Growth inhibitory activity of extracts and compounds from Cimicifuga species on human breast cancer cells

The purpose of this report is to explore the growth inhibitory effect of extracts and compounds from black cohosh and related Cimicifuga species on human breast cancer cells and to determine the nature of the active components. Black cohosh fractions enriched for triterpene glycosides and purified components from black cohosh and related Asian species were tested for growth inhibition of the ER⁻ Her2 overexpressing human breast cancer cell line MDA-MB-453. Growth inhibitory activity was assayed using the Coulter Counter, MTT and colony formation assays.Results suggested that the growth inhibitory activity of black cohosh extracts appears to be related to their triterpene glycoside composition. The most potent Cimicifuga component tested was 25-acetyl-7,8-didehydrocimigenol 3-O-β-d-xylopyranoside, which has an acetyl group at position C-25. It had an IC₅₀ of 3.2 μg/ml (5 μM) compared to 7.2 μg/ml (12.1 μM) for the parent compound 7,8-didehydrocimigenol 3-O-β-d-xylopyranoside. Thus, the acetyl group at position C-25 enhances growth inhibitory activity.The purified triterpene glycoside actein (β-d-xylopyranoside), with an IC₅₀ equal to 5.7 μg/ml (8.4 μM), exhibited activity comparable to cimigenol 3-O-β-d-xyloside. MCF7 (ER⁺Her2 low) cells transfected for Her2 are more sensitive than the parental MCF7 cells to the growth inhibitory effects of actein from black cohosh, indicating that Her2 plays a role in the action of actein. The effect of actein on Her2 overexpressing MDA-MB-453 and MCF7 (ER⁺Her2 low) human breast cancer cells was examined by fluorescent microscopy. Treatment with actein altered the distribution of actin filaments and induced apoptosis in these cells.These findings, coupled with our previous evidence that treatment with the triterpene glycoside actein induced a stress response and apoptosis in human breast cancer cells, suggest that compounds from Cimicifuga species may be useful in the prevention and treatment of human breast cancer.     

The complexation between holothurian triterpene glycosides and Chl as the basis for lipid-saponin carriers of subunit protein antigens

The ability of holothurian triterpene glycosides (cucumarioside A₂-2 from Cucumaria japonica, cucumarioside G₁ from C. fraudatrix, frondoside A from C. frondosa, and holotoxin A₁ from Apostichopus japonicus) to form supramolecular lipid-saponin complexes was studied. TEM demonstrated that all the studied compounds form supramolecular cholesterol-saponin complexes (nanoparticles) in aqueous medium. The complexes formed by cucumarioside A₂-2, holotoxin A₁, and frondoside A had a tubular structure and fundamentally differed in the structure from the particles produced by cucumarioside G₁. The morphology of the nanoparticles formed by cucumarioside A₂-2, holotoxin A₁, and cucumarioside G₁ changed depending on the fraction of cholesterol in the lipid-saponin system; however, this pattern was not observed for frondoside A. At the same molar fraction of cholesterol in the lipid-saponin system, cucumarioside A₂-2 formed the particles with the most pronounced tubular structure; the cholesterol-saponin complexes of holotoxin A₁ had a less pronounced tubular structure, whereas the structure of frondoside A particles was extremely heterogeneous. Comparative analysis of the morphology of the described supramolecular complexes and specific structural features of the glycosides demonstrated that the structure of the corresponding nanoparticles depended on the degree of branching of the carbohydrate moiety in the glycoside molecule and the complexation with cholesterol was determined by the specific features of aglycone structure. Thus, the feasibility of producing new generation antigen carriers using the complexes in question was proved.     

Sea Cucumbers Triterpene Glycosides, the Recent Progress in Structural Elucidation and Chemotaxonomy

