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1.
Int J Mol Sci ; 24(2)2023 Jan 10.
Artigo em Inglês | MEDLINE | ID: mdl-36674844

RESUMO

Piper sarmentosum Roxb. (Piperaceae) is a traditional medicinal plant in South-East Asian countries. The chemical investigation of leaves from this species resulted in the isolation of three previously not described compounds, namely 4″-(3-hydroxy-3-methylglutaroyl)-2″-ß-D-glucopyranosyl vitexin (1), kadukoside (2), and 6-O-trans-p-coumaroyl-D-glucono-1,4-lactone (3), together with 31 known compounds. Of these known compounds, 21 compounds were isolated for the first time from P. sarmentosum. The structures were established by 1D and 2D NMR techniques and HR-ESI-MS analyses. The compounds were evaluated for their anthelmintic (Caenorhabditis elegans), antifungal (Botrytis cinerea, Septoria tritici and Phytophthora infestans), antibacterial (Aliivibrio fischeri) and cytotoxic (PC-3 and HT-29 human cancer cells lines) activities. Methyl-3-(4-methoxyphenyl)propionate (8), isoasarone (12), and trans-asarone (15) demonstrated anthelmintic activity with IC50 values between 0.9 and 2.04 mM. Kadukoside (2) was most active against S. tritici with IC50 at 5.0 µM and also induced 94% inhibition of P. infestans growth at 125 µM. Trans-asarone (15), piperolactam A (23), and dehydroformouregine (24) displayed a dose-dependent effect against B. cinerea from 1.5 to 125 µM up to more than 80% inhibition. Paprazine (19), cepharadione A (21) and piperolactam A (23) inhibited bacterial growth by more than 85% at 100 µM. Only mild cytotoxic effects were observed.


Assuntos
Derivados de Alilbenzenos , Piper , Humanos , Piper/química , Anisóis , Extratos Vegetais/farmacologia , Extratos Vegetais/química
2.
Braz J Biol ; 83: e269245, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-36629625

RESUMO

The present study sought to evaluate the antibacterial activity of trans-anethole against food-borne strains of Enterobacter cloacae and Enterococcus faecalis. The study was performed using Minimum Inhibitory Concentration (MIC), and Minimum Bactericidal Concentration (MBC) methods, in addition, disc diffusion technique was used to evaluate the association of trans-anethole with synthetic antimicrobials. Minimum Inhibitory Concentration for Adherence (MICA) testing was also performed. The results revealed that trans-anethole presents no antibacterial activity at any of the concentrations used against the E. cloacae strains tested. However, trans-anethole presented antibacterial effect against five of the six E. faecalis bacterial strains tested, with MIC values ranging from 500 µg/mL to 1000 µg/mL. Further, when analyzing the MBC results against E. faecalis, it was observed that the compound presented values ranging from 500 µg/mL to 1000 µg/mL. As for the associations, it was observed that trans-anethole when combined with the antimicrobials ampicillin, gentamicin, ciprofloxacin, and ceftriaxone presented synergistic effect against most strains of E. faecalis. However, both trans-anethole and the control chlorhexidine (0.12%) presented no antibiofilm effects against strains of E. faecalis. In short, trans-anethole presented potential antibacterial against E. faecalis strains of food origin, and may upon further study, it may be used alone or in association with synthetic antimicrobials to combat infections caused by this bacterium.


Assuntos
Anti-Infecciosos , Enterococcus faecalis , Enterococcus , Antibacterianos/farmacologia , Anisóis/farmacologia , Anti-Infecciosos/farmacologia , Testes de Sensibilidade Microbiana
3.
J Agric Food Chem ; 71(1): 884-894, 2023 Jan 11.
Artigo em Inglês | MEDLINE | ID: mdl-36584355

RESUMO

α-Asarone (αA) and ß-asarone (ßA) are often used as flavoring agents for alcoholic beverages and food supplements. They possess a double bond in the side chain with different configurations. Double bonds are a class of alert chemical group, due to their metabolic epoxidation to the corresponding epoxides eliciting liver injury. Little is known about changes of configuration on metabolic activation and related toxicity. Here, we report the insight into the mechanisms of hepatotoxicity of asarone with different configurations. In vitro and in vivo comparative studies demonstrated ßA displayed higher metabolic activation effectiveness. Apparently, the major metabolic pathway of ßA underwent epoxidation at C-1' and C-2', while αA was mainly metabolized to the corresponding alcohol resulting from the hydroxylation of C-3'. CYP1A2 dominated the metabolism of αA and ßA. The molecular simulation studies showed that the orientation of ßA at the active site of CYP1A2 favored the epoxidation of ßA over that of αA. These findings not only remind us that configuration is another important factor for toxicities but also facilitate the understanding of the mechanisms of toxic action of asarone. Additionally, these findings would benefit the risk assessment of αA and ßA exposure from foods.


