Molecules

15 pages, 3646 KiB

Open AccessArticle

Preparation and Application of Bioshell Calcium Oxide (BiSCaO) Nanoparticle-Dispersions with Bactericidal Activity

by Yoko Sato, Masayuki Ishihara, Shingo Nakamura, Koichi Fukuda, Tomohiro Takayama, Sumiyo Hiruma, Kaoru Murakami, Masanori Fujita and Hidetaka Yokoe

Molecules 2019, 24(18), 3415; https://doi.org/10.3390/molecules24183415 - 19 Sep 2019

Cited by 20 | Viewed by 3881

Abstract

Scallop-shell powder (SSP) heated at high temperature exhibits high pH and broad antimicrobial activity. Bioshell calcium oxide (BiSCaO) is an SSP composed mainly of calcium oxide. It is poorly water-soluble under alkaline conditions and the generated precipitate can plug spray nozzles. The aim [...] Read more.

Scallop-shell powder (SSP) heated at high temperature exhibits high pH and broad antimicrobial activity. Bioshell calcium oxide (BiSCaO) is an SSP composed mainly of calcium oxide. It is poorly water-soluble under alkaline conditions and the generated precipitate can plug spray nozzles. The aim of this study was to establish that BiSCaO dispersion caused no significant CaO loss and plugging of spray nozzles, and to evaluate its deodorization and microbicidal abilities and its ability to reduce the concentrations of NO₂⁻ and NO₃⁻. BiSCaO dispersions were prepared by mixing various concentrations of BiSCaO suspension, while phosphate compounds such as Na₃PO₄, Na₂HPO₄ or NaH₂PO₄ and the pH, average diameter, zeta potential, and form of the compounds with cryo-SEM were evaluated. We evaluated deodorization using tainted pork meat and microbicidal efficacy using contaminated suspension with normal bacterial flora. The concentration of NO₂⁻ and NO₃⁻ after mixing BiSCaO dispersion and pure water containing a high proportion of NO₂⁻ and NO₃⁻ were measured. BiSCaO dispersion formed with Na₂HPO₄, whose ratio to BiSCaO was 60%, showed a high pH (>12), a small particle diameter (>181 nm) and was stable for seven days. The BiSCaO dispersion showed higher deodorization and microbicidal activities than SSP-Ca(OH)₂, which was mainly composed of Ca(OH)₂. BiSCaO, but not SSP-Ca(OH)₂, could reduce the concentration of NO₂⁻ and NO₃⁻ by more than 90% within 15 min. We developed a stable BiSCaO dispersion, and it had high deodorization and microbicidal efficacy. These activities of BiSCaO might result from the high pH caused by CaO hydration and a reduction activity causing active radical species. Full article

(This article belongs to the Special Issue Frontiers of Antimicrobial Nanoparticles)

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19 pages, 3402 KiB

Open AccessArticle

Selectively Charged and Zwitterionic Analogues of the Smallest Immunogenic Structure of Streptococcus Pneumoniae Type 14

by Tiziana Gragnani, Doretta Cuffaro, Silvia Fallarini, Grazia Lombardi, Felicia D’Andrea and Lorenzo Guazzelli

Molecules 2019, 24(18), 3414; https://doi.org/10.3390/molecules24183414 - 19 Sep 2019

Cited by 1 | Viewed by 3399

Abstract

Zwitterionic polysaccharides (ZPs) have been shown in recent years to display peculiar immunological properties, thus attracting the interest of the carbohydrate research community. To fully elucidate the mechanisms underlying these properties and exploit the potential of this kind of structures, in depth studies [...] Read more.

Zwitterionic polysaccharides (ZPs) have been shown in recent years to display peculiar immunological properties, thus attracting the interest of the carbohydrate research community. To fully elucidate the mechanisms underlying these properties and exploit the potential of this kind of structures, in depth studies are still required. In this context, the preparation of two cationic, an anionic, as well as two zwitterionic tetrasaccharide analogues of the smallest immunogenic structure of Streptococcus pneumoniae type 14 (SP14) capsular polysaccharide are presented. By exploiting a block strategy, the negative charge has been installed on the non-reducing end of the lactose unit of the tetrasaccharide and the positive charge either on the non-reducing end of the lactosamine moiety or on an external linker. These structures have then been tested by competitive ELISA, showing that the structural variations we made do not modify the affinity of the neutral compound to binding to a specific antibody. However, lower efficacies than the natural SP14 compound were observed. The results obtained, although promising, point to the need to further elongate the polysaccharide structure, which is likely too short to cover the entire epitopes. Full article

(This article belongs to the Special Issue Carbohydrates in Synthesis)

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13 pages, 3323 KiB

Open AccessArticle

Design of Peptidomimetic Functionalized Cholesterol Based Lipid Nanoparticles for Efficient Delivery of Therapeutic Nucleic Acids

by Ehexige Ehexige, Tsogzolmaa Ganbold, Xiang Yu, Shuqin Han and Huricha Baigude

Molecules 2019, 24(18), 3413; https://doi.org/10.3390/molecules24183413 - 19 Sep 2019

Cited by 6 | Viewed by 4266

Abstract

Lipid nanoparticles (LNP) are the most potent carriers for the delivery of nucleic acid-based therapeutics. The first FDA approved a short interfering RNA (siRNA) drug that uses a cationic LNP system for the delivery of siRNA against human transthyretin (hTTR). However, preparation of [...] Read more.

Lipid nanoparticles (LNP) are the most potent carriers for the delivery of nucleic acid-based therapeutics. The first FDA approved a short interfering RNA (siRNA) drug that uses a cationic LNP system for the delivery of siRNA against human transthyretin (hTTR). However, preparation of such LNP involves tedious multi-step synthesis with relatively low yields. In the present study, we synthesized cationic peptidomimetic functionalized cholesterol (denote Chorn) in straightforward chemical approaches with high yield. When formulated with helper lipids, Chorn LNPs complexed with siRNA to form nanoparticles with an average diameter of 150 nm to 200 nm. Chorn LNP mediated transfection of a green fluorescence protein (GFP) expressing plasmid resulted in 60% GFP positive cells. Moreover, Chorn LNP delivered siRNA against polo-like kinase 1 (Plk1), a disease related gene in cancer cells and efficiently suppressed the expression of the gene, resulting in significant morphological changes in the cell nuclei. Our data suggested that cholesterol based cationic LNP, prepared through a robust chemical strategy, may provide a promising siRNA delivery system. Full article

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38 pages, 10970 KiB

Open AccessReview

Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

by Zhonglei Wang

Molecules 2019, 24(18), 3412; https://doi.org/10.3390/molecules24183412 - 19 Sep 2019

Cited by 28 | Viewed by 8466

Abstract

Chirality is one of the most important attributes for its presence in a vast majority of bioactive natural products and pharmaceuticals. Asymmetric organocatalysis methods have emerged as a powerful methodology for the construction of highly enantioenriched structural skeletons of the target molecules. Due [...] Read more.

Chirality is one of the most important attributes for its presence in a vast majority of bioactive natural products and pharmaceuticals. Asymmetric organocatalysis methods have emerged as a powerful methodology for the construction of highly enantioenriched structural skeletons of the target molecules. Due to their extensive application of organocatalysis in the total synthesis of bioactive molecules and some of them have been used in the industrial synthesis of drugs have attracted increasing interests from chemists. Among the chiral organocatalysts, chiral secondary amines (MacMillan’s catalyst and Jorgensen’s catalyst) have been especially considered attractive strategies because of their impressive efficiency. Herein, we outline advances in the asymmetric total synthesis of natural products and relevant drugs by using the strategy of chiral secondary amine catalyzed reactions of α,β-unsaturated aldehydes in the last eighteen years. Full article

(This article belongs to the Special Issue Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday)

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11 pages, 3980 KiB

Open AccessArticle

Non-Enzymatic Electrochemical Sensor Based on Sliver Nanoparticle-Decorated Carbon Nanotubes

by Dongqing Xu, Bingbing Hou, Lisheng Qian, Xueji Zhang and Guodong Liu

Molecules 2019, 24(18), 3411; https://doi.org/10.3390/molecules24183411 - 19 Sep 2019

Cited by 18 | Viewed by 3378

Abstract

The authors report a non-enzymatic electrochemical sensor based on a sliver nanoparticle-decorated carbon nanotube (AgNPs-MWCNT). Highly-dispersed AgNPs were loaded on the MWCNT surface though a simple and facile two-step method. The morphology, components, and the size of the AgNPs-MWCNT nanocomposite were characterized by [...] Read more.

