Brominated Diphenyl Ethers Including a New Tribromoiododiphenyl Ether from the Vietnamese Marine Sponge Arenosclera sp. and Their Antibacterial Activities

A new tribromoiododiphenyl ether ( 1 ) and eight known brominated diphenyl ethers ( 2 – 9 ) were isolated from the MeOH extract of the sponge Arenosclera sp. collected in Vietnam, using repeated open column chromatography and preparative thin layer chromatography. The chemical structure of the new compound 1 was determined by analyses of spectroscopic (1D‐ and 2D‐NMR, and MS) data and by comparison of our data with those reported in the literature. Compounds 1 , 3 , and 8 exhibited strong antibacterial activities against the Gram‐positive bacteria Bacillus subtilis and Staphylococcus aureus and the Gram‐negative bacterium Klebsiella pneumoniae with MIC values ranging from 0.8 to 6.3 μm , while compounds 5 and 7 only displayed activities against Gram‐positive bacteria with MIC values from 0.5 to 3.1 μm . Compound 2 showed activities against the four tested bacteria with MIC values ranging from 0.5 to 6.3 μm .     

鸦胆子化学成分及肿瘤细胞毒活性研究(英文)

从鸦胆子(Brucea javanica)种子的甲醇提取物中分离和鉴别得到11个化合物,经波谱数据分析分别鉴定为鸦胆子内酯A(1),鸦胆子素D(2),鸦胆子苷A(3),C(4),F(5),G(6),L(7),3β-羟基-孕甾-5-烯-20-酮(8),3β-羟基-5α-孕甾-20-酮(9),3-O-β-D-吡喃葡萄糖基-(1→2)-α-L-吡喃阿拉伯糖基-(20R)-孕甾-5-烯-3β,20-二醇(10)和6,22-二烯-3β-羟基5,8-过氧麦角甾(11)。其中化合物8、9和11为首次从该植物中分离得到。鸦胆子内酯A(1)和鸦胆子素D(2)对人类癌细胞株BGC-823,Huh-7,KE-97和Jurkat具有很好的细胞毒作用。     

海洋链霉菌S09的化学成分研究(英文)

从海洋链霉菌S09的发酵液提取物中分离得到6个化合物,通过波谱技术分别鉴定为:thymidine(1)、尿嘧啶(2)、3-甲基-2,5-哌嗪二酮(3)、2-吡咯甲酸(4)、卡拉霉素(5)和β-咔啉(6)。海虾致死实验结果显示:化合物5在10μg/mL的浓度下对丰年虾的致死率为87.6%,显示出较强的细胞毒活性。     

南海软海绵Halichondria sp.化学成分研究

为了寻找有生物活性的次生代谢产物,对从采集自中国南海的软海绵(Halichondria sp.)进行了化学成分研究,从中共分离得到了9个化合物,并对部分化合物进行了抗菌活性测试。根据现代波谱技术并结合文献数据,鉴定化合物的结构为:1,2,3,4-四氢-3-羧基-2-卡波林(1),色氨酸(2),环(异亮氨酸-脯氨酸)(3),开环(脯氨酸-缬氨酸)(4),环(丙氨酸-脯氨酸)(5),胆甾醇(6),二-(2-乙基己基)邻苯二甲酸酯(7),邻苯二甲酸正丁异丁酯(8)和邻苯二甲酸二异丁酯(9)。     

掘海绵属海绵的化学成分研究概述

到目前为止,已从掘海绵属中分离得到200多种化合物,主要特征化学成分为萜类,多卤代化合物,甾醇等物质;本文按照化合物结构类型进行了归纳,综述了该类海绵中化学成分并简述了它们的药理作用.     

Chemical Constituents of Primulina eburnea (Gesneriaceae) and Their Cytotoxic Activities

Two new ursane-type triterpenes, eburnealactones A and B ( 1 and 2 ), one new flavonoid, eburneatin A ( 6 ), and one new phenylethanoid glycoside, chiritoside D ( 7 ), along with 9 known compounds ( 3–5 , 8–13 ) were isolated from the whole plant of Primulina eburnea. Their structures were elucidated by comprehensive spectroscopic data analysis (IR, UV, NMR, and HR-ESI-MS). All the compounds were evaluated for their cytotoxic activities. Compound 1 showed significant cytotoxic activities against MKN-45 cell lines and 5637 cell lines with the IC₅₀ values of 9.57 μM and 8.30 μM, respectively. Compound 1 exhibited moderate cytotoxic activities against A549 and PATU8988T cell lines with the IC₅₀ values of 30.70 μM and 38.22 μM, respectively. Compound 6 exhibited moderate cytotoxic activities against MKN-45, HCT116, PATU8988T, 5637 and A-673 cell lines with the IC₅₀ values of 19.69 μM, 16.44 μM, 18.07 μM, 11.51 μM and 18.15 μM, respectively. Compound 5 showed moderate cytotoxic activities against A549 cell lines with the IC₅₀ values of 24.06 μM.     

