14 pages, 334 KiB  
Article
In Vitro Antioxidant Activities, Free Radical Scavenging Capacity, and Tyrosinase Inhibitory of Flavonoid Compounds and Ferulic Acid from Spiranthes sinensis (Pers.) Ames
by Chung Pin Liang 2, Chia Hao Chang 1, Chien Cheng Liang 3, Kuei Yu Hung 4 and Chang Wei Hsieh 1,*
1 Department of Medicinal Botanicals and Health Applications, Da-Yeh University, Changhua 51591, Taiwan
2 Cheng Ching General Hospital, Taichung 42881, Taiwan
3 Horien International Co., Ltd., Taichung 42881, Taiwan
4 Pemay Biomedical Technology Corp, Taichung 41348, Taiwan
Molecules 2014, 19(4), 4681-4694; https://doi.org/10.3390/molecules19044681 - 15 Apr 2014
Cited by 50 | Viewed by 8439
Abstract
In this study, ultrasound-assisted extraction (UAE) and other methods of extracting flavonoid compounds and ferulic acid (FA) from S. sinensis were investigated. Five different extraction methods, including water extraction (W), water extraction using UAE (W+U), 75% ethanol extraction (E), 75% ethanol extraction using [...] Read more.
In this study, ultrasound-assisted extraction (UAE) and other methods of extracting flavonoid compounds and ferulic acid (FA) from S. sinensis were investigated. Five different extraction methods, including water extraction (W), water extraction using UAE (W+U), 75% ethanol extraction (E), 75% ethanol extraction using UAE (E+U), and supercritical CO2 extraction (SFE) were applied in the extraction of bioactive compounds (flavonoids and ferulic acid) in order to compare their efficiency. The highest yield of flavonoids (4.28 mg/g) and ferulic acid (4.13 mg/g) content was detected in the E+U extract. Furthermore, S. sinensis extracts obtained by E+U show high antioxidant activity, and IC50 values of 0.47 mg/mL for DPPH radicals and 0.205 mg/mL for metal chelating activity. The total antioxidant assay shows superoxide radical scavenging capacity and in vitro mushroom tyrosinase inhibition in a dose-dependent manner, suggesting that E+U can be used for extraction of bioactive compounds from S. sinensis. Full article
(This article belongs to the Section Natural Products Chemistry)
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12 pages, 4099 KiB  
Article
Cornu Cervi Pantotrichum Supplementation Improves Exercise Performance and Protects against Physical Fatigue in Mice
by Chi-Chang Huang 1, Yi-Ming Chen 1,†, Nai-Wen Kan 2,3,†, Hui-Ling Chao 1, Chin-Shan Ho 1 and Mei-Chich Hsu 4,*
1 Graduate Institute of Sports Science, College of Exercise and Health Sciences, National Taiwan Sport University, Taoyuan 33301, Taiwan
2 Graduate Institute of Athletics and Coaching Science, College of Sports and Athletics, National Taiwan Sport University, Taoyuan 33301, Taiwan
3 Center for Liberal Arts, Taipei Medical University, Taipei 11031, Taiwan
4 Department of Sports Medicine, Kaohsiung Medical University, Kaohsiung 80708, Taiwan
These authors contributed equally to this work.
Molecules 2014, 19(4), 4669-4680; https://doi.org/10.3390/molecules19044669 - 15 Apr 2014
Cited by 21 | Viewed by 11148
Abstract
Cornu cervi pantotrichum (CCP) is a well-known yang-invigorating agent used in traditional Chinese medicine that can nourish the blood, tonify qi, and invigorate bones and tendons with multifunctional bioactivities. However, evidence on the effects of CCP on exercise performance and physical fatigue is [...] Read more.