The authors report a non-enzymatic electrochemical sensor based on a sliver nanoparticle-decorated carbon nanotube (AgNPs-MWCNT). Highly-dispersed AgNPs were loaded on the MWCNT surface though a simple and facile two-step method. The morphology, components, and the size of the AgNPs-MWCNT nanocomposite were characterized by transmission electron microscopy, X-ray diffraction, and ICP analysis. Benefitting from the synergistic effect between the AgNPs and MWCNT, the AgNPs-MWCNT nanocomposite exhibited high electrocatalytic activity for H₂O₂; the AgNPs-MWCNT electrochemical sensor was prepared by coating the AgNPs-MWCNT nanocomposite on a glassy carbon electrode, and it showed a fast and sensitive response to H₂O₂ with a linear range of 1 to 1000 μM. The detection limit was 0.38 μM (S/N = 3). The sensor was applied to detect H₂O₂ in spiked human blood serum samples with satisfactory results. Full article

(This article belongs to the Special Issue Recent Advances of Bioanalytical Electrochemistry of Molecules)

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34 pages, 1701 KiB

Open AccessReview

Nano-and Micromotors Designed for Cancer Therapy

by Luisa Sonntag, Juliane Simmchen and Veronika Magdanz

Molecules 2019, 24(18), 3410; https://doi.org/10.3390/molecules24183410 - 19 Sep 2019

Cited by 54 | Viewed by 8046

Abstract

Research on nano- and micromotors has evolved into a frequently cited research area with innovative technology envisioned for one of current humanities’ most deadly problems: cancer. The development of cancer targeting drug delivery strategies involving nano-and micromotors has been a vibrant field of [...] Read more.

Research on nano- and micromotors has evolved into a frequently cited research area with innovative technology envisioned for one of current humanities’ most deadly problems: cancer. The development of cancer targeting drug delivery strategies involving nano-and micromotors has been a vibrant field of study over the past few years. This review aims at categorizing recent significant results, classifying them according to the employed propulsion mechanisms starting from chemically driven micromotors, to field driven and biohybrid approaches. In concluding remarks of section 2, we give an insight into shape changing micromotors that are envisioned to have a significant contribution. Finally, we critically discuss which important aspects still have to be addressed and which challenges still lie ahead of us. Full article

(This article belongs to the Special Issue Nanomaterials for Cancer Diagnosis and Therapy)

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13 pages, 4878 KiB

Open AccessArticle

Drug Repurposing as an Antitumor Agent: Disulfiram-Mediated Carbonic Anhydrase 12 and Anion Exchanger 2 Modulation to Inhibit Cancer Cell Migration

by Soyoung Hwang, Dong Min Shin and Jeong Hee Hong

Molecules 2019, 24(18), 3409; https://doi.org/10.3390/molecules24183409 - 19 Sep 2019

Cited by 18 | Viewed by 3814

Abstract

Disulfiram has been used in the treatment of alcoholism and exhibits an anti-tumor effect. However, the intracellular mechanism of anti-tumor activity of Disulfiram remains unclear. In this study, we focused on the modulatory role of Disulfiram via oncogenic factor carbonic anhydrase CA12 and [...] Read more.

Disulfiram has been used in the treatment of alcoholism and exhibits an anti-tumor effect. However, the intracellular mechanism of anti-tumor activity of Disulfiram remains unclear. In this study, we focused on the modulatory role of Disulfiram via oncogenic factor carbonic anhydrase CA12 and its associated transporter anion exchanger AE2 in lung cancer cell line A549. The surface expression of CA12 and AE2 were decreased by Disulfiram treatment with a time-dependent manner. Disulfiram treatment did not alter the expression of Na⁺-bicarbonate cotransporters, nor did it affect autophagy regulation. The chloride bicarbonate exchanger activity of A549 cells was reduced by Disulfiram treatment in a time-dependent manner without change in the resting pH level. The expression and activity of AE2 and the expression of CA12 were also reduced by Disulfiram treatment in the breast cancer cell line. An invasion assay and cell migration assay revealed that Disulfiram attenuated the invasion and migration of A549 cells. In conclusion, the attenuation of AE2 and its supportive enzyme CA12, and the inhibitory effect on cell migration by Disulfiram treatment in cancer cells provided the molecular evidence supporting the potential of Disulfiram as an anticancer agent. Full article

(This article belongs to the Collection Efficient Pharmaceutical and Chemical Approaches for Anticancer Therapy: Design, Preliminary Evaluations, and Further Developments)

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15 pages, 1828 KiB

Open AccessArticle

Water Extraction Kinetics of Bioactive Compounds of Fucus vesiculosus

by Ricardo M. Ferreira, Ana Ramalho Ribeiro, Carla Patinha, Artur M. S. Silva, Susana M. Cardoso and Rui Costa

Molecules 2019, 24(18), 3408; https://doi.org/10.3390/molecules24183408 - 19 Sep 2019

Cited by 24 | Viewed by 4166

Abstract

Brown macroalgae, particularly those from Fucus genus, are a rich and balanced source of bioactive nutrients and phytochemicals, such as dietary fibres (fucoidans, laminarins, and/or alginates), phlorotannins, and fucoxanthin, and some minerals, such as iodine, which have been demonstrated to possess numerous health-promoting [...] Read more.

Brown macroalgae, particularly those from Fucus genus, are a rich and balanced source of bioactive nutrients and phytochemicals, such as dietary fibres (fucoidans, laminarins, and/or alginates), phlorotannins, and fucoxanthin, and some minerals, such as iodine, which have been demonstrated to possess numerous health-promoting properties. In fact, aqueous extracts of Fucus vesiculosus have been used as food supplements due to its rich content in bioactive compounds, though no study has been published on the optimization of this operation. Therefore, this study aimed to evaluate the impact of different extraction temperatures (25 °C, 50 °C, 75 °C, 100 °C, and 120 °C) and times (5 min, 1 h, 2 h, and 4 h) on the recovery of those bioactive compounds. The temperature was observed to positively influence the extraction of crude mass and of fucose polysaccharides only at 75 °C and above, and of iodine extraction at 50 °C and above. At these temperatures, time also showed to increase yields. Yields of crude extract, fucose, and iodine were successfully mathematically modelled with a power law, and its maximum yields were obtained at the highest temperature studied (120 °C) and longest extraction time (4 h). Iodine yield at these conditions provided extracts with relevant content to contribute to the recommended daily ingestion. Phlorotannins were significantly recovered at 120 °C though evidence of degradation was observed during time. Full article

(This article belongs to the Section Physical Chemistry)

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15 pages, 1970 KiB

Open AccessReview

Targeted Delivery of Plasminogen Activators for Thrombolytic Therapy: An Integrative Evaluation

by Yunn-Hwa Ma, Chih-Hsin Liu, Yueh Liang, Jyh-Ping Chen and Tony Wu

Molecules 2019, 24(18), 3407; https://doi.org/10.3390/molecules24183407 - 19 Sep 2019

Cited by 15 | Viewed by 4242

Abstract

In thrombolytic therapy, plasminogen activators (PAs) are still the only group of drug approved to induce thrombolysis, and therefore, critical for treatment of arterial thromboembolism, such as stroke, in the acute phase. Functionalized nanocomposites have attracted great attention in achieving target thrombolysis due [...] Read more.

