Synthesis and Antinematodal Activity of 3-n-Alkylphenols

Several 3-alkylphenols including 3-undecylphenol, which was isolated from a Sumatran rainforest plant, were synthesized to investigate their antinematodal activity against the phytopathogenic nematodes, Bursapherencus xylophilus. A three-step synthesis involving the treatment of 2-cyclohexen-1-one with the Grignard reagent, oxidation of the resulting 1-alkyl-2-cyclohexen-1-ol and subsequent aromatization of 3-alkyl-2-cyclohexen-1-one successfully afforded such phenols. Among the 3-alkylphenols, 3-nonylphenol showed the highest activity, while 3-decylphenol and 3-undecylphenol also showed high activity.     

Three antinematodal diterpenes from Euphorbia kansui

Three compounds, 20-O-acetyl-[3-O-(2'E,4'Z)-decadienoyl]-ingenol (1), 20-O-acetyl-[5-O-(2'E,4'Z)-decadienoyl]-ingenol (2) and 3-O-(2'E,4'Z)-decadienoylingenol (3), were isolated from Euphorbia kansui under the bioassay-guided method. Each compound showed the same antinematodal activity against the nematode, Bursaphelenchus xylophilus, at a minimum effective dose (MED) of 5 microg/cotton ball.     

Antinematodal activities of ingenane diterpenes from Euphorbia kansui and their derivatives against the pine wood nematode (Bursaphelenchus xylophilus)

Under the bioassay-guided method, two diterpenes, 3-O-(2",3"-dimethylbutanoyl)-13-O-dodecanoylingenol (1) and 3-O-(2",3"-dimethylbutanoyl)-13-O-decanoylingenol (2) isolated from Euphorbia kansui, showed a pronounced antinematodal activity against the nematode Bursaphelenchus xylophilus at the same minimum effective dose (MED) of 5 microg per cotton ball and still displayed antinematodal activity at a dose of 2.5 microg per cotton ball. Compounds 3-6 were obtained, and the structure of the new compound 6 was elucidated based on 1D- and 2D-NMR analyses and physicochemical data. Preliminary structure-biological activity relationships of ingenane-type compounds were deduced.     

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.     

宽叶大戟化学成分的研究

对宽叶大戟(Euphorbia latifolia)的化学成分进行研究。从其乙醇提取物的石油醚、乙酸乙酯部位分离得到10个化合物,经理化常数和波谱分析,分别鉴定为:山萘酚(kaempferol,1)、槲皮素(quercetin,2)、山萘酚-3-O-β-D-葡萄吡喃糖苷(kaempferol-3-O--βD-glucopyranoside,3)、槲皮素-3-O--βD-葡萄吡喃糖苷(quercetin-3-O--βD-glucopy-ranoside,4)、白桦酯酸(betulinic acid,5)、白桦酯醇(betulin,6)、齐墩果酸(oleanolic acid,7)、胡萝卜苷(daucosterol,8)、β-谷甾醇(-βsitosterol,9)、正二十八烷醇(1-octacosanol,10)。化合物1~10均是首次从该植物中获得。     

湖北大戟根中的环阿尔廷型三萜

从湖北神农架地区产湖北大戟(Euphorbia hylonomaHand.-Mazz.)根中分离得到4个环阿尔廷型三萜化合物,分别鉴定为:24-烯环阿尔廷软脂酸酯(1),环阿尔廷-23-烯-3β,25-二醇-3-乙酸酯(2),环阿尔廷-25-烯-3β,24ξ-二醇(3),环阿尔廷-23-烯-3β,25,28-三醇(4)。化合物1~4均为首次从该植物中得到。     

Termiticidal activity of diterpenes from the roots of Euphorbia kansui

Five ingenane compounds, 1-5, kansuinins A and B, isolated from Euphorbia kansui, and their derivatives 7 and 9 were tested for termiticidal activity against the Japanese termite, Reticulitermes speratus. At 72 hours after treatment, the ingenane compounds 1 to 5 caused 100% mortality in R. speratus at 50, 25 and 12.5 microg/disk, respectively, except for compound 1, which gave a mortality rate of (93.06 +/- 5.56)% at 12.5 microg/disk. At 36, 48 and 60 hours after treatment, compounds 1 to 5 showed more termiticidal activity than kansuinins A and B and their derivatives. The kansuinins showed no or only slight activity against termites in the filter paper bioassay under the conditions tested compared with a solvent control.     

