Lipophylic compounds from Euphorbia peplis L.--a halophytic plant from the Bulgarian Black Sea coast

The chemical composition of the lipophylic fraction from the halophytic plant Euphorbia peplis L. was investigated. Compared to other terrestrial higher plants an increase of triacylglycerols and especially of glycolipids was observed. The main phospholipid was phosphatidyl choline, followed by almost equal concentrations of phosphatidyl ethanolamine and phosphatidyl glycerol. A relatively high concentration of phosphatidic acids (6.5% of the total phospholipids) was found. The main sterol appeared to be sitosterol and significant amounts of tetracyclic triterpene alcohols were found. The composition of the volatile compounds is relatively simple and only one chlorinated compound, identified as 2,2-diethoxy-1-chloroethane, was found. There was a strong toxicity of the total lipophylic extract towards Artemia salina.     

Tumor promoting diterpenes from Euphorbia leuconeura L.

Diterpene esters of the phorbol and ingenol types are known to be highly active tumor promoting agents that typically occur in members of the Euphorbiaceae. In the present work, Euphorbia leuconeura, a rare indoor plant, is analyzed for its tumor promoting potential. Latex as well as total leaf extracts exhibited Epstein-Barr-virus (EBV) inducing activity comparable to 12-O-tetradecanoyl-phorbol-13-O-acetate, a well known tumor promoter. The activity of individual fractions correlated with their ingenol ester content. Three ingenol esters with EBV inducing activity could be isolated and identified. They belong to the milliamine type of diterpene esters that contain aromatic peptidyl groups. Two of them (milliamines L and M) are already known from E. milii. The third compound is identified as an isomer of milliamine F with a novel 3,20-diester arrangement. The data show a close relationship between E. leuconeura and the more popular indoor plant E. milii whose latex is also used as a powerful molluscicide.     

Micropropagation of Euphorbia Lathyris L.

Shoot tips of Euphorbia Lathyris L. are difficult to establish in vitro unless wounding is minimized and explants are oriented vertically. The cytokinin benzyladenine was not necessary for axillary shoot proliferation, but was needed for callus and adventitious shoot production. Etiolated microshoots rooted well on modified MS supplemental with 1 mg 1^-1 1-naphthalene acetic acid. Acclimatization to greenhouse conditions was not difficult.Graduate Assistant and Assistant Professor, respectively.     

Mushroom tyrosinase inhibitory activity of esculetin isolated from seeds of Euphorbia lathyris L

A tyrosinase inhibitor was isolated from the seeds of Euphorbia lathyris L. by bioassay-guided fractionation and purification, using silica gel column chromatography. It was identified as esculetin by comparing its physical properties and spectral data with those of an authentic sample. The IC50 value of esculetin in the mushroom tyrosinase activity test was 43 microM. The kinetic study indicates that esculetin exhibited competitive inhibition against the oxidation of 3-(3,4-dihydroxyphenyl)-alanine by mushroom tyrosinase. The structure-activity relationships among five esculetin analogs suggest that hydroxyl groups at the C6 and C7 positions of the coumarin skeleton played an important role in the expression of tyrosinase inhibitory activity.     

Laticifers and the classification of Euphorbia: the chemotaxonomy of Euphorbia esula L.

Laticifers and the classification of Euphorbia: the chemotaxonomy of Euphorbia esula L. Articulated and non-articulated laticifer cells represent distinctive cell types of relatively recent origin and occur in only a few families. Both types are of separate phylogenetic origin, reflecting independent evolutionary trends in the Euphorbiaceae. Supra-generic groupings of this family can be segregated into three taxonomic units using the laticifer character; with either articulated laticifers, non-articulated laticifers, or no laticifers. Such units may reflect more natural assemblages than now represented in the classification of this family. Laticifers possess chemical and morphological features of potential application as taxonomic characters to aid in delimiting species and interpreting evolutionary trends. The triterpenoid profile from latex of Euphorbia species has been shown to be diagnostic for a taxon. The qualitative and quantitative composition show a high level of stability under diverse environmental and physiological conditions indicating a genetic basis for triterpenoid synthesis. Triterpenoid profiles of known accessions of European E. esula L. and related presumptive taxa from North America readily separated them into distinctive chemotaxa that include one for E. esula L., whereas morphological features were found inadequate for separating accessions to presumptive taxa. Identification of adventive spurges in North America requires diagnostic analyses of Eurasian leafy spurges for comparison. Laticifer characters used in conjunction with relevant morphological features will provide a broadened insight into phylogenetic relationships with the Euphorbiaceae.     