Assuntos
Derivados de Alilbenzenos , Anisóis , Doença Hepática Induzida por Substâncias e Drogas , Humanos , Derivados de Alilbenzenos/toxicidade , Anisóis/toxicidade , Doença Hepática Induzida por Substâncias e Drogas/etiologia , Citocromo P-450 CYP1A2
4.
Sci Rep ; 12(1): 22217, 2022 12 23.
Artigo em Inglês | MEDLINE | ID: mdl-36564541

RESUMO

Β-asarone is a phenylpropane derivative present in the rhizomes of Acorus calamus, that was proved to exhibit toxic effects in humans. Because of its presence the whole plant that is commonly used in traditional medicine for its sedative, anti-inflammatory, neuroprotective and other properties has limited application nowadays. In the study, qualitative and quantitative analysis of a collection of nine essential oil (EO) samples of European and Asian origin was performed. The final content of ß-asarone in the tested samples ranged between 0.265 and 1.885 mg/mL. Having in mind a possible application of the EO as a biopesticide, this research aimed at the development of CPC-based purification protocol that could help remove ß-asarone from EO. It was proved that the biphasic solvent system composed of n-hexane/EtOAc/MeOH/water, 9:1:9:1 (v/v/v/v) was capable of the removal of the toxic constituent in the CPC chromatograph operated in the ascending elution mode with 2200 rpm and a flow rate of 5 mL/min. The chromatographic analysis that lasted only 144 min effectively separated ß-asarone (purity of 95.5%) and α-asarone (purity of 93.7%) directly from the crude Acorus calamus rhizome EO.


Assuntos
Acorus , Óleos Voláteis , Humanos , Óleos Voláteis/química , Anisóis/química , Cromatografia Líquida
5.
Molecules ; 27(24)2022 Dec 17.
Artigo em Inglês | MEDLINE | ID: mdl-36558147

RESUMO

Melt-cast explosive 2,4-dinitroanisole (DNAN) crystal and its cocrystals DNAN/1,3-dinitrobenzene (DNB) and DNAN/2-nitroaniline (NA) were used to identify the effects of cocrystallization on the crystal structure, non-covalent interactions, and melting points of the DNAN crystal through density functional theory and molecular dynamics. The components DNB and NA with subtle structure variations between the nitro group and amino group can significantly affect the non-covalent interactions, especially the π-π stacking and H-bonds, which can lead to different crystal stacking styles. The melting points of the DNAN crystal are decreased through the cocrystallization, which expands the utilization of the DNAN-based melt cast explosives. Our study deciphers the effects caused by the cocrystallization on the structure and properties of melt cast explosives and may help to design and optimize novel melt-cast explosives.


Assuntos
Substâncias Explosivas , Substâncias Explosivas/química , Anisóis/química , Compostos de Anilina
6.
Dalton Trans ; 51(43): 16668-16680, 2022 Nov 08.
Artigo em Inglês | MEDLINE | ID: mdl-36278834

RESUMO

trans-Anethole (trans-AN) is widely applied in food, daily necessities, and pharmaceuticals and is typically available from inefficient natural oil extraction or complex organic transformations over mineral acid or noble metals. Here, a green and sustainable route was developed to stereoselectively produce trans-AN (ca. 90% selectivity) over an organic polymeric phosphonate-hafnium catalyst (PAS-Hf) through the cascade transfer hydrogenation and dehydration of biomass-based 4'-methoxypropiophenone (4-MOPP), with an environmental impact factor (E-factor) of 47.73. The porous structure and the enhanced hydrophobicity of the spherical catalyst PAS-Hf ensured the formation of more accessible and stable Lewis (Hf4+) and Brønsted (SO3H) acid active sites, which could be used for rapid conversion of biomass-based 4-MOPP to AN (100% conversion, 97.2% yield) in 0.5-2 h (TOF: 9.3 h-1). Density functional theory (DFT) calculations elucidated that the addition of PAS-Hf could remarkably facilitate the overall conversion process by decreasing the reaction energy barrier (151.33 to 48.27 kJ mol-1) of the rate-determining step. The good thermal stability and heterogeneity of the bifunctional catalyst were responsible for its constant activity during at least five consecutive cycles. The synergistic/relay catalysis of Lewis acid-base and Brønsted acid species could be extended to more than ten kinds of aldehydes and ketones. This acid-base multi-catalytic protocol has considerable potential in cascade biomass conversion via heterogeneous catalysis without any base additive.


