Sesquiterpene compounds from Inula viscosa

Two new compounds, 2,5-dihydroxyisocostic acid and 2,3-dihydroxycostic acid together with three known sesquiterpene compounds, Isocostic acid, Carabrone and Tomentosin, have been isolated from the acetone extract of Inula viscosa (L.) Aiton. The structures of all new compounds were determined by spectroscopic methods, in particular 1D and 2D (1)H- and (13)C-NMR. The (13)C-NMR spectra of Isocostic acid and of Tomentosin are reported here for the first time.     

Four novel insecticidal sesquiterpene esters from Celastrus angulatus

Four new insecticidal sesquiterpene polyol esters with a beta-dihydroagarofuran sesquiterpene skeleton, celangulatin C (1), celangulatin D (2), celangulatin E (3), and celangulatin F (4), and five known compounds 5-9 were isolated from the low-polar toluene extracts of the root bark of Celastrus angulatus by bioassay-guided fractionation. Their chemical structures were elucidated mainly by analyses of MS and NMR spectral data. Celangulatin C, E and F showed LD(50) against Mythimna separata were 280.4, 1656.4 and 210.5 microg mL(-1), respectively.     

Antimicrobial,DPPH scavenging and tyrosinase inhibitory activities of Thymus vulgaris,Helichrysum arenarium and Rosa damascena mill. ethanol extracts by using TLC bioautography and chemical screening methods

Antimicrobial, DPPH scavenging and tyrosinase inhibitory activities of Thymus vulgaris, Helichrysum arenarium and Rosa damascena Mill. ethanol extracts by using TLC bioautography and chemical screening methods. The ethanol extracts of Thymus vulgaris (Tv), Helichrysum arenarium (Ha) and Rosa damascena Mill. (Rm) (red) were screened for their antimicrobial, 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and tyrosinase inhibitory activities. The test microorganisms included bacteria of Escherichia coli (ATCC 25922) and Staphylococcus aureus (ATCC 25923). Thin Layer Chromatography (TLC) - bioautography, disk diffusion and well diffusion methods were used for the antimicrobial activity assays. Rosa damascena Mill. extract was effective against E. coli and all plant extracts showed antimicrobial activity against S. aureus. The phenolic acids in the structure of the extracts were also identified by LC-MS analysis. Human blood agar well diffusion method and TLC-DPPH assays were used to identify the hemolytic and antioxidant activity of plant extracts, respectively, along with 10 compounds including phenolic acids as a standard. Among these compounds, caffeic acid (Rf = 0.68) was detected in all extracts while vanillic acid (Rf = 0.75), and gallic acid (Rf = 0.51) was found in Tv extract. Kojic acid (Rf = 0.36), on the other hand, was detected in Rm extract as a tyrosinase inhibitor. All plant extracts presented tyrosinase inhibitory activities on TLC-bioautography assay.     

New acyclic diterpenic acids from yacon (Smallanthus sonchifolius) leaves

Two new acyclic diterpenoids, smaditerpenic acid E (1a) and F (2a), along with nineteen melampolide-type sesquiterpene lactones, six of them not previously reported in yacon, were isolated from the methylene chloride leaf rinse extract. Their structures were elucidated from 1D and 2D NMR experiments and gas chromatography coupled to mass spectrometry.     

New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens

In bioassay-guided searches for novel bioactive natural products from higher plants of the Egyptian flora, two new eudesmane sesquiterpene derivatives, 3alpha-hydroxyilicic acid methyl ester (1) and 2alpha-hydroxy-4-epi-ilicic acid (2), together with 11 known sesquiterpenes were isolated from bioactive fractions of the active epigeal parts extracts of Dittrichia graveolens (L.) GREUTER (Asteraceae) growing in the coastal regions of northwestern Egypt. Four other known sesquiterpene lactones with different carbon skeletons, named 2alpha-hydroxy-2R-xanthalongin (8), 4-epi-isoinuviscolide (9), 8-epi-helenalin (10), and bigelovin (11), were also isolated for the first time from the same source. The stereochemical structures of the isolated compounds were elucidated on the basis of physical and spectroscopic methods including UV, IR, 1H-, 13C-NMR, distortionless enhancement by polarization transfer, 2D NMR, 1H-1H correlation spectroscopy, 1H-13C heteronuclear single-quantum coherence, 1H-13C heteronuclear multiple-bond connectivity, 1H-1H nuclear Overhauser effect spectroscopy experiments, and high-resolution mass spectrometry, as well as some chemical transformations. The antimicrobial, antiinflammatory, and antipyretic activities of D. graveolens extracts and chromatographic fractions were carried out and the various bioactivities of our findings are discussed.     

