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Molecules, Volume 20, Issue 7 (July 2015) – 106 articles , Pages 11632-13495

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1216 KiB  
Review
Secondary Metabolites from Rubiaceae Species
by Daiane Martins and Cecilia Veronica Nunez
Molecules 2015, 20(7), 13422-13495; https://doi.org/10.3390/molecules200713422 - 22 Jul 2015
Cited by 115 | Viewed by 19516
Abstract
This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, [...] Read more.
This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, anthraquinones, triterpenes, indole alkaloids as well as other varying alkaloid subclasses, have shown to be the most common. These compounds have been mostly isolated from the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. The occurrence and distribution of iridoids, alkaloids and anthraquinones point out their chemotaxonomic correlation among tribes and subfamilies. From an evolutionary point of view, Rubioideae is the most ancient subfamily, followed by Ixoroideae and finally Cinchonoideae. The chemical biosynthetic pathway, which is not so specific in Rubioideae, can explain this and large amounts of both iridoids and indole alkaloids are produced. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it produces indole alkaloids together with other alkaloids. The chemical biosynthetic pathway now supports this botanical conclusion. Full article
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4565 KiB  
Review
Molecular Docking and Structure-Based Drug Design Strategies
by Leonardo G. Ferreira, Ricardo N. Dos Santos, Glaucius Oliva and Adriano D. Andricopulo
Molecules 2015, 20(7), 13384-13421; https://doi.org/10.3390/molecules200713384 - 22 Jul 2015
Cited by 1415 | Viewed by 90465
Abstract
Pharmaceutical research has successfully incorporated a wealth of molecular modeling methods, within a variety of drug discovery programs, to study complex biological and chemical systems. The integration of computational and experimental strategies has been of great value in the identification and development of [...] Read more.
Pharmaceutical research has successfully incorporated a wealth of molecular modeling methods, within a variety of drug discovery programs, to study complex biological and chemical systems. The integration of computational and experimental strategies has been of great value in the identification and development of novel promising compounds. Broadly used in modern drug design, molecular docking methods explore the ligand conformations adopted within the binding sites of macromolecular targets. This approach also estimates the ligand-receptor binding free energy by evaluating critical phenomena involved in the intermolecular recognition process. Today, as a variety of docking algorithms are available, an understanding of the advantages and limitations of each method is of fundamental importance in the development of effective strategies and the generation of relevant results. The purpose of this review is to examine current molecular docking strategies used in drug discovery and medicinal chemistry, exploring the advances in the field and the role played by the integration of structure- and ligand-based methods. Full article
(This article belongs to the Special Issue Molecular Docking in Drug Design)
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755 KiB  
Article
In Vivo Antihyperglycemic Activity of a Lanosteryl Triterpene from Protorhus longifolia
by Rebamang A. Mosa, Nkosinathi D. Cele, Sihle E. Mabhida, Samkelisiwe C. Shabalala, Dambudzo Penduka and Andy R. Opoku
Molecules 2015, 20(7), 13374-13383; https://doi.org/10.3390/molecules200713374 - 22 Jul 2015
Cited by 24 | Viewed by 6013
Abstract
Control of postprandial hyperglycemia is crucial in the management of diabetes mellitus. Despite the use of the current hypoglycemic drugs, incidence of diabetes and related diseases continue to increase. This study aimed at evaluating the in vivo antihyperglycemic activity of methyl-3β-hydroxylanosta-9,24-dien-21-oate (RA-3 [...] Read more.
Control of postprandial hyperglycemia is crucial in the management of diabetes mellitus. Despite the use of the current hypoglycemic drugs, incidence of diabetes and related diseases continue to increase. This study aimed at evaluating the in vivo antihyperglycemic activity of methyl-3β-hydroxylanosta-9,24-dien-21-oate (RA-3), a lanosteryl triterpene isolated, and characterized from Protorhus longifolia stem bark. Spectroscopic data analysis was used to establish and verify the structure of the triterpene. The antihyperglycemic activity of the triterpene was evaluated in an STZ-induced diabetes rat model. The experimental animals were orally administered with RA-3 (100 mg/kg body weight) daily for 14 days. An oral glucose tolerance test was also performed. The animals were euthanized and biochemical analysis of antioxidant status, some glycolytic enzymes and glycogen content were conducted on serum and liver samples, respectively. RA-3 exhibited hypoglycemic activity by reducing blood glucose levels by 37%. The triterpene also improved glucose tolerance in the diabetic rats. Relatively higher hepatic glycogen content, hexokinase and glucokinase activity with a decrease in glucose-6-phosphatase activity were observed in the triterpene-treated diabetic group when compared with the diabetic control group. The triterpene treatment further increased antioxidant status of the diabetic animals; increased activity of superoxide dismutase and catalase were observed along with a decrease in malondialdehyde content. The results indicate potential pharmaceutical effects of lanosteryl triterpene in the management of diabetes mellitus. Full article
(This article belongs to the Section Medicinal Chemistry)
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1514 KiB  
Article
Modeling the Photocatalytic Mineralization in Water of Commercial Formulation of Estrogens 17-β Estradiol (E2) and Nomegestrol Acetate in Contraceptive Pills in a Solar Powered Compound Parabolic Collector
by José Colina-Márquez, Fiderman Machuca-Martínez and Gianluca Li Puma
Molecules 2015, 20(7), 13354-13373; https://doi.org/10.3390/molecules200713354 - 22 Jul 2015
Cited by 19 | Viewed by 6481
Abstract
Endocrine disruptors in water are contaminants of emerging concern due to the potential risks they pose to the environment and to the aquatic ecosystems. In this study, a solar photocatalytic treatment process in a pilot-scale compound parabolic collector (CPC) was used to remove [...] Read more.
