Adjacent Hydroxyphenol Compounds and Their Anticomplementary Activities from the Fruits of Berberis atrocarpa

Chemistry of Natural Compounds -     

HESI-MS/MS Analysis of Phenolic Compounds from Calendula aegyptiaca Fruits Extracts and Evaluation of Their Antioxidant Activities

Considering medicinal plants as an inexhaustible source of active ingredients that may be easily isolated using simple and inexpensive techniques, phytotherapy is becoming increasingly popular. Various experimental approaches and analytical methods have been used to demonstrate that the genus Calendula (Asteraceae) has a particular richness in active ingredients, especially phenolic compounds, which justifies the growing interest in scientific studies on this genus’ species. From a chemical and biological viewpoint, Calendula aegyptiaca is a little-studied plant. For the first time, high-performance liquid chromatography combined with negative electrospray ionization mass spectrometry (HPLC-HESI-MS) was used to analyze methanolic extracts of Calendula aegyptiaca (C. aegyptiaca) fruits. Thirty-five molecules were identified. Flavonoids (47.87%), phenolic acids (5.18%), and saponins (6.47%) formed the majority of these chemicals. Rutin, caffeic acid hexoside, and Soyasaponin βg’ were the most abundant molecules in the fruit methanolic extract, accounting for 17.49% of total flavonoids, 2.32 % of total phenolic acids, and 0.95% of total saponins, respectively. The antioxidant activity of the fruit extracts of C. aegyptiaca was investigated using FRAP, TAC, and DPPH as well as flavonoids and total phenols content. Because the phenolic components were more extractable using polar solvents, the antioxidant activity of the methanolic extract was found to be higher than that of the dichloromethane and hexane extracts. The IC50 value for DPPH of methanolic extract was found to be 0.041 mg·mL⁻¹. Our findings showed that C. aegyptiaca is an important source of physiologically active compounds.     

Phenolic Derivatives from Fruits of Dipteryx lacunifera Ducke and Evaluation of Their Antiradical Activities

The fruits of Dipteryx lacunifera, known as ‘fava de morcego’ and ‘garampara’, comprise pleasant tasting kernels that contain high amounts of fatty acids (mainly oleic acid) and are commonly consumed by inhabitants of the northeast of Brazil. In the present study, the crude EtOH extract of the fruit kernels was separated into hexane‐, Et₂O‐, AcOEt‐, and H₂O‐soluble fractions. The Et₂O fraction was found to exhibit the highest 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) radical‐scavenging activity in vitro, and was subjected to further fractionation. Column chromatography over silica gel and Sephadex LH‐20, followed by preparative HPLC‐C₁₈, afforded (?)‐eriodictyol ( 1 ), (?)‐butin ( 2 ), luteolin ( 3 ), 3′,4′,7‐trihydroxyflavone ( 4 ), butein ( 5 ), and sulfuretin ( 6 ). The antiradical activities of compounds 1, 2, 4 , and 6 , together with the positive controls rutin, butylated hydroxy toluene (BHT), and tert‐butylhydroquinone (TBHQ), were evaluated with the DPPH assay and were found to decrease in the order rutin> 4 > 1 > 6 > 2 >TBHQ>BHT.     

New Compounds from the Roots and Stems of Trigonostemon lii and Their Cytotoxic Activities

A new carboline alkaloid, Trifiline D ( 1 ) and a new degraded diterpenoid, Trigoxyphin X ( 4 ) were isolated from the roots and stems of Trigonostemon lii. Their structures were elucidated by extensive spectroscopic analyses including 1D‐ and 2D‐NMR techniques. Compound 1 exhibited weak inhibitory activity against MCF‐7, A‐549, MGC‐803, and COLO‐205 with IC₅₀ values ranging from 27.4 to 35.4 μm .     

Anticancer Activities of Marine-Derived Phenolic Compounds and Their Derivatives

Since the middle of the last century, marine organisms have been identified as producers of chemically and biologically diverse secondary metabolites which have exerted various biological activities including anticancer, anti-inflammatory, antioxidant, antimicrobial, antifouling and others. This review primarily focuses on the marine phenolic compounds and their derivatives with potent anticancer activity, isolated and/or modified in the last decade. Reports on the elucidation of their structures as well as biosynthetic studies and total synthesis are also covered. Presented phenolic compounds inhibited cancer cells proliferation or migration, at sub-micromolar or nanomolar concentrations (lamellarins D (37), M (38), K (39), aspergiolide B (41), fradimycin B (62), makulavamine J (66), mayamycin (69), N-acetyl-N-demethylmayamycin (70) or norhierridin B (75)). In addition, they exhibited anticancer properties by a diverse biological mechanism including induction of apoptosis or inhibition of cell migration and invasive potential. Finally, phlorotannins 1–7 and bromophenols 12–29 represent the most researched phenolic compounds, of which the former are recognized as protective agents against UVB or gamma radiation-induced skin damages. Finally, phenolic metabolites were assorted into six main classes: phlorotannins, bromophenols, flavonoids, coumarins, terpenophenolics, quinones and hydroquinones. The derivatives that could not be attributed to any of the above-mentioned classes were grouped in a separate class named miscellaneous compounds.     

