Antiproliferative activity of three methoxylated flavonoids isolated from Zeyheria montana Mart. (Bignoniaceae) leaves

The present study isolated three major active flavonoids, two flavones named 4',5,7-trimethoxy-luteolin (1) and 6-hydroxy-5,7-dimethoxyflavone (2) and the flavanone 5-hydroxy-6,7-dimethoxyflavanone (3) from Zeyheria montana dichloromethane leaf extract. Isolation and purification were conducted with the application of column chromatography and structures were assigned by spectral analysis. All compounds were evaluated for cytotoxic activities against human tumor cell lines UACC-62 (melanoma), MCF-7 (breast), NCI-ADR/RES (breast expressing phenotype multiple drug resistance), 786-0 (renal), NCI-H460 (lung, non-small cells), PC-3 (prostate), OVCAR-3 (ovarian), HT-29 (colon) and K562 (leukemia) in vitro. All compounds were active in different degrees on several tumor cell lines and flavanone 3 showed cytotoxicity against almost all cell lines, particularly against human NCI-ADR/RES and K562 cell lines. In conclusion, three antiproliferative compounds were isolated for the first time from Zeyheria montana and its leaves were characterized as an important source of methoxylated flavones and flavanone as potential antitumor compounds.     

Irisones A and B: two new isoflavones from Iris missouriensis

Two new isoflavones, irisones A and B, together with the known compound, 5,7-dihydroxy-2',6-dimethoxy isoflavone, were isolated from the roots of Iris missouriensis. With the help of 2D-homonuclear-J-correlation and 2D-nOe experiments the structure of irisone A was deduced to be 5-hydroxy-2'-methoxy-6,7-methylenedioxy isoflavone. The structure of irisone B was elucidated by spectral analyses as 2',5-dihydroxy-6,7-methylenedioxy isoflavone and was confirmed by chemical conversion to irisone A.     

毛莲蒿的化学成分

 目的：对毛莲蒿的化学成分进行研究。方法：采用硅胶和聚酰胺柱层析进行分离，运用红外光谱、紫外光谱、质谱、核磁共振谱与标准品对照的方法鉴定15个化合物。结果：分离鉴定了3个倍半萜类：taurin（1）、1，11-bis-epi-artesin（2）、yomogin（3）；3个黄酮类：5，7，3′，4′-四羟基-6，8-二甲氧基黄酮（4）、5，7，3′，4′-四羟基-6-甲氧基黄酮（5）、5，6，3′，4′-四羟基-7-甲氧基黄酮（6）；3个三萜类：蒲公英赛醇乙酸酯（7）、木栓酮（8）、α-香树脂醇（9）；2个甾体类：β-谷甾醇（10）、胡萝卜苷（11），2个香豆素类：莨菪亭（12）、7-羟基-6，8-二甲氧基香豆素（13）；2个有机酸类：异阿魏酸（14）、咖啡酸（15）。结论：所有化合物均为首次从该植物中分得。     

Antihyperglycemic activity and chemical constituents of Eysenhardtia platycarpa

The methanolic extracts from branches (BEP) and leaves (LEP) of Eysenhardtia platycarpa significantly decreased the blood glucose levels in normal and streptozotocin (STZ)-induced diabetic rats. One new flavone, (1"R)-5,4',1"-trihydroxy-6,7-(3",3"-dimethylchroman)flavone (1), together with the known compounds 5,7-dihydroxy-6-methyl-8-prenylflavanone (3), 5,7-dihydroxy-8-methyl-6-prenylflavanone (4), 5,7-dihydroxy-6-prenylflavanone (5), 5,7-dihydroxy-8-prenylflavanone (6), 3-O-acetyloleanolic acid (7), oleanolic acid, 3beta-acetoxy-11alpha,12alpha-epoxy-oleanan-28,13beta-olide, lupeol, betulinic acid, beta-sitosterol, beta-sitosteryl beta-D-glucopyranoside, beta-sitosteryl palmitate, and 3-O-methyl-myo-inositol were isolated from BEP. Additionally, one new flavanone, (2S)-4'-O-methyl-6-methyl-8-prenylnaringenin (2), as well as the known compounds 3, 4, 6, 4'-O-methyl-8-prenylnaringenin (8), and 5-hydroxy-7-methoxy-8-prenylflavanone (9) were isolated from LEP. 3-O-Acetyloleanolic acid (7), identified as the major constituent of BEP, showed a significant decrease (31 mg/kg of body weight, P < 0.05) in the glucose level of STZ-induced diabetic rats. The obtained results correlate with the traditional use of this species.     

Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia

Three new [n-pentyl beta-carboline-1-propionate (1), 5-hydroxymethyl-9-methoxycanthin-6-one (2), and 1-hydroxy-9-methoxycanthin-6-one (3)] and 19 known beta-carboline alkaloids were isolated from the roots of Eurycoma longifolia. The new structures were determined by comprehensive analyses of their 1D and 2D NMR and mass spectral data and by chemical transformation. These compounds were screened for in vitro cytotoxic and antimalarial activities, and 9-methoxycanthin-6-one (4) and canthin-6-one (5) demonstrated significant cytotoxicity against human lung cancer (A-549) and human breast cancer (MCF-7) cell lines.     

A novel 2-hydroxyflavanone from collinsonia canadensis

A new flavonoid, 2,5-dihydroxy-6,7-dimethoxyflavanone (1), was isolated from the leaf and stem exudates of Collinsonia canadensis along with three known flavones, baicalein-6,7-dimethyl ether (2), norwogenin-7,8-dimethyl ether (3), and tectochrysin (5-hydroxy-7-methoxyflavone).     

Cytotoxicities of some flavonoid analogues.

An array of 55 flavones having a variety of substituents was evaluated for cytotoxicity in five cancer cell cultures: A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, and MLM melanoma. Fifteen of the 55 flavone derivatives were significantly active against at least one of these cell cultures, and 4'-[(t-butyldi-methylsily)oxy]-7,8-dihydroxy-3',5'- dimethoxyflavone [40] was the most active of all. Structure-activity relationships of these compounds are discussed.     

丁癸草的异黄酮类化学成分研究

 目的 研究丁癸草的化学成分。方法 通过硅胶柱色谱、Sephdex LH20凝胶柱色谱、反相硅胶C-18及高压液相色谱等方法对丁癸草进行分离,运用现代光谱技术鉴定化合物结构;并通过MTT法对其抑制人食管癌细胞TE13和小鼠黑色素瘤细胞B16的增殖进行了研究。结果 从丁癸草中分离得到6个具有抗肿瘤作用的异黄酮类化合物,分别鉴定为7,4′-二甲氧基异黄酮（1）;7-羟基-4′-甲氧基异黄酮（2）;7,3′-二羟基-4′-甲氧基异黄酮（3）;7,8-二羟基-4′-甲氧基异黄酮（4）;7,4′-二羟基-8-甲氧基异黄酮（5）;7,4′-二羟基异黄酮（6）。结论 所有化合物均首次从丁癸草植物中分离得到,并且具有抑制人食管癌TE13细胞的作用,其中化合物3对小鼠黑色素瘤B16细胞的增殖也有抑制作用。     

New dihydrophenanthrene and phenyldihydroisocoumarin constituents of Trema orientalis.

In the course of the chemical investigation of extracts of the trunk bark and root bark of Trema orientalis, three new compounds were isolated, namely, (9S*,10S*)-3-[7-(3,10-dihydroxy-9-hydroxymethyl-2,5-dimethoxy)-9,10-dihydrophenanthrenyl]propenal (1), (9S*,10S*)-3-[7-(5-O-beta-glucopyranosyl-10-hydroxy-9-hydroxymethyl-2,6-dimethoxy)-9,10-dihydrophenanthrenyl]propenal (2), and (3R*,3aR*,4R*,5S*)-6-O-alpha-arabinopyranosyl-8-hydroxy-3-(4-hydroxyphenyl)-4-(4-hydroxyphenyl)-5-(3,5-dihydroxyphenyl)-3,3a-dihydrocyclopenta[1,2,3-de]isobenzopyran-1-one (3, orientoside A). The structures of 1-3 were determined by spectral methods.     

Chemical constituents from the mangrove plant, Aegiceras corniculatum

From the stems and twigs of the mangrove plant, Aegiceras corniculatum, seven new compounds, namely, 2-methoxy-3-nonylresorcinol (1), 5-O-ethylembelin (2), 2-O-acetyl-5-O-methylembelin (3), 3,7-dihydroxy-2,5-diundecylnaphthoquinone (4), 2,7-dihydroxy-8-methoxy-3,6-diundecyldibenzofuran-1,4-dione (5), 2,8-dihydroxy-7-methoxy-3,9-diundecyldibenzofuran-1,4-dione (6), and 10-hydroxy-4-O-methyl-2,11-diundecylgomphilactone (7), were isolated together with three known compounds, 5-O-methylembelin (8), 3-undecylresorcinol, and 2-dehydroxy-5-O-methylembelin. The structures of 1-7 were determined by spectroscopic methods. Compound 2 and 5-O-methylembelin showed in vitro cytotoxicity against the HL-60, Bel(7402), U937, and Hela cell lines.     

