猴耳环化学成分研究

目的:研究猴耳环的化学成分。方法:采用硅胶、Sephadex LH-20对猴耳环乙酸乙酯部位进行分离纯化,根据理化性质与光谱数据进行结构鉴定。结果:共分离得到9个化合物,分别鉴定为:β-谷甾醇(1)、正三十三烷(2)、5-羟基-3,7,3',4'-四甲氧基黄酮(3)、齐墩果酸(4)、5,4'-二羟基-3,7,3'-三甲氧基黄酮(5)、α-香树脂醇(6)、木犀草素(7)、熊果酸(8)、木犀草苷(9)。结论:其中化合物3、5为首次从该植物中分离得到。     

猴耳环化学成分研究

目的:对猴耳环的化学成分进行研究.方法:采用柱色谱分离,通过理化性质、色谱和光谱分析法鉴定化合物的结构.结果:从猴耳环的叶和嫩枝中分离鉴定出一对黄烷异构体7,3′-二-O-没食子酰基特利色黄烷(Ⅰ)和7,4′-二-O-没食子酰基特利色黄烷(Ⅱ),及一个儿茶酚类化合物7-O-没食子酰基表没食子儿茶素(Ⅲ).结论:化合物Ⅰ为新结构,化合物Ⅲ为首次从该属植物中分离得到,且化合物Ⅲ的碳谱数据由本文首次报道.     

不同产地猴耳环总黄酮含量比较研究△

目的：测定不同产地猴耳环药材中的总黄酮含量。方法：以芦丁为对照品,三氯化铝（AlCl3）比色,采用紫外可见分光光度法（UV）测定样品总黄酮含量,检测波长406nm。结果：总黄酮在5．09～50．90μg·mL^-1线性关系良好,回归方程为Y=0．0267X＋0．0072,r=0．9991;平均加样回收率为101．23％,RSD=1．93％（n=6）。结论：AlCl3,比色法准确、简便,具有良好的重复性和稳定性,可用于猴耳环药材中总黄酮的含量测定;不同产地猴耳环中总黄酮的含量存在一定的差异。     

广东从化猴耳环栽培基地土壤肥力综合评价△

目的:对广东从化猴耳环栽培基地土壤肥力进行综合评价。方法:对基地4个坡向0～20cm和20～40cm的土壤样品进行理化性状测定和分析,并采用改进的内梅罗综合指数对土壤肥力进行了综台评价。结果:土壤pH偏低,有机质含量贫乏,全氮、全磷和全钾含量低。有效氮和有效钾含量丰富,有效磷含量较低,矿质元素含量偏低。东坡和西坡的有效氮,有效钾与有机质含量比南坡和北坡高。结论:所有样品的土壤综合肥力系数均低于0.9,土壤肥力处于贫瘠水平。     

Antiviral activity-guided fractionation from Araucaria angustifolia leaves extract

Ethnopharmacological relevance

Araucaria angustifolia (Bert.) O. Kuntze (Araucariaceae) is a Brazilian medicinal plant traditionally used for the treatment of various illnesses including dried skin, wounds, shingles, and sexually transmitted diseases.

Aim of the study

The rationale of the study was to provide evidence of its antiherpes activity in order to confirm its popular use that could be related to herpes disease.

Materials and methods

The crude hydroethanolic extract (HE) obtained from Araucaria angustifolia leaves was submitted to a sequential liquid–liquid extraction with solvents of increased polarity. The HE and fractions obtained were evaluated for cytotoxicity and antiherpes activity (Herpes Simplex Virus type 1) by MTT assay. The most active fractions were selected to perform an in vitro antiviral activity-guided chromatographic fractionation.

Results

The ethyl acetate (EA) and n-butanol (NB) fractions have shown the best results for antiherpetic activity and their further fractionation yielded 22 subfractions. From these subfractions, 14 were active, and the most potent antiherpetic activity was obtained for NB1-4 subfraction with selectivity index (SI) of 57.51. Chemical analysis of NB1-4 subfractions revealed the presence of proanthocyanidins and the known biflavonoids (bilobetin, II-7-O-methyl-robustaflavone and cupressuflavone). The same biflavonoids have been detected in EA subfractions.

Conclusion

The present study has shown that the hydroethanolic extract from Araucaria angustifolia leaves as well as many different fractions and subfractions exhibited antiherpes activity, supporting the use of this plant species in folk medicine.     