Cornu cervi pantotrichum (CCP) is a well-known yang-invigorating agent used in traditional Chinese medicine that can nourish the blood, tonify qi, and invigorate bones and tendons with multifunctional bioactivities. However, evidence on the effects of CCP on exercise performance and physical fatigue is limited. We evaluated the potential beneficial effects of ethanolic extract from CCP on ergogenic and antifatigue functions following a physiological challenge. Male ICR mice from four groups (n = 8 per group) were orally administered CCP for 14 days at 0, 2054, and 4108 mg/kg/day, and were respectively designated as the vehicle, CCP-1X, and CCP-2X groups. The physical performance and antifatigue function were evaluated using forelimb grip strength and exhaustive swimming time as well as serum levels of lactate, ammonia, glucose, and creatine kinase after a 15-min swimming exercise. The results indicated that CCP-1X supplementation significantly improved grip strength; reduced fatigue-associated biochemical indices, including lactate and ammonia levels; and ameliorated skeletal muscle injury induced by acute exercise challenge. A trend analysis revealed that CCP supplementation significantly increased grip strength and dose-dependently reduced serum alkaline phosphatase, uric acid, triacylglycerol, and glucose levels in healthy mice. Therefore, CCP is a potential agent with an antifatigue pharmacological effect. Full article
(This article belongs to the Section Natural Products Chemistry)
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15 pages, 4711 KiB  
Article
Silymarin Induces Expression of Pancreatic Nkx6.1 Transcription Factor and β-Cells Neogenesis in a Pancreatectomy Model
by Claudia Soto 1,*, Luis Raya 2, Julia Pérez 1, Imelda González 1 and Salud Pérez 1
1 Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Xochimilco, México City 04960, Mexico
2 Facultad de Medicina, Universidad Nacional Autónoma de México, México City 04510, Mexico
Molecules 2014, 19(4), 4654-4668; https://doi.org/10.3390/molecules19044654 - 15 Apr 2014
Cited by 29 | Viewed by 7594
Abstract
A physio-pathological feature of diabetes mellitus is a significant reduction of β-pancreatic cells. The growth, differentiation and function maintenance of these cells is directed by transcription factors. Nkx6.1 is a key transcription factor for the differentiation, neogenesis and maintenance of β-pancreatic cells. We [...] Read more.
A physio-pathological feature of diabetes mellitus is a significant reduction of β-pancreatic cells. The growth, differentiation and function maintenance of these cells is directed by transcription factors. Nkx6.1 is a key transcription factor for the differentiation, neogenesis and maintenance of β-pancreatic cells. We reported that silymarin restores normal morphology and endocrine function of damaged pancreatic tissue after alloxan-induced diabetes mellitus in rats. The aim of this study was to analyze the effect of silymarin on Nkx6.1 transcription factor expression and its consequence in β cells neogenesis. Sixty male Wistar rats were partially pancreatectomized and divided into twelve groups. Six groups were treated with silymarin (200 mg/Kg p.o) for periods of 3, 7, 14, 21, 42 and 63 days. Additionally, an unpancreatectomized control group was used. Nkx6.1 and insulin gene expression were assessed by RT-PCR assay in total pancreatic RNA. β-Cell neogenesis was determined by immunoperoxidase assay. Silymarin treated group showed an increase of Nkx6.1 and insulin genic expression. In this group, there was an increment of β-cell neogenesis in comparison to pancreatectomized untreated group. Silymarin treatment produced a rise in serum insulin and serum glucose normalization. These results suggest that silymarin may improve the reduction of β pancreatic cells observed in diabetes mellitus. Full article
(This article belongs to the Section Medicinal Chemistry)
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19 pages, 488 KiB  
Review
Magnetically Recoverable Ruthenium Catalysts in Organic Synthesis
by Dong Wang and Didier Astruc *
ISM, UMR CNRS No. 5255, Université Bordeaux, Talence Cedex 33405, France
Molecules 2014, 19(4), 4635-4653; https://doi.org/10.3390/molecules19044635 - 15 Apr 2014
Cited by 36 | Viewed by 8194
Abstract
Magnetically recyclable catalysts with magnetic nanoparticles (MNPs) are becoming a major trend towards sustainable catalysts. In this area, recyclable supported ruthenium complexes and ruthenium nanoparticles occupy a key place and present great advantages compared to classic catalysts. In this micro-review, attention is focused [...] Read more.
Magnetically recyclable catalysts with magnetic nanoparticles (MNPs) are becoming a major trend towards sustainable catalysts. In this area, recyclable supported ruthenium complexes and ruthenium nanoparticles occupy a key place and present great advantages compared to classic catalysts. In this micro-review, attention is focused on the fabrication of MNP-supported ruthenium catalysts and their catalytic applications in various organic syntheses. Full article
(This article belongs to the Special Issue Ruthenium Complex)
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11 pages, 506 KiB  
Article
Green Synthesis of Silver Nanoparticles using Achillea biebersteinii Flower Extract and Its Anti-Angiogenic Properties in the Rat Aortic Ring Model
by Javad Baharara 1,2, Farideh Namvar 3,4,*, Tayebe Ramezani 5, Nasrin Hosseini 1 and Rosfarizan Mohamad 3,6
1 Research Center for Animal Development Applied Biology, Mashhad Branch, Islamic Azad University, Mashhad, Iran
2 Department of Biology, Mashhad Branch, Islamic Azad University, Mashhad, Iran
3 Institute of Tropical Forestry and Forest Products (INTROP), Universiti Putra Malaysia, Serdang, Selangor 43400 UPM, Malaysia
4 Research Center for Animal Development Applied Biology & Department of Medicine, Mashhad Branch, Islamic Azad University, Mashhad, Iran
5 Faculty of Biological Sciences, Kharazmi University, Tehran 31979-37551, Iran
6 Department of Bioprocess Technology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, Serdang, Selangor 43400 UPM, Malaysia
Molecules 2014, 19(4), 4624-4634; https://doi.org/10.3390/molecules19044624 - 15 Apr 2014
Cited by 108 | Viewed by 11281
Abstract
Silver nanoparticles display unique physical and biological properties which have attracted intensive research interest because of their important medical applications. In this study silver nanoparticles (Ab.Ag-NPs) were synthesized for biomedical applications using a completely green biosynthetic method using Achillea biebersteinii flowers [...] Read more.
