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1.
Artigo em Chinês | MEDLINE | ID: mdl-35545602

RESUMO

Allyl alcohol is an intermediate widely used in industrial production activities, which has caused many occupational damage in China. In this paper, the data of a case of skin damage and clinical cure of inhalation pneumonia caused by occupational allyl alcohol exposure were analyzed and summarized. The patient accidentally inhaled large amounts of allyl alcohol at work and had skin exposure, which was mainly manifested as aspiration pneumonia, respiratory failure, eye damage and skin bullae. After short-term hormone shock therapy, mechanical ventilation, infection prevention, local treatment and other comprehensive treatment, the patient was clinically cured. This case suggests that chemical pneumonia and respiratory failure may be caused by inhalation of allyl alcohol, and skin bullae may be caused by skin contact. Early treatment and hormone use should be emphasized.


Assuntos
Pneumonia , Insuficiência Respiratória , Vesícula , Hormônios , Humanos , Propanóis
3.
Chem Commun (Camb) ; 58(37): 5578-5581, 2022 May 05.
Artigo em Inglês | MEDLINE | ID: mdl-35436779

RESUMO

Allylic alcohol epoxidation and dehydrogenation reactivity is distinguished when VO(acac)2 is used in solution or anchored in a metal-organic framework (MOF). The chemical mechanism depends on the electronic profile of alkene substituents when the vanadyl complex is used in the homogenous phase. However, confinement effects imparted by MOF channels allow gaining control of the chemoselectivity toward the dehydrogenation product.


Assuntos
Estruturas Metalorgânicas , Catálise , Compostos de Epóxi , Propanóis
4.
J Chem Ecol ; 48(4): 347-358, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35366125

RESUMO

We describe the identification and field testing of 3-methylthiopropan-1-ol (methionol) as a male-produced aggregation-sex pheromone for the cerambycid beetle Knulliana cincta cincta (Drury) (subfamily Cerambycinae, tribe Bothriospilini). The corresponding sulfoxide, 3-methylsulfinylpropan-1-ol, was also produced sex-specifically by males, but its function remains unclear because the measured release rates of this compound from five different types of release devices were very low to undetectable. Unexpectedly, adults of the cerambycine Elaphidion mucronatum (Say) (Elaphidiini), primarily females, also were attracted by methionol, despite males of this species producing an aggregation-sex pheromone of entirely different structure, (2E,6Z,9Z)-2,6,9-pentadecatrienal.


Assuntos
Besouros , Atrativos Sexuais , Animais , Feminino , Masculino , América do Norte , Feromônios , Propanóis , Atrativos Sexuais/química , Sulfetos , Enxofre
5.
Inorg Chem ; 61(13): 5326-5334, 2022 Apr 04.
Artigo em Inglês | MEDLINE | ID: mdl-35311288

RESUMO

The B(9)-H halogenation of o-carborane and m-carborane was achieved with excellent selectivities in hexafluoroisopropanol (HFIP) under simple reaction conditions: single reagent [trichloroisocyanuric acid (TCCA), tribromoisocyanuric acid (TBCA) or N-iodosuccinimide (NIS)], catalyst-free, air-/moisture-tolerant, and convenient work-up. With this method, a variety of 9-halogenated o-carboranes and m-carboranes were obtained in good to excellent yields with broad tolerance of functional groups.


Assuntos
Boranos , Catálise , Halogenação , Hidrocarbonetos Fluorados , Propanóis
6.
Food Res Int ; 152: 110898, 2022 02.
Artigo em Inglês | MEDLINE | ID: mdl-35181075

