17 pages, 1342 KiB  
Article
Synthesis, Characterization, Antimicrobial and Antiproliferative Activity Evaluation of Cu(II), Co(II), Zn(II), Ni(II) and Pt(II) Complexes with Isoniazid-Derived Compound
by Elena Pahonțu 1,*, Diana-Carolina Ilieș 2,*, Sergiu Shova 3, Camelia Oprean 4,5, Virgil Păunescu 5,6, Octavian Tudorel Olaru 7, Flavian Ștefan Rădulescu 8, Aurelian Gulea 9, Tudor Roșu 10 and Doina Drăgănescu 11
1 Inorganic Chemistry Department, Faculty of Pharmacy, University of Medicine and Pharmacy “Carol Davila”, 6 Traian Vuia Street, 020956 Bucharest, Romania
2 Organic Chemistry Department, Faculty of Pharmacy, University of Medicine and Pharmacy “Carol Davila”, 6 Traian Vuia Street, 020956 Bucharest, Romania
3 Institute of Macromolecular Chemistry “Petru Poni”, 41A Grigore Ghica Voda Alley, 700487 Iasi, Romania
4 Environmental and Food Chemistry Department, Faculty of Pharmacy, University of Medicine and Pharmacy “Victor Babeş”, 2nd Eftimie Murgu Sq., 300041 Timişoara, Romania
5 “Pius Brinzeu” Timișoara County Emergency Clinical Hospital, Oncogen Institute, 156 Liviu Rebreanu, 300723 Timişoara, Romania
6 Functional Sciences Department, Faculty of Medicine, University of Medicine and Pharmacy “Victor Babeş”, 2 Eftimie Murgu Square, 300041 Timişoara, Romania
7 Pharmaceutical Botany and Cell Biology Department, Faculty of Pharmacy, University of Medicine and Pharmacy “Carol Davila”, 6 Traian Vuia Street, 020956 Bucharest, Romania
8 Pharmaceutical Biotechnology Department, Faculty of Pharmacy, University of Medicine and Pharmacy “Carol Davila”, 6 Traian Vuia Street, 020956 Bucharest, Romania
9 Coordination Chemistry Department, Moldova State University, 60 Mateevici Street, 2009 Chisinau, Moldova
10 Inorganic Chemistry Department, Faculty of Chemistry, University of Bucharest, 23 Dumbrava Rosie Street, 020462 Bucharest, Romania
11 Pharmaceutical Physics Department, Faculty of Pharmacy, University of and Pharmacy “Carol Davila”, 6 Traian Vuia Street, 020956 Bucharest, Romania
add Show full affiliation list remove Hide full affiliation list
Molecules 2017, 22(4), 650; https://doi.org/10.3390/molecules22040650 - 19 Apr 2017
Cited by 57 | Viewed by 6475
Abstract
Hydrazone complexes of Cu(II), Co(II), Zn(II), Ni(II) and Pt(II) with N-isonicotinoyl-N′-(3-metoxy-2 hydroxybenzaldehyde)-hydrazone (HL) were synthesized and characterized by different physico-chemical techniques including elemental and thermal analysis, magnetic susceptibility measurements, molar electric conductivity, as well as IR (infrared), 1 [...] Read more.
Hydrazone complexes of Cu(II), Co(II), Zn(II), Ni(II) and Pt(II) with N-isonicotinoyl-N′-(3-metoxy-2 hydroxybenzaldehyde)-hydrazone (HL) were synthesized and characterized by different physico-chemical techniques including elemental and thermal analysis, magnetic susceptibility measurements, molar electric conductivity, as well as IR (infrared), 1H-NMR and 13C-NMR (hydrogen and carbon nuclear magnetic resonance, UV-Vis (ultraviolet-visible), FAB (fast atom bombardment), EPR (electron paramagnetic resonance), and mass spectroscopies. The crystal structure of ligand was determined by single crystal X-ray diffraction studies. Spectral data showed that hydrazone behaves as an ONO tridentate ligand through the azomethine nitrogen, phenolate and keto oxygen atoms. For the copper(II) complexes, metal–ligand bonding parameters were evaluated from the EPR spectra. These parameters indicate the presence of in-plane π bonding. In addition, the f values of complexes 1–4 indicate small distortion from planarity. The effect of these complexes on proliferation of human breast cancer (MCF-7 and SKBR-3), human melanoma (A375), lung adenocarcinoma cells (NCI-H1573) and their antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Candida albicans strains were studied and compared with those of free ligand. The ligand and complexes 1–3 showed significant antimicrobial activity against the Gram-positive bacteria Staphylococcus aureus and Candida albicans in comparison to the control drugs. The complexes 2–4 could be potential antitumor agents, leading to a significant improvement of the cytotoxic activity when compared with HL. Full article
(This article belongs to the Special Issue Metal Based Drugs: Opportunities and Challenges)
►▼ Show Figures