Silver nanoparticles display unique physical and biological properties which have attracted intensive research interest because of their important medical applications. In this study silver nanoparticles (Ab.Ag-NPs) were synthesized for biomedical applications using a completely green biosynthetic method using Achillea biebersteinii flowers extract. The structure and properties of Ab.Ag-NPs were investigated using UV-visible spectroscopic techniques, transmission electron microscopy (TEM), zeta potential and energy dispersive X-ray spectrometers (EDS). The UV-visible spectroscopic analysis showed the absorbance peak at 460 nm, which indicates the synthesis of silver nanoparticles. The average particle diameter as determined by TEM was found to be 12 ± 2 nm. The zeta potential analysis indicated that Ab.Ag-NPs have good stability EDX analysis also exhibits presentation of silver element. As angiogenesis is an important phenomenon and as growth factors imbalance in this process causes the acceleration of several diseases including cancer, the anti-angiogenic properties of Ab.Ag-NPs were evaluated using the rat aortic ring model. The results showed that Ab.Ag-NPs (200 μg/mL) lead to a 50% reduction in the length and number of vessel-like structures. The synthesized silver nanoparticles from the Achillea biebersteinii flowers extract, which do not involve any harmful chemicals were well-dispersed and stabilized through this green method and showed potential therapeutic benefits against angiogenesis. Full article
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16 pages, 445 KiB  
Article
Anti-Inflammatory Triterpenoids from the Stems of Microtropis Fokienensis
by I-Hsiao Chen 1, Ying-Chi Du 2, Tsong-Long Hwang 3, I-Fen Chen 4, Yu-Hsuan Lan 5, Hsin-Fu Yen 6, Fang-Rong Chang 7,8,9,* and Yang-Chang Wu 5,7,10,11,*
1 School of Chinese Medicine for Post Baccalaureate, College of Medicine, I Shou University, Kaohsiung 82445, Taiwan
2 Department of Botanicals, Medical and Pharmaceutical Industry Technology and Development Center, New Taipei City 248, Taiwan
3 Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan
4 Department of Biomedical Engineering, College of Medicine, I Shou University, Kaohsiung 82445, Taiwan
5 School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan
6 National Museum of Natural Science, Taichung 404, Taiwan
7 Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
8 Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan
9 Cancer Center, Kaohsiung Medical University Hospital, No. 100 Tz-You First Road, Kaohsiung 807, Taiwan
10 Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan
11 Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan
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Molecules 2014, 19(4), 4608-4623; https://doi.org/10.3390/molecules19044608 - 14 Apr 2014
Cited by 18 | Viewed by 7427
Abstract
Three new ursane- and four new oleanane- type triterpenoids 17 were isolated, along with six known compounds 813, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates [...] Read more.
