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Molecules, Volume 24, Issue 21 (November-1 2019)

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Cover Story (view full-size image) A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal [...] Read more.
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Open AccessArticle
A Ratiometric and Colorimetric Hemicyanine Fluorescent Probe for Detection of SO2 Derivatives and Its Applications in Bioimaging
Molecules 2019, 24(21), 4011; https://doi.org/10.3390/molecules24214011 - 05 Nov 2019
Abstract
Based upon the intramolecular charge transfer (ICT) mechanism, a novel ratiometric fluorescent probe EB was developed to detect SO32−/HSO3. The probe displayed both colorimetric and ratiometric responses toward SO32−/HSO3. It displayed [...] Read more.
Based upon the intramolecular charge transfer (ICT) mechanism, a novel ratiometric fluorescent probe EB was developed to detect SO32−/HSO3. The probe displayed both colorimetric and ratiometric responses toward SO32−/HSO3. It displayed a quick response (within 60 s), good selectivity and high sensitivity (a detection limit of 28 nM) towards SO32−/HSO3. The SO32−/HSO3 sensing mechanism was confirmed as the Michael addition reaction by ESI-MS. Moreover, the probe could be applied to measure the level of sulfite in real samples, like sugar and chrysanthemum, and it could also be used to detect SO32−/HSO3 in HepG2 cells through confocal fluorescence microscopy, which proved its practical application in clinical diagnosis. Full article
(This article belongs to the Special Issue Fluorescence Spectroscopy of Biomolecules)
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Open AccessArticle
Synthesis, Surface and Antimicrobial Activity of New Lactose-Based Surfactants
Molecules 2019, 24(21), 4010; https://doi.org/10.3390/molecules24214010 - 05 Nov 2019
Abstract
This work presents a synthesis method for new surfactants based on lactose. The compounds obtained belong to the homologous series of O-β-D-Galactopyranosyl-(1→4)-N-alkyl-(3-sulfopropyl)-D-glucosamine hydrochloride, containing 12 and 14 carbon atoms in the alkyl chain, and they may serve as an example of [...] Read more.
This work presents a synthesis method for new surfactants based on lactose. The compounds obtained belong to the homologous series of O-β-D-Galactopyranosyl-(1→4)-N-alkyl-(3-sulfopropyl)-D-glucosamine hydrochloride, containing 12 and 14 carbon atoms in the alkyl chain, and they may serve as an example of cationic surfactants. The newly synthesized compounds exhibit good surface properties, low value of CMC (Critical Micelle Concentration) and good wetting properties. These surfactants’ ability to produce foam is considerably higher than in the commercial surfactants. Moreover, antibacterial and fungistatic activity was carried out by well diffusion assay against the selected bacteria (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa), yeasts (Candida albicans) and filamentous fungi (Fusarium graminearum, F. avenaceum, F. oxysporum, F. culmorum, F. equiseti, Alternaria alternata and Botrytis cinerea). It was shown that the resulting quaternary salts significantly inhibit the growth of tested microorganisms. Antibacterial and fungistatic activity of the surfactant compounds varied depending on the species of bacteria or fungi. The results of antimicrobial activity of new lactose derivatives indicate that the compounds exhibit larger or similar antagonistic activity against tested bacteria and fungi than typical cationic surfactant cetylpyridinium chloride. Full article
(This article belongs to the Section Green Chemistry)
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Open AccessFeature PaperArticle
Synthesis and Antimicrobial Evaluation of Novel Pyrazolopyrimidines Incorporated with Mono- and Diphenylsulfonyl Groups
Molecules 2019, 24(21), 4009; https://doi.org/10.3390/molecules24214009 - 05 Nov 2019
Abstract
A novel series of pyrazolo[1,5-a]pyrimidine ring systems containing phenylsulfonyl moiety have been synthesized via the reaction of 2-(phenylsulfonyl)-1-(4-(phenylsulfonyl) phenyl)ethan-1-one, 2-benzenesulfonyl-1-(4-benzenesulfonyl-phenyl)-3-dimethylamino-propenone and 3-(dimethylamino)-1-(4-(phenylsulfonyl)phenyl)prop-2-en-1-one each with various substituted aminoazopyrazole derivatives in one pot reaction strategy. The proposed structure as well as the mechanism [...] Read more.
A novel series of pyrazolo[1,5-a]pyrimidine ring systems containing phenylsulfonyl moiety have been synthesized via the reaction of 2-(phenylsulfonyl)-1-(4-(phenylsulfonyl) phenyl)ethan-1-one, 2-benzenesulfonyl-1-(4-benzenesulfonyl-phenyl)-3-dimethylamino-propenone and 3-(dimethylamino)-1-(4-(phenylsulfonyl)phenyl)prop-2-en-1-one each with various substituted aminoazopyrazole derivatives in one pot reaction strategy. The proposed structure as well as the mechanism of their reactions were discussed and proved with all possible spectral data. The results of antimicrobial activities of the new sulfone derivatives revealed that several derivatives showed activity exceeding the activity of reference drug. Contrary to expectations, we found that derivatives containing one sulfone group are more effective against all bacteria and fungi used than those contain two sulfone groups. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessReview
Halogenating Enzymes for Active Agent Synthesis: First Steps Are Done and Many Have to Follow
Molecules 2019, 24(21), 4008; https://doi.org/10.3390/molecules24214008 - 05 Nov 2019
Abstract
Halogens can be very important for active agents as vital parts of their binding mode, on the one hand, but are on the other hand instrumental in the synthesis of most active agents. However, the primary halogenating compound is molecular chlorine which has [...] Read more.
