Determination of a new chromone from Aurantii Fructus Immaturus by DFT/GIAO method

Investigation of EtOAc fraction from the 95% ethanol extract of Aurantii Fructus Immaturus led to the isolation of one new chromone (1) and seven known flavonoids (2–8). Their structures were elucidated mainly by NMR and HR-ESI-MS, as well as on comparison with the reported NMR data. The final substituent pattern of 1 was defined by comparison of ¹³C NMR data calculated by DFT/GIAO with those of experimental NMR data.     

反相高效液相法测定枳实、枳壳中橙皮甙和柚皮甙的含量

 采用高效液相法测定了枳实和枳壳中的橙皮甙和柚皮甙含量。柱为HypersilODS1柱(250mm×4 6mmi d ),流动相为乙腈 0 5%乙酸溶液(体积比为22∶78),流速为1 0mL/min,检测波长为283nm。柚皮甙和橙皮甙的线性范围分别为0 060g/L～0 604g/L和0 0125g/L～0 125g/L,柚皮甙和橙皮甙的平均回收率分别为97 1%和95 3%。该方法具有操作简便、分析快速、准确等优点。     

A new phenolic glycoside from Saprosma merrillii

A new phenolic glycoside derivative, saproglucoside (1), along with five known phenolic glycoside derivatives (2–6) were isolated from the stems of Saprosma merrillii. The structure of the new compound 1 was determined by 1D and 2D NMR as well as by HRESIMS and hydrolysis. The inhibitory activities of all compounds against seven pathogenic bacteria and two cancer cell lines were evaluated.     

毛细管电泳电化学检测法测定中药枳实和枳壳中的辛弗林和3种黄酮

采用毛细管电泳电化学检测法同时测定了枳实和枳壳中的辛弗林和3种黄酮即橙皮甙、柚皮素和柚皮甙的含量。考察了工作电极的氧化电位、分离电压和进样时间,运行缓冲的浓度和pH值对分离和检测的影响。在优化条件下,以300μm直径的碳圆盘电极为检测电极,检测电位为 0.85 V(vs.SCE),在80 mmol/L硼酸盐(pH 8.45)的运行缓冲液中,被测物浓度与峰电流在3个数量级范围内呈良好线性,检出限(S/N=3)在1×10-4~5×10-4g/L之间,该法简单、可靠、快速,单次测定可在20 m in内完成,已经成功应用于实际样品枳实和枳壳中4组分的测定,样品处理简单,无须预富集,检测结果令人满意。     

A new phenolic glycoside from the Idesia polycarpa Maxim. leaves

Phytochemical investigation on the ethyl acetate extract of Idesia polycarpa Maxim. Leaves led to the isolation of four phenolic glycoside isomers (1–4). Compound 2 appeared to be new reported phenolic glycoside, while compound 1 was the first time isolated from the titled species. Their structures were established by IR, UV, HRESI-MS and 1D and 2D NMR spectroscopies analysis and comparison of spectral data with previously reported data. The compounds 3 and 4 showed stronger activity of scavenging the DPPH free radical than the other two compounds, while the compounds 1 and 2 showed a significant activity of scavenging the ABTS free radical. Compounds 2 and 4 exhibited stronger cytotoxicity against HepG2 cell lines compared to compounds 1 and 3. Moreover, compound 3 presented the highest cytotoxicity against MCF cell lines with IC₅₀ value of 37.17?±?0.26?μg/mL than compounds 1, 2 and 4.     

Application of an efficient strategy based on MAE,HPLC‐DAD‐MS/MS and HSCCC for the rapid extraction,identification, separation and purification of flavonoids from Fructus Aurantii Immaturus

This study presents an efficient strategy based on microwave‐assisted extraction (MAE), HPLC‐DAD‐MS/MS and high‐speed counter‐current chromatography (HSCCC) for the rapid extraction, identification, separation and purification of active components from the traditional Chinese medicine Fructus Aurantii Immaturus. An LC‐DAD‐MS/MS method was applied for the screening and structural identification of main components in crude extract, and five components were preliminarily identified as neoeriocitrin, narirutin, naringin, hesperidin and neohesperidin according to their UV and mass spectra. An efficient MAE method for the extraction of the three most abundant components (narirutin, naringin and neohesperidin) was optimized by the combination of univariate and multivariate approaches. The crude extract was then separated and purified by HSCCC and a total of 61.6 mg of narirutin, 207.3 mg of naringin and 159.5 mg of neohesperidin at high purities of 98.1, 97.2 and 99.5%, respectively, were obtained from 1.42 g of crude extract. The recoveries of these compounds were 86, 93 and 89%, respectively. Copyright © 2009 John Wiley & Sons, Ltd.     