Chemical Constituents of Crinum asiaticum L. var. sinicum Baker and Their Cytotoxic Activities

A phytochemical investigation of the bulbs of Crinum asiaticum L. var. sinicum Baker resulted in the isolation of two new alkaloids, asiaticumines A and B ( 1 and 2 , resp.), together with 21 known compounds, including nine alkaloids, four amides, five phenolic compounds, and three flavonoids. All 23 compounds were isolated for the first time from Crinum asiaticum L. var. sinicum Baker . Their structures were elucidated by spectroscopic methods. In addition, ten alkaloids, 1 – 10 , were evaluated for their cytotoxic activities against human tumor cell lines A549, LOVO, HL‐60, and 6T‐CEM. Compounds 3, 4 , and 7 – 10 selectively showed remarkable inhibition against one or more of the tested cell lines.     

海绵共附生疣孢菌FIM06031细胞毒活性代谢产物的研究

利用正相硅胶、葡聚糖凝胶Sephadex LH-20和反相C18柱层析等方法,从海绵共附生疣孢菌FIM06031的发酵菌丝体提取液中分离到三个化合物(1～3)。通过波谱方法鉴定其中一个化合物harrucomicin C(1)为新倍半萜,另外两个已知化合物为cyperusol C(2)和Nb-乙酰色胺(3)。活性研究表明harrucomicin C对肿瘤细胞株HepG2、EC109和HeLa具显著增殖抑制活性,其IC50值分别为16.99、25.33μM和34.64μM;cyperusol C对肿瘤细胞HeLa和HepG2增殖抑制作用的IC50值分别为149.99μM和167.78μM。     

Sesquiterpenes from the Leaves of Magnolia delavayi Franch. and Their Cytotoxic Activities

Thirteen sesquiterpenes including eight new ones, magnodelavins A?H ( 1 – 8 ), were obtained from the 95 % ethanolic extract of the leaves of Magnolia delavayi Franch . The structures of the new compounds were determined by exhaustive ¹H‐, ¹³C‐, 2D‐NMR, UV, IR, and HR‐ESI‐MS data, as well as X‐ray crystallographic analysis. Compounds 9 and 10 showed potent cytotoxic activities against HL‐60, A‐549, SMMC‐7721, MCF‐7, and SW480 human cancer cell lines in vitro using MTS assay.     

Melanogenesis‐Inhibitory and Cytotoxic Activities of Chemical Constituents from the Leaves of Sauropus androgynus L. Merr. (Euphorbiaceae)

A new steroid, 20‐hydroxyisofucosterol (stigmasta‐5,24(28)‐diene‐3β,20β‐diol) ( 7 ), along with six known compounds 1 – 6 were isolated from the MeOH extract of the leaves of Sauropus androgynus L. Merr . (Euphorbiaceae). The structure of new steroid was determined by HR‐APCI‐MS and various NMR techniques in combination with literature data. Subsequently, their anti‐inflammatory, cytotoxic activities against five human cell lines, as well as inhibitory activities against the α‐MSH induced melanogenesis on the B16 cell line were evaluated. As the results, steroid compounds, 6 and 7 exhibited moderate cytotoxic to HL60, AZ521, SKBR3, and A549 tumor cell lines (IC₅₀ 26.9 – 45.1 μm ) with high tumor selectivity for A549 relative to WI38 cell lines (SI 2.6 and 3.0, resp.). And, flavonoid compounds, 4 and 5 exhibited superior inhibitory activities against melanogenesis (67.0 – 94.7% melanin content), even with no or low toxicity to the cells (90.1 – 99.6% cell viability) at the concentrations from 10 to 100 μm . Furthermore, Western blot analysis suggested that compound 5 could inhibit melanogenesis by suppressing the protein expressions of MITF, TRP‐1, TRP‐2, and tyrosinase.     