Assuntos
Derivados de Alilbenzenos , Catálise , Anisóis , Bases de Lewis , Interações Hidrofóbicas e Hidrofílicas
7.
Molecules ; 27(19)2022 Sep 26.
Artigo em Inglês | MEDLINE | ID: mdl-36234876

RESUMO

Agastache rugosa (baechohyang) is one of the most important aromatic plants native to the Republic of Korea. A. rugosa fragrance has been used to prepare incense since the Goryeo Dynasty in Korea. The present study aimed to explore the variation in the composition of essential oils from A. rugosa among native populations in Korea. The seeds of A. rugosa were collected from 90 different sites in Korea and seedlings were raised in the nursery. Essential oils were extracted from these populations by the steam distillation extraction method and their chemical compositions were analyzed by GC-MS. The yield of essential oils of A. rugosa ranged between 0.11% and 0.86%. A total of 204 components were identified from 90 populations of A. rugosa. Out of 204 components, 32 components were common in more than 40 individuals of A. rugosa and these 32 components were selected for principal component analysis (PCA). On the basis of the essential oil compositions, six chemotypes-estragole, pulegone, methyl eugenol, menthone, isopulegone, and nepetalactone-were distinguished according to their major components. As a result of the cluster analysis, 90 individuals of A. rugosa could be classified into three groups: estragole, methyl eugenol, and pulegone. A. rugosa exhibited significant chemical diversity among the individuals. The distribution of chemotypes is associated with the collection of seeds, suggesting that genetic diversity may influence the variations in the chemical compositions and concentrations within the species. This chemical diversity serves as the background to select cultivars for the cultivation and industrial applications of A. rugosa cultivars with high essential oil yield and concentration of its chemical components.


Assuntos
Agastache , Mentha , Óleos Voláteis , Agastache/química , Derivados de Alilbenzenos , Anisóis , Monoterpenos Cicloexânicos , Eugenol/análogos & derivados , Humanos , Óleos Voláteis/química , Vapor
8.
Int J Mol Sci ; 23(18)2022 Sep 09.
Artigo em Inglês | MEDLINE | ID: mdl-36142377

RESUMO

Bemisia tabaci is a threat to agriculture worldwide because of its potential to cause devastating damage to various crops. ß-asarone is a bioactive pesticidal chemical originating from Acorus calamus (or "Sweet Flag") plants, and it displays significant lethal effects against insect pests. In this study, we established a baseline of susceptibility to ß-asarone from China and patterns of cross-resistance to other popular insecticides. We found that all the 12 field-collected B. tabaci populations exhibited high susceptibility to ß-asarone, and there was no cross-resistance detected for other tested insecticides. We subsequently evaluated the sublethal effects of ß-asarone on physiology and biochemistry via LC25 treatment (4.7 mg/L). LC25 of ß-asarone resulted in prolonged developmental duration and decreased survival rates in B. tabaci nymphs, pseudopupae, and adults. Significant reductions in oviposition duration, fecundity, and hatchability were also observed. Additionally, the metabolic enzyme activity and expression profiles of selected cytochrome P450 monooxygenase (P450) genes following the LC25 treatment of ß-asarone suggest that enhanced detoxification via P450s could be involved in the observed sublethal effects. These findings demonstrate the strong toxicity and significant sublethal effects of ß-asarone on B. tabaci and suggest that the induced overexpression of P450 genes could be associated with the response to ß-asarone.


Assuntos
Derivados de Alilbenzenos , Hemípteros , Inseticidas , Animais , Anisóis , Sistema Enzimático do Citocromo P-450/genética , Sistema Enzimático do Citocromo P-450/metabolismo , Feminino , Hemípteros/genética , Resistência a Inseticidas/genética , Inseticidas/farmacologia
9.
Chemosphere ; 308(Pt 2): 136421, 2022 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-36108757