RESUMO

The widespread presence of 3-monochloropropane-1,2-diol (3-MCPD) and glycidol in refined edible oils have raised food industrial and public health concerns, but their specific biomarkers of exposure and urinary metabolic pathways indicating nephrotoxicity remain largely unknown. Here, we unraveled the in vivo biotransformation of these two contaminants and revealed how they affect metabolic pathways in rats. Urine metabolomes in rats administered with glycidol or 3-MCPD were investigated using ultra-high performance liquid chromatography combined with a quadrupole-orbitrap high-resolution mass spectrometry. Compared to the currently acknowledged metabolite which is only 2,3-dihydroxypropyl mercapturic acid, we identified 8 and 4 new specific exposure biomarkers of glycidol and 3-MCPD, respectively, via mapping the glyceryl polymerization and glutathione and sulfur conjugation. The changes of metabolites in the surrounding metabolic network were investigated to further gain insight into their metabolic fates. Exposure to glycidol up-regulated citrate, isocitrate, ketoglutarate, malate, and pyruvate in the tricarboxylic acid cycle and glycolysis pathways, while 3-MCPD intake down-regulated these signal molecules in both pathways. Nonetheless, L-cysteine, proline, and arginine were significantly decreased by the effect of either glycidol or 3-MCPD. Our findings first map the urinary metabolomics of both contaminants from edible oils and advance the omics-level recognition for their observational health hazards.


Assuntos
alfa-Cloridrina , Acetilcisteína/análogos & derivados , Animais , Compostos de Epóxi , Óleos Vegetais/química , Propanóis , Ratos , Toxicocinética , alfa-Cloridrina/análise , alfa-Cloridrina/toxicidade
7.
J Dairy Sci ; 105(5): 4064-4082, 2022 May.
Artigo em Inglês | MEDLINE | ID: mdl-35221072

RESUMO

The objective of this study was to investigate whether the CH4 mitigation potential of 3-nitrooxypropanol (3-NOP) in dairy cattle was affected by basal diet (BD) composition. The experiment involved 64 Holstein-Friesian dairy cows (146 ± 45 d in milk at the start of trial; mean ± SD) in 2 overlapping crossover trials, each consisting of 2 measurement periods. Cows were blocked according to parity, d in milk, and milk yield, and randomly allocated to 1 of 3 diets: a grass silage-based diet (GS) consisting of 30% concentrates and 70% grass silage (DM basis), a grass silage- and corn silage-mixed diet (GSCS) consisting of 30% concentrates, 42% grass silage, and 28% corn silage (DM basis), or a corn silage-based diet (CS) consisting of 30% concentrates, 14% grass silage, and 56% corn silage (DM basis). Two types of concentrates were formulated, viz. a concentrate for the GS diet and a concentrate for the CS diet, to meet the energy and protein requirements for maintenance and milk production. The concentrate for the GSCS diet consisted of a 50:50 mixture of both concentrates. Subsequently, the cows within each type of BD received 2 treatments in a crossover design: either 60 mg of 3-NOP/kg of DM (NOP60) and a placebo with 0 mg of 3-NOP/kg of DM (NOP0) in one crossover or 80 mg of 3-NOP/kg of DM (NOP80) and NOP0 in the other crossover. Diets were provided as total mixed ration in feed bins, which automatically recorded feed intake. Additional concentrate was fed in the GreenFeed system that was used to measure emissions of CH4 and H2. The CS diets resulted in a reduced CH4 yield (g/kg DMI) and CH4 intensity (g/kg milk). Feeding 3-NOP resulted in a decreased DMI. Milk production and composition did not differ between NOP60 and NOP0, whereas milk yield and the yield of major components decreased for NOP80 compared with NOP0. Feed efficiency was not affected by feeding 3-NOP. Interactions between BD and supplementation of 3-NOP were observed for the production (g/d) and yield (g/kg DMI) of both CH4 and H2, indicating that the mitigating effect of 3-NOP depended on the composition of the BD. Emissions of CH4 decreased upon 3-NOP supplementation for all BD, but the decrease in CH4 emissions was smaller for GS (-26.2% for NOP60 and -28.4% for NOP80 in CH4 yield) compared with both GSCS (-35.1% for NOP60 and -37.9% for NOP80 for CH4 yield) and CS (-34.8% for NOP60 and -41.6% for NOP80 for CH4 yield), with no difference between the latter 2 BD. Emissions of H2 increased upon 3-NOP supplementation for all BD, but the H2 yield (g/kg DMI) increased 3.16 and 3.30-fold, respectively, when NOP60 and NOP80 were supplemented to GS, and 4.70 and 4.96 fold, respectively, when NOP60 and NOP80 were supplemented to CS. In conclusion, 3-NOP can effectively decrease CH4 emissions in dairy cows across diets, but the level of CH4 mitigation is greater when supplemented in a corn silage-based diet compared with a grass silage-based diet.