味觉化合物的构象与活性的关系

味觉化合物的构象与活性的关系许禄,姚喻元（中国科学院长春应用化学研究所应用谱学开放实验室,长春,１３００２２）关键词味觉化合物,分子力学,构象分析分子结构和味觉的相关性是一个非常活跃的研究领域,许多人从不同的侧面进行这方面的研究,并总结出一定的规律［...     

新型苄基氨基甲酸酯类化合物的合成及其抗菌活性

以邻氯苄胺为原料,经6步反应制得中间体2-氯-5-［1-(氧丙炔基亚氨基)乙基］苄基氨基甲酸甲酯（7）;取代芳基肟经氯化后再分别与7经环合反应合成了一系列新型的苄基氨基甲酸酯类化合物（10a~10l）,其结构经¹H NMR表征。初步的抗菌活性测试表明：在用药量为200 mg·L^-1时,大部分化合物对水稻纹枯病显示出较好的抗菌活性,其中10f的抑菌活性最高,抑制率95%。     

新型1,4-二苯并二氮杂酮类衍生物的合成及其抗癌活性

以取代邻硝基苯甲酸为起始原料,与二氯亚砜反应制得邻硝基苯甲酰氯,再与苯胺在碱性条件下反应制得酰胺衍生物(6a~6d);以醋酸钯为催化剂,6a~6d经NBS溴代制得溴代衍生物(7a~7d); 7a~7d依次经N-烷基化反应,还原反应和分子内C-N键环合反应合成了10个新型的1,4-二苯并二氮杂酮类化合物(10a~10j),产率61%~78%,其结构经¹H NMR, ¹³C NMR和HR-MS(ESI)表征。初步体外活性测试结果表明:10a~10j对非小细胞肺癌细胞（A549）,人乳腺癌细胞（MDA-MB-231）和宫颈癌细胞(HeLa)均有抑制作用。其中,10g和10i对A549, 10g对MDA-MB-231, 10h和10i对HeLa的抑制率大于50%。     

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

A series of novel indole Schiff base derivatives (2a–2t) containing a 1,3,4-thiadiazole scaffold modified with a thioether group were synthesized, and their structures were confirmed using FT-IR, ¹H NMR, ¹³C NMR, and HR-MS. In addition, the antifungal activity of synthesized indole derivatives was investigated against Fusarium graminearum (F. graminearum), Fusarium oxysporum (F. oxysporum), Fusarium moniliforme (F. moniliforme), Curvularia lunata (C. lunata), and Phytophthora parasitica var. nicotiana (P. p. var. nicotianae) using the mycelium growth rate method. Among the synthesized indole derivatives, compound 2j showed the highest inhibition rates of 100%, 95.7%, 89%, and 76.5% at a concentration of 500 μg/mL against F. graminearum, F. oxysporum, F. moniliforme, and P. p. var. nicotianae, respectively. Similarly, compounds 2j and 2q exhibited higher inhibition rates of 81.9% and 83.7% at a concentration of 500 μg/mL against C. lunata. In addition, compound 2j has been recognized as a potential compound for further investigation in the field of fungicides.     

新型含醚结构噻唑类化合物的合成及其抑菌活性

根据活性基团拼接原理,以对羟基硫代苯甲酰胺和4,4,4-三氟-2-氯乙酰乙酸乙酯为原料,经环化反应制得中间体2-(4'-羟基)苯基-4-三氟甲基-5-噻唑甲酸乙酯(3);3与取代苄基氯或氯乙酸反应合成了5个新型的含醚结构噻唑类化合物(5a~5e),其结构经1H NMR,ESI-MS和元素分析表征。用离体平皿法考察了5a~5e对小麦赤霉病和纹枯病细菌的抑菌活性。结果表明,5a~5e均有一定的抑制活性。其中2-(4'-间氟苄氧基苯基)-4-三氟甲基噻唑-5-甲酸乙酯5c抑菌活性最好,对小麦赤霉病和纹枯病细菌的抑菌活性分别为37.8%和53.3%。     

新型含硅唑类化合物的合成及其生物活性的研究

新型含硅唑类化合物的合成及其生物活性的研究李文明,陈馥衡（北京农业大学应用化学系,北京,１０００９４）关键词有机硅化合物,唑类化合物,硅烷化,杀菌活性唑类化合物具有较强的生物活性,已作为杀菌剂广泛地应用于医药和农药,近年来,有机硅化合物作为生物活性物...     