Endocrine disruptors in water are contaminants of emerging concern due to the potential risks they pose to the environment and to the aquatic ecosystems. In this study, a solar photocatalytic treatment process in a pilot-scale compound parabolic collector (CPC) was used to remove commercial estradiol formulations (17-β estradiol and nomegestrol acetate) from water. Photolysis alone degraded up to 50% of estradiol and removed 11% of the total organic carbon (TOC). In contrast, solar photocatalysis degraded up to 57% of estrogens and the TOC removal was 31%, with 0.6 g/L of catalyst load (TiO2 Aeroxide P-25) and 213.6 ppm of TOC as initial concentration of the commercial estradiols formulation. The adsorption of estrogens over the catalyst was insignificant and was modeled by the Langmuir isotherm. The TOC removal via photocatalysis in the photoreactor was modeled considering the reactor fluid-dynamics, the radiation field, the estrogens mass balance, and a modified Langmuir–Hinshelwood rate law, that was expressed in terms of the rate of photon adsorption. The optimum removal of the estrogens and TOC was achieved at a catalyst concentration of 0.4 g/L in 29 mm diameter tubular CPC reactors which approached the optimum catalyst concentration and optical thickness determined from the modeling of the absorption of solar radiation in the CPC, by the six-flux absorption-scattering model (SFM). Full article
(This article belongs to the Special Issue Photocatalysis)
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1074 KiB  
Article
Iminoiodane- and Brønsted Base-Mediated Cross Dehydrogenative Coupling of Cyclic Ethers with 1,3-Dicarbonyl Compounds
by Ciputra Tejo, Xiao Rong Sim, Bo Ra Lee, Benjamin James Ayers, Chung-Hang Leung, Dik-Lung Ma and Philip Wai Hong Chan
Molecules 2015, 20(7), 13336-13353; https://doi.org/10.3390/molecules200713336 - 22 Jul 2015
Cited by 8 | Viewed by 9348
Abstract
A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Brønsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers [...] Read more.
A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Brønsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers and 1,3-dicarbonyl compounds, affording the corresponding coupled products in moderate to good yields of up to 80% over two steps. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
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1130 KiB  
Article
Bioactive Cembranoids from the South China Sea Soft Coral Sarcophyton elegans
by Xin Liu, Junsheng Zhang, Qiao Liu, Guihua Tang, Hongsheng Wang, Chengqi Fan and Sheng Yin
Molecules 2015, 20(7), 13324-13335; https://doi.org/10.3390/molecules200713324 - 22 Jul 2015
Cited by 22 | Viewed by 5413
Abstract
Four new cembranoids, sarcophelegans A–D (14) and six known analogues (510) were isolated from the South China Sea soft coral Sarcophyton elegans. Their structures were elucidated through detailed spectroscopic analysis, and the absolute configuration [...] Read more.
Four new cembranoids, sarcophelegans A–D (14) and six known analogues (510) were isolated from the South China Sea soft coral Sarcophyton elegans. Their structures were elucidated through detailed spectroscopic analysis, and the absolute configuration of 1 was confirmed by single-crystal X-ray diffraction. The antimigratory potential of compounds 110 were evaluated and compounds 2 and 6 were found to inhibit human breast tumor MDA-MB-231 cell migration at 10 μM. Full article
(This article belongs to the Section Natural Products Chemistry)
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1290 KiB  
Review
Cell-Penetrating Peptides: Possibilities and Challenges for Drug Delivery in Vitro and in Vivo
by Tore Skotland, Tore Geir Iversen, Maria Lyngaas Torgersen and Kirsten Sandvig
Molecules 2015, 20(7), 13313-13323; https://doi.org/10.3390/molecules200713313 - 22 Jul 2015
Cited by 53 | Viewed by 8938
Abstract
In this review, we discuss how cell-penetrating peptides (CPPs) might get access to their intracellular targets. We specifically focus on the challenge of deciding whether the positively-charged CPPs are just bound to the negatively-charged cell surface and subsequently endocytosed or actually transported into [...] Read more.
In this review, we discuss how cell-penetrating peptides (CPPs) might get access to their intracellular targets. We specifically focus on the challenge of deciding whether the positively-charged CPPs are just bound to the negatively-charged cell surface and subsequently endocytosed or actually transported into the cytosol, either by direct plasma membrane penetration or after endocytosis. This discussion includes comments about pitfalls when using pharmacological inhibitors in such studies. The possibility of exploiting CPPs as carriers for the delivery of drugs of different sizes in vitro is discussed, as is the use of CPPs as carriers for therapeutic drugs or contrast agents in vivo. We conclude that in many cases, more studies are needed to demonstrate conclusively whether increased delivery of a substance attached to CPPs is due to a membrane-penetrating property or whether the increase is a consequence of just changing the charge of the substance to be delivered. Finally, the expected dose needed for the use of such conjugates in vivo is discussed, including aspects to consider in order to bring potential products into clinical use. Full article
(This article belongs to the Special Issue Cell Penetrating Peptides (CPPs))
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1375 KiB  
Article
Extractions of Oil from Descurainia sophia Seed Using Supercritical CO2, Chemical Compositions by GC-MS and Evaluation of the Anti-Tussive, Expectorant and Anti-Asthmatic Activities
by Jian-Hong Gong, Yan-Li Zhang, Jin-Li He, Xiao-Ke Zheng, Wei-Sheng Feng, Xiao-Lan Wang, Hai-Xue Kuang, Chun-Ge Li and Yan-Gang Cao
Molecules 2015, 20(7), 13296-13312; https://doi.org/10.3390/molecules200713296 - 22 Jul 2015
Cited by 19 | Viewed by 7071
Abstract
Descurainia sophia is widely distributed in China and is one of the most troublesome annual weeds. It has diverse medicinal usage. D. sophia has abundant oil, making it an important oil plant in China. The main goal of this study was to obtain [...] Read more.
Descurainia sophia is widely distributed in China and is one of the most troublesome annual weeds. It has diverse medicinal usage. D. sophia has abundant oil, making it an important oil plant in China. The main goal of this study was to obtain the maximum yield of the oil by an optimal selection of supercritical fluid extraction parameters. According to the central composite design and response surface methodology for supercritical fluid extraction method, a quadratic polynomial model was used to predict the yield of D. sophia seed oil. A series of runs was performed to assess the optimal extraction conditions. The results indicated that the extraction pressure had the greatest impact on oil yield within the range of the operating conditions studied. A total of approximately 67 compounds were separated in D. sophia seed oil by GC-MS, of which 51 compounds represented 98.21% of the total oils, for the first time. This study was also aimed at evaluating the anti-asthmatic, anti-tussive and expectorant activities in vivo of D. sophia seed oil which supplied for further research on bioactive constituents and pharmacological mechanisms. Full article
(This article belongs to the Collection Recent Advances in Flavors and Fragrances)
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1397 KiB  
Article
The Antioxidant Activity and Their Major Antioxidant Compounds from Acanthopanax senticosus and A. koreanum
by Young-Hyun Kim, Myoung Lae Cho, Dan-Bi Kim, Gi-Hae Shin, Jin-Ha Lee, Jong Seok Lee, Sun-Ok Park, Sang-Jong Lee, Hyun Mu Shin and Ok-Hwan Lee
Molecules 2015, 20(7), 13281-13295; https://doi.org/10.3390/molecules200713281 - 22 Jul 2015
Cited by 64 | Viewed by 7722
Abstract
The antioxidant activity and chlorogenic acid and caffeic acid contents were investigated from different parts of Acanthopanax senticosus and A. koreanum. Antioxidant activity was assessed by various in vitro assays such as DPPH, ABTS, FRAP, reducing power assays and ORAC, and the [...] Read more.
