Vapor Pressure of Methyl Salicylate and n-Hexadecane

DTIC Science & Technology

2014-01-01

VAPOR PRESSURE OF METHYL SALICYLATE AND N-HEXADECANE ECBC-TR-1184 David E. Tevault Leonard C. Buettner...REPORT TYPE Final 3. DATES COVERED (From - To) Mar 2000-Dec 2001 4. TITLE AND SUBTITLE Vapor Pressure of Methyl Salicylate and n-Hexadecane 5a...ABSTRACT Vapor pressure data are reported for O-hydroxybenzoic acid, methyl ester, more commonly known as methyl salicylate (MeS), and n-hexadecane in

Methyl salicylate overdose

MedlinePlus

Methyl salicylate (oil of wintergreen) is a chemical that smells like wintergreen. It is used in many over- ... muscle ache creams. It is related to aspirin. Methyl salicylate overdose occurs when someone swallows a dangerous amount ...

Functional analysis of a tomato salicylic acid methyl transferase and its role in synthesis of the flavor volatile methyl salicylate

USDA-ARS?s Scientific Manuscript database

Methyl salicylate (MeSA) is a volatile plant secondary metabolite that is an important contributor to taste and scent of many fruits and flowers. It is synthesized from salicylic acid (SA), a phytohormone that contributes to plant pathogen defense. MeSA is synthesized by members of a family of O-met...

Ovicidal and larvicidal activity and possible mode of action of phenylpropanoids and ketone identified in Syzygium aromaticum bud against Bradysia procera.

PubMed

Hong, Tae-Kyun; Perumalsamy, Haribalan; Jang, Kyoung-Hwa; Na, Eun-Shik; Ahn, Young-Joon

2018-02-01

Bradysia procera is a serious insect pest of Panax ginseng plants. This study was conducted to determine the toxicity and mechanism of action of three phenylpropanoids, three terpenoids, and a ketone from Syzygium aromaticum bud methanol extract and hydrodistillate against third-instar larvae and eggs of B. procera. In a filter-paper mortality bioassay, methyl salicylate (LC 50 , 5.26μg/cm 2 ) was the most toxic compound, followed by 2-nonanone, eugenol, and eugenyl acetate (8.77-15.40μg/cm 2 ). These compounds were significantly less toxic than either thiamethoxam, clothianidin, or cypermethrin. Egg hatching was inhibited by 97, 85, and 40% at 11.7μg/cm 2 of methyl salicylate, 2-nonanone, and eugenol, respectively. The egg-hatching inhibition of these insecticides was between 90 and 94% at 0.09μg/cm 2 . These constituents were consistently more toxic in closed versus open containers, indicating that toxicity was achieved mainly through the action of vapor. The mechanism of larvicidal action of methyl salicylate, eugenol, and eugenyl acetate might be primarily due to interference with the octopaminergic system. 2-Heptyl acetate and 2-nonanone might act on both acetylcholinesterase and the octopaminergic receptor. 2-Heptanone might act primarily on acetylcholinesterase. Further studies will warrant possible applications of S. aromaticum bud-derived products as potential larvicides and ovicides for the control of B. procera. Copyright © 2018. Published by Elsevier Inc.

Modification of Poly(vinyl butyral) Coatings Using Bis-silanes (Postprint)

DTIC Science & Technology

2010-04-01

parent coating to 2-chloroethyl ethyl sulfide (2-CEES), dimethyl methylphosphonate (DMMP), diisopropyl methylphosphonate, and methyl salicylate ; the...methylphosphonate (DMMP), diisopropyl methylphos- phonate, and methyl salicylate ; the most significant reduction was observed for 2-CEES and DMMP at...dimethyl methylphosphonate (DMMP), diisopropyl methylphosphonate (DIMP), dibutyltin dilaurate (DBTDL), and methyl salicylate (MS)wereobtained

Static liquid permeation cell method for determining the migration parameters of low molecular weight organic compounds in polyethylene terephthalate.

PubMed

Song, Yoon S; Koontz, John L; Juskelis, Rima O; Zhao, Yang

2013-01-01

The migration of low molecular weight organic compounds through polyethylene terephthalate (PET) films was determined by using a custom permeation cell assembly. Fatty food simulant (Miglyol 812) was added to the receptor chamber, while the donor chamber was filled with 1% and 10% (v/v) migrant compounds spiked in simulant. The permeation cell was maintained at 40°C, 66°C, 100°C or 121°C for up to 25 days of polymer film exposure time. Migrants in Miglyol were directly quantified without a liquid-liquid extraction step by headspace-GC-MS analysis. Experimental diffusion coefficients (DP) of toluene, benzyl alcohol, ethyl butyrate and methyl salicylate through PET film were determined. Results from Limm's diffusion model showed that the predicted DP values for PET were all greater than the experimental values. DP values predicted by Piringer's diffusion model were also greater than those determined experimentally at 66°C, 100°C and 121°C. However, Piringer's model led to the underestimation of benzyl alcohol (Áp = 3.7) and methyl salicylate (Áp = 4.0) diffusion at 40°C with its revised "upper-bound" Áp value of 3.1 at temperatures below the glass transition temperature (Tg) of PET (<70°C). This implies that input parameters of Piringer's model may need to be revised to ensure a margin of safety for consumers. On the other hand, at temperatures greater than the Tg, both models appear too conservative and unrealistic. The highest estimated Áp value from Piringer's model was 2.6 for methyl salicylate, which was much lower than the "upper-bound" Áp value of 6.4 for PET. Therefore, it may be necessary further to refine "upper-bound" Áp values for PET such that Piringer's model does not significantly underestimate or overestimate the migration of organic compounds dependent upon the temperature condition of the food contact material.

Parthenolide accumulation and expression of genes related to parthenolide biosynthesis affected by exogenous application of methyl jasmonate and salicylic acid in Tanacetum parthenium.

PubMed

Majdi, Mohammad; Abdollahi, Mohammad Reza; Maroufi, Asad

2015-11-01

Up-regulation of germacrene A synthase and down-regulation of parthenolide hydroxylase genes play key role in parthenolide accumulation of feverfew plants treated with methyl jasmonate and salicylic acid. Parthenolide is an important sesquiterpene lactone due to its anti-migraine and anti-cancer properties. Parthenolide amount was quantified by high-performance liquid chromatography after foliar application of methyl jasmonate (100 µM) or salicylic acid (1.0 mM) on feverfew leaves in time course experiment (3-96 h). Results indicate that exogenous application of methyl jasmonate or salicylic acid activated parthenolide biosynthesis. Parthenolide content reached its highest amount at 24 h after methyl jasmonate or salicylic acid treatments, which were 3.1- and 1.96-fold higher than control plants, respectively. Parthenolide transiently increased due to methyl jasmonate or salicylic acid treatments until 24 h, but did not show significant difference compared with control plants at 48 and 96 h time points in both treatments. Also, the transcript levels of early pathway (upstream) genes of terpene biosynthesis including 3-hydroxy-3-methylglutaryl-coenzyme A reductase, 1-deoxy-D-xylulose-5-phosphate reductoisomerase and hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase and the biosynthetic genes of parthenolide including germacrene A synthase, germacrene A oxidase, costunolide synthase and parthenolide synthase were increased by methyl jasmonate and salicylic acid treatments, but with different intensity. The transcriptional levels of these genes were higher in methyl jasmonate-treated plants than salicylic acid-treated plants. Parthenolide content measurements along with expression pattern analysis of the aforementioned genes and parthenolide hydroxylase as side branch gene of parthenolide suggest that the expression patterns of early pathway genes were not directly consistent with parthenolide accumulation pattern; hence, parthenolide accumulation is probably further modulated by the expression of its biosynthetic genes, especially germacrene A synthase and also its side branch gene, parthenolide hydroxylase.

Methyl Salicylate Level Increase in Flax after Fusarium oxysporum Infection Is Associated with Phenylpropanoid Pathway Activation

PubMed Central

Boba, Aleksandra; Kostyn, Kamil; Kostyn, Anna; Wojtasik, Wioleta; Dziadas, Mariusz; Preisner, Marta; Szopa, Jan; Kulma, Anna

2017-01-01

Flax (Linum usitatissimum) is a crop plant valued for its oil and fiber. Unfortunately, large losses in cultivation of this plant are caused by fungal infections, with Fusarium oxysporum being one of its most dangerous pathogens. Among the plant's defense strategies, changes in the expression of genes of the shikimate/phenylpropanoid/benzoate pathway and thus in phenolic contents occur. Among the benzoates, salicylic acid, and its methylated form methyl salicylate play an important role in regulating plants' response to stress conditions. Upon treatment of flax plants with the fungus we found that methyl salicylate content increased (4.8-fold of the control) and the expression profiles of the analyzed genes suggest that it is produced most likely from cinnamic acid, through the β-oxidative route. At the same time activation of some genes involved in lignin and flavonoid biosynthesis was observed. We suggest that increased methyl salicylate biosynthesis during flax response to F. oxysporum infection may be associated with phenylpropanoid pathway activation. PMID:28163709

Mouthwash overdose

MedlinePlus

... are: Chlorhexidine gluconate Ethanol (ethyl alcohol) Hydrogen peroxide Methyl salicylate ... amounts of alcohol (drunkenness). Swallowing large amounts of methyl salicylate and hydrogen peroxide may also cause serious stomach ...

The Herbivore-Induced Plant Volatile Methyl Salicylate Negatively Affects Attraction of the Parasitoid Diadegma semiclausum

PubMed Central

Mumm, Roland; Poelman, Erik H.; Yang, Yue; Pichersky, Eran; Dicke, Marcel

2010-01-01

The indirect defense mechanisms of plants comprise the production of herbivore-induced plant volatiles that can attract natural enemies of plant attackers. One of the often emitted compounds after herbivory is methyl salicylate (MeSA). Here, we studied the importance of this caterpillar-induced compound in the attraction of the parasitoid wasp Diadegma semiclausum by using a mutant Arabidopsis line. Pieris rapae infested AtBSMT1-KO mutant Arabidopsis plants, compromised in the biosynthesis of MeSA, were more attractive to parasitoids than infested wild-type plants. This suggests that the presence of MeSA has negative effects on parasitoid host-finding behavior when exposed to wild-type production of herbivore-induced Arabidopsis volatiles. Furthermore, in line with this, we recorded a positive correlation between MeSA dose and repellence of D. semiclausum when supplementing the headspace of caterpillar-infested AtBSMT1-KO plants with synthetic MeSA. Electronic supplementary material The online version of this article (doi:10.1007/s10886-010-9787-1) contains supplementary material, which is available to authorized users. PMID:20407809

Development of the 2007 Chemical Decontaminant Source Document

DTIC Science & Technology

2009-03-01

Chemical Agent Simulant Specific DEM diethyl malonate MeS methyl salicylate PEG200 Polyethylene glycol 200 TEP triethyl phosphate Group 6...simulants • H-agent simulants o Methyl salicylate (MeS) o Chloroethyl phenyl sulfide (CEPS) o Chloroethyl ethyl sulfide (CEES) • VX simulants... Methyl bromide Ethyl phosphonothioic dichloride Sulfur dioxide Methyl chloroformate Ethyl phosphonic dichloride Sulfuric acid Methyl chlorosilane

Rotational Spectrum of the Methyl Salicylate-Water Complex: the Missing Conformer and the Tunneling Motions

NASA Astrophysics Data System (ADS)

Ghosh, Supriya; Thomas, Javix; Xu, Yunjie; Jäger, Wolfgang

2015-06-01

Methyl salicylate is a naturally occurring organic ester produced by wintergreen and other plants. It is also found in many over-the-counter remedies, such as muscle ache creams. The rotational spectrum of the methyl salicylate monomer was reported previously, where the most stable, dominant conformer was identified. The methyl salicylate-water complex was first studied using fluorescence-detected infrared spectroscopy; only one monohydrate conformer was found in that work. In the present study, we employed both broadband chirped and cavity based Fourier transform microwave spectroscopy to examine the competition between intra- and intermolecular hydrogen-bonding interactions and possible large amplitude motions associated with the methyl group and the water subunit. In contrast to the previous infrared study, two monohydrate conformers were identified, with carbonyl O or hydroxyl O as the hydrogen bond acceptors. Detailed analyses of the observed hyperfine structures will be presented, as well as our efforts to extend the study to larger methyl salicylate hydration clusters. S. Melandri, B. M. Giuliano, A. Maris, L. B. Favero, P. Ottaviani, B. Velino, W. Caminati, J. Phys. Chem. A. 2007, 111, 9076. A. Mitsuzuka, A. Fujii, T. Ebata, N. Mikami, J. Phys. Chem. A 1998, 102, 9779.

Collective Protection (ColPro) Field Testing

DTIC Science & Technology

2011-09-28

It is recommended that methyl salicylate (MeS) or similar simulants that are not difficult to decontaminate should be used for this purpose. 4.4.3...ce nt ra tio n (m g/ m 3 ) Figure 3. Analysis of ppbRAE® and Solid Sorbent Tube (SST) Data, Methyl Salicylate (MeS) Challenge to the Interior of...the Vehicle. Figure 4. Gasmet™ Analysis of the Methyl Salicylate (MeS) Challenge in the Simulant- Exposure Area (SEA). TOP 08-2-198 28 September

Design, synthesis and antileishmanial in vitro activity of new series of chalcones-like compounds: a molecular hybridization approach.

PubMed

Barbosa, Ticiano P; Sousa, Suervy C O; Amorim, Francianne M; Rodrigues, Yara K S; de Assis, Priscilla A C; Caldas, John P A; Oliveira, Márcia R; Vasconcellos, Mário L A A

2011-07-15

The chalcone-like series 1a-1g was efficiently synthesized from Morita-Baylis-Hillman reaction (52-74% yields). Compounds 1a-1g were designed by molecular hybridization based on the anti-inflammatory drug methyl salicylate (3) and the antileishmanial moiety of the Morita-Baylis-Hillman adducts 2a-2g. The 1a-1g compounds were much more actives than precursor series 2a-2g, for example, IC(50)=7.65 μM on Leishmania amazonensis and 10.14 μM on Leishmania chagasi (compound 1c) when compared to IC(50)=50.08 μM on L. amazonensis and 82.29 μM on L. chagasi (compound 2c). The IC(50) values of compound 3 (228.49 μM on L. amazonensis and 261.45 μM on L. chagasi) and acryloyl salicylate 4 (108.50 μM on L. amazonensis and 118.83 μM on L. chagasi) were determined here, by the first time, on Leishmania. Copyright © 2011 Elsevier Ltd. All rights reserved.

Effect of methyl salicylate and methyl jasmonate pre-treatment on the volatile profile in tomato fruit subjected to chilling temperature

USDA-ARS?s Scientific Manuscript database

Tomato fruits exposed to chilling temperatures suffer aroma loss prior to visual chilling injury (CI) symptoms. Methyl salicylate (MeSA) and methyl jasmonate (MeJA) treatments were reported to alleviate the development of visual CI, however, it is unknown if the treatments alleviate internal CI in t...

Transgenic soybean overexpressing GmSamT1 exhibits resistance to multiple-HG types of soybean cyst nematode Heterodera glycines

USDA-ARS?s Scientific Manuscript database

Soybean (Glycine max (L.) Merr.) salicylic acid methyl transferase (GmSAMT1) catalyzes the conversion of salicylic acid to methyl salicylate. Prior results showed that when GmSAMT1 was overexpressed in transgenic soybean hairy roots, resistance is conferred against soybean cyst nematode (SCN), Heter...

Growth Media Affect Assessment of Antimicrobial Activity of Plant-Derived Polyphenols.

PubMed

Xu, Xin; Ou, Zhen M; Wu, Christine D

2018-01-01

This study aimed to investigate the effects of different microbial growth media on the laboratory assessment of antimicrobial activity of natural polyphenolic compounds. The inhibition of the tea polyphenol EGCG on growth of selected oral microorganisms was evaluated in complex media and a protein-free chemically defined medium (CDM). Other antimicrobial agents (polyphenolic grape seed extract, plant alkaloid berberine, methyl salicylate, and chlorhexidine gluconate) were also tested in the study. The presence of proteins and their effects on the antimicrobial activity of EGCG were investigated by the addition of BSA to the CDM. The MICs of EGCG against test oral microorganisms were 4 to 64 times higher in complex media than in CDM. The polyphenolic grape seed extract exhibited similar discrepancies. However, the MICs of the nonpolyphenolic compounds (berberine, methyl salicylate, and chlorhexidine) were not significantly different between the two growth media. The MIC of EGCG against S. mutans UA159 in CDM with added BSA was 16 times higher than that in CDM alone. Therefore, nonproteinaceous CDM should be used to avoid interference of proteins with the active ingredients when testing the antimicrobial activity of plant-derived polyphenolic compounds against microorganisms. This will also minimize the discrepancies noted in results obtained by different investigators.

Event Record for the Joint Chemical Agent Detector (JCAD) Increment 2 Chamber Upgrades

DTIC Science & Technology

2009-05-27

trials began. The simulants [ methyl salicylate (MeS) and dimethyl methyl phosphate (DMMP)] were chosen for their similarity to CWA evaporation...rate and the measured con- centration. 2. The temperature in the evaporation zone was controlled at 150ºC. Figure 2. Methyl Salicylate (MeS

Topical Pain Relievers May Cause Burns

MedlinePlus

... and joint pain relievers containing the active ingredients menthol, methyl salicylate and capsaicin. These cases were uncovered ... of people who purchase these products, Tan notes. Menthol, methyl salicylate and capsaicin create sensations of local ...

Overexpression of a soybean salicylic acid methyltransferase gene confers resistance to soybean cyst nematode

USDA-ARS?s Scientific Manuscript database

Salicylic acid plays a critical role in activating plant defence responses after pathogen attack. Salicylic acid methyltransferase (SAMT) modulates the level of salicylic acid by converting salicylic acid to methyl salicylate. Here, we report that a SAMT gene from soybean (GmSAMT1) plays a role in s...

Effect of elicitors on the production of gossypol and methylated gossypol in cotton hairy roots

USDA-ARS?s Scientific Manuscript database

The effect of two-chemical elicitors, salicylic acid and methyl jasmonate, on the production of gossypol, 6-methoxy gossypol, and 6,6'-dimethoxy gossypol in Gossypium barbadense hairy roots was examined. Methyl jasmonate, but not salicylic acid, was found to increase the production of gossypol and ...

Gas Chromatographic Determination of Methyl Salicylate in Rubbing Alcohol: An Experiment Employing Standard Addition.

ERIC Educational Resources Information Center

Van Atta, Robert E.; Van Atta, R. Lewis

1980-01-01

Provides a gas chromatography experiment that exercises the quantitative technique of standard addition to the analysis for a minor component, methyl salicylate, in a commercial product, "wintergreen rubbing alcohol." (CS)

The role of methyl salicylate in prey searching behavior of the predatory mite phytoseiulus persimilis.

PubMed

De Boer, Jetske G; Dicke, Marcel

2004-02-01

Many carnivorous arthropods use herbivore-induced plant volatiles to locate their prey. These plant volatiles are blends of up to hundreds of compounds. It is often unknown which compounds in such a complex volatile blend represent the signal to the foraging carnivore. We studied the role of methyl salicylate (MeSA) as part of the volatile blend in the foraging behavior of the predatory mite Phytoseiulus persimilis by using a Y-tube olfactometer. MeSA is one of the compounds released by lima bean, infested with Tetranychus urticae--a prey species of the predatory mite. MeSA attracted satiated predatory mites in a dose-dependent way with optimum attraction at a dose of 0.2 microg. Predatory mites did not discriminate between a prey-induced lima bean volatile blend (that contains MeSA) and a prey-induced volatile blend to which an extra amount of synthetic MeSA had been added. However, they preferred a MeSA-containing volatile blend (induced by T. urticae) to an otherwise similar but MeSA-free blend (induced by jasmonic acid). Adding synthetic MeSA to the MeSA-free blend significantly increased the mites' choice for this odor, suggesting an important role for MeSA. This study is a new step toward unraveling the role of herbivore-induced plant volatiles in the foraging behavior of predatory arthropods.

Maintaining postharvest quality of cold stored 'Hass' avocados by altering the fatty acids content and composition with the use of natural volatile compounds - methyl jasmonate and methyl salicylate.

PubMed

Glowacz, Marcin; Bill, Malick; Tinyane, Peter P; Sivakumar, Dharini

2017-12-01

Low temperatures are often used to reduce metabolic processes and extend the storage life of fruit; however, in the case of avocado, a temperature below 3 °C will often result in the development of physiological disorders associated with chilling injury. The objective of this study was to investigate the ability of methyl jasmonate (MeJA) and methyl salicylate (MeSA) vapours to alleviate chilling injury in 'Hass' avocado fruit kept at 2 °C for 21 days followed by 6-7 days of shelf-life at 20 °C, simulating supply chain conditions. The incidence and severity of chilling injury were significantly reduced in MeJA- and MeSA-exposed fruit, especially at 100 µmol L -1 . The mechanism involved improved membrane integrity via alteration of the fatty acid content and composition, down-regulation of LOX gene expression and reduced activity of lipoxygenase. MeJA and MeSA have the potential for being used with 'Hass' avocado fruit shipped at low temperature to reduce its susceptibility to chilling injury. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Zinc complexes supported by methyl salicylato ligands: synthesis, structure, and application in ring-opening polymerization of L-lactide.

PubMed

Petrus, Rafał; Sobota, Piotr

2013-10-14

Two novel zinc alkoxides supported by chelating methyl salicylato (MesalO; MesalOH = methyl salicylate) ligands were successfully synthesized and characterized. Reaction of MesalOH with ZnEt2 (2:1) gives a tetranuclear cluster [Zn(MesalO)2]4 (1), which by addition of pyridine is transformed to the mononuclear compound [Zn(MesalO)2(py)2] (2). Compounds 1 and 2 were characterized by elemental analysis, NMR, IR, and single crystal X-ray diffraction. The catalytic activity of both compounds was tested for the ring-opening polymerization (ROP) of L-lactide (L-LA). It was found that compounds 1 and 2 are efficient initiators of the ROP of L-LA, yielding cyclic PLLA with weight average molecular weights up to 100 kDa for 2. The treatment of 2 with 1 equiv. of BnOH in toluene afforded a dimeric compound [Zn(OBn)(MesalO)(py)]2 (3). The addition of L-LA to a combination of 1 and 4 equiv. of BnOH in THF or 2 and 1 equiv. of BnOH in toluene led to the rapid and efficient generation of PLLA with end-capped BnO groups.

Functionalized Nano and Micro Structured Composite Coatings

DTIC Science & Technology

2011-06-01

created. Contact angles for water, hexadecane and warfare simulants (tributyl phosphate (TBP), methyl salicylate (MS) and 2-chloroethyl ethyl sulfide... methyl salicylate PAA-POEGMA polyacrylic acid-co-poly(oligoethylene glycol methacrylate) PBMA poly(butyl methacrylate) PD-TDES commercial mixture of...polymerized radically (according to a procedure published elsewhere1) to give PGMA, Mn = 300,000 kDa, PDI = 2. The polymerization was carried out in methyl

Aqueous-phase oxidation of green leaf volatiles by hydroxyl radical as a source of SOA: Product identification from methyl jasmonate and methyl salicylate oxidation

NASA Astrophysics Data System (ADS)

Hansel, Amie K.; Ehrenhauser, Franz S.; Richards-Henderson, Nicole K.; Anastasio, Cort; Valsaraj, Kalliat T.

2015-02-01

Green leaf volatiles (GLVs) are a group of biogenic volatile organic compounds (BVOCs) released into the atmosphere by vegetation. BVOCs produce secondary organic aerosol (SOA) via gas-phase reactions, but little is known of their aqueous-phase oxidation as a source of SOA. GLVs can partition into atmospheric water phases, e.g., fog, mist, dew or rain, and be oxidized by hydroxyl radicals (˙OH). These reactions in the liquid phase also lead to products that have higher molecular weights, increased polarity, and lower vapor pressures, ultimately forming SOA after evaporation of the droplet. To examine this process, we investigated the aqueous, ˙OH-mediated oxidation of methyl jasmonate (MeJa) and methyl salicylate (MeSa), two GLVs that produce aqueous-phase SOA. High performance liquid chromatography/electrospray ionization mass spectrometry (HPLC-ESI-MS) was used to monitor product formation. The oxidation products identified exhibit higher molecular mass than their parent GLV due to either dimerization or the addition of oxygen and hydroxyl functional groups. The proposed structures of potential products are based on mechanistic considerations combined with the HPLC/ESI-MS data. Based on the structures, the vapor pressure and the Henry's law constant were estimated with multiple methods (SPARC, SIMPOL, MPBPVP, Bond and Group Estimations). The estimated vapor pressures of the products identified are significantly (up to 7 orders of magnitude) lower than those of the associated parent compounds, and therefore, the GLV oxidation products may remain as SOA after evaporation of the water droplet. The contribution of the identified oxidation products to SOA formation is estimated based on measured HPLC-ESI/MS responses relative to previous aqueous SOA mass yield measurements.

Fermentation Products of Solvent Tolerant Marine Bacterium Moraxella spp. MB1 and Its Biotechnological Applications in Salicylic Acid Bioconversion

PubMed Central

Wahidullah, Solimabi; Naik, Deepak N.; Devi, Prabha

2013-01-01

As part of a proactive approach to environmental protection, emerging issues with potential impact on the environment is the subject of ongoing investigation. One emerging area of environmental research concerns pharmaceuticals like salicylic acid, which is the main metabolite of various analgesics including aspirin. It is a common component of sewage effluent and also an intermediate in the degradation pathway of various aromatic compounds which are introduced in the marine environment as pollutants. In this study, biotransformation products of salicylic acid by seaweed, Bryopsis plumosa, associated marine bacterium, Moraxella spp. MB1, have been investigated. Phenol, conjugates of phenol and hydroxy cinnamic acid derivatives (coumaroyl, caffeoyl, feruloyl and trihydroxy cinnamyl) with salicylic acid (3–8) were identified as the bioconversion products by electrospray ionization mass spectrometry. These results show that the microorganism do not degrade phenolic acid but catalyses oxygen dependent transformations without ring cleavage. The degradation of salicylic acid is known to proceed either via gentisic acid pathway or catechol pathway but this is the first report of biotransformation of salicylic acid into cinnamates, without ring cleavage. Besides cinnamic acid derivatives (9–12), metabolites produced by the bacterium include antimicrobial indole (13) and β-carbolines, norharman (14), harman (15) and methyl derivative (16), which are beneficial to the host and the environment. PMID:24391802

JSTO Science and Technology Update. Volume 1, Number 2, Winter 2011

DTIC Science & Technology

2011-01-01

Figure 2. Passage of methyl salicylate simulant through an expanded Teflon control (blue), the open IPN (black) and the closed IPN (pink). The...membrane (blue). ET is used in breathable sports clothing. The materials were challenged using vapor from the CW agent simulant methyl salicylate (MS). The...was challenged with vapor from chloroethyl ethyl sulfide (a mus- tard gas simulant), benzene, and liquid with dissolved methyl parathion (a V-agent

Induction of a Pregnancy-Like Mammary Gland Differentiation by Docosapentaenoic Omega-3 Fatty Acid

DTIC Science & Technology

2008-09-01

xylenes, and stored in methyl salicylate . Morphological Assessment of Mammary Gland—Whole inguinal mammary glands were removed from virgin control as...respectively, defatted in xylenes, and stored in methyl salicylate . Quantitative RT-PCR analyses RNA was isolated and subjected to real time PCR analysis... methylation , and fatty acid analysis were performed as previously described [28,48]. Briefly, an ali- quot of mammary tissue homogenate in a glass

40 CFR 180.1189 - Methyl salicylate; exemption from the requirement of a tolerance.

Code of Federal Regulations, 2011 CFR

2011-07-01

... food or feed when used as an insect repellant in food packaging and animal feed packaging at an application rate that does not exceed 0.2 mg of methyl salicylate per square inch of packaging materials. [62... AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR PESTICIDE CHEMICAL RESIDUES IN FOOD...

40 CFR 180.1189 - Methyl salicylate; exemption from the requirement of a tolerance.

Code of Federal Regulations, 2010 CFR

2010-07-01

... food or feed when used as an insect repellant in food packaging and animal feed packaging at an application rate that does not exceed 0.2 mg of methyl salicylate per square inch of packaging materials. [62... AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR PESTICIDE CHEMICAL RESIDUES IN FOOD...

Data Fusion Analysis For Test Validation System

DTIC Science & Technology

2009-11-16

triethyl phosphate (TEP), methyl salicylate (MeS), and acetic acid (AA). A total of 29 release scenarios were conducted: fifteen TEP releases of 30...N2 - north second. bA - 2, 3, 6, 7, 10, and 11; B - 1 through 12; NA - not available. cTEP - triethyl phosphate; MeS - methyl salicylate ; AA

Evaluation of methyl salicylate lures on populations of Typhlodromus pyri (Acari: Phytoseiidae) and other natural enemies in vineyards

USDA-ARS?s Scientific Manuscript database

Methyl salicylate (MeSA), an herbivore induced plant volatile, can potentially elicit control of pests through attraction of beneficial arthropods. This study evaluates the effect of synthetic MeSA lures (PredaLure) on arthropod populations during the 2009 and 2010 seasons in two Oregon vineyards (...

Effect of Methyl Salicylate-Based Lures on Beneficial and Pest Arthropods in Strawberry

USDA-ARS?s Scientific Manuscript database

Methyl salicylate (MeSA) is a common herbivore-induced plant volatile that, when applied to crops, has the potential to enhance natural enemy abundance and pest control. The impacts of MeSA in the strawberry system were unknown and examined in this study. Strawberry plots contained no lures (contr...

40 CFR 180.1189 - Methyl salicylate; exemption from the requirement of a tolerance.

Code of Federal Regulations, 2012 CFR

2012-07-01

... food or feed when used as an insect repellant in food packaging and animal feed packaging at an application rate that does not exceed 0.2 mg of methyl salicylate per square inch of packaging materials. [62... AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR PESTICIDE CHEMICAL RESIDUES IN FOOD...

40 CFR 180.1189 - Methyl salicylate; exemption from the requirement of a tolerance.

Code of Federal Regulations, 2014 CFR

2014-07-01

... food or feed when used as an insect repellant in food packaging and animal feed packaging at an application rate that does not exceed 0.2 mg of methyl salicylate per square inch of packaging materials. [62... AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR PESTICIDE CHEMICAL RESIDUES IN FOOD...

40 CFR 180.1189 - Methyl salicylate; exemption from the requirement of a tolerance.

Code of Federal Regulations, 2013 CFR

2013-07-01

... food or feed when used as an insect repellant in food packaging and animal feed packaging at an application rate that does not exceed 0.2 mg of methyl salicylate per square inch of packaging materials. [62... AGENCY (CONTINUED) PESTICIDE PROGRAMS TOLERANCES AND EXEMPTIONS FOR PESTICIDE CHEMICAL RESIDUES IN FOOD...

Residual impact of methyl salicylate fumigation at the breaker stage on C6 volatile biopathway in red tomato fruit

USDA-ARS?s Scientific Manuscript database

Flavor, which is comprised of aroma and taste, is an important tomato characteristic. Methyl salicylate (MeSA), acting as a critical mobile signal, plays an important role in tomato stress responses and ripening processes. However, less is studied on the impact of its application at early ripening s...

Field responses of predaceous arthropods to methyl salicylate: a meta-analysis and case study in cranberries

USDA-ARS?s Scientific Manuscript database

Methyl salicylate (MeSA) is an herbivore-induced plant volatile (HIPV) that has shown potential in attracting natural enemies. Here, we conducted a meta-analysis to evaluate the magnitude of natural enemy response to MeSA in the field, and tested its attractiveness to insect predators in commercial...

Evaluation of airborne methyl salicylate for improved conservation biological control of two-spotted spider mite and hop aphid in Oregon hop yards

USDA-ARS?s Scientific Manuscript database

The use of synthetic herbivore-induced plant volatiles (HIPV) to attract natural enemies has received interest as a tool to enhance conservation biological control (CBC). Methyl salicylate (MeSA) is a HIPV that is attractive to several key predators of two-spotted spider mite, Tetranychus urticae K...

Evaluation of airborne methyl salicylate for improved conservation biological control of two-spotted spider mites and hop aphid in Oregon hop yards

USDA-ARS?s Scientific Manuscript database

The use of synthetic herbivore-induced plant volatiles (HIPV) to attract natural enemies has received interest as a tool to enhance conservation biological control (CBC). Methyl salicylate (MeSA) is a HIPV that is attractive to several key predators of two-spotted spider mite, Tetranychus urticae K...

21 CFR 369.20 - Drugs; recommended warning and caution statements.

Code of Federal Regulations, 2014 CFR

2014-04-01

..., INCLUDING ASPIRIN AND SALICYLAMIDE (EXCEPT METHYL SALICYLATE, EFFERVESCENT SALICYLATE PREPARATIONS, AND... out of reach of children.” If the article is an aspirin preparation, it should bear the first of the... aspirin tablets, but such a statement is not required on the labels of other salicylates clearly offered...

21 CFR 369.20 - Drugs; recommended warning and caution statements.

Code of Federal Regulations, 2012 CFR

2012-04-01

..., INCLUDING ASPIRIN AND SALICYLAMIDE (EXCEPT METHYL SALICYLATE, EFFERVESCENT SALICYLATE PREPARATIONS, AND... out of reach of children.” If the article is an aspirin preparation, it should bear the first of the... aspirin tablets, but such a statement is not required on the labels of other salicylates clearly offered...

21 CFR 369.20 - Drugs; recommended warning and caution statements.

Code of Federal Regulations, 2013 CFR

2013-04-01

..., INCLUDING ASPIRIN AND SALICYLAMIDE (EXCEPT METHYL SALICYLATE, EFFERVESCENT SALICYLATE PREPARATIONS, AND... out of reach of children.” If the article is an aspirin preparation, it should bear the first of the... aspirin tablets, but such a statement is not required on the labels of other salicylates clearly offered...

21 CFR 369.20 - Drugs; recommended warning and caution statements.

Code of Federal Regulations, 2011 CFR

2011-04-01

..., INCLUDING ASPIRIN AND SALICYLAMIDE (EXCEPT METHYL SALICYLATE, EFFERVESCENT SALICYLATE PREPARATIONS, AND... out of reach of children.” If the article is an aspirin preparation, it should bear the first of the... aspirin tablets, but such a statement is not required on the labels of other salicylates clearly offered...

Exogenous application of methyl jasmonate and salicylic acid on citrus foliage: Effecs on foliar volatiles and aggregation behavior of Asian citrus psyllid (Diaphorina citri)

USDA-ARS?s Scientific Manuscript database

Methyl jasmonate (MeJA) and salicylic acid (SA) are well-known activators of chemical defenses in plants. The SA pathway is involved in citrus response to infection by Candidatus Liberibacter asiaticus (CLas); less is known about the role of jasmonates in citrus defense response. We examined the eff...

QM/MM Free Energy Simulations of Salicylic Acid Methyltransferase: Effects of Stabilization of TS-like Structures on Substrate Specificity

DOE Office of Scientific and Technical Information (OSTI.GOV)

Yao, Jianzhuang; Xu, Qin; Chen, Feng

2010-01-01

Salicylic acid methyltransferases (SAMTs) synthesize methyl salicylate (MeSA) using salicylate as the substrate. MeSA synthesized in plants may function as an airborne signal to activate the expression of defense-related genes and could also be a critical mobile signaling molecule that travels from the site of plant infection to establish systemic immunity in the induction of disease resistance. Here the results of QM/MM free energy simulations for the methyl transfer process in Clarkia breweri SAMT (CbSAMT) are reported to determine the origin of the substrate specificity of SAMTs. The free energy barrier for the methyl transfer from S-adenosyl-l-methionine (AdoMet) to 4-hydroxybenzoatemore » in CbSAMT is found to be about 5 kcal/mol higher than that from AdoMet to salicylate, consistent with the experimental observations. It is suggested that the relatively high efficiency for the methylation of salicylate compared to 4-hydroxybenzoate is due, at least in part, to the reason that a part of the stabilization of the transition state (TS) configuration is already reflected in the reactant complex, presumably, through the binding. The results seem to indicate that the creation of the substrate complex (e.g., through mutagenesis and substrate modifications) with its structure closely resembling TS might be fruitful for improving the catalytic efficiency for some enzymes. The results show that the computer simulations may provide important insights into the origin of the substrate specificity for the SABATH family and could be used to help experimental efforts in generating engineered enzymes with altered substrate specificity.« less

Simultaneous determination of salicylic, 3-methyl salicylic, 4-methyl salicylic, acetylsalicylic and benzoic acids in fruit, vegetables and derived beverages by SPME-LC-UV/DAD.

PubMed

Aresta, Antonella; Zambonin, Carlo

2016-03-20

Salicylic and benzoic acid are phenolic acids occurring in plant cells, thus they can be present in fruit and vegetables at various levels. They possess anti-inflammatory and antimicrobial properties, however they may induce symptoms and health problems in a small percentage of the population. Therefore, a low phenolic acid diet may be of clinical benefit to such individuals. In order to achieve this goal, the concentration of these substances in different food and beverages should be assessed. The present work describes for the first time a new method, based on solid phase microextraction (polydimethylsiloxane-divinylbenzene fiber) coupled to liquid chromatography with UV diode array detection, for the simultaneous determination of salicylic acid, 3-methyl salicylic acid, 4-methyl salicylic acid, acetylsalicylic acid and benzoic acid in selected fruit, vegetables and beverages. All the aspects influencing fiber adsorption (time, temperature, pH, salt addition) and desorption (desorption and injection time, desorption solvent mixture composition) of the analytes have been investigated. An isocratic separation was performed using an acetonitrile-phosphate buffer (pH 2.8; 2 mM) mixture (70:30, v/v) as the mobile phase. The estimated LOD and LOQ values (μg/mL) were in the range 0.002-0.028 and 0.007-0.095. The within-day and day-to-day precision values (RSD%) were between 4.7-6.1 and 6.6-9.4, respectively. The method has been successfully applied to the analysis of fava beans, blueberries, kiwi, tangerines, lemons, oranges and fruit juice (lemon and blueberry) samples. The major advantage of the method is that it only requires simple homogenization and/or centrifugation and dilution steps prior to SPME and injection in the LC system. Copyright © 2016 Elsevier B.V. All rights reserved.

Protonation switching to the least-basic heteroatom of carbamate through cationic hydrogen bonding promotes the formation of isocyanate cations.

PubMed

Kurouchi, Hiroaki; Sumita, Akinari; Otani, Yuko; Ohwada, Tomohiko

2014-07-07

We found that phenethylcarbamates that bear ortho-salicylate as an ether group (carbamoyl salicylates) dramatically accelerate OC bond dissociation in strong acid to facilitate generation of isocyanate cation (N-protonated isocyanates), which undergo subsequent intramolecular aromatic electrophilic cyclization to give dihydroisoquinolones. To generate isocyanate cations from carbamates in acidic media as electrophiles for aromatic substitution, protonation at the ether oxygen, the least basic heteroatom, is essential to promote CO bond cleavage. However, the carbonyl oxygen of carbamates, the most basic site, is protonated exclusively in strong acids. We found that the protonation site can be shifted to an alternative basic atom by linking methyl salicylate to the ether oxygen of carbamate. The methyl ester oxygen ortho to the phenolic (ether) oxygen of salicylate is as basic as the carbamate carbonyl oxygen, and we found that monoprotonation at the methyl ester oxygen in strong acid resulted in the formation of an intramolecular cationic hydrogen bond (>CO(+) H⋅⋅⋅O<) with the phenolic ether oxygen. This facilitates OC bond dissociation of phenethylcarbamates, thereby promoting isocyanate cation formation. In contrast, superacid-mediated diprotonation at the methyl ester oxygen of the salicylate and the carbonyl oxygen of the carbamate afforded a rather stable dication, which did not readily undergo CO bond dissociation. This is an unprecedented and unknown case in which the monocation has greater reactivity than the dication. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Stimulation of the Salicylic Acid Pathway Aboveground Recruits Entomopathogenic Nematodes Belowground

PubMed Central

Filgueiras, Camila Cramer; Willett, Denis S.; Junior, Alcides Moino; Pareja, Martin; Borai, Fahiem El; Dickson, Donald W.; Stelinski, Lukasz L.; Duncan, Larry W.

2016-01-01

Plant defense pathways play a critical role in mediating tritrophic interactions between plants, herbivores, and natural enemies. While the impact of plant defense pathway stimulation on natural enemies has been extensively explored aboveground, belowground ramifications of plant defense pathway stimulation are equally important in regulating subterranean pests and still require more attention. Here we investigate the effect of aboveground stimulation of the salicylic acid pathway through foliar application of the elicitor methyl salicylate on belowground recruitment of the entomopathogenic nematode, Steinernema diaprepesi. Also, we implicate a specific root-derived volatile that attracts S. diaprepesi belowground following aboveground plant stimulation by an elicitor. In four-choice olfactometer assays, citrus plants treated with foliar applications of methyl salicylate recruited S. diaprepesi in the absence of weevil feeding as compared with negative controls. Additionally, analysis of root volatile profiles of citrus plants receiving foliar application of methyl salicylate revealed production of d-limonene, which was absent in negative controls. The entomopathogenic nematode S. diaprepesi was recruited to d-limonene in two-choice olfactometer trials. These results reinforce the critical role of plant defense pathways in mediating tritrophic interactions, suggest a broad role for plant defense pathway signaling belowground, and hint at sophisticated plant responses to pest complexes. PMID:27136916

The Herbivore-Induced Plant Volatiles Methyl Salicylate and Menthol Positively affect Growth and Pathogenicity of Entomopathogenic Fungi

PubMed Central

Lin, Yongwen; Qasim, Muhammad; Hussain, Mubasher; Akutse, Komivi Senyo; Avery, Pasco Bruce; Dash, Chandra Kanta; Wang, Liande

2017-01-01

Some herbivore-induced-plant volatiles (HIPVs) compounds are vital for the functioning of an ecosystem, by triggering multi-trophic interactions for natural enemies, plants and herbivores. However, the effect of these chemicals, which play a crucial role in regulating the multi-trophic interactions between plant-herbivore-entomopathogenic fungi, is still unknown. To fill this scientific gap, we therefore investigated how these chemicals influence the entomopathogenic fungi growth and efficacy. In this study, Lipaphis erysimi induced Arabidopsis thaliana HIPVs were collected using headspace system and detected with GC-MS, and then analyzed the effects of these HIPVs chemicals on Lecanicillium lecanii strain V3450. We found that the HIPVs menthol and methyl salicylate at 1 and 10 nmol·ml−1 improved many performance aspects of the fungus, such as germination, sporulation, appressorial formation as well as its pathogenicity and virulence. These findings are not only important for understanding the multi-trophic interactions in an ecosystem, but also would contribute for developing new and easier procedures for conidial mass production as well as improve the pathogenicity and virulence of entomopathogenic fungi in biological pest management strategies. PMID:28079180

The Herbivore-Induced Plant Volatiles Methyl Salicylate and Menthol Positively affect Growth and Pathogenicity of Entomopathogenic Fungi

NASA Astrophysics Data System (ADS)

Lin, Yongwen; Qasim, Muhammad; Hussain, Mubasher; Akutse, Komivi Senyo; Avery, Pasco Bruce; Dash, Chandra Kanta; Wang, Liande

2017-01-01

Some herbivore-induced-plant volatiles (HIPVs) compounds are vital for the functioning of an ecosystem, by triggering multi-trophic interactions for natural enemies, plants and herbivores. However, the effect of these chemicals, which play a crucial role in regulating the multi-trophic interactions between plant-herbivore-entomopathogenic fungi, is still unknown. To fill this scientific gap, we therefore investigated how these chemicals influence the entomopathogenic fungi growth and efficacy. In this study, Lipaphis erysimi induced Arabidopsis thaliana HIPVs were collected using headspace system and detected with GC-MS, and then analyzed the effects of these HIPVs chemicals on Lecanicillium lecanii strain V3450. We found that the HIPVs menthol and methyl salicylate at 1 and 10 nmol·ml-1 improved many performance aspects of the fungus, such as germination, sporulation, appressorial formation as well as its pathogenicity and virulence. These findings are not only important for understanding the multi-trophic interactions in an ecosystem, but also would contribute for developing new and easier procedures for conidial mass production as well as improve the pathogenicity and virulence of entomopathogenic fungi in biological pest management strategies.

The Herbivore-Induced Plant Volatiles Methyl Salicylate and Menthol Positively affect Growth and Pathogenicity of Entomopathogenic Fungi.

PubMed

Lin, Yongwen; Qasim, Muhammad; Hussain, Mubasher; Akutse, Komivi Senyo; Avery, Pasco Bruce; Dash, Chandra Kanta; Wang, Liande

2017-01-12

Some herbivore-induced-plant volatiles (HIPVs) compounds are vital for the functioning of an ecosystem, by triggering multi-trophic interactions for natural enemies, plants and herbivores. However, the effect of these chemicals, which play a crucial role in regulating the multi-trophic interactions between plant-herbivore-entomopathogenic fungi, is still unknown. To fill this scientific gap, we therefore investigated how these chemicals influence the entomopathogenic fungi growth and efficacy. In this study, Lipaphis erysimi induced Arabidopsis thaliana HIPVs were collected using headspace system and detected with GC-MS, and then analyzed the effects of these HIPVs chemicals on Lecanicillium lecanii strain V3450. We found that the HIPVs menthol and methyl salicylate at 1 and 10 nmol·ml -1 improved many performance aspects of the fungus, such as germination, sporulation, appressorial formation as well as its pathogenicity and virulence. These findings are not only important for understanding the multi-trophic interactions in an ecosystem, but also would contribute for developing new and easier procedures for conidial mass production as well as improve the pathogenicity and virulence of entomopathogenic fungi in biological pest management strategies.

Predatory Mite Attraction to Herbivore-induced Plant Odors is not a Consequence of Attraction to Individual Herbivore-induced Plant Volatiles

PubMed Central

De Bruijn, Paulien J. A.; Sabelis, Maurice W.

2008-01-01

Predatory mites locate herbivorous mites, their prey, by the aid of herbivore-induced plant volatiles (HIPV). These HIPV differ with plant and/or herbivore species, and it is not well understood how predators cope with this variation. We hypothesized that predators are attracted to specific compounds in HIPV, and that they can identify these compounds in odor mixtures not previously experienced. To test this, we assessed the olfactory response of Phytoseiulus persimilis, a predatory mite that preys on the highly polyphagous herbivore Tetranychus urticae. The responses of the predatory mite to a dilution series of each of 30 structurally different compounds were tested. They mites responded to most of these compounds, but usually in an aversive way. Individual HIPV were no more attractive (or less repellent) than out-group compounds, i.e., volatiles not induced in plants fed upon by spider-mites. Only three samples were significantly attractive to the mites: octan-1-ol, not involved in indirect defense, and cis-3-hexen-1-ol and methyl salicylate, which are both induced by herbivory, but not specific for the herbivore that infests the plant. Attraction to individual compounds was low compared to the full HIPV blend from Lima bean. These results indicate that individual HIPV have no a priori meaning to the mites. Hence, there is no reason why they could profit from an ability to identify individual compounds in odor mixtures. Subsequent experiments confirmed that naive predatory mites do not prefer tomato HIPV, which included the attractive compound methyl salicylate, over the odor of an uninfested bean. However, upon associating each of these odors with food over a period of 15 min, both are preferred. The memory to this association wanes within 24 hr. We conclude that P. persimilis possesses a limited ability to identify individual spider mite-induced plant volatiles in odor mixtures. We suggest that predatory mites instead learn to respond to prey-associated mixtures of volatiles and, thus, to odor blends as a whole. PMID:18521678

Inhibition of Xenobiotic-Degrading Hydrolases by Organophosphinates

DTIC Science & Technology

1985-07-01

transient increase in the salicylic acid hydrolysis product was observed. Pretreatment with 4-nitrophenyl methyl(phenyl)phosphinate had no significant...h. Hydroly- sis of aspirin was not reduced in pretreated mice, although a transient increase in the salicylic acid hydrolysis product was observed...26 Figure 1. Pathways of aspirin metabolism in mammals: CE is carboxylester hydrolase, SA is salicylic acid, SU is salicyluric

[Effects of azadirachtin on rice plant volatiles induced by Nilaparvata lugens].

PubMed

Lu, Hai-Yan; Liu, Fang; Zhu, Shu-De; Zhang, Qing

2010-01-01

With the method of solid phase microextraction (SPME), a total of twenty-five volatiles were collected from rice plants induced by Nilaparvata lugens, and after applying azadirachtin fourteen of them were qualitatively identified by gas chromatography coupled by mass spectrometry (GC-MS), mainly of nine kinds of sesquiterpenes. Comparing with healthy rice plants, the plants attacked by N. lugens had more kinds of volatiles, including limonene, linalool, methyl salicylate, unknown 6, unknown 7, zingiberene, nerolidol, and hexadecane. Applying azadirachtin did not result in the production of new kind volatiles, but affected the relative concentrations of the volatiles induced by N. lugens. The proportions of limonene, linalool, methyl salicylate, unknown 6, zingiberene, and hexadecane changed obviously with the concentration of applied azadirachtin, while those of methyl salicylate, unknown 6, unknown 7, zingiberene, and nerolidol changed significantly with the days after azadirachtin application. Azadirachtin concentration, rice variety, and N. lugens density had significant interactions on the relative concentrations of all test N. lugens-induced volatiles.

Chelation and effectiveness of salicylate related compounds on pyresis, sedimentation rate and hematocrit

DOE Office of Scientific and Technical Information (OSTI.GOV)

Schubert, J.; Rosenthal, M.W.; Fried, J.F.

1984-01-01

The mechanism of action and identification of sites of salicylates and related compounds in antipyresis were studied. Structure-activity investigations of antipyresis were made using Sprague-Dawley rats. Results showed copper was chelated by the salicylate, passes through the cell membrane, and repairs the lesion. 13 references, 2 figures. (ACR)

Control of anthracnose disease via increased activity of defence related enzymes in 'Hass' avocado fruit treated with methyl jasmonate and methyl salicylate.

PubMed

Glowacz, Marcin; Roets, Nico; Sivakumar, Dharini

2017-11-01

Development of anthracnose disease caused by Colletotrichum gloeosporioides Penz. is one of the major issues within the avocado supply chain. Exposure to methyl jasmonate (MeJA) and methyl salicylate (MeSA) vapours at 10 and 100µmoll -1 was investigated as an alternative solution to commercial fungicide - prochloraz® that is currently being used by the industry. The incidence of anthracnose disease was found to be significantly reduced in 'Hass' avocado fruit treated with MeJA or MeSA vapours, especially at 100μmoll -1 . The mechanism involved enhanced activity of defence related enzymes, i.e. chitinase, β-1,3-glucanase and PAL, and higher content of epicatechin. Copyright © 2017. Published by Elsevier Ltd.

Cross-kingdom effects of plant-plant signaling via volatile organic compounds emitted by tomato (Solanum lycopersicum) plants infested by the greenhouse whitefly (Trialeurodes vaporariorum).

PubMed

Ángeles López, Yesenia Ithaí; Martínez-Gallardo, Norma Angélica; Ramírez-Romero, Ricardo; López, Mercedes G; Sánchez-Hernández, Carla; Délano-Frier, John Paul

2012-11-01

Volatile organic compounds (VOCs) emitted from plants in response to insect infestation can function as signals for the attraction of predatory/parasitic insects and/or repulsion of herbivores. VOCs also may play a role in intra- and inter-plant communication. In this work, the kinetics and composition of VOC emissions produced by tomato (Solanum lycopersicum) plants infested with the greenhouse whitefly Trialeurodes vaporariorum was determined within a 14 days period. The VOC emission profiles varied concomitantly with the duration of whitefly infestation. A total of 36 different VOCs were detected during the experiment, 26 of which could be identified: 23 terpenoids, plus decanal, decane, and methyl salicylate (MeSA). Many VOCs were emitted exclusively by infested plants, including MeSA and 10 terpenoids. In general, individual VOC emissions increased as the infestation progressed, particularly at 7 days post-infestation (dpi). Additional tunnel experiments showed that a 3 days exposure to VOC emissions from whitefly-infested plants significantly reduced infection by a biotrophic bacterial pathogen. Infection of VOC-exposed plants induced the expression of a likely tomato homolog of a methyl salicylate esterase gene, which preceded the expression of pathogenesis-related protein genes. This expression pattern correlated with reduced susceptibility in VOC-exposed plants. The observed cross-kingdom effect of plant-plant signaling via VOCs probably represents a generalized defensive response that contributes to increased plant fitness, considering that resistance responses to whiteflies and biotrophic bacterial pathogens in tomato share many common elements.

UV-C–Irradiated Arabidopsis and Tobacco Emit Volatiles That Trigger Genomic Instability in Neighboring Plants[W

PubMed Central

Yao, Youli; Danna, Cristian H.; Zemp, Franz J.; Titov, Viktor; Ciftci, Ozan Nazim; Przybylski, Roman; Ausubel, Frederick M.; Kovalchuk, Igor

2011-01-01

We have previously shown that local exposure of plants to stress results in a systemic increase in genome instability. Here, we show that UV-C–irradiated plants produce a volatile signal that triggers an increase in genome instability in neighboring nonirradiated Arabidopsis thaliana plants. This volatile signal is interspecific, as UV-C–irradiated Arabidopsis plants transmit genome destabilization to naive tobacco (Nicotiana tabacum) plants and vice versa. We report that plants exposed to the volatile hormones methyl salicylate (MeSA) or methyl jasmonate (MeJA) exhibit a similar level of genome destabilization as UV-C–irradiated plants. We also found that irradiated Arabidopsis plants produce MeSA and MeJA. The analysis of mutants impaired in the synthesis and/or response to salicylic acid (SA) and/or jasmonic acid showed that at least one other volatile compound besides MeSA and MeJA can communicate interplant genome instability. The NONEXPRESSOR OF PATHOGENESIS-RELATED GENES1 (npr1) mutant, defective in SA signaling, is impaired in both the production and the perception of the volatile signals, demonstrating a key role for NPR1 as a central regulator of genome stability. Finally, various forms of stress resulting in the formation of necrotic lesions also generate a volatile signal that leads to genomic instability. PMID:22028460

Detection of Methyl Salicylate Transforted by Honeybees (Apis mellifera) Using Solid Phase Microextration (SPME) Fibers

DOE Office of Scientific and Technical Information (OSTI.GOV)

BENDER, SUSAN FAE ANN; RODACY, PHILIP J.; BARNETT, JAMES L.

The ultimate goal of many environmental measurements is to determine the risk posed to humans or ecosystems by various contaminants. Conventional environmental monitoring typically requires extensive sampling grids covering several media including air, water, soil and vegetation. A far more efficient, innovative and inexpensive tactic has been found using honeybees as sampling mechanisms. Members from a single bee colony forage over large areas ({approx}2 x 10{sup 6} m{sup 2}), making tens of thousands of trips per day, and return to a fixed location where sampling can be conveniently conducted. The bees are in direct contact with the air, water, soilmore » and vegetation where they encounter and collect any contaminants that are present in gaseous, liquid and particulate form. The monitoring of honeybees when they return to the hive provides a rapid method to assess chemical distributions and impacts (1). The primary goal of this technology is to evaluate the efficiency of the transport mechanism (honeybees) to the hive using preconcentrators to collect samples. Once the extent and nature of the contaminant exposure has been characterized, resources can be distributed and environmental monitoring designs efficiently directed to the most appropriate locations. Methyl salicylate, a chemical agent surrogate was used as the target compound in this study.« less

Jasminum flexile flower absolute from India--a detailed comparison with three other jasmine absolutes.

PubMed

Braun, Norbert A; Kohlenberg, Birgit; Sim, Sherina; Meier, Manfred; Hammerschmidt, Franz-Josef

2009-09-01

Jasminum flexile flower absolute from the south of India and the corresponding vacuum headspace (VHS) sample of the absolute were analyzed using GC and GC-MS. Three other commercially available Indian jasmine absolutes from the species: J. sambac, J. officinale subsp. grandiflorum, and J. auriculatum and the respective VHS samples were used for comparison purposes. One hundred and twenty-one compounds were characterized in J. flexile flower absolute, with methyl linolate, benzyl salicylate, benzyl benzoate, (2E,6E)-farnesol, and benzyl acetate as the main constituents. A detailed olfactory evaluation was also performed.

Exogenous application of the plant signalers methyl jasmonate and salicylic acid induces changes in volatile emissions from citrus foliage and influences the aggregation behavior of Asian citrus psyllid (Diaphorina citri), vector of Huanglongbing

PubMed Central

Robbins, Paul S.; Niedz, Randy; McCollum, Greg; Alessandro, Rocco

2018-01-01

Huanglongbing, also known as citrus greening, is a destructive disease that threatens citrus production worldwide. It is putatively caused by the phloem-limited bacterium Candidatus Liberibacter asiaticus (Las). Currently, the disease is untreatable and efforts focus on intensive insecticide use to control the vector, Asian citrus psyllid (Diaphorina citri). Emerging psyllid resistance to multiple insecticides has generated investigations into the use of exogenously applied signaling compounds to enhance citrus resistance to D. citri and Las. In the present study, we examined whether foliar applications of methyl jasmonate (MJ), a volatile signaling compound associated with the induced systemic resistance pathway, and salicylic acid, a constituent of the systemic acquired resistance pathway, would elicit the emission of defense-related volatiles in citrus foliage, and what effect this might have on the host-plant searching behavior of D. citri. Comparisons were made of volatiles emitted from growing shoots of uninfected and Las-infected ‘Valencia’ sweet orange (Citrus sinensis) trees over two consecutive sampling days. A settling behavioral assay was used to compare psyllid attraction to MJ-treated vs. Tween-treated citrus sprigs. All three main effects, Las infection status, plant signaler application, and sampling day, influenced the proportions of individual volatile compounds emitted in different treatment groups. MJ- and SA-treated trees had higher emission rates than Tween-treated trees. Methyl salicylate (MeSA) and β-caryophyllene were present in higher proportions in the volatiles collected from Las-infected + trees. On the other hand, Las-infected + MJ-treated trees emitted lower proportions of MeSA than did Las-infected + Tween-treated trees. Because MeSA is a key D. citri attractant, this result suggests that MJ application could suppress MeSA emission from Las-infected trees, an approach that could be used to discourage psyllid colonization during shoot growth. MJ application enhanced emission of E-β-ocimene, indole, volatiles attractive to many of the psyllid’s natural enemies, indicating that MJ application could be used in an ‘attract and reward’ conservation biological control strategy. Volatile emissions in SA-treated trees were dominated by MeSA. MJ application elicited aggregation behavior in D. citri. Similar numbers of psyllids settled on MJ-treated versus Tween-treated sprigs, but a significantly greater percentage of the MJ-treated sprigs had aggregations of nine or more psyllids on them. Taken together, the results of this study indicate that exogenous applications of MJ or SA could be used to influence Asian citrus psyllid settling behavior and attract its natural enemies. PMID:29596451

Exogenous application of the plant signalers methyl jasmonate and salicylic acid induces changes in volatile emissions from citrus foliage and influences the aggregation behavior of Asian citrus psyllid (Diaphorina citri), vector of Huanglongbing.

PubMed

Patt, Joseph M; Robbins, Paul S; Niedz, Randy; McCollum, Greg; Alessandro, Rocco

2018-01-01

Huanglongbing, also known as citrus greening, is a destructive disease that threatens citrus production worldwide. It is putatively caused by the phloem-limited bacterium Candidatus Liberibacter asiaticus (Las). Currently, the disease is untreatable and efforts focus on intensive insecticide use to control the vector, Asian citrus psyllid (Diaphorina citri). Emerging psyllid resistance to multiple insecticides has generated investigations into the use of exogenously applied signaling compounds to enhance citrus resistance to D. citri and Las. In the present study, we examined whether foliar applications of methyl jasmonate (MJ), a volatile signaling compound associated with the induced systemic resistance pathway, and salicylic acid, a constituent of the systemic acquired resistance pathway, would elicit the emission of defense-related volatiles in citrus foliage, and what effect this might have on the host-plant searching behavior of D. citri. Comparisons were made of volatiles emitted from growing shoots of uninfected and Las-infected 'Valencia' sweet orange (Citrus sinensis) trees over two consecutive sampling days. A settling behavioral assay was used to compare psyllid attraction to MJ-treated vs. Tween-treated citrus sprigs. All three main effects, Las infection status, plant signaler application, and sampling day, influenced the proportions of individual volatile compounds emitted in different treatment groups. MJ- and SA-treated trees had higher emission rates than Tween-treated trees. Methyl salicylate (MeSA) and β-caryophyllene were present in higher proportions in the volatiles collected from Las-infected + trees. On the other hand, Las-infected + MJ-treated trees emitted lower proportions of MeSA than did Las-infected + Tween-treated trees. Because MeSA is a key D. citri attractant, this result suggests that MJ application could suppress MeSA emission from Las-infected trees, an approach that could be used to discourage psyllid colonization during shoot growth. MJ application enhanced emission of E-β-ocimene, indole, volatiles attractive to many of the psyllid's natural enemies, indicating that MJ application could be used in an 'attract and reward' conservation biological control strategy. Volatile emissions in SA-treated trees were dominated by MeSA. MJ application elicited aggregation behavior in D. citri. Similar numbers of psyllids settled on MJ-treated versus Tween-treated sprigs, but a significantly greater percentage of the MJ-treated sprigs had aggregations of nine or more psyllids on them. Taken together, the results of this study indicate that exogenous applications of MJ or SA could be used to influence Asian citrus psyllid settling behavior and attract its natural enemies.

Efficient synthesis of anacardic acid analogues and their antibacterial activities.

PubMed

Mamidyala, Sreeman K; Ramu, Soumya; Huang, Johnny X; Robertson, Avril A B; Cooper, Matthew A

2013-03-15

Anacardic acid derivatives exhibit a broad range of biological activities. In this report, an efficient method for the synthesis of anacardic acid derivatives was explored, and a small set of salicylic acid variants synthesised retaining a constant hydrophobic element (a naphthyl tail). The naphthyl side chain was introduced via Wittig reaction and the aldehyde installed using directed ortho-metalation reaction of the substituted o-anisic acids. The failure of ortho-metalation using unprotected carboxylic acid group compelled us to use directed ortho-metalation in which a tertiary amide was used as a strong ortho-directing group. In the initial route, tertiary amide cleavage during final step was challenging, but cleaving the tertiary amide before Wittig reaction was beneficial. The Wittig reaction with protected carboxylic group (methyl ester) resulted in side-products whereas using sodium salt resulted in higher yields. The novel compounds were screened for antibacterial activity and cytotoxicity. Although substitution on the salicylic head group enhanced antibacterial activities they also enhanced cytotoxicity. Copyright © 2013 Elsevier Ltd. All rights reserved.

Differential expression of calcium/calmodulin-regulated SlSRs in response to abiotic and biotic stresses in tomato fruit.

PubMed

Yang, Tianbao; Peng, Hui; Whitaker, Bruce D; Jurick, Wayne M

2013-07-01

Calcium has been shown to enhance stress tolerance, maintain firmness and reduce decay in fruits. Previously we reported that seven tomato SlSRs encode calcium/calmodulin-regulated proteins, and that their expressions are developmentally regulated during fruit development and ripening, and are also responsive to ethylene. To study their expressions in response to stresses encountered during postharvest handling, tomato fruit at the mature-green stage was subjected to chilling and wounding injuries, infected with Botrytis cinerea and treated with salicylic acid or methyl jasmonate. Gene expression studies revealed that the seven SlSRs differentially respond to different stress signals. SlSR2 was the only gene upregulated by all the treatments. SlSR4 acted as a late pathogen-induced gene; it was upregulated by salicylic acid and methyl jasmonate, but downregulated by cold treatment. SlSR3L was cold- and wound-responsive and was also induced by salicylic acid. SlSR1 and SlSR1L were repressed by cold, wounding and pathogen infection, but were upregulated by salicylic acid and methyl jasmonate. Overall, results of these expression studies indicate that individual SlSRs have distinct roles in responses to the specific stress signals, and SlSRs may act as a coordinator(s) connecting calcium-mediated signaling with other stress signal transduction pathways during fruit ripening and storage. © 2013 Scandinavian Plant Physiology Society.

Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity.

PubMed

Jiménez-Díaz, I; Molina-Molina, J M; Zafra-Gómez, A; Ballesteros, O; Navalón, A; Real, M; Sáenz, J M; Fernández, M F; Olea, N

2013-10-01

UV-filters are widely used in many personal care products and cosmetics. Recent studies indicate that some organic UV-filters can accumulate in biota and act as endocrine disruptors, but there are few studies on the occurrence and fate of these compounds in humans. In the present work, a new liquid chromatography-tandem mass spectrometry (LC-MS/MS) method to assess the presence of six UV-filters in current use (benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor, and 3-benzylidene camphor) in human placental tissue is proposed. The method involves the extraction of the analytes from the samples using ethyl acetate, followed by a clean-up step using centrifugation prior to their quantification by LC-MS/MS using an atmospheric pressure chemical ionization (APCI) interface. Bisphenol A-d16 was used as surrogate for the determination of benzyl salicylate, phenyl salicylate, octyl salicylate and homosalate in negative mode and benzophenone-d10, was used as surrogate for the determination of 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in positive mode. The found limits of detection ranged from 0.4 to 0.6ngg(-1) and the limits of quantification ranged from 1.3 to 2.0ngg(-1), while variability was under 13.7%. Recovery rates for spiked samples ranged from 97% to 104%. Moreover, the interactions of these compounds with the human estrogen receptor alpha (hERα) and androgen receptor (hAR), using two in vitro bioassays based on reporter gene expression and cell proliferation assessment, were also investigated. All tested compounds, except benzyl salicylate and octyl salicylate, showed estrogenic activity in the E-Screen bioassay whereas only homosalate and 3-(4-methylbenzylidene) camphor were potent hAR antagonists. Although free salicylate derivatives and free camphor derivatives were not detected in the human placenta samples analyzed, the observed estrogenic and anti-androgenic activities of some of these compounds support the analysis of their occurrence and their role as endocrine disrupters in humans. Copyright © 2013 Elsevier B.V. All rights reserved.

Salicylate toxicity from ingestion of traditional massage oil

PubMed Central

Muniandy, Rajesh Kumar; Sinnathamby, Vellan

2012-01-01

A 16-month-old child developed a brief generalised tonic–clonic fitting episode and vomiting at home, after accidental ingestion of traditional massage oil. As the patient presented with clinical features of salicylate toxicity, appropriate management was instituted. He was admitted to the intensive care unit for multiorgan support. The child was discharged well 1 week after the incident. Methyl-salicylate is a common component of massage oils which are used for topical treatment of joint and muscular pains. However, these massage oils may be toxic when taken orally. Early recognition of the salicylate toxicity is very important in producing a good patient outcome. PMID:22922924

Feeding by emerald ash borer larvae induces systemic changes in black ash foliar chemistry.

PubMed

Chen, Yigen; Whitehill, Justin G A; Bonello, Pierluigi; Poland, Therese M

2011-11-01

The exotic wood-boring pest, emerald ash borer (EAB), Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), has been threatening North American ash (Fraxinus spp.) resources, this being recognized since its first detection in Michigan, USA and Ontario, Canada in 2002. Ash trees are killed by larval feeding in the cambial region, which results in disruption of photosynthate and nutrient translocation. In this study, changes in volatile and non-volatile foliar phytochemicals of potted 2-yr-old black ash, Fraxinus nigra Marshall, seedlings were observed in response to EAB larval feeding in the main stem. EAB larval feeding affected levels of six compounds [hexanal, (E)-2-hexenal, (Z)-3-hexenyl acetate, (E)-β-ocimene, methyl salicylate, and (Z,E)-α-farnesene] with patterns of interaction depending upon compounds of interest and time of observation. Increased methyl salicylate emission suggests similarity in responses induced by EAB larval feeding and other phloem-feeding herbivores. Overall, EAB larval feeding suppressed (Z)-3-hexenyl acetate emission, elevated (E)-β-ocimene emission in the first 30days, but emissions leveled off thereafter, and generally increased the emission of (Z,E)-α-farnesene. Levels of carbohydrates and phenolics increased overall, while levels of proteins and most amino acids decreased in response to larval feeding. Twenty-three amino acids were consistently detected in the foliage of black ash. The three most abundant amino acids were aspartic acid, glutamic acid, glutamine, while the four least abundant were α-aminobutyric acid, β-aminoisobutyric acid, methionine, and sarcosine. Most (16) foliar free amino acids and 6 of the 9 detected essential amino acids decreased with EAB larval feeding. The ecological consequences of these dynamic phytochemical changes on herbivores harbored by ash trees and potential natural enemies of these herbivores are discussed. Copyright © 2011 Elsevier Ltd. All rights reserved.

Transcriptional Profiling of Sorghum Induced by Methyl Jasmonate, Salicylic Acid, and Aminocyclopropane Carboxylic Acid Reveals Cooperative Regulation and Novel Gene Responses1[w

PubMed Central

Salzman, Ron A.; Brady, Jeff A.; Finlayson, Scott A.; Buchanan, Christina D.; Summer, Elizabeth J.; Sun, Feng; Klein, Patricia E.; Klein, Robert R.; Pratt, Lee H.; Cordonnier-Pratt, Marie-Michèle; Mullet, John E.

2005-01-01

We have conducted a large-scale study of gene expression in the C4 monocot sorghum (Sorghum bicolor) L. Moench cv BTx623 in response to the signaling compounds salicylic acid (SA), methyl jasmonate (MeJA), and the ethylene precursor aminocyclopropane carboxylic acid. Expression profiles were generated from seedling root and shoot tissue at 3 and 27 h, using a microarray containing 12,982 nonredundant elements. Data from 102 slides and quantitative reverse transcription-PCR data on mRNA abundance from 171 genes were collected and analyzed and are here made publicly available. Numerous gene clusters were identified in which expression was correlated with particular signaling compound and tissue combinations. Many genes previously implicated in defense responded to the treatments, including numerous pathogenesis-related genes and most members of the phenylpropanoid pathway, and several other genes that may represent novel activities or pathways. Genes of the octadecanoic acid pathway of jasmonic acid (JA) synthesis were induced by SA as well as by MeJA. The resulting hypothesis that increased SA could lead to increased endogenous JA production was confirmed by measurement of JA content. Comparison of responses to SA, MeJA, and combined SA+MeJA revealed patterns of one-way and mutual antagonisms, as well as synergistic effects on regulation of some genes. These experiments thus help further define the transcriptional results of cross talk between the SA and JA pathways and suggest that a subset of genes coregulated by SA and JA may comprise a uniquely evolved sector of plant signaling responsive cascades. PMID:15863699

Influence of design, physico-chemical and environmental parameters on pharmaceuticals and fragrances removal by constructed wetlands.

PubMed

Hijosa-Valsero, M; Matamoros, V; Sidrach-Cardona, R; Pedescoll, A; Martín-Villacorta, J; García, J; Bayona, J M; Bécares, E

2011-01-01

The ability of several mesocosm-scale and full-scale constructed wetlands (CWs) to remove pharmaceuticals and personal care products (PPCPs) from urban wastewater was assessed. The results of three previous works were considered as a whole to find common patterns in PPCP removal. The experiment took place outdoors under winter and summer conditions. The mesocosm-scale CWs differed in some design parameters, namely the presence of plants, the vegetal species chosen (Typha angustifolia versus Phragmites australis), the flow configuration (surface flow versus subsurface flow), the primary treatment (sedimentation tank versus HUSB), the feeding regime (batch flow versus continuous saturation) and the presence of gravel bed. The full-scale CWs consisted of a combination of various subsystems (ponds, surface flow CWs and subsurface flow CWs). The studied PPCPs were ketoprofen, naproxen, ibuprofen, diclofenac, salicylic acid, carbamazepine, caffeine, methyl dihydrojasmonate, galaxolide and tonalide. The performance of the evaluated treatment systems was compound dependent and varied as a function of the CW-configuration. In addition, PPCP removal efficiencies were lower during winter. The presence of plants favoured naproxen, ibuprofen, diclofenac, salicylic acid, caffeine, methyl dihydrojasmonate, galaxolide and tonalide removal. Significant positive correlations were observed between the removal of most PPCPs and temperature or redox potential. Accordingly, microbiological pathways appear to be the most likely degradation route for the target PPCPs in the CWs studied.

Development of supercritical CO2 extraction of bioactive phytochemicals from black poplar (Populus nigra L.) buds followed by GC-MS and UHPLC-DAD-QqTOF-MS.

PubMed

Kuś, Piotr M; Okińczyc, Piotr; Jakovljević, Martina; Jokić, Stela; Jerković, Igor

2018-05-25

The supercritical CO 2 (SC-CO 2 ) extraction process of black poplar (Populus nigra L.) buds was optimized (pressure, temperature) based on the yields of major phytochemicals (volatiles and non-volatiles). The optimal settings were 30 MPa/60 °C. Major volatiles determined by GC-MS in the optimized SC-CO 2 extract (mg of benzyl salicylate equivalent (BSE) per 100 g of buds) were: pinostrobin chalcone (1574.2), β-eudesmol (640.8), α-eudesmol (581.9), 2-methyl-2-butenyl-p-coumarate (289.9), pentyl-p-coumarate (457.0), γ-eudesmol (294.4), and benzyl salicylate (289.2). Partial qualitative similarity was observed between SC-CO 2 extracts and corresponding hydrodistilled essential oil dominated by sesquiterpenes, but with lower yields. Major compounds (mg per 100 g of buds) identified by UHPLC-DAD-QqTOF-MS in the optimized SC-CO 2 extract were: pinostrobin (751.7), pinocembrin (485.6), 3-O-pinobanksin acetate and methyl-butenyl-p-coumarate (290.2; 144.9 of pinobanksin and p-coumaric acid equivalents, respectively). SC-CO 2 extraction was found useful for green, efficient and simultaneous extraction of both volatile/non-volatile, bioactive phytochemicals of poplar buds - precursors of poplar-type propolis. Copyright © 2018 Elsevier B.V. All rights reserved.

Assessment of the UV/Cl2 advanced oxidation process for the degradation of the emerging contaminants amitriptyline hydrochloride, methyl salicylate and 2-phenoxyethanol in water systems.

PubMed

Javier Benitez, F; Real, Francisco J; Acero, Juan L; Casas, Francisco

2017-10-01

Three emerging contaminants (amitriptyline hydrochloride (AH), methyl salicylate (MS) and 2-phenoxyethanol (PE)) frequently found in wastewaters were selected to be individually degraded in ultra-pure water by the advanced oxidation process (AOP) constituted by the combination of UV radiation and chlorine. The influence of pH, initial chlorine concentration and nature of the contaminants was firstly explored. The trend for the reactivity of the selected compounds was deduced: AH > MS > PE. A later kinetic study was carried out focused on the evaluation of the first-order rate constants and the determination of the partial contribution to the global reaction of the direct photochemical pathway and the radical pathway. In a second stage, the simultaneous oxidation of mixtures of the selected contaminants in several types of water was also performed by the same combination UV/Cl 2 . The efficiency of this combined system UV/Cl 2 was compared to other oxidants such as the UV/[Formula: see text] and UV/H 2 O 2 AOPs, and the influence of the operating variables was discussed. Results confirmed that the UV/Cl 2 system provides higher elimination efficiencies among the AOPs tested. The presence of dissolved organic matter and bicarbonate ions in the water matrix caused a decrease in the treatment efficiency.

Priming of seeds with methyl jasmonate induced resistance to hemi-biotroph Fusarium oxysporum f.sp. lycopersici in tomato via 12-oxo-phytodienoic acid, salicylic acid, and flavonol accumulation.

PubMed

Król, P; Igielski, R; Pollmann, S; Kępczyńska, E

2015-05-01

Methyl jasmonate (MeJA) was tested by seed treatment for its ability to protect tomato seedlings against fusarium wilt caused by the soil-borne fungal pathogen Fusarium oxysporum f.sp. lycopersici. Isolated from Solanum lycopersicon L. seeds, cv. Beta fungus was identified as F. oxysporum f.sp. lycopersici Race 3 fungus by using phytopathological and molecular methods. MeJA applied at 0.01, 0.1 and 1 mM reduced spore germination and mycelial growth in vitro. Soaking of tomato seeds in MeJA solution at 0.1 mM for 1 h significantly enhanced the resistance level against the tested fungus in tomato seedlings 4 weeks after inoculation. The extracts from leaves of 15-day-old seedlings obtained from previously MeJA soaked seeds had the ability to inhibit in vitro spore germination of tested fungus. In these seedlings a significant increase in the levels phenolic compounds such as salicylic acid (SA), kaempferol and quercetin was observed. Up-regulation of phenylalanine ammonia-lyase (PAL5) and benzoic acid/salicylic acid carboxyl methyltransferase (BSMT) genes and down-regulation of the isochorysmate synthase (ICS) gene in response to exogenous MeJA application indicate that the phenylalanine ammonia-lyase (PAL), not the isochorismate (IC) pathway, is the primary route for SA production in tomato. Moreover, the increased accumulation of the flavonols quercetin and kaempferol appears closely related to the increase of PAL5, chalcone synthase (CHS) and flavonol synthase/flavanone 3-hydroxylase-like (FLS) genes. Elevated levels of salicylic acid in seedlings raised from MeJA-soaked seeds were simultaneously accompanied by a decrease of jasmonic acid, the precursor of MeJA, and an increase of 12-oxo-phytodienoic acid (OPDA), the precursor of jasmonic acid. The present results indicate that the priming of tomato seeds with 0.1mM MeJA before sowing enables the seedlings grown from these seeds to reduce the attack of the soil-borne fungal pathogen F. oxysporum f.sp. lycopersici, so it can be applied in practice. Copyright © 2015 Elsevier GmbH. All rights reserved.

Inoculation of the nonlegume Capsicum annuum L. with Rhizobium strains. 2. Changes in sterols, triterpenes, fatty acids, and volatile compounds.

PubMed

Silva, Luís R; Azevedo, Jessica; Pereira, Maria J; Carro, Lorena; Velazquez, Encarna; Peix, Alvaro; Valentão, Patrícia; Andrade, Paula B

2014-01-22

Peppers (Capsicum spp.) are consumed worldwide, imparting flavor, aroma, and color to foods, additionally containing high concentrations of biofunctional compounds. This is the first report about the effect of the inoculation of two Rhizobium strains on sterols, triterpenes, fatty acids, and volatile compounds of leaves and fruits of pepper (Capsicum annuum L.) plants. Generally, inoculation with strain TVP08 led to the major changes, being observed a decrease of sterols and triterpenes and an increase of fatty acids, which are related to higher biomass, growth, and ripening of pepper fruits. The increase of volatile compounds may reflect the elicitation of plant defense after inoculation, since the content on methyl salicylate was significantly increased in inoculated material. The findings suggest that inoculation with Rhizobium strains may be employed to manipulate the content of interesting metabolites in pepper leaves and fruits, increasing potential health benefits and defense abilities of inoculated plants.

Comparative study of volatile components from male and female flower buds of Populus × tomentosa by HS-SPME-GC-MS.

