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1.
Top Curr Chem (Cham) ; 380(1): 1, 2021 Nov 08.
Artigo em Inglês | MEDLINE | ID: mdl-34746982

RESUMO

This review article focuses on the α-functionalization of acetophenones involving Kornblum oxidation and C-H functionalizations. Although various other strategies, such as classical approaches, enamine approaches and umpolung strategy are also known for this functionalization, here we discuss mainly the Kornblum oxidation approach and C-H functionalization strategy as they have advantages over the others. In Kornblum oxidation, the reaction uses iodine and dimethylsulfoxide and proceeds through the formation of arylglyoxal as the key intermediate. In C-H functionalization, the reaction requires metal, or metal-free catalyst, and generates radical intermediate in most cases. α-Functionalization of acetophenones is very important because of their huge applications in the synthesis of various natural products and pharmaceuticals and, therefore, a number of research articles have been published in this area. However, no review articles are available so far. In this article, we present a succinct discussion of various important and novel reactions, along with their mechanisms, published since 2012 to date. We believe that this first review article in this field will give readers one-stop information on this topic and encourage further intriguing work in this area.


Assuntos
Acetofenonas , Iodo , Catálise , Metais , Oxirredução
2.
Biofouling ; 37(8): 922-937, 2021 09.
Artigo em Inglês | MEDLINE | ID: mdl-34615415

RESUMO

This study aimed to evaluate the mono- and dual- antifungal activities of paeonol (PAE) and fluconazole (FLZ)/amphotericin B (AmB). To this end, the effects of PAE and FLZ/AmB on cell surface hydrophobicity, hydrolase activity, morphological transition were investigated in vitro and in a Galleria mellonella infection model. The results showed a relatively high minimum inhibitory concentration (MIC) and sessile MIC (SMIC) of PAE alone. However, compared with the single drug, the combined use of PAE and FLZ/AmB had a potent synergistic potential to inhibit the virulence factors for Candida. The concomitant use of two drugs was consistently more effective than either drug alone for increasing survival rate, decreasing the fungal burden, and alleviating the pathological features of G. mellonella infected by the fungus. Taken together, these findings demonstrate the anti-Candida effects of PAE plus FLZ/AmB and their potential to increase the sensitivity of C. albicans to FLZ/AmB of PAE.


Assuntos
Anfotericina B , Fluconazol , Acetofenonas , Anfotericina B/farmacologia , Antifúngicos/farmacologia , Candida albicans , Fluconazol/farmacologia , Testes de Sensibilidade Microbiana , Virulência , Fatores de Virulência
3.
Phytochemistry ; 192: 112960, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34598045

RESUMO

Seven undescribed condensation derivatives of 4-isopropylbenzaldehyde with acetophenone, including one 1,3,5-trisubstituted pentane-1,5-dione, two 1,3,4,5,7-pentasubstituted heptane-1,7-diones and four 1,2,3,4,5-pentasubstituted cyclohexanols, together with two known flavonoids, were obtained from the red alga Laurencia tristicha. The relative configurations were elucidated by extensive spectroscopic data analysis of MS, 1D and 2D NMR, while the absolute configurations were determined by comparing the experimental and calculated electronic circular dichroism spectra. All the isolates were proven to be naturally occurring in the red alga by LC-MS analysis, and these 1,3,5-trisubstituted-pentane-1,5-dione, 1,3,4,5,7-pentasubstituted-heptane-1,7-diones and 1,2,3,4,5-pentasubstituted-cyclohexanols were reported from natural sources for the first time. The proposed biogenetic pathway of the isolates was also discussed.


