云南红豆杉的化学成分研究及1-去羟基巴卡亭VI的结构修饰

目的 研究云南红豆杉(Taxus yunnanensis)心木的化学成分并对1-去羟基巴卡亭VI进行了结构修饰.方法 采用各种现代色谱技术进行分离纯化,根据化合物的理化性质和波谱数据进行结构鉴定.并对1-去羟基巴卡亭VI进行了选择性的去乙酰化反应.结果 从云南红豆杉心木的95%乙醇提取物中分离并鉴定了7个紫杉烷类化合物.对其中一个含量较高的化合物进行了结构修饰,得到两个去乙酰化的产物,并鉴定了其结构.结论 结构修饰所得到的13位去乙酰产物是我们所需要的,它为今后进一步合成符合紫杉醇构效关系的产物提供了物质基础.     

Phenolic constituents from Parakmeria yunnanensis and their anti-HIV-1 activity

Three new phenolic compounds, yunnanensins A–C (1–3), together with fourteen known ones (4–17), were isolated from the leaves and stems of Parakmeria yunnanensis. The structures of new compounds were established on the basis of extensive spectroscopic analyses. Several compounds showed weak anti-HIV-1 activity.     

DPPH radical scavenging and nitric oxide inhibitory activities of the constituents from the wood of Taxus yunnanensis

The H2O, H2O/MeOH (1 : 1) and MeOH extracts of the wood of Taxus yunnanensis possessed significant DPPH radical scavenging and nitric oxide (NO) inhibitory activities. Chemical investigation of these extracts led us to isolation of nineteen compounds, i. e., five lignans, two simple phenolics, and twelve taxane-type diterpenes. Isotaxiresinol and seco-isolariciresinol, two major lignans of the wood, possessed potent DPPH radical scavenging activities with IC 50 values of 21.7 and 28.9 microM, respectively. Similarly, coniferyl aldehyde, taxusin, 10-deacetyltaxuyunnanine C, hongdoushan A, and 2alpha,5alpha,10beta-triacetoxy-14beta-[( S)-2-methylbutyryloxy]-4(20),11-taxadiene showed potent NO inhibitory activity with IC 50 values of 18.0, 22.1, 28.5, 15.0 and 26.4 microM, respectively, which were either equal or lower than the positive control NG-monomethyl- L-arginine ( L -NMMA) with an IC 50 value of 28.5 microM.     

Anti-hepatotoxic activity of extracts and constituents of Buddleja species

The aqueous extracts of three species of Buddleja which are used in traditional medicine for the treatment of liver ailments have shown an inhibitory effect against induced cytotoxicity of cultured hepatocytes. Fractionation of one of these extracts, from B. globosa leaves, resulted in the isolation of five iridoids, two phenylpropide glycosides, and a flavonoid glycoside. Two of the iridoids were found to be novel compounds, 7-p-methoxycinnamoylaucubin (1) and 7-p-methoxycinnamoylcatalposide (2). One of the phenylpropides, echinacoside, has not previously been reported from Buddleja. Testing of the isolated compounds in the cultured hepatocyte system indicated that the activity is most likely due to the flavonoid and phenylpropide constituents. Phenylpropide glycosides have not previously been shown to have a liver-protectant effect.     

Non-taxane compounds from the bark of Taxus yunnanensis

From the bark of Taxus yunnanensis , 15 non-taxane compounds were isolated. Through spectroscopic methods such as 1D and 2D NMR and MS experiments, one of them was determined as a new abietane-type diterpenoid named taxayunnin ( 1 ). The other 14 known compounds were identified as taxamairin C ( 2 ), taxamairin A ( 3 ), 3 g -hydroxy-sandaracopimaric acid ( 4 ), (+)-3-hydroxy-isodrimenin ( 5 ), rubrosterone ( 6 ), ponasterone A ( 7 ), ecdysterone ( 8 ), 20-hydroxy-echysone-20,22-monoacetonide ( 9 ), 7-oxositosterol ( 10 ), stigmast-4-en-6 g -ol-3-one ( 11 ), 5 f ,6 g -dihydroxy-daucosterol ( 12 ), g -sitosterol ( 13 ), daucosterol ( 14 ), 1- O - g - d -glucopyranosyl-(2 S , 3 R , 4 E , 8 Z )-2- N -(2'-hydroxypalmitoyl)-octadeca-sphinga-4,8-dienine ( 15 ), respectively. Compounds 4 - 6 , 9 - 12 and 15 were isolated from Taxus plants for the first time.     