Chemical composition, antifungal and antitumor properties of ether extracts of Scapania verrucosa Heeg. and its endophytic fungus Chaetomium fusiforme

An endophytic fungus Chaetomium fusiforme was obtained from a liverwort, Scapania verrucosa. A comparison of the constituents of the ether extracts between S. verrucosa and the C. fusiforme culture was investigated by gas chromatography-mass spectrometry (GC/MS). The yield of ether extract based on dried plant material was 0.6% and 59 compounds were found in S. verrucosa. (+)-Aromadendrene (9.12%), hexadecanoic acid (6.92%), 6-isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol (5.97%), s-tetrachloroethane (5.61%) and acetic acid (5.30%) were found to be the most abundant components among the 49 characterized compounds in S. verrucosa, which represented 84.64% of the total extract. However, the constituents of the cultured endophyte extract contained mainly acetic acid (35.05%), valeric acid, 3-methyl-, methyl ester (21.25%), and butane-2, 3-diol (12.24%). Although the extracts of S. verrucosa and its endophyte showed little chemical composition correlation, both of them demonstrated antifungal and antitumor activities. Furthermore, C. fusiforme has displayed a wider range of antimicrobial and antitumor activities, which were better than the host plant. These results could support the suggestion of endophytes as an alternative of the host for medicinal activity.     

Antibacterial and cytotoxic activities of the sesquiterpene lactones cnicin and onopordopicrin

The antimicrobial and cytotoxic activities of chloroform extracts from the weeds Centaurea tweediei and C. diffusa, and the main sesquiterpene lactones isolated from these species, onopordopicrin and cnicin, respectively, were assayed. Results show that the chloroform extracts from both Centaurea species possess antibacterial activities against a panel of Gram-positive and Gram-negative bacteria. Remarkable antibacterial activity against methicillin-resistant Staphylococcus aureus was also measured. Both the extracts and the purified sesquiterpene lactones show high cytotoxicity against human-derived macrophages. Despite this cytotoxicity, C. diffusa chloroform extract and cnicin are attractive candidates for evaluation as antibiotics in topical preparations against skin-associated pathogens.     

Essential oil composition and antioxidant activities of the various extracts of Tanacetum sonbolii Mozaff. (Asteraceae) from Iran

This study is designed to examine the chemical composition of the essential oil and antioxidant activities of the different extracts of Tanacetum sonbolii Mozaff. from Iran for the first time. The essential oil was isolated by hydrodistillation and its gas chromatography and gas chromatography-mass spectrometry analyses resulted in the identification of 26 components, representing 96.5% of the oil. The major components were characterised to be α-cadinol (35.3%), globulol (20.1%) and 1,8-cineole (8.6%). Antioxidant activities of the various extracts of the plant were determined by two different test systems; 1,1-diphenyl-2-picrylhydrazyl (DPPH) and β-carotene-linoleic acid. Also, their total phenolic and flavonoid contents were determined. DPPH radical-scavenging activities of test samples followed the order water?>?chloroform?>?ethyl acetate?>?butanol?>?BHT?>?methanol. Moreover, the ethyl acetate extract showed better β-carotene bleaching capacity than the other extracts and the amount of total phenolics was very high in ethyl acetate extract.     

