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1.
Chemosphere ; 357: 141915, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38582162

RESUMO

Standard OECD tests are used to generate data on biodegradation (OECD 307) and sorption (OECD 106) of test chemicals in soil. In such tests, data on abiotic degradation using sterile samples are utilised to investigate any losses due to abiotic processes. The data from sterile samples are also used to interpret results and findings of non-sterile samples, especially in the context of sorption and non-extractable residue (NER) formation. However, to ensure the comparability of the data obtained from sterile and non-sterile experiments, effects of sterilisation on the soil matrix should be minimal. The objective of this study was to investigate the efficiencies of different sterilisation techniques and the impact of the sterilisation on sorption and NER formation in soil. In this study, experiments in accordance with OECD 307 and OECD 106 guidelines were performed with two soils covering wide range of soil characteristics and treated with the three sterilisation techniques autoclaving, gamma(γ)-radiation and adding 1% (w/w) sodium azide. As a test item, 14C-labelled phenanthrene and bromoxynil was used for OECD 307 test, whereas non-labelled phenanthrene and atrazine was used for OECD 106. The sterilisation efficiencies were investigated using traditional viable plate count and molecular approaches (RNA extraction method). The results suggest that none of the tested techniques resulted in completely sterilised soil with autoclaving being the most efficient technique. Adding sodium azide led to most inefficient sterilisation and a significant increase (0.56 units) in soil pH. OECD 307 results showed differences in NER formation of the test chemicals, especially for soil poisoning and γ-radiation, which could be due to inefficient sterilisation and/or change in soil physico-chemical properties. OECD 106 results suggest that none of the sterilisation techniques considerably affected sorption behaviour of the test chemicals. Based on our results, we recommend autoclaving as most suitable sterilisation technique.


Assuntos
Biodegradação Ambiental , Poluentes do Solo , Solo , Esterilização , Poluentes do Solo/química , Poluentes do Solo/análise , Esterilização/métodos , Solo/química , Adsorção , Raios gama , Fenantrenos/química
2.
Int J Pharm ; 656: 124096, 2024 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-38583821

RESUMO

Pulmonary fibrosis (PF) is a chronic, progressive and irreversible interstitial lung disease that seriously threatens human life and health. Our previous study demonstrated the unique superiority of traditional Chinese medicine cryptotanshinone (CTS) combined with sustained pulmonary drug delivery for treating PF. In this study, we aimed to enhance the selectivity, targeting efficiency and sustained-release capability based on this delivery system. To this end, we developed and evaluated CTS-loaded modified liposomes-chitosan (CS) microspheres SM(CT-lipo) and liposome-exosome hybrid bionic vesicles-CS microspheres SM(LE). The prepared nano-in-micro particles system integrates the advantages of the carriers and complements each other. SM(CT-lipo) and SM(LE) achieved lung myofibroblast-specific targeting through CREKA peptide binding specifically to fibronectin (FN) and the homing effect of exosomes on parent cells, respectively, facilitating efficient delivery of anti-fibrosis drugs to lung lesions. Furthermore, compared with daily administration of conventional microspheres SM(NC) and positive control drug pirfenidone (PFD), inhaled administration of SM(CT-lipo) and SM(LE) every two days still attained similar efficacy, exhibiting excellent sustained drug release ability. In summary, our findings suggest that the developed SM(CT-lipo) and SM(LE) delivery strategies could achieve more accurate, efficient and safe therapy, providing novel insights into the treatment of chronic PF.


Assuntos
Quitosana , Exossomos , Fibronectinas , Lipossomos , Fibrose Pulmonar , Piridonas , Animais , Fibronectinas/administração & dosagem , Fibrose Pulmonar/tratamento farmacológico , Exossomos/química , Quitosana/química , Quitosana/administração & dosagem , Administração por Inalação , Microesferas , Liberação Controlada de Fármacos , Masculino , Preparações de Ação Retardada , Fenantrenos/administração & dosagem , Fenantrenos/química , Fenantrenos/farmacocinética , Camundongos , Sistemas de Liberação de Medicamentos/métodos , Humanos , Pulmão/metabolismo , Pulmão/efeitos dos fármacos , Ratos Sprague-Dawley , Antifibróticos/administração & dosagem , Antifibróticos/química
3.
Int J Mol Sci ; 25(8)2024 Apr 13.
Artigo em Inglês | MEDLINE | ID: mdl-38673898

RESUMO

The absolute configuration and stability of two thianthrene chiral sulfoxides has been determined by means of X-ray single-crystal structure determinations. The analyses and configurations allow verification that the diastereomeric sulfoxides are stable in solution and are not interconverting, which has been suggested in some studies of sulfoxides. The two thianthrene sulfoxides have slightly different Rf values, which allowed their separation using flash chromatography on silica. The spots run back-to-back, which posed a challenge for their separation. The pure, separated compounds in solution remain as separate, single spots on a Thin Layer Chromatography (TLC) plate.