Graphical abstract

10 pages, 423 KiB  
Article
Growth Inhibition of Sulfate-Reducing Bacteria in Produced Water from the Petroleum Industry Using Essential Oils
by Pamella Macedo de Souza 1, Fátima Regina de Vasconcelos Goulart 1, Joana Montezano Marques 1,2, Humberto Ribeiro Bizzo 3, Arie Fitzgerald Blank 4, Claudia Groposo 5, Maíra Paula de Sousa 5, Vanessa Vólaro 6, Celuta Sales Alviano 1, Daniela Sales Alviano Moreno 1 and Lucy Seldin 1,*
1 Instituto de Microbiologia Paulo de Góes, Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941-590, Brazil
2 Instituto de Ciências Biológicas, Universidade Federal do Pará, Pará 66075-900, Brazil
3 Embrapa, Agroindústria de Alimentos, Rio de Janeiro 23020-470 Brazil
4 Departamento de Engenharia Agronômica, Universidade Federal de Sergipe, Sergipe 49.100-000, Brazil
5 CENPES/Petrobras, Rio de Janeiro 21941-915, Brazil
6 Grupo Falcão Bauer, São Paulo 05036-070, Brazil
Molecules 2017, 22(4), 648; https://doi.org/10.3390/molecules22040648 - 19 Apr 2017
Cited by 20 | Viewed by 7000
Abstract
Strategies for the control of sulfate-reducing bacteria (SRB) in the oil industry involve the use of high concentrations of biocides, but these may induce bacterial resistance and/or be harmful to public health and the environment. Essential oils (EO) produced by plants inhibit the [...] Read more.
Strategies for the control of sulfate-reducing bacteria (SRB) in the oil industry involve the use of high concentrations of biocides, but these may induce bacterial resistance and/or be harmful to public health and the environment. Essential oils (EO) produced by plants inhibit the growth of different microorganisms and are a possible alternative for controlling SRB. We aimed to characterize the bacterial community of produced water obtained from a Brazilian petroleum facility using molecular methods, as well as to evaluate the antimicrobial activity of EO from different plants and their major components against Desulfovibrio alaskensis NCIMB 13491 and against SRB growth directly in the produced water. Denaturing gradient gel electrophoresis revealed the presence of the genera Pelobacter and Marinobacterium, Geotoga petraea, and the SRB Desulfoplanes formicivorans in our produced water samples. Sequencing of dsrA insert-containing clones confirmed the presence of sequences related to D. formicivorans. EO obtained from Citrus aurantifolia, Lippia alba LA44 and Cymbopogon citratus, as well as citral, linalool, eugenol and geraniol, greatly inhibited (minimum inhibitory concentration (MIC) = 78 µg/mL) the growth of D. alaskensis in a liquid medium. The same MIC was obtained directly in the produced water with EO from L. alba LA44 (containing 82% citral) and with pure citral. These findings may help to control detrimental bacteria in the oil industry. Full article
(This article belongs to the Special Issue Essential Oils: Chemistry and Bioactivity)
►▼ Show Figures

