蓍草化学成分研究

研究蓍草Achillea alpine L.全草的化学成分。采用大孔树脂、ODS、Sephadex LH-20凝胶柱色谱和pre-HPLC等方法分离与纯化,运用NMR、MS等波谱技术鉴定化合物结构。从蓍草95%乙醇提取物中分离得到16个化合物,分别是(2 E,4 E)-N-(2-methylbutyl)deca-2,4-dienamide(1)、墙草碱(2)、(E,E,Z)-2,4,8-decatrienoicacid isobutylamide-8,9-dehydropellitorine(3)、N-2′-methylbutyl-(E,E)-2,4-decadienam(4)、methyl-(E,E)-2,4,9-oxooctadeca-10,12-dienoate(5)、(S)-14-(E,E)-10,12-methyl 14-hydroxy-9-oxo-octadeca-10,12-dienoate(6)、(E,E)-2,4-undecadiene-8,10-diynamide-N-(2-methylpropyl)(7)、(E,E)-2,4-decadienoic acid p-hydroxyphenethylamide(8)、sinapyl alcohol diisovalerate(9)、(S)-13-hydroxyoctadeca-(Z,E)-9,11-dienoic acid(10)、(E,E)-2,4-decadienamide acid p-methoxyphenethylamide(11)、erythro-N-isobutyl-4,5-dihydroxy-2-(E)-decenamide(12)、3-O-阿魏酰-奎宁酸(13)、肉桂酸(14)、绿原酸(15)、3-O-咖啡酰-5-O-阿魏酰奎宁酸(16)。化合物1是一个新的酰胺类化合物;化合物4~6、9、10、12、13、16为首次从该属植物中分离得到;化合物8、11为首次从蓍草中分离得到。化合物1~11在四种不同的胃癌细胞株上进行细胞毒活性筛选,结果显示化合物2、5与9在50μM时对MGC-803细胞株具有较弱抑制活性,其抑制率依次为38.7%、34.7%、31.5%。     

大叶吊兰中一个新的甾体皂甙

从百合科植物大叶吊兰（Ｃｈｌｏｍｐｈｙｔｕｍ ｍａｌａｙｅｎｓｅ）根茎中分离得到１个新的呋甾烷型甾体皂甙,命名为大叶吊兰甙Ｅ（ｃｈｌｏｒｏｍａｌｏｓｉｄｅ Ｅ）。经波谱和化学方法证明明其结构为：２６－０－β－Ｄ－ｇｌｕｃｏｐｙｒａｎｏｓｙｌ－２２－ｈｙｄｒｏｘｙ－２５（Ｓ）－５ａ－ｆｕｒｏｓｔａｎ－１２－ｏｘｏ－３β,２６－ｄｉｏｌ－３－β－Ｄ－ｘｙｌｏｐｙｒａｎｏｓｙｌ（１→３）〖α－Ｌ－ａｒａ     

Cytotoxic hydroazulene diterpenes from the brown alga Dictyota dichotoma

Two new hydroazulenoid (prenyl guaiane) diterpenes, dictyone acetate (2) and 3,4-epoxy 13-hydroxy pachydictyol A (4) were isolated from the petroleum ether fraction of the alcoholic extract of the brown alga, Dictyota dichotoma (Hudson) Lamouroux, which was collected from the Red Sea coasts at Hurgada, Egypt, together with three known ones, pachydictyol A (1), dictyone (3) and 11-hydroxypachydictyol A (dictyol E) (5). In addition, the steroidal compound, stigmasta-5,(E)-24(28)-dien-3-beta-ol (fucosterol) (6) was also isolated. The structures of the isolated compounds have been determined on the basis of spectroscopic evidences as well as physical and chemical correlation with known compounds. Compounds 1, 2, 3 and 5 showed moderate cytotoxic activity.     

牛尾草中一新的对映-贝壳杉烷型二萜

从牛尾草[Isodon ternifolius(D.Don)Kudo]的地上部分分离得到一个新的对映－贝壳杉烷型二萜,命名为牛尾草素H（1）,通过波谱方法鉴定了它的结构。此外,还分离得到5个已知的对映－贝壳杉烷型二萜化合物：香茶菜醛（2）,长管香茶菜素A,E和G（3－5）,开展香茶菜素E（6）,以及木樨草素（7）,芹菜素（8）,α－香树脂醇（9）,乌索酸（10）和2α－羟基乌索酸（11）。     

Isolation and structural determination of a novel bicyclic taxane diterpene from needles of the Chinese yew, Taxus mairei.

