic phenol metabolism in a denitrifying Pseudomonas sp.

Anaerobic phenol degradation has been shown to proceed via carboxylation of phenol to 4-hydroxybenzoate. However, in vitro the carboxylating enzyme was inactive with phenol; only phenylphosphate (phosphoric acid monophenyl ester) was readily carboxylated. We demonstrate in a denitrifying Pseudomonas strain that phenylphosphate is the first detectable product formed from phenol in whole cells and that subsequent phenylphosphate consumption parallels 4-hydroxybenzoate formation. These kinetics are consistent with phosphorylation being the first step in anaerobic phenol degradation. Various cosubstrates failed so far to act as phosphoryl donor for net phosphorylation of phenol in cell extracts. Yet, cells anaerobically grown with phenol contained an enzyme that catalyzed an isotope exchange between [U-14C]phenol and phenylphosphate. This transphosphorylation activity was anaerobically induced by phenol but was stable under aerobic conditions and required Mn2+ and polyethylene glycol. Activity was optimal at pH 5.5 and half-maximal with 0.6 mM Mn2+, 0.2 mM phenylphosphate, and 1 mM phenol. It is proposed that the phenol exchange/transphosphorylation reaction is catalyzed as partial reaction by an inducible phenol phosphorylating enzyme. The isotope exchange demands that a phosphorylated enzyme was formed in the course of the reaction, which might be similar to the phosphotransferase system of sugar transport.

Anaerobiosis↗
PubMed1987

Anaerobic degradation of phenol by pure cultures of newly isolated denitrifying pseudomonads.

From various oxic or anoxic habitats several strains of bacteria were isolated which in the absence of molecular oxygen oxidized phenol to CO2 with nitrate as the terminal electron acceptor. All strains grew in defined mineral salts medium; two of them were further characterized. The bacteria were facultatively anaerobic Gram-negative rods; metabolism was strictly oxidative with molecular oxygen, nitrate, or nitrite as electron acceptor. The isolates were tentatively identified as pseudomonads. Besides phenol many other benzene derivatives like cresols or aromatic acids were anaerobically oxidized in the presence of nitrate. While benzoate or 4-hydroxybenzoate was degraded both anaerobically and aerobically, phenol was oxidized under anaerobic conditions only. Reduced alicyclic compounds were not degraded. Preliminary evidence is presented that the first reaction in anaerobic phenol oxidation is phenol carboxylation to 4-hydroxybenzoate.

Anaerobiosis↗
PubMed1985

Contraluminal sulfate transport in the proximal tubule of the rat kidney. IV. Specificity: salicylate analogs.

In order to study the specificity of the contraluminal sulfate transport system the inhibitory potency of salicylate analogs (5 mmol/l each) on the 35SO4(2-) influx from the interstitium into cortical tubular cells in situ has been determined. The following was found: 2-hydroxybenzoate (salicylate), per se, did not inhibit contraluminal 35SO4(2-) influx. The same holds when an additional NH2-group was introduced in position 4 or 5, or when an additional Cl-group was introduced in position 4. When an additional Cl- or NO2-group was introduced in position 5 a moderate inhibition was seen (app. Ki approximately equal to 4 mmol/l). However, introduction of 2 Cl- or 2NO2-groups in position 3 and 5 creates compounds with strong inhibitory potency (app. Ki approximately equal to 0.5 mmol/l). 2-hydroxy-3,5-iodobenzoate inhibited too, but with a smaller inhibitory potency (app. Ki approximately equal to 2.3 mmol/l). 2-hydroxybenzoate analogs, which have a carboxy- or sulfo-group in position 5, exerted strong inhibition, those with a acetyl- or butyryl-group exerted moderate inhibition. 1-Naphthol-2-carboxylate did not inhibit, while 1-naphthol-4-sulfamoyl-2-carboxylate did. Amongst the dihydroxybenzoates, 2,3- and 2,5-dihydroxybenzoate did not inhibit contraluminal 35SO4(2-) influx, while 2,4- and 2,6-dihydroxybenzoate did. The data indicate that a hydroxy-group in ortho-position and an electro-negative group in the meta-position to the carboxyl group and paraposition to the hydroxy-group are essential for interaction with the contraluminal sulfate transport system. The ability of 2,6-dihydroxybenzoate to inhibit might be explained by its ability to undergo mesomeric conformation.

Animals↗
PubMed1992

Anoxygenic degradation of aromatic substances by Rhodopseudomonas palustris.

Three strains of the phototrophic purple nonsulfur bacterium Rhodopseudomonas palustris were isolated from different environments and were evaluated for their aromatic degradative potential under phototrophic conditions. All three strains (PFR1, PNR4, and MRL1) utilized benzoate, 4-hydroxybenzoate, 4-aminobenzoate, 4-aminophenol, cinnamate, ferulate, phloroglucinol, and 4-dimethylaminobenzaldehyde in the absence of exogenous CO2. 4-Aminobenzoate and 4-aminophenol served as a carbon and nitrogen source for all the three strains. Utilization of 4-aminophenol was enhanced in the presence of 4-hydroxybenzoate. Salicylate was utilized by PFR1 and MRL1 strains, and phenol was utilized by the MRL1 strain only in the presence of exogenous CO2.

Anaerobiosis↗
PubMed2005

Immunobiological [correction of Immunobioloical] activity of a new benzyl benzoate from the aerial parts of Solidago virga-aurea var. gigantea.

The chromatographic separation of the hexane soluble fraction of the methanol extract of the aerial parts of Solidago virga-aurea var. gigantea M(IQ*) (Compositae) led to the isolation of a new benzylbenzoate (1) together with four known benzylbenzoates (2-5). Their structures were determined as 2-methoxybenzyl-2-hydroxybenzoate (1), benzyl-2-hydroxy-6-methoxybenzoate (2), 2-methoxybenzyl-2,6-dimethoxybenzoate (3), 2-methoxybenzyl-2-methoxy-6-hydroxybenzoate (4), and benzyl-2,6-dimethoxybenzoate (5). Their structures were established by spectroscopic methods. Biological effects of compounds, 1 and 2, were investigated in vitro using mouse peritoneal macrophages. The benzylbenzoates (1 and 2) could serve as immunotherapeutic agents by stimulating macrophage functions, with potential use in the treatment of infectious diseases.

Adjuvants, Immunologic↗