In thrombolytic therapy, plasminogen activators (PAs) are still the only group of drug approved to induce thrombolysis, and therefore, critical for treatment of arterial thromboembolism, such as stroke, in the acute phase. Functionalized nanocomposites have attracted great attention in achieving target thrombolysis due to favorable characteristics associated with the size, surface properties and targeting effects. Many PA-conjugated nanocomposites have been prepared and characterized, and some of them has been demonstrated with therapeutic efficacy in animal models. To facilitate future translation, this paper reviews recent progress of this area, especially focus on how to achieve reproducible thrombolysis efficacy in vivo. Full article

(This article belongs to the Special Issue Cardiovascular Nanomedicines and Nanomaterials )

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18 pages, 1765 KiB

Open AccessArticle

E-Beam Irradiation and Ozonation as an Alternative to the Sulphuric Method of Wine Preservation

by Magdalena Błaszak, Agata Nowak, Sabina Lachowicz, Wojciech Migdał and Ireneusz Ochmian

Molecules 2019, 24(18), 3406; https://doi.org/10.3390/molecules24183406 - 19 Sep 2019

Cited by 12 | Viewed by 3461

Abstract

Potassium metabisulphite is usually used for microbial stabilization in the process of vinification and wine preservation, but it is considered to be allergenic. The objective of the present study was to assess the efficiency of ozonation and ionizing radiation as alternatives to wine [...] Read more.

Potassium metabisulphite is usually used for microbial stabilization in the process of vinification and wine preservation, but it is considered to be allergenic. The objective of the present study was to assess the efficiency of ozonation and ionizing radiation as alternatives to wine sulphurization. The efficiency of yeast removal and the retention of the chemical quality of wine were evaluated. Wine was subjected to 60 min of ozonation, and radiation doses were set at 1–10 kGy. Moreover, a combination of ozonation and ionizing radiation treatment was used. The ozonation of wine did not produce the expected results. That is, it did not limit the number of yeast cells. From the sixth minute, a significant deterioration in the taste and the color of the wine was found. Ionizing radiation at a dose of 1 kGy reduced the yeast count by 95.5%, and a reduction of 99.9% was seen after the application of 2.5 kGy. Moreover, these doses did not have a significant effect on the organoleptic properties or the chemical composition of wine. The total amount of polyphenols reduced from the maximum of 1127.15 to 1023.73 mg at the dose of 5 kGy. Radiation is widely used to preserve food products. Its use for finished wine preservation may be an alternative to sulphurization. Full article

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10 pages, 1555 KiB

Open AccessArticle

Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles

by Jakub Adamek, Anna Węgrzyk-Schlieter, Klaudia Steć, Krzysztof Walczak and Karol Erfurt

Molecules 2019, 24(18), 3405; https://doi.org/10.3390/molecules24183405 - 19 Sep 2019

Cited by 6 | Viewed by 3383

Abstract

In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of [...] Read more.

In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and N-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided. Full article

(This article belongs to the Special Issue Recent Developments in the Synthesis and Utilization of Organophosphorus Compounds)

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13 pages, 1609 KiB

Open AccessArticle

Synthesis, Characterization and Solubility Determination of 6-Phenyl-pyridazin-3(2H)-one in Different Pharmaceutical Solvents

by Faiyaz Shakeel, Mohd Imran, Nazrul Haq, Sultan Alshehri and Md. Khalid Anwer

Molecules 2019, 24(18), 3404; https://doi.org/10.3390/molecules24183404 - 19 Sep 2019

Cited by 23 | Viewed by 3055

Abstract

The current research work proposed the solubility data and solution thermodynamic properties of the cardiovascular agent 6-phenylpyridazin-3(2H)-one [PPD] in twelve pharmaceutical solvents at “T = 298.2 K to 318.2 K” and “p = 0.1 MPa”. The measured solubilities of [...] Read more.

The current research work proposed the solubility data and solution thermodynamic properties of the cardiovascular agent 6-phenylpyridazin-3(2H)-one [PPD] in twelve pharmaceutical solvents at “T = 298.2 K to 318.2 K” and “p = 0.1 MPa”. The measured solubilities of PPD were regressed well with “van’t Hoff and Apelblat models”. The solid phases of pure and equilibrated PPD were characterized using differential scanning calorimetry and powder X-ray differactometry, and the results suggested no transformation of PPD into solvates/hydrates/polymorphs after equilibrium. The solubilities of PPD in a mole fraction at “T = 318.2 K” were noted at a maximum in dimethyl sulfoxide (DMSO, 4.73 × 10⁻¹), followed by polyethylene glycol-400 (PEG-400, 4.12 × 10⁻¹), Transcutol^® (3.46 × 10⁻¹), ethyl acetate (EA, 81 × 10⁻²), 2-butanol (2.18 × 10⁻²), 1-butanol (2.11 × 10⁻²), propylene glycol (PG, 1.50 × 10⁻²), isopropyl alcohol (IPA, 1.44 × 10⁻²), ethylene glycol (EG, 1.27 × 10⁻²), ethanol (8.22 × 10⁻³), methanol (5.18 × 10⁻³) and water (1.26 × 10⁻⁵). Similar tendencies were also noted at other studied temperatures. The results of the “apparent thermodynamic analysis” showed an endothermic and entropy-driven dissolution of PPD in all pharmaceutical solvents. The results of the activity coefficients suggested a maximum interaction at the molecular level in PPD-DMSO, PPD-PEG-400 and PPD-Transcutol, compared with other combination of the solute and solvents. Full article

(This article belongs to the Section Physical Chemistry)

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14 pages, 4418 KiB

Open AccessArticle

Deepening Inside the Pictorial Layers of Etruscan Sarcophagus of Hasti Afunei: An Innovative Micro-Sampling Technique for Raman/SERS Analyses

by Rossella Gagliano Candela, Livia Lombardi, Alessandro Ciccola, Ilaria Serafini, Armandodoriano Bianco, Paolo Postorino, Lorella Pellegrino and Maurizio Bruno

Molecules 2019, 24(18), 3403; https://doi.org/10.3390/molecules24183403 - 19 Sep 2019

Cited by 5 | Viewed by 4434

Abstract

The Hasti Afunei sarcophagus is a large Etruscan urn, made up of two chalky alabaster monoliths. Dated from the last quarter of the third century BC, it was found in 1826 in the small town of Chiusi (Tuscany- Il Colle place) by a [...] Read more.

The Hasti Afunei sarcophagus is a large Etruscan urn, made up of two chalky alabaster monoliths. Dated from the last quarter of the third century BC, it was found in 1826 in the small town of Chiusi (Tuscany- Il Colle place) by a landowner, Pietro Bonci Casuccini, who made it part of his private collection. The noble owner’s collection was sold in 1865 to the Royal Museum of Palermo (today under the name of Antonino Salinas Regional Archaeological Museum), where it is still displayed. The sarcophagus is characterized by a complex iconography that is meticulously illustrated through an excellent sculptural technique, despite having subjected to anthropic degradation and numerous restorative actions during the last century. During the restoration campaign carried out between 2016 and 2017, a targeted diagnostic campaign was carried out to identify the constituent materials of the artefact, the pigments employed and the executive technique, in order to get an overall picture of conservation status and conservative criticalities. In particular, this last intervention has allowed the use of the innovative micro-sampling technique, patented by the Cultural Heritage research group of Sapienza, in order to identify the employee of lake pigments through SERS analyses. Together with this analysis, Raman and NMR technique have completed the information requested by restorers, for what concerns the wax employed as protective layers, and allowed to rebuild the conservation history of the sarcophagus. In fact, together with the identification of red ocher and yellow ocher, carbon black, Egyptian blue and madder lake, pigments compatible with the historical period of the work, modern pigments (probably green Paris, chrome orange, barium yellow, blue phtalocyanine) have been recognized, attributable with not documented intervention during the eighteenth and twentieth centuries. Full article

(This article belongs to the Special Issue Natural Dyes)

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13 pages, 1228 KiB

Open AccessArticle

Fractionated Antioxidant and Anti-inflammatory Kernel Oil from Torreya fargesii

by Xianrong Zhou, Jin Shang, Mingyi Qin, Jianhua Wang, Bo Jiang, Hui Yang and Yan Zhang

Molecules 2019, 24(18), 3402; https://doi.org/10.3390/molecules24183402 - 19 Sep 2019

Cited by 12 | Viewed by 3098

Abstract

Polymethylene-interrupted polyunsaturated fatty acids (PMI-PUFAs) are emerging functional lipids with proven antioxidant and anti-inflammatory effects. In this study, a typical PMI-PUFA, sciadonic acid (C20:3, 5c 11c 14c), was enriched in the kernel oil of Torreya fargesii (T. fargesii) by fractionation. Fractionated [...] Read more.

