楮实子的化学成分研究

目的对桑科构树属植物构树的果实——楮实子的化学成分进行研究。方法采用柱色谱法进行分离、精制,通过理化性质和波谱分析方法鉴定化合物的结构。结果从楮实子95％乙醇冷浸物中分离得到7个化合物,分别鉴定为胡萝5苷棕榈酸酯（Ⅰ）、胡萝卜苷（Ⅱ）、苯丙氨酸（Ⅲ）、色氨酸（Ⅳ）、壬二酸（Ⅴ）、β-谷甾醇（Ⅵ）、蔗糖（Ⅶ）。结论化合物Ⅰ、Ⅱ、Ⅲ、Ⅳ和Ⅴ均首次在楮实子中分得。     

Bioactive constituents from Asparagus cochinchinensis

Bioassay-directed fractionation of the dried roots of Asparagus cochinchinensis led to the isolation of a new spirostanol saponin, asparacoside (1), two new C-27 spirosteroids, asparacosins A (2) and B (3), a new acetylenic derivative, 3' '-methoxyasparenydiol (4), and a new polyphenol, 3'-hydroxy-4'-methoxy-4'-dehydroxynyasol (6), as well as five known phenolic compounds, asparenydiol (5), nyasol (7), 3' '-methoxynyasol (8), 1,3-bis-di-p-hydroxyphenyl-4-penten-1-one (9), and trans-coniferyl alcohol (10). Compounds 1, 6, and 8 demonstrated moderate cytotoxicities in a panel comprised of KB, Col-2, LNCaP, Lu-1, and HUVEC cells, with IC(50) values ranging from 4 to 12 microg/mL. The structures were determined by spectroscopic and chemical methods.     

Bioactive constituents from Iryanthera megistophylla

Activity-guided fractionation of the 95% ethanol extract from the stem bark of Iryanthera megistophylla led to the isolation of two new compounds, named megislignan [2,3-dimethyl-4-(4-methoxyphenyl)-6-hydroxynaphthalene] (1) and megislactone [(2R,3R,4R)-3-hydroxy-4-methyl-2-(hexacos-17-enyl)butanolide] (2), along with seven known compounds, grandinolide (3), iryantherin K (4), iryantherin L (5), cinchonain I b (6), cinchonain I a (7), procyanidin B-2 (8), and cinchonain IIa (9). The structures of the new compounds were elucidated by spectral data interpretation. Isolates were evaluated for their antibacterial, antifungal, antiviral, and antiacetylcholinesterase activities.     

构树叶中的细胞毒成分（英文）

目的：研究构树叶的化学成分。方法：采用D101型大孔吸附树脂、硅胶、ODS和半制备型高效液相色谱等分离方法对构树叶提取物分离纯化,通过1D,2DNMR技术确定其结构,并采用MTT法对分得化合物进行细胞毒活性测定,同时比色法和采用高效液相色谱法建立了对构树叶中总黄酮和cosmosiin的含量测定方法。结果：分离鉴定了6个化合物,它们的结构鉴定为：（＋）-pinoresinol-4′-O-β-D-glucopyransyl-4″-O-β-D-apiofuranoside（1）,cosmosiin（2）,luteolin-7-O-β-D-glucopyranoside（3）,liriodendrin（4）,3,5,4′-trihydroxy-bibenzyl-3-O-β-D-glucoside（5）,apigenin-6-C-β-D-glycopyranside（6）。结论：化合物1为一个新的木脂素,化合物5,6为首次从该属植物中分离,化合物1,4,6对HepG-2细胞株有不同程度的抑制活性,而化合物2,3,5对HepG-2细胞株没有活性;根据含量测定结果得知,确定构树叶的最佳采收时间为9月份。     

Bioactive constituents from three Vismia species

Bioassay-guided fractionation of the methanolic extracts of Vismia baccifera, V. jefensis, and V. macrophylla against human breast, CNS, and lung cancer cell lines resulted in the isolation of a new compound, ferruginin C (1), and seven known compounds, ferruginins A (2) and B (3), vismin (4), harunganin (5), vismione B (6), deacetylvismione H (7), and deacetylvismione A (8), as active constituents. In addition, bivismiaquinone (9) and vismiaquinone (10) were obtained as inactive constituents. The structure of ferruginin C was elucidated by spectroscopic means. Compounds 6-8 were the most active, and the cytotoxic activity of compounds 2-5 and 7 is reported for the first time.     

