The asymmetric unit of the three-component title compound, 2,2'-di-thiodi-benzoic acid-2-chloro-benzoic acid-N,N-di-methyl-formamide (1/1/1), C14H10O4S2·C7H5ClO2·C3H7NO, contains a mol-ecule each of 2,2'-di-thiodi-benzoic acid (DTBA), 2-chloro-benzoic acid (2CBA) and di-methyl-formamide (DMF). The DTBA mol-ecule is twisted [the C-S-S-C torsion angle is 88.37 (17)°] and each carb-oxy-lic group is slightly twisted from the benzene ring to which it is connected [CO2/C6 dihedral angles = 7.6 (3) and 12.5 (3)°]. A small twist is evident in the mol-ecule of 2CBA [CO2/C6 dihedral angle = 4.4 (4)°]. In the crystal, the three mol-ecules are connected by hydrogen bonds with the two carb-oxy-lic acid residues derived from DTBA and 2CBA forming a non-symmetric eight-membered {⋯HOCO}2 synthon, and the second carb-oxy-lic acid of DTBA linked to the DMF mol-ecule via a seven-membered {⋯HOCO⋯HCO} heterosynthon. The three-mol-ecule aggregates are connected into a supra-molecular chain along the a axis via DTBA-C-H⋯O(hydroxyl-2CBA), 2CBA-C-H⋯O(hydroxyl-DTBA) and DTBA-C-H⋯S(DTBA) inter-actions. Supra-molecular layers in the ab plane are formed as the chains are linked via DMF-C-H⋯S(DTBA) contacts, and these inter-digitate along the c-axis direction without specific points of contact between them. A Hirshfeld surface analysis points to additional but, weak contacts to stabilize the three-dimensional architecture: DTBA-C=O⋯H(phenyl-DTBA), 2CBA-Cl⋯H(phenyl-DTBA), as well as a π-π contact between the delocalized eight-membered {⋯HOC=O}2 carb-oxy-lic dimer and the phenyl ring of 2CBA. The latter was confirmed by electrostatic potential (ESP) mapping.
In the title compound, C26H22N2O2, the dihedral angles between the 1-methyl-indole units (A and B) and the benzoic acid moiety (C) are A/B = 64.87 (7), A/C = 80.92 (8) and B/C = 75.05 (8)°. An intra-molecular C-H⋯O inter-action arising from the methyne group helps to establish the conformation. In the crystal, R22(8) carb-oxy-lic acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds are observed. A Hirshfeld surface analysis shows that the greatest contributions are from H⋯H, C⋯H/H⋯C and O⋯H/H⋯O contacts (percentage values = 54.6%, 29.6% and 10.1%, respectively).
The development of new alternatives strategies to synthetic insecticides aimed at reducing pest populations by developing pesticides based on plant extracts without negative effects in non target organisms and environment. The present study was undertaken in order to assess the insecticidal activity of the crude methanolic extract of the Algerian Asteraceae Cotula cinerea, against the larval and the pupal stage of Culex pipiens (Diptera: Culicidae). It is also to determine the chemical composition of the used extract, and to understand the mechanism of toxic action of the tested extract. Based on the preliminary tests, five concentrations of the crude methanolic extract of C. cinerea (0.62, 1.25, 2.50, 3.75, and 5 mg/mL) were tested for their insecticidal activity according to the protocol recommended by the World Health Organization. The chemical profile of the extract was also obtained by high performance liquid chromatography (HPLC). Histopathological effects and inhibition of acetylcholinesterase activity in treated mosquitoes with LC90 were examined to elucidate the mechanism of the toxic effect of the tested extract (48 h post treatment). Eight compounds have been identified by HPLC. That includes four flavonoids (rutin, quercetin, myrcetin and cathechin), three phenolic acids (benzoic acid, vanillic acid, p-coumaric acid) and one alkaloid (berberine). C. cinerea methanolic extract showed good larvicidal and pupicidal activities with LC50 and LC90 values of 1.10 and 4.37 mg/mL respectively against pupae, 24h post treatment and 1.26, 2.35 mg/mL respectively against the fourth instar larvae. Data of enzymatic assay performed on LC50 and LC90 pupae and larvae revealed prominent neurotoxic effects. C. cinerea extract reduced the activity of acetylcholinesterase (AChE) enzyme in a concentration dependent manner. Obtained inhibition percentages, 48 h after treatment, were 35.11 ± 7.44 and 51.83 ± 4.04% for pupal stage and 30.98 ± 2.97 % and 48.77 ± 4.72% for the fourth instar larvae for LC50 and LC90 values respectively. Treated larvae and pupae showed also histopathological damages in the pupal cuticle and larval midgut. The results of this study showed that C. cinerea crude methanolic extract could be considered as an eco-friendly alternative for mosquito control.