PubMed

Xu, Liang; Liu, Haiping; Ma, Yucui; Wu, Cui; Li, Ruiqi; Chao, Zhimao

2018-06-13

The differences of volatile components in male (MFB) and female flower buds (FFB) of Populus × tomentosa were analysed and compared by HS-SPME with GC-MS for the first time. A total of 34 compounds were identified. Two clusters were clearly divided into male and female by hierarchical clustering analysis. Both the male and female flower buds showed methyl salicylate (22.83 and 24.09%, respectively) and 2-hydroxy-benzaldehyde (10.05 and 12.41%, respectively) as the main volatile constituents. The content of 2-cyclohexen-1-one, benzyl benzoate, and methyl benzoate in FFB was remarkably higher than in MFB. In contrast, the content of ethyl benzoate in MFB was greater than that in FFB. The phenomena showed the characteristic differences between MFB and FFB of P. × tomentosa, which enriched the basic studies on dioecious plant.

SALICYLATE INCREASES THE GAIN OF THE CENTRAL AUDITORY SYSTEM

PubMed Central

Sun, W.; Lu, J.; Stolzberg, D.; Gray, L.; Deng, A.; Lobarinas, E.; Salvi, R. J.

2009-01-01

High doses of salicylate, the anti-inflammatory component of aspirin, induce transient tinnitus and hearing loss. Systemic injection of 250 mg/kg of salicylate, a dose that reliably induces tinnitus in rats, significantly reduced the sound evoked output of the rat cochlea. Paradoxically, salicylate significantly increased the amplitude of the sound-evoked field potential from the auditory cortex (AC) of conscious rats, but not the inferior colliculus (IC). When rats were anesthetized with isoflurane, which increases GABA-mediated inhibition, the salicylate-induced AC amplitude enhancement was abolished, whereas ketamine, which blocks N-methyl-d-aspartate receptors, further increased the salicylate-induced AC amplitude enhancement. Direct application of salicylate to the cochlea, however, reduced the response amplitude of the cochlea, IC and AC, suggesting the AC amplitude enhancement induced by systemic injection of salicylate does not originate from the cochlea. To identify a behavioral correlate of the salicylate-induced AC enhancement, the acoustic startle response was measured before and after salicylate treatment. Salicylate significantly increased the amplitude of the startle response. Collectively, these results suggest that high doses of salicylate increase the gain of the central auditory system, presumably by down-regulating GABA-mediated inhibition, leading to an exaggerated acoustic startle response. The enhanced startle response may be the behavioral correlate of hyperacusis that often accompanies tinnitus and hearing loss. Published by Elsevier Ltd on behalf of IBRO. PMID:19154777

Abundance of volatile organic compounds in white ash phloem and emerald ash borer larval frass does not attract Tetrastichus planipennisi in a Y-tube olfactometer.

PubMed

Chen, Yigen; Ulyshen, Michael D; Poland, Therese M

2016-10-01

Many natural enemies employ plant- and/or herbivore-derived signals for host/prey location. The larval parasitoid Tetrastichus planipennisi Yang (Hymenoptera: Eulophidae) is 1 of 3 biocontrol agents currently being released in an effort to control the emerald ash borer (EAB), Agrilus planipennis Fairmaire (Coloeptera: Burprestidae) in North America. To enhance its efficiency, allelochemicals that attract it need to be assessed. In this study, ash phloem volatile organic compounds (VOCs) of black, green, and white ash, and EAB larval frass were compared. Foraging behavior of T. planipennisi females in response to VOCs of white ash or frass from EAB larvae feeding on white ash phloem was tested using a Y-tube olfactometer. Results indicated that the 3 ash species had similar VOC profiles. EAB larval frass generally contained greater levels of VOCs than phloem. Factor analysis indicated that the 11 VOCs could be broadly divided into 2 groups, with α-bisabolol, β-caryophyllene, (E)-2-hexenal, (Z)-3-hexenal, limonene, methyl benzoate, methyl indole-3-acetic acid, methyl jasmonate, methyl salicylate as the first group and the rest (i.e., methyl linoleate and methyl linolenate) as a second. Abundance of VOCs in white ash phloem tissue and frass, nevertheless, did not attract T. planipennisi females. The concealed feeding of EAB larvae might explain the selection for detectable and reliable virbrational signals, instead of undetectable and relatively unreliable VOC cues from phloem and frass, in short-range foraging by T. planipennisi. Alternatively, it is possible that T. planipennisi is not amenable to the Y-tube olfactometer assay employed. © 2015 Institute of Zoology, Chinese Academy of Sciences.

Resonance electron attachment to plant hormones and its likely connection with biochemical processes

NASA Astrophysics Data System (ADS)

Pshenichnyuk, Stanislav A.; Modelli, Alberto

2014-01-01

Gas-phase formation of temporary negative ion states via resonance attachment of low-energy (0-6 eV) electrons into vacant molecular orbitals of salicylic acid (I) and its derivatives 3-hydroxy- (II) and 4-hydroxybenzoic acid (III), 5-cloro salicylic acid (IV) and methyl salicylate (V) was investigated for the first time by electron transmission spectroscopy. The description of their empty-level structures was supported by density functional theory and Hartree-Fock calculations, using empirically calibrated linear equations to scale the calculated virtual orbital energies. Dissociative electron attachment spectroscopy (DEAS) was used to measure the fragment anion yields generated through dissociative decay channels of the parent molecular anions of compounds I-V, detected with a mass filter as a function of the incident electron energy in the 0-14 eV energy range. The most intense negative fragment produced by DEA to isomers I-III is the dehydrogenated molecular anion [M-H]-, mainly formed at incident electron energies around 1 eV. The vertical and adiabatic electron affinities were evaluated at the B3LYP/6-31+G(d) level as the anion/neutral total energy difference. The same theoretical method was also used for evaluation of the thermodynamic energy thresholds for production of the negative fragments observed in the DEA spectra. The gas-phase DEAS data can provide support for biochemical reaction mechanisms in vivo.

Swallowing sunscreen

MedlinePlus

... any of these ingredients: Cinnamates Padimate-O Salicylates (aspirin-like compounds) Zinc oxide Sunscreen may also contain ... from salicylates could cause a condition similar to aspirin overdose .

Disruption of Vector Host Preference with Plant Volatiles May Reduce Spread of Insect-Transmitted Plant Pathogens.

PubMed

Martini, Xavier; Willett, Denis S; Kuhns, Emily H; Stelinski, Lukasz L

2016-05-01

Plant pathogens can manipulate the odor of their host; the odor of an infected plant is often attractive to the plant pathogen vector. It has been suggested that this odor-mediated manipulation attracts vectors and may contribute to spread of disease; however, this requires further broad demonstration among vector-pathogen systems. In addition, disruption of this indirect chemical communication between the pathogen and the vector has not been attempted. We present a model that demonstrates how a phytophathogen (Candidatus Liberibacter asiaticus) can increase its spread by indirectly manipulating the behavior of its vector (Asian citrus psyllid, Diaphorina citri Kuwayama). The model indicates that when vectors are attracted to pathogen-infected hosts, the proportion of infected vectors increases, as well as, the proportion of infected hosts. Additionally, the peak of infected host populations occurs earlier as compared with controls. These changes in disease dynamics were more important during scenarios with higher vector mortality. Subsequently, we conducted a series of experiments to disrupt the behavior of the Asian citrus psyllid. To do so, we exposed the vector to methyl salicylate, the major compound released following host infection with the pathogen. We observed that during exposure or after pre-exposure to methyl salicylate, the host preference can be altered; indeed, the Asian citrus psyllids were unable to select infected hosts over uninfected counterparts. We suggest mechanisms to explain these interactions and potential applications of disrupting herbivore host preference with plant volatiles for sustainable management of insect vectors.

Diaphorina citri Induces Huanglongbing-Infected Citrus Plant Volatiles to Repel and Reduce the Performance of Propylaea japonica.

PubMed

Lin, Yongwen; Lin, Sheng; Akutse, Komivi S; Hussain, Mubasher; Wang, Liande

2016-01-01

Transmission of plant pathogens through insect vectors is a complex biological process involving interactions between the host plants, insects, and pathogens. Simultaneous impact of the insect damage and pathogenic bacteria in infected host plants induce volatiles that modify not only the behavior of its insect vector but also of their natural enemies, such as parasitoid wasps. Therefore, it is essential to understand how insects such as the predator ladybird beetle responds to volatiles emitted from a host plant and how the disease transmission alters the interactions between predators, vector, pathogens, and plants. In this study, we investigated the response of Propylaea japonica to volatiles from citrus plants damaged by Diaphorina citri and Candidatus Liberibacter asiaticus through olfactometer bioassays. Synthetic chemical blends were also used to determine the active compounds in the plant volatile. The results showed that volatiles emitted by healthy plants attracted more P. japonica than other treatments, due to the presence of high quantities of D-limonene and beta-ocimene, and the lack of methyl salicylate. When using synthetic chemicals in the olfactory tests, we found that D-limonene attracted P. japonica while methyl salicylate repelled the predator. However, beta-ocimene attracted the insects at lower concentrations but repelled them at higher concentrations. These results indicate that P. japonica could not efficiently search for its host by using volatile cues emitted from psyllids- and Las bacteria-infected citrus plants.

Mechanisms of Decreased Moisture Uptake in ortho- Methylated Di(Cyanate Esters)

DTIC Science & Technology

2014-10-01

Distribution A: Approved for public release; distribution is unlimited. 1 Mechanisms of Decreased Moisture Uptake in ortho- Methylated Di(Cyanate...when analogous networks containing a single methyl group ortho- to each aryl- cyanurate linkage were prepared by reduction and acid-catalyzed coupling...of salicylic acid followed by treatment with cyanogen bromide and subsequent cyclotrimerization. The differences in water uptake were observed

VvMJE1 of the grapevine (Vitis vinifera) VvMES methylesterase family encodes for methyl jasmonate esterase and has a role in stress response

USDA-ARS?s Scientific Manuscript database

The known members of the plant methyl esterase (MES) family catalyze hydrolysis of a C-O ester linkage of methyl esters of several phytohormones including indole-3-acetic acid, salicylic acid, and jasmonic acid. The genome of grapevine (Vitis vinifera) was found to contain 15 MES genes, designated V...

Preliminary evaluation of military, commercial and novel skin decontamination products against a chemical warfare agent simulant (methyl salicylate).

PubMed

Matar, Hazem; Guerreiro, Antonio; Piletsky, Sergey A; Price, Shirley C; Chilcott, Robert P

2015-08-13

Rapid decontamination is vital to alleviate adverse health effects following dermal exposure to hazardous materials. There is an abundance of materials and products which can be utilised to remove hazardous materials from the skin. In this study, a total of 15 products were evaluated, 10 of which were commercial or military products and five were novel (molecular imprinted) polymers. The efficacies of these products were evaluated against a 10 µl droplet of 14 C-methyl salicylate applied to the surface of porcine skin mounted on static diffusion cells. The current UK military decontaminant (Fuller's earth) performed well, retaining 83% of the dose over 24 h and served as a benchmark to compare with the other test products. The five most effective test products were Fuller's earth (the current UK military decontaminant), Fast-Act® and three novel polymers [based on itaconic acid, 2-trifluoromethylacrylic acid and N,N-methylenebis(acrylamide)]. Five products (medical moist-free wipes, 5% FloraFree™ solution, normal baby wipes, baby wipes for sensitive skin and Diphotérine™) enhanced the dermal absorption of 14 C-methyl salicylate. Further work is required to establish the performance of the most effective products identified in this study against chemical warfare agents.

Preliminary evaluation of military, commercial and novel skin decontamination products against a chemical warfare agent simulant (methyl salicylate).

PubMed

Matar, Hazem; Guerreiro, Antonio; Piletsky, Sergey A; Price, Shirley C; Chilcott, Robert P

2016-01-01

Rapid decontamination is vital to alleviate adverse health effects following dermal exposure to hazardous materials. There is an abundance of materials and products which can be utilised to remove hazardous materials from the skin. In this study, a total of 15 products were evaluated, 10 of which were commercial or military products and five were novel (molecular imprinted) polymers. The efficacies of these products were evaluated against a 10 µl droplet of (14)C-methyl salicylate applied to the surface of porcine skin mounted on static diffusion cells. The current UK military decontaminant (Fuller's earth) performed well, retaining 83% of the dose over 24 h and served as a benchmark to compare with the other test products. The five most effective test products were Fuller's earth (the current UK military decontaminant), Fast-Act® and three novel polymers [based on itaconic acid, 2-trifluoromethylacrylic acid and N,N-methylenebis(acrylamide)]. Five products (medical moist-free wipes, 5% FloraFree™ solution, normal baby wipes, baby wipes for sensitive skin and Diphotérine™) enhanced the dermal absorption of (14)C-methyl salicylate. Further work is required to establish the performance of the most effective products identified in this study against chemical warfare agents.

Ear swelling test by using laser speckle imaging with a long exposure time

NASA Astrophysics Data System (ADS)

Kalchenko, Vyacheslav; Kuznetsov, Yuri; Preise, Dina; Meglinski, Igor; Harmelin, Alon

2014-06-01

Laser speckle imaging with long exposure time has been applied noninvasively to visualize the immediate reaction of cutaneous vessels in mice in response to a known primary irritant and potential allergen-methyl salicylate. The compound has been used topically on the surface of the pinna and the reaction of the vascular network was examined. We demonstrate that irritant-induced acute vascular reaction can be effectively and accurately detected by laser speckle imaging technique. The current approach holds a great promise for application in routine screening of the cutaneous vascular response induced by contact agents, screenings of mouse ear swelling test, and testing the allergenic potential of new synthetic materials and healthcare pharmaceutical products.

Identification of Key Root Volatiles Signaling Preference of Tomato Over Spinach by the Root Knot Nematode Meloidogyne incognita.

PubMed

Murungi, Lucy K; Kirwa, Hillary; Coyne, Danny; Teal, Peter E A; Beck, John J; Torto, Baldwyn

2018-06-25

The root knot nematode, Meloidogyne incognita (Kofoid and White) Chitwood, is a serious pest of tomato (Solanum lycopersicum) and spinach (Spinacea oleracea) in sub-Saharan Africa. In East Africa these two crops are economically important and are commonly intercropped by smallholder farmers. The role of host plant volatiles in M. incognita interactions with these two commodities is currently unknown. Here, we investigate the olfactory basis of attraction of tomato and spinach roots by the infective second stage juveniles (J2s) of M. incognita. In olfactometer assays, J2s were attracted to root volatiles from both crops over moist sand (control), but in choice tests using the two host plants, volatiles of tomato roots were more attractive than those released by spinach. Root volatiles sampled by solid phase micro-extraction (SPME) fiber and analysed by gas chromatography/mass spectrometry (GC/MS) identified a total of eight components, of which five (2-isopropyl-3-methoxypyrazine, 2-(methoxy)-3-(1-methylpropyl)pyrazine, tridecane, and α- and β-cedrene) occurred in the root-emitted volatiles of both plants, with three (δ-3-carene, sabinene and methyl salicylate) being specific to tomato root volatiles. In a series of bioassays, methyl salicylate contributed strongly to the attractiveness of tomato, whereas 2-isopropyl-3-methoxypyrazine and tridecane contributed to the attractiveness of spinach. M. incognita J2s were also more attracted to natural spinach root volatiles when methyl salicylate was combined, than to spinach volatiles alone, indicating that the presence of methyl salicylate in tomato volatiles strongly contributes to its preference over spinach. Our results indicate that since both tomato and spinach roots are attractive to M. incognita, identifying cultivars of these two plant species that are chemically less attractive can be helpful in the management of root knot nematodes.

Consumption study and identification of methyl salicylate in spicy cassava chips

NASA Astrophysics Data System (ADS)

Nirjana, Marlene; Anggadiredja, Kusnandar; Damayanti, Sophi

2015-09-01

Spicy cassava chips is a popular snack. However, some news in electronic media reported addition of balsam which is a banned food additives in that product to give extra spicy flavor. This study aimed to determine ITB students' pattern of consumption, health problems caused by spicy chips consumption, and knowledge about illicit use of food additives in that product, and identify the main content of balsam namely methyl salicylate in 10 samples of spicy cassava chips taken from inside and outside about ITB campus. A total of 300 questionnaires distributed to ITB students then data processing was performed. Spicy cassava chips sample macerated in 50 mL of methanol for 24 hours at room temperature, filtered and analyzed using gas chromatography capillary column with OV-1, nitrogen carrier gas and flame ionization detector. Based on questionnaires, 292 (97%) of 300 respondents had consumed spicy chips. A total of 247 (85%) from 292 respondents spicy chips consumed less than 3 times a week. A total of 195 respondents (67%) had experienced health problems after eating spicy chips. There were 137 (47%) of the 292 respondents who knew about the illicit addition of food additives into spicy chips; only 35 respondents (12%) who knew about balsam's addition. There were 126 respondents (43%) who did not pay attention to their health because they will keep eating spicy chips despite the addition of banned food additives. Through the verification of the standard addition method in gas chromatography system with a hydrogen pressure of 1.5 bar, injector temperature 200 °C, detector temperature 230 °C, oven temperature 60 °C for 2 minutes and then increased to 230 °C with rate 6 °C/menit; linearity, limit of detection, limit of quantitation, accuracy, precision, and specificity parameters met the acceptance limits. From 10 spicy cassava chips samples which were analyzed, they did not reveal any content of methyl salicylate. Methyl salicylate contained in the positive control was 1.273 mg/mL.

Discovery of novel, high potent, ABC type PTP1B inhibitors with TCPTP selectivity and cellular activity.

PubMed

Liu, Peihong; Du, Yongli; Song, Lianhua; Shen, Jingkang; Li, Qunyi

2016-08-08

Protein tyrosine phosphatase 1B (PTP1B) as a key negative regulator of both insulin and leptin receptor pathways has been an attractive therapeutic target for the treatment of type 2 diabetes mellitus (T2DM) and obesity. With the goal of enhancing potency and selectivity of the PTP1B inhibitors, a series of methyl salicylate derivatives as ABC type PTP1B inhibitors (P1-P7) were discovered. More importantly, compound P6 exhibited high potent inhibitory activity (IC50 = 50 nM) for PTP1B with 15-fold selectivity over T-cell PTPase (TCPTP). Further studies on cellular activities revealed that compound P6 could enhance insulin-mediated insulin receptor β (IRβ) phosphorylation and insulin-stimulated glucose uptake. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

27 CFR 21.151 - List of denaturants authorized for denatured spirits.

Code of Federal Regulations, 2012 CFR

2012-04-01

....A. 38-B, 38-F. Cinchonidine S.D.A. 39-A. Cinchonidine sulfate, N.F.IX S.D.A. 39-A. Cinnamic aldehyde... ketone C.D.A. 18, 19; S.D.A. 1, 23-H. Methyl n-butyl ketone C.D.A. 18, 19; S.D.A. 1. Methyl salicylate, N...

27 CFR 21.151 - List of denaturants authorized for denatured spirits.

Code of Federal Regulations, 2014 CFR

2014-04-01

....A. 38-B, 38-F. Cinchonidine S.D.A. 39-A. Cinchonidine sulfate, N.F.IX S.D.A. 39-A. Cinnamic aldehyde... ketone C.D.A. 18, 19; S.D.A. 1, 23-H. Methyl n-butyl ketone C.D.A. 18, 19; S.D.A. 1. Methyl salicylate, N...

27 CFR 21.151 - List of denaturants authorized for denatured spirits.

Code of Federal Regulations, 2013 CFR

2013-04-01

....A. 38-B, 38-F. Cinchonidine S.D.A. 39-A. Cinchonidine sulfate, N.F.IX S.D.A. 39-A. Cinnamic aldehyde... ketone C.D.A. 18, 19; S.D.A. 1, 23-H. Methyl n-butyl ketone C.D.A. 18, 19; S.D.A. 1. Methyl salicylate, N...

Molecular plant volatile communication.

PubMed

Holopainen, Jarmo K; Blande, James D

2012-01-01

Plants produce a wide array of volatile organic compounds (VOCs) which have multiple functions as internal plant hormones (e.g., ethylene, methyl jasmonate and methyl salicylate), in communication with conspecific and heterospecific plants and in communication with organisms of second (herbivores and pollinators) and third (enemies of herbivores) trophic levels. Species specific VOCs normally repel polyphagous herbivores and those specialised on other plant species, but may attract specialist herbivores and their natural enemies, which use VOCs as host location cues. Attraction of predators and parasitoids by VOCs is considered an evolved indirect defence, whereby plants are able to indirectly reduce biotic stress caused by damaging herbivores. In this chapter we review these interactions where VOCs are known to play a crucial role. We then discuss the importance of volatile communication in self and nonself detection. VOCs are suggested to appear in soil ecosystems where distinction of own roots from neighbours roots is essential to optimise root growth, but limited evidence of above-ground plant self-recognition is available.

[Study on hydrothermal stability of the collagen].

PubMed

Wang, Yajuan; Chen, Hui; Shan, Zhihua

2009-02-01

The low hydrothermal stability of the raw collagen restricts its usage. To improve the hydrothermal stability of collagen, two kinds of materials with weak astringency were used by experts. The research proved that the synergistic effect was formed during the process. In this study, by using UV, FT-IR, 13CNMR spectra and elemental analysis on the salicylic acid and metal-salicylic complexes, we could get the structural formula of every compound. And then, the hide powder was treated with the compounds. At last, the treated hide powder was tested by DSC. It could be presumed that the Rigid Matrix formed between the collagen doses can increase the hydrothermal stability of raw collagen, The result indicated that salicylic-chrome with large stable constant was better than others in improving the heat resistance of raw collagen, and the denaturalization temperature of hide powder treated with salicylic-chrome was 146.7 degrees C. Salicylic-aluminum was in the second place, the relevant temperature being 145.7 degrees C.

Resonance electron attachment to plant hormones and its likely connection with biochemical processes

DOE Office of Scientific and Technical Information (OSTI.GOV)

Pshenichnyuk, Stanislav A., E-mail: sapsh@anrb.ru; Modelli, Alberto

Gas-phase formation of temporary negative ion states via resonance attachment of low-energy (0–6 eV) electrons into vacant molecular orbitals of salicylic acid (I) and its derivatives 3-hydroxy- (II) and 4-hydroxybenzoic acid (III), 5-cloro salicylic acid (IV) and methyl salicylate (V) was investigated for the first time by electron transmission spectroscopy. The description of their empty-level structures was supported by density functional theory and Hartree-Fock calculations, using empirically calibrated linear equations to scale the calculated virtual orbital energies. Dissociative electron attachment spectroscopy (DEAS) was used to measure the fragment anion yields generated through dissociative decay channels of the parent molecular anionsmore » of compounds I–V, detected with a mass filter as a function of the incident electron energy in the 0–14 eV energy range. The most intense negative fragment produced by DEA to isomers I–III is the dehydrogenated molecular anion [M–H]{sup −}, mainly formed at incident electron energies around 1 eV. The vertical and adiabatic electron affinities were evaluated at the B3LYP/6-31+G(d) level as the anion/neutral total energy difference. The same theoretical method was also used for evaluation of the thermodynamic energy thresholds for production of the negative fragments observed in the DEA spectra. The gas-phase DEAS data can provide support for biochemical reaction mechanisms in vivo.« less

What are Warts?

MedlinePlus

... about which treatment is right for you. Applying salicylic acid. You can treat warts on places such as the hands, feet or knees by putting salicylic acid (one brand name: Compound W) on the warts. ...

Transgenic soybean overexpressing GmSAMT1 exhibits resistance to multiple-HG types of soybean cyst nematode Heterodera glycines

DOE PAGES

Lin, Jingyu; Mazarei, Mitra; Zhao, Nan; ...

2016-05-23

Soybean ( Glycine max (L.) Merr.) salicylic acid methyl transferase (GmSAMT1) catalyses the conversion of salicylic acid to methyl salicylate. Prior results showed that when GmSAMT1 was overexpressed in transgenic soybean hairy roots, resistance is conferred against soybean cyst nematode (SCN), Heterodera glycines Ichinohe. In this study, we produced transgenic soybean overexpressing GmSAMT1 and characterized their response to various SCN races. Transgenic plants conferred a significant reduction in the development of SCN HG type 1.2.5.7 (race 2), HG type 0 (race 3) and HG type 2.5.7 (race 5). Among transgenic lines, GmSAMT1 expression in roots was positively associated with SCNmore » resistance. In some transgenic lines, there was a significant decrease in salicylic acid titer relative to control plants. No significant seed yield differences were observed between transgenics and control soybean plants grown in one greenhouse with 22 °C day/night temperature, whereas transgenic soybean had higher yield than controls grown a warmer greenhouse (27 °C day/23 °C night) temperature. In a 1-year field experiment in Knoxville, TN, there was no significant difference in seed yield between the transgenic and nontransgenic soybean under conditions with negligible SCN infection. We hypothesize that GmSAMT1 expression affects salicylic acid biosynthesis, which, in turn, attenuates SCN development, without negative consequences to soybean yield or other morphological traits. Furthermore, we conclude that GmSAMT1 overexpression confers broad resistance to multiple SCN races, which would be potentially applicable to commercial production.« less

Transgenic soybean overexpressing GmSAMT1 exhibits resistance to multiple-HG types of soybean cyst nematode Heterodera glycines

DOE Office of Scientific and Technical Information (OSTI.GOV)

Lin, Jingyu; Mazarei, Mitra; Zhao, Nan

Soybean ( Glycine max (L.) Merr.) salicylic acid methyl transferase (GmSAMT1) catalyses the conversion of salicylic acid to methyl salicylate. Prior results showed that when GmSAMT1 was overexpressed in transgenic soybean hairy roots, resistance is conferred against soybean cyst nematode (SCN), Heterodera glycines Ichinohe. In this study, we produced transgenic soybean overexpressing GmSAMT1 and characterized their response to various SCN races. Transgenic plants conferred a significant reduction in the development of SCN HG type 1.2.5.7 (race 2), HG type 0 (race 3) and HG type 2.5.7 (race 5). Among transgenic lines, GmSAMT1 expression in roots was positively associated with SCNmore » resistance. In some transgenic lines, there was a significant decrease in salicylic acid titer relative to control plants. No significant seed yield differences were observed between transgenics and control soybean plants grown in one greenhouse with 22 °C day/night temperature, whereas transgenic soybean had higher yield than controls grown a warmer greenhouse (27 °C day/23 °C night) temperature. In a 1-year field experiment in Knoxville, TN, there was no significant difference in seed yield between the transgenic and nontransgenic soybean under conditions with negligible SCN infection. We hypothesize that GmSAMT1 expression affects salicylic acid biosynthesis, which, in turn, attenuates SCN development, without negative consequences to soybean yield or other morphological traits. Furthermore, we conclude that GmSAMT1 overexpression confers broad resistance to multiple SCN races, which would be potentially applicable to commercial production.« less

Comparison of salicylate and D-phenylalanine for detection of hydroxyl radicals in chemical and biological reactions.

PubMed

Bailey, S M; Fauconnet, A L; Reinke, L A

1997-02-01

Hydroxylation of salicylate and D-phenylalanine was measured to test the usefulness of these compounds for hydroxyl radical (HO(•)) detection in chemical and biological systems. When HO(•) were produced by the photolytic decomposition of hydrogen peroxide, nearly equal amounts of 2,5- and 2,3-dihydroxybenzoic acid (DHBA) were produced from salicylate, with catechol as a minor product. In the photolytic reaction, nearly equal concentrations of p-,m-, and o-tyrosine were formed from D-phenylalanine. When salicylate or D-phenylalanine was present with Fenton reagents or in iron(II) autoxidation systems, the relative proportions of hydroxylated products were similar to those observed after photolysis, although less total products were usually detected. In contrast, when similar experiments were conducted with isolated hepatic microsomes and perfused livers, 2,5-DHBA was the primary product from salicylate, and p-tyrosine was the major product from D-phenylalanine. Cytochrome P-450 enzymes can hydroxylate salicylate to produce 2,5-DHBA, and it is likely that phenylalanine hydroxylase produces most of the p-tyrosine detected in hepatic tissues. Thus, although both salicylate and D-phenylalanine are useful probes for hydroxyl radical formation in chemical systems, hydroxylated products formed from enzymatic reactions complicate interpretation of data from both compounds in vivo.

Desorption of sulphur mustard simulants methyl salicylate and 2-chloroethyl ethyl sulphide from contaminated scalp hair after vapour exposure.

PubMed

Spiandore, Marie; Souilah-Edib, Mélanie; Piram, Anne; Lacoste, Alexandre; Josse, Denis; Doumenq, Pierre

2018-01-01

Chemical warfare agents have been used to incapacitate, injure or kill people, in a context of war or terrorist attack. It has previously been shown that hair could trap the sulphur mustard simulants methyl salicylate and 2-chloroethyl ethyl sulphide. In order to investigate simulants persistency in hair after intense vapour exposure, their desorption kinetics were studied by using two complementary methods: hair residual content measurement and desorbed vapour monitoring. Results showed that both simulants were detected in air and could be recovered from hair 2 h after the end of exposure. Longer experiments with methyl salicylate showed that it could still be recovered from hair after 24 h. Our data were fitted with several kinetic models and best correlation was obtained with a bimodal first-order equation, suggesting a 2-step desorption kinetics model: initial fast regime followed by a slower desorption. 2-chloroethyl ethyl sulphide was also detected in the immediate environment after hair exposure for 2 h, and hair simulant content decreased by more than 80%. Our results showed that hair ability to release formerly trapped chemical toxics could lead to health hazard. Their persistency however confirmed the potentiality of hair analysis as a tool for chemical exposure assessment. Copyright © 2017 Elsevier Ltd. All rights reserved.

Identification and Biochemical Characterization of Small-Molecule Inhibitors of Clostridium Botulinum Neurotoxin Serotype A

DTIC Science & Technology

2009-08-01

the BoNT/A protease activity were selected. Database search queries of the best candidate hit [7-((4-nitro- anilino)(phenyl) methyl )-8-quinolinol (NSC...therapeutic challenges. Trends Mol. Med. 9:291–299. 18. Gershon, H., and R. Parmegiani. 1963. Antimicrobial activity of 8-quinoli- nol, its salts with salicylic ...Parmegiani. 1962. Antimicrobial activity of 8-quinoli- nols, salicylic acids, hydroxynaphthoic acids, and salts of selected quinolinols with selected

Control of Citrus Huanglongbing via Trunk Injection of Plant Defense Activators and Antibiotics.

PubMed

Hu, J; Jiang, J; Wang, N

2018-02-01

Citrus huanglongbing (HLB) or greening is a devastating disease of citrus worldwide and no effective control measure is currently available. Plant defense activators environmentally friendly compounds capable of inducing resistance against many plant pathogens. Earlier studies showed that foliar spray of plant defense inducers could slow down HLB disease progress. In this study, eight plant defense activators and three antibiotics were evaluated in three field trials for their effect to control HLB by trunk injection of young and mature sweet orange trees. Results showed that four trunk injections of several activators, including salicylic acid, oxalic acid, acibenzolar-S-methyl, and potassium phosphate, provided significant control of HLB by suppressing 'Candidatus Liberibacter asiaticus' titer and disease progress. Trunk injection of penicillin, streptomycin, and oxytetracycline hydrochloride resulted in excellent control of HLB. In general, antibiotics were more effective in reduction of 'Ca. L. asiaticus' titer and HLB symptom expressions than plant defense activators. These treatments also resulted in increased yield and better fruit quality. Injection of both salicylic acid and acibenzolar-S-methyl led to significant induction of pathogenesis-related (PR) genes PR-1 and PR-2 genes. Meanwhile, injection of either potassium phosphate or oxalic acid resulted in significant induction of PR-2 or PR-15 gene expression, respectively. These results suggested that HLB diseased trees remained inducible for systemic acquired resistance under field conditions. In summary, this study presents information regarding controlling HLB via trunk injection of plant defense activators and antibiotics, which helps citrus growers in decision making regarding developing an effective HLB management program.

Selective sensing of vapors of similar dielectric constants using peptide-capped gold nanoparticles on individual multivariable transducers.

PubMed

Nagraj, Nandini; Slocik, Joseph M; Phillips, David M; Kelley-Loughnane, Nancy; Naik, Rajesh R; Potyrailo, Radislav A

2013-08-07

Peptide-capped AYSSGAPPMPPF gold nanoparticles were demonstrated for highly selective chemical vapor sensing using individual multivariable inductor-capacitor-resistor (LCR) resonators. Their multivariable response was achieved by measuring their resonance impedance spectra followed by multivariate spectral analysis. Detection of model toxic vapors and chemical agent simulants, such as acetonitrile, dichloromethane and methyl salicylate, was performed. Dichloromethane (dielectric constant εr = 9.1) and methyl salicylate (εr = 9.0) were discriminated using a single sensor. These sensing materials coupled to multivariable transducers can provide numerous opportunities for tailoring the vapor response selectivity based on the diversity of the amino acid composition of the peptides, and by the modulation of the nature of peptide-nanoparticle interactions through designed combinations of hydrophobic and hydrophilic amino acids.

Induction of phenolic compounds in Hypericum perforatum L. cells by Colletotrichum gloeosporioides elicitation.

PubMed

Conceição, Luis F R; Ferreres, Federico; Tavares, Rui M; Dias, Alberto C P

2006-01-01

Changes in phenolic metabolism after elicitation with Colletotrichum gloeosporioides (CG) has been studied in Hypericum perforatum L. (HP) cell suspension cultures. Soluble phenolics were analysed by HPLC-DAD and HPLC-DAD-MS/MS. HP cultures elicited with the CG elicitor showed a significant increase in xanthone accumulation. Xanthone accumulation increased twelve fold when the cells were primed with methyl-jasmonate (MeJ) or salicylic acid (SA), before elicitation. HP cultures exposed only to MeJ produced a set of flavonoids, the flavones which represent a substantial part (approx. 40%) of the total flavonoids accumulated in these cells. The possible importance of xanthones as a component of defence mechanism of HP against biotic stress is discussed.

Aqueous Oxidation of Green Leaf Volatiles as a Source of Secondary Organic Aerosol

NASA Astrophysics Data System (ADS)

Richards-Henderson, N. K.; Hansel, A.; Pham, A. T.; Vempati, H. S.; Valsaraj, K. T.; Anastasio, C.

2013-12-01

Vegetation emits volatile oxygenated hydrocarbons - the green leaf volatiles (GLVs) - which are formed from the biochemical conversion of linoleic and linolenic acids within plant cells. Stress or damage to vegetation can significantly elevate emission fluxes of these compounds, some of which are fairly water soluble. Aqueous-phase reactions of the GLVs with photochemically generated oxidants - such as hydroxyl radical (OH), singlet oxygen (1O2) and excited triplet states of organic compounds (3C*) _ might then form low-volatility products that can act as secondary organic aerosol (SOA). In order to determine if GLVs can be a significant source of secondary organic carbon in fogwater, studies of GLVs in laboratory solutions are needed to elucidate the oxidation kinetics and the corresponding SOA mass yields. In this study we are determining the second-order rate constants, and SOA mass yields, for five GLVs (cis-3-hexen-1-ol, cis-3-hexenylacetate, methyl salicylate, methyl jasmonate, and 2-methyl-3-butene-2-ol) reacting with OH,1O2 and 3C*. Experiments are performed at relevant fog water pHs, temperatures, and oxidant concentrations. Rate constants are determined using a relative rate approach in which the decay of GLVs and reference compounds are monitored as function of time by HPLC. The capacity of GLVs to form aqueous SOA was determined by following the formation of their decomposition products with HPLC-UV/DAD and HPLC-ESI/MS. SOA mass yields are measured gravimetrically from laboratory solutions containing atmospherically relevant concentrations of photooxidants and GLVs, and irradiated with simulated sunlight. We will use our results to assess the potential contribution of aqueous GLV reactions as a source of SOA in cloudy or foggy atmospheres.

Sports cream overdose

MedlinePlus

Sports creams are creams or ointments used to treat aches and pains. Sports cream overdose can occur if someone uses this ... Two ingredients in sports creams that can be poisonous are: Menthol Methyl salicylate

Dissecting the Transcriptional Response to Elicitors in Vitis vinifera Cells

PubMed Central

Belchí-Navarro, Sarai; Bru, Roque; Martínez-Zapater, José M.; Lijavetzky, Diego; Pedreño, María A.

2014-01-01

The high effectiveness of cyclic oligosaccharides like cyclodextrins in the production of trans-resveratrol in Vitis vinifera cell cultures is enhanced in the presence of methyl jasmonate. In order to dissect the basis of the interactions among the elicitation responses triggered by these two compounds, a transcriptional analysis of grapevine cell cultures treated with cyclodextrins and methyl jasmonate separately or in combination was carried out. The results showed that the activation of genes encoding enzymes from phenylpropanoid and stilbene biosynthesis induced by cyclodextrins alone was partially enhanced in the presence of methyl jasmonate, which correlated with their effects on trans-resveratrol production. In addition, protein translation and cell cycle regulation were more highly repressed in cells treated with cyclodextrins than in those treated with methyl jasmonate, and this response was enhanced in the combined treatment. Ethylene signalling was activated by all treatments, while jasmonate signalling and salicylic acid conjugation were activated only in the presence of methyl jasmonate and cyclodextrins, respectively. Moreover, the combined treatment resulted in a crosstalk between the signalling cascades activated by cyclodextrins and methyl jasmonate, which, in turn, provoked the activation of additional regulatory pathways involving the up-regulation of MYB15, NAC and WRKY transcription factors, protein kinases and calcium signal transducers. All these results suggest that both elicitors cause an activation of the secondary metabolism in detriment of basic cell processes like the primary metabolism or cell division. Crosstalk between cyclodextrins and methyl jasmonate-induced signalling provokes an intensification of these responses resulting in a greater trans-resveratrol production. PMID:25314001

First Characterisation of Volatile Organic Compounds Emitted by Banana Plants.

PubMed

Berhal, Chadi; De Clerck, Caroline; Fauconnier, Marie-Laure; Levicek, Carolina; Boullis, Antoine; Kaddes, Amine; Jijakli, Haïssam M; Verheggen, François; Massart, Sébastien

2017-05-16

Banana (Musa sp.) ranks fourth in term of worldwide fruit production, and has economical and nutritional key values. The Cavendish cultivars correspond to more than 90% of the production of dessert banana while cooking cultivars are widely consumed locally around the banana belt production area. Many plants, if not all, produce Volatile Organic Compounds (VOCs) as a means of communication with their environment. Although flower and fruit VOCs have been studied for banana, the VOCs produced by the plant have never been identified despite their importance in plant health and development. A volatile collection methodology was optimized to improve the sensitivity and reproducibility of VOCs analysis from banana plants. We have identified 11 VOCs for the Cavendish, mainly (E,E)-α-farnesene (87.90 ± 11.28 ng/μl), methyl salicylate (33.82 ± 14.29) and 6-methyl-5-hepten-2-one (29.60 ± 11.66), and 14 VOCs for the Pacific Plantain cultivar, mainly (Z,E)-α-farnesene (799.64 ± 503.15), (E,E)-α-farnesene (571.24 ± 381.70) and (E) β ocimene (241.76 ± 158.49). This exploratory study paves the way for an in-depth characterisation of VOCs emitted by Musa plants.

Bacterial Chemotaxis to Naphthalene and Nitroarene Compounds

DTIC Science & Technology

2008-07-31

Qualitative capillary assays showing chemotaxis of succinate-grown 17 (uninduced) and induced (succinate plus salicylate -grown) Acidovorax sp. JS42...succinate plus 2NT- or succinate plus salicylate -grown) wild-type Acidovorax sp. JS42 cells List of Tables Table 1. Summary of chemotaxis...mM salicylate , or naphthalene crystals. Noble agar (1.8%; Difco) was used to solidify MSB medium for plates. For plasmid selection and maintenance

Methyl Jasmonate and Salicylic Acid Enhanced the Production of Ursolic and Oleanolic Acid in Callus Cultures of Lepechinia Caulescens

PubMed Central

Vergara Martínez, Víctor M.; Estrada-Soto, Samuel E.; Arellano-García, José de Jesús; Rivera-Leyva, Julio C.; Castillo-España, Patricia; Flores, Angélica Flores; Cardoso-Taketa, Alexandre T.; Perea-Arango, Irene

2017-01-01

Background: The production of triterpenes from plants for pharmacological purposes varies in concentration, due to genetic and environmental factors. In vitro culture enables the control and increase of these bioactive molecules. Objective: To evaluate the effect of plant growth regulators and elicitors in the induction of calli and the production of ursolic acid (UA) and oleanolic acid (OA) in Lepechinia caulescens. Materials and Methods: Leaf explants were exposed for the induction of calli at different concentrations and combinations of 2,4-dichlorophenoxyacetic acid (2,4-D) and 6-benzylaminopurine (BAP). Methyl jasmonate (MJ) and salicylic acid were used as elicitors. High-performance liquid chromatography method was used to quantify UA and OA content in each treatment. Results: Treatment with 3.0 mg/L of 2,4-D and 0.1 mg/L of BAP produced the best results for calli induction and production of UA (1.57 mg/g dry weight [DW]) and OA (1.13 mg/g DW). Both elicitors facilitated the accumulation of triterpenes. Conclusion: The combination of auxins and cytokinins showed favorable results for the induction of calli. Variation concerning the accumulation of UA and OA was observed between treatments. MJ increased the production of triterpenes five times after 8 h of exposure, compared to control treatment. There is a greater accumulation of UA (16.58 mg/g DW) and OA (1.94 mg/g DW) in leaves of wild plants. SUMMARY Callus cultures of Lepechinia caulescens were obtained from leaf explants treated with 2,4-dichlorophenoxyacetic acid and 6-bencylaminopurineResulting cultures were elicited with methyl jasmonate (MJ) and salicylic acid to increase the production of the triterpenes, ursolic acid (UA), and oleanolic acid (OA)The cultures elicited with MJ increased the production of UA and OA five times, as compared to the control. Abbreviations used: 2,4-D: 2,4-dichlorophenoxyacetic acid, BAP: 6-benzylaminopurine, DW: Dry weight, MJ: Methyl jasmonate, OA: Oleanolic acid, PGRs: Plant growth regulators, UA: Ursolic acid, SA: Salicylic acid. PMID:29491649

Consumption study and identification of methyl salicylate in spicy cassava chips

DOE Office of Scientific and Technical Information (OSTI.GOV)

Nirjana, Marlene, E-mail: marlenenirjana@gmail.com; Anggadiredja, Kusnandar; Damayanti, Sophi

Spicy cassava chips is a popular snack. However, some news in electronic media reported addition of balsam which is a banned food additives in that product to give extra spicy flavor. This study aimed to determine ITB students’ pattern of consumption, health problems caused by spicy chips consumption, and knowledge about illicit use of food additives in that product, and identify the main content of balsam namely methyl salicylate in 10 samples of spicy cassava chips taken from inside and outside about ITB campus. A total of 300 questionnaires distributed to ITB students then data processing was performed. Spicy cassavamore » chips sample macerated in 50 mL of methanol for 24 hours at room temperature, filtered and analyzed using gas chromatography capillary column with OV-1, nitrogen carrier gas and flame ionization detector. Based on questionnaires, 292 (97%) of 300 respondents had consumed spicy chips. A total of 247 (85%) from 292 respondents spicy chips consumed less than 3 times a week. A total of 195 respondents (67%) had experienced health problems after eating spicy chips. There were 137 (47%) of the 292 respondents who knew about the illicit addition of food additives into spicy chips; only 35 respondents (12%) who knew about balsam’s addition. There were 126 respondents (43%) who did not pay attention to their health because they will keep eating spicy chips despite the addition of banned food additives. Through the verification of the standard addition method in gas chromatography system with a hydrogen pressure of 1.5 bar, injector temperature 200 °C, detector temperature 230 °C, oven temperature 60 °C for 2 minutes and then increased to 230 °C with rate 6 °C/menit; linearity, limit of detection, limit of quantitation, accuracy, precision, and specificity parameters met the acceptance limits. From 10 spicy cassava chips samples which were analyzed, they did not reveal any content of methyl salicylate. Methyl salicylate contained in the positive control was 1.273 mg/mL.« less

Transgenic soybean overexpressing GmSAMT1 exhibits resistance to multiple-HG types of soybean cyst nematode Heterodera glycines.

PubMed

Lin, Jingyu; Mazarei, Mitra; Zhao, Nan; Hatcher, Catherine N; Wuddineh, Wegi A; Rudis, Mary; Tschaplinski, Timothy J; Pantalone, Vincent R; Arelli, Prakash R; Hewezi, Tarek; Chen, Feng; Stewart, Charles Neal

2016-11-01

Soybean (Glycine max (L.) Merr.) salicylic acid methyl transferase (GmSAMT1) catalyses the conversion of salicylic acid to methyl salicylate. Prior results showed that when GmSAMT1 was overexpressed in transgenic soybean hairy roots, resistance is conferred against soybean cyst nematode (SCN), Heterodera glycines Ichinohe. In this study, we produced transgenic soybean overexpressing GmSAMT1 and characterized their response to various SCN races. Transgenic plants conferred a significant reduction in the development of SCN HG type 1.2.5.7 (race 2), HG type 0 (race 3) and HG type 2.5.7 (race 5). Among transgenic lines, GmSAMT1 expression in roots was positively associated with SCN resistance. In some transgenic lines, there was a significant decrease in salicylic acid titer relative to control plants. No significant seed yield differences were observed between transgenics and control soybean plants grown in one greenhouse with 22 °C day/night temperature, whereas transgenic soybean had higher yield than controls grown a warmer greenhouse (27 °C day/23 °C night) temperature. In a 1-year field experiment in Knoxville, TN, there was no significant difference in seed yield between the transgenic and nontransgenic soybean under conditions with negligible SCN infection. We hypothesize that GmSAMT1 expression affects salicylic acid biosynthesis, which, in turn, attenuates SCN development, without negative consequences to soybean yield or other morphological traits. Thus, we conclude that GmSAMT1 overexpression confers broad resistance to multiple SCN races, which would be potentially applicable to commercial production. © 2016 The Authors. Plant Biotechnology Journal published by Society for Experimental Biology and The Association of Applied Biologists and John Wiley & Sons Ltd.

Induced Release of a Plant-Defense Volatile ‘Deceptively’ Attracts Insect Vectors to Plants Infected with a Bacterial Pathogen

PubMed Central

Mann, Rajinder S.; Ali, Jared G.; Hermann, Sara L.; Tiwari, Siddharth; Pelz-Stelinski, Kirsten S.; Alborn, Hans T.; Stelinski, Lukasz L.

2012-01-01

Transmission of plant pathogens by insect vectors is a complex biological process involving interactions between the plant, insect, and pathogen. Pathogen-induced plant responses can include changes in volatile and nonvolatile secondary metabolites as well as major plant nutrients. Experiments were conducted to understand how a plant pathogenic bacterium, Candidatus Liberibacter asiaticus (Las), affects host preference behavior of its psyllid (Diaphorina citri Kuwayama) vector. D. citri were attracted to volatiles from pathogen-infected plants more than to those from non-infected counterparts. Las-infected plants were more attractive to D. citri adults than non-infected plants initially; however after feeding, psyllids subsequently dispersed to non-infected rather than infected plants as their preferred settling point. Experiments with Las-infected and non-infected plants under complete darkness yielded similar results to those recorded under light. The behavior of psyllids in response to infected versus non-infected plants was not influenced by whether or not they were carriers of the pathogen. Quantification of volatile release from non-infected and infected plants supported the hypothesis that odorants mediate psyllid preference. Significantly more methyl salicylate, yet less methyl anthranilate and D-limonene, was released by infected than non-infected plants. Methyl salicylate was attractive to psyllids, while methyl anthranilate did not affect their behavior. Feeding on citrus by D. citri adults also induced release of methyl salicylate, suggesting that it may be a cue revealing location of conspecifics on host plants. Infected plants were characterized by lower levels of nitrogen, phosphorus, sulfur, zinc, and iron, as well as, higher levels of potassium and boron than non-infected plants. Collectively, our results suggest that host selection behavior of D. citri may be modified by bacterial infection of plants, which alters release of specific headspace volatiles and plant nutritional contents. Furthermore, we show in a laboratory setting that this apparent pathogen-mediated manipulation of vector behavior may facilitate pathogen spread. PMID:22457628

Induced release of a plant-defense volatile 'deceptively' attracts insect vectors to plants infected with a bacterial pathogen.

PubMed

Mann, Rajinder S; Ali, Jared G; Hermann, Sara L; Tiwari, Siddharth; Pelz-Stelinski, Kirsten S; Alborn, Hans T; Stelinski, Lukasz L

2012-01-01

Transmission of plant pathogens by insect vectors is a complex biological process involving interactions between the plant, insect, and pathogen. Pathogen-induced plant responses can include changes in volatile and nonvolatile secondary metabolites as well as major plant nutrients. Experiments were conducted to understand how a plant pathogenic bacterium, Candidatus Liberibacter asiaticus (Las), affects host preference behavior of its psyllid (Diaphorina citri Kuwayama) vector. D. citri were attracted to volatiles from pathogen-infected plants more than to those from non-infected counterparts. Las-infected plants were more attractive to D. citri adults than non-infected plants initially; however after feeding, psyllids subsequently dispersed to non-infected rather than infected plants as their preferred settling point. Experiments with Las-infected and non-infected plants under complete darkness yielded similar results to those recorded under light. The behavior of psyllids in response to infected versus non-infected plants was not influenced by whether or not they were carriers of the pathogen. Quantification of volatile release from non-infected and infected plants supported the hypothesis that odorants mediate psyllid preference. Significantly more methyl salicylate, yet less methyl anthranilate and D-limonene, was released by infected than non-infected plants. Methyl salicylate was attractive to psyllids, while methyl anthranilate did not affect their behavior. Feeding on citrus by D. citri adults also induced release of methyl salicylate, suggesting that it may be a cue revealing location of conspecifics on host plants. Infected plants were characterized by lower levels of nitrogen, phosphorus, sulfur, zinc, and iron, as well as, higher levels of potassium and boron than non-infected plants. Collectively, our results suggest that host selection behavior of D. citri may be modified by bacterial infection of plants, which alters release of specific headspace volatiles and plant nutritional contents. Furthermore, we show in a laboratory setting that this apparent pathogen-mediated manipulation of vector behavior may facilitate pathogen spread.

Measurement of volatile plant compounds in field ambient air by thermal desorption-gas chromatography-mass spectrometry.

PubMed

Cai, Xiao-Ming; Xu, Xiu-Xiu; Bian, Lei; Luo, Zong-Xiu; Chen, Zong-Mao

2015-12-01

Determination of volatile plant compounds in field ambient air is important to understand chemical communication between plants and insects and will aid the development of semiochemicals from plants for pest control. In this study, a thermal desorption-gas chromatography-mass spectrometry (TD-GC-MS) method was developed to measure ultra-trace levels of volatile plant compounds in field ambient air. The desorption parameters of TD, including sorbent tube material, tube desorption temperature, desorption time, and cold trap temperature, were selected and optimized. In GC-MS analysis, the selected ion monitoring mode was used for enhanced sensitivity and selectivity. This method was sufficiently sensitive to detect part-per-trillion levels of volatile plant compounds in field ambient air. Laboratory and field evaluation revealed that the method presented high precision and accuracy. Field studies indicated that the background odor of tea plantations contained some common volatile plant compounds, such as (Z)-3-hexenol, methyl salicylate, and (E)-ocimene, at concentrations ranging from 1 to 3400 ng m(-3). In addition, the background odor in summer was more abundant in quality and quantity than in autumn. Relative to previous methods, the TD-GC-MS method is more sensitive, permitting accurate qualitative and quantitative measurements of volatile plant compounds in field ambient air.

Salicylate Poisoning Potential of Topical Pain Relief Agents: From Age Old Remedies to Engineered Smart Patches

PubMed Central

Anderson, Ashleigh; McConville, Aaron; Fanthorpe, Laura; Davis, James

2017-01-01

The pain relief capabilities of methyl salicylate are well established and a multitude of over-the-counter products populate pharmacy shelves. Over-application of the topical preparation containing the drug, or its accidental ingestion, invariably result in salicylate poisoning and in severe cases can be fatal. The drug has been a regular feature of the US National Poison Database Survey over the past decade and continues to pose a risk to children and adults alike. The aim of the review has been to cast a spotlight on the drug and assess why its use remains problematic, how technology could offer more efficacious delivery regimes, and minimise the possibility of accidental or intentional misuse. PMID:28930263

Salicylate Poisoning Potential of Topical Pain Relief Agents: From Age Old Remedies to Engineered Smart Patches.

PubMed

Anderson, Ashleigh; McConville, Aaron; Fanthorpe, Laura; Davis, James

2017-06-30

The pain relief capabilities of methyl salicylate are well established and a multitude of over-the-counter products populate pharmacy shelves. Over-application of the topical preparation containing the drug, or its accidental ingestion, invariably result in salicylate poisoning and in severe cases can be fatal. The drug has been a regular feature of the US National Poison Database Survey over the past decade and continues to pose a risk to children and adults alike. The aim of the review has been to cast a spotlight on the drug and assess why its use remains problematic, how technology could offer more efficacious delivery regimes, and minimise the possibility of accidental or intentional misuse.

Salicylate poisoning: an evidence-based consensus guideline for out-of-hospital management.

PubMed

Chyka, Peter A; Erdman, Andrew R; Christianson, Gwenn; Wax, Paul M; Booze, Lisa L; Manoguerra, Anthony S; Caravati, E Martin; Nelson, Lewis S; Olson, Kent R; Cobaugh, Daniel J; Scharman, Elizabeth J; Woolf, Alan D; Troutman, William G

2007-01-01

A review of U.S. poison center data for 2004 showed over 40,000 exposures to salicylate-containing products. A guideline that determines the conditions for emergency department referral and pre-hospital care could potentially optimize patient outcome, avoid unnecessary emergency department visits, reduce health care costs, and reduce life disruption for patients and caregivers. An evidence-based expert consensus process was used to create the guideline. Relevant articles were abstracted by a trained physician researcher. The first draft of the guideline was created by the lead author. The entire panel discussed and refined the guideline before distribution to secondary reviewers for comment. The panel then made changes based on the secondary review comments. The objective of this guideline is to assist poison center personnel in the appropriate out-of-hospital triage and initial out-of-hospital management of patients with a suspected exposure to salicylates by 1) describing the process by which a specialist in poison information should evaluate an exposure to salicylates, 2) identifying the key decision elements in managing cases of salicylate exposure, 3) providing clear and practical recommendations that reflect the current state of knowledge, and 4) identifying needs for research. This guideline is based on an assessment of current scientific and clinical information. The expert consensus panel recognizes that specific patient care decisions may be at variance with this guideline and are the prerogative of the patient and the health professionals providing care, considering all of the circumstances involved. This guideline does not substitute for clinical judgment. Recommendations are in chronological order of likely clinical use. The grade of recommendation is in parentheses: 1) Patients with stated or suspected self-harm or who are the victims of a potentially malicious administration of a salicylate, should be referred to an emergency department immediately. This referral should be guided by local poison center procedures. In general, this should occur regardless of the dose reported (Grade D). 2) The presence of typical symptoms of salicylate toxicity such as hematemesis, tachypnea, hyperpnea, dyspnea, tinnitus, deafness, lethargy, seizures, unexplained lethargy, or confusion warrants referral to an emergency department for evaluation (Grade C). 3) Patients who exhibit typical symptoms of salicylate toxicity or nonspecific symptoms such as unexplained lethargy, confusion, or dyspnea, which could indicate the development of chronic salicylate toxicity, should be referred to an emergency department (Grade C). 4) Patients without evidence of self-harm should have further evaluation, including determination of the dose, time of ingestion, presence of symptoms, history of other medical conditions, and the presence of co-ingestants. The acute ingestion of more than 150 mg/kg or 6.5 g of aspirin equivalent, whichever is less, warrants referral to an emergency department. Ingestion of greater than a lick or taste of oil of wintergreen (98% methyl salicylate) by children under 6 years of age and more than 4 mL of oil of wintergreen by patients 6 years of age and older could cause systemic salicylate toxicity and warrants referral to an emergency department (Grade C). 5) Do not induce emesis for ingestions of salicylates (Grade D). 6) Consider the out-of-hospital administration of activated charcoal for acute ingestions of a toxic dose if it is immediately available, no contraindications are present, the patient is not vomiting, and local guidelines for its out-of-hospital use are observed. However, do not delay transportation in order to administer activated charcoal (Grade D). 7) Women in the last trimester of pregnancy who ingest below the dose for emergency department referral and do not have other referral conditions should be directed to their primary care physician, obstetrician, or a non-emergent health care facility for evaluation of maternal and fetal risk. Routine referral to an emergency department for immediate care is not required (Grade C). 8) For asymptomatic patients with dermal exposures to methyl salicylate or salicylic acid, the skin should be thoroughly washed with soap and water and the patient can be observed at home for development of symptoms (Grade C). 9) For patients with an ocular exposure of methyl salicylate or salicylic acid, the eye(s) should be irrigated with room-temperature tap water for 15 minutes. If after irrigation the patient is having pain, decreased visual acuity, or persistent irritation, referral for an ophthalmological examination is indicated (Grade D). 10) Poison centers should monitor the onset of symptoms whenever possible by conducting follow-up calls at periodic intervals for approximately 12 hours after ingestion of non-enteric-coated salicylate products, and for approximately 24 hours after the ingestion of enteric-coated aspirin (Grade C).

Apple Fool! An Introduction to Artificial Flavors.

ERIC Educational Resources Information Center

Journal of Chemical Education, 2003

2003-01-01

Presents a science activity on consumer chemistry in which students explore artificial flavors that are commonly used in foods, such as isoamyl acetate and methyl salicylate. Includes instructor information and a student worksheet. (YDS)

Studies on saponin production in tropical medicinal plants Maesa argentea and Maesa lanceolata

NASA Astrophysics Data System (ADS)

Faizal, Ahmad; Geelen, Danny

2015-09-01

The continuous need for new compounds with important medicinal activities has lead to the identification and characterization of various plant-derived natural products. As a part of this program, we studied the saponin production from two tropical medicinal plants Maesa argentea and M. lanceolata and evaluated several treatments to enhance their saponin production. In this experiment, we present the analyses of saponin production from greenhouse grown plants by means of TLC and HPLC-MS. We observed that the content of saponin from these plants varied depending on organ and physiological age of the plants. In addition, the impact of elicitors on saponin accumulation on in vitro grown plants was analyzed using TLC. The production of saponin was very stable and not affected by treatment with methyl jasmonate, and salicylic acid. In conclusion, Maesa saponins are constitutively produced in plants and the level of these compounds in plants is mainly affected by the developmental or physiological stage.

The Thermal Decomposition of Some Organic Lead Compounds

DTIC Science & Technology

1957-11-01

either of salicylic anhydride or of its pyrolysis fragments which are reported to be a mixture of carbon dioxide , phenol and phenyl salicylate. Other...7) have studied the decomposition of the mono-salicylate in vacuo at 400°C. and have found that one molecule of carbon dioxide is evolved per...of lead nitrate and nitrosalicylic acid, though seme of the latter is decarboxylated with evolution of carbon dioxide . These points are considered

Salicylic acid and nitric oxide alleviate high temperature induced oxidative damage in Lablab purpureus L plants by regulating bio-physical processes and DNA methylation.

PubMed

Rai, Krishna Kumar; Rai, Nagendra; Rai, Shashi Pandey

2018-07-01

Salicylic acid (SA) and sodium nitroprusside (SNP, NO donor) modulates plant growth and development processes and recent findings have also revealed their involvement in the regulation of epigenetic factors under stress condition. In the present study, some of these factors were comparatively studied in hyacinth bean plants subjected to high temperature (HT) environment (40-42 °C) with and without exogenous application of SA and SNP under field condition. Exogenous application of SA and SNP substantially modulated the growth and biophysical process of hyacinth bean plants under HT environment. Exogenous application of SA and SNP also remarkably regulated the activities of antioxidant enzymes, modulated mRNA level of certain enzymes, improves plant water relation, enhance photosynthesis and thereby increasing plant defence under HT. Coupled restriction enzyme digestion-random amplification (CRED-RA) technique revealed that many methylation changes were "dose dependent" and HT significantly increased DNA damages as evidenced by both increase and decrease in bands profiles, methylation and de-methylation pattern. Thus, the result of the present study clearly shows that exogenous SA and SNP regulates DNA methylation pattern, modulates stress-responsive genes and can impart transient HT tolerance by synchronizing growth and physiological acclimatization of plants, thus narrowing the gaps between physio-biochemical and molecular events in addressing HT tolerance. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Studies on the mechanism of salicylate-induced increase of insulin secretion in man.

PubMed

Giugliano, D; Cozzolino, D; Ceriello, A; Cerciello, T; Varano, R; Saccomanno, F; Torella, R

1988-01-01

Salicylate compounds are known to increase basal and stimulated insulin secretion in man. In our studies, infusion of lysine acetylsalicylate (72 mg/min) increased basal insulin levels and amplified insulin responses to glucose (5 g i.v.), arginine (5 g i.v.) and tolbutamide (1 g i.v.). Verapamil, an organic calcium antagonist, did not modify LAS-induced increase of basal insulin levels, but reduced the effect of LAS on glucose-induced insulin secretion. Calcitonin and somatostatin, two agents that inhibit basal and glucose-stimulated insulin secretion, inhibited the insulin response to glucose in presence of LAS infusion. The ability of salicylate compounds to augment insulin secretion might be due to multiple sites of action in the Beta-cells.

Evaluation of an ex vivo murine local lymph node assay: multiple endpoint comparison.

PubMed

Piccotti, Joseph R; Knight, Stephanie A; Gillhouse, Kimberly; Lagattuta, Mark S; Bleavins, Michael R

2006-01-01

The local lymph node assay (LLNA) is used to assess the skin sensitization potential of chemicals. In the standard assay, mice are treated topically on the dorsum of both ears with test substance for 3 days. Following 2 days of rest, the initiation of the hypersensitivity response is evaluated by injecting (3)H-thymidine into a tail vein, and then measuring the levels of radioisotope incorporated into the DNA of lymph node cells draining the ears. In the current study, BALB/c mice were treated with the contact sensitizers hexylcinnamic aldehyde (HCA) and oxazolone, and the nonsensitizer methyl salicylate. The proliferative response of lymph node cells was evaluated in an ex vivo assay, in which isolated cells were cultured in vitro with (3)H-thymidine. Treatment of mice with HCA at 5-50% resulted in concentration-related increases in (3)H-thymidine incorporation, with stimulation indices ranging from 3 to 14. Low animal-to-animal variability was seen in three replicate assays testing HCA at 25%. As anticipated, the proliferative response induced by the potent sensitizer oxazolone at 0.25% was greater than HCA at all concentrations tested. Stimulation indices of 1.5 and 3 were seen in two independent experiments with methyl salicylate. These equivocal findings were likely due to the irritancy properties of the compound. Importantly, measuring ex vivo (3)H-thymidine incorporation was more sensitive than evaluating lymph node weight and cellularity, and in vitro bromodeoxyuridine incorporation. Furthermore, the results of the ex vivo LLNA were comparable to the standard assay. This study provided evidence that supports the use of an ex vivo LLNA for hazard assessment of contact hypersensitivity. Copyright 2006 John Wiley & Sons, Ltd.

Membrane-bound guaiacol peroxidases from maize (Zea mays L.) roots are regulated by methyl jasmonate, salicylic acid, and pathogen elicitors

PubMed Central

Mika, Angela; Boenisch, Marike Johanne; Hopff, David; Lüthje, Sabine

2010-01-01

Plant peroxidases are involved in numerous cellular processes in plant development and stress responses. Four plasma membrane-bound peroxidases have been identified and characterized in maize (Zea mays L.) roots. In the present study, maize seedlings were treated with different stresses and signal compounds, and a functional analysis of these membrane-bound class III peroxidases (pmPOX1, pmPOX2a, pmPOX2b, and pmPOX3) was carried out. Total guaiacol peroxidase activities from soluble and microsomal fractions of maize roots were compared and showed weak changes. By contrast, total plasma membrane and washed plasma membrane peroxidase activities, representing peripheral and integral membrane proteins, revealed strong changes after all of the stresses applied. A proteomic approach using 2D-PAGE analysis showed that pmPOX3 was the most abundant class III peroxidase at plasma membranes of control plants, followed by pmPOX2a >pmPOX2b >pmPOX1. The molecular mass (63 kDa) and the isoelectric point (9.5) of the pmPOX2a monomer were identified for the first time. The protein levels of all four enzymes changed in response to multiple stresses. While pmPOX2b was the only membrane peroxidase down-regulated by wounding, all four enzymes were differentially but strongly stimulated by methyl jasmonate, salicylic acid, and elicitors (Fusarium graminearum and Fusarium culmorum extracts, and chitosan) indicating their function in pathogen defence. Oxidative stress applied as H2O2 treatment up-regulated pmPOX2b >pmPOX2a, while pmPOX3 was down-regulated. Treatment with the phosphatase inhibitor chantharidin resulted in distinct responses. PMID:20032108

Characterization and Antimicrobial Activity of Volatile Constituents from Fresh Fruits of Alchornea cordifolia and Canthium subcordatum

PubMed Central

Essien, Emmanuel E.; Newby, Jennifer Schmidt; Walker, Tameka M.; Setzer, William N.; Ekundayo, Olusegun

2015-01-01

Bacterial resistance has been increasingly reported worldwide and is one of the major causes of failure in the treatment of infectious diseases. Natural-based products, including plant secondary metabolites (phytochemicals), can be exploited to ameliorate the problem of microbial resistance. The fruit essential oils of Alchornea cordifolia and Canthium subcordatum were obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS). The essential oils were subjected to in vitro antibacterial, antifungal and cytotoxic activity screening. Thirty-eight compounds comprising 97.7% of A. cordifolia oil and forty-six constituents representing 98.2% of C. subcordatum oil were identified. The major components in A. cordifolia oil were methyl salicylate (25.3%), citronellol (21.4%), α-phellandrene (7.4%), terpinolene (5.7%) and 1,8-cineole (5.5%). Benzaldehyde (28.0%), β-caryophyllene (15.5%), (E,E)-α-farnesene (5.3%) and methyl salicylate (4.5%) were the quantitatively significant constituents in C. subcordatum fruit essential oil. A. cordifolia essential oil demonstrated potent in vitro antibacterial activity against Staphylococcus aureus (MIC = 78 μg/mL) and marginal antifungal activity against Aspergillus niger (MIC = 156 μg/mL). C. subcordatum showed antibacterial activity against Bacillus cereus and S. aureus (MIC = 156 μg/mL) and notable antifungal activity against A. niger (MIC = 39 μg/mL). However, no appreciable cytotoxic effects on human breast carcinoma cells (Hs 578T) and human prostate carcinoma cells (PC-3) were observed for either essential oil. The antimicrobial activities of A. cordifolia and C. subcordatum fruit essential oils are a function of their distinct chemical profiles; their volatiles and biological activities are reported for the first time. PMID:28930111

Untargeted metabolomics analysis reveals dynamic changes in azelaic acid- and salicylic acid derivatives in LPS-treated Nicotiana tabacum cells.

PubMed

Mhlongo, M I; Tugizimana, F; Piater, L A; Steenkamp, P A; Madala, N E; Dubery, I A

2017-01-22

To counteract biotic stress factors, plants employ multilayered defense mechanisms responsive to pathogen-derived elicitor molecules, and regulated by different phytohormones and signaling molecules. Here, lipopolysaccharide (LPS), a microbe-associated molecular pattern (MAMP) molecule, was used to induce defense responses in Nicotiana tabacum cell suspensions. Intracellular metabolites were extracted with methanol and analyzed using a liquid chromatography-mass spectrometry (UHPLC-qTOF-MS/MS) platform. The generated data were processed and examined with multivariate and univariate statistical tools. The results show time-dependent dynamic changes and accumulation of glycosylated signaling molecules, specifically those of azelaic acid, salicylic acid and methyl-salicylate as contributors to the altered metabolomic state in LPS-treated cells. Copyright © 2016 Elsevier Inc. All rights reserved.

Embedded Piezoresistive Microcantilever Sensors Functionalized for the Detection of Methyl Salicylate

DOE Office of Scientific and Technical Information (OSTI.GOV)

Porter, Timothy L.; Venedam, Richard J.

2013-03-01

Sensors designed to detect the presence of methyl salicylate (MeS) have been tested. These sensors use a sensor platform based on the embedded piezoresistive microcantilever (EPM) design. Sensing materials tested in this study included the polymer poly (ethylene vinyl acetate), or PEVA as well as a composite sensing material consisting of the enzyme SA-binding protein 2, or SABP-2. The SABP-2 was immobilized within a biocompatible Hypol gel matrix. The PEVA-based sensors exhibited slower but reversible responses to MeS vapors, recovering fully to their initial state after the analyte was removed. SABP-2 sensors exhibited faster overall response to the introduction ofmore » MeS, responding nearly instantly. These sensors, however, do not recover after exposures have ended. Sensors using the SABP-2 sensing materials act instead as integrating sensors, measuring irreversibly the total MeS dose obtained.« less

PubMed Central

RALLI, M.; TROIANI, D.; PODDA, M.V.; PACIELLO, F.; ERAMO, S.L.M.; DE CORSO, E.; SALVI, R.; PALUDETTI, G.; FETONI, A.R.

2014-01-01

SUMMARY Short-term tinnitus develops shortly after the administration of a high dose of salicylate. Since salicylate selectively potentiates N-methyl- D-aspartate (NMDA) currents in spiral ganglion neurons, it may play a vital role in tinnitus by amplifying NMDA-mediated neurotransmission. The aim of this study was to determine whether systemic treatment with a NMDA channel blocker, memantine, could prevent salicylate-induced tinnitus in animals. Additional experiments were performed to evaluate the effect of memantine on the auditory brainstem response (ABR) and distortion product otoacoustic emissions (DPOAE) to test for changes in hearing function. Thirty-six rats were divided into 3 groups and treated daily for four consecutive days. One group (n = 12) was injected with salicylate (300 mg/kg/d, IP), the second (n = 12) was treated with memantine (5 mg/kg/d, IP) and the third group (n = 12) was injected with salicylate and memantine. All rats were tested for tinnitus and hearing loss at 2, 24, 48 and 72 h after the first drug administration and 24 h post treatment; tinnituslike behaviour was assessed with gap prepulse inhibition of acoustic startle (GPIAS), and hearing function was measured with DPOAE, ABR and noise burst prepulse inhibition of acoustic startle (NBPIAS). Rats in the salicylate group showed impaired GPIAS indicative of transient tinnitus-like behaviour near 16 kHz that recovered 24 h after the last salicylate treatment. Memantine did not cause a significant change in GPIAS. Combined injection of salicylate and memantine significantly attenuated GPIAS tinnitus-like behaviour at 48 hours after the first injection. None of the treatments induced permanent threshold shifts in the ABR and DPOAE, which recovered completely within one day post treatment. Animals treated with salicylate plus memantine showed results comparable to animals treated with salicylate alone, confirming that there is no effect of memantine on DPOAE which reflects OHC function. The present study confirms the role of cochlear NMDA receptors in the induction of salicylate-induced tinnitus. PMID:24882929

Monoterpenes Support Systemic Acquired Resistance within and between Plants

PubMed Central

Ghirardo, Andrea; Knappe, Claudia; Koch, Kerstin; Dey, Sanjukta; Parker, Jane E.

2017-01-01

This study investigates the role of volatile organic compounds in systemic acquired resistance (SAR), a salicylic acid (SA)-associated, broad-spectrum immune response in systemic, healthy tissues of locally infected plants. Gas chromatography coupled to mass spectrometry analyses of SAR-related emissions of wild-type and non-SAR-signal-producing mutant plants associated SAR with monoterpene emissions. Headspace exposure of Arabidopsis thaliana to a mixture of the bicyclic monoterpenes α-pinene and β-pinene induced defense, accumulation of reactive oxygen species, and expression of SA- and SAR-related genes, including the SAR regulatory AZELAIC ACID INDUCED1 (AZI1) gene and three of its paralogs. Pinene-induced resistance was dependent on SA biosynthesis and signaling and on AZI1. Arabidopsis geranylgeranyl reductase1 mutants with reduced monoterpene biosynthesis were SAR-defective but mounted normal local resistance and methyl salicylate-induced defense responses, suggesting that monoterpenes act in parallel with SA. The volatile emissions from SAR signal-emitting plants induced defense in neighboring plants, and this was associated with the presence of α-pinene, β-pinene, and camphene in the emissions of the “sender” plants. Our data suggest that monoterpenes, particularly pinenes, promote SAR, acting through ROS and AZI1, and likely function as infochemicals in plant-to-plant signaling, thus allowing defense signal propagation between neighboring plants. PMID:28536145

Salicylic acid and jasmonic acid are essential for systemic resistance against tobacco mosaic virus in Nicotiana benthamiana.

PubMed

Zhu, Feng; Xi, De-Hui; Yuan, Shu; Xu, Fei; Zhang, Da-Wei; Lin, Hong-Hui

2014-06-01

Systemic resistance is induced by pathogens and confers protection against a broad range of pathogens. Recent studies have indicated that salicylic acid (SA) derivative methyl salicylate (MeSA) serves as a long-distance phloem-mobile systemic resistance signal in tobacco, Arabidopsis, and potato. However, other experiments indicate that jasmonic acid (JA) is a critical mobile signal. Here, we present evidence suggesting both MeSA and methyl jasmonate (MeJA) are essential for systemic resistance against Tobacco mosaic virus (TMV), possibly acting as the initiating signals for systemic resistance. Foliar application of JA followed by SA triggered the strongest systemic resistance against TMV. Furthermore, we use a virus-induced gene-silencing-based genetics approach to investigate the function of JA and SA biosynthesis or signaling genes in systemic response against TMV infection. Silencing of SA or JA biosynthetic and signaling genes in Nicotiana benthamiana plants increased susceptibility to TMV. Genetic experiments also proved the irreplaceable roles of MeSA and MeJA in systemic resistance response. Systemic resistance was compromised when SA methyl transferase or JA carboxyl methyltransferase, which are required for MeSA and MeJA formation, respectively, were silenced. Moreover, high-performance liquid chromatography-mass spectrometry analysis indicated that JA and MeJA accumulated in phloem exudates of leaves at early stages and SA and MeSA accumulated at later stages, after TMV infection. Our data also indicated that JA and MeJA could regulate MeSA and SA production. Taken together, our results demonstrate that (Me)JA and (Me)SA are required for systemic resistance response against TMV.

Methyl salicylate 2-O-β-D-lactoside, a novel salicylic acid analogue, acts as an anti-inflammatory agent on microglia and astrocytes

PubMed Central

2011-01-01

Background Neuroinflammation has been known to play a critical role in the pathogenesis of Alzheimer's disease (AD). Activation of microglia and astrocytes is a characteristic of brain inflammation. Epidemiological studies have shown that long-term use of non-steroidal anti-inflammatory drugs (NSAIDs) delays the onset of AD and suppresses its progression. Methyl salicylate-2-O-β-D-lactoside (DL0309) is a new molecule chemically related to salicylic acid. The present study aimed to evaluate the anti-inflammatory effects of DL0309. Findings Our studies show that DL0309 significantly inhibits lipopolysaccharide (LPS)-induced release of the pro-inflammatory cytokines IL-6, IL-1β, and TNF-α; and the expression of the inflammation-related proteins iNOS, COX-1, and COX-2 by microglia and astrocytes. At a concentration of 10 μM, DL0309 prominently inhibited LPS-induced activation of NF-κB in glial cells by blocking phosphorylation of IKK and p65, and by blocking IκB degradation. Conclusions We demonstrate here for the first time that DL0309 exerts anti-inflammatory effects in glial cells by suppressing different pro-inflammatory cytokines and iNOS/NO. Furthermore, it also regulates the NF-κB signaling pathway by blocking IKK and p65 activation and IκB degradation. DL0309 also acts as a non-selective COX inhibitor in glial cells. These studies suggest that DL0309 may be effective in the treatment of neuroinflammatory disorders, including AD. PMID:21831328

Bioinspired Surface Treatments for Improved Decontamination: Silicon and Latex Polymer SLIPS Treatments

DTIC Science & Technology

2017-06-27

of the simulants paraoxon, methyl salicylate, dimethyl methylphosphate, and diisopropyl fluorophosphates following treatment of contaminated surfaces...Biological Defense Program (CBDP) seeks to provide protection of forces in a contaminated environment including contamination avoidance, individual

TSCA Environmental Release Application (TERA) for Modified Pseudomonas Fluorescens

EPA Pesticide Factsheets

TERA submitted by Micro Systems Technologies, LLC and given the tracking designations of R-02-0001. The microorganism has been genetically modified to contain a bioluminescent gene that is activated upon metabolism of naphthalene and/or methyl salicylate.

Oxygen transfer rate identifies priming compounds in parsley cells.

PubMed

Schilling, Jana Viola; Schillheim, Britta; Mahr, Stefan; Reufer, Yannik; Sanjoyo, Sandi; Conrath, Uwe; Büchs, Jochen

2015-11-25

In modern agriculture, the call for an alternative crop protection strategy increases because of the desired reduction of fungicide and pesticide use and the continuously evolving resistance of pathogens and pests to agrochemicals. The direct activation of the plant immune system does not provide a promising plant protection measure because of high fitness costs. However, upon treatment with certain natural or synthetic compounds, plant cells can promote to a fitness cost-saving, primed state of enhanced defense. In the primed state, plants respond to biotic and abiotic stress with faster and stronger activation of defense, and this is often associated with immunity and abiotic stress tolerance. Until now, the identification of chemical compounds with priming-inducing activity (so-called plant activators) relied on tedious and invasive approaches, or required the late detection of secreted furanocoumarin phytoalexins in parsley cell cultures. Thus, simple, fast, straightforward, and noninvasive techniques for identifying priming-inducing compounds for plant protection are very welcome. This report demonstrates that a respiration activity-monitoring system (RAMOS) can identify compounds with defense priming-inducing activity in parsley cell suspension in culture. RAMOS relies on the quasi-continuous, noninvasive online determination of the oxygen transfer rate (OTR). Treatment of parsley culture cells with the known plant activator salicylic acid (SA), a natural plant defense signal, resulted in an OTR increase. Addition of the defense elicitor Pep13, a cell wall peptide of Phythophthora sojae, induced two distinctive OTR peaks that were higher in SA-primed cells than in unprimed cells upon Pep13 challenge. Both, the OTR increase after priming with SA and the Pep13 challenge were dose-dependent. Furthermore, there was a close correlation of a compound's activity to enhance the oxygen consumption in parsley cells and its capacity to prime Pep13-induced furanocoumarin secretion as evaluated by fluorescence spectroscopy. RAMOS noninvasively determines the OTR as a measure of the metabolic activity of plant cells. Chemical enhancement of oxygen consumption by salicylic derivatives in parsley cell suspension cultures correlates with the induction of the primed state of enhanced defense that enhances the quantity of Pep13-induced furanocoumarin phytoalexins. Treatment with the priming-active compounds methyl jasmonate and pyraclostrobin also resulted in an enhanced respiration activity. Thus, RAMOS is a novel technology for identifying priming-inducing compounds for agriculture.