The antioxidant activity and chlorogenic acid and caffeic acid contents were investigated from different parts of Acanthopanax senticosus and A. koreanum. Antioxidant activity was assessed by various in vitro assays such as DPPH, ABTS, FRAP, reducing power assays and ORAC, and the chlorogenic acid and caffeic acid were validated by HPLC chromatography. Among the various extracts, the fruit extracts of A. senticosus and A. koreanum exhibited strongest antioxidant activities including ABTS, FRAP, reducing power and ORAC, however, strongest DPPH radical scavenging activity was observed from the leaf extract of A. senticosus. In addition, the antioxidant activities of various extracts were correlated with total phenolic and proanthocyanidin contents. The major phenolic contents from various parts of these plants observed that leaf extract of A. senticosus expressed higher levels of chlorogenic acid (14.86 mg/dry weigh g) and caffeic acid (3.09 mg/dry weigh g) than other parts. Therefore, these results suggest that the leaf of A. senticosus may be an excellent natural source for functional foods and pharmaceutical agents, and the validated method was useful for the quality control of A. senticosus. Full article
(This article belongs to the Section Medicinal Chemistry)
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1729 KiB  
Article
Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives
by Luciana Nalone Andrade, Tamires Cardoso Lima, Ricardo Guimarães Amaral, Cláudia Do Ó Pessoa, Manoel Odorico de Moraes Filho, Bruno Marques Soares, Lázaro Gomes do Nascimento, Adriana Andrade Carvalho and Damião Pergentino De Sousa
Molecules 2015, 20(7), 13264-13280; https://doi.org/10.3390/molecules200713264 - 21 Jul 2015
Cited by 39 | Viewed by 7494
Abstract
Compounds isolated from essential oils play an important role in the prevention and treatment of cancer. Monoterpenes are natural products, and the principal constituents of many essential oils. The aim of this study was to investigate the cytotoxic potential of p-menthane derivatives. [...] Read more.
Compounds isolated from essential oils play an important role in the prevention and treatment of cancer. Monoterpenes are natural products, and the principal constituents of many essential oils. The aim of this study was to investigate the cytotoxic potential of p-menthane derivatives. Additionally, analogues of perillyl alcohol, a monoterpene with known anticancer activity, were evaluated to identify the molecular characteristics which contribute to their cytotoxicity, which was tested against OVCAR-8, HCT-116, and SF-295 human tumor cell lines, using the MTT assay. The results of this study showed that (−)-perillaldehyde 8,9-epoxide exhibited the highest percentage inhibition of cell proliferation (GI = 96.32%–99.89%). Perillyl alcohol exhibited high cytotoxic activity (90.92%–95.82%), while (+)-limonene 1,2-epoxide (GI = 58.48%–93.10%), (−)-perillaldehyde (GI = 59.28%–83.03%), and (−)-8-hydroxycarvotanacetone (GI = 61.59%–94.01%) showed intermediate activity. All of the compounds tested were less cytotoxic than perillyl alcohol, except (−)-perillaldehyde 8,9-epoxide (IC50 = 1.75–1.03 µL/mg). In general, replacement of C-C double bonds by epoxide groups in addition to the aldehyde group increases cytotoxicity. Furthermore, stereochemistry seems to play an important role in cytotoxicity. We have demonstrated the cytotoxic influence of chemical substituents on the p-menthane structure, and analogues of perillyl alcohol. Full article
(This article belongs to the Section Natural Products Chemistry)
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2323 KiB  
Article
Synthesis, Spectroscopic Investigations (X-ray, NMR and TD-DFT), Antimicrobial Activity and Molecular Docking of 2,6-Bis(hydroxy(phenyl)methyl)cyclohexanone
by Assem Barakat, Hazem A. Ghabbour, Abdullah Mohammed Al-Majid, Saied M. Soliman, M. Ali, Yahia Nasser Mabkhot, Mohammed Rafi Shaik and Hoong-Kun Fun
Molecules 2015, 20(7), 13240-13263; https://doi.org/10.3390/molecules200713240 - 21 Jul 2015
Cited by 4 | Viewed by 6828
Abstract
The synthesis of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone 1 is described. The molecular structure of the title compound 1 was confirmed by NMR, FT-IR, MS, CHN microanalysis, and X-ray crystallography. The molecular structure was also investigated by a set of computational studies and found to be in [...] Read more.
The synthesis of 2,6-bis(hydroxy(phenyl)methyl)cyclohexanone 1 is described. The molecular structure of the title compound 1 was confirmed by NMR, FT-IR, MS, CHN microanalysis, and X-ray crystallography. The molecular structure was also investigated by a set of computational studies and found to be in good agreement with the experimental data obtained from the various spectrophotometric techniques. The antimicrobial activity and molecular docking of the synthesized compound was investigated. Full article
(This article belongs to the Section Organic Chemistry)
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999 KiB  
Article
The Enhanced Inhibitory Effect of Different Antitumor Agents in Self-Microemulsifying Drug Delivery Systems on Human Cervical Cancer HeLa Cells
by Zoltán Ujhelyi, Azin Kalantari, Miklós Vecsernyés, Eszter Róka, Ferenc Fenyvesi, Róbert Póka, Bence Kozma and Ildikó Bácskay
Molecules 2015, 20(7), 13226-13239; https://doi.org/10.3390/molecules200713226 - 21 Jul 2015
Cited by 35 | Viewed by 7367
Abstract
The aim of this study was to develop topical self-microemulsifying drug delivery systems (SMEDDS) containing antitumor agents (bleomycin, cisplatin and ifosfamide) and to investigate their inhibitory potential in SMEDDS on human cervical cancer HeLa cells. The physicochemical properties of cytostatic drug loaded SMEDDS [...] Read more.
