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.     

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.     

黑莓清汁贮藏期间二次沉淀的研究

分析了黑莓清汁贮藏六个月后二次沉淀的化学成分,讨论了影响二次沉淀的主要因素。结果表明,冷冻干燥的二次沉淀中含有蛋白质15.67%、多酚50.39%、总糖13.19%、灰分1.73%。氨基酸分析表明黑莓含有较多的脯氨酸等混浊活性蛋白质,而含有组氨酸较多的蛋白质也容易形成二次沉淀。采用气相色谱(GC)、高效液相色谱-质谱联用技术(HPLC-MS)分别分析了黑莓清汁二次沉淀的糖和酚类物质成分。与贮藏前相比,贮藏六个月后,黑莓清汁中的酚酸类、儿茶素及其衍生物大为减少。固体核磁共振检测发现,黑莓清汁二次沉淀中的聚合物是缩合单宁类化合物。在黑莓清汁的贮存过程中,花色苷的C8亲核进攻儿茶素或者表儿茶素的C4,或者儿茶素、表儿茶素的C8亲核进攻花色苷的C4生成缩合单宁,并可能进一步聚合形成多聚体,这些多聚体也会与蛋白质发生相互作用生成二次沉淀。     

茶多酚含量与儿茶素含量关系研究

研究了不同规格茶多酚产品中表没食子儿茶素(EGC)、儿茶素(DL-C)、表没食子儿茶素没食子酸酯(EGCG)、表儿茶素(EC)、没食子儿茶素没食子酸酯(GCG)、表儿茶素没食子酸酯(ECG)6种儿茶素含量及其总量与茶多酚含量的关系.结果发现,对于同种规格用同种原料和同种工艺生产的茶多酚产品,其茶多酚含量与6种儿茶素总量成一定的比例关系.茶多酚含量用酒石酸亚铁分光光度法测定,儿茶素含量用高效液相色谱法测定.     

黑茶水提取物的碳谱分析

通过文献查找和标准样测定,将茶叶的九种化学成分的碳谱特征峰进行整理归属,以此为标准,将十六种黑茶水提取物的碳谱进行对照分析,可将黑茶中的各类成分做出定性确认,但其中仍有许多未知成分,需要使用其他方法分离分析。     

Chemistry of Secondary Polyphenols Produced during Processing of Tea and Selected Foods

This review will discuss recent progress in the chemistry of secondary polyphenols produced during food processing. The production mechanism of the secondary polyphenols in black tea, whisky, cinnamon, and persimmon fruits will be introduced. In the process of black tea production, tea leaf catechins are enzymatically oxidized to yield a complex mixture of oxidation products, including theaflavins and thearubigins. Despite the importance of the beverage, most of the chemical constituents have not yet been confirmed due to the complexity of the mixture. However, the reaction mechanisms at the initial stages of catechin oxidation are explained by simple quinone–phenol coupling reactions. In vitro model experiments indicated the presence of interesting regio- and stereoselective reactions. Recent results on the reaction mechanisms will be introduced. During the aging of whisky in oak wood barrels, ellagitannins originating from oak wood are oxidized and react with ethanol to give characteristic secondary ellagitannins. The major part of the cinnamon procyanidins is polymerized by copolymerization with cinnamaldehyde. In addition, anthocyanidin structural units are generated in the polymer molecules by oxidation which accounts for the reddish coloration of the cinnamon extract. This reaction is related to the insolubilization of proanthocyanidins in persimmon fruits by condensation with acetaldehyde. In addition to oxidation, the reaction of polyphenols with aldehydes may be important in food processing.