Cytotoxic triterpenoid saponins acylated with monoterpenic acid from Pithecellobium lucidum

Three new oleanane-type triterpene saponins, named pithelucosides A-C (1-3), together with two known saponins (4, 5) were isolated from the roots of Pithecellobium lucidum. The structures of the new saponins were established on the basis of extensive 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. Compounds 1-5 and 7 (pro-sapogenin obtained from the mild alkaline hydrolysate of 1) were evaluated for cytotoxic activity on five human tumoral cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) and for hemolytic property against rabbit erythrocytes. Compounds 2-5 showed significant cytotoxic activities with IC50 values of 0.61-7.56 microM. All tested compounds did not exhibit any hemolytic activity in the concentration range 0.01-100 microM.     

丰城鸡血藤异黄酮及黄烷类化学成分的研究

对丰城鸡血藤的化学成分进行分离及鉴定.利用硅胶柱色谱、反相硅胶柱色谱、凝胶柱色谱和制备液相色谱等各种色谱技术对丰城鸡血藤进行化学成分分离和纯化,并经核磁共振等现代波谱技术对得到的化合物进行结构鉴定.从丰城鸡血藤中分离鉴定了9个异黄酮类化合物和2个黄烷类化合物,分别为:5-O-methy genistein(1)、7-hydroxy-3',4'-dimethoxyi soflavone(2)、芒柄花苷(3)、儿茶素(4)、刺芒柄花素(5)、染料木素(6)、毛蕊异黄酮(7)、没食子儿茶素(8)、sissotrin(9)、Wistin(10)、大豆苷(11).其中,化合物1,2,9是首次从该属植物中分离得到,化合物4,8是首次从该植物中分离得到.     

猴耳环高效液相色谱指纹图谱及化学模式识别研究

目的建立猴耳环高效液相色谱(HPLC)指纹图谱分析方法,为其真伪鉴别及质量评价提供参考。方法以HPLC法建立猴耳环的指纹图谱。采用YMC C18色谱柱(4.6 mm×100 mm,2.7μm);流动相为乙腈(A)-0.2%磷酸水(B),梯度洗脱;流速1.0 mL·min^-1;柱温25℃;进样量10μL;检测波长为300 nm。通过相似度评价、聚类分析和主成分分析对指纹图谱进行评价。结果获得猴耳环HPLC指纹图谱10个共有峰,结合对照品定位和紫外光谱分析,指认出没食子酸、杨梅苷、槲皮苷、7-没食子酰基特利色黄烷及7,3’-和7,4’-二没食子酰基特利色黄烷异构体6个共有峰;51批猴耳环药材有44批相似度大于0.90;聚类分析和主成分分析可将51批猴耳环聚为4类,显示猴耳环药材质量受外观性状、产地、采收时间等因素综合影响。结论所建立的方法简单准确,指纹图谱结合化学模式识别技术能够系统、全面地评价猴耳环的质量。     

Antiviral flavonoids from the seeds of Aesculus chinensis

A bioassay-guided fractionation of an ethanol extract of the seeds of Aesculus chinensis led to the isolation of two new flavanoids (1 and 2), along with eight known ones (3-10). The structures of the new compounds were elucidated by spectroscopic methods including 2D NMR. All compounds were tested for antiviral activity against respiratory syncytial virus (RSV), parainfluenza virus type 3 (PIV 3), and influenza virus type A (Flu A). Compounds 1, 2, and 6 showed significant antiviral activities against RSV with IC(50) values of 4.5, 6.7, and 4.1 microg/mL and selective index (SI) values of 15.8, 32, and 63.8, respectively. Compound 8 demonstrated significant antiviral activity against Flu A with an IC(50) of 24.5 microg/mL and a SI of 16.0, respectively.     

Antiviral saponins from Tieghemella heckelii

Arganine C (1) and a new saponin, tieghemelin (2), were isolated from Tieghemella heckelii fruits. Arganine C (1) strongly inhibited HIV entry into cells in a cell fusion assay. The less potent tieghemelin (2) was converted into arganine C (1) by reduction of its ethyl ester with sodium borohydride. The removal of the four-sugar chains from arganine C (1) and tieghemelin (2) to give 16alpha-hydroxyprotobassic acid 3-O-beta-D-glucopyranoside (3) and 16alpha-hydroxyprotobassic acid 3-O-beta-D-glucuronopyranoside (4), respectively, caused total loss of activity in both cases. Arganine C (1) was not significantly cytotoxic to HeLa-CD4(+) cells at the level required to reduce the syncytium count to zero, suggesting it to be a promising candidate for further study as an antiviral drug.     

Acutifolins A-F, a new flavan-derived constituent and five new flavans from Brosimum acutifolium.

Acutifolin A (1), a novel constituent with a bicyclo[3.3.1]non-3-ene-2,9-dione ring, acutifolins B-F (2-6), five new flavans, and three known flavans were isolated from the bark of Brosimum acutifolium, a Brazilian folk medicine ("Mururé"). Their structures were elucidated by spectroscopic methods, including 2D NMR.     

