Molecules

14 pages, 1433 KiB

Open AccessArticle

RNA Secondary Structure-Based Design of Antisense Peptide Nucleic Acids for Modulating Disease-Associated Aberrant Tau Pre-mRNA Alternative Splicing

by Alan Ann Lerk Ong, Jiazi Tan, Malini Bhadra, Clément Dezanet, Kiran M. Patil, Mei Sian Chong, Ryszard Kierzek, Jean-Luc Decout, Xavier Roca and Gang Chen

Molecules 2019, 24(16), 3020; https://doi.org/10.3390/molecules24163020 - 20 Aug 2019

Cited by 17 | Viewed by 5287

Abstract

Alternative splicing of tau pre-mRNA is regulated by a 5′ splice site (5′ss) hairpin present at the exon 10–intron 10 junction. Single mutations within the hairpin sequence alter hairpin structural stability and/or the binding of splicing factors, resulting in disease-causing aberrant splicing of [...] Read more.

Alternative splicing of tau pre-mRNA is regulated by a 5′ splice site (5′ss) hairpin present at the exon 10–intron 10 junction. Single mutations within the hairpin sequence alter hairpin structural stability and/or the binding of splicing factors, resulting in disease-causing aberrant splicing of exon 10. The hairpin structure contains about seven stably formed base pairs and thus may be suitable for targeting through antisense strands. Here, we used antisense peptide nucleic acids (asPNAs) to probe and target the tau pre-mRNA exon 10 5′ss hairpin structure through strand invasion. We characterized by electrophoretic mobility shift assay the binding of the designed asPNAs to model tau splice site hairpins. The relatively short (10–15 mer) asPNAs showed nanomolar binding to wild-type hairpins as well as a disease-causing mutant hairpin C+19G, albeit with reduced binding strength. Thus, the structural stabilizing effect of C+19G mutation could be revealed by asPNA binding. In addition, our cell culture minigene splicing assay data revealed that application of an asPNA targeting the 3′ arm of the hairpin resulted in an increased exon 10 inclusion level for the disease-associated mutant C+19G, probably by exposing the 5′ss as well as inhibiting the binding of protein factors to the intronic spicing silencer. On the contrary, the application of asPNAs targeting the 5′ arm of the hairpin caused an increased exon 10 exclusion for a disease-associated mutant C+14U, mainly by blocking the 5′ss. PNAs could enter cells through conjugation with amino sugar neamine or by cotransfection with minigene plasmids using a commercially available transfection reagent. Full article

(This article belongs to the Special Issue Peptide Nucleic Acids: Applications in Biomedical Sciences)

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21 pages, 3559 KiB

Open AccessReview

Recent Advances in Conjugated Graft Copolymers: Approaches and Applications

by Tomasz Jarosz, Karolina Gebka and Agnieszka Stolarczyk

Molecules 2019, 24(16), 3019; https://doi.org/10.3390/molecules24163019 - 20 Aug 2019

Cited by 12 | Viewed by 4978

Abstract

The main goal of this mini review is to summarise the most recent progress in the field of conjugated graft copolymers featuring conjugation across the main chain, across side chains or across both. The main approaches to the synthesis of conjugated graft copolymers [...] Read more.

The main goal of this mini review is to summarise the most recent progress in the field of conjugated graft copolymers featuring conjugation across the main chain, across side chains or across both. The main approaches to the synthesis of conjugated graft copolymers are highlighted, and the various trends in the development of new copolymer materials and the intended directions of their applications are explored. Full article

(This article belongs to the Special Issue New Studies of Conjugated Compounds)

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15 pages, 3007 KiB

Open AccessArticle

Self-Assembly of Covalently Linked Porphyrin Dimers at the Solid–Liquid Interface

by Thomas Habets, Dennis Lensen, Sylvia Speller and Johannes A.A.W. Elemans

Molecules 2019, 24(16), 3018; https://doi.org/10.3390/molecules24163018 - 20 Aug 2019

Cited by 6 | Viewed by 3945

Abstract

The synthesis and surface self-assembly behavior of two types of metal-porphyrin dimers is described. The first dimer type consists of two porphyrins linked via a rigid conjugated spacer, and the second type has an alkyne linker, which allows rotation of the porphyrin moieties [...] Read more.

The synthesis and surface self-assembly behavior of two types of metal-porphyrin dimers is described. The first dimer type consists of two porphyrins linked via a rigid conjugated spacer, and the second type has an alkyne linker, which allows rotation of the porphyrin moieties with respect to each other. The conjugated dimers were equipped with two copper or two manganese centers, while the flexible dimers allowed a modular built-up that also made the incorporation of two different metal centers possible. The self-assembly of the new porphyrin dimers at a solid–liquid interface was investigated at the single-molecule scale using scanning tunneling microscopy (STM). All dimers formed monolayers, of which the stability and the internal degree of ordering of the molecules depended on the metal centers in the porphyrins. While in all monolayers the dimers were oriented coplanar with respect to the underlying surface (‘face-on’), the flexible dimer containing a manganese and a copper center could be induced, via the application of a voltage pulse in the STM setup, to self-assemble into monolayers in which the porphyrin dimers adopted a non-common perpendicular (‘edge-on’) geometry with respect to the surface. Full article

(This article belongs to the Special Issue Spatial Organization of Multi-Porphyrins for Pre-Defined Properties)

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12 pages, 1483 KiB

Open AccessArticle

One Pot and Metal-Free Approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones

by Jiaqi Yuan, Qian He, Shanshan Song, Xiaofei Zhang, Zehong Miao and Chunhao Yang

Molecules 2019, 24(16), 3017; https://doi.org/10.3390/molecules24163017 - 20 Aug 2019

Cited by 4 | Viewed by 3761

Abstract

Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency, mild conditions, and benign functional group compatibility was reported. A variety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert [...] Read more.

Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency, mild conditions, and benign functional group compatibility was reported. A variety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities. Full article

(This article belongs to the Collection Heterocyclic Compounds)

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10 pages, 1357 KiB

Open AccessArticle

Determination of Flavonoid Glycosides by UPLC-MS to Authenticate Commercial Lemonade

by Ying Xue, Lin-Sen Qing, Li Yong, Xian-Shun Xu, Bin Hu, Ming-Qing Tang and Jing Xie

Molecules 2019, 24(16), 3016; https://doi.org/10.3390/molecules24163016 - 20 Aug 2019

Cited by 12 | Viewed by 3844

Abstract

So far, there is no report on the quality evaluation of lemonade available in the market. In this study, a sample preparation method was developed for the determination of flavonoid glycosides by ultra-performance liquid chromatography–mass spectrometry (UPLC-MS) based on vortex-assisted dispersive liquid-liquid microextraction. [...] Read more.