Antioxidant,Antibacterial, and Antifungal Activities of the Ethanolic Extract Obtained from Berberis vulgaris Roots and Leaves

This work assessed the phenolic and flavonoid components and their antioxidant, antifungal, and antibacterial effects in the ethanolic extract of barberry leaf and roots. The antibactericidal activity of root and leaf extracts against pathogenic bacteria was tested using agar diffusion and microdilution broth production for the lowest inhibitory concentration (MIC). Berberis vulgaris root and leaf extracts inhibited Staphylococcus aureus ATCC9973, Escherichia coli HB101, Staphylococcus enteritis, and Escherichia coli Cip812. The disc assay technique was used to assess the bactericidal activity of the extracts versus both pathogenic Gram-positive and Gram-negative strains. Hydro alcoholic extract was more effective against bacterial than fungal strains. The results showed that Berberis vulgaris leaf and roots extract had similar antifungal activities. Berberis vulgaris root extract inhibited the mycelial growth of Penicillium verrucosum, Fusarium proliferatum, Aspergillus ochraceous, Aspergillus niger, and Aspergillus flavus. Berberis vulgaris root extract has excellent antioxidant, antibacterial, and antifungal effects. Berberis vulgaris exhibited antimicrobial activity in vitro, and MIC showed that Berberis vulgaris parts efficiently affected pathogens in vitro. In conclusion, both Berberis vulgaris roots and leaves have considerable antibacterial activity and can be used as a source of antibacterial, antioxidant, and bioactive compounds to benefit human health.     

金鸡纳碱类化合物在不对称合成中的应用

综述了近年来金鸡纳碱及其部分衍生物在不对称合成中的应用.参考文献34篇.     

N－亚硝基化合物的结构／致癌活性的三维构效关系研究

用比较力场分析研究了Ｎ－亚硝基化合物的结构与致癌活性的关系，考察了网络结构和探针原子对结果的影响．结果表明，立体效应和静电作用场是描述其致癌活性和进行结构性能关系研究的最重要的结构参数。     

Reactive Organometallic Compounds Obtained from Metallocenes and Related Compounds and Their Synthetic Applications

Progress in the synthesis of organometallic compounds via the partial or total degradation of metallocenes and related compounds under mild reaction conditions is reviewed. These degradation reactions permit highly reactive organo-transition metal complexes to be prepared which can in turn be used in a wide range of synthetic reactions. Examples include catalytic reactions such as the cobalt-catalyzed hydrogenation of benzene and the manganese-catalyzed cyclotrimerization of butadiene as well as stoichiometric syntheses of mono- and polynuclear transition metal complexes, some of which have novel structural features.     

Guaiane Sesquiterpenoids Isolated from the Fruits of Torilis japonica and Their Cytotoxic Activity

Two new guaiane sesquiterpenoids, 11‐(acetyloxy)‐1,8‐dihydroxyguai‐4‐en‐3‐one ( 5 ) and (1α,6β)‐1,6‐dihydroxytorilin ( 6 ), were isolated from the fruits of Torilis japonica (Umbelliferae), along with four known sesquiterpenes, torilin ( 1 ), torilolone ( 2 ), (1β)‐1‐hydroxytorilin ( 3 ), and (1α)‐1‐hydroxytorilin ( 4 ). During the phytochemical investigation, daucosterol, friedelin, and epifriedelanol were also isolated from the plant for the first time. The structures of the new sesquiterpenoids 5 and 6 were determined by comprehensive analyses of MS and NMR spectroscopic data. These isolates were evaluated against human breast cancer cells (MCF‐7) and Lewis lung carcinoma (LLC) cells. Compounds 1, 3 , and 4 exhibited cytotoxic activity against the LLC cells with IC₅₀ values of 31.3, 32.5, and 34.0 μg/ml, respectively. However, no significant cytotoxicity was found against the MCF‐7 cells for any of the compounds tested.     

Preparation of Resorcinarene-Functionalized Gold Nanoparticles and Their Catalytic Activities for Reduction of Aromatic Nitro Compounds

Resorcinarene‐functionalized gold nanoparticles (AuNPs) were prepared conveniently in aqueous solution in the presence of amphiphilic tetramethoxyresorcinarene tetraaminoamide. The obtained AuNPs were characterized and analyzed by UV‐vis, FT‐IR, XRD and TEM, respectively. The results showed that the size of AuNPs and the standard deviations were all decreasing with the increase of resorcinarene concentration. In addition, the catalytic activity of the obtained AuNPs in the reduction of aromatic nitro compounds was also investigated. In aqueous solution the reaction follows a first order kinetics and the size of AuNPs has influence on the rate of reduction.     

Diterpenoids from Blumea balsamifera and Their Anti-Inflammatory Activities

Six new diterpenoids, blusamiferoids A–F (1–6), including four pimarane-type diterpenoids, one rosane-type diterpenoid (3), and one rearranged abietane-type diterpenoid (6), were isolated from the dry aerial parts of Blumea balsamifera. Their structures were characterized by spectroscopic and computational methods. In particular, the structures of 1 and 4 were confirmed by X-ray crystallography. Compounds 5 and 6 were found to dose-dependently inhibit the production of TNF-α, IL-6, and nitrite oxide, and compound 5 also downregulated NF-κB phosphorylation in lipopolysaccharide (LPS)-induced RAW 264.7 cells.