Sphingolipids with neuritogenic activity from Euphorbia sororia

Two groups of sphingolipids 1 and 2 were isolated from the aerial parts of Euphorbia sororia. On the basis of spectroscopic data, chemical methods and GC-MS analysis, the structures of 1 and 2 were characterized as 1-O-beta-D-glucopyranosyl-(2S,3S,4R,8Z)-2-[(2'R)-2'-hydroxydocosanoyl approximately hexacosanoyl, octacosanoyl amino]-1,3,4-octadecanetriol-8-ene and (2S,3S,4R,8E)-2-[(2'R)-2'-hydroxyeicosanoyl approximately hexacosanoyl amino]-1,3,4-octadecanetriol-8-ene, respectively. Both of them exhibited marked neuritogenic activity on the rat pheochromocytoma PC12 cell line.     

Jatrophane and lathyrane diterpenoids from Euphorbia hyberna L

A new diterpene tetraester, from the jatrophane family, and two new diterpene triesters, with a lathyrane skeleton, have been isolated from the chloroform extract of the roots of Euphorbia hyberna L. The structures of these compounds have been established by spectroscopic methods, including 2D NMR experiments.     

斑地锦的化学成分

斑地锦 (ＥｕｐｈｏｒｂｉａｍａｃｕｌａｔａＬ .)系大戟科 (Ｅｕｐｈｏｒｂｉａｃｅａｅ)植物 ,一年生匍匐小草本 ,具有清湿热、止血、通乳的功效 ,常用以治疗痢疾、疳积、外伤出血、痈肿疮毒。药典上将其作为地锦草入药 ,近代药理研究表明斑地锦具有抗菌及抗寄生虫的作用[1 ,2 ] 。文献[3～ 6 ] 报道斑地锦的化学成分主要为黄酮、甾醇、三萜及鞣质类化合物。为进一步寻找斑地锦的抗菌活性物质 ,进行了化学成分分析 ,从中分离得到 9个化合物 ,经理化性质和波谱分析鉴定为 :槲皮素 (Ⅰ )、山柰酚 (Ⅱ )、芹菜素 7 Ｏ 葡萄糖甙 (Ⅲ )、木犀…     

New Bioactive Macrocyclic Diterpenoids from Euphorbia helioscopia

Three new macrocyclic diterpenoids, euphoscopoids A – C ( 1 – 3 ), including two new jatrophanes and a new lathyrane, were isolated from the whole plant of Euphorbia helioscopia. Their structures were elucidated by spectroscopic methods. Antifeedant and cytotoxic activities of these isolates were evaluated. All compounds showed significant antifeedant activity against a generalist plant‐feeding insect, Helicoverpa armigera, with EC₅₀ values ranging from 2.05 to 4.34 μg/cm². In addition, compound 2 showed moderate cytotoxicity against tumor cell lines NCI‐H1975, HepG2, and MCF‐2, while compounds 1 and 3 were not active at 80 μm . The results suggested not only the defensive function of macrocyclic diterpenoids in E. helioscopia against insect herbivores, but also their potential applications as new natural insect antifeedants.     

New sesquiterpenes from the endophyte Microdiplodia sp. TT-12 and their antimicrobial activity

Four new compounds, phomadecalin F (1), 8α-monoacetoxyphomadecalin D (2), 3-epi-phomadecalin D (3), and 13-hydroxylmacrophorin A (4), were isolated from the endophyte, Microdiplodia sp. TT-12 together with two known compounds, phomadecalins C (5) and D (6). The structures of the compounds were elucidated by NMR spectroscopic and mass spectrometric analyses in combination with chemical means. The antibacterial activities of the isolated compounds were evaluated. Compound 4 was weakly active against Raffaelea quercivora.     

Diterpenoids from Euphorbia paralias.

Two segatane diterpenoids containing a bicyclic [4,3,1] ring system were isolated, together with 11 known diterpenoids, four segetanes, five jatrophanes and two paralianes, from the aerial parts of Euphorbia paralias. The structures of the new compounds were established by spectroscopic means, including by 2D NMR and CD spectroscopic analyses. The antifeedant and antiviral activities of the isolated compounds are also described.     