Polymethylene-interrupted polyunsaturated fatty acids (PMI-PUFAs) are emerging functional lipids with proven antioxidant and anti-inflammatory effects. In this study, a typical PMI-PUFA, sciadonic acid (C20:3, 5c 11c 14c), was enriched in the kernel oil of Torreya fargesii (T. fargesii) by fractionation. Fractionated kernel oil of T. fargesii (containing 25% sciadonic acid) showed equal stability and similar radical scavenging ability compared with the non-fractionated oil. In anti-inflammatory tests, fractionated kernel oil was shown to inhibit the activity of phosphodiesterase (PDE-5, efficiency 80% at 133.7 μg/mL) and lipoxygenase-5 (LOX-5, efficiency 65% at 66.7 μg/mL) more effectively than the non-fractionated oil. This shows that increasing the amount of sciadonic acid can enhance the anti-inflammatory effect of the kernel oil. This research also indicates that fractionation is a feasible way to obtain sciadonic acid–rich functional oil with potential pharmacological effects. Full article

(This article belongs to the Section Natural Products Chemistry)

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12 pages, 1006 KiB

Open AccessFeature PaperArticle

Castanea sativa Mill. Shells Aqueous Extract Exhibits Anticancer Properties Inducing Cytotoxic and Pro-Apoptotic Effects

by Nunzio Antonio Cacciola, Giuseppe Squillaci, Mariella D’Apolito, Orsolina Petillo, Francesco Veraldi, Francesco La Cara, Gianfranco Peluso, Sabrina Margarucci and Alessandra Morana

Molecules 2019, 24(18), 3401; https://doi.org/10.3390/molecules24183401 - 19 Sep 2019

Cited by 29 | Viewed by 4353

Abstract

In this study, chestnut shells (CS) were used in order to obtain bioactive compounds through different extraction procedures. The aqueous extracts were chemically characterized. The highest extraction yield and total phenolic content was obtained by conventional liquid extraction (CLE). Gallic and protocatechuic acids [...] Read more.

In this study, chestnut shells (CS) were used in order to obtain bioactive compounds through different extraction procedures. The aqueous extracts were chemically characterized. The highest extraction yield and total phenolic content was obtained by conventional liquid extraction (CLE). Gallic and protocatechuic acids were the main simple phenols in the extract, with 86.97 and 11.20 mg/g chestnut shells dry extract (CSDE), respectively. Six tumor cell lines (DU 145, PC-3, LNCaP, MDA-MB-231, MCF-7, and HepG2) and one normal prostate epithelial cell line (PNT2) were exposed to increasing concentration of CSDE (1–100 µg/mL) for 24 h, and cell viability was evaluated using 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide MTT assay. A reduced rate in cell viability was observed in DU 145, PC-3, LNCaP, and MCF-7 cells, while viability of the other assessed cells was not affected, except for PNT2 cells at a concentration of 100 μg/mL. Furthermore, CSDE—at concentrations of 55.5 and 100 µg/mL—lead to a significant increase of apoptotic cells in DU 145 cells of 28.2% and 61%, respectively. In conclusion, these outcomes suggested that CS might be used for the extraction of several polyphenols that may represent good candidates for alternative therapies or in combination with current chemotherapeutics. Full article

(This article belongs to the Special Issue Herbal Medicines–Unraveling Their Molecular Mechanism)

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20 pages, 921 KiB

Open AccessReview

Petroleum Hydrocarbon Contamination in Terrestrial Ecosystems—Fate and Microbial Responses

by Adam Truskewycz, Taylor D. Gundry, Leadin S. Khudur, Adam Kolobaric, Mohamed Taha, Arturo Aburto-Medina, Andrew S. Ball and Esmaeil Shahsavari

Molecules 2019, 24(18), 3400; https://doi.org/10.3390/molecules24183400 - 19 Sep 2019

Cited by 149 | Viewed by 9349

Abstract

Petroleum hydrocarbons represent the most frequent environmental contaminant. The introduction of petroleum hydrocarbons into a pristine environment immediately changes the nature of that environment, resulting in reduced ecosystem functionality. Natural attenuation represents the single, most important biological process which removes petroleum hydrocarbons from [...] Read more.

Petroleum hydrocarbons represent the most frequent environmental contaminant. The introduction of petroleum hydrocarbons into a pristine environment immediately changes the nature of that environment, resulting in reduced ecosystem functionality. Natural attenuation represents the single, most important biological process which removes petroleum hydrocarbons from the environment. It is a process where microorganisms present at the site degrade the organic contaminants without the input of external bioremediation enhancers (i.e., electron donors, electron acceptors, other microorganisms or nutrients). So successful is this natural attenuation process that in environmental biotechnology, bioremediation has developed steadily over the past 50 years based on this natural biodegradation process. Bioremediation is recognized as the most environmentally friendly remediation approach for the removal of petroleum hydrocarbons from an environment as it does not require intensive chemical, mechanical, and costly interventions. However, it is under-utilized as a commercial remediation strategy due to incomplete hydrocarbon catabolism and lengthy remediation times when compared with rival technologies. This review aims to describe the fate of petroleum hydrocarbons in the environment and discuss their interactions with abiotic and biotic components of the environment under both aerobic and anaerobic conditions. Furthermore, the mechanisms for dealing with petroleum hydrocarbon contamination in the environment will be examined. When petroleum hydrocarbons contaminate land, they start to interact with its surrounding, including physical (dispersion), physiochemical (evaporation, dissolution, sorption), chemical (photo-oxidation, auto-oxidation), and biological (plant and microbial catabolism of hydrocarbons) interactions. As microorganism (including bacteria and fungi) play an important role in the degradation of petroleum hydrocarbons, investigations into the microbial communities within contaminated soils is essential for any bioremediation project. This review highlights the fate of petroleum hydrocarbons in tertial environments, as well as the contributions of different microbial consortia for optimum petroleum hydrocarbon bioremediation potential. The impact of high-throughput metagenomic sequencing in determining the underlying degradation mechanisms is also discussed. This knowledge will aid the development of more efficient, cost-effective commercial bioremediation technologies. Full article

(This article belongs to the Special Issue Biodegradation of Conventional and Emerging Pollutants)

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19 pages, 2139 KiB

Open AccessFeature PaperReview

Corilagin in Cancer: A Critical Evaluation of Anticancer Activities and Molecular Mechanisms

by Ashutosh Gupta, Amit Kumar Singh, Ramesh Kumar, Risha Ganguly, Harvesh Kumar Rana, Prabhash Kumar Pandey, Gautam Sethi, Anupam Bishayee and Abhay K. Pandey

Molecules 2019, 24(18), 3399; https://doi.org/10.3390/molecules24183399 - 19 Sep 2019

Cited by 65 | Viewed by 6747

Abstract

Corilagin (β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-d-glucose), an ellagitannin, is one of the major bioactive compounds present in various plants. Ellagitannins belong to the hydrolyzable tannins, a group of polyphenols. Corilagin shows broad-spectrum biological, and therapeutic activities, such as antioxidant, anti-inflammatory, hepatoprotective, [...] Read more.