Assuntos
Sulfóxidos , Estereoisomerismo , Sulfóxidos/química , Cristalografia por Raios X/métodos , Modelos Moleculares , Cromatografia em Camada Fina/métodos , Fenantrenos/química , Estrutura Molecular
4.
Mol Pharm ; 21(5): 2473-2483, 2024 May 06.
Artigo em Inglês | MEDLINE | ID: mdl-38579335

RESUMO

In recent years, the drainage of fluids, immune cells, antigens, fluorescent tracers, and other solutes from the brain has been demonstrated to occur along lymphatic outflow pathways to the deep cervical lymph nodes in the neck. To the best of our knowledge, no studies have evaluated the lymphatic transport of therapeutics from the brain. The objective of this study was to determine the lymphatic transport of model therapeutics of different molecular weights and lipophilicity from the brain using cervical lymph cannulation and ligation models in rats. To do this, anesthetized Sprague-Dawley rats were cannulated at the carotid artery and cannulated, ligated, or left intact at the cervical lymph duct. Rats were administered 14C-ibuprofen (206.29 g/mol, logP 3.84), 3H-halofantrine HCl (536.89 g/mol, logP 8.06), or 3H-albumin (∼65,000 g/mol) via direct injection into the brain striatum at a rate of 0.5 µL/min over 16 min. Plasma or cervical lymph samples were collected for up to 6-8 h following dosing, and brain and lymph nodes were collected at 6 or 8 h. Samples were subsequently analyzed for radioactivity levels via scintillation counting. For 14C-ibuprofen, plasma concentrations over time (plasma AUC0-6h) were >2 fold higher in lymph-ligated rats than in lymph-intact rats, suggesting that ibuprofen is cleared from the brain primarily via nonlymphatic routes (e.g., across the blood-brain barrier) but that this clearance is influenced by changes in lymphatic flow. For 3H-halofantrine, >73% of the dose was retained at the brain dosing site in lymph-intact and lymph-ligated groups, and plasma AUC0-8h values were low in both groups (<0.3% dose.h/mL), consistent with the high retention in the brain. It was therefore not possible to determine whether halofantrine undergoes lymphatic transport from the brain within the duration of the study. For 3H-albumin, plasma AUC0-8h values were not significantly different between lymph-intact, lymph-ligated, and lymph-cannulated rats. However, >4% of the dose was recovered in cervical lymph over 8 h. Lymph/plasma concentration ratios of 3H-albumin were also very high (up to 53:1). Together, these results indicate that 3H-albumin is transported from the brain not only via lymphatic routes but also via the blood. Similar to other tissues, the lymphatics may thus play a significant role in the transport of macromolecules, including therapeutic proteins, from the brain but are unlikely to be a major transport pathway from the brain for small molecule drugs that are not lipophilic. Our rat cervical lymph cannulation model can be used to quantify the lymphatic drainage of different molecules and factors from the brain.


Assuntos
Encéfalo , Ibuprofeno , Linfonodos , Ratos Sprague-Dawley , Animais , Ratos , Encéfalo/metabolismo , Masculino , Linfonodos/metabolismo , Ibuprofeno/farmacocinética , Ibuprofeno/administração & dosagem , Ibuprofeno/química , Fenantrenos/farmacocinética , Fenantrenos/química , Fenantrenos/administração & dosagem , Transporte Biológico/fisiologia , Albuminas/farmacocinética , Albuminas/metabolismo
5.
Biomater Adv ; 160: 213852, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38636118