Three new ursane- and four new oleanane- type triterpenoids 17 were isolated, along with six known compounds 813, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates 410 and known compounds 1417 that were previously isolated from this material were evaluated for anti-inflammatory activity based on effects against superoxide anion generation and elastase release by neutrophils in response to fMLP/CB. 11α,30-Dihydroxy-2,3-seco-olean-12-en-2,3-dioic anhydride (7) was the first triterpene anhydride from the genus of Microtropis to have the ring A expanded to a seven-membered ring; it showed significant anti-inflammatory activity against superoxide anion generation and elastase release. Unexpectedly, 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17) showed the best effect against superoxide anion generation and elastase release with IC50 values of 0.06 ± 0.01 and 1.03 ± 0.35 µg/mL, respectively. Compound 17 had a dioic acid function, and compound 7 had an anhydride function modification in ring A; both showed promising activity in the target assays. Full article
(This article belongs to the Section Natural Products Chemistry)
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13 pages, 247 KiB  
Article
In Vitro Antioxidant and Cytotoxic Activity of Some Synthetic Riparin-Derived Compounds
by Geandra B. L. Nunes 1, Paola R. Policarpo 1, Luciana M. Costa 1, Teresinha G. Da Silva 2, Gardenia Carmen G. Militão 2, Celso A. Câmara 3, José Maria Barbosa Filho 4, Stanley Juan C. Gutierrez 5, Mohammed T. Islam 6 and Rivelilson M. De Freitas 1,*
1 Laboratory for Research in Experimental Neurochemistry, Campus Ministro Petrônio Portella, Federal University of Piauí, Teresina, PI 64049550, Brazil
2 Laboratory of Bioassays for Drug Research, Federal University of Pernambuco, Recife, PE 50670-901, Brazil
3 Department of Chemistry, Federal Rural University of Pernambuco, Recife, PE 52171900, Brazil
4 Laboratory of Pharmaceutical Technology Federal University of Paraíba, João Pessoa, PB 58051-900, Brazil
5 Laboratory Chemistry of Bioactive Natural and Synthetic Products, Federal University of Piauí, Teresina, PI 64049550, Brazil
6 Department of Pharmacy, Faculty of Science and Engineering, Southern University Bangladesh, Mededibag, Chittagong-4000, Bangladesh
Molecules 2014, 19(4), 4595-4607; https://doi.org/10.3390/molecules19044595 - 11 Apr 2014
Cited by 22 | Viewed by 6711
Abstract
This study aimed to study the in vitro antioxidant activity and cytotoxicity on tumor cells lines of six synthetic substances derived from riparins. All the substances showed antioxidant activity and riparins C, D, E, F presented cell growth inhibition rates greater than 70%, [...] Read more.
This study aimed to study the in vitro antioxidant activity and cytotoxicity on tumor cells lines of six synthetic substances derived from riparins. All the substances showed antioxidant activity and riparins C, D, E, F presented cell growth inhibition rates greater than 70%, suggesting that these molecules have antitumor properties. These substances also caused greater than 80% releases of cytoplasmic lactate dehydrogenase enzyme (LDH). Although the antioxidant and antitumor properties presented herein require further assessment, the outcomes indicate that these novel riparins are promising biologically active compounds. Full article
(This article belongs to the Section Medicinal Chemistry)
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17 pages, 812 KiB  
Article
MALDI-TOF MS Analysis of Cellodextrins and Xylo-oligosaccharides Produced by Hindgut Homogenates of Reticulitermes santonensis
by Catherine Brasseur 1,2,*, Julien Bauwens 3, Cédric Tarayre 4, Christel Mattéotti 5, Philippe Thonart 4, Jacqueline Destain 4, Frédéric Francis 3, Eric Haubruge 3, Daniel Portetelle 5, Micheline Vandenbol 5, Jean-François Focant 2 and Edwin De Pauw 1
1 Mass Spectrometry Laboratory, Department of Chemistry, University of Liège, Allée du Six Aout, B6c, Sart-Tilman, B-4000 Liège, Belgium
2 Organic and Biological Analytical Chemistry, Department of Chemistry, University of Liège, Allée du Six Aout, B6c, Sart-Tilman, B-4000 Liège, Belgium
3 Department of Functional and Evolutionary Entomology, Gembloux Agro-Bio Tech, University of Liège, 2 Passage des Déportés, B-5030 Gembloux, Belgium
4 Department of Bio-Industries, Gembloux Agro-Bio Tech, University of Liège, 2 Passage des Déportés, B-5030 Gembloux, Belgium
5 Department of Microbiology and Genomics, Gembloux Agro-Bio Tech, University of Liège, 6 Avenue Maréchal Juin, B-5030 Gembloux, Belgium
Molecules 2014, 19(4), 4578-4594; https://doi.org/10.3390/molecules19044578 - 11 Apr 2014
Cited by 16 | Viewed by 8862
Abstract
Hindgut homogenates of the termite Reticulitermes santonensis were incubated with carboxymethyl cellulose (CMC), crystalline celluloses or xylan substrates. Hydrolysates were analyzed with matrix-assisted laser desorption/ionization coupled to time-of-flight mass spectrometry (MALDI-TOF MS). The method was first set up using acid hydrolysis analysis to [...] Read more.
Hindgut homogenates of the termite Reticulitermes santonensis were incubated with carboxymethyl cellulose (CMC), crystalline celluloses or xylan substrates. Hydrolysates were analyzed with matrix-assisted laser desorption/ionization coupled to time-of-flight mass spectrometry (MALDI-TOF MS). The method was first set up using acid hydrolysis analysis to characterize non-enzymatic profiles. Commercial enzymes of Trichoderma reesei or T. longibrachiatum were also tested to validate the enzymatic hydrolysis analysis. For CMC hydrolysis, data processing and visual display were optimized to obtain comprehensive profiles and allow rapid comparison and evaluation of enzymatic selectivity, according to the number of substituents of each hydrolysis product. Oligosaccharides with degrees of polymerization (DPs) ranging from three to 12 were measured from CMC and the enzymatic selectivity was demonstrated. Neutral and acidic xylo-oligosaccharides with DPs ranging from three to 11 were measured from xylan substrate. These results are of interest for lignocellulose biomass valorization and demonstrated the potential of termites and their symbiotic microbiota as a source of interesting enzymes for oligosaccharides production. Full article
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
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18 pages, 326 KiB  
Article
Seasonal Variation of the Chemical Composition and Antimicrobial and Cytotoxic Activities of the Essential Oils from Inga laurina (Sw.) Willd.