Assuntos
Lactação , Metano , Animais , Bovinos , Dieta/veterinária , Feminino , Poaceae/metabolismo , Gravidez , Propanóis , Silagem/análise , Zea mays/metabolismo
8.
Molecules ; 27(3)2022 Jan 21.
Artigo em Inglês | MEDLINE | ID: mdl-35163964

RESUMO

The forensic toxicologist is challenged to provide scientific evidence to distinguish the source of ethanol (antemortem ingestion or microbial production) determined in the postmortem blood and to properly interpret the relevant blood alcohol concentration (BAC) results, in regard to ethanol levels at death and subsequent behavioral impairment of the person at the time of death. Higher alcohols (1-propanol, 1-butanol, isobutanol, 2-methyl-1-butanol (isoamyl-alcohol), and 3-methyl-2-butanol (amyl-alcohol)) are among the volatile compounds that are often detected in postmortem specimens and have been correlated with putrefaction and microbial activity. This brief review investigates the role of the higher alcohols as biomarkers of postmortem, microbial ethanol production, notably, regarding the modeling of postmortem ethanol production. Main conclusions of this contribution are, firstly, that the higher alcohols are qualitative and quantitative indicators of microbial ethanol production, and, secondly that the respective models of microbial ethanol production are tools offering additional data to interpret properly the origin of the ethanol concentrations measured in postmortem cases. More studies are needed to clarify current uncertainties about the origin of higher alcohols in postmortem specimens.


Assuntos
Álcoois/análise , Autopsia/métodos , Etanol/análise , Toxicologia Forense/métodos , Concentração Alcoólica no Sangue , Butanóis , Etanol/sangue , Humanos , Pentanóis , Mudanças Depois da Morte , Propanóis
9.
J Org Chem ; 87(5): 3804-3809, 2022 03 04.
Artigo em Inglês | MEDLINE | ID: mdl-35041421

RESUMO

Prochiral racemic allylic alcohols are converted to enantioenriched chiral alcohols bearing adjacent stereocenters catalyzed by a diamine diphosphine Ru complex in the presence of tBuOK. The protocol features a broad substrate scope (56 examples) and high diastereo- and enantioselectivities (up to >99:1 dr, >99% ee) and could be applied to the synthesis of enantioenriched chromane and indane compounds. Mechanistic studies suggest that the reaction proceeds via tBuOK-promoted allylic alcohol isomerization followed by Ru-catalyzed hydrogenative dynamic kinetic resolution.


Assuntos
Álcoois , Catálise , Hidrogenação , Isomerismo , Propanóis , Estereoisomerismo
10.
Environ Res ; 209: 112746, 2022 06.
Artigo em Inglês | MEDLINE | ID: mdl-35063427

RESUMO

In this study, we investigated the association of 2,3-dihydroxypropyl mercapturic acid (DHPMA), a urinary biomarker of environmental and dietary exposure to 3-monochloropropane-1,2-diol and glycidol, with prevalent MetS in a Chinese middle-aged and elderly population. The urinary DHPMA concentrations were determined by ultra-high performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS) analysis and further calibrated by the urinary creatinine content. MetS cases were defined by the Adult Treatment Panel III criteria for Asian-Americans of National Cholesterol Education Program (NCEP/ATPIII). Multivariate-adjusted modified Poisson regression models were used to analyze the associations between the urinary DHPMA concentrations and MetS prevalence. Of the 1613 participants aged 45-75 years, we documented 552 (34.2%) MetS cases. After adjustment for potential risk factors, the relative risks (95% confidence intervals) of MetS prevalence across the increasing quartiles of DHPMA concentrations were 1.14 (0.93-1.39), 1.29 (1.06-1.56), and 1.50 (1.25-1.80), respectively, compared with the lowest quartile. We also observed strong positive association between urinary DHPMA concentrations and hypertriglyceridemia prevalence (P < 0.001 for trend). These positive associations remained unchanged in the subgroups stratified by general demographic, dietary and behavioral risk factors. These results suggested that urinary DHPMA was associated with higher prevalence of MetS among Chinese elderly people.