桦褐孔菌的化学成分及抗炎活性

本实验研究了桦褐孔菌的化学成分及其抗炎活性。方法是采用溶剂法和柱色谱法提取分离桦褐孔菌的化学成分,根据化合物的理化性质及核磁共振氢谱、碳谱、质谱对其化学结构进行鉴定,然后采用二甲苯致小鼠耳肿胀和二甲苯致小鼠腹膜炎模型对所得化合物的抗炎活性进行考察。最终从桦褐孔菌的乙醇提取物中分离得到3个羊毛脂烷型三萜类化合物,分别鉴定为羊毛甾醇(1)、inotodiol(2)和trametenolic acid(3)。化合物1、2、3在10 mg/kg均显著抑制二甲苯致小鼠耳肿胀,化合物1和2在10 mg/kg时显著降低血管通透性。由此得出化合物1～3均有抗炎活性,其中trametenolic acid(3)的抗炎活性最强。     

Chemical Constituents of Dactylicapnos torulosa and Their Antithrombotic Activities

Dactylicapnos torulosa (D. torulosa) has been traditionally used as a therapeutic remedy. Here, a combined strategy using both phytochemical and biological approaches was conducted to discern the effective components of D. torulosa. Three new alkaloids, namely, (1–3), Torulosine A, 1-Methoxypseudoprotopine and 1,14-Dimethoxyprechilenine together with 33 (4–36) known compounds were isolated. The structures of the new compounds were fully established by extensive analysis of HR-ESI-MS NMR and CD spectroscopic data. These compounds were then screened using zebrafish bioassay methods for antithrombotic activities. Compounds 5 and 7 had the best antithrombotic effect with prevention rates of 100% at 50 μM, and Compounds 8, 4, 9 and 11 at 50 μM had prevention rates of 81.3%, 79.4%, 84.4% and 79.3%, respectively. The antithrombotic effect of compounds may be related to their inhibitory effect on platelet aggregation. The present study contributes to the diverse chemical and bioactivity data of the Dactylicapnos genus.     

刺孢吸水链霉菌发酵液的化学成分及抗炎活性研究

研究一株刺孢吸水链霉菌(Streptosporangium hygroscopicus n.sp.)发酵液的化学成分及其抗炎活性。应用多种色谱方法进行分离和纯化,并用NMR、IR和MS等方法解析其结构;然后采用叉菜胶所致大鼠足趾肿胀模型对所得化合物的抗炎活性进行了考察。最终从刺孢吸水链霉菌代谢产物中分离得到5个单体化合物,它们的结构分别为芒柄花素(1),N-乙酰基-2-(4-羟苯基)乙胺(2),阿魏酸(3),3,4,5-三甲基-1,2-苯二酚(4),7,3’-二羟基-4’-甲氧基黄酮(5)。化合物1、2、4和5在15 mg/(kg·d)时,对交叉菜胶所致大鼠足趾肿胀的抑制率分别为47.3%、16.8%、13.6%和50.4%。化合物1、4和5首次从该菌中分离得到;化合物1和5具有较强的抗炎作用。     

Diastereoselective Sonochemical Synthesis of Spirocyclopropaneoxindoles and Evaluation of Their Antioxidant and Cytotoxic Activities

An efficient diastereoselective synthesis of spirocyclopropaneoxindoles is reported using three‐component reactions of various phenacylidenetriphenylphosphorane, isatins and phenacyl bromide under ultrasonic irradiation. The structures of synthesized spirocyclopropaneoxindoles were characterized by their spectral data. The antioxidant activities of the synthesized compounds were evaluated by 1,1‐diphenyl‐2‐picrylhydrazyl radical scavenging assay. Among the products, those with NH group in their structure exhibited higher antioxidant activities than other derivatives. Also, in vitro cytotoxicity of compounds 4b , 4e , 4j , 4k were examined against heLa cancer cell lines using MTT assay. The results revealed that compound 4j with chlorine substituent on phenyl group displayed higher cytotoxicity activity (IC₅₀=4.50±0.30 μg/mL) after 48 h.     

