Triterpenoid prosapogenols and prosapogenins from the husks of Xanthoceras sorbifolia

Two new prosapogenins, 16-O-acetyl-21-O-(4-angeloyl)-alpha-l-rhamnopyranosyl barringtogenol C (1), 28-O-beta-d-glucopyranosyl 16-deoxybarringtogenol C (2), were isolated from the acid hydrolyzate of the crude saponin obtained from the husks of Xanthoceras sorbifolia Bunge, along with six known triterpenoids. These structures were established on the basis of chemical and detailed spectral evidences. Compounds 1 and 2 showed cytotoxic activity against human cell lines (A375-S2, HeLa).     

Two new isoxazolines from the husks of Xanthoceras sorbifolia Bunge

Two new isoxazoline compounds, 1-oxa-2-azaspiro[4.5]dec-2-ene-8β-ol (1) and 1-oxa-2-azaspiro[4.5]dec-2-ene-8α-ol (2), were isolated from the husks of fruits of Xanthoceras sorbifolia Bunge and their structures were determined by spectroscopic analyses, including X-ray crystallography, HRESI-MS, UV, IR, and 1D and 2D NMR (HSQC, HMBC, NOESY) methods. Neither compound showed significant inhibitory effects on butyrylcholinesterase (BuchE) and acetylcholinesterase (AChE), nor the selected tumor cells growth. Based on an online activity prediction program (PASS ONLINE), the structures with isoxazoline skeletons were found to show potential anti-asthmatic (AM) and anti-anaphylaxis (AP) activities; moreover, compounds 1 and 2 were predicted to possess high affinities for many enzymes involved in AM and AP according to the RCSB Protein Data Bank. High-affinity binding to phosphodiesterase IV (PDE-4), an important inflammatory modulator in asthma, was demonstrated experimentally, beside that, the predicted structures based on compounds 1 and 2 were analyzed for PDE-4 interactions using the molecular docking methodology of Discovery Studio 3.0 (DS 3.0). The predicted structure 2A-6 exhibited much higher affinity and stability of PDE-4 binding than the clinical PDE-4 inhibitor rolipram.     

文冠果果壳的化学成分

目的对文冠果(XanthocerassorbifoliaBunge)果壳乙醇提取物的化学成分进行研究。方法利用硅胶柱色谱,SephadexLH20凝胶柱色谱等进行分离纯化,根据理化性质和波谱数据分析进行结构鉴定。结果得到6个化合物,分别鉴定为:5α,8α表二氧(22E,24R)麦角甾6,22二烯3β醇(Ⅰ)、东莨菪素(Ⅱ)、异秦皮啶(Ⅲ)、对羟基苯甲醛(Ⅳ)、3,4,5三甲氧基苯甲酸(Ⅴ)、原儿茶酸乙酯(Ⅵ)。结论化合物Ⅰ～Ⅵ均为首次从该属植物中分离得到。     

文冠果种皮化学成分的分离与鉴定

目的对文冠果(Xanthoceras sorbifolia Bunge)种皮乙醇提取物的化学成分进行研究。方法采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱等方法进行分离纯化,根据化合物的理化性质和波谱数据进行结构鉴定。结果从文冠果种皮中分离得到8个已知化合物,分别鉴定为:秦皮素(fraxetin,1)、秦皮苷(fraxin,2)、异嗪皮啶(isofraxidin,3)、原儿茶酸(protocatechuic acid,4)、香草酸(vanillic acid,5)、对甲氧基苯甲酸(4-methoxybenzoic acid,6)、β-谷甾醇(β-sitosterol,7)、胡萝卜苷(daucosterol,8)。结论化合物3~7均为首次从文冠果种皮中分离得到,化合物6为首次从该属植物中分离得到。     

高效液相色谱法测定文冠木各部位中杨梅树皮素和槲皮素的含量

应用高效液相色谱法测定文冠木各部位中杨梅树皮素和槲皮素的含量 ,色谱柱采用SUNTEKAccusiLC 18柱 ,流动相为甲醇∶水∶磷酸 (4 0∶6 0∶0 4,V∶V∶V) ,柱温为 40℃ .回收率分别为 10 1 3 %和 94 9% ,RSD分别为 1 4%和 3 5 %     