Halogens can be very important for active agents as vital parts of their binding mode, on the one hand, but are on the other hand instrumental in the synthesis of most active agents. However, the primary halogenating compound is molecular chlorine which has two major drawbacks, high energy consumption and hazardous handling. Nature bypassed molecular halogens and evolved at least six halogenating enzymes: Three kind of haloperoxidases, flavin-dependent halogenases as well as α-ketoglutarate and S-adenosylmethionine (SAM)-dependent halogenases. This review shows what is known today on these enzymes in terms of biocatalytic usage. The reader may understand this review as a plea for the usage of halogenating enzymes for fine chemical syntheses, but there are many steps to take until halogenating enzymes are reliable, flexible, and sustainable catalysts for halogenation. Full article
(This article belongs to the Special Issue Biocatalytic Synthesis of Bioactive Compounds)
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Open AccessCommunication
Separation, Identification, and Antioxidant Activity of Polyphenols from Lotus Seed Epicarp
Molecules 2019, 24(21), 4007; https://doi.org/10.3390/molecules24214007 - 05 Nov 2019
Abstract
Lotus seed epicarp, the main by-product of lotus seed processing, is abundant in polyphenols. In this study, polyphenols in lotus seed epicarp were separated by Sephadex LH-20 gel filtration chromatography to yield Fraction-I (F-I), Fraction-II (F-II), and Fraction-III (F-III). The polyphenol compounds in [...] Read more.
Lotus seed epicarp, the main by-product of lotus seed processing, is abundant in polyphenols. In this study, polyphenols in lotus seed epicarp were separated by Sephadex LH-20 gel filtration chromatography to yield Fraction-I (F-I), Fraction-II (F-II), and Fraction-III (F-III). The polyphenol compounds in the three fractions were identified by UPLC-MI-TOF-MS. Six kinds of polyphenol compounds including cyanidin-3-O-glucoside, procyanidin trimer, and phlorizin were identified in F-I, and prodelphinidin dimer B, procyanidin dimer, and quercetin hexoside isomer were found in F-II. However, there was only procyanidin dimer identified in F-III. The in vitro antioxidant activities of the three fractions were also investigated. We found F-I, F-II, and F-III had strong potential antioxidant activities in the order of F-III > F-II > F-I. Our results suggested that polyphenols from lotus seed epicarp might be suitable for use as a potential food additive. Full article
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Open AccessFeature PaperReview
An Appraisal of Developments in Allium Sulfur Chemistry: Expanding the Pharmacopeia of Garlic
Molecules 2019, 24(21), 4006; https://doi.org/10.3390/molecules24214006 - 05 Nov 2019
Abstract
Alliums and allied plant species are rich sources of sulfur compounds that have effects on vascular homeostasis and the control of metabolic systems linked to nutrient metabolism in mammals. In view of the multiple biological effects ascribed to these sulfur molecules, researchers are [...] Read more.
Alliums and allied plant species are rich sources of sulfur compounds that have effects on vascular homeostasis and the control of metabolic systems linked to nutrient metabolism in mammals. In view of the multiple biological effects ascribed to these sulfur molecules, researchers are now using these compounds as inspiration for the synthesis and development of novel sulfur-based therapeutics. This research has led to the chemical synthesis and biological assessment of a diverse array of sulfur compounds representative of derivatives of S-alkenyl-l-cysteine sulfoxides, thiosulfinates, ajoene molecules, sulfides, and S-allylcysteine. Many of these synthetic derivatives have potent antimicrobial and anticancer properties when tested in preclinical models of disease. Therefore, the current review provides an overview of advances in the development and biological assessment of synthetic analogs of allium-derived sulfur compounds. Full article
(This article belongs to the Special Issue Sulfur Compounds and Human Health)
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Open AccessArticle
Isolation, Structure Elucidation, and Antiproliferative Activity of Butanolides and Lignan Glycosides from the Fruit of Hernandia nymphaeifolia
Molecules 2019, 24(21), 4005; https://doi.org/10.3390/molecules24214005 - 05 Nov 2019
Abstract
Seven new butanolides, peltanolides A–G (17), and two lignan glucosides, peltasides A (8) and B (9), along with eleven known compounds, 1020, were isolated from a crude CH3OH/CH2Cl [...] Read more.
Seven new butanolides, peltanolides A–G (17), and two lignan glucosides, peltasides A (8) and B (9), along with eleven known compounds, 1020, were isolated from a crude CH3OH/CH2Cl2 (1:1) extract of the fruit of Hernandia nymphaeifolia (Hernandiaceae). The structures of 19 were characterized by extensive 1D and 2D NMR spectroscopic and HRMS analysis. The absolute configurations of newly isolated compounds 19 were determined from data obtained by optical rotation and electronic circular dichroism (ECD) exciton chirality methods. Butanolides and lignan glucosides have not been isolated previously from this genus. Several isolated compounds were evaluated for antiproliferative activity against human tumor cell lines. Lignans 15 and 16 were slightly active against chemosensitive tumor cell lines A549 and MCF-7, respectively. Furthermore, both compounds displayed significant activity (IC50 = 5 µM) against a P-glycoprotein overexpressing multidrug-resistant tumor cell line (KB-VIN) but were less active against its parent chemosensitive cell line (KB). Full article
(This article belongs to the Special Issue Antitumor and Anti-HIV Agents from Natural Products)
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Open AccessFeature PaperArticle
Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis
Molecules 2019, 24(21), 4004; https://doi.org/10.3390/molecules24214004 - 05 Nov 2019
Abstract
GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl [...] Read more.
GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitoring using NMR. The results, corroborated by theoretical calculations, indicate that a solution of piperidines in GVL should be prepared daily for a better Fmoc removal. Full article
(This article belongs to the Special Issue Peptide Chemistry Ⅱ)
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Open AccessArticle
Novel C7-Substituted Coumarins as Selective Monoamine Oxidase Inhibitors: Discovery, Synthesis and Theoretical Simulation
Molecules 2019, 24(21), 4003; https://doi.org/10.3390/molecules24214003 - 05 Nov 2019
Abstract
There is a continued need to develop new selective human monoamine oxidase (hMAO) inhibitors that could be beneficial for the treatment of neurological diseases. However, hMAOs are closely related with high sequence identity and structural similarity, which hinders the development [...] Read more.