The Combined Effects of Ethylene and MeJA on Metabolic Profiling of Phenolic Compounds in Catharanthus roseus Revealed by Metabolomics Analysis

PubMed Central

Liu, Jia; Liu, Yang; Wang, Yu; Zhang, Zhong-Hua; Zu, Yuan-Gang; Efferth, Thomas; Tang, Zhong-Hua

2016-01-01

Phenolic compounds belong to a class of secondary metabolites and are implicated in a wide range of responsive mechanisms in plants triggered by both biotic and abiotic elicitors. In this study, we approached the combinational effects of ethylene and MeJA (methyl jasmonate) on phenolic compounds profiles and gene expressions in the medicinal plant Catharanthus roseus. In virtue of a widely non-targeted metabolomics method, we identified a total of 34 kinds of phenolic compounds in the leaves, composed by 7 C6C1-, 11 C6C3-, and 16 C6C3C6 compounds. In addition, 7 kinds of intermediates critical for the biosynthesis of phenolic compounds and alkaloids were identified and discussed with phenolic metabolism. The combinational actions of ethylene and MeJA effectively promoted the total phenolic compounds, especially the C6C1 compounds (such as salicylic acid, benzoic acid) and C6C3 ones (such as cinnamic acid, sinapic acid). In contrast, the C6C3C6 compounds displayed a notably inhibitory trend in this case. Subsequently, the gene-to-metabolite networks were drawn up by searching for correlations between the expression profiles of 5 gene tags and the accumulation profiles of 41 metabolite peaks. Generally, we provide an insight into the controlling mode of ethylene-MeJA combination on phenolic metabolism in C. roseus leaves. PMID:27375495

The Combined Effects of Ethylene and MeJA on Metabolic Profiling of Phenolic Compounds in Catharanthus roseus Revealed by Metabolomics Analysis.

PubMed

Liu, Jia; Liu, Yang; Wang, Yu; Zhang, Zhong-Hua; Zu, Yuan-Gang; Efferth, Thomas; Tang, Zhong-Hua

2016-01-01

Phenolic compounds belong to a class of secondary metabolites and are implicated in a wide range of responsive mechanisms in plants triggered by both biotic and abiotic elicitors. In this study, we approached the combinational effects of ethylene and MeJA (methyl jasmonate) on phenolic compounds profiles and gene expressions in the medicinal plant Catharanthus roseus. In virtue of a widely non-targeted metabolomics method, we identified a total of 34 kinds of phenolic compounds in the leaves, composed by 7 C6C1-, 11 C6C3-, and 16 C6C3C6 compounds. In addition, 7 kinds of intermediates critical for the biosynthesis of phenolic compounds and alkaloids were identified and discussed with phenolic metabolism. The combinational actions of ethylene and MeJA effectively promoted the total phenolic compounds, especially the C6C1 compounds (such as salicylic acid, benzoic acid) and C6C3 ones (such as cinnamic acid, sinapic acid). In contrast, the C6C3C6 compounds displayed a notably inhibitory trend in this case. Subsequently, the gene-to-metabolite networks were drawn up by searching for correlations between the expression profiles of 5 gene tags and the accumulation profiles of 41 metabolite peaks. Generally, we provide an insight into the controlling mode of ethylene-MeJA combination on phenolic metabolism in C. roseus leaves.

sal Genes Determining the Catabolism of Salicylate Esters Are Part of a Supraoperonic Cluster of Catabolic Genes in Acinetobacter sp. Strain ADP1

PubMed Central

Jones, Rheinallt M.; Pagmantidis, Vassilis; Williams, Peter A.

2000-01-01

A 5-kbp region upstream of the are-ben-cat genes was cloned from Acinetobacter sp. strain ADP1, extending the supraoperonic cluster of catabolic genes to 30 kbp. Four open reading frames, salA, salR, salE, and salD, were identified from the nucleotide sequence. Reverse transcription-PCR studies suggested that these open reading frames are organized into two convergent transcription units, salAR and salDE. The salE gene, encoding a protein of 239 residues, was ligated into expression vector pET5a. Its product, SalE, was shown to have esterase activity against short-chain alkyl esters of 4-nitrophenol but was also able to hydrolyze ethyl salicylate to ethanol and salicylic acid. A mutant of ADP1 with a Kmr cassette introduced into salE had lost the ability to utilize only ethyl and methyl salicylates of the esters tested as sole carbon sources, and no esterase activity against ethyl salicylate could be detected in cell extracts. SalE was induced during growth on ethyl salicylate but not during growth on salicylate itself. salD encoded a protein of undetermined function with homologies to the Escherichia coli FadL membrane protein, which is involved in facilitating fatty acid transport, and a number of other proteins detected during aromatic catabolism, which may also function in hydrocarbon transport or uptake processes. A Kmr cassette insertion in salD deleteriously affected cell growth and viability. The salA and salR gene products closely resemble two Pseudomonas proteins, NahG and NahR, respectively encoding salicylate hydroxylase and the LysR family regulator of both salicylate and naphthalene catabolism. salA was cloned into pUC18 together with salR and salE, and its gene product showed salicylate-inducible hydroxylase activity against a range of substituted salicylates, with the same relative specific activities as found in wild-type ADP1 grown on salicylate. Mutations involving insertion of Kmr cassettes into salA and salR eliminated expression of salicylate hydroxylase activity and the ability to grow on either salicylate or ethyl salicylate. Studies of mutants with disruptions of genes of the β-ketoadipate pathway with or without an additional salE mutation confirmed that ethyl salicylate and salicylate were channeled into the β-ketoadipate pathway at the level of catechol and thence dissimilated by the cat gene products. SalR appeared to regulate expression of salA but not salE. PMID:10715011

A retention index calculator simplifies identification of plant volatile organic compounds.

PubMed

Lucero, Mary; Estell, Rick; Tellez, María; Fredrickson, Ed

2009-01-01

Plant volatiles (PVOCs) are important targets for studies in natural products, chemotaxonomy and biochemical ecology. The complexity of PVOC profiles often limits research to studies targeting only easily identified compounds. With the availability of mass spectral libraries and recent growth of retention index (RI) libraries, PVOC identification can be achieved using only gas chromatography coupled to mass spectrometry (GCMS). However, RI library searching is not typically automated, and until recently, RI libraries were both limited in scope and costly to obtain. To automate RI calculation and lookup functions commonly utilised in PVOC analysis. Formulae required for calculating retention indices from retention time data were placed in a spreadsheet along with lookup functions and a retention index library. Retention times obtained from GCMS analysis of alkane standards and Koeberlinia spinosa essential oil were entered into the spreadsheet to determine retention indices. Indices were used in combination with mass spectral analysis to identify compounds contained in Koeberlinia spinosa essential oil. Eighteen compounds were positively identified. Total oil yield was low, with only 5 ppm in purple berries. The most abundant compounds were octen-3-ol and methyl salicylate. The spreadsheet accurately calculated RIs of the detected compounds. The downloadable spreadsheet tool developed for this study provides a calculator and RI library that works in conjuction with GCMS or other analytical techniques to identify PVOCs in plant extracts.

New Approaches for Prostate Cancer Combination Therapy

DTIC Science & Technology

2009-04-01

promoter methylation have been frequently observed in several types of human cancer (60, 61). In conclusion, the ability of NSAIDs to induce apoptosis...drug. Clin Pharmacokinet 1999; 36:115–26. 31. Yin MJ, Yamamoto Y, Gaynor RB. The anti- inflammatory agents aspirin and salicylate inhibit the activity...expression of the growth inhibitory gene GADD45g, in human pituitary adenomas, is asso- ciated with CpG island methylation . Oncogene 2004;23: 936–44. 61

Mobility and Molecular Ions of Dimethyl Methyl Phosphonate, Methyl Salicylate, and Acetone.

DTIC Science & Technology

1983-06-01

MICRCOP REOUIO.ET1HR NICOCOPY BRESOUIO EST CHAR T AD .-..., CHEMICOL f.. SYSTEMS US Army Armament 11..: LABORATORY Research and Development Command _NTR...ORGANIZATION NAME AND ADDRESS 10. PROGRAM ELEMENT PROJECT, TASK Commnde, Cemicl Sstes LaoraoryAREA & WORK U NIT’NUMBERS CommNder DARCemia Systems Laborato...Chemical Systems Laboratory, ATTN: DRDAR-CLJ-IR, Aberdeen Proving Ground, Maryland 21010. However, the Defense Technical Information Center and National

Substrate-Assisted Catalysis in the Reaction Catalyzed by Salicylic Acid Binding Protein 2 (SABP2), a Potential Mechanism of Substrate Discrimination for Some Promiscuous Enzymes.

PubMed

Yao, Jianzhuang; Guo, Haobo; Chaiprasongsuk, Minta; Zhao, Nan; Chen, Feng; Yang, Xiaohan; Guo, Hong

2015-09-01

Although one of an enzyme's hallmarks is the high specificity for their natural substrates, substrate promiscuity has been reported more frequently. It is known that promiscuous enzymes generally show different catalytic efficiencies to different substrates, but our understanding of the origin of such differences is still lacking. Here we report the results of quantum mechanical/molecular mechanical simulations and an experimental study of salicylic acid binding protein 2 (SABP2). SABP2 has promiscuous esterase activity toward a series of substrates but shows a high activity toward its natural substrate, methyl salicylate (MeSA). Our results demonstrate that this enzyme may use substrate-assisted catalysis involving the hydroxyl group from MeSA to enhance the activity and achieve substrate discrimination.

Substrate-Assisted Catalysis in the Reaction Catalyzed by Salicylic Acid Binding Protein 2 (SABP2), a Potential Mechanism of Substrate Discrimination for Some Promiscuous Enzymes

DOE Office of Scientific and Technical Information (OSTI.GOV)

Yao, Jianzhuang; Guo, Haobo; Chaiprasongsuk, Minta

Although one of an enzyme’s hallmarks is the high specificity for their natural substrates, substrate promiscuity has been reported more frequently. We know that promiscuous enzymes generally show different catalytic efficiencies to different substrates, but our understanding of the origin of such differences is still lacking. We report the results of quantum mechanical/molecular mechanical simulations and an experimental study of salicylic acid binding protein 2 (SABP2). SABP2 has promiscuous esterase activity toward a series of substrates but shows a high activity toward its natural substrate, methyl salicylate (MeSA). Finally, our results demonstrate that this enzyme may use substrate-assisted catalysis involvingmore » the hydroxyl group from MeSA to enhance the activity and achieve substrate discrimination.« less

Substrate-Assisted Catalysis in the Reaction Catalyzed by Salicylic Acid Binding Protein 2 (SABP2), a Potential Mechanism of Substrate Discrimination for Some Promiscuous Enzymes

DOE PAGES

Yao, Jianzhuang; Guo, Haobo; Chaiprasongsuk, Minta; ...

2015-08-05

Although one of an enzyme’s hallmarks is the high specificity for their natural substrates, substrate promiscuity has been reported more frequently. We know that promiscuous enzymes generally show different catalytic efficiencies to different substrates, but our understanding of the origin of such differences is still lacking. We report the results of quantum mechanical/molecular mechanical simulations and an experimental study of salicylic acid binding protein 2 (SABP2). SABP2 has promiscuous esterase activity toward a series of substrates but shows a high activity toward its natural substrate, methyl salicylate (MeSA). Finally, our results demonstrate that this enzyme may use substrate-assisted catalysis involvingmore » the hydroxyl group from MeSA to enhance the activity and achieve substrate discrimination.« less

Salicylate-induced changes in immediate-early genes in the hippocampal CA1 area

PubMed Central

WU, HAO; XU, FENG-LEI; YIN, YONG; DA, PENG; YOU, XIAO-DONG; XU, HUI-MIN; TANG, YAN

2015-01-01

Studies have suggested that salicylate affects neuronal function via interactions with specific membrane channels/receptors. However, the effect of salicylate on activity and synaptic morphology of the hippocampal Cornu Ammonis (CA) 1 area remains to be elucidated. The activation of immediate-early genes (IEGs) was reported to correlate with neuronal activity, in particular activity-regulated cytoskeleton-associated protein and early growth response gene 1. The aim of the present study was to evaluate the expression of these IEGs, as well that of N-methyl D-aspartate (NMDA) receptor subunit 2B in rats following acute and chronic salicylate treatment. Protein and messenger RNA levels of all three genes were increased in rats following chronic administration of salicylate (300 mg/kg for 10 days), returning to baseline levels 14 days post-cessation of treatment. The transient upregulation of gene expression following treatment was accompanied by ultrastructural alterations in hippocampal CA1 area synapses. An increase in synaptic interface curvature was observed as well as an increased number of presynaptic vesicles; in addition, postsynaptic densities thickened and lengthened. In conclusion, the results of the present study indicated that chronic exposure to salicylate may lead to structural alteration of hippocampal CA1 neurons, and it was suggested that this process occurs through induced expression of IEGs via NMDA receptor activation. PMID:25873216

Floral benzenoid carboxyl methyltransferases: From in vitro to in planta function

PubMed Central

Effmert, Uta; Saschenbrecker, Sandra; Ross, Jeannine; Negre, Florence; Fraser, Chris M.; Noel, Joseph P.; Dudareva, Natalia; Piechulla, Birgit

2010-01-01

Benzenoid carboxyl methyltransferases synthesize methyl esters (e.g., methyl benzoate and methyl salicylate), which are constituents of aromas and scents of many plant species and play important roles in plant communication with the surrounding environment. Within the past five years, eleven such carboxyl methyltransferases were isolated and most of them were comprehensively investigated at the biochemical, molecular and structural level. Two types of enzymes can be distinguished according to their substrate preferences: the SAMT-type enzymes isolated from Clarkia breweri, Stephanotis floribunda, Antirrhinum majus, Hoya carnosa, and Petunia hybrida, which have a higher catalytic efficiency and preference for salicylic acid, while BAMT-type enzymes from A. majus, Arabidopsis thaliana, Arabidopsis lyrata, and Nicotiana suaveolens prefer benzoic acid. The elucidation of C. breweri SAMT’s three-dimensional structure allowed a detailed modelling of the active sites of the carboxyl methyltransferases and revealed that the SAM binding pocket is highly conserved among these enzymes while the methyl acceptor binding site exhibits some variability, allowing a classification into SAMT-type and BAMT-type enzymes. The analysis of expression patterns coupled with biochemical characterization showed that these carboxyl methyltransferases are involved either in floral scent biosynthesis or in plant defense responses. While the latter can be induced by biotic or abiotic stress, the genes responsible for floral scent synthesis exhibit developmental and rhythmic expression pattern. The nature of the product and efficiency of its formation in planta depend on the availability of substrates, the catalytic efficiency of the enzyme toward benzoic acid and/or salicylic acid, and the transcriptional, translational, and post-translational regulation at the enzyme level. The biochemical properties of benzenoid carboxyl methyltransferases suggest that the genes involved in plant defenses might represent the ancestor for the presently existing floral genes which during evolution gained different expression profiles and encoded enzymes with the ability to accept structurally similar substrates. PMID:15946712

Redirection of metabolite biosynthesis from hydroxybenzoates to volatile terpenoids in green hairy roots of Daucus carota.

PubMed

Mukherjee, Chiranjit; Samanta, Tanmoy; Mitra, Adinpunya

2016-02-01

A metabolic shift in green hairy root cultures of carrot from phenylpropanoid/benzenoid biosynthesis toward volatile isoprenoids was observed when compared with the metabolite profile of normal hairy root cultures. Hairy roots cultures of Daucus carota turned green under continuous illumination, while the content of the major phenolic compound p-hydroxybenzoic acid (p-HBA) was reduced to half as compared to normal hairy roots cultured in darkness. p-Hydroxybenzaldehyde dehydrogenase (HBD) activity was suppressed in the green hairy roots. However, comparative volatile analysis of 14-day-old green hairy roots revealed higher monoterpene and sesquiterpene contents than found in normal hairy roots. Methyl salicylate content was higher in normal hairy roots than in green ones. Application of clomazone, an inhibitor of 1-deoxy-D-xylulose 5-phosphate synthase (DXS), reduced the amount of total monoterpenes and sesquiterpenes in green hairy roots compared to normal hairy roots. However, methyl salicylate content was enhanced in both green and normal hairy roots treated with clomazone as compared to their respective controls. Because methyl-erythritol 4-phosphate (MEP) and phenylpropanoid pathways, respectively, contribute to the formation of monoterpenes and phenolic acids biosynthesis, the activities of enzymes regulating those pathways were measured in terms of their in vitro activities, in both green and normal hairy root cultures. These key enzymes were 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), an early regulatory enzyme of the MEP pathway, pyruvate kinase (PK), an enzyme of primary metabolism related to the MEP pathway, shikimate dehydrogenase (SKDH) which is involved in biosynthesis of aromatic amino acids, and phenylalanine ammonia-lyase (PAL) that catalyzes the first step of phenylpropanoid biosynthesis. Activities of DXR and PK were higher in green hairy roots as compared to normal ones, whereas the opposite trend was observed for SKDH and PAL activities. Gene expression analysis of DXR and PAL showed trends similar to those for the respective enzyme activities. Based on these observations, we suggest a possible redirection of metabolites from the primary metabolism toward isoprenoid biosynthesis, limiting the phenolic biosynthetic pathway in green hairy roots grown under continuous light.

Effects of C-phycocyanin and Spirulina on Salicylate-Induced Tinnitus, Expression of NMDA Receptor and Inflammatory Genes

PubMed Central

Hwang, Juen-Haur; Chen, Jin-Cherng; Chan, Yin-Ching

2013-01-01

Effects of C-phycocyanin (C-PC), the active component of Spirulina platensis water extract on the expressions of N-methyl D-aspartate receptor subunit 2B (NR2B), tumor necrosis factor–α (TNF-α), interleukin-1β (IL-1β), and cyclooxygenase type 2 (COX-2) genes in the cochlea and inferior colliculus (IC) of mice were evaluated after tinnitus was induced by intraperitoneal injection of salicylate. The results showed that 4-day salicylate treatment (unlike 4-day saline treatment) caused a significant increase in NR2B, TNF-α, and IL-1β mRNAs expression in the cochlea and IC. On the other hand, dietary supplementation with C-PC or Spirulina platensis water extract significantly reduced the salicylate-induced tinnitus and down-regulated the mRNAs expression of NR2B, TNF-α, IL-1β mRNAs, and COX-2 genes in the cochlea and IC of mice. The changes of protein expression levels were generally correlated with those of mRNAs expression levels in the IC for above genes. PMID:23533584

Increase of Chamazulene and α-Bisabolol Contents of the Essential Oil of German Chamomile (Matricaria chamomilla L.) Using Salicylic Acid Treatments under Normal and Heat Stress Conditions.

PubMed

Ghasemi, Mojtaba; Babaeian Jelodar, Nadali; Modarresi, Mohammad; Bagheri, Nadali; Jamali, Abbas

2016-08-27

The chamazulene and α-(-)-bisabolol contents and quality of the chamomile oil are affected by genetic background and environmental conditions. Salicylic acid (SA), as a signaling molecule, plays a significant role in the plant physiological processes. The aim of this study was to evaluate the chemical profile, quantity, and improve the essential oil quality as a consequence of the increase of chamazulene and α-(-)-bisabol using salicylic acid under normal and heat stress conditions by the gas chromatography-mass spectrometry (GC-MS) technique. The factorial experiments were carried out during the 2011-2012 hot season using a randomized complete block design with three replications. The factors include four salicylic acid concentrations (0 (control), 10, 25 and 100 mg·L -1 ), and three chamomile cultivars (Bushehr, Bona, Bodegold) were sown on two different planting dates under field conditions. Fourteen compounds were identified from the extracted oil of the samples treated with salicylic acid under normal and heat stress conditions. The major identified oil compositions from chamomile cultivars treated with salicylic acid were chamazulene, α-(-)-bisabolol, bisabolone oxide, β-farnesene, en-yn-dicycloether, and bisabolol oxide A and B. Analysis of variance showed that the simple effects (environmental conditions, cultivar and salicylic acid) and their interaction were significant on all identified compounds, but the environmental conditions had no significant effect on bisabolol oxide A. The greatest amount of chamazulene obtained was 6.66% at the concentration of 10 mg·L -1 SA for the Bona cultivar under heat stress conditions, whereas the highest α-(-)-bisabolol amount attained was 3.41% at the concentration of 100 mg·L -1 SA for the Bona cultivar under normal conditions. The results demonstrated that the application of exogenous salicylic acid increases the quantity and essential oil quality as a consequence of the increase of chamazulene and α-(-)-bisabolol under normal and heat stress conditions.

Comparison of the therapeutic efficacy of double-modality therapy, phonophoresis and cryotherapy in the management of musculoskeletal injuries in adult Nigerian subjects.

PubMed

Onuwe, H A; Amadi, K; Odeh, S O

2013-12-20

This study was designed to compare the efficacy of double-modality therapy, phonophoresis and cryotherapy in the management of pain among subjects who suffered from musculoskeletal injuries (MSIs).Sixty (60) subjects were assigned randomly to one of three groups: DMT group (n=20) received cryotherapy and 15% methyl salicylate phonophoresis, PHONO group (n=20) received 15% methyl salicylate phonophoresis and CRYO group (n=20) received cryotherapy and "sham‟ phonophoresis. Ultrasound at an intensity of 1.5 W/cm² and frequency of 1MHz was used to apply methyl salicylate while intermittent cryotherapy was the mode of application. Subjects‟ pre- and post-treatment pain perception scores (PPS) using visual analogue scale (VAS) were assessed and the sessions of treatment in all groups were recorded. Treatment was administered on alternate days and discharges were made in all groups when subjects were pain free. A total of 275 treatment sessions was recorded - 72 (26.2%) in DMT, 105 (38.2%) in PHONO and 98 (35.6%) in CRYO group respectively which indicated no significant difference (P>0.05). Nineteen (19), thirteen (13) and twelve (12) subjects were pain free in DMT, CRYO or PHONO groups respectively after 1 to 5 treatments. The difference in the severity of pain was significant (P<0.05) in each group post-treatment which suggests that DMT, phonophoresis and cryotherapy were equally effective. The study has demonstrated therapeutic efficacy of DMT, but it was not superior to the single treatment protocol of phonophoresis or cryotherapy. However, it might take fewer sessions in the DMT group to treat and make more than 90% of the subjects pain free and fit to return to active performance.

Jasmonic Acid Is a Key Regulator of Spider Mite-Induced Volatile Terpenoid and Methyl Salicylate Emission in Tomato1[w

PubMed Central

Ament, Kai; Kant, Merijn R.; Sabelis, Maurice W.; Haring, Michel A.; Schuurink, Robert C.

2004-01-01

The tomato (Lycopersicon esculentum) mutant def-1, which is deficient in induced jasmonic acid (JA) accumulation upon wounding or herbivory, was used to study the role of JA in the direct and indirect defense responses to phytophagous mites (Tetranychus urticae). In contrast to earlier reports, spider mites laid as many eggs and caused as much damage on def-1 as on wild-type plants, even though def-1 lacked induction of proteinase inhibitor activity. However, the hatching-rate of eggs on def-1 was significantly higher, suggesting that JA-dependent direct defenses enhanced egg mortality or increased the time needed for embryonic development. As to gene expression, def-1 had lower levels of JA-related transcripts but higher levels of salicylic acid (SA) related transcripts after 1 d of spider mite infestation. Furthermore, the indirect defense response was absent in def-1, since the five typical spider mite-induced tomato-volatiles (methyl salicylate [MeSA], 4,8,12-trimethyltrideca-1,3,7,11-tetraene [TMTT], linalool, trans-nerolidol, and trans-β-ocimene) were not induced and the predatory mite Phytoseiulus persimilis did not discriminate between infested and uninfested def-1 tomatoes as it did with wild-type tomatoes. Similarly, the expression of the MeSA biosynthetic gene salicylic acid methyltransferase (SAMT) was induced by spider mites in wild type but not in def-1. Exogenous application of JA to def-1 induced the accumulation of SAMT and putative geranylgeranyl diphosphate synthase transcripts and restored MeSA- and TMTT-emission upon herbivory. JA is therefore necessary to induce the enzymatic conversion of SA into MeSA. We conclude that JA is essential for establishing the spider mite-induced indirect defense response in tomato. PMID:15310835

Enhancement of anti-inflammatory activity of Aloe vera adventitious root extracts through the alteration of primary and secondary metabolites via salicylic acid elicitation.

PubMed

Lee, Yun Sun; Ju, Hyun Kyoung; Kim, Yeon Jeong; Lim, Tae-Gyu; Uddin, Md Romij; Kim, Yeon Bok; Baek, Jin Hong; Kwon, Sung Won; Lee, Ki Won; Seo, Hak Soo; Park, Sang Un; Yang, Tae-Jin

2013-01-01

Aloe vera (Asphodeloideae) is a medicinal plant in which useful secondary metabolites are plentiful. Among the representative secondary metabolites of Aloe vera are the anthraquinones including aloe emodin and chrysophanol, which are tricyclic aromatic quinones synthesized via a plant-specific type III polyketide biosynthesis pathway. However, it is not yet clear which cellular responses can induce the pathway, leading to production of tricyclic aromatic quinones. In this study, we examined the effect of endogenous elicitors on the type III polyketide biosynthesis pathway and identified the metabolic changes induced in elicitor-treated Aloe vera adventitious roots. Salicylic acid, methyl jasmonate, and ethephon were used to treat Aloe vera adventitious roots cultured on MS liquid media with 0.3 mg/L IBA for 35 days. Aloe emodin and chrysophanol were remarkably increased by the SA treatment, more than 10-11 and 5-13 fold as compared with untreated control, respectively. Ultra-performance liquid chromatography-electrospray ionization mass spectrometry analysis identified a total of 37 SA-induced compounds, including aloe emodin and chrysophanol, and 3 of the compounds were tentatively identified as tricyclic aromatic quinones. Transcript accumulation analysis of polyketide synthase genes and gas chromatography mass spectrometry showed that these secondary metabolic changes resulted from increased expression of octaketide synthase genes and decreases in malonyl-CoA, which is the precursor for the tricyclic aromatic quinone biosynthesis pathway. In addition, anti-inflammatory activity was enhanced in extracts of SA-treated adventitious roots. Our results suggest that SA has an important role in activation of the plant specific-type III polyketide biosynthetic pathway, and therefore that the efficacy of Aloe vera as medicinal agent can be improved through SA treatment.

Enhancement of Anti-Inflammatory Activity of Aloe vera Adventitious Root Extracts through the Alteration of Primary and Secondary Metabolites via Salicylic Acid Elicitation

PubMed Central

Lee, Yun Sun; Ju, Hyun Kyoung; Kim, Yeon Jeong; Lim, Tae-Gyu; Uddin, Md Romij; Kim, Yeon Bok; Baek, Jin Hong; Kwon, Sung Won; Lee, Ki Won; Seo, Hak Soo; Park, Sang Un; Yang, Tae-Jin

2013-01-01

Aloe vera (Asphodeloideae) is a medicinal plant in which useful secondary metabolites are plentiful. Among the representative secondary metabolites of Aloe vera are the anthraquinones including aloe emodin and chrysophanol, which are tricyclic aromatic quinones synthesized via a plant-specific type III polyketide biosynthesis pathway. However, it is not yet clear which cellular responses can induce the pathway, leading to production of tricyclic aromatic quinones. In this study, we examined the effect of endogenous elicitors on the type III polyketide biosynthesis pathway and identified the metabolic changes induced in elicitor-treated Aloe vera adventitious roots. Salicylic acid, methyl jasmonate, and ethephon were used to treat Aloe vera adventitious roots cultured on MS liquid media with 0.3 mg/L IBA for 35 days. Aloe emodin and chrysophanol were remarkably increased by the SA treatment, more than 10–11 and 5–13 fold as compared with untreated control, respectively. Ultra-performance liquid chromatography-electrospray ionization mass spectrometry analysis identified a total of 37 SA-induced compounds, including aloe emodin and chrysophanol, and 3 of the compounds were tentatively identified as tricyclic aromatic quinones. Transcript accumulation analysis of polyketide synthase genes and gas chromatography mass spectrometry showed that these secondary metabolic changes resulted from increased expression of octaketide synthase genes and decreases in malonyl-CoA, which is the precursor for the tricyclic aromatic quinone biosynthesis pathway. In addition, anti-inflammatory activity was enhanced in extracts of SA-treated adventitious roots. Our results suggest that SA has an important role in activation of the plant specific-type III polyketide biosynthetic pathway, and therefore that the efficacy of Aloe vera as medicinal agent can be improved through SA treatment. PMID:24358188

Enhancing monoterpene alcohols in sweet potato shochu using the diglycoside-specific β-primeverosidase.

PubMed

Sato, Yuichiro; Han, Jinshun; Fukuda, Hisashi; Mikami, Shigeaki

2018-02-01

Monoterpene alcohols (MTAs) are characteristic flavour-imparting compounds in sweet potato shochu (Japanese distilled spirit) that are liberated following hydrolysis by specific enzymes during fermentation. In the present study, we evaluated the effect of an exogenously added diglycoside-specific β-glycosidase (β-primeverosidase) on aroma formation during shochu brewing using various sweet potato species to address whether MTAs are predominantly present as diglycosidic precursors in raw materials. The results showed that the amount of MTAs produced from enzyme-treated mash was dramatically increased by 2- to 9-fold compared with untreated controls, and the increase varied with sweet potato species. In addition, levels of methyl salicylate, 1-octene-3-ol and ethyl benzoate were also elevated by enzyme treatment. These results indicate that a large amount of MTAs and other volatile aroma compounds are stored in the form of disaccharide β-glycosides such as β-primeverosides in sweet potato. This enzyme may therefore be useful for controlling aroma formation during shochu manufacturing, and may ultimately contribute to diversifying shochu quality. Copyright © 2017 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

A reagent-assisted method in SERS detection of methyl salicylate

NASA Astrophysics Data System (ADS)

Li, Yali; Li, Qianwen; Wang, Yanan; Oh, Joohee; Jin, Sila; Park, Yeonju; Zhou, Tieli; Zhao, Bing; Ruan, Weidong; Jung, Young Mee

2018-04-01

With the explosive application of methyl salicylate (MS) molecules in food and cosmetics, the further detection of MS molecules becomes particularly important. Here we investigated the detection of MS molecules based on surface-enhanced Raman scattering (SERS) in a novel molecule/assistant/metal system constructed with MS, 4,4‧-(hexafluoroisopropylidene) bis (benzoic acid) and Ag nanoparticles (AgNPs). The minimum detection concentration is 10-4 M. To explore the function of assisted reagent, we also referred another system without assistant molecules. The result demonstrates that SERS signals were not acquired, which proves that the assistant molecules are critical for the capture of MS molecules. Two possible mechanisms of MS/assistant/AgNPs system were speculated through two patterns of hydrogen bonds. The linker molecules acted as the role of the bridge between metallic substrates and target molecules through the molecular recognition. This strategy is very beneficial to the expanding of MS detection techniques and other hydrogen bond based coupling detections with SERS.

UV-C-Induced alleviation of transcriptional gene silencing through plant-plant communication: Key roles of jasmonic acid and salicylic acid pathways.

PubMed

Xu, Wei; Wang, Ting; Xu, Shaoxin; Li, Fanghua; Deng, Chenguang; Wu, Lijun; Wu, Yuejin; Bian, Po

2016-08-01

Plant stress responses at the epigenetic level are expected to allow more permanent changes of gene expression and potentially long-term adaptation. While it has been reported that plants subjected to adverse environments initiate various stress responses in their neighboring plants, little is known regarding epigenetic responses to external stresses mediated by plant-plant communication. In this study, we show that DNA repetitive elements of Arabidopsis thaliana, whose expression is inhibited epigenetically by transcriptional gene silencing (TGS) mechanism, are activated by UV-C irradiation through airborne plant-plant and plant-plant-plant communications, accompanied by DNA demethylation at CHH sites. Moreover, the TGS is alleviated by direct treatments with exogenous methyl jasmonate (MeJA) and methyl salicylate (MeSA). Further, the plant-plant and plant-plant-plant communications are blocked by mutations in the biosynthesis or signaling of jasmonic acid (JA) or salicylic acid (SA), indicating that JA and SA pathways are involved in the interplant communication for epigenetic responses. For the plant-plant-plant communication, stress cues are relayed to the last set of receiver plants by promoting the production of JA and SA signals in relaying plants, which exhibit upregulated expression of genes for JA and SA biosynthesis and enhanced emanation of MeJA and MeSA. Copyright © 2016 Elsevier B.V. All rights reserved.

Therapeutic potentials of Crataegus azarolus var. eu- azarolus Maire leaves and its isolated compounds.

PubMed

Abu-Gharbieh, Eman; Shehab, Naglaa Gamil

2017-04-18

Hyperglycemia is a complicated condition accompanied with high incidence of infection and dyslipidemia. This study aimed to explore the phyto-constituents of Crataegus azarolus var. eu- azarolus Maire leaves, and to evaluate the therapeutic potentials particularly antimicrobial, antihyperglycemic and antihyperlipidemic of the extract and the isolated compound (3β-O-acetyl ursolic acid). Total phenolics and flavonoidal contents were measured by RP-HPLC analysis. Free radicals scavenging activity of different extraction solvents was tested in-vitro on DPPH free radicals. The antimicrobial activity of the ethanolic extract and its fractions as well as the isolated compounds were evaluated in-vitro on variable microorganisms. Animal models were used to evaluate the antihyperglycemic and antihyperlipidemic activities of the ethanolic extract along with the isolated compound (3β-O acetyl ursolic acid). RP- HPLC analysis of the phenolics revealed high content of rutin, salicylic and ellagic acids. Six compounds belonging to triterpenes and phenolics were isolated from chloroform and n-butanol fractions namely: ursolic acid, 3β-O-acetyl ursolic acid, ellagic acid, quercetin 3-O-β methyl ether, rutin and apigenin7-O-rutinoside. Ethanolic extract showed the highest DPPH radical scavenger activity compared to other solvents. Ethanolic extract, hexane fraction, ursolic acid, 3β-O acetyl ursolic acid and quercetin 3-O-methyl ether showed variable antimicrobial activity against E. coli, P. aeruginosa, S. aureus, and C. albicans. Administration of the ethanolic extract or 3β-O acetyl ursolic acid orally to the mice reduced blood glucose significantly in a time- and dose-dependent manner. Ethanolic extract significantly reduced LDL-C, VLDL-C, TC and TG and increased HDL-C in rats. Ethanolic extract and 3β-O acetyl ursolic acid reduced in-vitro activity of pancreatic lipase. This study reveals that Crataegus azarolus var. eu- azarolus Maire has the efficiency to control hyperglycemia with its associated complications. This study is the first to evaluate antihyperglycemic and antihyperlipidemic potentials of 3β-O acetyl ursolic acid.

Optical biosensor for environmental on-line monitoring of naphthalene and salicylate bioavailability with an immobilized bioluminescent catabolic reporter bacterium.

PubMed Central

Heitzer, A; Malachowsky, K; Thonnard, J E; Bienkowski, P R; White, D C; Sayler, G S

1994-01-01

An optical whole-cell biosensor based on a genetically engineered bioluminescent catabolic reporter bacterium was developed for continuous on-line monitoring of naphthalene and salicylate bioavailability and microbial catabolic activity potential in waste streams. The bioluminescent reporter bacterium, Pseudomonas fluorescens HK44, carries a transcriptional nahG-luxCDABE fusion for naphthalene and salicylate catabolism. Exposure to either compound resulted in inducible bioluminescence. The reporter culture was immobilized onto the surface of an optical light guide by using strontium alginate. This biosensor probe was then inserted into a measurement cell which simultaneously received the waste stream solution and a maintenance medium. Exposure under defined conditions to both naphthalene and salicylate resulted in a rapid increase in bioluminescence. The magnitude of the response and the response time were concentration dependent. Good reproducibility of the response was observed during repetitive perturbations with either naphthalene or salicylate. Exposure to other compounds, such as glucose and complex nutrient medium or toluene, resulted in either minor bioluminescence increases after significantly longer response times compared with naphthalene or no response, respectively. The environmental utility of the biosensor was tested by using real pollutant mixtures. A specific bioluminescence response was obtained after exposure to either an aqueous solution saturated with JP-4 jet fuel or an aqueous leachate from a manufactured-gas plant soil, since naphthalene was present in both pollutant mixtures. PMID:8017932

Monoterpenes Support Systemic Acquired Resistance within and between Plants.

PubMed

Riedlmeier, Marlies; Ghirardo, Andrea; Wenig, Marion; Knappe, Claudia; Koch, Kerstin; Georgii, Elisabeth; Dey, Sanjukta; Parker, Jane E; Schnitzler, Jörg-Peter; Vlot, A Corina

2017-06-01

This study investigates the role of volatile organic compounds in systemic acquired resistance (SAR), a salicylic acid (SA)-associated, broad-spectrum immune response in systemic, healthy tissues of locally infected plants. Gas chromatography coupled to mass spectrometry analyses of SAR-related emissions of wild-type and non-SAR-signal-producing mutant plants associated SAR with monoterpene emissions. Headspace exposure of Arabidopsis thaliana to a mixture of the bicyclic monoterpenes α-pinene and β-pinene induced defense, accumulation of reactive oxygen species, and expression of SA- and SAR-related genes, including the SAR regulatory AZELAIC ACID INDUCED1 ( AZI1 ) gene and three of its paralogs. Pinene-induced resistance was dependent on SA biosynthesis and signaling and on AZI1 Arabidopsis geranylgeranyl reductase1 mutants with reduced monoterpene biosynthesis were SAR-defective but mounted normal local resistance and methyl salicylate-induced defense responses, suggesting that monoterpenes act in parallel with SA The volatile emissions from SAR signal-emitting plants induced defense in neighboring plants, and this was associated with the presence of α-pinene, β-pinene, and camphene in the emissions of the "sender" plants. Our data suggest that monoterpenes, particularly pinenes, promote SAR, acting through ROS and AZI1 , and likely function as infochemicals in plant-to-plant signaling, thus allowing defense signal propagation between neighboring plants. © 2017 American Society of Plant Biologists. All rights reserved.

Salicylic acid deficiency in NahG transgenic lines and sid2 mutants increases seed yield in the annual plant Arabidopsis thaliana

PubMed Central

Abreu, Maria Elizabeth; Munné-Bosch, Sergi

2009-01-01

Salicylic acid-deficient NahG transgenic lines and sid2 mutants were used to evaluate the role of this compound in the development of the short-lived, annual plant Arabidopsis thaliana, with a particular focus on the interplay between salicylic acid and other phytohormones. Low salicylic acid levels led to increased growth, as well as to smaller abscisic acid levels and reduced damage to PSII (as indicated by Fv/Fm ratios) during the reproductive stages in rosette leaves of NahG transgenic lines and sid2 mutants, compared with wild-type plants. Furthermore, salicylic acid deficiency highly influenced seed yield and composition. Seed production increased by 4.4-fold and 3.5-fold in NahG transgenic lines and sid2 mutants, respectively, compared to the wild type. Salicylic acid deficiency also improved seed composition in terms of antioxidant vitamin concentrations, seeds of salicylic acid-deficient plants showing higher levels of α- and γ-tocopherol (vitamin E) and β-carotene (pro-vitamin A) than seeds of wild-type plants. Seeds of salicylic acid-deficient plants also showed higher nitrogen concentrations than seeds of wild-type plants. It is concluded that (i) the sid2 gene, which encodes for isochorismate synthase, plays a central role in salicylic acid biosynthesis during plant development in A. thaliana, (ii) salicylic acid plays a role in the regulation of growth, senescence, and seed production, (iii) there is a cross-talk between salicylic acid and other phytohormones during plant development, and (iv) the concentrations of antioxidant vitamins in seeds may be influenced by the endogenous levels of salicylic acid in plants. PMID:19188277

The Analysis of Cyanide and Its Breakdown Products in Biological Samples

DTIC Science & Technology

2010-01-01

simultaneous GC-mass spectrometric (MS) analysis of cyanide and thiocyanate, and Funazo et al. (53) quantita- tively methylated cyanide and thiocyanate for...selective membrane electrode for thiocyanate ion based on a bis-taurine- salicylic binuclear copper(II) complex as ionophore. Chinese Journal of Chemistry

Factors Affecting Quality and Health Promoting Compounds during Growth and Postharvest Life of Sweet Cherry (Prunus avium L.)

PubMed Central

Correia, Sofia; Schouten, Rob; Silva, Ana P.; Gonçalves, Berta

2017-01-01

Sweet cherries are attractive fruits due to their taste, color, nutritional value, and beneficial health effects. Sweet cherry is a highly perishable fruit and all quality attributes and the level of health promoting compounds are affected by growth conditions, picking, packing, transport, and storage. During production, the correct combination of scion × rootstock will produce fruits with higher firmness, weight, sugars, vitamins, and phenolic compounds that boost the fruit antioxidant activity. Orchard management, such as applying drip irrigation and summer pruning, will increase fruit sugar levels and total phenolic content, while application of growth regulators can result in improved storability, increased red coloring, increased fruit size, and reduced cracking. Salicylic acid, oxalic acid, acetylsalicylic acid, and methyl salicylate are promising growth regulators as they also increase total phenolics, anthocyanins, and induce higher activity of antioxidant enzymes. These growth regulators are now also applied as fruit coatings that improve shelf-life with higher antioxidant enzyme activities and total phenolics. Optimizing storage and transport conditions, such as hydro cooling with added CaCl2, chain temperature and relative humidity control, are crucial for slowing down decay of quality attributes and increasing the antioxidant capacity. Application of controlled atmosphere during storage is successful in delaying quality attributes, but lowers ascorbic acid levels. The combination of low temperature storage in combination with modified atmosphere packaging (MAP) is successful in reducing the incidence of fruit decay, while preserving taste attributes and stem color with a higher antioxidant capacity. A new trend in MAP is the use of biodegradable films such as micro-perforated polylactic acid film that combine significant retention of quality attributes, high consumer acceptability, and a reduced environmental footprint. Another trend is to replace MAP with fruit edible coatings. Edible coatings, such as various lipid composite coatings, have advantages in retaining quality attributes and increasing the antioxidant activity (chitosan) and are regarded as approved food additives, although studies regarding consumer acceptance are needed. The recent publication of the sweet cherry genome will likely increase the identification of more candidate genes involved in growing and maintaining health related compounds and quality attributes. PMID:29312407

Chemometric profile, antioxidant and tyrosinase inhibitory activity of Camel's foot creeper leaves (Bauhinia vahlii).

PubMed

Panda, Pritipadma; Dash, Priyanka; Ghosh, Goutam

2018-03-01

The present study is the first effort to a comprehensive evaluation of antityrosinase activity and chemometric analysis of Bauhinia vahlii. The experimental results revealed that the methanol extract of Bauhinia vahlii (BVM) possesses higher polyphenolic compounds and total antioxidant activity than those reported elsewhere for other more conventionally and geographically different varieties. The BVM contain saturated fatty acids such as hexadecanoic acid (10.15%), octadecanoic acid (1.97%), oleic acid (0.61%) and cis-vaccenic acid (2.43%) along with vitamin E (12.71%), α-amyrin (9.84%), methyl salicylate (2.39%) and β-sitosterol (17.35%), which were mainly responsible for antioxidant as well as tyrosinase inhibitory activity. Tyrosinase inhibitory activity of this extract was comparable to that of Kojic acid. These findings suggested that the B. vahlii leaves could be exploited as potential source of natural antioxidant and tyrosinase inhibitory agent, as well.

Fragrances as new contaminants in the Venice lagoon.

PubMed

Vecchiato, Marco; Cremonese, Simone; Gregoris, Elena; Barbaro, Elena; Gambaro, Andrea; Barbante, Carlo

2016-10-01

Fragrance Materials (FMs) are omnipresent components of household and Personal Care Products (PCPs). In spite of their widespread use, little is known about their environmental occurrence. We selected 17 among the longest-lasting and most stable fragrance ingredients that are commercially available, namely: Amberketal, Ambrofix, Amyl Salicylate, Benzyl Salicylate, Bourgeonal, Dupical, Hexyl Salicylate, Isobutavan, Lemonile, Mefranal, Myraldene, Okoumal, Oranger Crystals, Pelargene, Peonile, Tridecene-2-Nitrile, Ultravanil. A new analytical method was developed to quantify FMs in water samples and it was applied to perform the first study about the distribution of these compounds in the surface waters of the city of Venice and its lagoon. Total FMs concentrations range from about 30ngL(-1) to more than 10μgL(-1) in polluted canals during the low tide. Sewage discharges were supposed to be the main sources of the selected FMs in the environment. Salicylates, oestrogenic and allergenic compounds, were in general the most abundant and widespread components. This study reports for the first time the detection of most of the selected FMs in surface waters and represent the first step to understand their environmental fate. Copyright © 2016 Elsevier B.V. All rights reserved.

Interactive Effects of Jasmonic Acid, Salicylic Acid, and Gibberellin on Induction of Trichomes in Arabidopsis1

PubMed Central

Traw, M. Brian; Bergelson, Joy

2003-01-01

Leaf trichomes protect plants from attack by insect herbivores and are often induced following damage. Hormonal regulation of this plant induction response has not been previously studied. In a series of experiments, we addressed the effects of artificial damage, jasmonic acid, salicylic acid, and gibberellin on induction of trichomes in Arabidopsis. Artificial damage and jasmonic acid caused significant increases in trichome production of leaves. The jar1-1 mutant exhibited normal trichome induction following treatment with jasmonic acid, suggesting that adenylation of jasmonic acid is not necessary. Salicylic acid had a negative effect on trichome production and consistently reduced the effect of jasmonic acid, suggesting negative cross-talk between the jasmonate and salicylate-dependent defense pathways. Interestingly, the effect of salicylic acid persisted in the nim1-1 mutant, suggesting that the Npr1/Nim1 gene is not downstream of salicylic acid in the negative regulation of trichome production. Last, we found that gibberellin and jasmonic acid had a synergistic effect on the induction of trichomes, suggesting important interactions between these two compounds. PMID:14551332

TSCA Environmental Release Application (TERA) for Pseudomonas fluorescens strains HK44 and 5RL

EPA Pesticide Factsheets

TERAs submitted by the University of Tennessee and Micro Systems Technologies, LLC and given the tracking designation of R-04-01 and R-04-02. The strain will be tested to examine its ability to detect and monitor naphthalene and methyl salicylate.

Attraction of Plecia nearctica (dipter:bibionidae) to floral lures containing phenylacetaldehyde

USDA-ARS?s Scientific Manuscript database

We observed that the floral odorant, phenylacetaldehyde (PAA), was attractive to both sexes of adult lovebugs (Plecia nearctica, Diptera: Bibionidae) in central and southern Florida. The addition of ß-myrcene and methyl salicylate to PAA did not improve the numbers of P. nearctica caught in delta tr...

Exogenous Methyl Jasmonate and Salicylic Acid Induce Subspecies-Specific Patterns of Glucosinolate Accumulation and Gene Expression in Brassica oleracea L.

PubMed

Yi, Go-Eun; Robin, Arif Hasan Khan; Yang, Kiwoung; Park, Jong-In; Hwang, Byung Ho; Nou, Ill-Sup

2016-10-24

Glucosinolates have anti-carcinogenic properties. In the recent decades, the genetics of glucosinolate biosynthesis has been widely studied, however, the expression of specific genes involved in glucosinolate biosynthesis under exogenous phytohormone treatment has not been explored at the subspecies level in Brassica oleracea . Such data are vital for strategies aimed at selective exploitation of glucosinolate profiles. This study quantified the expression of 38 glucosinolate biosynthesis-related genes in three B. oleracea subspecies, namely cabbage, broccoli and kale, and catalogued associations between gene expression and increased contents of individual glucosinolates under methyl jasmonate (MeJA) and salicylic acid (SA) treatments. Glucosinolate accumulation and gene expression in response to phytohormone elicitation was subspecies specific. For instance, cabbage leaves showed enhanced accumulation of the aliphatic glucoiberin, progoitrin, sinigrin and indolic neoglucobrassicin under both MeJA and SA treatment. MeJA treatment induced strikingly higher accumulation of glucobrassicin (GBS) in cabbage and kale and of neoglucobrassicin (NGBS) in broccoli compared to controls. Notably higher expression of ST5a (Bol026200), CYP81F1 (Bol028913, Bol028914) and CYP81F4 genes was associated with significantly higher GBS accumulation under MeJA treatment compared to controls in all three subspecies. CYP81F4 genes, trans-activated by MYB34 genes, were expressed at remarkably high levels in all three subspecies under MeJA treatment, which also induced in higher indolic NGBS accumulation in all three subspecies. Remarkably higher expression of MYB28 (Bol036286), ST5b , ST5c , AOP2 , FMOGS-OX5 (Bol031350) and GSL-OH (Bol033373) was associated with much higher contents of aliphatic glucosinolates in kale leaves compared to the other two subspecies. The genes expressed highly could be utilized in strategies to selectively increase glucosinolate compounds in B. oleracea subspecies. These results promote efforts to develop genotypes of B. oleracea and other species with enhanced levels of desired glucosinolates.

Vitex negundo inhibits cyclooxygenase-2 inflammatory cytokine-mediated inflammation on carrageenan-induced rat hind paw edema

PubMed Central

Chattopadhyay, Pronobesh; Hazarika, Soilyadhar; Dhiman, Sunil; Upadhyay, Aadesh; Pandey, Anurag; Karmakar, Sanjeev; Singh, Lokendra

2012-01-01

Background: Vitex negundo L. (Verbenaceae) is a hardy plant widely distributed in the Indian subcontinent and used for treatment of a wide spectrum of health disorders in traditional and folk medicine, some of which have been experimentally validated. In present study, we aimed to investigate the anti-inflammatory effects of V. negundo in carrageenan-induced paw edema in rats, and to investigate the probable mechanism of anti-inflammatory action. Materials and Methods: Paw edema was produced by injecting 1% solution of carrageenan, and the paw volume was measured before and after carrageenan injection up to 5 h. V. negundo leaf oil was extracted using a Clevenger apparatus and administered by a trans-dermal route to Wistar rats and the percentage of inhibition of inflammation was observed using a Plethysmometer by comparing a compound aerosol-based formulation with 1 mg diclofinac diethylamine BP and 7 mg methyl salicylate IP/kg body weight served as a standard drug whereas paraffin oil served as the placebo group. After withdrawing of blood, serum was separated and cyclooxygenase (COX)-1 and COX-2 inhibitory activities were measured by the enzyme immuno assay (EIA) method by using a COX inhibitor screening assay kit. Results and Discussion: V. negundo leaf oil significantly (P < 0.05) reduced the carrageenan-induced paw edema as compared to the placebo group (paraffin oil) and 1 mg diclofinac diethylamine BP and 7 mg methyl salicylate IP showed the maximum inhibition of paw edema as compared to the V. negundo leaf oil treated group and the control group. Also in the present study V. negundo leaf oil showed significantly (P < 0.05) inhibits COX-1 pathways rather than COX-2 pathways as compared to the V. negundo leaf oil treated group. Conclusion: It is suggested that the V. negundo leaf oil is a potent anti-inflammatory agent and acts via inhibition of COX-2 without much interfering COX-1 pathways. PMID:22923950

Increase of Chamazulene and α-Bisabolol Contents of the Essential Oil of German Chamomile (Matricaria chamomila L.) Using Salicylic Acid Treatments under Normal and Heat Stress Conditions

PubMed Central

Ghasemi, Mojtaba; Babaeian Jelodar, Nadali; Modarresi, Mohammad; Bagheri, Nadali; Jamali, Abbas

2016-01-01

The chamazulene and α-(−)-bisabolol contents and quality of the chamomile oil are affected by genetic background and environmental conditions. Salicylic acid (SA), as a signaling molecule, plays a significant role in the plant physiological processes. The aim of this study was to evaluate the chemical profile, quantity, and improve the essential oil quality as a consequence of the increase of chamazulene and α-(−)-bisabol using salicylic acid under normal and heat stress conditions by the gas chromatography-mass spectrometry (GC-MS) technique. The factorial experiments were carried out during the 2011–2012 hot season using a randomized complete block design with three replications. The factors include four salicylic acid concentrations (0 (control), 10, 25 and 100 mg·L−1), and three chamomile cultivars (Bushehr, Bona, Bodegold) were sown on two different planting dates under field conditions. Fourteen compounds were identified from the extracted oil of the samples treated with salicylic acid under normal and heat stress conditions. The major identified oil compositions from chamomile cultivars treated with salicylic acid were chamazulene, α-(−)-bisabolol, bisabolone oxide, β-farnesene, en-yn-dicycloether, and bisabolol oxide A and B. Analysis of variance showed that the simple effects (environmental conditions, cultivar and salicylic acid) and their interaction were significant on all identified compounds, but the environmental conditions had no significant effect on bisabolol oxide A. The greatest amount of chamazulene obtained was 6.66% at the concentration of 10 mg·L−1 SA for the Bona cultivar under heat stress conditions, whereas the highest α-(−)-bisabolol amount attained was 3.41% at the concentration of 100 mg·L−1 SA for the Bona cultivar under normal conditions. The results demonstrated that the application of exogenous salicylic acid increases the quantity and essential oil quality as a consequence of the increase of chamazulene and α-(−)-bisabolol under normal and heat stress conditions. PMID:28231151

Interaction of Salicylate and a Terpenoid Plant Extract with Model Membranes: Reconciling Experiments and Simulations

PubMed Central

Khandelia, Himanshu; Witzke, Sarah; Mouritsen, Ole G.

2010-01-01

We investigate the effects of two structurally similar small cyclic molecules: salicylic acid and perillic acid on a zwitterionic model lipid bilayer, and show that both molecules might have biological activity related to membrane thinning. Salicylic acid is a nonsteroidal antiinflammatory drug, some of the pharmacological properties of which arise from its interaction with the lipid bilayer component of the plasma membrane. Prior simulations show that salicylate orders zwitterionic lipid membranes. However, this is in conflict with Raman scattering and vesicle fluctuation analysis data, which suggest the opposite. We show using extensive molecular dynamics simulations, cumulatively >2.5 μs, that salicylic acid indeed disorders membranes with concomitant membrane thinning and that the conflict arose because prior simulations suffered from artifacts related to the sodium-ion induced condensation of zwitterionic lipids modeled by the Berger force field. Perillic acid is a terpenoid plant extract that has antiinfective and anticancer properties, and is extensively used in eastern medicine. We found that perillic acid causes large-scale membrane thinning and could therefore exert its antimicrobial properties via a membrane-lytic mechanism reminiscent of antimicrobial peptides. Being more amphipathic, perillic acid is more potent in disrupting lipid headgroup packing, and significantly modifies headgroup dipole orientation. Like salicylate, the membrane thinning effect of perillic acid is masked by the presence of sodium ions. As an alternative to sodium cations, we advocate the straightforward solution of using larger countercations like potassium or tetra-methyl-ammonium that will maintain electroneutrality but not interact strongly with, and thus not condense, the lipid bilayer. PMID:21156130

Percutaneous penetration, melanin activation and toxicity evaluation of a phytotherapic formulation for vitiligo therapeutic.

PubMed

Truite, Cecília Valente Rodrigues; Philippsen, Gisele Strieder; Ueda-Nakamura, Tânia; Natali, Maria Raquel Marçal; Dias Filho, Benedito Prado; Bento, Antonio Carlos; Baesso, Mauro Luciano; Nakamura, Celso Vataru

2007-01-01

The aim of this work was to apply photoacoustic spectroscopy for the ex vivo determination of the penetration rate of a phytotherapic formulation for vitiligo therapeutic, with or without salicylic acid as the promoter agent. In addition, the compound toxicity and morphophysiology effects were evaluated for different concentrations of salicylic acid. The experiments were performed as a function of the period of time of treatment in a well-controlled group of rabbits. Toxic effects were not observed with any of the tested products. All formulations containing salicylic acid induced cutaneous reaction which was dose dependent. The histological analysis showed that the use of the medication was associated with an increased comedogenic effect in relation to the control group, regardless of salicylic acid concentration. Inflammatory reactions and acanthosis were observed only in the animals treated with formulations containing higher concentrations of salicylic acid, while none of these effects were detected with the use of the formulation containing 2.5% (wt/vol) of salicylic acid. Photoacoustic depth monitoring showed that both formulations, with or without salicylic acid, propagated through the skin up to the melanocytes region, suggesting that the transport of the active agent may occur through the epithelial structure without the need of using queratinolitic substances, which are known to induce side effects in the animals.

Salicylyl Fluorene Derivatives as Fluorescent Sensors for Cu(II) Ions.

PubMed

Khaokeaw, Chenwit; Sukwattanasinitt, Mongkol; Rashatasakhon, Paitoon

2016-03-01

Two derivatives of fluorene containing salicylic acid groups are successfully synthesized by palladium-catalyzed coupling reactions and subsequent hydrolysis of salicylate esters. The compounds are characterized by various spectroscopic methods. In phosphate buffer (pH 8.0) solutions, these compounds are well soluble. They show maximum absorption wavelengths in the range of 304-330 nm and exhibit maximum emission wavelength around 420 and 430 nm with the quantum yields of 2.7 and 4.4 %, respectively. The compound with alkynyl salicylate groups (2) exhibits a selective fluorescence quenching towards Cu(II) and Fe(II) with a relatively similar sensitivity. The selectivity favoring Cu(II) over Fe(II) and other metal ions can be achieved upon the addition of 30 μM Triton X-100. The Cu(II) detection limit in solution phase is 1.47 ppb. The fluorescence signal recovery upon the addition of EDTA indicate a reversible complexation between 2 and Cu(II) ion. Fabrication of 2 on filter paper using a 50 μM solution in THF affords a naked-eye detection for Cu(II) and Fe(II) in aqueous media at picomole level.

An improvement of LLNA:DA to assess the skin sensitization potential of chemicals.

PubMed

Zhang, Hongwei; Shi, Ying; Wang, Chao; Zhao, Kangfeng; Zhang, Shaoping; Wei, Lan; Dong, Li; Gu, Wen; Xu, Yongjun; Ruan, Hongjie; Zhi, Hong; Yang, Xiaoyan

2017-01-01

We developed a modified local lymph node assay based on ATP (LLNA:DA), termed the Two-Stage LLNA:DA, to further reduce the animal numbers in the identification of sensitizers. In the Two-Stage LLNA:DA procedure, 13 chemicals ranging from non-sensitizers to extreme sensitizers were selected. The first stage used reduced LLNA:DA (rLLNA:DA) to screen out sensitive chemicals. The second stage used LLNA:DA based on OECD 442 (A) to classify those potential sensitizers screened out in the first stage. In the first stage, the SIs of the methyl methacrylate, salicylic acid, methyl salicylate, ethyl salicylate, isopropanol and propanediol were below 1.8 and need not to be tested in the second step. Others continued to be tested by LLNA:DA. In the second stage, sodium lauryl sulphate and xylene were classified as weak sensitizers. a-hexyl cinnamic aldehyde and eugenol were moderate sensitizers. Benzalkonium chloride and glyoxal were strong sensitizers, and phthalic anhydride was an extreme sensitizer. The 9/9, 11/12, 10/11, and 8/13 (positive or negative only) categories of the Two-Stage LLNA:DA were consistent with those from the other methods (LLNA, LLNA:DA, GPMT/BT and HMT/HPTA), suggesting that Two-Stage LLNA:DA have a high coincidence rate with reported data. In conclusion, The Two-Stage LLNA:DA is in line with the "3R" rules, and can be a modification of LLNA:DA but needs more study.

DFT studies of the vibrational spectra of salicylic acid and related compounds

USDA-ARS?s Scientific Manuscript database

Compounds that exhibit intra- and intermolecular hydrogen bonds can have infrared and Raman spectra that show evidences of these hydrogen bonds. In modeling the vibrational spectra of such compounds, the addition of explicit hydrogen bonding species (e.g. solvent molecules) can often improve agreeme...

Mercury photolytic transformation affected by low-molecular-weight natural organics in water.

PubMed

He, Feng; Zheng, Wang; Liang, Liyuan; Gu, Baohua

2012-02-01

Mechanisms by which dissolved organic matter (DOM) mediates the photochemical reduction of Hg(II) in aquatic ecosystems are not fully understood, owing to the heterogeneous nature and complex structural properties of DOM. In this work, naturally occurring aromatic compounds including salicylic, 4-hydrobenzoic, anthranilic, 4-aminobenzoic, and phthalic acid were systematically studied as surrogates for DOM in order to gain an improved mechanistic understanding of these compounds in the photoreduction of Hg(II) in water. We show that the photoreduction rates of Hg(II) are influenced not only by the substituent functional groups such as -OH, -NH(2) and -COOH on the benzene ring, but also the positioning of these functional groups on the ring structure. The Hg(II) photoreduction rate decreases in the order anthranilic acid>salicylic acid>phthalic acid according to the presence of the -NH(2), -OH, -COOH functional groups on benzoic acid. The substitution position of the functional groups affects reduction rates in the order anthranilic acid>4-aminobenzoic acid and salicylic acid>4-hydroxybenzoic acid. Reduction rates correlate strongly with ultraviolet (UV) absorption of these compounds and their concentrations, suggesting that the formation of organic free radicals during photolysis of these compounds is responsible for Hg(II) photoreduction. These results provide insight into the role of low-molecular-weight organic compounds and possibly DOM in Hg photoredox transformation and may thus have important implications for understanding Hg geochemical cycling in the environment. Copyright © 2011 Elsevier B.V. All rights reserved.

Bioinspired Surface Treatments for Improved Decontamination: Commercial Products

DTIC Science & Technology

2017-07-28

simulants paraoxon, methyl salicylate, dimethyl methylphosphate, and diisopropyl fluorophosphates following treatment of contaminated surfaces with a...treatment of contaminated surfaces with a soapy water solution is reported along with droplet diffusion on the surfaces and wetting angles...Defense Program (CBDP) seeks to provide protection of forces in a contaminated environment including contamination avoidance, individual protection

Preparation of Oil of Wintergreen from Commercial Aspirin Tablets: A Microscale Experiment Highlighting Acyl Substitutions

ERIC Educational Resources Information Center

Hartel, Aaron M.; Hanna, James M., Jr.

2009-01-01

A single-pot procedure for the preparation of methyl salicylate (oil of wintergreen) from commercial aspirin tablets has been developed. The synthesis proceeds via a tandem transesterification-Fischer esterification using acidic methanol and can be carried out using either conventional or microwave heating. The experiment helps demonstrate acyl…

Efficacy of scalp hair decontamination following exposure to vapours of sulphur mustard simulants 2-chloroethyl ethyl sulphide and methyl salicylate.

PubMed

Spiandore, Marie; Piram, Anne; Lacoste, Alexandre; Prevost, Philippe; Maloni, Pascal; Torre, Franck; Asia, Laurence; Josse, Denis; Doumenq, Pierre

2017-04-01

Chemical warfare agents are an actual threat and victims' decontamination is a main concern when mass exposure occurs. Skin decontamination with current protocols has been widely documented, as well as surface decontamination. However, considering hair ability to trap chemicals in vapour phase, we investigated hair decontamination after exposure to sulphur mustard simulants methyl salicylate and 2-chloroethyl ethyl sulphide. Four decontamination protocols were tested on hair, combining showering and emergency decontamination (use of Fuller's earth or Reactive Skin Decontamination Lotion RSDL ® ). Both simulants were recovered from hair after treatment, but contents were significantly reduced (42-85% content allowance). Showering alone was the least efficient protocol. Concerning 2-chloroethyl ethyl sulphide, protocols did not display significant differences in decontamination efficacy. For MeS, use of emergency decontaminants significantly increased showering efficacy (10-20% rise), underlining their usefulness before thorough decontamination. Our results highlighted the need to extensively decontaminate hair after chemical exposure. Residual amounts after decontamination are challenging, as their release from hair could lead to health issues. Copyright © 2016. Published by Elsevier B.V.

Postharvest biology and technology of pomegranate.

PubMed

Pareek, Sunil; Valero, Daniel; Serrano, María

2015-09-01

Pomegranate is a subtropical and tropical fruit of great importance from a health point of view. Despite increasing consumer awareness of the health benefits of pomegranate, consumption of the fruit is still limited owing to poor postharvest handling, storage recommendations, short shelf life and quality deterioration during transportation, storage and marketing. The occurrence of physiological disorders such as husk scald, splitting and chilling injury is another challenge reducing marketability and consumer acceptance. Recently, notable work on postharvest biology and technology has been done. Pomegranate is highly sensitive to low-oxygen (<5 kPa) atmospheres, chilling injury and decay. One of the major problems associated with pomegranate fruit is excessive weight loss, which may result in hardening of the husk and browning of the rind and arils. To reduce chilling injury incidence and to extend storability and marketing of pomegranates, good results were obtained with polyamine, heat, salicylic acid, methyl jasmonate or methyl salicylate treatments prior to cold storage. This article reviews the maturity indices, changes during maturation and ripening, postharvest physiology and technology of pomegranate fruit as well as the various postharvest treatments for maintaining fruit quality. © 2015 Society of Chemical Industry.

A NAD(P) reductase like protein is the salicylic acid receptor in the appendix of the Sauromatum guttatum inflorescence

PubMed Central

Skubatz, Hanna; Orellana, Mónica V; Howald, William N

2013-01-01

The mode of action of the thermogenic inducers (salicylic acid, aspirin, and 2,6-dihydroxybenzoic acid) in the appendix of the Sauromatum guttatum inflorescence is poorly understood. Using ESI-MS and light scattering analysis, we have demonstrated that NAD(P) reductase like protein (RL) is the salicylic acid receptor in the Sauromatum appendix. RL was self-assembled in water into a large unit with a hydrodynamic diameter of 800 nm. In the presence of 1 pM salicylic acid, RL exhibited discontinuous and reversible volume phase transitions. The volume phase changed from 800 to 300 nm diameter and vice versa. RL stayed at each volume phase for ~4–5 min with a fast relaxation time between the 2 phases. ESI-MS analysis of RL extracted from appendices treated with salicylic acid, aspirin, and 2,6-DHBA at a micromolar range demonstrated that these compounds are capable of inducing graded conformational changes that are concentration-dependent. A strong correlation between RL conformations and heat-production induced by salicylic acid was also observed. These preliminary findings reveal structural and conformational roles for RL by which plants regulate their temperature and synchronize their time keeping mechanisms. PMID:28516022

Human GAPDH Is a Target of Aspirin’s Primary Metabolite Salicylic Acid and Its Derivatives

PubMed Central

Manohar, Murli; Harraz, Maged M.; Park, Sang-Wook; Schroeder, Frank C.; Snyder, Solomon H.; Klessig, Daniel F.

2015-01-01

The plant hormone salicylic acid (SA) controls several physiological processes and is a key regulator of multiple levels of plant immunity. To decipher the mechanisms through which SA’s multiple physiological effects are mediated, particularly in immunity, two high-throughput screens were developed to identify SA-binding proteins (SABPs). Glyceraldehyde 3-Phosphate Dehydrogenase (GAPDH) from plants (Arabidopsis thaliana) was identified in these screens. Similar screens and subsequent analyses using SA analogs, in conjunction with either a photoaffinity labeling technique or surface plasmon resonance-based technology, established that human GAPDH (HsGAPDH) also binds SA. In addition to its central role in glycolysis, HsGAPDH participates in several pathological processes, including viral replication and neuronal cell death. The anti-Parkinson’s drug deprenyl has been shown to suppress nuclear translocation of HsGAPDH, an early step in cell death and the resulting cell death induced by the DNA alkylating agent N-methyl-N’-nitro-N-nitrosoguanidine. Here, we demonstrate that SA, which is the primary metabolite of aspirin (acetyl SA) and is likely responsible for many of its pharmacological effects, also suppresses nuclear translocation of HsGAPDH and cell death. Analysis of two synthetic SA derivatives and two classes of compounds from the Chinese medicinal herb Glycyrrhiza foetida (licorice), glycyrrhizin and the SA-derivatives amorfrutins, revealed that they not only appear to bind HsGAPDH more tightly than SA, but also exhibit a greater ability to suppress translocation of HsGAPDH to the nucleus and cell death. PMID:26606248

Fragmentation of molecular ions in differential mobility spectrometry as a method for identification of chemical warfare agents.

PubMed

Maziejuk, M; Puton, J; Szyposzyńska, M; Witkiewicz, Z

2015-11-01

The subject of the work is the use of differential mobility spectrometry (DMS) for the detection of chemical warfare agents (CWA). Studies were performed for mustard gas, i.e., bis(2-chloroethyl)sulfide (HD), sarin, i.e., O-isopropyl methylphosphonofluoridate (GB) and methyl salicylate (MS) used as test compounds. Measurements were conducted with two ceramic DMS analyzers of different constructions allowing the generation of an electric field with an intensity of more than 120 Td. Detector signals were measured for positive and negative modes of operation in a temperature range from 0 to 80 °C. Fragmentations of ions containing analyte molecules were observed for all tested compounds. The effective temperatures of fragmentation estimated on the basis of dispersion plots were equal from about 148 °C for GB to 178 °C for MS. It was found that values of separation voltage (SV) and compensation voltage (CV) at which the fragmentation of sample ions is observed may be the parameters improving the certainty of detection for different analytes. The DMS analyzers enabling the observation of ion fragmentation can be successfully used for effective CWA detection. Copyright © 2015. Published by Elsevier B.V.

Dual actions of a novel bifunctional compound to lower glucose in mice with diet-induced insulin resistance

PubMed Central

Chen, Katherine; Jih, Alice; Kavaler, Sarah T.; Lagakos, William S.; Oh, Dayoung; Watkins, Steven M.

2015-01-01

Docosahexaenoic acid (DHA 22:6n-3) and salicylate are both known to exert anti-inflammatory effects. This study investigated the effects of a novel bifunctional drug compound consisting of DHA and salicylate linked together by a small molecule that is stable in plasma but hydrolyzed in the cytoplasm. The components of the bifunctional compound acted synergistically to reduce inflammation mediated via nuclear factor κB in cultured macrophages. Notably, oral administration of the bifunctional compound acted in two distinct ways to mitigate hyperglycemia in high-fat diet-induced insulin resistance. In mice with diet-induced obesity, the compound lowered blood glucose by reducing hepatic insulin resistance. It also had an immediate glucose-lowering effect that was secondary to enhanced glucagon-like peptide-1 (GLP-1) secretion and abrogated by the administration of exendin(9–39), a GLP-1 receptor antagonist. These results suggest that the bifunctional compound could be an effective treatment for individuals with type 2 diabetes and insulin resistance. This strategy could also be employed in other disease conditions characterized by chronic inflammation. PMID:26058862

Expression of Immediate-Early Genes in the Inferior Colliculus and Auditory Cortex in Salicylate-Induced Tinnitus in Rat

PubMed Central

Hu, S.S.; Mei, L.; Chen, J.Y.; Huang, Z.W.; Wu, H.

2014-01-01

Tinnitus could be associated with neuronal hyperactivity in the auditory center. As a neuronal activity marker, immediate-early gene (IEG) expression is considered part of a general neuronal response to natural stimuli. Some IEGs, especially the activity-dependent cytoskeletal protein (Arc) and the early growth response gene-1 (Egr-1), appear to be highly correlated with sensory-evoked neuronal activity. We hypothesize, therefore, an increase of Arc and Egr-1 will be observed in a tinnitus model. In our study, we used the gap prepulse inhibition of acoustic startle (GPIAS) paradigm to confirm that salicylate induces tinnitus-like behavior in rats. However, expression of the Arc gene and Egr-1 gene were decreased in the inferior colliculus (IC) and auditory cortex (AC), in contradiction of our hypothesis. Expression of N-methyl D-aspartate receptor subunit 2B (NR2B) was increased and all of these changes returned to normal 14 days after treatment with salicylate ceased. These data revealed long-time administration of salicylate induced tinnitus markedly but reversibly and caused neural plasticity changes in the IC and the AC. Decreased expression of Arc and Egr-1 might be involved with instability of synaptic plasticity in tinnitus. PMID:24704997

Charging Effects on Fluid Stream Droplets for Momentum Exchange Between Spacecraft

DTIC Science & Technology

2009-01-01

DC705 have similar density; 1070 kg/m 3 for DC704 and 1097 kg/m 3 for DC705. The fluids differ chemically by a single methyl group, which is replaced...measured as a function of photon energy. The relative light intensity was monitored by the fluorescence of Sodium Salicylate . Division of the current by

Liquid Droplet Thrusters to Provide Constant Momentum Exchange Between Formation Flying Spacecraft

DTIC Science & Technology

2010-03-01

density; 1070 kg/m3 for DC704 and 1097 kg/m3 for DC705. The fluids differ chemically by a single methyl group, which is replaced by a fifth Benzene...of photon energy. The relative light intensity was monitored by the fluorescence of Sodium Salicylate . Division of the current by the intensity of

Olfactoryresponse of the predatory mite Typhlodromus pyri (Acari: Phytoseiidae) to methyl salicylate in laboratory bioassays

USDA-ARS?s Scientific Manuscript database

The response of Typhlodromus pyri, a key predator of grapevine rust mite (Calepitrimerus vitis), to MeSA was tested using a Y-tube olfactometer in laboratory bioassays. Six doses ranging from 200 to 0.002 µg of diluted MeSA were tested. Significantly higher proportions of T. pyri preferred MeSA at ...

Effect of foliar application of chitosan and salicylic acid on the growth of soybean (Glycine max (L.) Merr.) varieties

NASA Astrophysics Data System (ADS)

Hasanah, Y.; Sembiring, M.

2018-02-01

Elicitors such as chitosan and salicylic acid could be used not only to increase isoflavone concentration of soybean seeds, but also to increase the growth and seed yield. The objective of the present study was to determine the effects of foliar application of elicitor compounds (i.e. chitosan, and salicylic acid)on the growth of two soybean varieties under dry land conditions. Experimental design was a randomized block design with 2 factors and 3 replications. The first factor was soybean varieties (Wilis and Devon). The second factor was foliar application of elicitors consisted of without elicitor; chitosan at V4 (four trifoliate leaves are fully developed); chitosan at R3 (early podding); chitosan at V4 and R3; salicylic acid at V4; salicylic acid at R3 and salicylic acid at V4 and R3. Parameters observed was plant height at 2-7 week after planting (WAP), shoot dry weight and root dry weight. The results suggest that the Wilis variety had higher plant height 7 WAP than Devon. The foliar application of chitosan increased the plant height at 7 WAP, shoot dry weight and root dry weight. The foliar application of chitosan at V4 and R3 on Devon variety increased shoot dry weight.

Non-invasive method for quantitative evaluation of exogenous compound deposition on skin.

PubMed

Stamatas, Georgios N; Wu, Jeff; Kollias, Nikiforos

2002-02-01

Topical application of active compounds on skin is common to both pharmaceutical and cosmetic industries. Quantification of the concentration of a compound deposited on the skin is important in determining the optimum formulation to deliver the pharmaceutical or cosmetic benefit. The most commonly used techniques to date are either invasive or not easily reproducible. In this study, we have developed a noninvasive alternative to these techniques based on spectrofluorimetry. A mathematical model based on diffusion approximation theory is utilized to correct fluorescence measurements for the attenuation caused by endogenous skin chromophore absorption. The limitation is that the compound of interest has to be either fluorescent itself or fluorescently labeled. We used the method to detect topically applied salicylic acid. Based on the mathematical model a calibration curve was constructed that is independent of endogenous chromophore concentration. We utilized the method to localize salicylic acid in epidermis and to follow its dynamics over a period of 3 d.

ImprimatinC1, a novel plant immune-priming compound, functions as a partial agonist of salicylic acid

PubMed Central

Noutoshi, Yoshiteru; Jikumaru, Yusuke; Kamiya, Yuji; Shirasu, Ken

2012-01-01

Plant activators are agrochemicals that protect crops from pathogens. They confer durable resistance to a broad range of diseases by activating intrinsic immune mechanisms in plants. To obtain leads regarding useful compounds, we have screened a chemical library using an established method that allows selective identification of immune-priming compounds. Here, we report the characterisation of one of the isolated chemicals, imprimatinC1, and its structural derivative imprimatinC2. ImprimatinC1 functions as a weak analogue of salicylic acid (SA) and activates the expression of defence-related genes. However, it lacks antagonistic activity toward jasmonic acid. Structure-activity relationship analysis suggests that imprimatinC1 and C2 can be metabolised to 4-chlorobenzoic acid and 3,4-chlorobenzoic acid, respectively, to function in Arabidopsis. We also found that imprimatinC1 and C2 and their potential functional metabolites acted as partial agonists of SA. Thus, imprimatinC compounds could be useful tools for dissecting SA-dependent signal transduction pathways. PMID:23050089

Design, synthesis, and anti-inflammatory activity of caffeoyl salicylate analogs as NO production inhibitors.

PubMed

Yu, Pan; Xia, Chao-Jie; Li, Dong-Dong; Ni, Jun-Jun; Zhao, Lin-Guo; Ding, Gang; Wang, Zhen-Zhong; Xiao, Wei

2018-05-28

Chlorogenic acid (CGA) has been reported to exhibit potent anti-inflammatory activity. However, the development of anti-inflammatory agent based on CGA has not been investigated. In this paper, a series of caffeoyl salicylate compounds derived from CGA were designed, synthesized, and evaluated by LPS-induced nitric oxide synthase inhibition and QRT-PCR technique. Most compounds showed modest activity to inhibit production of nitric oxide (NO) in RAW 264.7 cells induced by lipopolysaccharides (LPS). Among these compounds, QRT-PCR and western blotting results indicated that compounds 6b, 6c, 6f, 6g and D104 that possess 5-member ring or 6-member ring caused a significant inhibition against expression of the iNOS2 in LPS-induced macrophages. In addition, cytotoxic assay displayed most derivatives have good safety in vitro. This new promising scaffold could be further exploited for the development of anti-inflammatory agent in the future. Copyright © 2017. Published by Elsevier B.V.

ImprimatinC1, a novel plant immune-priming compound, functions as a partial agonist of salicylic acid.

PubMed

Noutoshi, Yoshiteru; Jikumaru, Yusuke; Kamiya, Yuji; Shirasu, Ken

2012-01-01

Plant activators are agrochemicals that protect crops from pathogens. They confer durable resistance to a broad range of diseases by activating intrinsic immune mechanisms in plants. To obtain leads regarding useful compounds, we have screened a chemical library using an established method that allows selective identification of immune-priming compounds. Here, we report the characterisation of one of the isolated chemicals, imprimatinC1, and its structural derivative imprimatinC2. ImprimatinC1 functions as a weak analogue of salicylic acid (SA) and activates the expression of defence-related genes. However, it lacks antagonistic activity toward jasmonic acid. Structure-activity relationship analysis suggests that imprimatinC1 and C2 can be metabolised to 4-chlorobenzoic acid and 3,4-chlorobenzoic acid, respectively, to function in Arabidopsis. We also found that imprimatinC1 and C2 and their potential functional metabolites acted as partial agonists of SA. Thus, imprimatinC compounds could be useful tools for dissecting SA-dependent signal transduction pathways.

Electroantennographic and behavioral responses of the sphinx moth Manduca sexta to host plant headspace volatiles.

