Molecules

5 pages, 273 KiB

Open AccessEditorial

Recent Progress in Understanding the Health Benefits of Curcumin

by Chiara Porro and Maria Antonietta Panaro

Molecules 2023, 28(5), 2418; https://doi.org/10.3390/molecules28052418 - 06 Mar 2023

Cited by 1 | Viewed by 1994

Nutrients and their potential benefits are a new field of study in modern medicine due to their positive impact on health [...] Full article

(This article belongs to the Special Issue Recent Progress in Health Benefits from Curcumin)

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21 pages, 4567 KiB

Open AccessArticle

Aspirin-Triggered Resolvin D1 (AT-RvD1) Protects Mouse Skin against UVB-Induced Inflammation and Oxidative Stress

by Cristina P. B. Melo, Priscila Saito, Renata M. Martinez, Larissa Staurengo-Ferrari, Ingrid C. Pinto, Camilla C. A. Rodrigues, Stephanie Badaro-Garcia, Josiane A. Vignoli, Marcela M. Baracat, Allan J. C. Bussmann, Sandra R. Georgetti, Waldiceu A. Verri and Rubia Casagrande

Molecules 2023, 28(5), 2417; https://doi.org/10.3390/molecules28052417 - 06 Mar 2023

Cited by 1 | Viewed by 2070

Abstract

Intense exposure to UVB radiation incites excessive production of reactive oxygen species (ROS) and inflammation. The resolution of inflammation is an active process orchestrated by a family of lipid molecules that includes AT-RvD1, a specialized proresolving lipid mediator (SPM). AT-RvD1 is derived from [...] Read more.

Intense exposure to UVB radiation incites excessive production of reactive oxygen species (ROS) and inflammation. The resolution of inflammation is an active process orchestrated by a family of lipid molecules that includes AT-RvD1, a specialized proresolving lipid mediator (SPM). AT-RvD1 is derived from omega-3, which presents anti-inflammatory activity and reduces oxidative stress markers. The present work aims to investigate the protective effect of AT-RvD1 on UVB-induced inflammation and oxidative stress in hairless mice. Animals were first treated with 30, 100, and 300 pg/animal AT-RvD1 (i.v.) and then exposed to UVB (4.14 J/cm²). The results showed that 300 pg/animal of AT-RvD1 could restrict skin edema, neutrophil and mast cell infiltration, COX-2 mRNA expression, cytokine release, and MMP-9 activity and restore skin antioxidant capacity as per FRAP and ABTS assays and control O₂^•− production, lipoperoxidation, epidermal thickening, and sunburn cells development. AT-RvD1 could reverse the UVB-induced downregulation of Nrf2 and its downstream targets GSH, catalase, and NOQ-1. Our results suggest that by upregulating the Nrf2 pathway, AT-RvD1 promotes the expression of ARE genes, restoring the skin’s natural antioxidant defense against UVB exposition to avoid oxidative stress, inflammation, and tissue damage. Full article

(This article belongs to the Section Bioactive Lipids)

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14 pages, 3354 KiB

Open AccessArticle

Anti-Inflammatory Activity of Panax notoginseng Flower Saponins Quantified Using LC/MS/MS

by Junchen Liu, Yuehang Wu, Wenrui Ma, Hongyan Zhang, Xianyao Meng, Huirong Zhang, Miaomiao Guo, Xiao Ling and Li Li

Molecules 2023, 28(5), 2416; https://doi.org/10.3390/molecules28052416 - 06 Mar 2023

Cited by 4 | Viewed by 2088

Abstract

Panax notoginseng (Burk) F. H. Chen is a traditional Chinese medicinal and edible plant. However, Panax notoginseng flower (PNF) is rarely used. Therefore, the purpose of this study was to explore the main saponins and the anti-inflammatory bioactivity of PNF saponins (PNFS). We [...] Read more.

Panax notoginseng (Burk) F. H. Chen is a traditional Chinese medicinal and edible plant. However, Panax notoginseng flower (PNF) is rarely used. Therefore, the purpose of this study was to explore the main saponins and the anti-inflammatory bioactivity of PNF saponins (PNFS). We explored the regulation of cyclooxygenase 2 (COX–2), a key mediator of inflammatory pathways, in human keratinocyte cells treated with PNFS. A cell model of UVB-irradiation-induced inflammation was established to determine the influence of PNFS on inflammatory factors and their relationship with LL–37 expression. An enzyme-linked immunosorbent assay and Western blotting analysis were used to detect the production of inflammatory factors and LL37. Finally, liquid chromatography–tandem mass spectrometry was employed to quantify the main active components (ginsenosides Rb1, Rb2, Rb3, Rc, Rd, Re, Rg1, and notoginsenoside R1) in PNF. The results show that PNFS substantially inhibited COX–2 activity and downregulated the production of inflammatory factors, indicating that they can be used to reduce skin inflammation. PNFS also increased the expression of LL-37. The contents of ginsenosides Rb1, Rb2, Rb3, Rc, and Rd in PNF were much higher than those of Rg1, and notoginsenoside R1. This paper provides data in support of the application of PNF in cosmetics. Full article

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12 pages, 1893 KiB

Open AccessArticle

Isolation and Characterization of an Unknown Process-Related Impurity in Furosemide and Validation of a New HPLC Method

by Ao Xu, Yunlin Xue, Yuyu Zeng, Jing Li, Huiling Zhou, Zhen Wang, Yin Chen, Hui Chen, Jian Jin and Tao Zhuang

Molecules 2023, 28(5), 2415; https://doi.org/10.3390/molecules28052415 - 06 Mar 2023

Viewed by 1978

Abstract

Furosemide is a widely used loop diuretic in the treatment of congestive heart failure and edema. During the preparation of furosemide, a new process-related impurity G in the levels ranging from 0.08% to 0.13% was detected in pilot batches by a new high [...] Read more.