纳米ZnO对白僵菌孢子的紫外保护及与孢子的生物相容性

用沉淀法制备经油酸表面修饰的纳米ZnO,测定其紫外吸收性能及对油悬浮剂型白僵菌孢子的抗紫外保护效率;用扫描电子显微镜观察纳米ZnO与孢子的混合状态,通过对含纳米ZnO的白僵菌制剂在贮存期间孢子萌发率差异显著性的分析,确定其与白僵菌孢子的生物相容性.结果表明：制备的纳米ZnO的平均粒径为27nm,其对波长200nm～370nm范围的紫外光具有良好的吸收性能.含纳米ZnO质量分数为1.0%、2.0%和5.0%的油悬浮剂型白僵菌,紫外灯照射8h,对孢子保护效率均大于60%,不含纳米ZnO为9.7％. 纳米ZnO被吸附包覆于孢子表面,屏蔽紫外线,保护孢子免受紫外线的杀伤.含0.5%、1.0%和2.0%纳米ZnO的油悬浮剂型白僵菌制剂室温贮存10个月,其孢子萌发率与不含纳米ZnO的差异不显著;纳米ZnO与白僵菌孢子生物相容性好.油悬浮剂型白僵菌制剂中纳米ZnO的适宜含量为1.0%～2.0%.     

Essential oil composition, antimicrobial and cytotoxic activities of two endemic Stachys cretica subspecies (Lamiaceae) from Turkey

The chemical compositions of the water-distilled essential oil of Stachys cretica ssp. lesbiaca Rech. fil. and S. cretica ssp. trapezuntica Rech. fil. were determined by GC and GC-MS. Altogether 63 compounds were identified. The sesquiterpene hydrocarbon, germacrene D (20.3% and 12.9% respectively) was the main component identified in both oils. Furthermore, ethanol, light petroleum, dichloromethane, ethyl acetate and n-butanol extracts prepared from the aerial parts of the plants were tested for their antimicrobial activities against six bacterial strains and the yeast Candida albicans. The extracts exhibited no antibacterial activity, but the light petroleum and n-butanolic fractions showed low antifungal activities. Crude ethanolic extracts of the two subspecies were tested for their ability to inhibit the growth of HL-60 and Ishikawa human tumor cell lines. The IC50 values were 100 microg/mL for the HL-60 cell line and 200 microg/mL for the Ishikawa cell line.     

In vitro antioxidant activity of the water and ethanol extracts of Forsythia koreana flowers

The antioxidant activities of the water and ethanol extracts of F. koreana flowers were evaluated using DPPH, superoxide anion (?O(-2)), and nitric oxide (?NO) radical scavenging activity assays. The SC(50) values of the water extract of F. koreana on DPPH, ?O(-2) and ?NO were 48.39, 24.36 and 100.21 μg mL(-1), respectively. The SC(50) values of the ethanol extract of F. koreana on the aforesaid free radicals were 57.50, 49.00 and 146.08 μg mL(-1), respectively. Further, the total phenolic contents of both extracts were determined and expressed as milligram gallic acid equivalent (GAE) per gram of extract. The water extract exhibited a higher phenolic content (113.78 mg GAE?g(-1)), while the ethanol extract showed 94.53?mg GAE?g(-1). Our findings demonstrate that the water and ethanol extracts of F. koreana flowers might be potential natural sources of antioxidative additives for use in the food and other allied industries.     

Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia

Three new pseudoguaiane-type sesquiterpenes, dichrocepholides A-C, and two new pseudoguaiane-type sesquiterpene dimers, dichrocepholides D and E, were isolated from the aerial part of Dichrocephala integrifolia. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, the extract and its principal sesquiterpene constituent, parthenin, showed an inhibitory activity on nitric oxide (NO) production and on induction of inducible NO synthase.     

Identification and quantification of two antihepatotoxic coumarinolignoids cleomiscosin A and cleomiscosin B in the seeds of Cleome viscosa using liquid chromatography-tandem mass spectrometry

A sensitive liquid chromatography/electrospray ionization tandem mass spectrometric (LC/ESI-MS/MS) method was developed for the identification and quantification of two antihepatotoxic coumarinolignoids cleomiscosin A and cleomiscosin B in different extracts of the seeds of Cleome viscosa. The separation of cleomiscosin A and cleomiscosin B was achieved on an RP(18) column using a solvent system consisting of a mixture of acetonitrile-methanol (1:2, v/v) and acetonitrile-water-formic acid (5:95:0.3, v/v) as a mobile phase in a gradient elution mode. A multiple-reaction monitoring (MRM) method was developed for quantification of cleomiscosin A and cleomiscosin B in the seed extracts of Cleome viscosa. On the basis of signal-to-noise ratio of 3, the limit of detection in MRM mode for cleomiscosin A and cleomiscosin B were 1.0 and 4.0 ng/mL respectively. The method was validated in terms of linearity, accuracy and precision for 6 days. The method developed was found to be useful for identification and quantification of cleomiscosin A and cleomiscosin B in the different extracts of the seeds of Cleome viscosa.     