Non-taxane compounds from the bark of Taxus yunnanensis

From the bark of Taxus yunnanensis, 15 non-taxane compounds were isolated. Through spectroscopic methods such as ID and 2D NMR and MS experiments, one of them was determined as a new abietane-type diterpenoid named taxayunnin (1). The other 14 known compounds were identified as taxamairin C (2), taxamairin A (3), 3beta-hydroxy-sandaracopimaric acid (4), (+)-3-hydroxy-isodrimenin (5), rubrosterone (6), ponasterone A (7), ecdysterone (8), 20-hydroxy-echysone-20,22-monoacetonide (9), 7-oxositosterol (10), stigmast-4-en-6beta-ol-3-one (11), 5alpha,6beta-dihydroxy-daucosterol (12), beta-sitosterol (13), daucosterol (14), 1-O-beta-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-N-(2'-hydroxypalmitoy])-octadeca-sphinga-4,8-dienine (15), respectively. Compounds 4-6, 9-12 and 15 were isolated from Taxus plants for the first time.     

Growth inhibitory activity of wood of Taxus yunnanensis and its liquid chromatography Fourier-transform mass spectrometry analysis

The wood of Taxus yunnanensis (Taxaceae) showed growth inhibitory activities against human cancer cell lines, such as cervical HeLa adenocarcinoma. The morphological changes indicated that the cellular growth inhibitions were caused by apoptosis. To determine the active components, T. yunnanensis wood was analyzed by using a liquid chromatography-Fourier-transform MS (LC/FT-MS) technique. As a result, taxane-type diterpenes, such as 10-deacetylcephalomannine and 10-deacetyltaxol, were found to be present in amounts consistent with the growth inhibitory activity.     

云南石仙桃的化学成分

目的分离并鉴定兰科植物云南石仙桃(Pholidota yunnanensisRolfe)全草的体积分数为60%乙醇提取物中的化学成分。方法采用硅胶柱色谱法、凝胶柱色谱法、反相硅胶柱色谱法以及高效液相色谱法进行分离和纯化,并根据理化常数和光谱分析进行结构鉴定。结果分离得到了6个化合物,分别为4(3羟基2甲氧基苯基)2丁酮(4(3 hydroxy 2 methoxyphenyl)2 butanone,Ⅰ)、4(3羟基苯基)2丁酮(4(3 hydroxyphenyl)2 butanone,Ⅱ)、(R)(+)lasiodiploidin(Ⅲ)、(-)松脂素((-)pinoresinol,Ⅳ)、(-)丁香脂素((-)syringaresinol,Ⅴ)和β谷甾醇(βsitosterol)(Ⅵ)。结论化合物Ⅰ和Ⅱ为首次从植物中分离得到,Ⅲ~Ⅴ为首次从该属植物中分离得到。     

Antiallergic activity of omega-nitroacetophenones.

Selected omega-nitroacetophenones, formed by the alcoholic cleavage of 2-nitroindandiones, have been shown to inhibit the homocytotropic antibody-antigen induced passive cutaneous analhylaxis reaction in the rat. The enzymatic cyclization of these derivatives to the parent nitroindandione has been demonstrated both in vivo and in vitro and this process is suggested as a possible prerequisite to biological activity.     

Taxuyunnanines S-V, new taxoids from Taxus yunnanensis

Four new 11(15-->1)-abeotaxoids with an opened oxetane ring system, taxuyunnanines S, T, U and V (1 - 4) were isolated from the bark of Taxus yunnanensis. Taxuyunnanine S (1), is the most hydroxylated abeotaxoid discovered to date from Taxus species. The structures were determined by spectroscopic means including 1D and 2D NMR experiments.     