Furosemide is a widely used loop diuretic in the treatment of congestive heart failure and edema. During the preparation of furosemide, a new process-related impurity G in the levels ranging from 0.08% to 0.13% was detected in pilot batches by a new high performance liquid chromatography (HPLC) method. The new impurity was isolated and characterized by comprehensive analysis of FT-IR, Q-TOF/LC-MS, 1D-NMR (¹H, ¹³C, and DEPT), and 2D-NMR (¹H-¹H-COSY, HSQC, and HMBC) spectroscopy data. The possible formation pathway of impurity G was also discussed in detail. Moreover, a novel HPLC method was developed and validated for the determination of impurity G and the other six known impurities registered in the European Pharmacopoeia as per ICH guidelines. The HPLC method was validated with respect to system suitability, linearity, the limit of quantitation, the limit of detection, precision, accuracy, and robustness. The characterization of impurity G and the validation of its quantitative HPLC method were reported for the first time in this paper. Finally, the toxicological properties of impurity G were predicted by the in silico webserver ProTox-II. Full article

(This article belongs to the Special Issue Advanced Analytical Tools for Characterization and Quality Control of Food, Drugs, and Natural Active Ingredients)

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16 pages, 2631 KiB

Open AccessArticle

Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline

by Sandra Hernández-Ibáñez, Ana Sirvent, Miguel Yus and Francisco Foubelo

Molecules 2023, 28(5), 2414; https://doi.org/10.3390/molecules28052414 - 06 Mar 2023

Cited by 1 | Viewed by 1313

Abstract

The stereocontrolled synthesis of 1-substituted homotropanones, using chiral N-tert-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehydes, decarboxylative Mannich reaction with [...] Read more.

The stereocontrolled synthesis of 1-substituted homotropanones, using chiral N-tert-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehydes, decarboxylative Mannich reaction with β-keto acids of these aldimines, and organocatalyzed L-proline intramolecular Mannich cyclization are key steps of this methodology. The utility of the method was demonstrated with a synthesis of the natural product (−)-adaline, and its enantiomer, (+)-adaline. Full article

(This article belongs to the Special Issue A Journey of Organic Chemistry in Spain)

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31 pages, 14207 KiB

Open AccessReview

Therapeutic Effects of Coumarins with Different Substitution Patterns

by Virginia Flores-Morales, Ana P. Villasana-Ruíz, Idalia Garza-Veloz, Samantha González-Delgado and Margarita L. Martinez-Fierro

Molecules 2023, 28(5), 2413; https://doi.org/10.3390/molecules28052413 - 06 Mar 2023

Cited by 27 | Viewed by 6340

Abstract

The use of derivatives of natural and synthetic origin has gained attention because of their therapeutic effects against human diseases. Coumarins are one of the most common organic molecules and are used in medicine for their pharmacological and biological effects, such as anti-inflammatory, [...] Read more.

The use of derivatives of natural and synthetic origin has gained attention because of their therapeutic effects against human diseases. Coumarins are one of the most common organic molecules and are used in medicine for their pharmacological and biological effects, such as anti-inflammatory, anticoagulant, antihypertensive, anticonvulsant, antioxidant, antimicrobial, and neuroprotective, among others. In addition, coumarin derivates can modulate signaling pathways that impact several cell processes. The objective of this review is to provide a narrative overview of the use of coumarin-derived compounds as potential therapeutic agents, as it has been shown that substituents on the basic core of coumarin have therapeutic effects against several human diseases and types of cancer, including breast, lung, colorectal, liver, and kidney cancer. In published studies, molecular docking has represented a powerful tool to evaluate and explain how these compounds selectively bind to proteins involved in various cellular processes, leading to specific interactions with a beneficial impact on human health. We also included studies that evaluated molecular interactions to identify potential biological targets with beneficial effects against human diseases. Full article

(This article belongs to the Section Medicinal Chemistry)

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15 pages, 3286 KiB

Open AccessArticle

LncRNA JHDM1D-AS1 Is a Key Biomarker for Progression and Modulation of Gemcitabine Sensitivity in Bladder Cancer Cells

by Isadora Oliveira Ansaloni Pereira, Glenda Nicioli da Silva, Tamires Cunha Almeida, Ana Paula Braga Lima, André Luiz Ventura Sávio, Katia Ramos Moreira Leite and Daisy Maria Fávero Salvadori

Molecules 2023, 28(5), 2412; https://doi.org/10.3390/molecules28052412 - 06 Mar 2023

Cited by 1 | Viewed by 1665

Abstract

Long non-coding RNAs are frequently found to be dysregulated and are linked to carcinogenesis, aggressiveness, and chemoresistance in a variety of tumors. As expression levels of the JHDM1D gene and lncRNA JHDM1D-AS1 are altered in bladder tumors, we sought to use their combined [...] Read more.

Long non-coding RNAs are frequently found to be dysregulated and are linked to carcinogenesis, aggressiveness, and chemoresistance in a variety of tumors. As expression levels of the JHDM1D gene and lncRNA JHDM1D-AS1 are altered in bladder tumors, we sought to use their combined expression to distinguish between low-and high-grade bladder tumors by RTq-PCR. In addition, we evaluated the functional role of JHDM1D-AS1 and its association with the modulation of gemcitabine sensitivity in high-grade bladder-tumor cells. J82 and UM-UC-3 cells were treated with siRNA-JHDM1D-AS1 and/or three concentrations of gemcitabine (0.39, 0.78, and 1.56 µM), and then submitted to cytotoxicity testing (XTT), clonogenic survival, cell cycle progression, cell morphology, and cell migration assays. When JHDM1D and JHDM1D-AS1 expression levels were used in combination, our findings indicated favorable prognostic value. Furthermore, the combined treatment resulted in greater cytotoxicity, a decrease in clone formation, G0/G1 cell cycle arrest, morphological alterations, and a reduction in cell migration capacity in both lineages compared to the treatments alone. Thus, silencing of JHDM1D-AS1 reduced the growth and proliferation of high-grade bladder-tumor cells and increased their sensitivity to gemcitabine treatment. In addition, the expression of JHDM1D/JHDM1D-AS1 indicated potential prognostic value in the progression of bladder tumors. 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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20 pages, 1291 KiB

Open AccessReview

Hexavalent Chromium Removal from Water and Wastewaters by Electrochemical Processes: Review

by Işık Kabdaşlı and Olcay Tünay

Molecules 2023, 28(5), 2411; https://doi.org/10.3390/molecules28052411 - 06 Mar 2023

Cited by 5 | Viewed by 2068

Abstract

Hexavalent chromium (Cr(VI)) is a toxic, mutagenic, teratogenic, and carcinogenic species. Its origin is in industrial activities. Therefore, its effective control is realized on a source basis. Although chemical methods proved effective in removing Cr(VI) from wastewaters, more economic solutions with a minimum [...] Read more.