Cytotoxic flavonol glycosides from Triplaris cumingiana

Three new compounds, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl-4,6-bis-O-beta-D-(3,4,5-trihydroxybenzoyl)glucopyranoside (1), 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl-5-O-alpha-L-(3,4,5-trihydroxybenzoyl)arabinofuranoside (2), and 2-hydroxy-4-O-alpha-L-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenylarabinofuranoside (3), were isolated from the young leaves of Triplaris cumingiana, together with two known compounds, quercetin 3-O-alpha-L-(5"-O-galloyl)arabinofuranoside (4) and quercetin 3-O-beta-D-(6"-O-galloyl)glucopyranoside (5). The structures of 1-3 were established by spectroscopic methods. Compounds 1-5 were evaluated for their cytotoxic activities against the MCF-7, H-460, and SF-268 human cancer cell lines.     

草豆蔻的化学成分（英文）

目的：研究草豆蔻的化学成分。方法：采用硅胶和Sephadex LH-20柱色谱方法进行化合物的分离和纯化, 根据理化性质和光谱数据鉴定化合物结构。结果：从草豆蔻提取物中分离得到了10个化合物, 经鉴定分别为：1, 7-双苯-5-羟基-4, 6-庚烯-3-酮 （trans, trans-1, 7-diphenyl-5-hydroxy-4, 6-hepten-3-one, 1）, 乔松素 （pinocembrin, 2）, 山姜素 （alpinetin, 3）, 7, 4′-二羟基-5-甲氧基二氢黄酮 （4）, 蜡菊亭（helichrysetin, 5）, 2′, 4′-二羟基-6′-甲氧基二氢查尔酮 （uvangoletin, 6）, （1E, 4Z）-5-hydroxy-1-phenylhexa-1, 4-dien-3-one （7）, katsumadain B（8）, 羊踯躅素I（rhodomollein I, 9）和金色酰胺醇酯（aurantiamide acetate,10）。结论：化合物7为一个新天然产物, 化合物9和10为首次从该属中分离得到。     

Cytotoxic flavonoids from Platymiscium floribundum

Two new isoflavonoids, 7-hydroxy-6,4'-dimethoxy-isoflavonequinone (1) and 2'-hydroxy-6,4',6' ',4' '-tetramethoxy-[7-O-7' ']-bisisoflavone (2), and seven other known flavonoids, 3-hydroxy-9-methoxypterocarpan (medicarpin), 3,10-dihydroxy-9-methoxypterocarpan, 3,9-dimethoxypterocarpan (homopterocarpin) (3), 2,3,9-trimethoxypterocarpan (4), 3,4-dihydroxy-9-methoxypterocarpan (vesticarpan) (5), 2',4,4'-trihydroxychalcone (isoliquiritigenin), and 7,4'-dihydroxyflavanone (liquiritigenin) (6), were isolated from the heartwood of Platymiscium floribundum. The structures of compounds 1 and 2 were established by spectroscopic methods. Compounds 3-6 showed cytotoxic activity when evaluated against five human cancer cell lines in vitro.     

Filiasparosides A-D, cytotoxic steroidal saponins from the roots of Asparagus filicinus

Four new steroidal saponins, filiasparosides A-D (1-4), together with known aspafiliosides A (5) and B (6) were isolated from the roots of Asparagus filicinus. The structures of these new compounds were elucidated by detailed spectroscopic study and chemical analysis. Compounds 1-6 were cytotoxic against human lung carcinoma (A549) and breast adenocarcinoma (MCF-7) tumor cell lines with EC(50) values of 2.3-16.8 microg/mL. Compound 3 showed the most potent cytotoxicity, with EC(50) values of 2.3 and 3.0 microg/mL toward A549 and MCF-7 cell lines, respectively.     

Cytotoxic activity of 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol from Eulophia nuda against human cancer cells

Ethnopharmacological relevance

Eulophia nuda L. (Orchidaceae) is a medicinally important terrestrial orchid used for the treatment of tumours and various health problems by the local healers throughout the Western Ghats region in Maharashtra (India).

Aim of the study

To isolate the active molecule from Eulophia nuda and to study its cytotoxic potential against human cancer cells.

Materials and methods

The crude methanolic extract of Eulophia nuda tubers was fractionated by stepwise gradient of the solvents—chloroform–methanol to isolate the pure compound. Isolated pure compound was assessed for its cytotoxic potential against human breast cancer cell lines, MCF-7 and MDA-MB-231 using MTT assay. Structure elucidation of the isolated active compound was carried out by extensive spectroscopic analysis including ¹H NMR, ¹³C NMR, NOESY, COSY, LC–MS and IR.

Results

The isolated active molecule was identified as phenanthrene derivative 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol. This compound showed good antiproliferative activity against human breast cancer cell lines MCF-7 (91%) and MDA-MB-231 (85%) at 1000 μg/ml concentration.