by Fabiana B. Furtado 1, Francisco J. T. De Aquino 1, Evandro A. Nascimento 1, Carla De M. Martins 2, Sérgio A. L. De Morais 1, Roberto Chang 1, Luís C. S. Cunha 1, Luís F. Leandro 3, Carlos H. G. Martins 3, Mário M. Martins 1, Claudio V. da Silva 4, Fabrício C. Machado 4 and Alberto De Oliveira 1,*
1 Laboratory of Natural Products and Chromatography, Chemistry Institute, Federal University of Uberlândia, Uberlândia, Minas Gerais 38408-144, Brazil
2 Federal Institute Goiano, Morrinhos, Goiás 75650-000, Brazil
3 Nucleus of Research in Sciences and Technology, Laboratory of Research in Applied Microbiology (LaPeMA), University of Franca, Franca, São Paulo 14404-600, Brazil
4 Institute of Biomedical Sciences, Laboratory of Trypanosomatids, Federal University of Uberlândia, Uberlândia, Minas Gerais 38400-902, Brazil
Molecules 2014, 19(4), 4560-4577; https://doi.org/10.3390/molecules19044560 - 11 Apr 2014
Cited by 27 | Viewed by 7805
Abstract
The seasonal chemical composition of essential oils from Inga laurina was determined by GC/MS. In the stem bark’s essential oil extracted during the dry season, the presence of terpenoids (30.05%) stood out, and phytol (9.76%) was the major compound identified. For the stem [...] Read more.
The seasonal chemical composition of essential oils from Inga laurina was determined by GC/MS. In the stem bark’s essential oil extracted during the dry season, the presence of terpenoids (30.05%) stood out, and phytol (9.76%) was the major compound identified. For the stem bark oil obtained during the rainy season, in addition to terpenoids (26.63%), a large amount of fatty acids (46.84%) were identified, in particular palmitic acid (25.40%). Regarding the leaves’ essential oil obtained in the dry season, esters (42.35%) were the main components. The main ester present was (Z)-hex-3-enyl benzoate (10.15%) and the major compound of this oil was (Z)-hex-3-en-1-ol (14.23%). Terpenoids (33.84%), long-chain alkanes (27.04%) and fatty acids (21.72%) were the main components of the essential oil from leaves in the rainy season. Phytol (33.21%), nonacosane (21.95%) and palmitic acid (15.20%) were the major compounds identified. The antimicrobial activity against aerobic and anaerobic oral bacteria was evaluated by the microdilution broth method and cytotoxic activity was carried out with Vero cells. The essential oils from the rainy season showed a better inhibition of the bacterial growth with Minimal Inhibitory Concentrations (MIC) values of 25 or 50 µg·mL−1 for aerobic bacteria, and high selectivity against bacteria was observed. The large amount of fatty acids in rainy season oils may be related to the better inhibitory effects observed. Full article
(This article belongs to the Section Natural Products Chemistry)
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12 pages, 630 KiB  
Article
Five Withanolides from the Leaves of Datura metel L. and Their Inhibitory Effects on Nitric Oxide Production
by Bing-You Yang, Rui Guo, Ting Li, Yan Liu, Chang-Fu Wang, Zun-Peng Shu, Zhi-Bin Wang, Jing Zhang, Yong-Gang Xia, Hai Jiang, Qiu-Hong Wang * and Hai-Xue Kuang *
1 Key Laboratory of Chinese Materia Medica (Ministry of Education), Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin 150040, China
These authors contributed equally to this work.
Molecules 2014, 19(4), 4548-4559; https://doi.org/10.3390/molecules19044548 - 11 Apr 2014
Cited by 36 | Viewed by 7896
Abstract
Four new withanolides named dmetelins A–D (compounds 14), along with the known compound 7α,27-dihydroxy-1-oxo-witha-2,5,24-trienolide (5) were isolated from the leaves of Datura metel L. (Solanaceae). Their structures were elucidated on the basis of detailed analysis of [...] Read more.