Hexavalent chromium (Cr(VI)) is a toxic, mutagenic, teratogenic, and carcinogenic species. Its origin is in industrial activities. Therefore, its effective control is realized on a source basis. Although chemical methods proved effective in removing Cr(VI) from wastewaters, more economic solutions with a minimum sludge production have been sought. Among them, the use of electrochemical processes has emerged as a viable solution to the problem. Much research was conducted in this area. The aim of this review paper is to make a critical evaluation of the literature on Cr(VI) removal by electrochemical methods, particularly electrocoagulation with sacrificial electrodes, and to assess the present data as well as to point out the areas that need further elaboration. Following the review of the theoretical concepts of electrochemical processes, the literature on the electrochemical removal of Cr(VI) was evaluated on the basis of important elements of the system. Among them are initial pH, initial Cr(VI) concentration, current density, type and concentration of supporting electrolyte, and the material of electrodes and their operating characteristics and process kinetics. Dimensionally stable electrodes that realize the reduction process without producing any sludge were evaluated separately. Applications of electrochemical methods to a wide spectrum of industrial effluents were also assessed. Full article

(This article belongs to the Special Issue Chemical-Based Removal of Heavy Metal Ions from Wastewater)

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11 pages, 1043 KiB

Open AccessReview

Ensemble Learning, Deep Learning-Based and Molecular Descriptor-Based Quantitative Structure–Activity Relationships

by Yasunari Matsuzaka and Yoshihiro Uesawa

Molecules 2023, 28(5), 2410; https://doi.org/10.3390/molecules28052410 - 06 Mar 2023

Cited by 3 | Viewed by 2344

Abstract

A deep learning-based quantitative structure–activity relationship analysis, namely the molecular image-based DeepSNAP–deep learning method, can successfully and automatically capture the spatial and temporal features in an image generated from a three-dimensional (3D) structure of a chemical compound. It allows building high-performance prediction models [...] Read more.

A deep learning-based quantitative structure–activity relationship analysis, namely the molecular image-based DeepSNAP–deep learning method, can successfully and automatically capture the spatial and temporal features in an image generated from a three-dimensional (3D) structure of a chemical compound. It allows building high-performance prediction models without extracting and selecting features because of its powerful feature discrimination capability. Deep learning (DL) is based on a neural network with multiple intermediate layers that makes it possible to solve highly complex problems and improve the prediction accuracy by increasing the number of hidden layers. However, DL models are too complex when it comes to understanding the derivation of predictions. Instead, molecular descriptor-based machine learning has clear features owing to the selection and analysis of features. However, molecular descriptor-based machine learning has some limitations in terms of prediction performance, calculation cost, feature selection, etc., while the DeepSNAP–deep learning method outperforms molecular descriptor-based machine learning due to the utilization of 3D structure information and the advanced computer processing power of DL. Full article

(This article belongs to the Special Issue Drug Design with Advanced Computational Strategies and Artificial Intelligence)

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19 pages, 6241 KiB

Open AccessReview

Nematode Pheromones: Structures and Functions

by Biyuan Yang, Jie Wang, Xi Zheng and Xin Wang

Molecules 2023, 28(5), 2409; https://doi.org/10.3390/molecules28052409 - 06 Mar 2023

Cited by 2 | Viewed by 2218

Abstract

Pheromones are chemical signals secreted by one individual that can affect the behaviors of other individuals within the same species. Ascaroside is an evolutionarily conserved family of nematode pheromones that play an integral role in the development, lifespan, propagation, and stress response of [...] Read more.

Pheromones are chemical signals secreted by one individual that can affect the behaviors of other individuals within the same species. Ascaroside is an evolutionarily conserved family of nematode pheromones that play an integral role in the development, lifespan, propagation, and stress response of nematodes. Their general structure comprises the dideoxysugar ascarylose and fatty-acid-like side chains. Ascarosides can vary structurally and functionally according to the lengths of their side chains and how they are derivatized with different moieties. In this review, we mainly describe the chemical structures of ascarosides and their different effects on the development, mating, and aggregation of nematodes, as well as how they are synthesized and regulated. In addition, we discuss their influences on other species in various aspects. This review provides a reference for the functions and structures of ascarosides and enables their better application. Full article

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12 pages, 1733 KiB

Open AccessArticle

Mitochondrial Damage Induced by T-2 Mycotoxin on Human Skin—Fibroblast Hs68 Cell Line

by Edyta Janik-Karpinska, Michal Ceremuga, Marcin Niemcewicz, Ewelina Synowiec, Tomasz Sliwiński and Michal Bijak

Molecules 2023, 28(5), 2408; https://doi.org/10.3390/molecules28052408 - 06 Mar 2023

Cited by 5 | Viewed by 1415

Abstract

T-2 toxin is produced by different Fusarium species and belongs to the group of type A trichothecene mycotoxins. T-2 toxin contaminates various grains, such as wheat, barley, maize, or rice, thus posing a risk to human and animal health. The toxin has toxicological [...] Read more.

T-2 toxin is produced by different Fusarium species and belongs to the group of type A trichothecene mycotoxins. T-2 toxin contaminates various grains, such as wheat, barley, maize, or rice, thus posing a risk to human and animal health. The toxin has toxicological effects on human and animal digestive, immune, nervous and reproductive systems. In addition, the most significant toxic effect can be observed on the skin. This in vitro study focused on T-2 toxicity on human skin fibroblast Hs68 cell line mitochondria. In the first step of this study, T-2 toxin’s effect on the cell mitochondrial membrane potential (MMP) was determined. The cells were exposed to T-2 toxin, which resulted in dose- and time-dependent changes and a decrease in MMP. The obtained results revealed that the changes of intracellular reactive oxygen species (ROS) in the Hs68 cells were not affected by T-2 toxin. A further mitochondrial genome analysis showed that T-2 toxin in a dose- and time-dependent manner decreased the number of mitochondrial DNA (mtDNA) copies in cells. In addition, T-2 toxin genotoxicity causing mtDNA damage was evaluated. It was found that incubation of Hs68 cells in the presence of T-2 toxin, in a dose- and time-dependent manner, increased the level of mtDNA damage in both tested mtDNA regions: NADH dehydrogenase subunit 1 (ND1) and NADH dehydrogenase subunit 5 (ND5). In conclusion, the results of the in vitro study revealed that T-2 toxin shows adverse effects on Hs68 cell mitochondria. T-2 toxin induces mitochondrial dysfunction and mtDNA damage, which may cause the disruption of adenosine triphosphate (ATP) synthesis and, in consequence, cell death. Full article

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24 pages, 3620 KiB

Open AccessArticle

Novel Xanomeline-Containing Bitopic Ligands of Muscarinic Acetylcholine Receptors: Design, Synthesis and FRET Investigation

by Carlo Matera, Michael Kauk, Davide Cirillo, Marco Maspero, Claudio Papotto, Daniela Volpato, Ulrike Holzgrabe, Marco De Amici, Carsten Hoffmann and Clelia Dallanoce

Molecules 2023, 28(5), 2407; https://doi.org/10.3390/molecules28052407 - 06 Mar 2023

Cited by 1 | Viewed by 1732

Abstract

In the last few years, fluorescence resonance energy transfer (FRET) receptor sensors have contributed to the understanding of GPCR ligand binding and functional activation. FRET sensors based on muscarinic acetylcholine receptors (mAChRs) have been employed to study dual-steric ligands, allowing for the detection [...] Read more.