In Vitro Antidiabetic and Antioxidant Effects of Different Extracts of Catharanthus roseus and Its Indole Alkaloid,Vindoline

The Catharanthus roseus plant has been used traditionally to treat diabetes mellitus. Scientific evidence supporting the antidiabetic effects of this plant’s active ingredient-vindoline has not been fully evaluated. In this study, extracts of C. roseus and vindoline were tested for antioxidant activities, alpha amylase and alpha glucosidase inhibitory activities and insulin secretory effects in pancreatic RIN-5F cell line cultured in the absence of glucose, at low and high glucose concentrations. The methanolic extract of the plant showed the highest antioxidant activities in addition to the high total polyphenolic content (p < 0.05). The HPLC results exhibited increased concentration of vindoline in the dichloromethane and the ethylacetate extracts. Vindoline showed noticeable antioxidant activity when compared to ascorbic acid at p < 0.05 and significantly improved the in vitro insulin secretion. The intracellular reactive oxygen species formation in glucotoxicity-induced cells was significantly reduced following treatment with vindoline, methanolic and the dichloromethane extracts when compared to the high glucose untreated control (p < 0.05). Plant extracts and vindoline showed weaker inhibitory effects on the activities of carbohydrate metabolizing enzymes when compared to acarbose, which inhibited the activities of the enzymes by 80%. The plant extracts also exhibited weak alpha amylase and alpha glucosidase inhibitory effects.     

Anti-inflammatory and antioxidant activities and constituents of Platostoma africanum P. Beauv

Hexane and dichloromethane extracts of Platostoma africanum P. Beauv., a plant popularly employed in Nigeria in the treatment of rheumatic symptoms, were evaluated for anti-inflammatory and antioxidant activities. Acute inflammatory effects were studied in the egg-albumin-induced rat paw edema. Both extracts produced significant (p < 0.05) and dose-dependent inhibition of the egg-albumin-induced pedal edema with the 400 mg kg(-1) dose being markedly better than piroxicam. The hexane and dichloromethane extracts also showed significant antioxidant activity with the dichloromethane extract exhibiting an IC(50) comparable to that of BHT, a synthetic antioxidant. Phytochemical investigation of the extracts afforded eight acidic pentacyclic triterpenes, namely, ursolic acid, oleanolic acid, epimaslinic acid, maslinic acid, corosolic acid, hyptadienic, euscaphic acid and tomentic acid, and a mixture of beta-sitosterol and stigmasterol. These constituents are reported for the first time in the genus.     

杯菊中的倍半萜内酯

摘要杯菊(Cyathocline purpurea)是云南民间民族药, 全株用于治疗各种炎症和肺结核. 采用L1210细胞系对杯菊的粗提物、 分步萃取物的成分进行了细胞毒试验; 用柱层色谱法同步对活性组分进行化学成分分离纯化; 通过理化数据测定及波谱分析鉴定单体结构. 杯菊的氯仿及乙酸乙酯萃取物具有细胞毒活性, 其IC50分别为3.5和2.8 μg/mL. 从活性组分中分离出3种成分, 分别鉴定为Santamarin(1)、 9β-乙酰基广木香内酯(9β-acetoxycostunolide, 2)和9β-乙酰基小白菊内酯(9β-acetoxypathenolide, 3), 其IC50分别为0.41, 0.89, 0.59 μg/mL. 这三个化合物都有较强的抗癌活性, 其中化合物3为新化合物.     

