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Molecules (Basel, Switzerland) Jun 2024L. (Apiaceae) is a medicinal plant with a well-documented history in phytotherapy. The aim of the present work was to isolate isopimpinellin (5,8-methoxypsoralen; IsoP)...
L. (Apiaceae) is a medicinal plant with a well-documented history in phytotherapy. The aim of the present work was to isolate isopimpinellin (5,8-methoxypsoralen; IsoP) from the fruit of this plant and evaluate its biological activity against selected tumor cell lines. The methanol extract obtained with the use of an accelerated solvent extraction (ASE) method was the most suitable for the quantitative analysis of coumarins in the fruit matrix. The coumarin content was estimated by RP-HPLC/DAD, and the amount of IsoP was found to be 404.14 mg/100 g dry wt., constituting 24.56% of the total coumarin fraction (1.65 g/100 g). This, along with the presence of xanthotoxin (368.04 mg/100 g, 22.36%) and bergapten (253.05 mg/100 g, 15.38%), confirmed fruits as an excellent source of these compounds. IsoP was isolated (99.8% purity) by combined liquid chromatography/centrifugal partition chromatography (LC/CPC) and tested for the first time on its antiproliferative activity against human colorectal adenocarcinoma (HT29, SW620), osteosarcoma (Saos-2, HOS), and multiple myeloma (RPMI8226, U266) cell lines. MTT assay results (96 h incubation) demonstrated a dose- and cell line-dependent decrease in cell proliferation/viability, with the strongest effect of IsoP against the Saos-2 cell line (IC50; 42.59 µM), medium effect against U266, HT-29, and RPMI8226 (IC50 = 84.14, 95.53, and 105.0 µM, respectively), and very weak activity against invasive HOS (IC50; 321.6 µM) and SW620 (IC50; 711.30 µM) cells, as well as normal human skin fibroblasts (HSFs), with IC50; 410.7 µM. The mechanistic study on the Saos-2 cell line showed that IsoP was able to reduce DNA synthesis and trigger apoptosis via caspase-3 activation. In general, IsoP was found to have more potency towards cancerous cells (except for HOS and SW620) than against healthy cells. The Selective Index (SI) was determined, underlining the higher selectivity of IsoP towards cancer cells compared to healthy cells (SI = 9.62 against Saos-2). All these results suggest that IsoP might be a promising molecule in the chemo-prevention and treatment of primary osteosarcoma.
Topics: Humans; Fruit; Cell Line, Tumor; Furocoumarins; Plant Extracts; Ammi; Cell Proliferation; Antineoplastic Agents, Phytogenic; Apoptosis; Chromatography, High Pressure Liquid; Cell Survival
PubMed: 38930940
DOI: 10.3390/molecules29122874 -
Molecules (Basel, Switzerland) Jun 2024A promising method was established for the determination of nine halobenzoquinones (HBQs) in potable water by membrane solid-phase extraction (MSPE) pretreatment and the...
A promising method was established for the determination of nine halobenzoquinones (HBQs) in potable water by membrane solid-phase extraction (MSPE) pretreatment and the liquid chromatography-mass spectrometry (LC-MS) method. A 500 mL water sample was taken for enrichment by the SDB-RPS membrane, which was previously activated by methanol and ultrapure water. The sample was eluted with methanol and re-dissolved with the initial mobile phase after nitrogen blowing. Then, it was detected in negative ion mode using the working curve, and HBQs were quantified by the external standard method. The linearity was satisfactory in the concentration range of 4-1000 ng/L, with correlation coefficients of 0.9963~0.9994. The recoveries were 73.5~126.6% at three spiked levels, with relative standard deviations (RSDs) of 6.8~15.5%. The limits of detection (LOD, S/N = 3) values were 0.1~0.7 ng/L. The results demonstrate that the MSPE-LC-MS method is reliable, rapid, and sensitive for the simultaneous analysis of nine HBPs in potable water.