The asymmetric unit of the title 1:2 co-crystal, C14H10O4S2·2C7H6O2, comprises half a mol-ecule of di-thiodi-benzoic acid [systematic name: 2-[(2-carb-oxy-phen-yl)disulfan-yl]benzoic acid, DTBA], as the mol-ecule is located about a twofold axis of symmetry, and a mol-ecule of benzoic acid (BA). The DTBA mol-ecule is twisted about the di-sulfide bond [the C-S-S-C torsion angle is -83.19 (8)°] resulting in a near perpendicular relationship between the benzene rings [dihedral angle = 71.19 (4)°]. The carb-oxy-lic acid group is almost co-planar with the benzene ring to which it is bonded [dihedral angle = 4.82 (12)°]. A similar near co-planar relationship pertains for the BA mol-ecule [dihedral angle = 3.65 (15)°]. Three-mol-ecule aggregates are formed in the crystal whereby two BA mol-ecules are connected to a DTBA mol-ecule via hy-droxy-O-H⋯O(hydroxy) hydrogen bonds and eight-membered {⋯HOC=O}2 synthons. These are connected into a supra-molecular layer in the ab plane through C-H⋯O inter-actions. The inter-actions between layers to consolidate the three-dimensional architecture are π-π stacking inter-actions between DTBA and BA rings [inter-centroid separation = 3.8093 (10) Å] and parallel DTBA-hy-droxy-O⋯π(BA) contacts [O⋯ring centroid separation = 3.9049 (14) Å]. The importance of the specified inter-actions as well as other weaker contacts, e.g. π-π and C-H⋯S, are indicated in the analysis of the calculated Hirshfeld surface and inter-action energies.
Cresol Red, a commercial dye that used widely to color nylon, wool, cotton, and polyacrylonitrile-modified nylon in the massive textile manufacture is toxic recalcitrant. Absidia spinosa M15, a novel fungal strain isolated from a tropical rain forest, was found to decolorize Cresol Red 65% within 30 d under agitation condition. UV-Vis spectroscopy, TLC analysis and mass spectra of samples after decolorization process in culture medium confirmed final decolorization of Cresol Red. Two metabolites were identified in the treated medium: benzeneacetic acid (tR 9.6 min and m/z 136) and benzoic acid (tR 5.7 min and m/z 122). Laccase showed the significant activity (133.8 U/L) in biomass obtained at the end of experiment demonstrates role of the enzyme in the decolorization process.
Fabrication of a test strip for detection of benzoic acid was successfully implemented by immobilizing tyrosinase, phenol and 3-methyl-2-benzothiazolinone hydrazone (MBTH) onto filter paper using polystyrene as polymeric support. The sensing scheme was based on the decreasing intensity of the maroon colour of the test strip when introduced into benzoic acid solution. The test strip was characterized using optical fiber reflectance and has maximum reflectance at 375 nm. It has shown a highly reproducible measurement of benzoic acid with a calculated RSD of 0.47% (n = 10). The detection was optimized at pH 7. A linear response of the biosensor was obtained in 100 to 700 ppm of benzoic acid with a detection limit (LOD) of 73.6 ppm. At 1:1 ratio of benzoic acid to interfering substances, the main interfering substance is boric acid. The kinetic analyses show that, the inhibition of benzoic is competitive inhibitor and the inhibition constant (K(i)) is 52.9 ppm. The activity of immobilized tyrosinase, phenol, and MBTH in the test strip was fairly sustained during 20 days when stored at 3 °C. The developed test strip was used for detection of benzoic acid in food samples and was observed to have comparable results to the HPLC method, hence the developed test strip can be used as an alternative to HPLC in detecting benzoic acid in food products.