Identification of volatile components of liverwort (Porella cordaeana) extracts using GC/MS-SPME and their antimicrobial activity

Chemical constituents of liverwort (Porella cordaeana) extracts have been identified using solid-phase microextraction-gas chromatography mass spectrometry (SPME-GC/MS). The methanol, ethanol and ethyl acetate extracts were rich in terpenoids such as sesquiterpene hydrocarbons (53.12%, 51.68%, 23.16%), and monoterpene hydrocarbons (22.83%, 18.90%, 23.36%), respectively. The dominant compounds in the extracts were β-phellandrene (15.54%, 13.66%, 12.10%) and β-caryophyllene (10.72%, 8.29%, 7.79%, respectively). The antimicrobial activity of the extracts was evaluated against eleven food microorganisms using the microdilution and disc diffusion methods. The minimum inhibitory concentration (MIC) varied from 0.50 to 2.00 mg/mL for yeast strains (Saccharomyces cerevisiae 635, Zygosacharomyces bailii 45, Aerobasidium pullulans L6F, Pichia membranaefaciens OC 71, Pichia membranaefaciens OC 70, Pichia anomala CBS 5759, Pichia anomala DBVPG 3003 and Yarrowia lipolytica RO13), and from 1.00 to 3.00 mg/mL for bacterial strains (Salmonella enteritidis 155, Escherichia coli 555 and Listeria monocytogenes 56Ly). Methanol extract showed better activity in comparison with ethanol and ethyl acetate extracts. High percentages of monoterpene and sesquiterpene hydrocarbons could be responsible for the better antimicrobial activity.     

Biological screening of some Turkish medicinal plant extracts for antimicrobial and toxicity activities

Screening of antibacterial activity and toxicity of 22 aqueous plant extracts from 17 Turkish plants was conducted. Antibacterial activity was performed with six bacteria including Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Streptococcus pyogenes, Staphylococcus aureus and Staphylococcus epidermidis. Extracts of Tussilago farfara leaves, Helichyrsum plicatum flowers, Solanum dulcamara aerial parts and Urtica dioica leaves gave the best inhibitory activity against S. pyogenes, S. aureus and S. epidermidis. Of the 22 plant extracts, 20 extracts displayed toxicity (LC50 was <1000 mg L(-1)) in the brine shrimp bioassay. For radish seed bioassay, two different determinations (root length and seed germination) were performed with a comparison between two concentrations (50,000 mg L(-1) and 10,000 mg L(-1)). At low concentration (10,000 mg L(-1)), S. dulcamara aerial parts and Primula vulgaris leaf extracts were observed to inhibit the root length more than the other plant extracts. Also, the most inhibitive plant extract for seed germination was obtained with S. dulcamara aerial parts.     

Antimalarial activity of sesquiterpene lactones from Vernonia cinerea

Two new sesquiterpene lactones, vernolides C and D as well as six known ones were isolated from the dichloromethane fraction of an aqueous extract from Vernonia cinerea. Their structures were elucidated by spectroscopic methods. Among the known sesquiterpene lactones, three of them were described in this plant for the first time. In vitro antiplasmodial evaluation showed that the three major compounds 1, 7 and 8 were active against chloroquine resistant Plasmodium falciparum strain (W2) with IC(50) 3.9, 3.7 and 3.5 microM, respectively.     

Phytochemical profile and biological activities of Deverra tortuosa (Desf.)DC.: a desert aromatic shrub widespread in Northern Region of Saudi Arabia

The present study describes the chemical composition of the essential oil of different plant parts of Devrra tortuosa; in vivo and in vitro biological activities of plant extract and essential oils. Apiol was found to be the major component of the oil (between 65.73% and 74.41%). The best antioxidant activities were observed for the oil of flowers (IC50 = 175 μg/ml). The samples of stems and roots exhibit lower antioxidant activity (IC50 = 201 μg/ml and 182 μg/ml, respectively). The values of IC50 showed that the extracts of methanol exhibit the highest antioxidants activities (IC50 = 64.8 102 μg/ml). EOs showed excellent antifungal activity against yeasts with low azole susceptibilities (i.e. Malassezia spp. and Candida krusei). The MIC values of oils varied between 2.85 mg/mL and 27 mg/mL. The obtained results also showed that the plant extracts inhibited the germination and the shoot and root growth of Triticum æstivum seedlings.