1,2,3,4,6-penta-O-galloyl-β-D-glucose Protects PC12 Cells from MPP^+-mediated Cell Death by Inducing Heme Oxygenase-1 in an ERK- and Akt-dependent Manner

This study examined the ability of 1,2,3,4,6-penta-O-galloyl-β-D-glucose (β-PGG) to induce the expression of heme oxygenase-1 (HO-1) in the PC12 cells and its regulation in the PC12 cells.One week before treatment with the drug,nerve growth factor (NGF) was added to the cultures at a final concentration of 50 ng/mL to induce neuronal differentiation.After drug treatment,HO-1 gene transcription was analyzed by reverse transcription polymerase chain reaction (RT-PCR).Expression of HO-1 and NF-E2-related factor2 (Nrf2) and activation of extracellular signal-regulated kinase (ERK) and Akt were detected by Western blotting.The viability of the PC12 cells treated with different medicines was examined by MTT assay.The oxidative stress in the PC12 cells was evaluated qualitatively and quantitatively by DCFH-DA.The results showed that β-PGG up-regulated HO-1 expression and this increased expression provided neuroprotection against MPP+-induced oxidative injury.Moreover,β-PGG induced Nrf2 nuclear translocation,which was found to be upstream of β-PGG-induced HO-1 expression,and the activation of ERK and Akt,a pathway that is involved in β-PGG-induced Nrf2 nuclear translocation,HO-1 expression and neuroprotection.In conclusion,β-PGG up-regulates HO-1 expression by stimulating Nrf2 nuclear translocation in an ERK-and Akt-dependent manner,and HO-1 expression by β-PGG may provide the PC12 cells with an acquired antioxidant defense capacity to survive the oxidative stress.

DNA Methyltransferases Directed Anti-Cancerous Plant Medicine (Xanthomicrol and Galloyl) Based Molecular Docking and Dynamics Simulation

DNA methyltransferases 1 (DNMT1) has been looked as crucial targets against various types of cancers. MD simulations have advanced to a point where the atomic level information of biological macromolecule (protein or DNA-protein or protein-protein) can easily be advantageous to predict the functionality. In this study we utilize xanthomicrol and galloyl compounds to investigate potential compounds for the inhibition of DNMT1, and the results of these two compounds are compared with drug decitabine. Xanthomicrol and galloyl are found to dock successfully within the active site of DNMT1. A comparison of the inhibitory potential of screened xanthomicrol inhibited DNMT1 approximately is identical with those of their corresponding drugs, decitabine. The stability of the DNMT1 with the best docked xanthomicrol, were further analysed in molecular dynamics (MD) simulation and compared with those of the respective drugs namely decitabine which revealed stabilization of these complexes within 300 ns of simulation with better stability of DNMT1.

Effects of 1,2,4,6-tetra-O-galloyl-β-D-glucose from P. emblica on HBsAg and HBeAg Secretion in HepG2.2.15 Cell Culture

A polyphenolic compound, 1,2,4,6-tetra-O-galloyl-β-D-glucose (1246TGG), was isolated from the traditional Chinese medicine Phyllanthus emblica L. (Euphorbiaceae) and assayed for its potential as an anti-hepatitis B virus (HBV) agent. The cytotoxicity of 1246TGG on HepG2.2.15 as well as HepG2 cells was determined by observing cytopathic effects, and the effects of 1246TGG on secretion of HBsAg and HBeAg in HepG2.2.15 cells were assayed by enzyme immunoassay. Results indicates that treatment with 1246TGG (6.25 μg/mL, 3.13 μg/mL), reduced both HBsAg and HBeAg levels in culture supernatant, yet the inhibitory effects tend to decline with the assay time. This study provides a basis for further investigation of the anti-HBV activity and possible mechanism of action of 1246TGG.

