Cytotoxic constituents fromSolanum lyratum

Activity-guided fractionation of the ethanol extract of the whole plant from Solanum lyratum resulted in the isolation of a new pregnane derivative glycoside, 16-dehydropregnenolone 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosid uronic acid (2), as well as other six known compounds: 16-dehydropregnenolone (1), allopregenolone (3), protocatechuic acid (4), vanillic acid (5), caffeic acid (6), and scopoletin (7). The structures of the isolated compounds were elucidated on the basis of their spectral data and chemical evidences. Compounds 1, 3, 4 were isolated for the first time from this plant. Cytotoxic activities of the isolated compounds were evaluated. Compound 1 exhibited significant cytotoxic activity against A375-S2, HeLa, SGC-7901, and Bel-7402 with IC50 values of 13.1 +/- 0.9, 21.5 +/- 1.0, 40.2 +/- 0.7, and 49.8 +/- 1.2 microg/mL, respectively.     

Cytotoxic constituents ofSaussurea lappa

The crude extract ofSaussurea lappa displayed significant lethality to brine shrimp larvae. Investigation of the causative components by bioactivity-directed fractionation resulted in the isolation of three C₁₇-polyene alcohols. Based on various nmr spectral data, these compounds were idenfitied as shikokiols which had been previously isolated fromCirsium nipponicum and/orCentaurea aegyptica. These C₁₇-polyene alcohols exhibited moderate cytotoxicities against the human tumor cell lines, A549, SK-OV-3, SK-MEL-2, XF498, and HCT15.     

Cytotoxic constituents ofPsoralea corylifolia

A coumestan derivative, psoralidin (1) was found to be a cytotoxic principle of the seeds of Psoralea corylifolia L. (Leguminosae) with the IC50 values of 0.3 and 0.4 microg/ml against the HT-29 (colon) and MCF-7 (breast) human cancer cell lines, respectively. A coumarin, angelicin (2) was also isolated as a marginally cytotoxic agent along with an inactive compound, psoralen (3) from the plant. The isolates 1-3 were not active against the A541 (lung) and HepG2 (liver hepatoma) cancer cell lines.     

Cytotoxic constituents from Aquilegia ecalcarata

A new alkaloid, 7-hydroxy-4-(5'-hydroxymethylfuran-2'-yl)-2-quinolone (1), and a new nitrile derivative, 3alpha,4beta-dihydroxy-6-oxo-1-cyclohexene-1-acetonitrile (2), together with three known oxoaporphine alkaloids, were isolated from the whole plant of Aquilegia ecalcarata. Their structures were established on the basis of spectral evidence. Their in vitro cytotoxicity against different classes of cancer cell lines, including GLC-82 and HCT were determined. The new alkaloid 1 [IC 50 (GLC-82) 8.8 +/- 0.2 microM, IC 50 (HCT) 10.1 +/- 0.3 microM] and hernandonine ( 3) [IC 50 (GLC-82) 7.6 +/- 0.5 microM, IC 50 (HCT) 8.2 +/- 0.5 microM] exhibited cytotoxicity towards the cancer cell lines.     

四合木中的三萜类化学成分研究

目的：研究四合木Tetraena mongolica的化学成分。方法：采用硅胶柱色谱、凝胶柱色谱和HPLC制备色谱方法分离纯化得到单体化合物,采用有机波谱方法鉴定化合物结构。结果：从四合木醋酸乙酯提取物中分离得到5个化合物,分别为11α,12α：13β,28-diepoxyoleanane-3β-caffeate（1）,3β-hydroxy-11α,12α：13β,28-diepoxyoleanane（2）,3β-（3,4-dihydroxy-cinnamoyl）-erythrodiol（3）,槲皮素（4）,（E）-22-（3-（4-hydroxy-3-methoxyphenyl）acryloyloxy）docosanoic acid（5）。结论：化合物1～5均为首次从该属中分离得到,化合物1为未见报道的新化合物,化合物2为新天然产物。     