文冠果花化学成分的分离与鉴定

目的研究文冠果(Xanthoceras sorbifolia Bunge)花的化学成分。方法采用制备薄层色谱、反复硅胶柱色谱、Sephadex LH-20柱色谱、ODS柱色谱等方法进行分离纯化;根据理化性质及光谱数据确定化合物的结构。结果分离得到13个化合物,分别鉴定为对羟基苯甲酸甲酯(methyl 4-hydroxybenzoate,1)、白桦脂醇(betulin,2)、山柰酚(kaempferol,3)、槲皮素(quercetin,4)、槲皮苷(quercitrin,5)、东莨菪素(scopoletin,6)、鼠李柠檬素(rhamnocitrin,7)、芦丁(rutin,8)、异杨梅树皮苷(myricetin-3-O-β-D-glucopyranoside,9)、1-O-甲基-肌-肌醇(1-O-methyl-myo-inositol,10)、柚皮素(naringenin,11)、柯依利素(chrysoeriol,12)、山柰酚-3-O-(2-O-α-L-鼠李糖基)-β-D-葡萄糖苷(kaempferol-3-O-(2-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside,13)。结论化合物1、7、9、12-13为首次从文冠果属植物中分离得到。     

文冠果化学成分及药理作用研究进展

目的对文冠果 (XanthocerassorbifoliaBunge )化学成分及药理作用研究进展进行综述。 方法按照化学成分和药理作用类型进行分类综述。结果与结论文冠果中主要含有三萜皂苷、黄酮、香豆素等类型成分 ,并且具有抗炎、抑制HIV 1蛋白酶、改善学习记忆功能等药理活性     

文冠果果柄的化学成分

目的首次研究文冠果果柄的化学成分。方法采用大孔树脂、硅胶柱色谱分离化学成分,IR1、H-NMR1、3C-NMR等方法进行结构鉴定。结果从文冠果果柄95%(φ)大孔树脂乙醇(φ=95%)洗脱物中分离鉴定了6个化合物,分别为β-谷甾醇(-βsitosterolⅠ)、α-菠甾醇(-αspinaste-rolⅡ)、白桦脂醇(betulinⅢ)、21-O-angeloyl-R1-barrigenolⅣ、21,22-O-di-angeloyl-R1-barri-genolⅤ、胡萝卜苷(daucosterolⅥ)。结论化合物Ⅲ首次从本属植物中分得。     

文冠木正丁醇提取物的抗炎作用

文冠木正丁醇提取物对二甲苯致小鼠耳肿胀、蛋清致大鼠足肿胀、角叉菜胶致小鼠足肿胀、醋酸致小鼠腹腔毛细血管通透性增加、小鼠羧甲基纤维素囊中白细胞游走、小鼠棉球肉芽肿生长均有显著的抑制作用 ,同样剂量下 ,文冠木正丁醇提取物对角叉菜胶致去双侧肾上腺小鼠足肿胀仍有显著的抑制作用 ,且对小鼠肾上腺重量及肾上腺中维生素C的含量没有明显影响     

UPLC-QTOF-MS法同时测定春季文冠果叶中11种黄酮类化合物的含量

目的 建立UPLC-QTOF-MS法同时测定春季文冠果叶中11种黄酮类化合物的含量.方法 采用ACQUITY UPLC HSS T3色谱柱(100 mm ×2.1 mm,1.8μm),以体积分数0.05％甲酸水为流动相A,体积分数0.05％甲酸乙腈为流动相B,梯度洗脱,流速0.4 mL· min-1,电喷雾离子源(ES...     

Triterpenoids from the husks of Xanthoceras sorbifolia Bunge

A new triterpenoid saponin, 3-O-[(3-O-alpha-l-arabinofuranosyl-2-O-beta-d-galactopyranosyl)-beta-d-glucuronopyranosyl]-21,22-di-O-angeloyl-R1-barrigenol (1), together with four known triterpenoids, have been isolated from the husks of Xanthoceras sorbifolia Bunge. Their structures were elucidated based on chemical and spectral analysis. Among them, 1 was found to have activity of inhibiting the proliferation of six human tumour cell lines (IC50 10-40 mug/ml).     

文冠木超微饮片的药材鉴别和表儿茶素的含量测定

目的 建立文冠木超微饮片的质量标准.方法 用薄层色谱法,以表儿茶素为对照品进行薄层鉴别;采用HPLC法测定文冠木超微饮片中主要活性成分表儿茶素的含量.结果 薄层色谱斑点清晰,重复性好;表儿茶素含量为0.44％ ～2.21％(平均0.83％).结论 所用方法操作简单、准确可靠、重复性好,可用于蒙药文冠木超微饮片的内在质量控制.     

文冠果的化学成分与生物活性研究进展

文冠果为我国特有的珍稀木本油料作物,是绿化、食用、药用和制作生物燃料油的重要木本油料树种,近年来广泛受到学术界关注.其果仁、果皮、枝叶等药用部位富含三萜、黄酮、香豆素、甾醇等化学成分.现代医学研究表明,文冠果具有抗炎、抗肿瘤、抑制HIV蛋白酶、促进NGF介导的神经突触生长、改善学习记忆等药理作用和生物活性.对近年来有关...     