Assuntos
Laurencia , Rodófitas , Acetofenonas , Espectroscopia de Ressonância Magnética , Estrutura Molecular
4.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3943-3948, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472271

RESUMO

The study aims to investigate the effect of the compatibility of paeonol and paeoniflorin(hereinafter referred to as the compatibility) on the expression of myocardial proteins in rats with myocardial ischemia injury and explore the underlying mechanism of the compatibility against myocardial ischemia injury. First, the acute myocardial infarction rat model was established by ligation of the anterior descending branch of the left coronary artery. The model rats were given(ig) paeonol and paeoniflorin. Then protein samples were collected from rat cardiac tissue and quantified by tandem mass tags(TMT) to explore the differential proteins after drug intervention. The experimental results showed that differential proteins mainly involved phagocytosis engulfment, extracellular space, and antigen binding, as well as Kyoto encyclopedia of genes and genomes(KEGG) pathways of complement and coagulation cascades, syste-mic lupus erythematosus, and ribosome. In this study, the target proteins and related signaling pathways identified by differential proteomics may be the biological basis of the compatibility against myocardial ischemia injury in rats.


Assuntos
Isquemia Miocárdica , Traumatismo por Reperfusão Miocárdica , Acetofenonas , Animais , Glucosídeos , Monoterpenos , Isquemia Miocárdica/tratamento farmacológico , Isquemia Miocárdica/genética , Proteômica , Ratos , Ratos Sprague-Dawley
5.
Int J Mol Sci ; 22(18)2021 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-34576127

RESUMO

Free radical-mediated activation of inflammatory macrophages remains ambiguous with its limitation to study within biological systems. U-937 and HL-60 cell lines serve as a well-defined model system known to differentiate into either macrophages or dendritic cells in response to various chemical stimuli linked with reactive oxygen species (ROS) production. Our present work utilizes phorbol 12-myristate-13-acetate (PMA) as a stimulant, and factors such as concentration and incubation time were considered to achieve optimized differentiation conditions. ROS formation likely hydroxyl radical (HO●) was confirmed by electron paramagnetic resonance (EPR) spectroscopy combined with confocal laser scanning microscopy (CLSM). In particular, U-937 cells were utilized further to identify proteins undergoing oxidation by ROS using anti-DMPO (5,5-dimethyl-1-pyrroline N-oxide) antibodies. Additionally, the expression pattern of NADPH Oxidase 4 (NOX4) in relation to induction with PMA was monitored to correlate the pattern of ROS generated. Utilizing macrophages as a model system, findings from the present study provide a valuable source for expanding the knowledge of differentiation and protein expression dynamics.


Assuntos
Diferenciação Celular , Radicais Livres/metabolismo , Monócitos/citologia , Monócitos/metabolismo , Proteínas/metabolismo , Acetofenonas/farmacologia , Diferenciação Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Forma Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Espectroscopia de Ressonância de Spin Eletrônica , Células HL-60 , Humanos , Radical Hidroxila , Monócitos/efeitos dos fármacos , NADP/metabolismo , Coloração e Rotulagem , Acetato de Tetradecanoilforbol/farmacologia , Células U937
6.
Chem Commun (Camb) ; 57(74): 9370-9373, 2021 Sep 16.
Artigo em Inglês | MEDLINE | ID: mdl-34528955

RESUMO

Herein, a framework for the estimation of the thermodynamic properties of molecular crystals via the refinement of frequencies from density functional theory calculations against X-ray diffraction data is presented. The framework provides an efficient approach to including the contribution of acoustic modes in the thermodynamic properties. The obtained heat capacities for urea, the α- and ß-glycine polymorphs, benzoic acid, and 4'-hydroxyacetophenone are in good agreement with those from adiabatic calorimetry.


Assuntos
Acetofenonas/química , Ácido Benzoico/química , Teoria da Densidade Funcional , Glicina/química , Calorimetria , Termodinâmica , Difração de Raios X
7.
Molecules ; 26(16)2021 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-34443598