The aim of this study was to develop topical self-microemulsifying drug delivery systems (SMEDDS) containing antitumor agents (bleomycin, cisplatin and ifosfamide) and to investigate their inhibitory potential in SMEDDS on human cervical cancer HeLa cells. The physicochemical properties of cytostatic drug loaded SMEDDS were characterized. The cytotoxicity of main components of SMEDDS was also investigated. Their IC50 values were determined. HeLa cells were treated by different concentrations of cisplatin, bleomycin and ifosfamide alone and in various SMEDDS. The inhibitory effect on cell growth was analyzed by MTT cell viability assay. Inflammation is a driving force that accelerates cancer development. The inhibitory effect of these antitumor agents has also been tested on HeLa cells in the presence of inflammatory mediators (IL-1-β, TNF-α) as an in vitro model of inflamed human cervix. Significant differences in the cytotoxicity of cytostatic drugs alone and in SMEDDS have been found in a concentration-dependent manner. The self-micro emulsifying system may potentiate the effectiveness of bleomycin, cisplatin and ifosfamide topically. The effect of SMEDDS containing antitumor agents was decreased significantly in the presence of inflammatory mediators. According to our experiments, the optimal SMEDDS formulation is 1:1:2:6:2 ratios of Isopropyl myristate, Capryol 90, Kolliphor RH 40, Cremophor RH40, Transcutol HP and Labrasol. It can be concluded that SMEDDS may increase the inhibitory effect of bleomycin, ifosfamide and cisplatin on human cervical cancer HeLa cells. Inflammation on HeLa cells hinders the effectiveness of SMEDDS containing antitumor agents. Our results might ensure useful data for development of optimal antitumor formulations. Full article
(This article belongs to the Collection Poorly Soluble Drugs)
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1056 KiB  
Article
Separation of Polyphenols and Caffeine from the Acetone Extract of Fermented Tea Leaves (Camellia sinensis) Using High-Performance Countercurrent Chromatography
by Soo Jung Choi, Yong Deog Hong, Bumjin Lee, Jun Seong Park, Hyun Woo Jeong, Wan Gi Kim, Song Seok Shin and Kee Dong Yoon
Molecules 2015, 20(7), 13216-13225; https://doi.org/10.3390/molecules200713216 - 21 Jul 2015
Cited by 16 | Viewed by 6376
Abstract
Leaves from Camellia sienensis are a popular natural source of various beverage worldwide, and contain caffeine and polyphenols derived from catechin analogues. In the current study, caffeine (CAF, 1) and three tea polyphenols including (−)-epigallocatechin 3-O-gallate (EGCg, 2), (−)-gallocatechin [...] Read more.
Leaves from Camellia sienensis are a popular natural source of various beverage worldwide, and contain caffeine and polyphenols derived from catechin analogues. In the current study, caffeine (CAF, 1) and three tea polyphenols including (−)-epigallocatechin 3-O-gallate (EGCg, 2), (−)-gallocatechin 3-O-gallate (GCg, 3), and (−)-epicatechin 3-O-gallate (ECg, 4) were isolated and purified by flow-rate gradient high-performance countercurrent chromatography (HPCCC) using a two-phase solvent system composed of n-hexane–ethyl acetate–methanol–water (1:9:1:9, v/v). Two hundred milligrams of acetone-soluble extract from fermented C. sinensis leaves was separated by HPCCC to give 1 (25.4 mg), 2 (16.3 mg), 3 (11.1 mg) and 4 (4.4 mg) with purities over 98%. The structures of 14 were elucidated by QTOF-MS, as well as 1H- and 13C-NMR, and the obtained data were compared to the previously reported values. Full article
(This article belongs to the Section Natural Products Chemistry)
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875 KiB  
Article
New Cembranoid Diterpenes from the Cultured Octocoral Nephthea columnaris
by Ting-Hsi Hsiao, Ching-Hsiao Cheng, Tung-Ying Wu, Mei-Chin Lu, Wu-Fu Chen, Zhi-Hong Wen, Chang-Feng Dai, Yang-Chang Wu and Ping-Jyun Sung
Molecules 2015, 20(7), 13205-13215; https://doi.org/10.3390/molecules200713205 - 21 Jul 2015
Cited by 16 | Viewed by 5491
Abstract
Two new 15-hydroxycembranoid diterpenes, 2β-hydroxy-7β,8α-epoxynephthenol (1) and 2β-hydroxy-11α,12β-epoxynephthenol (2), were isolated from extracts of the octocoral Nephthea columnaris along with a new natural cembrane, epoxynephthenol (3) and a known sterol, nephalsterol A (4). The structures [...] Read more.
Two new 15-hydroxycembranoid diterpenes, 2β-hydroxy-7β,8α-epoxynephthenol (1) and 2β-hydroxy-11α,12β-epoxynephthenol (2), were isolated from extracts of the octocoral Nephthea columnaris along with a new natural cembrane, epoxynephthenol (3) and a known sterol, nephalsterol A (4). The structures of cembranes 13 were elucidated by spectroscopic methods and comparison of the spectroscopic data with those of related analogues. The cytotoxicity of metabolites 14 against a panel of tumor cells is also described. Full article
(This article belongs to the Section Natural Products Chemistry)
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4535 KiB  
Article
Molecular Docking and Multivariate Analysis of Xanthones as Antimicrobial and Antiviral Agents
by Freddy A. Bernal and Ericsson Coy-Barrera
Molecules 2015, 20(7), 13165-13204; https://doi.org/10.3390/molecules200713165 - 21 Jul 2015
Cited by 16 | Viewed by 9271
Abstract
Xanthones are secondary metabolites which have drawn considerable interest over the last decades due to their antimicrobial properties, among others. A great number of this kind of compounds has been therefore reported, but there is a limited amount of studies on screening for [...] Read more.
Xanthones are secondary metabolites which have drawn considerable interest over the last decades due to their antimicrobial properties, among others. A great number of this kind of compounds has been therefore reported, but there is a limited amount of studies on screening for biological activity. Thus, as part of our research on antimicrobial agents of natural origin, a set of 272 xanthones were submitted to molecular docking (MD) calculations with a group of seven fungal and two viral enzymes. The results indicated that prenylated xanthones are important hits for inhibition of the analyzed enzymes. The MD scores were also analyzed by multivariate statistics. Important structural details were found to be crucial for the inhibition of the tested enzymes by the xanthones. In addition, the classification of active xanthones can be achieved by statistical analysis on molecular docking scores by an affinity-antifungal activity relationship approach. The obtained results therefore are a suitable starting point for the development of antifungal and antiviral agents based on xanthones. Full article
(This article belongs to the Special Issue Molecular Docking in Drug Design)
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713 KiB  
Review
Allergenic Proteins in Enology: A Review on Technological Applications and Safety Aspects
by Elena Peñas, Chiara Di Lorenzo, Francesca Uberti and Patrizia Restani
Molecules 2015, 20(7), 13144-13164; https://doi.org/10.3390/molecules200713144 - 21 Jul 2015
Cited by 36 | Viewed by 7332
Abstract
Proteinaceous products are widely used as fining agents during winemaking to remove unwanted insoluble particles and undissolved microscopic particles (colloidal material) from the must or wine to improve stability. Some of them (egg white, caseinates, and fish gelatine) have allergenic potential and the [...] Read more.
