Bioactive lignans from Peperomia heyneana

Four new compounds, including three secolignans (1-3) and one tetrahydrofuran lignan (4), were isolated from the petroleum ether and EtOAc fractions of Peperomia heyneana. These compounds were accompanied by eight known secolignans, one known tetrahydrofuran lignan, one known cyclohexenone, and one known amide. The structures were elucidated mainly by 1D and 2D NMR and MS experiments, and the relative configurations by NOE techniques. Five compounds were evaluated for their inhibitory activities against HIV-1 in infected C8166 cells.     

Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum

Bioassay-guided fractionation of the DCM extract from the roots of Endiandra anthropophagorum resulted in the isolation of a new cyclobutane lignan, endiandrin A (1), together with the known natural products nectandrin B (2) and (-)-dihydroguaiaretic acid (3). The structure of 1 was determined by extensive 1D and 2D NMR and MS data analyses. Acetylation and methylation of 1 yielded di-O-acetylendiandrin A (4) and di-O-methylendiandrin A (5), respectively. All compounds were tested in a glucocorticoid receptor binding assay and displayed IC50 values ranging from 0.9 to 35 microM.     

石南藤中木脂素和新木脂素成分的研究

目的:对石南藤的化学成分进行研究.方法:采用各种色谱技术进行分离纯化,并利用理化常数和波谱数据鉴定化合物结构.结果:从石南藤50%乙醇提取物的二氯甲烷萃取部位分离并鉴定了9个化合物,其中包括1个木脂素(-)-gal-belgin(1)和8个新木脂素:玉兰脂B(2),山蒟素D(3),(+)-licarin A(4),海风藤酮(5),南藤素(6),山蒟素C(7),山蒟素B(8),(+)-burchellin(9).结论:化合物1,3,4,8,9为首次从该植物中分离得到.     

小花五味子中抗HIV活性的木脂素类化合物

目的：从小花五味子中发现具有抗HW活性的化学成分。方法：采用多种柱层析分离进行化合物的分离和纯化．通过波谱分析鉴定化合物的结构，化合物的抗HIV-1活性通过对HIV-1感染C8166细胞致细胞病变的抑制试验得到。结果：从小花五味子的茎藤部分分离得到了4个木脂素，分别鉴定为micrantherin A(1)，gomisin K3(2)，gomisin G(3)和vladinol F(4)。化舍物4具有显著的抗HIV-1活性，IC50=3.51μg／mL，选择指数为27、45。结论：化合物1为新的木脂素，化合物4的抗HIV-1活性值得进一步研究。     

Cytotoxic constituents of roots of Chaerophyllum hirsutum

Two new lignan derivatives (1 and 2), along with the known scopoletin (3), methyl caffeate (4), falcarindiol (5), 3,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic methyl ester, chlorogenic acid, p-hydroxyphenylethyl-trans-ferulate, and vanillin, were isolated from extracts of the roots of Chaerophyllum hirsutum. Structure elucidation of the new compounds was carried out by 1D and 2D NMR experiments and by HRMS analysis. Several of the isolated compounds were tested for their cytotoxic activity against the HL-60, HT-1080, LoVo, and LoVo/Doxo cell lines.     

Microbial transformations of aryltetralone and aryltetralin lignans by Cunninghamella echinulata and Beauveria bassiana

Microbiological transformation of the aryltetralone lignan (-)-8'-epi-aristoligone (1) with Cunninghamella echinulata ATCC 10028B afforded two known natural lignans, (-)-holostyligone (3) and (-)-arisantetralone (4). Incubation of the aryltetralin lignan (-)-isogalbulin (2), obtained by chemical transformation of 1, with C. echinulata ATCC 10028B afforded the known lignan aryltetralol (5) and seven new metabolites, (-)-8-hydroxyisogalbulin (6), (-)-7-methoxyisogalbulin (7), (-)-4'-O-demethyl-8-hydroxyisogalbulin (8), (-)-7-methoxy-8-hydroxyisogalbulin (9), (-)-4'-O-demethyl-7-methoxyisogalbulin (10), (-)-4',5-O-didemethylcyclogalgravin (11), and (-)-4'-O-demethylcyclogalgravin (12). When 2 was subjected to biotransformation with Beauveria bassiana ATCC 7159, (-)-8-hydroxyisogalbulin (6) was the only isolable product. The structures of all new compounds were established by detailed analysis of their spectroscopic data.     

Potent cytotoxic lignans from Justicia procumbens and their effects on nitric oxide and tumor necrosis factor-alpha production in mouse macrophages

A new lignan glycoside, 4-O-alpha-L-arabinopyranosyl-(1' "-->2' ')-beta-D-apiofuranosyldiphyllin (2), named procumbenoside A, and 11 known compounds were isolated from the whole plant of Justicia procumbens. The structure of 2 was established by spectral analysis and chemical methods. The known compounds justicidin A (1), diphyllin (3), and tuberculatin (4) showed potent cytotoxic effects against a number of cancer cells in vitro. Compounds 1 and 4 also strongly enhanced tumor-necrosis factor-alpha (TNF-alpha) generation from mouse macrophage-like RAW 264.7 cells stimulated with lipopolysaccharide (LPS).     