Assuntos
Síndrome Metabólica , alfa-Cloridrina , Acetilcisteína/análogos & derivados , Adulto , Idoso , Compostos de Epóxi , Humanos , Síndrome Metabólica/epidemiologia , Pessoa de Meia-Idade , Prevalência , Propanóis , Fatores de Risco , Espectrometria de Massas em Tandem/métodos
11.
Appl Environ Microbiol ; 88(6): e0190821, 2022 03 22.
Artigo em Inglês | MEDLINE | ID: mdl-35080908

RESUMO

3-Nitrooxypropanol (3-NOP) is effective at reducing ruminal methane emissions in ruminants. But it also causes a drastic increase in hydrogen accumulation, resulting in feed energy waste. Fumarate is a key precursor for propionate formation and plays an important role in rumen hydrogen metabolism. Therefore, this study examined the effects of 3-NOP combined with fumarate on volatile fatty acids, methanogenesis, and microbial community structures in dairy cows in vitro. The in vitro culture experiment was performed using a 2-by-2 factorial design, two 3-NOP levels (0 or 2 mg/g dry matter [DM]) and two fumarate levels (0 or 100 mg/g DM), including 3 runs with 4 treatments, 4 replicates, and 4 blanks containing only the inoculum. Rumen fluid was collected from three lactating Holstein cows with permanent ruminal fistulas. The combination of 3-NOP and fumarate reduced methane emissions by 11.48% without affecting dry matter degradability. The propionate concentration increased and the acetate/propionate ratio decreased significantly. In terms of bacteria, the combination of 3-NOP and fumarate reduced the abundances of Ruminococcus and Lachnospiraceae_NK3A20_group and increased the abundances of Prevotella and Succiniclasticum. For archaea, the combination of 3-NOP and fumarate significantly increased the abundances of Methanobrevibacter_sp._AbM4, while the abundance of operational taxonomic unit 581 (OTU581) (belonging to an uncultured_rumen_methanogen_g__Methanobrevibacter strain) was significantly decreased. These results indicated that the combination of 3-NOP and fumarate could alleviate the accumulation of hydrogen and enhance the inhibition of methanogenesis compared with 3-NOP only in dairy cows. IMPORTANCE The global problem of climate change and the greenhouse effect has become increasingly severe, and the abatement of greenhouse gases has received great attention from the international community. Methane produced by ruminants during digestion not only aggravates the greenhouse effect but also causes a waste of feed energy. As a methane inhibitor, 3-nitrooxypropanol can effectively reduce methane emissions from ruminants. However, when it inhibits methane emissions, the emission of hydrogen increases sharply, resulting in the waste of feed resources. Fumarate is a propionic acid precursor that can promote the metabolism of hydrogen to propionic acid in animals. Therefore, we studied the effects of the combined addition of 3-nitrooxypropanol and fumarate on methanogenesis, rumen fermentation, and rumen flora. It is of great significance to inhibit methane emission from ruminants and slow down the greenhouse effect.


Assuntos
Lactação , Rúmen , Ração Animal/análise , Animais , Bovinos , Dieta/veterinária , Feminino , Fermentação , Fumaratos/metabolismo , Fumaratos/farmacologia , Metano/metabolismo , Leite/metabolismo , Propanóis , Propionatos/metabolismo , Propionatos/farmacologia , Rúmen/metabolismo
12.
Molecules ; 27(1)2022 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-35011551

