Hypohalous acid-mediated halogenation of resveratrol and its role in antioxidant and antimicrobial activities

The reactions of resveratrol with proinflammatory oxidants including hypochlorous and hypobromous acids in phosphate-buffered saline/methanol solution were carried out and eight halogenated resveratrol derivatives differing in the number and position of halogen atoms, and the configuration of double bond were obtained. Halogenation of resveratrol took place only at the aromatic A ring, and interestingly, the halogenation increased antioxidant activity of this parent molecule in the 2,2'-azobis(2-amidinopropane) hydrochloride-induced RBC haemolysis model. Additionally, antimicrobial activity of the derivatives against Gram-positive bacteria, Gram-negative bacteria and fungi were tested, and toward Candida albicans, 2-chloro-resveratrol and 2-bromo-resveratrol were more active than the unmodified form and the reference compound fluconazole.     

Isolation and identification of ent-kaurane-type diterpenoids from Rabdosia serra (MAXIM.) HARA leaf and their inhibitory activities against HepG-2, MCF-7, and HL-60 cell lines

A phytochemical investigation was conducted on Rabdosia serra leaf in this work. A new ent-kaurane-type diterpenoid named 6β,14α-dihydroxy-1α,7β-diacetoxy-7α,20-epoxy-ent-kaur-16-en-15-one, together with 6 known compounds were identified, including parvifolin G, effusanin E, lasiodin, nodosin, β-sitosterol, and stigmasterol. It was the first time that parvifolin G and effusanin E were found in R. serra. The assay of inhibition activity against HepG-2, MCF-7, and HL-60 cell lines indicated that 10 compounds (including rosmarinic acid, methyl rosmarinate and pedalitin which were isolated previously), except parvifolin G and stigmasterol, exhibited cytotoxicity against the tested tumour cells. The tumour inhibitory effects of ent-kaurane-type diterpenoids (except parvifolin G) were more effective than those of sterols and phenolics. Both 6β,14α-dihydroxy-1α,7β-diacetoxy-7α,20-epoxy-ent-kaur-16-en-15-one and lasiodin (IC₅₀ < 5 μM) displayed strong cytotoxicity against the tested tumour cells, indicating the potential for new chemotherapeutic drugs.     

剑桥滤片-液-液捕集系统各部分烟气捕集物的细胞毒性比较

为考察烟气捕集在卷烟主流烟气体外细胞毒性检测中的作用,采用3种捕集系统:剑桥滤片-pH7.0 PBS-丙酮、剑桥滤片-pH7.2 PBS-乙酸乙酯和剑桥滤片-pH7.4 PBS-70％甘油捕集同一卷烟主流烟气的粒相物和气相物,用中性红细胞毒性法检测了各部分烟气捕集物对中国仓鼠卵巢细胞(CHO)的毒性作用,气相色谱-质谱法检测了3种有机溶剂烟气捕集物的化学成分.结果表明:①细胞毒性的大小顺序为:剑桥滤片捕集物＞ PBS捕集物＞有机溶剂捕集物;②在第2级捕集物中,pH7.4 PBS烟气捕集物的细胞毒性显著大于pH7.0和pH7.2 PBS烟气捕集物;③在第3级捕集物中,70％甘油烟气捕集物的细胞毒性最大,丙酮和乙酸乙酯的较小,且二者比较接近;④3种有机溶剂捕集的烟气气相物部分主要是醛类、酯类、烷烃和苯系物,70％甘油捕集了较多的烷烃和苯系物.剑桥滤片捕集的烟气冷凝物反映了部分烟气对CHO细胞的中性红细胞毒性,剑桥滤片-pH7.4 PBS溶液-70％甘油捕集的烟气物质可以较全面地反映烟气的细胞毒性.     

Chemical fingerprinting and bioactivity of Amazonian Ecuador Croton lechleri Müll. Arg. (Euphorbiaceae) stem bark essential oil: A new functional food ingredient?