Proteinaceous products are widely used as fining agents during winemaking to remove unwanted insoluble particles and undissolved microscopic particles (colloidal material) from the must or wine to improve stability. Some of them (egg white, caseinates, and fish gelatine) have allergenic potential and the presence of their residues in the final product could represent a risk for allergic individuals. Moreover, lysozyme (an egg allergen) is included among wine additives to control the fermentation processes and avoid spoiling during winemaking. The aim of this paper is to review the experimental/clinical data on the use of allergenic products in enology and the measurement of relative risk for sensitized subjects. In addition, methods developed specifically for the quantification of allergenic residues in must and wine are described. Full article
(This article belongs to the Collection Wine Chemistry)
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357 KiB  
Article
A New Furofuran Lignan Diglycoside and Other Secondary Metabolites from the Antidepressant Extract of Castilleja tenuiflora Benth
by Maribel Herrera-Ruiz, Ricardo López-Rodríguez, Gabriela Trejo-Tapia, Blanca Eda Domínguez-Mendoza, Manases González-Cortazar, Jaime Tortoriello and Alejandro Zamilpa
Molecules 2015, 20(7), 13127-13143; https://doi.org/10.3390/molecules200713127 - 21 Jul 2015
Cited by 15 | Viewed by 6855
Abstract
Castilleja tenuiflora has been used for the treatment of several Central Nervous System (CNS) diseases. Herein we report the antidepressant activity of the methanol extract from the leaves of this medicinal plant. The oral administration of MeOH extract (500 mg/kg) induced a significant [...] Read more.
Castilleja tenuiflora has been used for the treatment of several Central Nervous System (CNS) diseases. Herein we report the antidepressant activity of the methanol extract from the leaves of this medicinal plant. The oral administration of MeOH extract (500 mg/kg) induced a significant (p < 0.05) decrement of the immobility parameter on Forced Swimming Test (FST) and an increment in the latency and duration of the hypnosis, induced by administration of sodium pentobarbital (Pbi, 40 mg/kg, i.p.). Chemical analysis of this antidepressant extract allowed the isolation of (+)-piperitol-4-O-xylopyranosyl-(1→6)-O-glucopyranoside. This new furofuran lignan diglycoside was named tenuifloroside (1) and its complete chemical structure elucidation on the basis of 1D and 2D NMR spectra analysis of the natural compound 1 and its peracetylated derivative 1a is described. This compound was found together with two flavones—apigenin and luteolin 5-methyl ether—a phenylethanoid—verbascoside—and three iridoids—geniposide, caryoptoside and aucubin. All these compounds were purified by successive normal and reverse phase column chromatography. Tenuifloroside, caryoptoside and luteolin 5-methyl ether were isolated from Castilleja genus for the first time. These findings demonstrate that C. tenuiflora methanol extract has beneficial effect on depressive behaviors, and the knowledge of its chemical constitution allows us to propose a new standardized treatment for future investigations of this species in depressive illness. Full article
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883 KiB  
Article
The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their 68Ga Labelling Properties
by Gábor Máté, Jakub Šimeček, Miroslav Pniok, István Kertész, Johannes Notni, Hans-Jürgen Wester, László Galuska and Petr Hermann
Molecules 2015, 20(7), 13112-13126; https://doi.org/10.3390/molecules200713112 - 21 Jul 2015
Cited by 16 | Viewed by 7311
Abstract
In order to compare the coordination properties of 1,4,7-triazacyclononane (tacn) derivatives bearing varying numbers of phosphinic/carboxylic acid pendant groups towards 68Ga, 1,4,7-triazacyclononane-7-acetic-1,4-bis(methylenephosphinic) acid (NOPA) and 1,4,7- triazacyclononane-4,7-diacetic-1-[methylene(2-carboxyethyl)phosphinic] acid (NO2AP) were synthesized using Mannich reactions with trivalent or pentavalent forms of H-phosphinic [...] Read more.
In order to compare the coordination properties of 1,4,7-triazacyclononane (tacn) derivatives bearing varying numbers of phosphinic/carboxylic acid pendant groups towards 68Ga, 1,4,7-triazacyclononane-7-acetic-1,4-bis(methylenephosphinic) acid (NOPA) and 1,4,7- triazacyclononane-4,7-diacetic-1-[methylene(2-carboxyethyl)phosphinic] acid (NO2AP) were synthesized using Mannich reactions with trivalent or pentavalent forms of H-phosphinic acids as phosphorus components. Stepwise protonation constants logK1–3 12.06, 3.90 and 1.95, and stability constants with GaIII and CuII, logKGaL 24.01 and logKCuL 16.66, were potentiometrically determined for NOPA. Both ligands were labelled with 68Ga and compared with NOTA (tacn-N,N′,N-triacetic acid) and NOPO, a TRAP-type [tacn-N,N′,N- tris(methylenephosphinic acid)] chelator. At pH 3, NOPO and NOPA showed higher labelling efficiency (binding with lower ligand excess) at both room temperature and 95 °C, compared to NO2AP and NOTA. Labelling efficiency at pH = 0–3 correlated with a number of phosphinic acid pendants: NOPO >> NOPA > NO2AP >> NOTA; however, it was more apparent at 95 °C than at room temperature. By contrast, NOTA was found to be labelled more efficiently at pH > 4 compared to the ligands with phosphinic acids. Overall, replacement of a single phosphinate donor with a carboxylate does not challenge 68Ga labelling of TRAP-type chelators. However, the presence of carboxylates facilitates labelling at neutral or weakly acidic pH. Full article
(This article belongs to the Special Issue Preparation of Radiopharmaceuticals and Their Use in Drug Development)
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1524 KiB  
Article
Identification and Expression Analysis of Glucosinolate Biosynthetic Genes and Estimation of Glucosinolate Contents in Edible Organs of Brassica oleracea Subspecies
by Go-Eun Yi, Arif Hasan Khan Robin, Kiwoung Yang, Jong-In Park, Jong-Goo Kang, Tae-Jin Yang and Ill-Sup Nou
Molecules 2015, 20(7), 13089-13111; https://doi.org/10.3390/molecules200713089 - 20 Jul 2015
Cited by 56 | Viewed by 9931
Abstract
Glucosinolates are anti-carcinogenic, anti-oxidative biochemical compounds that defend plants from insect and microbial attack. Glucosinolates are abundant in all cruciferous crops, including all vegetable and oilseed Brassica species. Here, we studied the expression of glucosinolate biosynthesis genes and determined glucosinolate contents in the [...] Read more.