In the last few years, fluorescence resonance energy transfer (FRET) receptor sensors have contributed to the understanding of GPCR ligand binding and functional activation. FRET sensors based on muscarinic acetylcholine receptors (mAChRs) have been employed to study dual-steric ligands, allowing for the detection of different kinetics and distinguishing between partial, full, and super agonism. Herein, we report the synthesis of the two series of bitopic ligands, 12-Cn and 13-Cn, and their pharmacological investigation at the M₁, M₂, M₄, and M₅ FRET-based receptor sensors. The hybrids were prepared by merging the pharmacophoric moieties of the M₁/M₄-preferring orthosteric agonist Xanomeline 10 and the M₁-selective positive allosteric modulator 77-LH-28-1 (1-[3-(4-butyl-1-piperidinyl)propyl]-3,4-dihydro-2(1H)-quinolinone) 11. The two pharmacophores were connected through alkylene chains of different lengths (C3, C5, C7, and C9). Analyzing the FRET responses, the tertiary amine compounds 12-C5, 12-C7, and 12-C9 evidenced a selective activation of M₁ mAChRs, while the methyl tetrahydropyridinium salts 13-C5, 13-C7, and 13-C9 showed a degree of selectivity for M₁ and M₄ mAChRs. Moreover, whereas hybrids 12-Cn showed an almost linear response at the M₁ subtype, hybrids 13-Cn evidenced a bell-shaped activation response. This different activation pattern suggests that the positive charge anchoring the compound 13-Cn to the orthosteric site ensues a degree of receptor activation depending on the linker length, which induces a graded conformational interference with the binding pocket closure. These bitopic derivatives represent novel pharmacological tools for a better understanding of ligand-receptor interactions at a molecular level. Full article

(This article belongs to the Special Issue Recent Advances in the Modulation of Cholinergic Signaling II)

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17 pages, 9633 KiB

Open AccessArticle

Ergosterol Isolated from Antrodia camphorata Suppresses LPS-Induced Neuroinflammatory Responses in Microglia Cells and ICR Mice

by Ping Sun, Weiling Li, Jiazheng Guo, Qian Peng, Xiansheng Ye, Song Hu, Yuchen Liu, Wei Liu, Haifeng Chen, Jialu Qiao and Binlian Sun

Molecules 2023, 28(5), 2406; https://doi.org/10.3390/molecules28052406 - 06 Mar 2023

Cited by 3 | Viewed by 2237 | Correction

Abstract

Inflammation caused by microglial activation is important in neurodegenerative diseases. In this research, we tried to identify safe and effective anti-neuroinflammatory agents by screening a natural compounds library and found that Ergosterol can inhibit the nuclear factor kappa-light-chain enhancer of the activated B [...] Read more.

Inflammation caused by microglial activation is important in neurodegenerative diseases. In this research, we tried to identify safe and effective anti-neuroinflammatory agents by screening a natural compounds library and found that Ergosterol can inhibit the nuclear factor kappa-light-chain enhancer of the activated B cells (NF-κB) pathway induced by lipopolysaccharide (LPS) in microglia cells. Ergosterol has been reported to be an effective anti-inflammatory agent. Nevertheless, the potential regulatory role of Ergosterol in neuroinflammatory responses has not been fully investigated. We further investigated the mechanism of Ergosterol that regulates LPS-induced microglial activation and neuroinflammatory reactions both in vitro and in vivo. The results showed that Ergosterol can significantly decrease the pro-inflammatory cytokines induced by LPS in BV2 and HMC3 microglial cells, possibly by inhibiting the NF-κB, protein kinase B (AKT), and mitogen-activated protein kinase (MAPK) signaling pathways. In addition, we treated Institute of Cancer Research (ICR) mice with a safe concentration of Ergosterol following LPS injection. Ergosterol treatment significantly decreased microglial activation–associated ionized calcium-binding adapter molecule-1 (IBA-1), NF-κB phosphorylation, and pro-inflammatory cytokine levels. Moreover, Ergosterol pretreatment clearly reduced LPS-induced neuron damage by restoring the expression of synaptic proteins. Our data may provide insight into possible therapeutic strategies for neuroinflammatory disorders. Full article

(This article belongs to the Section Chemical Biology)

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17 pages, 9287 KiB

Open AccessArticle

QM/MM Modeling of the Flavin Functionalization in the RutA Monooxygenase

by Bella Grigorenko, Tatiana Domratcheva and Alexander Nemukhin

Molecules 2023, 28(5), 2405; https://doi.org/10.3390/molecules28052405 - 06 Mar 2023

Cited by 1 | Viewed by 1545

Abstract

Oxygenase activity of the flavin-dependent enzyme RutA is commonly associated with the formation of flavin-oxygen adducts in the enzyme active site. We report the results of quantum mechanics/molecular mechanics (QM/MM) modeling of possible reaction pathways initiated by various triplet state complexes of the [...] Read more.

Oxygenase activity of the flavin-dependent enzyme RutA is commonly associated with the formation of flavin-oxygen adducts in the enzyme active site. We report the results of quantum mechanics/molecular mechanics (QM/MM) modeling of possible reaction pathways initiated by various triplet state complexes of the molecular oxygen with the reduced flavin mononucleotide (FMN) formed in the protein cavities. According to the calculation results, these triplet-state flavin-oxygen complexes can be located at both re-side and si-side of the isoalloxazine ring of flavin. In both cases, the dioxygen moiety is activated by electron transfer from FMN, stimulating the attack of the arising reactive oxygen species at the C4a, N5, C6, and C8 positions in the isoalloxazine ring after the switch to the singlet state potential energy surface. The reaction pathways lead to the C(4a)-peroxide, N(5)-oxide, or C(6)-hydroperoxide covalent adducts or directly to the oxidized flavin, depending on the initial position of the oxygen molecule in the protein cavities. Full article

(This article belongs to the Special Issue Molecular Modeling: Insights into the Enzymatic Reactions and Photochemical Processes in Biomacromolecules)

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14 pages, 2230 KiB

Open AccessArticle

Unraveling the Variability of Essential Oil Composition in Different Accessions of Bunium persicum Collected from Different Temperate Micro-Climates

by Mudasir Hafiz Khan, Niyaz Ahmad Dar, Bashir Ahmad Alie, Sher Ahmad Dar, Ajaz Ahmad Lone, Ghulam Hassan Mir, Uzma Fayaz, Sajad Ali, Anshika Tyagi, Mohamed A. El-Sheikh and Saleh Alansi

Molecules 2023, 28(5), 2404; https://doi.org/10.3390/molecules28052404 - 06 Mar 2023

Cited by 1 | Viewed by 1356

Abstract

The present investigation was performed to evaluate the variability of the essential oil composition present in the seed extract of Kala zeera (Bunium persicum Bioss.) obtained from different geographical zones of Northwestern-Himalayan using Gas Chromatography-Mass Spectrum (GC-MS). The results of the GC-MS [...] Read more.