Graphical abstract

12 pages, 556 KiB  
Article
Chemical Constituents of Supercritical Extracts from Alpinia officinarum and the Feeding Deterrent Activity against Tribolium castaneum
by Mintong Xin 1, Shanshan Guo 1, Wenjuan Zhang 1, Zhufeng Geng 1,2, Junyu Liang 1, Shushan Du 1,*, Zhiwei Deng 2 and Yongyan Wang 1
1 Beijing Key Laboratory of Traditional Chinese Medicine Protection and Utilization, Faculty of Geographical Science, Beijing Normal University, Beijing 100875, China
2 Analytical and Testing Center, Beijing Normal University, Beijing 100875, China
Molecules 2017, 22(4), 647; https://doi.org/10.3390/molecules22040647 - 18 Apr 2017
Cited by 18 | Viewed by 6292
Abstract
Alpinia officinarum has been confirmed to possess bioactivities against some pests. In this work, a sample was obtained from A. officinarum rhizomes by supercritical fluid CO2 extraction (SFE). According to GC-MS analysis, the main chemical components for SFE-sample included benzylacetone (26.77%), 1,7-diphenyl-5-hydroxy-3-heptanone [...] Read more.
Alpinia officinarum has been confirmed to possess bioactivities against some pests. In this work, a sample was obtained from A. officinarum rhizomes by supercritical fluid CO2 extraction (SFE). According to GC-MS analysis, the main chemical components for SFE-sample included benzylacetone (26.77%), 1,7-diphenyl-5-hydroxy-3-heptanone (17.78%), guaiacylacetone (10.03%) and benzenepropanal (7.42%). The essential oil of A. officinarum rhizomes (LD50 = 20.71 μg/adult) exhibited more contact toxicity than SFE extract (LD50 = 82.72 μg/adult) against Tribolium castaneum. From SFE extracts, one new compound, 1-phenyl-4-(16,17-dimethyl-9,13-octadiene)-5-isopentenyl-7-(4”-methoxyl-3”-hydroxyl-phenyl)-3-heptanone (3), together with five known compounds identified as 5-hydroxy-1,7-diphenyl-3-heptanone (1), 1,7-diphenyl-4-hepten-3-one (2), galangin (4), galangin-3-methyl ether (5) and pinocembrin (6), were isolated and their feeding deterrent activities against T. castaneum adults were assessed. It was found that compounds 1–6 had feeding deterrent activities against T. castaneum with feeding deterrent indices of 18.21%, 18.94%, 19.79%, 26.99%, 20.34%, and 35.81%, respectively, at the concentration of 1500 ppm. Hence, the essential oil and SFE extracts/compounds of A. officinarum rhizomes represent promising alternatives in the control of T. castaneum adults. Full article
►▼ Show Figures

Figure 1

8 pages, 1220 KiB  
Article
Metajapogenins A–C, Pregnane Steroids from Shells of Metaplexis japonica
by Hui-Li Yao, Yang Liu, Xiao-Hong Liu, Hua Gao, Kun Liu, Yan-Lin Shao, Xin-Yu Fang and Wei Wang *
School of Pharmacy, Qingdao University, Qingdao 266021, Shandong, China
Molecules 2017, 22(4), 646; https://doi.org/10.3390/molecules22040646 - 17 Apr 2017
Cited by 5 | Viewed by 3951
Abstract
Phytochemical investigation of the shells of Metaplexis japonica (Thunb.) Makino, belonging to the family of Apocynaceae, afforded three new pregnane steroids, metajapogenins A–C, along with three known compounds. The structures of the new compounds were elucidated as 12β,14β,17β-trihydroxypregna-3,5-dien-7,20-dione, 12β,14β,17β,20β-tetrahydroxypregna-3,5-dien-7-one; 3β,12β,14β,17β-tetrahydroxypregn-5-ene-7,20-dione on the basis [...] Read more.
Phytochemical investigation of the shells of Metaplexis japonica (Thunb.) Makino, belonging to the family of Apocynaceae, afforded three new pregnane steroids, metajapogenins A–C, along with three known compounds. The structures of the new compounds were elucidated as 12β,14β,17β-trihydroxypregna-3,5-dien-7,20-dione, 12β,14β,17β,20β-tetrahydroxypregna-3,5-dien-7-one; 3β,12β,14β,17β-tetrahydroxypregn-5-ene-7,20-dione on the basis of extensive spectroscopic evidence derived from 1D; 2D-NMR experiments and mass spectrometry. The known compounds included pergularin; 12-O-acetylpergularin; and pergularin-3-O-β-d-oleandropyranose; which were identified for the first time in the shells of M. japonica. Full article
(This article belongs to the Section Natural Products Chemistry)
►▼ Show Figures