There is a continued need to develop new selective human monoamine oxidase (hMAO) inhibitors that could be beneficial for the treatment of neurological diseases. However, hMAOs are closely related with high sequence identity and structural similarity, which hinders the development of selective MAO inhibitors. “Three-Dimensional Biologically Relevant Spectrum (BRS-3D)” method developed by our group has demonstrated its effectiveness in subtype selectivity studies of receptor and enzyme ligands. Here, we report a series of novel C7-substituted coumarins, either synthesized or commercially purchased, which were identified as selective hMAO inhibitors. Most of the compounds demonstrated strong activities with IC50 values (half-inhibitory concentration) ranging from sub-micromolar to nanomolar. Compounds, FR1 and SP1, were identified as the most selective hMAO-A inhibitors, with IC50 values of 1.5 nM (selectivity index (SI) < −2.82) and 19 nM (SI < −2.42), respectively. FR4 and FR5 showed the most potent hMAO-B inhibitory activity, with IC50 of 18 nM and 15 nM (SI > 2.74 and SI > 2.82). Docking calculations and molecular dynamic simulations were performed to elucidate the selectivity preference and SAR profiles. Full article
(This article belongs to the Special Issue Design, Synthesis, and Biological Evaluation of Enzyme Inhibitors)
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Open AccessArticle
Oleanolic Acid Acetate Exerts Anti-Inflammatory Activity via IKKα/β Suppression in TLR3-Mediated NF-κB Activation
Molecules 2019, 24(21), 4002; https://doi.org/10.3390/molecules24214002 - 05 Nov 2019
Abstract
Oleanolic acid acetate (OAA), a major triterpenoid compound of Vigna angularis (azuki bean, V. angularis), has been shown to downregulate inflammatory responses in macrophages. Here, we show the molecular basis for the effect of OAA on Toll-like receptor (TLR) downstream signaling. OAA [...] Read more.
Oleanolic acid acetate (OAA), a major triterpenoid compound of Vigna angularis (azuki bean, V. angularis), has been shown to downregulate inflammatory responses in macrophages. Here, we show the molecular basis for the effect of OAA on Toll-like receptor (TLR) downstream signaling. OAA treatment significantly inhibited the secretion of embryonic alkaline phosphatase (SEAP) induced by polyinosinic acid (poly(I), TLR3 ligand) in a dose-dependent manner and without cytotoxicity in THP1-XBlue cells. In addition, OAA downregulated the gene expression of poly(I) induced pro-inflammatory cytokines and chemokines genes such as MCP-1, IL-1β, IL-8, VCAM-1 and ICAM-1. Furthermore, we found that the inhibition activity of OAA was accompanied by decreased activation of not only nuclear factor-kappa B (NF-κB) signaling but also mitogen-activated protein kinase (MAPK) signaling upon stimulation with the TLR3 agonist. Interestingly, the interaction of OAA with IκB kinase α/β (IKKα/β) strongly attenuated the production of certain proteins and inflammatory cytokines in the TLR3 signaling pathway, such as nuclear factor of kappa light polypeptide gene enhancer in B-cells inhibitor, alpha (IkBα), extracellular regulated kinases (ERK), and p38, in an in vitro model. The action of OAA was regulated by TLR3, demonstrating that TLR3 plays a critical role in mediating the physiologically-relevant anti-inflammatory action of OAA and that the interaction with IKKα/β is modulated through TLR3. These results reveal new insight into the understanding of the regulatory mechanisms of the downstream TLR3 signaling pathway and consequent inflammatory responses that are involved in the development and progression of inflammatory diseases. Full article
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Open AccessArticle
Flavanol Glycoside Content of Grape Seeds and Skins of Vitis vinifera Varieties Grown in Castilla-La Mancha, Spain
Molecules 2019, 24(21), 4001; https://doi.org/10.3390/molecules24214001 - 05 Nov 2019
Abstract
Glycosylated flavanols (monoglycosides and diglycosides) in skin and seed extracts of Vitis vinifera grapes grown in Castilla-La Mancha (Spain) were investigated using ultra-high-performance liquid chromatography—tandem mass spectrometry (UHPLC-ESI-QQQ-MS/MS). Six grape varieties (Airén, Tempranillo, the recently identified Albillo Dorado, Montonera del Casar, Moribel, and [...] Read more.
Glycosylated flavanols (monoglycosides and diglycosides) in skin and seed extracts of Vitis vinifera grapes grown in Castilla-La Mancha (Spain) were investigated using ultra-high-performance liquid chromatography—tandem mass spectrometry (UHPLC-ESI-QQQ-MS/MS). Six grape varieties (Airén, Tempranillo, the recently identified Albillo Dorado, Montonera del Casar, Moribel, and Tinto Fragoso) were studied over two consecutive years (2016 and 2017). A total of twenty monomeric flavanol monoglycosides, four diglycosylated monomers, and three dimeric flavanol monoglycosides were detected in all grape samples. The diversity observed in the composition of glycosylated flavanol in the grape berries suggests a strong influence of variety and grape tissue (skin or seed). Monomeric flavanol glycosides were more abundant in grape seed extracts, in contrast with monoglycosylated dimeric forms. In addition, the glycosylated flavanol content was related to berry color in grape skins, with higher concentrations measured in black grape varieties. Full article
(This article belongs to the Special Issue Tannin Analysis, Chemistry, and Functions)
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Open AccessArticle
Synthesis and Bioactivity of Hydrazide-Hydrazones with the 1-Adamantyl-Carbonyl Moiety
Molecules 2019, 24(21), 4000; https://doi.org/10.3390/molecules24214000 - 05 Nov 2019
Abstract
Reaction of 1-adamantyl carbohydrazide (1) with various substituted benzaldehydes and acetophenones yielded the corresponding hydrazide-hydrazones with a 1-adamantane carbonyl moiety. The new synthesized compounds were tested for activities against some Gram-negative and Gram-positive bacteria, and the fungus Candida albicans. Compounds [...] Read more.
Reaction of 1-adamantyl carbohydrazide (1) with various substituted benzaldehydes and acetophenones yielded the corresponding hydrazide-hydrazones with a 1-adamantane carbonyl moiety. The new synthesized compounds were tested for activities against some Gram-negative and Gram-positive bacteria, and the fungus Candida albicans. Compounds 4a, 4b, 5a, and 5c displayed potential antibacterial activity against tested Gram-positive bacteria and C. albicans, while compounds 4e and 5e possessed cytotoxicity against tested human cancer cell lines. Full article
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Open AccessArticle
TMSBr-Promoted Cascade Cyclization of ortho-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications
Molecules 2019, 24(21), 3999; https://doi.org/10.3390/molecules24213999 - 05 Nov 2019
Abstract
Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared ortho-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups compatibility. Notably, TMSBr not only acted as an [...] Read more.
Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared ortho-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups compatibility. Notably, TMSBr not only acted as an acid-promoter to initiate the reaction, and also as a nucleophile. In addition, 4-bromo quinolines as key intermediates could further undergo the coupling reactions or nucleophilic reactions to provide a variety of functionalized compounds with molecular diversity at C4 position of quinolines. Full article
(This article belongs to the Special Issue Modern Strategies for Heterocycle Synthesis)
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Open AccessArticle
Structural Analysis of Gluco-Oligosaccharides Produced by Leuconostoc lactis and Their Prebiotic Effect
Molecules 2019, 24(21), 3998; https://doi.org/10.3390/molecules24213998 - 05 Nov 2019
Abstract
Leuconostoc lactis CCK940, which exhibits glycosyltransferase activity, produces oligosaccharides using sucrose and maltose as donor and receptor molecules, respectively. The oligosaccharides produced were purified by Bio-gel P2 chromatography and the purified oligosaccharides (CCK-oligosaccharides) consisted of only glucose. 1H-NMR analysis revealed that the [...] Read more.
Leuconostoc lactis CCK940, which exhibits glycosyltransferase activity, produces oligosaccharides using sucrose and maltose as donor and receptor molecules, respectively. The oligosaccharides produced were purified by Bio-gel P2 chromatography and the purified oligosaccharides (CCK-oligosaccharides) consisted of only glucose. 1H-NMR analysis revealed that the CCK-oligosaccharides were composed of 77.6% α-1,6 and 22.4% α-1,4 glycosidic linkages, and the molecular weight of the CCK-oligosaccharides was found to be 9.42 × 102 Da. To determine the prebiotic effect of the CCK-oligosaccharides, various carbon sources were added in modified media. Growth of six probiotic strains, Lactobacillus casei, L. pentosus, L. plantarum, Weissella cibaria, Bifidobacterim animalis, and Saccharomyces cerevisiae, was better when the CCK-oligosaccharides were used as the sole carbon source compared to fructo-oligosaccharides, which are widely used as prebiotics. These results showed that the CCK-oligosaccharides produced from Leu. lactis CCK940 could serve as good candidates for novel prebiotics. Full article
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Open AccessArticle
Evaluation of the Strain Bacillus amyloliquefaciens YP6 in Phoxim Degradation via Transcriptomic Data and Product Analysis
Molecules 2019, 24(21), 3997; https://doi.org/10.3390/molecules24213997 - 05 Nov 2019
Abstract
Phoxim, a type of organophosphorus pesticide (OP), is widely used in both agriculture and fisheries. The persistence of phoxim has caused serious environmental pollution problems. In this study, Bacillus amyloliquefaciens YP6 (YP6), which is capable of promoting plant growth and degrading broad-spectrum OPs, [...] Read more.
Phoxim, a type of organophosphorus pesticide (OP), is widely used in both agriculture and fisheries. The persistence of phoxim has caused serious environmental pollution problems. In this study, Bacillus amyloliquefaciens YP6 (YP6), which is capable of promoting plant growth and degrading broad-spectrum OPs, was used to study phoxim degradation. Different culture media were applied to evaluate the growth and phoxim degradation of YP6. YP6 can grow rapidly and degrade phoxim efficiently in Luria–Bertani broth (LB broth) medium. Furthermore, it can also utilize phoxim as the sole phosphorus source in a mineral salt medium. Response surface methodology was performed to optimize the degradation conditions of phoxim by YP6 in LB broth medium. The optimum biodegradation conditions were 40 °C, pH 7.20, and an inoculum size of 4.17% (v/v). The phoxim metabolites, O,O-diethylthiophosphoric ester, phoxom, and α-cyanobenzylideneaminooxy phosphonic acid, were confirmed by liquid chromatography–mass spectrometry. Meanwhile, transcriptome analysis and qRT-PCR were performed to give insight into the phoxim-stress response at the transcriptome level. The hydrolase-, oxidase-, and NADPH-cytochrome P450 reductase-encoding genes were significantly upregulated for phoxim hydrolysis, sulfoxidation, and o-dealkylation. Furthermore, the phoxim biodegradation pathways by YP6 were proposed, for the first time, based on transcriptomic data and product analysis. Full article
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Open AccessFeature PaperArticle
Magnetic Behavior of Carbon Materials Made from Biomass by Fe-Assisted Hydrothermal Carbonization
Molecules 2019, 24(21), 3996; https://doi.org/10.3390/molecules24213996 - 05 Nov 2019
Abstract
Biomass magnetic materials were synthesized by several hydrothermal carbonization methods, by which iron was provided in different ways: as FeCl3 prior to or during hydrothermal carbonization, as pure Fe particles, or as magnetic ferrofluid, followed or not by pyrolysis processes. The materials [...] Read more.
Biomass magnetic materials were synthesized by several hydrothermal carbonization methods, by which iron was provided in different ways: as FeCl3 prior to or during hydrothermal carbonization, as pure Fe particles, or as magnetic ferrofluid, followed or not by pyrolysis processes. The materials were thoughtfully characterized in terms of elemental composition, thermal degradation, porosity (N2 adsorption, SEM micrography), surface chemistry (FTIR spectroscopy, XRD diffraction), and magnetization curves on a self-made installation. The results indicated that the process design can significantly improve the structure and chemistry of the material, as well as the magnetization effect induced on the adsorbent. Fe as FeCl3 was more interesting in regards to the development of porosity, mainly creating micropores, although it did not provide magnetism to the material unless a further pyrolysis was applied. Thermal treatment at 600 °C did not only increase the BET-specific surface (SBET) (262 m2 g−1) of the hydrochar, but also involved the transformation of Fe into magnetite, providing magnetic behavior of the hydrochar. Increasing pyrolyisis temperature to 800 °C even enhanced a better development of porosity (SBET of 424 m2 g−1) and also increased the specific magnetic susceptibility of the hydrochar as a result of the further transition of Fe into wustite and hydroxi-ferrite. Full article
(This article belongs to the Special Issue Advances in Porous Materials)
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Open AccessArticle
Lasianosides A–E: New Iridoid Glucosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. and Their Antioxidant Activity
Molecules 2019, 24(21), 3995; https://doi.org/10.3390/molecules24213995 - 05 Nov 2019
Abstract
The genus Lasianthus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the Lasianthus species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. Lasianthus verticillatus (Lour.) Merr. (Syn. [...] Read more.