Glucosinolates are anti-carcinogenic, anti-oxidative biochemical compounds that defend plants from insect and microbial attack. Glucosinolates are abundant in all cruciferous crops, including all vegetable and oilseed Brassica species. Here, we studied the expression of glucosinolate biosynthesis genes and determined glucosinolate contents in the edible organs of a total of 12 genotypes of Brassica oleracea: three genotypes each from cabbage, kale, kohlrabi and cauliflower subspecies. Among the 81 genes analyzed by RT-PCR, 19 are transcription factor-related, two different sets of 25 genes are involved in aliphatic and indolic biosynthesis pathways and the rest are breakdown-related. The expression of glucosinolate-related genes in the stems of kohlrabi was remarkably different compared to leaves of cabbage and kale and florets of cauliflower as only eight genes out of 81 were expressed in the stem tissues of kohlrabi. In the stem tissue of kohlrabi, only one aliphatic transcription factor-related gene, Bol036286 (MYB28) and one indolic transcription factor-related gene, Bol030761 (MYB51), were expressed. The results indicated the expression of all genes is not essential for glucosinolate biosynthesis. Using HPLC analysis, a total of 16 different types of glucosinolates were identified in four subspecies, nine of them were aliphatic, four of them were indolic and one was aromatic. Cauliflower florets measured the highest number of 14 glucosinolates. Among the aliphatic glucosinolates, only gluconapin was found in the florets of cauliflower. Glucoiberverin and glucobrassicanapin contents were the highest in the stems of kohlrabi. The indolic methoxyglucobrassicin and aromatic gluconasturtiin accounted for the highest content in the florets of cauliflower. A further detailed investigation and analyses is required to discern the precise roles of each of the genes for aliphatic and indolic glucosinolate biosynthesis in the edible organs. Full article
(This article belongs to the Section Molecular Diversity)
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Communication
The Complete Chloroplast Genome of Capsicum annuum var. glabriusculum Using Illumina Sequencing
by Sebastin Raveendar, Young-Wang Na, Jung-Ro Lee, Donghwan Shim, Kyung-Ho Ma, Sok-Young Lee and Jong-Wook Chung
Molecules 2015, 20(7), 13080-13088; https://doi.org/10.3390/molecules200713080 - 20 Jul 2015
Cited by 23 | Viewed by 7187
Abstract
Chloroplast (cp) genome sequences provide a valuable source for DNA barcoding. Molecular phylogenetic studies have concentrated on DNA sequencing of conserved gene loci. However, this approach is time consuming and more difficult to implement when gene organization differs among species. Here we report [...] Read more.
Chloroplast (cp) genome sequences provide a valuable source for DNA barcoding. Molecular phylogenetic studies have concentrated on DNA sequencing of conserved gene loci. However, this approach is time consuming and more difficult to implement when gene organization differs among species. Here we report the complete re-sequencing of the cp genome of Capsicum pepper (Capsicum annuum var. glabriusculum) using the Illumina platform. The total length of the cp genome is 156,817 bp with a 37.7% overall GC content. A pair of inverted repeats (IRs) of 50,284 bp were separated by a small single copy (SSC; 18,948 bp) and a large single copy (LSC; 87,446 bp). The number of cp genes in C. annuum var. glabriusculum is the same as that in other Capsicum species. Variations in the lengths of LSC; SSC and IR regions were the main contributors to the size variation in the cp genome of this species. A total of 125 simple sequence repeat (SSR) and 48 insertions or deletions variants were found by sequence alignment of Capsicum cp genome. These findings provide a foundation for further investigation of cp genome evolution in Capsicum and other higher plants. Full article
(This article belongs to the Section Molecular Diversity)
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Article
New Fluorescence Probes for Biomolecules
by Katarzyna Jurek, Janina Kabatc, Katarzyna Kostrzewska and Marlena Grabowska
Molecules 2015, 20(7), 13071-13079; https://doi.org/10.3390/molecules200713071 - 20 Jul 2015
Cited by 12 | Viewed by 5725
Abstract
Steady state fluorescence measurements have been used for the investigation of interaction between the bovine serum albumin (BSA) and fluorescence probes: 3-hydroxy-2,4- bis[(3-methyl-1,3-benzoxazol-2(3H)-ylidene)methyl]cyclobut-2-en-1-one (SQ6), 3-hydroxy- 2,4-bis[(3-methyl-1,3-benzothiazol-2(3H)-ylidene)methyl]cyclobut-2-en-1-one (SQ7) and 3-hydroxy-2,4-bis[(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)methyl]cyclobut-2-en-1-one (SQ8). The binding constant between bovine serum albumin [...] Read more.
Steady state fluorescence measurements have been used for the investigation of interaction between the bovine serum albumin (BSA) and fluorescence probes: 3-hydroxy-2,4- bis[(3-methyl-1,3-benzoxazol-2(3H)-ylidene)methyl]cyclobut-2-en-1-one (SQ6), 3-hydroxy- 2,4-bis[(3-methyl-1,3-benzothiazol-2(3H)-ylidene)methyl]cyclobut-2-en-1-one (SQ7) and 3-hydroxy-2,4-bis[(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)methyl]cyclobut-2-en-1-one (SQ8). The binding constant between bovine serum albumin and squarine dyes has been determined by using both the Benesi-Hildebrand and Stern-Volmer equations. The negative value of free energy change indicates the existence of a spontaneous complexation process of BSA with squarine dyes. Full article
(This article belongs to the Section Molecular Diversity)
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722 KiB  
Review
Cell-Type Specific Penetrating Peptides: Therapeutic Promises and Challenges
by Maliha Zahid and Paul D. Robbins
Molecules 2015, 20(7), 13055-13070; https://doi.org/10.3390/molecules200713055 - 20 Jul 2015
Cited by 69 | Viewed by 9999
Abstract
Cell penetrating peptides (CPP), also known as protein transduction domains (PTD), are small peptides able to carry peptides, proteins, nucleic acid, and nanoparticles, including viral particles, across the cellular membranes into cells, resulting in internalization of the intact cargo. In general, CPPs can [...] Read more.