Figure 1

27 pages, 9131 KiB  
Article
Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction
by Bing Lin 1,†, Gen Zhou 1,†, Yi Gong 1, Qi-Di Wei 1, Min-Yi Tian 1, Xiong-Li Liu 1,*, Ting-Ting Feng 1, Ying Zhou 1,* and Wei-Cheng Yuan 2
1 Guizhou Medicine Edicine Edible Plant Resources Research and Development Center, College of Pharmacy, Guizhou University, Guiyang 550025, China
2 Key Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
† These two authors contributed equally to this work.
Molecules 2017, 22(4), 645; https://doi.org/10.3390/molecules22040645 - 17 Apr 2017
Cited by 9 | Viewed by 5478
Abstract
Described herein is the development of a facile and efficient methodology for the synthesis of novel turmerone motif-fused 3,3′-pyrrolidinyl-dispirooxindoles 3–5 via a multicomponent 1,3-dipolar cycloaddition of dienones 2 with azomethine ylides (thermally generated in situfrom isatins and proline or thioproline or sarcosine). Products [...] Read more.
Described herein is the development of a facile and efficient methodology for the synthesis of novel turmerone motif-fused 3,3′-pyrrolidinyl-dispirooxindoles 3–5 via a multicomponent 1,3-dipolar cycloaddition of dienones 2 with azomethine ylides (thermally generated in situfrom isatins and proline or thioproline or sarcosine). Products bearing four or three consecutive stereocenters consist of two oxindole moieties and a pyrrolidinyl core, including vicinal spiroquaternary stereocenters fused in one ring structure were smoothly obtained in high yields (up to 93% yield) with good diastereoselectivity (up to >20:1). Another valuable application of this method was for the design of new hybrid architectures for biological screening through the adequate fusion of these sub-units of turmerone and 3,3′-pyrrolidinyl-dispirooxindole, generating drug-like molecules. Full article
(This article belongs to the Collection Heterocyclic Compounds)
►▼ Show Figures

Graphical abstract

10 pages, 1859 KiB  
Article
Systematic Understanding of the Mechanism of Salvianolic Acid A via Computational Target Fishing
by Shao-Jun Chen * and Ming-Chao Cui
Department of Traditional Chinese Medicine, Zhejiang Pharmaceutical College, 888 Yinxian Avenue Eastern Section, Ningbo 315100, China
Molecules 2017, 22(4), 644; https://doi.org/10.3390/molecules22040644 - 17 Apr 2017
Cited by 35 | Viewed by 7230
Abstract
Salvianolic acid A (SAA) is one of the most abundant water-soluble and potent anti-oxidative compounds isolated from Danshen, a traditional Chinese medicine. A systematic overview of its mechanism of action is yet to be performed. In the present study, the druggability of SAA [...] Read more.
Salvianolic acid A (SAA) is one of the most abundant water-soluble and potent anti-oxidative compounds isolated from Danshen, a traditional Chinese medicine. A systematic overview of its mechanism of action is yet to be performed. In the present study, the druggability of SAA was measured using the TCMSP server, and potential targets of SAA were identified by PharmMapper and DRAR-CPI. Intersecting targets were then assessed by GeneMANIA and GO pathway analysis, and drug-target-pathway networks were constructed to give a visual view. The results showed that SAA has good druggability, and 13 putative protein targets were identified. Network analysis showed that these targets were associated with cancer, metabolism and other physiological processes. In summary, SAA is predicted to target multiple proteins and pathways to form a network that exerts systematic pharmacological effects. Full article
►▼ Show Figures

Figure 1

8 pages, 1257 KiB  
Communication
An Expedient Total Synthesis of Triciribine
by Chen Hu, Zhizhong Ruan, Haixin Ding, Yirong Zhou and Qiang Xiao *
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China
Molecules 2017, 22(4), 643; https://doi.org/10.3390/molecules22040643 - 17 Apr 2017
Cited by 7 | Viewed by 4491
Abstract
In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid [...] Read more.
In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) group and ring closure reaction together to give a tricyclic nucleobase motif. Full article
(This article belongs to the Section Organic Chemistry)
►▼ Show Figures