So far, there is no report on the quality evaluation of lemonade available in the market. In this study, a sample preparation method was developed for the determination of flavonoid glycosides by ultra-performance liquid chromatography–mass spectrometry (UPLC-MS) based on vortex-assisted dispersive liquid-liquid microextraction. First, potential flavonoids in lemonade were scanned and identified by ultra-performance liquid chromatography–time of flight mass spectrometry (UPLC-TOF/MS). Five flavonoid glycosides were identified as eriocitrin, narirutin, hesperidin, rutin, and diosmin according to the molecular formula provided by TOF/MS and subsequent confirmation of the authentic standard. Then, an ultra-performance liquid chromatography–triple quadrupole mass spectrometry (UPLC-QqQ/MS) method was developed to determine these five flavonoid glycosides in lemonade. The results showed that the content of rutin in some lemonade was unreasonably high. We suspected that many illegal manufacturers achieved the goal of low-cost counterfeiting lemonade by adding rutin. This suggested that it was necessary for relevant departments of the state to make stricter regulations on the quality standards of lemonade beverages. Full article

(This article belongs to the Special Issue Advances in Chemical Analysis Procedures (Part I): Extraction and Instrument Configuration)

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29 pages, 3598 KiB

Open AccessArticle

Eosin Removal by Cetyl Trimethylammonium-Cloisites: Influence of the Surfactant Solution Type and Regeneration Properties

by Fethi Kooli, Souad Rakass, Yan Liu, Mostafa Abboudi, Hicham Oudghiri Hassani, Sheikh Muhammad Ibrahim, Fahd Al Wadaani and Rawan Al-Faze

Molecules 2019, 24(16), 3015; https://doi.org/10.3390/molecules24163015 - 20 Aug 2019

Cited by 7 | Viewed by 3431

Abstract

The effect of the counteranion of hexadecyltrimethylammonium salts on the physico-chemical properties of organoclays was investigated, using a selected natural clay mineral with a cation exchange capacity of 95 meq/100 g. The uptake amount of C₁₆ cations was dependent on the hexadecyltrimethylammonium [...] Read more.

The effect of the counteranion of hexadecyltrimethylammonium salts on the physico-chemical properties of organoclays was investigated, using a selected natural clay mineral with a cation exchange capacity of 95 meq/100 g. The uptake amount of C₁₆ cations was dependent on the hexadecyltrimethylammonium (C₁₆) salt solution used, the organoclay prepared from C₁₆Br salt solution exhibited a value of 1. 05 mmole/g higher than those prepared from C₁₆Cl and C₁₆OH salt solutions. The basal spacing of these organoclays was in the range of 1.81 nm to 2.10 nm, indicating a similar orientation of the intercalated surfactants, and could indicated that the excess amount of surfactants, above the cation exchange capacity of 0.95 meq/g could be adsorbed on the external surface of the clay mineral sheets. These organoclays were found to be stable in neutral, acidic, and basic media. The thermal stability of these organoclays was carried out using thermogravimetric analysis and in-situ X-ray diffraction (XRD) techniques. The decomposition of the surfactant occurred at a maximum temperature of 240 °C, accompanied with a decrease of the basal spacing value close to 1.42 nm. The application of these organoclays was investigated to remove an acidic dye, eosin. The removal amount was related to the initial used concentrations, the amount of the surfactants contents, and to the preheated temperatures of the organoclays. The removal was found to be endothermic process with a maximum amount of 55 mg of eosin/g of organoclay. The value decreased to 25 mg/g, when the intercalated surfactants were decomposed. The reuse of these organoclays was limited to four regeneration recycles with a reduction of 20 to 30%. However, noticeable reduction between 35% to 50% of the initial efficiency, was achieved after the fifth cycle, depending of the used organoclays. Full article

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17 pages, 1206 KiB

Open AccessArticle

Rapid Characterization of Chemical Components in Edible Mushroom Sparassis crispa by UPLC-Orbitrap MS Analysis and Potential Inhibitory Effects on Allergic Rhinitis

by Zhixin Wang, Jingyu Liu, Xiangjian Zhong, Jinjie Li, Xin Wang, Linlin Ji and Xiaoya Shang

Molecules 2019, 24(16), 3014; https://doi.org/10.3390/molecules24163014 - 20 Aug 2019

Cited by 18 | Viewed by 4507

Abstract

Sparassis crispa is a kind of edible fungus widely grows in the north temperate zone, which shows various medicinal properties. Due to the complexity of chemical constitutes of this species, few investigations have acquired a comprehensive configuration for the chemical profile of it. [...] Read more.

Sparassis crispa is a kind of edible fungus widely grows in the north temperate zone, which shows various medicinal properties. Due to the complexity of chemical constitutes of this species, few investigations have acquired a comprehensive configuration for the chemical profile of it. In this study, a strategy based on ultra-high performance liquid chromatography (UPLC) combined with Orbitrap mass spectrometer (MS) was established for rapidly characterizing various chemical components in S. crispa. Through the summarized MS/MS fragmentation patterns of reference compounds and systematic identification strategy, a total of 110 components attributed to six categories were identified for the first time. Moreover, allergic rhinitis (AR) is a worldwide inflammatory disease seriously affecting human health, and the development of drugs to treat AR has been a topic of interest. It has been reported that the extracts of S. crispa showed obvious inhibitory effects on degranulation of mast cell- and allergen-induced IgE and proinflammatory mediators, but the active components and specific mechanism were still not clear. Src family kinases (SFKs) participate in the initial stage of allergy occurrence, which are considered the targets of AR treatment. Herein, on the basis of that self-built chemical database, virtual screening was applied to predict the potential SFKs inhibitors in S. crispa, using known crystal structures of Hck, Lyn, Fyn, and Syk as receptors, followed by the anti-inflammatory activity evaluation for screened hits by intracellular calcium mobilization assay. As results, sparoside A was directly confirmed to have strong anti-inflammatory activity with an IC₅₀ value of 5.06 ± 0.60 μM. This study provides a useful elucidation for the chemical composition of S. crispa, and demonstrated its potential inhibitory effects on AR, which could promote the research and development of effective agents from natural resources. Full article

(This article belongs to the Section Natural Products Chemistry)

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9 pages, 1017 KiB

Open AccessArticle

Modeling Solid State Stability for Speciation: A Ten-Year Long Study

by Roberta Risoluti, Giuseppina Gullifa, Elena Carcassi, Francesca Buiarelli, Li W. Wo and Stefano Materazzi

Molecules 2019, 24(16), 3013; https://doi.org/10.3390/molecules24163013 - 20 Aug 2019

Cited by 3 | Viewed by 2495

Abstract

Speciation studies are based on fundamental models that relate the properties of biomimetic coordination compounds to the stability of the complexes. In addition to the classic approach based on solution studies, solid state properties have been recently proposed as supporting tools to understand [...] Read more.

Speciation studies are based on fundamental models that relate the properties of biomimetic coordination compounds to the stability of the complexes. In addition to the classic approach based on solution studies, solid state properties have been recently proposed as supporting tools to understand the bioavailability of the involved metal. A ten-year long systematic study of several different complexes of imidazole substituted ligands with transition metal ions led our group to the definition of a model based on experimental evidences. This model revealed to be a useful tool to predict the stability of such coordination complexes and is based on the induced behavior under thermal stress. Several different solid state complexes were characterized by Thermally Induced Evolved Gas Analysis by Mass Spectrometry (TI-EGA-MS). This hyphenated technique provides fundamental information to determine the solid state properties and to create a model that relates stability to coordination. In this research, the model resulting from our ten-year long systematic study of complexes of transition metal ions with imidazole substituted ligands is described. In view of a systematic addition of information, new complexes of Cu(II), Zn(II), or Cd(II) with 2-propyl-4,5-imidazoledicarboxylic acid were precipitated, characterized, and studied by means of Thermally Induced Evolved Gas Analysis performed by mass spectrometry (TI-EGA-MS). The hyphenated approach was applied to enrich the information related to thermally induced steps, to confirm the supposed decomposition mechanism, and to determine the thermal stability of the studied complexes. Results, again, allowed supporting the theory that only two main characteristic and common thermally induced decomposition behaviors join the imidazole substituted complexes studied by our group. These two behaviors could be considered as typical trends and the model allowed to predict coordination behavior and to provide speciation information. Full article

(This article belongs to the Special Issue Chemical Speciation of Organic and Inorganic components of Environmental and Biological Interest in Natural Fluids: Behaviour, Interaction and Sequestration)

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13 pages, 3313 KiB

Open AccessArticle

Nitrogen Self-Doped Activated Carbons Derived from Bamboo Shoots as Adsorbent for Methylene Blue Adsorption

by Bingbing Mi, Jingxin Wang, Hongzhong Xiang, Fang Liang, Jianfei Yang, Zixing Feng, Tao Zhang, Wanhe Hu, Xianmiao Liu, Zhijia Liu and Benhua Fei

Molecules 2019, 24(16), 3012; https://doi.org/10.3390/molecules24163012 - 20 Aug 2019

Cited by 23 | Viewed by 4795

Abstract

Bamboo shoots, a promising renewable biomass, mainly consist of carbohydrates and other nitrogen-related compounds, such as proteins, amino acids and nucleotides. In this work, nitrogen self-doped activated carbons derived from bamboo shoots were prepared via a simultaneous carbonization and activation process. The adsorption [...] Read more.