Essential Oils of Polyalthia suberosa Leaf and Twig and Their Cytotoxic and Antimicrobial Activities

Essential oils from the leaf and twig of Polyalthia suberosa (Roxb.) Thwaites were analyzed using GC/MS/FID. A total of sixty-three constituents were namely identified accounting for 96.03 and 94.12 % in the hydrodistilled oils of the leaf and twig, respectively. Monoterpenes, monoterpenoids, sesquiterpenes, and sesquiterpenoids were characteristic derivatives of P. suberosa essential oils. Sesquiterpenes bicyclogermacrene (26.26 %) and (E)-caryophyllene (7.79 %), and monoterpene β-pinene (12.71 %) were the major constituents of the leaf oil. Sesquiterpenes (E)-caryophyllene (17.17 %) and α-humulene (9.55 %), sesquiterpenoid caryophyllene oxide (9.41 %), and monoterpenes camphene (8.16 %) and tricyclene (6.35 %) were to be main components in the twig oil. The leaf oil indicated cytotoxic activity against three cancer cell lines HepG2, MCF7 and A549 with the IC₅₀ values of 60.96–69.93 μg/mL, while the twig oil inhibited MCF7 with the IC₅₀ value of 66.70 μg/mL. Additionally, the twig oil successfully suppressed the growth of the negative Gram bacterium Pseudomonas aeruginosa, fungus Aspergillus niger, and yeast Candida albicans with the same MIC value of 50 μg/mL, whereas the leaf oil had the same result on the negative Gram bacterium Escherichia coli.     

鸢尾属植物的化学成分及其生物活性

鸢尾科鸢尾属植物的主要化学成分是黄酮类化合物,这类化合物具有广泛的生物活性。本文对近年来该属植物的分布,化学成分的分类及生物活性进行了综述。     

Cytotoxic Spliceostatin Analogs from Pseudomonas sp.

Two new spliceostatin analogs, designed as spliceostatins J and K ( 1 and 2 ), were isolated and identified from the culture of Pseudomonas sp., along with two known ones, FR901464 ( 3 ) and spliceostatin E ( 4 ). Their structures were elucidated by detailed interpretation of their spectroscopic data, especially 2D‐NMR and HR‐ESI‐MS. Spliceostatin J ( 1 ) represented the first example of spliceostatins bearing an unusual hexahydrofuro[3,4‐b]furan moiety. Biological assay showed all the isolated compounds except 1 displayed potent cytotoxic activities against two cancer cell lines (MDA‐MB‐231 and A‐549). Structure‐activity‐relationship studies revealed that the tetrahydropyran ring in spliceostatin analogs was necessary for their bioactive retention.     

Phloroglucinol Derivatives from the Fruits of Eucalyptus globulus and Their Cytotoxic Activities

A new phloroglucinol derivative, named eucalyptin B ( 1 ), along with five related known compounds ( 2 – 6 ), was isolated from the fruits of Eucalyptus globulus. Their structures were elucidated by means of 1D‐ and 2D‐NMR spectroscopy, with the absolute configuration of 1 determined by electronic circular dichroism (ECD) calculations. All isolated compounds ( 1 – 6 ) were evaluated for their cytotoxic activities against lung (A549), breast (4T1), and skin (B16F10) cancer cell lines. On the basis of cell viability assay, the cytotoxic activity of eucalyptin B ( 1 ) was further confirmed by apoptosis assay. Additionally, after treatment with eucalyptin B ( 1 ), the apoptosis factor proteins (Bcl2 and Bax) and caspase‐3 levels in A549 cells were also determined by Western‐blot analysis. By cytotoxic assay, eucalyptin B ( 1 ) exhibited potent cytotoxicity against A549 cells with an IC₅₀ value of 1.51 μm and induced concentration dependent apoptosis of up to 49%. Additionally, eucalyptin B ( 1 ) inhibited 5‐fold and increased 10‐folds in the level of Bcl2 and Bax, respectively. Furthermore, the 11‐fold increase in the level of caspase‐3 confirmed eucalyptin B ( 1 ) activated caspase dependent apoptosis pathway. In conclusion, the isolated compound eucalyptin B ( 1 ) has promising cytotoxic activity in tumor cells, especially in A549.     

没药的化学成分及其生物活性

没药属(Commiphora)植物分泌的胶状树脂作为没药(myrrh)为世界多个国家常用植物药,其所含成分包括萜类、甾体、黄酮、木脂素等次生代谢产物.现代药理研究表明没药提取物和所含的化学成分具有细胞毒、抗细菌、抗真菌、镇痛、抗氧化、抗炎等生物活性.本文综述了国内外没药化学成分和生物活性的研究概况.