PubMed

Fraser, Ann M; Mechaber, Wendy L; Hildebrand, John G

2003-08-01

Coupled gas chromatography with electroantennographic detection (GC-EAD) using antennae of adult female Manduca sexta was employed to screen for olfactory stimulants present in headspace collections from four species of larval host plants belonging to two families: Solanaceae--Lycopersicon esculentum (tomato), Capiscum annuum (bell pepper), and Datura wrightii; and Martyniaceae--Pronboscideaparviflora. Headspace volatiles were collected from undamaged foliage of potted, living plants. GC-EAD revealed 23 EAD-active compounds, of which 15 were identified by GC-mass spectrometry. Identified compounds included aliphatic, aromatic, and terpenoid compounds bearing a range of functional groups. Nine EAD-active compounds were common to all four host plant species: (Z)-3-hexenyl acetate, nonanal, decanal, phenylacetaldehyde, methyl salicylate, benzyl alcohol, geranyl acetone, (E)-nerolidol, and one unidentified compound. Behavioral responses of female moths to an eight-component synthetic blend of selected tomato headspace volatiles were tested in a laboratory wind tunnel. Females were attracted to the blend. A comparison of responses from antennae of males and females to bell pepper headspace volatiles revealed that males responded to the same suite of volatiles as females, except for (Z)-3-hexenyl benzoate. EAD responses of males also were lower for (Z)-and (E)-nerolidol and one unidentified compound. Electroantennogram EAG dose-response curves for the 15 identified EAD-active volatiles were recorded. At the higher test doses (10-100 microg), female antennae yielded larger EAG responses to terpenoids and to aliphatic and aromatic esters. Male antennae did respond to the higher doses of (Z)-3-hexenyl benzoate, indicating that they can detect this compound. On the basis of ubiquity of the EAD-active volatiles identified to date in host plant headspace collections, we suggest that M. sexta uses a suite of volatiles to locate and identify appropriate host plants.

Postharvest treatments with salicylic acid, acetylsalicylic acid or oxalic acid delayed ripening and enhanced bioactive compounds and antioxidant capacity in sweet cherry.

PubMed

Valero, Daniel; Díaz-Mula, Huertas M; Zapata, Pedro Javier; Castillo, Salvador; Guillén, Fabián; Martínez-Romero, Domingo; Serrano, María

2011-05-25

Sweet cherry cultivars ('Cristalina' and 'Prime Giant') harvested at commercial ripening stage were treated with salicylic acid (SA), acetylsalicylic acid (ASA) or oxalic acid (OA) at 1 mM and then stored for 20 days under cold temperature. Results showed that all treatments delayed the postharvest ripening process, manifested by lower acidity, color changes and firmness losses, and maintained quality attributes for longer periods than controls. In addition, total phenolics, anthocyanins and antioxidant activity increased in untreated fruit during the first 10 days of storage and then decreased, while in fruits of all treatments, these parameters increased continuously during storage without significant differences among treatments. Thus, postharvest treatments with natural compounds, such as SA, ASA or OA, could be innovative tools to extend the storability of sweet cherry with higher content of bioactive compounds and antioxidant activity as compared with control fruits.

Analysis of defense signals in Arabidopsis thaliana leaves by ultra-performance liquid chromatography/tandem mass spectrometry: jasmonates, salicylic acid, abscisic acid.

PubMed

Stingl, Nadja; Krischke, Markus; Fekete, Agnes; Mueller, Martin J

2013-01-01

Defense signaling compounds and phytohormones play an essential role in the regulation of plant responses to various environmental abiotic and biotic stresses. Among the most severe stresses are herbivory, pathogen infection, and drought stress. The major hormones involved in the regulation of these responses are 12-oxo-phytodienoic acid (OPDA), the pro-hormone jasmonic acid (JA) and its biologically active isoleucine conjugate (JA-Ile), salicylic acid (SA), and abscisic acid (ABA). These signaling compounds are present and biologically active at very low concentrations from ng/g to μg/g dry weight. Accurate and sensitive quantification of these signals has made a significant contribution to the understanding of plant stress responses. Ultra-performance liquid chromatography (UPLC) coupled with a tandem quadrupole mass spectrometer (MS/MS) has become an essential technique for the analysis and quantification of these compounds.

Biological relevance of volatile organic compounds emitted during the pathogenic interactions between apple plants and Erwinia amylovora.

PubMed

Cellini, Antonio; Buriani, Giampaolo; Rocchi, Lorenzo; Rondelli, Elena; Savioli, Stefano; Rodriguez Estrada, Maria T; Cristescu, Simona M; Costa, Guglielmo; Spinelli, Francesco

2018-01-01

Volatile organic compounds emitted during the infection of apple (Malus pumila var. domestica) plants by Erwinia amylovora or Pseudomonas syringae pv. syringae were studied by gas chromatography-mass spectrometry and proton transfer reaction-mass spectrometry, and used to treat uninfected plants. Infected plants showed a disease-specific emission of volatile organic compounds, including several bio-active compounds, such as hexenal isomers and 2,3-butanediol. Leaf growth promotion and a higher resistance to the pathogen, expressed as a lower bacterial growth and migration in plant tissues, were detected in plants exposed to volatile compounds from E. amylovora-infected plants. Transcriptional analysis revealed the activation of salicylic acid synthesis and signal transduction in healthy plants exposed to volatiles produced by E. amylovora-infected neighbour plants. In contrast, in the same plants, salicylic acid-dependent responses were repressed after infection, whereas oxylipin metabolism was activated. These results clarify some metabolic and ecological aspects of the pathogenic adaptation of E. amylovora to its host. © 2016 BSPP AND JOHN WILEY & SONS LTD.

Monosialotetrahexosylganglioside Inhibits the Expression of p-CREB and NR2B in the Auditory Cortex in Rats with Salicylate-Induced Tinnitus.

PubMed

Song, Rui-Biao; Lou, Wei-Hua

2015-01-01

This study investigated the effects of monosialotetrahexosylganglioside (GM1) on the expression of N-methyl-D-aspartate receptor subunit 2B (NR2B) and phosphorylated (p)-cyclic AMP response element-binding protein (CREB) in the auditory cortex of rats with tinnitus. Tinnitus-like behavior in rats was tested with the gap prepulse inhibition of acoustic startle paradigm. We then investigated the NR2B mRNA and protein and p-CREB protein levels in the auditory cortex of tinnitus rats compared with normal rats. Rats treated for 4 days with salicylate exhibited tinnitus. NR2B mRNA and protein and p-CREB protein levels were upregulated in these animals, with expression returning to normal levels 14 days after cessation of treatment; baseline levels of NR2B and p-CREB were also restored by GM1 administration. These data suggest that chronic salicylate administration induces tinnitus via upregulation of p-CREB and NR2B expression, and that GM1 can potentially be used to treat tinnitus.

Exogenous application of the plant signalers methyl jasmonate & salicylic acid induces changes in volatile emissions from citrus foliage & influences the aggregation behavior of ACP (Diaphorina citri), vector of Huanglongbing

USDA-ARS?s Scientific Manuscript database

Huanglongbing or citrus greening is a destructive disease that threatens citrus production worldwide; it is putatively caused by the phloem-limited bacterium Candidatus Liberibacter asiaticus (Las). Currently the disease is untreatable and control efforts focus on intensive insecticide use to contro...

Fourier transform mid-infrared (MIR) and near-infrared (NIR) spectroscopy for rapid quality assessment of Chinese medicine preparation Honghua Oil.

PubMed

Wu, Yan-Wen; Sun, Su-Qin; Zhou, Qun; Leung, Hei-Wun

2008-02-13

Honghua Oil (HHO), a traditional Chinese medicine (TCM) oil preparation, is a mixture of several plant essential oils. In this text, the extended ranges of Fourier transform mid-infrared (FT-MIR) and near infrared (FT-NIR) were recorded for 48 commercially available HHOs of different batches from nine manufacturers. The qualitative and quantitative analysis of three marker components, alpha-pinene, methyl salicylate and eugenol, in different HHO products were performed rapidly by the two vibrational spectroscopic methods, i.e. MIR with horizontal attenuated total reflection (HATR) accessory and NIR with direct sampling technique, followed by partial least squares (PLS) regression treatment of the set of spectra obtained. The results indicated that it was successful to identify alpha-pinene, methyl salicylate and eugenol in all of the samples by simple inspection of the MIR-HATR spectra. Both PLS models established with MIR-HATR and NIR spectral data using gas chromatography (GC) peak areas as calibration reference showed a good linear correlation for each of all three target substances in HHO samples. The above spectroscopic techniques may be the promising methods for the rapid quality assessment/quality control (QA/QC) of TCM oil preparations.

Methyl salicylate: a reactive chemical warfare agent surrogate to detect reaction with hypochlorite.

PubMed

Salter, W Bruce; Owens, Jeffery R; Wander, Joseph D

2011-11-01

Methyl salicylate (MeS) has a rich history as an inert physical simulant for the chemical warfare agents sulfur mustard and soman, where it is used extensively for liquid- and vapor-permeation testing. Here we demonstrate possible utility of MeS as a reactivity simulant for chlorine-based decontaminants. In these experiments MeS was reacted with sodium hypochlorite varying stoichiometry, temperature, reaction time, and pH. No colored oxidation products were observed; however, chlorination of the aromatic ring occurred ortho (methyl 3-chlorosalicylate) and para (methyl 5-chlorosalicylate) to the position bearing the -OH group in both the mono- and disubstituted forms. The monosubstituted para product accumulated initially, and the ortho and 3,5-dichloro products formed over the next several hours. Yields from reactions conducted below pH 11 declined rapidly with decreasing pH. Reactions run at 40 °C produced predominantly para substitution, while those run at 0 °C produced lower yields of ortho- and para-substituted products. Reactions were also carried out on textile substrates of cotton, 50/50 nylon-cotton, and a meta aramid. The textile data broadly reproduced reaction times and stoichiometry observed in the liquid phase, but are complicated by physical and possibly chemical interactions with the fabric. These data indicate that, for hypochlorite-containing neutralizing agents operating at strongly alkaline pH, one can expect MeS to react stoichiometrically with the hypochlorite it encounters. This suggests utility of MeS in lieu of such highly hazardous surrogates as monochloroalkyl sulfides as a simulant for threat scenarios involving the stoichiometric decomposition of sulfur mustard. Specifically, the extent of coverage of the simulant on a fabric by the neutralizing agent can be directly measured. Similar reactivity toward other halogen oxidizing agents is likely but remains to be demonstrated.

Electroantennogram Responses to Plant Volatiles Associated with Fenvalerate Resistance in the Diamondback Moth, Plutella xylostella (Lepidoptera: Plutellidae).

PubMed

Houjun, Tian; Lin, Shuo; Chen, Yong; Chen, Yixin; Zhao, Jianwei; Gu, Xiaojun; Wei, Hui

2018-05-28

The diamondback moth (DBM), Plutella xylostella (L.) (Lepidoptera: Plutellidae), is the main destructive insect pest of brassica vegetables around the world, and has developed resistance to numerous insecticides. Although host plant volatiles are important in pest control, the mechanism of low-level insecticide resistance in P. xylostella due to plant volatiles has not been examined. Here, electroantennograms (EAGs) were used to compare the responses of adult male and female DBMs of a susceptible strain (S-strain) and a derived resistant strain, Fen-R-strain (6.52-fold more resistant than the S-strain), to different concentrations of nine plant volatiles. We found significantly different relative EAG responses between S-strain and Fen-R-strain males to different concentrations of methyl jasmonate, methyl salicylate, and octanal. The relative EAG responses of S-strain and Fen-R-strain females to different concentrations of β-myrcene, methyl jasmonate, methyl salicylate, and allyl isothiocyanate were significantly different. Fen-R-strain females showed lower EAG responses to most of the tested plant volatiles (at concentrations of 1:10) than males, except for allyl isothiocyanate. A larger difference in relative EAG response to α-farnesene and β-myrcene was found between S-strain and Fen-R-strain females than between males of the two strains. A larger difference in relative EAG response to octanal, nonanal, and octan-1-ol was found between S-strain and Fen-R-strain males than between females of the two strains. These results illustrate the relationship between the function of plant volatiles and resistance in an insect pest species, and provide a scientific basis for resistance evolutionary theory in pest management research.

Drought stress leads to systemic induced susceptibility to a nectrotrophic fungus associated with mountain pine beetle in Pinus banksiana seedlings.

PubMed

Klutsch, Jennifer G; Shamoun, Simon Francis; Erbilgin, Nadir

2017-01-01

Conifers have complex defense responses to initial attacks by insects and pathogens that can have cascading effects on success of subsequent colonizers. However, drought can affect a plant's ability to respond to biotic agents by potentially altering the resources needed for the energetically costly production of induced defense chemicals. We investigated the impact of reduced water on induced chemical defenses of jack pine (Pinus banksiana) seedlings from initial attack by biotic agents and resistance to subsequent challenge inoculation with a pathogenic fungal associate of mountain pine beetle (Dendroctonus ponderosae), Grosmannia clavigera. Applications of phytohormones (methyl salicylate and methyl jasmonate) and G. clavigera were used for initial induction of defenses. Monoterpene concentrations varied with initial induction from fungal and phytohormone application while watering treatment had no effect. Seedlings treated with G. clavigera and methyl jasmonate had the greatest monoterpene concentrations compared to the control and methyl salicylate-treated seedlings. However, the monoterpene response to the challenge inoculation varied with watering treatments, not with prior induction treatments, with lower monoterpene concentrations in fungal lesions on seedlings in the low to moderate watering treatments compared to normal watering treatment. Furthermore, prior induction from phytohormones resulted in systemic cross-induction of resistance to G. clavigera under normal watering treatment but susceptibility under low watering treatment. Seedlings stressed by low water conditions, which also had lower stomatal conductance than seedlings in the normal watering treatment, likely allocated resources to initial defense response but were left unable to acquire further resources for subsequent responses. Our results demonstrate that drought can affect interactions among tree-infesting organisms through systemic cross-induction of susceptibility.

Drought stress leads to systemic induced susceptibility to a nectrotrophic fungus associated with mountain pine beetle in Pinus banksiana seedlings

PubMed Central

Shamoun, Simon Francis; Erbilgin, Nadir

2017-01-01

Conifers have complex defense responses to initial attacks by insects and pathogens that can have cascading effects on success of subsequent colonizers. However, drought can affect a plant’s ability to respond to biotic agents by potentially altering the resources needed for the energetically costly production of induced defense chemicals. We investigated the impact of reduced water on induced chemical defenses of jack pine (Pinus banksiana) seedlings from initial attack by biotic agents and resistance to subsequent challenge inoculation with a pathogenic fungal associate of mountain pine beetle (Dendroctonus ponderosae), Grosmannia clavigera. Applications of phytohormones (methyl salicylate and methyl jasmonate) and G. clavigera were used for initial induction of defenses. Monoterpene concentrations varied with initial induction from fungal and phytohormone application while watering treatment had no effect. Seedlings treated with G. clavigera and methyl jasmonate had the greatest monoterpene concentrations compared to the control and methyl salicylate-treated seedlings. However, the monoterpene response to the challenge inoculation varied with watering treatments, not with prior induction treatments, with lower monoterpene concentrations in fungal lesions on seedlings in the low to moderate watering treatments compared to normal watering treatment. Furthermore, prior induction from phytohormones resulted in systemic cross-induction of resistance to G. clavigera under normal watering treatment but susceptibility under low watering treatment. Seedlings stressed by low water conditions, which also had lower stomatal conductance than seedlings in the normal watering treatment, likely allocated resources to initial defense response but were left unable to acquire further resources for subsequent responses. Our results demonstrate that drought can affect interactions among tree-infesting organisms through systemic cross-induction of susceptibility. PMID:29216258

Concentration evolution of pharmaceutically active compounds in raw urban and industrial wastewater.

PubMed

Camacho-Muñoz, Dolores; Martín, Julia; Santos, Juan Luis; Aparicio, Irene; Alonso, Esteban

2014-09-01

The distribution of pharmaceutically active compounds in the environment has been reported in several works in which wastewater treatment plants have been identified as the main source of these compounds to the environment. The concentrations of these compounds in influent wastewater can vary widely not only during the day but also along the year, because of the seasonal-consumption patterns of some pharmaceuticals. However, only few studies have attempted to assess the hourly variability of the concentrations of pharmaceutically active compounds in wastewater. In this work, the distribution and seasonal and hourly variability of twenty-one pharmaceuticals, belonging to seven therapeutic groups, have been investigated in urban and industrial wastewater. The highest concentrations of pharmaceutically active compounds, except salicylic acid, were found in urban wastewater, especially in the case of anti-inflammatory drugs and caffeine. The highest concentrations of salicylic acid were measured in industrial wastewater, reaching concentration levels up to 3295μgL(-)(1). The studied pharmaceutically active compounds showed different distribution patterns during winter and summer periods. Temporal variability of pharmaceutically active compounds during a 24-h period showed a distribution in concordance with their consumption and excretion patterns, in the case of urban wastewater, and with the schedule of industrial activities, in the case of industrial wastewater. Copyright © 2014 Elsevier Ltd. All rights reserved.

Impact of sludge stabilization processes and sludge origin (urban or hospital) on the mobility of pharmaceutical compounds following sludge landspreading in laboratory soil-column experiments.

PubMed

Lachassagne, Delphine; Soubrand, Marilyne; Casellas, Magali; Gonzalez-Ospina, Adriana; Dagot, Christophe

2015-11-01

This study aimed to determine the effect of sludge stabilization treatments (liming and anaerobic digestion) on the mobility of different pharmaceutical compounds in soil amended by landspreading of treated sludge from different sources (urban and hospital). The sorption and desorption potential of the following pharmaceutical compounds: carbamazepine (CBZ), ciprofloxacin (CIP), sulfamethoxazole (SMX), salicylic acid (SAL), ibuprofen (IBU), paracetamol (PAR), diclofenac (DIC), ketoprofen (KTP), econazole (ECZ), atenolol (ATN), and their solid-liquid distribution during sludge treatment (from thickening to stabilization) were investigated in the course of batch testing. The different sludge samples were then landspread at laboratory scale and leached with an artificial rain simulating 1 year of precipitation adapted to the surface area of the soil column used. The quality of the resulting leachate was investigated. Results showed that ibuprofen had the highest desorption potential for limed and digested urban and hospital sludge. Ibuprofen, salicylic acid, diclofenac, and paracetamol were the only compounds found in amended soil leachates. Moreover, the leaching potential of these compounds and therefore the risk of groundwater contamination depend mainly on the origin of the sludge because ibuprofen and diclofenac were present in the leachates of soils amended with urban sludge, whereas paracetamol and salicylic acid were found only in the leachates of soils amended with hospital sludge. Although carbamazepine, ciprofloxacin, sulfamethoxazole, ketoprofen, econazole, and atenolol were detected in some sludge, they were not present in any leachate. This reflects either an accumulation and/or (bio)degradation of these compounds (CBZ, CIP, SMX, KTP, ECZ, and ATN ), thus resulting in very low mobility in soil. Ecotoxicological risk assessment, evaluated by calculating the risk quotients for each studied pharmaceutical compound, revealed no high risk due to the application on the soil of sludge stabilized by liming or anaerobic digestion.

INVESTIGATION OF CE/LIF AS A TOOL IN THE ...

EPA Pesticide Factsheets

The investigation of emerging contaminant issues is a proactive effort in environmental analysis. As a part of this effort, sewage effluent is of current analytical interest because of the presence of pharmaceuticals and their metabolites and personal care products The environmental impact of these components is still under investigation but their constant perfusion into receiving waters and their potential effect on biota is of concern. This paper examines a tool for the characterization of sewage effluent using capillary electrophoresis/laser-induced fluorescence (CE/LIF) with a frequency-doubled laser operated in the ultraviolet (UV). Fluorescent acidic analytes are targeted because they present special problems for techniques such as gas chromatography/mass spectrometry (GC/MS) but are readily accessible to CE/LIF. As an example of the application of this tool, salicylic acid is determined near the 100 ng/L level in sewage effluent. Salicylic acid is a metabolite of various analgesics Relatively stable in the environment, it is a common contaminant of municipal sewage systems. Salicylic acid was recovered from freshly collected samples of the effluent by liquid-liquid extraction as part of a broad characterization effort. Confirmation of identity was by electron ionization GC/MS after conversion of the salicylic acid to the methyl ester by means of trimethylsilyidiazomethane CE/LIF in the UV has revealed more than 50 individual peaks in the extract and a bac

Variability in the composition of phenolic compounds in winter-dormant Salix pyrolifolia in relation to plant part and age.

PubMed

Lavola, Anu; Maukonen, Merja; Julkunen-Tiitto, Riitta

2018-06-12

The phenolic phytochemicals of winter-dormant Salix pyrolifolia were determined from the vegetative buds, and the bark and wood of different-aged twigs by HPLC-DAD and UHPLC-QTOF-MS analyses. All the plant parts were composed of salicylate glucosides and the other Salix-specific, simple phenolic glucosides as well as of phenolic acids, flavonoids and the high molecular-weight condensed tannins. The flavonoid composition was most diverse in buds and they also contained a large amount of chlorogenic acid (5-caffeoylquinic acid IUPAC), while salicylate glucosides and simple phenolic glucosides predominated in bark. The wooden interior part of the twigs contained fewer components and the lowest concentrations of compounds. Salicortin was the main compound in winter-dormant S. pyrolifolia (over 10% of bark biomass), but the concentrations of picein, salireposide, isosalipurposide, catechin and condensed tannins were also high. The flavonoid composition was highly naringenin- and quercetin-biassed. The composition of phytochemicals was organ-specific and remained relatively similar between different-aged trees. However, there were compound-specific fluctuations in the concentrations of phytochemicals with the age of the trees and within plant parts. Generally, the one-year-old plants differed from the older trees in their high concentration of condensed tannins in all the plant parts studied and in the highest concentration of isosalipurposide in bark, while the total amounts of salicylate glucosides in plant parts, and of naringenin glucosides in buds, tended to be highest in 20 year-old-trees. Copyright © 2018 Elsevier Ltd. All rights reserved.

Surface-Streamline Flow Visualization

NASA Technical Reports Server (NTRS)

Langston, L.; Boyle, M.

1985-01-01

Matrix of ink dots covers matte surface of polyester drafting film. Film placed against wind-tunnel wall. Layer of methyl salicylate (oil of wintergreen) sprayed over dotted area. Ink dot streaklines show several characteristics of flow, including primary saddle point of separations, primary horseshoe vortex and smaller vortex at cylinder/ endwall junction. Surface streamline flow visualization technique suitable for use in low-speed windtunnels or other low-speed gas flows.

Bioinspired Surface Treatments for Improved Decontamination: Silicate-Based Slippery Liquid-Infused Porous Surfaces (SLIPS)

DTIC Science & Technology

2017-07-20

methyl salicylate, dimethyl methylphosphate, and diisopropyl fluorophosphates following treatment of contaminated surfaces with a soapy water solution...and diisopropyl fluorophosphate following treatment of contaminated surfaces with a soapy water solution is reported along with droplet diffusion on...SURFACES (SLIPS) INTRODUCTION The DoD Chemical and Biological Defense Program (CBDP) seeks to provide protection of forces in a contaminated

Use of Methyl Salicylates As a Trialing Chemical Agent Simulant

DTIC Science & Technology

1990-05-01

phocomelia of the hind-limbs were frequently seen after injection on day 11. Hydronephrosis , ectoplc kidneys, and exencephaly were occasionally observed...Oapparent hydronephrosis " late in gestition. This apparent abnormality decreases by steady lengthening of the renal papilla with advancing fetal anw...treated fetuses at weaning., This persistent condition, suggestive, of hydronephrosis or hypoplasia, was not noted in control fetuses. Monie (1970

Methyl Salicylate: A Reactive Chemical Warfare Agent Surrogate to Detect Reaction with Hypochlorite (POSTPRINT)

DTIC Science & Technology

2011-05-01

DMeS11,12 (tR = 14.83 min). The 3,5- DMeS crystallized spontaneously11 as colorless needles, melting point 143 146 C; 1HNMRdata: δ 7.785, 1Hd, J = 2.6 Hz, H...dichloro-phenol. Figure 2 shows two possible mecha- nisms, both promoted by the phenolic oxygen center— tautomerization to a β- keto acid and β

Bioinspired Surface Treatments for Improved Decontamination: Icephobic Surfaces

DTIC Science & Technology

2017-06-26

standing droplets of water (left) and methyl salicylate (right) immediately following liquid application (top) and 5 min after liquid application...average of nine measurements for each liquid ). Geometric surface energy was calculated based on the water and ethylene glycol interactions using software...supporting platform angle was gradually increased up to 60°. Sliding angles for each of the liquids were identified as the angle for which movement

Aromatic Hydroxylation of Salicylic Acid and Aspirin by Human Cytochromes P450

PubMed Central

Bojić, Mirza; Sedgeman, Carl A.; Nagy, Leslie D.; Guengerich, F. Peter

2015-01-01

Aspirin (acetylsalicylic acid) is a well-known and widely-used analgesic. It is rapidly deacetylated to salicylic acid, which forms two hippuric acids—salicyluric acid and gentisuric acid—and two glucuronides. The oxidation of aspirin and salicylic acid has been reported with human liver microsomes, but data on individual cytochromes P450 involved in oxidation is lacking. In this study we monitored oxidation of these compounds by human liver microsomes and cytochrome P450 (P450) using UPLC with fluorescence detection. Microsomal oxidation of salicylic acid was much faster than aspirin. The two oxidation products were 2,5-dihydroxybenzoic acid (gentisic acid, documented by its UV and mass spectrum) and 2,3-dihydroxybenzoic acid. Formation of neither product was inhibited by desferrioxamine, suggesting a lack of contribution of oxygen radicals under these conditions. Although more liphophilic, aspirin was oxidized less efficiently, primarily to the 2,5-dihydroxy product. Recombinant human P450s 2C8, 2C9, 2C19, 2D6, 2E1, and 3A4 all catalyzed the 5-hydroxylation of salicylic acid. Inhibitor studies with human liver microsomes indicated that all six of the previously mentioned P450s could contribute to both the 5- and 3-hydroxylation of salicylic acid and that P450s 2A6 and 2B6 have contributions to 5-hydroxylation. Inhibitor studies indicated that the major human P450 involved in both 3- and 5-hydroxylation of salicylic acid is P450 2E1. PMID:25840124

Early biotic stress detection in tomato (Solanum lycopersicum) by BVOC emissions.

PubMed

Kasal-Slavik, Tina; Eschweiler, Julia; Kleist, Einhard; Mumm, Roland; Goldbach, Heiner E; Schouten, Alexander; Wildt, Jürgen

2017-12-01

We investigated impacts of early and mild biotic stress on Biogenic Volatile Organic Compounds (BVOC) emissions from tomato in order to test their potential for early (biotic) stress detection. Tomato plants were exposed to two common fungal pathogens, Botrytis cinerea and Oidium neolycopesici and the sap-sucking aphid Myzus persicae. Furthermore, plants were exposed to methyl jasmonate (MeJA) in order to identify BVOC emissions related to activation of jasmonic acid (JA) signalling pathway. These emissions where then used as a reference for identifying active JA signalling pathway in plants at early stages of biotic stress. After infection by the necrotrophic fungus B. cinerea, changes in BVOC emissions indicated that tomato plants had predominantly activated the jasmonic acid (JA) signalling pathway. The plants were able to modify their defence pathways in order to overcome fungal infection. When tomato plants were infected with the biotrophic fungus O. neolycopersici, only minor changes in BVOC emissions were observed with additional emissions of the sesquiterpene α-copaene. α-copaene emissions allowed the identification of general biotic stress in the plants, without pinpointing the actual triggered defence pathway. BVOC emissions during M. persicae attack had changed before the occurrence of visual symptoms. Despite low infestation rates, plants emitted methyl salicylate indicating activation of the SA-mediated defence pathway. Copyright © 2017 Elsevier Ltd. All rights reserved.

Heterologous pathway assembly reveals molecular steps of fungal terreic acid biosynthesis.

PubMed

Kong, Chuixing; Huang, Hezhou; Xue, Ying; Liu, Yiqi; Peng, Qiangqiang; Liu, Qi; Xu, Qin; Zhu, Qiaoyun; Yin, Ying; Zhou, Xiangshan; Zhang, Yuanxing; Cai, Menghao

2018-02-01

Terreic acid is a potential anticancer drug as it inhibits Bruton's tyrosine kinase; however, its biosynthetic molecular steps remain unclear. In this work, the individual reactions of terreic acid biosynthesis were determined by stepwise pathway assembly in a heterologous host, Pichia pastoris, on the basis of previous knockout studies in a native host, Aspergillus terreus. Polyketide synthase AtX was found to catalyze the formation of partially reduced polyketide 6-methylsalicylic acid, followed by 3-methylcatechol synthesis by salicylate 1-monooxygenase AtA-mediated decarboxylative hydroxylation of 6-methylsalicylic acid. Our results show that cytochrome P450 monooxygenase AtE hydroxylates 3-methylcatechol, thus producing the next product, 3-methyl-1,2,4-benzenetriol. A smaller putative cytochrome P450 monooxygenase, AtG, assists with this step. Then, AtD causes epoxidation and hydroxyl oxidation of 3-methyl-1,2,4-benzenetriol and produces a compound terremutin, via which the previously unknown function of AtD was identified as cyclooxygenation. The final step involves an oxidation reaction of a hydroxyl group by a glucose-methanol-choline oxidoreductase, AtC, which leads to the final product: terreic acid. Functions of AtD and AtG were determined for the first time. All the genes were reanalyzed and all intermediates and final products were isolated and identified. Our model fully defines the molecular steps and corrects previous results from the literature.

Aphid-induced Defences in Chilli Affect Preferences of the Whitefly, Bemisia tabaci (Hemiptera: Aleyrodidae).

PubMed

Saad, Khalid A; Mohamad Roff, M N; Hallett, Rebecca H; Idris, A B

2015-09-03

The sweetpotato whitefly (WF), Bemisia tabaci, is a major pest that damages a wide range of vegetable crops in Malaysia. WF infestation is influenced by a variety of factors, including previous infestation of the host plant by other insect pests. This study investigated the effects of previous infestation of host chilli plants by the green peach aphid (Myzus persicae) on the olfactory behavioural response of B. tabaci, using free-choice bioassay with a Y-tube olfactometer. We analysed volatile organic compounds (VOCs) emitted by non-infested and M. persicae-infested chilli plants using solid-phase microextraction and gas chromatography-mass spectrometry. Our results showed that female WFs preferred non-infested to pre-infested plants. Collection and analysis of volatile compounds emitted by infested plants confirmed that there were significant increases in the production of monoterpenes (cymene; 1,8-cineole), sesquiterpenes (β-cadinene, α-copaene), and methyl salicylate (MeSA) compared to non-infested plants. Our results suggest that host plant infestation by aphids may induce production of secondary metabolites that deter B. tabaci from settling on its host plants. These results provide important information for understanding WF host selection and dispersal among crops, and also for manipulating WF behaviour to improve IPM in chilli.

Extent of cutaneous metabolism during percutaneous absorption of xenobiotics.

PubMed

Bronaugh, R L; Stewart, R F; Storm, J E

1989-07-01

In vitro percutaneous absorption studies generally do not determine whether biotransformation occurs during passage of a substance through the skin. Since it has recently been demonstrated that several chemicals are metabolized during skin permeation, we investigated the metabolism of five additional compounds (14C-labeled) after application to fuzzy rat skin: caffeine, p,p'-DDT, butylated hydroxytoluene (BHT), salicylic acid, and acetyl ethyl tetramethyltetralin (AETT). The viability of skin was maintained with a tissue culture medium. Radioactivity of each substrate and any metabolites in skin and receptor fluid was measured so that the absorption and metabolism of water-insoluble compounds would be accurately determined. Percutaneous absorption ranged from a low of 13% of the applied dose for BHT to a high of 49% for DDT. BHT was metabolized in skin to 4-hydroxy-BHT and an unknown metabolite. Of the absorbed radioisotope, 6.6% was isolated in biotransformed products found mainly in the receptor fluid. AETT was also metabolized during absorption, with 1.9% of the absorbed radioisotope found in two unknown peaks. Caffeine, DDT, and salicylic acid were not metabolized during skin permeation. Skin and liver microsomal metabolism was measured for all compounds except DDT. Metabolism in skin was observed only for the compounds also biotransformed in the diffusion cell; BHT and AETT were metabolized at 113 and 2.5 pmol/min/mg protein, respectively. In this study, as in others, skin metabolism was substantially less than the corresponding metabolism in liver. Therefore, a low rate of liver metabolism such as that found for caffeine, salicylic acid, and DDT might often be predictive of the absence of measurable metabolism during skin permeation. It seems likely that for many compounds, the biotransformations in skin will be small in terms of the percentage of absorbed material that is metabolized. Nevertheless, with potent compounds, even small quantities of a metabolite can be important and for pharmacokinetic studies, viability of skin must be maintained.

Identification of didecyldimethylammonium salts and salicylic acid as antimicrobial compounds in commercial fermented radish kimchi.

PubMed

Li, Jing; Chaytor, Jennifer L; Findlay, Brandon; McMullen, Lynn M; Smith, David C; Vederas, John C

2015-03-25

Daikon radish (Raphanus sativus) fermented with lactic acid bacteria, especially Leuconostoc or Lactobacillus spp., can be used to make kimchi, a traditional Korean fermented vegetable. Commercial Leuconostoc/radish root ferment filtrates are claimed to have broad spectrum antimicrobial activity. Leuconostoc kimchii fermentation products are patented as preservatives for cosmetics, and certain strains of this organism are reported to produce antimicrobial peptides (bacteriocins). We examined the antimicrobial agents in commercial Leuconostoc/radish root ferment filtrates. Both activity-guided fractionation with Amberlite XAD-16 and direct extraction with ethyl acetate gave salicylic acid as the primary agent with activity against Gram-negative bacteria. Further analysis of the ethyl acetate extract revealed that a didecyldimethylammonium salt was responsible for the Gram-positive activity. The structures of these compounds were confirmed by a combination of (1)H- and (13)C NMR, high-performance liquid chromatography, high-resolution mass spectrometry, and tandem mass spectrometry analyses. Radiocarbon dating indicates that neither compound is a fermentation product. No antimicrobial peptides were detected.

Ozone-Induced Responses in Croton floribundus Spreng. (Euphorbiaceae): Metabolic Cross-Talk between Volatile Organic Compounds and Calcium Oxalate Crystal Formation

PubMed Central

Cardoso-Gustavson, Poliana; Bolsoni, Vanessa Palermo; de Oliveira, Debora Pinheiro; Guaratini, Maria Tereza Gromboni; Aidar, Marcos Pereira Marinho; Marabesi, Mauro Alexandre; Alves, Edenise Segala; de Souza, Silvia Ribeiro

2014-01-01

Here, we proposed that volatile organic compounds (VOC), specifically methyl salicylate (MeSA), mediate the formation of calcium oxalate crystals (COC) in the defence against ozone (O3) oxidative damage. We performed experiments using Croton floribundus, a pioneer tree species that is tolerant to O3 and widely distributed in the Brazilian forest. This species constitutively produces COC. We exposed plants to a controlled fumigation experiment and assessed biochemical, physiological, and morphological parameters. O3 induced a significant increase in the concentrations of constitutive oxygenated compounds, MeSA and terpenoids as well as in COC number. Our analysis supported the hypothesis that ozone-induced VOC (mainly MeSA) regulate ROS formation in a way that promotes the opening of calcium channels and the subsequent formation of COC in a fast and stable manner to stop the consequences of the reactive oxygen species in the tissue, indeed immobilising the excess calcium (caused by acute exposition to O3) that can be dangerous to the plant. To test this hypothesis, we performed an independent experiment spraying MeSA over C. floribundus plants and observed an increase in the number of COC, indicating that this compound has a potential to directly induce their formation. Thus, the tolerance of C. floribundus to O3 oxidative stress could be a consequence of a higher capacity for the production of VOC and COC rather than the modulation of antioxidant balance. We also present some insights into constitutive morphological features that may be related to the tolerance that this species exhibits to O3. PMID:25165889

Salicylic Acid Treatment Increases the Levels of Triterpene Glycosides in Black Cohosh (Actaea Racemosa) Rhizomes.

PubMed

De Capite, Annette; Lancaster, Tyler; Puthoff, David

2016-01-01

Black cohosh (Actaea racemosa) serves as the host plant for the Appalachian azure butterfly, Celastrina neglectamajor. Overharvesting of Black cohosh for the dietary supplement industry may result in its extirpation, and may also cause the elimination of the dependent butterfly. One way to increase or maintain the number of host plants in forested environments would be to reduce the number harvested, for example by increasing the levels of the desired metabolites in Black cohosh rhizomes. The secondary metabolites actein and deoxyactein are triterpene glycosides and are among the compounds associated with the putative activity of Black cohosh extracts. Acetein and deoxyacetein are used to standardize Black cohosh supplements. To gain an understanding of mechanisms that may control actein and deoxyactein accumulation, Black cohosh rhizomes were treated with exogenous salicylic acid, jasmonic acid, or ethylene, or were mechanically wounded. Salicylic acid treatment significantly increased the levels of actein and deoxyactein in the rhizome of Black cohosh, suggesting that the synthesis of triterpene glycosides is controlled in part by salicylic acid. Using salicylic acid or related chemicals to increase the levels of actein and deoxyactein in rhizomes may help supply the supplement industry and, simultaneously, help conserve Black cohosh and species dependent upon it.

DOE Office of Scientific and Technical Information (OSTI.GOV)

Zhao, Nan; Guan, Ju; Ferrer, Jean-Luc

Two benzenoid esters, methyl salicylate (MeSA) and methyl benzoate (MeBA), were detected from insect-damaged rice plants. By correlating metabolite production with gene expression analysis, five candidate genes encoding putative carboxyl methyltransferases were identified. Enzymatic assays with Escherichia coli-expressed recombinant proteins demonstrated that only one of the five candidates, OsBSMT1, has salicylic acid (SA) methyltransferase (SAMT) and benzoic acid (BA) methyltransferase (BAMT) activities for producing MeSA and MeBA, respectively. Whereas OsBSMT1 is phylogenetically relatively distant from dicot SAMTs, the three-dimensional structure of OsBSMT1, which was determined using homology-based structural modeling, is highly similar to those of characterized SAMTs. Analyses of OsBSMT1more » expression in wild-type rice plants under various stress conditions indicate that the jasmonic acid (JA) signaling pathway plays a critical role in regulating the production and emission of MeSA in rice. Further analysis using transgenic rice plants overexpressing NH1, a key component of the SA signaling pathway in rice, suggests that the SA signaling pathway also plays an important role in governing OsBSMT1 expression and emission of its products, probably through a crosstalk with the JA signaling pathway. The role of the volatile products of OsBSMT1, MeSA and MeBA, in rice defense against insect herbivory is discussed.« less

Comparative transcriptional profiling of Gracilariopsis lemaneiformis in response to salicylic acid- and methyl jasmonate-mediated heat resistance

PubMed Central

Wang, Chongbin; Zou, Tonglei; Xu, Nianjun; Sun, Xue

2017-01-01

Culturing the economically important macroalga Gracilariopsis lemaneiformis (Rhodophyta) is limited due to the high temperatures in the summertime on the southern Chinese coast. Previous studies have demonstrated that two phytohormones, salicylic acid (SA) and methyl jasmonate (MJ), can alleviate the adverse effects of high-temperature stress on Gp. lemaneiformis. To elucidate the molecular mechanisms underlying SA- and MJ-mediated heat tolerance, we performed comprehensive analyses of transcriptome-wide gene expression profiles using RNA sequencing (RNA-seq) technology. A total of 14,644 unigenes were assembled, and 10,501 unigenes (71.71%) were annotated to the reference databases. In the SA, MJ and SA/MJ treatment groups, 519, 830, and 974 differentially expressed unigenes were detected, respectively. Unigenes related to photosynthesis and glycometabolism were enriched by SA, while unigenes associated with glycometabolism, protein synthesis, heat shock and signal transduction were increased by MJ. A crosstalk analysis revealed that 216 genes were synergistically regulated, while 18 genes were antagonistically regulated by SA and MJ. The results indicated that the two phytohormones could mitigate the adverse effects of heat on multiple pathways, and they predominantly acted synergistically to resist heat stress. These results will provide new insights into how SA and MJ modulate the molecular mechanisms that counteract heat stress in algae. PMID:28464018

Neuropeptide Receptors NPR-1 and NPR-2 Regulate Caenorhabditis elegans Avoidance Response to the Plant Stress Hormone Methyl Salicylate

PubMed Central

Luo, Jintao; Xu, Zhaofa; Tan, Zhiping; Zhang, Zhuohua; Ma, Long

2015-01-01

Methyl salicylate (MeSa) is a stress hormone released by plants under attack by pathogens or herbivores . MeSa has been shown to attract predatory insects of herbivores and repel pests. The molecules and neurons underlying animal response to MeSa are not known. Here we found that the nematode Caenorhabditis elegans exhibits a strong avoidance response to MeSa, which requires the activities of two closely related neuropeptide receptors NPR-1 and NPR-2. Molecular analyses suggest that NPR-1 expressed in the RMG inter/motor neurons is required for MeSa avoidance. An NPR-1 ligand FLP-18 is also required. Using a rescuing npr-2 promoter to drive a GFP transgene, we identified that NPR-2 is expressed in multiple sensory and interneurons. Genetic rescue experiments suggest that NPR-2 expressed in the AIZ interneurons is required for MeSa avoidance. We also provide evidence that the AWB sensory neurons might act upstream of RMGs and AIZs to detect MeSa. Our results suggest that NPR-2 has an important role in regulating animal behavior and that NPR-1 and NPR-2 act on distinct interneurons to affect C. elegans avoidance response to MeSa. PMID:25527285

Lipoxygenase in Caragana jubata responds to low temperature, abscisic acid, methyl jasmonate and salicylic acid.

PubMed

Bhardwaj, Pardeep Kumar; Kaur, Jagdeep; Sobti, Ranbir Chander; Ahuja, Paramvir Singh; Kumar, Sanjay

2011-09-01

Lipoxygenase (LOX) catalyses oxygenation of free polyunsaturated fatty acids into oxylipins, and is a critical enzyme of the jasmonate signaling pathway. LOX has been shown to be associated with biotic and abiotic stress responses in diverse plant species, though limited data is available with respect to low temperature and the associated cues. Using rapid amplification of cDNA ends, a full-length cDNA (CjLOX) encoding lipoxygenase was cloned from apical buds of Caragana jubata, a temperate plant species that grows under extreme cold. The cDNA obtained was 2952bp long consisting of an open reading frame of 2610bp encoding 869 amino acids protein. Multiple alignment of the deduced amino acid sequence with those of other plants demonstrated putative LH2/ PLAT domain, lipoxygenase iron binding catalytic domain and lipoxygenase_2 signature sequences. CjLOX exhibited up- and down-regulation of gene expression pattern in response to low temperature (LT), abscisic acid (ABA), methyl jasmonate (MJ) and salicylic acid (SA). Among all the treatments, a strong up-regulation was observed in response to MJ. Data suggests an important role of jasmonate signaling pathway in response to LT in C. jubata. Copyright © 2011 Elsevier B.V. All rights reserved.

Identification of New Cocrystal Systems with Stoichiometric Diversity of Salicylic Acid Using Thermal Methods.

PubMed

Zhou, Zhengzheng; Chan, Hok Man; Sung, Herman H-Y; Tong, Henry H Y; Zheng, Ying

2016-04-01

The purpose of this work was to develop thermal methods to identify cocrystal systems with stoichiometric diversity. Differential scanning calorimetry (DSC) and hot stage microscopy (HSM) have been applied to study the stoichiometric diversity phenomenon on cocrystal systems of the model compound salicylic acid (SA) with different coformers (CCFs). The DSC method was particularly useful in the identification of cocrystal re-crystallization, especially to improve the temperature resolution using a slower heating rate. HSM was implemented as a complementary protocol to confirm the DSC results. The crystal structures were elucidated by single-crystal X-ray diffraction (SXRD). Two new cocrystal systems consisting of salicylic acid-benzamide (SA-BZD, 1:1, 1:2) and salicylic acid-isonicotinamide (SA-ISN, 1:1, 2:1) have been identified in the present work. The chemical structures of the newly discovered cocrystals SA-BZD (1:2) and SA-ISN (2:1) have been elucidated using X-ray single crystal and powder diffraction methods. The developed thermal methods could rapidly identify cocrystal systems with stoichiometric diversity, with the potential to discover new pharmaceutical cocrystals in the future.

Microbiological Defacement of Navy Buildings.

DTIC Science & Technology

1982-10-01

ethylbenzyl ammnonium cyclohexyl sulfamate trans-1,2 bis (propylsulfonyl) etherie Bis( tributyltin ) oxide Captan Chlorothalonil (also called...3,4 ,5-Tribromosalicylanilide Tributyltin fluoride Tributyltin salicylate 2,3,5-Trichloro-4-(propylsulfonyl) pyridine *Source: EPA; compounds may

Effects of legislation restricting pack sizes of paracetamol and salicylate on self poisoning in the United Kingdom: before and after study

PubMed Central

Hawton, Keith; Townsend, Ellen; Deeks, Jonathan; Appleby, Louis; Gunnell, David; Bennewith, Olive; Cooper, Jayne

2001-01-01

Objective To evaluate the effects on suicidal behaviour of legislation limiting the size of packs of paracetamol and salicylates sold over the counter. Design Before and after study. Setting UK population, with detailed monitoring of data from five liver units and seven general hospitals, between September 1996 and September 1999. Subjects People who died by suicidal or accidental overdose with paracetamol or salicylates or who died of undetermined causes; patients admitted to liver units with hepatic paracetamol poisoning; patients presenting to general hospitals with self poisoning after taking paracetamol or salicylates. Main outcome measures Mortality from paracetamol or salicylate overdose; numbers of patients referred to liver units or listed for liver transplant; numbers of transplantations; numbers of overdoses and tablets taken; blood concentrations of the drugs; prothrombin times; sales to pharmacies and other outlets of paracetamol and salicylates. Results Numbers of tablets per pack of paracetamol and salicylates decreased markedly in the year after the change in legislation on 16 September 1998. The annual number of deaths from paracetamol poisoning decreased by 21% (95% confidence interval 5% to 34%) and the number from salicylates decreased by 48% (11% to 70%). Liver transplant rates after paracetamol poisoning decreased by 66% (55% to 74%). The rate of non-fatal self poisoning with paracetamol in any form decreased by 11% (5% to 16%), mainly because of a 15% (8% to 21%) reduction in overdoses of paracetamol in non-compound form. The average number of tablets taken in paracetamol overdoses decreased by 7% (0% to 12%), and the proportion involving >32 tablets decreased by 17% (4% to 28%). The average number of tablets taken in salicylate overdoses did not decrease, but 34% fewer (2% to 56%) salicylate overdoses involved >32 tablets. After the legislation mean blood concentrations of salicylates after overdose decreased, as did prothrombin times; mean blood concentrations of paracetamol did not change. Conclusion Legislation restricting pack sizes of paracetamol and salicylates in the United Kingdom has had substantial beneficial effects on mortality and morbidity associated with self poisoning using these drugs. What is already known on this topicParacetamol and salicylate overdoses are very common in the United Kingdom and are associated with high levels of mortality and morbidityInternational comparison shows that national mortality from paracetamol overdose may be related to the maximum number of tablets in individual preparationsLegislation to limit the size of packs of paracetamol and salicylates was introduced in the United Kingdom in September 1998What this study addsThe number of tablets in packets of paracetamol and salicylate preparations decreased markedly in the 12 months after the legislationThe number of deaths from self poisoning with paracetamol alone and with salicylates alone decreased after the legislationThere was also a decrease in the number of liver transplants and admissions to liver units with hepatic paracetamol poisoning and in the number of overdoses of paracetamol and salicylates in which large numbers of tablets were taken PMID:11358770

Chromatographic analysis of salicylic compounds in different species of the genus Salix.

PubMed

Pobłocka-Olech, Loretta; van Nederkassel, Anne-Marie; Vander Heyden, Yvan; Krauze-Baranowska, Mirosława; Glód, Daniel; Baczek, Tomasz

2007-11-01

The separation of nine phenol glycosides--salicin, salicortin, 2'-acetylsalicortin, populin, tremulacin, salidroside, triandrin, picein and helicin--by normal phase (NP), reversed phase (RP) HPLC techniques and a coupling of NP and RP monolithic silica columns was studied. Among the above nine compounds only five--salicin, populin, tremulacin, salidroside and triandrin--were resolved in an NP system with a mobile phase comprising hexane/isopropanol/methanol (87:12:1, v/v/v). Optimized separation was performed with two coupled monolithic silica columns of different polarity (bare silica and RP-18). The method was applied to verify the presence of salicylic compounds and other phenolic derivatives in the bark of six species from the genus Salix, namely S. purpurea, S. daphnoides clone 1095, S. alba clone 1100, S. triandra, S. viminalis, and S. herbacea. Gradient elution with a mobile phase composed of acetonitrile and water containing 0.05% of trifluoroacetic acid, with increasing acetonitrile concentration from 3% to 48%, was chosen as optimal. For the selective detection of the salicylic compounds, an evaporative light scattering detector was employed along with a UV detector. The differences in the composition of phenols in the different plant materials were confirmed. Additionally, it must be emphasized that for the first time the presence of 2'-acetylsalicortin was revealed in S. alba clone 1100. Furthermore, an SPE-HPLC method was developed for the rapid analysis of the salicin content, analyzed as free and total fraction, in willow barks. The determined concentrations of total salicin varied from 25.4 mg/g in S. alba clone 1100 to 96.47 mg/g in S. daphnoides clone 1095.

Lead-Free Double-Base Propellant for the 2.75 Inch Rocket Motor

NASA Technical Reports Server (NTRS)

Magill, B. T.; Nauflett, G. W.; Furrow, K. W.

2000-01-01

The current MK 66 2.75 inch Rocket Motor double-base propellant contains the lead-based ballistic modifier LC-12-15 to achieve the desired plateau and mesa burning rate characteristics. The use of lead compounds poses a concern for the environment and for personal safety due to the metal's toxic nature when introduced into the atmosphere by propellant manufacture, rocket motor firing, and disposal. Copper beta-resorcylate (copper 2,4-di-hydroxy-benzoate) was successfully used in propellant as a simple modifier in the mid 1970's. This and other compounds have also been mixed with lead salts to obtain more beneficial ballistic results. Synthesized complexes of lead and copper compounds soon replaced the mixtures. The complexes incorporate the lead, copper lack of organic liquids, which allows for easier propellant processing. About ten years ago, the Indian Head Division, Naval Surface Warfare Center (NSWC), initiated an effort to develop a lead-free propellant for use in missile systems. Several lead-free propellant candidate formulations were developed. About five years ago, NSWC, in conjunction with Alliant Techsystems, Radford Army Ammunition Plant, continued ballistic modifier investigations. A four component ballistic modifier system without lead for double-base propellants that provide adequate plateau and mesa burn rate characteristics was developed and patented. The ballistic modifier's system contains bismuth subsalicylate, 1.5 percent; copper salicylate, 1.0 percent, copper stannate, 0.77 percent; and carbon black, 0.1 percent. Action time and impulse data obtained through multiple static firings indicate that the new lead-free double-base propellant, while not a match for NOSIH-AA-2, will be a very suitable replacement in the 2.75 inch Rocket Motor. Accelerated aging of the double-base propellant containing the lead-free ballistic modifier showed that it had a much higher rate of stabilizer depletion than the AA-2. A comprehensive study showed that an increased rate of stabilizer depletion occurred in propellants containing monobasic copper salicylate. The study also showed that propellants containing a mixture of bismuth subsalicylate and copper salicylate, had only about one-half the stabilizer depletion rate than those with copper salicylate alone. The copper salicylate catalyzes the decomposition of nitroglycerin, which triggers a chain of events leading to the increased rate of stabilizer depletion. A program has been initiated to coat the ballistic modifier, thus isolating it from the nitroglycerin.

Salicylic acid metabolites and derivatives inhibit CDK activity: Novel insights into aspirin's chemopreventive effects against colorectal cancer

PubMed Central

Dachineni, Rakesh; Kumar, D. Ramesh; Callegari, Eduardo; Kesharwani, Siddharth S.; Sankaranarayanan, Ranjini; Seefeldt, Teresa; Tummala, Hemachand; Bhat, G. Jayarama

2017-01-01

Aspirin's potential as a drug continues to be evaluated for the prevention of colorectal cancer (CRC). Although multiple targets for aspirin and its metabolite, salicylic acid, have been identified, no unifying mechanism has been proposed to clearly explain its chemopreventive effects. Our goal here was to investigate the ability of salicylic acid metabolites, known to be generated through cytochrome P450 (CYP450) enzymes, and its derivatives as cyclin dependent kinase (CDK) inhibitors to gain new insights into aspirin's chemopreventive actions. Using in vitro kinase assays, for the first time, we demonstrate that salicylic acid metabolites, 2,3-dihydroxy-benzoic acid (2,3-DHBA) and 2,5-dihydroxybenzoic acid (2,5-DHBA), as well as derivatives 2,4-dihydroxybenzoic acid (2,4-DHBA), 2,6-dihydroxybenzoic acid (2,6-DHBA), inhibited CDK1 enzyme activity. 2,3-DHBA and 2,6-DHBA did not inhibit CDK2 and 4; however, both inhibited CDK-6 activity. Interestingly, another derivative, 2,4,6-trihydroxybenzoic acid (2,4,6-THBA) was highly effective in inhibiting CDK1, 2, 4 and 6 activity. Molecular docking studies showed that these compounds potentially interact with CDK1. Immunoblotting experiments showed that aspirin acetylated CDK1, and pre-incubation with salicylic acid and its derivatives prevented aspirin-mediated CDK1 acetylation, which supported the data obtained from molecular docking studies. We suggest that intracellularly generated salicylic acid metabolites through CYP450 enzymes within the colonic epithelial cells, or the salicylic acid metabolites generated by gut microflora may significantly contribute to the preferential chemopreventive effect of aspirin against CRC through inhibition of CDKs. This novel hypothesis and mechanism of action in aspirin's chemopreventive effects opens a new area for future research. In addition, structural modification to salicylic acid derivatives may prove useful in the development of novel CDK inhibitors in cancer prevention and treatment. PMID:29075787

PLUTONIUM COMPOUNDS AND PROCESS FOR THEIR PREPARATION

DOEpatents

Wolter, F.J.; Diehl, H.C. Jr.

1958-01-01

This patent relates to certain new compounds of plutonium, and to the utilization of these compounds to effect purification or separation of the plutonium. The compounds are organic chelate compounds consisting of tetravalent plutonium together with a di(salicylal) alkylenediimine. These chelates are soluble in various organic solvents, but not in water. Use is made of this property in extracting the plutonium by contacting an aqueous solution thereof with an organic solution of the diimine. The plutonium is chelated, extracted and effectively separated from any impurities accompaying it in the aqueous phase.

Physcomitrella patens activates reinforcement of the cell wall, programmed cell death and accumulation of evolutionary conserved defence signals, such as salicylic acid and 12-oxo-phytodienoic acid, but not jasmonic acid, upon Botrytis cinerea infection.

PubMed

Ponce De León, Inés; Schmelz, Eric A; Gaggero, Carina; Castro, Alexandra; Álvarez, Alfonso; Montesano, Marcos

2012-10-01

The moss Physcomitrella patens is an evolutionarily basal model system suitable for the analysis of plant defence responses activated after pathogen assault. Upon infection with the necrotroph Botrytis cinerea, several defence mechanisms are induced in P. patens, including the fortification of the plant cell wall by the incorporation of phenolic compounds and the induced expression of related genes. Botrytis cinerea infection also activates the accumulation of reactive oxygen species and cell death with hallmarks of programmed cell death in moss tissues. Salicylic acid (SA) levels also increase after fungal infection, and treatment with SA enhances transcript accumulation of the defence gene phenylalanine ammonia-lyase (PAL) in P. patens colonies. The expression levels of the genes involved in 12-oxo-phytodienoic acid (OPDA) synthesis, including lipoxygenase (LOX) and allene oxide synthase (AOS), increase in P. patens gametophytes after pathogen assault, together with a rise in free linolenic acid and OPDA concentrations. However, jasmonic acid (JA) could not be detected in healthy or infected tissues of this plant. Our results suggest that, although conserved defence signals, such as SA and OPDA, are synthesized and are probably involved in the defence response of P. patens against B. cinerea infection, JA production appears to be missing. Interestingly, P. patens responds to OPDA and methyl jasmonate by reducing moss colony growth and rhizoid length, suggesting that jasmonate perception is present in mosses. Thus, P. patens can provide clues with regard to the evolution of different defence pathways in plants, including signalling and perception of OPDA and jasmonates in nonflowering and flowering plants. © 2012 THE AUTHORS. MOLECULAR PLANT PATHOLOGY © 2012 BSPP AND BLACKWELL PUBLISHING LTD.

Complexation induced fluorescence and acid-base properties of dapoxyl dye with γ-cyclodextrin: a drug-binding application using displacement assays.

PubMed

Pal, Kaushik; Mallick, Suman; Koner, Apurba L

2015-06-28

Host-guest complexation of dapoxyl sodium sulphonate (DSS), an intramolecular charge transfer dye with water-soluble and non-toxic macrocycle γ-cyclodextrin (γ-CD), has been investigated in a wide pH range. Steady-state absorption, fluorescence and time-resolved fluorescence measurements confirm the positioning of DSS into the hydrophobic cavity of γ-CD. A large fluorescence enhancement ca. 30 times, due to 1 : 2 complex formation and host-assisted guest-protonation have been utilised for developing a method for the utilisation of CD based drug-delivery applications. A simple fluorescence-displacement based approach is implemented at physiological pH for the assessment of binding strength of pharmaceutically useful small drug molecules (ibuprofen, paracetamol, methyl salicylate, salicylic acid, aspirin, and piroxicam) and six important antibiotic drugs (resazurin, thiamphenicol, chloramphenicol, ampicillin, kanamycin, and sorbic acid) with γ-CD.

Chemical Agent Monitor (CAM) Follow-On Operational Test and Evaluation Simulant Test Strategy

DTIC Science & Technology

1990-06-01

the CAM’s follow-on test and evaluation. 5 Blank CONTENTS Page 1. INTRODUCTION .................................................... 9 1.1 Purpose...SIMULANT TEST STRATEGY 1. INTRODUCTION 1.1 Purpose. The purpose of this report is to provide methyl salicylate (MS) and dipropylene glycol monomethyl...Syringe Hamilton, 50 pL 10 Hamilton Dispenser Model# PB 600 2 Syringe Needle 26 jauge 20 MS ** 30 gallons DPGME ** 40 gallons Ethanol ** 10 gallons * Item

Citramalic acid and salicylic acid in sugar beet root exudates solubilize soil phosphorus

PubMed Central

2011-01-01

Background In soils with a low phosphorus (P) supply, sugar beet is known to intake more P than other species such as maize, wheat, or groundnut. We hypothesized that organic compounds exuded by sugar beet roots solubilize soil P and that this exudation is stimulated by P starvation. Results Root exudates were collected from plants grown in hydroponics under low- and high-P availability. Exudate components were separated by HPLC, ionized by electrospray, and detected by mass spectrometry in the range of mass-to-charge ratio (m/z) from 100 to 1000. Eight mass spectrometric signals were enhanced at least 5-fold by low P availability at all harvest times. Among these signals, negative ions with an m/z of 137 and 147 were shown to originate from salicylic acid and citramalic acid. The ability of both compounds to mobilize soil P was demonstrated by incubation of pure substances with Oxisol soil fertilized with calcium phosphate. Conclusions Root exudates of sugar beet contain salicylic acid and citramalic acid, the latter of which has rarely been detected in plants so far. Both metabolites solubilize soil P and their exudation by roots is stimulated by P deficiency. These results provide the first assignment of a biological function to citramalic acid of plant origin. PMID:21871058

Pharmaceutical removal in tropical subsurface flow constructed wetlands at varying hydraulic loading rates.

PubMed

Zhang, Dong Qing; Gersberg, Richard M; Hua, Tao; Zhu, Junfei; Tuan, Nguyen Anh; Tan, Soon Keat

2012-04-01

Determining the fate of emerging organic contaminants in an aquatic ecosystem is important for developing constructed wetlands (CWs) treatment technology. Experiments were carried out in subsurface flow CWs in Singapore to evaluate the fate and transport of eight pharmaceutical compounds. The CW system included three parallel horizontal subsurface flow CWs and three parallel unplanted beds fed continuously with synthetic wastewater at different hydraulic retention times (HRTs). The findings of the tests at 2-6 d HRTs showed that the pharmaceuticals could be categorized as (i) efficiently removed compounds with removal higher than 85% (ketoprofen and salicylic acid); (ii) moderately removed compounds with removal efficiencies between 50% and 85% (naproxen, ibuprofen and caffeine); and (iii) poorly removed compounds with efficiency rate lower than 50% (carbamazepine, diclofenac, and clofibric acid). Except for carbamazepine and salicylic acid, removal efficiencies of the selected pharmaceuticals showed significant (p<0.05) enhancement in planted beds as compared to the unplanted beds. Removal of caffeine, ketoprofen and clofibric acid were found to follow first order decay kinetics with decay constants higher in the planted beds than the unplanted beds. Correlations between pharmaceutical removal efficiencies and log K(ow) were not significant (p>0.05), implying that their removal is not well related to the compound's hydrophobicity. Copyright © 2011 Elsevier Ltd. All rights reserved.

Optimization of Substituted 6-Salicyl-4-Anilinoquinazoline Derivatives as Dual EGFR/HER2 Tyrosine Kinase Inhibitors

PubMed Central

Sun, Jian; Li, Jing-Ran; Fang, Fei; Du, Qian-Ru; Qian, Yong; Gong, Hai-Bin; Zhu, Hai-Liang

2013-01-01

4-Anilinoquinazolines as an important class of protein kinase inhibitor are widely investigated for epidermal growth factor receptor (EGFR) tyrosine kinase or epidermal growth factor receptor 2 (HER2) inhibition. A series of novel 6-salicyl-4-anilinoquinazoline derivatives 9–27 were prepared and evaluated for their EGFR/HER2 tyrosine kinase inhibitory activity as well as their antiproliferative properties on three variant cancer cell lines (A431, MCF-7, and A549). The bioassay results showed most of the designed compounds exhibited moderate to potent in vitro inhibitory activity in the enzymatic and cellular assays, of which compound 21 revealed the most potent dual EGFR/HER2 inhibitory activity, with IC50 values of 0.12 µM and 0.096 µM, respectively, comparable to the control compounds Erlotinib and Lapatinib. Furthermore, the kinase selectivity profile of 21 was accessed and demonstrated its good selectivity over the majority of the close kinase targets. Docking simulation was performed to position compound 21 into the EGFR/HER2 active site to determine the probable binding pose. These new findings along with molecular docking observations could provide an important basis for further development of compound 21 as a potent EGFR/HER2 dual kinase inhibitor. PMID:23936329

Development of Inhibitors of Salicylic Acid Signaling.

PubMed

Jiang, Kai; Kurimoto, Tetsuya; Seo, Eun-kyung; Miyazaki, Sho; Nakajima, Masatoshi; Nakamura, Hidemitsu; Asami, Tadao

2015-08-19

Salicylic acid (SA) plays important roles in the induction of systemic acquired resistance (SAR) in plants. Determining the mechanism of SAR will extend our understanding of plant defenses against pathogens. We recently reported that PAMD is an inhibitor of SA signaling, which suppresses the expression of the pathogenesis-related PR genes and is expected to facilitate the understanding of SA signaling. However, PAMD strongly inhibits plant growth. To minimize the side effects of PAMD, we synthesized a number of PAMD derivatives, and identified compound 4 that strongly suppresses the expression of the PR genes with fewer adverse effects on plant growth than PAMD. We further showed that the adverse effects on plant growth were partially caused the stabilization of DELLA, which is also related to the pathogen responses. These results indicate that compound 4 would facilitate our understanding of SA signaling and its cross talk with other plant hormones.

Jasmonic and salicylic acids enhanced phytochemical production and biological activities in cell suspension cultures of spine gourd (Momordica dioica Roxb).

PubMed

Chung, Ill-Min; Rekha, Kaliyaperumal; Rajakumar, Govindasamy; Thiruvengadam, Muthu

2017-03-01

In vitro cell suspension culture was established for the production of commercially valuable phytochemicals in Momordica dioica. The influence of elicitors in jasmonic acid (JA) and salicylic acid (SA) increased their effect on phytochemical production and biomass accumulation in M. dioica. The results indicate that compared with non-elicited cultures, JA- and SA-elicited cell suspension cultures had significantly enhanced phenolic, flavonoid, and carotenoid production, as well as antioxidant, antimicrobial, and antiproliferative activities. Furthermore, elicited cultures produced 22 phenolic compounds, such as flavonols, hydroxycinnamic acids, and hydroxybenzoic acids. Greater biomass production, phytochemical accumulation, and biological activity occurred in JA- than in SA-elicited cell cultures. This study is the first to successfully establish M. dioica cell suspension cultures for the production of phenolic compounds and carotenoids, as well as for biomass accumulation.

Certain Aliphatic Nitramines and Related Compounds

DTIC Science & Technology

1944-11-29

I N02 This reaction served in positively establishing the nature . the alkyl group attachment as N- methyl and not 0- methyl . Also N...dinitroplperazine» • • 76 Reaction of N- methyl - ethylenedinitramine and Ethylcne •Dibromide. ; 73 Structure of High-Melting Compound Formed in...Alkylatiori of N- methyl - ethyl enedinitramine 80 Structure of Low-Melting Compound Formed in Alkylation • of N- methyl -ethylcnedinitramine. . 0

Interactions of low molecular weight aromatic acids and amino acids with goethite, kaolinite and bentonite with or without organic matter coating

NASA Astrophysics Data System (ADS)

Gao, Jiajia; Jansen, Boris; Cerli, Chiara; Kalbitz, Karsten

2015-04-01

Interaction of organic matter molecules with the soil's solid phase is a key factor influencing the stabilization of carbon in soils and thus forms a crucial aspect of the global carbon cycle. While subject of much research attention so far, we still have much to learn about such interactions at the molecular level; in particular in the light of competition between different classes of organic molecules and in the presence of previously adsorbed soil organic matter. We studied the interaction of a group of low molecular weight (LMW) aromatic acids (salicylic, syringic, vanillic and ferulic acid) and amino acids (lysine, glutamic, leucine and phenylalanine) on goethite, kaolinite and bentonite with and without previously adsorbed dissolved organic matter (DOM). For this we used batch experiments at pH = 6.0 where some of the organic compounds were positively charged (i.e. lysine) or negatively charged (i.e. glutamic and salicylic acid) while the minerals also displayed positively (i.e. goethite) or negatively charged surfaces (i.e. bentonite). We found much higher sorption of salicylic acid and lysine than other compounds. On the bare minerals we found a great variety of sorption strength, with salicylic acid strongly adsorbed, while syringic, vanillic and ferulic acid showed little or no adsorption. For the amino acids, protonated lysine showed a stronger affinity to negatively charged kaolinite and bentonite than other amino acids. While deprotonated glutamic acid showed the strongest adsorption on goethite. Leucine and phenylalanine showed hardly any adsorption on any of the minerals. When present concurrently, amino acids decreased the sorption of salicylic acid on the three types of mineral, while the presence of LMW aromatic acids increased the sorption of lysine on kaolinite and bentonite and the sorption of glutamic acid on goethite. The presence of previously adsorbed DOM reduced the sorption of salicylic acid and lysine. The results confirm that interactions of different classes of organic molecules with solid soil phases cannot be understood in isolation, but must be interpreted in the context of the presence of other classes of molecules. It seems that the presence of methoxy groups decreases the adsorption of aromatic acids to minerals. We did not find evidence for protein conditioning of any mineral surface, i.e. increased adsorption of aromatic acids after adsorption of amino acids.

Investigating the chlorination of acidic pharmaceuticals and by-product formation aided by an experimental design methodology.

PubMed

Quintana, José Benito; Rodil, Rosario; López-Mahía, Purificación; Muniategui-Lorenzo, Soledad; Prada-Rodríguez, Darío

2010-01-01

The degradation of seven acidic drugs and two metabolites during chlorination was investigated by liquid chromatography-mass spectrometry (LC-MS). A triple-quadrupole (QqQ) system was used to follow the time course of the pharmaceuticals and by-products, while a quadrupole time-of-flight (Q-TOF) system was also used for the identification of the by-products. Under strong chlorination conditions (10mg/L Cl(2), 24h), only four of the target compounds were significantly degraded: salicylic acid, naproxen, diclofenac and indomethacine. The degradation kinetics of these four compounds were investigated at different concentrations of chlorine, bromide and pH by means of a Box-Behnken experimental design. Depending on these factors, measured pseudo-first order half-lives were in the ranges: 23-573h for salicylic acid, 13-446min for naproxen, 5-328min for diclofenac and 0.4-13.4min for indomethacine. Also, it was observed that chlorine concentration was the overall most significant factor, followed by the bromide concentration (except for indomethacine), resulting in increased degradation kinetics as they are increased. The degradation path of salicylic acid, naproxen and diclofenac consisted of aromatic substitution of one or two hydrogens by chlorine and/or bromide. Moreover, for diclofenac, two other by-products corresponding to a decarboxylation/hydroxylation pathway from the monohalogenated products were also identified. On the other hand, indomethacine degradation did not lead to halogenation products but to oxidation ones. The investigation of these by-products in real samples by LC-MS/MS (QqQ) showed that the halogenated derivates of salicylic acid occurred in all the drinking water and wastewater samples analysed.

Herbivore specificity and the chemical basis of plant-plant communication in Baccharis salicifolia (Asteraceae).

PubMed

Moreira, Xoaquín; Nell, Colleen S; Katsanis, Angelos; Rasmann, Sergio; Mooney, Kailen A

2016-09-06

It is well known that plant damage by leaf-chewing herbivores can induce resistance in neighbouring plants. It is unknown whether such communication occurs in response to sap-feeding herbivores, whether communication is specific to herbivore identity, and the chemical basis of communication, including specificity. We carried out glasshouse experiments using the California-native shrub Baccharis salicifolia and two ecologically distinct aphid species (one a dietary generalist and the other a specialist) to test for specificity of plant-plant communication and to document the underlying volatile organic compounds (VOCs). We show specificity of plant-plant communication to herbivore identity, as each aphid-damaged plant only induced resistance in neighbours against the same aphid species. The amount and composition of induced VOCs were markedly different between plants attacked by the two aphid species, providing a putative chemical mechanism for this specificity. Furthermore, a synthetic blend of the five major aphid-induced VOCs (ethanone, limonene, methyl salicylate, myrcene, ocimene) triggered resistance in receiving plants of comparable magnitude to aphid damage of neighbours, and the effects of the blend exceeded those of individual compounds. This study significantly advances our understanding of plant-plant communication by demonstrating the importance of sap-feeding herbivores and herbivore identity, as well as the chemical basis for such effects. © 2016 The Authors. New Phytologist © 2016 New Phytologist Trust.

The respiratory local lymph node assay as a tool to study respiratory sensitizers.

PubMed

Arts, Josje H E; de Jong, Wim H; van Triel, Jos J; Schijf, Marcel A; de Klerk, Arja; van Loveren, Henk; Kuper, C Frieke

2008-12-01

The local lymph node assay (LLNA) is used to test the potential of low molecular weight (LMW) compounds to induce sensitization via the skin. In the present study, a respiratory LLNA was developed. Male BALB/c mice were exposed head/nose-only during three consecutive days for 45, 90, 180, or 360 min/day to various LMW allergens. Ear application (skin LLNA) was used as a positive control. Negative controls were exposed to the vehicle. Three days after the last exposure, proliferation was determined in the draining mandibular lymph nodes, and the respiratory tract was examined microscopically. Upon inhalation, the allergens trimellitic anhydride, phthalic anhydride, hexamethylene diisocyanate, toluene diisocyanate, isophorone diisocyanate (IPDI), dinitrochlorobenzene, and oxazolone were positive and showed stimulation indices (SIs) up to 11, whereas trimeric IPDI, formaldehyde, and methyl salicylate were negative (viz. SI < 3). All compounds, except trimeric IPDI, induced histopathological lesions predominantly in the upper respiratory tract. Exposure by inhalation is a realistic approach to test respiratory allergens. However, based on the local toxicity, the dose that can be applied is (generally) much lower than can be achieved by skin application. It is concluded that strong LMW allergens, regardless their immunological nature, besides the skin can also sensitize the body via the respiratory tract. In addition, the contact allergens were as potent as the respiratory allergens, although the potency ranking differed from that in a skin LLNA.

Synthesis, spectroscopic characterizations, crystal structures and DFT studies of nalidixic acid carbonyl hydrazones derivatives

NASA Astrophysics Data System (ADS)

Bergamini, F. R. G.; Ribeiro, M. A.; Lancellotti, M.; Machado, D.; Miranda, P. C. M. L.; Cuin, A.; Formiga, A. L. B.; Corbi, P. P.

2016-09-01

This article describes the synthesis and characterization of the 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazide (hzd) and six carbonyl hydrazones derivatives of the nalidixic with 1H-pyrrol-2-ylmethylidene (hpyrr), 1H-imidazol-2-ylmethylidene (h2imi), pyridin-2-ylmethylidene (h2py), pyridin-3-ylmethylidene (h3py), pyridin-4-ylmethylidene(h4py) and (2-hydroxyphenyl)methylidene (hsali). The carbonyl hydrazones were characterized by elemental and ESI-QTOF-MS analyses, IR and detailed NMR spectroscopic measurements. The 2D NMR experiments allowed the unambiguous assignment of the hydrogen, carbon and nitrogen atoms, which have not been reported for nalidixic acid carbonyl hydrazone derivatives so far. Crystal structures of hzd and the new carbonyl hydrazones h2imi, hpyrr and h3py were determined by X-ray diffraction studies. Although the synthesis of hzd was reported decades ago, the hzd crystal structure have not been reported yet. Geometric optimizations of all the characterized structures were performed with the aid of DFT studies. Despite the fact that the hydrazones with 2-pyridine carboxylic acid (h2py) and salicyl aldehyde (hsali) were already reported by literature, a detailed spectroscopic study followed by DFT studies are also reported for such compounds in this manuscript. Antimicrobial studies of the compounds are also presented.

The Jasmonate Pathway Is a Key Player in Systemically Induced Defense against Root Knot Nematodes in Rice1[C

PubMed Central

Nahar, Kamrun; Kyndt, Tina; De Vleesschauwer, David; Höfte, Monica; Gheysen, Godelieve

2011-01-01

Complex defense signaling pathways, controlled by different hormones, are involved in the reaction of plants to a wide range of biotic and abiotic stress factors. We studied the ability of salicylic acid, jasmonate (JA), and ethylene (ET) to induce systemic defense in rice (Oryza sativa) against the root knot nematode Meloidogyne graminicola. Exogenous ET (ethephon) and JA (methyl jasmonate) supply on the shoots induced a strong systemic defense response in the roots, exemplified by a major up-regulation of pathogenesis-related genes OsPR1a and OsPR1b, while the salicylic acid analog BTH (benzo-1,2,3-thiadiazole-7-carbothioic acid S-methyl ester) was a less potent systemic defense inducer from shoot to root. Experiments with JA biosynthesis mutants and ET-insensitive transgenics showed that ET-induced defense requires an intact JA pathway, while JA-induced defense was still functional when ET signaling was impaired. Pharmacological inhibition of JA and ET biosynthesis confirmed that JA biosynthesis is needed for ET-induced systemic defense, and quantitative real-time reverse transcription-polymerase chain reaction data revealed that ET application onto the shoots strongly activates JA biosynthesis and signaling genes in the roots. All data provided in this study point to the JA pathway to play a pivotal role in rice defense against root knot nematodes. The expression of defense-related genes was monitored in root galls caused by M. graminicola. Different analyzed defense genes were attenuated in root galls caused by the nematode at early time points after infection. However, when the exogenous defense inducers ethephon and methyl jasmonate were supplied to the plant, the nematode was less effective in counteracting root defense pathways, hence making the plant more resistant to nematode infection. PMID:21715672

Enzymatic production and emission of floral scent volatiles in Jasminum sambac.

PubMed

Bera, Paramita; Mukherjee, Chiranjit; Mitra, Adinpunya

2017-03-01

Floral scent composed of low molecular weight volatile organic compounds. The sweet fragrance of any evening blooming flower is dominated by benzenoid and terpenoid volatile compounds. Floral scent of Jasminum sambac (Oleaceae) includes three major benzenoid esters - benzylacetate, methylbenzoate, and methylsalicylate and three major terpene compounds viz. (E)-β-ocimene, linalool and α-farnesene. We analyzed concentrations and emission rates of benzenoids and terpenoids during the developmental stages of J. sambac flower. In addition to spatial emission from different floral parts, we studied the time-course mRNA accumulations of phenylalanine ammonia-lyase (PAL) and the two representative genes of terpenoid pathway, namely 1-deoxy-d-xylulose 5-phosphate reductoisomerase (DXR) and terpene synthase (TPS). Further, in vitro activities of several enzymes of phenylpropanoid/benzenoid pathway viz., PAL and acetyl-coenzyme A: benzylalcohol acetyltransferase (BEAT), S-adenosyl-l-methionine: benzoic acid carboxyl methyl transferase (BAMT) and S-adenosyl-l-methionine: salicylic acid carboxyl methyltransferase (SAMT) were studied. All the above enzyme activities along with the in vitro activities of DXR and TPS were found to follow a certain rhythm as observed in the emission of different benzenoid and terpenoid compounds. Linalool emission peaked after petal opening and coincided with maximal expression of JsTPS gene as evidenced from RT-PCR analyses (semi-quantitative). The maximum transcript accumulation of this gene was observed in flower petals, indicating that the petals of J. sambac flower play an important role as a major contributor of volatile precursors. The transcripts accumulation of JsDXR and JsTPS in different developmental stages and in different floral part showed that emissions of terpenoid volatiles in J. sambac flower are partially regulated at transcription levels. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Volatile emissions from Aesculus hippocastanum induced by mining of larval stages of Cameraria ohridella influence oviposition by conspecific females.

PubMed

Johne, A Bettina; Weissbecker, Bernhard; Schütz, Stefan

2006-10-01

Larval stages of the horse chestnut leafminer Cameraria ohridella can completely destroy the surface of horse chestnut leaves, Aesculus hippocastanum. This study investigated the effect of the degree of leaf browning caused by the insect's larvae on olfactory detection, aggregation, and oviposition of C. ohridella adults. The influence of A. hippocastanum flower scent on oviposition of the first generation was also evaluated. Utilizing gas chromatography coupled with parallel detection by mass spectrometry and electroantennography (GC-MS/EAD), more than 30 compounds eliciting responses from antennae of C. ohridella were detected. Oviposition and mining by C. ohridella caused significant changes in the profile of leaf volatiles of A. hippocastanum. After oviposition and subsequent mining by early larval stages (L1-L3), substances such as benzaldehyde, 1,8-cineole, benzyl alcohol, 2-phenylethanol, methyl salicylate, (E)-beta-caryophyllene, and (E,E)-alpha-farnesene were emitted in addition to the compounds emitted by uninfested leaves. Insects were able to detect these compounds. The emitted amount of these substances increased with progressive larval development. During late larval stages (L4, L5) and severe loss of green leaf area, (E,E)-2,4-hexadienal, (E/Z)-linalool oxide (furanoid), nonanal, and decanal were also released by leaves. These alterations of the profile of volatiles caused modifications in aggregation of C. ohridella on leaves. In choice tests, leaves in early infestation stages showed no significant effect on aggregation, whereas insects avoided leaves in late infestation stages. Further choice tests with leaves treated with single compounds led to the identification of substances mediating an increase or decrease in oviposition.

Molecular mechanisms of transformation of C3H/10T1/2 C1 8 mouse embryo cells and diploid human fibroblasts by carcinogenic metal compounds.