Bamboo shoots, a promising renewable biomass, mainly consist of carbohydrates and other nitrogen-related compounds, such as proteins, amino acids and nucleotides. In this work, nitrogen self-doped activated carbons derived from bamboo shoots were prepared via a simultaneous carbonization and activation process. The adsorption properties of the prepared samples were evaluated by removing methylene blue from waste water. The factors that affect the adsorption process were examined, including initial concentration, contact time and pH of methylene blue solution. The resulting that BSNC-800-4 performed better in methylene blue removal from waste water, due to its high specific surface area (2270.9 m² g⁻¹), proper pore size (2.19 nm) and relatively high nitrogen content (1.06%). Its equilibrium data were well fitted to Langmuir isotherm model with a maximum monolayer adsorption capacity of 458 mg g⁻¹ and a removal efficiency of 91.7% at methylene blue concentration of 500 mg L⁻¹. The pseudo-second-order kinetic model could be used to accurately estimate the carbon material’s (BSNC-800-4) adsorption process. The adsorption mechanism between methylene blue solution and BSNC-800-4 was controlled by film diffusion. This study provides an alternative way to develop nitrogen self-doped activated carbons to better meet the needs of the adsorption applications. Full article

(This article belongs to the Special Issue Advances in Porous Materials)

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16 pages, 2446 KiB

Open AccessArticle

A Mass Spectrometry-Based Study Shows that Volatiles Emitted by Arthrobacter agilis UMCV2 Increase the Content of Brassinosteroids in Medicago truncatula in Response to Iron Deficiency Stress

by Idolina Flores-Cortez, Robert Winkler, Arturo Ramírez-Ordorica, Ma. Isabel Cristina Elizarraraz-Anaya, María Teresa Carrillo-Rayas, Eduardo Valencia-Cantero and Lourdes Macías-Rodríguez

Molecules 2019, 24(16), 3011; https://doi.org/10.3390/molecules24163011 - 20 Aug 2019

Cited by 5 | Viewed by 3676

Abstract

Iron is an essential plant micronutrient. It is a component of numerous proteins and participates in cell redox reactions; iron deficiency results in a reduction in nutritional quality and crop yields. Volatiles from the rhizobacterium Arthrobacter agilis UMCV2 induce iron acquisition mechanisms in [...] Read more.

Iron is an essential plant micronutrient. It is a component of numerous proteins and participates in cell redox reactions; iron deficiency results in a reduction in nutritional quality and crop yields. Volatiles from the rhizobacterium Arthrobacter agilis UMCV2 induce iron acquisition mechanisms in plants. However, it is not known whether microbial volatiles modulate other metabolic plant stress responses to reduce the negative effect of iron deficiency. Mass spectrometry has great potential to analyze metabolite alterations in plants exposed to biotic and abiotic factors. Direct liquid introduction-electrospray-mass spectrometry was used to study the metabolite profile in Medicago truncatula due to iron deficiency, and in response to microbial volatiles. The putatively identified compounds belonged to different classes, including pigments, terpenes, flavonoids, and brassinosteroids, which have been associated with defense responses against abiotic stress. Notably, the levels of these compounds increased in the presence of the rhizobacterium. In particular, the analysis of brassinolide by gas chromatography in tandem with mass spectrometry showed that the phytohormone increased ten times in plants grown under iron-deficient growth conditions and exposed to microbial volatiles. In this mass spectrometry-based study, we provide new evidence on the role of A. agilis UMCV2 in the modulation of certain compounds involved in stress tolerance in M. truncatula. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)

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15 pages, 6352 KiB

Open AccessArticle

Optimization of Degradation Conditions with PRG, a Polysaccharide from Phellinus ribis, by RSM and the Neuroprotective Activity in PC12 Cells Damaged by Aβ_25–35

by Pei Yang, Juan Jin, Qian Liu, Dongmei Ma, Jia Li, Yongqing Zhang and Yuhong Liu

Molecules 2019, 24(16), 3010; https://doi.org/10.3390/molecules24163010 - 20 Aug 2019

Cited by 18 | Viewed by 3387

Abstract

In the previous work, we found PRG, a polysaccharide from Phellinus ribis, exhibited neurotrophic activity. To obtain an active structural unit with lower molecular weight, PRG was degraded to prepare the degraded PRG (DPRG) using ascorbic acid and H₂O₂ [...] Read more.

In the previous work, we found PRG, a polysaccharide from Phellinus ribis, exhibited neurotrophic activity. To obtain an active structural unit with lower molecular weight, PRG was degraded to prepare the degraded PRG (DPRG) using ascorbic acid and H₂O₂. The aim of the paper was to obtain DPRG by optimizing the degradation conditions using response surface methodology (RSM) and to study its protective effects of PC12 cells induced by Aβ_25–35. The optimum conditions were as follows; the concentration of H₂O₂-Vc was 17 mM and degradation temperature was 50 °C; when degradation time was 1.6 h, the experimental response value of PC12 cell viability was 83.4 ± 0.15%, which was in accordance with the predicted value (83.5%). We also studied the protective effects of DPRG against the Aβ_25–35-induced neurotoxicity and explored the underlying mechanism. The results showed that treatment with DPRG could attenuate PC12 cells death. The mechanism was relative to the inhibition of cell apoptosis by increasing the MMP level and decreasing the protein expression of cytochrome C (Cytc) in PC12 cells. In conclusion, DPRG with lower molecular weight was obtained successfully. It possessed neuroprotective properties and might be a candidate for neurodegenerative disease treatment. Full article

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17 pages, 441 KiB

Open AccessReview

Application of Chitosan in Bone and Dental Engineering

by Alicia Aguilar, Naimah Zein, Ezeddine Harmouch, Brahim Hafdi, Fabien Bornert, Damien Offner, François Clauss, Florence Fioretti, Olivier Huck, Nadia Benkirane-Jessel and Guoqiang Hua

Molecules 2019, 24(16), 3009; https://doi.org/10.3390/molecules24163009 - 19 Aug 2019

Cited by 196 | Viewed by 10549

Abstract

Chitosan is a deacetylated polysaccharide from chitin, the natural biopolymer primarily found in shells of marine crustaceans and fungi cell walls. Upon deacetylation, the protonation of free amino groups of the d-glucosamine residues of chitosan turns it into a polycation, which can [...] Read more.