A novel bicyclic taxane diterpene with a rare 12-membered ring was isolated from needles of the Chinese yew, Taxus mairei, and its structure was established as (3E, 8E)-2 alpha, 7 beta, 9, 10 beta, 13 alpha, 20-hexaacetoxy-5(2'-acetoxy-cinnamoyloxy)-3,8-secotaxa -3,8,11-triene (1) with the help of 1D and 2D NMR data. The relative stereochemistry was deduced from a NOESY experiment.     

New cerebrosides from Euphorbia peplis L.: antimicrobial activity evaluation

The less polar fraction of the methanolic extract from the plant Euphorbia peplis L. exhibited interesting antifungal and antitubercular activity. A complex mixture of four glucocerebrosides was responsible for this activity. Two new cerebrosides were isolated for the first time from Euphorbiaceae, 4 was assigned as 1-O-(beta-D-glucopyranosyl)-(2S,3S,4E,8E)-2N-[(2'R)-2'-hydroxy-hexadecanoyl]-4 (E), 8 (E)-octadecadiene-1,3-diol and 3 as the 1-O-(beta-D-glucopyranosyl)-(2S,3S,4R,8Z)-2N-[(2'R)-2'-hydroxytetracosanoyl]-8 (Z)-octadecene-1,3,4-triol. The structures were determined on the basis of chemical and spectroscopic evidences. Mass spectrometry of dimethyl disulfide derivatives was useful for the determination of the double-bond positions in the long-chain bases.     

Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel

Three novel meroterpenoids, insuetolides A-C (1-3) and four drimane sesquiterpenes, the new (E)-6-(4'-hydroxy-2'-butenoyl)-strobilactone A (4) and the known 2α, 9α, 11-trihydroxy-6-oxodrim-7-ene (5), strobilactone A (6) and (E,E)-6-(6',7'-dihydroxy-2',4'-octadienoyl)-strobilactone A (7), were isolated from the EtOAc extract of the culture medium of the marine-derived fungus Aspergillus insuetus (OY-207), which was isolated from the Mediterranean sponge Psammocinia sp. The structures of the compounds were determined by spectroscopic methods. Insuetolides A-C reveal a new carbon skeleton derived from the cyclization of farnesyl and 3, 5-dimethylorsellinic acid. Compounds 1, 6, and 7 exhibited anti-fungal activity towards Neurospora crassa with MIC values of 140, 242, and 162 μM, respectively; and compounds 3, 4, and 7 exhibited mild cytotoxicity towards MOLT-4 human leukemia cells.     

红汁乳菇中一个新的薁类色素

从担子菌红汁乳菇的子实体中分离得到一个新的绿色薁类色素,其化学结构通过波谱学方法包括二维核磁共振鉴定为:1-[(15E)-丁烯-17-酮]-4-甲基-7-异丙基薁。同时还从该菌中分离得到其它三个红紫色的薁类色素。     

A novel antiproliferative agent, phenylpyridineylbutenol, isolated from Streptomyces sp

A novel compound showing antiproliferative effect was isolated from Streptomyces sp. Its structure was determined based on the interpretation of the NMR spectra, and its conformation was elucidated using molecular modeling and 2D NOESY. It was determined to be (E)-4-phenyl-3-(pyridine-2-yl)but-2-en-1-ol.     