The genus Lasianthus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the Lasianthus species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. Lasianthus verticillatus (Lour.) Merr. (Syn. Lasianthus trichophlebus auct. non Hemsl.) is a shrub, branchlets terete about 1.5–3 m in height. This paper studies the chemical composition of the leaves of L. verticillatus for the first time, which resulted in the isolation of five undescribed iridoid glucosides, lasianosides A–E (15), together with three known compounds (68). The undescribed structures of isolated compounds (15) were characterized by physical and spectroscopic data analyses, including one-dimensional (1D) and two-dimensional (2D) NMR, IR, UV, and high-resolution electrospray ionization mass spectra (HR-ESI-MS). Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The free radical scavenging properties of isolated compounds was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and their cytotoxicity was assessed toward human lung cancer cell line A549 by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the isolated compounds, 3 and 4 displayed potent radical scavenging activities with IC50 values of 30.2 ± 1.8 and 32.0 ± 1.2 µM, which were comparable to that of Trolox (29.2 ± 0.39 µM), respectively, while 5 possessed moderate activity with an IC50 value of 46.4 ± 2.3 µM. None of the isolated compounds exerted cytotoxicity against human cell line A549. As a result, lasianosides C, D, and E have the potential to be non-toxic safe antioxidant agents. Full article
(This article belongs to the Special Issue Biological Activities of Plant Secondary Metabolites)
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Open AccessArticle
In Vivo and In Vitro Study of Immunostimulation by Leuconostoc lactis-Produced Gluco-Oligosaccharides
Molecules 2019, 24(21), 3994; https://doi.org/10.3390/molecules24213994 - 05 Nov 2019
Abstract
Glycosyltransferase-producing Leuconostoc lactis CCK940 produces CCK- oligosaccharides, gluco-oligosaccharide molecules, using sucrose and maltose as donor and acceptor molecules, respectively. In this study, the immunostimulatory activities of CCK-oligosaccharides on RAW264.7 macrophages and BALB/c mice were evaluated. CCK-oligosaccharides induced the expression of phosphorylated-p38, extracellular-signal-regulated kinase [...] Read more.
Glycosyltransferase-producing Leuconostoc lactis CCK940 produces CCK- oligosaccharides, gluco-oligosaccharide molecules, using sucrose and maltose as donor and acceptor molecules, respectively. In this study, the immunostimulatory activities of CCK-oligosaccharides on RAW264.7 macrophages and BALB/c mice were evaluated. CCK-oligosaccharides induced the expression of phosphorylated-p38, extracellular-signal-regulated kinase (ERK), and c-Jun N-terminal kinase (JNK) and upregulation of phagocytic activity in RAW264.7 macrophages, suggesting their involvement in mitogen-activated protein kinase (MAPK) signaling pathway and phagocytosis. When CCK-oligosaccharides were administered to mice intraperitoneally injected with cyclophosphamide (CY), spleen indices and expressions of interleukin (IL)-6, IL–10, and tumor necrosis factor-α increased, compared with those in only CY-treated group. These findings suggest that CCK-oligosaccharides can be used as an effective immunostimulating agent. Full article
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Open AccessArticle
Early Celastrol Administration Prevents Ketamine-Induced Psychotic-Like Behavioral Dysfunctions, Oxidative Stress and IL-10 Reduction in The Cerebellum of Adult Mice
Molecules 2019, 24(21), 3993; https://doi.org/10.3390/molecules24213993 - 05 Nov 2019
Abstract
Administration of subanesthetic doses of ketamine during brain maturation represents a tool to mimic an early insult to the central nervous system (CNS). The cerebellum is a key player in psychosis pathogenesis, to which oxidative stress also contributes. Here, we investigated the impact [...] Read more.
Administration of subanesthetic doses of ketamine during brain maturation represents a tool to mimic an early insult to the central nervous system (CNS). The cerebellum is a key player in psychosis pathogenesis, to which oxidative stress also contributes. Here, we investigated the impact of early celastrol administration on behavioral dysfunctions in adult mice that had received ketamine (30 mg/kg i.p.) at postnatal days (PNDs) 7, 9, and 11. Cerebellar levels of 8-hydroxydeoxyguanosine (8-OHdG), NADPH oxidase (NOX) 1 and NOX2, as well as of the calcium-binding protein parvalbumin (PV), were also assessed. Furthermore, celastrol effects on ketamine-induced alterations of proinflammatory (TNF-α, IL-6 and IL-1β) and anti-inflammatory (IL-10) cytokines in this brain region were evaluated. Early celastrol administration prevented ketamine-induced discrimination index decrease at adulthood. The same was found for locomotor activity elevations and increased close following and allogrooming, whereas no beneficial effects on sniffing impairment were detected. Ketamine increased 8-OHdG in the cerebellum of adult mice, which was also prevented by early celastrol injection. Cerebellar NOX1 levels were enhanced at adulthood following postnatal ketamine exposure. Celastrol per se induced NOX1 decrease in the cerebellum. This effect was more significant in animals that were early administered with ketamine. NOX2 levels did not change. Ketamine administration did not affect PV amount in the cerebellum. TNF-α levels were enhanced in ketamine-treated animals; however, this was not prevented by early celastrol administration. While no changes were observed for IL-6 and IL-1β levels, ketamine determined a reduction of cerebellar IL-10 expression, which was prevented by early celastrol treatment. Our results suggest that NOX inhibition during brain maturation prevents the development of psychotic-like behavioral dysfunctions, as well as the increased cerebellar oxidative stress and the reduction of IL-10 in the same brain region following ketamine exposure in postnatal life. This opens novel neuroprotective opportunities against early detrimental insults occurring during brain development. Full article
(This article belongs to the Special Issue Natural Products and Drug Discovery)
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Open AccessFeature PaperReview
Circulating Metabolites Originating from Gut Microbiota Control Endothelial Cell Function
Molecules 2019, 24(21), 3992; https://doi.org/10.3390/molecules24213992 - 05 Nov 2019
Abstract
Cardiovascular functionality strictly depends on endothelial cell trophism and proper biochemical function. Any condition (environmental, pharmacological/toxicological, physical, or neuro-humoral) that changes the vascular endothelium has great consequences for the organism’s wellness and on the outcome and evolution of severe cardiovascular pathologies. Thus, knowledge [...] Read more.
