Towards molecular-imprint based SPE of local anaesthetics

Summary Solidago canadensis L., Canadian goldenrod (Asteraceae) has been used in European phytotheraphy for centuries as a component of urological and antiphlogistical remedies. High-performance liquid chromatography (HPLC) coupled with diode-array detection (DAD) and online mass spectrometry (MS) has been used for the separation and quantification of phenolics (chlorogenic acid, caffeic acid, kaempferol-3-O-α-L-rutinoside (nicotiflorin), quercetin-3-O-β-D-rutinoside (rutin), quercetin-3-O-β-D-galactoside (hyperoside), quercetin-3-O-β-D-glucoside (isoquercitrin), quercetin-3-O-β-D-rhamnoside (quercitrin), kaempferol-3-O-α-L-rhamnoside (afzelin) and quercetin from Solidaginis herba. Extracts have been obtained using different technologies. Three aqueous and three alcoholic extracts were studied separately. Reversedphase high-performance liquid chromatography separation of polyphenols on octadecyl sorbent Hypersil was performed, using acetonitrile: acetic acid 2.5 v/v % as eluent in gradient elution. Our results confirm previous reports concerning the presence of several flavonoids. Quantification of the main quercetin glycosides in pharmaceuticals is also reported. Presented at Balaton Symposium '01 on High-Performance Separation Methods, Siófok, Hungary, September 2–4, 2001     

Determination of Cytotoxic Activity of Sanguinaria canadensis Extracts against Human Melanoma Cells and Comparison of Their Cytotoxicity with Cytotoxicity of Some Anticancer Drugs

Melanoma is an enormous global health burden, and should be effectively addressed with better therapeutic strategies. Therefore, new therapeutic agents are needed for the management of this disease. The aim of this study was the investigation of cytotoxic activity of some isoquinoline alkaloid standards and extracts obtained from Sanguinaria canadensis—collected before, during, and after flowering—against three different human melanoma cells (A375, G361, SK-MEL-3). The cytotoxicity of these extracts was not previously tested on these melanoma cell lines. Determination of alkaloid contents was performed by HPLC-DAD using Polar RP column and mobile phase containing acetonitrile, water, and 1-butyl-3-methylimidazolium tetrafluoroborate. The cytotoxicity of alkaloid standards was investigated by determination of cell viability and calculation of IC₅₀ values. Significant differences were observed in the alkaloids content and cytotoxic activity of the extracts, depending on the season of collection of the plant material. In the Sanguinaria canadensis extracts high contents of sanguinarine (from 4.8543 to 9.5899 mg/g of dry plant material) and chelerythrine (from 42.7224 to 6.8722 mg/g of dry plant material) were found. For both of these alkaloids, very high cytotoxic activity against the tested cell lines were observed. The IC₅₀ values were in the range of 0.11–0.54 µg/mL for sanguinarine and 0.14 to 0.46 µg/mL for chelerythrine. IC₅₀ values obtained for Sanguinaria canadensis extracts against all tested cell lines were also very low (from 0.88 to 10.96 µg/mL). Cytotoxic activity of alkaloid standards and Sanguinaria canadensis extracts were compared with the cytotoxicity of anticancer drugs—etoposide, cisplatin, and hydroxyurea. In all cases except the one obtained for cisplatin against A375, which was similar to that obtained for Sanguinaria canadensis after flowering against the same cell line, IC₅₀ values obtained for anticancer drugs were higher than the IC₅₀ values obtained for sanguinarine, chelerythrine, and Sanguinaria canadensis extracts. Our results showed that Sanguinaria canadensis extracts and isoquinoline alkaloids, especially sanguinarine and chelerythrine, could be recommended for further in vivo experiments in order to confirm the possibility of their application in the treatment of human melanomas.     

加拿大一枝黄花总酚超声提取工艺

利用超声提取的方法,通过单因素和正交实验分析了溶液浓度、超声时间、料液比、提取次数4个主要因素对总酚提取率的影响。确立了加拿大一枝黄花总酚的最佳提取工艺条件为:60%甲醇、超声50min、料液比1∶20、提取3次。在此条件下,总酚的提取率为44.61mg/g。     

微波辅助萃取加拿大一枝黄花的花中总黄酮的工艺研究

对加拿大一枝黄花的花进行微波处理,考察微波辅助萃取对加拿大一枝黄花的花中总黄酮提取率的影响.以卢丁为标准品,用硝酸铝做显色剂,采用分光光度法在530nm波长处测定了加拿大一枝黄花的花中总黄酮的含量,探讨了料液比、乙醇浓度、微波功率、微波处理时间等因素对加拿大一枝黄花的花中总黄酮提取率的影响.结果表明,在料液比1:10、乙醇浓度70%、微波功率700W、微波处理时间15min最优条件下,加拿大一枝黄花的花中总黄酮的提取率为17.86%.     

The Analysis of Cell Contents of Some Papaveraceous Plants by Newly Devised Automated Histochemical Chromatography

Abstract

Contents of the colored cells (alkaloidal cells¹) found in Macleaya cordata root and Sanguinaria canadensis rhizome were analysed quantitatively by histochemical chromatography (HC) with the help of newly modified automated micromanipulator.