RESUMO

Immunotherapy is an emerging approach for the treatment of solid tumors. Although chemotherapy is generally considered immunosuppressive, specific chemotherapeutic agents can induce tumor immunity. In this study, we developed a targeted, acid-sensitive peptide nanoparticle (DT/Pep1) to deliver doxorubicin (DOX) and triptolide (TPL) to breast cancer cells via the enhanced permeability and retention (EPR) effect and the breast cancer-targeting effect of peptide D8. Compared with administration of the free drugs, treatment with the DT/Pep1 system increased the accumulation of DOX and TPL at the tumor site and achieved deeper penetration into the tumor tissue. In an acidic environment, DT/Pep1 transformed from spherical nanoparticles to aggregates with a high aspect ratio, which successfully extended the retention of the drugs in the tumor cells and bolstered the anticancer effect. In both in vivo and in vitro experiments, DT/Pep1 effectively blocked the cell cycle and induced apoptosis. Importantly, the DT/Pep1 system efficiently suppressed tumor development in mice bearing 4T1 tumors while simultaneously promoting immune system activation. Thus, the results of this study provide a system for breast cancer therapy and offer a novel and promising platform for peptide nanocarrier-based drug delivery.


Assuntos
Antineoplásicos , Apoptose , Diterpenos , Doxorrubicina , Peptídeos , Animais , Apoptose/efeitos dos fármacos , Doxorrubicina/farmacologia , Doxorrubicina/química , Doxorrubicina/administração & dosagem , Feminino , Peptídeos/farmacologia , Peptídeos/química , Peptídeos/administração & dosagem , Camundongos , Humanos , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/administração & dosagem , Linhagem Celular Tumoral , Diterpenos/farmacologia , Diterpenos/química , Diterpenos/administração & dosagem , Imunomodulação/efeitos dos fármacos , Compostos de Epóxi/farmacologia , Compostos de Epóxi/química , Compostos de Epóxi/administração & dosagem , Nanopartículas/química , Fenantrenos/farmacologia , Fenantrenos/química , Fenantrenos/administração & dosagem , Fenantrenos/uso terapêutico , Neoplasias da Mama/tratamento farmacológico , Neoplasias da Mama/imunologia , Neoplasias da Mama/patologia , Sistemas de Liberação de Medicamentos/métodos , Camundongos Endogâmicos BALB C
6.
J Hazard Mater ; 470: 134109, 2024 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-38547751

RESUMO

Polycyclic aromatic hydrocarbons (PAHs) are prevalent environmental contaminants that are harmful to ecological and human health. Bioremediation is a promising technique for remediating PAHs in the environment, however bioremediation often results in the accumulation of toxic PAH metabolites. The objectives of this research were to demonstrate the cometabolic treatment of a mixture of PAHs by a pure bacterial culture, Rhodococcus rhodochrous ATCC 21198, and investigate PAH metabolites and toxicity. Additionally, the surfactant Tween ® 80 and cell immobilization techniques were used to enhance bioremediation. Total PAH removal ranged from 70-95% for fluorene, 44-89% for phenanthrene, 86-97% for anthracene, and 6.5-78% for pyrene. Maximum removal was achieved with immobilized cells in the presence of Tween ® 80. Investigation of PAH metabolites produced by 21198 revealed a complex mixture of hydroxylated compounds, quinones, and ring-fission products. Toxicity appeared to increase after bioremediation, manifesting as mortality and developmental effects in embryonic zebrafish. 21198's ability to rapidly transform PAHs of a variety of molecular structures and sizes suggests that 21198 can be a valuable microorganism for catalyzing PAH remediation. However, implementing further treatment processes to address toxic PAH metabolites should be pursued to help lower post-remediation toxicity in future studies.


Assuntos
Biodegradação Ambiental , Células Imobilizadas , Hidrocarbonetos Policíclicos Aromáticos , Rhodococcus , Tensoativos , Peixe-Zebra , Rhodococcus/metabolismo , Tensoativos/toxicidade , Tensoativos/química , Tensoativos/metabolismo , Hidrocarbonetos Policíclicos Aromáticos/toxicidade , Hidrocarbonetos Policíclicos Aromáticos/química , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Animais , Células Imobilizadas/metabolismo , Polissorbatos/toxicidade , Polissorbatos/química , Poluentes Ambientais/toxicidade , Poluentes Ambientais/metabolismo , Poluentes Ambientais/química , Fenantrenos/toxicidade , Fenantrenos/metabolismo , Fenantrenos/química , Embrião não Mamífero/efeitos dos fármacos
7.
Environ Pollut ; 347: 123712, 2024 Apr 15.
Artigo em Inglês | MEDLINE | ID: mdl-38460593