Chitosan is a deacetylated polysaccharide from chitin, the natural biopolymer primarily found in shells of marine crustaceans and fungi cell walls. Upon deacetylation, the protonation of free amino groups of the d-glucosamine residues of chitosan turns it into a polycation, which can easily interact with DNA, proteins, lipids, or negatively charged synthetic polymers. This positive-charged characteristic of chitosan not only increases its solubility, biodegradability, and biocompatibility, but also directly contributes to the muco-adhesion, hemostasis, and antimicrobial properties of chitosan. Combined with its low-cost and economic nature, chitosan has been extensively studied and widely used in biopharmaceutical and biomedical applications for several decades. In this review, we summarize the current chitosan-based applications for bone and dental engineering. Combining chitosan-based scaffolds with other nature or synthetic polymers and biomaterials induces their mechanical properties and bioactivities, as well as promoting osteogenesis. Incorporating the bioactive molecules into these biocomposite scaffolds accelerates new bone regeneration and enhances neovascularization in vivo. Full article

(This article belongs to the Special Issue Chitosan-Based Nanomaterials for Biomedical Applications)

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16 pages, 1072 KiB

Open AccessArticle

Qualitative and Quantitative Evaluation of Heat-Induced Changes in Polyphenols and Antioxidant Capacity in Prunus domestica L. By-products

by Anna Michalska, Aneta Wojdyło, Joanna Majerska, Krzysztof Lech and Jessica Brzezowska

Molecules 2019, 24(16), 3008; https://doi.org/10.3390/molecules24163008 - 19 Aug 2019

Cited by 14 | Viewed by 3793

Abstract

Plum pomace, an agro-industrial waste product has received attention due to the worldwide popularity of plums. During convection, the content of flavan-3-ols decrease, except drying at 90 °C, whereas the content of i.e., chlorogenic, 3-p- and 4-p-coumaroylquinic acids, quercetin [...] Read more.

Plum pomace, an agro-industrial waste product has received attention due to the worldwide popularity of plums. During convection, the content of flavan-3-ols decrease, except drying at 90 °C, whereas the content of i.e., chlorogenic, 3-p- and 4-p-coumaroylquinic acids, quercetin rutinoside, and galactoside was observed to increase along with the increase in process temperature. The highest content of all identified polyphenols was found in plum pomace powders obtained using a combination of convective at 90 °C and microwave vacuum drying (MVD) at 120 W, whereas the highest retention of the group consisted of phenolic acids, flavonols, and anthocyanins was noted when CD 70 °C/MVD 120 W was used, pointing to a strong influence of the type of polyphenols on their changes caused by drying. The correlations between TEAC ABTS and the sum of flavonoids (r = 0.634) and anthocyanins (r = 0.704) were established. The multiple regression analysis showed that polyphenol content was more strongly affected by drying time than by maximum temperature, whereas antioxidant capacity was more influenced by maximum temperature of sample than by drying time. Full article

(This article belongs to the Special Issue Physicochemical Properties of Food)

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27 pages, 3495 KiB

Open AccessReview

Review of Alternative Solvents for Green Extraction of Food and Natural Products: Panorama, Principles, Applications and Prospects

by Farid Chemat, Maryline Abert Vian, Harish Karthikeyan Ravi, Boutheina Khadhraoui, Soukaina Hilali, Sandrine Perino and Anne-Sylvie Fabiano Tixier

Molecules 2019, 24(16), 3007; https://doi.org/10.3390/molecules24163007 - 19 Aug 2019

Cited by 346 | Viewed by 25788

Abstract

In recent years, almost all extraction processes in the perfume, cosmetic, pharmaceutical, food ingredients, nutraceuticals, biofuel and fine chemical industries rely massively on solvents, the majority of which have petroleum origins. The intricate processing steps involved in the industrial extraction cycle makes it [...] Read more.

In recent years, almost all extraction processes in the perfume, cosmetic, pharmaceutical, food ingredients, nutraceuticals, biofuel and fine chemical industries rely massively on solvents, the majority of which have petroleum origins. The intricate processing steps involved in the industrial extraction cycle makes it increasingly difficult to predict the overall environmental impact; despite the tremendous energy consumption and the substantial usage of solvents, often the yields are indicated in decimals. The ideal alternative solvents suitable for green extraction should have high solvency, high flash points with low toxicity and low environmental impacts, be easily biodegradable, obtained from renewable (non-petrochemical) resources at a reasonable price and should be easy to recycle without any deleterious effect to the environment. Finding the perfect solvent that meets all the aforementioned requirements is a challenging task, thus the decision for the optimum solvent will always be a compromise depending on the process, the plant and the target molecules. The objective of this comprehensive review is to furnish a vivid picture of current knowledge on alternative, green solvents used in laboratories and industries alike for the extraction of natural products focusing on original methods, innovation, protocols, and development of safe products. Full article

(This article belongs to the Special Issue Green Extraction of Natural Products)

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15 pages, 2035 KiB

Open AccessArticle

Eruca sativa Meal against Diabetic Neuropathic Pain: An H₂S-Mediated Effect of Glucoerucin

by Elena Lucarini, Eleonora Pagnotta, Laura Micheli, Carmen Parisio, Lara Testai, Alma Martelli, Vincenzo Calderone, Roberto Matteo, Luca Lazzeri, Lorenzo Di Cesare Mannelli and Carla Ghelardini

Molecules 2019, 24(16), 3006; https://doi.org/10.3390/molecules24163006 - 19 Aug 2019

Cited by 26 | Viewed by 4999

Abstract

The management of pain in patients affected by diabetic neuropathy still represents an unmet therapeutic need. Recent data highlighted the pain-relieving efficacy of glucosinolates deriving from Brassicaceae. The purpose of this study was to evaluate the anti-hyperalgesic efficacy of Eruca sativa defatted seed [...] Read more.

The management of pain in patients affected by diabetic neuropathy still represents an unmet therapeutic need. Recent data highlighted the pain-relieving efficacy of glucosinolates deriving from Brassicaceae. The purpose of this study was to evaluate the anti-hyperalgesic efficacy of Eruca sativa defatted seed meal, along with its main glucosinolate, glucoerucin (GER), on diabetic neuropathic pain induced in mice by streptozotocin (STZ). The mechanism of action was also investigated. Hypersensitivity was assessed by paw pressure and cold plate tests after the acute administration of the compounds. Once bio-activated by myrosinase, both E. sativa defatted meal (1 g kg⁻¹ p.o.) and GER (100 µmol kg⁻¹ p.o., equimolar to meal content) showed a dose-dependent pain-relieving effect in STZ-diabetic mice, but the meal was more effective than the glucosinolate. The co-administration with H₂S scavengers abolished the pain relief mediated by both E. sativa meal and GER. Their effect was also prevented by selectively blocking Kv7 potassium channels. Repeated treatments with E. sativa meal did not induce tolerance to the anti-hypersensitive effect. In conclusion, E. sativa meal can be suggested as a new nutraceutical tool for pain relief in patients with diabetic neuropathy. Full article

(This article belongs to the Special Issue Natural Products and Drug Discovery)

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21 pages, 4201 KiB

Open AccessReview

Hydrogels Based on Schiff Base Linkages for Biomedical Applications

by Junpeng Xu, Yi Liu and Shan-hui Hsu

Molecules 2019, 24(16), 3005; https://doi.org/10.3390/molecules24163005 - 19 Aug 2019

Cited by 320 | Viewed by 19311

Abstract

Schiff base, an important family of reaction in click chemistry, has received significant attention in the formation of self-healing hydrogels in recent years. Schiff base reversibly reacts even in mild conditions, which allows hydrogels with self-healing ability to recover their structures and functions [...] Read more.