Bioactive constituents from the marine crinoid Himerometra magnipinna

A new tetrabromospirocyclohexadienylisoxazole, (+)-12-hydroxyhomoaerothionin (1), together with the known compounds (+)-aerothionin (2) and crinemodin-rhodoptilometrin bianthrone (3), were isolated from the marine crinoid Himerometra magnipinna, which had been collected in the South China Sea, Malaysia. The structure of 1 was elucidated by interpretation of 1D 1H and 13C NMR spectra and 2D 1H-1H COSY, HMQC, and HMBC spectra. This is the first report of tetrabromospirocyclohexadienylisoxazole compounds from a crinoid of Himerometra. Compounds 1-3 were evaluated for their inhibitory activity with the hyphae formation inhibition assay in Streptomyces 85E.     

Bioactive constituents from the twigs of Asimina parviflora.

The EtOH extract of Asimina parviflora (Annonaceae), when subjected to activity-directed fractionation using lethality to brine shrimp, led to the isolation and identification of five bioactive compounds: asimicilone [1], which is a new 2-quinolone alkaloid, 6-cis-docosenamide [2], which is a new amide of a long hydrocarbon chain fatty acid, and three known compounds, asimicin, (+)-syringaresinol, and beta-sitosterol-beta-D- glucopyranoside. The structure determination of the new alkaloid was performed by extensive nmr analyses, including HMQC and HMBC. Selective cytotoxic activities of these compounds in three human solid tumor cell lines are also reported.     

Bioactive constituents of Thuja occidentalis

An ethyl acetate-soluble extract of the combined leaves and twigs of Thuja occidentalis was found to inhibit 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase (ODC) in cultured mouse epidermal ME 308 cells. Bioassay-guided fractionation of this extract led to the isolation of six active constituents (1-6), namely, (+)-7-oxo-13-epi-pimara-14,15-dien-18-oic acid (1), (+)-7-oxo-13-epi-pimara-8,15-dien-18-oic acid (2), (+)-isopimaric acid (3), (1S,2S,3R)-(+)-isopicrodeoxypodophyllotoxin (4), (-)-deoxypodophyllotoxin (5), and (-)-deoxypodorhizone (6). Compounds 1 and 4 are new natural products, and their structures and stereochemistry were determined using spectroscopic methods. Compounds 1-6 were evaluated for inhibition of the transformation of murine epidermal JB6 cells, inhibition of ornithine decarboxylase induction with murine epidermal ME 308 cells, and cytotoxic activity against KB cells.     

Bioactive constituents of Cedrelopsis microfoliata

The stem bark of Cedrelopsis microfoliata has yielded the new compounds microfolian (1), microfolione (2), and microfolicoumarin (6) along with the known compounds agrandol (3), cedrecoumarin A (4), obliquin (5), and sesquichamaenol (7). Compounds 2-4 were found to show agonistic activity on both alpha- and beta-estrogenic receptors, and compounds 1, 3, and 4 were shown to inhibit the chemiluminescence of reactive oxygen metabolites and showed superoxide scavenging activity.     

乳香抗哮喘有效部位化学成分的研究

目的研究乳香抗哮喘活性部位的化学成分。方法以抗哮喘活性为追踪,采用硅胶柱色谱对乳香抗哮喘有效部位进行分离,运用IR、MS、NMR等方法进行结构鉴定。结果从乳香的抗哮喘活性部位分离并鉴定了8个化合物,分别为β乙酰乳香酸(acetyl β-boswellic acid,Ⅰ)、β-乳香酸(B-boswellic acid,Ⅱ)、pinnicolic acid A(3-ox-olanosta-8,24-dien-21-oic acid,Ⅲ)、栓菌酸β(3β-hydroxylanosta-8,24-dien-21-oic acid,Ⅳ)、α-乳香酸(α-boswellic acid,Ⅴ)、11-羰基-β-乙酰乳香酸(11-keto-β-boswellic acid,Ⅵ)、脱氢松香酸(Ⅶ)、山达海松酸(Ⅷ)。结论化合物Ⅶ、Ⅷ均为首次从该植物中分离得到。     

Bioactive chemical constituents from Alchornea laxiflora (benth) pax and hoffman

Quercetin-7,4'-disulphate (1) quercetin (2) quercetin-3',4'-disulphate (3) quercetin-3,4'-diacetate (4) rutin (5) and quercetrin (6) were isolated from the ethyl acetate soluble fraction (ESM) of the crude methanolic leaf extract of Alchornea laxiflora. Purification of these compounds was carried out by column chromatography utilising sephadex LH 20 and various mixtures of water, methanol, ethanol and toluene as eluents. Structural elucidation was by UV, IR, (1)HNMR and (13)CNMR spectroscopy as well as by FAB-MS. Antimicrobial activity of isolated compounds was detected in Gram-positive, Gram-negative and fungal organisms.     