RESUMO

Anisole (methoxybenzene) represents an important marker compound of lignin pyrolysis and a starting material for many chemical products. In this study, secondary organic aerosols (SOA) formed by anisole via various atmospheric processes, including homogeneous photooxidation with varying levels of OH• and NOx and subsequent heterogeneous NO3• dark reactions, were investigated. The yields of anisole SOA, particle-bound organoperoxides, particle-induced oxidative potential (OP), and cytotoxicity were characterized in view of the atmospheric fate of the anisole precursor. Anisole SOA yields ranged between 0.12 and 0.35, depending on the reaction pathways and aging degrees. Chemical analysis of the SOA suggests that cleavage of the benzene ring is the main reaction channel in the photooxidation of anisole to produce low-volatility, highly oxygenated small molecules. Fresh anisole SOA from OH• photooxidation are more light-absorbing and have higher OP and organoperoxide content. The high correlation between SOA OP and organoperoxide content decreases exponentially with the degree of OH• aging. However, the contribution of organoperoxides to OP is minor (<4%), suggesting that other, non-peroxide oxidizers play a central role in anisole SOA OP. The particle-induced OP and particulate organoperoxides yield both reach a maximum value after ∼2 days' of photooxidation, implicating the potential long impact of anisole during atmospheric transport. NOx-involved photooxidation and nighttime NO3• reactions facilitate organic nitrate formation and enhance particle light absorption. High NOx levels suppress anisole SOA formation and organoperoxides yield in photooxidation, with decreased aerosol OP and cellular oxidative stress. In contrast, nighttime aging significantly increases the SOA toxicity and reactive oxygen species (ROS) generation in lung cells. These dynamic properties and the toxicity of anisole SOA advocate consideration of the complicated and consecutive aging processes in depicting the fate of VOCs and assessing the related effects in the atmosphere.


Assuntos
Poluentes Atmosféricos , Nitratos , Aerossóis/análise , Poluentes Atmosféricos/análise , Anisóis/análise , Anisóis/toxicidade , Benzeno/análise , Lignina/análise , Nitratos/química , Oxirredução , Espécies Reativas de Oxigênio/análise
10.
Eur Rev Med Pharmacol Sci ; 26(17): 6344-6350, 2022 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-36111936

RESUMO

OBJECTIVE: Alzheimer's disease (AD) is a neurological ailment that causes memory loss and impairments and is linked to a drop-in acetylcholine level. Acetylcholinesterase (AChE) inhibitors are used for the management of AD. In our ongoing research to search for natural AChE inhibitors from medicinal plants, we found that the Acorus calamus possesses memory-enhancing properties. α-Asarone is the major compound isolated from the Acorus calamus and it has neuroprotective action in animal models, nonetheless, its anticholinesterase activity in different brain regions was not fully understood. The purpose of this research was to determine the anti-amnesic and anti-cholinesterase activities of α-asarone against scopolamine-induced memory impairments in rats. MATERIALS AND METHODS: The anti-cholinesterase activity of α-asarone was determined using Ellman's method in different brain areas, such as the cortex, hippocampus, and striatum. In addition, the anti-amnesic effect of α-asarone was also investigated using elevated plus-maze, passive avoidance, and active avoidance tests. RESULTS: The effect of α-asarone on memory impairment against scopolamine-induced (1 mg/kg body weight) amnesia was evaluated. Administration of α-asarone (15 and 30 mg/kg body weight) for 14 days to rats significantly ameliorated the scopolamine-induced memory impairment as measured in the elevated plus-maze, passive avoidance, and avoidance active tests compared to the scopolamine-treated group. In this study, we also show that α-asarone treatment significantly (p<0.05) reduced brain acetylcholinesterase activity in the cortex, hippocampus, and striatum brain regions of amnesic rats. CONCLUSIONS: These results confirmed that α-asarone has anti-amnesic and anti-cholinesterase potential which may be useful for the management of AD.


Assuntos
Derivados de Alilbenzenos , Doença de Alzheimer , Amnésia , Anisóis , Inibidores da Colinesterase , Transtornos da Memória , Escopolamina , Acetilcolina/metabolismo , Acetilcolinesterase/metabolismo , Derivados de Alilbenzenos/farmacologia , Doença de Alzheimer/induzido quimicamente , Doença de Alzheimer/tratamento farmacológico , Amnésia/induzido quimicamente , Amnésia/tratamento farmacológico , Animais , Anisóis/farmacologia , Aprendizagem da Esquiva , Peso Corporal , Inibidores da Colinesterase/farmacologia , Aprendizagem em Labirinto , Transtornos da Memória/induzido quimicamente , Transtornos da Memória/tratamento farmacológico , Ratos , Escopolamina/efeitos adversos
11.
Chem Biol Interact ; 366: 110129, 2022 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-36067825

