AIM To establish the HPLC fingerprints of Kangfuxin Liquid (extract of Periplaneta americana L.) and to determine the contents of six constituents.METHODS The analysis of this drug was performed on a TOSOH TSK-GEL ODS column (250 mm × 4.6 mm,5 μm),with the mobile phase comprising of acetonitrile-water (containing 0.07% acetic acid) flowing at 1.0 mL/min in a gradient elution manner,and the detection wavelength was set at 280 nm.RESULTS There were twenty-four common peaks in the fingerprints of ten batches of samples (Ⅰ-Ⅹ) with the similarities of 0.932-0.993 (except for sample Ⅰ).Uracil,hypoxanthine,xanthine,inosine,protocatechuic acid and Cyclo (Gly-Tyr) showed good linear relationships within the ranges of 3.460-173.0,3.960-198.0,3.596-179.8,1.338-66.9,3.672-183.6 and 3.552-177.6 μg/mL,whose average recoveries (RSDS) were99.8% (2.65%),98.0% (2.55%),99.7% (1.59%),100.7% (2.80%),102.0% (2.09%) and 99.6% (1.88%),respectively.CONCLUSION This accurate,stable and simple method can be used for the quality control of Kangfuxin Liquid.
2′-Z auraptene ( 1 ) is a synthesized monoterpene coumarin with anticancer activity against human gastric cancer cells. In order to find new potential anticancer agent, Mucor polymorphosporus was used to transform cis -auraptene. Four new terpene coumarins with notable changes in the skeletal backbone, 2′-Z auraptene A-D ( 2 – 5 ), were obtained and evaluated for their antiproliferative effects against human normal gastric epithelium cells and human gastric cancer cells. These new compounds showed selective cytotoxic activity against MGC-803 cells with IC 50 values from 0.78 ± 0.13 to 10.78 ± 1.83 μM and the therapeutic index could also be significantly improved (TI = 59.0) compared with that of 1 (TI = 5.5). The structures of these metabolites were elucidated through extensive spectroscopic methods, and the possible biotransformation pathway of 1 by Mucor polymorphosporus was also proposed. Furthermore, the mechanism of the antiproliferative effects against MGC-803 cells of the most potent compound, 2′-Z auraptene A ( 2 ), was characterized. Annexin V/PI staining and abnormal expression of apoptosis-related protein suggested that compound 2 induces apoptosis in gastric cancer MGC-803 cells. Therefore, it is possible that compound 2 has the potential to be applied in gastric cancer therapy.
Objective:To study the chemical constituents of Kangfuxin Liquid.Methods:The chemical constituents were isolated and purified on silica gel column chromatography,Sephadex LH20 and semi-preparing liquid chromatography,and identified by MS and NMR.Results:Thirteen compounds were obtained and identified as following:uracil(1),hypoxanthine (2),cyclo-(Tyr-Gly) (3),protocatechuic acid (4),inosine (5),glycerol (6),leucine (7),isoleucine (8),phenylalanine (9),tyrosine (10),valine (11),alanine (12),glycine (13).Conclusion:Compounds 3 and 4 are isolated from Periplaneta americana for the first time.
Periplaneta America are the folk traditional medicine derived from southwest area.Until now there have been four related postmarketing drugs on sale-"Kangfuxin Liquid","Xinmailong Injection","Ganlong Capsule" and "Xiaozheng Yigan Tablet".The modem studies show they have obvious effects on inflammation and tumefaction,wound surface,cardio-cerebrovascular diseases,Hepatitis B and liver cancer.But it's very little known about the active ingredients and mechanisms of action,this will significantly limit its usage in future.So,at present,many researchers are engaged in this field and make some progress by extracting secondary metabolites like isoflavones and isocoumarins from the crude materials.Also some of them consider that the mechanism is the result of multiple factors and cytokines.This review outlines recent advances of Periplaneta America in related aspects and is expected to provide a support to the thorough research of Periplaneta America.
综合运用硅胶柱色谱、Sephadex LH-20凝胶柱色谱及制备型高效液相等分离技术,结合化合物理化性质及其波谱数据等多种结构鉴定手段对天山假狼毒地上部分进行化学成分研究.最终,从天山假狼毒地上部分分离鉴定得到了16个化合物,分别为:西瑞香素(1)、西瑞香素-7-O-β-D-葡萄糖苷(2)、繸状芸香甙酯(3)、9'-甲氧基繸状芸香甙酯(4)、7,7'-二羟基-6,8'-双香豆素(5)、Bicoumol-7'-O-β-glucopyranoside(6)、7,8-二羟基香豆素(7)、genkwanol B (8)、Viburnolide A(9)、对羟基苯甲酸(10)、白桦脂醇(11)、胡萝卜苷(12)\β-谷甾醇(13)、正二十四烷醇(14)、正二十三烷醇(15)、正三十五烷醇(16).化合物1~16均为首次从假狼毒属植物中分离得到.