Cardiovascular functionality strictly depends on endothelial cell trophism and proper biochemical function. Any condition (environmental, pharmacological/toxicological, physical, or neuro-humoral) that changes the vascular endothelium has great consequences for the organism’s wellness and on the outcome and evolution of severe cardiovascular pathologies. Thus, knowledge of the mechanisms, both endogenous and external, that affect endothelial dysfunction is pivotal to preventing and treating these disorders. In recent decades, significant attention has been focused on gut microbiota and how these symbiotic microorganisms can influence host health and disease development. Indeed, dysbiosis has been reported to be at the base of a range of different pathologies, including pathologies of the cardiovascular system. The study of the mechanism underlying this relationship has led to the identification of a series of metabolites (released by gut bacteria) that exert different effects on all the components of the vascular system, and in particular on endothelial cells. The imbalance of factors promoting or blunting endothelial cell viability and function and angiogenesis seems to be a potential target for the development of new therapeutic interventions. This review highlights the circulating factors identified to date, either directly produced by gut microbes or resulting from the metabolism of diet derivatives as polyphenols. Full article
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Open AccessArticle
Anti-Bacterial Effect and Cytotoxicity Assessment of Lipid 430 Isolated from Algibacter sp.
Molecules 2019, 24(21), 3991; https://doi.org/10.3390/molecules24213991 - 05 Nov 2019
Abstract
Two bacterial isolates from the Barents Sea, both belonging to the genus Algibacter, were found to yield extracts with anti-bacterial bioactivity. Mass spectrometry guided dereplication and purification of the active extracts lead to the isolation of the same active principle in both [...] Read more.
Two bacterial isolates from the Barents Sea, both belonging to the genus Algibacter, were found to yield extracts with anti-bacterial bioactivity. Mass spectrometry guided dereplication and purification of the active extracts lead to the isolation of the same active principle in both extracts. The structure of the bioactive compound was identified via mass spectrometry and nuclear resonance spectroscopy and it turned out to be the known lipopeptide Lipid 430. We discovered and determined its previously unknown anti-bacterial activity against Streptococcus agalactiae and revealed a cytotoxic effect against the A2058 human melanoma cell line at significantly lower concentrations compared to its anti-bacterial concentration. Flow cytometry and microscopy investigations of the cytotoxicity against the melanoma cell line indicated that Lipid 430 did not cause immediate cell lysis. The experiments with melanoma cells suggest that the compound functions trough more complex pathways than acting as a simple detergent. Full article
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Open AccessArticle
Investigation of Potential Amorphisation and Co-Amorphisation Behaviour of the Benzene Di-Carboxylic Acids upon Cryo-Milling
Molecules 2019, 24(21), 3990; https://doi.org/10.3390/molecules24213990 - 05 Nov 2019
Abstract
Multi-component formulations offer a way to modulate the physico-chemical properties of drug molecules and thereby enhance their efficacy as medicines compared to using only the raw drug, with mechano-chemical synthesis being an increasingly popular way to create these novel materials in a research [...] Read more.
Multi-component formulations offer a way to modulate the physico-chemical properties of drug molecules and thereby enhance their efficacy as medicines compared to using only the raw drug, with mechano-chemical synthesis being an increasingly popular way to create these novel materials in a research setting. However, to date studies have focussed on employing pharmaceutically acceptable components, which has led to the literature featuring chemically diverse pairings of drug and excipient. Here we investigate the outcome of cryo-milling and co-cryo-milling of a series of three simple geometrical isomers of benzene di-carboxylic acid with a view to developing a chemically simple model system to investigate areas including cryo-milling, co-cryo-milling, co-amorphous formulation, etc. All three single-component materials exhibit differing behaviour upon cryo-milling and subsequent storage, as do the two-component mixtures. The surprisingly differing behaviours of these chemically similar species upon cryo-milling and co-cryo-milling suggest that molecular chemistry may not be the dominant influence on the outcome of mechano-chemical syntheses, and that other properties should be explored to develop a predictive model for the outcomes of these types of reactions. Full article
(This article belongs to the Special Issue Recent Development of Mechanochemical Synthesis)
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Open AccessArticle
Study on the Mechanical Properties and Strengthening Mechanism of Interface-Modified Carbon Fiber Mesh Reinforced Cement-Based Composites with SCA&HMC
Molecules 2019, 24(21), 3989; https://doi.org/10.3390/molecules24213989 - 05 Nov 2019
Abstract
Carbon fiber mesh reinforced cement-based composites (CMCCs) have received extensive attention in the field of engineering repair and structural reinforcement due to their outstanding properties such as two-way force, rust prevention, high specific strength, and low base surface requirements. However, the development of [...] Read more.