1,2,3,4,6-penta-O-galloyl-β-D-glucose up-regulates heme oxygenase-1 expression by stimulating Nrf2 nuclear translocation in an extracellular signal-regulated kinase-dependent manner in HepG2 cells

AIM: To examine the potency of 1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG) as a hepatic heme oxygen-ase-1(HO-1) inducer and its regulation in HepG2 cells. METHODS: Expression of HO-1 and NF-E2-related factor 2 (Nrf2) and activation of mitogen-activated protein (MAP) kinases were analyzed by Western blot, immuno-fluorescence assay, and flow cytometry. Transfections of HO-1 gene, small interfering RNAs for HO-1 and Nrf2, and dominant-negative gene for MAP/extracellular signal-regulated kinase (ERK) were carried out to dissect the signaling pathways leading to HO-1 expression in HepG 2 cells. RESULTS: PGG up-regulated HO-1 expression and this expression conferred cytoprotection against oxidative injury induced by t-butyl hydroperoxide. Moreover, PGG induced Nrf2 nuclear translocation, which was found to be an upstream step of PGG-induced HO-1 expression, and ERK activation, of which pathway was involved in PGG-induced Nrf2 nuclear translocation, HO-1 expression and cytoprotection. CONCLUSION: PGG up-regulates HO-1 expression by stimulating Nrf2 nuclear translocation in an ERK-depen-dent manner, and HO-1 expression by PGG may serve as one of the important mechanisms for its hepatoprotective effects.

Metabolite characterization of Penta-O-galloyl-β-D-glucose in rat biofluids by HPLC-QTOF-MS

Objective： To understand the in vivo metabolic fate of 1,2,3,4,6-Penta-O-galloyl-β-d-glucose（PGG）naturally existed in many medicinal herbs and food plants such as Rhus chinensis,Paeonia suffruticosa,Paeonia lactiflora and Mango.Methods： The metabolites of PGG in rat biofluids were characterized using high performance liquid chromatography combined with quadrupole time-of-flight tandem mass spectrometry（HPLC-QTOF-MS）.Results： Ten metabolites in urine,five metabolites in feces and two metabolites in plasma,were observed when the rats were administrated with a single intravenous injection of PGG（20 mg/kg）.Conclusion： PGG is firstly metabolized to gallic acid,then gallic acid undergoes sulfation,glucuronidation and methylation by rat liver.The determination of metabolites and the proposed metabolic pathway of PGG in vivo will be benefit to gain deeper insights into its pharmacological activities.

galloyl pedunculagin作为C-激酶自动磷酸化有效抑制剂的进一步研究

galloyl pedunculagin(GP)从化香树(Platycarya strobilacea)中分离得到。本次检测了GP体外对两种C-激酶亚型（C-激酶α和C-激酶η)自动磷酸化及其酶活性的抑制作用。实验包括：①GP对两种C-激酶亚型自动磷酸化的有效抑制。②GP体外抑制C-激酶活性的动力学。③圆二色性(CD)分析：用合成的含脯氨酸片段(PVLTPP)研究GP在C-激酶上的结合位点。

茶树单宁酶CsTA的理化性质及其在绿茶饮料中的应用

茶叶中的酯型儿茶素对于绿茶滋味有着重要的影响,但是夏秋季节茶树中积累过多的酯型儿茶素会降低茶叶感官品质。前期发现的茶树单宁酶CsTA具有水解酯型儿茶素的功能,但其理化性质以及能否在绿茶饮料加工中发挥一定作用尚不清楚。在前期试验结果的基础上利用液相色谱技术对CsTA进行进一步探究。结果表明,单宁酶CsTA的最适反应温度为45℃、热稳定范围在60℃以下、最适反应pH为7.0,Mg^(2+)对单宁酶CsTA活性有明显的激活作用,Cu2+可使其完全失活,Mn^(2+)、Zn^(2+)、Al^(3+)、Fe^(3+)、Fe^(2+)、Li^(+)对单宁酶CsTA活性具有一定抑制作用,CsTA在冷冻干燥后有很好的贮存稳定性。将茶树单宁酶CsTA应用于绿茶茶汤后发现,当茶树单宁酶CsTA添加量为11μg、料液比为1∶100、作用时间20 min、温度为35℃时对绿茶茶汤中酯型儿茶素的降解效果最好。本研究为今后利用CsTA在绿茶饮料生产中降低苦涩味,提升品质提供理论参考。