Bioactive constituents of the roots of Cynanchum atratum

A novel biphenylneolignan, 2,6,2',6'-tetramethoxy-4,4'-bis(2,3-epoxy-1-hydroxypropyl)biphenyl (1), and two new glycosides named atratoglaucosides A (2) and B (3), were isolated from the roots of Cynanchum atratum, and their structures were determined on the basis of chemical and spectroscopic evidence. The aglycons of 2 and 3 were identified as glaucogenin C and 7-desoxyneocynapanogenin A, a new disecopregnane. A known compound, glaucogenin C 3-O-beta-D-cymaropyranosyl-(1-->4)-alpha-L-diginopyranosyl-(1-->4)-beta-D-thevetopyranoside (4), isolated from the same source, showed a significant cytotoxic effect against 212 cells. This substance also gave a significant inhibitory effect on TNF-alpha (tumor necrosis factor-alpha) formation from the RAW 264.7 mouse macrophage-like cell line stimulated with LPS (lipopolysaccharide) and on the N9 microglial cell line stimulated with LPS/IFN-gamma (interferon-gamma).     

Bioactive diterpenes and other constituents of Croton steenkampianus

A new indanone derivative (1) and two new diterpenoids (2 and 3), together with three known flavonoids, have been isolated from an ethanol extract of the leaves of Croton steenkampianus. The structure of 2 was solved by single-crystal X-ray diffraction analysis, whereas those of 1 and 3 were established mainly by 1D and 2D NMR spectroscopic methods. The isolated compounds were tested for their antiplasmodial activity and cytotoxicity. Antiplasmodial assays against chloroquine-susceptible strains (D10 and D6) and the chloroquine-resistant strains (Dd2 and W2) of Plasmodium falciparum showed that compound 2 gave moderate activities at 9.1-15.8 μM, while none of the compounds were cytotoxic against Vero cells.     

Bioactive constituents of the roots of Polyalthia cerasoides

A new dimeric aporphine alkaloid, bidebiline E (1), and a new natural product, octadeca-9,11,13-triynoic acid (2), along with three known sesquiterpenes, alpha-humulene (3), caryophyllene oxide (4), and (-)-alpha-cadinol (5), and four known isoquinoline alkaloids, laudanosine (6), codamine (7), laudanidine (8), and reticuline (9), were isolated from the roots of Polyalthia cerasoides. The structures of compounds 1 and 2 were established on the basis of their 1D and 2D NMR spectroscopic data. Among these isolates, 1, 2, 4, 7, and 8 exhibited antimalarial activity against Plasmodium falciparum, while 1- 3 showed antimycobacterial activity against Mycobacterium tuberculosis using in vitro assays.     

Bioactive constituents of the roots of Licania intrapetiolaris

Fractionation of a methanol extract of the roots of Licania intrapetiolaris, as directed by activity against the KB assay, has led to the isolation of two novel clerodane diterpenoids, intrapetacins A (1) and B (2), and the known triterpenoid cucurbitacin B (3). The structures of 1 and 2 were deduced from one- and two-dimensional NMR experiments, including relative stereochemical assignments based on NOESY correlations and COSY coupling constants. Compound 3 was the most potent against the KB assay, but both 1 and 2 displayed moderate cytotoxicity. When evaluated against an antifungal assay using Aspergillus niger, 2 caused a significant zone of inhibition of fungal growth, while 1 was completely inactive. To the best of our knowledge, this is the first report of the isolation of bioactive compounds from the genus Licania.     

Aromatase inhibitors from Broussonetia papyrifera.