Carbon fiber mesh reinforced cement-based composites (CMCCs) have received extensive attention in the field of engineering repair and structural reinforcement due to their outstanding properties such as two-way force, rust prevention, high specific strength, and low base surface requirements. However, the development of this material has been slowed down to some extent due to the poor interfacial bonding between the carbon fiber mesh and the cement matrix. In this paper, a novel fabrication strategy was proposed in which the carbon fiber mesh was modified with epoxy resin and silane coupling agent (SCA) to increase its surface chemical activity. Meanwhile, the hydroxymethyl cellulose (HMC) was also filled into the concrete matrix to improve the mechanical strength of the matrix as well as the load transfer behaviors between the mortar and carbon fiber (CF) mesh. The potential to employ SCA and HMC was evaluated for the making of CMCCs via the above methods. The results showed that the longitudinal shear strength of composites with SCA and SCA&HMC increased by 26.6% and 56.1% compared to those of CF with epoxy resin (EP) reinforced composites, respectively. The flexural strength of composite with SCA&HMC increases by 147.6% compared to I-(F) without CF. The novel II-HCM&CF/EP-SCA composites with excellent performance are promised to be applied in practical uses. Full article
(This article belongs to the Special Issue Fibre Reinforced Composites: Interfacial Modifications and Property)
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Open AccessFeature PaperArticle
Synthesis and Antiviral Activity of Novel 1,3,4-Thiadiazole Inhibitors of DDX3X
Molecules 2019, 24(21), 3988; https://doi.org/10.3390/molecules24213988 - 04 Nov 2019
Abstract
The human ATPase/RNA helicase X-linked DEAD-box polypeptide 3 (DDX3X) emerged as a novel therapeutic target in the fight against both infectious diseases and cancer. Herein, a new family of DDX3X inhibitors was designed, synthesized, and tested for its inhibitory action on the ATPase [...] Read more.
The human ATPase/RNA helicase X-linked DEAD-box polypeptide 3 (DDX3X) emerged as a novel therapeutic target in the fight against both infectious diseases and cancer. Herein, a new family of DDX3X inhibitors was designed, synthesized, and tested for its inhibitory action on the ATPase activity of the enzyme. The potential use of the most promising derivatives it has been investigated by evaluating their anti-HIV-1 effects, revealing inhibitory activities in the low micromolar range. A preliminary ADME analysis demonstrated high metabolic stability and good aqueous solubility. The promising biological profile, together with the suitable in vitro pharmacokinetic properties, make these novel compounds a very good starting point for further development. Full article
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Open AccessArticle
Mechanism of Action of Non-Synonymous Single Nucleotide Variations Associated with α-Carbonic Anhydrase II Deficiency
Molecules 2019, 24(21), 3987; https://doi.org/10.3390/molecules24213987 - 04 Nov 2019
Abstract
Human carbonic anhydrase II (CA-II) is a Zinc (Zn 2 + ) metalloenzyme responsible for maintenance of acid-base balance within the body through the reversible hydration of CO 2 to produce protons (H + ) and bicarbonate (BCT). Due to its importance, alterations [...] Read more.
Human carbonic anhydrase II (CA-II) is a Zinc (Zn 2 + ) metalloenzyme responsible for maintenance of acid-base balance within the body through the reversible hydration of CO 2 to produce protons (H + ) and bicarbonate (BCT). Due to its importance, alterations to the amino acid sequence of the protein as a result of single nucleotide variations (nsSNVs) have detrimental effects on homeostasis. Six pathogenic CA-II nsSNVs, K18E, K18Q, H107Y, P236H, P236R and N252D were identified, and variant protein models calculated using homology modeling. The effect of each nsSNV was analyzed using motif analysis, molecular dynamics (MD) simulations, principal component (PCA) and dynamic residue network (DRN) analysis. Motif analysis identified 11 functionally important motifs in CA-II. RMSD data indicated subtle SNV effects, while PCA analysis revealed that the presence of BCT results in greater conformational sampling and free energy in proteins. DRN analysis showed variant allosteric effects, and the average betweenness centrality (BC) calculations identified Glu117 as the most important residue for communication in CA-II. The presence of BCT was associated with a reduction to Glu117 usage in all variants, suggesting implications for Zn 2 + dissociation from the CA-II active site. In addition, reductions to Glu117 usage are associated with increases in the usage of the primary and secondary Zn 2 + ligands; His94, His96, His119 and Asn243 highlighting potential compensatory mechanisms to maintain Zn 2 + within the active site. Compared to traditional MD simulation investigation, DRN analysis provided greater insights into SNV mechanism of action, indicating its importance for the study of missense mutation effects in proteins and, in broader terms, precision medicine related research. Full article
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Open AccessFeature PaperArticle
Single-Step Methylation of Chitosan Using Dimethyl Carbonate as a Green Methylating Agent
Molecules 2019, 24(21), 3986; https://doi.org/10.3390/molecules24213986 - 04 Nov 2019
Abstract
N,N,N-Trimethyl chitosan (TMC) is one chitosan derivative that, because of its improved solubility, has been studied for industrial and pharmaceutic applications. Conventional methods for the synthesis of TMC involve the use of highly toxic and harmful reagents, such as methyl iodide and [...] Read more.
N,N,N-Trimethyl chitosan (TMC) is one chitosan derivative that, because of its improved solubility, has been studied for industrial and pharmaceutic applications. Conventional methods for the synthesis of TMC involve the use of highly toxic and harmful reagents, such as methyl iodide and dimethyl sulfate (DMS). Although the methylation of dimethylated chitosan to TMC by dimethyl carbonate (DMC, a green and benign methylating agent) was reported recently, it involved a formaldehyde-based procedure. In this paper we report the single-step synthesis of TMC from chitosan using DMC in an ionic liquid. The TMC synthesised was characterised by 1H NMR spectroscopy and a functionally meaningful degree of quaternisation of 9% was demonstrated after a 12-h reaction time. Full article
(This article belongs to the Special Issue Advances in Conversion of Biomass and Waste to Chemicals and Fuels)
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Open AccessFeature PaperArticle
One-Pot Cu/TiO2 Nanoparticles Synthesis for Trans-Ferulic Acid Conversion into Vanillin
Molecules 2019, 24(21), 3985; https://doi.org/10.3390/molecules24213985 - 04 Nov 2019
Abstract
In this study, the co-synthesis of TiO2 and Cu metallic nanoparticles obtained via one-pot cost-efficient hydrothermal process has been addressed. Different nanocatalysts with Cu contents were characterized by X-ray diffraction, nitrogen porosimetry, scanning electron microscopy, and transmission electron microscopy. The TiO2 [...] Read more.