Topics: Solid Phase Extraction; Chromatography, Liquid; Benzoquinones; Drinking Water; Mass Spectrometry; Limit of Detection; Water Pollutants, Chemical; Liquid Chromatography-Mass Spectrometry
PubMed: 38930920
DOI: 10.3390/molecules29122856 -
Molecules (Basel, Switzerland) Jun 2024Organic phosphoester (OPE) antioxidants are currently required due to their contribution to enhancing the quality of polymers, including polypropylene (PP). In this...
Organic phosphoester (OPE) antioxidants are currently required due to their contribution to enhancing the quality of polymers, including polypropylene (PP). In this research, an integral methodology is presented for the efficient extraction of bis(2,4-dicumylphenyl) pentaerythritol diphosphite from industrial wastewater. Upon employing the solid-phase extraction (SPE) technique, the recovered compound is subjected to a comprehensive analysis of the recovered compound using high-performance liquid chromatography (HPLC), mass spectrometry (MS), thermal analysis (TGA), Fourier transforms infrared spectroscopy (FTIR), and differential scanning calorimetry (DSC). Subsequently, purified Bis(2,4-dicumylphenyl) pentaerythritol diphosphite was evaluated as a thermo-oxidative stabilizer after incorporation into PP resins. The relative standard deviation (RSD), Error (Er), linearity (R), and percentage (%) recovery were less than 2.6, 2.5, more significant than 0.9995, and greater than 96%, respectively, for the inter-day and intra-day tests of the chromatographic method and the SPE. Except for chloroform, which was necessary due to the solubility properties of the investigated analyte, the use of environmentally friendly solvents, such as methanol and acetonitrile, was considered during the development of this research. The OPE extracted from industrial wastewater was characterized by FTIR, UV-Vis, DSC, TGA, and MS, allowing the elucidation of the structure of Bis(2,4-dicumylphenyl) pentaerythritol diphosphite (BDPD). The recovered OPE was mixed with PP resins, allowing it to improve its thermal properties and minimize its thermo-oxidative degradation. Organophosphorus flame retardant (OPE)' concentration in wastewater is alarming, ranging from 1179.0 to 4709.6 mg L. These exceed toxicity thresholds for aquatic organisms, emphasizing global environmental risks. Using a validated solid-phase extraction (SPE) technique with over 94% recovery, the study addresses concerns by removing organic contaminants and supporting circular economy principles. The high economic and environmental significance of recovering BDPD underscores the need for urgent global attention and intervention.
PubMed: 38930844
DOI: 10.3390/molecules29122780 -
Molecules (Basel, Switzerland) Jun 2024The formation of nitrogen-containing organic interstellar molecules is of great importance to reveal chemical processes and the origin of life on Earth. Benzonitrile...
The formation of nitrogen-containing organic interstellar molecules is of great importance to reveal chemical processes and the origin of life on Earth. Benzonitrile (BN) is one of the simplest nitrogen-containing aromatic molecules in the interstellar medium (ISM) that has been detected in recent years. Methanol (CHOH) exists widely in interstellar space with high reactivity. Herein, we measured the infrared (IR) spectra of neutral and cationic BN-CHOH clusters by vacuum ultraviolet (VUV) photoionization combined with time-of-flight mass spectrometry. Combining IR spectra with the density functional theory calculations, we reveal that the BN-CHOH intends to form a cyclic H-bonded structure in neutral clusters. However, after the ionization of BN-CHOH clusters, proton-shared N···H···O and N···H···C structures are confirmed to form between BN and CHOH, with the minor coexistence of H-bond and O-π structures. The formation of the proton-shared structure expands our knowledge of the evolution of the life-related nitrogen-containing molecules in the universe and provides a possible pathway to the further study of biorelevant aromatic organic macromolecules.
PubMed: 38930810
DOI: 10.3390/molecules29122744 -
Molecules (Basel, Switzerland) Jun 2024The current study was designed to uncover the chemistry and bioactivity potentials of growing wild in Jordan. In this context, the fresh aerial parts obtained from the...