RESUMO

Humic acid (HA) from different organic solid waste (OSW) compost has been shown good adsorption properties for phenanthrene. However, the raw material of HA can affect its structure, resulting in differences in adsorption capacity. Therefore, this study focused on the adsorption characteristics of phenanthrene by HA from different OSW compost. In this work, chicken manure (CM), rice straw (RS) and lawn waste (LW) were selected as sources of composted HA. The adsorption mechanism of HA from different OSW compost were revealed through analytical techniques including three-dimensional fluorescence spectroscopy (EEM), two-dimensional correlation spectroscopy (2DCOS), and Fourier-transform infrared spectroscopy (FTIR). The results suggested that HA from LW compost had a better adsorption affinity for phenanthrene because of its more complex fluorescent component, where C1 as a simple component determined the adsorption process specifically. Furthermore, after HA from LW compost adsorbed phenanthrene, the increase in aromatic -COOH and -NH was the main reason for fluorescence quenching. These results indicated that HA from LW compost had better adsorption effect for phenanthrene. The results of this study were expected to provide a selection scheme for the control of phenanthrene pollution and environmental remediation.


Assuntos
Compostagem , Fenantrenos , Substâncias Húmicas/análise , Solo/química , Resíduos Sólidos , Adsorção , Espectrometria de Fluorescência , Fenantrenos/química
8.
Phytochemistry ; 221: 114035, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38401672

RESUMO

A group of phenanthrene derivatives with different deformed types, including four previously undescribed derivatives (1-4), an undescribed natural product (5) and five known compounds (6-10), were isolated from the leaves and stems of Strophioblachia fimbricalyx by molecular networking based on UPLC-MS/MS method. Their structures were established by 1D/2D NMR spectroscopy, HRESIMS, quantum chemistry calculation, and single crystal X-ray diffraction. In biogenic pathways, series of deformed phenanthrenes were all suspected to be derived from 6/6/6 tricyclic phenanthrenes with a gem-dimethyl unit in one ring as characteristic components of Strophioblachia. Fimbricalyxone (1) and trigoxyphin M (6) with a 6/6/5 tricyclic carbon skeleton were reported for the first time from the genus and fimbricalyxanhydride C (2) is the first example of anhydride type bearing a rare 8,9-oxycycle. All the isolates were evaluated for their cytotoxic activity against three tumor cell lines, and compounds 8 and 10 exhibited significant activity with IC50 values of 4.65-9.02 µM, and the structure-activity relationship of the deformed phenanthrenes was discussed. In addition, the X-ray structure of 8 and 10 and the antineoplastic activity of 10 are reported herein for the first time. Trigohowilol G (10) inhibiting the proliferation of A549 cells might be related to cell cycle distribution and the induction of S phase arrest, and it induced cell apoptosis through Bad/Bax/Cleaved PARP1 pathway.


Assuntos
Antineoplásicos Fitogênicos , Antineoplásicos , Fenantrenos , Estrutura Molecular , Antineoplásicos Fitogênicos/química , Fenantrenos/química , Cromatografia Líquida , Espectrometria de Massas em Tandem , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Apoptose
9.
J Med Chem ; 67(2): 1093-1114, 2024 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-38169372

RESUMO

Triptolide has a significant antitumor activity, but its toxicity limits its clinical application. As the mitochondrion-targeting strategy showed an advantage in selective antitumor effect based on the higher mitochondrial membrane potential (MMP) in tumor cells than normal cells, the lipophilic cations triphenylphosphonium and E-4-(1H-indol-3-yl vinyl)-N-methylpyridinium iodide (F16) were selected as targeting carriers for structural modification of triptolide. The derivatives bearing F16 generally retained most antitumor activities, overcame its inhibition plateau phenomena, and enhanced its selective antitumor effect in lung cancer. The representative derivative F9 could accumulate in the mitochondria of NCI-H1975 cells, inducing apoptosis and a dose-dependent increase in intracellular reactive oxygen species and reducing MMP. Moreover, no effects were observed in normal cells BEAS-2B. In vivo studies showed that the developmental, renal, and liver toxicities of F9 to zebrafish were significantly lower than those of triptolide. This study provides a promising idea to relieve the toxicity problem of triptolide.