Dihydroagarofuranoid sesquiterpenes, a lignan derivative, a benzenoid, and antitubercular constituents from the stem of Microtropis japonica

Four new compounds, including two new dihydroagarofuranoid sesquiterpenes, 8-benzoyloxymutangin (1) and 15-acetoxyorbiculin G (2), a new lignan derivative, 9,9'- O-di-(Z)-feruloyl-(-)-secoisolariciresinol (3), and a new benzenoid, 5'-methoxyevofolin B (4), have been isolated from the stem of Microtropis japonica, together with 20 known compounds (5- 24). 3-Ethoxy-4-hydroxybenzaldehyde (5) was identified from a natural source for the first time. The structures of these new compounds were determined through analyses of physical data. 15-Acetoxyorbiculin G (2), celahin C (6), and salasol A (7) exhibit antituberculosis activities (MICs < or = 39.6 microM) against Mycobacterium tuberculosis H 37Rv in vitro.     

Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell lines

A new monoepoxylignan, dysosmarol (1), along with eight known compounds, podophyllotoxin (2), 4'-demethylpodophyllotoxin (3), deoxypodophyllotoxin (4), 4'-demethyldeoxypodophyllotoxin (5), diphyllin (6), kaempferol, quercetin, and beta-sitosterol, were isolated from the roots of Dysosma versipellis. The structure of 1 was elucidated by spectroscopic methods. Aryltetralin lignans 2-4 showed the most potent inhibitory activities against the growth of androgen-sensitive (LNCaP) and androgen-independent (PC-3) human prostate cancer cell lines, with IC50 values in the ranges 0.030-0.056 and 0.032-0.082 microM, respectively. A quantitative HPLC analysis showed that compound 2 occurred at the highest concentration in the plant (37.21 mg/g) followed by compound 4 (5.01 mg/g) and compound 3 (2.75 mg/g). Furthermore, D. versipellis roots contain a similar content of compound 2 as compared with the rhizomes and roots of Podophyllum hexandrum, a commercial source of the lignan. Thus, cultivation of D. versipellis in suitable locations may serve as an alternative source for podophyllotoxin (2) production.     

Antidiabetic dimeric guianolides and a lignan glycoside from Lactuca indica

Three novel sesquiterpene lactones, lactucain A (1), B (2), and C (3), and a new furofuran lignan, lactucaside (4), were isolated from Lactuca indica along with nine known compounds, 11beta,13-dihydrolactucin, cichoriosides B, quercetin, quercetin 3-O-glucoside, rutin, apigenin, luteolin, luteolin 7-O-glucuronide, and chlorogenic acid. Among these compounds, latucain C (3) and lactucaside (4) showed significant antidiabetic activity.     

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。     

Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae

Eight new compounds, including four new neolignans, (7' S,8' S)-bilagrewin ( 1), (7' S,8' S)-5-demethoxybilagrewin ( 2), (7' S,8' S)-5- O-demethyl-4'- O-methylbilagrewin ( 3), and (7' S,8' S)-nocomtal ( 4), a new coumarinolignan, (7' S,8' S)-4'- O-methylcleomiscosin D ( 5), two new lignan derivatives, (+)-9'- O-( Z)-feruloyl-5,5'-dimethoxylariciresinol ( 6) and (+)-9'- O-( E)-feruloyl-5,5'-dimethoxylariciresinol ( 7), and a new chromene, ( E)-3-(2,2-dimethyl-2 H-chromen-6-yl)prop-2-enal ( 8), have been isolated from the stem wood of Zanthoxylum avicennae, together with 18 known compounds ( 9- 26). The structures of these new compounds were determined through spectroscopic and MS analyses. (7' S,8' S)-4'- O-Methylcleomiscosin D ( 5), cleomiscosin D ( 9), skimmianine ( 18), robustine ( 19), and integrifoliolin ( 23) exhibited inhibition (IC 50 < or = 18.19 microM) of superoxide anion generation by human neutrophils in response to formyl- l-methionyl- l-leucyl- l-phenylalanine/cytochalasin B (FMLP/CB). In addition, skimmianine ( 18) inhibited FMLP/CB-induced elastase release with an IC 50 value of 19.15 +/- 0.66 microM.     

Cytotoxic and other compounds from Didymochlaena truncatula from the Madagascar rain forest

Bioassay-guided fractionation of the EtOH extracts obtained from a plant identified as Didymochlaena truncatula led to the isolation of two cytotoxic alkaloids, camptothecin and 9-methoxycamptothecin. A second plant collection yielded three lignan derivatives, didymochlaenone A (1), didymochlaenone B (2), and (-)-wikstromol, one stilbene, (E)-3-methoxy-5-hydroxystilbene, and two stigmasterol derivatives, stigmast-4-en-3beta-ol and stigmast-4-en-3-one, but no camptothecins, and it is probable that a coding error led to a mistaken identification of the original extract. The structures of the new compounds 1 and 2 were established on the basis of extensive interpretation of one- and two-dimensional NMR spectroscopic data.     