RESUMO

Apocynin (APO) is a known multi-enzymatic complexed compound, employed as a viable NADPH oxidase (NOX) inhibitor, extensively used in both traditional and modern-day therapeutic strategies to combat neuronal disorders. However, its therapeutic efficacy is limited by lower solubility and lesser bioavailability; thus, a suitable nanocarrier system to overcome such limitations is needed. The present study is designed to fabricate APO-loaded polymeric nanoparticles (APO-NPs) to enhance its therapeutic efficacy and sustainability in the biological system. The optimized APO NPs in the study exhibited 103.6 ± 6.8 nm and -13.7 ± 0.43 mV of particle size and zeta potential, respectively, along with further confirmation by TEM. In addition, the antioxidant (AO) abilities quantified by DPPH and nitric oxide scavenging assays exhibited comparatively higher AO potential of APO-NPs than APO alone. An in-vitro release profile displayed a linear diffusion pattern of zero order kinetics for APO from the NPs, followed by its cytotoxicity evaluation on the PC12 cell line, which revealed minimal toxicity with higher cell viability, even after treatment with a stress inducer (H2O2). The stability of APO-NPs after six months showed minimal AO decline in comparison to APO only, indicating that the designed nano-formulation enhanced therapeutic efficacy for modulating NOX-mediated ROS generation.


Assuntos
Acetofenonas/química , Acetofenonas/farmacologia , Peróxido de Hidrogênio/farmacologia , NADPH Oxidases/metabolismo , Nanopartículas/química , Neurônios/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Animais , Sobrevivência Celular/efeitos dos fármacos , Neurônios/citologia , Neurônios/metabolismo , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/farmacologia , Células PC12 , Ratos
8.
Molecules ; 26(16)2021 Aug 17.
Artigo em Inglês | MEDLINE | ID: mdl-34443563

RESUMO

Paeonol is a naturally existing bioactive compound found in the root bark of Paeonia suffruticosa and it is traditionally used in Chinese medicine for the prevention and management of cardiovascular diseases. To date, a great deal of studies has been reported on the pharmacological effects of paeonol and its mechanisms of action in various diseases and conditions. In this review, the underlying mechanism of action of paeonol in cardiovascular disease has been elucidated. Recent studies have revealed that paeonol treatment improved endothelium injury, demoted inflammation, ameliorated oxidative stress, suppressed vascular smooth muscle cell proliferation, and repressed platelet activation. Paeonol has been reported to effectively protect the cardiovascular system either employed alone or in combination with other traditional medicines, thus, signifying it could be a hypothetically alternative or complementary atherosclerosis treatment. This review summarizes the biological and pharmacological activities of paeonol in the treatment of cardiovascular diseases and its associated underlying mechanisms for a better insight for future clinical practices.


Assuntos
Acetofenonas/farmacologia , Doenças Cardiovasculares/tratamento farmacológico , Acetofenonas/uso terapêutico , Animais , Doenças Cardiovasculares/metabolismo , Doenças Cardiovasculares/patologia , Doenças Cardiovasculares/fisiopatologia , Humanos
9.
Redox Biol ; 46: 102098, 2021 10.
Artigo em Inglês | MEDLINE | ID: mdl-34418601

RESUMO

Diabetes disrupts mitochondrial function and often results in diabetic cardiomyopathy (DCM). Paeonol is a bioactive compound that has been reported to have pharmacological potential for cardiac and mitochondrial protection. This study aims to explore the effects of paeonol on mitochondrial disorderes in DCM and the underlying mechanisms. We showed that paeonol promoted Opa1-mediated mitochondrial fusion, inhibited mitochondrial oxidative stress, and preserved mitochondrial respiratory capacity and cardiac performance in DCM in vivo and in vitro. Knockdown of Opa1 blunted the above protective effects of paeonol in both diabetic hearts and high glucose-treated cardiomyocytes. Mechanistically, inhibitor screening, siRNA knockdown and chromatin immunoprecipitation experiments showed that paeonol-promoted Opa1-mediated mitochondrial fusion required the activation of Stat3, which directly bound to the promoter of Opa1 to upregulate its transcriptional expression. Moreover, pharmmapper screening and molecular docking studies revealed that CK2α served as a direct target of paeonol that interacted with Jak2 and induced the phosphorylation and activation of Jak2-Stat3. Knockdown of CK2α blunted the promoting effect of paeonol on Jak2-Stat3 phosphorylation and Opa1-mediated mitochondrial fusion. Collectively, we have demonstrated for the first time that paeonol is a novel mitochondrial fusion promoter in protecting against hyperglycemia-induced mitochondrial oxidative injury and DCM at least partially via an Opa1-mediated mechanism, a process in which paeonol interacts with CK2α and restores its kinase activity that subsequently increasing Jak2-Stat3 phosphorylation and enhancing the transcriptional level of Opa1. These findings suggest that paeonol or the promotion of mitochondrial fusion might be a promising strategy for the treatment of DCM.


