Inhibitory Effect of Flavonoid Glycosides from Chlorophytum comosum on Nasopharyngeal Carcinoma 5-8F Cells and Its Mechanism

[Objectives]To study the inhibitory activity of two flavonoid glycosides isolated from Chlorophytum comosum Laxum R.Br on human nasopharyngeal carcinoma(NPC)cell line 5-8F in vitro and its mechanism.[Methods]The flavonoid glycosides were isolated and purified from the ethanol alcoholic extract of the roots of Liliaceae plant Chlorophytum comosum by silica gel column chromatography,macroporous resin column chromatography,Sephadex LH-20,and reverse column chromatography(ODS).The inhibitory activity of flavonoid glycosides on human nasopharyngeal carcinoma cells was analyzed by CCK-8 method,and the potential mechanism was preliminarily analyzed by molecular docking.[Results]Two flavonoid glycosides were identified as isovitexin 2″-0-rhamnoside and 7-2″-di-O-β-glucopyranosylisovitexin.Two flavonoid glycosides showed promising inhibitory effect on human nasopharyngeal carcinoma cell line 5-8F,with IC_(50) values of 24.8 and 27.5μmol/L,respectively.Molecular docking results showed that the potential targets of two flavonoid glycosides include CyclinD1,Bcl-2β-Catenin,ILK,TGF-β,in addition,two glycosides showed higher predicted binding affinity towards CyclinD1,which verifies the cytotoxicity of the two compounds on human nasopharyngeal carcinoma cell line 5-8F in vitro.[Conclusions]Two flavonoid glycosides are the active molecules in Chlorophytum comosum that can inhibit the proliferation of human nasopharyngeal carcinoma cells,and have the potential to be used in the research and development of anti nasopharyngeal carcinoma drugs.

Two New Flavonoid Glycosides from Chrysanthemum morifolium

Two new flavonoid glycosides were isolated from the flowering heads of Chrysanthemum morifolium. Their structures were determined to be luteolin 4＇-methoxy-7- O-（6＂-O-acetyl）-β-D-glucopyranoside （1） and acacetin 7-O-（3＂-O-acetyl）-β-D-glucopyranoside （2） by means of 1H and 13C NMR spectroscopic analysis, including 2D NMR technique.

New Flavonoid Glycoside from Thalictrum przewalskii

A new flavonoid glycoside, 5, 7-dihydroxy-4'-methoxyflavonoid 7-Q-[6-O-(4-O-acetyl-alpha-L-rhamnosyl)-3-O-beta-D-glucosyl]-6-O-acetyl-beta-D-glucoside was isolated from Thalictrum przewalskii. Its structure was determined on basis of spectroscopic evidences.

Isolation and Confirmation of Quercetin-3-O-Glycosides from Rubber Cassava Leaves

The core of the natural product chemistry laboratory is isolation secondary metabolites. One of the potential secondary metabolites for isolation in the natural product chemistry laboratory is routine (quercetin-3-O-glycosides). Routine (Quercetin-3-O-glycoside) has been isolated from ethanol extract of rubber cassava leaves (Manihot glaziovii MA). Isolation was done by maceration and recrystallization. The isolation method used in this study is complemented by the isolation method published. The isolated (Quercetin-3-O-glycoside) routine using this method obtained a yield of 0.118% of the total dried leaf extract. The routine (Quercetin-3-O-glycoside) was identified using a standard routine. Routine can be further utilized in the world of medicine as an amplifier of capillary structure, reducing the permeability and fragility of blood vessels.

NMR Spectral Analysis and Hydrolysis Studies of Rebaudioside N, a Minor Steviol Glycoside of <i>Stevia rebaudiana</i>Bertoni

The complete proton and carbon NMR spectral assignments of a diterpene glycoside isolated from the commercial extract of the leaves of Stevia rebaudiana Bertoni, 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] entkaur-16-en-19-oic acid-[(2-O-α-L-rhamnopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester] (1);also known as rebaudioside N, was achieved by the extensive 1D and 2D NMR (1H and 13C, COSY, HMQC, HMBC) as well as mass spectral data. Further, hydrolysis studies were performed on rebaudioside N using acid and enzymatic studies to identify aglycone and sugar residues in its structure.