The present investigation was performed to evaluate the variability of the essential oil composition present in the seed extract of Kala zeera (Bunium persicum Bioss.) obtained from different geographical zones of Northwestern-Himalayan using Gas Chromatography-Mass Spectrum (GC-MS). The results of the GC-MS analysis revealed significant differences in the essential oil content. Significant variability was observed in the chemical constituents of the essential oils mainly for p-cymene, D-limonene, Gamma-terpinene, Cumic aldehyde and 1, 4-p-menthadien-7-al. Among these compounds, the highest average percentage across the locations was observed for gamma-terpinene (32.08%) which was followed by cumic aldehyde (25.07%), and 1, 4-p-menthadien-7-al (15.45%). Principal component analysis (PCA) also grouped the 4 highly significant compounds i.e., p-Cymene, Gamma-Terpinene, Cumic aldehyde, and 1,4-p-Menthadien-7-al into same cluster which are mainly distributed in Shalimar Kalazeera-1, and Atholi Kishtwar zones. The highest value of gamma-terpinene was recorded in Atholi accession (40.66%). However, among climatic zones Zabarwan Srinagar and Shalimar Kalazeera-1 was found to have highly positive significant correlation (0.99). The cophenetic correlation coefficient (c) was found to be 0.8334 during hierarchical clustering for 12 essential oil compounds showing that our results are highly correlated. Network analysis also showed the overlapping pattern and similar interaction between the 12 compounds as shown by hierarchical clustering analysis. From the results, it could be concluded that existence of variability among the various bioactive compounds of B. persicum which are probably to be incorporated to the potential list of drugs and may serve as good genetic source for various modern breeding programs. Full article

(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)

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17 pages, 1722 KiB

Open AccessArticle

Efficient Synthesis of 1H-Benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one Derivatives Using Ag₂CO₃/TFA-Catalyzed 6-endo-dig Cyclization: Reaction Scope and Mechanistic Study

by Abdelkarim El Qami, Badr Jismy, Mohamed Akssira, Johan Jacquemin, Abdellatif Tikad and Mohamed Abarbri

Molecules 2023, 28(5), 2403; https://doi.org/10.3390/molecules28052403 - 06 Mar 2023

Viewed by 1381

Abstract

A small library of 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one derivatives was prepared in good to excellent yields, involving a Ag₂CO₃/TFA-catalyzed intramolecular oxacyclization of N-Boc-2-alkynylbenzimidazole substrates. In all experiments, the 6-endo-dig cyclization was exclusively achieved since [...] Read more.

A small library of 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one derivatives was prepared in good to excellent yields, involving a Ag₂CO₃/TFA-catalyzed intramolecular oxacyclization of N-Boc-2-alkynylbenzimidazole substrates. In all experiments, the 6-endo-dig cyclization was exclusively achieved since the possible 5-exo-dig heterocycle was not observed, indicating the high regioselectivity of this process. The scope and limitations of the silver catalyzed 6-endo-dig cyclization of N-Boc-2-alkynylbenzimidazoles as substrates, bearing various substituents, were investigated. While ZnCl₂ has shown limits for alkynes with an aromatic substituent, Ag₂CO₃/TFA demonstrated its effectiveness and compatibility regardless of the nature of the starting alkyne (aliphatic, aromatic or heteroaromatic), providing a practical regioselective access to structurally diverse 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-ones in good yields. Moreover, the rationalization of oxacyclization selectivity in favor of 6-endo-dig over 5-exo-dig was explained by a complementary computational study. Full article

(This article belongs to the Special Issue Recent Progress in Heteroorganic Chemistry)

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17 pages, 5450 KiB

Open AccessArticle

Deep Eutectic Liquids as a Topical Vehicle for Tadalafil: Characterisation and Potential Wound Healing and Antimicrobial Activity

by Bayan Alkhawaja, Faisal Al-Akayleh, Ashraf Al-Khateeb, Jehad Nasereddin, Bayan Y. Ghanim, Albert Bolhuis, Nisrein Jaber, Mayyas Al-Remawi and Nidal A. Qinna

Molecules 2023, 28(5), 2402; https://doi.org/10.3390/molecules28052402 - 06 Mar 2023

Cited by 8 | Viewed by 2116

Abstract

Deep eutectic solvents (DESs) and ionic liquids (ILs) offer novel opportunities for several pharmaceutical applications. Their tunable properties offer control over their design and applications. Choline chloride (CC)-based DESs (referred to as Type III eutectics) offer superior advantages for various pharmaceutical and therapeutic [...] Read more.

Deep eutectic solvents (DESs) and ionic liquids (ILs) offer novel opportunities for several pharmaceutical applications. Their tunable properties offer control over their design and applications. Choline chloride (CC)-based DESs (referred to as Type III eutectics) offer superior advantages for various pharmaceutical and therapeutic applications. Here, CC-based DESs of tadalafil (TDF), a selective phosphodiesterase type 5 (PDE-5) enzyme inhibitor, were designed for implementation in wound healing. The adopted approach provides formulations for the topical application of TDF, hence avoiding systemic exposure. To this end, the DESs were chosen based on their suitability for topical application. Then, DES formulations of TDF were prepared, yielding a tremendous increase in the equilibrium solubility of TDF. Lidocaine (LDC) was included in the formulation with TDF to provide a local anaesthetic effect, forming F01. The addition of propylene glycol (PG) to the formulation was attempted to reduce the viscosity, forming F02. The formulations were fully characterised using NMR, FTIR and DCS techniques. According to the obtained characterisation results, the drugs were soluble in the DES with no detectable degradation. Our results demonstrated the utility of F01 in wound healing in vivo using cut wound and burn wound models. Significant retraction of the cut wound area was observed within three weeks of the application of F01 when compared with DES. Furthermore, the utilisation of F01 resulted in less scarring of the burn wounds than any other group including the positive control, thus rendering it a candidate formula for burn dressing formulations. We demonstrated that the slower healing process associated with F01 resulted in less scarring potential. Lastly, the antimicrobial activity of the DES formulations was demonstrated against a panel of fungi and bacterial strains, thus providing a unique wound healing process via simultaneous prevention of wound infection. In conclusion, this work presents the design and application of a topical vehicle for TDF with novel biomedical applications. Full article

