A novel bio‐based phthalonitrile resin derived from catechin: synthesis and comparison of curing behavior with petroleum‐based counterpart

The development of bio‐based thermosetting resins with good thermal stability can potentially afford sustainable polymers as replacements for petroleum‐based polymers. We report a practical route to a novel catechin‐based phthalonitrile resin precursor (CA‐Ph), which contains free phenolic hydroxyl groups that result in ‘self‐curing’ at elevated temperatures to afford a thermostable polymer. Comparison of the performance of this CA‐Ph resin with that of a conventional petroleum‐based bisphenol A phthalonitrile resin (BPA‐Ph; containing 5 wt% of the curing agent 4,4′‐diaminodiphenylsulfone) revealed that CA‐Ph exhibits a lower melting point and curing temperature. Cured CA‐Ph resin retains 95% of its weight at 520 °C under a nitrogen atmosphere, which compares favorably with results obtained for BPA‐Ph resin that retains 95% of its weight at a lower temperature of 484 °C. Kinetic results indicated that the curing reactions of both CA‐Ph and BPA‐Ph systems follow an autocatalytic mechanism. These results suggest that catechin is a useful bio‐based feedstock for the preparation of self‐curing and thermally stable phthalonitrile resins for advanced technological applications. © 2017 Society of Chemical Industry     

Epigallocatechin-3-Gallate-Loaded Liposomes Favor Anti-Inflammation of Microglia Cells and Promote Neuroprotection

Microglia-mediated neuroinflammation is recognized to mainly contribute to the progression of neurodegenerative diseases. Epigallocatechin-3-gallate (EGCG), known as a natural antioxidant in green tea, can inhibit microglia-mediated inflammation and protect neurons but has disadvantages such as high instability and low bioavailability. We developed an EGCG liposomal formulation to improve its bioavailability and evaluated the neuroprotective activity in in vitro and in vivo neuroinflammation models. EGCG-loaded liposomes have been prepared from phosphatidylcholine (PC) or phosphatidylserine (PS) coated with or without vitamin E (VE) by hydration and membrane extrusion method. The anti-inflammatory effect has been evaluated against lipopolysaccharide (LPS)-induced BV-2 microglial cells activation and the inflammation in the substantia nigra of Sprague Dawley rats. In the cellular inflammation model, murine BV-2 microglial cells changed their morphology from normal spheroid to activated spindle shape after 24 h of induction of LPS. In the in vitro free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, EGCG scavenged 80% of DPPH within 3 min. EGCG-loaded liposomes could be phagocytized by BV-2 cells after 1 h of cell culture from cell uptake experiments. EGCG-loaded liposomes improved the production of BV-2 microglia-derived nitric oxide and TNF-α following LPS. In the in vivo Parkinsonian syndrome rat model, simultaneous intra-nigral injection of EGCG-loaded liposomes attenuated LPS-induced pro-inflammatory cytokines and restored motor impairment. We demonstrated that EGCG-loaded liposomes exert a neuroprotective effect by modulating microglia activation. EGCG extracted from green tea and loaded liposomes could be a valuable candidate for disease-modifying therapy for Parkinson’s disease (PD).     

A polyphenolic biomacromolecule prepared from a flavonoid: Catechin as degradable microparticles

Catechin (CAT) was crosslinked with trimethylolpropane triglycidyl ether (TMPTGE) to obtain degradable poly(CAT) particles in a single step. Spherical p(CAT) particles with tens of micrometer size range and an isoelectronic point at pH 1.2 were obtained. The hydrolytic degradation of p(CAT) particles provided sustainable and extended release with 264 mg/g CAT release within 10 days at pH 7.4. The antioxidant capacity of 55.0 ± 0.9 μg/ml gallic acid equivalent in terms of total phenol content, and 0.88 ± 0.3 μmol/g trolox equivalent were estimated for p(CAT) particles displaying strong radical scavenging capability. Blood clotting and hemolysis assays demonstrated dose-dependent blood compatibility revealing higher blood compatibility for p(CAT) particles up to 10 μg/ml concentration. The cytotoxicity results show that p(CAT) particles have almost no toxicity for CCD841 normal colon cells at 250 μg/ml concentration in 24 h incubation time giving ~97% cell viability, whereas CAT molecules only provide ~34% cell viability.     

Green and gold kiwifruit peel ethanol extracts potentiate pentobarbital-induced sleep in mice via a GABAergic mechanism

Kiwifruit is one of the most popular fruits worldwide, and it has various biological properties, including antioxidant, anti-allergic, and cardiovascular protective effects. The peel of kiwifruit, which is a by-product of processing, is a good source of flavonoids; however, its bioactivity has not been widely investigated. In this study, we evaluated the hypnotic effects of green (GRPE, Actinidia deliciosa) and gold (GOPE, Actinidia chinensis) kiwifruit peel ethanol extracts and their solvent fractions, and the possible underlying mechanisms. Oral GRPE and GOPE administration (125–1000 mg/kg) produced a dose-dependent decrease in sleep latency and an increase in sleep duration in pentobarbital-treated mice. Among three different solvent fractions of GRPE and GOPE, ethyl acetate (EA) fractions had the greatest effect on sleep duration at 250 mg/kg. The total flavonoid contents of solvent fractions were proportional to sleep duration. Like diazepam (a GABA_A–benzodiazepine (BZD) receptor agonist), the hypnotic effects of GRPE, GOPE, and their EA fractions were fully inhibited by flumazenil (a GABA_A–BZD receptor antagonist). These results suggest that potentiation effects of GRPE and GOPE on pentobarbital-induced sleep in mice may be modulated by a GABAergic mechanism.     