Four new withanolides named dmetelins A–D (compounds 14), along with the known compound 7α,27-dihydroxy-1-oxo-witha-2,5,24-trienolide (5) were isolated from the leaves of Datura metel L. (Solanaceae). Their structures were elucidated on the basis of detailed analysis of 1D and 2D NMR and mass spectrometry data. All the compounds were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells. Compounds 1, 4 and 5 showed significant inhibitory activities, and compounds 2 and 3 showed moderate inhibitory activities with IC50 values of 17.8, 11.6, 14.9, 33.3 and 28.6 μM, respectively. Full article
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24 pages, 960 KiB  
Article
Comparative Study of Tributyltin Adsorption onto Mesoporous Silica Functionalized with Calix[4]arene, p-tert-Butylcalix[4]arene and p-Sulfonatocalix[4]arene
by Sana Alahmadi 1,2,*, Sharifah Mohamad 1 and Mohd Jamil Maah 1
1 Department of Chemistry, Faculty of Science, University Malaya, Kuala Lumpur 50603, Malaysia
2 Department of Chemistry, Faculty of Science, Taibah University, Almadina Almonwara 30001, Saudi Arabia
Molecules 2014, 19(4), 4524-4547; https://doi.org/10.3390/molecules19044524 - 10 Apr 2014
Cited by 12 | Viewed by 6839
Abstract
The adsorption of tributyltin (TBT), onto three mesoporous silica adsorbents functionalized with calix[4]arene, p-tert-butylcalix[4]arene and p-sulfonatocalix[4]arene (MCM-TDI-C4, MCM-TDI-PC4 and MCM-TDI-C4S, respectively) has been compared. Batch adsorption experiments were carried out and the effect of contact time, initial TBT concentration, pH and [...] Read more.
The adsorption of tributyltin (TBT), onto three mesoporous silica adsorbents functionalized with calix[4]arene, p-tert-butylcalix[4]arene and p-sulfonatocalix[4]arene (MCM-TDI-C4, MCM-TDI-PC4 and MCM-TDI-C4S, respectively) has been compared. Batch adsorption experiments were carried out and the effect of contact time, initial TBT concentration, pH and temperature were studied. The Koble–Corrigan isotherm was the most suitable for data fitting. Based on a Langmuir isotherm model, the maximum adsorption capacities were 12.1212, 16.4204 and 7.5757 mg/g for MCM-TDI-C4, MCM-TDI-PC4 and MCM-TDI-C4S, respectively. The larger uptake and stronger affinity of MCM-TDI-PC4 than MCM-TDI-C4 and MCM-TDI-C4S probably results from van der Waals interactions and the pore size distribution of MCM-TDI-PC4. Gibbs free energies for the three adsorption processes of TBT presented a negative value, reflecting that TBT/surface interactions are thermodynamic favorable and spontaneous. The interaction processes were accompanied by an increase of entropy value for MCM-TDI-C4 and MCM-TDI-C4S (43.7192 and 120.7609 J/mol K, respectively) and a decrease for MCM-TDI-PC4 (−37.4704 J/mol K). It is obviously observed that MCM-TDI-PC4 spontaneously adsorbs TBT driven mainly by enthalpy change, while MCM-TDI-C4 and MCM-TDI-C4S do so driven mainly by entropy changes. Full article
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14 pages, 424 KiB  
Article
Different Accumulation Profiles of Multiple Components Between Pericarp and Seed of Alpinia oxyphylla Capsular Fruit as Determined by UFLC-MS/MS
by Feng Chen 1,2,3,†, Hai-Long Li 1,2,3,†, Yin-Feng Tan 1,2,3, Wei-Wei Guan 1,2,3, Jun-Qing Zhang 1,2,3,*, Yong-Hui Li 1,2,3,*, Yuan-Sheng Zhao 4 and Zhen-Miao Qin 1,2,3
1 School of Pharmacy, Hainan Medical University, Haikou 571101, China
2 Hainan Provincial Key Laboratory of R&D of Tropical Herbs, Hainan Medical University, Haikou 571101, China
3 Haikou Municipal Key Laboratory of R&D of Li Nationality Herbs, Hainan Medical University, Haikou 571101, China
4 The Hamner Institutes for Health Sciences, Research Triangle Park, NC 27709, USA
These authors contributed equally to this work.
Molecules 2014, 19(4), 4510-4523; https://doi.org/10.3390/molecules19044510 - 10 Apr 2014
Cited by 31 | Viewed by 7665
Abstract
Plant secondary metabolites are known to not only play a key role in the adaptation of plants to their environment, but also represent an important source of active pharmaceuticals. Alpinia oxyphylla capsular fruits, made up of seeds and pericarps, are commonly used in [...] Read more.