New drimane-type sesquiterpene cryptoporol A (1), cryptoporic acid derivative 6′-cryptoporic acid E methyl ester (2), and pseudouridine derivative cryptoporine A (3), as well as a known ergosterol 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol (4), were isolated from a 90 % alcohol extract of the fruiting bodies of Cryptoporus volvatus. The structures of these compounds were established by spectroscopic analysis and circular dichroism. 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol (4) exhibited antiviral activity against porcine reproductive and respiratory syndrome virus, and all compounds showed weak antioxidant activities.
A new drimane-type sesquiterpene with an isocitric acid moiety, cryptoporic acid S (1), together with six known compounds, cryptoporic acid D (2), β-sitosterol (3), β-daucosterol (4), stigmast-4-en-3-one (5), ergosterol (6), and (22E,24R)-ergosta-7,22-diene-3β,5α,6β-triol (7), was isolated from the fruiting bodies of Cryptoporus volvatus. The structures of these compounds were established on the basis of UV, IR, MS, 1D and 2D NMR analysis. In the meanwhile, compounds 1 and 2 were evaluated for antioxidant activity using the methods of 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity (DPPH-RSA) and ferric reducing antioxidant power (FRAP) assay, and they exhibited moderate antioxidant activities.
目的:优化新疆阿魏种子中总倍半萜香豆素的提取工艺.方法:以乙醇体积分数、料液比、提取时间为自变量,在单因素试验的基础上,应用Box-Behnken中心组合设计建立数学模型,以总倍半萜香豆素提取率为响应值,进行响应面分析.结果:最佳提取工艺条件为80%乙醇加热回流提取40 min,料液比为1∶40.总倍半萜香豆素提取率预测值为6.60%,实际值为6.62%,相对误差为0.3%.结论:该优选工艺稳定可靠,为新疆阿魏资源的合理利用提供参考.
Effective chemicals isolated from folk medicine are commonly used in the treatment of cancer in Asian countries like China and India.
Two new sesquiterpene coumarins, namely, sinkiangenorin F (1) and 8-O-acetyl sinkiangenorin F (2) were isolated from the seeds of Ferula sinkiangensis. The structures of the new compounds, including the relative stereochemistry and the absolute configuration were elucidated through extensive spectroscopic methods. The two compounds were tested against the K562, HeLa, and AGS human cancer cell lines and showed cytotoxic activities with 50% inhibitory concentration values between 27.1 and 62.7μM.
A new sesquiterpene coumarin with a novel sesquiterpene carbon framework, Sinkiangenorin D, and ten known sesquiterpene coumarins were isolated from the seeds of Ferula sinkiangensis. The structures of these compounds, including the relative stereochemistry, were elucidated on the basis of spectroscopic data. All of the isolated compounds were tested against the AGS, HeLa, and K562 human cancer cell lines and showed cytotoxic activities with 50% inhibitory concentration values between 12.7 and 226.6 μM.
Two new cryptoporic acid derivatives, cryptoporic acid R (1) and 6',6 '''-cryptoporic acid G dimethyl ester (2), together with two known compounds, cryptoporic acid E (3) and cryptoporic acid E pentamethyl ester (4), were isolated from a 90% alcohol extract of the fruiting bodies of Cryptoporus volvatus. Their structures were established on the basis of NMR spectroscopic and mass spectrometry data. Cryptoporic acid E (3) and cryptoporic acid E pentamethyl ester (4) exhibited antiviral activity against porcine reproductive and respiratory syndrome virus. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
Objective: To analyze the caffeoylquinic acids and to develop an HPLC method for simultaneous determination of neochlorogenic acid,chlorogenic acid and cryptochlorogenin acid in Huahong capsules. Methods: A UPLC / Q- TOF- MS / MS method was developed to rapidly identify the caffeoylquinic acids in Huahong capsules. And the UPLC separation was performed on a Thermo BEH C 18 column( 2. 1 mm × 100 mm,1. 7 μm) with 0. 1% formic acid acetonitrile- 0. 1% formic acid as the mobile phase in gradient elution at a flow rate of 0. 4 μL · min- 1. The column temperature was set at 40 °C. The MS spectrometry detection was performed with electrospray ionization in negative ion mode,and using the following operating parameters: scan range,100- 1500 m / z; capillary voltage,2. 5 kV; skimmer voltage,40 kV; ion source temperature,120 °C; drying gas temperature,450 °C and sample collision energy,15- 40 eV. Besides,HPLC was performed on a Phenomenex C18( 250 mm ×4. 6 mm,4 μm)column with 0. 1% formic acid acetonitrile- 0. 1% formic acid as the mobile phase in gradient elution( 0- 7 min,5% →8% A; 7- 17 min,8% →15% A; 17- 45 min,15% →30% A; 45- 55 min,30% →50% A; 55- 60 min,50% →100% A) at a flow rate of 1. 0 mL·min- 1. The detect wavelength was set at 326 nm,and the column temperature was set at 30 °C. Results: Based on the UPLC / Q- TOF- MS / MS analysis,four caffeoylquinic acids,neochlorogenic acid,chlorogenic acid and cryptochlorogenin acid and isochlorogenic acid A,were identified from Huahong capsules. In addition,by using HPLC method,the correlation between the concentration and the chromatographic peak area of neochlorogenic acid,chlorogenic acid and cryptochlorogenin acid was linear in ranges of 3. 54-176. 80 μg·mL- 1( r = 0. 9999),6. 98- 348. 80 μg·mL- 1( r= 0. 9999),4. 06- 202. 80 μg·mL- 1( r =0. 9999),respectively. The average recoveries of the three caffeoylquinic acids were in the range of 101. 5%-102. 2%,and the relative standard deviations( RSD) were in the range of 1. 9%- 2. 4%. Conclusion: The UPLC /Q- TOF- MS / MS and HPLC methods do not only pave a way for further understanding of the chemical constituents in Huahong capsules,but also provide scientific evidences for the quality control of Huahong capsules.