PubMed Central

Landolph, J R

1994-01-01

Carcinogenic arsenic, nickel, and chromium compounds induced morphological and neoplastic transformation but no mutation to ouabain resistance in 10T1/2 mouse embryo cells; lead chromate also did not induce mutation to ouabain or 6-thioguanine resistance in Chinese hamster ovary cells. The mechanism of metal-induced morphological transformation was likely not due to the specific base substitution mutations measured in ouabain resistance mutation assays, and for lead chromate, likely not due to this type of base substitution mutation or to frameshift mutations. Preliminary data indicate increases in steady-state levels of c-myc RNA in arsenic-, nickel-, and chromium-transformed cell lines. We also showed that carcinogenic nickel, chromium, and arsenic compounds and N-methyl-N-nitro-N-nitrosoguanidine (MNNG) induced stable anchorage independence (Al) in diploid human fibroblasts (DHF) but no focus formation or immortality. Nickel subsulfide and lead chromate induced Al but not mutation to 6-thioguanine resistance. The mechanism of induction of Al by metal salts in DHF was likely not by the type of base substitution or frameshift mutations measured in these assays. MNNG induced Al, mutation to 6-thioguanine resistance, and mutation to ouabain resistance, and might induce Al by base substitution or frameshift mutations. Dexamethasone, aspirin, and salicylic acid inhibited nickel subsulfide, MNNG, and 12-O-tetrade-canoylphorbol-13-acetate (TPA)-induced Al in DHF, suggesting that arachidonic acid metabolism and oxygen radical generation play a role in induction of Al. We propose that nickel compounds stimulate arachidonic acid metabolism, consequent oxygen radical generation, and oxygen radical attack upon DNA.(ABSTRACT TRUNCATED AT 250 WORDS) Images Figure 1. PMID:7843085

Data Fusion Analysis for Range Test Validation System

DTIC Science & Technology

2010-07-14

simulants were released during the RTVS ’08 test series: triethyl phosphate (TEP), methyl salicylate (MeS), and acetic acid (AA). A total of 29 release...the combination of a grid of point sensors at ground level and a standoff FTIR system monitoring above ground areas proved effective in detecting the...presence of simulants over the test grid. A Dempster-Shafer approach for data fusion was selected as the most effective strategy for RTVS data fusion

Bioinspired Surface Treatments for Improved Decontamination: Fluoro-Plasma Treatment

DTIC Science & Technology

2017-07-21

methyl salicylate (right) immediately following liquid application (top) and 5 min after liquid application (bottom): painted coupon (A), C2F6, 50 W...applied at 0° after which the supporting platform angle was gradually increased up to 60°. Sliding angles for each of the liquids were identified as the...angle for which movement of the droplet was identified. Shedding angles for each liquid were determined using 12 µL droplets initiated 2.5 cm above

Methyl salicylate 2-O-β-d-lactoside alleviates the pathological progression of pristane-induced systemic lupus erythematosus-like disease in mice via suppression of inflammatory response and signal transduction

PubMed Central

He, Yang-Yang; Yan, Yu; Zhang, Hui-Fang; Lin, Yi-Huang; Chen, Yu-Cai; Yan, Yi; Wu, Ping; Fang, Jian-Song; Yang, Shu-Hui; Du, Guan-Hua

2016-01-01

Systemic lupus erythematosus (SLE), with a high incidence rate and insufficient therapy worldwide, is a complex disease involving multiple organs characterized primarily by inflammation due to deposition of immunocomplexes formed by production of autoantibodies. The mechanism of SLE remains unclear, and the disease still cannot be cured. We used pristane to induce SLE in female BALB/c mice. Methyl salicylate 2-O-β-d-lactoside (MSL; 200, 400, and 800 mg/kg) was orally administered 45 days after pristane injection for 4.5 months. The results showed that MSL antagonized the increasing levels of multiple types of antibodies and cytokines in lupus mice. MSL was found to suppress joint swelling and have potent inhibitory effect on arthritis-like symptoms. MSL also significantly decreased the spleen index and expression of inflammatory markers in the lupus mice. MSL protected the kidneys of lupus mice from injury through inhibiting the expression of inflammatory cytokines and reducing the IgG and C3 immunocomplex deposits. Further Western blot assays revealed that the downregulation of the intracellular inflammatory signals of NFκB and JAK/STAT3 might be the potential molecular mechanisms of the pharmacological activity of MSL against SLE in vivo. These findings may demonstrate that MSL has the potential to be a useful and highly effective treatment for SLE. PMID:27729775

Expression of Allene Oxide Synthase Determines Defense Gene Activation in Tomato1

PubMed Central

Sivasankar, Sobhana; Sheldrick, Bay; Rothstein, Steven J.

2000-01-01

Allene oxide synthase (AOS; hydroperoxide dehydratase; EC 4.2.1.92) catalyzes the first step in the biosynthesis of jasmonic acid from lipoxygenase-derived hydroperoxides of free fatty acids. Using the AOS cDNA from tomato (Lycopersicon esculentum), in which the role of jasmonic acid in wound-induced defense gene activation has been best described, we examined the kinetics of AOS induction in response to wounding and elicitors, in parallel with that of the wound-inducible PIN II (proteinase inhibitor II) gene. AOS was induced in leaves by wounding, systemin, 12-oxophytodienoic acid, and methyl jasmonate. The levels of AOS mRNA started declining by 4 h after induction, whereas the levels of PIN II mRNA continued to increase up to 20 h after induction. Salicylic acid inhibited AOS and PIN II expression, and the addition of 12-oxophytodienoic acid or methyl jasmonate did not prevent the inhibition of PIN II expression in the presence of salicylic acid. Ethylene induced the expression of AOS, but the presence of ethylene alone did not produce an optimal induction of PIN II. The addition of silver thiosulfate, an ethylene action inhibitor, prevented the wound-induced expression of both AOS and PIN II. Products of hydroperoxide lyase affected neither AOS nor PIN II, but induced expression of prosystemin. Based on these results, we propose an updated model for defense gene activation in tomato. PMID:10759530

Avocado roots treated with salicylic acid produce phenol-2,4-bis (1,1-dimethylethyl), a compound with antifungal activity.

PubMed

Rangel-Sánchez, Gerardo; Castro-Mercado, Elda; García-Pineda, Ernesto

2014-02-15

We demonstrated the ability of salicylic acid (SA) to induce a compound in avocado roots that strengthens their defense against Phytophthora cinnamomi. The SA content of avocado roots, before and after the application of exogenous SA, was determined by High-Performance Liquid Chromatography (HPLC). After 4h of SA feeding, the endogenous level in the roots increased to 223 μg g(-1) FW, which was 15 times the amount found in control roots. The methanolic extract obtained from SA-treated avocado roots inhibited the radial growth of P. cinnamomi. A thin layer chromatographic bioassay with the methanolic extract and spores of Aspergillus showed a distinct inhibition zone. The compound responsible for the inhibition was identified as phenol-2,4-bis (1,1-dimethylethyl) by gas chromatography and mass spectrometry. At a concentration of 100 μg/mL, the substance reduced germinative tube length in Aspergillus and radial growth of P. cinnamomi. A commercial preparation of phenol-2,4-bis (1,1-dimethylethyl) caused the same effects on mycelium morphology and radial growth as our isolate, confirming the presence of this compound in the root extracts. This is the first report of the induction of this compound in plants by SA, and the results suggest that it plays an important role in the defense response of avocado. Copyright © 2013 Elsevier GmbH. All rights reserved.

Development of Candidate Chemical Simulant List: The Evaluation of Candidate Chemical Simulants Which May Be Used in Chemically Hazardous Operations

DTIC Science & Technology

1982-12-01

generation FDA Food and Drug Administration (U.S.A.) FEMA Flavoring Extract Manufacturer’s Associatic. FID Flame ionization detector FPD Flame...medicinally in the form of local analgesic or anti-inflammatory ointmer,ts or liniments S (Collins et al., 1971). It was given GRAS status by the Flavor ...methyl salicylate is considered safe for use as a flavoring agent in various foods when added in low concentrations, it has been found to be acutely

Expression of tumor necrosis factor-α and interleukin-1β genes in the cochlea and inferior colliculus in salicylate-induced tinnitus

PubMed Central

2011-01-01

Background Changes in the gene expressions for tumor necrosis factor-α (TNF-α) and/or interleukin-1β (IL-1β) during tinnitus have not been previously reported. We evaluated tinnitus and mRNA expression levels of TNF-α, IL-1β, and N-methyl D-aspartate receptor subunit 2B (NR2B) genes in cochlea and inferior colliculus (IC) of mice after intraperitoneal injections of salicylate. Methods Forty-eight 3-month-old male SAMP8 mice were randomly and equally divided into two groups: salicylate-treated and saline-treated. All mice were trained to perform an active avoidance task for 5 days. Once conditioned, an active avoidance task was performed 2 hours after daily intraperitoneal injections of saline, either alone or containing 300 mg/kg sodium salicylate. Total numbers of times (tinnitus score) the mice climbed during the inter-trial silent period for 10 trials were recorded daily for 4 days (days 7 to 10), and then mice were euthanized for determination of mRNA expression levels of TNF-α, IL-1β, and NR2B genes in cochlea and IC at day 10. Results Tinnitus scores increased in response to daily salicylate treatments. The mRNA expression levels of TNF-α increased significantly for the salicylate-treated group compared to the control group in both cochlea (1.89 ± 0.22 vs. 0.87 ± 0.07, P < 0.0001) and IC (2.12 ± 0.23 vs. 1.73 ± 0.22, p = 0.0040). mRNA expression levels for the IL-1β gene also increased significantly in the salicylate group compared to the control group in both cochlea (3.50 ± 1.05 vs. 2.80 ± 0.28, p < 0.0001) and IC (2.94 ± 0.51 versus 1.24 ± 0.52, p = 0.0013). Linear regression analysis revealed a significant positive association between tinnitus scores and expression levels of TNF-α, IL-1β, and NR2B genes in cochlea and IC. In addition, expression levels of the TNF-α gene were positively correlated with those of the NR2Bgene in both cochlea and IC; whereas, the expression levels of the IL-1β gene was positively correlated with that of the NR2B gene in IC, but not in cochlea. Conclusion We conclude that salicylate treatment resulting in tinnitus augments expression of the TNF-α and IL-1β genes in cochlea and IC of mice, and we suggest that these proinflammatory cytokines might lead to tinnitus directly or via modulating the NMDA receptor. PMID:21477330

Percutaneous absorption of several chemicals, some pesticides included, in the red-winged blackbird

USGS Publications Warehouse

Rogers, J.G.; Cagan, R.H.; Kare, M.R.

1974-01-01

Percutaneous absorption in vivo through the skin of the feet of the red-winged blackbird (Agelaius phoeniceus) has been investigated. Absorption after 18-24 hours exposure to 0.01 M solutions of salicylic acid, caffeine, urea, 2,4-D, dieldrin, diethylstilbesterol, and DDT was measured. Of these, only DDT and diethylstilbesterol were not absorbed to a measurable degree. The solvents ethanol, dimethylsulfoxide (DMSO), and vegetable oil were compared with water in their effects on the absorption ofcaffeine, urea, and salicylic acid. Ethanol, DMSO,and oil each decreased percutaneous absorption of salicylic acid. DMSO increased absorption of caffeine, and ethanol had no effect on it. Neither DMSO nor ethanol affected penetration of urea. Partition coefficients (K) (epidermis/water) were determined for all seven penetrants. Compounds with higher values of K showed lower percutaneous absorption. These findings suggest that K may be useful to predict percutaneous absorption in vivo. It appears unlikely that percutaneous absorption contributes greatly to the body burden of 2,4-D and dieldrin in A. phoeniceus.

REMOVAL BY COAGULATION OF TRACE ORGANICS FROM MISSISSIPPI RIVER WATER

EPA Science Inventory

In the study alum and ferric sulfate were evaluated for their effectiveness in removing four low-molecular-weight organic compounds - C14-labeled octanoic acid, salicylic acid, phenol, and benzoic acid - from Mississippi River water and from water samples free of natural organic ...

Induction of gentisic acid 5-O-beta-D-xylopyranoside in tomato and cucumber plants infected by different pathogens.

PubMed

Fayos, Joaquín; Bellés, José María; López-Gresa, M Pilar; Primo, Jaime; Conejero, Vicente

2006-01-01

Tomato plants infected with the citrus exocortis viroid exhibited strongly elevated levels of a compound identified as 2,5-dihydroxybenzoic acid (gentisic acid, GA) 5-O-beta-D-xylopyranoside. The compound accumulated early in leaves expressing mild symptoms from both citrus exocortis viroid-infected tomato, and prunus necrotic ringspot virus-infected cucumber plants, and progressively accumulated concomitant with symptom development. The work presented here demonstrates that GA, mainly associated with systemic infections in compatible plant-pathogen interactions [Bellés, J.M., Garro, R., Fayos, J., Navarro, P., Primo, J., Conejero, V., 1999. Gentisic acid as a pathogen-inducible signal, additional to salicylic acid for activation of plant defenses in tomato. Mol. Plant-Microbe Interact. 12, 227-235], is conjugated to xylose. Notably, this result contrasts with those previously found in other plant-pathogen interactions in which phenolics analogues of GA as benzoic or salicylic acids, are conjugated to glucose.

Thermal Decomposition of Methyl Esters in Biodiesel Fuel: Kinetics, Mechanisms and Products

NASA Astrophysics Data System (ADS)

Chai, Ming

Biodiesel continues to enjoy increasing popularity. However, recent studies on carbonyl compounds emissions from biodiesel fuel are inconclusive. Emissions of carbonyl compounds from petroleum diesel fuels were compared to emissions from pure biodiesel fuels and petroleum-biodiesel blends used in a non-road diesel generator. The concentration of total carbonyl compounds was the highest when the engine was idling. The carbonyl emissions, as well as ozone formation potential, from biodiesel fuel blends were higher than those emitted from petroleum diesel fuel. The sulfur content of diesel fuel and the source of biodiesel fuel were not found to have a significant impact on emissions of carbonyl compounds. Mechanism parameters of the thermal decomposition of biodiesel-range methyl esters were obtained from the results of thermal gravimetric analysis (TGA). The overall reaction orders are between 0.49 and 0.71 and the energies of activation are between 59.9 and 101.3 kJ/mole. Methyl esters in air have lower activation energies than those in nitrogen. Methyl linoleate has the lowest activation energy, followed by methyl oleate, and methyl stearate. The pyrolysis and oxidation of the three methyl esters were investigated using a semi-isothermal tubular flow reactor. The profiles of major products versus reaction temperature are presented. In the pyrolysis of methyl stearate, the primary reaction pathway is the decarboxylic reaction at the methyl ester functional group. Methyl oleate's products indicate more reactions on its carbon-carbon double bond. Methyl linoleate shows highest reactivity among the three methyl esters, and 87 products were detected. The oxidation of three methyl esters resulted in more products in all compound classes, and 55, 114, and 127 products were detected, respectively. The oxidation of methyl esters includes decarboxylation on ester group. The methyl ester's carbon chain could be oxidized as a hydrocarbon compound and form oxidized esters and unsaturated esters, which have been observed in methyl ester's oxidation products. The oxidation of methyl stearate, methyl oleate and methyl linoleate produces 16, 28 and 34 types of carbonyl compounds, respectively. The unsaturated methyl ester forms more carbonyl compounds compared to the saturated methyl ester, which indicates the formation of carbonyl compounds might be more related to the unsaturated carbon bond rather than the methyl ester group. Good agreement between results for total carbon (TC) generally has been found, but the organic and elemental carbon (OC and EC) fractions determined by different methods often disagree. Lack of reference materials has impeded progress on method standardization and understanding method biases. As part of this dissertation, uniform carbon distribution for the filter sets is prepared by using a simply aerosol generation and collection method. The relative standard deviations for the mean TC, OC, and EC results reported by the seven laboratories were below 10%, 11% and 12% (respectively). The method of filter generation is generally applicable and reproducible. Depending on the application, different filter loadings and types of OC materials can be employed. Matched filter sets prepared by this approach can be used for determining the accuracy of various OC-EC methods and thereby contribute to method standardization.

Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran.

PubMed

Wang, Wei; Guo, Jia; Zhang, Junnan; Peng, Jie; Liu, Tianxing; Xin, Zhihong

2015-03-15

The bound phenolic compounds in rice bran were released and extracted with ethyl acetate based on alkaline digestion. An investigation of the chemical constituents of EtOAc extract has led to the isolation of a new compound, para-hydroxy methyl benzoate glucoside (8), together with nine known compounds, cycloeucalenol cis-ferulate (1), cycloeucalenol trans-ferulate (2), trans-ferulic acid (3), trans-ferulic acid methyl ester (4), cis-ferulic acid (5), cis-ferulic acid methyl ester (6), methyl caffeate (7), vanillic aldehyde (9) and para-hydroxy benzaldehyde (10). The structures of these compounds were determined using a combination of spectroscopic methods and chemical analysis. Among the compounds isolated, compound 3, 5 and 7 exhibited strong DPPH and ABTS(+) radical scavenging activities, followed by compounds 4 and 6. Compound 1 and 2 showed potent DPPH and ABTS(+) radical scavenging activities, compound 8 displayed moderate antioxidant activity against ABTS(+) radical, whereas compound 9 and 10 showed weak antioxidant activity. Copyright © 2014 Elsevier Ltd. All rights reserved.

Synthesis and characterization of copper complexes of Schiff base derived from isatin and salicylic hydrazide

DOE Office of Scientific and Technical Information (OSTI.GOV)

Lekshmy, R. K., E-mail: lekshmyulloor@gmail.com, E-mail: tharapradeepkumar@yahoo.com; Thara, G. S., E-mail: lekshmyulloor@gmail.com, E-mail: tharapradeepkumar@yahoo.com

A series of novel metal complexes of Schiff base have been prepared by the interaction of Cu(II) with isatin salicylic hydrazide. All the new compounds were characterized by elemental analysis, conductance measurement, magnetic moment determination, IR, UV, NMR, Mass and EPR spectral studies, thermal studies and microbial activities. The results indicate that the ligand acts as a tridentate chelating ligand coordinating through nitrogen and oxygen atoms. The ligand and complexes show inactive against Escherichia coli and active against Staphylococcus aureus and B.substilis. By analyzing the results of spectral, thermal and elemental analysis square planar geometry is proposed for all themore » complexes.« less

Salicylic acid regulates basal resistance to Fusarium head blight in wheat.

PubMed

Makandar, Ragiba; Nalam, Vamsi J; Lee, Hyeonju; Trick, Harold N; Dong, Yanhong; Shah, Jyoti

2012-03-01

Fusarium head blight (FHB) is a destructive disease of cereal crops such as wheat and barley. Previously, expression in wheat of the Arabidopsis NPR1 gene (AtNPR1), which encodes a key regulator of salicylic acid (SA) signaling, was shown to reduce severity of FHB caused by Fusarium graminearum. It was hypothesized that SA signaling contributes to wheat defense against F. graminearum. Here, we show that increased accumulation of SA in fungus-infected spikes correlated with elevated expression of the SA-inducible pathogenesis-related 1 (PR1) gene and FHB resistance. In addition, FHB severity and mycotoxin accumulation were curtailed in wheat plants treated with SA and in AtNPR1 wheat, which is hyper-responsive to SA. In support of a critical role for SA in basal resistance to FHB, disease severity was higher in wheat expressing the NahG-encoded salicylate hydroxylase, which metabolizes SA. The FHB-promoting effect of NahG was overcome by application of benzo (1,2,3), thiadiazole-7 carbothioic acid S-methyl ester, a synthetic functional analog of SA, thus confirming an important role for SA signaling in basal resistance to FHB. We further demonstrate that jasmonate signaling has a dichotomous role in wheat interaction with F. graminearum, constraining activation of SA signaling during early stages of infection and promoting resistance during the later stages of infection.

Antiprotozoal and antimicrobial compounds from the plant pathogen Septoria pistaciarum.

PubMed

Kumarihamy, Mallika; Khan, Shabana I; Jacob, Melissa; Tekwani, Babu L; Duke, Stephen O; Ferreira, Daneel; Nanayakkara, N P Dhammika

2012-05-25

Four new 1,4-dihydroxy-5-phenyl-2-pyridinone alkaloids, 17-hydroxy-N-(O-methyl)septoriamycin A (1), 17-acetoxy-N-(O-methyl)septoriamycin A (2), 13-(S)-hydroxy-N-(O-methyl)septoriamycin A (3), and 13-(R)-hydroxy-N-(O-methyl)septoriamycin A (4), together with the known compounds (+)-cercosporin (5), (+)-14-O-acetylcercosporin (6), (+)-di-O-acetylcercosporin (7), lumichrome, and brassicasterol, were isolated from an ethyl acetate extract of a culture medium of Septoria pistaciarum. Methylation of septoriamycin A (8) with diazomethane yielded three di-O-methyl analogues, two of which existed as mixtures of rotamers. We previously reported antimalarial activity of septoriamycin A. This compound also exhibited significant activity against Leishmania donovani promastigotes. Compounds 5-7 showed moderate in vitro activity against L. donovani promastigotes and chloroquine-sensitive (D6) and -resistant (W2) strains of Plasmodium falciparum, whereas compound 5 was fairly active against methicillin-sensitive and methicillin-resistant strains of Staphylococcus aureus. Compounds 5-7 also displayed moderate phytotoxic activity against both a dicot (lettuce, Lactuca sativa) and a monocot (bentgrass, Agrostis stolonifera) and cytotoxicity against a panel of cell lines.

Chemodiversity and biodiversity of fungi associated with the pine weevil Hylobius abietis.

PubMed

Azeem, Muhammad; Terenius, Olle; Rajarao, Gunaratna Kuttuva; Nagahama, Kazuhiro; Nordenhem, Henrik; Nordlander, Göran; Borg-Karlson, Anna-Karin

2015-08-01

The pine weevil Hylobius abietis is a severe pest of conifer seedlings in reforestation areas. Weevils lay eggs in the root bark or in the soil near roots of recently dead trees and cover the eggs with frass (feces combined with chewed bark), possibly to avoid conspecific egg predation. The aim of the present investigation focused on isolation, identification, and volatile production of fungi from pine-weevil feces and frass. Fungi were isolated from weevil frass and feces separately, followed by identification based on ITS sequencing. Fifty-nine isolates belonging to the genera Penicillium, Ophiostoma, Mucor, Leptographium, Eucasphaeria, Rhizosphaera, Debaryomyces, and Candida were identified. Volatile organic compounds (VOCs) produced by the fungal community and fungal isolates cultured on weevil-frass broth were identified by SPME-GCMS. Major VOCs emitted from the fungal community and pure isolates were species- and strain specific and included isopentylalcohol, styrene, 3-octanone, 6-protoilludene, methyl salicylate, 3-methylanisole, 2-methoxyphenol, and phenol. Some of these are known to influence the orientation of pine weevils when tested among highly attractive newly planted conifer seedlings. Copyright © 2015 The British Mycological Society. Published by Elsevier Ltd. All rights reserved.

Vapor containment tests of the rapid response system glovebox. Final report, December 1995-April 1996

DOE Office of Scientific and Technical Information (OSTI.GOV)

Arca, V.J.; Blewett, W.K.; Kinne, W.E.

1996-10-01

The Rapid Response System (RRS) is a trailer-mounted facility for demilitarizing Chemical Agent Identification Sets (CAIS), obsolete training kits containing ampules and/or bottles of chemical warfare agents (mustard and lewisite), or other industrial chemical compounds. The main component of the RRS is a glovebox divided into three areas - an airlock station, unpack station, and neutralization station, and the CAIS items are processed through each station by use of 11 glove ports. The glovebox is maintained at negative pressure differential by a gas-particulate filter-blower unit. To measure the performance of the glovebox in containing chemical vapors/gases, a series of testsmore » was conducted on 811 April 1996 at Tooele Army Depot, UT, with methyl salicylate, a simulant for mustard. This testing addressed performance in steady state operation, airlock cycling, waste barrel changeout, and glove changeout. Two trials were also conducted in a simulated power-failure condition to determine the rate of leakage if system airflow is interrupted. The glovebox and its engineering controls provided a very high level of protection. Some procedural changes were recommended to increase the protection factor in glove and barrel changeout operations.« less

The plastidial retrograde signal methyl erythritol cyclopyrophosphate is a regulator of salicylic acid and jasmonic acid crosstalk

PubMed Central

Lemos, Mark; Xiao, Yanmei; Bjornson, Marta; Wang, Jin-zheng; Hicks, Derrick; de Souza, Amancio; Wang, Chang-Quan; Yang, Panyu; Ma, Shisong; Dinesh-Kumar, Savithramma; Dehesh, Katayoon

2016-01-01

The exquisite harmony between hormones and their corresponding signaling pathways is central to prioritizing plant responses to simultaneous and/or successive environmental trepidations. The crosstalk between jasmonic acid (JA) and salicylic acid (SA) is an established effective mechanism that optimizes and tailors plant adaptive responses. However, the underlying regulatory modules of this crosstalk are largely unknown. Global transcriptomic analyses of mutant plants (ceh1) with elevated levels of the stress-induced plastidial retrograde signaling metabolite 2-C-methyl-D-erythritol cyclopyrophosphate (MEcPP) revealed robustly induced JA marker genes, expected to be suppressed by the presence of constitutively high SA levels in the mutant background. Analyses of a range of genotypes with varying SA and MEcPP levels established the selective role of MEcPP-mediated signal(s) in induction of JA-responsive genes in the presence of elevated SA. Metabolic profiling revealed the presence of high levels of the JA precursor 12-oxo-phytodienoic acid (OPDA), but near wild type levels of JA in the ceh1 mutant plants. Analyses of coronatine-insensitive 1 (coi1)/ceh1 double mutant plants confirmed that the MEcPP-mediated induction is JA receptor COI1 dependent, potentially through elevated OPDA. These findings identify MEcPP as a previously unrecognized central regulatory module that induces JA-responsive genes in the presence of high SA, thereby staging a multifaceted plant response within the environmental context. PMID:26733689

Suitability of macrophage inflammatory protein-1beta production by THP-1 cells in differentiating skin sensitizers from irritant chemicals.

PubMed

Lim, Yeon-Mi; Moon, Seong-Joon; An, Su-Sun; Lee, Soo-Jin; Kim, Seo-Young; Chang, Ih-Seop; Park, Kui-Lea; Kim, Hyoung-Ah; Heo, Yong

2008-04-01

Worldwide restrictions in animal use for research have driven efforts to develop alternative methods. The study aimed to test the efficacy of the macrophage inflammatory protein-1beta (MIP-1beta) assay for testing chemicals' skin-sensitizing capacity. The assay was performed using 9 chemicals judged to be sensitizing and 7 non-sensitizing by the standard in vivo assays. THP-1 cells were cultured in the presence or absence of 4 doses, 0.01x, 0.1x, 0.5x, or 1x IC(50) (50% inhibitory concentration for THP-1 cell proliferation) of these chemicals for 24 hr, and the MIP-1beta level in the supernatants was determined. Skin sensitization by the test chemicals was determined by MIP-1beta production rates. The MIP-1beta production rate was expressed as the relative increase in MIP-1beta production in response to chemical treatment compared with vehicle treatment. When the threshold MIP-1beta production rate used was 100% or 105% of dimethyl sulfoxide, all the sensitizing chemicals tested (dinitrochlorobenzene, hexyl cinnamic aldehyde, eugenol, hydroquinone, dinitrofluorobenzene, benzocaine, nickel, chromium, and 5-chloro-2-methyl-4-isothiazolin-3-one) were positive, and all the non-sensitizing chemicals (methyl salicylate, benzalkonium chloride, lactic acid, isopropanol, and salicylic acid), with the exception of sodium lauryl sulfate, were negative for MIP-1beta production. These results indicate that MIP-1beta could be a biomarker for classification of chemicals as sensitizers or non-sensitizers.

Low concentrations of salicylic acid delay methyl jasmonate-induced leaf senescence by up-regulating nitric oxide synthase activity.

PubMed

Ji, Yingbin; Liu, Jian; Xing, Da

2016-09-01

In plants, extensive efforts have been devoted to understanding the crosstalk between salicylic acid (SA) and jasmonic acid (JA) signaling in pathogen defenses, but this crosstalk has scarcely been addressed during senescence. In this study, the effect of SA application on methyl jasmonate (MeJA)-induced leaf senescence was assessed. We found that low concentrations of SA (1-50 μM) played a delayed role against the senescence promoted by MeJA. Furthermore, low concentrations of SA enhanced plant antioxidant defenses and restricted reactive oxygen species (ROS) accumulation in MeJA-treated leaves. When applied simultaneously with MeJA, low concentrations of SA triggered a nitric oxide (NO) burst, and the elevated NO levels were linked to the nitric oxide associated 1 (NOA1)-dependent pathway via nitric oxide synthase (NOS) activity. The ability of SA to up-regulate plant antioxidant defenses, reduce ROS accumulation, and suppress leaf senescence was lost in NO-deficient Atnoa1 plants. In a converse manner, exogenous addition of NO donors increased the plant antioxidant capacity and lowered the ROS levels in MeJA-treated leaves. Taken together, the results indicate that SA at low concentrations counteracts MeJA-induced leaf senescence through NOA1-dependent NO signaling and strengthening of the antioxidant defense. © The Author 2016. Published by Oxford University Press on behalf of the Society for Experimental Biology. All rights reserved. For permissions, please email: journals.permissions@oup.com.

Thermal Stability Characteristics of Nitroaromatic Compounds.

DTIC Science & Technology

1986-09-15

of a methyl ortho to the nitro group in nitroaromatic compounds introduces a new element into the decomposition behavior of such compounds. Inasmuch...thus without the aid of acid, base or photon catalysis. It is clear that the presence of a methyl ortho to the nitro group in nitroaromatic compounds...particular interest in terms of the substance of this work is the drastic change in reaction product when a methyl group is ortho to the nitro . Furthermore

Antiprotozoal and antimicrobial compounds from the plant pathogen Septoria pistaciarum

USDA-ARS?s Scientific Manuscript database

Four new 1,4-dihydroxy-5-phenyl-2-pyridinone alkaloids, 17-hydroxy-N-(O-methyl)septoriamycin A (1), 17-acetoxy-N-(O-methyl)septoriamycin A (2), 13-(S)-hydroxy-N-(O-methyl)septoriamycin A (3) and 13-(R)-hydroxy-N-(O-methyl)septoriamycin A (4), together with the known compounds (+)-cercosporin (5), ...

Herbivore Damage and Prior Egg Deposition on Host Plants Influence the Oviposition of the Generalist Moth Trichoplusia ni (Lepidoptera: Noctuidae).

PubMed

Coapio, Guadalupe G; Cruz-López, Leopoldo; Guerenstein, Pablo; Malo, Edi A; Rojas, Julio C

2016-12-01

Female insects have the difficult task of locating host plants that maximize the survival and success of their offspring. In this study, the oviposition preferences of the cabbage looper moth, Trichoplusia ni (Hübner), for soybean plants, Glycine max (L.), under various treatments-undamaged, mechanically damaged, damaged by T. ni or Spodoptera frugiperda (Smith) larvae or by Bemisia tabaci (Gennadius) adults, egg-free plants, and plants previously oviposited by conspecific or heterospecific females (S. frugiperda)-were investigated using two-choice tests. Additionally, the volatile compounds emitted by the plants under the different treatments were identified by gas chromatography-mass spectrometry. Our results showed that females showed no preferences for undamaged or mechanically damaged plants. However, they oviposited more often on undamaged plants than on those previously damaged by T. ni, S. frugiperda, or B. tabaci. In contrast, females preferred to oviposit on plants previously oviposited by conspecific and heterospecific females than on egg-free plants. Plants damaged by conspecific or heterospecific larvae emitted methyl salicylate, indole, and octyl butyrate, compounds not released by undamaged or mechanically damaged plants. Whitefly damage induced the release of higher quantities of Z(3)-hexenyl acetate, (R)-(+)-limonene, and (E)-β-ocimene compared to plants damaged by larvae and suppressed the emission of linalool. Egg deposition by conspecific and heterospecific moths induced the emission of (R)-(+)-limonene, octyl butyrate, and geranyl acetone but suppressed the release of linalool. This study showed that a generalist moth species can discriminate between plants of different quality, and suggests that females use volatile compounds as cues during this process. © The Authors 2016. Published by Oxford University Press on behalf of Entomological Society of America. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

Response of predatory mites to a herbivore-induced plant volatile: genetic variation for context-dependent behaviour.

PubMed

Sznajder, Beata; Sabelis, Maurice W; Egas, Martijn

2010-07-01

Plants infested with herbivores release specific volatile compounds that are known to recruit natural enemies. The response of natural enemies to these volatiles may be either learned or genetically determined. We asked whether there is genetic variation in the response of the predatory mite Phytoseiulus persimilis to methyl salicylate (MeSa). MeSa is a volatile compound consistently produced by plants being attacked by the two-spotted spider mite, the prey of P. persimilis. We predicted that predators express genetically determined responses during long-distance migration where previously learned associations may have less value. Additionally, we asked whether these responses depend on odors from uninfested plants as a background to MeSa. To infer a genetic basis, we analyzed the variation in response to MeSa among iso-female lines of P. persimilis by using choice-tests that involved either (1) MeSa presented as a single compound or (2) MeSa with background-odor from uninfested lima bean plants. These tests were conducted for starved and satiated predators, i.e., two physiological states, one that approximates migration and another that mimics local patch exploration. We found variation among iso-female lines in the responses to MeSa, thus showing genetic variation for this behavior. The variation was more pronounced in the starved predators, thus indicating that P. persimilis relies on innate preferences when migrating. Background volatiles of uninfested plants changed the predators' responses to MeSa in a manner that depended on physiological state and iso-female line. Thus, it is possible to select for context-dependent behavioral responses of natural enemies to plant volatiles.

Response of Predatory Mites to a Herbivore-Induced Plant Volatile: Genetic Variation for Context-Dependent Behaviour

PubMed Central

Sabelis, Maurice W.; Egas, Martijn

2010-01-01

Plants infested with herbivores release specific volatile compounds that are known to recruit natural enemies. The response of natural enemies to these volatiles may be either learned or genetically determined. We asked whether there is genetic variation in the response of the predatory mite Phytoseiulus persimilis to methyl salicylate (MeSa). MeSa is a volatile compound consistently produced by plants being attacked by the two-spotted spider mite, the prey of P. persimilis. We predicted that predators express genetically determined responses during long-distance migration where previously learned associations may have less value. Additionally, we asked whether these responses depend on odors from uninfested plants as a background to MeSa. To infer a genetic basis, we analyzed the variation in response to MeSa among iso-female lines of P. persimilis by using choice-tests that involved either (1) MeSa presented as a single compound or (2) MeSa with background-odor from uninfested lima bean plants. These tests were conducted for starved and satiated predators, i.e., two physiological states, one that approximates migration and another that mimics local patch exploration. We found variation among iso-female lines in the responses to MeSa, thus showing genetic variation for this behavior. The variation was more pronounced in the starved predators, thus indicating that P. persimilis relies on innate preferences when migrating. Background volatiles of uninfested plants changed the predators’ responses to MeSa in a manner that depended on physiological state and iso-female line. Thus, it is possible to select for context-dependent behavioral responses of natural enemies to plant volatiles. PMID:20574785

Individual Protection Testing (Task 5 - Qualitative Fit Test Simulants)

DTIC Science & Technology

1990-04-01

2- octanol 0 .00026(b) 506,000 * 2- octanone 248 4 A n-octylacetate 0.21 2,500 A Paracresol 0.001 D Pelargonic acid .00084(b) 164,000 * n-pentane 990...77 Unpleasant [107-92-6] Cinnamaldehyde-CgH80 2.5 53,000 -- 246 ---- [104-55-2] Methyl salicylate-C8H803 0.58 113,400 -- 224 99 -- [119-36-8] 2- octanol ...of the literature assessment are summarized in Table 2. Bromoacetone was eliminated because of its high acute toxicity. The candidate, 2- octanol , was

Lack of dose dependent kinetics of methyl salicylate-2-O-β-D-lactoside in rhesus monkeys after oral administration.

PubMed

He, Yangyang; Yan, Yu; Zhang, Tiantai; Ma, Yinzhong; Zhang, Wen; Wu, Ping; Song, Junke; Wang, Shuang; Du, Guanhua

2015-04-22

Methyl salicylate-2-O-β-d-lactoside (MSL) is one of the main active components isolated from Gaultheria yunnanensis, which is a traditional Chinese medicine used to treat arthritis and various aches and pains. Pharmacological researches showed that MSL had various effective activities in both in vivo and in vitro experiments. However, the pharmacokinetics features and oral bioavailability of MSL in primates were not studied up to now. To study the pharmacokinetics of different doses of MSL in rhesus monkeys and investigate the absolute bioavailability of MSL after oral administration. Male and female rhesus monkeys were either orally administrated with MSL 200, 400 and 800 mg/kg or received an intravenous dose of 20mg/kg randomly. The levels of MSL and salicylic acid (SA) in plasma were simultaneous measured by a simple, sensitive and reproducible high performance liquid chromatography method. Mean peak plasma concentration values for groups treated with 200, 400 and 800 mg/kg doses ranged from 48.79 to 171.83 μg/mL after single-dose oral administration of MSL, and mean area under the concentration-time curve values ranged from 195.16 to 1107.76 μg/mL h. Poor linearity of the kinetics of SA after oral administration of MSL was observed in the regression analysis of the Cmax-dose plot (r(2)=0.812), CL-dose plot (r(2)=0.225) and AUC(0-t)-dose plot (r(2)=0.938). Absolute bioavailability of MSL was assessed to be 118.89 ± 57.50, 213.54 ± 58.98 and 168.72 ± 76.58%, respectively. Bioavailability of MSL after oral administration in rhesus monkeys was measured for the first time. Pharmacokinetics parameters did not appear to be dose proportional among the three oral doses of treatments, and MSL showed an apparent absolute bioavailability in excess of 100% in rhesus monkeys based on the present study. In addition, a rapid, sensitive and reliable HPLC method was established and demonstrated for the research of traditional Chinese medicine in this study. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

Mercury methylation in mine wastes collected from abandoned mercury mines in the USA

USGS Publications Warehouse

Gray, J.E.; Hines, M.E.; Biester, H.; Lasorsa, B.K.; ,

2003-01-01

Speciation and transformation of Hg was studied in mine wastes collected from abandoned Hg mines at McDermitt, Nevada, and Terlingua, Texas, to evaluate formation of methyl-Hg, which is highly toxic. In these mine wastes, we measured total Hg and methyl-Hg contents, identified various Hg compounds using a pyrolysis technique, and determined rates of Hg methylation and methyl-Hg demethylation using isotopic-tracer methods. Mine wastes contain total Hg contents as high as 14000 ??g/g and methyl-Hg concentrations as high as 88 ng/g. Mine wastes were found to contain variable amounts of cinnabar, metacinnabar, Hg salts, Hg0, and Hg0 and Hg2+ sorbed onto matrix particulates. Samples with Hg0 and matrix-sorbed Hg generally contained significant methyl-Hg contents. Similarly, samples containing Hg0 compounds generally produced significant Hg methylation rates, as much as 26%/day. Samples containing mostly cinnabar showed little or no Hg methylation. Mine wastes with high methyl-Hg contents generally showed low methyl-Hg demethylation, suggesting that Hg methylation was dominant. Methyl-Hg demethylation was by both oxidative and microbial pathways. The correspondence of mine wastes containing Hg0 compounds and measured Hg methylation suggests that Hg0 oxidizes to Hg2+, which is subsequently bioavailable for microbial Hg methylation.

rgs-CaM Detects and Counteracts Viral RNA Silencing Suppressors in Plant Immune Priming

PubMed Central

Jeon, Eun Jin; Tadamura, Kazuki; Murakami, Taiki; Inaba, Jun-ichi; Kim, Bo Min; Sato, Masako; Atsumi, Go; Kuchitsu, Kazuyuki; Masuta, Chikara

2017-01-01

ABSTRACT Primary infection of a plant with a pathogen that causes high accumulation of salicylic acid in the plant typically via a hypersensitive response confers enhanced resistance against secondary infection with a broad spectrum of pathogens, including viruses. This phenomenon is called systemic acquired resistance (SAR), which is a plant priming for adaption to repeated biotic stress. However, the molecular mechanisms of SAR-mediated enhanced inhibition, especially of virus infection, remain unclear. Here, we show that SAR against cucumber mosaic virus (CMV) in tobacco plants (Nicotiana tabacum) involves a calmodulin-like protein, rgs-CaM. We previously reported the antiviral function of rgs-CaM, which binds to and directs degradation of viral RNA silencing suppressors (RSSs), including CMV 2b, via autophagy. We found that rgs-CaM-mediated immunity is ineffective against CMV infection in normally growing tobacco plants but is activated as a result of SAR induction via salicylic acid signaling. We then analyzed the effect of overexpression of rgs-CaM on salicylic acid signaling. Overexpressed and ectopically expressed rgs-CaM induced defense reactions, including cell death, generation of reactive oxygen species, and salicylic acid signaling. Further analysis using a combination of the salicylic acid analogue benzo-(1,2,3)-thiadiazole-7-carbothioic acid S-methyl ester (BTH) and the Ca2+ ionophore A23187 revealed that rgs-CaM functions as an immune receptor that induces salicylic acid signaling by simultaneously perceiving both viral RSS and Ca2+ influx as infection cues, implying its autoactivation. Thus, secondary infection of SAR-induced tobacco plants with CMV seems to be effectively inhibited through 2b recognition and degradation by rgs-CaM, leading to reinforcement of antiviral RNA silencing and other salicylic acid-mediated antiviral responses. IMPORTANCE Even without an acquired immune system like that in vertebrates, plants show enhanced whole-plant resistance against secondary infection with pathogens; this so-called systemic acquired resistance (SAR) has been known for more than half a century and continues to be extensively studied. SAR-induced plants strongly and rapidly express a number of antibiotics and pathogenesis-related proteins targeted against secondary infection, which can account for enhanced resistance against bacterial and fungal pathogens but are not thought to control viral infection. This study showed that enhanced resistance against cucumber mosaic virus is caused by a tobacco calmodulin-like protein, rgs-CaM, which detects and counteracts the major viral virulence factor (RNA silencing suppressor) after SAR induction. rgs-CaM-mediated SAR illustrates the growth versus defense trade-off in plants, as it targets the major virulence factor only under specific biotic stress conditions, thus avoiding the cost of constitutive activation while reducing the damage from virus infection. PMID:28724770

Antimicrobial Activity of 8-Quinolinols, Salicylic Acids, Hydroxynaphthoic Acids, and Salts of Selected Quinolinols with Selected Hydroxy-Acids

PubMed Central

Gershon, Herman; Parmegiani, Raulo

1962-01-01

Seventy-seven compounds were screened by the disc-plate method against strains of five bacteria and five fungi. A new constant was proposed to describe the antimicrobial activity of a compound in a defined system of organisms. This constant includes not only the inhibitory level of activity of the material but also the number of organisms inhibited. This constant, the antimicrobial spectrum index, was compared with the antimicrobial index of Albert. PMID:13898066

METHYLATED ASIII COMPOUNDS AS POTENTIAL PROXIMATE/ULTIMATE GENOTOXIC METABOLITES OF INORGANIC ARSENIC

EPA Science Inventory

METHYLATED Asm COMPOUNDS AS POTENTIAL PROXIMATE/ULTIMATE GENOTOXIC METABOLITES OF INORGANIC ARSENIC.

The methylation of inorganic arsenic has typically been viewed as a detoxification process. Genotoxicity tests have generally shown that arsenite has greater mutagenic p...

Strategy of Pseudomonas pseudoalcaligenes C70 for effective degradation of phenol and salicylate

PubMed Central

Heinaru, Eeva; Naanuri, Eve; Mehike, Maris; Leito, Ivo; Heinaru, Ain

2017-01-01

Phenol- and naphthalene-degrading indigenous Pseudomonas pseudoalcaligenes strain C70 has great potential for the bioremediation of polluted areas. It harbours two chromosomally located catechol meta pathways, one of which is structurally and phylogenetically very similar to the Pseudomonas sp. CF600 dmp operon and the other to the P. stutzeri AN10 nah lower operon. The key enzymes of the catechol meta pathway, catechol 2,3-dioxygenase (C23O) from strain C70, PheB and NahH, have an amino acid identity of 85%. The metabolic and regulatory phenotypes of the wild-type and the mutant strain C70ΔpheB lacking pheB were evaluated. qRT-PCR data showed that in C70, the expression of pheB- and nahH-encoded C23O was induced by phenol and salicylate, respectively. We demonstrate that strain C70 is more effective in the degradation of phenol and salicylate, especially at higher substrate concentrations, when these compounds are present as a mixture; i.e., when both pathways are expressed. Moreover, NahH is able to substitute for the deleted PheB in phenol degradation when salicylate is also present in the growth medium. The appearance of a yellow intermediate 2-hydroxymuconic semialdehyde was followed by the accumulation of catechol in salicylate-containing growth medium, and lower expression levels and specific activities of the C23O of the sal operon were detected. However, the excretion of the toxic intermediate catechol to the growth medium was avoided when the growth medium was supplemented with phenol, seemingly due to the contribution of the second meta pathway encoded by the phe genes. PMID:28257519

Evaluation of salicylic acid fatty ester prodrugs for UV protection.

PubMed

Im, Jong Seob; Balakrishnan, Prabagar; Oh, Dong Hoon; Kim, Jung Sun; Jeon, Eun-Mi; Kim, Dae-Duk; Yong, Chul Soon; Choi, Han-Gon

2011-07-01

The purpose of this study was to investigate the physicochemical properties and in vitro evaluation of fatty ester prodrugs of salicylic acid for ultraviolet (UV) protection. The physicochemical properties such as lipophilicity, chemical stability and enzymatic hydrolysis were investigated with the following fatty ester prodrugs of salicylic acid: octanoyl (C8SA), nonanoyl (C9SA), decanoyl (C10SA), lauroyl (C12SA), myristoyl (C14SA) and palmitoyl oxysalicylate (C16SA). Furthermore, their skin permeation and accumulation were evaluated using a combination of common permeation enhancing techniques such as the use of a lipophilic receptor solution, removal of stratum corneum and delipidization of skin. Their k' values were proportional to the degree of carbon-carbon saturation in the side chain. All these fatty esters were highly stable in 2-propanol, acetonitrile and glycerin, but unstable in methanol and ethanol. They were relatively unstable in liver and skin homogenates. In particular, C16SA was mostly hydrolyzed to its parent compound in hairless mouse liver and skin homogenates, suggesting that it might be converted to salicylic acid after its topical administration. In the skin permeation and accumulation study, C16SA showed the poorest permeation in all skins, suggesting that it could not be permeated in the skin. Furthermore, C14SA and C16SA were less accumulated in delipidized skin compared with normal skin or stripped skin, suggesting that these esters had relatively strong affinities for lipids compared with the other prodrugs in the skin. C16SA showed significantly higher dermal accumulation in all skins compared with its parent salicylic acid. Thus, the palmitoyl oxysalicylate (C16SA) might be a potential candidate for UV protection due to its absence of skin permeation, smaller uptake in the lipid phase and relatively lower skin accumulation.

BIODEGRADATION DURING CONTAMINANT TRANSPORT IN POROUS MEDIA. 4. IMPACT OF MICROBIAL LAG AND BACTERIAL CELL GROWTH. (R825415)

EPA Science Inventory

Abstract

Miscible-displacement experiments were conducted to examine the impact of microbial lag and bacterial cell growth on the transport of salicylate, a model hydrocarbon compound. The impacts of these processes were examined separately, as well as jointly, to dete...

The application of bioactive compounds from the food industry to control mold growth in indoor waterborne coatings.

PubMed

Bellotti, N; Salvatore, L; Deyá, C; Del Panno, M T; del Amo, B; Romagnoli, R

2013-04-01

Microbial growth in indoor environments creates health problems, especially in people with asthma; approximately 80% of these patients are allergic to mold. Antimicrobial coatings are formulated to generate surfaces that are easy to clean and may also incorporate active agents, commonly called biocides, which inhibit microbial colonization, subsequent growth and bio-deterioration of the substrates. Some research lines seek to replace traditional organometallic and organochlorines biocides with environmentally acceptable ones. The aim of this research was, primarily, to explore the possible application of different compounds used in food industry like preservatives to be used as antimicrobial additives for antimicrobial coatings. Four biocides were tested against two different ambient molds isolated from an interior painted wall (Chaetomium globosum and Alternaria alternate). The selected biocides were zinc salicylate, zinc benzoate, calcium benzoate and potassium sorbate. The resulting paints were subjected to biological and physical tests (viscosity, hiding power, humidity absorption and biocides leaching rate). Bioassays revealed that zinc benzoate and zinc salicylate resulted active against both fungi. Copyright © 2012 Elsevier B.V. All rights reserved.

A salicylic acid-based small molecule inhibitor for the oncogenic Src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2)

PubMed Central

Zhang, Xian; He, Yantao; Liu, Sijiu; Yu, Zhihong; Jiang, Zhong-Xing; Yang, Zhenyun; Dong, Yuanshu; Nabinger, Sarah C.; Wu, Li; Gunawan, Andrea M.; Wang, Lina; Chan, Rebecca J.; Zhang, Zhong-Yin

2010-01-01

The Src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2) plays a pivotal role in growth factor and cytokine signaling. Gain-of-function SHP2 mutations are associated with Noonan syndrome, various kinds of leukemias and solid tumors. Thus there is considerable interest in SHP2 as a potential target for anti-cancer and anti-leukemia therapy. We report a salicylic acid-based combinatorial library approach aimed to bind both active site and unique nearby sub-pockets for enhanced affinity and selectivity. Screening of the library led to the identification of a SHP2 inhibitor II-B08 (compound 9) with highly efficacious cellular activity. Compound 9 blocks growth factor stimulated ERK1/2 activation and hematopoietic progenitor proliferation, providing supporting evidence that chemical inhibition of SHP2 may be therapeutically useful for anti-cancer and anti-leukemia treatment. X-ray crystallographic analysis of the structure of SHP2 in complex with 9 reveals molecular determinants that can be exploited for the acquisition of more potent and selective SHP2 inhibitors. PMID:20170098

[Application of cantharidin, podophyllotoxin, and salicylic acid in recalcitrant plantar warts. A preliminary study].

PubMed

López-López, Daniel; Agrasar-Cruz, Carlos; Bautista-Casasnovas, Adolfo; Álvarez-Castro, Carlos Javier

2015-01-01

Plantar warts often are refractory to any treatment and can last for decades in adults. Recalcitrant warts are defined as those that have persisted for more than two years, or after at least two treatment modalities. A total of 15 consecutive patients with recalcitrant plantar warts were included in this preliminary study. The treatment consisted of applying one to two sessions that comprised compounding 1% cantharidin, 5% of podophyllotoxin, and 30% salicylic acid (CPS), with an interval between applications of four weeks. With treatment and subsequent follow-up for six months, there was complete eradication of lesions in 15 patients, eight (53.3%) required a single application of the solution, and seven (46.7%) two applications, with no side effects. Patient satisfaction related to treatment was measured by a visual analog scale (VAS) of 10 cm in length, with an average score 9.73 ± 0.46, and all said they would proceed with the treatment again if necessary. Topical treatment by compounding is safe, effective, and a promising therapeutic modality when applied in recalcitrant plantar warts.

Preparation and analysis of deuterium-labeled aspirin: application to pharmacokinetic studies

DOE Office of Scientific and Technical Information (OSTI.GOV)

Pedersen, A.K.; FitzGerald, G.A.

Inhibition of endogenous prostacyclin and thromboxane biosynthesis by aspirin is critically dose-dependent in humans. Gastrointestinal and hepatic hydrolysis may limit systemic availability of aspirin, especially in low doses, perhaps contributing to the biochemical selectivity of aspirin. Existing analytical methods do not permit determination of systemic bioavailability when low (less than 100 mg) doses of aspirin are administered. Deuterium-labeled aspirin (2-acetoxy(3,4,5,6-/sup 2/H4)benzoic acid) was synthesized from salicylic acid by catalytic exchange and subsequent acetylation. Analysis of the compounds as benzyl esters by GC-MS followed extractive alkylation from plasma. Heptadeuterated compounds were used as internal standards. Simultaneous administration of tetradeuterated aspirin intravenouslymore » with native aspirin orally to anesthetized dogs permitted kinetic studies of both aspirin and salicylic acid. The sensitivity of the method is superior to published methods using HPLC and, thus, more applicable to studies of low dose aspirin. Pulse administration of stable isotope-labeled aspirin permits detailed and repeated studies of dose-related aspirin pharmacokinetics in humans.« less

Assessment of the aroma impact of major odor-active thiols in pan-roasted white sesame seeds by calculation of odor activity values.

PubMed

Tamura, Hitoshi; Fujita, Akira; Steinhaus, Martin; Takahisa, Eisuke; Watanabe, Hiroyuki; Schieberle, Peter

2011-09-28

Eleven odor-active thiols, namely, 2-methyl-1-propene-1-thiol, (Z)-3-methyl-1-butene-1-thiol, (E)-3-methyl-1-butene-1-thiol, (Z)-2-methyl-1-butene-1-thiol, (E)-2-methyl-1-butene-1-thiol, 2-methyl-3-furanthiol, 3-mercapto-2-pentanone, 2-mercapto-3-pentanone, 4-mercapto-3-hexanone, 3-mercapto-3-methylbutyl formate, and 2-methyl-3-thiophenethiol, recently identified in an extract prepared from white sesame seeds, were quantitated in sesame using stable isotope dilution analyses. For that purpose, the following deuterium-labeled compounds were synthesized and used as internal standards in the quantitation assays: [2H6]-2-methyl-1-propene-1-thiol, [2H3]-(E)- and [2H3]-(Z)-2-methyl-1-butene-1-thiol, [2H3]-2-methyl-3-furanthiol, [2H2]-3-mercapto-2-pentanone, [2H3]-4-mercapto-3-hexanone, [2H6]-3-mercapto-3-methylbutyl formate, and [2H3]-2-methyl-3-thiophenethiol. On the basis of the results obtained, odor activity values (OAVs) were calculated as ratio of the concentration and odor threshold of the individual compounds in cooking oil. According to their high OAVs, particularly the 3-methyl-1-butene-1-thiols (OAV: 2400) and the 2-methyl-1-butene-1-thiols (OAV: 960) were identified as the most odor-active compounds in pan-roasted white sesame seeds. These compounds were therefore suggested to be mainly responsible for the characteristic but rather unstable sulfury aroma of freshly pan-roasted white sesame seeds.

Fouling Resistant CA/PVA/TiO2 Imprinted Membranes for Selective Recognition and Separation Salicylic Acid from Waste Water

PubMed Central

Yu, Xiaopeng; Mi, Xueyang; He, Zhihui; Meng, Minjia; Li, Hongji; Yan, Yongsheng

2017-01-01

Highly selective cellulose acetate (CA)/poly (vinyl alcohol) (PVA)/titanium dioxide (TiO2) imprinted membranes were synthesized by phase inversion and dip coating technique. The CA blend imprinted membrane was synthesized by phase inversion technique with CA as membrane matrix, polyethyleneimine (PEI) as the functional polymer, and the salicylic acid (SA) as the template molecule. The CA/PVA/TiO2 imprinted membranes were synthesized by dip coating of CA blend imprinted membrane in PVA and different concentration (0.05, 0.1, 0.2, 0.4 wt %) of TiO2 nanoparticles aqueous solution. The SEM analysis showed that the surface morphology of membrane was strongly influenced by the concentration of TiO2 nanoparticles. Compared with CA/PVA-TiO2(0.05, 0.1, 0.2%)-MIM, the CA/PVA-TiO2(0.4%)-MIM possessed higher membrane flux, kinetic equilibrium adsorption amount, binding capacity and better selectivity for SA. It was found that the pseudo-second-order kinetic model was studied to describe the kinetic of CA/PVA-TiO2(0.2%)-MIM judging by multiple regression analysis. Adsorption isotherm analysis indicated that the maximum adsorption capacity for SA were 24.43 mg g−1. Moreover, the selectivity coefficients of CA/PVA-TiO2 (0.2%)-MIM for SA relative to p-hydroxybenzoic acid (p-HB) and methyl salicylate (MS) were 3.87 and 3.55, respectively. PMID:28184369

Signals of Systemic Immunity in Plants: Progress and Open Questions

PubMed Central

Ádám, Attila L.; Nagy, Zoltán Á.; Kátay, György; Mergenthaler, Emese; Viczián, Orsolya

2018-01-01

Systemic acquired resistance (SAR) is a defence mechanism that induces protection against a wide range of pathogens in distant, pathogen-free parts of plants after a primary inoculation. Multiple mobile compounds were identified as putative SAR signals or important factors for influencing movement of SAR signalling elements in Arabidopsis and tobacco. These include compounds with very different chemical structures like lipid transfer protein DIR1 (DEFECTIVE IN INDUCED RESISTANCE1), methyl salicylate (MeSA), dehydroabietinal (DA), azelaic acid (AzA), glycerol-3-phosphate dependent factor (G3P) and the lysine catabolite pipecolic acid (Pip). Genetic studies with different SAR-deficient mutants and silenced lines support the idea that some of these compounds (MeSA, DIR1 and G3P) are activated only when SAR is induced in darkness. In addition, although AzA doubled in phloem exudate of tobacco mosaic virus (TMV) infected tobacco leaves, external AzA treatment could not induce resistance neither to viral nor bacterial pathogens, independent of light conditions. Besides light intensity and timing of light exposition after primary inoculation, spectral distribution of light could also influence the SAR induction capacity. Recent data indicated that TMV and CMV (cucumber mosaic virus) infection in tobacco, like bacteria in Arabidopsis, caused massive accumulation of Pip. Treatment of tobacco leaves with Pip in the light, caused a drastic and significant local and systemic decrease in lesion size of TMV infection. Moreover, two very recent papers, added in proof, demonstrated the role of FMO1 (FLAVIN-DEPENDENT-MONOOXYGENASE1) in conversion of Pip to N-hydroxypipecolic acid (NHP). NHP systemically accumulates after microbial attack and acts as a potent inducer of plant immunity to bacterial and oomycete pathogens in Arabidopsis. These results argue for the pivotal role of Pip and NHP as an important signal compound of SAR response in different plants against different pathogens. PMID:29642641

Determination of suspected allergens in cosmetic products by headspace-programmed temperature vaporization-fast gas chromatography-quadrupole mass spectrometry.

PubMed

del Nogal Sánchez, Miguel; Pérez-Pavón, José Luis; Moreno Cordero, Bernardo

2010-07-01

In the present work, a strategy for the qualitative and quantitative analysis of 24 volatile compounds listed as suspected allergens in cosmetics by the European Union is reported. The list includes benzyl alcohol, limonene, linalool, methyl 2-octynoate, beta-citronellol, geraniol, citral (two isomers), 7-hydroxycitronellal, anisyl alcohol, cinnamal, cinnamyl alcohol, eugenol, isoeugenol (two isomers), coumarin, alpha-isomethyl ionone, lilial, alpha-amylcinnamal, lyral, alpha-amylcinnamyl alcohol, farnesol (three isomers), alpha-hexyl cinnamal, benzyl cinnamate, benzyl benzoate, and benzyl salicylate. The applicability of a headspace (HS) autosampler in combination with a gas chromatograph (GC) equipped with a programmable temperature vaporizer (PTV) and a quadrupole mass spectrometry (qMS) detector is explored. By using a headspace sampler, sample preparation is reduced to introducing the sample into the vial. This reduces the analysis time and the experimental errors associated with this step of the analytical process. Two different injection techniques were used: solvent-vent injection and hot-split injection. The first offers a way to improve sensitivity at the same time maintaining the simple headspace instrumentation and it is recommended for compounds at trace levels. The use of a liner packed with Tenax-TA allowed the compounds of interest to be retained during the venting process. The signals obtained when hot-split injection was used allowed quantification of all the compounds according to the thresholds of the European Cosmetics Directive. Monodimensional gas chromatography coupled to a conventional quadrupole mass spectrometry detector was used and the 24 analytes were separated appropriately along a run time of about 12 min. Use of the standard addition procedure as a quantification technique overcame the matrix effect. It should be emphasized that the method showed good precision and accuracy. Furthermore, it is rapid, simple, and--in view of the results--highly suitable for the determination of suspected allergens in different cosmetic products.

Priming of Wheat with the Green Leaf Volatile Z-3-Hexenyl Acetate Enhances Defense against Fusarium graminearum But Boosts Deoxynivalenol Production1

PubMed Central

Ameye, Maarten; Audenaert, Kris; De Zutter, Nathalie; Steppe, Kathy; Van Meulebroek, Lieven; Vanhaecke, Lynn; De Vleesschauwer, David; Haesaert, Geert; Smagghe, Guy

2015-01-01

Priming refers to a mechanism whereby plants are sensitized to respond faster and/or more strongly to future pathogen attack. Here, we demonstrate that preexposure to the green leaf volatile Z-3-hexenyl acetate (Z-3-HAC) primed wheat (Triticum aestivum) for enhanced defense against subsequent infection with the hemibiotrophic fungus Fusarium graminearum. Bioassays showed that, after priming with Z-3-HAC, wheat ears accumulated up to 40% fewer necrotic spikelets. Furthermore, leaves of seedlings showed significantly smaller necrotic lesions compared with nonprimed plants, coinciding with strongly reduced fungal growth in planta. Additionally, we found that F. graminearum produced more deoxynivalenol, a mycotoxin, in the primed treatment. Expression analysis of salicylic acid (SA) and jasmonic acid (JA) biosynthesis genes and exogenous methyl salicylate and methyl jasmonate applications showed that plant defense against F. graminearum is sequentially regulated by SA and JA during the early and later stages of infection, respectively. Interestingly, analysis of the effect of Z-3-HAC pretreatment on SA- and JA-responsive gene expression in hormone-treated and pathogen-inoculated seedlings revealed that Z-3-HAC boosts JA-dependent defenses during the necrotrophic infection stage of F. graminearum but suppresses SA-regulated defense during its biotrophic phase. Together, these findings highlight the importance of temporally separated hormone changes in molding plant health and disease and support a scenario whereby the green leaf volatile Z-3-HAC protects wheat against Fusarium head blight by priming for enhanced JA-dependent defenses during the necrotrophic stages of infection. PMID:25713338

The plastidial retrograde signal methyl erythritol cyclopyrophosphate is a regulator of salicylic acid and jasmonic acid crosstalk.

PubMed

Lemos, Mark; Xiao, Yanmei; Bjornson, Marta; Wang, Jin-Zheng; Hicks, Derrick; Souza, Amancio de; Wang, Chang-Quan; Yang, Panyu; Ma, Shisong; Dinesh-Kumar, Savithramma; Dehesh, Katayoon

2016-03-01

The exquisite harmony between hormones and their corresponding signaling pathways is central to prioritizing plant responses to simultaneous and/or successive environmental trepidations. The crosstalk between jasmonic acid (JA) and salicylic acid (SA) is an established effective mechanism that optimizes and tailors plant adaptive responses. However, the underlying regulatory modules of this crosstalk are largely unknown. Global transcriptomic analyses of mutant plants (ceh1) with elevated levels of the stress-induced plastidial retrograde signaling metabolite 2-C-methyl-D-erythritol cyclopyrophosphate (MEcPP) revealed robustly induced JA marker genes, expected to be suppressed by the presence of constitutively high SA levels in the mutant background. Analyses of a range of genotypes with varying SA and MEcPP levels established the selective role of MEcPP-mediated signal(s) in induction of JA-responsive genes in the presence of elevated SA. Metabolic profiling revealed the presence of high levels of the JA precursor 12-oxo-phytodienoic acid (OPDA), but near wild type levels of JA in the ceh1 mutant plants. Analyses of coronatine-insensitive 1 (coi1)/ceh1 double mutant plants confirmed that the MEcPP-mediated induction is JA receptor COI1 dependent, potentially through elevated OPDA. These findings identify MEcPP as a previously unrecognized central regulatory module that induces JA-responsive genes in the presence of high SA, thereby staging a multifaceted plant response within the environmental context. © The Author 2016. Published by Oxford University Press on behalf of the Society for Experimental Biology.

Carnivore Attractant or Plant Elicitor? Multifunctional Roles of Methyl Salicylate Lures in Tomato Defense.

PubMed

Rowen, Elizabeth; Gutensohn, Michael; Dudareva, Natalia; Kaplan, Ian

2017-06-01

Synthetic plant volatile lures attract natural enemies, but may have non-target effects due to the multifunctional nature of volatile signals. For example, methyl salicylate (MeSA) is used to attract predators, yet also serves as a signaling hormone involved in plant pathogen defense. We investigated the consequences of deploying MeSA lures to attract predators for tomato (Solanum lycopersicum) defense against herbivores. To understand the spatial distribution of the lure's effect, we exposed tomatoes in the field to MeSA along a linear distance gradient and induced defenses by simulating feeding by hornworm caterpillars in a fully crossed factorial design (+/- MeSA, +/- herbivory). Subsequently, we analyzed activity of several defensive proteins (protease inhibitors, polyphenol oxidase, peroxidase), development of hornworm larvae (Manduca sexta), growth of fungal pathogens (Cladosporium and Alternaria), and attractiveness to herbivores and predators. Overall, MeSA-exposed plants were more resistant to both insects and pathogens. Secondary pathogen infection was reduced by 25% in MeSA exposed plants, possibly due to elevated polyphenol oxidase activity. Interestingly, we found that lures affected plant pathogen defenses equivalently across all distances (up to 4 m away) indicating that horizontal diffusion of a synthetic volatile may be greater than previously assumed. While thrips avoided colonizing hornworm- damaged tomato plants, this induced resistance was not observed upon pre-exposure to MeSA, suggesting that MeSA suppresses the repellant effect induced by herbivory. Thus, using MeSA lures in biological control may inadvertently protect crops from pathogens, but has mixed effects on plant resistance to insect herbivores.

Jasmonic Acid Signaling Modulates Ozone-Induced Hypersensitive Cell Death

PubMed Central

Rao, Mulpuri V.; Lee, Hyung-il; Creelman, Robert A.; Mullet, John E.; Davis, Keith R.

2000-01-01

Recent studies suggest that cross-talk between salicylic acid (SA)–, jasmonic acid (JA)–, and ethylene-dependent signaling pathways regulates plant responses to both abiotic and biotic stress factors. Earlier studies demonstrated that ozone (O3) exposure activates a hypersensitive response (HR)–like cell death pathway in the Arabidopsis ecotype Cvi-0. We now have confirmed the role of SA and JA signaling in influencing O3-induced cell death. Expression of salicylate hydroxylase (NahG) in Cvi-0 reduced O3-induced cell death. Methyl jasmonate (Me-JA) pretreatment of Cvi-0 decreased O3-induced H2O2 content and SA concentrations and completely abolished O3-induced cell death. Cvi-0 synthesized as much JA as did Col-0 in response to O3 exposure but exhibited much less sensitivity to exogenous Me-JA. Analyses of the responses to O3 of the JA-signaling mutants jar1 and fad3/7/8 also demonstrated an antagonistic relationship between JA- and SA-signaling pathways in controlling the magnitude of O3-induced HR-like cell death. PMID:11006337

Jasmonic acid signaling modulates ozone-induced hypersensitive cell death.

PubMed

Rao, M V; Lee, H; Creelman, R A; Mullet, J E; Davis, K R

2000-09-01

Recent studies suggest that cross-talk between salicylic acid (SA)-, jasmonic acid (JA)-, and ethylene-dependent signaling pathways regulates plant responses to both abiotic and biotic stress factors. Earlier studies demonstrated that ozone (O(3)) exposure activates a hypersensitive response (HR)-like cell death pathway in the Arabidopsis ecotype Cvi-0. We now have confirmed the role of SA and JA signaling in influencing O(3)-induced cell death. Expression of salicylate hydroxylase (NahG) in Cvi-0 reduced O(3)-induced cell death. Methyl jasmonate (Me-JA) pretreatment of Cvi-0 decreased O(3)-induced H(2)O(2) content and SA concentrations and completely abolished O(3)-induced cell death. Cvi-0 synthesized as much JA as did Col-0 in response to O(3) exposure but exhibited much less sensitivity to exogenous Me-JA. Analyses of the responses to O(3) of the JA-signaling mutants jar1 and fad3/7/8 also demonstrated an antagonistic relationship between JA- and SA-signaling pathways in controlling the magnitude of O(3)-induced HR-like cell death.

Metabolism of aspirin and procaine in mice pretreated with O-4-nitrophenyl methyl(phenyl)phosphinate or O-4-nitrophenyl diphenylphosphinate

DOE Office of Scientific and Technical Information (OSTI.GOV)

Joly, J.M.; Brown, T.M.

Concentrations of (carboxyl-/sup 14/C)procaine in blood of mice were increased threefold for 27 min by exposure to O-4-nitrophenyl diphenylphosphinate 2 hr prior to (carboxyl-/sup 14/C)procaine injection ip, while there was no effect of O-4-nitrophenyl methyl(phenyl)phosphinate pretreatment. There was no effect of either organophosphinate on the primary hydrolysis of (acetyl-l-/sup 14/C)aspirin when assessed by the expiration of (/sup 14/C)carbon dioxide; however, O-4-nitrophenyl diphenylphosphinate pretreatment produced transient increases in blood concentrations of both (carboxyl-/sup 14/C)aspirin and (carboxyl-/sup 14/C)salicylic acid following administration of (carboxyl-/sup 14/C)aspirin. Liver carboxylesterase activity in O-4-nitrophenyl diphenylphosphinate pretreated mice was 11% of control activity. These results indicate the potentialmore » for drug interaction with O-4-nitrophenyl diphenylphosphinate but not with O-4-nitrophenyl methyl(phenyl)phosphinate. It appears that liver carboxylesterase activity has a minor role in hydrolysis of aspirin in vivo, but may be more important in procaine metabolism.« less

Synthesis and odor evaluation of five new sulfur-containing ester flavor compounds from 4-ethyloctanoic acid.

PubMed

Liu, Yuping; Chen, Haitao; Yin, Decai; Sun, Baoguo

2010-07-29

Five sulfur-containing flavor compounds were synthesized for the first time by the reaction of 4-ethyloctanoyl chloride with sulfur-containing alcohols or mercaptans. The synthesized compounds are 3-(methylthio)propyl 4-ethyloctanoate, 2-methyl-3-tetrahydro-furanthiol 4-ethyloctanoate, 4-methyl-5-thiazoleethanol 4-ethyloctanoate, 2-furan-methanethiol 4-ethyloctanoate and 2-methyl-3-furanthiol 4-ethyloctanoate. These five synthetic sulfur-containing ester flavor compounds all have meaty odor and might be used in foods if approved for this purpose in the future.

The crystallographic, spectroscopic and theoretical studies on (E)-2-(((4-chlorophenyl)imino)methyl)-5-(diethylamino)phenol and (E)-2-(((3-chlorophenyl)imino)methyl)-5-(diethylamino)phenol molecules

NASA Astrophysics Data System (ADS)

Demirtaş, Güneş; Dege, Necmi; Ağar, Erbil; Uzun, Sümeyye Gümüş

2018-01-01

Two new salicylideneaniline (SA) derivative compounds (E)-2-(((4-chlorophenyl)imino)methyl)-5-(diethylamino)phenol, compound (I), and (E)-2-(((3-chlorophenyl)imino)methyl)-5-(diethylamino)phenol, compound (II), have been synthesized and characterized by single crystal X-ray diffraction, IR spectroscopy, 1H NMR, 13C NMR and theoretical methods. Both of the compounds which are Schiff base derivatives are isomer of each other. While the compound (I) crystallizes in centrosymmetric monoclinic space group P 21/c, the compound (II) crystallizes in orthorhombic space group P 212121. The theoretical parameters of the molecules have been calculated by using Hartree-Fock (HF) and density functional theory (DFT/B3LYP) with 6-31G (d,p) basis set. These theoretical parameters have been compared with the experimental parameters obtained by XRD. The experimental geometries of the compounds have been superimposed with the theoretical geometries calculated by HF and DFT methods. Furthermore, the theoretical IR calculations, molecular electrostatic potential maps (MEP) and frontier molecular orbitals have been created for the compounds.

Autoignition Studies of Diesel Alternative Biofuels

NASA Astrophysics Data System (ADS)

Wang, Weijing

The autoignition of biofuel compounds that offer potential as diesel fuel alternatives was studied under high-pressure engine-like conditions using the shock tube technique. Ignition delay times were determined in reflected shock experiments using measured pressure and electronically-excited OH emission. Measurements were made at conditions ranging from 650 to 1350 K, pressures from 6 to 50 atm, and for fuel/air/diluent mixtures at equivalence ratios from 0.5 to 2. The wide range of temperatures examined provides observation of autoignition in three reactivity regimes, including the negative temperature coefficient (NTC) regime which is characteristic of fuels containing alkyl functionalities. Compounds studied include biodiesel-related compounds and real biodiesel fuels, dimethyl ether, and 3-methylheptane which is representative of compounds found in synthetic diesel fuels produced using the Fischer-Tropsch and hydrotreatment processes. Biodiesel compounds studied include biodiesel surrogates, methyl decanoate, methyl-5-decenoate, and methyl-9-decenoate; compounds found in large quantities in biodiesels, methyl palmitate, methyl stearate, methyl oleate, and methyl linoleate; and soy-based and animal fat based methyl ester biodiesels. Comparison of biodiesel compounds illustrates the influence of molecular structure (e.g., chain length, double bonds, and ester functionality) on reactivity. For methyl decanoate, the effect of high pressure exhaust gas recirculation (EGR) conditions relevant to internal combustion engines was also determined. Results showed that the first-order influence of EGR by displacing fuel and O2 to decrease radical branching. Measurements were compared to kinetic modeling results from models available in the literature providing varying degrees of model validation. Reaction flux analyses were also carried out to further examine the kinetic differences in different temperature regimes for fuel compounds. For example, reaction flux analyses illustrates the importance of the long alkyl chain in controlling the overall reactivity of methyl ester biodiesel compounds and the subtle role the ester group has on inhibiting low-temperature reactivity as well as the influence of branching on reactivity for lightly branched alkanes. This thesis work provides a rich database of kinetic information for biofuel-related compounds at conditions relevant to real engine operations, offering quantitative kinetic targets for the development and evaluation of future kinetic models for important alternative fuel compounds. The results quantify the reactivity variability of biodiesel alternatives and illustrate that at temperature greater than 900 to 1000 K fuel structure has little influence on reactivity, as fuel fragmentation results in an intermediate pool that is largely the same for the fuels studied. On the other hand at temperature lower than 900 K, where fuel-specific low-temperature chemistry plays a role, different fuel structures can result in vast differences in reactivity, up to factors of three or more in ignition delay.

Acetylsalicylic acid (aspirin) and salicylic acid interaction with the human erythrocyte membrane bilayer induce in vitro changes in the morphology of erythrocytes.

PubMed

Suwalsky, Mario; Belmar, Jessica; Villena, Fernando; Gallardo, María José; Jemiola-Rzeminska, Malgorzata; Strzalka, Kazimierz

2013-11-01

Despite the well-documented information, there are insufficient reports concerning the effects of salicylate compounds on the structure and functions of cell membranes, particularly those of human erythrocytes. With the aim to better understand the molecular mechanisms of the interaction of acetylsalicylic acid (ASA) and salicylic acid (SA) with cell membranes, human erythrocyte membranes and molecular models were utilized. These consisted of bilayers of dimyristoylphosphatidylcholine (DMPC) and dimyristoylphosphatidylethanolamine (DMPE), representative of phospholipid classes located in the outer and inner monolayers of the human erythrocyte membrane, respectively. The capacity of ASA and SA to perturb the multibilayer structures of DMPC and DMPE was evaluated by X-ray diffraction while DMPC unilamellar vesicles (LUV) were studied by fluorescence spectroscopy. Moreover, we took advantage of the capability of differential scanning calorimetry (DSC) to detect the changes in the thermotropic phase behavior of lipid bilayers resulting from ASA and SA interaction with PC and PE molecules. In an attempt to further elucidate their effects on cell membranes, the present work also examined their influence on the morphology of intact human erythrocytes by means of defocusing and scanning electron microscopy, while isolated unsealed human erythrocyte membranes (IUM) were studied by fluorescence spectroscopy. Results indicated that both salicylates interact with human erythrocytes and their molecular models in a concentration-dependent manner perturbing their bilayer structures. Copyright © 2013 Elsevier Inc. All rights reserved.

Suitability of pharmaceuticals and personal care products (PPCPs) and artificial sweeteners (ASs) as wastewater indicators in the Pearl River Delta, South China.

PubMed

Yang, Yuan-Yuan; Liu, Wang-Rong; Liu, You-Sheng; Zhao, Jian-Liang; Zhang, Qian-Qian; Zhang, Min; Zhang, Jin-Na; Jiang, Yu-Xia; Zhang, Li-Juan; Ying, Guang-Guo

2017-07-15

Wastewater indicator is a useful tool for evaluating the wastewater impact on natural water, but there is little information about the suitability of wastewater indicators for different regions. This study aimed to select suitable wastewater indicators in the Pearl River Delta region, south China by screening a range of wastewater related organic compounds. The screening campaign was carried out by investigating the occurrence and removal efficiencies of 93 pharmaceuticals and personal care products (PPCPs) and 5 artificial sweeteners (ASs) in nine wastewater treatment plants (WWTPs) located in the region, and the occurrence of these target compounds in the contaminated and clean surface water of the Pearl River. An ideal wastewater indicator should be hydrophilic, source-specific for domestic wastewater, ubiquitous in contaminated surface water with detection frequency (DF) >80% and absent in background water samples. For liable indicators, high removal rates (>90%) should be observed in WWTPs and they should be detected in all the influent samples at concentrations fifty times higher than their limits of quantification. For conservative indicators, low removal rates (<50%) should be observed in WWTPs and they should be detected in all the effluent samples at concentrations fifty times higher than their limits of quantification. Based on the above criteria, sucralose and fluconazole were selected as conservative indicators in the region, while cyclamate, saccharin, methyl paraben, ethyl paraben, propyl paraben, paracetamol, salicylic acid and caffeine were selected as liable indicators. Copyright © 2017 Elsevier B.V. All rights reserved.

Review of Allergic and Photoallergic Contact Dermatitis from an Ingredient in a Medicament Vehicle Consisting of a Compress, Poultice, Plaster, and Tape

PubMed Central

Oiso, Naoki; Kawada, Akira

2011-01-01

The topical application of a medicament vehicle consisting of a compress, poultice, plaster, and tape containing a nonsteroidal anti-inflammatory drug or methyl salicylate is prevalent in Japan. The method is effective for conveying ingredients to the muscles via the skin for the relief of muscular pain. However, an ingredient in the occlusive vehicle can cause allergic and photoallergic contact dermatitis. We summarize cases reported over the past decade and discuss the current strategy for diminishing the risk of allergic and photoallergic contact dermatitis. PMID:21603165

The effects of CO2 on the negative reactant ions of IMS

NASA Technical Reports Server (NTRS)

Spangler, Glenn E.

1995-01-01

In the presence of CO2, the negative reactant ions of ion mobility spectrometry (IMS) are ion clusters of CO4(-) and CO3(-). Methyl salicylate is ionized by the CO4(-)(H2O(n))(N2(m)) reactant ions, but not by the CO3(-)(H2O(n))(N2(m)) reactant ions. While the CO4(-) ions are formed by direct association, the CO3(-) ions require additional energy to be formed. The additional energy is provided by either excited neutral gas molecules in a metastable state or UV (ultraviolet) radiation.