219份茶树资源1,2,6-三没食子酰葡萄糖变异分析

为探究1,2,6-TGGP(1,2,6-tri-O-galloyl-β-D-glucopyranose,1,2,6-三没食子酰葡萄糖)变异特性,以2019—2021年浙江杭州和嵊州两个地区的219份茶树资源为材料,利用高效液相色谱法测定样品中的1,2,6-TGGP含量。结果表明,这些茶树资源的1,2,6-TGGP变化范围为0.34~53.63 mg/g,平均值为9.53 mg/g;其中高1,2,6-TGGP(1,2,6-TGGP≥30 mg/g)茶树资源13份,占比5.94%。相关性分析结果显示,1,2,6-TGGP与EGCG和ECG呈极显著正相关,与EGC和EC呈极显著负相关。本研究可为选育高1,2,6-TGGP含量茶树品种提供理论基础。

萹蓄抑菌活性及化学成分研究

本文研究萹蓄Polygonum aviculare L.乙酸乙酯萃取部位的抑菌活性和化学成分。采用打孔法进行抑菌活性实验,采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱等方法进行分离和纯化,并根据理化性质、光谱数据进行结构鉴定。结果萹蓄乙酸乙酯部位对五种试验菌均显示一定的抑菌活性,并从中分离得到10个化合物,分别鉴定为没食子酸甲酯(1)、β-胡萝卜甙(2)、山柰酚(3)、槲皮素(4)、没食子酸(5)、萹蓄苷(6)、槲皮苷(7)、myricetin 3-O-(3''-O-galloyl)-rhamnopyranoside(8)、杨梅树皮苷(9)、胡桃宁(10)。其中化合物1和8为首次从该植物中分离得到,化合物8为首次从蓼科蓼属植物中分离得到。

萹蓄乙酸乙酯部位化学成分的抑菌活性研究（英文）

萹蓄(Polygonum aviculare L.)是一种常用中药,具有杀虫止痒,治疗黄疸等功效。本文采用打孔法分别对其乙酸乙酯部位分离得到的十个化合物进行了抑菌活性实验,结果表明,除化合物1、2、9、10外,其它化合物均对不同的菌种呈现出不同的抑菌活性,并且呈一定的剂量效应。本实验为萹蓄及其化学成分作为天然的抑菌活性物质研究开发提供理论依据。

β-1,2,3,4,6-五-O-倍酰-D-葡萄糖与人血清白蛋白的相互作用研究

应用红外光谱和荧光光谱方法研究了人血清白蛋白 (HSA)与 β 1,2 ,3 ,4,6 五 O 倍酰 D 葡萄糖 (PGG)的相互作用 .荧光光谱结果显示 ,PGG在CPGG/CHSA<0 5和 0 5 <CPGG/CHSA<3两个浓度范围内在HSA分子上分别有一个和两个结合位点 ,结合常数分别为 1 66× 10 4和 8 98× 10 8L·mol-1.运用蛋白质红外光谱酰氨Ⅲ带和酰氨Ⅰ带结合的方法对HSA与PGG作用后二级结构的变化进行了定量分析 .随着药物浓度的增加 ,PGG和HSA之间的相互作用主要使HSA的二级结构发生了由α 螺旋向 β 转角和无规结构的转化 .结合荧光光谱和红外光谱结果 ,探讨了HSA与不同浓度PGG作用引起的荧光猝灭与二级结构变化之间的关系 。

河套大黄的蒽醌类成分研究

从河套大黄干燥根与根茎的甲醇提取物中分得 10个蒽醌类成分。经化学方法和波谱学鉴定 ,确定它们的结构分别为 :大黄酚 (chrysophanol, )、大黄素甲醚 (physcion, )、大黄素 (emodin, )、芦荟大黄素 (aloe-emodin, )、大黄酸 (rhein, )、大黄酚 - 1和 8- O- β- D-吡喃葡萄糖苷 (chrysophanol- 1and 8- O- β- D-glucopyranoside, a和 b)、大黄酚 - 8- O-β- D- (6′- O-没食子酰 ) -吡喃葡萄糖苷〔chrysophanol- 8- O-β- D- (6′- O-galloyl) - glucopyranoside, 〕、大黄素甲醚 - 8- O- β- D-吡喃葡萄糖苷 (physcion- 8- O- β- D- glucopyranoside, )、芦荟大黄素 - 8- O- β- D-吡喃葡萄糖苷 (aloe- emodin- 8- O- β- D- glucopyranoside, )。其中 为一新化合物 , 、 、 系首次从该植物中分得。