Corilagin (β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-d-glucose), an ellagitannin, is one of the major bioactive compounds present in various plants. Ellagitannins belong to the hydrolyzable tannins, a group of polyphenols. Corilagin shows broad-spectrum biological, and therapeutic activities, such as antioxidant, anti-inflammatory, hepatoprotective, and antitumor actions. Natural compounds possessing antitumor activities have attracted significant attention for treatment of cancer. Corilagin has shown inhibitory activity against the growth of numerous cancer cells by prompting cell cycle arrest at the G₂/M phase and augmented apoptosis. Corilagin-induced apoptosis and autophagic cell death depends on production of intracellular reactive oxygen species in breast cancer cell line. It blocks the activation of both the canonical Smad and non-canonical extracellular-signal-regulated kinase/Akt (protein kinase B) pathways. The potential apoptotic action of corilagin is mediated by altered expression of procaspase-3, procaspase-8, procaspase-9, poly (ADP ribose) polymerase, and Bcl-2 Bax. In nude mice, corilagin suppressed cholangiocarcinoma growth and downregulated the expression of Notch1 and mammalian target of rapamycin. The aim of this review is to summarize the anticancer efficacy of corilagin with an emphasis on the molecular mechanisms involving various signaling pathways in tumor cells. Full article

(This article belongs to the Special Issue From Ethnobotany to Ecopharmacognosy: Chemical Characterization and Bioactivity Evaluation of Medicinal and Aromatic Plants)

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13 pages, 3334 KiB

Open AccessArticle

Dual-Purpose Materials Based on Carbon Xerogel Microspheres (CXMs) for Delayed Release of Cannabidiol (CBD) and Subsequent Aflatoxin Removal

by Farid B. Cortés, Karol Zapata, Benjamín A. Rojano, Francisco Carrasco-Marín, Jaime Gallego, M. Alejandra Hernández and Camilo A. Franco

Molecules 2019, 24(18), 3398; https://doi.org/10.3390/molecules24183398 - 19 Sep 2019

Cited by 6 | Viewed by 4197

Abstract

The main objective of this study is to develop a novel dual-purpose material based on carbon xerogel microspheres (CXMs) that permits the delayed release of cannabidiol (CBD) and the removal of aflatoxin. The CXMs were prepared by the sol-gel method and functionalized with [...] Read more.

The main objective of this study is to develop a novel dual-purpose material based on carbon xerogel microspheres (CXMs) that permits the delayed release of cannabidiol (CBD) and the removal of aflatoxin. The CXMs were prepared by the sol-gel method and functionalized with phosphoric acid (CXMP) and melamine (CXMN). The support and the modified materials were characterized by scanning electronic microscopy (SEM), N₂ adsorption at −196 °C, X-ray photoelectron spectroscopy (XPS), and zeta potential. For the loading of the cannabidiol (CBD) in the porous samples, batch–mode adsorption experiments at 25 °C were performed, varying the concentration of CBD. The desorption kinetics was performed at two conditions for simulating the gastric (pH of 2.1) and intestinal (pH of 7.4) conditions at 37 °C based on in vitro CBD release. Posteriorly, the samples obtained after desorption were used to study aflatoxin removal, which was evaluated through adsorption experiments at pH = 7.4 and 37 °C. The adsorption isotherms of CBD showed a type I(b) behavior, with the adsorbed uptake being higher for the support than for the modified materials with P and N. Meanwhile, the desorption kinetics of CBD at gastric conditions indicated release values lower than 8%, and the remaining amount was desorbed at pH = 7.4 in three hours until reaching 100% based on the in vitro experiments. The results for aflatoxin showed total removal in less than 30 min for all the materials evaluated. This study opens a broader landscape in which to develop dual-purpose materials for the delayed release of CBD, improving its bioavailability and allowing aflatoxin removal in gastric conditions. Full article

(This article belongs to the Special Issue Porous Organic Polymers for Adsorption, Storage, Separation and Catalysis)

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15 pages, 3678 KiB

Open AccessArticle

A Monte Carlo Method for Determining the Response Relationship between Two Commonly Used Detectors to Indirectly Measure Alpha Particle Radiation Activity

by Christopher J. Tichacek, Mikalai M. Budzevich, Thaddeus J. Wadas, David L. Morse and Eduardo G. Moros

Molecules 2019, 24(18), 3397; https://doi.org/10.3390/molecules24183397 - 19 Sep 2019

Cited by 11 | Viewed by 4396

Abstract

Using targeted ligands to deliver alpha-emitting radionuclides directly to tumor cells has become a promising therapeutic strategy. To calculate the radiation dose to patients, activities of parent and daughter radionuclides must be measured. Scintillation detectors can be used to quantify these activities; however, [...] Read more.

Using targeted ligands to deliver alpha-emitting radionuclides directly to tumor cells has become a promising therapeutic strategy. To calculate the radiation dose to patients, activities of parent and daughter radionuclides must be measured. Scintillation detectors can be used to quantify these activities; however, activities found in pre-clinical and clinical studies can exceed their optimal performance range. Therefore, a method of correcting scintillation detector measurements at higher activities was developed using Monte Carlo modeling. Because there are currently no National Institute of Standards and Technology traceable Actinium-225 (²²⁵Ac) standards available, a well-type ionization chamber was used to measure 70.3 ± 7.0, 144.3 ± 14.4, 222.0 ± 22.2, 299.7 ± 30.0, 370.0 ± 37.0, and 447.7 ± 44.7 kBq samples of ²²⁵Ac obtained from Oak Ridge National Lab. Samples were then placed in a well-type NaI(Tl) scintillation detector and spectra were obtained. Alpha particle activity for each species was calculated using gamma abundance per alpha decay. MCNP6 Monte Carlo software was used to simulate the 4π-geometry of the NaI(Tl) detector. Using the ionization chamber reading as activity input to the Monte Carlo model, spectra were obtained and compared to NaI(Tl) spectra. Successive simulations of different activities were run until a spectrum minimizing the mean percent difference between the two was identified. This was repeated for each sample activity. Ionization chamber calibration measurements showed increase in error from 3% to 10% as activities decreased, resulting from decreasing detection efficiency. Measurements of ²²⁵Ac using both detector types agreed within 7% of Oak Ridge stated activities. Simulated Monte Carlo spectra of ²²⁵Ac were successfully generated. Activities obtained from these spectra differed with ionization chamber readings up to 156% at 147.7 kBq. Simulated spectra were then adjusted to correct NaI(Tl) measurements to be within 1%. These were compared to ionization chamber readings and a response relationship was determined between the two instruments. Measurements of ²²⁵Ac and daughter activity were conducted using a NaI(Tl) scintillation detector calibrated for energy and efficiency and an ionization chamber calibrated for efficiency using a surrogate calibration reference. Corrections provided by Monte Carlo modeling improve the accuracy of activity quantification for alpha-particle emitting radiopharmaceuticals in pre-clinical and clinical studies. Full article

(This article belongs to the Special Issue Radiopharmaceutical Chemistry and Radiotherapy)

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15 pages, 2019 KiB

Open AccessFeature PaperArticle

Effects of the Ethanol Extract of Dipterocarpus alatus Leaf on the Unpredictable Chronic Mild Stress-Induced Depression in ICR Mice and Its Possible Mechanism of Action

by Supawadee Daodee, Orawan Monthakantirat, Kanlaya Ruengwinitwong, Kankrittanon Gatenakorn, Juthamart Maneenet, Charinya Khamphukdee, Nazim Sekeroglu, Yaowared Chulikhit and Anake Kijjoa

Molecules 2019, 24(18), 3396; https://doi.org/10.3390/molecules24183396 - 18 Sep 2019

Cited by 22 | Viewed by 4902

Abstract

Treatment of the unpredictable chronic mild stress (UCMS) mice with the ethanol extract of Dipterocarpus alatus leaf attenuated anhedonia (increased sucrose preference) and behavioral despair (decreased immobility time in tail suspension test (TST) and forced swimming test (FST)). The extract not only decreased [...] Read more.