Two new steroidal esters with an unusual framework, Sinkiangenorin A and B, a new organic acid glycoside, Sinkiangenorin C, and four known lignin compounds were isolated from the seeds of Ferula sinkiangensis. The structures of these compounds were established by spectroscopic analysis and single-crystal X-ray diffraction. All of the isolated compounds were tested against Hela, K562 and AGS human cancer cell lines. Sinkiangenorin C showed cytotoxic activity against AGS cells with an IC50 of 36.9 mu M. (C) 2014 Elsevier B.V. All rights reserved.
目的:研究一点红的HPLC指纹图谱,并测定该药材中新绿原酸①、绿原酸②、隐绿原酸③这3个咖啡酰奎宁酸类的含量,为其质量控制提供参考.方法:采用Phenomenex C18色谱柱(250mm×4.6mm,4μm),0.1%甲酸乙腈-0.1%甲酸水为流动相,梯度洗脱,流速1.0mL/min,检测波长326nm,柱温为30℃.对10批不同产地的一点红药材的HPLC图谱进行相似度评价.采用外标法,利用①-③的混合对照品测定其在10批药材中的含量.结果:确定该10批不同产地的一点红药材具有18个共有峰,10批药材的相似度范围为0.851-0.992;测定了10批一点红中的3个咖啡酰奎宁酸类成分的含量,结果显示,不同产地一点红中3个成分的含量差异明显.结论:HPLC指纹图谱方法与3个成分的含量测定方法准确、稳定、简单,可为一点红质量控制提供参考.
In order to find the cardiotonic constituents of lateral roots of Aconitum carmichaelii Debx., the investigation was carried out. Silica gel column chromatography, Sephadex LH-20, medium-pressure MCI and reverse phase ODS column chromatography were used to separate the 90% EtOH extract of the lateral roots of Aconitum carmichaelii Debx. The structures of the isolated compounds have been identified by chemical properties and spectroscopic analyses. Ten compounds were isolated and their structures were elucidated as benzoic acid-5-hydroxy-2-benzoyl-amino methyl ester (1), honokiol (2), pinoresinol (3), salicylic acid (4), p-hydroxy-cinnamic acid (5), songorine (6), karakoline (7), mesaconitine (8), hypaconitine (9) and 14-benzoylhypaconitine (10), separetely. Compound 1 is a new compound and its structure has been established by NMR, HR-ESI-MS, UV, IR and X-Ray. Compound 2-5 are isolated from the lateral roots of Aconitum carmichaelii Debx. for the first time.
Objective To study the chemical constituents from the roots and rhizomes of Acorus tatarinowii. Methods Using different chromatographic methods to isolate and purify the constituents of A. tatarinowii, and their structures were identified by physicochemical properties and spectroscopic technology. Results Thirteen compounds were isolated and identified as fumaric acid (1), nicotinic acid (2), p-hydroxybenzonic acid (3), uracil (4), N-trans-feruloyltyramine (5), thymine (6), variecolorquinone A (7), butanedioic acid (8), tatarol (9), tataroside-12-β-D-glucoside (10), β-sitosterol (11), 2, 5-dimethoxy benzoquinone (12), and 5-hydroxymethyl-2-furaldehyde (13). Conclusion Compounds 1—7 are isolated from the plants in Acorus L. for the first time.
A new pyrrolidine alkaloid, Emiline (1), was isolated from the 90% EtOH extract of the aerial parts of Emilia sonchifolia. Its structure was established by various spectroscopic methods, including NMR, IR, HR-ESI-MS and X-ray crystallography. It was characterized by its skeleton derived from a bicyclo-[2.2.2]-oct-5-one ring and a pyrrolidine unit. The racemic mixture, (+/-)-Emiline, displayed good neuroprotective effect against the corticosterone-induced apoptosis in PC12 cells. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
A new cyclohexylacetic acid derivative, named 2-{4-hydroxy-7-oxabicyclo [2.2.1] heptanyl}-acetic acid (1), was isolated from Emilia sonchifolia, together with a known analogue, 2-(1,4-dihydroxy cyclohexanyl)-acetic acid (2). Their structures were determined on the basis of spectroscopic techniques including IR, NMR, HR-ESI-MS and X-ray diffraction.