Bioassay-guided fractionation of an ethyl acetate-soluble extract from the whole plants of Broussonetia papyrifera, using an in vitro aromatase inhibition assay, led to the isolation of five new active compounds, 5,7,2',4'-tetrahydroxy-3-geranylflavone (1), isogemichalcone C (8), 3'-[gamma-hydroxymethyl-(E)-gamma-methylallyl]-2,4,2',4'-tetrahydroxychalcone 11'-O-coumarate (9), demethylmoracin I (10), and (2S)-2',4'-dihydroxy-2' '-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanone (11), and 10 known (12-21) compounds which were also found to be active. Of these compounds, the most potent were 9 (IC(50) 0.5 microM), 11 (IC(50) 0.1 microM), isolicoflavonol (12, IC(50) 0.1 microM), and (2S)-abyssinone II (13, IC(50) 0.4 microM). Additionally, six new compounds, 5,7,3',4'-tetrahydroxy-6-geranylflavonol (2), 5,7,3',4'-tetrahydroxy-3-methoxy-6-geranylflavone (3), (2S)-7,4'-dihydroxy-3'-prenylflavan (4), 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propane (5), 1-(2,4-dihydroxy-3-prenylphenyl)-3-(4-hydroxyphenyl)propane (6), and 1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxy-3-prenylphenyl)propane (7), were isolated and characterized, but proved to be inactive as aromatase inhibitors, as were an additional 21 known compounds. The structures of the new compounds (1-11) were elucidated by spectroscopic methods. Structure-activity relationships in the aromatase assay were determined for the benzofurans, biphenylpropanoids, coumarins, and various types of flavonoids (chalcones, flavans, flavanones, and flavones) obtained among a total of 42 constituents of B. papyrifera.     

Bioactive diterpenoids, a new jatrophane and two ent-abietanes, and other constituents from Euphorbia pubescens

A new jatrophane diterpene, pubescenol (1), known ent-abietane lactones, helioscopinolide A (2) and B (3), and taraxerone, 24-methylenecycloartanol, and vanillin have been isolated from Euphorbia pubescens. Diterpenes 1-3 and previously described pubescene D (4) were shown to be moderate inhibitors of the growth of MCF-7, NCI-H460, and SF-268 human tumor cell lines, whereas compounds 2 and 3 also exhibited significant antibacterial activity against Staphylococcus aureus.     

Bioactive constituents of the leaves of Phyllanthus polyphyllus var. siamensis

A dichloromethane extract of the leaves of Phyllanthus polyphyllus var. siamensis afforded two new monoacetylated triterpene arabinosides (1 and 2) and 15 known compounds. The structures of the new compounds were elucidated on the basis of spectroscopic data interpretation. The isolates and some chemical transformation products were evaluated biologically, and the presence of an arabinosyl moiety among the hederagenin glycosides evaluated was found to be important for the modulation of cytotoxic activity against cancer cells.     

构树叶的化学成分

目的:对构树Broussonetia papyrifera(L.)Vent.叶的化学成分进行分离和鉴定。方法:采用硅胶柱层析、sephadex LH-20柱层析和重结晶等方法分离纯化,根据理化性质和光谱鉴定化合物的结构。结果:从构树叶乙酸乙酯部位分离得到11个化合物,分别为:芹菜素(apigenin,1)、大波斯菊苷(cosmosiin,2)、牡荆苷(vitexin,3)、木犀草素(luteolin,4)、木犀草素-7-O-β-D-葡萄糖苷(luteolin-7-O-β-D-glucopyranoside,5)、7-甲氧基香豆素(7-methoxycoumarin,6)、东莨菪素(scopoletin,7)、三十一烷醇(1-hentriacontanol,8)、槲皮素(quercetin,9)、7-甲氧基芹菜素(7-methoxyapigenin,10)、β-胡萝卜苷(daucosterol,11)。结论:化合物1~8首次从构树中分离得到。     

构树皮中的酚性化合物研究

目的:研究构树皮的酚性化学成分。方法:通过硅胶柱层析、ODS柱、Sephadex LH-20等色谱技术对构树皮的化学成分进行分离纯化,并根据理化性质与波谱数据对化合物进行结构鉴定。结果:从构树皮中分离鉴定了11个酚性化合物,分别为:松脂素-4'-O-β-D-吡喃葡萄糖苷(1)、黑立脂素苷(2)、松脂素-4'-O-β-D-吡喃葡糖基-4″-O-β-D-呋喃芹菜苷(3)、di-O-methylcrenatin(4)、leonuriside A(5)、3,4,5-三甲氧基苯基-β-D-吡喃葡萄糖苷(6)、kelampayoside A(7)、咖啡酸甲酯(8)、槲皮素(9)、槲皮素-3-O-α-L-吡喃鼠李糖苷(10)、对羟基苯甲酸-β-D-吡喃葡萄糖酯苷(11)。结论:其中,化合物4~8、10、11为首次从该植物中分离得到。