Plant secondary metabolites are known to not only play a key role in the adaptation of plants to their environment, but also represent an important source of active pharmaceuticals. Alpinia oxyphylla capsular fruits, made up of seeds and pericarps, are commonly used in traditional East Asian medicines. In clinical utilization of these capsular fruits, inconsistent processing approaches (i.e., hulling pericarps or not) are employed, with the potential of leading to differential pharmacological effects. Therefore, an important question arises whether the content levels of pharmacologically active chemicals between the seeds and pericarps of A. oxyphylla are comparable. Nine secondary metabolites present in A. oxyphylla capsular fruits, including flavonoids (e.g., tectochrysin, izalpinin, chrysin, apigenin-4',7-dimethylether and kaempferide), diarylheptanoids (e.g., yakuchinone A and B and oxyphyllacinol) and sesquiterpenes (e.g., nootkatone), were regarded as representative constituents with putative pharmacological activities. This work aimed to investigate the abundance of the nine constituents in the seeds and pericarps of A. oxyphylla. Thirteen batches of A. oxyphylla capsular fruits were gathered from different production regions. Accordingly, an ultra-fast high performance liquid chromatography/quadrupole tandem mass spectrometry (UFLC-MS/MS) method was developed and validated. We found that: (1) the nine secondary metabolites were differentially concentrated in seeds and fruit capsules; (2) nootkatone is predominantly distributed in the seeds; in contrast, the flavonoids and diarylheptanoids are mainly deposited in the capsules; and (3) the content levels of the nine secondary metabolites occurring in the capsules varied greatly among different production regions, although the nootkatone levels in the seeds were comparable among production regions. These results are helpful to evaluating and elucidating pharmacological activities of A. oxyphylla capsular fruits. Additionally, it may be of interest to elucidate the mechanisms involved in the distinct accumulation profiles of these secondary metabolites between seeds and pericarps. Full article
(This article belongs to the Section Medicinal Chemistry)
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19 pages, 2040 KiB  
Article
Inhibition and Biochemical Characterization of Methicillin-Resistant Staphylococcus aureus Shikimate Dehydrogenase: An in Silico and Kinetic Study
by Claudia Avitia-Domínguez 1, Erick Sierra-Campos 2,*, José Manuel Salas-Pacheco 3, Hugo Nájera 4, Arturo Rojo-Domínguez 4, Jorge Cisneros-Martínez 1 and Alfredo Téllez-Valencia 1,*
1 Facultad de Medicina y Nutrición, Universidad Juárez del Estado de Durango, Av. Universidad y Fanny Anitúa S/N, Durango, Durango, C.P. 34000, Mexico
2 Facultad de Ciencias Químicas, Universidad Juárez del Estado de Durango, Av. Artículo 123 S/N Fracc. Filadelfia, Gómez Palacio, Durango, CP. 35010, Mexico
3 Instituto de Investigación Científica, Universidad Juárez del Estado de Durango, Av. Universidad S/N., Durango, Durango, C.P. 34000, Mexico
4 Departamento de Ciencias Naturales, Universidad Autónoma Metropolitana, Unidad Cuajimalpa. Av. Vasco de Quiroga 4871, Colonia Santa Fe Cuajimalpa, Delegación Cuajimalpa de Morelos, Distrito Federal, C.P. 05300, Mexico
Molecules 2014, 19(4), 4491-4509; https://doi.org/10.3390/molecules19044491 - 10 Apr 2014
Cited by 18 | Viewed by 8471
Abstract
Methicillin-resistant Staphylococcus auerus (MRSA) strains are having a major impact worldwide, and due to their resistance to all β-lactams, an urgent need for new drugs is emerging. In this regard, the shikimate pathway is considered to be one of the metabolic features of [...] Read more.