Isolation and Identification of Antioxidative Active Component from Total Flavonoids of Mimenghua

In this study, bioassay-guided isolation, identification and biological evaluation of antioxidant components from total flavonoids of Chinese herbal plant Mimenghua were performed. 1, 1-Diphenyl-2-picrylhydrazyl(DPPH) radical scavenging test was adopted as the bioassay-guided method, Sephadex LH-20 column chromatography and high performance liquid chromatography were used as the purification tools for the acquisition of antioxidant components. One compound was obtained and identified as acteoside by its physicochemical properties and spectral characteristics. Antioxidant activity in vitro of acteoside was determined by evaluation of the scavenging activity on DPPH radical and hydroxyl radical, reducing power and total antioxidant capability.The results showed that acteoside had significant antioxidative activity and possessed higher activity with the increase of concentration, which provides the potential application of acteoside in food, pharmaceutical and cosmetic industries.

New flavan and unusual chalcone glycosides from Drypetes parvifolia

Two new compounds 7-hydroxy-5-O-（β-D-glucopyranoside） flavan （1） and （Z）-4＇,6＇-dihydroxy-2＇-O-（β-D-glucopyranoside） chalcone （2）, along with eight known compounds, were isolated from the stem bark of Drypetes parvifolia （Euphorbiaceae）. Their structures were established on the basis of spectroscopic analysis and chemical evidence.

A New Flavone Glycoside from Isodon enanderianus

A new flavone glycoside, 5,8-dihydroxy-4',6,7-trimethoxyflavone 8-O-(-D-glucopyranoside 1, together with three known flavonoids, pedalitin 2, cirsimartin 3 and genkwanin 4, were isolated from the aerial parts of Isodon enanderianus. Their structures were determined on the basis of spectral data.

A new hydroxybenzoic acid glycosides from the plant of Trifolium lupinaster

A new 5-O-(β-D-glucopyranosyl)-6 -O-benzoyl-2,5-dihydroxybenzoic acid was isolated from the ethyl acetate extract from the whole plants of Trifolium lupinaster L.Its structure was determined and deduced on the basis of their spectral data.

The First Total Synthesis of Isoliquiritin

A first total synthesis of isoliquiritin was accomplished starting from p-hydroxybenzaldehyde and 2,4-dihydroxyacetylphenone. The key step is condensation reaction. In synthetic process need not protect the hydroxy group of reacting substance.

山银花茎叶化学成分及其抗炎活性研究

目的对山银花茎叶化学成分进行分离和结构鉴定,并进行体外抗炎活性评价。方法山银花茎叶80%甲醇提取物采用Diaion HP20SS、Sephadex LH-20、高速逆流色谱、反相半制备液相色谱等进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。通过测定单体化合物抑制LPS诱导小鼠巨噬细胞RAW264.7释放NO水平评价其抗炎活性。结果从山银花茎叶中分离得到13个化合物,分别鉴定为苄醇-O-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖苷(1)、獐牙菜苷(2)、表断马钱子苷半缩醛内酯(3)、马钱子苷半缩醛内酯(4)、裂环马钱苷(5)、断氧化马钱苷(6)、裂马钱素二甲基乙缩醛(7)、绿原酸甲酯(8)、芹菜素-7-O-β-D-葡萄糖苷(9)、木犀草素-7-O-β-D-葡萄糖苷(10)、野漆树苷(11)、木犀草素-7-O-α-L-吡喃阿拉伯糖(1→6)-β-D-吡喃葡萄糖苷(12)、忍冬苷(13);化合物2~8、11~13可抑制LPS诱导RAW264.7细胞释放NO。结论化合物1首次从忍冬属植物中分离得到,化合物3、5、7、9、11~12首次从山银花茎叶中发现。化合物2~8、11~13具有一定的抗炎活性。

何首乌叶不同萃取物的抗炎活性及其化学成分鉴定

目的:研究何首乌叶的成分,为其功能食品的研发提供基础数据。方法:对何首乌叶醇提取物进行有机溶剂萃取,分别得到何首乌叶石油醚、二氯甲烷、乙酸乙酯、正丁醇、水等不同萃取物,并对不同萃取物进行抗炎活性检测,后续通过硅胶柱色谱、C18柱色谱结合半制备液相等方法对抗炎活性较好的成分进行分离、纯化以及结构鉴定,结果:在质量浓度0~100μg/mL范围内,乙酸乙酯萃取物对RAW264.7细胞存活率无明显的抑制作用,且剂量依赖地抑制NO的生成。石油醚和二氯甲烷萃取物在质量浓度0~25μg/mL时,均无明显细胞毒性,并在25μg/mL时,二氯甲烷萃取物对NO的抑制率(51.47%)高于石油醚萃取物的抑制率(43.91%)。从二氯甲烷和乙酸乙酯萃取物中分离、鉴定出11个化合物,分别为2,3,4,6-三羟基苯乙酮-3-O-β-D-glucoside(1)、杨梅苷(2)、槲皮苷(3)、阿福豆苷(4)、β-谷甾醇(5)、正十六烷-5,8,11三烯酸(6)、二十六烷(7)、α-亚麻酸(8)、山柰酚-3-O-芸香糖苷(9)、肉豆蔻酸(10)和槲皮素(11)。结论:何首乌叶具有很好的抗炎活性,化合物2,4,6,7,8,9,10,11均为首次从何首乌中分离得到。