Graphical abstract

8 pages, 2128 KiB  
Article
Anti-Proliferative Effect of Triterpenoidal Glycosides from the Roots of Anemone vitifolia through a Pro-Apoptotic Way
by Changcai Bai 1,*,†, Yunyun Ye 1,2,†, Xiao Feng 2,†, Ruifeng Bai 2, Lu Han 1, Xiuping Zhou 1, Xinyao Yang 2, Pengfei Tu 2 and Xingyun Chai 2,*
1 Key Laboratory of Hui Medicine Modernization, Ministry of Education, Ningxia Medical University Pharmacy College, Yinchuan 750004, China
2 Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100029, China
† These authors contributed to the paper equally.
Molecules 2017, 22(4), 642; https://doi.org/10.3390/molecules22040642 - 17 Apr 2017
Cited by 10 | Viewed by 4429
Abstract
A cytotoxicity-guided phytochemical investigation of Anemone vitifolia roots led to the isolation of six oleanane saponins (1–6), which were reported from the species for the first time. Their structures were determined by comparing its MS and NMR data with [...] Read more.
A cytotoxicity-guided phytochemical investigation of Anemone vitifolia roots led to the isolation of six oleanane saponins (1–6), which were reported from the species for the first time. Their structures were determined by comparing its MS and NMR data with those in literature. Compounds 1–4 showed significant inhibitory effects on the proliferation of hepatocellular carcinoma HepG2 cells with IC50 values ranging from 2.0 to 8.5 μM, compared to positive control methotrexate with IC50 value of 15.8 μM. Flow cytometry analysis revealed that compounds 1–4 exerted anti-proliferative effects through a pro-apoptotic way of hepatocellular carcinoma cells. Full article
►▼ Show Figures

Figure 1

10 pages, 6177 KiB  
Article
Establishing Reliable Cu-64 Production Process: From Target Plating to Molecular Specific Tumor Micro-PET Imaging
by Qinghua Xie 1,2,†, Hua Zhu 2,†, Feng Wang 2, Xiangxi Meng 3, Qiushi Ren 3, Chuanqin Xia 1,* and Zhi Yang 2,*
1 College of Chemistry, Sichuan University, Chengdu 610064, China
2 Key Laboratory of Carcinogenesis and Translational Research (Ministry of Education), Department of Nuclear Medicine, Peking University Cancer Hospital & Institute, Beijing 100142, China
3 Department of Biomedical Engineering, College of Engineering, Peking University, Beijing 100871, China
† These authors contributed equally to this work.
Molecules 2017, 22(4), 641; https://doi.org/10.3390/molecules22040641 - 17 Apr 2017
Cited by 44 | Viewed by 8634
Abstract
Copper-64 is a useful radioisotope for positron emission tomography (PET). Due to the wide range of applications, the demand of 64Cu with low metallic impurities is increasing. Here we report a simple method for the efficient production of high specific activity 64 [...] Read more.
Copper-64 is a useful radioisotope for positron emission tomography (PET). Due to the wide range of applications, the demand of 64Cu with low metallic impurities is increasing. Here we report a simple method for the efficient production of high specific activity 64Cu using a cyclotron for biomedical application. We designed new equipment based on the plating of enriched 64Ni as the target, and used automated ion exchange chromatography to purify copper-64 efficiently after irradiation and dissolution of the target in good radiochemical and chemical yield and purity. The 64Cu radionuclide produced using 99.32% enriched 64Ni with a density of 61.4 ± 5.0 mg/cm2, reaching a total radioactivity greater than 200 mCi, with specific activity up to 5.6 GBq/μmoL. It was further incorporated into modified monoclonal antibody DOTA-rituximab to synthesize 64Cu-DOTA-rituximab, which was used successfully for micro-PET imaging. Full article
►▼ Show Figures