Treatment of the unpredictable chronic mild stress (UCMS) mice with the ethanol extract of Dipterocarpus alatus leaf attenuated anhedonia (increased sucrose preference) and behavioral despair (decreased immobility time in tail suspension test (TST) and forced swimming test (FST)). The extract not only decreased the elevation of serum corticosterone level and the index of over-activation of the hypothalamic-pituitary-adrenal (HPA) axis, caused by UCMS, but also ameliorated UCMS-induced up-regulation of serum- and glucocorticoid-inducible kinase 1 (SGK1) mRNA expression and down-regulation of cyclic AMP-responsive element binding (CREB) and brain-derived neurotrophic factor (BDNF) mRNAs in frontal cortex and hippocampus. In vitro monoamine oxidase (MAO) inhibition assays showed that the extract exhibited the partial selective inhibition on MAO-A. HPLC analysis of the extract showed the presence of flavonoids (luteolin-7-O-glucoside, kaempferol-3-glucoside, rutin) and phenolic acids (gallic acid, ferulic acid, and caffeic acid) as major constituents. Full article

(This article belongs to the Special Issue Selected Papers from the Joint Symposia of MESMAP-5 & ISPBS-5)

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15 pages, 3106 KiB

Open AccessArticle

Formation and Stabilization of Gold Nanoparticles in Bovine Serum Albumin Solution

by Iulia Matei, Cristina Maria Buta, Ioana Maria Turcu, Daniela Culita, Cornel Munteanu and Gabriela Ionita

Molecules 2019, 24(18), 3395; https://doi.org/10.3390/molecules24183395 - 18 Sep 2019

Cited by 35 | Viewed by 5438

Abstract

The formation and growth of gold nanoparticles (AuNPs) were investigated in pH 7 buffer solution of bovine serum albumin (BSA) at room temperature. The processes were monitored by UV-Vis, circular dichroism, Raman and electron paramagnetic resonance (EPR) spectroscopies. TEM microscopy and dynamic light [...] Read more.

The formation and growth of gold nanoparticles (AuNPs) were investigated in pH 7 buffer solution of bovine serum albumin (BSA) at room temperature. The processes were monitored by UV-Vis, circular dichroism, Raman and electron paramagnetic resonance (EPR) spectroscopies. TEM microscopy and dynamic light scattering (DLS) measurements were used to evidence changes in particle size during nanoparticle formation and growth. The formation of AuNPs at pH 7 in the absence of BSA was not observed, which proves that the albumin is involved in the first step of Au(III) reduction. Changes in the EPR spectral features of two spin probes, CAT16 and DIS3, with affinity for BSA and AuNPs, respectively, allowed us to monitor the particle growth and to demonstrate the protective role of BSA for AuNPs. The size of AuNPs formed in BSA solution increases slowly with time, resulting in nanoparticles of different morphologies, as revealed by TEM. Raman spectra of BSA indicate the interaction of albumin with AuNPs through sulfur-containing amino acid residues. This study shows that albumins act as both reducing agents and protective corona of AuNPs. Full article

(This article belongs to the Special Issue Biomimetic Radical Chemistry and Applications)

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15 pages, 2382 KiB

Open AccessArticle

(10Z)-Debromohymenialdisine from Marine Sponge Stylissa sp. Regulates Intestinal Inflammatory Responses in Co-Culture Model of Epithelial Caco-2 Cells and THP-1 Macrophage Cells

by Seon Min Lee, Na-Hyun Kim, Sangbum Lee, Yun Na Kim, Jeong-Doo Heo, Jung-Rae Rho and Eun Ju Jeong

Molecules 2019, 24(18), 3394; https://doi.org/10.3390/molecules24183394 - 18 Sep 2019

Cited by 19 | Viewed by 5583

Abstract

Crohn’s disease (CD) and ulcerative colitis (UC), collectively referred to as inflammatory bowel disease (IBD), are autoimmune diseases characterized by chronic inflammation within the gastrointestinal tract. Debromohymenialdisine is an active pyrrole alkaloid that is well known to serve as a stable and effective [...] Read more.

Crohn’s disease (CD) and ulcerative colitis (UC), collectively referred to as inflammatory bowel disease (IBD), are autoimmune diseases characterized by chronic inflammation within the gastrointestinal tract. Debromohymenialdisine is an active pyrrole alkaloid that is well known to serve as a stable and effective inhibitor of Chk2. In the present study, we attempted to investigate the anti-inflammatory properties of (10Z)-debromohymenialdisine (1) isolated from marine sponge Stylissa species using an intestinal in vitro model with a transwell co-culture system. The treatment with 1 attenuated the production and gene expression of lipopolysaccharide (LPS)-induced Interleukin (IL)-6, IL-1β, prostaglandin E2 (PGE2), and tumor necrosis factor-α in co-cultured THP-1 macrophages at a concentration range of 1–5 μM. The protein expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 were down-regulated in response to the inhibition of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-kB) translocation into the nucleus in cells. In addition, we observed that 1 markedly promoted the nuclear translocation of nuclear factor erythroid 2 related factor 2 (Nrf2) and subsequent increase of heme oxygenase-1 (HO-1) expression. These findings suggest the potential use of 1 as a pharmaceutical lead in the treatment of inflammation-related diseases including IBD. Full article

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15 pages, 3989 KiB

Open AccessArticle

Proanthocyanidin-Rich Fractions from Red Rice Extract Enhance TNF-α-Induced Cell Death and Suppress Invasion of Human Lung Adenocarcinoma Cell A549

by Chayaporn Subkamkaew, Pornngarm Limtrakul (Dejkriengkraikul) and Supachai Yodkeeree

Molecules 2019, 24(18), 3393; https://doi.org/10.3390/molecules24183393 - 18 Sep 2019

Cited by 8 | Viewed by 4322

Abstract

Tumor necrosis factor-alpha (TNF-α) plays a key role in promoting tumor progression, such as stimulation of cell proliferation and metastasis via activation of NF-κB and AP-1. The proanthocyanidin-rich fraction obtained from red rice (PRFR) has been reported for its anti-tumor effects in cancer [...] Read more.

Tumor necrosis factor-alpha (TNF-α) plays a key role in promoting tumor progression, such as stimulation of cell proliferation and metastasis via activation of NF-κB and AP-1. The proanthocyanidin-rich fraction obtained from red rice (PRFR) has been reported for its anti-tumor effects in cancer cells. This study investigated the molecular mechanisms associated with PRFR on cell survival and metastasis of TNF-α-induced A549 human lung adenocarcinoma. Notably, PRFR enhanced TNF-α-induced A549 cell death when compared with PRFP alone and caused a G0-G1 cell cycle arrest. Although, PRFR alone enhanced cell apoptosis, the combination treatment induced the cells that had been enhanced with PRFR and TNF-α to apoptosis that was less than PRFR alone and displayed a partial effect on caspase-8 activation and PARP cleavage. By using the autophagy inhibitor; 3-MA attenuated the effect of how PRFR enhanced TNF-α-induced cell death. This indicates that PRFR not only enhanced TNF-α-induced A549 cell death by apoptotic pathway, but also by induction autophagy. Moreover, PRFR also inhibited TNF-α-induced A549 cell invasion. This effect was associated with PRFR suppressed the TNF-α-induced level of expression for survival, proliferation, and invasive proteins. This was due to reduce of MAPKs, Akt, NF-κB, and AP-1 activation. Taken together, our results suggest that TNF-α-induced A549 cell survival and invasion are attenuated by PRFR through the suppression of the MAPKs, Akt, AP-1, and NF-κB signaling pathways. Full article