A reversed-phased HPLC method that allows the separation and simultaneous determination of the preservatives benzoic (BA) and sorbic acids (SA), methyl- (MP) and propylparabens (PP) is described. The separations were effected by using an initial mobile phase of methanol-acetate buffer (pH 4.4) (35:65) to elute BA, SA and MP and changing the mobile phase composition to methanol-acetate buffer (pH 4.4) (50:50) thereafter. The detector wavelength was set at 254 nm. Under these conditions, separation of the four components was achieved in less than 23 min. Analytical characteristics of the separation such as limit of detection, limit of quantification, linear range and reproducibility were evaluated. The developed method was applied to the determination of 67 foodstuffs (mainly imported), comprising soft drinks, jams, sauces, canned fruits/vegetables, dried vegetables/fruits and others. The range of preservatives found were from not detected (nd)--1260, nd--1390, nd--44.8 and nd--221 mg kg(-1) for BA, SA, MP and PP, respectively.
A biotechnological route via enzymatic esterification was proposed as an alternative way to synthesize the problematic anti-oxidant eugenyl benzoate. The new method overcomes the well-known drawbacks of the chemical route in favor of a more sustainable reaction process. The present work reports a Box-Behnken design (BBD) optimization process to synthesize eugenyl benzoate by esterification of eugenol and benzoic acid catalyzed by the chitosan-chitin nanowhiskers supported Rhizomucor miehei lipase (RML-CS/CNWs). Effects of four reaction parameters: reaction time, temperature, substrate molar ratio of eugenol: benzoic acid and enzyme loading were assessed. Under optimum conditions, a maximum conversion yield as high as 66% at 50°C in 5h using 3mg/mL of RML-CS/CNWs, and a substrate molar ratio (eugenol: benzoic acid) of 3:1. Kinetic assessments revealed the RML-CS/CNWs catalyzed the reaction via a ping-pong bi-bi mechanism with eugenol inhibition, characterized by a Vmax of 3.83mMmin-1. The Michaelis-Menten constants for benzoic acid (Km,A) and eugenol (Km,B) were 34.04 and 138.28mM, respectively. The inhibition constant for eugenol (Ki,B) was 438.6mM while the turnover number (kcat) for the RML-CS/CNWs-catalyzed esterification reaction was 40.39min-1. RML-CS/CNWs were reusable up to 8 esterification cycles and showed higher thermal stability than free RML.
Hoja santa (Piper auritum) refers to an important presence in Mexican cuisine. The information of this review article was gathered from several electronic sources such as Scopus, Medline, Scielo, ScienceDirect, SciFinder, Web of Science, Google Scholar and Lilacs. Phytochemical studies have revealed the presence of benzoic acid derivatives, phenylpropanoids and triterpenoids, while the essential oils have shown its richness in safrole, hence it has several activities, such as antioxidant, toxicity, insecticidal, anti-diabetic and cytotoxic properties. This review is expected to draw the attention of medical professionals and the general public towards P. auritum as well as to open the door for detailed research in the future.
For the rapid simultaneous determination of monosodium glutamate (MSG), benzoic acid (BA), and sorbic acid (SA) in canned food and other processed food samples, we developed a method that combines in-capillary derivatization with separation by capillary electrophoresis. This method employs the rapid derivatization of MSG with o-phthalaldehyde (OPA) in the presence of 3-mercaptopropionic acid (3-MPA) and enables the detection of the resulting OPA-MSG derivative and of non-derivatized BA and SA at 230nm. The composition of the background electrolyte and the parameters of derivatization and separation are as follows: 25mM borax containing 5mM OPA and 6mM 3-MPA, separation voltage 25mV, injection at 30mbar for 20s, and column temperature 25°C. Because of the high reaction rate and suitably adapted effective electrophoretic mobilities, band broadening due to the derivatization reaction at the start of the separation process is kept to a minimum. The optimized method is validated with respect to LOD, LOQ, linearity, recovery, and precision. This method can be applied to real samples such as soy, fish, oyster and sweet and sour chili sauces after application of appropriate clean-up steps. Mechanisms of zone broadening and zone focusing are discussed showing the validity of the employed theoretical approach regarding the dependence of the peak shape for OPA-MSG on the concentration of MSG in the sample.
