铁篱巴果中的三萜成分研究

为研究铁篱巴果的化学成分, 利用柱色谱技术进行分离纯化, 得到3个三萜类化合物, 根据理化性质、光谱数据鉴定其结构为: 22S, 23R-环氧-甘遂烷-7-烯-3α, 24, 25-三醇 (1), 21S, 23R-epoxy-21, 24S, 25-trihydroxy- apotirucalla-7-ene-3-one (2), 21R, 23R-epoxy-21-ethoxy-24S, 25-dihydroxy-apotirucalla-7-ene-3-one (3)。化合物1为新化合物, 化合物2和3为首次从该属植物中分离得到。     

桑叶中的黄酮类化合物

为了研究桑叶的化学成分与生物活性之间的相关性, 采用硅胶、Sephadex LH-20、RP-C₁₈等色谱方法分离纯化, 通过核磁共振谱、质谱等波谱分析手段鉴定化合物结构。从长穗桑的95%乙醇提取物中分离到4个Diels-Alder类加合物, 分别鉴定为mulberrofuran F₁ (1)、mulberrofuran F (2)、chalcomoracin (3) 和kuwanon J (4); 2个查耳酮类化合物, 鉴定为morachalcone A (5) 和isobavachalcone (6); 3个黄酮类化合物, 鉴定为 norartocarpetin (7)、kuwanon C (8) 和6-geranylapigenin (9)。化合物1和6为首次从该种植物中分离, 化合物4～5、7～9为首次从桑叶中分离得到, 其中化合物1为新化合物。采用MTT法对化合物1～5进行了抗肿瘤活性筛选, 结果显示化合物1～3对人肿瘤细胞A549、Bel7402、BGC823、HCT-8以及A2780具有抑制作用。     

玉竹中新的高双氢异黄酮

为了研究玉竹的化学成分, 利用各种柱色谱及高压液相色谱等方法进行分离和纯化, 根据理化性质和光谱数据鉴定化合物结构。从玉竹提取物中分离得到9个化合物, 其中3个为新的双氢高异黄酮类化合物, 分别为5,7-dihydroxy-6-methoxyl-8-methyl-3-(2′,4′-dihydroxybenzyl)chroman-4-one (1), 5,7-dihydroxy-6-methyl-3-(2′, 4′-dihydroxybenzyl)-chroman-4-one (2), 5,7-dihydroxy-6-methoxyl-8-methyl-3-(4′-methoxybenzyl)chroman-4-one (3), 其余化合物分别为disporopsin (4), 柯伊利素 (chrysoeriol, 5), 5,4′-dihydroxy-7-methoxy-6-methylflavane (6), N-trans-feruloyltyramine (7), N-trans-feruloyloctopamine (8), (+)-syringaresinol (9)。化合物1～3为未见文献报道的新化合物, 化合物4～9为该植物中首次分离得到。     

丰城鸡血藤异黄酮类化合物的分离鉴定

为建立丰城鸡血藤质量控制方法提供对照品, 对其化学成分进行了研究, 从中分离鉴定了8个化合物, 分别为丰城鸡血藤异黄酮苷F (1), 芒柄花素 (2), 芒柄花苷 (3), 奥刀拉亭7-O-β-D-吡喃葡萄糖苷 (4), 澳白檀苷 (5), 阿夫罗摩辛 (6), 圆荚草双糖苷 (7) 和丰城鸡血藤异黄酮苷B (8)。化合物1为新化合物, 化合物3～5和7为首次从本属植物中分离得到, 2为首次从本植物中分离得到。     

红厚壳叶中口山酮类成分

为了研究红厚壳叶中的酮类成分, 采用多种色谱方法对红厚壳叶95%乙醇提取物进行分离纯化, 从氯仿萃取物中分离得到1个新化合物inophyxanthone A (1) 以及4个已知化合物pancixanthone A (2)、gerontoxanthone B (3)、jacareubin (4) 和pyranojacareubin (5), 其中化合物2为首次从该植物中分离得到, 化合物3为首次从红厚壳属植物中分离得到。经波谱数据分析鉴定inophyxanthone A (1) 的结构为1, 3, 5-三羟基-2-(1, 1-二甲基-烯丙基) 酮。     