Antiviral triterpenoids from the medicinal plant Schefflera heptaphylla

Schefflera heptaphylla (L.) Frodin is a principal ingredient of an herbal tea formulation widely used for the treatment of common cold in southern China. An extract of the long leafstalk of the compound leaf of S. heptaphylla exhibited the most potent antiviral activity against respiratory syncytial virus (RSV). Further antiviral-guided fractionation and isolation of the leafstalk extract of S. heptaphylla led to obtain two highly active pure triterpenoids, namely 3alpha-hydroxylup-20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid 3-O-sulfate, together with an inactive saponin, 3alpha-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-alpha-l-rhamnopyranosyl-(1-->4)-O-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside. An antiviral assay using a cytopathic effect (CPE) reduction method showed that the two triterpenoids possessed broader antiviral activity against respiratory syncytial virus (RSV) with a similar 50% inhibition concentration (IC(50)) value of 6.25 microg/mL, influenza A (H1N1) virus with IC(50) values of 25 and 31.3 microg/mL, Coxsackie B3 (Cox B3) virus with IC(50) values of 12.5 and 20 microg/mL and herpes simplex virus type 1 (HSV-1) with IC(50) values of 18.8 and 25 microg/mL, respectively, whereas the saponin did not have antiviral activity against these four viruses at a concentration of 100 microg/mL.     

New flavans,spirostanol sapogenins,and a pregnane genin from Tupistra chinensis and their cytotoxicity

Seven new compounds, including three new flavans [tupichinol A-C (1-3)], three new spirostanol sapogenins [tupichigenin D-F (4-6)], and one new pregnane genin [tupipregnenolone (7)], together with 18 known compounds, were isolated from the underground parts of Tupistra chinensis. The structures of the new compounds were elucidated by spectroscopic analysis and chemical evidence. The structures and relative stereochemistry of 1 and 9 were further confirmed by single-crystal X-ray crystallographic analysis. Compounds Delta(25(27))-pentrogenin, 10, and ranmogenin A showed 100%, 96%, and 80% inhibition, respectively, against human gastric tumor (NUGC) cells at a concentration of 50 microM. Delta(25(27))-pentrogenin showed 100% inhibition against human nasopharyngeal carcinoma (HONE-1) cells at a concentration of 50 microM.     

华中枸骨黄烷类成分体外抗炎与自由基清除活性

为研究华中枸骨中多个黄烷类成分(1～6)体外抗炎与自由基清除活性,并初步分析其构效关系.采用脂多糖诱导小鼠RAW264.7巨噬细胞炎症模型,MTT法测定细胞毒性作用,Griess法测定NO生成量,ELISA法检测细胞上清液中TNF-α,IL-1β,IL-6,PGE2的含量;体外测定清除DPPH自由基,超氧阴离子自由基和羟自由基活性.结果表明黄烷1,3,4,6体外显示很强的抗炎活性,能显著抑制NO,TNF-α,IL-1ββ和IL-6的分泌,化合物1的抑制作用最强,黄烷2和5显示相对较弱的抑制活性,体外自由基清除活性顺序与抗炎活性相似.因此,黄烷1,3,4,6是华中枸骨抗炎和自由基清除活性的活性成分,构效关系初步分析表明4'-羟基为黄烷类化合物显示抗炎和自由基清除活性的主要结构部位.     

Cembranolides from the leaves of Croton gratissimus

Ten new cembranolides, (-)-(1R*,4R*,10R*)-4-methoxycembra-2E,7E,11Z-trien-20,10-olide (1), (-)-(1S*,4R*,10R*)-1-hydroxy-4-methoxycembra-2E,7E,11Z-trien-20,10-olide (2), (-)-(1S*,4S*,10R*)-1,4-dihydroxycembra-2E,7E,11Z-trien-20,10-olide (3), (-)-(1S*,4S*,10R*)-1,4-dihydroxycembra-2E,7E,11Z-trien-20,10-olide (4), (+)-(10R*)-cembra-1E,3E,7E,11Z,16-pentaen-20,10-olide (5), (+)-(10R*)-cembra-1Z,3Z,7E,11Z,15-pentaen-20,10-olide (6), (+)-(5R*,10R*)-5-methoxycembra-1E,3E,7E,11Z,15-pentaen-20,10-olide (7), (+)-(1S*,4S*,7R*,10R*)-1,4,7-trihydroxycembra-2E,8(19),11Z-trien-20,10-olide (8), (-)-(1S*,4S*,7S*,10R*)-1,4,7-trihydroxycembra-2E,8(19),11Z-trien-20,10-olide (9), and (+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide (10), together with six known compounds, lupeol, 4(15)-eudesmene-1β,6α-diol, α-glutinol, 24-ethylcholesta-4,22-dien-3-one, (+)-(1R*,10R*)-cembra-2E,4E,7E,11Z-tetraen-20,10-olide, and (+)-(1R*,4S*,10R*)-4-hydroxycembra-2E,7E,11Z-trien-20,10-olide (4a), have been isolated from the leaves of Croton gratissimus. The acetyl derivatives of 8 and 4a were evaluated against a chloroquine-sensitive strain of Plasmodium falciparum (D10).     