To overcome drawbacks in the conventional chemical route to synthesize eugenyl benzoate, immobilized Rhizomucor miehei lipase (RML) as the biocatalyst was proposed. The RML conjugated to a hybrid support consisting of biopolymers, chitosan (CS) and chitin nanowhiskers (CNWs). 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDAC) was used as the crosslinker to bind the lipase. Immobilization of RML was the highest on crosslinked CS/CNWs which gave a protein loading of ∼8.12 mg/g, corresponding to specific and residual activity of 537 U/g and 137%, respectively. Fourier transform infrared spectroscopy, thermogravimetric analysis-differential thermogravimetry, field emission scanning electron and atomic force microscopy of RML-CS/CNWs revealed that RML was successfully attached to the surface of crosslinked CS/CNWs. Under an optimized condition, the highest yield of eugenyl benzoate (56.3%) was attained after 5 h using 3 mg/mL of RML-CS/CNWs with molar ratio of eugenol: benzoic acid of 3:1, as compared to only 47.3% for the free RML. Analyses of FTIR and NMR on purified eugenyl benzoate affirmed that the ester was successfully produced in the enzymatic esterification. Therefore, the use of the RML-CS/CNWs biocatalysts appears promising to afford good yields of eugenyl benzoate within a relatively shorter reaction time.
Detail chemical studies on Carcinia maingayi have yielded one xanthone, 1,3,7-trihydroxy-2-(3-methylbut-2-enyl)-xanthone, one benzophenone, isoxanthochymol, one benzoic acid derivative 3,4-dihydroxy-methylbenzoate and two triterpenoids, stigmasterol and sitosterol. Meanwhile, investigations on Carcinia parvifolia have afforded one triterpenoid, a-amyrin and two xanthones, cowanin and rubraxanthone. Their structures were derived based on spectroscopic evidence, mainly ID and 2D NMR spectroscopy. Acetylation reaction was carried out on rubraxanthone to yield triacetate rubraxanthone. It was found that the pure rubraxanthone was strongly active against the larvae of Aedes aegypti with LC50 value of 15.49 {lg/ ml and HL-60 cells line with an IC50 value of 7.5 {lg/ ml.
Liquid-liquid extraction (LLE) of methylene blue (MB) from industrial wastewater using benzoic acid (extractant) in xylene has been studied at 27 degrees C. The extraction of the dye increased with increasing extractant concentration. The extraction abilities have been studied on benzoic acid concentration in the range of 0.36-5.8x10(-2) M. The distribution ratio of the dye is reasonably high (D=49.5) even in the presence of inorganic salts. Irrespective of the concentration of dye, extraction under optimal conditions was 90-99% after 15 min of phase separation. The extracted dye in the organic phase can be back extracted into sulphuric acid solution. The resultant recovered organic phase can be reused in succeeding extraction of dye with the yield ranging from 99 to 87% after 15 times reused, depending on the concentration of the initial feed solution. Experimental parameters examined were benzoic acid concentration, effect of diluent, effect of pH, effect of initial dye concentration, effect of equilibration time, various stripping agents, aqueous to organic phase ratio in extraction, organic to aqueous phase ratio in stripping and reusability of solvent.