八种国产大戟属植物的核型报道

8种大戟属Euphorbia L．植物的核型分析结果表明,大戟属不同亚属的染色体基数与其形态变 异的复杂性有一定关系。地锦草亚属subgen．Chamaesyce 3个种染色体基数分别为x=8,9,11;一品红 亚属subgen．Poinsettia两个种染色体基数均为x=7,分别为四倍体和八倍体;乳浆大戟亚属subgen． Esula 3个种,染色体基数分别为x=7,10,10。根据以前学者发表的资料分析,一品红亚属和大戟亚属 Subgen. Euphorbia的染色体基数是很稳定的,分别为x=7和x=10;通奶草E．hypericifolia为x=8 的四倍体,它不仅有染色体整倍性的变异,还有异基数性的变化。结合以前学者的研究,笔者支持x= 10为大戟属的最原始基数的观点。齿裂大戟E．dentata和通奶草具不同的染色体倍性,猫眼草E． esula的细胞染色体数目观察证实了我国存在四倍体的居群,与欧洲和北美的植物构成一个典型的多倍体复合体。     

Karyotypes of eight species of Euphorbia L. (Euphorbiaceae) from China

In this paper, eight species of the genus Euphorbia L. were cytologically studied. The three species of the subgenus Chamaesyce Raf., E. hirta, E. humifusa and E. hypericifolia, had chromosome numbers of 2n = 18, 22 and 32, with their basic chromosome numbers being x = 9, 11 and 8 respectively. The two species of the subgenus Poinsettia (Grah.) House. E. dentata, with 2n=28, a tetraploid, and E. cyathophora, with 2n= 56, a octoploid, had both the basic chromosome number of x= 7. The three species of the subgenus Esula Pers, E. lathyris, E. helioscopia and E. hylonoma, had chromosome number of 2n= 20, 42 and 20, with their basic numbers being x= 10, 7 and 10 respectively. The basic chromosome number of x = 8 is new for E. hypericifolia, in which x = 7 was previously reported. This indicates that this species had both ploidy(2n = 4x = 28, 8x = 56) and dysploidy(x = 7, 8) variations. In E. dentata, there occurred also ploidy variation (2n = 2x, 4x and 8x). A tetraploid cytotype of E. esula was found in China, its diploid cytotype and hexaploid cytotype being previously reported in North America, the Iberian Peninsula and some other European areas. Based on our results and those previously reported, we support the viewpoint that x＝10 may be the original basic chromosome number of Euphorbiaand discuss the role of polyploidy and dysploidy in the speciation and evolution of this genus     

Chemical composition and antimicrobial activity of Satureja hortensis L. essential oil

Essential oil of Satureja hortensis L. was analyzed by GC and GC/MS and tested by a broth micro-well dilution method for activity against multiresistant clinical isolates of pathogenic bacteria from 10 different genera: Klebsiella, Escherichia, Proteus, Staphylococcus, Streptococcus, Pseudomonas, Enterococcus, Enterobacter, Citrobacter and Acinetobacter. The main compounds in the oil were carvacrol (67%), γ-terpinene (15.3%) and p-cymene (6.73%). The oil showed activity against all tested strains. MIC/MBC values were in the range of 0.78-25 μl/ml, with the exception of the strain P. aeruginosa. Microbicidal concentration for this particular strain (50 μl/ml) was the highest tested concentration. The oil showed inhibitory and bactericidal effect at the same concentration (MIC=MBC) for all but three strains.     

九牛造杀虫活性成分研究

无公害农药具有杀虫活性高、无污染、与环境相容性好等特点,开发此类农药具有重要意义[1,2].     

泽漆化学成分及其体外抗肿瘤活性研究

利用正相硅胶柱层析、葡聚糖凝胶Sephadex LH-20、制备薄层层析、反相制备色谱等离手段和1H、13C NMR等波谱技术,从泽漆(Euphorbia helioscopia L.)中分离鉴定了10个化合物,分别为β-谷甾醇(β-sitosterol,1),大戟甘(euphornin,2),大戟甘D(euphomin D,3),A(euphohelioscopin A,4),槲皮素(quercetin,5),没食子酸(gallic acid,6),咖啡酸(caffeie acid,7),没食子酸乙酯(ethyl gallate,8),杨梅素(myrecetin,9),金丝桃苷(hypero-side,10),其中化合物7、8、9是首次从该植物中分得,通过体外抗肿瘤活性研究,化合物6和10作为泽漆的抗肿瘤活性成分属首次报道.     