大花八角果皮中两个新的倍半萜内酯类化合物

为了研究大花八角的化学成分, 通过硅胶柱色谱等方法进行化合物的分离纯化, 利用色谱和多种波谱技术鉴定化合物结构。从甲醇浸提物的二氯甲烷-乙酸乙酯 (1∶1) 部分和乙酸乙酯部分, 分离得到11个化合物, 其中2个新化合物, 分别命名为6-去氧新大八角素 (6-deoxyneomajucin, 1)、2-氧代-6-去氧新大八角素 (2-oxo-6-deoxyneomajucin, 2), 9个为已知化合物: 6-去氧伪莽草毒素 (3)、伪莽草毒素 (4)、莽草毒素 (5)、伪大八角素 (6)、原儿茶酸 (7)、莽草酸 (8)、莽草酸甲酯 (9)、β-谷甾醇 (10) 和胡萝卜苷 (11)。化合物1和2为新的大八角素型倍半萜内酯类化合物, 其余化合物均为首次从本植物中分离得到。     

番石榴叶中一个新的没食子酰苷类成分

为了研究番石榴叶Psidium guajava L.的化学成分, 用各种柱色谱方法从其乙醇水提取物中分离得到5个具有没食子酰结构的酚酸类化合物, 并采用光谱、质谱及文献对照等方法鉴定其结构, 分别为1-O-(6-O-没食子酰基-β-D-葡萄糖)-1,2-丙二醇 (1)、没食子酸 (2)、鞣花酸 (3)、鞣花酸-4-O-β-D-葡萄糖 (4)、槲皮素-3-O-(6"-没食子酰基) β-D-半乳糖 (5)。化合物4与5为首次在该植物中分离得到, 化合物1为一新的酚酸类化合物。     

芳烷醇哌啶类化合物的合成及抗抑郁活性研究

为寻找新型具有抗抑郁活性的单胺递质再摄取抑制剂, 设计合成了15个芳烷醇哌啶类未见文献报道的新化合物, 结构经¹H NMR及HR-MS分析确证。大鼠脑突触体对5-HT、NA和DA再摄取抑制作用体外活性测试结果表明, 化合物4、5和8对5-HT、NA和DA再摄取抑制作用较强。小鼠强迫游泳实验发现, 化合物4、5和13具有显著的体内抗抑郁效果, 化合物4和5值得进一步研究。     

川楝子中的柠檬苦素成分研究

为研究川楝子的化学成分, 利用硅胶柱色谱及制备型高效液相色谱等方法对川楝子的乙酸乙酯提取物进行分离纯化, 得到3个柠檬苦素类化合物, 根据理化性质及一维和二维核磁共振谱鉴定其结构分别为: 24, 25, 26, 27-tetranorapotirucalla-(apoeupha)-1α-tigloyloxy-3α, 7α-dihydroxyl-12α-acetoxyl-14, 20, 22-trien-21, 23-epoxy-6, 28-epoxy (1)、nimbolinin B (2) 和trichilinin D (3)。其中化合物1为新化合物, 化合物2为首次从川楝子中分离得到。     