Cell penetrating peptides (CPP), also known as protein transduction domains (PTD), are small peptides able to carry peptides, proteins, nucleic acid, and nanoparticles, including viral particles, across the cellular membranes into cells, resulting in internalization of the intact cargo. In general, CPPs can be broadly classified into tissue-specific and non-tissue specific peptides, with the latter further sub-divided into three types: (1) cationic peptides of 6–12 amino acids in length comprised predominantly of arginine, lysine and/or ornithine residues; (2) hydrophobic peptides such as leader sequences of secreted growth factors or cytokines; and (3) amphipathic peptides obtained by linking hydrophobic peptides to nuclear localizing signals. Tissue-specific peptides are usually identified by screening of large peptide phage display libraries. These transduction peptides have the potential for a myriad of diagnostic as well as therapeutic applications, ranging from delivery of fluorescent or radioactive compounds for imaging, to delivery of peptides and proteins of therapeutic potential, and improving uptake of DNA, RNA, siRNA and even viral particles. Here we review the potential applications as well as hurdles to the tremendous potential of these CPPs, in particular the cell-type specific peptides. Full article
(This article belongs to the Special Issue Cell Penetrating Peptides (CPPs))
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Article
Anti-Inflammatory Activities of Licorice Extract and Its Active Compounds, Glycyrrhizic Acid, Liquiritin and Liquiritigenin, in BV2 Cells and Mice Liver
by Ji-Yeon Yu, Jae Yeo Ha, Kyung-Mi Kim, Young-Suk Jung, Jae-Chul Jung and Seikwan Oh
Molecules 2015, 20(7), 13041-13054; https://doi.org/10.3390/molecules200713041 - 20 Jul 2015
Cited by 205 | Viewed by 15859
Abstract
This study provides the scientific basis for the anti-inflammatory effects of licorice extract in a t-BHP (tert-butyl hydrogen peroxide)-induced liver damage model and the effects of its ingredients, glycyrrhizic acid (GA), liquiritin (LQ) and liquiritigenin (LG), in a lipopolysaccharide (LPS)-stimulated [...] Read more.
This study provides the scientific basis for the anti-inflammatory effects of licorice extract in a t-BHP (tert-butyl hydrogen peroxide)-induced liver damage model and the effects of its ingredients, glycyrrhizic acid (GA), liquiritin (LQ) and liquiritigenin (LG), in a lipopolysaccharide (LPS)-stimulated microglial cell model. The GA, LQ and LG inhibited the LPS-stimulated elevation of pro-inflammatory mediators, such as inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), tumor necrosis factor (TNF)-alpha, interleukin (IL)-1beta and interleukin (IL)-6 in BV2 (mouse brain microglia) cells. Furthermore, licorice extract inhibited the expression levels of pro-inflammatory cytokines (TNF-α, IL-1β and IL-6) in the livers of t-BHP-treated mice models. This result suggested that mechanistic-based evidence substantiating the traditional claims of licorice extract and its three bioactive components can be applied for the treatment of inflammation-related disorders, such as oxidative liver damage and inflammation diseases. Full article
(This article belongs to the Section Metabolites)
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Article
Bioaccumulation of Trace Metals in Mussel (Mytilus galloprovincialis) from Mali Ston Bay during DSP Toxicity Episodes
by Ivana Ujević, Nenad Vuletić, Jelena Lušić, Nikša Nazlić and Grozdan Kušpilić
Molecules 2015, 20(7), 13031-13040; https://doi.org/10.3390/molecules200713031 - 17 Jul 2015
Cited by 13 | Viewed by 5882
Abstract
The Croatian National Monitoring Program revealed the presence of Diarrhetic Shellfish Poisoning (DSP) toxicity in Mediterranean blue mussel (Mytilus galloprovincialis) from breeding farms in southern Adriatic Sea through January to June 2011. The mouse bioassay tests (MBA; at the time the [...] Read more.
The Croatian National Monitoring Program revealed the presence of Diarrhetic Shellfish Poisoning (DSP) toxicity in Mediterranean blue mussel (Mytilus galloprovincialis) from breeding farms in southern Adriatic Sea through January to June 2011. The mouse bioassay tests (MBA; at the time the official method for DSP toxins) were accompanied by atypical symptomatology in the animals and this caused doubts about the assay results. Consequently, in parallel studies reported here, the concentration of Cd, Cr, Cu, Ni, Pb and Zn in soft tissue of DSP positive and negative mussels samples was determined. Cd, Cr, Zn and Ni show higher values in approximately 75% of the DSP positive samples, whereas for Pb and Cr the values were 26% and 34%, respectively. This trend was unchanged during the whole observation period. Full article
(This article belongs to the Section Natural Products Chemistry)
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2687 KiB  
Review
Carrier Modulation Layer-Enhanced Organic Light-Emitting Diodes
by Jwo-Huei Jou, Sudhir Kumar, Meenu Singh, Yi-Hong Chen, Chung-Chia Chen and Meng-Ting Lee
Molecules 2015, 20(7), 13005-13030; https://doi.org/10.3390/molecules200713005 - 17 Jul 2015
Cited by 41 | Viewed by 9199
Abstract
Organic light-emitting diode (OLED)-based display products have already emerged in the market and their efficiencies and lifetimes are sound at the comparatively low required luminance. To realize OLED for lighting application sooner, higher light quality and better power efficiency at elevated luminance are [...] Read more.
Organic light-emitting diode (OLED)-based display products have already emerged in the market and their efficiencies and lifetimes are sound at the comparatively low required luminance. To realize OLED for lighting application sooner, higher light quality and better power efficiency at elevated luminance are still demanded. This review reveals the advantages of incorporating a nano-scale carrier modulation layer (CML), also known as a spacer, carrier-regulating layer, or interlayer, among other terms, to tune the chromaticity and color temperature as well as to markedly improve the device efficiency and color rendering index (CRI) for numerous OLED devices. The functions of the CML can be enhanced as multiple layers and blend structures are employed. At proper thickness, the employment of CML enables the device to balance the distribution of carriers in the two emissive zones and achieve high device efficiencies and long operational lifetime while maintaining very high CRI. Moreover, we have also reviewed the effect of using CML on the most significant characteristics of OLEDs, namely: efficiency, luminance, life-time, CRI, SRI, chromaticity, and the color temperature, and see how the thickness tuning and selection of proper CML are crucial to effectively control the OLED device performance. Full article
(This article belongs to the Section Molecular Diversity)
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Article
Phytochemical Properties and Anti-Proliferative Activity of Olea europaea L. Leaf Extracts against Pancreatic Cancer Cells
by Chloe D. Goldsmith, Quan V. Vuong, Elham Sadeqzadeh, Costas E. Stathopoulos, Paul D. Roach and Christopher J. Scarlett
Molecules 2015, 20(7), 12992-13004; https://doi.org/10.3390/molecules200712992 - 17 Jul 2015
Cited by 58 | Viewed by 9831
Abstract
Olea europaea L. leaves are an agricultural waste product with a high concentration of phenolic compounds; especially oleuropein. Oleuropein has been shown to exhibit anti-proliferative activity against a number of cancer types. However, they have not been tested against pancreatic cancer, the [...] Read more.