Schiff base, an important family of reaction in click chemistry, has received significant attention in the formation of self-healing hydrogels in recent years. Schiff base reversibly reacts even in mild conditions, which allows hydrogels with self-healing ability to recover their structures and functions after damages. Moreover, pH-sensitivity of the Schiff base offers the hydrogels response to biologically relevant stimuli. Different types of Schiff base can provide the hydrogels with tunable mechanical properties and chemical stabilities. In this review, we summarized the design and preparation of hydrogels based on various types of Schiff base linkages, as well as the biomedical applications of hydrogels in drug delivery, tissue regeneration, wound healing, tissue adhesives, bioprinting, and biosensors. Full article

(This article belongs to the Special Issue Self-Healing Materials)

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11 pages, 1880 KiB

Open AccessArticle

Purification and Identification of Antioxidant Peptides from Schizochytrium Limacinum Hydrolysates by Consecutive Chromatography and Electrospray Ionization-Mass Spectrometry

by Xiao Hu, Xianqing Yang, Qiong Wu, Laihao Li, Yanyan Wu, Shengjun Chen, Ruijie Li and Jiaoyan Ren

Molecules 2019, 24(16), 3004; https://doi.org/10.3390/molecules24163004 - 19 Aug 2019

Cited by 19 | Viewed by 3612

Abstract

Schizochytrium limacinum residue was hydrolyzed with various proteases (papain, trypsin, Flavourzyme, Protamex, and Alcalase 2.4L) to obtain antioxidative peptides. The results showed that the S. limacinum hydrolysates (SLHs) prepared with compound proteases (Protamex and Alcalase 2.4L) had the highest antioxidant activity, which was [...] Read more.

Schizochytrium limacinum residue was hydrolyzed with various proteases (papain, trypsin, Flavourzyme, Protamex, and Alcalase 2.4L) to obtain antioxidative peptides. The results showed that the S. limacinum hydrolysates (SLHs) prepared with compound proteases (Protamex and Alcalase 2.4L) had the highest antioxidant activity, which was measured using methods such as 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging ability (IC₅₀ = 1.28 mg/mL), hydroxyl radical scavenging ability (IC₅₀ = 1.66 mg/mL), and reducing power (1.42 at 5.0 mg/mL). The hydrolysates were isolated and purified by ultrafiltration, gel filtration chromatography, and reverse-phase high-performance liquid chromatography (RP-HPLC). Through analysis of electrospray ionization-mass spectrometer (ESI-MS/MS), the purified antioxidant peptide was identified as Pro-Tyr-Lys (406 Da). Finally, the identified peptide was synthesized for evaluating its antioxidant activity. The •OH scavenging ability and reducing power of Pro-Tyr-Lys were comparable to those of reduced L-glutathione (GSH). These results demonstrated that the antioxidant peptides from SLHs could potentially be used as effective antioxidants. Full article

(This article belongs to the Special Issue The Optimized Production, Purification, Characterization and Application of Proteins/Enzymes)

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18 pages, 1735 KiB

Open AccessArticle

Comparative Analysis of Phytochemical Composition of Gamma-Irradiated Mutant Cultivars of Chrysanthemum morifolium

by Jaihyunk Ryu, Bomi Nam, Bo-Ram Kim, Sang Hoon Kim, Yeong Deuk Jo, Joon-Woo Ahn, Jin-Baek Kim, Chang Hyun Jin and Ah-Reum Han

Molecules 2019, 24(16), 3003; https://doi.org/10.3390/molecules24163003 - 19 Aug 2019

Cited by 31 | Viewed by 5237

Abstract

The flowers of chrysanthemum species are used as a herbal tea and in traditional medicine. In addition, members of the genus have been selected to develop horticultural cultivars of diverse floral colors and capitulum forms. In this research, we investigated the phytochemical composition [...] Read more.

The flowers of chrysanthemum species are used as a herbal tea and in traditional medicine. In addition, members of the genus have been selected to develop horticultural cultivars of diverse floral colors and capitulum forms. In this research, we investigated the phytochemical composition of eight gamma-irradiation mutant cultivars of Chrysanthemum morifolium and their original cultivars. The mutant chrysanthemum cultivars were generated by treatment with various doses of ⁶⁰Co gamma irradiation of stem cuttings of three commercial chrysanthemum cultivars as follows: ‘ARTI-Dark Chocolate’ (50Gy), ‘ARTI-Purple Lady’ (30 Gy), and ‘ARTI-Yellow Star’ (50 Gy) derived from ‘Noble Wine’; ‘ARTI-Red Star’ (50 Gy) and ‘ARTI-Rising Sun’ (30 Gy) from ‘Pinky’; ‘ARTI-Purple’ (40 Gy) and ‘ARTI-Queen’ (30 Gy) from ‘Argus’; and ‘ARTI-Rollypop’ (70 Gy) from ‘Plaisir d’amour’. Quantitative analysis of flavonoids, phenolic acids, anthocyanins, and carotenoids in the flowers of the 12 chrysanthemum cultivars was performed using high performance liquid chromatography-diode array detector-electrospray ionization mass spectrometry (HPLC-DAD-ESIMS). Essential oils from the flowers of these cultivars were analyzed by gas chromatography–mass spectrometry (GC-MS). The mutant cultivars, ‘ARTI-Dark Chocolate’, ‘ARTI-Purple Lady’, ‘ARTI-Purple’, and ‘ARTI-Queen’ showed higher total amounts of flavonoid and phenolic acid compared with those of the respective original cultivars. The mutant cultivars, ‘ARTI-Dark Chocolate’, ‘ARTI-Purple Lady’ and ‘ARTI-Purple’, which produce purple to pink petals, contained more than two-times higher amounts of anthocyanins compared with those of their original cultivars. Of the mutant cultivars, ‘ARTI-Yellow Star’ in which petal color was changed to yellow, showed the greatest accumulation of carotenoids. Ninety-nine volatile compounds were detected, of which hydrocarbons and terpenoids were abundant in all cultivars analyzed. This is the first report that demonstrated the phytochemical analysis of novel chrysanthemum cultivars derived from C. morifolium hydrid using HPLC-DAD-ESIMS and GC-MS. These findings suggest that the selected mutant chrysanthemum cultivars show potential as a functional source of phytochemicals associated with the abundance of health-beneficial components, as well as good source for horticulture and pigment industries. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products)

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14 pages, 2333 KiB

Open AccessFeature PaperArticle

Protective Effects Induced by Two Polyphenolic Liquid Complexes from Olive (Olea europaea, mainly Cultivar Coratina) Pressing Juice in Rat Isolated Tissues Challenged with LPS

by Lucia Recinella, Annalisa Chiavaroli, Giustino Orlando, Luigi Menghini, Claudio Ferrante, Lorenzo Di Cesare Mannelli, Carla Ghelardini, Luigi Brunetti and Sheila Leone

Molecules 2019, 24(16), 3002; https://doi.org/10.3390/molecules24163002 - 19 Aug 2019

Cited by 24 | Viewed by 3719

Abstract

MOMAST^(®) HY100 and MOMAST^(®) HP30 are polyphenolic liquid complexes from olive pressing juice with a total polyphenolic content of 100 g/kg (at least 50% as hydroxytyrosol) and 36 g/kg (at least 30% as hydroxytyrosol), respectively. We investigated the potential protective role [...] Read more.