Key Aroma Compounds in Lippia dulcis (Dushi Button).

PubMed

Schmitt, Rainer; Cappi, Michael; Pollner, Gwendola; Greger, Veronika

2018-03-14

An aroma extract dilution analysis (AEDA) applied on aroma extracts prepared from the edible flower Dushi Button ( Lippia dulcis) resulted in the detection of 34 odor-active compounds. The highest flavor dilution (FD) factors were determined for methyl 2-methylbutanoate, ethyl 2-methylbutanoate, 4-mercapto-4-methyl-2-pentanone, an unknown caramel-like compound, and vanillin. Quantitative measurements performed by application of stable isotope dilution assays (SIDA), followed by a calculation of odor activity values (OAVs), resulted in the revelation of 4-mercapto-4-methyl-2-pentanone, linalool, myrcene, ethyl 2-methylbutanoate, methyl 2-methylbutanoate, and ( Z)-3-hexenal as important contributors to the flavor of Dushi Buttons.

Host plant volatiles serve to increase the response of male European grape berry moths, Eupoecilia ambiguella, to their sex pheromone.

PubMed

Schmidt-Büsser, Daniela; von Arx, Martin; Guerin, Patrick M

2009-09-01

The European grape berry moth is an important pest in vineyards. Males respond to the female-produced sex pheromone released from a piezo nebulizer in a dose-dependent manner in a wind tunnel: <50% arrive at the source at 5-50 pg/min (underdosed), 80% arrive at 100 pg/min to 10 ng/min (optimal) and <20% arrive at 100 ng/min (overdosed). Males responding to overdosed pheromone show in flight arrestment at 80 cm from the source. Host plant chemostimuli for Eupoecilia ambiguella increase the responses of males to underdosed and overdosed pheromone. (Z)-3-hexen-1-ol, (+)-terpinen-4-ol, (E)-beta-caryophyllene and methyl salicylate released with the underdosed pheromone cause a significant increase in male E. ambiguella flying to the source. Time-event analysis indicates a positive correlation between faster activation and probability of source contact by the responding males. The four host plant compounds added to the overdosed pheromone permitted males to take off faster and with a higher probability of flying to the source. This suggests that perception of host plant products with the sex pheromone facilitates male E. ambiguella to locate females on host plants, lending credence to the hypothesis that plant products can signal rendezvous sites suitable for mating.

Facility monitoring of chemical warfare agent simulants in air using an automated, field-deployable, miniature mass spectrometer.

PubMed

Smith, Jonell N; Noll, Robert J; Cooks, R Graham

2011-05-30

Vapors of four chemical warfare agent (CWA) stimulants, 2-chloroethyl ethyl sulfide (CEES), diethyl malonate (DEM), dimethyl methylphosphonate (DMMP), and methyl salicylate (MeS), were detected, identified, and quantitated using a fully automated, field-deployable, miniature mass spectrometer. Samples were ionized using a glow discharge electron ionization (GDEI) source, and ions were mass analyzed with a cylindrical ion trap (CIT) mass analyzer. A dual-tube thermal desorption system was used to trap compounds on 50:50 Tenax TA/Carboxen 569 sorbent before their thermal release. The sample concentrations ranged from low parts per billion [ppb] to two parts per million [ppm]. Limits of detection (LODs) ranged from 0.26 to 5.0 ppb. Receiver operating characteristic (ROC) curves are presented for each analyte. A sample of CEES at low ppb concentration was combined separately with two interferents, bleach (saturated vapor) and diesel fuel exhaust (1%), as a way to explore the capability of detecting the simulant in an environmental matrix. Also investigated was a mixture of the four CWA simulants (at concentrations in air ranging from 270 to 380 ppb). Tandem mass (MS/MS) spectral data were used to identify and quantify the individual components. Copyright © 2011 John Wiley & Sons, Ltd.

Implications of Chirality of Drugs and Excipients in Physical Pharmacy.

NASA Astrophysics Data System (ADS)

Duddu, Sarma P.

1993-01-01

The interactions of enantiomers of a chiral drug with other chemical entities, which may lead to changes and stereoselective differences in the physicochemical properties of the drug, were investigated. The various interactions described below employed ephedrine, pseudoephedrine and some of their salts, and to a minor extent, propranolol hydrochloride. The interaction of ephedrinium or pseudoephedrinium with the achiral anion, salicylate, yielded crystalline salts with the notable exception of homochiral ephedrine. Racemic ephedrinium salicylate exists as a centrosymmetric crystal (P2_1/n) whereas racemic pseudoephedrinium salicylate is a mixture of homochiral crystals (P2 _1). The inability of ephedrinium to exist as a homochiral salicylate salt is attributed to a high energy conformation of the ephedrinium cation, following conformational analysis. Arising from conformationally favorable interactions, the crystallization of racemic ephedrinium salicylate from aqueous solutions was utilized to improve the enantiomeric purity of a partially resolved mixture of ephedrine from 60% to 82% in one crystallization step. Interaction of the opposite enantiomers of ephedrine and pseudoephedrine in the solid, liquid, solution and vapor state produced the respective racemic compounds. The formation of racemic ephedrine in the solid state as predominantly second order (k = 392 mol^{-1} hr^{-1}), probably mediated by the vapor phase. The formation of racemic pseudoephedrine was predominantly diffusion-controlled in the solid state via an intermediate non-crystalline phase. The interaction with traces of the opposite enantiomer during crystallization of (RS)-(-)-ephedrinium 2-naphthalenesulfonate and (SS)-(+)-pseudoephedrinium salicylate changed pharmaceutically important solid state properties, including dissolution rate. Uptake of the enantiomeric impurity was measured by a new, sensitive HPLC method. The enantiomeric impurity, at mole fractions <= 0.0027 greatly increased the lattice disorder, i.e. entropy, measured calorimetrically. The release of propranolol hydrochloride from a sustained-release matrix containing HPMC and racemic propranolol hydrochloride was stereoselective, though variable, suggesting a differential interaction of the two enantiomers with the hydrated chiral matrix. Thus, the interaction of a chiral drug with other chemical entities leads to significant, interpretable changes in the physicochemical properties of the drug, which may have important implications in the design and development of reliable and effective solid dosage forms.

Effect of salicylic acid and structurally related compounds in the accumulation of phytoalexins in cotyledons of common bean (Phaseolus vulgaris L.) cultivars.

PubMed

Durango, Diego; Pulgarin, Natalia; Echeverri, Fernando; Escobar, Gustavo; Quiñones, Winston

2013-09-02

In the present work, isoflavonoid phytoalexin production in response to the application of salicylic acid in cotyledons of four common bean (Phaseolus vulgaris) cultivars (SA) was evaluated. The time-course and dose-response profiles of the induction process were established by quantifying the isoflavonoids by HPLC. Cotyledons of anthracnose-resistant cultivars induced by SA produced substantially higher phytoalexin contents as compared to the susceptible ones. In addition, maximum levels of phytoalexins (50-100 fold increases) were reached between 96 and 144 h, and when a concentration of SA from 3.62 to 14.50 mM was used. The observations also indicate that there was a relatively good correlation between the phytoalexin contents and the inhibitory effect against C. lindemuthianum; the higher antifungal activity was observed during the first 48 hours for extracts from cotyledons treated with SA at 1.45 and 3.62 mM, and between 96 and 144 h after induction. Finally, compounds structurally related to SA (dihydro-quinazolinones and some imines) showed a strong elicitor effect. Moreover, induced extracts from cotyledons treated with these potential elicitors, besides the properly elicitors, displayed a weak to moderated antifungal activity. These compounds may be considered good candidates for developing of new phytoprotectants. Furthermore, phytoalexin-eliciting substances may contribute for selecting disease resistant cultivars.

Effect of antacid and ascorbic acid on serum salicylate concentration.

PubMed

Hansten, P D; Hayton, W L

1980-01-01

To determine the effect of antacid or ascorbic acid administration on plateau serum salicylate concentrations, nine healthy subjects were given each of the following treatments by balanced block design: choline salicylate (equivalent to 3.76 or 5.62 Gm/day of aspirin); choline salicylate plus magnesium-aluminum hydroxide (120 ml/day); or choline salicylate plus ascorbic acid (3 Gm/day). In subjects developing a control serum salicylate level above 10 mg/dl, antacid administration produced a decrease in serum salicylate level (mean 19.8 mg/dl vs. 15.8 mg/dl) (P less than 0.01). Ascorbic acid administration was not associated with a significant change in serum salicylate. The reduction in serum salicylate following antacid appears to be due to antacid-induced alkalinization of the urine with resultant increase in renal salicylate clearance. Antacid administration should be considered a potential cause of altered serum salicylate concentration in patients receiving large doses of salicylate.

[Anti-platelet actions of salicylates: in vivo, ex vivo and in vitro effects of choline salicylate].

PubMed

Irino, O; Saitoh, K; Ohkubo, K

1985-07-01

Effects of choline salicylate, sodium salicylate, choline chloride and acetylsalicylic acid on platelet aggregation in vivo, ex vivo and in vitro in mice were studied. These drugs all inhibited adenosine diphosphate (ADP)-induced respiratory depression, which is closely related to platelet aggregation in vivo, with choline salicylate showing the strongest inhibitory effect. Choline salicylate had a tendency to reduce the mortality of animals injected intravenously with endotoxin, but the other drugs had no such effect. The inhibitory effects of these drugs on ADP-induced platelet aggregation ex vivo were in the order of choline salicylate greater than acetylsalicylic acid congruent to sodium salicylate greater than choline chloride congruent to no effect, and plasma concentrations of protein-unbound salicylic acid at 1 hr after oral administration of drugs were in the order of choline salicylate greater than acetylsalicylic acid congruent to sodium salicylate. The in vitro effects of these drugs were in the order of choline salicylate congruent to sodium salicylate greater than choline chloride congruent to acetylsalicylic acid congruent to no effect. Therefore, it was considered that salicylic acid played an important role on the in vivo, ex vivo and in vitro effects of choline salicylate and that choline increased plasma concentrations of salicylic acid and consequently enhanced the in vivo and ex vivo effects of salicylic acid. Furthermore, the ex vivo effects of choline salicylate were found when ADP-induced platelet aggregation was measured with platelet-rich plasma prepared from blood collected with heparin as anti-coagulant, but not when blood was collected with citrate.(ABSTRACT TRUNCATED AT 250 WORDS)

New chemical constituents from Oryza sativa straw and their algicidal activities against blue-green algae.

PubMed

Ahmad, Ateeque; Kim, Seung-Hyun; Ali, Mohd; Park, Inmyoung; Kim, Jin-Seog; Kim, Eun-Hye; Lim, Ju-Jin; Kim, Seul-Ki; Chung, Ill-Min

2013-08-28

Five new constituents, 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-β-D-xylopyranosyl-(2a→1b)-2a-O-β-D-xylopyranosyl-(2b→1c)-2b-O-β-D-xylopyranosyl-2c-octadecanoate (1), 5,4'-dihydroxy-7,3'-dimethoxyflavone-4'-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-2d-octadecanoate (2), kaempferol-3-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-2d-hexadecanoate (3), methyl salicylate-2-O-α-D-xylopyranosyl-(2a→1b)-2a-O-α-D-xylopyranosyl-(2b→1c)-2b-O-α-D-xylopyranosyl-(2c→1d)-2c-O-α-D-xylopyranosyl-(2d→1e)-2d-O-α-D-xylopyranosyl-(2e→1f)-2e-O-α-D-xylopyranosyl-(2f→1g)-2f-O-α-D-xylopyranosyl-(2g→1h)-2g-O-α-D-xylopyranosyl-2h-geranilan-8',10'-dioic acid-1'-oate (4), and oleioyl-β-D-arabinoside (5), along with eight known compounds, were isolated from a methanol extract of Oryza sativa straw. The structures of the new compounds were elucidated using one- and two-dimensional NMR spectroscopies in combination with IR, ESI/MS, and HR-ESI/FTMS. In bioassays with blue-green algae, the efficacies of the algicidal activities of the five new compounds (1-5) were evaluated at concentrations of 1, 10, and 100 mg/L. Compound 5 had the highest growth inhibition (92.6 ± 0.3%) for Microcystis aeruginosa UTEX 2388 at a concentration of 100 ppm (mg/L). Compound 5 has high potential for the ecofriendly control of weeds and algae harmful to water-logged rice.

Bacteria-Triggered Systemic Immunity in Barley Is Associated with WRKY and ETHYLENE RESPONSIVE FACTORs But Not with Salicylic Acid1[C][W

PubMed Central

Dey, Sanjukta; Wenig, Marion; Langen, Gregor; Sharma, Sapna; Kugler, Karl G.; Knappe, Claudia; Hause, Bettina; Bichlmeier, Marlies; Babaeizad, Valiollah; Imani, Jafargholi; Janzik, Ingar; Stempfl, Thomas; Hückelhoven, Ralph; Kogel, Karl-Heinz; Mayer, Klaus F.X.

2014-01-01

Leaf-to-leaf systemic immune signaling known as systemic acquired resistance is poorly understood in monocotyledonous plants. Here, we characterize systemic immunity in barley (Hordeum vulgare) triggered after primary leaf infection with either Pseudomonas syringae pathovar japonica (Psj) or Xanthomonas translucens pathovar cerealis (Xtc). Both pathogens induced resistance in systemic, uninfected leaves against a subsequent challenge infection with Xtc. In contrast to systemic acquired resistance in Arabidopsis (Arabidopsis thaliana), systemic immunity in barley was not associated with NONEXPRESSOR OF PATHOGENESIS-RELATED GENES1 or the local or systemic accumulation of salicylic acid. Instead, we documented a moderate local but not systemic induction of abscisic acid after infection of leaves with Psj. In contrast to salicylic acid or its functional analog benzothiadiazole, local applications of the jasmonic acid methyl ester or abscisic acid triggered systemic immunity to Xtc. RNA sequencing analysis of local and systemic transcript accumulation revealed unique gene expression changes in response to both Psj and Xtc and a clear separation of local from systemic responses. The systemic response appeared relatively modest, and quantitative reverse transcription-polymerase chain reaction associated systemic immunity with the local and systemic induction of two WRKY and two ETHYLENE RESPONSIVE FACTOR (ERF)-like transcription factors. Systemic immunity against Xtc was further associated with transcriptional changes after a secondary/systemic Xtc challenge infection; these changes were dependent on the primary treatment. Taken together, bacteria-induced systemic immunity in barley may be mediated in part by WRKY and ERF-like transcription factors, possibly facilitating transcriptional reprogramming to potentiate immunity. PMID:25332505

A computational study on choline benzoate and choline salicylate ionic liquids in the pure state and after CO2 adsorption.

PubMed

Aparicio, Santiago; Atilhan, Mert

2012-08-02

Choline-based ionic liquids show very adequate environmental, toxicological, and economical profiles for their application in many different technological areas. We report in this work a computational study on the properties of choline benzoate and choline salicylate ionic liquids, as representatives of this family of compounds, in the pure state and after CO(2) adsorption. Quantum chemistry calculations using the density functional theory approach for ionic pairs and ions, CO(2) pairs, were carried out, and the results analyzed using natural bond orbital and atoms in a molecule approaches. Classical molecular dynamics simulations of ionic liquids were done as a function of pressure, temperature, and CO(2) concentration. Microscopic structuring and intermolecular forces are analyzed together with the dynamic behavior of the studied fluids.

Novel Broad Spectrum Inhibitors Targeting the Flavivirus Methyltransferase

PubMed Central

Liu, Binbin; Banavali, Nilesh K.; Jones, Susan A.; Zhang, Jing; Li, Zhong; Kramer, Laura D.; Li, Hongmin

2015-01-01

The flavivirus methyltransferase (MTase) is an essential enzyme that sequentially methylates the N7 and 2’-O positions of the viral RNA cap, using S-adenosyl-L-methionine (SAM) as a methyl donor. We report here that small molecule compounds, which putatively bind to the SAM-binding site of flavivirus MTase and inhibit its function, were identified by using virtual screening. In vitro methylation experiments demonstrated significant MTase inhibition by 13 of these compounds, with the most potent compound displaying sub-micromolar inhibitory activity. The most active compounds showed broad spectrum activity against the MTase proteins of multiple flaviviruses. Two of these compounds also exhibited low cytotoxicity and effectively inhibited viral replication in cell-based assays, providing further structural insight into flavivirus MTase inhibition. PMID:26098995

Biodegradation of Mordant orange-1 using newly isolated strain Trichoderma harzianum RY44 and its metabolite appraisal.

PubMed

Hadibarata, Tony; Syafiuddin, Achmad; Al-Dhabaan, Fahad A; Elshikh, Mohamed Soliman; Rubiyatno

2018-05-01

Herein, we systematically reported the capability of T. harzianum RY44 for decolorization of Mordant orange-1. The fungi strains were isolated from the Universiti Teknologi Malaysia tropical rain forest. For initial screening, the decolorization was conducted using 50 strains of the fungi for 20 days incubation time and the best performance was selected. Then, the decolorization capability and fungal biomass were evaluated using different dye concentrations, namely, 0, 50, 75 and 100 ppm. Effects of the carbon sources (fructose, glucose, and galactose), nitrogen sources (ammonium nitrate, ammonium sulfate and yeast extract), surfactant (tween 80), aromatic compounds (benzoic acid, catechol and salicylic acid), and pH on the decolorization efficiency were examined. This study has found that the employed carbon sources, nitrogen sources, and aromatic compounds strongly enhance the decolorization efficiency. In addition, increasing the surfactant volume and pH generally decreased the decolorization efficiencies from 19.5 to 9.0% and 81.7 to 60.5%, respectively. In the mechanism philosophy, the present work has found that Mordant orange-1 were initially degraded by T. harzianum RY44 to benzoic acid and finally transformed into salicylic acid.

Semisynthesis, cytotoxicity, antiviral activity, and drug interaction liability of 7-O-methylated analogues of flavonolignans from milk thistle.

PubMed

Althagafy, Hanan S; Graf, Tyler N; Sy-Cordero, Arlene A; Gufford, Brandon T; Paine, Mary F; Wagoner, Jessica; Polyak, Stephen J; Croatt, Mitchell P; Oberlies, Nicholas H

2013-07-01

Silymarin, an extract of the seeds of milk thistle (Silybum marianum), is used as an herbal remedy, particularly for hepatoprotection. The main chemical constituents in silymarin are seven flavonolignans. Recent studies explored the non-selective methylation of one flavonolignan, silybin B, and then tested those analogues for cytotoxicity and inhibition of both cytochrome P450 (CYP) 2C9 activity in human liver microsomes and hepatitis C virus infection in a human hepatoma (Huh7.5.1) cell line. In general, enhanced bioactivity was observed with the analogues. To further probe the biological consequences of methylation of the seven major flavonolignans, a series of 7-O-methylflavonolignans were generated. Optimization of the reaction conditions permitted selective methylation at the phenol in the 7-position in the presence of each metabolite's 4-5 other phenolic and/or alcoholic positions without the use of protecting groups. These 7-O-methylated analogues, in parallel with the corresponding parent compounds, were evaluated for cytotoxicity against Huh7.5.1 cells; in all cases the monomethylated analogues were more cytotoxic than the parent compounds. Moreover, parent compounds that were relatively non-toxic and inactive or weak inhibitors of hepatitis C virus infection had enhanced cytotoxicity and anti-HCV activity upon 7-O-methylation. Also, the compounds were tested for inhibition of major drug metabolizing enzymes (CYP2C9, CYP3A4/5, UDP-glucuronsyltransferases) in pooled human liver or intestinal microsomes. Methylation of flavonolignans differentially modified inhibitory potency, with compounds demonstrating both increased and decreased potency depending upon the compound tested and the enzyme system investigated. In total, these data indicated that monomethylation modulates the cytotoxic, antiviral, and drug interaction potential of silymarin flavonolignans. Copyright © 2013 Elsevier Ltd. All rights reserved.

Release and uptake of volatile organic compounds by human hepatocellular carcinoma cells (HepG2) in vitro

PubMed Central

2013-01-01

Background Volatile organic compounds (VOCs) emitted by human body offer a unique insight into biochemical processes ongoing in healthy and diseased human organisms. Unfortunately, in many cases their origin and metabolic fate have not been yet elucidated in sufficient depth, thus limiting their clinical application. The primary goal of this work was to identify and quantify volatile organic compounds being released or metabolized by HepG2 hepatocellular carcinoma cells. Methods The hepatocellular carcinoma cells were incubated in specially designed head-space 1-L glass bottles sealed for 24 hours prior to measurements. Identification and quantification of volatiles released and consumed by cells under study were performed by gas chromatography with mass spectrometric detection (GC-MS) coupled with head-space needle trap device extraction (HS-NTD) as the pre-concentration technique. Most of the compounds were identified both by spectral library match as well as retention time comparison based on standards. Results A total of nine compounds were found to be metabolised and further twelve released by the cells under study (Wilcoxon signed-rank test, p<0.05). The former group comprised 6 aldehydes (2-methyl 2-propenal, 2-methyl propanal, 2-ethylacrolein, 3-methyl butanal, n-hexanal and benzaldehyde), n-propyl propionate, n-butyl acetate, and isoprene. Amongst the released species there were five ketones (2-pentanone, 3-heptanone, 2-heptanone, 3-octanone, 2-nonanone), five volatile sulphur compounds (dimethyl sulfide, ethyl methyl sulfide, 3-methyl thiophene, 2-methyl-1-(methylthio)- propane and 2-methyl-5-(methylthio) furan), n-propyl acetate, and 2-heptene. Conclusions The emission and uptake of the aforementioned VOCs may reflect the activity of abundant liver enzymes and support the potential of VOC analysis for the assessment of enzymes function. PMID:23870484

CO-OCCURRENCE OF METHYL- TERT-BUTYL ETHER (MTBE) AND BTEX COMPOUNDS AT MARINAS IN A LARGE RESEVOIR

EPA Science Inventory

Methyl tert-butyl ether (MTBE) is released into the environment as one of some gasoline components, not as a pure compound. BTEX compounds (benzene, tolune, ethylbenzene, and xylenes) are major volatile constituents found in gasoline and are water soluble and mobile. This study...

The Extent to Which Methyl Salicylate Is Required for Signaling Systemic Acquired Resistance Is Dependent on Exposure to Light after Infection1[OA

PubMed Central

Liu, Po-Pu; von Dahl, Caroline C.; Klessig, Daniel F.

2011-01-01

Systemic acquired resistance (SAR) is a state of heightened defense to a broad spectrum of pathogens that is activated throughout a plant following local infection. Development of SAR requires the translocation of one or more mobile signals from the site of infection through the vascular system to distal (systemic) tissues. The first such signal identified was methyl salicylate (MeSA) in tobacco (Nicotiana tabacum). Subsequent studies demonstrated that MeSA also serves as a SAR signal in Arabidopsis (Arabidopsis thaliana) and potato (Solanum tuberosum). By contrast, another study suggested that MeSA is not required for SAR in Arabidopsis and raised questions regarding its signaling role in tobacco. Differences in experimental design, including the developmental age of the plants, the light intensity, and/or the strain of bacterial pathogen, were proposed to explain these conflicting results. Here, we demonstrate that the length of light exposure that plants receive after the primary infection determines the extent to which MeSA is required for SAR signaling. When the primary infection occurred late in the day and as a result infected plants received very little light exposure before entering the night/dark period, MeSA and its metabolizing enzymes were essential for SAR development. In contrast, when infection was done in the morning followed by 3.5 h or more of exposure to light, SAR developed in the absence of MeSA. However, MeSA was generally required for optimal SAR development. In addition to resolving the conflicting results concerning MeSA and SAR, this study underscores the importance of environmental factors on the plant’s response to infection. PMID:22021417

Enhanced aerodynamic reach of vapor and aerosol sampling for real-time mass spectrometric detection using Venturi-assisted entrainment and ionization

PubMed Central

Forbes, Thomas P.; Staymates, Matthew

2017-01-01

Venturi-assisted ENTrainment and Ionization (VENTI) was developed, demonstrating efficient entrainment, collection, and transport of remotely sampled vapors, aerosols, and dust particulate for real-time mass spectrometry (MS) detection. Integrating the Venturi and Coandă effects at multiple locations generated flow and analyte transport from non-proximate locations and more importantly enhanced the aerodynamic reach at the point of collection. Transport through remote sampling probes up to 2.5 m in length was achieved with residence times on the order of 10-2 s to 10-1 s and Reynolds numbers on the order of 103 to 104. The Venturi-assisted entrainment successfully enhanced vapor collection and detection by greater than an order of magnitude at 20 cm stand-off (limit of simple suction). This enhancement is imperative, as simple suction restricts sampling to the immediate vicinity, requiring close proximity to the vapor source. In addition, the overall aerodynamic reach distance was increased by approximately 3-fold over simple suction under the investigated conditions. Enhanced aerodynamic reach was corroborated and observed with laser-light sheet flow visualization and schlieren imaging. Coupled with atmospheric pressure chemical ionization (APCI), the detection of a range of volatile chemical vapors; explosive vapors; explosive, narcotic, and mustard gas surrogate (methyl salicylate) aerosols; and explosive dust particulate was demonstrated. Continuous real-time Venturi-assisted monitoring of a large room (approximately 90 m2 area, 570 m3 volume) was demonstrated for a 60-minute period without the remote sampling probe, exhibiting detection of chemical vapors and methyl salicylate at approximately 3 m stand-off distances within 2 minutes of exposure. PMID:28107830

Antiseptic mouth rinses: an update on comparative effectiveness, risks and recommendations.

PubMed

Osso, Diane; Kanani, Nehal

2013-02-01

Antiseptic mouth rinses are widely recommended and marketed to improve oral health. This article summarizes current studies on the comparative effectiveness of selected antiseptic mouth rinses in controlling plaque and gingivitis, as well as risks associated with daily exposure, including salivary flow rate, oral cancer and wear of composite restorations. Electronic database searches were conducted using Google Scholar and PubMed to identify articles comparing the effectiveness of 4 commercially marketed antiseptic mouth rinses differing in active ingredients (0.12% chlorhexidine gluconate, essential oils (menthol, thymol and eucalyptol) and methyl salicylate, 0.7% cetylpyridinium chloride and 20% aloe vera gel) for controlling plaque and gingivitis. Criteria for inclusion included controlled clinical trials and systematic reviews appearing in English language publications evaluating the comparative effectiveness of the mouth rinses in controlling plaque and gingivitis, as well as risks associated with daily usage. The majority of studies have shown mouth rinses containing chlorhexidine gluconate or essential oils and methyl salicylate provide clinically significant anti-gingivitis and anti-plaque benefits. Cetylpyridinium chloride has been found to provide only limited clinical benefits compared to inactive control mouth rinse. Inadequate evidence is available to evaluate the clinical effectiveness of aloe vera gel. Chlorhexidine, essential oils and cetylpyridinium have been found to be safe. However, limited data are available on the effects of the mouth rinse on wear patterns of dental restorations. Studies reviewed reported no significant difference in salivary flow rate related to alcohol based mouth rinse. Research supports the effectiveness of antiseptic mouth rinses in reducing plaque and gingivitis as an adjunct to home care. Insufficient evidence is available to support the claim that oral antiseptics can reduce the risk of developing periodontitis or the rate of progression of periodontitis.

Evaluation and Selection of Candidate Reference Genes for Normalization of Quantitative RT-PCR in Withania somnifera (L.) Dunal

PubMed Central

Singh, Varinder; Kaul, Sunil C.; Wadhwa, Renu; Pati, Pratap Kumar

2015-01-01

Quantitative real-time PCR (qRT-PCR) is now globally used for accurate analysis of transcripts levels in plants. For reliable quantification of transcripts, identification of the best reference genes is a prerequisite in qRT-PCR analysis. Recently, Withania somnifera has attracted lot of attention due to its immense therapeutic potential. At present, biotechnological intervention for the improvement of this plant is being seriously pursued. In this background, it is important to have comprehensive studies on finding suitable reference genes for this high valued medicinal plant. In the present study, 11 candidate genes were evaluated for their expression stability under biotic (fungal disease), abiotic (wounding, salt, drought, heat and cold) stresses, in different plant tissues and in response to various plant growth regulators (methyl jasmonate, salicylic acid, abscisic acid). The data as analyzed by various software packages (geNorm, NormFinder, Bestkeeper and ΔCt method) suggested that cyclophilin (CYP) is a most stable gene under wounding, heat, methyl jasmonate, different tissues and all stress conditions. T-SAND was found to be a best reference gene for salt and salicylic acid (SA) treated samples, while 26S ribosomal RNA (26S), ubiquitin (UBQ) and beta-tubulin (TUB) were the most stably expressed genes under drought, biotic and cold treatment respectively. For abscisic acid (ABA) treated samples 18S-rRNA was found to stably expressed gene. Finally, the relative expression level of the three genes involved in the withanolide biosynthetic pathway was detected to validate the selection of reliable reference genes. The present work will significantly contribute to gene analysis studies in W. somnifera and facilitate in improving the quality of gene expression data in this plant as well as and other related plant species. PMID:25769035

Enhanced aerodynamic reach of vapor and aerosol sampling for real-time mass spectrometric detection using Venturi-assisted entrainment and ionization.

PubMed

Forbes, Thomas P; Staymates, Matthew

2017-03-08

Venturi-assisted ENTrainment and Ionization (VENTI) was developed, demonstrating efficient entrainment, collection, and transport of remotely sampled vapors, aerosols, and dust particulate for real-time mass spectrometry (MS) detection. Integrating the Venturi and Coandă effects at multiple locations generated flow and analyte transport from non-proximate locations and more importantly enhanced the aerodynamic reach at the point of collection. Transport through remote sampling probes up to 2.5 m in length was achieved with residence times on the order of 10 -2  s to 10 -1  s and Reynolds numbers on the order of 10 3 to 10 4 . The Venturi-assisted entrainment successfully enhanced vapor collection and detection by greater than an order of magnitude at 20 cm stand-off (limit of simple suction). This enhancement is imperative, as simple suction restricts sampling to the immediate vicinity, requiring close proximity to the vapor source. In addition, the overall aerodynamic reach distance was increased by approximately 3-fold over simple suction under the investigated conditions. Enhanced aerodynamic reach was corroborated and observed with laser-light sheet flow visualization and schlieren imaging. Coupled with atmospheric pressure chemical ionization (APCI), the detection of a range of volatile chemical vapors; explosive vapors; explosive, narcotic, and mustard gas surrogate (methyl salicylate) aerosols; and explosive dust particulate was demonstrated. Continuous real-time Venturi-assisted monitoring of a large room (approximately 90 m 2 area, 570 m 3 volume) was demonstrated for a 60-min period without the remote sampling probe, exhibiting detection of chemical vapors and methyl salicylate at approximately 3 m stand-off distances within 2 min of exposure. Published by Elsevier B.V.

Structure-activity relationships of sandalwood odorants: synthesis and odour of methyl-beta-santalol.

PubMed

Buchbauer, G; Zechmeister-Machhart, F; Weiss-Greiler, P; Wolschann, P

1997-04-01

The synthesis and odour properties of the new santalol analogue, methyl-beta-santalol, are described. The additional methyl group adjacent to the hydroxyl function of the standard molecule, beta-santalol, deprives the new compound of the sandalwood note. The synthesis and the odour evaluation of this compound supports the proposed model for sandalwood fragrance as it shows that the methyl group located at the osmophoric center prevents association of the molecule with the hypothetical receptor.

A general method for N-methylation of amines and nitro compounds with dimethylsulfoxide.

PubMed

Jiang, Xue; Wang, Chao; Wei, Yawen; Xue, Dong; Liu, Zhaotie; Xiao, Jianliang

2014-01-03

DMSO methylates a broad range of amines in the presence of formic acid, providing a novel, green and practical method for amine methylation. The protocol also allows the one-pot transformation of aromatic nitro compounds into dimethylated amines in the presence of a simple iron catalyst. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Determination of drugs in surface water and wastewater samples by liquid chromatography-mass spectrometry: Methods and preliminary results including toxicity studies with Vibrio fischeri

USGS Publications Warehouse

Farre, M.; Ferrer, I.; Ginebreda, A.; Figueras, M.; Olivella, L.; Tirapu, L.; Vilanova, M.; Barcelo, D.

2001-01-01

In the present work a combined analytical method involving toxicity and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) was developed for the determination of pharmaceutical compounds in water samples. The drugs investigated were the analgesics: ibuprofen, ketoprofen, naproxen, and diclofenac, the decomposition product of the acetyl salicylic acid: salicylic acid and one lipid lowering agent, gemfibrozil. The selected compounds are acidic substances, very polar and all of them are analgesic compounds that can be purchased without medical prescription. The developed protocol consisted, first of all, on the use Microtox?? and ToxAlert??100 toxicity tests with Vibrio fischeri for the different pharmaceutical drugs. The 50% effective concentration (EC50) values and the toxicity units (TU) were determined for every compound using both systems. Sample enrichment of water samples was achieved by solid-phase extraction procedure (SPE), using the Merck LiChrolut?? EN cartridges followed by LC-ESI-MS. Average recoveries loading 1 l of samples with pH=2 varied from 69 to 91% and the detection limits in the range of 15-56 ng/l. The developed method was applied to real samples from wastewater and surface-river waters of Catalonia (north-east of Spain). One batch of samples was analyzed in parallel also by High Resolution Gas Chromatography coupled with Mass Spectrometry (HRGC-MS) and the results have been compared with the LC-ESI-MS method developed in this work. ?? 2001 Elsevier Science B.V. All rights reserved.

Synthetic versatility of 2-substituted-6-methyl 2,3-dihydropyridinones in the synthesis of polyfunctional piperidine-based compounds and related β amino acid derivatives.

PubMed

Yang, Yang; Hardman, Clayton

2017-10-18

Chiral 2-substituted-6-methyl 2,3-dihydropyidinones 9, which can be facilely obtained from an asymmetric vinylogous Mannich reaction (VMR) with 1,3-bis-trimethysily enol ether, were used as versatile intermediates in constructing chiral polyfunctional piperidine-based compounds. The 6-methyl group of such compounds can be conveniently functionalized via alkylation and acylation reactions to provide efficient entries to the synthesis of a variety of chiral multi-substituted piperidine-based compounds. Further elaboration of the corresponding intermediates also provided access to polyfunctional indolizidine-based compounds. These methods were showcased in an asymmetric synthesis of 2,6-di-substituted piperidine compound 13, reported as the key intermediate in the synthesis of (+)-calvine and a natural alkaloid (-)-indolizidine 209D. Furthermore, selective C5 iodination of compound 9 enabled the installation of additional functional groups at this position. Finally, we demonstrated that the oxidative cleavage of 2-substituted-6-methyl-2,3-dihydropyidinones is a practical and efficient method for the enantioselective synthesis of β-amino acids, which can undergo further intra-molecular cyclization to give the corresponding chiral four-membered β-lactam derivatives.

The 1-((diorganooxyphosphonyl)-methyl)-2,4- and -2,6-diamido benzenes

NASA Technical Reports Server (NTRS)

Mikroyannidis, John A. (Inventor); Kourtides, Demetrius A. (Inventor)

1989-01-01

1-((Diorgano oxyphosphonyl) methyl)-2,4- and -2,6-dinitro and diamino benzenes are prepared by nitrating an (organophosphonyl) methyl benzene to produce the dinitro compounds which are then reduced to the diamino compounds. The organo grounds (alkyl, haloalkyl, aryl) on the phosphorus may be removed to give the free acids (HO)2P(double bond O)single bond. The diamino compounds may be polymerized with dianhydrides or diacyl halides to produce fire and flame resistant polymers which are useful in the manufacture of aircraft structures.

The 1-((diorganooxy phosphonyl) methyl)-2,4- and -2,6-diamino benzenes and their derivatives

NASA Technical Reports Server (NTRS)

Mikroyannidis, John A. (Inventor); Kourtides, Demetrius A. (Inventor)

1987-01-01

The 1-((diorganooxy phosphonyl) methyl)-2,4- and -2,6-dinitro- and diamino benzenes are prepared by nitrating an (organo phosphenyl) methyl benzene to produce the dinitro compounds which are then reduced to the diamino compounds. The organo groups (alkyl, haloalkyl, aryl) on the phosphorus may be removed to give the free acids (HO)2P(=0)-. The diamino compounds may be polymerized with dianhydrides or diacyl halides to produce fire and flame resistant polymers which are useful in the manufacture of aircraft structures.

Biologic poisons for pain.

PubMed

Reisner, Lori

2004-12-01

Pain therapies from natural sources date back thousands of years to the use of plant and animal extracts for a variety of painful conditions and injuries. We certainly are all familiar with modern uses of plant-derived analgesic compounds such as opium derivatives from papaverum somniferum and salicylates from willow bark (Salix species). Local anesthetics were isolated from coca leaves in the late 1800s. Sarapin, derived from carnivorous pitcher plants, has been injected for regional analgesia in human and veterinary medicine, but efficacy is controversial. Biologic organisms can play important roles in developing an understanding of pain mechanisms, either from isolation of compounds that are analgesic or of compounds that produce pain, hyperalgesia, and allodynia.

Assessing the potential for rhizoremediation of PCB contaminated soils in northern regions using native species

PubMed Central

Slater, Heather; Gouin, Todd; Leigh, Mary Beth

2011-01-01

Rhizosphere bioremediation of polychlorinated biphenyls (PCBs) offers a potentially inexpensive approach to remediating contaminated soils that is particularly attractive in remote regions including the Arctic. We assessed the abilities of two tree species native to Alaska, Salix alaxensis (felt-leaf willow) and Picea glauca (white spruce), to promote microbial biodegradation of PCBs via the release of phytochemicals upon fine root death. Crushed fine roots, biphenyl (PCB analogue) or salicylate (willow secondary compound) were added to microcosms containing soil spiked with PCBs and resultant PCB disappearance, soil toxicity and microbial community changes were examined. After 180 d, soil treated with willow root crushates showed a significantly greater PCB loss than untreated soils for some PCB congeners, including the toxic congeners, PCB 77, 105 and 169, and showed a similar PCB loss pattern (in both extent of degradation and congeners degraded) to biphenyl-treated microcosms. Neither P. glauca (white spruce) roots nor salicylate enhanced PCB loss, indicating that biostimulation is plant species specific and was not mediated by salicylate. Soil toxicity assessed using the Microtox bioassay indicated that the willow treatment resulted in a less toxic soil environment. Molecular microbial community analyses indicated that biphenyl and salicylate promoted shifts in microbial community structure and composition that differed distinctly from each other and from the crushed root treatments. The biphenyl utilizing bacterium, Cupriavidus spp. was isolated from the soil. The findings suggest that S. alaxensis may be an effective plant for rhizoremediation by altering microbial community structure, enhancing the loss of some PCB congeners and reducing the toxicity of the soil environment. PMID:21596420

Differential presence of anthropogenic compounds dissolved in the marine waters of Puget Sound, WA and Barkley Sound, BC.

PubMed

Keil, Richard; Salemme, Keri; Forrest, Brittany; Neibauer, Jaqui; Logsdon, Miles

2011-11-01

Organic compounds were evaluated in March 2010 at 22 stations in Barkley Sound, Vancouver Island Canada and at 66 locations in Puget Sound. Of 37 compounds, 15 were xenobiotics, 8 were determined to have an anthropogenic imprint over natural sources, and 13 were presumed to be of natural or mixed origin. The three most frequently detected compounds were salicyclic acid, vanillin and thymol. The three most abundant compounds were diethylhexyl phthalate (DEHP), ethyl vanillin and benzaldehyde (∼600 n g L(-1) on average). Concentrations of xenobiotics were 10-100 times higher in Puget Sound relative to Barkley Sound. Three compound couplets are used to illustrate the influence of human activity on marine waters; vanillin and ethyl vanillin, salicylic acid and acetylsalicylic acid, and cinnamaldehyde and cinnamic acid. Ratios indicate that anthropogenic activities are the predominant source of these chemicals in Puget Sound. Published by Elsevier Ltd.

An Overview of Plant Phenolic Compounds and Their Importance in Human Nutrition and Management of Type 2 Diabetes.

PubMed

Lin, Derong; Xiao, Mengshi; Zhao, Jingjing; Li, Zhuohao; Xing, Baoshan; Li, Xindan; Kong, Maozhu; Li, Liangyu; Zhang, Qing; Liu, Yaowen; Chen, Hong; Qin, Wen; Wu, Hejun; Chen, Saiyan

2016-10-15

In this paper, the biosynthesis process of phenolic compounds in plants is summarized, which include the shikimate, pentose phosphate and phenylpropanoid pathways. Plant phenolic compounds can act as antioxidants, structural polymers (lignin), attractants (flavonoids and carotenoids), UV screens (flavonoids), signal compounds (salicylic acid, flavonoids) and defense response chemicals (tannins, phytoalexins). From a human physiological standpoint, phenolic compounds are vital in defense responses, such as anti-aging, anti-inflammatory, antioxidant and anti-proliferative activities. Therefore, it is beneficial to eat such plant foods that have a high antioxidant compound content, which will cut down the incidence of certain chronic diseases, for instance diabetes, cancers and cardiovascular diseases, through the management of oxidative stress. Furthermore, berries and other fruits with low-amylase and high-glucosidase inhibitory activities could be thought of as candidate food items in the control of the early stages of hyperglycemia associated with type 2 diabetes.

Fragrances in oolong tea that enhance the response of GABAA receptors.

PubMed

Hossain, Sheikh Julfikar; Aoshima, Hitoshi; Koda, Hirofumi; Kiso, Yoshinobu

2004-09-01

We electrophysiologically investigated the effect of some fragrant compounds in oolong tea on the response of ionotropic gamma-aminobutyric acid (GABA) receptors (GABAA receptors) which were expressed in Xenopus oocytes. Of the tested fragrances in oolong tea, cis-jasmone, jasmine lactone, linalool oxide and methyl jasmonate significantly potentiated the response. Among these, cis-jasmone and methyl jasmonate potently potentiated the response, having a respective dissociation constant of the compound (Kp) and maximum potentiation (Vm) of 0.49 mM and 322% for cis-jasmone, and 0.84 mM and 450% for methyl jasmonate. Inhalation of 0.1% cis-jasmone or methyl jasmonate significantly increased the sleeping time of mice induced by pentobarbital, suggesting that these fragrant compounds were absorbed by the brain and thereby potentiated the GABAA receptor response. Both of these compounds may therefore have a tranquillizing effect on the brain.

BnNHL18A shows a localization change by stress-inducing chemical treatments

DOE Office of Scientific and Technical Information (OSTI.GOV)

Lee, Suk-Bae; Ham, Byung-Kook; Park, Jeong Mee

2006-01-06

The two genes, named BnNHL18A and BnNHL18B, showing sequence homology with Arabidopsis NDR1/HIN1-like (NHL) genes, were isolated from cDNA library prepared with oilseed rape (Brassica napus) seedlings treated with NaCl. The transcript level of BnNHL18A was increased by sodium chloride, ethephon, hydrogen peroxide, methyl jasmonate, or salicylic acid treatment. The coding regions of BnNHL18A and BnNHL18B contain a sarcolipin (SLN)-like sequence. Analysis of the localization of smGFP fusion proteins showed that BnNHL18A is mainly localized to endoplasmic reticulum (ER). This result suggests that the SLN-like sequence plays a role in retaining proteins in ER membrane in plants. In response tomore » NaCl, hydrogen peroxide, ethephon, and salicylic acid treatments, the protein localization of BnNHL18A was changed. Our findings suggest a common function of BnNHL18A in biotic and abiotic stresses, and demonstrate the presence of the shared mechanism of protein translocalization between the responses to plant pathogen and to osmotic stress.« less

GC-MS studies on the regioisomeric methoxy-methyl-phenethylamines related to MDEA, MDMMA, and MBDB.

PubMed

Thigpen, Ashley; Awad, Tamer; Deruiter, Jack; Clark, C Randall

2008-01-01

Three regioisomeric 3,4-methylenedioxyphenethylamines having the same molecular weight and major mass spectral fragments of equal mass have been reported as drugs of abuse in forensic studies in recent years. These compounds are 3,4-methylenedioxy-N-ethylamphetamine (MDEA), 3,4-methylenedioxy-N-N-dimethylamphetamine (MDMMA), and N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (MBDB). The mass spectra of the regioisomers (4-methoxy-3-methyl and 4-methoxy-2-methyl-phenethylamines) are essentially equivalent to the three compounds reported as drugs of abuse. This project focused on the synthesis, mass spectral characterization, and chromatographic analysis of these six regioisomeric methoxy methyl phenethylamines. Additionally, the mass spectral and chromatographic properties of these compounds will be compared to the isobaric 2,3- and 3,4-methylenedioxyphenethyl-amines of the same side chain. The six regioisomeric methoxy-methyl-phenethylamines were synthesized from commercially available starting materials. Side chain differentiation by mass spectrometry was possible after the formation of the perfluoroacyl derivatives, pentafluoropropionylamides (PFPA) and heptafluorobutrylamides (HFBA). Gas chromatographic separation on Rtx-1 was successful at resolving the perfluoroacyl derivatives of the 4-methoxy-3-methyl phenethylamines from those of the 4-methoxy-2-methyl phenethylamines. The 4-methoxy-3-methyl-phenethylamine derivatives eluted before the 4-methoxy-2-methyl-phenethylamine derivatives as both the PFPA and HFBA derivatives.

Kinetics of the gas-phase reaction between ozone and three unsaturated oxygenated compounds: Ethyl 3,3-dimethyl acrylate, 2-methyl-2-pentenal and 6-methyl-5-hepten-2-one at atmospheric pressure

NASA Astrophysics Data System (ADS)

Gaona Colmán, Elizabeth; Blanco, María B.; Barnes, Ian; Teruel, Mariano A.

2015-05-01

Rate coefficients for the gas-phase reactions of O3 molecules with three unsaturated oxygenated compounds have been determined using the relative kinetic technique in an environmental chamber with FTIR detection of the reactants at (298 ± 2) K in 760 Torr total pressure of synthetic air. The following rate coefficients (in units of 10-17 cm3 molecule-1 s-1) were determined: ethyl 3,3-dimethyl acrylate (0.82 ± 0.19), 2-methyl-2-pentenal (0.71 ± 0.16) and 6-methyl-5-hepten-2-one (26 ± 7). The different reactivity of the unsaturated oxygenated compounds toward O3 is discussed in terms of their chemical structure. In addition, a correlation between the reactivity of structurally different unsaturated compounds (alkenes and unsaturated oxygenated VOCs, such as ethers, esters, aldehydes, ketones and alcohols) toward O3 molecules and the HOMO (Highest Occupied Molecular Orbital) of the compounds is presented. Using the kinetic parameters determined in this work, residence times of these unsaturated compounds in the atmosphere with respect to reaction with O3 have been calculated. In urban and rural areas the main sink of 6-methyl-5-hepten-2-one is reaction with O3 molecules with a residence time in the order of few minutes.

A review of toxicity from topical salicylic acid preparations.

PubMed

Madan, Raman K; Levitt, Jacob

2014-04-01

Topical salicylic acid is often used in dermatologic conditions because of its keratolytic, bacteriostatic, fungicidal, and photoprotective properties. The bioavailability of salicylic acid differs depending on the vehicle used and pH of transcellular fluids. Although rare, salicylic acid toxicity (salicylism) can occur from topical application. Physicians should be mindful of the potential for salicylism or even death from topically applied salicylic acid. Copyright © 2013 American Academy of Dermatology, Inc. Published by Mosby, Inc. All rights reserved.

Zebrafish embryos as a screen for DNA methylation modifications after compound exposure

DOE Office of Scientific and Technical Information (OSTI.GOV)

Bouwmeester, Manon C.; Ruiter, Sander; Lommelaars, Tobias

Modified epigenetic programming early in life is proposed to underlie the development of an adverse adult phenotype, known as the Developmental Origins of Health and Disease (DOHaD) concept. Several environmental contaminants have been implicated as modifying factors of the developing epigenome. This underlines the need to investigate this newly recognized toxicological risk and systematically screen for the epigenome modifying potential of compounds. In this study, we examined the applicability of the zebrafish embryo as a screening model for DNA methylation modifications. Embryos were exposed from 0 to 72 h post fertilization (hpf) to bisphenol-A (BPA), diethylstilbestrol, 17α-ethynylestradiol, nickel, cadmium, tributyltin,more » arsenite, perfluoroctanoic acid, valproic acid, flusilazole, 5-azacytidine (5AC) in subtoxic concentrations. Both global and site-specific methylation was examined. Global methylation was only affected by 5AC. Genome wide locus-specific analysis was performed for BPA exposed embryos using Digital Restriction Enzyme Analysis of Methylation (DREAM), which showed minimal wide scale effects on the genome, whereas potential informative markers were not confirmed by pyrosequencing. Site-specific methylation was examined in the promoter regions of three selected genes vasa, vtg1 and cyp19a2, of which vasa (ddx4) was the most responsive. This analysis distinguished estrogenic compounds from metals by direction and sensitivity of the effect compared to embryotoxicity. In conclusion, the zebrafish embryo is a potential screening tool to examine DNA methylation modifications after xenobiotic exposure. The next step is to examine the adult phenotype of exposed embryos and to analyze molecular mechanisms that potentially link epigenetic effects and altered phenotypes, to support the DOHaD hypothesis. - Highlights: • Compound induced effects on DNA methylation in zebrafish embryos • Global methylation not an informative biomarker • Minimal genome wide site specific changes as detected with DREAM • Compound/class specific effects suggested by pyrosequence of specific targets • Zebrafish embryo may be a screening model for epigenetic effects.« less

Heptyl vicianoside and methyl caramboside from sour star fruit.

PubMed

Yang, Dan; Jia, Xuchao; Xie, Haihui

2018-04-23

Two new alkyl glycosides, heptyl vicianoside (1) and methyl 2-O-β-d-fucopyranosyl-α-l-arabinofuranoside (methyl caramboside, 4), were isolated from the sour fruit of Averrhoa carambola L. (Oxalidaceae), along with octyl vicianoside (2), cis-3-hexenyl rutinoside (3), and methyl α-d-fructofuranoside (5). Their structures were determined by spectroscopic and chemical methods. Compounds 2, 3, and 5 were obtained from the genus Averrhoa for the first time. All the compounds were evaluated for in vitro α-glucosidase, pancreatic lipase, and acetylcholinesterase inhibitory activities, but none of them were potent.

Effect of Salicylate on the Elasticity, Bending Stiffness, and Strength of SOPC Membranes

PubMed Central

Zhou, Yong; Raphael, Robert M.

2005-01-01

Salicylate is a small amphiphilic molecule which has diverse effects on membranes and membrane-mediated processes. We have utilized micropipette aspiration of giant unilamellar vesicles to determine salicylate's effects on lecithin membrane elasticity, bending rigidity, and strength. Salicylate effectively reduces the apparent area compressibility modulus and bending modulus of membranes in a dose-dependent manner at concentrations above 1 mM, but does not greatly alter the actual elastic compressibility modulus at the maximal tested concentration of 10 mM. The effect of salicylate on membrane strength was investigated using dynamic tension spectroscopy, which revealed that salicylate increases the frequency of spontaneous defect formation and lowers the energy barrier for unstable hole formation. The mechanical and dynamic tension experiments are consistent and support a picture in which salicylate disrupts membrane stability by decreasing membrane stiffness and membrane thickness. The tension-dependent partitioning of salicylate was utilized to calculate the molecular volume of salicylate in the membrane. The free energy of transfer for salicylate insertion into the membrane and the corresponding partition coefficient were also estimated, and indicated favorable salicylate-membrane interactions. The mechanical changes induced by salicylate may affect several biological processes, especially those associated with membrane curvature and permeability. PMID:15951377

[Chalcones from Bauhinia glauca subsp. pernervosa].

PubMed

Wu, Zengbao; Wang, Bin; Zhao, Yuying; Yang, Xiuwei; Liang, Hong

2009-07-01

To study the chemical constituents of Bauhinia glauca subsp. pernervosa. The coulis of B. glauca subsp. pernervosa were extracted with 95% EtOH at room temperature. The compounds were isolated and separated by chromatographic techniques, and structures were identified by spectroscopic methods. Seven chalcones were isolated and identified: butein-4-methyl ether (1), isoliquiritigenin (2), butein (3), isoliquiritigenin-2'-methyl ether (4), 2',4'-dihydroxychalcone (5), isoliquiritigenin-4-methyl ether (6), 4-hydroxy-2',4'-dimethoxychalcone (7). Compounds 1, 3, and 7 were isolated from the genus Bauhinia for the first time, the other compounds were obtained from this plant for the first time.

Synthesis and radical scavenging activity of 6-hydroxyl-4-methylcoumarin and its derivatives

NASA Astrophysics Data System (ADS)

Jumal, Juliana; Ayomide, Adetunji Fridaos

2018-06-01

Four compounds of coumarin derivatives namely 6-hydroxyl-4-methylcoumarin (I), 6-hydroxyl-4-methyl-5-(p-nitrophenyl azocoumarin) (II), 6-hydroxyl-4-methyl-5,7-(bis-p-nitrophenyl azocoumarin) (III) and 6-hydroxyl-4-methyl-5,7-(bis-p-chlorophenyl azocoumarin) (IV) were successfully synthesized. These compounds were prepared by reacting hydroquinone with ethylacetoacetate and selected anilines which are chloro and nitro aniline. All synthesized compounds were characterized by CHN micro-elemental analysis, 1H Nuclear Magnetic Resonance (NMR) and Fourier Transform Infrared (FTIR) spectroscopic methods. The infrared spectra of these compounds exhibited five important stretching vibrations: ʋ(-OH), ʋ(C=O), ʋ(C=C), ʋ(C-O) and ʋ(C-N) at 3441-3359 cm-1, 1604-1632 cm-1, 1581-1496 cm-1, 1331-1225 cm-1, 1251-1109 cm-1, respectively. 1H NMR spectra of these compounds show the presence of proton aromatic, proton methyl and proton pyrone ring with the chemical shift at δH 7.00-8.70 ppm, δH 2.20-2.50 ppm and δH 6.10-6.90 ppm, respectively. CHN analysis results of all compounds are in good agreement with the calculated values. All the synthesized compounds were evaluated for their antioxidant activity using DPPH method and ascorbic acid used as the standard. UV-Vis spectroscopic technique was used to investigate the absorbance of these compounds. Compound (II) shows high antioxidant activities compared to compound (I), (III) and (IV) which show moderate to low activities.

Role of salicylic acid in resistance to cadmium stress in plants.

PubMed

Liu, Zhouping; Ding, Yanfei; Wang, Feijuan; Ye, Yaoyao; Zhu, Cheng

2016-04-01

We review and introduce the importance of salicylic acid in plants under cadmium stress, and provide insights into potential regulatory mechanisms for alleviating cadmium toxicity. Cadmium (Cd) is a widespread and potentially toxic environmental pollutant, originating mainly from rapid industrial processes, the application of fertilizers, manures and sewage sludge, and urban activities. It is easily taken up by plants, resulting in obvious toxicity symptoms, including growth retardation, leaf chlorosis, leaf and root necrosis, altered structures and ultrastructures, inhibition of photosynthesis, and cell death. Therefore, alleviating Cd toxicity in plants is a major aim of plant research. Salicylic acid (SA) is a ubiquitous plant phenolic compound that has been used in many plant species to alleviate Cd toxicity by regulating plant growth, reducing Cd uptake and distribution in plants, protecting membrane integrity and stability, scavenging reactive oxygen species and enhancing antioxidant defense system, improving photosynthetic capacity. Furthermore, SA functions as a signaling molecule involved in the expression of several important genes. Significant amounts of research have focused on understanding SA functions and signaling in plants under Cd stress, but several questions still remain unanswered. In this article, the influence of SA on Cd-induced stress in plants and the potential regulation mechanism for alleviating Cd toxicity are reviewed.

Volatile compounds in whole meal bread crust: The effects of yeast level and fermentation temperature.

PubMed

Nor Qhairul Izzreen, M N; Hansen, Se S; Petersen, Mikael A

2016-11-01

The influence of fermentation temperatures (8°C, 16°C, and 32°C) and yeast levels (2%, 4%, and 6% of the flour) on the formation of volatile compounds in the crust of whole meal wheat bread was investigated. The fermentation times were regulated to optimum bread height for each treatment. The volatile compounds were extracted by dynamic headspace extraction and analyzed by gas chromatography-mass spectrometry. The results were evaluated using multivariate data analysis and ANOVA. In all crust samples 28 volatile compounds out of 58 compounds were identified and the other 30 compounds were tentatively identified. Higher fermentation temperatures promoted the formation of Maillard reaction products 3-methyl-1-butanol, pyrazine, 2-ethylpyrazine, 2-ethyl-3-methylpyrazine, 2-vinylpyrazine, 3-hydroxy-2-butanone, 3-(methylsulfanyl)-propanal, and 5-methyl-2-furancarboxaldehyde whereas at lower temperature (8°C) the formation of 2- and 3-methylbutanal was favored. Higher levels of yeast promoted the formation of 3-methyl-1-butanol, 2-methyl-1-propanol and 3-(methylsulfanyl)-propanal, whereas hexanal was promoted in the crust fermented with lower yeast level. Copyright © 2016 Elsevier Ltd. All rights reserved.

Studies on the structural, optical and dielectric properties of samarium coordinated with salicylic acid single crystal

NASA Astrophysics Data System (ADS)

Singh, Harjinder; Slathia, Goldy; Gupta, Rashmi; Bamzai, K. K.

2018-04-01

Samarium coordinated with salicylic acid was successfully grown as a single crystal by low temperature solution technique using mixed solvent of methanol and water in equal ratio. Structural characterization was carried out by single crystal X-ray diffraction analysis and it crystallizes in centrosymmetric space group P121/c1. FTIR and UV-Vis-NIR spectroscopy confirmed the compound formation and help to determine the mode of binding of the ligand to the rare earth-metal ion. Dielectric constant and dielectric loss have been measured over the frequency range 100 Hz - 30MHz. The decrease in dielectric constant with increases in frequency is due to the transition from interfacial polarization to dipolar polarization. The small value of dielectric constant at higher frequency ensures that the crystal is good candidate for NLO devices. Dielectric loss represents the resistive nature of the material.

Catabolism of benzoate and monohydroxylated benzoates by Amycolatopsis and Streptomyces spp.

PubMed Central

Grund, E; Knorr, C; Eichenlaub, R

1990-01-01

Eight actinomycetes of the genera Amycolatopsis and Streptomyces were tested for the degradation of aromatic compounds by growth in a liquid medium containing benzoate, monohydroxylated benzoates, or quinate as the principal carbon source. Benzoate was converted to catechol. The key intermediate in the degradation of salicylate was either catechol or gentisate, while m-hydroxybenzoate was metabolized via gentisate or protocatechuate. p-Hydroxybenzoate and quinate were converted to protocatechuate. Catechol, gentisate, and protocatechuate were cleaved by catechol 1,2-dioxygenase, gentisate 1,2-dioxygenase, and protocatechuate 3,4-dioxygenase, respectively. The requirement for glutathione in the gentisate pathway was dependent on the substrate and the particular strain. The conversion of p-hydroxybenzoate to protocatechuate by p-hydroxybenzoate hydroxylase was gratuitously induced by all substrates that were metabolized via protocatechuate as an intermediate, while protocatechuate 3,4-dioxygenase was gratuitously induced by benzoate and salicylate in two Amycolatopsis strains. PMID:2339895

9-methoxycanthin-6-one production in elicited hairy roots culture of Eurycoma longifolia

NASA Astrophysics Data System (ADS)

Abdullah, Nazirah; Ismail, Ismanizan; Hassan, Nor Hasnida; Basherudin, Norlia

2016-11-01

Eurycoma longifolia (Tongkat Ali) is a highly sought after medicinal plant in Malaysia. Propagation of E. longifolia through tissue culture has been reported in order to cater the industry demands for planting and raw materials as well as for conservation purposes. E. longifolia hairy roots culture has been developed using Agrobacterium rhizogenes for the production of Tongkat Ali phytochemicals. Effects of three elicitors; methyl jasmonate, salicylic acid, and yeast extract at different concentrations were evaluated on the production of 9-methoxycanthin-6-one in E. longifolia hairy roots. The cultures were elicited at early exponential growth phase, followed by extraction of 9-methoxycanthin-6-one using methanol and HPLC analysis. Elicitation with methyl jasmonate at all concentrations increased 9-methoxycanthin-6-one up to 1-3 fold and treatment with (0.1 mM) was most efficient in enhancing 9-methoxycanthin-6-one production up to 3.902 mg/g dry weight after 7 days (168 hours) elicitation.

Isolation, characterization and mode of antimicrobial action against Vibrio cholerae of methyl gallate isolated from Acacia farnesiana.

PubMed

Sánchez, E; Heredia, N; Camacho-Corona, M Del R; García, S

2013-12-01

The antimicrobial activity of Acacia farnesiana against Vibrio cholerae has been demonstrated; however, no information regarding its active compound or its mechanism of action has been documented. The active compound was isolated from A. farnesiana by bioassay-guided fractionation and identified as methyl gallate by nuclear magnetic resonance (NMR) techniques ((1) H NMR and (13) C NMR). The minimum bactericidal concentration (MBC) of methyl gallate and its effect on membrane integrity, cytoplasmic pH, membrane potential, ATP synthesis and gene expression of cholera toxin (ctx) from V. cholerae were determined. The MBC of methyl gallate ranged from 30 ± 1 to 50 ± 1 μg ml(-1) . Methyl gallate affected cell membrane integrity, causing a decrease in cytoplasmic pH (pHin , from 7·3 to <3·0), and membrane hyperpolarization, and ATP was no longer produced by the treated cells. However, methyl gallate did not affect ctx gene expression. Methyl gallate is a major antimicrobial compound from A. farnesiana that disturbs the membrane activity of V. cholerae. The effects of methyl gallate validate several traditional antimicrobial uses of A. farnesiana, and it is an attractive alternative to control V. cholerae. © 2013 The Society for Applied Microbiology.

Meadowsweet Teas as New Functional Beverages: Comparative Analysis of Nutrients, Phytochemicals and Biological Effects of Four Filipendula Species.

PubMed

Olennikov, Daniil N; Kashchenko, Nina I; Chirikova, Nadezhda K

2016-12-26

In recent years, the increased popularity of functional beverages such as herbal teas and decoctions has led to the search for new sources of raw materials that provide appropriate taste and functionality to consumers. The objective of this study was to investigate the nutritional, phytochemical profiles and bioactivities of possible functional beverages produced from F. ulmaria and its alternative substitutes ( F. camtschatica , F. denudata , F. stepposa ). The investigated decoctions were analyzed regarding their macronutrient, carbohydrate, organic acid, amino acid and mineral composition. Quantification of the main phenolic compounds in the decoctions of meadowsweet floral teas was performed by a microcolumn RP-HPLC-UV procedure; the highest content was revealed in F. stepposa tea. The investigation of the essential oil of four meadowsweet teas revealed the presence of 28 compounds, including simple phenols, monoterpenes, sesquiterpenes and aliphatic components. The dominance of methyl salicylate and salicylaldehyde was noted in all samples. Studies on the water soluble polysaccharides of Filipendula flowers allowed us to establish their general affiliation to galactans and/or arabinogalactans with an admixture of glucans of the starch type and galacturonans as minor components. The bioactivity data demonstrated a good ability of meadowsweet teas to inhibit amylase, α-glucosidase and AGE formation. Tea samples showed antioxidant properties by the DPPH • , ABTS •+ and Br • free radicals scavenging assays and the carotene bleaching assay, caused by the presence of highly active ellagitannins. The anti-complement activity of the water-soluble polysaccharide fraction of meadowsweet teas indicated their possible immune-modulating properties. Filipendula beverage formulations can be expected to deliver beneficial effects due to their unique nutritional and phytochemical profiles. Potential applications as health-promoting functional products may be suggested.

Quantification of selected volatile organic compounds in human urine by gas chromatography selective reagent ionization time of flight mass spectrometry (GC-SRI-TOF-MS) coupled with head-space solid-phase microextraction (HS-SPME).

PubMed

Mochalski, Paweł; Unterkofler, Karl

2016-08-07

Selective reagent ionization time of flight mass spectrometry with NO(+) as the reagent ion (SRI-TOF-MS(NO(+))) in conjunction with gas chromatography (GC) and head-space solid-phase microextraction (HS-SPME) was used to determine selected volatile organic compounds in human urine. A total of 16 volatiles exhibiting high incidence rates were quantified in the urine of 19 healthy volunteers. Amongst them there were ten ketones (acetone, 2-butanone, 3-methyl-2-butanone, 2-pentanone, 3-methyl-2-pentanone, 4-methyl-2-pentanone, 2-hexanone, 3-hexanone, 2-heptanone, and 4-heptanone), three volatile sulphur compounds (dimethyl sulfide, allyl methyl sulfide, and methyl propyl sulfide), and three heterocyclic compounds (furan, 2-methylfuran, 3-methylfuran). The concentrations of the species under study varied between 0.55 nmol L(-1) (0.05 nmol mmol(-1)creatinine) for allyl methyl sulfide and 11.6 μmol L(-1) (1.54 μmol mmol(-1)creatinine) for acetone considering medians. Limits of detection (LODs) ranged from 0.08 nmol L(-1) for allyl methyl sulfide to 1.0 nmol L(-1) for acetone and furan (with RSDs ranging from 5 to 9%). The presented experimental setup assists both real-time and GC analyses of volatile organic compounds, which can be performed consecutively using the same analytical system. Such an approach supports the novel concept of hybrid volatolomics, an approach which combines VOC profiles obtained from two or more body fluids to improve and complement the chemical information on the physiological status of an individual.

Novel synthetic kojic acid-methimazole derivatives inhibit mushroom tyrosinase and melanogenesis.

PubMed

Chen, Ming-Jen; Hung, Chih-Chuan; Chen, Yan-Ru; Lai, Shih-Ting; Chan, Chin-Feng

2016-12-01

In this study, two kojic acid-methimazole (2-mercapto-1-methylimidazole, MMI, 1) derivatives, 5-hydroxy-2-{[(1-methyl-1H-imidazol-2-yl)thio]methyl}-4H-pyran-4-one (compound 4) and 5-methoxy-2-{[(1-methyl-1H-imidazol-2-yl)thio]methyl}-4H-pyran-4-one (compound 5), were synthesized to examine their inhibitory kinetics on mushroom tyrosinase. Compound 4 exhibited a potent inhibitory effect on monophenolase activity in a dose-dependent manner, with an IC 50 value of 0.03 mM. On diphenolase activity, compound 4 exhibited a less inhibitory effect (IC 50  = 1.29 mM) but was stronger than kojic acid (IC 50  = 1.80 mM). Kinetic analysis indicated that compound 4 was both as a noncompetitive monophenolase and diphenolase inhibitor. By contrast, compound 5 exhibited no inhibitory effects on mushroom tyrosinase activity. The IC 50 value of compound 4 for the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity was 4.09 mM, being much higher than the IC 50 of compound 4 for inhibiting the tyrosinase activity. The results indicated that the antioxidant activity of compound 4 may be partly related to the potent inhibitory effect on mushroom tyrosinase. Compound 4 also exerted a potent inhibitory effect on intracellular melanin formation in B16/F10 murine melanoma cells, and caused no cytotoxicity. Furthermore, compound 4 induced no adverse effects on the Hen's egg test-chorioallantoic membrane (HET-CAM). Copyright © 2016 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

Repellency of Naturally Occurring or Related Compounds, DEET, and Para-Menthane-3,8-Diol to Bed Bugs (Hemiptera: Cimicidae).

PubMed

Anderson, John F; Ferrandino, Francis J; Vasil, Michael P; Bedoukian, Robert H; Maher, Marie; McKenzie, Karen

2018-05-04

Bed bugs, Cimex lectularius L. (Hemiptera: Cimicidae), have become a major health nuisance in the past 20 ysin cities and elsewhere throughout many areas of the world. Few studies have reported on repellent compounds that could reduce their transport in luggage. We evaluated the repellency of six naturally occurring or related compounds used in flavor/fragrance applications or structurally related compounds, para-menthane-3,8-diol, and N,N-diethyl-meta-toluamide (DEET) to bed bugs in a 183 × 183-cm arena . Repellency was assessed using soft-sided polyester lunch bags serving as surrogates of luggage and barrier cloth towels upon which rested untreated lunch bags. We report for the first time repellency of delta dodecalactone, 2-(3, 7-dimethyl-2, 6-nonadien-1-yl)-cyclopentanone (a.k.a. 'methyl apritone'), gamma dodecalactone, and para-menthane-3,8-diol to bed bugs. Propyl dihydrojasmonate, 3-methyl-5-hexyl-2-cyclohexenone, gamma methyl tridecalactone, and DEET are also documented to be repellent to bed bugs. These compounds provided relatively long-term protection. Propyl dihydrojasmonate prevented bed bugs from seeking refuge in treated lunch bags 27 d after treatment, and when applied to cloth towels repelled harborage-seeking bed bugs for 146 d. Methyl apritone blended with 3-methyl-5-hexyl-2-cyclohexenone and delta dodecalactone as an individual compound applied to cloth towels repelled bed bugs for 190 and 276 d, respectively. The above-mentioned compounds, either individually or as blends, may reduce risk of bed bugs seeking harborage in treated suitcases or towels upon which untreated luggage is placed.

Analysis of salicylic acid-dependent pathways in Arabidopsis thaliana following infection with Plasmodiophora brassicae and the influence of salicylic acid on disease.

PubMed

Lovelock, David A; Šola, Ivana; Marschollek, Sabine; Donald, Caroline E; Rusak, Gordana; van Pée, Karl-Heinz; Ludwig-Müller, Jutta; Cahill, David M

2016-10-01

Salicylic acid (SA) biosynthesis, the expression of SA-related genes and the effect of SA on the Arabidopsis-Plasmodiophora brassicae interaction were examined. Biochemical analyses revealed that, in P. brassicae-infected Arabidopsis, the majority of SA is synthesized from chorismate. Real-time monitored expression of a gene for isochorismate synthase was induced on infection. SA can be modified after accumulation, either by methylation, improving its mobility, or by glycosylation, as one possible reaction for inactivation. Quantitative reverse transcription-polymerase chain reaction (qPCR) confirmed the induction of an SA methyltransferase gene, whereas SA glucosyltransferase expression was not changed after infection. Col-0 wild-type (wt) did not provide a visible phenotypic resistance response, whereas the Arabidopsis mutant dnd1, which constitutively activates the immune system, showed reduced gall scores. As dnd1 showed control of the pathogen, exogenous SA was applied to Arabidopsis in order to test whether it could suppress clubroot. In wt, sid2 (SA biosynthesis), NahG (SA-deficient) and npr1 (SA signalling-impaired) mutants, SA treatment did not alter the gall score, but positively affected the shoot weight. This suggests that SA alone is not sufficient for Arabidopsis resistance against P. brassicae. Semi-quantitative PCR revealed that wt, cpr1, dnd1 and sid2 showed elevated PR-1 expression on P. brassicae and SA + P. brassicae inoculation at 2 and 3 weeks post-inoculation (wpi), whereas NahG and npr1 showed no expression. This work contributes to the understanding of SA involvement in the Arabidopsis-P. brassicae interaction. © 2015 BSPP and John Wiley & Sons Ltd.

Bacteria-triggered systemic immunity in barley is associated with WRKY and ETHYLENE RESPONSIVE FACTORs but not with salicylic acid.

PubMed

Dey, Sanjukta; Wenig, Marion; Langen, Gregor; Sharma, Sapna; Kugler, Karl G; Knappe, Claudia; Hause, Bettina; Bichlmeier, Marlies; Babaeizad, Valiollah; Imani, Jafargholi; Janzik, Ingar; Stempfl, Thomas; Hückelhoven, Ralph; Kogel, Karl-Heinz; Mayer, Klaus F X; Vlot, A Corina

2014-12-01

Leaf-to-leaf systemic immune signaling known as systemic acquired resistance is poorly understood in monocotyledonous plants. Here, we characterize systemic immunity in barley (Hordeum vulgare) triggered after primary leaf infection with either Pseudomonas syringae pathovar japonica (Psj) or Xanthomonas translucens pathovar cerealis (Xtc). Both pathogens induced resistance in systemic, uninfected leaves against a subsequent challenge infection with Xtc. In contrast to systemic acquired resistance in Arabidopsis (Arabidopsis thaliana), systemic immunity in barley was not associated with NONEXPRESSOR OF PATHOGENESIS-RELATED GENES1 or the local or systemic accumulation of salicylic acid. Instead, we documented a moderate local but not systemic induction of abscisic acid after infection of leaves with Psj. In contrast to salicylic acid or its functional analog benzothiadiazole, local applications of the jasmonic acid methyl ester or abscisic acid triggered systemic immunity to Xtc. RNA sequencing analysis of local and systemic transcript accumulation revealed unique gene expression changes in response to both Psj and Xtc and a clear separation of local from systemic responses. The systemic response appeared relatively modest, and quantitative reverse transcription-polymerase chain reaction associated systemic immunity with the local and systemic induction of two WRKY and two ETHYLENE RESPONSIVE FACTOR (ERF)-like transcription factors. Systemic immunity against Xtc was further associated with transcriptional changes after a secondary/systemic Xtc challenge infection; these changes were dependent on the primary treatment. Taken together, bacteria-induced systemic immunity in barley may be mediated in part by WRKY and ERF-like transcription factors, possibly facilitating transcriptional reprogramming to potentiate immunity. © 2014 American Society of Plant Biologists. All Rights Reserved.

Conversion of ethanolamine, monomethylethanolamine and dimethylethanolamine to choline-containing compounds by neurons in culture and by the rat brain.

PubMed Central

Andriamampandry, C; Freysz, L; Kanfer, J N; Dreyfus, H; Massarelli, R

1989-01-01

The incubation of neurons from chick embryos in primary culture with [3H]ethanolamine revealed the conversion of this base into monomethyl, dimethyl and choline derivatives, including the corresponding free bases. Labelling with [methyl-3H]monomethylethanolamine and [methyl-3H]dimethylethanolamine supported the conclusion that in chick neuron cultures, phosphoethanolamine appears to be the preferential substrate for methylation, rather than ethanolamine or phosphatidylethanolamine. The methylation of the latter two compounds, in particular that of phosphatidylethanolamine, was seemingly stopped at the level of their monomethyl derivatives. Fetal rat neurons in primary culture incubated with [3H]ethanolamine showed similar results to those observed with chick neurones. However, phosphoethanolamine and phosphatidylethanolamine and, to a lesser extent, free ethanolamine, appeared to be possible substrates for methylation reactions. The methylation of water-soluble ethanolamine compounds de novo was further confirmed by experiments performed in vivo by intraventricular injection of [3H]ethanolamine. Phosphocholine and the monomethyl and dimethyl derivatives of ethanolamine were detected in the brain 15 min after injection. PMID:2604731

Synthesis and biological evaluation of sulfur-containing cinnamate and salicylate derivatives.

PubMed

Chiang, Chih-Chia; Chang, Tsu-Chung; Tsai, Hou-Jen; Hsu, Ling-Yih

2008-03-01

UV irradiation induced formation of reactive oxygen radical species and matrix metalloproteinases (MMPs) are thought to be involved in photo-damage to the skin. MMP-1 is the major collagenolytic enzyme responsible for collagen destruction in skin tissue. To develop new anti-photoaging agents, a series of 2,2'-dithiocinnamate derivatives and 2,2'-dithio or 2-thiobenzoate derivatives were designed and synthesized. The biological activities of the synthesized compounds were assayed for ABTS [2,2'-azinobis-(3-ethyl-benzo-thiazoline-6-sulfonic acid)] radical scavenging activity, MMP-1 inhibitory activity, and cytotoxicity to human dermal fibroblast cells. Compounds with potential of resistance to UV irradiation were identified. These compounds are expected to be useful for preventing photo-damage to the skin.

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

PubMed Central

Bruns, Hilke; Riclea, Ramona

2011-01-01

Summary The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC–MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω−1)-branched, (ω−2)-branched, α- and (ω−1)-branched, γ- and (ω−1)-branched, γ- and (ω−2)-branched, and γ- and (ω−3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [2H10]leucine, [2H10]isoleucine, [2H8]valine, [2H5]sodium propionate, and [methyl-2H3]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM). PMID:22238549

Phenolic metabolites in plasma and tissues of rats fed with a grape pomace extract as assessed by liquid chromatography-tandem mass spectrometry.

PubMed

Rodriguez Lanzi, Cecilia; Perdicaro, Diahann J; Antoniolli, Andrea; Piccoli, Patricia; Vazquez Prieto, Marcela A; Fontana, Ariel

2018-05-31

Grape pomace extract (GPE) is a rich and relatively low-cost source of phenolic compounds. However, little is known about the main GPE metabolites in mammals, which could help explain the observed health-promoting effects. This study investigated the presence of parent compounds from flavanol, flavonol and stilbene families and their metabolites in rat plasma and tissues after an acute intake of GPE in doses of 300 and 600 mg kg/body weight. The measurement of free compounds and their metabolites was performed by ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). Results showed the presence of epicatechin, epicatechin methyl-glucuronide, epicatechin methyl-sulphate, catechin, catechin-glucuronide, quercetin methyl-glucuronide, resveratrol-3-glucuronide, resveratrol-4-glucuronide and resveratrol-3-sulphate in plasma, which was dose dependent. The most abundant measured compound in plasma was epicatechin-glucuronide. The presence of glucuronidated and methyl-glucuronidated forms of catechin were observed in the liver at both doses, while epicatechin-glucuronide and methyl-glucuronide were detected only upon intake of 600 mg GPE/kg body weight. At this dose epicatechin-glucuronide and methyl-glucuronide were also detected in muscle, and catechin methyl-glucuronide in adipose tissue. Results show the main GPE metabolites present in rat tissues after oral consumption, contributing to better understand the health benefits of GPE and its potential utilization as a functional ingredient. Copyright © 2018. Published by Elsevier Inc.

Aspergillus niger Enhance Bioactive Compounds Biosynthesis As Well As Expression of Functional Genes in Adventitious Roots of Glycyrrhiza uralensis Fisch.

PubMed

Li, Jing; Wang, Juan; Li, Jinxin; Liu, Dahui; Li, Hongfa; Gao, Wenyuan; Li, Jianli; Liu, Shujie

2016-02-01

In the present study, the culture conditions for the accumulation of Glycyrrhiza uralensis adventitious root metabolites in balloon-type bubble bioreactors (BTBBs) have been optimized. The results of the culture showed that the best culture conditions were a cone angle of 90° bioreactor and 0.4-0.6-0.4-vvm aeration volume. Aspergillus niger can be used as a fungal elicitor to enhance the production of defense compounds in plants. With the addition of a fungal elicitor (derived from Aspergillus niger), the maximum accumulation of total flavonoids (16.12 mg g(-1)) and glycyrrhetinic acid (0.18 mg g(-1)) occurred at a dose of 400 mg L(-1) of Aspergillus niger resulting in a 3.47-fold and 1.8-fold increase over control roots. However, the highest concentration of polysaccharide (106.06 mg g(-1)) was achieved with a mixture of elicitors (Aspergillus niger and salicylic acid) added to the medium, resulting in a 1.09-fold increase over Aspergillus niger treatment alone. Electrospray ionization tandem mass spectrometry (ESI-MS(n)) analysis was performed, showing that seven compounds were present after treatment with the elicitors, including uralsaponin B, licorice saponin B2, liquiritin, and (3R)-vestitol, only identified in the mixed elicitor treatment group. It has also been found that elicitors (Aspergillus niger and salicylic acid) significantly upregulated the expression of the cinnamate 4-hydroxylase (C4H), β-amyrin synthase (β-AS), squalene epoxidase (SE) and a cytochrome P450 monooxygenase (CYP72A154) genes, which are involved in the biosynthesis of bioactive compounds, and increased superoxide dismutase (SOD), catalase (CAT), and peroxidase (POD) activity.