Cytotoxic constituents from Cratoxylum arborescens

A new natural xanthone, 1,3-dihydroxy-6,7-dimethoxy-2,8-diprenylxanthone, together with four known compounds, fuscaxanthone C, 1,7-dihydroxyxanthone, 3-geranyloxy-6-methyl-1,8-dihydroxyanthraquinone and 2-geranylemodin were isolated from the stem bark of Cratoxylum arborescens (Vahl) Blume. The structure elucidations were achieved through spectroscopic analyses. Compounds 1 and 5 showed moderate activity against the human small cell lung cancer NCI-H187 cell line with the IC50 values of 3.69 +/- 1.27 microg/mL and 3.08 +/- 0.73 microg/mL, respectively.     

Cytotoxic phenolic constituents ofAcer tegmentosum maxim

The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-alpha-L-lyxoside (5), p-hydroxy phenylethyl-O-beta-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-beta-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-beta-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl beta-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with ED50 values ranging from 1.32 to 3.85 microM.     

Cytotoxic constituents from Angelicae Sinensis radix

Cytotoxic bioassay-guided fractionation of methanol extract of Angelicae Sinensis Radix led to the isolation of a new dimeric Z-ligustilide, named neodiligustilide (1), together with three known compounds, Z-ligustilide (2), 11(S),16(R)-dihydroxy-octadeca-9Z, 17-dien-12,14-diyn-1-yl acetate (3), and 3(R),8(S)-falcarindiol (4). Among them, 2 showed the strongest cytotoxicity against L1210 and K562 cell lines with IC50 values of 2.27 +/- 0.10 and 4.78 +/- 0.18 microM, respectively, while 1 showed moderate cytotoxicity with IC50 values of 5.45 +/- 0.19 and 9.87 +/- 0.14 microM. Two polyacetylenes, 3 and 4, showed cytotoxicity only against L1210 cell line with IC50 values of 2.60 +/- 0.90 and 2.87 +/- 0.49 microM, respectively.     

Cytotoxic constituents of the octocoralDendronephthya gigantea

A known monoalkyl glycerol ether, (+/-)-1-nonadecyloxy-2,3-propanediol (1) was isolated from the ethyl acetate extract of a soft coral Dendronephthya gigantea as a weakly cytotoxic constituent against four human cancer cell lines, A549, HT-29, HT-1080, and SNU-638. In addition, a known ceramide, (2S,3R,4E,8E)-N-hexadecanoyl-2-amino-4,8-octadecadiene-1,3-diol (2), was also isolated as an inactive constituent. This is the first report on the isolation of the compounds 1 and 2 from the octocoral, Dendronephthya species.     

New eudesmane sesquiterpene and other constituents from Artemisia mongolica

The aerial parts of Artemisia mongolica afforded the eudesmane derivative ludovicin B, two coumarins, umbelliferone and esculetin, two methoxylated flavones, eupatilin and pectolinarigenin, as well as a new eudesmane sesquiterpene, 6alpha,8alpha-dihydroxyisocostic acid methyl ester. Structures were elucidated by highfield 1D and 2D NMR techniques.     

Cytotoxic constituents from the roots ofAnthriscus sylvestris

Activity-guided fractionation of the roots of Anthriscus sylvestris resulted in the isolation and characterization of five cytotoxic compounds, deoxypodophyllotoxin (1), falcarindiol (2), and angeloyl podophyllotoxin (5) from the hexane soluble fraction and morelensin (3), bursehernin (4) from the chloroform soluble fraction. It is the first report of the occurrence of compound 5 in nature.     

Cytotoxic constituents ofSorbaria sorbifolia var.stellipila

The acivity-guided fractionation upon the MeOH extract of the aerial parts ofSorbaria sorbifolia var.stellipila led to the isolation of two cucurbitacin-compounds, cucurbitacin D and cucurbitacin F, as active principles. Two compounds were shown to exhibit significant cytotoxicity against cultured human tumor cell lines, A-549, SK-OV-3, SK-MEL-2, XF-498, and HCT 15.     