MOMAST^(®) HY100 and MOMAST^(®) HP30 are polyphenolic liquid complexes from olive pressing juice with a total polyphenolic content of 100 g/kg (at least 50% as hydroxytyrosol) and 36 g/kg (at least 30% as hydroxytyrosol), respectively. We investigated the potential protective role of MOMAST^(®) HY100 and MOMAST^(®) HP30 on isolated rat colon, liver, heart, and prefrontal cortex specimens treated with Escherichia coli lipopolysaccharide (LPS), a validated ex vivo model of inflammation, by measuring the production of prostaglandin (PG)E₂, 8-iso-PGF_2α, lactate dehydrogenase (LDH), as well as cyclooxygenase (COX)-2, tumor necrosis factor α (TNFα), and inducible nitric oxide synthase (iNOS) mRNA levels. MOMAST^(®) HY100 decreased LPS-stimulated PGE₂ and LDH levels in all tested tissues. Following treatment with MOMAST^(®) HY100, we found a significant reduction in iNOS levels in prefrontal cortex and heart specimens, COX-2 and TNFα mRNA levels in heart specimens, and 8-iso-PGF_2α levels in liver specimens. On the other hand, MOMAST^(®) HP30 was found to blunt COX-2, TNFα, and iNOS mRNA levels, as well as 8-iso-PGF_2α in cortex, liver, and colon specimens. MOMAST^(®) HP30 was also found to decrease PGE₂ levels in liver specimens, while it decreased iNOS mRNA, LDH, and 8-iso-PGF_2α levels in heart specimens. Both MOMAST^(®) HY100 and MOMAST^(®) HP30 exhibited protective effects on multiple inflammatory and oxidative stress pathways. Full article

(This article belongs to the Special Issue Plant Extracts: Biological and Pharmacological Activity)

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9 pages, 3108 KiB

Open AccessCommunication

Understanding Conformational Preferences of Atropisomeric Hydrazides and Its Influence on Excited State Transformations in Crystalline Media

by Akila Iyer, Angel Ugrinov and J. Sivaguru

Molecules 2019, 24(16), 3001; https://doi.org/10.3390/molecules24163001 - 19 Aug 2019

Cited by 4 | Viewed by 3336

Abstract

Hydrazides derivatives were evaluated to understand the role of N–N bond in dictating the outcome of photoreactions in the solid state. Full article

(This article belongs to the Special Issue Supramolecular Organic Photochemistry)

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14 pages, 1441 KiB

Open AccessArticle

In Vitro Inhibitory Effects of APINACA on Human Major Cytochrome P450, UDP-Glucuronosyltransferase Enzymes, and Drug Transporters

by Sunjoo Kim, Won-Gu Choi, Mihwa Kwon, Sowon Lee, Yong-Yeon Cho, Joo Young Lee, Han Chang Kang, Im-Sook Song and Hye Suk Lee

Molecules 2019, 24(16), 3000; https://doi.org/10.3390/molecules24163000 - 19 Aug 2019

Cited by 11 | Viewed by 3372

Abstract

APINACA (known as AKB48, N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide), an indazole carboxamide synthetic cannabinoid, has been used worldwide as a new psychoactive substance. Drug abusers take various drugs concomitantly, and therefore, it is necessary to characterize the potential of APINACA-induced drug–drug interactions due to the modulation [...] Read more.

APINACA (known as AKB48, N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide), an indazole carboxamide synthetic cannabinoid, has been used worldwide as a new psychoactive substance. Drug abusers take various drugs concomitantly, and therefore, it is necessary to characterize the potential of APINACA-induced drug–drug interactions due to the modulation of drug-metabolizing enzymes and transporters. In this study, the inhibitory effects of APINACA on eight major human cytochrome P450s (CYPs) and six uridine 5′-diphospho-glucuronosyltransferases (UGTs) in human liver microsomes, as well as on the transport activities of six solute carrier transporters and two efflux transporters in transporter-overexpressed cells, were investigated. APINACA exhibited time-dependent inhibition of CYP3A4-mediated midazolam 1′-hydroxylation (K_i, 4.5 µM; k_inact, 0.04686 min⁻¹) and noncompetitive inhibition of UGT1A9-mediated mycophenolic acid glucuronidation (K_i, 5.9 µM). APINACA did not significantly inhibit the CYPs 1A2, 2A6, 2B6, 2C8/9/19, or 2D6 or the UGTs 1A1, 1A3, 1A4, 1A6, or 2B7 at concentrations up to 100 µM. APINACA did not significantly inhibit the transport activities of organic anion transporter (OAT)1, OAT3, organic anion transporting polypeptide (OATP)1B1, OATP1B3, organic cation transporter (OCT)1, OCT2, P-glycoprotein, or breast cancer resistance protein at concentrations up to 250 μM. These data suggest that APINACA can cause drug interactions in the clinic via the inhibition of CYP3A4 or UGT1A9 activities. Full article

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13 pages, 1366 KiB

Open AccessArticle

Drug-Target Interaction Prediction Based on Drug Fingerprint Information and Protein Sequence

by Yang Li, Yu-An Huang, Zhu-Hong You, Li-Ping Li and Zheng Wang

Molecules 2019, 24(16), 2999; https://doi.org/10.3390/molecules24162999 - 19 Aug 2019

Cited by 25 | Viewed by 3854

Abstract

The identification of drug-target interactions (DTIs) is a critical step in drug development. Experimental methods that are based on clinical trials to discover DTIs are time-consuming, expensive, and challenging. Therefore, as complementary to it, developing new computational methods for predicting novel DTI is [...] Read more.

The identification of drug-target interactions (DTIs) is a critical step in drug development. Experimental methods that are based on clinical trials to discover DTIs are time-consuming, expensive, and challenging. Therefore, as complementary to it, developing new computational methods for predicting novel DTI is of great significance with regards to saving cost and shortening the development period. In this paper, we present a novel computational model for predicting DTIs, which uses the sequence information of proteins and a rotation forest classifier. Specifically, all of the target protein sequences are first converted to a position-specific scoring matrix (PSSM) to retain evolutionary information. We then use local phase quantization (LPQ) descriptors to extract evolutionary information in the PSSM. On the other hand, substructure fingerprint information is utilized to extract the features of the drug. We finally combine the features of drugs and protein together to represent features of each drug-target pair and use a rotation forest classifier to calculate the scores of interaction possibility, for a global DTI prediction. The experimental results indicate that the proposed model is effective, achieving average accuracies of 89.15%, 86.01%, 82.20%, and 71.67% on four datasets (i.e., enzyme, ion channel, G protein-coupled receptors (GPCR), and nuclear receptor), respectively. In addition, we compared the prediction performance of the rotation forest classifier with another popular classifier, support vector machine, on the same dataset. Several types of methods previously proposed are also implemented on the same datasets for performance comparison. The comparison results demonstrate the superiority of the proposed method to the others. We anticipate that the proposed method can be used as an effective tool for predicting drug-target interactions on a large scale, given the information of protein sequences and drug fingerprints. Full article

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14 pages, 1562 KiB

Open AccessArticle

Fish Scale Valorization by Hydrothermal Pretreatment Followed by Enzymatic Hydrolysis for Gelatin Hydrolysate Production

by Yiqi Zhang, Dan Tu, Qing Shen and Zhiyuan Dai

Molecules 2019, 24(16), 2998; https://doi.org/10.3390/molecules24162998 - 19 Aug 2019

Cited by 47 | Viewed by 6525

Abstract

Protein hydrolysates from fish by-products have good process suitability and bioavailability in the food industry. The objective of this work was to develop a method for protein recovery from fish scales and evaluate the hydrolysis of the scale protein. The effect of the [...] Read more.