缩醛/酮的无气味硫缩醛/酮化反应

在甲醇介质中,氯化乙酰存在下,易制备和稳定的2-（1,3-二噻）亚甲基-3-氧代丁酸作无气味代硫醇试剂能与缩醛/酮有效进行硫缩醛/酮化反应。该反应条件温和,操作简单,产率高,且反应和后处理过程中,无硫醇的恶臭气味。     

微胶囊化儿茶素对阿霉素肾病大鼠总抗氧化能力的影响

目的:探讨微胶囊化儿茶素对阿霉素肾病大鼠总抗氧化能力的影响。方法:将60只雌性SD大鼠随机分为对照组、肾病组、激素组、VE组、儿茶素组和微胶囊组共六组,尾静脉一次性注射阿霉素(5mg/kg)制备肾病模型;实验第六周末杀鼠取尿、血、肾及肝脏,利用生化法测定血、肾及肝脏总抗氧化能力和·OH,利用考马斯亮蓝法测定24h尿蛋白的排泄量。结果:微胶囊组大鼠血、肾及肝脏中总抗氧化能力显著高于儿茶素组(p<0.01);微胶囊组大鼠·OH的浓度在肾与肝脏中显著低于儿茶素组(p分别<0.05,0.01),在血清中无显著性差异;微胶囊化儿茶素治疗组24h尿蛋白排泄量显著低于儿茶素治疗组(p>0.05)。结论:微胶囊化儿茶素可能是通过提高肾病大鼠总抗氧化能力,有效清除·OH,达到降低肾病大鼠尿蛋白排泄的目的。     

Green Tea Formulations with Vitamin C and Xylitol on Enhanced Intestinal Transport of Green Tea Catechins

The effect of green tea formulated with vitamin C and xylitol on intestinal cell transport of gallated and nongallated catechin was studied. The transport of catechins from both apical to basolateral and basolateral to apical directions was measured. The effect of vitamin C (4, 10, 20 ppm), xylitol (11, 27.5, 55 ppm), and combinations of both on the intestinal transport rate of catechins was examined. The efflux value (Pb→a/Pa→b) of (–)‐epigallocatechin (EGC), (–)‐epigallocatechin gallate (EGCG), (–)‐epicatechin (EC), and (–)‐epicatechin gallate (ECG) was 0.26, 0.22, 1.22, and 0.17, respectively, indicating that EC appeared to be less absorbed compared with other catechins. The addition of xylitol (11, 27.5, 55 ppm) and vitamin C (4, 10, 20 ppm) and in combination enhanced transport rate of nongallated catechins such as EC and EGC. For EC, vitamin C was revealed to be the most effective on intestinal transport, implying the inhibition of the efflux transport mechanism of EC. Intestinal transport of gallated catechins significantly increased from catechins formulated with vitamin C and xylitol in a dose‐dependent manner compared to the catechin‐only formulation. Results provide a potential strategy to enhance the delivery and bioavailability of catechins in humans by modulating green tea formulation with vitamin C and xylitol.     

Evaluation of the antioxidant and antiproliferative activities of extracted saponins and flavonols from germinated black beans (Phaseolus vulgaris L.)

Flavonoids and saponins from common beans have been widely studied due to their bioactivity. This research evaluated the effect of germination of black beans (Phaseolus vulgaris L.) on the antioxidant capacity and antiproliferative activity against cancer cell lines of saponins and flavonoids extracted from seed coats, cotyledons and sprouts. Principal component analysis was performed to achieve punctual associations between the black bean saponins and flavonoids concentrations to the antioxidant capacity and the antiproliferative activities. Total phenolic content and antioxidant capacity of extracts were higher when obtained from seed coats, mainly from the 3rd germination day. The extracts obtained from seed coats after 3 and 5 germination days inhibited all cancer cell lines proliferation with no cytotoxicity against control cells. Genistein was related with the activity against mammary cancer cells but flavonols and group B saponins were more related with hepatic and colon cancers. Non-glycosilated flavonols were related with antioxidant capacity.     

Metabolic profile and biological activities of Lavandula pedunculata subsp. lusitanica (Chaytor) Franco: Studies on the essential oil and polar extracts

We investigated the metabolic profile and biological activities of the essential oil and polar extracts of Lavandula pedunculata subsp. lusitanica (Chaytor) Franco collected in south Portugal. Gas chromatography–mass spectrometry (GC–MS) analysis revealed that oxygen-containing monoterpenes was the principal group of compounds identified in the essential oil. Camphor (40.6%) and fenchone (38.0%) were found as the major constituents. High-performance liquid chromatography with diode array detection (HPLC–DAD) analysis allowed the identification of hydroxycinnamic acids (3-O-caffeoylquinic, 4-O-caffeoylquinic, 5-O-caffeoylquinic and rosmarinic acids) and flavones (luteolin and apigenin) in the polar extracts, with rosmarinic acid being the main compound in most of them. The bioactive compounds from L. pedunculata polar extracts were the most efficient free-radical scavengers, Fe²⁺ chelators and inhibitors of malondialdehyde production, while the essential oil was the most active against acetylcholinesterase. Our results reveal that the subspecies of L. pedunculata studied is a potential source of active metabolites with a positive effect on human health.