Classification of Aurantii Fructus samples by multivariate analysis

Twenty commercial samples of Aurantii Fructus Immaturus (Poncitrus trifoliata) and 30 of Aurantii Fructus Maturus (Citrus aurantium and C. wilsonii) were collected from the Taiwan and China herbal markets. The contents of 12 constituents in these samples were determined by HPLC and were used to assess the potential relationships with their plant origins. Multivariate analysis including principal component analysis (PCA), cluster analysis (CA), and linear discriminant analysis (LDA) were used as classification procedures. Natural groupings of the samples divided into three sets successfully, 20 P. trifoliata, 15 C. aurantium, and 15 C. wilsonii, were observed by using PCA and CA. The application of LDA gave correct assignation percentages of 100.0% for all three groups.     

Origin identification on the commercial samples of Aurantii Fructus

A total of 50 commercial samples of Aurantii Fructus, originating from Poncitrus trifoliata for Aurantii Fructus Immaturus, Citrus aurantium, and C. wilsonii for Aurantii Fructus Maturus, respectively, were collected from Taiwan and China herbal markets. Contents of the constituents in the samples were determined within 60 min using a developed HPLC method, which had been validated in terms of precision, repeatability, and accuracy. The results of the analyses showed that the constituents were closely related to the species and also the degree of maturity of the fruits, especially in the case of hesperidin (HE), naringin (NG), neohesperidin (NE), naringenin-7-glucoside (NGC), narirutin (NR), and quercetin (QU). The mature fruits (C. aurantium and C. wilsonii) contained chiefly NG, HE, and NE and the immature ones (P. trifoliata) had NG, NR, and QU majorly. Within the mature samples, the ratios of HE/NE and NGC/NE values were higher than 2.94 and 0.21 in C. aurantium and lower than 1.31 and 0.02 in C. wilsonii, respectively. A flowchart that is useful for identifying Aurantii Fractus was devised, based on the various chemical identification methods.     

枳实、枳壳用于复方治疗冠心病的临床疗效观察

目的观察枳实、枳壳用于复方治疗冠心病的临床疗效对比分析。方法观察260例冠心病心绞痛患者,随机分为对照组、复方组(分1~4小组)、阴性组(分a~d小组)、考察组(分Ⅰ~Ⅳ小组),疗程8周。结果各项评价指标显示,复方组(1~4)、考察组(Ⅰ、Ⅱ)明显优于对照组(P0.05),复方各小组与对应考察组比较无显著性差异(P0.05),但考察组(Ⅲ、Ⅳ)不良反应率高于对应的复方组。阴性组疾病疗效、心电图与对照组比较无显著性差异,中医症状改善明显优于对照组。复方组与对应阴性组比较有明显差异。结论枳实、枳壳用于复方中治疗冠心病心绞痛有重要作用,能明显缓解心绞痛症状,改善中医症状,提高疾病疗效,两者之间不可完全相互替代。     

高效液相色谱-电喷雾质谱法测定枳壳中黄酮苷类化合物

利用高效液相色谱与电喷雾质谱联用技术研究了枳壳中的黄酮苷类化合物。实验采用反相C18色谱柱，二元线性梯度洗脱，分离并检测了枳壳中的6种黄酮苷类化合物；它们分别是新圣草苷（neoeriocitrin）、异柚皮苷（isonaringin）、柚皮苷（naringin）、橙皮苷（hesperidin）、新橙皮苷（neohesperidin）和新枸橘苷（neoponcirin）；通过与电喷雾质谱联用获得了这6种黄酮苷的准分子离子峰（[M＋H]^＋）及分子加钠峰（[M＋Na]^＋），利用质谱的碰撞诱导解离技术获得了碎片裂解信息。通过这此质谱信息并结合文献，对这6种化合物进行了结构鉴定。     

The young fruit of Citrus aurantium L. or Citrus sinensis Osbeck as a natural health food: A deep insight into the scientific evidence of its health benefits

Fruits are consumed as foods or medicines to supply people with nutrition or treat diseases. Zhishi, the dried young fruit of Citrus aurantium L. or Citrus sinensis Osbeck, is one of the most representative health food from the fruit of the Citrus genus. It is widely used in flavorings, canned food, beverages, and medicines because of its outstanding curative effects. The bidirectional regulating effect of Zhishi on the gastrointestinal tract for treating food stagnation or diarrhea has been confirmed. Its active ingredients, including synephrine and N-methyltyramine, have been used clinically as blood pressure boosting and anti-shock drugs. Flavonoids and alkaloids of Zhishi also make it potential weight loss and beauty products due to their definite effectiveness and safety. This paper intends to review the different therapeutic applications of Zhishi and the phytochemicals associated with its medicinal values. Besides, up-to-date information on its botany and analytical methods for the quality control of the medicine is supplied. To conclude, numerous independent research on Zhishi have been conducted in the past decades, but most of them are not deep enough in elucidating its scientific evidence of its health benefits. Further studies may unveil additional pharmacological activities and is beneficial to the mankind.     