Simultaneous determination of seven alkaloids and two flavonoid glycosides in Wuzhuyu decoction by RP-HPLC-DAD

A reversed-phase high-performance liquid chromatography （RP-HPLC） method with diode array detector was established to simultaneously determine nine bioactive compounds in Wuzhuyu decoction, namely dehydroevodiamine, isorhanmetin-7-O- rutinoside, 10-hydroxyrutaecarpine, diosmetin-7-O-13-D-glucopyranoside, evodiamine, rutaecarpine, 1-metbyl-2-n-nonyl-4（1H） quinolone, evocarpine, and dihydroevocarpine. The RP-HPLC assay was performed on a reversed-phase Cl8 column with a gradient elution. The mobile phases consisted of methanol and water containing 1% （v/v） acetic acid. The flow rate was 1.0 mL/min and the detection wavelength was set at 300 nm. All calibration curves showed good linearity （r2〉0.9941） within test ranges. The results of intra-day precision, inter-day precision, and accuracy were satisfactory. The overall recoveries were in the range of 90.13%-102.48%. The method was successfully applied to quantify nine bioactive compounds in six samples. Baseline resolution for all nine major compounds was achieved. This method could be used as a suitable quality control assay for Wuzhuyu decoction.

不同来源金线莲组培苗中总黄酮、多糖和内酯苷含量分析

目的比较不同来源金线莲组培苗中总黄酮、多糖和内酯苷的含量。方法采用紫外分光光度法测定不同来源金线莲组培苗中总黄酮和多糖的含量,采用HPLC-ELSD法测定不同来源金线莲组培苗中2种内酯苷含量。结果不同来源金线莲组培苗中总黄酮含量范围为(8.21~16.50)mg·g^(-1),多糖含量范围为(41.40~112.89)mg·g^(-1),金线莲苷含量范围为(83.68~171.67)mg·g^(-1),3(R)-O-β-D-吡喃葡萄糖基-4-羟基-丁酸含量范围为(12.41~29.45)mg·g^(-1)。结论不同来源金线莲组培苗中总黄酮、多糖和内酯苷含量存在差异。

马鞭草苯乙醇苷类成分研究

目的研究马鞭草Verbenae Herba的苯乙醇苷类成分。方法马鞭草80%乙醇提取物采用硅胶、Sephadex LH-20、TLC、半制备HPLC进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到9个化合物,分别鉴定为verbofficoside A(1)、肉苁蓉苷D(2)、广防风苷A(3)、毛蕊花糖苷(4)、异毛蕊花糖苷(5)、肉苁蓉苷C(6)、肉苁蓉苷F(7)、去咖啡酰基毛蕊花苷(8)、jionoside C(9)。结论化合物1为新化合物,化合物3、6~9均首次从该植物中分离得到。

盐肤木叶中化学成分及抗氧化活性研究

研究盐肤木Rhus chinensis Mill.叶的化学成分。利用硅胶柱色谱、Sephadex LH-20柱色谱和半制备高效液相色谱等技术,从盐肤木叶95%乙醇提取物中分离纯化得到了15个化合物。根据化合物的理化性质和波谱数据确定了它们的结构,分别为3-hydroxy-5-methylphenol 1-O-β-D-(6′-benzoyl)glucopyranoside(1)、对羟基苯乙醇(2)、松脂素(3)、(3 S,5 R,6 S,7 E)-3,5,6-trihydroxy-7-megastigmen-9-one(4)、丁香脂素(5)、2,4,6-三羟基苯乙酮(6)、野漆树双黄酮(7)、去氢吐叶醇(8)、槲皮素(9)、没食子酸乙酯(10)、7 S,8 R-二氢去氢双松柏醇(11)、贝壳杉黄酮(12)、4,6-二羟基-2-O-(β-D-吡喃葡萄糖苷)苯乙酮(13)、3-hydroxy-5-methylphenol 1-O-β-D-(6′-galloyl)glucopyranoside(14)、debiloside A(15)。其中化合物1为新化合物,化合物2、4、6、7、8、13、15为首次从盐肤木属中分离得到。DPPH、ABTS自由基清除实验结果显示,化合物9、10、11、14对DPPH、ABTS自由基均表现出良好的清除活性,其中化合物9和10活性最为显著,强于阳性对照V C。