The current study was designed to uncover the chemistry and bioactivity potentials of growing wild in Jordan. In this context, the fresh aerial parts obtained from the plant material were subjected to hydrodistillation followed by GC/MS analysis. The main components of the HDEO were γ-patchoulene (23.79%), β-dihydro agarofuran (23.50%), α-guaiene (14.11%), and valencene (13.28%). Moreover, the crude thanolic extract was partitioned to afford two main major fractions, the aqueous methanol (BLM) and butanol (BLB). Phytochemical investigation of both fractions, using conventional chromatographic techniques followed by careful inspection of the spectral data for the isolated compounds (NMR, IR, and UV-Vis), resulted in the characterization of five known compounds, including α-spinasteryl (), ethyl arachidate (), ethyl myristate (), quercetin-3--β-d-glucopyranosyl-(1-4")-α-L-rhamnopyranosyl (), and isorhamnetin-3--β-d-glucopyranosyl-(1-4")-α-L-rhamnopyranosyl (). The TPC, TFC, and antioxidant activity testing of both fractions and HDEO revealed an interesting ABTS scavenging potential of the BLB fraction compared to the employed positive controls, which is in total agreement with its high TP and TF contents. Cytotoxic evaluation tests revealed that BLM had interesting cytotoxic effects on the normal breast cell line MDA-MB-231 (ATCC-HTB-26) and the normal dermal fibroblast (ATCC PCS-201-012) and normal African green monkey kidney Vero (ATCC-CCL-81) cell lines. Despite both the BLB and BLM fractions showing interesting AChE inhibition activities (IC = 217.9 ± 5.3 µg/mL and 139.1 ± 5.6 µg/mL, respectively), the HDEO revealed an interestingly high AChE inhibition power (43.8 ± 2.7 µg/mL) that far exceeds the one observed for galanthamine (91.4 ± 5.2 µg/mL). The HDEO, BLM, and BLB exhbitied no interesting antimicrobial activity against , , , , or .
Topics: Jordan; Plant Extracts; Antioxidants; Animals; Bupleurum; Humans; Vero Cells; Phytochemicals; Chlorocebus aethiops; Cell Line, Tumor; Plant Components, Aerial; Gas Chromatography-Mass Spectrometry; Cell Survival; Antineoplastic Agents, Phytogenic
PubMed: 38930796
DOI: 10.3390/molecules29122730 -
Microorganisms Jun 2024Developing new anti-human immunodeficiency virus (HIV) drug candidates that target different sites in HIV-1 replication, with better resistance profiles and lower drug...
Developing new anti-human immunodeficiency virus (HIV) drug candidates that target different sites in HIV-1 replication, with better resistance profiles and lower drug toxicity, is essential to eradicating HIV. This study investigated the potential of fractionated crude extracts of as immunomodulatory or anti-HIV drug candidates. Solid-phase extraction (SPE) was used to fractionate PO4PR2 using three different columns: MAX (Mixed-mode, strong Anion-eXchange), MCX (Mixed-mode, strong Cation-eXchange), and HLB (Hydrophilic-Lipophilic Balance) with methanol gradient methods (5%, 45%, and 95%). An MTT (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide) assay was used to assess the cell viability and cytotoxicity of the fractionated crude extract PO4PR2 in the TZM-bl cell lines. This was followed by a luciferase-based antiviral assay to assess the antiviral activity of PO4PR2. A time of addition (TOA) assay was performed to ascertain the mechanism of inhibition employed by the fractionated crude extract of PO4PR2 in the HIV life cycle. The p24 titer was determined using an ELISA, while a luciferase-based antiviral assay was used to evaluate the HIV percentage inhibition for different HIV-1 replication cycles. The TOA assay was established using antiviral drugs that target different sites in the HIV replication cycle. These included maraviroc, azidothymidine, raltegravir, and amprenavir. The immunomodulatory effect of the fractionated crude extracts on CD4+ T cells was measured by a flow cytometric analysis, for which fluorochrome-labelled monoclonal antibodies were used as markers for activation (CD38 and HLA-DR) and exhaustion (PD-1). The MCX fraction demonstrated a more significant anti-HIV inhibition than that of the fractions generated in other columns, with an IC of 0.3619 µg/mL, an HIV inhibition of 77%, 5% HLB (IC: 0.7232 µg/mL; HIV inhibition of 64%), and 5% MAX (IC: 5.240 µg/mL; HIV inhibition of 67%). It was evident from the time of addition data that the crude extract and the 5% MCX fraction inhibited viral binding (68%), reverse transcription (75%), integration (98%), and proteolysis (77%). It was shown that (the MCX fraction) have a significant inhibitory effect on reverse transcription (75% HIV inhibition) and integration (100% HIV inhibition). The 5% MCX ( = 0.0062), 5% HLB ( = 0.0269), and 5% MAX ( = 0.0117) fractionated crude extracts had low levels of CD4+ T cell (CD38 + HLA-DR+) activation compared to those of the AZT treatment, while CD4+ T cell activation was insignificant. The 5% MAX and HLB fractions may possess immunomodulatory compounds with less anti-HIV-1 activity. could be a key source of innovative anti-HIV drugs with immunomodulatory characteristics.