西南远志中皂苷类成分的分离与鉴定

采用乙醇回流提取,通过硅胶柱、HPD100大孔树脂、Sephadex LH-20、半制备HPLC分离方法,运用现代谱学方法从西南远志中分离并鉴定了4个齐墩果酸型皂苷类化合物,均为顺反异构体,所用实验方法并不能有效分开。他们分别是:(E/Z)-PolygalasaponinXLIV(1),3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-galactopyr-anosyl-(1→4)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-D-glucopyranosyl-(1→3)]-{4-O-([E/Z)-3,4-dimethoxycinnamoyl}]-β-D-fucopyranosyl ester(2),(E/Z)-PolygalasaponinXXX(3)(,E/Z)-senegasaponin C(4),均为首次从该种植物中分离得到。     

Flavonoid glycosides and saponins from Astragalus shikokianus

A new flavonol glycoside, kaempferol 3-O-alpha-L-rhamnopyranosyl -(1-->6)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-7-O-a lpha-L-rhamnopyranoside, named astrasikokioside I, was isolated from aerial part of Astragalus shikokianus, together with two flavonol glycosides, kaempferol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-7-O-alpha-L- rhamnopyranoside, robinin, and three triterpenoid glycosides, soyasaponin I, sophoraflavoside II and robinioside E.     

Hyrtioreticulins A-E, indole alkaloids inhibiting the ubiquitin-activating enzyme, from the marine sponge Hyrtios reticulatus

Hyrtioreticulins A-E (1-5) were isolated from the marine sponge Hyrtios reticulatus, along with a known alkaloid, hyrtioerectine B (6). Structural elucidation on the basis of spectral data showed that 1, 2, and 5 are new tetrahydro-β-carboline alkaloids, while 3 and 4 are new azepinoindole-type alkaloids. Hyrtioreticulins A and B (1 and 2) inhibited ubiquitin-activating enzyme (E1) with IC(50) values of 0.75 and 11μg/mL, respectively, measured by their inhibitory abilities against the formation of an E1-ubiquitin intermediate. So far, only five E1 inhibitors, panapophenanthrine, himeic acid A, largazole, and hyrtioreticulins A and B (1 and 2), have been isolated from natural sources and, among them, 1 is the most potent E1 inhibitor.     

Lyconadins D and E, and complanadine E, new Lycopodium alkaloids from Lycopodium complanatum

Three new Lycopodium alkaloids, lyconadins D (1) and E (2), and complanadine E (3), were isolated from the club moss Lycopodium complanatum. Lyconadin D (1) was the first example of fastigiatine-type alkaloid isolated from Lycopodium complanatum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Complanadine E (3) enhanced mRNA expression for NGF.     

6-[omega-arylalkenyl]-5,6-dihydro-alpha-pyrones from Cryptocarya moschata (Lauraceae)

Eleven 6-[omega-arylalkenyl]-5,6-dihydro-alpha-pyrones, cryptomoscatones D2, E1, E2, E3 and F1 and cryptopyranmoscatones A1, A2, A3, B1, B2 and B4, in addition to goniothalamin and cryptofolione, were isolated from branch and stem bark of Cryptocarya moschata, Lauraceae. Their structures were established by spectroscopic methods.     

Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana

Four phenylpropanoid esters of rhamnose, buergerisides A1, B1, B2 and C1 were isolated from roots of Scrophularia huergeriana MIQ. (Scrophulariaceae), and were characterized as 2-O-acetyl-3,4-di-O-(E)-p-methoxycinnamoyl-alpha-L-rhamnopyranosid e, 2-O-acetyl-3-O-(E)-p-methoxycinnamoyl-alpha-L-rhamnopyranoside, 2-O-acetvl-3-O-(Z)-p-methoxycinnamoyl-alpha-L-rhamnopyranosi de and 4-O-(E)-p-methoxycinnamoyl-alpha-L-rhamnopyranoside, respectively. In addition, six known phenylpropanoids were authenticated as: (E)-cinnamic acid, (E)-p-methoxycinnamic acid, (E)-p-methoxycinnamic acid methyl ester, (E)-p-coumaric acid, (E)-caffeic acid, (E)-ferulic acid and a phenylalcohol, 2-(3-hydroxy-4-methoxyphenyl)ethanol. These ten phenylpropanoids all attenuated glutamate-induced neurotoxicity when added to primary cultures of rat cortical cells in a dose-dependent manner. These results demonstrate that phenylpropanoids isolated from S. buergeriana may exert significant protective effects against glutamate-induced neurodegeneration in primary cultures of cortical neurons.     