Cytotoxic constituents from the bark of Salix hulteni

Eight compounds were isolated from the bark of Salix hulteni. Based on spectral data, the isolated compounds were identified as 4-hydroxyacetophenone (1), naringenin (2), aromadendrin (3), catechin (4), picein (5), sachaliside 1 (6), 1-p-coumaroyl-beta-D-glucoside (7), and dihydromyricetin (8). Their cytotoxic activities against brine shrimp and a human lung cancer cell line (H1299) were evaluated.     

Cytotoxic constituents of the leaves of Ixeris sonchifolia

The ethyl acetate extract of the leaves of Ixeris sonchifolia afforded two new and two known sesquiterpene lactone glucosides of the guaiane-type, together with a known alkenol glucoside. The known compounds were identified as ixerin Z (1), ixerin Z-6'-p-hydroxyphenylacetate (2), and (Z)-3-hexen-1-ol-beta-D-glucopyranoside (3), respectively. The structures of the new compounds were elucidated as 11,13a-dihydroixerin Z [4, 3-hydroxy-2-oxo-guaia-1(10), 3-dien-5alpha,6beta,7alpha, 11betaH-12,6-olide-3-O-beta-D-glucopyranoside], and 3,10beta-dihydroxy-2-oxo-guaia-3,11(13)-dien-1alpha,5alpha,6alpha,7aH-12,6-olide-10-O-beta-D-glucopyranoside (5), respectively. The cytotoxicity of these compounds against human hepatocellular carcinoma cell (HepG2) and human melanoma cell (SK-MEL-2) was evaluated.     

Cytotoxic constituents from the whole plant ofcorydalis pallida

Here we report the cytotoxic activity of three known compounds isolated for the first time from Corydalis pallida (Papaveraceae). An isoquinoline alkaloid, berberine, exhibited cytototoxic activity against two human cancer cell lines, HT-1080 (human fibrosarcoma) and SNU-638 (human stomach adenocarcinoma), with IC50 values of 3.2 and 3.4 microg/mL, respectively. N-trans-feruloyltyramine and N-trans-feruloylmethoxytyramine were also isolated from this plant but were inactive.     

Cytotoxic C-benzylated chalcone and other constituents ofEllipeiopsis cherrevensis

A new natural C-benzylated chalcone, 2',4'-dihydroxy-3'-(2-hydroxybenzyl)-6'-methoxychalcone (2), along with two other flavonoids, tiliroside and kaempferol 3-O-rutinoside, and an oxoaporphine alkaloid, lanuginosine were isolated from the aerial parts of Ellipeiopsis cherrevensis (Annonaceae). Two known polyoxygenated cyclohexene derivatives, ferrudiol and zeylenol, and a new analog, ellipeiopsol D, were also isolated. The chalcone 2 exhibited cytotoxic activity against human small-cell lung-cancer (NCI-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines with IC50 values of 1.40, 5.31 and 13.92 microg/mL, respectively. This compound also showed antimalarial activity against Plasmodium falciparum with an IC50 value of 7.1 microg/mL as well as antimicrobacterial activity against Mycobacterium tuberculosis with a MIC of 25 mg/mL.     

Cytotoxic activity and chemical constituents of Anthemis mirheydari

Context The genus Anthemis L. (Asteraceae) comprises about 195 species which are widely used in the pharmaceutical, cosmetic and food industries.

Objective Anthemis mirheydari Iranshar, an endemic plant from Iran, was investigated for its cytotoxic properties and chemical constituents.

Materials and methods The whole parts of the plant (320?g) were extracted by dichloromethane and methanol for four days, successively. The cytotoxic activity of both dichloromethane and methanol extracts were assayed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric methods against three human cancer cell lines including LS180, MCF-7 and MOLT-4. Different concentrations (10–100?μg/mL) of the plant extracts were tested to obtain IC₅₀ values. The dichloromethane extract of A. mirheydari was subjected to silica gel-column and thin layer chromatography for purification of its chemical constituents and the isolated compounds were further tested against MOLT-4 cells. The structures of the pure compounds were elucidated using different spectral data including nuclear magnetic resonance and electron impact mass spectra.