Figure 1

12 pages, 6893 KiB  
Article
Synthesis and Antiproliferative Activity of Novel All-Trans-Retinoic Acid-Podophyllotoxin Conjugate towards Human Gastric Cancer Cells
by Lei Zhang *, Jing Wang *, Lai Liu, Chengyue Zheng and Yang Wang
School of Pharmacy, Zunyi Medical University, 201 Dalian Road, Zunyi 563003, Guizhou, China
Molecules 2017, 22(4), 628; https://doi.org/10.3390/molecules22040628 - 17 Apr 2017
Cited by 20 | Viewed by 6280
Abstract
With the purpose of creating a multifunctional drug for gastric cancer treatment, a novel all-trans-retinoic acid (ATRA) conjugate with podophyllotoxin (PPT) was designed and synthesized, and its in vitro antiproliferative activity was evaluated against human gastric cancer cell [...] Read more.
With the purpose of creating a multifunctional drug for gastric cancer treatment, a novel all-trans-retinoic acid (ATRA) conjugate with podophyllotoxin (PPT) was designed and synthesized, and its in vitro antiproliferative activity was evaluated against human gastric cancer cell lines using CCK-8 assay. The conjugate, P-A, exhibited significant anticancer activity against MKN-45 and BGC-823 cells with IC50 values of 0.419 ± 0.032 and 0.202 ± 0.055 μM, respectively. Moreover, P-A efficiently triggered cell cycle arrest and induced apoptosis in MKN-45 and BGC-823 cells due to modulation of cell cycle arrest- (CDK1, CDK2, CyclinA and CyclinB1) and apoptosis- (cleaved caspase-3, -8 and -9) related proteins, respectively. Further mechanism studies revealed that P-A could increase the expression levels of RARα and RARβ, and decrease the level of RARγ in MKN-45 and BGC-823 cells. Finally, P-A inhibited the ERK1/2 and AKT signaling in the above two cancer cell lines. More importantly, the underlying mechanisms of P-A were similar to those of precursor PPT but different with the other precursor ATRA. Together, the conjugate P-A was a promising candidate for the potential treatment of human gastric cancer. Full article
(This article belongs to the Collection Efficient Pharmaceutical and Chemical Approaches for Anticancer Therapy: Design, Preliminary Evaluations, and Further Developments)
►▼ Show Figures

Figure 1

9 pages, 1955 KiB  
Article
Expeditious Synthesis of Dianionic-Headed 4-Sulfoalkanoic Acid Surfactants
by Jianhui Jiang 1,2 and Jiaxi Xu 1,*
1 State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, China
2 Engineering Laboratory of Chemical Resources Utilization in South Xinjiang of Xinjiang Production and Construction Corps, College of Life Sciences, Tarim University, Alar, Xinjiang 843300, China
Molecules 2017, 22(4), 640; https://doi.org/10.3390/molecules22040640 - 16 Apr 2017
Cited by 2 | Viewed by 4255
Abstract
4-Sulfoalkanoic acids are a class of important dianionic-headed surfactants. Various 4-sulfoalkanoic acids with straight C8, C10, C12, C14, C16, and C18 chains were synthesized expeditiously through the radical addition of methyl 2-((ethoxycarbonothioyl)thio)acetate to linear terminal olefins and subsequent oxidation with peroxyformic acid. This [...] Read more.
4-Sulfoalkanoic acids are a class of important dianionic-headed surfactants. Various 4-sulfoalkanoic acids with straight C8, C10, C12, C14, C16, and C18 chains were synthesized expeditiously through the radical addition of methyl 2-((ethoxycarbonothioyl)thio)acetate to linear terminal olefins and subsequent oxidation with peroxyformic acid. This is a useful and convenient strategy for the synthesis of dianionic-headed surfactants with a carboxylic acid and sulfonic acid functionalities in the head group region. Full article
(This article belongs to the Section Organic Chemistry)
►▼ Show Figures

