A New Sesquiterpene Lactone Glucoside from Ixeris Sonchifolia

A new sesquiterpene lactone glucoside, Ixerin Z₁ (1), was isolated from the whole plants of Ixeris sonchifolia (Bge.) Hance, along with 15 known compounds. The structure of 1 was elucidated as 1(10),3,11(13)-guaiatriene-12,6-olide-2- one-3-O-[6'-(p-hydroxyphenylaceryl)]-gluco-pyranoside by spectroscopic methods including 2D-NMR techniques.     

A new sesquiterpene lactone glucoside with inhibitory effect on K562 cells from Ixeris sonchifolia (Bge) Hance

A new minor sesquiterpene lactone glucoside, ixerin Z_A (1), together with 16 known compounds, were isolated from the whole plants of Ixeris sonchifolia (Bge) Hance. The structure of 1 was elucidated as 1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3-O-[6′-(p-metheoxyphenylacetyl)]-β-glucopyranoside on the basis of spectroscopic and chemical evidence. Compound 1 exhibited an inhibitory effect on K₅₆₂ cells.     

苦碟子中的新倍半萜内酯

苦碟子为菊科植物抱茎苦荬菜［Ｉｘｅｒｉｓｓｏｎｃｈｉｆｏｌｉａ（Ｂｇｅ．）Ｈａｎｃｅ］的当年生干燥全草,主要分布于东北、内蒙古等地．具清热解毒、消肿止痛之功效〔１〕．文献〔２,３〕对其化学成分进行了一系列的报道．本文对其氯仿萃取层进行化学研究,并分离鉴定了一个新化合物,命名为苦碟内酯Ａ（ｓｏｎｃｈｉｆｏｌｉａｃｔｏｎｅＡ,Ｉ）．分离提取苦碟子全草５ｋｇ,用７０％的乙醇加热回流提取,过滤,滤液回收乙醇,经真空干燥后,浓缩物混悬于水中,依次用氯仿、乙酸乙酯、正丁醇萃取,取氯仿萃取层８０ｇ经硅胶柱色谱…     

A new sesquiterpene lactone glucoside with inhibitory effect on K562 cells from Ixeris sonchifolia (Bge) Hance

A new minor sesquiterpene lactone glucoside, ixerin Z_A (1), together with 16 known compounds, were isolated from the whole plants of Ixeris sonchifolia (Bge) Hance. The structure of 1 was elucidated as 1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3-O-[6'-(p-metheoxyphenylacetyl)]-β-glucopyranoside on the basis of spectroscopic and chemical evidence. Compound 1 exhibited an inhibitory effect on K₅₆₂ cells.     

Sesquiterpene lactones from Ixeris sonchifolia (Bge.) Hance II

Four new sesquiterpene lactones, sonchifoliasolides D (1), E (2), F (3) and G (4) were isolated from the aerial parts of Ixeris sonchifolia (Bge.) Hance. The structures of compounds 1–4 were established on the basis of their spectroscopic data.     

Two new compounds from Ixeris sonchifolia

Two new compounds, named as sonchifolactone E (1) and sonchifolinin B (2), have been isolated from the whole plant of Ixeris sonchifolia, along with one known compound, sonchifolatone A (3). Their structures and stereochemistry were determined by spectroscopic methods.     

抱茎苦荬菜的化学成分研究

目的研究抱茎苦荬菜Ixeris sonchifolia Hance的化学成分。方法用硅胶及SephadexLH-20凝胶柱色谱法分离纯化化合物,运用波谱学方法确定化合物的结构。结果从抱茎苦荬菜中分离鉴定了13个化合物,分别为3β-acetoxy-20-taraxasten-22-one(1),乙酸降香萜烯醇酯(2),3β-acetoxy-11-oxours-12-ene(3),齐墩果酸(4),齐墩果烷(5),8-去氧青蒿内酯(6),七叶内酯(7),阿魏酸(8),香草酸(9),抱茎苦荬菜素(10),正二十六醇(11),β-谷甾醇(12),胡萝卜苷(13)。结论化合物1、5、8为首次从苦荬菜属(Ixeris)中分离得到,化合物7首次从该植物中分离得到。     