Results The IC₅₀ values of the dichloromethane extract were 30.8?±?6.7, 25.2?±?6.5 and 8.6?±?1.1?μg/mL (means?±?standard error) for the above-mentioned cell lines, respectively. Two triterpenoids, taraxasterol (1) and pseudotaraxasterol (2), one sterol, β-sitosterol (3) and one coumarin, 7-methoxycoumarin (4) were isolated from the extract. The IC₅₀ of the mixture of compounds 1 and 2 as well as compounds 3 and 4 were higher (>100?μM) than that reported for the dichloromethane extract against MOLT-4 cells.

Conclusion The dichloromethane extract was the most active one among the tested material.     

Cytotoxic constituents fromSolidago virga-aurea var.gigantea MIQ

Activity-guided fractionation of the whole plant of Solidago virga-aurea var. gigantea M(IQ). (Compositae) has led to the isolation of three cytotoxic compounds, erythrodiol-3-acetate (1), alpha-tocopherol-quinone (2), and trans-phytol (3) from the hexane soluble fraction. It is the first report of those compounds from the genus.     

Cytotoxic constituents from the seeds of Vietnamese Caesalpinia sappan

Abstract

Context: Caesalpinia sappan Linn. (Leguminosae) has been used in folk medicines for the treatment of many diseases. The heartwood of this plant contains various phenolic components with interesting biological applications; however, the chemical and biological potentials of the seed of this plant have not been fully explored.

Objective: This study identified the cytotoxic activity of compounds from the seeds of C. sappan.

Materials and methods: The methanol extract of the seed of C. sappan was suspended in H₂O and then partitioned with CH₂Cl₂, EtOAc, and n-BuOH, successively. Diterpenoid compounds were isolated from the CH₂Cl₂-soluble fraction by silica gel column chromatography methods using organic solvents. The compound structures were determined by detailed analysis of NMR and MS spectral data. Cytotoxic activity was measured using a modified MTT assay against HL-60, HeLa, MCF-7, and LLC cancer cells. The activation of caspase-3 enzyme and western blotting assay were performed to confirm inhibitory mechanism of active compound.

Results: Five cassane-type diterpenoids were isolated and identified as phanginin I (1), phaginin A (2), phanginin D (3), phanginin H (4), and phanginin J (5). Compounds 1–4 showed effective inhibition against HL-60 cells with the IC₅₀ values of 16.4?±?1.5, 19.2?±?2.0, 11.7?±?1.6, and 22.5?±?5.1?μM. Compounds 1–3 exhibited cytotoxic activity against HeLa cells with the IC₅₀ values of 28.1?±?3.6, 37.2?±?3.4, and 22.7?±?2.8?μM. Treatment of HL-60 cell lines with various concentrations of 3 (0–30?μM) resulted in the growth inhibition and induction of apoptosis.

Conclusion: These findings demonstrate that compound 3 (phanginin D) is one of the main active components of the seed of C. sappan activating caspases-3 which contribute to apoptotic cell death.     

Cytotoxic and antitumor constituents in pericarps of Mallotus japonicus

A variety of phloroglucinol derivatives isolated from the pericarps of Mallotus japonicus were assessed for growth inhibiting activity against human larynx (HEp-2) and lung (PC-13) carcinoma cells as well as mouse B16 melanoma, leukemia P388, and L5178Y cells. Most of these derivatives were proved to be significantly cytotoxic in culture. One of them, 3-(3,3-dimethylallyl)-5-(3-acetyl-2,4-dihydroxy-5-methyl-6-methoxybenzyl )- phloracetophenone showed an excellent cytotoxicity against all target tumor cells and a marked prolongation of life-span in mice bearing L5178Y leukemia.