Oxygenated N-Acyl Alanine Methyl Esters (NAMEs) from the Marine Bacterium Roseovarius tolerans EL-164.

PubMed

Bruns, Hilke; Herrmann, Jennifer; Müller, Rolf; Wang, Hui; Wagner Döbler, Irene; Schulz, Stefan

2018-01-26

The marine bacterium Roseovarius tolerans EL-164 (Rhodobacteraceae) can produce unique N-acylalanine methyl esters (NAMEs) besides strucutrally related N-acylhomoserine lactones (AHLs), bacterial signaling compounds widespread in the Rhodobacteraceae. The structures of two unprecedented NAMEs carrying a rare terminally oxidized acyl chain are reported here. The compounds (Z)-N-16-hydroxyhexadec-9-enoyl-l-alanine methyl ester (Z9-16-OH-C16:1-NAME, 3) and (Z)-N-15-carboxypentadec-9-enoyl-l-alanine methyl ester (16COOH-C16:1-NAME, 4) were isolated, and the structures were determined by NMR and MS experiments. Both compounds were synthesized to prove assignments and to test their biological activity. Finally, non-natural, structurally related Z9-3-OH-C16:1-NAME (18) was synthesized to investigate the mass spectroscopy of structurally related NAMEs. Compound 3 showed moderate antibacterial activity against microorganisms such as Bacillus, Streptococcus, Micrococcus, or Mucor strains. In contrast to AHLs, quorum-sensing or quorum-quenching activity was not observed.

Novel Energetic Compounds Based on 3-Methyl-1,2,5-Oxadiazole 2-Oxide

NASA Astrophysics Data System (ADS)

Xu, Zhen; Yang, Hongwei; Cheng, Guangbin

2018-01-01

Two derivatives of 3-methyl-1,2,5-oxadiazole 2-oxide, (E) 4-methyl-1,2,5-oxadiazole-3-carboxaldehyde 5-oxide (2,4,6-trinitrophenyl)hydrazone (1) and 2,2,2-trinitroethyl 4-methyl-1,2,5-oxadiazole-3-carboxylate 5-oxide (2), were designed, synthesized, and fully characterized. The structures of the new compounds were confirmed by single-crystal X-ray analysis. Physicochemical and energetic properties including density, thermal stability, and sensitivity were investigated, and energetic properties (e.g., detonation velocities and detonation pressures) were calculated using EXPLO5 code. The results indicated that compound 1 exhibits positive heat of formation of 448.0 kJ mol-1 and acceptable sensitivities (IS: 20 J, FS: 280 N). In addition, compound 2 possesses low melting point (99.92°C), moderate decomposition temperature (183.67°C), good detonation performances (D: 8430 m s-1; P: 31.5 GPa), and lower sensitivities (IS: 18 J; FS: 220 N), which suggest 2 has the potential to be melt-cast explosive.

THE EFFECT OF SALICYLATES ON THE PRECIPITATION OF ANTIGEN WITH ANTIBODY.

PubMed

Coburn, A F; Kapp, E M

1943-02-01

1. Sodium salicylate modifies the precipitation of normal rabbit serum protein by sodium tungstate, and partially inhibits the precipitation of horse serum euglobulin by rabbit antiserum. Sodium salicylate added to a system containing crystalline egg albumin and its antibody partly prevents the formation of precipitate, the degree of inhibition being related to the concentration of salicylate. 2. Precipitation in the equivalence zone is more readily prevented by salicylate than precipitation in the region of antibody excess, the immune system becoming progressively less sensitive to the action of salicylate as the excess of antibody becomes larger. 3. Formed precipitates were partly dissolved following resuspension in the presence of salicylate. 4. The salicylate effect on immune precipitation is reversible, and appears to be due to inactivation of antibody. 5. Salicylate was more effective in preventing specific precipitation than other anions of a lyotropic series tested.

THE EFFECT OF SALICYLATES ON THE PRECIPITATION OF ANTIGEN WITH ANTIBODY

PubMed Central

Coburn, Alvin F.; Kapp, Eleanor M.

1943-01-01

1. Sodium salicylate modifies the precipitation of normal rabbit serum protein by sodium tungstate, and partially inhibits the precipitation of horse serum euglobulin by rabbit antiserum. Sodium salicylate added to a system containing crystalline egg albumin and its antibody partly prevents the formation of precipitate, the degree of inhibition being related to the concentration of salicylate. 2. Precipitation in the equivalence zone is more readily prevented by salicylate than precipitation in the region of antibody excess, the immune system becoming progressively less sensitive to the action of salicylate as the excess of antibody becomes larger. 3. Formed precipitates were partly dissolved following resuspension in the presence of salicylate. 4. The salicylate effect on immune precipitation is reversible, and appears to be due to inactivation of antibody. 5. Salicylate was more effective in preventing specific precipitation than other anions of a lyotropic series tested. PMID:19871273

Neuroinhibitory meroterpenoid compounds from Cordia oncocalyx.

PubMed

Matos, Taynara S; Silva, Ana Karine O; Quintela, Amanda L; Francisco das Chagas Pinto, L; Canuto, Kirley M; Braz-Filho, Raimundo; Fonseca, Maria Júlia S; Luna-Costa, Angélica Maria; Paz, Iury A; Nascimento, Nilberto Robson F; Silveira, Edilberto R; Pessoa, Otilia Deusdênia L

2017-11-01

Five new meroterpenoid compounds designed as rel-10β,11β-epoxy-2,11-dimethoxy-8α-hydroxy-8aβ-methyl-5α,6,7,8,8a,9,10,10aβ-octahydro-1,4-anthracendione (1), rel-10β,11β-epoxy-8α,5-dihydroxy-2-methoxy-8aβ-methyl-5,6,7,8,8a,9,10,10aβ-octahydro -1.4-anthracendione (2), rel-1,4,8α-trihydroxy-5-furanyl-2-methoxy-8aβ-methyl-6,7,8, 8a,9,10-hexahydro-10-anthracenone (3), rel-10α,11α-epoxy-8α,11β-dihydroxy-8aβ-methyl-5β,6,7,8,8a,9,10,10aβ-octahydro-1,4-anthracenediol (4) and rel-1,4,8α-trihydroxy-5-carboxyethyl-2-methoxy-8aβ-methyl-6,7,8,8a,9,10-hexahydro-10-anthra-cenone (5), besides seven (6-12) known compounds were isolated from the heartwood and sapwood ethanol extracts of Cordia oncocalyx. Moreover, the main isolated compounds were screened using the electrically driven mice vas deferens bioassay, which has a rich pharmacological receptors diversity. Published by Elsevier B.V.

Anti-arthritic activity of 11-O-(4'-O-methyl galloyl)-bergenin and Crassula capitella extract in rats.

PubMed

El-Hawary, Seham S; Mohammed, Rabab; Abouzid, Sameh; Ali, Zeinab Y; Elwekeel, Ahlam

2016-06-01

Isolation and identification of phytochemicals of Crassula capitella (Thunberg), evaluation of the anti-arthritic potential of the extract and the major isolated compound; 11-O-(4'-O-methyl galloyl)-bergenin and underlying their mechanism on rat model of rheumatoid arthritis (RA). Different fractions were subjected to column chromatography giving fourteen compound identified by mass and NMR spectroscopic techniques. RA was induced by intraplantar injection of complete Freund's adjuvant into the right hind paw of rats. Influence of tested samples in comparable to methotrexate on paw oedema, body weight gain, serum diagnostic markers, cartilage and bone degeneration enzymes, pro-inflammatory mediators and oxidative stress biomarkers in arthritic rats. Fourteen phenolic compounds were isolated and identified for the first time from C. capitella. The major compound identified as 11-O-(4'-O-methyl galloyl)-bergenin. Treatment of arthritic rats with extract or 11-O-(4'-O-methyl galloyl)-bergenin with the tested doses can reduce the progression and severity of RA. Crassula capitella is a new natural and abundant source for 11-O-(4'-O-methyl galloyl)-bergenin for resolving chronic inflammatory diseases as RA through antioxidant, anti-inflammatory and membrane stabilizing mechanism. © 2016 Royal Pharmaceutical Society.

Hydroxyl radical scavenging assay of phenolics and flavonoids with a modified cupric reducing antioxidant capacity (CUPRAC) method using catalase for hydrogen peroxide degradation.

PubMed

Ozyürek, Mustafa; Bektaşoğlu, Burcu; Güçlü, Kubilay; Apak, Reşat

2008-06-02

Hydroxyl radicals (OH) generated in the human body may play an important role in tissue injury at sites of inflammation in oxidative stress-originated diseases. As a more convenient, efficient, and less costly alternative to HPLC/electrochemical detection techniques and to the nonspecific, low-yield deoxyribose (TBARS) test, we used a salicylate probe for detecting OH generated by the reaction of iron(II)-EDTA complex with H(2)O(2). The produced hydroxyl radicals attack both the salicylate probe and the hydroxyl radical scavengers that are incubated in solution for 10 min. Added radical scavengers compete with salicylate for the OH produced, and diminish chromophore formation from Cu(II)-neocuproine. At the end of the incubation period, the reaction was stopped by adding catalase. With the aid of this reaction, a kinetic approach was adopted to assess the hydroxyl radical scavenging properties of polyphenolics, flavonoids and other compounds (e.g., ascorbic acid, glucose, mannitol). A second-order rate constant for the reaction of the scavenger with OH could be deduced from the inhibition of colour formation due to the salicylate probe. In addition to phenolics and flavonoids, five kinds of herbs were evaluated for their OH scavenging activity using the developed method. The modified CUPRAC (cupric ion reducing antioxidant capacity) assay proved to be efficient for ascorbic acid, gallic acid and chlorogenic acid, for which the deoxyribose assay test is basically nonresponsive. An important contribution of this developed assay is the inhibition of the Fenton reaction with catalase degradation of hydrogen peroxide so that the remaining H(2)O(2) would neither give a CUPRAC absorbance nor involve in redox cycling of phenolic antioxidants, enabling the rapid assay of polyphenolics.

Assessing the potential for rhizoremediation of PCB contaminated soils in northern regions using native tree species.

PubMed

Slater, Heather; Gouin, Todd; Leigh, Mary Beth

2011-06-01

Rhizosphere bioremediation of polychlorinated biphenyls (PCBs) offers a potentially inexpensive approach to remediating contaminated soils that is particularly attractive in remote regions including the Arctic. We assessed the abilities of two tree species native to Alaska, Salix alaxensis (felt-leaf willow) and Picea glauca (white spruce), to promote microbial biodegradation of PCBs via the release of phytochemicals upon fine root death. Crushed fine roots, biphenyl (PCB analogue) or salicylate (willow secondary compound) were added to microcosms containing soil spiked with PCBs and resultant PCB disappearance, soil toxicity and microbial community changes were examined. After 180d, soil treated with willow root crushates showed a significantly greater PCB loss than untreated soils for some PCB congeners, including the toxic congeners, PCB 77, 105 and 169, and showed a similar PCB loss pattern (in both extent of degradation and congeners degraded) to biphenyl-treated microcosms. Neither P. glauca (white spruce) roots nor salicylate enhanced PCB loss, indicating that biostimulation is plant species specific and was not mediated by salicylate. Soil toxicity assessed using the Microtox bioassay indicated that the willow treatment resulted in a less toxic soil environment. Molecular microbial community analyses indicated that biphenyl and salicylate promoted shifts in microbial community structure and composition that differed distinctly from each other and from the crushed root treatments. The biphenyl utilizing bacterium, Cupriavidus spp. was isolated from the soil. The findings suggest that S. alaxensis may be an effective plant for rhizoremediation by altering microbial community structure, enhancing the loss of some PCB congeners and reducing the toxicity of the soil environment. Copyright © 2011 Elsevier Ltd. All rights reserved.

Solvatochromic studies on 4-Bromomethyl-7-methyl coumarins

NASA Astrophysics Data System (ADS)

Khanapurmath, Netravati; Kulkarni, Manohar V.; Pallavi, L.; Yenagi, Jayashree; Tonannavar, Jagdish

2018-05-01

Non- and dinitro 4-bromomethyl-7-methyl coumarins and new mono- and trinitro 4-bromomethyl-7-methyl coumarins have been synthesized. Effect of nitro groups on the photophysical properties of the parent 4-bromomethyl-7-methyl coumarin has been reported. Their ground and excited state dipole moments have been estimated by solvatochromic method using nine solvents. A reasonable agreement has been observed between calculated and observed dipole moments. Reduction in dipole moment has been observed for mono- and dinitro compounds where as the trinitro compound was found to have higher dipole moment in the excited state.

Development of a HS-SPME-GC/MS protocol assisted by chemometric tools to study herbivore-induced volatiles in Myrcia splendens.

PubMed

Souza Silva, Érica A; Saboia, Giovanni; Jorge, Nina C; Hoffmann, Camila; Dos Santos Isaias, Rosy Mary; Soares, Geraldo L G; Zini, Claudia A

2017-12-01

A headspace solid phase microextraction (HS-SPME) method combined with gas chromatography-mass spectrometry (GC/MS) was developed and optimized for extraction and analysis of volatile organic compounds (VOC) of leaves and galls of Myrcia splendens. Through a process of optimization of main factors affecting HS-SPME efficiency, the coating divivnilbenzene-carboxen-polydimethylsiloxane (DVB/Car/PDMS) was chosen as the optimum extraction phase, not only in terms of extraction efficiency, but also for its broader analyte coverage. Optimum extraction temperature was 30°C, while an extraction time of 15min provided the best compromise between extraction efficiencies of lower and higher molecular weight compounds. The optimized protocol was demonstrated to be capable of sampling plant material with high reproducibility, considering that most classes of analytes met the 20% RSD FDA criterion. The optimized method was employed for the analysis of three classes of M. splendens samples, generating a final list of 65 tentatively identified VOC, including alcohols, aldehydes, esters, ketones, phenol derivatives, as well as mono and sesquiterpenes. Significant differences were evident amongst the volatile profiles obtained from non-galled leaves (NGL) and leaf-folding galls (LFG) of M. splendens. Several differences pertaining to amounts of alcohols and aldehydes were detected between samples, particularly regarding quantities of green leaf volatiles (GLV). Alcohols represented about 14% of compounds detected in gall samples, whereas in non-galled samples, alcohol content was below 5%. Phenolic derived compounds were virtually absent in reference samples, while in non-galled leaves and galls their content ranged around 0.2% and 0.4%, respectively. Likewise, methyl salicylate, a well-known signal of plant distress, amounted for 1.2% of the sample content of galls, whereas it was only present in trace levels in reference samples. Chemometric analysis based on Heatmap associated with Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) provided a suitable tool to differentiate VOC profiles in vegetal material, and could open new perspectives and opportunities in agricultural and ecological studies for the detection and identification of herbivore-induced plant VOC emissions. Copyright © 2017 Elsevier B.V. All rights reserved.

Ozone-induced foliar damage and release of stress volatiles is highly dependent on stomatal openness and priming by low-level ozone exposure in Phaseolus vulgaris.

PubMed

Li, Shuai; Harley, Peter C; Niinemets, Ülo

2017-09-01

Acute ozone exposure triggers major emissions of volatile organic compounds (VOCs), but quantitatively, it is unclear how different ozone doses alter the start and the total amount of these emissions, and the induction rate of different stress volatiles. It is also unclear whether priming (i.e. pre-exposure to lower O 3 concentrations) can modify the magnitude and kinetics of volatile emissions. We investigated photosynthetic characteristics and VOC emissions in Phaseolus vulgaris following acute ozone exposure (600 nmol mol -1 for 30 min) under illumination and in darkness and after priming with 200 nmol mol -1 O 3 for 30 min. Methanol and lipoxygenase (LOX) pathway product emissions were induced rapidly, followed by moderate emissions of methyl salicylate (MeSA). Stomatal conductance prior to acute exposure was lower in darkness and after low O 3 priming than in light and without priming. After low O 3 priming, no MeSA and lower LOX emissions were detected under acute exposure. Overall, maximum emission rates and the total amount of emitted LOX products and methanol were quantitatively correlated with total stomatal ozone uptake. These results indicate that different stress volatiles scale differently with ozone dose and highlight the key role of stomatal conductance in controlling ozone uptake, leaf injury and volatile release. © 2017 John Wiley & Sons Ltd.

Ectopic accumulation of linalool confers resistance to Xanthomonas citri subsp. citri in transgenic sweet orange plants.

PubMed

Shimada, Takehiko; Endo, Tomoko; Rodríguez, Ana; Fujii, Hiroshi; Goto, Shingo; Matsuura, Takakazu; Hojo, Yuko; Ikeda, Yoko; Mori, Izumi C; Fujikawa, Takashi; Peña, Leandro; Omura, Mitsuo

2017-05-01

In order to clarify whether high linalool content in citrus leaves alone induces strong field resistance to citrus canker caused by Xanthomonas citri subsp. citri (Xcc), and to assess whether this trait can be transferred to a citrus type highly sensitive to the bacterium, transgenic 'Hamlin' sweet orange (Citrus sinensis L. Osbeck) plants over-expressing a linalool synthase gene (CuSTS3-1) were generated. Transgenic lines (LIL) with the highest linalool content showed strong resistance to citrus canker when spray inoculated with the bacterium. In LIL plants inoculated by wounding (multiple-needle inoculation), the linalool level was correlated with the repression of the bacterial titer and up-regulation of defense-related genes. The exogenous application of salicylic acid, methyl jasmonate or linalool triggered responses similar to those constitutively induced in LIL plants. The linalool content in Ponkan mandarin leaves was significantly higher than that of leaves from six other representative citrus genotypes with different susceptibilities to Xcc. We propose that linalool-mediated resistance might be unique to citrus tissues accumulating large amounts of volatile organic compounds in oil cells. Linalool might act not only as a direct antibacterial agent, but also as a signal molecule involved in triggering a non-host resistance response against Xcc. © The Author 2017. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

Defense Responses in Aspen with Altered Pectin Methylesterase Activity Reveal the Hormonal Inducers of Tyloses.

PubMed

Leśniewska, Joanna; Öhman, David; Krzesłowska, Magdalena; Kushwah, Sunita; Barciszewska-Pacak, Maria; Kleczkowski, Leszek A; Sundberg, Björn; Moritz, Thomas; Mellerowicz, Ewa J

2017-02-01

Tyloses are ingrowths of parenchyma cells into the lumen of embolized xylem vessels, thereby protecting the remaining xylem from pathogens. They are found in heartwood, sapwood, and in abscission zones and can be induced by various stresses, but their molecular triggers are unknown. Here, we report that down-regulation of PECTIN METHYLESTERASE1 (PtxtPME1) in aspen (Populus tremula × tremuloides) triggers the formation of tyloses and activation of oxidative stress. We tested whether any of the oxidative stress-related hormones could induce tyloses in intact plantlets grown in sterile culture. Jasmonates, including jasmonic acid (JA) and methyl jasmonate, induced the formation of tyloses, whereas treatments with salicylic acid (SA) and 1-aminocyclopropane-1-carboxylic acid (ACC) were ineffective. SA abolished the induction of tyloses by JA, whereas ACC was synergistic with JA. The ability of ACC to stimulate tyloses formation when combined with JA depended on ethylene (ET) signaling, as shown by a decrease in the response in ET-insensitive plants. Measurements of internal ACC and JA concentrations in wild-type and ET-insensitive plants treated simultaneously with these two compounds indicated that ACC and JA regulate each other's concentration in an ET-dependent manner. The findings indicate that jasmonates acting synergistically with ethylene are the key molecular triggers of tyloses. © 2017 American Society of Plant Biologists. All Rights Reserved.

Ozone-induced foliar damage and release of stress volatiles is highly dependent on stomatal openness and priming by low-level ozone exposure in Phaseolus vulgaris

PubMed Central

Li, Shuai; Harley, Peter C.; Niinemets, Ülo

2018-01-01

Acute ozone exposure triggers major emissions of volatile organic compounds (VOC), but quantitatively, it is unclear how different ozone doses alter the start and the total amount of these emissions, and the induction rate of different stress volatiles. It is also unclear whether priming (i.e., pre-exposure to lower O3 concentrations) can modify the magnitude and kinetics of volatile emissions. We investigated photosynthetic characteristics and VOC emissions in Phaseolus vulgaris following acute ozone exposure (600 nmol mol-1 for 30 min) under illumination and in darkness and after priming with 200 nmol mol-1 O3 for 30 min. Methanol and lipoxygenase (LOX) pathway product emissions were induced rapidly, followed by moderate emissions of methyl salicylate (MeSA). Stomatal conductance prior to acute exposure was lower in darkness and after low O3 priming than in light and without priming. After low O3 priming, no MeSA and lower LOX emissions were detected under acute exposure. Overall, maximum emission rates and the total amount of emitted LOX products and methanol were quantitatively correlated with total stomatal ozone uptake. These results indicate that different stress volatiles scale differently with ozone dose and highlight the key role of stomatal conductance in controlling ozone uptake, leaf injury and volatile release. PMID:28623868

Defense Responses in Aspen with Altered Pectin Methylesterase Activity Reveal the Hormonal Inducers of Tyloses1[OPEN

PubMed Central

Leśniewska, Joanna; Krzesłowska, Magdalena; Kushwah, Sunita; Sundberg, Björn; Moritz, Thomas

2017-01-01

Tyloses are ingrowths of parenchyma cells into the lumen of embolized xylem vessels, thereby protecting the remaining xylem from pathogens. They are found in heartwood, sapwood, and in abscission zones and can be induced by various stresses, but their molecular triggers are unknown. Here, we report that down-regulation of PECTIN METHYLESTERASE1 (PtxtPME1) in aspen (Populus tremula × tremuloides) triggers the formation of tyloses and activation of oxidative stress. We tested whether any of the oxidative stress-related hormones could induce tyloses in intact plantlets grown in sterile culture. Jasmonates, including jasmonic acid (JA) and methyl jasmonate, induced the formation of tyloses, whereas treatments with salicylic acid (SA) and 1-aminocyclopropane-1-carboxylic acid (ACC) were ineffective. SA abolished the induction of tyloses by JA, whereas ACC was synergistic with JA. The ability of ACC to stimulate tyloses formation when combined with JA depended on ethylene (ET) signaling, as shown by a decrease in the response in ET-insensitive plants. Measurements of internal ACC and JA concentrations in wild-type and ET-insensitive plants treated simultaneously with these two compounds indicated that ACC and JA regulate each other’s concentration in an ET-dependent manner. The findings indicate that jasmonates acting synergistically with ethylene are the key molecular triggers of tyloses. PMID:27923986

Understanding the Biosynthesis SF2575: A Potent Antitumor Compound With Novel Modes of Action

DTIC Science & Technology

2009-09-01

analyzed on HPLC and LCMS to try to identify any potential stable intermediates that may be present (Figure 3). Using selected ion monitoring, the... polyketides . One known example is that of thermorubin, in which the salicylate moiety is Figure 6: Proposed biosynthetic pathways for the pendants 30...DISTRIBUTION STATEMENT: (Check one ) X Approved for public release; distribution unlimited Distribution limited to U.S

Evaluation of nitrate-substituted pseudocholine esters of aspirin as potential nitro-aspirins.

PubMed

Gilmer, John F; Moriarty, Louise M; Clancy, John M

2007-06-01

Herein we explore some designs for nitro-aspirins, compounds potentially capable of releasing both aspirin and nitric oxide in vivo. A series of nitrate-bearing alkyl esters of aspirin were prepared based on the choline ester template preferred by human plasma butyrylcholinesterase. The degradation kinetics of the compounds were followed in human plasma solution. All compounds underwent hydrolysis rapidly (t(1/2) approximately 1min) but generating exclusively the corresponding nitro-salicylate. The one exception, an N-propyl, N-nitroxyethyl aminoethanol ester produced 9.2% aspirin in molar terms indicating that the nitro-aspirin objective is probably achievable if due cognisance can be paid to the demands of the activating enzyme. Even at this low level of aspirin release, this compound is the most successful nitro-aspirin reported to date in the key human plasma model.

Synthesis and antimicrobial activity of new 1-[(tetrazol-5-yl)methyl] indole derivatives, their 1,2,4-triazole thioglycosides and acyclic analogs.

PubMed

El-Sayed, Weal A; Abdel Megeid, Randa E; Abbas, Hebat-Allah S

2011-07-01

New 1-[(tetrazol-5-yl)methyl]indole derivatives, their acyclic nucleoside analogs and the corresponding glycoside derivatives were synthesized. Furthermore, the [)(1,2,4-triazol-3-yl)methyl])-2H-tetrazole derivative as well as the corresponding thioglucoside were prepared. The synthesized compounds were tested for their antimicrobial activity against Aspergillus Niger, Penicillium sp, Candida albican, Bacillus subtilis, Streptococcus lacti, Escherichia coli, Pseudomonas sp., and streptomyces sp. Compounds 3, 5 and 19b exhibited potent antibacterial activity and compounds 4, 5 and 10 exhibited high activities against the tested fungi compared with fusidic acid.

Microwave assisted synthesis and structure-activity relationship of 4-hydroxy-N'-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents.

PubMed

Ahmad, Naveed; Zia-ur-Rehman, Muhammad; Siddiqui, Hamid Latif; Ullah, Muhammad Fasih; Parvez, Masood

2011-06-01

A series of 4-hydroxy-N'-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides was synthesized from commercially available sodium saccharin. Base catalyzed ring expansion of methyl (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)acetate followed by ultrasound mediated hydrazinolysis and subsequent reaction with 1-phenylethanones under the influence of microwaves yielded the title compounds. Besides, microwave assisted synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide is also discussed. Most of the synthesized compounds were found to possess moderate to significant anti-microbial (anti-bacterial and anti-fungal) activities. It is found that compounds with greater lipophilicity (N-methyl analogues) possessed higher anti-bacterial activities. Copyright © 2011 Elsevier Masson SAS. All rights reserved.

DIPPR Project 871 For 1995 - Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Methyl Benzoate, Ethyl Benzoate, (R)-(+)-Limonene, Tert-Amyl Methyl Ether, Trans-Crotonaldehyde, and

DOE Office of Scientific and Technical Information (OSTI.GOV)

Steele, W.V.

2002-07-01

Ideal-gas enthalpies of formation of methyl benzoate, ethyl benzoate, (R)-(+)-limonene, tert-amyl methyl ether, trans-crotonaldehyde, and diethylene glycol are reported. The standard energy of combustion and hence standard enthalpy of formation of each compound in the liquid phase has been measured using an oxygen rotating-bomb calorimeter without rotation. Vapor pressures were measured to a pressure limit of 270 kPa or the lower decomposition point for each of the six compounds using a twin ebulliometric apparatus. Liquid-phase densities along the saturation line were measured for each compound over a range of temperature (ambient to a maximum of 548 K). A differential scanningmore » calorimeter was used to measure two-phase (liquid + vapor) heat capacities for each compound in the temperature region ambient to the critical temperature or lower decomposition point. For methyl benzoate and tert-amyl methyl ether, critical temperatures and critical densities were determined from the DSC results and corresponding critical pressures derived from the fitting procedures. Fitting procedures were used to derive critical temperatures, critical pressures, and critical densities for each of the remaining compounds. The results of the measurements were combined to derive a series of thermophysical properties including critical temperature, critical density, critical pressure, acentric factor, enthalpies of vaporization (restricted to within {+-}50 K of the temperature region of the experimentally determined vapor pressures), and heat capacities along the saturation line. Wagner-type vapor-pressure equations were derived for each compound. All measured and derived values were compared with those obtained in a search of the literature. Recommended critical parameters are listed for each of the compounds studied. Group-additivity parameters, useful in the application of the Benson gas-phase group-contribution correlations, were derived.« less

Mutational Analysis of a Role for Salicylic Acid in Iron Metabolism of Mycobacterium smegmatis

PubMed Central

Adilakshmi, Tadepalli; Ayling, Peter D.; Ratledge, Colin

2000-01-01

The role of salicylic acid in iron metabolism was examined in two wild-type strains (mc2155 and NCIMB 8548) and three mutant strains (mc21292 [lacking exochelin], SM3 [lacking iron-dependent repressor protein IdeR] and S99 [a salicylate-requiring auxotroph derived in this study]) of Mycobacterium smegmatis. Synthesis of salicylate in SM3 was derepressed even in the presence of iron, as was synthesis of the siderophores exochelin, mycobactin, and carboxymycobactin. S99 was dependent on salicylate for growth and failed to grow with the three ferrisiderophores, suggesting that salicylate fulfills an additional function(s) other than being a precursor of mycobactin and carboxymycobactin. Salicylic acid at 100 μg/ml repressed the formation of a 29-kDa cell envelope protein (putative exochelin receptor protein) in S99 grown both iron deficiently and iron sufficiently. In contrast, synthesis of this protein was affected only under iron-limited conditions in the parent strain, mc2155, and remained unaltered in SM3, suggesting an interaction between the IdeR protein and salicylate. Thus, salicylate may also function as a signal molecule for recognition of cellular iron status. Growth of all strains and mutants with p-aminosalicylate (PAS) at 100 μg/ml increased salicylate accumulation between three- and eightfold under both iron-limited and iron-sufficient growth conditions and decreased mycobactin accumulation by 40 to 80% but increased carboxymycobactin accumulation by 50 to 55%. Thus, although PAS inhibited salicylate conversion to mycobactin, presumptively by blocking salicylate AMP kinase, PAS also interferes with the additional functions of salicylate, as its effect was heightened in S99 when the salicylate concentration was minimal. PMID:10629169

Biochemical characterization in Norway spruce (Picea abies) of SABATH methyltransferases that methylate phytohormones.

PubMed

Chaiprasongsuk, Minta; Zhang, Chi; Qian, Ping; Chen, Xinlu; Li, Guanglin; Trigiano, Robert N; Guo, Hong; Chen, Feng

2018-05-01

Indole-3-acetic acid (IAA), gibberellins (GAs), salicylic acid (SA) and jasmonic acid (JA) exist in methyl ester forms in plants in addition to their free acid forms. The enzymes that catalyze methylation of these carboxylic acid phytohormones belong to a same protein family, the SABATH methyltransferases. While the genes encoding these enzymes have been isolated from a small number of flowering plants, little is known about their occurrence and evolution in non-flowering plants. Here, we report the systematic characterization of the SABATH family from Norway spruce (Picea abies), a gymnosperm. The Norway spruce genome contains ten SABATH genes (PaSABATH1-10). Full-length cDNA for each of the ten PaSABATH genes was cloned and expressed in Escherichia coli. Recombinant PaSABATHs were tested for activity with IAA, GA, SA, and JA. Among the ten PaSABATHs, five had activity with one or more of the four substrates. PaSABATH1 and PaSABATH2 had the highest activities with IAA and SA, respectively. PaSABATH4, PaSABATH5 and PaSABATH10 all had JA as a preferred substrate but with notable differences in biochemical properties. The structural basis of PaSABATHs in discriminating various phytohormone substrates was inferred based on structural models of the enzyme-substrate complexes. The phylogeny of PaSABATHs with selected SABATHs from other plants implies that the enzymes methylating IAA are conserved in seed plants whereas the enzymes methylating JA and SA have independent evolution in gymnosperms and angiosperms. Copyright © 2018 Elsevier Ltd. All rights reserved.

Biosynthesis of 8-O-methylated benzoxazinoid defense compounds in maize

USDA-ARS?s Scientific Manuscript database

Benzoxazinoids are important defense compounds in grasses. Here, we investigated the biosynthesis and biological roles of the 8-O-methylated benzoxazinoids, DIM2BOA-Glc and HDM2BOA-Glc. Using quantitative trait locus mapping and heterologous expression, we identified a 2-oxoglutarate-dependent dioxy...

Methylated silicates may explain the release of chlorinated methane from Martian soil

NASA Astrophysics Data System (ADS)

Bak, Ebbe N.; Jensen, Svend J. Knak; Nørnberg, Per; Finster, Kai

2016-01-01

The only organic compounds that have been detected in the Martian soil are simple chlorinated compounds released from heated surface material. However, the sources of the organic carbon are in dispute. Wind abraded silicates, which are widespread on the Martian surface, can sequester atmospheric methane which generates methylated silicates and thus could provide a mechanism for accumulation of reduced carbon in the surface soil. In this study we show that thermal volatilization of methylated silicates in the presence of perchlorate leads to the production of chlorinated methane. Thus, methylated silicates could be a source of the organic carbon released as chlorinated methane upon thermal volatilization of Martian soil samples. Further, our experiments show that the ratio of the different chlorinated compounds produced is dependent on the mass ratio of perchlorate to organic carbon in the soil.

The Incidence and Fate of Volatile Methyl Siloxanes in a Crewed Spacecraft Cabin

NASA Technical Reports Server (NTRS)

Perry, Jay L.; Kayatin, Matthew J.

2017-01-01

Volatile methyl siloxanes (VMS) arise from diverse, pervasive sources aboard crewed spacecraft ranging from materials offgassing to volatilization from personal care products. These sources lead to a persistent VMS compound presence in the cabin environment that must be considered for robust life support system design. Volatile methyl siloxane compound stability in the cabin environment presents an additional technical issue because degradation products such as dimethylsilanediol (DMSD) are highly soluble in water leading to a unique load challenge for water purification processes. The incidence and fate of VMS compounds as observed in the terrestrial atmosphere, water, and surface (soil) environmental compartments have been evaluated as an analogy for a crewed cabin environment. Volatile methyl siloxane removal pathways aboard crewed spacecraft are discussed and a material balance accounting for a DMSD production mechanism consistent with in-flight observations is presented.

Pigmentation, anesthesia, behavioral factors, and salicylate uptake.

PubMed

Jastreboff, P J; Issing, W; Brennan, J F; Sasaki, C T

1988-02-01

In four experiments, 54 pigmented rats were used to examine the time course of sodium salicylate uptake in serum, cerebrospinal fluid, and perilymph. Subjects were tested under sodium pentobarbital anesthesia or while conscious. Compared with previously reported data from albino rats, pigmented subjects generally showed increased salicylate uptake. Moreover, the data suggested two different, time-dependent clearance mechanisms in conscious animals not observed in anesthetized rats. Daily injections of salicylate did not produce an accumulation of salicylate in serum. Systematically higher levels of salicylate were observed in perilymph compared with cerebrospinal fluid. Behavioral procedures, including water deprivation and conditioned suppression of ongoing drinking levels, had no effect on salicylate levels.

Molecular structure, quantum mechanical calculation and radical scavenging activities of (E)-4,6-dibromo-2-[(3,5-dimethylphenylimino)methyl]-3-methoxyphenol and (E)-4,6-dibromo-2-[(2,6-dimethylphenylimino)methyl]-3-methoxyphenol compounds.

PubMed

Alaşalvar, Can; Soylu, Mustafa Serkan; Güder, Aytaç; Albayrak, Çiğdem; Apaydın, Gökhan; Dilek, Nefise

2014-09-15

In this study, (E)-4,6-dibromo-2-[(3,5-dimethylphenylimino)methyl]-3-methoxyphenol and (E)-4,6-dibromo-2-[(2,6-dimethylphenylimino)methyl]-3-methoxyphenol compounds have been synthesized and characterized by using X-ray crystallographic method, FT-IR and Density functional method. The molecular geometry, vibrational frequencies of the title compounds in the ground state have been calculated by using B3LYP with the 6-31G(d,p) basis set. The tautomeric form of the compounds has been demonstrated by using single crystal X-ray method, FT-IR spectrometer and DFT method. In addition, HOMO-LUMO energy gap, molecular electrostatic potential map and NBO analysis of the compounds are performed at B3LYP/6-31G(d,p) level. It may be remarked that the free radical scavenging activities of the title compounds were assessed using DPPH, DMPD+, and ABTS+ assays. The obtained results show that especially compound 2 has effective DPPH (SC50 1.52±0.14 μg/mL), DMPD+ (SC50 1.22±0.21 μg/mL), and ABTS+ (SC50 3.32±0.17 μg/mL) scavenging activities compared with standards (BHA, rutin, and trolox). Copyright © 2014 Elsevier B.V. All rights reserved.

Experimental investigation of the auto-ignition characteristics of oxygenated reference fuel compounds

NASA Astrophysics Data System (ADS)

Walton, Stephen Michael

The increased use of biofuels presents an opportunity to improve combustion performance while simultaneously reducing greenhouse gases and pollutant emissions. This work focused on improving the fundamental understanding of the auto-ignition chemistry of oxygenated reference fuel compounds. A systematic study of the effects of ester structure on ignition chemistry was performed using the University of Michigan Rapid Compression Facility. The ignition properties of the ester compounds were investigated over a broad range of pressures (P=5-20 atm) and temperatures (T=850-1150 K) which are directly relevant to advanced combustion engine strategies. Ignition delay times for five esters were determined using the RCF. The esters were selected to systematically consider the chemical structure of the compounds. Three esters were saturated: methyl butanoate, butyl methanoate, and ethyl propanoate; and two were unsaturated: methyl crotonate and methyl trans-3-hexenoate. The unsaturated esters were more reactive than their saturated counterparts, with the largest unsaturated ester, methyl trans-3-hexenoate having the highest reactivity. Two isomers of the saturated esters, butyl methanoate and ethyl propanoate, were more reactive than the isomer methyl butanoate. The results are explained if we assume that butyl methanoate and ethyl propanoate form intermediate ring structures which decompose more rapidly than esters such as methyl butanoate, which do not form ring structures. Modeling studies of the reaction chemistry were conducted for methyl butanoate and ethyl propanoate, for which detailed mechanisms were available in the literature. The new experimental data indicated that literature rate coefficients for some of the methyl butanoate/HO2 reactions were too fast. Modifying these within the theoretical uncertainties for the reaction rates, led to excellent agreement between the model predictions and the experimental data. Comparison of the modeling results with the intermediates measured during methyl butanoate ignition indicated that pathways leading to the formation of small hydrocarbons are relatively well represented in the reaction mechanism. The results of this work provide archival benchmark data for improved understanding of the dominant reaction pathways and species controlling the auto-ignition of oxygenated reference fuel compounds. These data also provide a path for continued development of chemical kinetic models to optimize practical combustion systems.

GABAergic Neural Activity Involved in Salicylate-Induced Auditory Cortex Gain Enhancement

PubMed Central

Lu, Jianzhong; Lobarinas, Edward; Deng, Anchun; Goodey, Ronald; Stolzberg, Daniel; Salvi, Richard J.; Sun, Wei

2011-01-01

Although high doses of sodium salicylate impair cochlear function, it paradoxically enhances sound-evoked activity in the auditory cortex (AC) and augments acoustic startle reflex responses, neural and behavioral metrics associated with hyperexcitability and hyperacusis. To explore the neural mechanisms underlying salicylate-induced hyperexcitability and “increased central gain”, we examined the effects of γ-aminobutyric acid (GABA) receptor agonists and antagonists on salicylate-induced hyperexcitability in the AC and startle reflex responses. Consistent with our previous findings, local or systemic application of salicylate significantly increased the amplitude of sound-evoked AC neural activity, but generally reduced spontaneous activity in the AC. Systemic injection of salicylate also significantly increased the acoustic startle reflex. S-baclofen or R-baclofen, GABA-B agonists, which suppressed sound-evoked AC neural firing rate and local field potentials, also suppressed the salicylate-induced enhancement of the AC field potential and the acoustic startle reflex. Local application of vigabatrin, which enhances GABA concentration in the brain, suppressed the salicylate-induced enhancement of AC firing rate. Systemic injection of vigabatrin also reduced the salicylate-induced enhancement of acoustic startle reflex. Collectively, these results suggest that the sound-evoked behavioral and neural hyperactivity induced by salicylate may arise from a salicylate-induced suppression GABAergic inhibition in the AC. PMID:21664433

Comparison between the impacts of two different modes of salicylic acid application on tomato (Solanum lycopersicum) responses to salinity.

PubMed

Gharbi, E; Lutts, S; Dailly, H; Quinet, M

2018-06-26

Exogenous application of salicylic acid may improve tolerance to salinity. To investigate whether exogenous salicylic acid application had similar protective effects when applied as a priming agent or concomitantly with NaCl, tomato seedlings primed or not with 10 µM salicylic acid were further treated with 125 mM NaCl, 10 µM salicylic acid or combined treatments. Both priming and concomitant application of salicylic acid increased plant growth of salt-stressed plants but their positive impact was not additive. The endogenous salicylic acid concentration increased in the leaves after concomitant application but not in response to priming, suggesting that salicylic acid accumulated during priming was metabolized subsequently. Priming increased Na + and K + accumulation in leaves of salt-treated plants while concomitant application had no impact on shoot Na + and K + accumulation. Both priming and concomitant salicylic acid decreased osmotic potential values in salt-treated plants. Carbon isotope discrimination showed that combination of both salicylic acid application methods were required to maintain a good water use efficiency in salt-treated plants. Our work demonstrated that both procedures of salicylic acid application have positive impact on salt resistance but that the underlying properties sustaining these adaptations differ according to application methods.

Ototoxicity of salicylate, nonsteroidal antiinflammatory drugs, and quinine.

PubMed

Jung, T T; Rhee, C K; Lee, C S; Park, Y S; Choi, D C

1993-10-01

Salicylates and most NSAIDS in high doses cause mild to moderate temporary hearing loss, either flat or greater in the high frequencies. Hearing loss is accompanied by tinnitus and suprathreshold changes. Salicylates may or may not exacerbate hearing loss and cochlear damage induced by noise. The mechanism of salicylate ototoxicity seems to be multifactorial. Morphologic studies suggest that no permanent cochlear damage occurs with salicylate ototoxicity. Electrophysiologic, morphologic, and in vitro data conclusively demonstrate that salicylate affects outer hair cells. In addition, salicylates appear to decrease cochlear blood flow. Salicylates and NSAIDs inhibit PG-forming cyclooxygenase, and recent studies suggest that abnormal levels of arachidonic acid metabolites consisting of decreased PGs and increased LTs may mediate salicylate ototoxicity. As with salicylate, quinine ototoxicity appears to be multifactorial in origin. The mechanism includes vasoconstriction and decreases in cochlear blood flow, as measured by laser Doppler flowmetry, motion photographic studies, and histologic studies. Reversible alterations of outer hair cells also appear to play an important role, as demonstrated by histology, electron microscopy, isolated hair cell studies, and cochlear potential evaluations. Unlike with salicylate, however, the role of prostaglandins in quinine ototoxicity has not been clearly demonstrated. Also, one of quinine's principal actions, antagonism of calcium-dependent potassium channels, has yet to be investigated for its potential role in ototoxicity.

Chemical Preparation Laboratory for IND Candidate Compounds

DTIC Science & Technology

1990-02-08

CLASSIFICATION lb. RESTRICTIVE MARKINGS Unclassified 2a. SECURITY CLASSIFICATION AUTHORITY 3 . DISTRIBUTION /AVAILABILITY OF REPORT 2b. DECLASSIFICATION... 3 III. Cumulative list of Compounds Delivered to U.S. Army Medical Research and Development (USAMRIID) from January 17, 1989 to...AVS 52) ............................................ 7 2. Selenazole (AVS 253) ............................................... 9 3 . Methyl-l,2,4

Methyl 3-amino-4-butanamido-5-methyl­benzoate

PubMed Central

Li, Xiang; Yuan, Lian-shan; Wang, Dan; Yao, Cheng

2008-01-01

The title compound, C13H18N2O3, is an inter­mediate in the synthesis of compounds with medicinial applications. The crystal structure is stabilized by inter­molecular N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds. PMID:21202582

Effect of added thiamine on the key odorant compounds and aroma of cooked ham.

PubMed

Thomas, Caroline; Mercier, Frédéric; Tournayre, Pascal; Martin, Jean-Luc; Berdagué, Jean-Louis

2015-04-15

This study shows that thiamine plays a major role in the formation of three key odorants of cooked ham: 2-methyl-3-furanthiol, 2-methyl-3-methyldithiofuran, and bis(2-methyl-3-furyl)disulphide. Analyses revealed that under identical cooking conditions, the productions of these three aroma compounds increase in a closely intercorrelated way when the dose of thiamine increases. Using a specific 2-methyl-3-furanthiol extraction-quantification method, it was possible to relate the amounts of thiamine added in model cooked hams to the amounts of 2-methyl-3-furanthiol produced in the cooking process. Sensory analyses highlighted the role of thiamine as a precursor of cooked ham aroma. Copyright © 2014 Elsevier Ltd. All rights reserved.

Oxidation of aqueous pharmaceuticals by pulsed corona discharge.

PubMed

Panorel, Iris; Preis, Sergei; Kornev, Iakov; Hatakka, Henry; Louhi-Kultanen, Marjatta

2013-01-01

Oxidation of aromatic compounds of phenolic (paracetamol, beta-oestradiol and salicylic acid) and carboxylic (indomethacin and ibuprofen) structure used in pharmaceutics was studied. Aqueous solutions were treated with pulsed corona discharge (PCD) as a means for advanced oxidation. Pulse repetition frequency, delivered energy dose and oxidation media were the main parameters studied for their influence on the process energy efficiency. The PCD treatment appeared to be effective in oxidation of the target compounds: complete degradation of pollutant together with partial mineralization was achieved at moderate energy consumption; oxidation proceeds faster in alkaline media. Low-molecular carboxylic acids were identified as ultimate oxidation by-products formed in the reaction.

cis-fumagillin, a new methionine aminopeptidase (type 2) inhibitor produced by Penicillium sp. F2757.

PubMed

Kwon, J Y; Jeong, H W; Kim, H K; Kang, K H; Chang, Y H; Bae, K S; Choi, J D; Lee, U C; Son, K H; Kwon, B M

2000-08-01

Selective inhibition against the yeast MetAP2 (methionine aminopeptidase type 2) was detected in the fermentation broth of a fungus F2757 that was later identified as Penicillium janczewskii. A new compound cis-fumagillin methyl ester (1) was isolated from the diazomethane treated fermentation extracts together with the known compound fumagillin methyl ester (2). The cis-fumagillin methyl ester, a stereoisomer of fumagillin methyl ester at the C2'-C3' position of the aliphatic side chain, selectively inhibited growth of the map1 mutant yeast strain (MetAP1 deletion strain) at a concentration as low as 1 ng. However, the wild type yeast w303 and the mutant map2 (MetAP2 deleted) strains were resistant up to 10 microg of the compound. In enzyme experiments, compound 1 inhibited the MetAP2 with an IC50 value of 6.3 nM, but it did not inhibit the MetAP1 (IC50 >200 microM). Compound 2 also inhibited the MetAP2 with an IC50 value of 9.2 nM and 105 microM against MetAP1.

Radiosynthesis and radiopharmacological evaluation of [N-methyl-11C]Org 34850 as a glucocorticoid receptor (GR)-binding radiotracer.

PubMed

Wuest, Frank; Kniess, Torsten; Henry, Brian; Peeters, Bernardus W M M; Wiegerinck, Peter H G; Pietzsch, Jens; Bergmann, Ralf

2009-02-01

The radiosynthesis of [N-methyl-(11)C]Org 34850 as a potential brain glucocorticoid receptor (GR)-binding radiotracer is described. The radiosynthesis was accomplished via N-methylation of the corresponding desmethyl precursor with [(11)C]methyl triflate in a remotely controlled synthesis module to give the desired compound in a radiochemical yield of 23+/-5% (decay-corrected, based upon [(11)C]CO(2)) at a specific activity of 47+/-12 GBq/micromol (n=15) at the end-of-synthesis (EOS). The radiochemical purity after semi-preparative HPLC purification exceeded 95%. The total synthesis time was 35-40 min after end-of-bombardment (EOB). The radiotracer is rapidly metabolized in rat plasma leading to the formation of two more hydrophilic metabolites as the major metabolites. Radiopharmacological evaluation involving biodistribution and small animal PET imaging in normal Wistar rats showed that the compound [N-methyl-(11)C]Org 34850 is not able to sufficiently penetrate the blood-brain barrier. Therefore, compound [N-methyl-(11)C]Org 34850 seems not to be a suitable PET radiotracer for imaging rat brain GRs. However, involvement of Pgp or species differences requires further clarification to establish whether the radiotracer [N-methyl-(11)C]Org 34850 may still represent a suitable candidate for imaging GRs in humans.

Differential DNA methylation at conserved non-genic elements and evidence for transgenerational inheritance following developmental exposure to mono(2-ethylhexyl) phthalate and 5-azacytidine in zebrafish.

PubMed

Kamstra, Jorke H; Sales, Liana Bastos; Aleström, Peter; Legler, Juliette

2017-01-01

Exposure to environmental stressors during development may lead to latent and transgenerational adverse health effects. To understand the role of DNA methylation in these effects, we used zebrafish as a vertebrate model to investigate heritable changes in DNA methylation following chemical-induced stress during early development. We exposed zebrafish embryos to non-embryotoxic concentrations of the biologically active phthalate metabolite mono(2-ethylhexyl) phthalate (MEHP, 30 µM) and the DNA methyltransferase 1 inhibitor 5-azacytidine (5AC, 10 µM). Direct, latent and transgenerational effects on DNA methylation were assessed using global, genome-wide and locus-specific DNA methylation analyses. Following direct exposure in zebrafish embryos from 0 to 6 days post-fertilization, genome-wide analysis revealed a multitude of differentially methylated regions, strongly enriched at conserved non-genic elements for both compounds. Pathways involved in adipogenesis were enriched with the putative obesogenic compound MEHP. Exposure to 5AC resulted in enrichment of pathways involved in embryonic development and transgenerational effects on larval body length. Locus-specific methylation analysis of 10 differentially methylated sites revealed six of these loci differentially methylated in sperm sampled from adult zebrafish exposed during development to 5AC, and in first and second generation larvae. With MEHP, consistent changes were found at 2 specific loci in first and second generation larvae. Our results suggest a functional role for DNA methylation on cis-regulatory conserved elements following developmental exposure to compounds. Effects on these regions are potentially transferred to subsequent generations.

Dosage of salicylates for children with juvenile rheumatoid arthritis. A preliminary report.

PubMed

Mäkelä, A L; Tryänä, T; Haapasaari, J

1975-01-01

The daily dosage of salicylates is traditionally very high for patients with juvenile rheumatoid arthritis. In order to achieve the optimal therapeutic effect, serum salicylate levels are kept at 30-35 mg/100 ml (2175-2540 mumol/l). The recommended daily dosage in the textbooks is about 100 mg/kg of body weight, and the reported dosage/m2 of body surface area has been 3.2 g/m2/day. These dosages are, however, too high in clinical routine. In the present investigation, 19 children were treated with salicylates for 15 days with daily check-ups of the serum salicylate levels. Seven of these children had symptoms of salicylate intoxication which corresponded closely to the serum salicylate levels. If the daily dosage of salicylates exceeds 3 g/m2 of body surface area, intoxication can be expected.

A KINETIC STUDY OF THE METHANOLYSIS OF THE SULFONYLUREAS BENSULFURON METHYL AND SULFOMETURON METHYL USING CAPILLARY ELECTROPHORESIS

EPA Science Inventory

The instability of sulfonylureas in solution in methanol has led us to a kinetic study of methanolysis of two sulfonylureas using capillary electrophoresis. In a preliminary experiment solutions of the seven compounds, bensulfuron methyl, sulfometuron methyl, nicosulfuron, chlori...

Use of ferric chloride to identify salicylate-containing poisons.

PubMed

Hoffman, Robert J; Nelson, Lewis S; Hoffman, Robert S

2002-01-01

Ferric chloride (FeCl3) is used to qualitatively test the urine of patients with presumed salicylate exposure. FeCl3 testing of an unidentified poison might provide evidence of salicylate exposure in situations where FeCl3 urine testing cannot be used. Such situations include the absence of a urine sample, immediately after ingestion before urine contains a detectable quantity of salicylate, or for patients chronically using salicylatesfor which FeCl3 testing is unhelpful. This study seeks to determine if FeCl3 can be used to identify salicylate-containing products. We assessed the reactivity of FeCl3 with commercially available salicylate-containing products. We applied 0.1 mL of 10% FeCl3 solution to each of 15 various salicylate-containing products including: regular and buffered acetylsalicylic acid, bismuth subsalicylate, methylsalicylate, physostigmine salicylate, salicylic acid, trolamine salicylate, and herbal tablets with salicin-containing white willow bark (Salix sp.). These products tested were: regular and enteric-coatedpills (n = 4), powder (n = 1), topical creams (n = 5), topical liquids (n = 4), and intravenous solution (n = 1). FeCl3 was applied to crushed tablets and added directly to liquids and creams. Fifteen salicylate-free controls including liquids, pills, and creams similar in appearance to experimental samples were also tested. Three blinded physiciansfamiliar with FeCl3 testing independently observed the addition of FeCl3 to each sample and rated a positive or negative result. All salicylate-containing products were interpreted to be clearly FeCl3 positive and all control samples were interpreted to be clearly FeCl3 negative. Salicylate-containing products may be identified using FeCl33. When using FeCl3

Molecular dynamics simulations of salicylate effects on the micro- and mesoscopic properties of a dipalmitoylphosphatidylcholine bilayer†

PubMed Central

Song, Yuhua; Guallar, Victor; Baker, Nathan A.

2008-01-01

Salicylate, an amphiphilic molecule and a popular member of non-steroidal antiinflammatory drug family, is known to affect hearing through reduction of the electromechanical coupling in the outer hair cells of the ear. This reduction of electromotility by salicylate has been widely studied but the molecular mechanism of the phenomenon is still unknown. In this study, we investigated one aspect of salicylate’s action; namely, the perturbation of electrical and mechanical membrane properties by salicylate in the absence of cytoskeletal or membrane-bound motor proteins such as prestin. In particular, we simulated the interaction of salicylate with a dipalmitoylphosphatidylcholine (DPPC) bilayer via atomically-detailed molecular dynamics simulations to observe the effect of salicylate on the microscopic and mesoscopic properties of the bilayer. The results demonstrate that salicylate interacts with the bilayer by associating at the water-DPPC interface in a nearly perpendicular orientation and penetrating more deeply into the bilayer than either sodium or chloride. This association has several affects on the membrane properties. First, binding of salicylate to the membrane displaces chloride from the bilayer-water interface. Second, salicylate influences the electrostatic potential and dielectric properties of the bilayer, with significant changes at the water-lipid bilayer interface. Third, salicylate association results in structural changes including decreased head group area per lipid and increased lipid tail order. However, salicylate does not significantly alter the mechanical properties of the DPPC bilayer; bulk compressibility, area compressibility, and bending modulus were only perturbed by small, statistically-insignificant amounts, by the presence of salicylate. The observations from these simulations are in qualitative agreement with experimental data and support the conclusion that salicylate influences the electrical but not the mechanical properties of DPPC membranes. PMID:16216066

A new isobenzofuranone from the mangrove endophytic fungus Penicillium sp. (ZH58).

PubMed

Yang, Jianxiang; Huang, Riming; Qiu, Sheng Xiang; She, Zhigang; Lin, Yongcheng

2013-10-01

A new isobenzofuranone, 4-(methoxymethyl)-7-methoxy-6-methyl-1(3H)-isobenzofuranone (1), together with seven known compounds, dilation (2), lumichrome (3), curvulari (4), 5,5'-oxy-dimethylene-bis(2-furaldehyde) (5), chromone (6), harman(1-methyl-β-carboline) (7), N9-methyl-1methyl-β-carboline (8), was isolated from the mangrove endophytic fungus, Penicillium sp. ZH58 obtained from the South China Sea coast. Their structures were determined by analysis of spectroscopic data. Compound 1 exhibited cytotoxicity against KB and KBV200 cells with IC50 values of 6 and 10 μg/mL, respectively.

NtPDR3, an iron-deficiency inducible ABC transporter in Nicotiana tabacum.

PubMed

Ducos, Eric; Fraysse, Staffan; Boutry, Marc

2005-12-19

In plants, the ABC transporter PDR (pleiotropic drug resistance) subfamily is composed of approximately 15 genes, few of which have been analyzed. We have identified NtPDR3, a Nicotiana tabacum PDR gene belonging to a cluster for which no functional data was previously available. NtPDR3 was found to be induced in suspension cells treated with methyl jasmonate, salicylic acid, 1-naphthalene acetic acid, or cembrene, a macrocyclic diterpene. In agreement with the identification of a putative iron deficiency element in the NtPDR3 transcription promoter region, we found that iron deficiency in the culture medium induced NtPDR3 expression, thus suggesting a new function of the PDR transporter family.

Polymer of phosphonylmethyl-2,4- and -2,6-diamino benzene and polyfunctional monomer

NASA Technical Reports Server (NTRS)

Mikroyannidis, J. A. (Inventor); Kourtides, D. A. (Inventor)

1986-01-01

A phosphonyl methyl benzene is prepared by nitration to produce a 2,4-dinitro phosphonyl methyl benzene, which is then reduced to a diamino compound. The diamino compound is then used to cure a polymerizable monomer. The diamino compound may be polymerized with polyfunctional epoxides to produce heat and fire resistant polymer structures for making flame and fire resistant polymer structures such as for aircraft secondary structures.

Process for the production of .sup.18 F-2-deoxy-2-fluoro-D-glucose

DOEpatents

Elmaleh, David R.; Levy, Shlomo; Shiue, Chyng-Yann; Wolf, Alfred P.

1986-01-01

Process for the production of 2-deoxy-2-fluoro-D-glucose and the corresponding .sup.18 F-compound in which methyl 4,6-O-benzylidine-3-O-methyl-2-O-trifluoromethanesulfonyl-.beta.-D-mannopy ranoside is reacted with a triflating reagent, the resulting compound reacted with CsHF.sub.2, RbF or the corresponding .sup.18 F-compounds, and thereafter the alkyl groups removed by hydrolysis.

Biodegradation of phenol, salicylic acid, benzenesulfonic acid, and iomeprol by Pseudomonas fluorescens in the capillary fringe

NASA Astrophysics Data System (ADS)

Hack, Norman; Reinwand, Christian; Abbt-Braun, Gudrun; Horn, Harald; Frimmel, Fritz H.

2015-12-01

Mass transfer and biological transformation phenomena in the capillary fringe were studied using phenol, salicylic acid, benzenesulfonic acid, and the iodinated X-ray contrast agent iomeprol as model organic compounds and the microorganism strain Pseudomonas fluorescens. Three experimental approaches were used: Batch experiments (uniform water saturation and transport by diffusion), in static columns (with a gradient of water saturation and advective transport in the capillaries) and in a flow-through cell (with a gradient of water saturation and transport by horizontal and vertical flow: 2-dimension flow-through microcosm). The reactors employed for the experiments were filled with quartz sand of defined particle size distribution (dp = 200…600 μm, porosity ε = 0.42). Batch experiments showed that phenol and salicylic acid have a high, whereas benzenesulfonic acid and iomeprol have a quite low potential for biodegradation under aerobic conditions and in a matrix nearly close to water saturation. Batch experiments under anoxic conditions with nitrate as electron acceptor revealed that the biodegradation of the model compounds was lower than under aerobic conditions. Nevertheless, the experiments showed that the moisture content was also responsible for an optimized transport in the liquid phase of a porous medium. Biodegradation in the capillary fringe was found to be influenced by both the moisture content and availability of the dissolved substrate, as seen in static column experiments. The gas-liquid mass transfer of oxygen also played an important role for the biological activity. In static column experiments under aerobic conditions, the highest biodegradation was found in the capillary fringe (e.g. βt/β0 (phenol) = 0 after t = 6 d) relative to the zone below the water table and unsaturated zone. The highest biodegradation occurred in the flow-through cell experiment where the height of the capillary fringe was largest.

Biodegradation of phenol, salicylic acid, benzenesulfonic acid, and iomeprol by Pseudomonas fluorescens in the capillary fringe.

PubMed

Hack, Norman; Reinwand, Christian; Abbt-Braun, Gudrun; Horn, Harald; Frimmel, Fritz H

2015-12-01

Mass transfer and biological transformation phenomena in the capillary fringe were studied using phenol, salicylic acid, benzenesulfonic acid, and the iodinated X-ray contrast agent iomeprol as model organic compounds and the microorganism strain Pseudomonas fluorescens. Three experimental approaches were used: Batch experiments (uniform water saturation and transport by diffusion), in static columns (with a gradient of water saturation and advective transport in the capillaries) and in a flow-through cell (with a gradient of water saturation and transport by horizontal and vertical flow: 2-dimension flow-through microcosm). The reactors employed for the experiments were filled with quartz sand of defined particle size distribution (dp=200...600 μm, porosity ε=0.42). Batch experiments showed that phenol and salicylic acid have a high, whereas benzenesulfonic acid and iomeprol have a quite low potential for biodegradation under aerobic conditions and in a matrix nearly close to water saturation. Batch experiments under anoxic conditions with nitrate as electron acceptor revealed that the biodegradation of the model compounds was lower than under aerobic conditions. Nevertheless, the experiments showed that the moisture content was also responsible for an optimized transport in the liquid phase of a porous medium. Biodegradation in the capillary fringe was found to be influenced by both the moisture content and availability of the dissolved substrate, as seen in static column experiments. The gas-liquid mass transfer of oxygen also played an important role for the biological activity. In static column experiments under aerobic conditions, the highest biodegradation was found in the capillary fringe (e.g. βt/β0 (phenol)=0 after t=6 d) relative to the zone below the water table and unsaturated zone. The highest biodegradation occurred in the flow-through cell experiment where the height of the capillary fringe was largest. Copyright © 2015 Elsevier B.V. All rights reserved.

Both Central and Peripheral Auditory Systems Are Involved in Salicylate-Induced Tinnitus in Rats: A Behavioral Study

PubMed Central

Liu, Zhi; Sun, Yongzhu; Chang, Haifeng; Cui, Pengcheng

2014-01-01

Objective This study was designed to establish a low dose salicylate-induced tinnitus rat model and to investigate whether central or peripheral auditory system is involved in tinnitus. Methods Lick suppression ratio (R), lick count and lick latency of conditioned rats in salicylate group (120 mg/kg, intraperitoneally) and saline group were first compared. Bilateral auditory nerves were ablated in unconditioned rats and lick count and lick latency were compared before and after ablation. The ablation was then performed in conditioned rats and lick count and lick latency were compared between salicylate group and saline group and between ablated and unablated salicylate groups. Results Both the R value and the lick count in salicylate group were significantly higher than those in saline group and lick latency in salicylate group was significantly shorter than that in saline group. No significant changes were observed in lick count and lick latency before and after ablation. After ablation, lick count and lick latency in salicylate group were significantly higher and shorter respectively than those in saline group, but they were significantly lower and longer respectively than those in unablated salicylate group. Conclusion A low dose of salicylate (120 mg/kg) can induce tinnitus in rats and both central and peripheral auditory systems participate in the generation of salicylate-induced tinnitus. PMID:25269067

Effects of jasmonic acid, ethylene, and salicylic acid signaling on the rhizosphere bacterial community of Arabidopsis thaliana.

PubMed

Doornbos, Rogier F; Geraats, Bart P J; Kuramae, Eiko E; Van Loon, L C; Bakker, Peter A H M

2011-04-01

Systemically induced resistance is a promising strategy to control plant diseases, as it affects numerous pathogens. However, since induced resistance reduces one or both growth and activity of plant pathogens, the indigenous microflora may also be affected by an enhanced defensive state of the plant. The aim of this study was to elucidate how much the bacterial rhizosphere microflora of Arabidopsis is affected by induced systemic resistance (ISR) or systemic acquired resistance (SAR). Therefore, the bacterial microflora of wild-type plants and plants affected in their defense signaling was compared. Additionally, ISR was induced by application of methyl jasmonate and SAR by treatment with salicylic acid or benzothiadiazole. As a comparative model, we also used wild type and ethylene-insensitive tobacco. Some of the Arabidopsis genotypes affected in defense signaling showed altered numbers of culturable bacteria in their rhizospheres; however, effects were dependent on soil type. Effects of plant genotype on rhizosphere bacterial community structure could not be related to plant defense because chemical activation of ISR or SAR had no significant effects on density and structure of the rhizosphere bacterial community. These findings support the notion that control of plant diseases by elicitation of systemic resistance will not significantly affect the resident soil bacterial microflora.

Defense to Sclerotinia sclerotiorum in oilseed rape is associated with the sequential activations of salicylic acid signaling and jasmonic acid signaling.

PubMed

Wang, Zheng; Tan, Xiaoli; Zhang, Zhiyan; Gu, Shoulai; Li, Guanying; Shi, Haifeng

2012-03-01

Signaling pathways mediated by salicylic acid (SA) and jasmonic acid (JA) are widely studied in various host-pathogen interactions. For oilseed rape (Brassica napus)-Sclerotinia sclerotiorum interaction, little information of the two signaling molecules has been described in detail. In this study, we showed that the level of SA and JA in B. napus leaves was increased with a distinct temporal profile, respectively, after S. sclerotiorum infection. The application of SA or methyl jasmonate enhanced the resistance to the pathogen. Furthermore, a set of SA and JA signaling marker genes were identified from B. napus and were used to monitor the signaling responses to S. sclerotiorum infection by examining the temporal expression profiles of these marker genes. The SA signaling was activated within 12h post inoculation (hpi) followed by the JA signaling which was activated around 24 hpi. In addition, SA-JA crosstalk genes were activated during this process. These results suggested that defense against S. sclerotiorum in oilseed rape is associated with a sequential activation of SA signaling and JA signaling, which provide important clues for designing strategies to curb diseases caused by S. sclerotioru. Copyright © 2011 Elsevier Ireland Ltd. All rights reserved.

Breakthrough behavior of granular ferric hydroxide (GFH) fixed-bed adsorption filters: modeling and experimental approaches.

PubMed

Sperlich, Alexander; Werner, Arne; Genz, Arne; Amy, Gary; Worch, Eckhard; Jekel, Martin

2005-03-01

Breakthrough curves (BTC) for the adsorption of arsenate and salicylic acid onto granulated ferric hydroxide (GFH) in fixed-bed adsorbers were experimentally determined and modeled using the homogeneous surface diffusion model (HSDM). The input parameters for the HSDM, the Freundlich isotherm constants and mass transfer coefficients for film and surface diffusion, were experimentally determined. The BTC for salicylic acid revealed a shape typical for trace organic compound adsorption onto activated carbon, and model results agreed well with the experimental curves. Unlike salicylic acid, arsenate BTCs showed a non-ideal shape with a leveling off at c/c0 approximately 0.6. Model results based on the experimentally derived parameters over-predicted the point of arsenic breakthrough for all simulated curves, lab-scale or full-scale, and were unable to catch the shape of the curve. The use of a much lower surface diffusion coefficient D(S) for modeling led to an improved fit of the later stages of the BTC shape, pointing on a time-dependent D(S). The mechanism for this time dependence is still unknown. Surface precipitation was discussed as one possible removal mechanism for arsenate besides pure adsorption interfering the determination of Freundlich constants and D(S). Rapid small-scale column tests (RSSCT) proved to be a powerful experimental alternative to the modeling procedure for arsenic.

A study of the mechanisms involved in the neurotoxic action of 3,4-methylenedioxymethamphetamine (MDMA, ‘ecstasy') on dopamine neurones in mouse brain

PubMed Central

Colado, M Isabel; Camarero, Jorge; Mechan, Annis O; Sanchez, Veronica; Esteban, Blanca; Elliott, J Martin; Green, A Richard

2001-01-01

Administration of 3,4-methylenedioxymethamphetamine (MDMA, ‘ecstasy') to mice produces acute hyperthermia and long-term degeneration of striatal dopamine nerve terminals. Attenuation of the hyperthermia decreases the neurodegeneration. We have investigated the mechanisms involved in producing the neurotoxic loss of striatal dopamine. MDMA produced a dose-dependent loss in striatal dopamine concentration 7 days later with 3 doses of 25 mg kg−1 (3 h apart) producing a 70% loss. Pretreatment 30 min before each MDMA dose with either of the N-methyl-D-aspartate antagonists AR-R15896AR (20, 5, 5 mg kg−1) or MK-801 (0.5 mg kg−1×3) failed to provide neuroprotection. Pretreatment with clomethiazole (50 mg kg−1×3) was similarly ineffective in protecting against MDMA-induced dopamine loss. The free radical trapping compound PBN (150 mg kg−1×3) was neuroprotective, but it proved impossible to separate neuroprotection from a hypothermic effect on body temperature. Pretreatment with the nitric oxide synthase (NOS) inhibitor 7-NI (50 mg kg−1×3) produced neuroprotection, but also significant hypothermia. Two other NOS inhibitors, S-methyl-L-thiocitrulline (10 mg kg−1×3) and AR-R17477AR (5 mg kg−1×3), provided significant neuroprotection and had little effect on MDMA-induced hyperthermia. MDMA (20 mg kg−1) increased 2,3-dihydroxybenzoic acid formation from salicylic acid perfused through a microdialysis tube implanted in the striatum, indicating increased free radical formation. This increase was prevented by AR-R17477AR administration. Since AR-R17477AR was also found to have no radical trapping activity this result suggests that MDMA-induced neurotoxicity results from MDMA or dopamine metabolites producing radicals that combine with NO to form tissue-damaging peroxynitrites. PMID:11739248

The occurrence and distribution of a group of organic micropollutants in Mexico City's water sources.

PubMed

Félix-Cañedo, Thania E; Durán-Álvarez, Juan C; Jiménez-Cisneros, Blanca

2013-06-01

The occurrence and distribution of a group of 17 organic micropollutants in surface and groundwater sources from Mexico City was determined. Water samples were taken from 7 wells, 4 dams and 15 tanks where surface and groundwater are mixed and stored before distribution. Results evidenced the occurrence of seven of the target compounds in groundwater: salicylic acid, diclofenac, di-2-ethylhexylphthalate (DEHP), butylbenzylphthalate (BBP), triclosan, bisphenol A (BPA) and 4-nonylphenol (4-NP). In surface water, 11 target pollutants were detected: same found in groundwater as well as naproxen, ibuprofen, ketoprofen and gemfibrozil. In groundwater, concentration ranges of salicylic acid, 4-NP and DEHP, the most frequently found compounds, were 1-464, 1-47 and 19-232 ng/L, respectively; while in surface water, these ranges were 29-309, 89-655 and 75-2,282 ng/L, respectively. Eleven target compounds were detected in mixed water. Concentrations in mixed water were higher than those determined in groundwater but lower than the detected in surface water. Different to that found in ground and surface water, the pesticide 2,4-D was found in mixed water, indicating that some pollutants can reach areas where they are not originally present in the local water sources. Concentration of the organic micropollutants found in this study showed similar to lower to those reported in water sources from developed countries. This study provides information that enriches the state of the art on the occurrence of organic micropollutants in water sources worldwide, notably in megacities of developing countries. Copyright © 2013 Elsevier B.V. All rights reserved.

ESTIMATES OF REGIONAL NATURAL VOLATILE ORGANIC COMPOUND FLUXES FROM ENCLOSURE AND AMBIENT MEASUREMENTS

EPA Science Inventory

The paper discusses results of an investigation at two forested sites in the Southeastern United States. A variety of VOC compounds including methanol, 2-methyl-3-buten-2-ol, 6-methyl-5-hepten-
2-one, isoprene, and 15 monoterpenes were emitted from vegetation at these sites. D...

Synthesis of small combinatorial libraries of natural products: identification and quantification of new long-chain 3-methyl-2-alkanones from the root essential oil of Inula helenium L. (Asteraceae).

PubMed

Radulović, Niko S; Denić, Marija S; Stojanović-Radić, Zorica Z

2014-01-01

Recently, a potent anti-staphylococcal activity of Inula helenium L. (Asteraceae) root essential oil was reported. Also, bioassay guided fractionation of the oil pointed to eudesmane sesquiterpene lactones and a series of unidentified constituents as the main carriers of the observed activity. To identify nine new constituents (long-chain 3-methyl-2-alkanones) from a fraction of this root essential oil with a low minimum inhibitory concentration value (0.8 µg/mL) by employing a synthetic methodology that leads to the formation of a small combinatorial library of these compounds. The identity of these constituents was inferred from mass spectral fragmentation patterns and GC retention data. A library of 3-methyl-2-alkanones (C11 -C19 homologous series) was synthesised in three steps starting from methyl acetoacetate and the corresponding alkyl halides. The synthetic library was also screened for in vitro anti-microbial activity. Gas chromatographic analyses of I. helenium essential oil samples with spiked compounds from the synthesised library corroborated the tentative identifications of the long-chain 3-methyl-2-alkanones. The availability of these anti-microbial compounds from this library made it possible to construct GC/FID calibration curves and determine their content in the plant material: 0.08 - 24.2 mg/100 g of dry roots. The small combinatorial library approach enabled the first unequivocal identification of long-chain 3-methyl-2-alkanones as plant secondary metabolites, and, also, allowed determination of not only a single compound and biological properties, but those of a group of structurally related compounds. Copyright © 2013 John Wiley & Sons, Ltd.

Introduction of a methyl group in alpha- or beta-position of 1-heteroarylethyl-4-phenylpiperazines affects their dopaminergic/serotonergic properties.

PubMed

Roglic, G; Andric, D; Kostic-Rajacic, S; Dukic, S; Soskic, V

2001-12-01

1-(2-Heteroarylalkyl)-4-phenylpiperazines containing methyl group in either the alpha- or the beta-position of the side alkyl chain were synthesized as racemic mixtures. They were evaluated for in vitro binding affinity at the D1 and D2 dopamine and 5-HT1A serotonin receptors using synaptosomal membranes of the bovine caudate nucleus and hippocampus, respectively, as a source of the corresponding receptors. Tritiated SCH 23390 (D1 receptor-selective), spiperone (D2 receptor-selective), and 8-OH-DPAT (5-HT1A receptor-selective) were employed as the radioligands. None of the new compounds expressed significant affinity for the D1 receptor. Introduction of the methyl group into the beta-position of the parent molecules increased the affinity for the D2 receptor (10b-13b), and decreased the affinity for the 5-HT1A receptor with the exception of imidazole (11b) which was a rather efficient displacer of 8-OH-DPAT. Most potent of the newly synthesized compounds in [3H]spiperone assay were compounds (+/-)6-[1-methyl-2- (4-phenylpiperazin-1-yl)-ethyl]-1,4-dihydroquinoxaline-2,3-dione (10b), Kd = 6.0 nM and (+/-)5-[1-methyl-2-(4-phenylpiperazin-1-yl)-ethyl]-1,3-dihydrobenzoimidazol- 2-thione (13b), Kd = 5.3 nM. However, compounds containing methyl group in alpha-position (10a-13a) of the parent molecules expressed a decreased affinity for the D2 receptor, while the affinity for the 5-HT1A receptor remained in the same range of concentrations as that of closely related achiral parent compounds (14-17) run in the same binding assays as references.

Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.

PubMed

Walle, U Kristina; Walle, Thomas

2007-11-01

Methoxylated flavones were recently shown to be promising cancer chemopreventive agents. Their high metabolic stability compared with the hydroxylated analogs was shown in our laboratory using the human hepatic S9 fraction with cofactors for glucuronidation, sulfation, and oxidation. In the present study, the resistance of methoxylated flavones toward oxidative metabolism was investigated with human liver microsomes and recombinant cytochrome P450 (P450) isoforms. Among 15 methoxylated flavones investigated, the two partially methylated compounds, tectochrysin and kaempferide, were among the most susceptible to microsomal oxidation (Cl(int) 283 and 82 ml/min/kg). Of the fully methylated compounds, 5,7-dimethoxyflavone and 5-methoxyflavone were the most stable (Cl(int) 13 and 18 ml/min/kg, respectively), whereas 4'-methoxyflavone, 3'-methoxyflavone, 5,4'-dimethoxyflavone, and 7,3'-dimethoxyflavone were the least stable (Cl(int) 161, 140, 119, and 92 ml/min/kg, respectively), emphasizing the importance of the positions of the methoxy substituents in the flavone ring system. Among the five P450 isoforms tested, CYP1A1 showed the highest rate of metabolism of fully methylated compounds, followed by CYP1A2 and CYP3A4. CYP2C9 and CYP2D6 gave minimal disappearance of the parent compound. Finally, in incubations with hepatic S9 fraction with cofactors for oxidation and both conjugation reactions, partially methylated flavones, as expected, were much less metabolically stable than fully methylated flavones, confirming that oxidative demethylation is the rate-limiting metabolic reaction for fully methylated flavones only. In summary, the rate of oxidative metabolism of methoxylated flavones, mainly involving CYP1A1 and CYP1A2, varied widely, even between compounds with very similar structures.

Salicylic acid as a peeling agent: a comprehensive review

PubMed Central

Arif, Tasleem

2015-01-01

Salicylic acid has been used to treat various skin disorders for more than 2,000 years. The ability of salicylic acid to exfoliate the stratum corneum makes it a good agent for peeling. In particular, the comedolytic property of salicylic acid makes it a useful peeling agent for patients with acne. Once considered as a keratolytic agent, the role of salicylic acid as a desmolytic agent, because of its ability to disrupt cellular junctions rather than breaking or lysing intercellular keratin filaments, is now recognized and is discussed here. Salicylic acid as a peeling agent has a number of indications, including acne vulgaris, melasma, photodamage, freckles, and lentigines. The efficacy and safety of salicylic acid peeling in Fitzpatrick skin types I–III as well as in skin types V and VI have been well documented in the literature. This paper reviews the available data and literature on salicylic acid as a peeling agent and its possible indications. Its properties, efficacy and safety, the peeling procedure, and possible side effects are discussed in detail. An account of salicylism is also included. PMID:26347269

Salicylic acid as a peeling agent: a comprehensive review.

PubMed

Arif, Tasleem

2015-01-01

Salicylic acid has been used to treat various skin disorders for more than 2,000 years. The ability of salicylic acid to exfoliate the stratum corneum makes it a good agent for peeling. In particular, the comedolytic property of salicylic acid makes it a useful peeling agent for patients with acne. Once considered as a keratolytic agent, the role of salicylic acid as a desmolytic agent, because of its ability to disrupt cellular junctions rather than breaking or lysing intercellular keratin filaments, is now recognized and is discussed here. Salicylic acid as a peeling agent has a number of indications, including acne vulgaris, melasma, photodamage, freckles, and lentigines. The efficacy and safety of salicylic acid peeling in Fitzpatrick skin types I-III as well as in skin types V and VI have been well documented in the literature. This paper reviews the available data and literature on salicylic acid as a peeling agent and its possible indications. Its properties, efficacy and safety, the peeling procedure, and possible side effects are discussed in detail. An account of salicylism is also included.