Two new triterpenes from the husks of Xanthoceras sorbifolia

Two new triterpenes, 22-angeloyl-21-epoxyangeloylbarringtogenol C (1) and 21,22-diangeloyl-24-hydroxy-R(1)-barrigenol (2), and the known 21,22-diangeloyl-R(1)-barrigenol (3) were isolated from the husks of Xanthoceras sorbifolia Bunge. Their structures were elucidated based on detailed NMR analysis. Compounds 1 and 2 inhibited significantly the growth of cancer cell lines (A375-S2, HeLa) with IC(50) values ranging from 2.9 to 76.3 micromol/L.     

文冠木超微粉对大鼠佐剂关节炎的影响

目的研究文冠木超微粉(BPX)和普通粉对大鼠佐剂性关节炎的影响,并对比超微粉与普通粉的药理学作用。方法氟氏完全佐剂诱导大鼠产生佐剂性关节炎,以关节肿胀程度和炎症细胞因子TNF-α、IL-6的变化为指标来观察低剂量BPX(普通粉剂量的1/4、1/8)和正常剂量普通粉对大鼠佐剂性关节炎的影响。结果 BPX在剂量相对较低时(普通粉剂量的1/4、1/8)能明显抑制佐剂关节炎大鼠的原发性肿胀(P<0.05),而且抑制作用优于普通粉(P<0.05);并可明显降低血清TNF-α、IL-6水平,且与普通粉作用相当。结论 BPX对大鼠佐剂性关节炎有明显抑制作用,且剂量小于普通粉,药效优于普通粉。     

HPLC法测定文冠果果仁中文冠果皂苷B的含量

目的:建立文冠果果仁中文冠果皂苷B测定方法,为文冠果果仁及其制剂的工艺研究与质量控制提供评价指标与评价方法。方法:采用反相高效液相色谱法,色谱柱为YMC C18(250×4．6mm,5μm),流动相为甲醇-0．1％磷酸溶液(60:40),流速1．0ml／min,检测波长为215nm。结果:文冠果皂苷B在0．204-1．02μg线性范围内有良好的线性关系,平均回收率为99．05％。结论:本方法准确可靠,重现性好,可作为文冠果果仁质量控制的依据。     

HPLC法测定文冠果果仁中文冠果皂苷B的含量

目的:建立文冠果果仁中文冠果皂苷B测定方法,为文冠果果仁及其制剂的工艺研究与质量控制提供评价指标与评价方法。方法:采用反相高效液相色谱法,色谱柱为YMC C18(250×4．6mm,5μm),流动相为甲醇-0．1％磷酸溶液(60:40),流速1．0ml／min,检测波长为215nm。结果:文冠果皂苷B在0．204-1．02μg线性范围内有良好的线性关系,平均回收率为99．05％。结论:本方法准确可靠,重现性好,可作为文冠果果仁质量控制的依据。     

文冠木中杨梅素的含量测定简

目的建立测定文冠木中杨梅素含量的高效液相色谱法。方法采用KromasilODSC·s色谱柱（250mm×4．6mm,5μm）,流动相为甲醇-水-冰醋酸（65：35：0．1）,流速为1．0mL／min,检测波长为295nm,柱温为30℃。结果杨梅素加样回收率为99．56％,RSD为2．04％,符合定量分析要求。结论该方法简便、准确,可作为文冠木药材的质量控制方法。     

Two new oleanane-type pentacyclic triterpenoid saponins from the husks of Xanthoceras sorbifolia Bunge

Two new triterpenoid saponins (1, 2) and a known saponin (3) were isolated from the husks of Xanthoceras sorbifolia Bunge., and their structures were elucidated as 3-O-β-D-glucopyranosyl(1 → 6)-[angeloyl(1 → 2)]-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl(1 → 2)-[β-D-glucopyranosyl(1 → 6)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (1), 3-O-β-D-glucopyranosyl-28-O-[β-D-glucopyranosyl(1 → 2)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (2), and 3-O-β-D-glucopyranosyl-28-O-[α-L-rhamnopyranosyl(1 → 2)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (3), on the basis of the spectral analysis of NMR and chemical methods. Cytotoxic assay indicated that none of them showed obvious inhibitory effect on the proliferation of two human tumor cell lines.     

文冠木中总氨基酸的含量测定

目的建立测定文冠木中总氨基酸含量的分光光度法。方法采用紫外-可见分光光度法对文冠木中总氨基酸的含量进行测定。结果线性回归方程为Y=0.958 4 X-0.009 4(r=0.999 8),平均回收率为98.98%,RSD为1.20%(n=6)。测得文冠木中总氨基酸的含量为0.64%。结论该方法灵敏、简便、快速、准确可靠,可用于文冠木中总氨基酸的含量测定。