Olea europaea L. leaves are an agricultural waste product with a high concentration of phenolic compounds; especially oleuropein. Oleuropein has been shown to exhibit anti-proliferative activity against a number of cancer types. However, they have not been tested against pancreatic cancer, the fifth leading cause of cancer related death in Western countries. Therefore, water, 50% ethanol and 50% methanol extracts of Corregiola and Frantoio variety Olea europaea L. leaves were investigated for their total phenolic compounds, total flavonoids and oleuropein content, antioxidant capacity and anti-proliferative activity against MiaPaCa-2 pancreatic cancer cells. The extracts only had slight differences in their phytochemical properties, and at 100 and 200 μg/mL, all decreased the viability of the pancreatic cancer cells relative to controls. At 50 μg/mL, the water extract from the Corregiola leaves exhibited the highest anti-proliferative activity with the effect possibly due to early eluting HPLC peaks. For this reason, olive leaf extracts warrant further investigation into their potential anti-pancreatic cancer benefits. Full article
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798 KiB  
Article
Chloro({2-[mesityl(quinolin-8-yl-κN)boryl]-3,5-dimethyl-phenyl}methyl-κC)palladium(II) as a Catalyst for Heck Reactions
by Sem Raj Tamang and James D. Hoefelmeyer
Molecules 2015, 20(7), 12979-12991; https://doi.org/10.3390/molecules200712979 - 17 Jul 2015
Cited by 9 | Viewed by 7192
Abstract
We recently reported an air and moisture stable 16-electron borapalladacycle formed upon combination of 8-quinolyldimesitylborane with bis(benzonitrile)dichloropalladium(II). The complex features a tucked mesityl group formed upon metalation of an ortho-methyl group on a mesityl; however it is unusually stable due to contribution [...] Read more.
We recently reported an air and moisture stable 16-electron borapalladacycle formed upon combination of 8-quinolyldimesitylborane with bis(benzonitrile)dichloropalladium(II). The complex features a tucked mesityl group formed upon metalation of an ortho-methyl group on a mesityl; however it is unusually stable due to contribution of the boron pz orbital in delocalizing the carbanion that gives rise to an η4-boratabutadiene fragment coordinated to Pd(II), as evidenced from crystallographic data. This complex was observed to be a highly active catalyst for the Heck reaction. Data of the catalyst activity are presented alongside data found in the literature, and initial comparison reveals that the borapalladacycle is quite active. The observed catalysis suggests the borapalladacycle readily undergoes reductive elimination; however the Pd(0) complex has not yet been isolated. Nevertheless, the ambiphilic ligand 8-quinolyldimesitylborane may be able to support palladium in different redox states. Full article
(This article belongs to the Special Issue The Reactivity of Frustrated Lewis Pairs)
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1054 KiB  
Article
Substituent Effects on the Stability and Antioxidant Activity of Spirodiazaselenuranes
by Devappa S. Lamani, Debasish Bhowmick and Govindasamy Mugesh
Molecules 2015, 20(7), 12959-12978; https://doi.org/10.3390/molecules200712959 - 17 Jul 2015
Cited by 13 | Viewed by 7295
Abstract
Spirodiazaselenuranes are structurally interesting compounds and the stability of these compounds depends highly on the nature of the substituents attached to the nitrogen atoms. Aromatic substituents are known to play important roles in stabilizing the Se-N bonds in spiro compounds. In this study, [...] Read more.
Spirodiazaselenuranes are structurally interesting compounds and the stability of these compounds depends highly on the nature of the substituents attached to the nitrogen atoms. Aromatic substituents are known to play important roles in stabilizing the Se-N bonds in spiro compounds. In this study, several spirodiazaselenuranes are synthesized by introducing benzylic and aliphatic substituents to understand their effect on the stability of the Se-N bonds and the antioxidant activity. Replacement of phenyl substituent by benzyl/alkyl groups significantly reduces the stability of the spirodiazaselenuranes and slows down the oxidative cyclization process. The selenium centre in the spiro compounds undergoes further oxidation to produce the corresponding selenurane oxides, which are stable at room temperature. Comparison of the glutathione peroxidase (GPx) mimetic activity of the compounds showed that the diaryl selenides having heterocyclic rings are significantly more active due to the facile oxidation of the selenium centre. However, the activity is reduced significantly for compounds having aliphatic substituents. In addition to GPx activity, the compounds also inhibit peroxynitrite-mediated nitration and oxidation reaction of protein and small molecules, respectively. The experimental observations suggest that the antioxidant activity is increased considerably upon substitution of the aromatic group with the benzylic/aliphatic substituents on the nitrogen atoms. Full article
(This article belongs to the Special Issue Selenium Catalysts and Antioxidants)
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3278 KiB  
Article
Sumac Silver Novel Biodegradable Nano Composite for Bio-Medical Application: Antibacterial Activity
by Parisa Ghorbani, Mozhgan Soltani, Masoud Homayouni-Tabrizi, Farideh Namvar, Susan Azizi, Rosfarizan Mohammad and Amin Boroumand Moghaddam
Molecules 2015, 20(7), 12946-12958; https://doi.org/10.3390/molecules200712946 - 17 Jul 2015
Cited by 27 | Viewed by 7381
Abstract
The development of reliable and ecofriendly approaches for the production of nanomaterials is a significant aspect of nanotechnology nowadays. One of the most important methods, which shows enormous potential, is based on the green synthesis of nanoparticles using plant extract. In this paper, [...] Read more.
The development of reliable and ecofriendly approaches for the production of nanomaterials is a significant aspect of nanotechnology nowadays. One of the most important methods, which shows enormous potential, is based on the green synthesis of nanoparticles using plant extract. In this paper, we aimed to develop a rapid, environmentally friendly process for the synthesis silver nanoparticles using aqueous extract of sumac. The bioactive compounds of sumac extract seem to play a role in the synthesis and capping of silver nanoparticles. Structural, morphological and optical properties of the nanoparticles were characterized using FTIR, XRD, FESEM and UV-Vis spectroscopy. The formation of Ag-NP was immediate within 10 min and confirmed with an absorbance band centered at 438 nm. The mean particle size for the green synthesized silver nanoparticles is 19.81 ± 3.67 nm and is fairly stable with a zeta potential value of −32.9 mV. The bio-formed Ag-NPs were effective against E. coli with a maximum inhibition zone of 14.3 ± 0.32 mm. Full article
(This article belongs to the Section Molecular Diversity)
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619 KiB  
Editorial
Special Issue—Towards Understanding the Mechanisms and Curing of Muscular Dystrophy Diseases
by Leonidas A. Phylactou
Molecules 2015, 20(7), 12944-12945; https://doi.org/10.3390/molecules200712944 - 16 Jul 2015
Viewed by 4300
Abstract
Muscular dystrophies are a heterogeneous group of inherited diseases with different molecular basss, but sharing similar clinical features and dystrophic changes. Full article
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