(This article belongs to the Special Issue Antitumoral Properties of Natural Products)

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9 pages, 1332 KiB

Open AccessFeature PaperArticle

Effect of Ethanol on the Adsorption of Volatile Sulfur Compounds on Solid Phase Micro-Extraction Fiber Coatings and the Implication for Analysis in Wine

by Peter M. Davis and Michael C. Qian

Molecules 2019, 24(18), 3392; https://doi.org/10.3390/molecules24183392 - 18 Sep 2019

Cited by 11 | Viewed by 3584

Abstract

Complications in the analysis of volatile sulfur compounds (VSC) in wine using solid-phase microextraction (SPME) arise from sample variability. Constituents of the wine matrix, including ethanol, affect the volatility and adsorption of sulfur volatiles on SPME fiber coatings (Carboxen- polydimethylsiloxane(PDMS); DVB-Carboxen-PDMS and DVB-PDMS), [...] Read more.

Complications in the analysis of volatile sulfur compounds (VSC) in wine using solid-phase microextraction (SPME) arise from sample variability. Constituents of the wine matrix, including ethanol, affect the volatility and adsorption of sulfur volatiles on SPME fiber coatings (Carboxen- polydimethylsiloxane(PDMS); DVB-Carboxen-PDMS and DVB-PDMS), which can impact sensitivity and accuracy. Here, several common wine sulfur volatiles, including hydrogen sulfide (H₂S), methanethiol (MeSH), dimethyl sulfide (DMS), dimethyl disulfide (DMDS), dimethyl trisulfide (DMTS), diethyl disulfide (DEDS), methyl thioacetate (MeSOAc), and ethyl thioacetate (EtSOAc) are analyzed, using SPME followed by gas chromatography (GC), using a system equipped with a pulsed-flame photometric detection (PFPD) system, at various ethanol concentrations in a synthetic wine matrix. Ethyl methyl sulfide (EMS), diethyl sulfide (DES), methyl isopropyl sulfide (MIS), ethyl isopropyl sulfide (EIS), and diisopropyl disulfide (DIDS) are evaluated as internal standards. The absorption of volatile compounds on the SPME fiber is greatly affected by ethanol. All compounds exhibit a stark decrease in detectability with the addition of ethanol, especially between 0.0 and 0.5% v/v. However, the ratio of interested sulfur compounds to the internal standard becomes more stable when the total alcohol concentration exceeds 2%. EMS was found to best resemble DMS. EIS and DES were found to best resemble DMDS, MeSOAc, and EtSOAc. DIDS was found to best resemble DEDS, DMTS, H₂S, and MeSH. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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15 pages, 2479 KiB

Open AccessArticle

Isothioureas, Ureas, and Their N-Methyl Amides from 2-Aminobenzothiazole and Chiral Amino Acids

by Itzia I. Padilla-Martínez, José Miguel González-Encarnación, Efrén V. García-Báez, Alejandro Cruz and Ángel Andrés Ramos-Organillo

Molecules 2019, 24(18), 3391; https://doi.org/10.3390/molecules24183391 - 18 Sep 2019

Cited by 5 | Viewed by 3049

Abstract

In this investigation, the reaction of 2-dithiomethylcarboimidatebenzothiazole with a series of six chiral amino-acids was studied. The reaction proceeds through the isolable sodium salt of SMe-isothiourea carboxylates as intermediates, whose reaction with methyl iodide in stirring DMF as solvent affords SMe-isothiourea methyl esters. [...] Read more.

In this investigation, the reaction of 2-dithiomethylcarboimidatebenzothiazole with a series of six chiral amino-acids was studied. The reaction proceeds through the isolable sodium salt of SMe-isothiourea carboxylates as intermediates, whose reaction with methyl iodide in stirring DMF as solvent affords SMe-isothiourea methyl esters. The presence of water in the reaction leads to the corresponding urea carboxylates as isolable intermediates, whose methyl esters were obtained. Finally, the urea N-methyl amide derivatives were isolated when SMe-isothiourea or urea methyl esters were reacted with methylamine in the presence of water. The structures of synthesized compounds were established by ¹H and ¹³C nuclear magnetic resonance and the structures of SMe-isothiourea methyl esters derived from (l)-glycine, (l)-alanine, (l)-phenylglycine, and (l)-leucine, by X-ray diffraction analysis. This methodology allows to functionalize 2-aminobenzothiazole with SMe-isothiourea, urea, and methylamide groups derived from chiral amino acids to get benzothiazole derivatives containing coordination sites and hydrogen bonding groups. Further research on the biological activities of some of these derivatives is ongoing. Full article

(This article belongs to the Section Organic Chemistry)

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13 pages, 2347 KiB

Open AccessArticle

Trilobatin, a Novel SGLT1/2 Inhibitor, Selectively Induces the Proliferation of Human Hepatoblastoma Cells

by Lujing Wang, Min Liu, Fei Yin, Yuanqiang Wang, Xingan Li, Yucui Wu, Cuilian Ye and Jianhui Liu

Molecules 2019, 24(18), 3390; https://doi.org/10.3390/molecules24183390 - 18 Sep 2019

Cited by 26 | Viewed by 4086

Abstract

Studies have indicated that Na⁺-d-glucose co-transporter (SGLT) inhibitors had anti-proliferative activity by attenuating the uptake of glucose in several tumor cell lines. In this study, the molecular docking showed that, trilobatin, one of the dihydrochalcones from leaves of Lithocarpus [...] Read more.

Studies have indicated that Na⁺-d-glucose co-transporter (SGLT) inhibitors had anti-proliferative activity by attenuating the uptake of glucose in several tumor cell lines. In this study, the molecular docking showed that, trilobatin, one of the dihydrochalcones from leaves of Lithocarpus polystachyus Rehd., might be a novel inhibitor of SGLT1 and SGLT2, which evidently attenuated the uptake of glucose in vitro and in vivo. To our surprise, we observed that trilobatin did not inhibit, but promoted the proliferation of human hepatoblastoma HepG2 and Huh 7 cells when it was present at high concentrations. At the same time, incubation with high concentrations of trilobatin arrested the cell cycle at S phase in HepG2 cells. We also found that treatment with trilobatin had no significant effect on the expression of hepatitis B x-interacting protein (HBXIP) and hepatocyte nuclear factor (HNF)-4α, the two key regulators of hepatocyte proliferation. Taken together, although trilobatin worked as a novel inhibitor of SGLTs to attenuate the uptake of glucose, it also selectively induced the cell proliferation of HepG2 cells, suggesting that not all the SGLT inhibitors inhibited the proliferation of tumor cells, and further studies are needed to assess the anti-cancer potentials of new glucose-lowering agents. Full article

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14 pages, 2828 KiB

Open AccessArticle

New Functional Ingredients Based on Microencapsulation of Aqueous Anthocyanin-Rich Extracts Derived from Black Rice (Oryza sativa L.)

by Iuliana Aprodu, Ștefania Adelina Milea, Roxana-Mădălina Anghel, Elena Enachi, Vasilica Barbu, Oana Crăciunescu, Gabriela Râpeanu, Gabriela Elena Bahrim, Anca Oancea and Nicoleta Stănciuc

Molecules 2019, 24(18), 3389; https://doi.org/10.3390/molecules24183389 - 18 Sep 2019

Cited by 20 | Viewed by 4344

Abstract

The aqueous anthocyanin-rich extract derived from black rice (Oryza sativa L.) was encapsulated by freeze drying using milk proteins and peptides as coating materials. The molecular modelling approach indicated that all major casein fractions and whey proteins were able to bind at [...] Read more.