奥扎格雷钠 苦蝶子注射液治疗急性脑梗死

目的观察奥扎格雷钠联合苦蝶子注射液治疗急性脑梗死的疗效。方法将120例急性脑梗死患者随机分为奥扎格雷钠组(32例)、苦碟子组(38例)和联合组(50例)。苦碟子组使用苦碟子40ml;奥扎格雷钠组使用奥扎格雷钠60～80mg;联合组联用奥扎格雷纳60～80mg和苦碟子40ml,三组均加入生理盐水或是5%葡萄糖注射液250ml,静脉注射,1天/次,连用21天。三组治疗前后均进行神经功能缺损程度评分、评价疗效和不良反应情况。结果联合组的总有效率(82.0%)明显高于奥扎格雷钠组(50.0%)和苦碟子组(55.3%)(P<0.05)。联合治疗组l例首次静脉输注时感轻度头胀,处理后恢复。结论奥扎格雷钠联合苦蝶子注射液治疗急性脑梗死疗效明显,安全。     

苦碟子中的两个新黄酮苷

从苦碟子（Ixeris sonchifolia Hance)的全草中分得5个黄酮,分别为木犀草素－7－O－β－D－葡萄糖醛酸苷甲酯（1）,芹菜素－7－O－β－D－葡萄糖醛酸苷甲酯（2）,木犀草素（3）,木犀草素－7－O－β－D－葡萄糖苷（4）,芹菜素（5）。它们的结构经各种光谱解析确定,其中化合物1和2为新黄酮。     

Sesquiterpene lactones from Ixeris sonchifolia Hance and their cytotoxicities on A549 human non-small cell lung cancer cells

A new sesquiterpene lactone glucoside, 11,13-dihydroixerinoside (1), together with the five known sesquiterpene lactones, ixerinoside (2), ixerin Z (3), 11,13α-dihydroixerin Z (4), ixerin Z1 (5), and 3-hydroxydehydroleucodin (6), respectively, were isolated from the whole plants of Ixeris sonchifolia Hance. The compounds were identified by spectral analysis and comparison with spectroscopic data reported in the literatures. When the in vitro cytotoxic activities of compounds 1–6 were evaluated against A549 human non-small cell lung cancer cells, all six compounds exhibited cytotoxic activity against A549 cells, with compounds 2, 3, and 6 showing good activities (inhibitory concentration (IC₅₀ values < 30 μg/ml) that are comparable with well-established chemotherapeutic drug, 5-fluorouracil.     

苦蝶子的化学成分研究

目的:研究菊科苦荬菜植物苦碟子(Ixeris sonchifolia(Bge.)Hance)的化学成分。方法:利用各种色谱技术进行分离,根据光谱数据鉴定结构。结果:从苦碟子中分离得到7个已知成分,分别鉴定为lir-ioresinol-A(1)、木犀草素(2)、芹菜素(3)、原儿茶酸乙酯(4)、香草醛(5)、对羟基苯甲酸(6)、香草酸(7)。结论:化合物4和7为首次从该植物中分离得到。     

A New Sesquiterpene Lactone from Tsoongiodendron Odorum Chun

Abstract

A new sesquiterpene lactone (1) was obtained from the cytotoxic fraction of 95% ethanol extract of root barks of Tsoongiodendron odorum Chun together with two known sesquiterpene lactones, costunolide (2) and parthenolide (3). The structure of 1 was elucidated as 5α, 6α, 7β, 10β-11α, 13-dihydro-4(15)-eudesmene-12, 6-olide on the basis of chemical and spectral evidence including X-ray diffraction analysis. Costunolide showed cytotoxic activity against human leukemia (HL-60) cell line. Parthenolide showed promising cytotoxic activities in vitro against HCT-8, Bel-7402, SKOV3, KB, HELA and EJ cell lines. Also, the cytotoxic ethyl acetate fraction of ethanol extract of the root barks from which three chemical components were isolated showed promising cytotoxic activities in vitro against KB, BGC-823, Bel-7402, HCT-8, HL-60 cell lines.     