云南红豆杉根的化学成分研究

从采地云南省保山的云南红豆杉Ｔａｘｕｓ ｙｕｎｎａｎｅｎｓｉｓ的树皮中分得５个紫杉烷类化合物,通过＾１Ｈ－ＮＭＲ,＾１３Ｃ ＮＭＲ ＭＳ、ＩＲ,ＤＯＲｄｅｃｏｕｐｌｉｎｇ,＾１３Ｃ－＾１Ｈｅｏｓｙ等方法鉴定其结构为,２α,７β,９α１０β,１３α,２０－ｈｅｘａａｃｅｔｏｘｙ－４　,５－呔ｄｉｈｙｄｒｏｘｙ ｔａｘｎ－１１（１２）ｅｎｅ（１）、Ｔａｘａ－４（２０）,１１－ｄｉｅｎｅ－２α,５α,１     

Antiallergic activity of ginseng and its ginsenosides

In this study, we measured the antiallergic activities of ginsenosides isolated from the root of Panax ginseng ( Araliaceae), and of their metabolites, as produced by human intestinal bacteria. Compound K, which was identified as a main metabolite, had the most potent inhibitory activity on beta-hexosaminidase release from RBL-2H3 cells and on the PCA reaction. The inhibitory activity of compound K was more potent than that of disodium cromoglycate, one of the commercial anti-allergic drugs. This compound demonstrated a membrane stabilizing action on differential scanning calorimetry. However, compound K did not inhibit the activation of hyaluronidase and did not scavenge active oxygen. These results suggest that the antiallergic action of compound K originates from its cell membrane stabilizing activity and that the ginsenosides of ginseng are prodrugs with extensive antiallergic properties. Abbreviations. compound K:20- O-beta- D-glucopyranosyl-20( S)-protopanaxadiol DNP:dinitrophenol DSCG:disodium cromoglycate DPPC:dipalmitoylphosphatidylcholine DPPH:1,1-diphenyl-2-picrylhydrazyl HSA:human serum albumin IC 50 :50% inhibitory concentration EC 50 :50% effective concentration XOD:xanthine oxidase ICR:Institute of Cancer Research PBS:phosphate buffered saline PCA:passive cutaneous anaphylaxis RAW264.7:mouse monocyte leukemiaRBL-2H3: rat basophil leukemia SD:Sprague-Dawley     

Anti-inflammatory activity of aqueous and ethanolic extracts of Zygophyllum gaetulum

Zygophylle or Zygophyllum gaetulum Emberger and. Maire is a Moroccan medicinal plant which has been used as an anti-inflammatory, antidiabetic, antispasmodic and antidiarrheic. The present study was carried out to study and compare the anti-inflammatory effect of ethanolic extract with aqueous extract of Z. gaetulum. Organic extract of Z. gaetulum was obtained in soxhlet apparatus. Aqueous extract was obtained by infusion. The Wistar albinos rats of either sex weighing 200-300 g aged 2-3 months were used for this experiment. The rats were housed under standard environmental conditions. The anti-inflammatory activity was estimated by measuring the oedema induced by carragenin according to the method of Winter and al. Ethanolic extract of Z. gaetulum reduced the increase of the paw volume with a percentage of inhibition of 46% (p<0.01), this percentage was 47.48% (p<0.01) with aqueous extract. The inhibition decrease in time, it arrived to 39% (p<0.01) at the sixth hour while the activity of aqueous extract decrease a lot. In conclusion, Z. gaetulum is an interesting plant which the aqueous and éthanolic extracts could be used scientifically in the treatment of inflammation.     

Antiallergic activity of ginsenoside Rh2

The antiallergic activities of ginsenosides, which were isolated from acid-treated ginseng (Panax ginseng, Araliaceae), and their metabolites by human intestinal bacteria were measured. Ginsenoside Rh2, which is a main metabolite, had the most potent inhibitory activity on beta-hexosaminidase release from RBL-2H3 cells and in the passive cutaneous anaphylaxis reaction. The inhibitory activity of ginsenoside Rh2 was more potent than that of disodium cromoglycate, a commercial antiallergic drug. This compound showed membrane stabilizing action upon differential scanning calorimetry and inhibited nitric oxide (NO) and prostaglandin E2 (PGE2) in lipopolysaccharide-stimulated RAW cells. However, this ginsenoside Rh2 did not inhibit the activation of hyaluronidase and did not scavenge active oxygen. These results suggest that ginsenoside Rh2 can exhibit antiallergic activity originating from cell membrane-stabilizing activity and antiinflammatory activity by the inhibition of NO and PGE2 production.     