Assuntos
Diterpenos , Compostos Organofosforados , Fenantrenos , Animais , Peixe-Zebra , Mitocôndrias , Apoptose , Diterpenos/toxicidade , Diterpenos/química , Fenantrenos/toxicidade , Fenantrenos/química , Linhagem Celular Tumoral , Compostos de Epóxi
10.
Environ Res ; 244: 117898, 2024 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-38092242

RESUMO

Sorption by soil is the fundamental basis for environment fate of hydrophobic organic contaminants (HOCs), which varies significantly depending on diverse properties of soils. Therefore, a generalized approach to predict HOC sorption by soils is required. In this study, 488 data points were extracted from references and adopted to develop models for estimating the sorption capacities of phenanthrene in soils using six different machine learning (ML) approaches. The extreme gradient boosting (XGBT) model demonstrated the most favorable performance, achieving a coefficient of determination of 0.91 and root-mean-square errors of 0.24 for the testing dataset. The XGBT model's performance was further demonstrated by comparing with experimental data from batch sorption tests conducted on 20 soil samples collected from 17 provinces of China. The differences between the predicted values and the experimental values were statistically equal to zero (p = 0.14). Leveraging the XBGT model together with soil properties from the Harmonized World Soil Database, the distribution of sorption capacities in Chinese soils was successfully depicted on a national scale. This research is expected to contribute to a deeper understanding of the migration of persistent organic pollutants in terrestrial system. Furthermore, the established model holds implications for more precise and scientific soil environmental management.


Assuntos
Fenantrenos , Poluentes do Solo , Solo , Adsorção , Poluentes do Solo/análise , Interações Hidrofóbicas e Hidrofílicas , Fenantrenos/química
11.
Chemosphere ; 349: 140860, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38052312

RESUMO

Phenanthrene is a persistent organic pollutant released by numerous industries. The purpose of the study is to construct a batch reactor for phenanthrene degradation using a bimetallic (BM) ZnS-SnS nanoparticle as a photocatalyst. ZnS-SnS BM NPs were used as a photocatalyst, employed from precursors Zinc acetate dihydrate and tin (II) chloride dihydrate, with crystalline cubic-shaped particle sizes. ZnS-SnS BM NPs were utilized in batch adsorption assays to assess the impact of phenanthrene degradation parameters on various PAHs (Polycyclic aromatic hydrocarbons) concentrations, pH levels, and irradiation sources. Adsorption kinetic and isotherm tests revealed that the pseudo-first order kinetic model, pseudo-second order kinetic model, and Langmuir isotherm model all fit effectively with the effective phenanthrene degradation using ZnS-SnS BM NPs. The degraded product were analyzed for GC-MS, revealing that organic pollutant phenanthrene was converted into harmless by-products like n-hexadecenoic acid, oleic acid, and octadecanoic acid. The toxicity of phenanthrene was observed to decrease with an increase in ZnS-SnS BM NPs concentration. ZnS-SnS BM NP concentration of 150 µg/mL, the zone of inhibition values was recorded highest zone of inhibition (19 ± 1.2 mm) against the strains S. epidermis followed by B. cereus and Clostridium spp. Further adult zebrafish were found to be less toxic to ZnS-SnS BM NPs after 96 h of exposure, with an LD50 of 100 µg/L. The toxicity escalated as concentrations increased. Behavior test showed normal swimming, learning, and memory in open tank and T-maze tests, while 100 µg/L showed pausing/frozen time in zebra fish therefore low doses are considered safe. Hence by employing ZnS-SnS BM NPs can be engaged in waste water treatment for PAH degradation.