大果大戟中的一个对映-贝壳杉烷型二萜

从大果大戟的根部首次分离得到一个对映-贝壳杉烷型二萜,利用波谱方法鉴定为ent-16α,17-dihydrox-ykauran-3-one(1)。首次对化合物1在甲醇中的碳谱和氢谱数据进行了全归属。     

霸王鞭乙酸乙酯部分化学成分研究

为了研究霸王鞭(Euphorbia royleana Boiss.)的化学成分及其卤虫致死活性,采用正相硅胶柱色谱、Sephadex LH-20凝胶柱色谱及半制备型高效液相色谱等方法从霸王鞭甲醇提取物的乙酸乙酯萃取部位中分离得到15个化合物。通过现代波谱学技术鉴定它们的结构分别为5(6)-guten-3α-ol(1)、蒲公英赛醇(2)、异蒲公英赛醇(3)、熊果酸(4)、齐墩果酸(5)、1-羟基-3,7,8-三甲氧基黄酮(6)、甲基獐牙菜素(7)、槲皮素(8)、胡萝卜苷(9)、β-谷甾醇(10)、豆甾醇(11)、香草醛(12)、十二烷醇(13)、植物醇(14)、1-[(12 E,16 E)-12,16-二十碳二烯酰基]-2-[(E,E)-7,11-十八碳二烯酰基]-3-硬脂酰基甘油(15)。化合物1、3、4、5、6、7、12、13、14和15均首次从该植物中分离得到。对所得到的化合物进行了卤虫致死活性研究,发现化合物4表现出较强卤虫致死活性,其LD₅₀为7.687μM。     

Ingenane diterpenoids from Euphorbia esula

An extensive study of metabolites present in Euphorbia esula led to isolation of 16 ingenane diterpenoids 1-16 together with the known ingenane derivative 17 and four known cycloartane triterpenoids. Their structures were elucidated on the basis of spectroscopic studies and comparison with known related compounds. All the compounds were assayed for their inhibitory activity against human HeLa cervical cancer cell line.     

地锦草脂溶性成分研究

采用硅胶柱层析的方法,从地锦草（Euphorbia humifusa Wild．）中分离得到5个化合物,经理化鉴别及波谱分析,鉴定为羽扇豆醇（1upeol,1）．cycloart-23E-en-3β,25-diol（2）．cycloart-23E-en-3β,25-diol（3）、cycloart-25-ene-3β,24-diol（4）、正十六碳酸α-甘油酯（1-glycerin hexadecylate,5）。化合物1～5均为首次从该植物中分离得到。     

安徽产大戟属植物叶表皮微形态

利用光镜和扫描电镜对安徽7种大戟属(Euphorbia)植物叶表皮进行了观察。发现该属7种植物叶表皮细胞为不规则形或多边形,垂周壁一般为平直、浅波状、深波状;气孔器通常为无规则型,有的种类叶表皮具单细胞毛或多细胞毛,表皮毛在电镜下具瘤状突起的纹饰。在扫描电镜下,角质层纹饰多具鳞片或颗粒等特征,种间有细微差别。结果表明该7种植物叶表皮微形态有明显差别,这些表皮特征有助于识别一些在外部形态较相近的种类。     

安徽产大戟属药用植物资源及其生物活性

对安徽产大戟属药用植物的资源状况及其生物活性进行了综述。安徽产大戟属药用植物约有9种,具有抗肿瘤、抗菌、抗氧化等生物活性,有些具有一定的毒性。     

Anatomical characteristics and antioxidant properties of Euphorbia nicaeensis ssp. glareosa