Assuntos
Diabetes Mellitus , Cardiomiopatias Diabéticas , Acetofenonas/farmacologia , Cardiomiopatias Diabéticas/tratamento farmacológico , Cardiomiopatias Diabéticas/genética , GTP Fosfo-Hidrolases/genética , GTP Fosfo-Hidrolases/metabolismo , Humanos , Dinâmica Mitocondrial , Simulação de Acoplamento Molecular , Fator de Transcrição STAT3/genética
10.
Life Sci ; 284: 119911, 2021 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-34450167

RESUMO

AIM: Male reproductive toxicity is becoming of growing significance due to clinical chemotherapy usage. Methotrexate (MTX) is an anti-folate used on a large scale for different tumors and autoimmune conditions. Despite its wide clinical use, MTX is associated with severe testicular intoxication. The exact underlying mechanism is unclear. METHODS: Our study was conducted to explore the pathogenesis mechanism of MTX-induced testicular damage and the potential testicular protective effects of apocynin (APO) on testicular injury induced by single i.p. MTX (20 mg/kg). APO was administered orally (100 mg/kg) for ten days. RESULTS: As compared to rats given MTX alone, co-administration of MTX with APO demonstrated multiple beneficial effects evidenced by a marked increase in testosterone, FSH, and LH and significantly restored testes histopathological alterations. Mechanistically, APO restored antioxidant status through up-regulation of Nrf2, cytoglobin, PPAR-γ, SIRT1, AKT, and p-AKT, while effectively lowering Keap-1. Moreover, APO significantly attenuated inflammation by down-regulating NF-κB-p65, iNOS, and TLR4 expressions confirmed by in-silico evidence. Additionally, network pharmacology analysis, a bioinformatics approach, was used to decipher various cellular processes' molecular mechanisms. SIGNIFICANCE: The current investigation proves the beneficial effects of APO in MTX-associated testicular damage through activation of cytoglobin, Keap-1/Nrf2/AKT, PPAR-γ, SIRT1, and suppressing of TLR4/NF-κB-p65 signal. Our data collectively encourage extending the investigation to the clinical setting to explore APO effects in MTX-treated patients.


Assuntos
Acetofenonas/farmacologia , Proteína 1 Associada a ECH Semelhante a Kelch/metabolismo , Metotrexato/efeitos adversos , Fator 2 Relacionado a NF-E2/metabolismo , NF-kappa B/metabolismo , Óxido Nítrico Sintase Tipo II/metabolismo , Testículo/patologia , Receptor 4 Toll-Like/metabolismo , Acetofenonas/química , Animais , Antioxidantes/metabolismo , Biomarcadores/metabolismo , Inflamação/patologia , Interleucina-6/metabolismo , Masculino , Simulação de Acoplamento Molecular , Óxido Nítrico/metabolismo , Oxidantes/metabolismo , Estresse Oxidativo/efeitos dos fármacos , PPAR gama/metabolismo , Peroxidase/metabolismo , Mapas de Interação de Proteínas/efeitos dos fármacos , Proteínas Proto-Oncogênicas c-akt/metabolismo , Ratos Sprague-Dawley , Transdução de Sinais/efeitos dos fármacos , Sirtuína 1/metabolismo , Testículo/efeitos dos fármacos , Testículo/metabolismo , Fator de Necrose Tumoral alfa/metabolismo
11.
Molecules ; 26(11)2021 Jun 02.
Artigo em Inglês | MEDLINE | ID: mdl-34199486