RESUMO

In the present work, dehydrodieugenol B (1) and its methyl ether (2), isolated from Nectandra leucantha twigs, were used as starting material for the preparation of two new derivatives (1a and 2a) containing an additional methoxycarbonyl unit on allyl side chains. Compounds 1a and 2a demonstrated activity against trypomastigotes (EC50 values of 13.5 and 23.0 µM, respectively) and against intracellular amastigotes (EC50 values of 10.2 and 6.1 µM, respectively). Additionally, compound 2a demonstrated no mammalian cytotoxicity up to 200 µM whereas compound 1a exhibited a CC50 value of 139.8 µM. The mechanism of action studies of compounds 1a and 2a demonstrated a significant depolarization of the plasma membrane potential in trypomastigotes, followed by a mitochondrial membrane potential collapse. Neither calcium level nor reactive oxygen species alterations were observed after a short-time incubation. Considering the potential of compound 2a against T. cruzi and its simple preparation from the natural product 2, isolated from N. leucantha, this compound could be considered a new hit for future drug design studies in Chagas disease.


Assuntos
Produtos Biológicos , Doença de Chagas , Trypanosoma cruzi , Anisóis/metabolismo , Produtos Biológicos/metabolismo , Cálcio/metabolismo , Membrana Celular/metabolismo , Humanos , Potencial da Membrana Mitocondrial , Espécies Reativas de Oxigênio/metabolismo , Trypanosoma cruzi/metabolismo
12.
Water Res ; 224: 119046, 2022 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-36096026

RESUMO

Thermally activated peroxydisulfate In Situ Chemical Oxidation (TAP-ISCO) is often applied for the remediation of soil-sorbed hydrophobic organic contaminants (HOCs) and nonaqueous phase liquids (NAPLs), which act as long-term sources of groundwater contamination. TAP-ISCO benefits from improved desorption/dissolution of organic contaminants into the aqueous phase and efficient activation of peroxydisulfate at elevated temperatures, but the primary limitation of TAP-ISCO is the short lifetime of peroxydisulfate (therefore the availability of reactive radical species). To resolve this problem, coupling of peroxide stabilizers with TAP were tested. The compatibility of seven representative commercial organic and inorganic peroxide stabilizers, including sodium stannate, trisodium phosphate, sodium pyrophosphate, sodium silicate, sodium citrate, ethylene diamine tetra methylene phosphonic acid and ethylenediaminetetraacetic acid disodium salt, with TAP in aqueous solutions and solutions containing goethite or soil particles were first studied. The effects of stabilizers on the formation, distribution and reactivity of reactive oxygen species were then investigated through electron paramagnetic resonance (EPR) spin-trapping experiments using 5,5-dimethyl-1-pyrroline-N-oxide, chemical probe experiments using anisole, nitrobenzene and hexachloroethane, and biphasic trichloroethylene (TCE) dense nonaqueous phase liquids (DNAPLs) TAP-ISCO mimicking experiments. The results indicate that organic stabilizers significantly accelerate peroxydisulfate decomposition at both ambient and elevated temperatures. In contrast, inorganic stabilizers can markedly increase peroxydisulfate longevity by suppressing the acid-catalyzed peroxydisulfate decomposition, quenching radical-chain acceleration, and sequestering transition metal species. In addition, TAP systems containing inorganic stabilizers can effectively generate a variety of reactive radical species, including SO4•-, HO•, and O2•-, and improve the oxidation of anisole and nitrobenzene, though suppressing the reduction of hexachloroethane to some extent. Especially, suitable inorganic stabilizers (e.g., trisodium phosphate) can effectively improve TAP oxidation of TCE DNAPL while suppressing peroxydisulfate decomposition. Overall, this study provides the fundamental basis of coupling TAP-ISCO with peroxide stabilizers.


Assuntos
Tricloroetileno , Poluentes Químicos da Água , Anisóis , Ácido Edético , Etano/análogos & derivados , Etilenos , Hidrocarbonetos Clorados , Nitrobenzenos , Oxirredução , Peróxidos/química , Fosfatos , Espécies Reativas de Oxigênio/química , Sódio , Citrato de Sódio , Solo/química , Tricloroetileno/química , Poluentes Químicos da Água/química
13.
Med Oncol ; 39(12): 243, 2022 Sep 30.
Artigo em Inglês | MEDLINE | ID: mdl-36180656