Part IV. 环丙沙星C-3羧基衍生物均三唑并噻二嗪及吡唑并均三唑的合成和抗肿瘤活性研究

基于抗菌氟喹诺酮的作用机制, 一个有效的转化其抗菌活性到抗肿瘤活性的修饰途径被进一步发展。用稠杂环均三唑并噻二嗪作为环丙沙星 (CFX) 羧基的生物电子等排体, 设计合成了1-环丙基-6-氟-7-哌嗪-1-基- 3-(6-取代苯基-7H-[1, 2, 4]三唑并[3, 4-b][1, 3, 4]噻二嗪-3-基)-喹啉-4(1H)-酮 (5a～5e) 及相应的N-乙酰稠杂环化合物 (6a～6e)。同时发现, 均三唑并噻二嗪在热醋酐中可发生噻二嗪环的缩环挤出硫反应到相应的三乙酰化吡唑并均三唑新稠环体系 (7a～7e)。用MTT法评价了新稠杂环化合物对L1210、CHO和HL60 3种癌细胞株的体外生长抑制活性。结果表明, 15个供试化合物的活性 (IC₅₀ < 25 μmol·L⁻¹) 均显著高于母体化合物CFX的活性(IC₅₀ > 150 μmol·L⁻¹), 而且活性按7a～7e > 5a～5e > 6a～6e顺序递减。     

糙海参中具有抗真菌活性的三萜皂苷(英文)

为了研究糙海参体内的化学成分,寻找结构新颖具有抗真菌活性的三萜皂苷类成分。应用多种色谱分离技术对糙海参体内的化学成分进行分离纯化,根据化合物的理化性质、波谱数据及化学方法鉴定其结构。分离得到3个三萜皂苷化合物,分别为scabraside A (1)、echinoside A (2) 和holothurin A₁ (3),并对其抗真菌活性进行了研究 (1≤MIC₈₀≤16 μg·mL⁻¹)。化合物1为新的三萜皂苷化合物,化合物2和3为首次从该海参中分离得到,它们均显示显著的抗真菌活性。     

怀槐树皮异黄酮苷类化学成分研究

研究怀槐 (Maackia amurensis) 树皮中的化学成分。利用大孔吸附树脂、硅胶、凝胶和ODS柱色谱等分离技术分离化合物, 根据化合物的理化性质和光谱数据鉴定其结构。从其70%乙醇提取物的正丁醇萃取部分分离得到了13个异黄酮苷类化合物, 分别为4′,6-二甲氧基-异黄酮-7-O-β-D-葡萄糖-(1→6)-β-D-吡喃葡糖苷 (1), 樱黄素- 4′-O-β-D-葡萄糖-(1→6)-β-D-吡喃葡糖苷 (2), 芒柄花苷 (3), 黄豆素苷 (4), 染料木苷 (5), saikoisoflavonoside A (6), 阿夫罗摩辛-7-O-β-D-吡喃葡糖苷 (7), 阿夫罗摩辛-7-O-β-D-木糖-(1→6)-β-D-吡喃葡糖苷 (8), 4′-甲氧基-异黄酮- 7-O-β-D-木糖-(1→6)-β-D-吡喃葡糖苷 (9), 4′,6-二甲氧基-异黄酮-7-O-β-D-芹糖-(1→6)-β-D-吡喃葡糖苷 (10), 鸢尾种苷 (11), 5-羟基-4′-甲氧基-异黄酮-7-O-β-D-葡萄糖-(1→6)-β-D-吡喃葡糖苷 (12) 和4′-甲氧基-异黄酮-7-O-β-D-芹糖-(1→6)-β-D-吡喃葡糖苷 (13)。化合物1为新化合物, 命名为怀槐异黄酮苷(maackiaisoflavonoside), 化合物2, 8, 9, 10, 12和13为该属内首次分离得到。     

Oleanane triterpenoids from Akebiae Caulis exhibit inhibitory effects on Aβ42 induced fibrillogenesis