In this study, the co-synthesis of TiO2 and Cu metallic nanoparticles obtained via one-pot cost-efficient hydrothermal process has been addressed. Different nanocatalysts with Cu contents were characterized by X-ray diffraction, nitrogen porosimetry, scanning electron microscopy, and transmission electron microscopy. The TiO2 and Cu metallic nanoparticles were synthesized with copper loading up to one (Cu/Ti atomic ratio). Synthesized catalysts exhibited pore sizes in the mesoporous range and high surface areas above 150 m2/g. The particle size for TiO2 presented a homogeneous distribution of approximately 8 nm, moreover, Cu nanoparticles varied from 12 to >100 nm depending on the metal loading. The nanostructured materials were successfully tested in the conversion of trans-ferulic acid into vanillin under sustainable conditions, achieving the best performance for 0.3 Cu/Ti atomic ratio (70% vanillin yield). Full article
(This article belongs to the Special Issue Nanomaterials for Catalysis)
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Open AccessArticle
Isorhamnetin Has Potential for the Treatment of Escherichia coli-Induced Sepsis
Molecules 2019, 24(21), 3984; https://doi.org/10.3390/molecules24213984 - 04 Nov 2019
Abstract
Isorhamnetin is a flavonoid that is abundant in the fruit of Hippophae rhamnoides L. It is widely studied for its ability to modulate inflammatory responses. In this study, we evaluated the potential of isorhamnetin to prevent gram-negative sepsis. We investigated its efficacy using [...] Read more.
Isorhamnetin is a flavonoid that is abundant in the fruit of Hippophae rhamnoides L. It is widely studied for its ability to modulate inflammatory responses. In this study, we evaluated the potential of isorhamnetin to prevent gram-negative sepsis. We investigated its efficacy using an Escherichia coli-induced sepsis model. Our study reveals that isorhamnetin treatment significantly enhances survival and reduces proinflammatory cytokine levels in the serum and lung tissue of E. coli-infected mice. Further, isorhamnetin treatment also significantly reduces the levels of aspartate aminotransferase, alanine amino transferase and blood urea nitrogen, suggesting that it can improve liver and kidney function in infected mice. Docking studies reveal that isorhamnetin binds deep in the hydrophobic binding pocket of MD-2 via extensive hydrophobic interactions and hydrogen bonding with Tyr102, preventing TLR4/MD-2 dimerization. Notably, binding and secreted alkaline phosphatase reporter gene assays show that isorhamnetin can interact directly with the TLR4/MD-2 complex, thus inhibiting the TLR4 cascade, which eventually causes systemic inflammation, resulting in death due to cytokine storms. We therefore presume that isorhamnetin could be a suitable therapeutic candidate to treat bacterial sepsis. Full article
(This article belongs to the Special Issue Flavonoids and Their Disease Prevention and Treatment Potential)
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Open AccessArticle
Comparison of the Fatty Acid and Triglyceride Profiles of Big Eye Tuna (Thunnus obesus), Atlantic salmon (Salmo salar) and Bighead Carp (Aristichthysnobilis) Heads
Molecules 2019, 24(21), 3983; https://doi.org/10.3390/molecules24213983 - 04 Nov 2019
Abstract
Big eye tuna (Thunnus obesus), Atlantic salmon (Salmo salar) and bighead carp (Aristichthys nobilis) are three representative marine and fresh water fishes. In this study, the content of total lipids (TL), triglyceride (TG) fraction, and the fatty [...] Read more.
Big eye tuna (Thunnus obesus), Atlantic salmon (Salmo salar) and bighead carp (Aristichthys nobilis) are three representative marine and fresh water fishes. In this study, the content of total lipids (TL), triglyceride (TG) fraction, and the fatty acid profiles in the corresponding fish heads were analyzed. Meanwhile, their complicated TG molecular species were further characterized. The results showed that TG was the major lipid in these three fish heads (60.58–86.69%). Compared with other two fish heads, big eye tuna head was the most abundant in polyunsaturated fatty acids, among which eicosapentaenoic acid (EPA) + docosahexaenoic acid (DHA) accounted for 64.29% and 32.77% in the TL and TG fraction, respectively. It is also worth noting that EPA+DHA/total fatty acid (TFA) value of TL and TG fraction from bighead carp head showed no significant difference with Atlantic salmon head, a typical marine fish. There were 146 TG molecules detected in big eye tuna head, 90 in Atlantic salmon and 87 in bighead carp heads. DHA or EPA accounted for 56.12%, 22.88%, and 5.46% of the total TG molecules in these three fish heads, respectively. According to principal component analysis, orthogonal projection to latent structures-discriminant analysis and the constructed heat map, the three samples could be completely differentiated based on their TG molecule fingerprints. This study is the first to compare marine and fresh water fish from the perspective of their heads’ fatty acid and TG molecule profiles. Full article
(This article belongs to the Special Issue Natural Products Used as Foods and Food Ingredients)
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Open AccessReview
The Polyphenols as Potential Agents in Prevention and Therapy of Prostate Diseases
Molecules 2019, 24(21), 3982; https://doi.org/10.3390/molecules24213982 - 04 Nov 2019
Abstract
In recent years, the progress of science and medicine greatly has influenced human life span and health. However, lifestyle habits, like physical activity, smoking cessation, moderate alcohol consumption, diet, and maintaining a normal body weight represent measures that greatly reduce the risk of [...] Read more.
In recent years, the progress of science and medicine greatly has influenced human life span and health. However, lifestyle habits, like physical activity, smoking cessation, moderate alcohol consumption, diet, and maintaining a normal body weight represent measures that greatly reduce the risk of various diseases. The type of diet is very important for disease development. Numerous epidemiological clinical data confirm that longevity is linked to predominantly plant-based diets and it is related to a long life; whereas the western diet, rich in red meat and fats, increases the risk of oxidative stress and thus the risk of developing various diseases and pre-aging. This review is focused on the bioavailability of polyphenols and the use of polyphenols for the prevention of prostate diseases. Special focus in this paper is placed on the isoflavonoids and flavan-3-ols, subgroups of polyphenols, and their protective effects against the development of prostate diseases. Full article
(This article belongs to the Special Issue Phytochemicals in Medicine and Food)
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