RESUMO

Esophageal cancer is one of the most common malignancies which induces cancer-related death. Cancer metastasis and recurrence are the main obstacle faced in esophageal cancer treatment. ß-Asarone has been shown to act as an anti-cancer reagent in various cancer types. However, the anti-cancer activities of ß-Asarone in esophageal cancer have not been shown. In the current study, we show that ß-Asarone suppressed the proliferation of esophageal squamous cancer cells (ESCC) in both dose- and time-dependent manners. Moreover, ß-Asarone treatment increases activated caspase 3, caspase 9, and cleaved poly ADP-ribose polymerase, and induces apoptosis in ESCC. Additionally, ß-Asarone also suppresses epithelial-mesenchymal transition (EMT) and the invasive and migratory abilities in ESCC. Interestingly, ß-Asarone suppresses TGF-ß/Smad signaling by inhibition of TGF-ß-induced phosphorylation of Smad2 and Smad3. Importantly, we show that inhibition of TGF-ß/Smad signaling activation is critical for ß-Asarone-suppressed EMT. Our data revealed a novel role of ß-Asarone which targets invasive properties by inhibiting TGF-ß/Smad signaling activation in ESCC. Our study suggests the potential application of ß-Asarone to reduce cancer metastasis and recurrence in esophageal cancer treatment.


Assuntos
Carcinoma de Células Escamosas , Neoplasias Esofágicas , Adenosina Difosfato Ribose , Derivados de Alilbenzenos , Anisóis , Carcinoma de Células Escamosas/tratamento farmacológico , Carcinoma de Células Escamosas/patologia , Caspase 3 , Caspase 9 , Linhagem Celular Tumoral , Movimento Celular , Transição Epitelial-Mesenquimal , Neoplasias Esofágicas/tratamento farmacológico , Neoplasias Esofágicas/patologia , Humanos , Proteínas Smad/metabolismo , Fator de Crescimento Transformador beta/metabolismo , Fator de Crescimento Transformador beta1/metabolismo , Fator de Crescimento Transformador beta1/farmacologia
14.
Artigo em Inglês | MEDLINE | ID: mdl-35997563

RESUMO

The use of deep eutectic solvents (DESs) has great prospects because of the green and efficient characteristics, which can be used for developing analytical methods for foods. In this research, assisted by ultrasonic waves, a liquid-liquid microextraction detection method combined with gas chromatography was established for three anaesthetics (eugenol, isoeugenol, and methyl isoeugenol) in aquatic food. The processing conditions including the components, ratio of hydrogen bond acceptor and hydrogen bond donor, DES volume, ultrasonic time, and pH were evaluated and optimised to improve the extraction efficiency, which was based on the DES structures and properties. In-house method validation was carried out by applying to real samples. A Thymol: levulinic acid DES (with a molar ratio of 1:2) was used as the extractant and the recoveries were as high as 93-101% for eugenol, 90-100% for methyl isoeugenol, and 86-94% for isoeugenol with RSDs <5% under optimum conditions. The limit of detection and quantification of the eugenol compounds were 0.08-0.10 µg/mL and 0.26-0.33 µg/mL, respectively. The method has green credentials and comparable LOD to homologous apparatus, which can be used for the determination of eugenol components in aquatic food.


Assuntos
Microextração em Fase Líquida , Anisóis , Cromatografia Líquida de Alta Pressão/métodos , Solventes Eutéticos Profundos , Eugenol/análogos & derivados , Interações Hidrofóbicas e Hidrofílicas , Limite de Detecção , Microextração em Fase Líquida/métodos , Solventes/química , Timol , Ultrassom
15.
J Pharm Biomed Anal ; 220: 114992, 2022 Oct 25.
Artigo em Inglês | MEDLINE | ID: mdl-35985134

RESUMO

Sweet fennel (Foeniculum vulgare Mill. var. dulce) and thyme (Zataria multiflora Boiss.) are regarded as the important supplies for pharmaceutical, food, cosmetic, and perfume industries. The major components trans-anethole and thymol are represented in fennel and thyme, respectively. The essential oils (EOs) content and the value of their related constituents should be given in strict quality control due to the storage conditions, source, and adulterations. In this study, we compared the validation of quantitative 1H NMR (qH NMR) method with the gas chromatography with flame ionization detection (GC-FID) to quantify the trans-anethole and thymol in fennel and thyme EOs and their related supplements. The current results showed that the quantification of trans-anethole and thymol by qH NMR method was successfully achieved from their EOs and supplements. All the validation parameters including linearity, robustness, repeatability, and stability were authenticated for thymol and trans-anethole quantification. Similar results were obtained in both qH NMR and conventional GC-FID methods. Therefore, according to the measured values, the qH NMR method was adequate to determine the constituents of the EOs, with the results being roughly comparable to those obtained by GC-FID, with the advantage of being simple, repeatable, rapid (8-10 min, while for GC-FID 55 min) and essential for quality control of commercial samples.