RESUMO

In this study, we aimed to design and synthesize novel molecules carrying both the thiazole and piperazine rings in their structures and to investigate their antinociceptive activity. Targeted compounds were obtained by reacting thiosemicarbazide derivative and appropriate 2-bromoacetophenone in ethanol. The structures of the obtained compounds were determined using data from various spectroscopic methods (IR, 1H-NMR, 13C-NMR, and LCMSMS). Experimental data from in vivo tests showed that test compounds 3a-3c, 3f, and 3g (50 mg/kg) significantly prolonged reaction times of animals in tail-clip and hot-plate tests compared to the controls, indicating that these compounds possess centrally mediated antinociceptive activities. Furthermore, these compounds reduced the number of writhing behaviors in the acetic acid-induced writhing tests, showing that the compounds also possess peripheral antinociceptive activity. In the mechanistic studies, naloxone pre-treatments abolished the antinociceptive activities of compounds 3a-3c, 3f, and 3g, indicating that opioidergic mechanisms were involved in their antinociceptive effects. Molecular docking studies demonstrating significant interactions between the active compounds and µ- and δ-opioid receptor proteins supported the pharmacological findings. This study is the first showing that molecules designed to bear thiazole and piperazine moieties together on their structure exert centrally and peripherally mediated antinociceptive effects by activating the opioid system.


Assuntos
Acetofenonas/química , Analgésicos/administração & dosagem , Analgésicos/síntese química , Dor/tratamento farmacológico , Receptores Opioides/metabolismo , Semicarbazidas/química , Analgésicos/química , Analgésicos/farmacologia , Animais , Modelos Animais de Doenças , Masculino , Camundongos , Modelos Moleculares , Simulação de Acoplamento Molecular , Estrutura Molecular , Naloxona/administração & dosagem , Naloxona/farmacologia , Dor/metabolismo , Conformação Proteica , Receptores Opioides/química , Receptores Opioides delta/química , Receptores Opioides delta/metabolismo , Receptores Opioides mu/química , Receptores Opioides mu/metabolismo
12.
Molecules ; 26(12)2021 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-34205355

RESUMO

Rottlerin is a natural product consisting of chalcone and flavonoid scaffolds, both of which have previously shown quorum sensing (QS) inhibition in various bacteria. Therefore, the unique rottlerin scaffold highlights great potential in inhibiting the QS system of Pseudomonas aeruginosa. Rottlerin analogues were synthesised by modifications at its chalcone- and methylene-bridged acetophenone moieties. The synthesis of analogues was achieved using an established five-step synthetic strategy for chalcone derivatives and utilising the Mannich reaction at C6 of the chromene to construct morpholine analogues. Several pyranochromene chalcone derivatives were also generated using aldol conditions. All the synthetic rottlerin derivatives were screened for QS inhibition and growth inhibition against the related LasR QS system. The pyranochromene chalcone structures displayed high QS inhibitory activity with the most potent compounds, 8b and 8d, achieving QS inhibition of 49.4% and 40.6% and no effect on bacterial growth inhibition at 31 µM, respectively. Both compounds also displayed moderate biofilm inhibitory activity and reduced the production of pyocyanin.


Assuntos
Acetofenonas/farmacologia , Benzopiranos/farmacologia , Produtos Biológicos/farmacologia , Percepção de Quorum/efeitos dos fármacos , Antibacterianos/farmacologia , Biofilmes/efeitos dos fármacos , Flavonoides/farmacologia , Testes de Sensibilidade Microbiana/métodos , Pseudomonas aeruginosa/efeitos dos fármacos , Piocianina/farmacologia
13.
Int J Mol Sci ; 22(13)2021 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-34281274