油丹化学成分的研究

从油丹Ａｌｓｅｏｄａｐｈｎｅ ｈａｉｎａｎｅｎｓｉｓ Ｍｅｒｒ,树皮中分离得到４个化合物,根据ＨＲ－ＳＩＭＳ、＾１ＨＮＭＲ、＾１３ＣＮＭＲ及二维核磁共振技术鉴定其结构分别为：一个木脂素ｅｕｓｉｄｅｒｉｎ Ａ「７Ｒ,８Ｒ）－３,４,５,３’－四甲氧基－△＾８’,９’－８－Ｏ－４‘,７－Ｏ－５’木脂素」（Ⅰ）;两个苄基异喹啉类生物碱（６,７－二甲氧基异喹啉基）－（４’－甲氧基苯基）甲酮（Ⅱ）、（６,７     

高效液相色谱法测定滇白珠木脂素甙的含量

目的：测定滇白珠根中木脂素甙的含量。方法：甲醇超声提取,聚酰胺处理制备样品液,C₁₈柱,甲醇-水为流动相。结果：建立了测定４种化学成分的流动相梯度程序和相应的保留时间。结论：可用于滇白珠根中４种木脂素甙的定量分析。     

Aglacins A-D, first representatives of a new class of aryltetralin cyclic ether lignans from Aglaia cordata.

Four new metabolites, aglacins A-D (1-4), were identified from the methanol extract of the stem bark of Aglaia cordata. These compounds represent a new class of aryltetralin cyclic ether lignan. The structure of aglacin A (1) including the absolute configuration was elucidated by interpretation of spectral data, X-ray crystal structure determination, and employing the modified Mosher's method. In addition, three other derivatives, aglacins B-D (2-4), were isolated and identified by spectral means.     

Lignan derivatives and a norditerpene from the seeds of Vitex negundo

A new phenyldihydronaphthalene-type lignan, vitedoin A (1), a new phenylnaphthalene-type lignan alkaloid, vitedoamine A (2), and a new trinorlabdane-type diterpene, vitedoin B (3), were isolated from the seeds of Vitex negundo along with five known lignan derivatives (4-8). Their chemical structures were determined mainly on the basis of NMR and MS data. Compounds 1, 2, and 4-7 showed stronger antioxidative activity than alpha-tocopherol using the ferric thiocyanate method. Compounds 1, 2, and 4-7 showed higher radical-scavenging effect on the stable free radical, 1,1-diphenyl-2-picrylhydrazyl, than L-cysteine.     

Low-density lipoprotein-antioxidant constituents of Saururus chinensis.

A new diarylbutane lignan, saururin A (1), and a known 8-O-4'-type neolignan, machilin D (2), were isolated from a total methanol extract of the underground parts of Saururus chinensis. The structures of 1 and 2 were elucidated by spectroscopic data analysis. Compounds 1, 2, and virolin (3) (the methyl ether of 2) exhibited significant low-density lipoprotein (LDL)-antioxidant activity in the thiobarbituric acid-reactive substance (TBARS) assay with IC(50) values of 8.5, 2.9, and 4.3 microM, respectively.     

Constituents of Boronia pinnata

A novel quinolone, pinolinone (1); seven new phenylpropanoids, boropinols A (2), B (3), C (4), boropinals A (5), B (6), C (7), and boropinic acid (8); and a new lignan, boropinan (9), were isolated from the roots of Boronia pinnata, and their structures were elucidated by NMR and MS analyses. In a search for novel cancer chemopreventive agents (antitumor-promoters), we screened 10 compounds isolated from the plant for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. Boropinic acid (8) and 4'-hydroxy-3'-prenylcinnamaldehyde were observed to significantly inhibit the EBV-EA activation.     

New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica

A new furofuran lignan, styraxlignolide B (1), and four new dibenzyl-gamma-butyrolactone lignans, styraxlignolides C-F (2-5), were isolated from the EtOAc-soluble fraction of stem bark of Styrax japonica. Known compounds, taraxerol (6), syringin (7), and (-)-pinoresinol glucoside (8), were also obtained. The structures of styraxligonolides B-F were determined as 2alpha-(4'-hydroxy-3'-methoxyphenyl)-6alpha-(3' ',4' '-methylenedioxyphenyl)-8-oxo-3,7-dioxabicyclo[3.3.0]octane 4'-O-(beta-D-glucopyranoside) (1), (2S,3S)-2alpha-(3' '-hydroxy-4' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (2), (2S,3S)-2alpha-(4' '-hydroxy-3' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (3), (2S,3S)-2alpha-(4' '-hydroxy-3' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4' '-O-(beta-D-glucopyranoside) (4), and (2S,3S)-2alpha-(3' ',4' '-dimethoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (5) by spectroscopic means including 2D NMR. Compounds 1-8 were tested in vitro for antioxidant activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Styraxlignolide C (2), styraxlignolide D (3), styraxlignolide E (4), and (-)-pinoresinol glucoside (8) exhibited weak radical-scavenging activity in the DPPH assay, with IC50 values of 380, 278, 194, and 260 microM, respectively.