Assuntos
Foeniculum , Óleos Voláteis , Perfumes , Thymus (Planta) , Derivados de Alilbenzenos , Anisóis , Cromatografia Gasosa , Ionização de Chama , Foeniculum/química , Óleos Voláteis/química , Perfumes/análise , Extratos Vegetais/química , Timol/análise
16.
Phytomedicine ; 105: 154363, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-35926378

RESUMO

BACKGROUND: Secondary brain injury (SBI) has been confirmed as a leading cause for the poor prognosis of patients suffering from intracerebral hemorrhage (ICH). SBI co-exists in ischemia and hemorrhagic stroke. Neuro-excitotoxicity is considered the initiating factor of ICH-induced SBI. Our previous research has revealed alpha-asarone (ASA)'s efficacy against cerebral ischemia-reperfusion stroke by mitigating neuro-excitotoxicity. It is not yet known if ASA exhibit neuroprotection against ICH. PURPOSE: This work aimed to investigate ASA's therapeutic effects and potential mechanisms of action against ICH in a classic rat model induced by collagenase Ⅶ injection. METHODS: An in vivo ICH model of Sprague-Dawley rats was established by collagenase Ⅶ injection. We administrated different ASA doses (10, 20, or 40 mg/kg, i.p.) at 2 h post-ICH. Then, rats' short- and long-term neurobehavioral function, bodyweight change, and learning and memory ability were blindly evaluated. Histological, Nissl, and flow cytometry were applied to assess the neuronal damage post-ICH. The wet/dry method and Evans blue extravasation estimated brain edema and blood-brain barrier function. Pathway-related proteins were investigated by immunofluorescence staining, enzyme-linked immunosorbent assay, and Western-blot analysis. RESULTS: The results demonstrated that ASA ameliorated neurological deterioration, bodyweight loss, and learning and memory ability of ICH rats. Histological, Nissl, and flow cytometry analyses showed that ASA reduced neuronal damage and apoptosis post-ICH. Besides, ASA probably mitigated brain edema and blood-brain barrier dysfunction via inhibiting astrocyte activation and consequent pro-inflammatory response. The mechanism investigation attributed ASA's efficacy to the following aspects: 1) promoting sodium ion excretion, thus blocking excitatory signal transduction along the axon; 2) preventing glutamate-involved pathways, i.e., decrease of N-methyl-d-aspartic acid receptor subunit 2B, increase of glutamate transporter-1, and alleviation of calcium-related cascades, mitochondrion-associated apoptosis, and neuronal autophagy; 3) enhancing the expression of GABAARs, thus abating neuronal excitotoxicity. CONCLUSION: Our study first confirmed the effect of ASA on ameliorating the neurobehavioral deterioration of ICH rats, possibly via alleviation of glutamate-involved neuro-excitotoxicity, i.e., calcium cascades, mitochondrion-involved apoptosis, neuronal autophagy, and astrocyte-related inflammation. These findings not only provided a promising drug candidate for clinical treatment of ICH but also shed light on the future drug discovery against ICH.


Assuntos
Edema Encefálico , Lesões Encefálicas , Derivados de Alilbenzenos , Animais , Anisóis , Apoptose , Cálcio , Hemorragia Cerebral , Modelos Animais de Doenças , Glutamatos , Ratos , Ratos Sprague-Dawley
17.
Molecules ; 27(16)2022 Aug 22.
Artigo em Inglês | MEDLINE | ID: mdl-36014580

RESUMO

Natural product (E)-anethole was isomerized to (Z)-anethole in a photocatalytic reaction. For this purpose, a self-designed cheap photoreactor was constructed. Among 11 photosensitizers (organo and metal complex compounds), Ir(p-tBu-ppy)3 led to the highest conversion. Triplet energies of (E)- and (Z)-anethole were predicted theoretically by DFT calculations to support the selection of appropriate photosensitizers. A catalyst loading of 0.1 mol% gave up to 90% conversion in gram scale. Further additives were not required and mild irradiation with light of 400 nm overnight was sufficient. As a proof of concept, (E)- and (Z)-anethole were dihydroxylated diastereoselectively to obtain diastereomerically pure like- and unlike-configured diols, respectively.