Methicillin-resistant Staphylococcus auerus (MRSA) strains are having a major impact worldwide, and due to their resistance to all β-lactams, an urgent need for new drugs is emerging. In this regard, the shikimate pathway is considered to be one of the metabolic features of bacteria and is absent in humans. Therefore enzymes involved in this route, such as shikimate dehydrogenase (SDH), are considered excellent targets for discovery of novel antibacterial drugs. In this study, the SDH from MRSA (SaSDH) was characterized. The results showed that the enzyme is a monomer with a molecular weight of 29 kDa, an optimum temperature of 65 °C, and a maximal pH range of 9–11 for its activity. Kinetic studies revealed that SDH showed Michaelis-Menten kinetics toward both substrates (shikimate and NADP+). Initial velocity analysis suggested that SaSDH catalysis followed a sequential random mechanism. Additionally, a tridimensional model of SaSDH was obtained by homology modeling and validated. Through virtual screening three inhibitors of SaSDH were found (compounds 238, 766 and 894) and their inhibition constants and mechanism were obtained. Flexible docking studies revealed that these molecules make interactions with catalytic residues. The data of this study could serve as starting point in the search of new chemotherapeutic agents against MRSA. Full article
(This article belongs to the Special Issue In-Silico Drug Design and In-Silico Screening)
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12 pages, 434 KiB  
Article
Studies on the Bioactive Flavonoids Isolated from Pithecellobium clypearia Benth
by Jie Kang, Chao Liu, Hongqing Wang, Baoming Li, Chao Li, Ruoyun Chen * and Ailin Liu *
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China
Molecules 2014, 19(4), 4479-4490; https://doi.org/10.3390/molecules19044479 - 10 Apr 2014
Cited by 30 | Viewed by 7747
Abstract
One new flavonoid named (2R,3R)-7-O-galloylplumbocatechin A (1) and three known flavonoids, (−)-5,3',4',5'-tetrahydroxyflavan-7-gallate (2), (+)-3,5,3',4',5'-penta-hydroxyflavan-7-gallate (3), and (−)-7,4'-di-O-galloyltricetiflavan (4), were isolated from Pithecellobium clypearia Benth. Their structures were [...] Read more.
One new flavonoid named (2R,3R)-7-O-galloylplumbocatechin A (1) and three known flavonoids, (−)-5,3',4',5'-tetrahydroxyflavan-7-gallate (2), (+)-3,5,3',4',5'-penta-hydroxyflavan-7-gallate (3), and (−)-7,4'-di-O-galloyltricetiflavan (4), were isolated from Pithecellobium clypearia Benth. Their structures were elucidated based on spectroscopic analysis, including homonuclear and heteronuclear correlation NMR (HSQC and HMBC) experiments. In vitro assays, compounds 1 and 2 showed moderate inhibitory effects against influenza H1N1 virus neuraminidase (NA). Compounds 14 were all found to inhibit the expression of proinflammatory cytokines IL-6 or MCP-1 induced by influenza H1N1 virus in human A549 lung carcinoma cells. Full article
(This article belongs to the Section Natural Products Chemistry)
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13 pages, 367 KiB  
Article
Quantitative Analysis of the Flavonoid Glycosides and Terpene Trilactones in the Extract of Ginkgo biloba and Evaluation of Their Inhibitory Activity towards Fibril Formation of β-Amyloid Peptide
by Haiyan Xie 1, Jing-Rong Wang 1,2, Lee-Fong Yau 1,2, Yong Liu 1, Liang Liu 1,2, Quan-Bin Han 1, Zhongzhen Zhao 1,* and Zhi-Hong Jiang 1,2,*
1 School of Chinese Medicine, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong, China
2 State Key Lab of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Macau, China
Molecules 2014, 19(4), 4466-4478; https://doi.org/10.3390/molecules19044466 - 10 Apr 2014
Cited by 52 | Viewed by 12719
Abstract
The standard extract of Ginkgo biloba leaves (EGb761) is used clinically in Europe for the symptomatic treatment of impaired cerebral function in primary degenerative dementia syndromes, and the results of numerous in vivo and in vitro studies have supported such clinical use. The [...] Read more.
The standard extract of Ginkgo biloba leaves (EGb761) is used clinically in Europe for the symptomatic treatment of impaired cerebral function in primary degenerative dementia syndromes, and the results of numerous in vivo and in vitro studies have supported such clinical use. The abnormal production and aggregation of amyloid β peptide (Aβ) and the deposition of fibrils in the brain are regarded as key steps in the onset of Alzheimer’s Disease (AD), and the inhibition of Aβ aggregation and destabilization of the preformed fibrils represent viable approaches for the prevention and treatment of AD. Flavonoid glycosides and terpene trilactones (TTLs) are the two main components of EGb761 which represent 24 and 6% of the overall content, respectively. In our research, seven abundant flavonoid glycosides 17 were isolated from the extract of Ginkgo biloba leaves and characterized by spectroscopic analysis. Furthermore, an ultra-high performance liquid chromatography method was established for the simultaneous quantification of these seven flavonoids. The inhibitory activities of these flavonoids, as well as four TTLs, i.e., ginkgolides A, B, and C and bilobalide (compounds 811), were evaluated towards Aβ42 fibril formation using a thioflavin T fluorescence assay. It was found that three flavonoids 1, 3 and 4 exhibited moderate inhibitory activities, whereas the other four flavonoids 2, 5, 6 and 7, as well as the four terpene trilactones, showed poor activity. This is the first report of the inhibition of Aβ fibril formation of two characteristic acylated flavonoid glycosides 6, 7 in Ginkgo leaves, on the basis of which the structure-activity relationship of these flavonoids 17 was discussed. Full article
(This article belongs to the Section Natural Products Chemistry)
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