Cytotoxic constituents of the leaves of Ixeris sonchifolia

The ethyl acetate extract of the leaves of Ixeris sonchifolia afforded two new and two known sesquiterpene lactone glucosides of the guaiane-type, together with a known alkenol glucoside. The known compounds were identified as ixerin Z (1), ixerin Z-6'-p-hydroxyphenylacetate (2), and (Z)-3-hexen-1-ol-beta-D-glucopyranoside (3), respectively. The structures of the new compounds were elucidated as 11,13a-dihydroixerin Z [4, 3-hydroxy-2-oxo-guaia-1(10), 3-dien-5alpha,6beta,7alpha, 11betaH-12,6-olide-3-O-beta-D-glucopyranoside], and 3,10beta-dihydroxy-2-oxo-guaia-3,11(13)-dien-1alpha,5alpha,6alpha,7aH-12,6-olide-10-O-beta-D-glucopyranoside (5), respectively. The cytotoxicity of these compounds against human hepatocellular carcinoma cell (HepG2) and human melanoma cell (SK-MEL-2) was evaluated.     

苦碟子化学成分的分离与鉴定

目的对菊科苦荬菜属植物抱茎苦荬菜[Ixeris sonchifolia(Bge.)Hance]的化学成分进行研究。方法运用硅胶﹑聚酰胺柱色谱﹑Sephadex LH-20柱色谱﹑ODS柱色谱、制备HPLC等分离手段进行化学成分的分离纯化,根据理化性质及波谱数据鉴定其结构。结果从苦碟子全草中分离得到4个化合物。分别鉴定为3β-hydroxyolean-12-en-11-one acetate(1)、3,4-dihydroxybenzalacetone(2)、7-O-β-D-glucopyranosyl-luteolin-3'-O-β-D-glucopyranoside(3)、5,7-dihydroxy-4'-methoxy-fla-vone-7-rutinoside(4)。结论这些化合物均为首次从该属植物中分离得到。     

苦碟子水提取液对大鼠离体胸主动脉环的舒张作用

目的研究苦碟子的内皮依赖性血管舒张作用,并探讨其可能机制。方法采用大鼠离体主动脉环灌流模型,观察累积浓度苦碟子对基础状态、去氧肾上腺素(PE)和氯化钾(KCl)预收缩的内皮完整血管环和去内皮血管环的舒张作用。结果苦碟子水提取液(苦碟子注射液,相当于含苦碟子原材料0.01～10g.L-1)对基础状态的内皮完整血管环和去内皮血管环的张力无影响。对PE预收缩的内皮完整血管环,苦碟子在累积浓度0.03～10g.L-1呈浓度依赖性舒张作用,分别用一氧化氮合酶抑制剂左旋硝基精氨酸甲酯(0.1mmol.L-1)和鸟苷酸环化酶抑制剂亚甲蓝(10μmol.L-1)预处理,此作用被抑制,用环氧合酶抑制剂吲哚美辛(10μmol.L-1)预处理亦被抑制。对KCl预收缩的内皮完整血管环和对PE或KCl预收缩的去内皮血管环,苦碟子在累积浓度0.01～10g.L-1无明显舒缩作用。结论苦碟子(0.03～10g.L-1)对主动脉具有内皮依赖性舒张作用。该作用可能是通过血管内皮细胞一氧化氮-鸟苷酸环化酶途径和血管内皮细胞环氧合酶途径介导的。     

中药败酱草的形态组织学研究——Ⅲ.菊科苦苣菜属、莴苣属和苦荬菜属植物

本文报道我国北方使用的来源于菊科植物的中药败酱草的生药形态组织学的研究结果,它们是:苣荬菜Sonchus arvensis L.S.、苦苣菜oleraceus L.圆耳苦苣菜S.asper (L.)Hill.紫花山莴苣Lactuca tatarica(L.)C.A.Mey.、中华苦荬菜Ixeris ccinensis(Thunb.)Nakai、抱茎苦荬菜I.sonchifolia Hance和苦荬菜I.denticulata(Houtt.)Stebb..文中附有生药组织图7幅以及上述生药的性状检索表和显微特征检索表.     