Assuntos
Fenantrenos , Hidrocarbonetos Policíclicos Aromáticos , Animais , Peixe-Zebra , Adsorção , Fenantrenos/toxicidade , Fenantrenos/química , Hidrocarbonetos Policíclicos Aromáticos/toxicidade
12.
Chemosphere ; 349: 140954, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38103656

RESUMO

Polycyclic aromatic hydrocarbons (PAHs) are persistent organic pollutants in the environment, which are teratogenic, carcinogenic, and mutagenic. Co-contamination of PAHs and heavy metal commonly exists in soil. In this study, 20 types of soils with different properties in China were collected and comprehensively characterized. Phenanthrene (Phe) and Cu (II) were selected as representatives of PAHs and heavy metals, respectively. The adsorption-desorption behaviors of Phe under Phe contamination and Cu (II)-Phe co-contamination in 20 types of soils were studied. The adsorption-desorption behaviors of Phe in 20 types of soils varied greatly, and adsorption of Phe in the soils followed both linear partitioning and nonlinear surface adsorption. Soil organic matter (SOM) plays an important role in the adsorption-desorption behavior of Phe. When the concentrations of Phe were >50 µg/L, soft carbon (SC) fraction of SOM not black carbon (BC) contributed more to the adsorption of Phe. Soil dissolved organic matter (DOM), especially fulvic acid and humic acid fractions, contributes to the adsorption of Phe. Under the effect of Cu (II) (60 mg/L in solution), the adsorption capacity of soil for Phe increased, which possibly resulted from lowered pH, the existence of the cation-π bonding and the "bonding bridge" effect. The systematic investigation of adsorption-desorption behaviors of Phe in soils under heavy metal-PAHs co-contamination will provide a scientific basis for the calculation of soil environmental capacity in the future.


Assuntos
Metais Pesados , Fenantrenos , Hidrocarbonetos Policíclicos Aromáticos , Poluentes do Solo , Solo/química , Adsorção , Poluentes do Solo/análise , Fenantrenos/química , Metais Pesados/análise , Carbono
13.
Sci Total Environ ; 905: 167305, 2023 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-37742959

RESUMO

Polycyclic aromatic hydrocarbons (PAHs) are highly toxic organic pollutants widely distributed in terrestrial environments and laccase was considered as an effective enzyme in PAHs bioremediation. However, laccase-assisted phytoremediation of PAHs-contaminated soil has not been reported. Moreover, the overuse of plastic films in agriculture greatly increased the risk of co-existence of PAHs and microplastics in soil. Microplastics can adsorb hydrophobic organics, thus altering the bioavailability of PAHs and ultimately affecting the removal of PAHs from soil. Therefore, this study aimed to evaluate the efficiency of laccase-assisted maize (Zea mays L.) in the remediation of phenanthrene (PHE)-contaminated soil and investigate the effect of microplastics on this remediation process. The results showed that the combined application of laccase and maize achieved a removal efficiency of 83.47 % for soil PHE, and laccase significantly reduced the accumulation of PHE in maize. However, microplastics significantly inhibited the removal of soil PHE (10.88 %) and reduced the translocation factor of PHE in maize (87.72 %), in comparison with PHE + L treatment. Moreover, microplastics reduced the laccase activity and the relative abundance of some PAHs-degrading bacteria in soil. This study provided an idea for evaluating the feasibility of the laccase-assisted plants in the remediation of PAHs-contaminated soil, paving the way for reducing the risk of secondary pollution in the process of phytoremediation.


Assuntos
Fenantrenos , Hidrocarbonetos Policíclicos Aromáticos , Poluentes do Solo , Biodegradação Ambiental , Lacase , Microplásticos , Plásticos , Poluentes do Solo/análise , Fenantrenos/química , Hidrocarbonetos Policíclicos Aromáticos/análise , Solo/química , Microbiologia do Solo
14.
J Nat Prod ; 86(5): 1294-1306, 2023 05 26.
Artigo em Inglês | MEDLINE | ID: mdl-37140218

RESUMO

Three new phenanthrene derivatives (1, 2, 4), one new fluorenone (3), and four known compounds (5-8) were isolated from the ethyl acetate extract of Dendrobium crumenatum Sw. stems using column chromatography. The chemical structures were elucidated by analysis of spectroscopic data. The absolute configuration of 4 was determined by electronic circular dichroism calculation. We also evaluated the immunomodulatory effects of compounds isolated from D. crumenatum in human peripheral blood mononuclear cells from healthy individuals and those from patients with multiple sclerosis in vitro. Dendrocrumenol B (2) and dendrocrumenol D (4) showed strong immunomodulatory effects on both CD3+ T cells and CD14+ monocytes. Compounds 2 and 4 could reduce IL-2 and TNF production in T cells and monocytes that were treated with phorbol-12-myristate-13-acetate and ionomycin (PMA/Iono). Deep immune profiling using high-dimensional single-cell mass cytometry could confirm immunomodulatory effects of 4, quantified by the reduction of activated T cell population under PMA/Iono stimulation, in comparison to the stimulated T cells without treatment.