Assuntos
Derivados de Alilbenzenos , Fármacos Fotossensibilizantes , Anisóis , Isomerismo
18.
J Agric Food Chem ; 70(36): 11412-11418, 2022 Sep 14.
Artigo em Inglês | MEDLINE | ID: mdl-36039915

RESUMO

The Rio defect is a coffee off-flavor associated to unpleasant medicinal, phenolic, and iodine-like notes. 2,4,6-Trichloroanisole (TCA) is the main marker of this alteration. A new approach for TCA detection in green coffee beans was evaluated using chemical ionization time-of-flight mass spectrometry and employing a Vocus ion source and ion-molecule reactor (IMR). The sample set consisted of 22 green Coffea arabica from different geographical origins, four of which presented the Rio defect according to an expert cup-tasting panel. Vocus CI-MS was able to perform TCA detection in 3 s, with a sensitivity comparable to that of a sensory panel and showed remarkably good correlation (R2 ≥ 0.9997) with SPME-GC-MS measurements carried out on coffee headspace and hydro-alcoholic extracts. The results demonstrate how the introduction of new quick and sensitive analytical tools could help provide a more comprehensive picture of the Rio coffee off-flavor.


Assuntos
Coffea , Anisóis , Coffea/química , Cromatografia Gasosa-Espectrometria de Massas , Sementes/química
19.
Molecules ; 27(14)2022 Jul 19.
Artigo em Inglês | MEDLINE | ID: mdl-35889486

RESUMO

Trichloroanisole (TCA) in wine results in a sensory defect called "cork taint", a significant problem for the wine industry. Wines can become contaminated by TCA absorption from the atmosphere through contaminated wood barrels, cork stoppers, and wood pallets. Air-depleted solvent-impregnated (ADSI) cork powder (CP) was used to mitigate TCA in wines. The ADSI CP (0.25 g/L) removed 91% of TCA (6 ng/L levels), resulting in an olfactory activity value of 0.14. A Freundlich isotherm described ADSI CP TCA adsorption with irreversible adsorption and a KF = 33.37. ADSI CP application had no significant impact on the phenolic profile and chromatic characteristics of red wine. Using headspace sampling with re-equilibration, an average reduction in the volatile abundance of 29 ± 15%, 31 ± 19%, and 37 ± 24% was observed for the 0.10, 0.25, and 0.50 g/L ADSI CP, respectively. The alkyl esters and acids were the most affected. The impact observed was much lower when using headspace sampling without re-equilibration. Isoamyl acetate, ethyl hexanoate, ethyl hexanoate, and ethyl decanoate abundances were not significantly different from the control wine and 0.25 g/L ADSI CP application. Thus, ADSI CP can be a new sustainable fining agent to remove this "off-flavor" from wine, with a reduced impact on the wine characteristics.


Assuntos
Vinho , Anisóis/análise , Pós , Solventes , Vinho/análise
20.
Parasitol Int ; 90: 102620, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-35792323

RESUMO

Mosquitoes are potent vectors by serving as agents to life-threatening diseases in humans. Increasing resistance in mosquitoes against existing insecticides and repellents brings new challenges and an opportunity to explore sustainable compounds. We chose six medicinal plants to screen potential bioactive compounds that could act as an insecticide. Among these, crude hexane leaf extract of Acorus calamus showed higher mortality percentage against Aedes aegypti and Culex quinquefasciatus. The LC50 and LC90 values were 151.86 ppm and 536.36 ppm, respectively, for the third instar A. aegypti larvae, and 174.70 ppm and 696.73 ppm, respectively, for C. quinquefasciatus. The treated larvae of both species showed morphological and physiological variations when compared to control. The GC-MS profile of purified fractions showed a single peak. Further, FT-IR and NMR analyses confirmed the propensity of the purified compound as trans asarone (phenylpropanoid; C12H16O3. LC50 and LC90 values of purified asasone-treated larvae were 2.35 ppm and 12.58 ppm, respectively, for A. aegypti and 2.15 ppm and 11.58 ppm, respectively, for C. quinquefasciatus. Treatment of different sub-lethal doses of asarone to mosquito larvae at various time intervals showed disruption of intestinal layers. By showing negligible toxicity to non-target organism, purified asarone has a great potential in vector management.


Assuntos
Acorus , Aedes , Anopheles , Culex , Inseticidas , Derivados de Alilbenzenos , Animais , Anisóis , Humanos , Inseticidas/química , Inseticidas/farmacologia , Larva , Mosquitos Vetores , Extratos Vegetais/química , Folhas de Planta , Espectroscopia de Infravermelho com Transformada de Fourier
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