The aqueous anthocyanin-rich extract derived from black rice (Oryza sativa L.) was encapsulated by freeze drying using milk proteins and peptides as coating materials. The molecular modelling approach indicated that all major casein fractions and whey proteins were able to bind at least one anthocyanin molecule. The hydrophobic interactions and hydrogen bonding across the interfaces appeared to be mainly responsible for the stabilizations of the complexes formed between the coating material and bioactive compounds. Two dark purple colored powders, differentiated by the ratio of the encapsulation materials used, rich in phytochemicals were obtained, with an encapsulation efficiency of up to 99%. The powders were tested for antioxidant activity, cytocompatibility, and thermal stability. The morphological structure of the powders highlighted the presence of encapsulated anthocyanins. Both powders showed a remarkable antioxidant activity of about 46 mM Trolox/g D.W., and cytocompatibility on the L929 fibroblast culture. At certain concentrations, both powders stimulated cell proliferation. The powders showed a good thermal stability between 75 and 100 °C for 15 min. The powders were tested in a food model system and checked for stability of phytochemicals during storage. The added value of the powders was demonstrated throughout the antioxidant activity, which remained unchanged during storage. Full article

(This article belongs to the Special Issue Antioxidants Chemistry and Applications)

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23 pages, 2584 KiB

Open AccessReview

Yeast Models for Amyloids and Prions: Environmental Modulation and Drug Discovery

by Tatiana A. Chernova, Yury O. Chernoff and Keith D. Wilkinson

Molecules 2019, 24(18), 3388; https://doi.org/10.3390/molecules24183388 - 18 Sep 2019

Cited by 19 | Viewed by 4909

Abstract

Amyloids are self-perpetuating protein aggregates causing neurodegenerative diseases in mammals. Prions are transmissible protein isoforms (usually of amyloid nature). Prion features were recently reported for various proteins involved in amyloid and neural inclusion disorders. Heritable yeast prions share molecular properties (and in the [...] Read more.

Amyloids are self-perpetuating protein aggregates causing neurodegenerative diseases in mammals. Prions are transmissible protein isoforms (usually of amyloid nature). Prion features were recently reported for various proteins involved in amyloid and neural inclusion disorders. Heritable yeast prions share molecular properties (and in the case of polyglutamines, amino acid composition) with human disease-related amyloids. Fundamental protein quality control pathways, including chaperones, the ubiquitin proteasome system and autophagy are highly conserved between yeast and human cells. Crucial cellular proteins and conditions influencing amyloids and prions were uncovered in the yeast model. The treatments available for neurodegenerative amyloid-associated diseases are few and their efficiency is limited. Yeast models of amyloid-related neurodegenerative diseases have become powerful tools for high-throughput screening for chemical compounds and FDA-approved drugs that reduce aggregation and toxicity of amyloids. Although some environmental agents have been linked to certain amyloid diseases, the molecular basis of their action remains unclear. Environmental stresses trigger amyloid formation and loss, acting either via influencing intracellular concentrations of the amyloidogenic proteins or via heterologous inducers of prions. Studies of environmental and physiological regulation of yeast prions open new possibilities for pharmacological intervention and/or prophylactic procedures aiming on common cellular systems rather than the properties of specific amyloids. Full article

(This article belongs to the Special Issue Amyloid Inhibitors and Modulators)

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10 pages, 2659 KiB

Open AccessArticle

Molecular Docking and Dynamics Simulation of Protein β-Tubulin and Antifungal Cyclic Lipopeptides

by Nubia Noemi Cob-Calan, Luz America Chi-Uluac, Filiberto Ortiz-Chi, Daniel Cerqueda-García, Gabriel Navarrete-Vázquez, Esaú Ruiz-Sánchez and Emanuel Hernández-Núñez

Molecules 2019, 24(18), 3387; https://doi.org/10.3390/molecules24183387 - 18 Sep 2019

Cited by 41 | Viewed by 6616

Abstract

To elucidate interactions between the antifungal cyclic lipopeptides iturin A, fengycin, and surfactin produced by Bacillus bacteria and the microtubular protein β-tubulin in plant pathogenic fungi (Fusarium oxysporum, Colletrotrichum gloeosporioides, Alternaria alternata, and Fusarium solani) in molecular docking [...] Read more.

To elucidate interactions between the antifungal cyclic lipopeptides iturin A, fengycin, and surfactin produced by Bacillus bacteria and the microtubular protein β-tubulin in plant pathogenic fungi (Fusarium oxysporum, Colletrotrichum gloeosporioides, Alternaria alternata, and Fusarium solani) in molecular docking and molecular dynamics simulations, we retrieved the structure of tubulin co-crystallized with taxol from the Protein Data Bank (PDB) (ID: 1JFF) and the structure of the cyclic lipopeptides from PubChem (Compound CID: 102287549, 100977820, 10129764). Similarity and homology analyses of the retrieved β-tubulin structure with those of the fungi showed that the conserved domains shared 84% similarity, and the root mean square deviation (RMSD) was less than 2 Å. In the molecular docking studies, within the binding pocket, residues Pro274, Thr276, and Glu27 of β-tubulin were responsible for the interaction with the cyclic lipopeptides. In the molecular dynamics analysis, two groups of ligands were formed based on the number of poses analyzed with respect to the RMSD. Group 1 was made up of 10, 100, and 500 poses with distances 0.080 to 0.092 nm and RMSDs of 0.10 to 0.15 nm. For group 2, consisting of 1000 poses, the initial and final distance was 0.1 nm and the RMSDs were in the range of 0.10 to 0.30 nm. These results suggest that iturin A and fengycin bind with higher affinity than surfactin to β-tubulin. These two lipopeptides may be used as lead compounds to develop new antifungal agents or employed directly as biorational products to control plant pathogenic fungi. Full article

(This article belongs to the Special Issue Computational Enzymology: Understanding the Properties, Dynamics, and Reactivity of Enzymes)

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12 pages, 2041 KiB

Open AccessArticle

Antifungal Effects and Potential Mechanism of Essential Oils on Collelotrichum gloeosporioides In Vitro and In Vivo

by Dan Wang, Jing Zhang, Xiaoman Jia, Li Xin and Hao Zhai

Molecules 2019, 24(18), 3386; https://doi.org/10.3390/molecules24183386 - 18 Sep 2019

Cited by 38 | Viewed by 4711

Abstract

The development of natural essential oil as an alternative to synthetic chemicals in the control of postharvest decay is currently in the spotlight. In the present study, the efficacy of seven essential oils in suppressing Collelotrichum gloeosporioides identified from sweet cherry was evaluated [...] Read more.

The development of natural essential oil as an alternative to synthetic chemicals in the control of postharvest decay is currently in the spotlight. In the present study, the efficacy of seven essential oils in suppressing Collelotrichum gloeosporioides identified from sweet cherry was evaluated in vitro and clove oil was proved to be the most promising inhibitor. Thus, the antifungal properties and potential mechanisms of clove oil in vitro and in vivo by fumigation and contact treatments were intensively investigated. For C. gloeosporioides, the minimal inhibitory concentrations (MIC) of clove oil in air and contact phase were 80 and 300 μL/L in vitro testing, respectively. Based on the radial growth of C. gloeosporioides mycelium in medium, the fumgitoxic ability of essential oil was observed in a dose-dependent manner, which was not as dramatic as that under in vivo conditions. Furthermore, scanning electron microscopy and transmission electron microscopy of C. gloeosporioides exposed to clove oil exhibited obviously deleterious morphological and ultrastructural alterations confirming the disruption of fungal cell wall and endomembrane system, which resulted in increasing in permeability and causing the loss of intracellular constituents. In future, essential oils, combined with nano-emulsification approaches, could be good candidates as safe and effective antifungal agents for fungal spoilage of fresh commodities. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products)

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