(This article belongs to the Special Issue Advanced Research on Natural Deep Eutectic Solvents)

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15 pages, 1893 KiB

Open AccessArticle

Effect of Immunomodulating Extract and Some Isolates from Etlingera rubroloba A.D. Poulsen Fruits on Diabetic Patients with Tuberculosis

by Muhammad Ilyas Y., Idin Sahidin, Asriullah Jabbar, Agung W. M. Yodha, Ajeng Diantini, Ivan Surya Pradipta, Riezki Amalia, Raden Maya Febrianti, Yuni Elsa Hadisaputri, Mohammad Ghozali and Euis Julaeha

Molecules 2023, 28(5), 2401; https://doi.org/10.3390/molecules28052401 - 06 Mar 2023

Viewed by 1308

Abstract

Diabetes mellitus (DM) is a disease easily complicated by tuberculosis (TB) due to impaired function of the innate immune response. The successes of the discovery of immunomodulatory compounds needs to be continued to introduce new insights into the innate immune response. In previous [...] Read more.

Diabetes mellitus (DM) is a disease easily complicated by tuberculosis (TB) due to impaired function of the innate immune response. The successes of the discovery of immunomodulatory compounds needs to be continued to introduce new insights into the innate immune response. In previous studies, plant compounds of Etlingera rubroloba A.D. Poulsen (E.rubroloba) were demonstrated to have potential as an immunomodulators. This study aims to isolate and identify the structure of the compounds of E.rubroloba fruit that could effectively improve the function of the innate immune response in individuals with DM infected with TB. The isolation and purification of the compounds of the E.rubroloba extract were carried out by radial chromatography (RC) and thin-layer chromatography (TLC). Identification of the isolated compound structures was determined by measuring the proton (¹H) and carbon (¹³C) nuclear magnetic resonance (NMR). In vitro testing was performed on the immunomodulating activity of the extracts and isolated compounds on DM model macrophages infected with TB antigens. This study succeeded at isolating and identifying the structures of two isolate compounds, namely Sinaphyl alcohol diacetat (BER-1), and Ergosterol peroxide (BER-6). The two isolates were more effective as immunomodulators than the positive controls were, which differed significantly (* p < 0.05) at the reducing interleukin-12 (IL-12) levels and Toll-like receptor-2 (TLR-2) protein expression and increasing the human leucocyte antigen-DR (HLA-DR) protein expression in DM infected with TB. The isolated compound was discovered in E. rubroloba fruits, which has been reported to have the potential to be developed as an immunomodulatory agent. Follow-up testing to determine the mechanism and effectiveness of these compounds as immunomodulators for DM patients is required so that they are not susceptible to TB infection. Full article

(This article belongs to the Special Issue Plant Bioactive Compounds: Extraction, Identification and Biological Activities)

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20 pages, 1622 KiB

Open AccessReview

Bruton’s Tyrosine Kinase Inhibitors (BTKIs): Review of Preclinical Studies and Evaluation of Clinical Trials

by Dariusz Rozkiewicz, Justyna Magdalena Hermanowicz, Iwona Kwiatkowska, Anna Krupa and Dariusz Pawlak

Molecules 2023, 28(5), 2400; https://doi.org/10.3390/molecules28052400 - 06 Mar 2023

Cited by 13 | Viewed by 5820

Abstract

In the last few decades, there has been a growing interest in Bruton’s tyrosine kinase (BTK) and the compounds that target it. BTK is a downstream mediator of the B-cell receptor (BCR) signaling pathway and affects B-cell proliferation and differentiation. Evidence demonstrating the [...] Read more.

In the last few decades, there has been a growing interest in Bruton’s tyrosine kinase (BTK) and the compounds that target it. BTK is a downstream mediator of the B-cell receptor (BCR) signaling pathway and affects B-cell proliferation and differentiation. Evidence demonstrating the expression of BTK on the majority of hematological cells has led to the hypothesis that BTK inhibitors (BTKIs) such as ibrutinib can be an effective treatment for leukemias and lymphomas. However, a growing body of experimental and clinical data has demonstrated the significance of BTK, not just in B-cell malignancies, but also in solid tumors, such as breast, ovarian, colorectal, and prostate cancers. In addition, enhanced BTK activity is correlated with autoimmune disease. This gave rise to the hypothesis that BTK inhibitors can be beneficial in the therapy of rheumatoid arthritis (RA), systemic lupus erythematosus (SLE), multiple sclerosis (MS), Sjögren’s syndrome (SS), allergies, and asthma. In this review article, we summarize the most recent findings regarding this kinase as well as the most advanced BTK inhibitors that have been developed to date and their clinical applications mainly in cancer and chronic inflammatory disease patients. Full article

(This article belongs to the Special Issue Design, Synthesis and Evaluation of Novel Anticancer Agents)

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19 pages, 8596 KiB

Open AccessArticle

TiO₂-Modified Montmorillonite-Supported Porous Carbon-Immobilized Pd Species Nanocomposite as an Efficient Catalyst for Sonogashira Reactions

by Yuli Chen, Kailang Sun, Taojun Zhang, Jie Zhou, Yonghong Liu, Minfeng Zeng, Xiaorong Ren, Ruokun Feng, Zhen Yang, Peng Zhang, Baoyi Wang and Xingzhong Cao

Molecules 2023, 28(5), 2399; https://doi.org/10.3390/molecules28052399 - 06 Mar 2023

Cited by 3 | Viewed by 1382

Abstract

In this study, a combination of the porous carbon (PCN), montmorillonite (MMT), and TiO₂ was synthesized into a composite immobilized Pd metal catalyst (TiO₂-MMT/PCN@Pd) with effective synergism improvements in catalytic performance. The successful TiO₂-pillaring modification for MMT, derivation [...] Read more.