PubMed: 38930532
DOI: 10.3390/microorganisms12061150 -
Microorganisms May 2024Two thermophilic spore-forming sulfate-reducing strains, 435 and 781, were isolated from oil and gas reservoirs in Western Siberia (Russia) about 50 years ago. Both...
Two thermophilic spore-forming sulfate-reducing strains, 435 and 781, were isolated from oil and gas reservoirs in Western Siberia (Russia) about 50 years ago. Both strains were found to be neutrophilic, chemoorganotrophic, anaerobic bacteria, growing at 45-70 °C (optimum, 55-60 °C) and with 0-4.5% (/) NaCl (optimum, 0.5-1% NaCl). The major fatty acids were iso-C, iso-C, C, and C. In sulfate-reducing conditions, the strains utilized H/CO, formate, lactate, pyruvate, malate, fumarate, succinate, methanol, ethanol, propanol, butanol, butyrate, valerate, and palmitate. In 2005, based on phenotypic characteristics and a 16S rRNA gene sequence analysis, the strains were described as '' sp. nov. However, this species was not validly published because the type strain was not deposited in two culture collections. In this study, a genomic analysis of strain 435 was carried out to determine its taxonomic affiliation. The genome size of strain 435 was 2.886 Mb with a 55.1% genomic G + C content. The average nucleotide identity and digital DNA-DNA hybridization values were highest between strain 435 and members of the genus , 78.7-93.3% and 25.0-52.2%, respectively; these values were below the species delineation cut-offs (<95-96% and <70%). The cumulative phenotypic and phylogenetic data indicate that two strains represent a novel species within the genus , for which the name sp. nov. is proposed. The type strain is 435 (=VKM B-1492 = DSM 23196). A genome analysis of strain 435 revealed the genes for dissimilatory sulfate reduction, autotrophic carbon fixation via the Wood-Ljungdahl pathway, hydrogen utilization, methanol and organic acids metabolism, and sporulation, which were confirmed by cultivation studies.
PubMed: 38930497
DOI: 10.3390/microorganisms12061115 -
Materials (Basel, Switzerland) Jun 2024This paper reports the results of our study on electrochemical polishing of titanium and a Ti-based alloy using non-aqueous electrolyte. It was shown that...
This paper reports the results of our study on electrochemical polishing of titanium and a Ti-based alloy using non-aqueous electrolyte. It was shown that electropolishing ensured the removal of surface defects, thereby providing surface smoothing and decreasing surface roughness. The research was conducted using samples made of titanium and TiAlV alloy, as well as implant system elements: implant analog, multiunit, and healing screw. Electropolishing was carried out under a constant voltage (10-15 V) with a specified current density. The electrolyte used contained methanol and sulfuric acid. The modified surface was subjected to a thorough analysis regarding its surface morphology, chemical composition, and physicochemical properties. Scanning electron microscope images and profilometer tests of roughness confirmed significantly smoother surfaces after electropolishing. The surface profile analysis of processed samples also yielded satisfactory results, showing less imperfections than before modification. The EDX spectra showed that electropolishing does not have significant influence on the chemical composition of the samples.