Croton lechleri essential oil has been obtained by steam distillation of fresh stem bark from Amazonian Ecuador adult plants (yield: 0.61 ml/kg [0.061%]; density: 1.01 g/ml), and then chemically characterised by GC (Gas Chromatography) and GC–MS (gas chromatography–mass spectrometry). Seventy-four chemicals were detected and identified; the most abundant in descending order, were the sesquiterpenes sesquicineole (17.29%), α-calacorene (11.29%), 1,10-di-epi-cubenol (4.75%), β-calacorene (4.34%) and epi-cedrol (4.09%). Monoterpenes checked with a relative peak area higher than 2.0% were α-pinene (2.01%), p-cymene (2.61%), limonene (4.20%) and borneol (2.67%). The structure of the main chemicals were confirmed by GC–MS and ¹H NMR analyses. Spectrophotometric 1,1-diphenyl-2-picrylhydrazyl (DPPH) and DPPH-(high performance) thin layer chromatography (DPPH-(HP)TLC) bioautographic assays showed a lower radical scavenging capacity (IC₅₀) with respect to commercial thyme essential oil and BHA (butylated hydroxyl anisole), pointing out, however, that the C. lechleri essential oil fraction, characterised by α-calacorene, β-calacorene and δ-cadalene, was the most involved in the bioactivity. Similar results were obtained with β-carotene bleaching assay, where the IC₅₀ values were 0.291 ± 0.024 mg/ml for C. lechleri essential oil, 0.164 ± 0.013 and 1.34 × 10⁻⁴ ± 10⁻⁵ mg/ml for thyme essential oil and BHA, respectively. (HP)TLC-bioautographic assay performed with Gram positive and Gram negative bacteria revealed a minimum inhibitory concentration (MIC) values comprised between 0.10 mg/ml (Escherichia coli) and 10.10 mg/ml (for e.g. Pseudomonas aeruginosa), and the fraction mainly characterised by sesquicineole (97.38%) as the most involved in antibacterial capacity. Ames test employing Salmonella typhimurium TA98 and TA100 with and without a metabolic activation mixture (S9 mix) demonstrated the absence of mutagenicity of the C. lechleri essential oil between a concentration range of 10⁻² and 100 mg/plate. The same results were achieved by Saccharomyces cerevisiae D7 strain assay. An interesting mutagen-protective efficacy was evidenced by a 30% and 33% revertants reduction of TA98 strain treated with 2-aminoanthracene and nitrofluorene (2 μg/plate), suggesting, above all, the possibility to employ C. lechleri essential oil as a new flavouring protective ingredient for foods or dietary supplements against potential mutagens formed during cooking and/or processing in general.     

A new cytotoxic cyclic pentadepsipeptide,neo-N-methylsansalvamide produced by Fusarium solani KCCM90040, isolated from potato

A new cytotoxic cyclic pentadepsipeptide, neo-N-methylsansalvamide, was produced by Fusarium solani KCCM90040, which was isolated from potato in Korea. The species of Fusarium was identified as F. solani by examining its morphological characteristics and by ITS-5.8rDNA sequence analysis. This compound was analysed for C₃₃H₅₂N₄O₆ by electrospray ionisation mass spectrometry and combined structural analysis. The one and two-dimensional NMR and the absolute configurations of amino acids spectral data allowed the resolution of five subunits linked in the following order: (S)-2-hydroxy-4-methylpentanoic acid, N-methyl-l-leucine, l-valine, l-leucine, and l-phenylalanine. The in vitro cytotoxic effect of the purified cyclic pentadepsipeptide was evaluated to establish the possibility that it would be a biohazard if present in foods. The concentrations of purified cyclic pentadepsipeptide required to inhibit cell growth in vitro by 50% for A549 (lung cancer), SK-OV-3 (ovarian cancer), SK-MEL-2 (skin melanoma), and MES-SA (uterine sarcoma) cell lines were 10.7 ± 0.15, 11.2 ± 1.23, 10.0 ± 0.53, and 14.0 ± 0.74 M, respectively (mean ± SE).     

Early determination of toxicant concentration in water supply using MHE

In this paper, a novel application of state estimation in environmental engineering is presented. The objective is to use on-line estimation techniques including moving horizon estimator (MHE) and extended Kalman filer (EKF) for an early concentration estimation of toxic agent presented in water supply. These estimation techniques (MHE and EKF) can be integrated in an early warning system of several features including the ability of early detection and quantification of the presence of toxicants in the water supply system. The estimation is based on dynamic measurements generated by a real-time cell electronic sensor (RT-CES) and on existing cytotoxicity mathematical dynamic models.     

The effect of humic acids on the cytotoxicity of silver nanoparticles to a natural aquatic bacterial assemblage

The effect of a terrestrial humic acid (HA) and a river HA on the cytotoxicity of silver nanoparticles (AgNPs) to natural aquatic bacterial assemblages (0 μM, 2.5 μM and 5 μM) was measured with spread plate counting. The effect of HA (20 and 40 ppm) on the cytotoxicity of AgNPs ranging in size between 15 and 25 nm was tested in the presence and in the absence of natural sunlight. The experiment was a full factorial, completely randomized design and the results were analyzed using the General Linear Model in SAS. LSMEANS was used to separate the means or combinations of means. Significant main effects of all independent variables, plus interaction effects in all cases except HA/LI and HA/AgNPs/LI were observed. The toxicity of AgNPs to natural aquatic bacterial assemblages appears to be concentration dependent for concentrations between 0 μM and 5 μM. The data indicate that the light exposure inhibited viability more than the darkness exposure. The HA treatment groups in the presence of light showed greater reduced viability count compared to darkness exposure groups. The inhibition of bacterial viability counts by AgNPs exposure was less in the light treatment groups containing a terrestrial HA compared to that with a river HA. Difference in the extent of reactive oxygen species formation and adsorption/binding of AgNPs was speculated to account for the observed phenomenon.     