In this study, a combination of the porous carbon (PCN), montmorillonite (MMT), and TiO₂ was synthesized into a composite immobilized Pd metal catalyst (TiO₂-MMT/PCN@Pd) with effective synergism improvements in catalytic performance. The successful TiO₂-pillaring modification for MMT, derivation of carbon from the biopolymer of chitosan, and immobilization of Pd species for the prepared TiO₂-MMT/PCN@Pd⁰ nanocomposites were confirmed using a combined characterization with X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), N₂ adsorption–desorption isotherms, high-resolution transition electron microscopy (HRTEM), X-ray photoelectron spectroscopy (XPS), and Raman spectroscopy. It was shown that the combination of PCN, MMT, and TiO₂ as a composite support for the stabilization of the Pd catalysts could synergistically improve the adsorption and catalytic properties. The resultant TiO₂-MMT₈₀/PCN₂₀@Pd⁰ showed a high surface area of 108.9 m²/g. Furthermore, it exhibited moderate to excellent activity (59–99% yield) and high stability (recyclable 19 times) in the liquid–solid catalytic reactions, such as the Sonogashira reactions of aryl halides (I, Br) with terminal alkynes in organic solutions. The positron annihilation lifetime spectroscopy (PALS) characterization sensitively detected the development of sub-nanoscale microdefects in the catalyst after long-term recycling service. This study provided direct evidence for the formation of some larger-sized microdefects during sequential recycling, which would act as leaching channels for loaded molecules, including active Pd species. Full article

(This article belongs to the Topic Catalysis: Homogeneous and Heterogeneous)

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14 pages, 3163 KiB

Open AccessArticle

A Fluorescent Molecularly Imprinted Polymer-Coated Paper Sensor for On-Site and Rapid Detection of Glyphosate

by Meng Wang, Jun Qiu, Chennuo Zhu, Yunyan Hua, Jie Yu, Lulu Jia, Jianhong Xu, Jianlin Li and Qianjin Li

Molecules 2023, 28(5), 2398; https://doi.org/10.3390/molecules28052398 - 06 Mar 2023

Cited by 5 | Viewed by 2134

Abstract

Due to the massive use and abuse of pesticides, practices which have led to serious threats to human health, the research community must develop on-site and rapid detection technology of pesticide residues to ensure food safety. Here, a paper-based fluorescent sensor, integrated with [...] Read more.

Due to the massive use and abuse of pesticides, practices which have led to serious threats to human health, the research community must develop on-site and rapid detection technology of pesticide residues to ensure food safety. Here, a paper-based fluorescent sensor, integrated with molecularly imprinted polymer (MIP) targeting glyphosate, was prepared by a surface-imprinting strategy. The MIP was synthesized by a catalyst-free imprinting polymerization technique and exhibited highly selective recognition capability for glyphosate. The MIP-coated paper sensor not only remained selective, but also displayed a limit of detection of 0.29 µmol and a linear detection range from 0.5 to 10 µmol. Moreover, the detection time only took about 5 min, which is beneficial for rapid detection of glyphosate in food samples. The detection accuracy of such paper sensor was good, with a spiked recovery rate of 92–117% in real samples. The fluorescent MIP-coated paper sensor not only has good specificity, which is helpful to reduce the food matrix interference and shorten the sample pretreatment time, but it also has the merits of high stability, low-cost and ease of operation and carrying, displaying great potential for application in the on-site and rapid detection of glyphosate for food safety. Full article

(This article belongs to the Special Issue Molecularly Imprinted Materials: New Vistas and Challenge)

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14 pages, 585 KiB

Open AccessArticle

Application of Green Technology to Extract Clean and Safe Bioactive Compounds from Tetradesmus obliquus Biomass Grown in Poultry Wastewater

by Jelena Vladić, Jelena Molnar Jazić, Alice Ferreira, Snežana Maletić, Dragoljub Cvetković, Jasmina Agbaba, Senka Vidović and Luisa Gouveia

Molecules 2023, 28(5), 2397; https://doi.org/10.3390/molecules28052397 - 06 Mar 2023

Cited by 3 | Viewed by 2149

Abstract

Microalgae are capable of assimilating nutrients from wastewater (WW), producing clean water and biomass rich in bioactive compounds that need to be recovered from inside the microalgal cell. This work investigated subcritical water (SW) extraction to collect high-value compounds from the microalga Tetradesmus [...] Read more.

Microalgae are capable of assimilating nutrients from wastewater (WW), producing clean water and biomass rich in bioactive compounds that need to be recovered from inside the microalgal cell. This work investigated subcritical water (SW) extraction to collect high-value compounds from the microalga Tetradesmus obliquus after treating poultry WW. The treatment efficiency was evaluated in terms of total Kjeldahl nitrogen (TKN), phosphate, chemical oxygen demand (COD) and metals. T. obliquus was able to remove 77% TKN, 50% phosphate, 84% COD, and metals (48–89%) within legislation values. SW extraction was performed at 170 °C and 30 bar for 10 min. SW allowed the extraction of total phenols (1.073 mg GAE/mL extract) and total flavonoids (0.111 mg CAT/mL extract) with high antioxidant activity (IC₅₀ value, 7.18 µg/mL). The microalga was shown to be a source of organic compounds of commercial value (e.g., squalene). Finally, the SW conditions allowed the removal of pathogens and metals in the extracts and residues to values in accordance with legislation, assuring their safety for feed or agriculture applications. Full article

(This article belongs to the Special Issue Green Chemistry in Portugal)

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13 pages, 1993 KiB

Open AccessArticle

Effects of Ultra-High-Pressure Jet Processing on Casein Structure and Curdling Properties of Skimmed Bovine Milk

by Fei Xu, Lu Xue, Yanfeng Ma, Tianjiao Niu, Pei Zhao, Zijian Wu and Yanfa Wang

Molecules 2023, 28(5), 2396; https://doi.org/10.3390/molecules28052396 - 06 Mar 2023

Cited by 1 | Viewed by 1688

Abstract

Ultra-high-pressure jet processing (UHPJ) is a new non-thermal processing technique that can be employed for the homogenization and the sterilization of dairy products. However, the effects on dairy products are unknown when using UHPJ for homogenization and sterilization. Thus, this study aimed to [...] Read more.