Graphical abstract

14 pages, 1646 KiB  
Article
Evaluation of Polyphenolic Content, Antioxidant and Diuretic Activities of Six Fumaria Species
by Ramona Păltinean 1,†, Andrei Mocan 1,2,†, Laurian Vlase 3,*, Ana-Maria Gheldiu 3, Gianina Crișan 1, Irina Ielciu 1, Oliviu Voștinaru 4 and Ovidiu Crișan 5
1 Department of Pharmaceutical Botany, “Iuliu Hațieganu” University of Medicine and Pharmacy, 400337 Cluj-Napoca, Romania
2 ICHAT and Institute for Life Sciences, University of Agricultural Sciences and Veterinary Medicine, Calea Mănăştur 3-5, 400372 Cluj-Napoca, Romania
3 Department of Pharmaceutical Technology and Biopharmaceutics, “Iuliu Hațieganu” University of Medicine and Pharmacy, 400010 Cluj-Napoca, Romania
4 Department of Pharmacology, Physiology and Physiopathology, “Iuliu Hațieganu” University of Medicine and Pharmacy, 400349 Cluj-Napoca, Romania
5 Department of Organic Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 400010 Cluj-Napoca, Romania
† These authors have equal contributions
Molecules 2017, 22(4), 639; https://doi.org/10.3390/molecules22040639 - 15 Apr 2017
Cited by 49 | Viewed by 6799
Abstract
Romanian traditional medicine describes the use of aerial parts of Fumaria species to treat hepatobiliary diseases as well as diuretic agents. The present study aims to investigate the chemical composition, antioxidant properties, and diuretic effects of several Fumaria species. LC/MS analysis revealed that [...] Read more.
Romanian traditional medicine describes the use of aerial parts of Fumaria species to treat hepatobiliary diseases as well as diuretic agents. The present study aims to investigate the chemical composition, antioxidant properties, and diuretic effects of several Fumaria species. LC/MS analysis revealed that Fumaria species contain phenolic acids and high amounts of flavonoids with rutin and isoquercitrin as main compounds. Concerning antioxidant capacity, the most significant results were obtained for F. capreolata and F. vailantii. Both species showed a good correlation between the antioxidant capacity and a high amount of flavonoids. Furthermore, the extracts of F. officinalis and F. schleicheri produced a strong increase in urinary volumetric excretion of saline-loaded rats, 24 h after the oral administration of a single dose of 250 mg/kg bw. Moreover, both extracts of F. officinalis and F. schleicheri increased the urinary excretion of Na+ and K+. Results from the present study offer a new perspective concerning the chemical composition and bioactivities of traditionally used fumitory species. Full article
(This article belongs to the Section Natural Products Chemistry)
►▼ Show Figures

Figure 1

13 pages, 1064 KiB  
Article
Optimization of Ultrasound-Assisted Extraction of Antioxidants from the Mung Bean Coat
by Yue Zhou 1,†, Jie Zheng 1,†, Ren-You Gan 2, Tong Zhou 1, Dong-Ping Xu 1 and Hua-Bin Li 1,3,*
1 Guangdong Provincial Key Laboratory of Food, Nutrition and Health, School of Public Health, Sun Yat-Sen University, Guangzhou 510080, China
2 School of Biological Sciences, The University of Hong Kong, Hong Kong 999077, China
3 South China Sea Bioresource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University, Guangzhou 510006, China
† These authors equally contributed to this paper.
Molecules 2017, 22(4), 638; https://doi.org/10.3390/molecules22040638 - 15 Apr 2017
Cited by 71 | Viewed by 6621
Abstract
Mung bean (Vigna radiata) sprout is commonly consumed as a vegetable, while the coat of the germinated mung bean is a waste. In this paper, an ultrasound-assisted extraction method has been developed to extract natural antioxidants from the seed coat of [...] Read more.
Mung bean (Vigna radiata) sprout is commonly consumed as a vegetable, while the coat of the germinated mung bean is a waste. In this paper, an ultrasound-assisted extraction method has been developed to extract natural antioxidants from the seed coat of mung bean. Several experimental parameters—which included ethanol concentration, solvent/material ratio, ultrasound extraction time, temperature, and power—were studied in single-factor experiments. The interaction of three key experimental parameters (ethanol concentration, solvent/material ratio, and ultrasonic extraction time) was further investigated by response surface method. Besides, traditional extracting methods, including maceration and Soxhlet extraction methods, were also carried out for comparison. The results suggested that the best extracting condition was 37.6% (v/v) of ethanol concentration, 35.1:1 mL/g of solvent/material ratio and ultrasonic extraction of 46.1 min at 70 °C under 500 W ultrasonic irradiation. The antioxidant capacity (178.28 ± 7.39 µmol Trolox/g DW) was much stronger than those obtained by the maceration extraction process (158.66 ± 4.73 µmol Trolox/g DW) and the Soxhlet extraction process (138.42 ± 3.63 µmol Trolox/g DW). In addition, several antioxidant components in the extract were identified and quantified. This study is helpful for value-added utilization of the waste from germinated mung bean. Full article
(This article belongs to the Special Issue Green Extraction of Natural Product: Innovative Techniques, Alternative Solvents and Original Procedures)
►▼ Show Figures