Previous phytochemical investigations of Akebiae Caulis resulted in the isolation of triterpenes, triterpene glycosides, phenylethanoid glycosides and megastigmane glycoside. Amyloid beta (Aβ), the main component of the senile plaques detected in Alzheimer’s disease, induces cell death. However, only a limited number of studies have addressed the biological and pharmacological effects of Akebiae Caulis. In particular, the inhibitory activity of Akebiae Caulis against Aβ42 fibrillogenesis remains unclear. Herein, a new triterpene glycoside, akequintoside F (1), along with nine known compounds pulsatilla saponin A (2), collinsonidin (3), akebonic acid (4), hederagenin (5), 1-(3′,4′-dihydroxycinnamoyl) cyclopentane-2,3-diol (6), asperosaponin C (7), leontoside A (8), quinatic acid (9), and quinatoside A (10) were isolated from Akebiae Caulis using repeated column chromatography with silica gel, LiChroprep RP-18, and MCI gel. The chemical structures of compounds 1–10 were illustrated based on 1D and 2D NMR spectroscopy, including ¹H-¹H COSY, HSQC, HMBC and NOESY spectroscopic analyses. Compound 1 a novel compound and known compounds 6 and 7 were isolated for the first time from this plant. Among these compounds, 1, 3, 4, 5 and 7 displayed significant inhibitory effects on Aβ42 induced fibrillogenesis. We present the first report of new compound 1 and the inhibitory effects of components from Akebiae Caulis on Aβ42 fibrillogenesis.     

Antioxidant and α-glucosidase inhibitory compounds from Pimpinella candolleana Wight et Arn.

EtOAc and MeOH different extracts of Pimpinella candolleana Wight et Arn. have shown the α-glucosidase inhibitory and antioxidant activities when they were assayed in vitro. Chemical constituents of both extracts were isolated by column chromatography, and identified by MS and NMR spectroscopic data. Nine compounds were isolated, including 3 sterols, 2 flavones, 1 triterpene, 1 glucoside, 1 phenol derivatives, and 1 other compound. Their structures were identified as ursolic acid (1), luteolin (2), urea (3), stigmasta-5,22-dien-3-ol acetate (4), erythrol (5), isovitexin (6), 1-(4-hydroxyphenyl)-1,2-ethanediol (7), daucosterol (8), and β-sitosterol (9). Compound 1 (IC₅₀?=?4.42?μg?ml^?1), 2 (IC₅₀?=?5.96?μg?ml^?1), 4 (IC₅₀?=?67.43?μg?ml^?1) and 6 (IC₅₀?=?68.71?μg?ml^?1) showed α-glucosidase inhibitory activity. Compound 2 (IC₅₀?=?0.99?μg?ml^?1) had antioxidant activity. All compounds except for 1 and 9 were isolated from this genus for the first time.     

Triterpenoid saponins from <Emphasis Type="Italic">Clinopodium chinense</Emphasis> (Benth.) O. Kuntze and their biological activity

Four new ursane-type triterpenoid saponins, clinopoursaponins A–D (1–4), six new oleanane-type triterpenoid saponins, clinopodiside VII–XII (5–10), as well as eight known triterpene analogues (11–18), were isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze. The structures of the new compounds were determined based on extensive spectral analyses, including 1D (¹H and ¹³C) and 2D NMR experiments (COSY, NOESY, HSQC, 2D TOCSY, HSQC-TOCSY and HMBC), HR-ESI-MS and chemical methods. Compounds 1–18 were evaluated for their protective effects against anoxia/reoxygenation-induced apoptosis in H9c2 cells and cytotoxicities against murine mammary carcinoma cell line 4T1. Compounds 8, 9 and 18 exhibited significant protective effects, while compound 1 exhibited cytotoxic activity with IC₅₀ value of 7.4 μm compared to 7.6 μm for the positive control 10-hydroxycamptothecin.     

Iridoid glucosides from Wendlandia ligustroides (Boiss. &Hohen.) Blakelock

Eight iridoid glucosides were reported from the aerial parts of Wendlandia ligustroides. 10-deoxygeniposidic acid (1), 7-deoxygardoside (2), geniposidic acid (3), 7-deoxy-8-epi-loganic acid (4), deacetyl-daphylloside (5), scandoside methyl ester (6), 6-O-methyl-deacetyl-daphylloside (7), 6-O-methyl-scandoside methyl ester (8). Compounds 3 – 8 were isolated as a pure form while 1 and 2 as a mixture. The structures of the compounds 1 – 8 were established by spectroscopic methods including 1D-NMR (¹H NMR, ¹³C NMR, DEPT-135), 2D-NMR (COSY, NOESY, HSQC, HMBC) and HRMS.     