Controlled drug release carriers based on PCL/PEO/PCL block copolymers

In order to create a new drug delivery system, the ibuprofen-loaded triblock copolymer PCL/PEO/PCL (PCEC) microspheres with a low PEO content (<2?wt%) were prepared by oil in water (o/w) solvent evaporation technique. The influence of PEO content, molecular weight of a polymer matrix and drug loading on the ibuprofen release profiles were evaluated. The interactions between polymer matrix and ibuprofen were detected by FTIR analysis. The presence of hydrophilic PEO segment in PCL chains caused the decrease in particle size, which further had a great impact on the drug release kinetics, i.e., initially faster release and significantly higher quantity of released drug compared to neat PCL. Ibuprofen release behavior from polymer matrix was governed by a diffusion process. In vitro cytotoxicity tests revealed that empty PCL and PCEC microspheres were not toxic at low concentrations, while ibuprofen-loaded microspheres exhibited cytotoxicity correlated with amounts of incorporated drug.     

Formulation of Superparamagnetic Iron Oxides by Nanoparticles of Biodegradable Polymers for Magnetic Resonance Imaging

A system of poly(lactide‐co‐glycolide)‐methoxy poly(ethylene glycol) (PLGA‐mPEG) nanoparticles is developed to formulate superparamagnetic iron oxides (IOs) for magnetic resonance imaging (MRI). This system improves the imaging effects, increases the half‐life of the IOs in circulation, and reduces their side effects. The IO‐loaded PLGA‐mPEG nanoparticles were prepared by a modified water‐in‐oil‐in‐water double‐emulsion technique. Their physicochemical and superparamagnetic properties were characterized by various techniques. In vitro IO release kinetics from the nanoparticles and stability of the IO‐loaded polymeric nanoparticles were also investigated. In vitro and ex vivo MRI of the IOs formulated in the PLGA‐mPEG nanoparticles show that the saturation magnetization and the r₂, r₂* relaxivities are enhanced, and the contrast effects are improved in comparison with commercial IOs (Resovist). It is proven that the enhanced superparamagnetic properties are caused by the polymeric nanoparticle formulation but not by the polymeric material itself. Moreover, the PLGA‐mPEG nanoparticle formulation achieves 36.9 and 35.6 % less cytotoxicity in comparison with the IOs (Resovist) after 48 h incubation at the same 20 and 50 μg mL^–1 Fe concentration, respectively. This research implies that formulation of IOs by nanoparticles of PLGA‐mPEG copolymer or other biodegradable polymers could be promising for more effective and sustainable MRI with reduced side effects, which, with targeting probes conjugated to the nanoparticle surface, can be further used to promote cellular and molecular MRI.     

In vitro study on equal channel angular pressing AZ31 magnesium alloy with and without back pressure

The equal channel angular pressing (ECAP) technique with and without back pressure (BP) was introduced in this paper to prepare biomedical AZ31 magnesium alloy, with the effect of pass number (from 1 to 4) on the corrosion properties as well as in vitro biocompatibility being investigated. The results indicated that ECAPed or BP-ECAPed AZ31 alloys exhibited similar corrosion rate to that of the as-extruded one, but the corrosion rate slightly increased after 1-2 passes ECAP or BP-ECAP and further decreased after 4-pass procedure. Additionally, severe local corrosion was observed for the 1-3 passes ECAPed or BP-ECAPed AZ31 alloy samples. Compared to the as-extruded AZ31 alloy, the samples after ECAP or BP-ECAP procedure showed much smaller sized corrosion pits on the surface after removing the corrosion product. The surface analysis after 20 days immersion in Hank's solution revealed that the composition of the corrosion product consisted of C, O, Mg, P, Ca whereas only weak signal of Mg(OH)₂ could be detected beside the dominant α(Mg) peak by X-ray diffraction. The cytotoxicity results suggested that the multi-pass ECAPed or BP-ECAPed AZ31 alloy exhibited Grade I-II cytotoxicity according to ISO 10993-5: 1999.