PubMed: 38930203
DOI: 10.3390/ma17122832 -
Life (Basel, Switzerland) May 2024Recent studies have shown that seagrasses could possess potential applications in the treatment of inflammatory disorders. Five seagrass species (, , , , and ) from the...
Recent studies have shown that seagrasses could possess potential applications in the treatment of inflammatory disorders. Five seagrass species (, , , , and ) from the Great Barrier Reef (QLD, Australia) were thus collected, and their preliminary antioxidant and anti-inflammatory activities were evaluated. From the acetone extracts of five seagrass species subjected to 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging antioxidant assay, the extract of had the highest activity (half minimal concentration of inhibition (IC) = 138 µg/mL), with the aerial parts (IC = 119 µg/mL) possessing significantly higher antioxidant activity than the roots (IC ≥ 500 µg/mL). A human peripheral blood mononuclear cells (PBMCs) assay with bacterial lipopolysaccharide (LPS) activation and LEGENDplex cytokine analysis showed that the aerial extract of significantly reduced the levels of inflammatory cytokines tumour necrosis factor alpha (TNF-α), interleukin (IL)-1β, and IL-6 by 29%, 74%, and 90%, respectively, relative to the LPS treatment group. The aerial extract was thus fractionated with methanol (MeOH) and hexane fraction, and purification of the MeOH fraction by HPLC led to the isolation of 4-hydroxybenzoic acid (), luteolin (), and apigenin () as its major constituents. These compounds have been previously shown to reduce levels of TNF-α, IL-1β, and IL-6 and represent some of the major bioactive components of aerial parts. This investigation represents the first study of the antioxidant and anti-inflammatory properties of and the first isolation of small molecules from this species. These results highlight the potential for using seagrasses in treating inflammation and the need for further investigation.
PubMed: 38929693
DOI: 10.3390/life14060710 -
Medicina (Kaunas, Lithuania) May 2024: Gemcitabine has been used to treat various solid cancers, including, since 1997, metastatic pancreatic cancer. Here, we developed an HPLC-UV method to determine serum...
: Gemcitabine has been used to treat various solid cancers, including, since 1997, metastatic pancreatic cancer. Here, we developed an HPLC-UV method to determine serum gemcitabine levels and use it in pharmacokinetic studies. : The analysis was performed after a single protein precipitation step on a reversed-phase column, isocratically eluted with sodium phosphate buffer and methanol. For the pharmacokinetic study, NOD/SCID mice received a single dose of gemcitabine at 100 mg/kg by either subcutaneous (SC) or intraperitoneal (IP) administration. Blood samples were collected at 5, 15, and 30 min and 1, 2, 4, and 6 h after the administration of gemcitabine for further analysis. : The duration of the analysis was ~12.5 min. The calibration curve was linear (r = 0.999) over the range of 1-400 μM. The mean recovery of GEM was 96.53% and the limit of detection was 0.166 μΜ. T, Tmax, Cmax, AUC, and clearance were 64.49 min, 5.00 min, 264.88 μmol/L, 9351.95 μmol/L*min, and 0.0103(mg)/(μmol/L)/min, respectively, for the SC administration. The corresponding values for the IP administration were 59.34 min, 5.00 min, 300.73 μmol/L, 8981.35 μmol/L*min and 0.0108(mg)/(μmol/L)/min (not statistically different from the SC administration). : A simple, valid, sensitive, and inexpensive method for the measurement of gemcitabine in serum has been developed. This method may be useful for monitoring gemcitabine levels in cancer patients as part of therapeutic drug monitoring.
Topics: Deoxycytidine; Gemcitabine; Chromatography, High Pressure Liquid; Animals; Mice; Reproducibility of Results; Mice, SCID; Antimetabolites, Antineoplastic; Mice, Inbred NOD
PubMed: 38929481
DOI: 10.3390/medicina60060864