Protein hydrolysates from fish by-products have good process suitability and bioavailability in the food industry. The objective of this work was to develop a method for protein recovery from fish scales and evaluate the hydrolysis of the scale protein. The effect of the hydrothermal process on protein recovery, degree of hydrolysis (DH) and structural properties of the hydrolysates was investigated. Results showed that hydrothermal treatment could enhance protein recovery of tilapia scales without demineralization and dramatically improve the DH of the hydrolysates. The hydrothermal treated scales showed a better protein recovery (84.81%) and DH (12.88%) and released peptides more efficiently than that of the conventional treated samples. The obtained gelatin hydrolysates mainly distributed in the range of 200–2000 Da with an angiotensin I-converting enzyme (ACE) IC₅₀ value of 0.73 mg/mL. The ACE inhibitory activity of gelatin hydrolysates was stable under high temperature, pH and gastrointestinal proteases. Hydrothermal treatment followed by enzymatic hydrolysis offers a potential solution for preparation of gelatin hydrolysates for food ingredients from fish processing by-products. Full article

(This article belongs to the Special Issue Bioactives from Bioprocessing: Sources and Production)

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13 pages, 1126 KiB

Open AccessFeature PaperReview

Bee Venom: Overview of Main Compounds and Bioactivities for Therapeutic Interests

by Rim Wehbe, Jacinthe Frangieh, Mohamad Rima, Dany El Obeid, Jean-Marc Sabatier and Ziad Fajloun

Molecules 2019, 24(16), 2997; https://doi.org/10.3390/molecules24162997 - 19 Aug 2019

Cited by 210 | Viewed by 23344

Abstract

Apitherapy is an alternate therapy that relies on the usage of honeybee products, most importantly bee venom for the treatment of many human diseases. The venom can be introduced into the human body by manual injection or by direct bee stings. Bee venom [...] Read more.

Apitherapy is an alternate therapy that relies on the usage of honeybee products, most importantly bee venom for the treatment of many human diseases. The venom can be introduced into the human body by manual injection or by direct bee stings. Bee venom contains several active molecules such as peptides and enzymes that have advantageous potential in treating inflammation and central nervous system diseases, such as Parkinson’s disease, Alzheimer’s disease, and amyotrophic lateral sclerosis. Moreover, bee venom has shown promising benefits against different types of cancer as well as anti-viral activity, even against the challenging human immunodeficiency virus (HIV). Many studies described biological activities of bee venom components and launched preclinical trials to improve the potential use of apitoxin and its constituents as the next generation of drugs. The aim of this review is to summarize the main compounds of bee venom, their primary biological properties, mechanisms of action, and their therapeutic values in alternative therapy strategies. Full article

(This article belongs to the Special Issue Natural Toxins/Molecules (and Derivatives) from Animal Venoms: from Basic Research to Therapeutic Applications 2019)

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14 pages, 4537 KiB

Open AccessArticle

Facile Formation of Anatase/Rutile TiO₂ Nanocomposites with Enhanced Photocatalytic Activity

by Jing He, Yi-en Du, Yang Bai, Jing An, Xuemei Cai, Yongqiang Chen, Pengfei Wang, Xiaojing Yang and Qi Feng

Molecules 2019, 24(16), 2996; https://doi.org/10.3390/molecules24162996 - 19 Aug 2019

Cited by 160 | Viewed by 7540

Abstract

Anatase/rutile mixed-phase TiO₂ nanoparticles were synthesized through a simple sol-gel route with further calcination using inexpensive titanium tetrachloride as a titanium source, which effectively reduces the production cost. The structural and optical properties of the prepared materials were characterized by X-ray diffraction [...] Read more.

Anatase/rutile mixed-phase TiO₂ nanoparticles were synthesized through a simple sol-gel route with further calcination using inexpensive titanium tetrachloride as a titanium source, which effectively reduces the production cost. The structural and optical properties of the prepared materials were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), and UV-vis adsorption. The specific surface area was also analyzed by Brunauer–Emmett–Teller (BET) method. The anatase/rutile mixed-phase TiO₂ nanocomposites containing of rod-like, cuboid, and some irregularly shaped anatase nanoparticles (exposed {101} facets) with sizes ranging from tens to more than 100 nanometers, and rod-like rutile nanoparticles (exposed {110} facets) with sizes ranging from tens to more than 100 nanometers. The photocatalytic activities of the obtained anatase/rutile mixed-phase TiO₂ nanoparticles were investigated and compared by evaluating the degradation of hazardous dye methylene blue (MB) under ultraviolet light illumination. Compared to the commercial Degussa P25-TiO₂, the mixed-phase TiO₂ nanocomposites show better photocatalytic activity, which can be attributed to the optimal anatase to rutile ratio and the specific exposed crystal surface on the surface. The anatase/rutile TiO₂ nanocomposites obtained at pH 1.0 (pH1.0-TiO₂) show the best photocatalytic activity, which can be attributed to the optimal heterojunction structure, the smaller average particle size, and the presence of a specific exposed crystal surface. The enhanced photocatalytic activity makes the prepared anatase/rutile TiO₂ photocatalysts a potential candidate in the removal of the organic dyes from colored wastewater. Full article

(This article belongs to the Special Issue Nanocatalysis)

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12 pages, 2526 KiB

Open AccessArticle

Development of Organelle Replacement Therapy Using a Stearyl-Polyhistidine Peptide against Lysosomal Storage Disease Cells

by Taiki Hayashi, Riku Okamoto, Tsuyoshi Kawano and Takashi Iwasaki

Molecules 2019, 24(16), 2995; https://doi.org/10.3390/molecules24162995 - 18 Aug 2019

Cited by 8 | Viewed by 4199

Abstract

We previously reported on a polyhistidine peptide, His16 peptide, as a new cell-penetrating peptide. This peptide is anticipated to be a new carrier for drug delivery systems (DDSs) for targeting intracellular lysosomes because it can transport macromolecules (e.g., liposomes) into these organelles. In [...] Read more.

We previously reported on a polyhistidine peptide, His16 peptide, as a new cell-penetrating peptide. This peptide is anticipated to be a new carrier for drug delivery systems (DDSs) for targeting intracellular lysosomes because it can transport macromolecules (e.g., liposomes) into these organelles. In the present study, we examined the application of His16 peptide as a DDS carrier against lysosomal storage disease (LSD) cells. LSDs are metabolic disorders caused by loss of specific lysosomal enzymes. For the treatment of LSD cells, we devised a system designated organelle replacement therapy (ORT). ORT is a strategy for transporting exogenous lysosomes containing all kinds of lysosomal enzymes from normal cells into endogenous lysosomes in LSD cells using His16 peptide. To develop the ORT system, we prepared His16 peptide-modified healthy lysosomes (His16-Lyso) by insertion of a stearyl-His16 peptide into a hydrophobic region in the lysosomal membrane. His16-Lyso showed cellular uptake and localization to endogenous lysosomes in LSD cells. His16-Lyso also restored the proliferation of LSD cells, which otherwise showed slower proliferation than normal cells. These results suggested that His16-Lyso replenished deficient lysosomal enzymes in LSD cells. The results further suggest that His16-Lyso are promising candidates as a treatment tool for LSD cells and to establish a foundation for ORT. Full article

(This article belongs to the Special Issue Cell-Penetrating Peptides (CPPs))

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12 pages, 1752 KiB

Open AccessArticle

Optimization of Ultrasonic-Assisted Extraction and Purification of Zeaxanthin and Lutein in Corn Gluten Meal

by Litao Wang, Weihang Lu, Jiali Li, Jinxia Hu, Ruifang Ding, Mei Lv and Qibao Wang

Molecules 2019, 24(16), 2994; https://doi.org/10.3390/molecules24162994 - 18 Aug 2019

Cited by 30 | Viewed by 6907

Abstract

Zeaxanthin and lutein have a wide range of pharmacological applications. In this study, we conducted systematic experimental research to optimize antioxidant extraction based on detection, extraction, process amplification, and purification. An ultrasonic-assisted method was used to extract zeaxanthin and lutein with high efficiency [...] Read more.