HPLC-DAD法同时测定褐变金银花中15种活性成分含量

目的阐释褐变对金银花药材质量的影响。方法采用HPLC-DAD法比较褐变和正常金银花样品中15种成分(5种酚酸类成分、4种黄酮类成分、6种环烯醚萜苷类成分)的含量,采用SIMCA14.1软件进行主成分(PCA)、正交偏最小二乘法分析(OPLS-DA)。结果褐变后,金银花中酚酸类成分、黄酮类成分及15种成分的总含量均显著下降,环烯醚萜苷类成分中断氧化马钱子苷、莫诺苷和獐牙菜苷含量及6种环烯醚萜苷类成分总含量也显著下降。PCA和OPLS-DA分析结果表明,正常样品与褐变样品各聚为一类,差异显著,VIP分析结果表明,绿原酸、异绿原酸A、断马钱子酸是区别正常样品和褐变样品的主要差异成分。结论褐变会导致金银花药材质量下降,在产地加工过程中应采用适宜方法降低褐变发生率,提升临床用金银花质量。

米糠油中呈色物质的分离和鉴定

米糠油的色泽是影响其品质的因素之一。该研究对米糠油中呈色物质的提取方法进行优化,并利用高效液相色谱串联质谱法对呈色物质进行分离和鉴定。以甲醇∶水(8∶2,体积比)为萃取剂,用液液萃取法提取米糠油中的强极性呈色物质,然后将样品皂化后利用正己烷提取弱极性呈色物质。强极性和弱极性提取液经质谱分别鉴定出9类物质,共37种,其中强极性提取液中二氢异黄酮类含量最多,弱极性提取液中二氢黄酮醇类为主要化合物。

莲子心中具有心肌细胞保护活性的化学成分研究

为了寻找莲子心(Nelumbinis Plumula)具有心肌细胞保护活性的化学成分,本研究采用多种柱色谱技术分离和纯化莲子心的80%乙醇提取物,运用^(1)H NMR、^(13)C NMR等波谱技术和文献数据比对鉴定化合物结构,并对化合物进行心肌细胞保护活性筛选。从莲子心80%乙醇提取物分离纯化得到14个化合物,分别鉴定为柚皮苷(1)、山柰酚-3-O-β-D-芸香糖苷(2)、芹菜素-6-C-β-L-阿拉伯糖-8-C-β-D-葡萄糖苷(3)、木犀草素-7-O-β-D-新橙皮苷(4)、木犀草素-3′-O-β-D-葡萄糖苷(5)、芹菜素-7-O-β-D-葡萄糖苷(6)、橙皮苷(7)、异夏佛塔苷(8)、松脂素-4-O-β-D-葡萄糖苷(9)、对香豆酸-4-O-β-D-葡萄糖苷(10)、对香豆酸(11)、苯乙基6-O-α-L-呋喃阿拉伯糖基-β-D-葡萄糖苷(12)、淫羊藿次苷D1(13)、淫羊藿次苷F2(14)。化合物1~6、9、11~14均为首次从莲子心中分离得到。黄酮类化合物1~8对缺氧/复氧损伤下的小鼠HL-1心肌细胞具有明显的保护作用,对小鼠HL-1-STAT3-Luc细胞中STAT3的表达也具有促进作用,且均具有剂量依赖性。

制何首乌的炮制工艺、化学成分和药理活性研究进展

制何首乌是何首乌Polygonum multiforum Thunb.的炮制加工品,主要成分包括二苯乙烯苷类、蒽醌类、黄酮类、生物碱类、酚酸类等,具有抗氧化、补血、抗肿瘤、降血糖、抗炎等药理作用,临床上使用广泛。炮制工艺主要为黑豆汁炖制、蒸制、九蒸九制和炆制,炮制后颜色加深,成分含量也会发生变化。通过查阅国内外文献,发现对制何首乌的研究相较于何首乌而言不够全面,因此对近20年来报道的制何首乌炮制工艺、化学成分、药理活性的研究进行系统综述,为进一步开发制何首乌提供参考。