Figure 1

8 pages, 2498 KiB  
Communication
Discovery of an Octahedral Silicon Complex as a Potent Antifungal Agent
by Chen Fu *, Bin Fu, Xixi Peng and Guojian Liao *
College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, China
Molecules 2017, 22(4), 637; https://doi.org/10.3390/molecules22040637 - 15 Apr 2017
Cited by 2 | Viewed by 5159
Abstract
Octahedral transition metal complexes have been shown to have tremendous applications in chemical biology and medicinal chemistry. Meanwhile, structural transition metals can be replaced by inert octahedral silicon in a proof-of-principle study. We here introduce the first example of octahedral silicon complexes, which [...] Read more.
Octahedral transition metal complexes have been shown to have tremendous applications in chemical biology and medicinal chemistry. Meanwhile, structural transition metals can be replaced by inert octahedral silicon in a proof-of-principle study. We here introduce the first example of octahedral silicon complexes, which can very well serve as an efficient antimicrobial agent. The typical silicon arenediolate complex 1 {[(phen)2Si(OO)](PF6)2, with phen = 1,10-phenanthroline, OO = 9,10-phenanthrenediolate} exhibited significant inhibition towards the growth of Cryptococcus neoformans with MIC and MFC values of 4.5 and 11.3 μM, respectively. Moreover, it was fungicidal against both proliferative and quiescent Cryptococcus cells. This work may set the stage for the development of novel antifungal drugs based upon hexacoodinate silicon scaffolds. Full article
(This article belongs to the Special Issue Advances in Silicon Chemistry)
►▼ Show Figures

Graphical abstract

15 pages, 1463 KiB  
Article
Stability of Bioactive Compounds in Broccoli as Affected by Cutting Styles and Storage Time
by Ana Mariel Torres-Contreras 1, Vimal Nair 2, Luis Cisneros-Zevallos 2 and Daniel A. Jacobo-Velázquez 1,*
1 Tecnológico de Monterrey, Escuela de Ingeniería y Ciencias, Centro de Biotecnología FEMSA, Av. Eugenio Garza Sada 2501 Sur, Monterrey 64849, Mexico
2 Department of Horticultural Sciences, Texas A&M University, College Station, TX 77843-2133, USA
Molecules 2017, 22(4), 636; https://doi.org/10.3390/molecules22040636 - 15 Apr 2017
Cited by 62 | Viewed by 9029
Abstract
Broccoli contains bioactive molecules and thus its consumption is related with the prevention of chronic and degenerative diseases. The application of wounding stress to horticultural crops is a common practice, since it is the basis for the fresh-cut produce industry. In this study, [...] Read more.
Broccoli contains bioactive molecules and thus its consumption is related with the prevention of chronic and degenerative diseases. The application of wounding stress to horticultural crops is a common practice, since it is the basis for the fresh-cut produce industry. In this study, the effect of four different cutting styles (CSs) (florets (CS1), florets cut into two even pieces (CS2), florets cut into four even pieces (CS3), and florets processed into chops (CS4)) and storage time (0 and 24 h at 20 °C) on the content of bioactive compounds in broccoli was evaluated. Immediately after cutting, 5-O-caffeoylquinic acid and caffeic acid content increased by 122.4% and 41.6% in CS4 and CS2, respectively. Likewise, after storage, 3-O-caffeoylquinic acid and 5-O-caffeoylquinic acid increased by 46.7% and 98.2%, respectively in CS1. Glucoerucin and gluconasturtiin content decreased by 62% and 50%, respectively in CS3; whereas after storage most glucosinolates increased in CS1. Total isothiocyanates, increased by 133% immediately in CS4, and after storage CS1 showed 65% higher levels of sulforaphane. Total ascorbic acid increased 35% after cutting in CS2, and remained stable after storage. Results presented herein would allow broccoli producers to select proper cutting styles that preserve or increase the content of bioactive molecules. Full article
(This article belongs to the Special Issue Recent Advances in Plant Phenolics)
►▼ Show Figures

Figure 1