RESUMO

Tomato is an economically crucial vegetable/fruit crop globally. Tomato is rich in nutrition and plays an essential role in a healthy human diet. Phenylpropanoid, a critical compound in tomatoes, reduces common degenerative and chronic diseases risk caused by oxidative stress. As an MYB transcription factor, ATMYB12 can increase phenylpropanoid content by activating phenylpropanoid synthesis related genes, such as PAL, C4H, 4CL, CHS. However, the heterologous expression of AtMYB12 in tomatoes can be altered through transgenic technologies, such as unstable expression vectors and promoters with different efficiency. In the current study, the efficiency of other fruit-specific promoters, namely E8S, 2A12, E4, and PG, were compared and screened, and we determined that the expression efficiency of AtMYB12 was driven by the E8S promoter was the highest. As a result, the expression of phenylpropanoid synthesis related genes was regulated by AtMYB12, and the phenylpropanoid accumulation in transgenic tomato fruits increased 16 times. Additionally, the total antioxidant capacity of fruits was measured through Trolox equivalent antioxidant capacity (TEAC) assay, which was increased by 2.4 times in E8S transgenic lines. TEAC was positively correlated with phenylpropanoid content. Since phenylpropanoid plays a crucial role in the human diet, expressing AtMYB12 with stable and effective fruit-specific promoter E8S could improve tomato's phenylpropanoid and nutrition content and quality. Our results can provide genetic resources for the subsequent improvement of tomato varieties and quality, which is significant for human health.


Assuntos
Frutas/genética , Frutas/metabolismo , Regulação da Expressão Gênica de Plantas , Lycopersicon esculentum/fisiologia , Regiões Promotoras Genéticas , Propanóis/metabolismo , Fatores de Transcrição/genética , Vias Biossintéticas , Cromatografia Líquida de Alta Pressão , Especificidade de Órgãos/genética , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo
13.
Chem Res Toxicol ; 35(2): 283-292, 2022 02 21.
Artigo em Inglês | MEDLINE | ID: mdl-35044764

RESUMO

Despite the increasing popularity of e-cigarettes, their long-term health effects remain unknown. In animal models, exposure to e-cigarette has been reported to result in pulmonary and cardiovascular injury, and in humans, the acute use of e-cigarettes increases heart rate and blood pressure and induces endothelial dysfunction. In both animal models and humans, cardiovascular dysfunction associated with e-cigarettes has been linked to reactive aldehydes such as formaldehyde and acrolein generated in e-cigarette aerosols. These aldehydes are known products of heating and degradation of vegetable glycerin (VG) present in e-liquids. Here, we report that in mice, acute exposure to a mixture of propylene glycol:vegetable glycerin (PG:VG) or to e-cigarette-derived aerosols significantly increased the urinary excretion of acrolein and glycidol metabolites─3-hydroxypropylmercapturic acid (3HPMA) and 2,3-dihydroxypropylmercapturic acid (23HPMA)─as measured by UPLC-MS/MS. In humans, the use of e-cigarettes led to an increase in the urinary levels of 23HPMA but not 3HPMA. Acute exposure of mice to aerosols derived from PG:13C3-VG significantly increased the 13C3 enrichment of both urinary metabolites 13C3-3HPMA and 13C3-23HPMA. Our stable isotope tracing experiments provide further evidence that thermal decomposition of vegetable glycerin in the e-cigarette solvent leads to generation of acrolein and glycidol. This suggests that the adverse health effects of e-cigarettes may be attributable in part to these reactive compounds formed through the process of aerosolizing nicotine. Our findings also support the notion that 23HPMA, but not 3HPMA, may be a relatively specific biomarker of e-cigarette use.


Assuntos
Acroleína/química , Sistemas Eletrônicos de Liberação de Nicotina , Compostos de Epóxi/química , Aromatizantes/química , Propanóis/química , Acroleína/metabolismo , Acroleína/urina , Aerossóis/química , Animais , Biomarcadores , Cromatografia Líquida de Alta Pressão , Compostos de Epóxi/metabolismo , Compostos de Epóxi/urina , Aromatizantes/metabolismo , Masculino , Espectrometria de Massas , Camundongos , Camundongos Endogâmicos C57BL , Propanóis/metabolismo , Propanóis/urina , Solventes , Vaping
14.
ChemSusChem ; 15(4): e202102441, 2022 Feb 18.
Artigo em Inglês | MEDLINE | ID: mdl-34978379