落叶松原花青素的没食子酰化及其抗氧化活性增强效应

对落叶松树皮提取分离的原花青素(PC)进行没食子酰化反应,在其分子结构中引入具有邻三酚羟基的没食子酰基,获得改性产物没食子酰化原花青素(GPC)。红外光谱分析表明:PC经过没食子酰化反应,产物GPC形成了原花青素没食子酯的结构,羟基的数量得到增加。通过HPLC法测定产物GPC水解后生成的没食子酸量,计算其没食子酰化度为63%。测定比较了PC和GPC对DPPH自由基(DPPH.)的清除能力以及对过渡金属离子的络合能力和对油脂抗氧化性能的效果。结果表明原花青素经过没食子酰化后,其改性产物的抗氧化活性得到显著增强。

茶树新梢中非酯型儿茶素及其合成酶的变化规律

对不同季节茶树新梢不同部位鲜叶中儿茶素组分和非酯型儿茶素合成酶的变化规律进行了研究。结果表明,在茶树新梢上,从芽到第四叶,四种非酯型儿茶素中除了GC外,C、EC和EGC含量均逐步增加;两种非酯型儿茶素合成酶中,DFR/LAR活性呈下降趋势,而ANR在第三叶中达到最高。相关分析进一步表明,不同部位鲜叶中儿茶素的总量变化与DFR/LAR活性变化呈显著正相关,而与ANR变化相关性不大。

三没食子酰吡喃葡糖作用于gp41抑制HIV与靶细胞的融合

目的检测来源于蛇菰科植物日本蛇菰中的单体化合物三没食子酰吡喃葡萄糖(TGGP)抑制HIV与靶细胞融合的活性,并探讨其作用靶点。方法用萃取和柱层析方法分离提纯TGGP,用酶联免疫测定法、天然聚丙烯酰胺凝胶电泳、分子排阻高效液相色谱法检测其抑制HIVgp41六螺旋束结构形成的作用,用细胞-细胞融合方法检测TGGP抑制HIV进入靶细胞的活性。结果酶联免疫测定法表明TGGP能有效地抑制gp41六螺旋束结构的形成,其半数抑制浓度(IC50)为(1.37±0.19)μg·ml-1。进一步用生物物理方法直观地确证了TGGP抑制gp41六螺旋束结构形成的作用。在生物学活性方面,50μg·ml-1的TGGP能有效地抑制HIV包膜糖蛋白介导的细胞-细胞融合。结论HIV进入靶细胞的过程由跨膜糖蛋白亚基gp41介导。三没食子酰吡喃葡糖(TGGP)能作用于gp41,抑制HIV与靶细胞的融合。该化合物可望作为阴道外用杀微生物剂,预防HIV的性传播。

中药大血藤的酚性化合物

目的对中药大血藤干燥藤茎的化学成分进行研究。方法采用现代色谱技术分离化合物,运用现代波谱技术(IR,MS,~1H NMR,^(13)C NMR,~2DNMR)对所得化合物的结构进行鉴定。结果从大血藤的藤茎中分得10个酚类化合物,分别鉴定为1-O-(香草酸)-6-(3″,5″-二-O-甲基-没食子酰基)-β-D-葡糖苷(Ⅰ)、(-)-表儿荣素(Ⅱ)、阿魏酸-对羟基苯乙醇酯(Ⅲ)、3-O-咖啡酰奎宁酸(Ⅳ)、3-O-咖啡酰奎宁酸甲酯(Ⅴ)、罗布麻宁(Ⅵ)、香草酸(Ⅶ)、原儿茶酸(Ⅷ)、3,4-二羟基-苯乙醇(Ⅸ)、4-羟基-苯乙醇(Ⅹ)。结论化合物Ⅰ为新化合物,化合物Ⅲ～Ⅵ和Ⅷ～Ⅹ为首次从该植物中分得。