The objective of this study was to determine the level of preservatives and microbiological loads in various brands of commercially available chili bo (paste). Fifteen different brands of chili bo obtained from the local market and hypermarkets were analyzed for pH, moisture and benzoic acid content, microbiological loads (aerobic, anaerobic, aerobic spores, and fungi), and thermophilic microorganisms. Results showed that both moisture content and pH vary among samples. The concentrations of benzoic acid detected in chili bo were found to be in the range of 537 to 5,435 mg/kg. Nine of fifteen brands were found to exceed the maximum level permitted by the Malaysian Food Law in accordance with the Codex Alimentarius (1,000 mg/kg for benzoic acid). An apparent correlation between benzoic acid concentration and microbiological loads present in the chili bo was observed. The microbiological loads were found to be relatively low in the end products containing high amounts of benzoic acid. The heat-resistant (70 to 80 degrees C) microorganisms present in chili bo were identified as Ochrobacterum tritici, Stenotrophomonas rhizophila, Microbacterium maritypicum, Roseomonas spp., CDC group II-E subgroup A, Flavimonas oryzihabitans, and Pseudomonas aeruginosa, with M. maritypicum being the most frequently found (in 9 of 15 samples) microorganism. Most of these identified microorganisms were not known to cause foodborne illnesses.
The present study aimed to screen plants for bioactive compounds with potential antibacterial activities. In our efforts to evaluate plants from Borneo, we isolated and elucidated the structures of four natural products from the bioactive fraction of a chloroform extract of Goniothalamus longistipetes using various chromatographic and spectroscopic techniques. The bioactive compounds were identified as a known styryllactone, (+)-altholactone ((2S,3R,3aS,7aS)-3-hydroxy-2-phenyl-2,3,3a,7a-tetrahydrobenzo-5(4H)-5-one) (1), a new styryllactone, (2S,3R,3aS,7aS)-3-hydroxy-2-phenyl-2,3,3a,7a-tetrahydrobenzo-5(4H)-5-one) (2) as well as a new alkaloid, 2,6-dimethoxyisonicotinaldehyde (3) and a new alkenyl-5-hydroxyl-phenyl benzoic acid (4). 1 and 4 showed broad-spectrum anti-bacterial activities against Gram-positive and Gram-negative bacteria as well as acid-fast model selected for this study. Compound 2 only demonstrated activities against Gram-positive bacteria whilst 3 displayed selective inhibitory activities against Gram-positive bacterial strains. Additionally, their mechanisms of anti-bacterial action were also investigated. Using Mycobacterium smegmatis as a fast-growing model of tubercle bacilli, compounds 1, 2 and 4 demonstrated inhibitory activities against whole-cell drug efflux and biofilm formation; two key intrinsic mechanisms of antibiotic resistance. Interestingly, the amphiphilic compound 4 exhibited inhibitory activity against the conjugation of plasmid pKM101 in Escherichia coli using a plate conjugation assay. Plasmid conjugation is a mechanism by which Gram-positive and Gram-negative-bacteria acquire drug resistance and virulence. These results indicated that bioactive compounds isolated from Goniothalamus longistipetes can be potential candidates as 'hits' for further optimisation.
Neurodegenerative diseases are linked to neuronal cell death and impairment of neurite outgrowth. An edible mushroom, Pleurotus giganteus was found to stimulate neurite outgrowth in vitro but the chemical constituents and the underlying mechanism is yet to be elucidated. The chemical constituents of P. giganteus (linoleic acid, oleic acid, cinnamic acid, caffeic acid, p-coumaric acid, succinic acid, benzoic acid, and uridine) were tested for neurite outgrowth activity. Uridine (100 μM) was found to increase the percentage of neurite-bearing cells of differentiating neuroblastoma (N2a) cells by 43.1 ± 0.5%, which was 1.8-fold higher than NGF (50 ng/mL)-treated cells. Uridine which was present in P. giganteus (1.80 ± 0.03 g/100g mushroom extract) increased the phosphorylation of extracellular-signal regulated kinases (ERKs) and protein kinase B (Akt). Further, phosphorylation of the mammalian target of rapamycin (mTOR) was also increased. MEK/ERK and PI3K-Akt-mTOR further induced phosphorylation of cAMP-response element binding protein (CREB) and expression of growth associated protein 43 (GAP43); all of which promoted neurite outgrowth of N2a cells. This study demonstrated that P. giganteus may enhance neurite outgrowth and one of the key bioactive molecules responsible for neurite outgrowth is uridine.