RESUMO

Although the use of light stimulating organic transformations has been known for more than a century, there is an increasing research interest on expanding the established knowledge. While [2+2] cycloadditions are promoted photochemically, literature precedent on the reaction between alkynes and maleimides is limited and only a handful of examples exist, focusing mainly on N-aliphatic maleimides. Herein, the differences in reactivity between N-alkyl and N-aryl maleimides were identified, and the use of hexafluoroisopropanol (HFIP) or trifluoroacetic acid (TFA) as viable solutions was proposed in order to achieve high yields. In the case of N-alkyl maleimides, both HFIP-mediated or TFA-promoted reactions were established using LED 370 nm irradiation, without the use of an external photocatalyst. In the case of N-aryl maleimides, thioxanthone (THX) was employed as the energy transfer photocatalyst along with LED 427 nm irradiation and HFIP. Mechanistic studies were performed, supporting the pivotal role of HFIP or TFA, in acquiring good to high yields in both classes of maleimides.


Assuntos
Alcinos , Propanóis , Reação de Cicloadição , Hidrocarbonetos Fluorados , Maleimidas
15.
J Org Chem ; 87(2): 1086-1097, 2022 01 21.
Artigo em Inglês | MEDLINE | ID: mdl-35015536

RESUMO

The regio- and chemoselective construction of indole bearing an all-carbon center at the C3-position, a versatile bioactive building block, by C(sp2)-C(sp3) formation with olefins has been achieved through utilization of hexafluoroisopropanol (HFIP) as the protonation reagent and solvent. The catalytic reactions are operationally simple and green compared with previous reports utilizing elaborated olefins and catalysts. This protocol allows for alkylation of a variety of substituted indoles with diverse of styrene type alkenes in excellent yields and with high selectivity. Application of this protocol to the synthesis of drug was pursued and with an improved yield in contrast to previous art. Catalytic kinetics and deuterium-labeling experiments suggest that the rate-determining step involves the protonation of olefin by HFIP to generate carbocation, followed by electrophilic addition to indole derivative.


Assuntos
Carbono , Indóis , Alquilação , Hidrocarbonetos Fluorados , Indicadores e Reagentes , Propanóis , Solventes
16.
Chemphyschem ; 23(1): e202100620, 2022 01 05.
Artigo em Inglês | MEDLINE | ID: mdl-34632686

RESUMO

Binary mixtures of hexafluoroisopropanol with either methanol or acetone are analyzed via classical molecular dynamics simulations and quantum cluster equilibrium calculations. In particular, their populations and thermodynamic properties are investigated with the binary quantum cluster equilibrium method, using our in-house code Peacemaker 2.8, upgraded with temperature-dependent parameters. A novel approach, where the final density from classical molecular dynamics, has been used to generate the necessary reference isobars. The hydrogen bond network in both type of mixtures at molar fraction of hexafluoroisopropanol of 0.2, 0.5, and 0.8 respectively is investigated via the molecular dynamics trajectories and the cluster results. In particular, the populations show that mixed clusters are preferred in both systems even at 0.2 molar fractions of hexafluoroisopropanol. Enthalpies and entropies of vaporization are calculated for the neat and mixed systems and found to be in good agreement with experimental values.


Assuntos
Metanol , Simulação de Dinâmica Molecular , Acetona , Análise por Conglomerados , Hidrocarbonetos Fluorados , Ligação de Hidrogênio , Propanóis , Termodinâmica , Volatilização
18.
J Org Chem ; 87(1): 613-627, 2022 01 07.
Artigo em Inglês | MEDLINE | ID: mdl-34904438

RESUMO

Herein, a highly regioselective domino skeletal-expansion process that transforms 2-aminothiazolidinone into six-membered S,N-heterocycle is developed with the aid of TMS-azide in hexafluoroisopropanol (HFIP) at ambient temperature. Functioning of the C2 tertiary amine as latent reactive group on thiazolidinone moiety was the key to this development, which allowed relay substitution with azide and imparted subsequent ring-expansion under metal/acid free-conditions. The reaction also underscored an intermolecular nitrogen-atom transfer process from TMS-azide leading to final products, where any intermediary azidothiazolidinone was absent. The strategy was extendable to analogous synthesis of Se,N-heterocycles, and furthermore, late-stage drug-modification and follow-up transformations were also performed. Density functional theory calculations and control experiments provided important mechanistic insights and highlighted potential roles of HFIP in the transformation.