RESUMO

It has been recognized that serotonin 2A receptor (5-HT2A) agonist 2,5-dimethoxy-4-iodo-amphetamine (DOI) impairs serotonergic homeostasis. However, the mechanism of DOI-induced serotonergic behaviors remains to be explored. Moreover, little is known about therapeutic interventions against serotonin syndrome, although evidence suggests that ginseng might possess modulating effects on the serotonin system. As ginsenoside Re (GRe) is well-known as a novel antioxidant in the nervous system, we investigated whether GRe modulates 5-HT2A receptor agonist DOI-induced serotonin impairments. We proposed that protein kinase Cδ (PKCδ) mediates serotonergic impairments. Treatment with GRe or 5-HT2A receptor antagonist MDL11939 significantly attenuated DOI-induced serotonergic behaviors (i.e., overall serotonergic syndrome behaviors, head twitch response, hyperthermia) by inhibiting mitochondrial translocation of PKCδ, reducing mitochondrial glutathione peroxidase activity, mitochondrial dysfunction, and mitochondrial oxidative stress in wild-type mice. These attenuations were in line with those observed upon PKCδ inhibition (i.e., pharmacologic inhibitor rottlerin or PKCδ knockout mice). Furthermore, GRe was not further implicated in attenuation mediated by PKCδ knockout in mice. Our results suggest that PKCδ is a therapeutic target for GRe against serotonergic behaviors induced by DOI.


Assuntos
Ginsenosídeos/farmacologia , Proteína Quinase C-delta/metabolismo , Antagonistas da Serotonina/farmacologia , Síndrome da Serotonina/prevenção & controle , Acetofenonas/farmacologia , Anfetaminas/toxicidade , Animais , Comportamento Animal/efeitos dos fármacos , Comportamento Animal/fisiologia , Benzopiranos/farmacologia , Hipotálamo/efeitos dos fármacos , Hipotálamo/metabolismo , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Camundongos Knockout , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Piperidinas/farmacologia , Proteína Quinase C-delta/deficiência , Proteína Quinase C-delta/genética , Inibidores de Proteínas Quinases/farmacologia , Serotonina/fisiologia , Agonistas do Receptor de Serotonina/farmacologia , Síndrome da Serotonina/induzido quimicamente , Síndrome da Serotonina/fisiopatologia
14.
Int J Mol Sci ; 22(14)2021 Jul 12.
Artigo em Inglês | MEDLINE | ID: mdl-34299072

RESUMO

Five new compounds, eupatodibenzofuran A (1), eupatodibenzofuran B (2), 6-acetyl-8-methoxy-2,2-dimethylchroman-4-one (3), eupatofortunone (4), and eupatodithiecine (5), have been isolated from the aerial part of Eupatorium fortunei, together with 11 known compounds (6‒16). Compounds 1 and 2 featured a new carbon skeleton with an unprecedented 1-(9-(4-methylphenyl)-6-methyldibe nzo[b,d]furan-2-yl)ethenone. Among the isolates, compound 1 exhibited potent inhibitory activity with IC50 values of 5.95 ± 0.89 and 5.55 ± 0.23 µM, respectively, against A549 and MCF-7 cells. The colony-formation assay demonstrated that compound 1 (5 µM) obviously decreased A549 and MCF-7 cell proliferation, and Western blot test confirmed that compound 1 markedly induced apoptosis of A549 and MCF-7 cells through mitochondrial- and caspase-3-dependent pathways.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Eupatorium/química , Neoplasias/tratamento farmacológico , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Acetofenonas/química , Antineoplásicos Fitogênicos/química , Apoptose , Benzofuranos/química , Proliferação de Células , Cromonas/química , Humanos , Estrutura Molecular , Neoplasias/patologia , Relação Estrutura-Atividade , Células Tumorais Cultivadas
15.
J Chem Ecol ; 47(8-9): 777-787, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34287796