Assuntos
Dendrobium , Fenantrenos , Humanos , Dendrobium/química , Leucócitos Mononucleares , Monócitos , Fenantrenos/farmacologia , Fenantrenos/química , Linfócitos T , Acetato de Tetradecanoilforbol/farmacologia , Fluorenos/química , Fluorenos/farmacologia
15.
Chem Biodivers ; 20(4): e202201068, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-36919925

RESUMO

An interesting class of compounds of natural origin is dihydrophenanthrene dimers, which are characterized by a series of remarkable biological properties. Considering the hypothesis that each dimer is obtained through a biosynthetic mechanism that involves the coupling of the corresponding radicals of the single dihydrophenanthrene unit, we identified 29 dihydrophenanthrenes. Of these dihydrophenanthrenes, 11 were new compounds that could be isolated from 10 different plant species; 11 had already been identified, but not yet isolated in the 17 different plant species from which the corresponding dimers had been isolated; and 7 were known and had been isolated in the same plant sources of the corresponding dimers. A targeted analysis of several natural extracts from specific plant sources would allow the identification of known or new molecules with potential and/or specific biological activities and, in a final analysis, would confirm the relative biosynthetic mechanism.


Assuntos
Fenantrenos , Fenantrenos/química , Plantas/química
16.
Artigo em Inglês | MEDLINE | ID: mdl-36834341

RESUMO

The bioavailability and mobility of phenanthrene (Phe) adsorbed by multi-walled carbon nanotubes (MWCNTs) may be substantially influenced by nonionic surfactants used both in the synthesis and dispersion of MWCNTs. The adsorption mechanisms of Phe adsorbed onto MWCNTs under the different nonionic surfactants Tween 80 (TW-80) and Triton X-100 (TX-100) in the aqueous phase were investigated in terms of changes in the MWCNTs' compositions and structures. The results showed that TW-80 and TX-100 were easily adsorbed onto MWCNTs. Phe adsorption data onto MWCNTs were better suited to the Langmuir equation than the Freundlich equation. Both TW-80 and TX-100 reduced the adsorption capacity of Phe onto MWCNTs. When TW-80 and TX-100 were added in the adsorption system, the saturated adsorption mass of Phe decreased from 35.97 mg/g to 27.10 and 29.79 mg/g, respectively, which can be attributed to the following three reasons. Firstly, the hydrophobic interactions between MWCNTs and Phe became weakened in the presence of nonionic surfactants. Secondly, the nonionic surfactants covered the adsorption sites of MWCNTs, which caused Phe adsorption to be reduced. Finally, nonionic surfactants can also promote the desorption of Phe from MWCNTs.


Assuntos
Nanotubos de Carbono , Fenantrenos , Nanotubos de Carbono/química , Adsorção , Octoxinol , Polissorbatos , Tensoativos/química , Fenantrenos/química
17.
Environ Pollut ; 322: 121121, 2023 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-36681379

RESUMO

Humic substances (HSs) play important roles in the transport and bioavailability of hydrophobic organic compounds (HOCs) in soils. The sorption of HOCs depends on the compositions and structures of HSs which may differ in different climatic zones, however, the sorption behavior of HOCs by HSs in soils from different climatic zones is poorly understood. In this study, different HS fractions (humic acids-HAs, fulvic acids-FAs and humin-HM) in soils from different climatic zones were extracted and used as sorbents for polycyclic aromatic hydrocarbons (PAHs). The results indicated that HSs (including HA, FA and HM fractions) from colder climatic zones contained more oxygen-containing functional groups and exhibited smaller molecular weight as well as higher aliphaticity and polarity than those from warmer climatic zones. The sorption affinity of HAs at the low given concentration (0.05 Sw) of naphthalene (Nap), phenanthrene (Phe), pyrene (Pyr) and benz(α)anthracene (BaA) from warmer climatic zones to colder ones increased from 26.3 to 43.9, from 36.7 to 114.0, from 125.8 to 388.8, and from 322.5 to 876.1, respectively, and the same trends were obtained for FAs and HM at the same PAH concentration. The results indicated that HSs from colder climatic zones showed higher sorption affinity than those from warmer climatic zones. Moreover, the weighted contributions of FAs, HAs and HM to the overall sorption from different climatic zones were 9.1-28.4%, 13.5-59.2% and 23.4-76.9%, respectively. This indicates FA fraction, a previously neglected component, is also an important contributor to binding PAHs in soils. This study suggests that the difference in sorption behaviors of HOCs to HSs among different climatic zones should be considered when predicting HOC fates and bioavailability in soils.