Free radical scavenging activity of red ginseng aqueous extracts

This study was performed to investigate the free radical scavenging activity of Panax red ginseng C.A. Meyer aqueous extract on 1,1-dipheny-2-picrylhydrazyl (DPPH), carbon-centered radical, hydroxyl and superoxide radicals using Electron Spin Resonance (ESR) spectrometer and spin-trapping techniques. Two different Red ginseng aqueous extracts prepared by boiling water or room temperature extraction exhibited no significant difference in free radical scavenging activity. Ginseng extracts completely eliminated DPPH radical at 2 mg/ml. About 0.5 mg/ml ginseng extracts quenched 80% carbon-centered free radicals generated from 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH). Hydroxyl radical and superoxide radical were generated by UV irradiation and trapped by 5,5-dimethyl-l-pyrroline-N oxide (DMPO). Ginseng extracts scavenged 40% of hydroxyl radical at 0.1 mg/ml. Two mg/ml ginseng extracts completely scavenged superoxide radical. Ginseng extracts did not scavenge nitric oxide. The ESR data demonstrate that red ginseng aqueous extract is not a strong free radical scavenger.     

HPLC法测定云南红豆杉枝叶中金松双黄酮的含量

目的:建立以高效液相色谱法测定云南红豆杉枝叶中金松双黄酮含量的方法。方法:色谱柱为Agilent Zorbax SB-C_(18) (250 mm×4.6 mm,5μm),流动相为甲醇-水(80:20),流速为1.0 mL·min~(-1),检测波长为272 nm,柱温为40℃结果:金松双黄酮的进样量在0.88～4.40μg·mL~(-1)范围内与峰面积积分值呈良好线性关系(r=0.9999);平均回收率为95.40%,RSD= 3.5%(n=6)。结论:本方法准确、可靠、稳定,可用于云南红豆杉的质量控制。     

云南红豆杉中BaccatinⅢ和10—去乙酰Baccatin Ⅲ的含量测定

报道了一种在C18高效液相色谱柱上分离紫杉醇（Taxol）的前体化合物BaccatinⅢ和10－去乙酰BaccatinⅢ的分析方法。所用流动相为甲醇－水（52：48），必要时可使用水－乙腈－四氢呋喃（67：25：8），流速1.0ml/min，检测波长227nm，运用此方法对云南红豆杉不同部位（干皮、枝、叶、心木）的若干样品进行了测定，发现BaccatinⅢ和10－去乙酰BaccatinⅢ在各部位间含量差异较大，即使同一部位也有很大差异。     

In vitro activity of extracts and constituents of Pelagonium against rapidly growing mycobacteria

Extracts of the roots of plants of the Geraniaceae family have been used for many years in South Africa as native herbal remedies and there is circumstantial evidence for efficacy in the treatment of pulmonary tuberculosis. We have examined dried roots of Pelargonium reniforme and P. sidoides for antibacterial activity against rapidly growing mycobacteria. Fractions with activity against Mycobacterium aurum and M. smegmatis were obtained from both plant species by bioassay-guided fractionation of n-hexane extracts and were found to contain mixtures of straight-chain fatty acids. Analysis by gas chromatography–mass spectrometry (GC–MS) of the corresponding fatty acid methyl esters revealed structures with chain lengths ranging from C12 to C26. Unsaturated compounds were analysed as the corresponding dimethyl disulfide adducts to determine double-bond positions. Active mixtures differed in the relative abundance of their components, but all contained 16:0 (palmitic), Δ⁹-18:1 (oleic) and Δ^9,12-18:2 (linoleic acid) as the major components. When tested against M. aurum, M. smegmatis and other rapidly growing mycobacteria (M. fortuitum, M. abscessus and M. phlei), all saturated compounds except 12:0 were devoid of antimycobacterial activity, whereas unsaturated compounds showed antimycobacterial activity related to their degree of unsaturation, their chain length and the bacterial species tested. The most potent compound was linoleic acid, with MIC of 2 mg/l against M. aurum.