Anatomical analyses found that leaves of Euphorbia nicaeensis ssp. glareosa are isolateral, amphistomatous, with two layers of palisade cells on the adaxial and one on the abaxial side. Laticifers are present by vascular bundles, in palisade and spongy tissue. Stem laticifers are located in the pericyclic ring, adjacent to the phloem, in cylinder parenchyma and medullar rays. The structure of pleiochasium and dichasium peduncle is similar to the stem structure. Plants from typical steppe habitat show more xeromorphic features. Phytochemical screening of extracts showed presence of catecholes, flavonoids, tannins, saponins, free quinone derivatives and absence of anthocyanins, leucoanthocyanins, alkaloids, steroid compounds and essential oils. Our results showed that the examined taxon was partially susceptible to the action of reactive oxygen species, such as O₂·⁻ and ·OH. The higher quantities of ROS thus provoked an antioxidative response from the plant, both in an enzymatic and non-enzymatic manner. Stable anatomical structure, presence and distribution of laticifers and effective antioxidant properties when exposed to ROS, make Euphorbia nicaeensis subsp. glareosa potentially interesting for further pharmaceutical and phytochemical examinations.     

Diterpenoids and triterpenoids from Euphorbia guyoniana

Two new compounds with tigliane and cycloartane skeletons: 4,12-dideoxy(4alpha)phorbol-13-hexadecanoate (1) and 24-methylenecycloartane-3,28-diol (2), respectively, in addition of four known diterpenoids and 13 triterpenoids: 3-benzoyloxy-5,15-diacetoxy-9,14-dioxojatropha-6(17),11-diene (4), ent-abieta-8(14),13(15)-dien-16,12-olide (5), ent-8alpha,14alpha-epoxyabieta-11,13(15)-dien-16,12-olide (6), ent-3-hydroxyatis-16(17)-ene-2,14-dione (7), 3beta-hydroxytaraxer-14-en-28-oic acid (8), beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (9), multiflorenyl acetate (10), multiflorenyl palmitate (11), peplusol (12), 24-methylenecycloartanol (3), lanosterol (13), euferol (14), butyrospermol (15), cycloartenol (16), obtusifoliol (17), cycloeucalenol (18) and beta-sitosterol (19), were isolated from the roots of Euphorbia guyoniana. Their structures were established on the basis of physical and spectroscopic analysis, including 1D and 2D homo- and heteronuclear NMR experiments (COSY, HSQC, HMBC and NOESY) and by comparison with the literature data.     

Pentacyclic triterpenes from Euphorbia stygiana

Two pentacyclic triterpenes, D-friedomadeir-14-en-3beta-yl acetate and D:C-friedomadeir-7-en-3beta-yl acetate, named madeiranyl acetate and isomadeiranyl acetate, respectively, were isolated from leaves of Euphorbia stygiana, together with the two known madeiranes, D-friedomadeir-14-en-3-one and D:C-friedomadeir-7-en-3-one, which were obtained from the stem bark. In addition, four known lupane and taraxerane-type triterpenes, namely lupenyl acetate, lupenone, taraxeryl acetate and taraxerone, were also isolated from the same source. Structures were elucidated by physical, chemical and spectroscopic methods (1H NMR, 13C NMR, IR and mass spectra) and by comparison with literature data, and in the case of D:C-friedomadeir-7-en-3beta-yl acetate by X-ray analysis as well.     

New nematicidal azaphilones from the aquatic fungus Pseudohalonectria adversaria YMF1.01019

Two new azaphilone metabolites, named pseudohalonectrin A (1) and B (2), were isolated from the culture of the aquatic fungus Pseudohalonectria adversaria YMF1.01019, originally separated from submerged wood in Yunnan Province, China. Pseudohalonectrin A and B were assessed for their nematicidal activity against the pine wood nematode Bursaphelenchus xylophilus and their structures were defined after spectral analysis. This is the first report of secondary metabolites from any member of the genus Pseudohalonectria.