Zeaxanthin and lutein have a wide range of pharmacological applications. In this study, we conducted systematic experimental research to optimize antioxidant extraction based on detection, extraction, process amplification, and purification. An ultrasonic-assisted method was used to extract zeaxanthin and lutein with high efficiency from corn gluten meal. Firstly, the effects of solid-liquid ratio, extraction temperature, and ultrasonic extraction time on the extraction of zeaxanthin were investigated in single-factor experiments. The optimization extraction parameters of zeaxanthin and lutein with ethanol solvent were obtained using the response surface methodology (RSM) as follows: liquid–solid ratio of 7.9:1, extraction temperature of 56 °C, and extraction time of 45 min. The total content of zeaxanthin and lutein was 0.501%. The optimum extraction experimental parameters were verified by process amplification, and we confirmed that the parameters of the extraction process optimized using the RSM design are reliable and precise. Zeaxanthin and lutein from crude extract of corn gluten were separated and purified using silica gel column chromatography with the purity of zeaxanthin increasing from 0.28% to 31.5% (about 110 times) and lutein from 0.25% to 16.3% (about 65 times), which could be used for large-scale industrial production of carotenoids. Full article

(This article belongs to the Special Issue Natural Additives in Food II)

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14 pages, 4823 KiB

Open AccessArticle

Study on the Material Basis of Neuroprotection of Myrica rubra Bark

by Shengnan Shen, Mengjun Zhao, Chenchen Li, Qi Chang, Xinmin Liu, Yonghong Liao and Ruile Pan

Molecules 2019, 24(16), 2993; https://doi.org/10.3390/molecules24162993 - 18 Aug 2019

Cited by 8 | Viewed by 3579

Abstract

Background: Increasing attention has been given to the search for neuroprotective ingredients from natural plants. Myrica rubra bark (MRB) has been used in traditional oriental medicine for over thousand years and has potential neuroprotection. Methods and Results: Ultra-performance liquid chromatography quadrupole [...] Read more.

Background: Increasing attention has been given to the search for neuroprotective ingredients from natural plants. Myrica rubra bark (MRB) has been used in traditional oriental medicine for over thousand years and has potential neuroprotection. Methods and Results: Ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS) was used to identify the compounds in MRB extract, and the MTT assay was performed to evaluate the neuroprotection of six major compounds from MRB against glutamate-induced damage in PC12 cells. The result displayed nineteen compounds were identified, and myricitrin and myricanol 11-sulfate were shown to have neuroprotection, which prevented cell apoptosis through alleviating oxidative stress by reducing the levels of reactive oxygen species and methane dicarboxylic aldehyde, as well as by enhancing the activities of superoxide dismutase. Conclusions: Several active compounds from MRB may offer neuroprotection and have the potential for the development of new drugs against central nervous system diseases. Full article

(This article belongs to the Section Analytical Chemistry)

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12 pages, 1397 KiB

Open AccessArticle

Chemical Constituents of Salix babylonica L. and Their Antibacterial Activity Against Gram-Positive and Gram-Negative Animal Bacteria

by Eddy Nathalye González-Alamilla, Manases Gonzalez-Cortazar, Benjamín Valladares-Carranza, Marco Antonio Rivas-Jacobo, Camelia Alejandra Herrera-Corredor, Deyanira Ojeda-Ramírez, Adrian Zaragoza-Bastida and Nallely Rivero-Perez

Molecules 2019, 24(16), 2992; https://doi.org/10.3390/molecules24162992 - 18 Aug 2019

Cited by 25 | Viewed by 5148

Abstract

The principle of animal wellbeing, which states that animals should be free from pain, injury, and disease, is difficult to maintain, because microorganisms are most frequently found to be resistant or multi-resistant to drugs. The secondary metabolites of plants are an alternative for [...] Read more.

The principle of animal wellbeing, which states that animals should be free from pain, injury, and disease, is difficult to maintain, because microorganisms are most frequently found to be resistant or multi-resistant to drugs. The secondary metabolites of plants are an alternative for the treatment of these microorganisms. The aim of this work was to determine the antibacterial effect of Salix babylonica L. hydroalcoholic extract (SBHE) against Escherichia coli, Staphylococcus aureus and Listeria monocytogenes, and identify the compounds associated with the activity. The SBHE showed activity against the three strains, and was subjected to a bipartition, obtaining aqueous fraction (ASB) with moderate activity and organic fraction (ACSB) with good activity against the three strains. The chromatographic separation of ACSB, allowed us to obtain ten fractions (F1AC to F10AC), and only three showed activity (F7AC, F8AC and F10AC). In F7AC, five compounds were identified preliminary by GC-MS, in F8AC and F10AC were identified luteolin (1) and luteolin 7-O-glucoside (2) by HPLC, respectively. The best antibacterial activity was obtained with F7AC (Listeria monocytogenes; MIC: 0.78 mg/mL, MBC: 0.78 mg/mL) and F8AC (Staphylococcus aureus; MIC: 0.39 mg/mL; MBC: 0.78 mg/mL). The results indicated that the compounds obtained from SBHE can be used as an alternative treatment against these microorganisms and, by this mechanism, contribute to animal and human health. Full article

(This article belongs to the Special Issue Implication of Natural Compounds in Animal Wellbeing)

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19 pages, 1523 KiB

Open AccessArticle

Bioactivity of Methoxylated and Methylated 1-Hydroxynaphthalene-2-Carboxanilides: Comparative Molecular Surface Analysis

by Hana Michnová, Šárka Pospíšilová, Tomáš Goněc, Iva Kapustíková, Peter Kollár, Violetta Kozik, Robert Musioł, Izabela Jendrzejewska, Ján Vančo, Zdeněk Trávníček, Alois Čížek, Andrzej Bąk and Josef Jampílek

Molecules 2019, 24(16), 2991; https://doi.org/10.3390/molecules24162991 - 18 Aug 2019

Cited by 15 | Viewed by 3712

Abstract

A series of twenty-six methoxylated and methylated N-aryl-1-hydroxynaphthalene- 2-carboxanilides was prepared and characterized as potential anti-invasive agents. The molecular structure of N-(2,5-dimethylphenyl)-1-hydroxynaphthalene-2-carboxamide as a model compound was determined by single-crystal X-ray diffraction. All the analysed compounds were tested against the reference [...] Read more.

A series of twenty-six methoxylated and methylated N-aryl-1-hydroxynaphthalene- 2-carboxanilides was prepared and characterized as potential anti-invasive agents. The molecular structure of N-(2,5-dimethylphenyl)-1-hydroxynaphthalene-2-carboxamide as a model compound was determined by single-crystal X-ray diffraction. All the analysed compounds were tested against the reference strain Staphylococcus aureus and three clinical isolates of methicillin-resistant S. aureus as well as against Mycobacterium tuberculosis and M. kansasii. In addition, the inhibitory profile of photosynthetic electron transport in spinach (Spinacia oleracea L.) chloroplasts was specified. In vitro cytotoxicity of the most effective compounds was tested on the human monocytic leukaemia THP-1 cell line. The activities of N-(3,5-dimethylphenyl)-, N-(3-fluoro-5-methoxy-phenyl)- and N-(3,5-dimethoxyphenyl)-1-hydroxynaphthalene-2-carbox- amide were comparable with or even better than the commonly used standards ampicillin and isoniazid. All promising compounds did not show any cytotoxic effect at the concentration >30 µM. Moreover, an in silico evaluation of clogP features was performed for the entire set of the carboxamides using a range of software lipophilicity predictors, and cross-comparison with the experimentally determined lipophilicity (log k), in consensus lipophilicity estimation, was conducted as well. Principal component analysis was employed to illustrate noticeable variations with respect to the molecular lipophilicity (theoretical/experimental) and rule-of-five violations. Additionally, ligand-oriented studies for the assessment of the three-dimensional quantitative structure–activity relationship profile were carried out with the comparative molecular surface analysis to determine electron and/or steric factors that potentially contribute to the biological activities of the investigated compounds. Full article

(This article belongs to the Special Issue ECSOC-22)

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