Triterpene glycosides are characteristic metabolites of sea cucumbers (Holothurioidea, Echinodermata). Majority of the glycosides belong to holostane type (lanostane derivatives with 18(20)-lactone). Carbohydrate chains of these glycosides contain xylose, glucose, quinovose, 3-O-methylglucose and 3-O-methyl sylose. During the last 5 years, main investigations were focused on holothurians belonging to the order Dendrochirotida collected in the North Pacific, North Atlantic, Antarctic and in subtropical waters. The glycosides of holothurians belonging to the order Aspidochirotida have also been studied. The most uncommon structural features of carbohydrate chains of new glycosides were: (1) the presence of quinovose as fifth terminal monosaccharide unit and the presence of two quinovose residues; (2) the presence of glucose instead of common xylose as fifth terminal monosaccharide unit; (3) trisaccharide carbohydrate chain; (4) the presence of two 3-O-methylxylose terminal monosaccharide units; (5) the presence of sulfate group at C-3 of quinovose residue. New glycosides without lactone or with 18(16)-lactone and having shortened side chains have also been isolated. The presence of 17α and 12α-hydroxyls, which are characteristic for glycosides from holothurians belonging to the family Holothuriidae (Aspidochirotida) in glycosides of dendrochirotids confirms parallel and relatively independent character of evolution of glycosides. All three families belonging to the order Aspidochirotida: Holothuriidae, Stichopodidae and Synallactidae have similar and parallel trends in evolution of the glycosides carbohydrate chains, namely from non-sulfated hexaosides to sulfated tetraosides. Sets of aglycones in glycosides from holothurians belonging to the genus Cucumaria (Cucumariidae, Dendrochirotida) are specific for each species. The carbohydrate chains are similar in all representatives of the genus Cucumaria.     

Aromatic Crown Ethers as Phase Transfer Catalysts in the Synthesis of N-Acetylglucosamine β-Aryl Glycosides

The crown ether-catalyzed glycosylation of phenol, 4-methoxyphenol, and 4-nitrophenol was studied under phase transfer conditions in solid–liquid system. The asymmetric dibenzocrown esters are superior to [3.3]dibenzo-18-crown-6 and 15-crown-5 in the catalysis of these reactions.     

一种新的肉苁蓉甙类化合物的分离方法

简单介绍了一种从肉苁蓉中提取得到肉苁蓉甙类化合物的方法,避免了乙酸乙酯和正丁醇的萃取,便于工业化应用,同时还可获得纯度较高有甜菜碱。     

紫菀属化学成分及药理活性研究进展

紫菀属所含化学成分主要是三萜皂甙 ,此外还含其它萜类、肽类、香豆素、甾醇等 ;其中一些成分具有抗瘤 ,抗菌 ,消炎等活性。本文对其近 2 0多年来国内外学者分离到的化学成分及其药理活性的研究结果作一综述 ,为该属植物资源的进一步研究和开发提供参考。     

仙茅中两个新的环阿尔廷醇型三萜皂苷

从仙茅(Curculigo orchioides）中分离得到2个新的环阿尔廷醉型三萜皂苷,通过波诺分析鉴定了它们的化学结构,即3β,11α,16β—三羟基环阿尔廷烷-24-酮-3-O-[β-D-吡喃葡糖(1→3)-β-D-吡喃葡糖(1→2)-β-吡喃葡糖]-16-O-α-L-阿拉伯糖苷(1)和(24S)-3β,11α,16β,24-四经基环阿尔廷烷-3-O-[β-D-吡喃葡糖(1→3)-β-D-吡喃葡糖(1→2)-β-D-吡喃葡糖]-24-O-β-D-吡喃葡糖苷(2)。     

Soil nutrients and water availability interact to influence willow growth and chemistry but not leaf beetle performance

We investigated the effects of soil nutrient and water availability on the growth and chemistry of the silky willow (Salix sericea Marshall), and on the performance of the imported willow leaf beetle (Plagiodera versicolora Laichartig). Our major aims were to determine whether there are nutrient–water interactions on plant traits and whether this leads to parallel interactions for herbivore performance. We used a 2 × 3 fully factorial design, which consisted of high and low nutrient treatments crossed with dry, field capacity, and flooded water treatments. We found that nutrient additions increased plant growth, but only in field capacity and flooded conditions (nutrient–water interaction). Leaf nitrogen content also depended on the interaction between soil nutrients and water: nutrient addition resulted in a larger increase in foliar nitrogen in the field capacity treatment than in the flooded and dry treatments. Of the two phenolic glycosides measured, salicortin and 2′‐cinnamoylsalicortin, only one was affected by the treatments. 2′‐cinnamoylsalicortin concentration was lower in the high nutrient–dry treatment compared with the other treatments. In contrast to plant responses, there were no interactions found for larval or pupal weight or development time. Nutrient addition led to an increase in female pupal weight, and foliar N was positively correlated with female pupal weight and negatively correlated with female development time. In addition, leaf water was positively correlated with female development time. The lack of interactions for insect performance may stem from the small absolute differences in foliar nitrogen content associated with the interaction between the nutrients and water. Taken together, our results suggest that nutrient–water interactions influence plant traits that are potentially important for insect performance (leaf nitrogen and water), but these interactions do not produce parallel interactions in beetle performance.