Sesquiterpene Glucosides from Anti-leukotriene B4 Release Fraction of Taraxacum Officinale

Abstract

Chemical examination of the MeOH extract of the root of Taraxacum officinale, which exhibited inhibitory activity on the formation of leukotriene B₄ from activated human neutrophils, has resulted in the isolation of 14-O-β-D-glucosyl-11,13-dihydro-taraxinic acid (1) and 14-O-β-D-glucosyl-taraxinic acid (2). The absolute stereostructure of 1 has been established by X-ray chrystallographic examination.     

高效液相色谱校正因子法测定苦碟子提取物中5种主要成分的含量

目的通过测定苦碟子提取物中咖啡酸、菊苣酸、木犀草素-7-O-β-D-葡萄糖苷-(1→6)-β-D-葡萄糖苷、芹菜素-7-O-β-D-葡萄糖醛酸苷与木犀草素-7-O-β-D-葡萄糖醛酸苷的校正因子,建立以1种对照品测定苦碟子提取物中5种主要成分的含量的方法。方法以Agilent TC-C18(250 mm×4.6 mm,5μm)为分析柱,柱温30℃,流动相为甲醇(A)-0.05%磷酸(B),梯度洗脱:0~10 min:30%A,10~30 min:30%~50%A,流速1.2 mL.min-1,检测波长350 nm。结果咖啡酸、菊苣酸、木犀草素-7-O-β-D-葡萄糖苷-(1→6)-β-D-葡萄糖苷、芹菜素-7-O-β-D-葡萄糖醛酸苷的校正因子分别为:1.129、0.873 3、1.320、1.129(RSD=1.6%~2.1%),苦碟子提取物中咖啡酸、菊苣酸、木犀草素-7-O-β-D-葡萄糖苷-(1→6)-β-D-葡萄糖苷、木犀草素-7-O-β-D-葡萄糖醛酸苷与芹菜素-7-O-β-D-葡萄糖醛酸苷的含量分别为4.2%、29.5%、6.5%、23.0%、5.0%。结论本法简便,灵敏,重现性好,可用于苦碟子提取物和制剂的定量分析及质量控制。     

苦碟子中的新黄酮苷

苦碟子为菊科植物抱茎苦荬菜［Ｉｘｅｒｉｓｓｏｎｃｈｉｆｏｌｉａ（Ｂｇｅ．）Ｈａｎｃｅ］的当年生干燥全草．具有清热解毒、排脓之功效．利用大孔树脂、硅胶柱层析及聚酰胺柱层析从中分离得到两个新的黄酮苷类成分,其中一个命名为木犀草素７ＯβＤ吡喃葡萄...     

Anti-inflammatory and Analgesic Effects of Drypemolundein A,a Sesquiterpene Lactone from Drypetes molunduana

Previous pharmacological screening in our laboratory showed analgesic and anti-inflammatory effects of a crude stem bark extract of Drypetes molunduana. Phytochemical studies of this plant led to the isolation an structural elucidation of seven pentacylic triterpenes and one lignan, which were already known compounds, and a new furanosesquiterpene lactone, Drypemolundein A. The purpose of this study was to examine the anti-inflammatory and analgesic activities of drypemolundein A. The compound was studied against carrageenan-induced acute edema. At doses of 10 and 20 mg/kg, orally administered, it significantly reduced (57.57 and 66.66% inhibition at 1 h intervals, respectively) paw edema. At the same doses, this sesquiterpene lactone also exhibited significant analgesic action in force-induced pain in rat paw. These results indicate that drypemolundein A functions as an effective anti-inflammatory and analgesic agent.