These were found to have 4 alkaloids viz protopine type protopine(1) and allocryptopine(2) and benzo- [c]phenanthridine type (sanguinarine(3) and cheleryth-rine(4)) in both the plants. Quantitatively the pro-topine alkaloids were 10-40 ng per cell while the benzo-[c]phenanthridines (as chlorides) were only 1-6 ng per cell in M. cordata root. However, in S. canadensis rhizome the relative quantities of the 4 alkaloids (1), (2), (3) and (4) were found to be 10, 13, 137 and 68 ng per cell respectively.     

加拿大一枝黄花的研究及应用现状

加拿大一枝黄花(Solidago Canadensis L.),是原产于北美的一种菊科多年生草本植物,20世纪30年代开始进入我国,现在这种植物已成为我国大部分境内迅速扩散传播的恶性杂草。目前,国内外的很多研究者已经利用各种方法从加拿大一枝黄花中提取出了倍半萜烯类、氨基酸、醇类等化学物质,对其生物性能进行了研究,并且对于控制这种植物的生长提出了各种解决方案。同时,加拿大一枝黄花已经在提炼精油、医学制药等方面得到广泛的应用。     

Insecticidal Activity of Organic Extracts of Solidago graminifolia and Its Main Metabolites (Quercetin and Chlorogenic Acid) against Spodoptera frugiperda: An In Vitro and In Silico Approach

Spodoptera frugiperda (S. frugiperda) remains a global primary pest of maize. Therefore, new options to combat this pest are necessary. In this study, the insecticidal activity of three crude foliar extracts (ethanol, dichloromethane, and hexane) and their main secondary metabolites (quercetin and chlorogenic acid) of the species Solidago graminifolia (S. graminifolia) by ingestion bioassays against S. frugiperda larvae was analyzed. Additionally, the extracts were phytochemically elucidated by ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) analysis. Finally, an in silico study of the potential interaction of quercetin on S. frugiperda acetylcholinesterase was performed. Organic extracts were obtained in the range from 5 to 33%. The ethanolic extract caused higher mortality (81%) with a half-maximal lethal concentration (LC₅₀) of 0.496 mg/mL. Flavonoid secondary metabolites such as hyperoside, quercetin, isoquercetin, kaempferol, and avicularin and some phenolic acids such as chlorogenic acid, solidagoic acid, gallic acid, hexoside, and rosmarinic acid were identified. In particular, quercetin had an LC₅₀ of 0.157 mg/mL, and chlorogenic acid did not have insecticidal activity but showed an antagonistic effect on quercetin. The molecular docking analysis of quercetin on the active site of S. frugiperda acetylcholinesterase showed a −5.4 kcal/mol binding energy value, lower than acetylcholine and chlorpyrifos (−4.45 and −4.46 kcal/mol, respectively). Additionally, the interactions profile showed that quercetin had π–π interactions with amino acids W198, Y235, and H553 on the active site.     

A new derivative of triterpene with anti-melanoma B16 activity from Conyza Canadensis

<正>A new derivative of triterpene named Erigeronol 1 was isolated from the EtOH extract of the aerial part of Conyza canadensis together with 15 known compounds for the first time from this plant.The structure of Erigeronol 1 was elucidated as 3-O-(hydroxyacetyl) -23,28-dihydroxy-β-amyrin by hydrolysis and spectroscopic analysis.Erigeronol 1 showed potent cytotoxic activity with IC_(50) value of 7.77±0.47μg/mL against melanoma B16 determined by the 3-(4,5-dimethylthiazo-2-yl)-2,5-diphenyltetrazolium bromide(MTT) method.     

Analysis of Cytotoxicity of Selected Asteraceae Plant Extracts in Real Time,Their Antioxidant Properties and Polyphenolic Profile

Plants from Asteraceae family are widely used for their therapeutic effects in the treatment of gastrointestinal diseases, but the consequences of excessive intake still need to be studied. The aims of this study were the evaluation of cytotoxicity, measurement of antioxidant properties and determination of polyphenolic profile of Tanacetum vulgare L. (tansy), Achillea millefolium L. (yarrow) and Solidago gigantea Ait. (goldenrod) ethanolic extracts. The cytotoxicity of extracts was monitored by xCELLigence system in real time by using porcine intestinal epithelial cell line (IPEC-1) and by measurement of changes in metabolic activity ((3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) (MTS) assay). The antioxidant properties were measured by spectrophotometric methods and polyphenolic profiles were determined by HPLC-DAD for 50% ethanol extracts (10% w/v). Strong cytotoxic effect was recorded for tansy and yarrow extracts (125–1000 µg/mL) by xCELLigence system and MTS assay. Conversely, a supportive effect on cell proliferation was recorded for goldenrod extracts (125 µg/mL) by the same methods (p < 0.001). The antioxidant activity was in good correlation with total polyphenolic content, and the highest value was recorded for goldenrod leaves, followed by tansy leaves, goldenrod flowers and yarrow leaf extracts. The goldenrod extracts were abundant with flavonoids, whereas phenolic acid derivatives predominated in the polyphenolic profile of tansy and yarrow.