Conclusion

9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol from Eulophia nuda tubers showed good growth suppressive effect against human cancer cell lines MCF-7 and MDA-MB-231 making it a potential biomolecule against human cancer.     

云南豆腐柴的化学成分研究

目的 研究产自云南省的豆腐柴的化学成分.方法 将云南豆腐柴地上部分粉碎后用95％的乙醇提取,所得浸膏分别以石油醚和乙酸乙酯萃取,乙酸乙酯部分经硅胶柱和RP-18柱色谱技术进行分离纯化,运用波谱法对所分离的化合物进行结构解析.结果 从云南豆腐柴中分离得到10个化合物,经波谱分析,鉴定为7-羟基-二氢黄酮(1)、松属素(2)、球松素(3)、3-甲氧基-高良姜素(4)、3,7-二甲氧基-高良姜素(5)、槲皮素3-O-β-D-吡喃木糖苷(6)、2’,4’-二羟基-查儿酮(7)、异甘草素(8)、4-甲氧基-异甘草素(9)、豆蔻素(10).结论 化合物1 ～ 10为首次从云南豆腐柴中分离得到.     

Cytotoxic 4-phenylcoumarins from the leaves of Marila pluricostata

Bioassay-guided fractionation of the CH(2)Cl(2) extract of the leaves of Marila pluricostata led to the isolation of 17 naturally occurring 4-phenylcoumarins, three of them, 5-hydroxy-8,8-dimethyl-4-phenyl-9,10-dihydro-8H-pyrano-[2,3-f]chromen-2-one (1), 5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f]chromen-2-one (2), and 5,7-dihydroxy-8-(3-methylbut-2-enyl)-4-phenylchromen-2-one (3), are new natural compounds; the remaining (4-17) are known mammea-type coumarins. Their structures were established by spectroscopic means. All compounds were tested in cytotoxicity assays against the MCF-7, H-460, and SF-268 human cancer cell lines.     

刮筋板乙酸乙酯部位化学成分

目的:研究刮筋板Excoecaria acerifclia的化学成分和生物活性.方法:采用色谱技术分离纯化,根据化学成分理化性质和波谱数据确定化学结构;MTT法测定化合物对人肝癌细胞系(human hepatocarcinoma cell line)HepG2的体外抑制作用,用半数抑制浓度(IC50)评价其抗肿瘤活性.结果:分离鉴定了8个化合物,分别为6-甲氧基-7-羟基香豆素(1),6,7-二甲氧基-8-羟基香豆素(2),山柰酚(3),山柰酚3-O-吡喃葡萄糖苷(4),槲皮素-3-O-β-D-葡萄糖糖苷(5),山奈酚-3-O-β-D-葡萄糖糖苷-2"-没食子酸酯(6),β-谷甾醇(7),胡萝卜苷(8).生物活性研究显示化合物5和6对人肝癌细胞系HepG 2的IC50分别为7.13,65.42μmol·L-1.结论:所有化合物均为首次从该植物中分得.化合物5具有较好的体外抑制HepG2作用.     

假奓包叶抗菌活性成分的研究(2)

目的:研究假奓包叶的抗菌活性成分.方法:在抗菌药理活性跟踪下,应用多种色谱技术进行化合物分离,运用波谱分析法和化学手段鉴定其结构.结果:从乙醚萃取部位和正丁醇萃取部位共分离得到7个化合物,分别鉴定为5,7-二羟基-4'-甲氧基黄酮(1)、槲皮素(2)、洋芹素-7-O-β-D-葡萄糖苷(3)、洋芹素-7-O-新橙皮苷(4)、木犀草素-7-O-新橙皮苷(5)、没食子酸(6)和β-胡萝卜苷(7).结论:化合物1～6为首次从假爹包叶属植物中得到,并有一定的抑制大肠杆菌的活性;化合物6还具有抑制金黄色葡萄球菌的活性.     

New isoprenylated flavones, artochamins A--E, and cytotoxic principles from Artocarpus chama

Five new isoprenylated flavones, artochamins A-E (1-5), together with eight known flavones (6-13), were isolated from the roots of Artocarpus chama. All structures were elucidated by spectroscopic methods. Artonin E (12) showed strong cytotoxicity against 1A9 (ovarian), significant activity against MCF-7 (breast adenocarcinoma), and moderate activity against HCT-8 (ileocecal) and MDA-MB-231 (breast adenocarcinoma) tumor cell lines. Artochamin C (3) was more potent against MCF-7, 1A9, HCT-8, and SK-MEL-2 (melanoma) than A549 (lung carcinoma), KB (epidermoid carcinoma of the nasopharynx), and its drug-resistant (KB-VIN) variant. Artocarpin (6) displayed weak but relatively broad inhibitory effects compared with 3 and 12.