Spectroscopic identification of new ellagitannins and a trigalloyl-glucosylkaempferol from an extract of Euphorbia cotinifolia L. with antitumour and antioxidant activity

From an extract of leaves and small branches of Euphorbia cotinifolia L., 17 polyphenols were isolated including two new ellagitannins and a trigalloyl-glucosylkaempferol. Based on extensive spectral data (UV, ESI-MS, 1H NMR, DEPT and 1D/2D NMR) and chemical studies, their structures were characterized as 1-O-galloyl-3,6-hexahydroxydiphenoyl-D-B1,4-glucopyranose (5), 1-O-galloyl-3,6-valoneoyl-D-B1,4-glucopyranose (6), and kaempferol 3-O-(2",3",6"-tri-O-galloyl)-beta-D-glucopyranoside (13). Biological evaluation indicated that the 80% aqueous methanol extract (AME), chloroform extract (CE), and some pure compounds have potent scavenging activity in the DPPH assay with SC50 values lower than that of ascorbic acid, especially 5, 7-9, and a mixture of hyperin 6"-gallate (11) and isoquercitrin 6"-gallate (12). Moreover, using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) cell viability assay, 6 and 8 exhibited the highest inhibition of human hepatocellular carcinoma cells (Hep-G2), while AME, CE, 5, 7, 9, and the mixture of 11 and 12 were found to be moderate growth inhibitors according to their IC50 values. In addition, AME, 5, and 8 exhibited significant antiproliferative activity against colon carcinoma cells (HCT-116); however, CE and the other examined compounds displayed moderate to low antitumour activity against HCT-116 cells.     

Jatrophane diterpenoids from Euphorbia peplus.

From the pro-inflammatory active extract of Euphorbia peplus, a new diterpene polyester (1) based on the jatrophane skeleton was isolated together with the known compounds 2-5. The irritant activities of some jatrophane diterpenes (2, 3 and 6-9) were also investigated: only compound 2 was found to exert a weak pro-inflammatory activity on mouse ear.     

New chitosan derivatives with potential antimicrobial activity

A series of four water-soluble chitosan derivatives differing in molecular mass, hydrophobicity, and charge was synthesized and tested for the intensity of their effects on Gram-negative and Gram-positive bacteria. It was shown that the tested compounds allowed the penetration of ethidium bromide into the bacteria, which showed increased permeability of their cell walls under the effect of chitosans. The tolerance to various chitosan derivatives differed in Gram-negative and Gram-positive bacteria. The Gram-negative bacteria were the most responsive to high-molecular chitosan and the Gram-positive ones, to N-,O-carboxypropylchitosan, whereas high-molecular chitosan had little effect. Research on the correlation between the structure and activity of the studied compounds revealed that depolymerization of chitosan reduced, and introduction of hydrophobic substantives in chitosan molecule significantly enhanced its permeability effect on bacterial cell walls. The obtained results provide a basis for the construction of new chitosan derivatives with antimicrobial activities.     

Production and selected fuel properties of biodiesel from promising non-edible oils: Euphorbia lathyris L., Sapium sebiferum L. and Jatropha curcas L

A comparative study on the composition, biodiesel production and fuel properties of non-edible oils from Euphorbia lathyris L. (EL), Sapium sebiferum L. (SS), and Jatropha curcas L. (JC) was conducted. Under optimal conditions, the FAME content and yield of the three oils were greater than 97.5 wt.% and 84.0%, respectively. The best biodiesel was produced from EL due to its high monounsaturation (82.66 wt.%, Cn: 1), low polyunsaturation (6.49 wt.%, Cn: 2, 3) and appropriate proportion of saturated components (8.78 wt.%, Cn: 0). Namely, EL biodiesel possessed a cetane number of 59.6, an oxidation stability of 10.4 h and a cold filter plug point of -11 °C. However, the cetane number (40.2) and oxidative stability (0.8 h) of dewaxed SS kernel oil (DSSK) biodiesel were low due to the high polyunsaturation (72.79 wt.%). In general, the results suggest that E. lathyris L. is a promising species for biodiesel feedstock.