鬼灯擎中丹宁类化合物的分离及结构的核磁共振分析(Ⅱ)

利用Toyopearl HW-40(C)凝胶反复柱层析,从鬼灯擎(Rodsersia aesculifolia Ba-tal.)根茎的70％Me_2CO提取物中分离得到六种丹宁类化合物,其中四种经化学及核磁共振分析分别确定其结构为3-0-没食子酰基-(-)-表儿茶素[3-0-galloyl-(-)-epicatechin]RA-11,1,3-0-没食子酰基-表儿茶素-(4β-8)-(3-0-没食子酰基)-表儿茶素[(3-0-galloyl)-epieatechin-(4β-8)-(3-0-Salloyl)-epicatechin]RA-13,2;1,2,4,6-四-0-没食子酰基-β-D-葡萄糖[1,2,4,6-tetra-0-galloyl-β-D-glucose]RA-14,3和没食子酸甲酯(methyl gallate)RA-16,4。RA-14为首次获得的结晶性没食子丹宁,这些成分均为首次从该植物中得到。

多酚羧酸合成功能高分子材料研究(Ⅱ)——没食子酰化改性纤维素合成及其功能特性试验

以没食子酰基为功能基团,以改性纤维素为骨架合成功能高分子材料没食子酰化改性纤维素(没食子酰基-1,6-己二亚胺基-羟丙基-纤维素,CG):先将纤维素与环氧氯丙烷反应,然后依次接上己二胺桥链和三乙酰基没食子酰基,最后将没食子酰基脱去乙酰基得到目标产物。功能试验表明,1g产物能结合明胶49.5mg,并可再生使用。1g产物络合金属离子的能力:Fe3+53.4mg,Cu2+38.7mg,Hg2+46.5mg,Mn2+6.8mg,Zn2+27.9mg,Pb2+57.2mg。产物在稀酸、稀碱、稀醇和热水中具有稳定性。

没食子酰基金丝桃甙的抗氧化性及其构效关系研究

目的 通过对没食子酰基金丝桃甙 (Gq)清除氧自由基作用的测定 ,探讨Gq的抗氧化性并对其抗氧化机理与结构之间的关系进行探讨。方法 分别采用黄嘌呤 黄嘌呤氧化酶体系及Fenton反应体系 ,测定Gq对超氧阴离子自由基 (SAFR)和羟基自由基 (HFR)的清除作用 ,得出清除率与浓度之间的相关关系 ,求出IC50 值 ,以表示其抗氧化能力。对比分析Gq及天然抗氧剂槲皮素和芦丁的化学结构 ,探讨抗氧化机理与结构之间的构效关系。 结果 Gq对氧自由基具有明显的清除活性 ,清除SAFR和HFR的IC50 值分别为 4 0 .8μmol·L-1和 33.5 μmol·L-1,远小于阳性对照物槲皮素 (分别为 114 .0 μmol·L-1和 10 0 .8μmol·L-1)及芦丁 (15 2 .0 μmol·L-1和 91.4 μmol·L-1)。结论 Gq具有明显的抗氧化性 ,其抗氧化活性与其分子结构中多元酚结构有关 。

粗叶悬钩子Rubus aleaefolius Poir.中三个新的细胞周期抑制剂 :一个新的和两个已知的水解鞣质(英文)

通过跟踪分离活性成分 ,从粗叶悬钩子RubusaleaefoliusPoir .中分到一个新的鞣花酸鞣质化合物 1和两个已知的没食子酸鞣质 1,2 ,3,6 tetra O galloyl β D glucopyranose(2 )和 1,2 ,3,4 ,6 penta O galloyl β D glucopyranose(3) ,并通过谱学手段确定了新化合物 1的化学结构。化合物 1～ 3将tsFT2 10癌细胞的细胞周期抑制在G0 /G1期 ,MIC值分别为2 2 1μmol·L-1(1) ,7 9μmol·L-1(2 )和 6 6 μmol·L-1(3) ,系三个新的G0 /G1期抑制剂。化合物 1～ 3作为鞣质类化合物的细胞周期抑制剂亦属首例 。