南岭栲叶黄酮类成分的研究

目的研究南岭栲Castanopsis fordii Hance叶的黄酮类成分。方法南岭栲叶80%乙醇提取物采用Sephadex LH-20、MCI、硅胶、半制备柱进行分离纯化,根据波谱数据鉴定所得化合物的结构。结果从中分离得到9个化合物,分别鉴定为槲皮素(1)、槲皮素-3-O-α-L-鼠李糖苷(2)、杨梅苷(3)、myricetin-3-O-(2″-O-galloyl)-α-rhamnopyranoside(4)、quercetin 3-O-(2″-O-galloyl)-α-rhamnopyranoside(5)、阿福豆苷(6)、3,5,7,3',5'-五羟基-(2R,3R)-二氢黄酮3-O-α-L-鼠李糖苷(7)、落新妇苷(8)、异落新妇苷(9)。结论化合物2、3为首次从该植物中分离得到,化合物1、4~9为首次从锥属植物中分离得到。     

膜荚黄芪叶黄酮类成分的研究

目的研究膜荚黄芪Astragalus membranaceus(Fish.)Bge.叶黄酮类成分。方法膜荚黄芪叶75%乙醇提取物的乙酸乙酯、正丁醇部位采用硅胶、ODS、制备型HPLC柱进行分离纯化,根据波谱数据鉴定所得化合物的结构。结果从中分离鉴定出13个化合物,分别为槲皮素(1)、槲皮素-3-O-β-D-葡萄糖苷(2)、鼠李柠檬素-3-O-β-D-葡萄糖苷(3)、rhamnocitrin-3-O-β-neohesperidoside(4)、rhamnocitrin-3-O-β-D-glucopyranoside(1→2″)-β-D-apiofuranosyl(5)、沙苑子苷(6)、黄豆黄素(7)、4',7-二羟基-3'-甲氧基异黄酮(8)、染料木素(9)、芒柄花素-7-O-β-D-葡萄糖苷(10)、染料木苷(11)、黄豆黄苷(12)、银椴苷(13)。结论化合物5、8、13为首次在黄芪属植物中分离得到,化合物2为首次在该植物中分离得到。     

Saponins from the leaves of Mimusops laurifolia

Fifteen new bidesmosidic triterpenoid saponins (1-15) were isolated from a methanol extract of the leaves of Mimusops laurifolia. Their structures were established using one- and two-dimensional NMR spectroscopy and mass spectrometry and determined to be bidesmosides of protobassic acid (2-4, 11, 12, and 15) and of 16alpha-hydroxyprotobassic acid (1, 5-10, 13, and 14).     

枸骨叶中的黄酮类成分(英文)

目的:研究枸骨Ilex cornuta Lindl.ex Paxt.叶的黄酮类成分。方法:利用硅胶柱色谱和半制备高效液相色谱对枸骨的叶进行分离纯化, 利用光谱学手段结合理化性质鉴定其结构。结果:分离鉴定了9个黄酮类化合物, 分别为:山柰酚-3-O-β-D-吡喃葡萄糖(1→2)-α-L-吡喃阿拉伯糖苷(1),槲皮素-3-O-β-D-吡喃葡萄糖(1→2)-α-L-吡喃阿拉伯糖苷(2),异鼠李素-3-O-β-D-吡喃葡萄糖苷(3),金丝桃苷(4),3’-甲氧基大豆苷(5),异鼠李素(6),芒柄花素(7),山柰酚(8),槲皮素(9).结论:化合物1为新的黄酮类成分。     

Alkamides from the leaves of Zanthoxylum syncarpum

Three alkamides (1-3) were isolated from the leaves of Zanthoxylum syncarpum. The structures of the new compounds 1 and 2 were established by spectroscopic data and chemical conversion, and by the X-ray crystallography of 1. Compound 3, the racemic form of the known compound syncarpamide, showed moderate antiplasmodial activity, with IC50 values of 4.2 and 6.1 microM against Plasmodium falciparum D6 clone and W2 clone, respectively.