RESUMO

The "River Disease" (RD), a disorder impacting honeybee colonies located close to waterways with abundant riparian vegetation (including Sebastiania schottiana, Euphorbiaceae), kills newly hatched larvae. Forager bees from RD-affected colonies collect honeydew excretions from Epormenis cestri (Hemiptera: Flatidae), a planthopper feeding on trees of S. schottiana. First-instar honeybee larvae fed with this honeydew died. Thus, we postulated that the nectars of RD-affected colonies had a natural toxin coming from either E. cestri or S. schottiana. An untargeted metabolomics characterization of fresh nectars extracts from colonies with and without RD allowed to pinpoint xanthoxylin as one of the chemicals present in higher amounts in nectar from RD-affected colonies than in nectars from healthy colonies. Besides, xanthoxylin was also found in the aerial parts of S. schottiana and the honeydew excreted by E. cestri feeding on this tree. A larva feeding assay where xanthoxylin-enriched diets were offered to 1st instar larvae showed that larvae died in the same proportion as larvae did when offered enriched diets with nectars from RD-colonies. These findings demonstrate that a xenobiotic can mimic the RD syndrome in honeybee larvae and provide evidence of an interspecific flow of xanthoxylin among three trophic levels. Further, our results give information that can be considered when implementing measures to control this honeybee disease.


Assuntos
Acetofenonas/análise , Abelhas/fisiologia , Euphorbiaceae/química , Acetofenonas/farmacologia , Animais , Abelhas/crescimento & desenvolvimento , Dieta/veterinária , Análise Discriminante , Euphorbiaceae/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Larva/efeitos dos fármacos , Larva/fisiologia , Análise dos Mínimos Quadrados , Espectroscopia de Ressonância Magnética , Metabolômica/métodos , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Néctar de Plantas/química
16.
Food Chem ; 365: 130384, 2021 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-34237572

RESUMO

Acetylferulic paeonol ester (APE) and ferulic paeonol ester (FPE) were synthesized, and their structures were confirmed by NMR, mass spectra, IR and UV-vis data. The antioxidant properties of the synthesized compounds were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and [(2-azino-bis (3-ethylbenzthiazoline)-6 -sulfonic acid] (ABTS) assay as well as the production of oxidation products (peroxides, conjugated dienes, thiobarbituric acid-reactive substances, free fatty acids and total aldehydes) in an elevated temperature (60 °C) storage trial of fish oil extracted from anchovy. Furthermore, the changes in fatty acid composition were monitored by gas chromatography-mass spectrometry. The results showed that APE was more effective in restraining fish oil oxidation compared to FPE, ferulic acid, paeonol and the commercial antioxidant-butylated hydroxytoluene (BHT). This study demonstrated molecular combinations obtained by covalent bonding two antioxidant active molecules can result in novel compounds with enhanced antioxidant activities.


Assuntos
Antioxidantes , Óleos de Peixe , Acetofenonas , Hidroxitolueno Butilado , Ésteres
17.
Cutis ; 107(5): 238-240, 2021 May.
Artigo em Inglês | MEDLINE | ID: mdl-34288849

RESUMO

The American Contact Dermatitis Society chose acetophenone azine (AA) as the 2021 Allergen of the Year. Acetophenone azine is an emerging contact allergen that often is associated with the use of sports equipment and footwear. The pattern of dermatitis initially starts locally at the site of contact but can develop into a generalized dermatitis. Strong suspicion is necessary to diagnose AA allergy, and patch testing should be completed with AA and to potentially relevant sports equipment and/or shoes. Acetophenone azine is not yet available as a commercial patch-test preparation, but the optimal concentration is 0.1% in acetone or petrolatum. This column serves as an introduction to AA as an emerging allergen and highlights diagnosis, management, and patch testing for AA contact allergy.


Assuntos
Alérgenos , Dermatite Alérgica de Contato , Acetofenonas/efeitos adversos , Dermatite Alérgica de Contato/diagnóstico , Dermatite Alérgica de Contato/etiologia , Humanos , Testes do Emplastro , Equipamentos Esportivos , Estados Unidos
18.
Biomolecules ; 11(6)2021 06 15.
Artigo em Inglês | MEDLINE | ID: mdl-34203655