Neuroprotective Properties of Compounds Extracted from Dianthus superbus L. against Glutamate-induced Cell Death in HT22 Cells

PubMed Central

Yun, Bo-Ra; Yang, Hye Jin; Weon, Jin Bae; Lee, Jiwoo; Eom, Min Rye; Ma, Choong Je

2016-01-01

Background: Dianthus superbus L. has been used in Chinese herbal medicine as a diuretic and anti-inflammatory agent. Objective: In this study, we isolated ten bioactive compounds from D. superbus and evaluated their neuroprotective activity against glutamate-induced cell death in the hippocampal neuronal HT22 cells. Materials and Methods: New compound, (E)-methyl-4-hydroxy-4-(8a-methyl-3-oxodecahydronaphthalen-4a-yl) (1) and, nine known compounds, diosmetin-7-O (2’’,6’’-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (2), 4-hydroxy-3-methoxy-pentyl ester benzenepropanoic acid (3), vanillic acid (4), 4-hydroxy-benzeneacetic acid (5), 4-methoxybenzeneacetic acid (6), (E)-4-methoxycinnamic acid (7), 3-methoxy-4-hydroxyphenylethanol (8), hydroferulic acid (9), and methyl hydroferulate (10), were isolated by bioactivity-guided separation. Structures of the isolated compounds were identified on the basis of 1H nuclear magnetic resonance (NMR), 13C NMR, and two-dimensional NMR spectra, while their neuroprotective properties were evaluated by performing the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Results: D. superbus extract had a neuroprotective effect and isolated 10 compounds. Among the compounds, compounds 5 and 6 effectively protected HT22 cells against glutamate toxicity. Conclusion: In conclusion, the extract of D. superbus and compounds isolated from it exhibited neuroprotective properties, suggesting therapeutic potential for applications in neurotoxic diseases. SUMMARY D. superbus extract significantly protected on glutamate-induced cell death in HT22 cellsNew compound, (E)-methyl-4-hydroxy-4-(8a-methyl-3-oxodecahydronaphthalen-4a-yl) (1) and, nine known compounds, diosmetin-7-O(2’’,6’’-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (2), 4-hydroxy-3-methoxy-pentyl ester benzenepropanoic acid (3), vanillic acid (4), 4-hydroxy-benzeneacetic acid (5), 4-methoxybenzeneacetic acid (6), (E)-4-methoxycinnamic acid (7), 3-methoxy-4-hydroxyphenylethanol (8), hydroferulic acid (9), and methyl hydroferulate (10) were isolated from D. superbus extract4-hydroxy-benzeneacetic acid and 4-methoxybenzeneacetic acid showed significant protective activity against glutamate-induced toxicity in HT22 cells. Abbreviations used: CNS: Central nervous system, ROS: Reactive oxygen species, CHCl3: Chloroform, EtOAc: Ethyl acetate, BuOH: Butanol, HPLC: High performance liquid chromatography, TLC: Thin layer chromatography, MPLC: Middle performance liquid chromatography, MeOH: Methanol, OD: Optical density, COSY: Correlation spectroscopy, HMQC: Heteronuclear multiple-quantum correlation, HMBC: Heteronuclear multiple-bond correlation, HR-MS: High-resolution molecular spectroscopy, MTT: 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide. PMID:27076746

Neuroprotective Properties of Compounds Extracted from Dianthus superbus L. against Glutamate-induced Cell Death in HT22 Cells.

PubMed

Yun, Bo-Ra; Yang, Hye Jin; Weon, Jin Bae; Lee, Jiwoo; Eom, Min Rye; Ma, Choong Je

2016-01-01

Dianthus superbus L. has been used in Chinese herbal medicine as a diuretic and anti-inflammatory agent. In this study, we isolated ten bioactive compounds from D. superbus and evaluated their neuroprotective activity against glutamate-induced cell death in the hippocampal neuronal HT22 cells. New compound, (E)-methyl-4-hydroxy-4-(8a-methyl-3-oxodecahydronaphthalen-4a-yl) (1) and, nine known compounds, diosmetin-7-O (2'',6''-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (2), 4-hydroxy-3-methoxy-pentyl ester benzenepropanoic acid (3), vanillic acid (4), 4-hydroxy-benzeneacetic acid (5), 4-methoxybenzeneacetic acid (6), (E)-4-methoxycinnamic acid (7), 3-methoxy-4-hydroxyphenylethanol (8), hydroferulic acid (9), and methyl hydroferulate (10), were isolated by bioactivity-guided separation. Structures of the isolated compounds were identified on the basis of (1)H nuclear magnetic resonance (NMR), (13)C NMR, and two-dimensional NMR spectra, while their neuroprotective properties were evaluated by performing the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. D. superbus extract had a neuroprotective effect and isolated 10 compounds. Among the compounds, compounds 5 and 6 effectively protected HT22 cells against glutamate toxicity. In conclusion, the extract of D. superbus and compounds isolated from it exhibited neuroprotective properties, suggesting therapeutic potential for applications in neurotoxic diseases. D. superbus extract significantly protected on glutamate-induced cell death in HT22 cellsNew compound, (E)-methyl-4-hydroxy-4-(8a-methyl-3-oxodecahydronaphthalen-4a-yl) (1) and, nine known compounds, diosmetin-7-O(2'',6''-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (2), 4-hydroxy-3-methoxy-pentyl ester benzenepropanoic acid (3), vanillic acid (4), 4-hydroxy-benzeneacetic acid (5), 4-methoxybenzeneacetic acid (6), (E)-4-methoxycinnamic acid (7), 3-methoxy-4-hydroxyphenylethanol (8), hydroferulic acid (9), and methyl hydroferulate (10) were isolated from D. superbus extract4-hydroxy-benzeneacetic acid and 4-methoxybenzeneacetic acid showed significant protective activity against glutamate-induced toxicity in HT22 cells. Abbreviations used: CNS: Central nervous system, ROS: Reactive oxygen species, CHCl3: Chloroform, EtOAc: Ethyl acetate, BuOH: Butanol, HPLC: High performance liquid chromatography, TLC: Thin layer chromatography, MPLC: Middle performance liquid chromatography, MeOH: Methanol, OD: Optical density, COSY: Correlation spectroscopy, HMQC: Heteronuclear multiple-quantum correlation, HMBC: Heteronuclear multiple-bond correlation, HR-MS: High-resolution molecular spectroscopy, MTT: 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide.

Emission of methyl bromide from biomass burning

DOE Office of Scientific and Technical Information (OSTI.GOV)

Manoe, S.; Andreae, M.O.

1994-03-04

Bromine is, per atom, far more efficient than chlorine in destroying stratospheric ozone, and methyl bromide is the single largest source of stratospheric bromine. The two main previously known sources of this compound are emissions from the ocean and from the compound's use as an agricultural pesticide. Laboratory biomass combustion experiments showed that methyl bromide was emitted in the smoke from various fuels tested. Methyl bromide was also found in smoke plumes from wildfires in savannas, chaparral, and boreal forest. Global emissions of methyl bromide from biomass burning are estimated to be in the range of 10 to 50 gigagramsmore » per year, which is comparable to the amount produced by ocean emission and pesticide use and represents a major contribution ([approximately]30 percent) to the stratospheric bromine budget.« less

In vitro microbiological evaluation of novel bis pyrazolones.

PubMed

Narayana Rao, D V; Raghavendra Guru Prasad, A; Spoorthy, Y N; Raghunatha Rao, D; Ravindranath, L K

2014-03-01

Two series of bis pyrazolones (one with 3-methyl substituent and the other one with 3-amino substituent on the pyrazolone ring) were synthesized by the cyclization reaction between various hydrazides with esters/cyano esters in ethanolic medium. Structures of newly synthesized compounds were confirmed by elemental analysis, IR, (1)H NMR and mass spectral data. These compounds were screened for antibacterial and antifungal activities. The compounds of series 3 with amino substituent demonstrated better activity than the compounds of series 2 with methyl substituent on the pyrazolone ring. Compounds "e, f, c and d" showed higher antimicrobial activity than the compounds "b and a". The antimicrobial potentials of the synthesized compounds were compared with that of standards. Copyright © 2013 Elsevier Masson SAS. All rights reserved.

Review of the chemistry and pharmacology of 7-Methyljugulone.

PubMed

Mbaveng, Armelle T; Kuete, Victor

2014-03-01

Naphthoquinone is a class of phenolic compounds derived from naphthalene. 7-Methyljuglone (7-MJ) is a naphthoquinone also known as ramentaceone or 6-Methyl-8-hydroxy-1,4-naphthoquinone or 5-Hydroxy-7-methyl-1,4-naphthoquinone or 7-Methyl-5-hydroxy-1,4-naphthoquinone or 5-Hydroxy-7-methyl-,1,4-naphtoquinone or 7-Methyl-5-hydroxynaphthalene-1,4-dione. This compound is a biologically active naphtoquinone, with a molecular weight of 188 g/mol mostly isolated in the genus Diospyros and Euclea. This review was aimed at providing available chemically and pharmacological data on 7-MJ. The chemical and pharmacological data were retrieved from the well-known scientific websites such as Pubmed, Google Scholar, Reaxys, Scirus, Scopus, Sciencedirect, Web-of-knowledge and Scifinder. 7-MJ was reported to have a variety of pharmacological activities such as antibacterial, antifungal, anticancer, antitubercular, anti-inflammatory and antiviral activities. The hemi-synthesis of the compound have been described. The present review pooled out together the knowledge on 7-MJ, and can serve as the start point for future research and valorization accomplishments.

Crystal structure, spectroscopic studies and quantum mechanical calculations of 2-[((3-iodo-4-methyl)phenylimino)methyl]-5-nitrothiophene.

PubMed

Özdemir Tarı, Gonca; Gümüş, Sümeyye; Ağar, Erbil

2015-04-15

The title compound, 2-[((3-iodo-4-methyl)phenylimino)methyl]-5-nitrothiophene, C12H9O2N2I1S1, was synthesized and characterized by IR, UV-Vis and single-crystal X-ray diffraction technique. The molecular structure was optimized at the B3LYP, B3PW91 and PBEPBE levels of the density functional method (DFT) with the 6-311G+(d,p) basis set. Using the TD-DFT method, the electronic absorption spectra of the title compound was computed in both the gas phase and ethanol solvent. The harmonic vibrational frequencies of the title compound were calculated using the same methods with the 6-311G+(d,p) basis set. The calculated results were compared with the experimental determination results of the compound. The energetic behavior such as the total energy, atomic charges, dipole moment of the title compound in solvent media were examined using the B3LYP, B3PW91 and PBEPBE methods with the 6-311G+(d,p) basis set by applying the Onsager and the polarizable continuum model (PCM). The molecular orbitals (FMOs) analysis, the molecular electrostatic potential map (MEP) and the nonlinear optical properties (NLO) for the title compound were obtained with the same levels of theory. And then thermodynamic properties for the title compound were obtained using the same methods with the 6-311G(d,p) basis set. Copyright © 2015 Elsevier B.V. All rights reserved.

Maternal exposure to anti-androgenic compounds, vinclozolin, flutamide and procymidone, has no effects on spermatogenesis and DNA methylation in male rats of subsequent generations

DOE Office of Scientific and Technical Information (OSTI.GOV)

Inawaka, Kunifumi; Kawabe, Mayumi; DIMS Institute of Medical Science, Inc., Ichinomiya

To verify whether anti-androgens cause transgenerational effects on spermatogenesis and DNA methylation in rats, gravid Crl:CD(SD) female rats (4 or 5/group, gestational day (GD) 0 = day sperm detected) were intraperitoneally treated with anti-androgenic compounds, such as vinclozolin (100 mg/kg/day), procymidone (100 mg/kg/day), or flutamide (10 mg/kg/day), from GD 8 to GD 15. Testes were collected from F1 male pups at postnatal day (PND) 6 for DNA methylation analysis of the region (210 bp including 7 CpG sites) within the lysophospholipase gene by bisulfite DNA sequencing method. F0 and F1 males underwent the sperm analysis (count, motility and morphology), followedmore » by DNA methylation analysis of the sperm. Remaining F1 males were cohabited with untreated-females to obtain F2 male pups for subsequent DNA methylation analysis of the testes at PND 6. These analyses showed no effects on spermatogenesis and fertility in F1 males of any treatment group. DNA methylation status in testes (F1 and F2 pups at PND 6) or sperms (F1 males at 13 weeks old) of the treatment groups were comparable to the control at all observation points, although DNA methylation rates in testes were slightly lower than those in sperm. In F0 males, no abnormalities in the spermatogenesis, fertility and DNA methylation status of sperm were observed. No transgenerational abnormalities of spermatogenesis and DNA methylation status caused by anti-androgenic compounds were observed.« less

Maternal exposure to anti-androgenic compounds, vinclozolin, flutamide and procymidone, has no effects on spermatogenesis and DNA methylation in male rats of subsequent generations.

PubMed

Inawaka, Kunifumi; Kawabe, Mayumi; Takahashi, Satoru; Doi, Yuko; Tomigahara, Yoshitaka; Tarui, Hirokazu; Abe, Jun; Kawamura, Satoshi; Shirai, Tomoyuki

2009-06-01

To verify whether anti-androgens cause transgenerational effects on spermatogenesis and DNA methylation in rats, gravid Crl:CD(SD) female rats (4 or 5/group, gestational day (GD) 0=day sperm detected) were intraperitoneally treated with anti-androgenic compounds, such as vinclozolin (100 mg/kg/day), procymidone (100 mg/kg/day), or flutamide (10 mg/kg/day), from GD 8 to GD 15. Testes were collected from F1 male pups at postnatal day (PND) 6 for DNA methylation analysis of the region (210 bp including 7 CpG sites) within the lysophospholipase gene by bisulfite DNA sequencing method. F0 and F1 males underwent the sperm analysis (count, motility and morphology), followed by DNA methylation analysis of the sperm. Remaining F1 males were cohabited with untreated-females to obtain F2 male pups for subsequent DNA methylation analysis of the testes at PND 6. These analyses showed no effects on spermatogenesis and fertility in F1 males of any treatment group. DNA methylation status in testes (F1 and F2 pups at PND 6) or sperms (F1 males at 13 weeks old) of the treatment groups were comparable to the control at all observation points, although DNA methylation rates in testes were slightly lower than those in sperm. In F0 males, no abnormalities in the spermatogenesis, fertility and DNA methylation status of sperm were observed. No transgenerational abnormalities of spermatogenesis and DNA methylation status caused by anti-androgenic compounds were observed.

Characterisation and optimisation of a sample preparation method for the detection and quantification of atmospherically relevant carbonyl compounds in aqueous medium

NASA Astrophysics Data System (ADS)

Rodigast, M.; Mutzel, A.; Iinuma, Y.; Haferkorn, S.; Herrmann, H.

2015-06-01

Carbonyl compounds are ubiquitous in the atmosphere and either emitted primarily from anthropogenic and biogenic sources or they are produced secondarily from the oxidation of volatile organic compounds. Despite a number of studies about the quantification of carbonyl compounds a comprehensive description of optimised methods is scarce for the quantification of atmospherically relevant carbonyl compounds. The method optimisation was conducted for seven atmospherically relevant carbonyl compounds including acrolein, benzaldehyde, glyoxal, methyl glyoxal, methacrolein, methyl vinyl ketone and 2,3-butanedione. O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine hydrochloride (PFBHA) was used as derivatisation reagent and the formed oximes were detected by gas chromatography/mass spectrometry (GC/MS). With the present method quantification can be carried out for each carbonyl compound originating from fog, cloud and rain or sampled from the gas- and particle phase in water. Detection limits between 0.01 and 0.17 μmol L-1 were found, depending on carbonyl compounds. Furthermore, best results were found for the derivatisation with a PFBHA concentration of 0.43 mg mL-1 for 24 h followed by a subsequent extraction with dichloromethane for 30 min at pH = 1. The optimised method was evaluated in the present study by the OH radical initiated oxidation of 3-methylbutanone in the aqueous phase. Methyl glyoxal and 2,3-butanedione were found to be oxidation products in the samples with a yield of 2% for methyl glyoxal and 14% for 2,3-butanedione after a reaction time of 5 h.

Synthesis of some potent immunomodulatory and anti-inflammatory metabolites by fungal transformation of anabolic steroid oxymetholone

PubMed Central

2012-01-01

Background Biotransformation of organic compounds by using microbial whole cells provides an efficient approach to obtain novel analogues which are often difficult to synthesize chemically. In this manuscript, we report for the first time the microbial transformation of a synthetic anabolic steroidal drug, oxymetholone, by fungal cell cultures. Results Incubation of oxymetholone (1) with Macrophomina phaseolina, Aspergillus niger, Rhizopus stolonifer, and Fusarium lini produced 17β-hydroxy-2-(hydroxy-methyl)-17α-methyl-5α-androstan-1-en-3-one (2), 2α,17α-di(hydroxyl-methyl)-5α-androstan-3β,17β-diol (3), 17α-methyl-5α-androstan-2α,3β,17β-triol (4), 17β-hydroxy-2-(hydroxymethyl)-17α-methyl-androst-1,4-dien-3-one (5), 17β-hydroxy-2α-(hydroxy-methyl)-17α-methyl-5α-androstan-3-one (6), and 2α-(hydroxymethyl)-17α-methyl-5α-androstan-3β-17β-diol (7). Their structures were deduced by spectral analyses, as well as single-crystal X-ray diffraction studies. Compounds 2–5 were identified as the new metabolites of 1. The immunomodulatory, and anti-inflammatory activities and cytotoxicity of compounds 1–7 were evaluated by observing their effects on T-cell proliferation, reactive oxygen species (ROS) production, and normal cell growth in MTT assays, respectively. These compounds showed immunosuppressant effect in the T-cell proliferation assay with IC50 values between 31.2 to 2.7 μg/mL, while the IC50 values for ROS inhibition, representing anti-inflammatory effect, were in the range of 25.6 to 2.0 μg/mL. All the compounds were found to be non-toxic in a cell-based cytotoxicity assay. Conclusion Microbial transformation of oxymetholone (1) provides an efficient method for structural transformation of 1. The transformed products were obtained as a result of de novo stereoselective reduction of the enone system, isomerization of double bond, insertion of double bond and hydroxylation. The transformed products, which showed significant immunosuppressant and anti-inflammatory activities, can be further studied for their potential as novel drugs. PMID:23237028

Synthesis and in vitro antiproliferative activity of 2-methyl-3-(2-piperazin-1-yl-ethyl)-pyrido[1,2-a]pyrimidin-4-one derivatives against human cancer cell lines.

PubMed

Mallesha, Lingappa; Mohana, Kikkeri N; Veeresh, Bantal; Alvala, Ravi; Mallika, Alvala

2012-01-01

A series of new 2-methyl-3-(2-piperazin-1-yl-ethyl)-pyrido[1,2-a]pyrimidin-4-one derivatives 6a-j were synthesized by a nucleophilic substitution reaction of 2-methyl-3-(2-piperazin-1-ylethyl)-pyrido[1,2-a]pyrimidin-4-one with various sulfonyl chlorides. The compounds were characterized by different spectral studies. All the compounds were evaluated for their antiproliferative effect using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay method against four human cancer cell lines (K562, Colo-205, MDA-MB 231, IMR-32) for the time period of 24 h. Among the series, compounds 6d, 6e and 6i showed good activity on all cell lines except K562, whereas the other compounds in the series exhibited moderate activity. Compound 6d could be a potential anticancer agent and therefore deserves further research.

Fatty acid synthase methylation levels in adipose tissue: effects of an obesogenic diet and phenolic compounds

USDA-ARS?s Scientific Manuscript database

DNA methylation is an epigenetic mechanism that can inhibit gene transcription. The aim of this study was to assess changes induced by an obesogenic diet in the methylation profile of genes involved in adipose tissue triacylglycerol metabolism, and to determine whether this methylation pattern can b...

The Synthesis and Characterization of Tetrakis [(p - amino phenoxy) methyl] methane

NASA Astrophysics Data System (ADS)

Peng, Yongli; Zou, Qian

2017-06-01

In order to solve the shortcomings of the cured epoxy resin poor toughness, this paper proceeded from the structural design of curing agent to synthesize a special curing agent tetrakis [(p-aminophenoxy) methyl] methane which containing both Benzene ring and amino group. A Symmetric compound of tetrakis [(p - acetamidophenoxy) methyl] methane was prepared by using simple and easy to get pentaerythritoltetratosylate and acetaminophen for raw materials, after Williamson etherification reaction intermediates for synthesis of a symmetrical structure of the compound tetrakis [(p-acetamido phenoxy) methyl] methane, then hydrolysed under acidic conditions it can be tetrakis [(p-amino phenoxy) methyl] methane. The influence of reaction time, reaction temperature and reactant ratio to production yield of tetrakis [(p - acetamidophenoxy) methyl] methane was studied by orthogonal experiment of three factors and three levels, and get the optimal process parameters: the reaction time: 16 h, the reaction temperature: 170 °C, reactant ratio, 1:5. The Structure of tetrakis [(p - acetamidophenoxy) methyl] methane and tetrakis [(p-amino phenoxy) methyl] methane were characterized by infrared and 1H-NMR.

Salicylate, an aspirin metabolite, specifically inhibits the current mediated by glycine receptors containing α1-subunits

PubMed Central

Lu, Y-G; Tang, Z-Q; Ye, Z-Y; Wang, H-T; Huang, Y-N; Zhou, K-Q; Zhang, M; Xu, T-L; Chen, L

2009-01-01

Background and purpose: Aspirin or its metabolite sodium salicylate is widely prescribed and has many side effects. Previous studies suggest that targeting neuronal receptors/ion channels is one of the pathways by which salicylate causes side effects in the nervous system. The present study aimed to investigate the functional action of salicylate on glycine receptors at a molecular level. Experimental approach: Whole-cell patch-clamp and site-directed mutagenesis were deployed to examine the effects of salicylate on the currents mediated by native glycine receptors in cultured neurones of rat inferior colliculus and by glycine receptors expressed in HEK293T cells. Key results: Salicylate effectively inhibited the maximal current mediated by native glycine receptors without altering the EC50 and the Hill coefficient, demonstrating a non-competitive action of salicylate. Only when applied simultaneously with glycine and extracellularly, could salicylate produce this antagonism. In HEK293T cells transfected with either α1-, α2-, α3-, α1β-, α2β- or α3β-glycine receptors, salicylate only inhibited the current mediated by those receptors that contained the α1-subunit. A single site mutation of I240V in the α1-subunit abolished inhibition by salicylate. Conclusions and implications: Salicylate is a non-competitive antagonist specifically on glycine receptors containing α1-subunits. This action critically involves the isoleucine-240 in the first transmembrane segment of the α1-subunit. Our findings may increase our understanding of the receptors involved in the side effects of salicylate on the central nervous system, such as seizures and tinnitus. PMID:19594751

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.

PubMed

Ueda, Setsuko; Mitsugi, Koichi; Ichige, Kazumi; Yoshida, Kenji; Sakuma, Tomoko; Ninomiya, Shin-ichi; Sudou, Tetsuji

2002-04-01

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.

Characterisation and optimisation of a method for the detection and quantification of atmospherically relevant carbonyl compounds in aqueous medium

NASA Astrophysics Data System (ADS)

Rodigast, M.; Mutzel, A.; Iinuma, Y.; Haferkorn, S.; Herrmann, H.

2015-01-01

Carbonyl compounds are ubiquitous in the atmosphere and either emitted primarily from anthropogenic and biogenic sources or they are produced secondarily from the oxidation of volatile organic compounds (VOC). Despite a number of studies about the quantification of carbonyl compounds a comprehensive description of optimised methods is scarce for the quantification of atmospherically relevant carbonyl compounds. Thus a method was systematically characterised and improved to quantify carbonyl compounds. Quantification with the present method can be carried out for each carbonyl compound sampled in the aqueous phase regardless of their source. The method optimisation was conducted for seven atmospherically relevant carbonyl compounds including acrolein, benzaldehyde, glyoxal, methyl glyoxal, methacrolein, methyl vinyl ketone and 2,3-butanedione. O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine hydrochloride (PFBHA) was used as derivatisation reagent and the formed oximes were detected by gas chromatography/mass spectrometry (GC/MS). The main advantage of the improved method presented in this study is the low detection limit in the range of 0.01 and 0.17 μmol L-1 depending on carbonyl compounds. Furthermore best results were found for extraction with dichloromethane for 30 min followed by derivatisation with PFBHA for 24 h with 0.43 mg mL-1 PFBHA at a pH value of 3. The optimised method was evaluated in the present study by the OH radical initiated oxidation of 3-methylbutanone in the aqueous phase. Methyl glyoxal and 2,3-butanedione were found to be oxidation products in the samples with a yield of 2% for methyl glyoxal and 14% for 2,3-butanedione.

Design, synthesis and biological evaluation of hybrids of β-carboline and salicylic acid as potential anticancer and apoptosis inducing agents

PubMed Central

Xu, Qi-Bing; Chen, Xiang-Fan; Feng, Jiao; Miao, Jie-Fei; Liu, Ji; Liu, Feng-Tao; Niu, Bi-Xi; Cai, Jin-Yang; Huang, Chao; Zhang, Yanan; Ling, Yong

2016-01-01

A novel series of hybrids (7a-l, 8a-l) from β-carboline and salicylic acid (SA) were designed and synthesized, and their in vitro biological activities were evaluated. Most of the hybrids displayed potent antiproliferative activity against five cancer cell lines in vitro, showing potencies superior to 5-FU and harmine. In particular, compound 8h selectively inhibited proliferation of liver cancer SMMC-7721 cells but not normal liver LO2 cells, and displayed greater inhibitory selectivity than intermediate 5h and SA. 8h also induced cancer cell apoptosis in an Annexin V-FITC/propidium iodide flow cytometry assay, and triggered the mitochondrial/caspase apoptosis by decreasing mitochondrial membrane potential which was associated with up-regulation of Bax, down-regulation of Bcl-2 and activation levels of the caspase cascade in a concentration-dependent manner. Our findings suggest that the β-carboline/SA hybrids may hold greater promise as therapeutic agents for the intervention of human cancers. PMID:27824091

Regulation of water, salinity, and cold stress responses by salicylic acid

PubMed Central

Miura, Kenji; Tada, Yasuomi

2014-01-01

Salicylic acid (SA) is a naturally occurring phenolic compound. SA plays an important role in the regulation of plant growth, development, ripening, and defense responses. The role of SA in the plant–pathogen relationship has been extensively investigated. In addition to defense responses, SA plays an important role in the response to abiotic stresses, including drought, low temperature, and salinity stresses. It has been suggested that SA has great agronomic potential to improve the stress tolerance of agriculturally important crops. However, the utility of SA is dependent on the concentration of the applied SA, the mode of application, and the state of the plants (e.g., developmental stage and acclimation). Generally, low concentrations of applied SA alleviate the sensitivity to abiotic stresses, and high concentrations of applied induce high levels of oxidative stress, leading to a decreased tolerance to abiotic stresses. In this article, the effects of SA on the water stress responses and regulation of stomatal closure are reviewed. PMID:24478784

Perception of the plant immune signal salicylic acid

PubMed Central

Yan, Shunping; Dong, Xinnian

2014-01-01

Salicylic acid (SA) plays a central role in plant innate immunity. The diverse functions of this simple phenolic compound suggest that plants may have multiple SA receptors. Several SA-binding proteins have been identified using biochemical approaches. However, genetic evidence supporting that they are the bona fide SA receptors has not been forthcoming. Mutant screens revealed that NPR1 is a master regulator of SA-mediated responses. Although NPR1 cannot bind SA in a conventional ligand-binding assay, its homologs NPR3 and NPR4 bind SA and function as SA receptors. During pathogen challenge, the SA gradient generated at the infection site is sensed by NPR3 and NPR4, which serve as the adaptors for the Cullin 3-based E3 ubiquitin ligase to regulate NPR1 degradation. Consequently, NPR1 is degraded at the infection site to remove its inhibition on effector-triggered cell death and defense, whereas NPR1 accumulates in neighboring cells to promote cell survival and SA-mediated resistance. PMID:24840293

Zosteric acid and salicylic acid bound to a low density polyethylene surface successfully control bacterial biofilm formation.

PubMed

Cattò, C; James, G; Villa, F; Villa, S; Cappitelli, F

2018-05-04

The active moieties of the anti-biofilm natural compounds zosteric (ZA) and salicylic (SA) acids have been covalently immobilized on a low density polyethylene (LDPE) surface. The grafting procedure provided new non-toxic eco-friendly materials (LDPE-CA and LDPE-SA) with anti-biofilm properties superior to the conventional biocide-based approaches and with features suitable for applications in challenging fields where the use of antimicrobial agents is limited. Microbiological investigation proved that LDPE-CA and LDPE-SA: (1) reduced Escherichia coli biofilm biomass by up to 61% with a mechanism that did not affect bacterial viability; (2) significantly affected biofilm morphology, decreasing biofilm thickness, roughness, substratum coverage, cell and matrix polysaccharide bio-volumes by >80% and increasing the surface to bio-volume ratio; (3) made the biofilm more susceptible to ampicillin and ethanol. Since no molecules were leached from the surface, they remained constantly effective and below the lethal level; therefore, the risk of inducing resistance was minimized.

Effects of salicylic acid on post-ischaemic ventricular function and purine efflux in isolated mouse hearts.

PubMed

Farthing, Don; Gehr, Lynne; Karnes, H Thomas; Sica, Domenic; Gehr, Todd; Larus, Terri; Farthing, Christine; Xi, Lei

2007-01-01

Acetyl salicylic acid (aspirin) is one of the most widely used drugs in the world. Various plasma concentrations of aspirin and its predominant metabolite, salicylic acid, are required for its antiarthritic (1.5-2.5 mM), anti-inflammatory (0.5-5.0 mM) or antiplatelet (0.18-0.36 mM) actions. A recent study demonstrated the inhibitory effects of both aspirin and salicylic acid on oxidative phosphorylation and ATP synthesis in isolated rat cardiac mitochondria in a dose-dependent manner (0-10 mM concentration range). In this context, the present study was conducted to determine the effects of salicylic acid on inosine efflux (a potential biomarker of acute cardiac ischaemia) as well as cardiac contractile function in the isolated mouse heart following 20 min of zero-flow global ischaemia. Inosine efflux was found at significantly higher concentrations in ischaemic hearts perfused with Krebs buffer fortified with 1.0 mM salicylic acid compared with those without salicylic acid (12575+/-3319 vs. 1437+/-348 ng ml(-1) min(-1), mean+/-SEM, n=6 per group, p<0.01). These results indicate that 1.0 mM salicylic acid potentiates 8.8-fold ATP nucleotide purine catabolism into its metabolites (e.g. inosine, hypoxanthine). Salicylic acid (0.1 or 1.0 mM) did not appreciably inhibit purine nucleoside phosphorylase (the enzyme converts inosine to hypoxanthine) suggesting the augmented inosine efflux was due to the salicylic acid effect on upstream elements of cellular respiration. Whereas post-ischaemic cardiac function was further depressed by 1.0 mM salicylic acid, perfusion with 0.1 mM salicylic acid led to a remarkable functional improvement despite moderately increased inosine efflux (2.7-fold). We conclude that inosine is a sensitive biomarker for detecting cardiac ischaemia and salicylic acid-induced effects on cellular respiration. However, the inosine efflux level appears to be a poor predictor of the individual post-ischaemic cardiac functional recovery in this ex vivo model.

Methyl Salicylate Lactoside Protects Neurons Ameliorating Cognitive Disorder Through Inhibiting Amyloid Beta-Induced Neuroinflammatory Response in Alzheimer’s Disease

PubMed Central

Li, Jinze; Ma, Xiaowei; Wang, Yu; Chen, Chengjuan; Hu, Min; Wang, Linlin; Fu, Junmin; Shi, Gaona; Zhang, Dongming; Zhang, Tiantai

2018-01-01

Neuroinflammatory reactions mediated by microglia and astrocytes have been shown to play a key role in early progression of Alzheimer’s disease (AD). Increased evidences have demonstrated that neurons exacerbate local inflammatory reactions by producing inflammatory mediators and act as an important participant in the pathogenesis of AD. Methyl salicylate lactoside (MSL) is an isolated natural product that is part of a class of novel non-steroidal anti-inflammatory drugs (NSAID). In our previous studies, we demonstrated that MSL exhibited therapeutic effects on arthritis-induced mice and suppressed the activation of glial cells. In the current study, we investigated the effects of MSL on cognitive function and neuronal protection induced by amyloid-beta peptides (Aβ) and explored potential underlying mechanisms involved. Amyloid precursor protein (APP) and presenilin 1 (PS1) double transgenic mice were used to evaluate the effects of MSL through behavioral testing and neuronal degenerative changes. In addition, copper-injured APP Swedish mutation overexpressing SH-SY5Y cells were used to determine the transduction of cyclooxygenase (COX) and mitogen-activated protein kinase (MAPK) pathways. Our results indicated that at an early stage, MSL treatment ameliorated cognitive impairment and neurodegeneration in APP/PS1 mice. Moreover, in an in vitro AD model, MSL treatment protected injured cells by increasing cell viability, improving mitochondrial dysfunction, and decreasing oxidative damage. In addition, MSL inhibited the phosphorylated level of c-Jun N-terminal kinase (JNK) and p38 MAPK, and suppressed the expression of COX-1/2. As a novel NSAIDs and used for the treatment in early stage of AD, MSL clearly demonstrated cognitive preservation by protecting neurons via a pleiotropic anti-inflammatory effect in the context of AD-associated deficits. Therefore, early treatment of anti-inflammatory therapy may be an effective strategy for treating AD. PMID:29636677

Leaf and root glucosinolate profiles of Chinese cabbage (Brassica rapa ssp. pekinensis) as a systemic response to methyl jasmonate and salicylic acid elicitation.

PubMed

Zang, Yun-xiang; Ge, Jia-li; Huang, Ling-hui; Gao, Fei; Lv, Xi-shan; Zheng, Wei-wei; Hong, Seung-beom; Zhu, Zhu-jun

2015-08-01

Glucosinolates (GSs) are an important group of defensive phytochemicals mainly found in Brassicaceae. Plant hormones jasmonic acid (JA) and salicylic acid (SA) are major regulators of plant response to pathogen attack. However, there is little information about the interactive effect of both elicitors on inducing GS biosynthesis in Chinese cabbage (Brassica rapa ssp. pekinensis). In this study, we applied different concentrations of methyl jasmonate (MeJA) and/or SA onto the leaf and root of Chinese cabbage to investigate the time-course interactive profiles of GSs. Regardless of the site of the elicitation and the concentrations of the elicitors, the roots accumulated much more GSs and were more sensitive and more rapidly responsive to the elicitors than leaves. Irrespective of the elicitation site, MeJA had a greater inducing and longer lasting effect on GS accumulation than SA. All three components of indole GS (IGS) were detected along with aliphatic and aromatic GSs. However, IGS was a major component of total GSs that accumulated rapidly in both root and leaf tissues in response to MeJA and SA elicitation. Neoglucobrassicin (neoGBC) did not respond to SA but to MeJA in leaf tissue, while it responded to both SA and MeJA in root tissue. Conversion of glucobrassicin (GBC) to neoGBC occurred at a steady rate over 3 d of elicitation. Increased accumulation of 4-methoxy glucobrassicin (4-MGBC) occurred only in the root irrespective of the type of elicitors and the site of elicitation. Thus, accumulation of IGS is a major metabolic hallmark of SA- and MeJA-mediated systemic response systems. SA exerted an antagonistic effect on the MeJA-induced root GSs irrespective of the site of elicitation. However, SA showed synergistic and antagonistic effects on the MeJA-induced leaf GSs when roots and leaves are elicitated for 3 d, respectively.

Experimental and computational approaches of a novel methyl (2E)-2-{[N-(2-formylphenyl)(4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl)prop-2-enoate: A potential antimicrobial agent and an inhibition of penicillin-binding protein

NASA Astrophysics Data System (ADS)

Murugavel, S.; Vetri velan, V.; Kannan, Damodharan; Bakthadoss, Manickam

2016-07-01

The title compound methyl(2E)-2-{[N-(2-formylphenyl) (4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl) prop-2-enoate (MFMSC) has been synthesized and single crystals were grown by slow evaporation solution growth technique at room temperature. Structural and vibrational spectroscopic studies were carried out by using single crystal X-ray diffraction, FT-IR and NMR spectral analysis together with DFT method using GAUSSIAN'03 software. The detailed interpretation of the vibrational spectra has been carried out by VEDA program. NBO analysis, Mulliken charge analysis, HOMO-LUMO, MEP, Global chemical reactivity descriptors and thermodynamic properties have been analyzed. The hyperpolarisability calculation reveals the present material has a reasonably good propensity for nonlinear optical activity. The obtained antimicrobial activity results indicate that the compound shows good to moderate activity against all tested bacterial and fungal pathogens. A computational study was also carried out to predict the drug-likeness and ADMET properties of the title compound. Due to the different potential biological activity of the title compound, molecular docking study is also reported and the compound might exhibit inhibitory activity against penicillin-binding protein PBP-2X.

Metal resistance sequences and transgenic plants

DOEpatents

Meagher, Richard Brian; Summers, Anne O.; Rugh, Clayton L.

1999-10-12

The present invention provides nucleic acid sequences encoding a metal ion resistance protein, which are expressible in plant cells. The metal resistance protein provides for the enzymatic reduction of metal ions including but not limited to divalent Cu, divalent mercury, trivalent gold, divalent cadmium, lead ions and monovalent silver ions. Transgenic plants which express these coding sequences exhibit increased resistance to metal ions in the environment as compared with plants which have not been so genetically modified. Transgenic plants with improved resistance to organometals including alkylmercury compounds, among others, are provided by the further inclusion of plant-expressible organometal lyase coding sequences, as specifically exemplified by the plant-expressible merB coding sequence. Furthermore, these transgenic plants which have been genetically modified to express the metal resistance coding sequences of the present invention can participate in the bioremediation of metal contamination via the enzymatic reduction of metal ions. Transgenic plants resistant to organometals can further mediate remediation of organic metal compounds, for example, alkylmetal compounds including but not limited to methyl mercury, methyl lead compounds, methyl cadmium and methyl arsenic compounds, in the environment by causing the freeing of mercuric or other metal ions and the reduction of the ionic mercury or other metal ions to the less toxic elemental mercury or other metals.

Synthesis, characterization and in silico designing of diethyl-3-methyl-5-(6-methyl-2-thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamido) thiophene-2,4-dicarboxylate derivative as anti-proliferative and anti-microbial agents.

PubMed

Malani, Kalpesh; Thakkar, Sampark S; Thakur, Mukund Chandra; Ray, Arabinda; Doshi, Hiren

2016-10-01

A series of eight compounds diethyl-3-methyl-5-(6-methyl-2-thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamido) thiophene-2,4-dicarboxilate (KM10-17) analogues have been prepared by conventional methods and characterized by IR, Mass, NMR and elemental analysis. In silico docking studies on Human topoisomerase IIbeta (PDB Id: 3QX3) have been performed for all molecules (KM10-17) synthesized. The compounds were tested for in vitro anti-proliferative activity on VERO and 786-O cell lines. Out of all the synthesized compounds, KM11 &KM16 showed moderate activity on both cell lines. In vitro anti-microbial activity was also checked against Bacillus subtilis (BS), Staphylococcus aurous (SA), Pseudomonas aeruginosa (PA), Escherichia coli (EC) and Candida albicans (CA) by well diffusion method. The compound KM11 was found to have highest zone of inhibition against BS, SA, PA and EC. The molecules KM13 and KM16 exhibited good activity against CA. The compounds KM14 and KM16 indicated good zone of inhibition against BS. Copyright © 2016 Elsevier Inc. All rights reserved.

Bioconversion of lutein by Enterobacter hormaechei to form a new compound, 8-methyl-α-ionone.

PubMed

Zhong, Guifang; Wang, Fangfang; Sun, Jianhong; Ye, Jianbin; Mao, Duobin; Ma, Ke; Yang, Xuepeng

2017-07-01

To investigate the final product of the bioconversion of lutein by a novel lutein-degrading bacterium, Enterobacter hormaechei A20, and the kinetics of the process. A new product, 8-methyl-α-ionone, was resolved by GC-MS. The compound was further identified by NMR. A conversion yield of 90% was achieved by E. hormaechei in 36 h with 10 g lutein l -1 . This is the first report of the bioconversion of lutein to form 8-methyl-α-ionone. A degradation pathway is proposed.

Flavonoids and stilbenoids from Derris eriocarpa.

PubMed

Zhang, Hong-Xia; Lunga, Paul-Keilah; Li, Zhi-Jian; Dai, Qin; Du, Zhi-Zhi

2014-06-01

One new resveratrol analogue, 1-(3',4',5'-trimethoxyphenyl)-2-methoxy-2-(4″-methoxyphenyl)-ethane-1-ol (1), and two new prenylisoflavones, 4'-hydroxy-5,7-dimethoxy-6-(3-methyl-2-butenyl)-isoflavone (2), and derrubon 5-methyl ether (3), together with 17 known compounds including one new natural product, 5,7-dihydroxy-3-[4'-O-(3-methyl-2-butenyl)-phenyl]-isoflavone (4), were isolated from the stems of ethnomedicinal plant Derris eriocarpa How. (Leguminosae). Their structures were elucidated based on chemical evidence and spectroscopic techniques including two-dimensional NMR methods. All compounds are reported from this species for the first time. Antimicrobial activities of the new compounds were evaluated. Compound 2 exhibited good inhibitory activities against Candida guilliermondii, C. albicans and Microsporium gypseum with the minimal inhibitory concentration (MIC) values of 12.5 μg/ml. Copyright © 2014 Elsevier B.V. All rights reserved.

The protective effect of salicylic acid on lysozyme against riboflavin-mediated photooxidation

NASA Astrophysics Data System (ADS)

Li, Kun; Wang, Hongbao; Cheng, Lingli; Zhu, Hui; Wang, Mei; Wang, Shi-Long

2011-06-01

As a metabolite of aspirin in vivo, salicylic acid was proved to protect lysozyme from riboflavin-mediated photooxidation in this study. The antioxidative properties of salicylic acid were further studied by using time-resolved laser flash photolysis of 355 nm. It can quench the triplet state of riboflavin via electron transfer from salicylic acid to the triplet state of riboflavin with a reaction constant of 2.25 × 10 9 M -1 s -1. Mechanism of antioxidant activities of salicylic acid on lysozyme oxidation was discussed. Salicylic acid can serve as a potential antioxidant to quench the triplet state of riboflavin and reduce oxidative pressure.

Salicylate enables cochlear arachidonic-acid-sensitive NMDA receptor responses.

PubMed

Ruel, Jérôme; Chabbert, Christian; Nouvian, Régis; Bendris, Rim; Eybalin, Michel; Leger, Claude Louis; Bourien, Jérôme; Mersel, Marcel; Puel, Jean-Luc

2008-07-16

Currently, many millions of people treated for various ailments receive high doses of salicylate. Consequently, understanding the mechanisms by which salicylate induces tinnitus is an important issue for the research community. Behavioral testing in rats have shown that tinnitus induced by salicylate or mefenamate (both cyclooxygenase blockers) are mediated by cochlear NMDA receptors. Here we report that the synapses between the sensory inner hair cells and the dendrites of the cochlear spiral ganglion neurons express NMDA receptors. Patch-clamp recordings and two-photon calcium imaging demonstrated that salicylate and arachidonate (a substrate of cyclooxygenase) enabled the calcium flux and the neural excitatory effects of NMDA on cochlear spiral ganglion neurons. Salicylate also increased the arachidonate content of the whole cochlea in vivo. Single-unit recordings of auditory nerve fibers in adult guinea pig confirmed the neural excitatory effect of salicylate and the blockade of this effect by NMDA antagonist. These results suggest that salicylate inhibits cochlear cyclooxygenase, which increased levels of arachidonate. The increased levels of arachidonate then act on NMDA receptors to enable NMDA responses to glutamate that inner hair cells spontaneously release. This new pharmacological profile of salicylate provides a molecular mechanism for the generation of tinnitus at the periphery of the auditory system.

ARSENIC (+3 OXIDATION STATE) METHYLTRANSFERASE AND THE INORGANIC ARSENIC METHYLATION PHENOTYPE

EPA Science Inventory

Inorganic arsenic is enzymatically methylated; hence, its ingestion results in exposure to the parent compound and various methylated arsenicals. Both experimental and epidemiological evidence suggest that some of the adverse health effects associated with chronic exposure to in...

Comparative plasma salicylate and urine salicylurate levels following administration of aspirin, magnesium salicylate, and choline magnesium trisalicylate.

PubMed

Mason, W D

1980-11-01

Eighteen healthy volunteers were administered single doses of commercially available solid dosage forms of aspirin, magnesium salicylate (I), and choline magnesium trisalicylate (II), equivalent to approximately 500 mg of salicylic acid, in a randomized, complete crossover design. Plasma salicylate and urine salicylurate levels were measured by high-pressure liquid chromatography at frequent intervals following dosing; the resultant profiles, areas under the curve (AUC), and percentages of dose excreted as salicylurate were statistically analyzed by an analysis of variance. The plasma salicylate levels following the two dosage forms containing I and II were virtually identical when corrected for small differences in the dose. The plasma salicylic acid level following aspirin was approximately 10% lower during the 1.5--3.0-hr interval due to a portion of unhydrolyzed aspirin, but the dose-corrected AUC for the products tested did not differ significantly (p < 0.05). During the 24 hr following dosing, 66.5 +/- 12.1 68.4 +/- 7.1, and 60.9 +/- 14.1% of the salicylic acid were excreted as urine salicylurate for aspirin, I, and II, respectively, with no significant difference (p < 0.05). Based on this study, there are no significant differences in the rate and extent of absorption of salicylate following the three dosage forms tested, and the elimination kinetics of salicylic acid are not altered by these dosage forms.

N-substituted methyl maleamates as larvicidal compounds against Aedes aegypti (Diptera: Culicidae).

PubMed

Harburguer, Laura; Gonzalez, Paula V; Gonzalez Audino, Paola; Zerba, Eduardo; Masuh, Héctor

2018-02-01

Severe human arboviral diseases can be transmitted by the mosquito Aedes aegypti (L.), including dengue, chikungunya, zika, and yellow fever. The use of larvicides in containers that can result as potential breeding places and cannot be eliminated is the main alternative in control programs. However, their continuous and widespread use caused an increase in insecticide-resistant populations of this mosquito. The aim of this study was to evaluate the effect of three N-substituted methyl maleamates as larvicides on Ae. aegypti, the N-propyl methyl maleamate (PMM), N-butyl methyl maleamate (BMM), and N-hexyl methyl maleamate (HMM). These compounds could have a different mode of action from those larvicides known so far. We evaluated the larva mortality after 1 and 24 h of exposure and we found that mortality was fast and occurs within the first 60 min. HMM was slightly more effective with LC 50 values of 0.7 and 0.3 ppm for 1 and 24 h of exposure and LC 95 of 11 and 3 ppm. Our results demonstrate that N-substituted methyl maleamates have insecticidal properties for the control of Ae. aegypti larvae. These compounds could become useful alternatives to traditional larvicides after studying their insecticidal mechanism as well as their toxicity towards non target organisms.

Epigenetic control of plant immunity.

PubMed

Alvarez, María E; Nota, Florencia; Cambiagno, Damián A

2010-07-01

In eukaryotic genomes, gene expression and DNA recombination are affected by structural chromatin traits. Chromatin structure is shaped by the activity of enzymes that either introduce covalent modifications in DNA and histone proteins or use energy from ATP to disrupt histone-DNA interactions. The genomic 'marks' that are generated by covalent modifications of histones and DNA, or by the deposition of histone variants, are susceptible to being altered in response to stress. Recent evidence has suggested that proteins generating these epigenetic marks play crucial roles in the defence against pathogens. Histone deacetylases are involved in the activation of jasmonic acid- and ethylene-sensitive defence mechanisms. ATP-dependent chromatin remodellers mediate the constitutive repression of the salicylic acid-dependent pathway, whereas histone methylation at the WRKY70 gene promoter affects the activation of this pathway. Interestingly, bacterial-infected tissues show a net reduction in DNA methylation, which may affect the disease resistance genes responsible for the surveillance against pathogens. As some epigenetic marks can be erased or maintained and transmitted to offspring, epigenetic mechanisms may provide plasticity for the dynamic control of emerging pathogens without the generation of genomic lesions.

Differential uptake of salicylate in serum, cerebrospinal fluid, and perilymph.

PubMed

Jastreboff, P J; Hansen, R; Sasaki, P G; Sasaki, C T

1986-10-01

After intraperitoneal administration of salicylate in anesthetized rats and guinea pigs, we found that salicylate levels in perilymph (PL) are closely related to both drug levels in cerebrospinal fluid (CSF) and in serum, with higher levels systematically observed in PL than in CSF. Further analysis suggests that salicylate is not passively transported into PL across CSF but, rather, is transported from blood directly to PL. The time course of salicylate uptake in rats reveals maximum levels at 1 1/2 hours (serum) and two to four hours (CSF and PL). On the other hand, salicylate uptake into serum and CSF of guinea pigs exhibits a longer time course, with maximum levels reached at four hours (serum) and five hours (CSF). These data, not previously available, are basic to our understanding of salicylate-related auditory effects.

Insight into magnesium coordination environments in benzoate and salicylate complexes through 25Mg solid-state NMR spectroscopy.

PubMed

Burgess, Kevin M N; Xu, Yang; Leclerc, Matthew C; Bryce, David L

2013-08-01

We report on the (25)Mg solid-state nuclear magnetic resonance (NMR) characterization of a series of magnesium complexes featuring Mg(2+) ions in organic coordination environments. Six compounds have been synthesized with benzoate and salicylate ligands, which are typically used as linkers in metal organic frameworks (MOFs). The use of ultrahigh-field solid-state NMR has revealed a relatively large range of values for the (25)Mg quadrupolar coupling constant, CQ((25)Mg), in these compounds. In contrast to some previously studied inorganic Mg(2+) complexes, the values of CQ((25)Mg) in organic Mg(2+) complexes are well rationalized by the degree of octahedral strain of the "MgO6" coordination polyhedra. (13)C and (25)Mg isotropic chemical shifts were also found to be sensitive to the binding mode of the carboxylate ligands. The experimental findings are corroborated by gauge-including projector-augmented-wave (GIPAW) density functional theory (DFT) computations, and these have allowed for an interpretation of the experimentally observed trend in the CQ((25)Mg) values and for the visualization of the EFG tensor principal components with respect to the molecular structure. These new insights may prove to be valuable for the understanding and interpretation of (25)Mg NMR data for Mg(2+) ions in organic binding environments such as those found in MOFs and protein-divalent metal binding sites.

Gaseous 3-pentanol primes plant immunity against a bacterial speck pathogen, Pseudomonas syringae pv. tomato via salicylic acid and jasmonic acid-dependent signaling pathways in Arabidopsis.

PubMed

Song, Geun C; Choi, Hye K; Ryu, Choong-Min

2015-01-01

3-Pentanol is an active organic compound produced by plants and is a component of emitted insect sex pheromones. A previous study reported that drench application of 3-pentanol elicited plant immunity against microbial pathogens and an insect pest in crop plants. Here, we evaluated whether 3-pentanol and the derivatives 1-pentanol and 2-pentanol induced plant systemic resistance using the in vitro I-plate system. Exposure of Arabidopsis seedlings to 10 μM and 100 nM 3-pentanol evaporate elicited an immune response to Pseudomonas syringae pv. tomato DC3000. We performed quantitative real-time PCR to investigate the 3-pentanol-mediated Arabidopsis immune responses by determining Pathogenesis-Related (PR) gene expression levels associated with defense signaling through salicylic acid (SA), jasmonic acid (JA), and ethylene signaling pathways. The results show that exposure to 3-pentanol and subsequent pathogen challenge upregulated PDF1.2 and PR1 expression. Selected Arabidopsis mutants confirmed that the 3-pentanol-mediated immune response involved SA and JA signaling pathways and the NPR1 gene. Taken together, this study indicates that gaseous 3-pentanol triggers induced resistance in Arabidopsis by priming SA and JA signaling pathways. To our knowledge, this is the first report that a volatile compound of an insect sex pheromone triggers plant systemic resistance against a bacterial pathogen.

40 CFR 721.10089 - Modified salicylic acid, zirconium complex (generic).

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Modified salicylic acid, zirconium... Specific Chemical Substances § 721.10089 Modified salicylic acid, zirconium complex (generic). (a) Chemical... as modified salicylic acid, zirconium complex (PMN P-00-552) is subject to reporting under this...

40 CFR 721.10089 - Modified salicylic acid, zirconium complex (generic).

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Modified salicylic acid, zirconium... Specific Chemical Substances § 721.10089 Modified salicylic acid, zirconium complex (generic). (a) Chemical... as modified salicylic acid, zirconium complex (PMN P-00-552) is subject to reporting under this...

Antiinflammatory and lipoxygenase inhibitory compounds from Vitex agnus-castus.

PubMed

Choudhary, M Iqbal; Jalil, Saima; Nawaz, Sarfraz Ahmad; Khan, Khalid Mohammed; Tareen, Rasool Bakhsh

2009-09-01

Several secondary metabolites, artemetin (1), casticin (2), 3,3'-dihydroxy-5,6,7,4'-tetramethoxy flavon (3), penduletin (4), methyl 4-hydroxybenzoate (5), p-hydroxybenzoic acid (6), methyl 3,4-dihydroxybenzoate (7), 5-hydroxy-2-methoxybenzoic acid (8), vanillic acid (9) and 3,4-dihydroxybenzoic acid (10) were isolated from a folkloric medicinal plant, Vitex agnus-castus. The structures of compounds 1-10 were identified with the help of spectroscopic techniques. Compounds 3-10 were isolated for the first time from this plant. These compounds were screened for their antiinflammatory and lipoxygenase inhibitory activities. Compounds 6, 7 and 10 were found to have significant antiinflammatory activity in a cell-based contemporary assay, whereas compounds 1 and 2 exhibited a potent lipoxygenase inhibition.

Fatty acid methyl ester from Neurospora intermedia N-1 isolated from Indonesian red peanut cake (oncom merah).

PubMed

Priatni, S; Hartati, S; Dewi, P; Kardono, L B S; Singgih, M; Gusdinar, T

2010-08-01

The objective of this study was to identify the Fatty Acid Methyl Ester (FAME) from Neurospora intermedia N-1 that isolated from Indonesian red peanut cake (oncom). FAME profiles have been used as biochemical characters to study many different groups of organisms, such as bacteria and yeasts. FAME from N. intermedia N-1 was obtained by some stages of extraction the orange spores and fractination using a chromatotron. The pure compound (1) was characterized by 500 mHz NMR (1H and 13C), FTIR and LC-MS. Summarized data's of 1H and 13C NMR spectra of compound 1 contained 19 Carbon, 34 Hydrogen and 2 Oxygen (C19H34O2). The position of the double bonds at carbon number 8 and 12 were indicated in the HMBC spectrum (2D-NMR). LC-MS spectrum indicates molecular weight of the compound 1 as 294 which is visible by the presence of protonated molecular ion [M+H] at m/z 295. Methyl esters of long chain fatty acids was presented by a 3 band pattern of IR spectrum with bands near 1249, 1199 and 1172 cm(-1). We suggested that the structure of the pure compound 1 is methyl octadeca-8,12-dienoate. The presence methyl octadeca-8,12-dienoate in N. intermedia is the first report.

"Sweeter than a rose", at least to Triatoma phyllosoma complex males (Triatominae: Reduviidae).

PubMed

May-Concha, Irving J; Cruz-López, Leopoldo C; Rojas, Julio C; Ramsey, Janine M

2018-02-17

The Triatoma phyllosoma complex of Trypanosoma cruzi vectors (Triatominae: Reduviidae) is distributed in both Neotropical and Nearctic bioregions of Mexico. Volatile organic compounds emitted by disturbed Triatoma longipennis, Triatoma pallidipennis and Triatoma phyllosoma, and from their Brindley's and metasternal glands, were identified using solid-phase microextraction coupled with gas chromatography-mass spectrometry. Disturbed bugs and the metasternal glands from T. phyllosoma released or had significantly fewer compounds than T. longipennis and T. pallidipennis. Isobutyric acid was the most abundant compound secreted by disturbed bugs of the three species, while Brindley's glands of all species produced another four compounds: propanoic acid, isobutyric acid, pentyl butanoate, and 2-methyl hexanoic acid. Two novel compounds, both rose oxide isomers, were produced in MGs and released only by disturbed females of all three species, making this the first report in Triatominae of these monoterpenes. The principal compound in MGs of both sexes of T. longipennis and T. phyllosoma was 3-methyl-2-hexanone, while cis-rose oxide was the principal compound in T. pallidipennis females. The major components in male effluvia of T. pallidipennis were 2-decanol and 3-methyl-2-hexanone. Discriminant analysis of volatile organic compounds was significant, separating the three species and was consistent with morphological and genetic evidence for species distinctions within the complex.

High-Throughput Analysis of Global DNA Methylation Using Methyl-Sensitive Digestion.

PubMed

Shiratori, Hiromi; Feinweber, Carmen; Knothe, Claudia; Lötsch, Jörn; Thomas, Dominique; Geisslinger, Gerd; Parnham, Michael J; Resch, Eduard

2016-01-01

DNA methylation is a major regulatory process of gene transcription, and aberrant DNA methylation is associated with various diseases including cancer. Many compounds have been reported to modify DNA methylation states. Despite increasing interest in the clinical application of drugs with epigenetic effects, and the use of diagnostic markers for genome-wide hypomethylation in cancer, large-scale screening systems to measure the effects of drugs on DNA methylation are limited. In this study, we improved the previously established fluorescence polarization-based global DNA methylation assay so that it is more suitable for application to human genomic DNA. Our methyl-sensitive fluorescence polarization (MSFP) assay was highly repeatable (inter-assay coefficient of variation = 1.5%) and accurate (r2 = 0.99). According to signal linearity, only 50-80 ng human genomic DNA per reaction was necessary for the 384-well format. MSFP is a simple, rapid approach as all biochemical reactions and final detection can be performed in one well in a 384-well plate without purification steps in less than 3.5 hours. Furthermore, we demonstrated a significant correlation between MSFP and the LINE-1 pyrosequencing assay, a widely used global DNA methylation assay. MSFP can be applied for the pre-screening of compounds that influence global DNA methylation states and also for the diagnosis of certain types of cancer.

Multiple roles of a male-specific compound in the sexual behavior of the dried bean beetle, Acanthoscelides obtectus.

PubMed

Vuts, József; Powers, Stephen J; Caulfield, John C; Pickett, John A; Birkett, Michael A

2015-03-01

Males of Acanthoscelides obtectus (Coleoptera: Chrysomelidae, Bruchinae) emit methyl (E,R)-2,4,5-tetradecatrienoate that attracts females for mating. This study identified further roles for this compound in the sexual behavior of A. obtectus. Earlier observations revealed that males touched females with their antennae while tandem-running with them and initiated mounting and copulation, whereas they showed no such behavior toward other males. A series of subsequent laboratory choice tests were set up to establish if certain cuticular compounds aid contact sex recognition in A. obtectus. Males chose virgin females over other males. The activity toward females could be eliminated by rinsing with hexane, but was regained by application of female extract onto previously rinsed females. Gas chromatographic (GC) comparison of hexane extracts revealed the presence of two male-specific compounds, methyl (E,R)-2,4,5-tetradecatrienoate and octadecanal, which were absent from the behaviorally active female samples. Of the two compounds, methyl (E,R)-2,4,5-tetradecatrienoate was found to be responsible for the inhibition of male sexual behavior, similar to that observed with crude male extracts applied to virgin females. Furthermore, males preferred virgin over mated females. GC analyses revealed the presence of methyl (E,R)-2,4,5-tetradecatrienoate in mated females in amounts sufficient to curtail mating attempts. It appears that methyl (E,R)-2,4,5-tetradecatrienoate, besides being a male-produced sex pheromone, acts as a male-recognition signal in A. obtectus. Males also transfer it onto females during mating, resulting in mated females being avoided by courting males.

Comparison of kappa opioids in rhesus monkeys: behavioral effects and receptor binding affinities.

PubMed

France, C P; Medzihradsky, F; Woods, J H

1994-01-01

Bremazocine, [5R-(5,7,8 beta)]-N-methyl-N-[7-(1-pyrrolidinyl)1-oxaspiro [4,5]dec-8-yl]-4-benzofuranacetamide (Cl-977), (+-)-trans-3,4-dichloro-N- methyl-(2-(pyrrolidin-1-yl)-5-methoxy-1,2,3,4-tetrahydronapth++ +-1-yl benzeneacetamide methanesulfonate (DUP 747), ethylketocyclazocine (EKC), nalorphine, (+/-)-trans-N-methyl-N-[2-(1- pyrrolidnyl)-cyclohexyl]benzo[b]thiophene-4-acetamide (PD117302), trans-(+/-)-3,4-dichloro-N-methyl-[2-(1-pyrrolidinyl)- cyclohexyl]benzeneacetamide (U-50,488), (5,7,8 beta)-N-methyl-N[2-(1- pyrrolidinyl), 1-oxaspiro[4,5]dec-8-yl benzeneacetamide (U-69,593) and spiradoline were compared in rhesus monkeys for their discriminative stimulus, analgesic and respiratory effects. Selected compounds also were studied for their binding affinities at mu [[3H](D-Ala2-Me-Phe4,Glyol5)enkephalin], kappa ([3H]U-69,593) and delta [[3H](D-Pen2-D-Pen5) enkephalin], opioid receptors in monkey brain membranes. All compounds substituted completely (> or = 90%) for EKC in monkeys discriminating between EKC and saline, with the exception that DUP 747 produced a maximum of 74% EKC responding. None of the compounds reversed naltrexone responding in morphine-abstinent monkeys; all of the compounds substituted for naltrexone in morphine-treated monkeys discriminating between naltrexone and saline, with the exception that spiradoline produced a maximum of 68% naltrexone responding. Eight compounds produced maximum analgesic effects in a tail withdrawal procedure and quadazocine antagonized these effects; nalorphine did not have analgesic effects, but it antagonized analgesic effects of several other compounds. U-50,488 did not decrease respiratory function, whereas U-69,593 decreased frequency of respiration and volume of respiration to less than 40% of control values; Cl-977, DUP 747, PD117302 and spiradoline had limited effects on respiratory function. Larger doses of each compound increased both respiration and motor activity.

Influence of modified atmosphere packaging on volatile compounds and physicochemical and antioxidant attributes of fresh-cut pineapple (Ananas comosus).

PubMed

Montero-Calderón, Marta; Rojas-Graü, María Alejandra; Aguiló-Aguayo, Ingrid; Soliva-Fortuny, Robert; Martín-Belloso, Olga

2010-04-28

The effects of modified atmosphere packaging on volatile compound content and physicochemical and antioxidant attributes of Gold cultivar fresh-cut pineapples were assessed throughout storage at 5 degrees C. Fresh-cut pineapple pieces were packed under LO (low oxygen, 12% O(2), 1% CO(2)), AIR (20.9% O(2)) and HO (high oxygen, 38% O(2)) headspace atmospheres. Methyl butanoate, methyl 2-methylbutanoate, and methyl hexanoate were the most abundant volatiles regardless of the packaging atmosphere and days of storage; whereas most odor active volatiles were methyl and ethyl 2-methylbutanoate, 2,5-dimethyl-4-methoxy-3(2H)-furanone and ethyl hexanoate. Physicochemical attributes of pineapple did not significantly vary, whereas vitamin C content and total antioxidant capacity were lower for fresh-cut pineapple in HO (488 +/- 38 mg/100 mg(fw) and 54.4 +/- 5.7%, respectively) than for LO and AIR packages. Storage life of fresh-cut pineapple was limited to 14 days by volatile compounds losses and fermentation processes.

Biochemical analysis of the biosynthetic pathway of an anticancer tetracycline SF2575.

PubMed

Pickens, Lauren B; Kim, Woncheol; Wang, Peng; Zhou, Hui; Watanabe, Kenji; Gomi, Shuichi; Tang, Yi

2009-12-09

SF2575 1 is a tetracycline polyketide produced by Streptomyces sp. SF2575 and displays exceptionally potent anticancer activity toward a broad range of cancer cell lines. The structure of SF2575 is characterized by a highly substituted tetracycline aglycon. The modifications include methylation of the C-6 and C-12a hydroxyl groups, acylation of the 4-(S)-hydroxyl with salicylic acid, C-glycosylation of the C-9 of the D-ring with D-olivose and further acylation of the C4'-hydroxyl of D-olivose with the unusual angelic acid. Understanding the biosynthesis of SF2575 can therefore expand the repertoire of enzymes that can modify tetracyclines, and facilitate engineered biosynthesis of SF2575 analogues. In this study, we identified, sequenced, and functionally analyzed the ssf biosynthetic gene cluster which contains 40 putative open reading frames. Genes encoding enzymes that can assemble the tetracycline aglycon, as well as installing these unique structural features, are found in the gene cluster. Biosynthetic intermediates were isolated from the SF2575 culture extract to suggest the order of pendant-group addition is C-9 glycosylation, C-4 salicylation, and O-4' angelylcylation. Using in vitro assays, two enzymes that are responsible for C-4 acylation of salicylic acid were identified. These enzymes include an ATP-dependent salicylyl-CoA ligase SsfL1 and a putative GDSL family acyltransferase SsfX3, both of which were shown to have relaxed substrate specificity toward substituted benzoic acids. Since the salicylic acid moiety is critically important for the anticancer properties of SF2575, verification of the activities of SsfL1 and SsfX3 sets the stage for biosynthetic modification of the C-4 group toward structure-activity relationship studies of SF2575. Using heterologous biosynthesis in Streptomyces lividans, we also determined that biosynthesis of the SF2575 tetracycline aglycon 8 parallels that of oxytetracycline 4 and diverges after the assembly of 4-keto-anhydrotetracycline 51. The minimal ssf polyketide synthase together with the amidotransferase SsfD produced the amidated decaketide backbone that is required for the formation of 2-naphthacenecarboxamide skeleton. Additional enzymes, such as cyclases C-6 methyltransferase and C-4/C-12a dihydroxylase, were functionally reconstituted.

Phytotoxicity, structural and computational analysis of 2-methyl-1,5-diarylpentadienones

NASA Astrophysics Data System (ADS)

Din, Zia Ud; Rodrigues-Filho, Edson; de Cassia Pereira, Viviane; Gualtieri, Sonia Cristina Juliano; Deflon, Victor Marcelo; da Silva Maia, Pedro Ivo; Kuznetsov, Aleksey E.

2017-08-01

In our studies aimed to produce new chemicals used in weed control, 2-methyl-1,5-diarylpentadienones were synthesized by the reaction of p-methoxybenzaldehyde, p-nitrobenzaldehyde and p-N,N-dimethylbenzaldehyde, respectively, with 2-butanone, resulting in four model compounds. The phytotoxicity of these compounds against wheat coleoptiles and Sesame seedling was observed at μM concentrations, indicating good potential for their usage in weed management in the field. Spectroscopic and computational studies were performed in order to gain understanding on their mechanisms of action and to clarify some structural complexities due existence of conformers and substituent effects. These compounds probably act as hydroxyphenylpyruvate dioxygenase inhibitors. The tested compounds were characterized by spectroscopic and single crystal X-ray diffraction analyses. Solid crystalline state of the compound A (2-Methyl-1-(p-methophyphenyl)-5-(phenyl)-diarylpentadienone) is observed in the monoclinic space group P21/c with unit cell dimensions a = 14.3366(4) Å, b = 11.3788(4) Å, c = 9.6319(3) Å, β = 96.596, V = 1560.88(9) Å3 and Z = 4. Compound C (2-Methyl-1-(p-methophyphenyl)-5-(p-nitrophenyl)-diarylpentadienone) crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 17.8276(9) Å, b = 7.3627(4) Å, c = 12.9740(6) Å, β = 107.6230(10), V = 1623.04(14) Å3 and Z = 4. LC-UV-MS analysis furnished important data helpful for their characterization. The spectroscopic data and computational (DFT) analysis revealed the fact that each of the compounds A-D occurs in solution as four conformers.

Salicylic acid derivatives: synthesis, features and usage as therapeutic tools.

PubMed

Ekinci, Deniz; Sentürk, Murat; Küfrevioğlu, Ömer İrfan

2011-12-01

In the field of medicinal chemistry, there is a growing interest in the use of small molecules. Although acetyl salicylic acid is well known for medical applications, little is known about other salicylic acid derivatives, and there is serious lack of data and information on the effects and biological evaluation that connect them. This review covers the synthesis and drug potencies of salicylic acid derivatives. After a brief overview of the information on salicylic acid and its features, a detailed review of salicylic acids as drugs and prodrugs, usage as cyclooxygenase inhibitors, properties in plants, synthesis and recent patents, is developed. Salicylic acid research is still an important area and innovations continue to arise, which offer hope for new therapeutics in related fields. It is anticipated that this review will guide the direction of long-term drug/nutraceutical safety trials and stimulate ideas for future research.

The distribution of triclosan and methyl-triclosan in marine sediments of Barker Inlet, South Australia.

PubMed

Fernandes, Milena; Shareef, Ali; Kookana, Rai; Gaylard, Sam; Hoare, Sonja; Kildea, Tim

2011-04-01

In this work, we investigated the transport and burial of triclosan and its methylated derivative, in surface sediments near the mouth of Barker Inlet in South Australia. The most likely source of this commonly used bactericide to the area is a wastewater outfall discharging at the confluence of the inlet with marine waters. Triclosan was detected in all samples, at concentrations (5-27 μg kg(-1)) comparable to values found in other surface sediments under the influence of marine wastewater outfalls. Its dispersal was closely associated with fine and organic-rich fractions of the sediments. Methyl-triclosan was detected in approximately half of the samples at concentrations <11 μg kg(-1). The occurrence of this compound was linked to both wastewater discharges and biological methylation of the parent compound. Wastewater-borne methyl-triclosan had a smaller spatial footprint than triclosan and was mostly deposited in close proximity to the outfall. In situ methylation of triclosan likely occurs at deeper depositional sites, whereas the absence of methyl-triclosan from shallower sediments was potentially explained by photodegradation of the parent compound. Based on partition equilibrium, a concentration of triclosan in the order of 1 μg L(-1) was estimated in sediment porewaters, a value lower than the threshold reported for harmful effects to occur in the couple of species of marine phytoplankton investigated to date. Methyl-triclosan presents a greater potential for bioaccumulation than triclosan, but the implications of its occurrence to aquatic ecosystem health are difficult to predict given the lack of ecotoxicological data in the current literature.

Phantom auditory sensation in rats: an animal model for tinnitus.

PubMed

Jastreboff, P J; Brennan, J F; Coleman, J K; Sasaki, C T

1988-12-01

In order to measure tinnitus induced by sodium salicylate injections, 84 pigmented rats, distributed among 14 groups in five experiments, were used in a conditioned suppression paradigm. In Experiment 1, all groups were trained with a conditioned stimulus (CS) consisting of the offset of a continuous background noise. One group began salicylate injections before Pavlovian training, a second group started injections after training, and a control group received daily saline injections. Resistance to extinction was profound when injections started before training, but minimal when initiated after training, which suggests that salicylate-induced effects acquired differential conditioned value. In Experiment 2 we mimicked the salicylate treatments by substituting a 7 kHz tone in place of respective injections, resulting in effects equivalent to salicylate-induced behavior. In a third experiment we included a 3 kHz CS, and again replicated the salicylate findings. In Experiment 4 we decreased the motivational level, and the sequential relation between salicylate-induced effects and suppression training was retained. Finally, no salicylate effects emerged when the visual modality was used. These findings support the demonstration of phantom auditory sensations in animals.

Salicylate-induced changes in spontaneous activity of single units in the inferior colliculus of the guinea pig.

PubMed

Jastreboff, P J; Sasaki, C T

1986-11-01

Changes in spontaneous neuronal activity of the inferior colliculus in albino guinea pigs before and after administration of sodium salicylate were analyzed. Animals were anesthetized with pentobarbital, and two microelectrodes separated by a few hundred microns were driven through the inferior colliculus. After collecting a sufficiently large sample of cells, sodium salicylate (450 mg/kg) was injected i.p. and recordings again made 2 h after the injection. Comparison of spontaneous activity recorded before and after salicylate administration revealed highly statistically significant differences (p less than 0.001). After salicylate, the mean rate of the cell population increased from 29 to 83 Hz and the median from 26 to 74 Hz. Control experiments in which sodium salicylate was replaced by saline injection revealed no statistically significant differences in cell discharges. Recordings made during the same experiments from lobulus V of the cerebellar vermis revealed no changes in response to salicylate. The observed changes in single-unit activity due to salicylate administration may represent the first systematic evidence of a tinnituslike phenomenon in animals.

Effects of Methyl Jasmonate on the Composition of Volatile Compounds in Pyropia yezoensis

NASA Astrophysics Data System (ADS)

He, Lihong; Wang, Liang; Wang, Linfang; Shen, Songdong

2018-04-01

Volatile organic compounds in marine algae have been reported to comprise characteristic flavor of algae and play an important role in their growth, development and defensive response. Yet their biogeneration remain largely unknown. Here we studied the composition of volatile compouds in Pyropia yezoensis and their variations in response to methyl jasmonate (MeJA) and diethyldithiocarbamic acid (DIECA) treatment using gas chromatography-mass spectrometry (GC-MS). A total of 44 compounds belonging to the following chemical classes (n) were identified, including aldehydes (11), alcohols (8), acids and esters (6), alkanes (5), ketones (5), alkenes (3), and S- or N-containing miscellaneous compounds (6). External treatment with plant hormone MeJA increased the content of 1-dodecanol, 4-heptenal, and 2-propenoic acid-2-methyl dodecylester, but decreased the content of phytol, 3-heptadecene, 2-pentadecanone, and isophytol. When pretreated with DIECA, an inhibitor of the octadecanoid pathway leading to the biosynthesis of endogeneous jasmonates and some secondary metabolites, phytol and isophytol were increased, while 4-heptenal, 1-dodecanol, and 2-propenoic acid-2-methyl dodecylester were decreased, both of which were negatively correlated with their variations under MeJA treatment. Collectively, these results suggest that MeJA does affect the volatile composition of P. yezoensis, and the octadecanoid pathway together with endogenous jasmonate pathway may be involved in the biosynthesis of volatile compounds, thereby providing some preliminary envision on the composition and biogeneration of volatile compounds in P. yezoensis.

Time-Resolved Fluorescence Resonance Energy Transfer Assay for Discovery of Small-Molecule Inhibitors of Methyl-CpG Binding Domain Protein 2.

PubMed

Wyhs, Nicolas; Walker, David; Giovinazzo, Hugh; Yegnasubramanian, Srinivasan; Nelson, William G

2014-08-01

Methylated DNA binding proteins such as Methyl-CpG Binding Domain Protein 2 (MBD2) can transduce DNA methylation alterations into a repressive signal by recruiting transcriptional co-repressor complexes. Interfering with MBD2 could lead to reactivation of tumor suppressor genes and therefore represents an attractive strategy for epigenetic therapy. We developed and compared fluorescence polarization (FP) and time-resolved fluorescence resonance energy transfer (TR-FRET)-based high-throughput screening (HTS) assays to identify small-molecule inhibitors of the interaction between the methyl binding domain of MBD2 (MBD2-MBD) and methylated DNA. Although both assays performed well in 96-well format, the TR-FRET assay (Z' factor = 0.58) emerged as a superior screening strategy compared with FP (Z' factor = 0.08) when evaluated in an HTS 384-well plate format. Using TR-FRET, we screened the Sigma LOPAC library for MBD2-MBD inhibitors and identified four compounds that also validated in a dose-response series. This included two known DNA intercalators (mitoxantrone and idarubicin) among two other inhibitory compounds (NF449 and aurintricarboxylic acid). All four compounds also inhibited the binding of SP-1, a transcription factor with a GC-rich binding sequence, to a methylated oligonucleotide, demonstrating that the activity was nonspecific. Our results provide proof of principle for using TR-FRET-based HTS to identify small-molecule inhibitors of MBD2 and other DNA-protein interactions. © 2014 Society for Laboratory Automation and Screening.

Methylation of ribonucleic acid by the carcinogens dimethyl sulphate, N-methyl-N-nitrosourea and N-methyl-N′-nitro-N-nitrosoguanidine. Comparisons of chemical analyses at the nucleoside and base levels

PubMed Central

Lawley, P. D.; Shah, S. A.

1972-01-01

1. The following methods for hydrolysis of methyl-14C-labelled RNA, and for chromatographic isolation and determination of the products, were investigated: enzymic digestion to nucleosides at pH6 or 8; alkaline hydrolysis and conversion into nucleosides; hydrolysis by acid to pyrimidine nucleotides and purine bases, or completely to bases; chromatography on Dowex 50 (NH4+ form) at pH6 or 8.9, or on Dowex 50 (H+ form), or on Sephadex G-10. 2. The suitability of the various methods for determination of methylation products was assessed. The principal product, 7-methylguanosine, was unstable under the conditions used for determinations of nucleosides. 3- and 7-Methyladenine and 3- and 7-methylguanine are best determined as bases; 1-methyladenine and 3-methylcytosine can be isolated as either nucleosides or bases; O6-methylguanine is unstable under the acid hydrolysis conditions used and can be determined as the nucleoside; 3-methyluracil was detected, but may be derived from methylation of the ionized form of uracil. 3. Differences between the patterns of methylation of RNA and homopolyribonucleotides by the N-methyl-N-nitroso compounds and dimethyl sulphate were found: the nitroso compounds were able to methylate O-6 of guanine, were relatively more reactive at N-7 of adenine and probably at N-3 of guanine, but less reactive at N-1 of adenine, N-3 of cytosine and probably at N-3 of uridine. They probably reacted more with the ribose–phosphate chain, but no products from this were identified. 4. The possible influences of these differences on biological action of the methylating agents is discussed. Nitroso compounds may differ principally in their ability to induce miscoding in the Watson–Crick sense by reaction at O-6 of guanine. Both types of agent may induce miscoding to a lesser extent through methylation at N-3 of guanine; both can methylate N atoms, presumably preventing Watson–Crick hydrogen-bonding. N-Methyl-N-nitrosourea can degrade RNA, possibly through phosphotriester formation, but this mechanism is not proven. PMID:4673570

Detection of chemical warfare simulants using Raman excitation at 1064 nm

NASA Astrophysics Data System (ADS)

Dentinger, Claire; Mabry, Mark W.; Roy, Eric G.

2014-05-01

Raman spectroscopy is a powerful technique for material identification. The technique is sensitive to primary and higher ordered molecular structure and can be used to identify unknown materials by comparison with spectral reference libraries. Additionally, miniaturization of opto-electronic components has permitted development of portable Raman analyzers that are field deployable. Raman scattering is a relatively weak effect compared to a competing phenomenon, fluorescence. Even a moderate amount of fluorescence background interference can easily prevent identification of unknown materials. A long wavelength Raman system is less likely to induce fluorescence from a wider variety of materials than a higher energy visible laser system. Compounds such as methyl salicylate (MS), diethyl malonate (DEM), and dimethyl methylphosphonate (DMMP) are used as chemical warfare agent (CWA) simulants for development of analytical detection strategies. Field detection of these simulants however poses unique challenges because threat identification must be made quickly without the turnaround time usually required for a laboratory based analysis. Fortunately, these CWA simulants are good Raman scatterers, and field based detection using portable Raman instruments is promising. Measurements of the CWA simulants were done using a 1064 nm based portable Raman spectrometer. The longer wavelength excitation laser was chosen relative to a visible based laser systems because the 1064 nm based spectrometer is less likely to induce fluorescence and more suitable to a wider range of materials. To more closely mimic real world measurement situations, different sample presentations were investigated.