Assuntos
Fenantrenos , Hidrocarbonetos Policíclicos Aromáticos , Poluentes do Solo , Substâncias Húmicas/análise , Solo/química , Hidrocarbonetos Policíclicos Aromáticos/análise , Adsorção , Fenantrenos/química , Poluentes do Solo/análise
18.
J Org Chem ; 88(1): 717-721, 2023 01 06.
Artigo em Inglês | MEDLINE | ID: mdl-36525632

RESUMO

We report a photoinduced phenanthrene synthesis from aryl iodides and styrenes through an arylation/cyclization cascade. Compared to prior methods, this approach obviates the need for hazardous reagents and provides access to unsymmetrical phenanthrenes with good functional group tolerance. Mechanistic studies revealed that photoexcitation of aryl iodides leads to homolytic C-I bond cleavage. Arylation of styrenes with the formed aryl radical species furnishes stilbene derivatives, which undergo photoinduced cyclization promoted by iodine generated in situ to yield phenanthrene products.


Assuntos
Iodetos , Fenantrenos , Estrutura Molecular , Fenantrenos/química , Estirenos/química
19.
Chemosphere ; 313: 137389, 2023 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-36455665

RESUMO

Oil pollution is one of the major environmental concerns in the petroleum industry. In this study, a cheap food-grade sodium caseinate (NaCas) was used as a pH-responsive washing fluid in the remediation of phenanthrene (PHE) affected peat moss. The effects of environmental factors on the removal of PHE were systematically investigated. The results showed that increasing NaCas concentration and washing temperature improved the PHE mobilization, while high salinity and humic acid dosage displayed a negative effect. The factorial analysis revealed that three individual factors and two interactions exhibited significant effects on the washing performance. Due to the pH-responsive property of NaCas, the turbidity, total organic carbon (TOC), and chemical oxygen demand (COD) of the washing effluent were remarkably reduced by simply adjusting the solution acidity, improving the practical application of such a washing method. Significantly, the toxicity modeling proved that NaCas can reduce the binding energy between PHE and superoxide dismutase (SOD) of the selected marine organism, and thus relieve the toxicity of PHE to the organisms. Given these advantages, NaCas-assisted washing can be a viable option for the remediation of contaminated peat moss.


Assuntos
Fenantrenos , Poluentes do Solo , Sphagnopsida , Fosfoproteínas , Fenantrenos/química , Concentração de Íons de Hidrogênio , Solo/química , Poluentes do Solo/química
20.
Chemosphere ; 313: 137374, 2023 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-36435320

RESUMO

The worldwide existing micro- and nano-plastics (MNPs) showed high sorption capacity for hydrophobic organic contaminants (HOCs), and thus leading to change of the environmental behaviors and fates of HOCs. However, there is a lack of general index for evaluating the sorption capacity of MNPs for HOCs. Herein, we investigated the sorption of chlorobenzene, naphthalene and phenanthrene to 10 MNPs of different polymer types with and without UV-aging, respectively. It was found that the sorption was well fitted by Freundlich isotherm model with coefficients R2 in the range of 0.892-1.00, and aging of most MNPs resulted in decreased sorption capacity for naphthalene and phenanthrene but slightly increased sorption capacity for chlorobenzene. More importantly, for the 8 MNPs commonly present in the environment and with measured total organic carbon (TOC) covering the range of 23.0-91.9%, the logarithm sorption constant (logKd) values of the studied HOCs positively correlated with TOC contents of MNPs, with a good determination coefficient (R2) of 0.923 for naphthalene, 0.694 for chlorobenzene, and 0.565 for phenanthrene. Our study demonstrated that the TOC content of MNPs is a good index for estimating the contribution of total MNPs to the sorption of nonpolar HOCs in the environmental media.


Assuntos
Microplásticos , Fenantrenos , Fenantrenos/química , Naftalenos , Carbono/química , Adsorção
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