A new coumarin glycoside from Daphne giraldii

A new coumarin glycoside was isolated from the ethanol extract of the barks of stem of Daphne giraldii Nitsche. Its structure was defined as daphnetin 8-O-b-D-glucopyranosyl-(1→6)-b-D-glucopyranoside on the basis of spectral evidences.     

A new iridoid glycoside from Gardenia jasminoides

A new iridoid glycoside,6′-O-sinapoylgeniposide,was isolated from Gardenia jasminoides Ellis and its structure was elucidated on the basis of 1D and 2D NMR,HR-ESI-MS techniques.     

A new iridoid glycoside from Veronica sibirica

A new iridoid glycoside,versibirioside（1）,and a known iridoid glycoside,verbaspinoside（2）,were isolated from the whole plant of Veronica sibirica L.Their structures were elucidated by spectroscopic methods,including 2D-NMR spectra.     

A new sesquiterpenoid glycoside from Saussurea involucrata

Abstract

Saussurea involucrata, known for the abundant bioactive components, is a precious traditional Chinese medicine. In this study, a novel guaiane sesquiterpenoid glycoside named (1R, 5R, 6R, 7R, 8S, 11S)-11, 13-dihydrodehydrocostuslactone-8-O-6'-2''(E)-butenoyl-β-D-glucopyranoside (1), together with seven known compounds (2–8) were isolated from the dried aerial part of S. involucrata. Their structures were elucidated by spectroscopic and physico-chemical analyses. The antioxidant and anti-inflammatory activities of compound 1 were investigated. And compound 1 showed weak radical scavenging activity and low inhibitory activity on nitric oxide (NO) production.     

A new neolignan glycoside from Dolomiaea souliei

Abstract

One new neolignan glycoside, dolomiside A (1), together with 11 known phenylpropanoid glycosides were isolated from Dolomiaea souliei (Franch.) Shih. The structures of these isolates were determined by UV, CD, HR-ESI-TOFMS, 1D and 2D NMR analysis.     

A new flavone glycoside from Selaginella moellendorffii Hieron.

From the ethanol extract of Selaginella moellendorffii Hieron., a new flavone O-glycoside and three known flavone C-glycosides have been isolated and identified as 5-carboxymethyl-4'-hydroxyflavone-7-O-β-D-glucopyranoside 1, 6,8-di-C-β-D-glucopyrano-sylapigenin 2, 6-C-β-D-glucopyranosyl-8-C-β-D-xylopyranosyl apigenin 3, 6-C-β-D-xylopyranosyl-8-C-β-D-glucopyranosylapi-genin 4, respectively. Their structures were elucidated by spectroscopic methods.     

A new flavanone glycoside isolated from Tournefortia sibirica

A new flavanone glycoside, (2S)-dihydrooroxylin A 7-O-[β-D-apiosyl(1→2)]-β-D-glucoside (1), and four known compounds (2–5) were isolated from Tournefortia sibirica L. The chemical structures of these compounds were determined by 1?D and 2?D NMR and HR-ESI-MS spectra, and results were compared with data from the literature. These five compounds (1–5) were isolated from the family Boraginaceae for the first time. Anti-inflammatory effects of compounds (1–5) were evaluated in terms of inhibition of production of NO, TNF-α, and IL-6 in LPS-induced RAW 264.7 cells.     

A new C27-steroidal glycoside from Ophiopogon japonicus

A new C27-steroidal glycoside with three known compounds were isolated from the tuber of Ophiopogonjaponicus （Thunb.） Ker-Gawl. Based on the spectral analysis, including HRMS, 1H NMR, 13C NMR, DEPT, 1H-1H COSY, HMQC and HMBC, their chemical structures were determined as pennogenin-3-O-α-L-rhamnopyranosyl-（1→ 2）-β-D-xylopyranosyl-（1→ 4）-13-D-gluco- pyranoside （1）, pennogenin-3-O-α-L-rhamnopyranosyl-（1→ 2）-β-D-glucopyranoside （2）, ophiopojaponin C （3） and ophiopogonin D （4）. 2007 Jian Zhong Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.     

A phenolic glycoside from Fagopyrum dibotrys (D.Don) Hara

A new phenolic constituent along with five known compounds were isolated from Fagopyrum dibotrys(D.Don)Hara.The new compound was characterized as 1,3-dimethoxy-2-O-β-xylo-pyranosyl-5-O-β-glucopyranosyl-benzene,by spectroscopic analysis and enzymatic hydrolysis.