RESUMO

Anxiety disorders are common mental health diseases affecting up to 7% of people around the world. Stress is considered one of the major environmental risk factors to promote anxiety disorders through mechanisms involving epigenetic changes. Moreover, alteration in redox balance and increased reactive oxygen species (ROS) production have been detected in anxiety patients and in stressed-animal models of anxiety. Here we tested if the administration of apocynin, a natural origin antioxidant, may prevent the anxiety-like phenotype and reduction of histone acetylation induced by a subchronic forced swimming stress (FSS) paradigm. We found that apocynin prevented the enhanced latency time in the novelty-suppressed feeding test, and the production of malondialdehyde induced by FSS. Moreover, apocynin was able to block the upregulation of p47phox, a key subunit of the NADPH oxidase complex. Finally, apocynin prevented the rise of hippocampal Hdac1, Hdac4 and Hdac5, and the reduction of histone-3 acetylation levels promoted by FSS exposure. In conclusion, our results provide evidence that apocynin reduces the deleterious effect of stress and suggests that oxidative stress may regulate epigenetic mechanisms.


Assuntos
Acetofenonas/farmacologia , Transtornos de Ansiedade/enzimologia , Comportamento Animal/efeitos dos fármacos , Regulação Enzimológica da Expressão Gênica/efeitos dos fármacos , Hipocampo/enzimologia , Histona Desacetilases/biossíntese , Estresse Psicológico/enzimologia , Animais , Transtornos de Ansiedade/tratamento farmacológico , Transtornos de Ansiedade/fisiopatologia , Hipocampo/fisiopatologia , Masculino , Camundongos , Estresse Psicológico/tratamento farmacológico , Estresse Psicológico/fisiopatologia
19.
Biofouling ; 37(6): 666-679, 2021 07.
Artigo em Inglês | MEDLINE | ID: mdl-34320877

RESUMO

Paeonol, the active ingredient of Paeonia lactiflora root bark, is widely used in traditional Chinese medicine. Few studies have reported the antibacterial activity of paeonol against bacterial pathogens. In this study, the antibacterial and anti-biofilm performance of paeonol against Klebsiella pneumoniae and Enterobacter cloacae was investigated as well as its mechanisms of action. Paeonol effectively inhibited the growth of K. pneumoniae and E. cloacae with a minimum inhibitory concentration of 64 µg ml-1 and it was shown to disrupt the integrity of bacterial cell membranes, and alter cell morphology. Moreover, paeonol exhibited a potent inhibitory effect against adhesion and biofilm formation by K. pneumoniae and E. cloacae. In particular, paeonol efficiently compromised cells within biofilms, and dispersed mature biofilms. Therefore, the present study suggests that paeonol is a promising alternative antibacterial and anti-biofilm agent for combating infections caused by planktonic and biofilm cells of K. pneumoniae and E. cloacae.


Assuntos
Enterobacter cloacae , Klebsiella pneumoniae , Acetofenonas , Antibacterianos/farmacologia , Biofilmes , Testes de Sensibilidade Microbiana
20.
Inorg Chem ; 60(12): 9192-9198, 2021 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-34105956

RESUMO

2-Aminoacetophenone (2-AA) is a metabolite produced in large quantities by the pathogenic bacteria Pseudomonas aeruginosa (PA), which is a biomarker for PA in water. State-of-the-art analytical techniques to detect PA usually require expensive instruments and a long analysis time which are not suitable for real-time water quality monitoring, especially for high-quality drinking water. Herein, we reported the application of a europium metal-organic framework (Eu-MOF) as a luminescent sensing material, which provides a facile, environmentally friendly and low-cost way for the fast detection of PA in water. Eu-MOF shows a high sensitivity toward 2-AA with a KSV value of 3.563 × 104 M-1, rapid luminescence response in 12 s and high-selectivity and anti-interference ability with the existence of common detection indexes in drinking water owing to the good match of the energy levels of Eu-MOF and 2-AA. A systematical optimization of the sensing conditions to enhance the sensing function of Eu-MOF for 2-AA was discussed in detail, to give fundamentals for the rational design of MOF-based sensing materials.


Assuntos
Acetofenonas/análise , Európio/química , Estruturas Metalorgânicas/química , Pseudomonas aeruginosa/química , Água/química , Biomarcadores/análise , Estruturas Metalorgânicas/síntese química
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