Isolates of Alpinia officinarum Hance as COX-2 inhibitors: Evidence from anti-inflammatory,antioxidant and molecular docking studies

BackgroundInflammation triggered by oxidative stress can cause various ailments, such as cancer, rheumatoid arthritis, asthma, diabetes etc. In the last few years, there has been a renewed interest in studying the antioxidant and anti-inflammatory action of plant constituents such as flavonoids and diarylheptanoids.AimTo evaluate the antioxidant, anti-inflammatory activity and the total phenolic content of isolated compounds from Alpinia officinarum rhizomes. Furthermore, molecular docking was performed to study the binding mode of these compounds into the active site of cyclooxygenase-2 (COX-2).MethodsA. officinarum rhizomes were extracted by maceration, using methanol. This extract was further fractionated by partitioning with hexane, chloroform and ethyl acetate and these fractions on further purification resulted in isolation of five pure compounds. Characterization was carried out by using ¹H NMR, ¹³C NMR and MS. They were further evaluated for antioxidant and anti-inflammatory activity using carrageenan-induced paw edema model in rats. Molecular docking study was performed using Glide module integrated in Schrodinger molecular modeling software.ResultsThe compounds were identified as 1,7-diphenylhept-4-en-3-one (1), 5-hydroxy-1,7-diphenyl-3-heptanone (2), 3,5,7-trihydroxyflavone (Galangin, 3), 3,5,7-trihydroxy-4′-methoxyflavone (Kaempferide, 4) and 5-hydroxy-7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3-heptanone (5). The compound-3 and compound-5 (10 mg/kg) showed significant (p < 0.001) antioxidant and anti-inflammatory potential. Moreover, total phenolic content was detected as 72.96 mg and 51.18 mg gallic acid equivalent respectively. All the five isolates were found to be good binders with COX-2 (average docking score − 9.03).ConclusionsGalangin and 5-hydroxy-7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3-heptanone exhibited anti-inflammatory and in-vitro antioxidant activity which may be due to presence of phenolic content in it. The molecular docking study revealed that these compounds have affinity towards COX-2 active site which can further be explored as selective COX-2 inhibitors. The results obtained in this work justify the use of A. officinarum in the treatment of inflammatory disorders like rheumatoid arthritis and inflammatory bowel diseases.     

Structural identification and characterization of potential degradants of zotarolimus on zotarolimus-coated drug-eluting stents

Identification and characterization of unknown zotarolimus impurities on zotarolimus-coated drug-eluting stents is an important aspect of product development since the presence of impurities can have a significant impact on quality and safety of the drug product. Four zotarolimus degradation products have been characterized by LC/UV/PDA, LC/MS, LC/MS/MS and NMR techniques in this work. Zotarolimus drug substance and zotarolimus-coated stents were subjected to degradation under heat, humidity, acid or base conditions. The HPLC separation was achieved on a Zorbax Eclipse XDB-C8 column using gradient elution and UV detection at 278 nm. All four impurities generated through the degradation were initially analyzed by LC/MS and/or LC/MS/MS for structural information. Then the isolation of these degradants was carried out by semi-preparative HPLC method followed by freeze-drying of the collected fractions. Finally the degradants were studied by ¹H and ¹³C NMR spectrometry. Based on LC/MS, ¹H NMR and ¹³C NMR data, the structures of these impurities were proposed and characterized as zotarolimus ring-opened isomer (1), zotarolimus hydrolysis product, 16-O-desmethyl ring-opened isomer (2) and zotarolimus lower fragment (3). Degradants 1, 2 and 3 have been observed on degraded zotarolimus-coated stent products.