鞭打绣球中的一个新单萜苷

从鞭打绣球(Hemiphragma heterophyllum Wall.)全草中分离到1个新单萜苷和7个已知化合物.通过波谱数据分析,新单萜苷的结构鉴定为(4S)-α-萜烯醇-8-O-β-D-比喃木糖-(1→6)-β-D-比喃葡萄糖苷,已知化合物分别鉴定为globularin(2)、(2S 3S,4R,9E)-1,3,4-trihydroxy-2-[(2'R)-hydroxy-tetracosanoylamino]-9-octadecene(3)、β-香树素(4)、齐墩果酸(5)、肉桂酸(6)、β-谷甾醇(7)和胡萝卜甙(8).除化合物2外,其余化合物均为首次从鞭打绣球中分离得到.     

A new ester isolated from Ferula assa-foetida L

A new caffeic acid cinnamyl ester (1) was isolated from the n-hexane-soluble fraction of an MeOH extract of the gum resin of Ferula assa-foetida L. The structure was determined to be (2E)-3,4-dimethoxycinnamyl-3-(3,4 diacetoxyphenyl) acrylate on the basis of spectroscopic data including 1D- and 2D-NMR. Compound 1 showed moderate activity for inhibiting LPS-induced nitric oxide production in murine macrophage RAW264.7 cells, with an IC50 value of 54.9 microm.     

Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium

From Glochidion zeylanicum, two megastigmane glucosides, 3- and 9-O-beta-D-glucopyranosides of (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol (1 and 2, respectively), were isolated. Their structures were different from those of kiwiionoside (3) and actinidioionoside (4), isolated from Actinidia chinensis and Actinidia polygama, respectively, in the stereochemistry at the 9-positions. Alangionosides E (5) and O (6), isolated from the leaves of Alangium premnifolium, are also megastigmane glucosides, and the latter is closely related to 1 and actinidioionoside (4). However, the absolute configurations of the 9-position remained to be determined. They were analyzed to be R by means of a modified Mosher's method. Alangionoside E (5) is identical with corchoionoside A in all aspects. The name of corchoionoside A must be retained thereafter.     

浆果楝中的新木脂素

从浆果楝（Cipadessa baccifera）中分离得到两个木脂素,其化学结构通过波谱方法鉴定为：（-）-9′-O-（E）-coumarate-5,5′-dimethoxylariciresinol（1）和（＋）-9′-O-（E）-feruloyl-5,5′-dimethoxylariciresinol（2）。其中化合物1为新化合物。     

Drug sensitivity of Enterococcus sp. strains isolated from clinical material or from healthy persons

The aim of this study was to evaluate the drug susceptibility of Enterococcus sp. strains isolated in 2000-2001, from patients of five Warsaw's hospitals (154 strains) and from fecal samples of healthy persons (33 strains). On biochemical reaction profiles species of clinical enterococci were identified as: E. faecalis--66.2%, E. faecium--29.2%, E. hirae--1.9%, E. gallinarum--1.3%, E. casseliflavus--0.6% and E. avium--0.6%. The species of enterococci from stool's samples were identified as: E. faecalis--28 strains, E. durans--2 strains and single strains: E. faecium, E. gallinarum and E. casseliflavus. Susceptibility to 20 antibiotics was tested by disc diffusion method. None of these 187 enterococcal strains was vancomycin resistant; 3 strains of E. gallinarum and 1--E. casseliflavus demonstrated intermediately susceptibility to vancomycin, but they were susceptible to teicoplanin--phenotype Van C. Among clinical strains were resistant to penicillin--33.3% of E. faecalis and 100% of E. faecium, to ampicillin--over 80% of E. faecium and 1 strain of E. faecalis. None of these strains produced beta-lactamase. High-level resistance to aminoglicoside was expressed by 48 strains (47.1%) E. faecalis and 36 (80%) E. faecium isolated from clinical specimens. Both--HLR to streptomycin and gentamycin were found in 28.3% of E. faecalis and 68.9% of E. faecium. Among 33 strains isolated from fecal samples of healthy persons--3 of E. faecalis were resistant to streptomycin and one was resistant to both gentamicin and streptomycin. In general, enterococcal strains isolated from samples of healthy persons were susceptible to the most of used antibiotics. But to rifampicin none of these strains were susceptible. There were about 40% of E. faecalis strains isolated from healthy persons, resistant to tetracyline.