Assuntos
Nitrogênio , Propanóis , Catálise , Hidrocarbonetos Fluorados , Temperatura
19.
Genes (Basel) ; 12(11)2021 10 29.
Artigo em Inglês | MEDLINE | ID: mdl-34828340

RESUMO

Excessive aluminum ions (Al3+) in acidic soil can have a toxic effect on watermelons, restricting plant growth and reducing yield and quality. In this study, we found that exogenous application of nitric oxide (NO) could increase the photochemical efficiency of watermelon leaves under aluminum stress by promoting closure of leaf stomata, reducing malondialdehyde and superoxide anion in leaves, and increasing POD and CAT activity. These findings showed that the exogenous application of NO improved the ability of watermelon to withstand aluminum stress. To further reveal the mitigation mechanism of NO on watermelons under aluminum stress, the differences following different types of treatments-normal growth, Al, and Al + NO-were shown using de novo sequencing of transcriptomes. In total, 511 differentially expressed genes (DEGs) were identified between the Al + NO and Al treatment groups. Significantly enriched biological processes included nitrogen metabolism, phenylpropane metabolism, and photosynthesis. We selected 23 genes related to antioxidant enzymes and phenylpropane metabolism for qRT-PCR validation. The results showed that after exogenous application of NO, the expression of genes encoding POD and CAT increased, consistent with the results of the physiological indicators. The expression patterns of genes involved in phenylpropanoid metabolism were consistent with the transcriptome expression abundance. These results indicate that aluminum stress was involved in the inhibition of the photosynthetic pathway, and NO could activate the antioxidant enzyme defense system and phenylpropane metabolism to protect cells and scavenge reactive oxygen species. This study improves our current understanding by comprehensively analyzing the molecular mechanisms underlying NO-induced aluminum stress alleviation in watermelons.


Assuntos
Alumínio/metabolismo , Alumínio/toxicidade , Citrullus/efeitos dos fármacos , Citrullus/fisiologia , Óxido Nítrico/farmacologia , Estresse Fisiológico/efeitos dos fármacos , Transcriptoma , Fenômenos Biológicos/efeitos dos fármacos , Regulação da Expressão Gênica de Plantas/efeitos dos fármacos , Genes de Plantas , Nitrogênio/metabolismo , Fotossíntese/efeitos dos fármacos , Folhas de Planta/metabolismo , Raízes de Plantas/metabolismo , Propanóis/metabolismo , Solo/química
20.
Org Biomol Chem ; 19(45): 9906-9909, 2021 11 25.
Artigo em Inglês | MEDLINE | ID: mdl-34734958

RESUMO

The copper-catalyzed substitution reaction of diethyl phosphate derived from TMSCCCH(OH)CH2CH2OTBDPS with 3-c-C5H9-4-MeOC6H3MgBr, followed by several transformations, afforded a tumor necrosis factor inhibitor possessing a Ph-acetylene moiety. The inhibitor was also synthesized from phenylacetylene phosphate PhCCCH(OP(O)(OEt)2)CH2CH2OTBDPS. Furthermore, the substitution of phosphates derived from TMSCCCH(OH)CH3 and TMSCCCH(OH)-i-Pr with 3-F-4-PhC6H3MgBr gave the corresponding substitution products, which were transformed to flurbiprofen and its i-Pr analogue, respectively. The copper-catalyzed substitutions in these syntheses proceeded in a regio- and stereoselective manner.


Assuntos
Alcinos/química , Cobre/química , Flurbiprofeno/síntese química , Indicadores e Reagentes/química , Propanóis/química , Fator de Necrose Tumoral alfa/antagonistas & inibidores , Catálise , Flurbiprofeno/química , Flurbiprofeno/farmacologia , Estereoisomerismo
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