Ultra-high-pressure jet processing (UHPJ) is a new non-thermal processing technique that can be employed for the homogenization and the sterilization of dairy products. However, the effects on dairy products are unknown when using UHPJ for homogenization and sterilization. Thus, this study aimed to investigate the effects of UHPJ on the sensory and curdling properties of skimmed milk and the casein structure in skimmed milk. Skimmed bovine milk was treated with UHPJ using different pressures (100, 150, 200, 250, 300 MPa) and casein was extracted by isoelectric precipitation. Subsequently, the average particle size, Zeta potential, contents of free sulfhydryl and disulfide bonds, secondary structure, and surface micromorphology were all used as evaluation indicators to explore the effects of UHPJ on the structure of casein. The results showed that with an increase of pressure, the free sulfhydryl group content changed irregularly, while the disulfide bond content increased from 1.085 to 3.0944 μmol/g. The content of α-helix and random coil in the casein decreased, while the β-sheet content increased at 100, 150, 200 MPa pressure. However, treatment with higher pressures of 250 and 300 MPa had the opposite effect. The average particle size of the casein micelles first decreased to 167.47 nm and then increased up to 174.63 nm; the absolute value of Zeta potential decreased from 28.33 to 23.77 mV. Scanning electron microscopy analysis revealed that the casein micelles had fractured into flat, loose, porous structures under pressure instead of into large clusters. After being ultra-high-pressure jet-processed, the sensory properties of skimmed milk and its fermented curd were analyzed concurrently. The results demonstrated that UHPJ could alter the viscosity and color of skimmed milk, shortening curdling time from 4.5 h to 2.67 h, and that the texture of the curd fermented with this skimmed milk could be improved to varying degrees by changing the structure of casein. Thus, UHPJ has a promising application in the manufacture of fermented milk due to its ability to enhance the curdling efficiency of skimmed milk and improve the texture of fermented milk. Full article

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

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15 pages, 1386 KiB

Open AccessArticle

Deep Eutectic Solvent Based Reversed-Phase Dispersive Liquid–Liquid Microextraction and High-Performance Liquid Chromatography for the Determination of Free Tryptophan in Cold-Pressed Oils

by Slavica Ražić, Tamara Bakić, Aleksandra Topić, Jelena Lukić and Antonije Onjia

Molecules 2023, 28(5), 2395; https://doi.org/10.3390/molecules28052395 - 05 Mar 2023

Cited by 5 | Viewed by 2208

Abstract

A fast and straightforward reversed-phase dispersive liquid–liquid microextraction (RP-DLLME) using a deep eutectic solvent (DES) procedure to determine free tryptophan in vegetable oils was developed. The influence of eight variables affecting the RP-DLLME efficiency has been studied by a multivariate approach. A Plackett–Burman [...] Read more.

A fast and straightforward reversed-phase dispersive liquid–liquid microextraction (RP-DLLME) using a deep eutectic solvent (DES) procedure to determine free tryptophan in vegetable oils was developed. The influence of eight variables affecting the RP-DLLME efficiency has been studied by a multivariate approach. A Plackett–Burman design for screening the most influential variables followed by a central composite response surface methodology led to an optimum RP-DLLME setup for a 1 g oil sample: 9 mL hexane as the diluting solvent, vortex extraction with 0.45 mL of DES (choline chloride–urea) at 40 °C, without addition of salt, and centrifugation at 6000 rpm for 4.0 min. The reconstituted extract was directly injected into a high-performance liquid chromatography (HPLC) system working in the diode array mode. At the studied concentration levels, the obtained method detection limits (MDL) was 11 mg/kg, linearity in matrix-matched standards was R² ≥ 0.997, relative standard deviations (RSD) was 7.8%, and average recovery was 93%. The combined use of the recently developed DES -based RP-DLLME and HPLC provides an innovative, efficient, cost-effective, and more sustainable method for the extraction and quantification of free tryptophan in oily food matrices. The method was employed to analyze cold-pressed oils from nine vegetables (Brazil nut, almond, cashew, hazelnut, peanut, pumpkin, sesame, sunflower, and walnut) for the first time. The results showed that free tryptophan was present in the range of 11–38 mg/100 g. This article is important for its contributions to the field of food analysis, and for its development of a new and efficient method for the determination of free tryptophan in complex matrices, which has the potential to be applied to other analytes and sample types. Full article

(This article belongs to the Special Issue Ionic Liquids and Deep Eutectic Solvents: Greener Approaches for Sustainable Chemistry)

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13 pages, 1781 KiB

Open AccessArticle

Recombinant Domain of Flagellin Promotes In Vitro a Chemotactic Inflammatory Profile in Human Immune Cells Independently of a Dendritic Cell Phenotype

by Roxana González-Stegmaier, Adam Aguirre, Constanza Cárcamo, Patricia Aguila-Torres and Franz Villarroel-Espíndola

Molecules 2023, 28(5), 2394; https://doi.org/10.3390/molecules28052394 - 05 Mar 2023

Viewed by 1597

Abstract

Flagellin is the major component of the flagellum in gram-positive and -negative bacteria and is also the ligand for the Toll-like receptor 5 (TLR5). The activation of TLR5 promotes the expression of proinflammatory cytokines and chemokines and the subsequent activation of T cells. [...] Read more.

Flagellin is the major component of the flagellum in gram-positive and -negative bacteria and is also the ligand for the Toll-like receptor 5 (TLR5). The activation of TLR5 promotes the expression of proinflammatory cytokines and chemokines and the subsequent activation of T cells. This study evaluated a recombinant domain from the amino-terminus D1 domain (rND1) of flagellin from Vibrio anguillarum, a fish pathogen, as an immunomodulator in human peripheral blood mononuclear cells (PBMCs) and monocyte-derived dendritic cells (MoDCs). We demonstrated that rND1 induced an upregulation of proinflammatory cytokines in PBMCs, characterized at the transcriptional level by an expression peak of 220-fold for IL-1β, 20-fold for IL-8, and 65-fold for TNF-α. In addition, at the protein level, 29 cytokines and chemokines were evaluated in the supernatant and were correlated with a chemotactic signature. MoDCs treated with rND1 showed low levels of co-stimulatory and HLA-DR molecules and kept an immature phenotype with a decreased phagocytosis of dextran. We probed that rND1 from a non-human pathogen promotes modulation in human cells, and it may be considered for further studies in adjuvant therapies based on pathogen-associated patterns (PAMPs). Full article

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20 pages, 2571 KiB

Open AccessArticle

Rhodococcus Strains from the Specialized Collection of Alkanotrophs for Biodegradation of Aromatic Compounds

by Anastasiia Krivoruchko, Maria Kuyukina, Tatyana Peshkur, Colin J. Cunningham and Irina Ivshina

Molecules 2023, 28(5), 2393; https://doi.org/10.3390/molecules28052393 - 05 Mar 2023

Cited by 2 | Viewed by 1927

Abstract

The ability to degrade aromatic hydrocarbons, including (i) benzene, toluene, o-xylene, naphthalene, anthracene, phenanthrene, benzo[a]anthracene, and benzo[a]pyrene; (ii) polar substituted derivatives of benzene, including phenol and aniline; (iii) N-heterocyclic compounds, including pyridine; 2-, 3-, and 4-picolines; 2- and 6-lutidine; 2- and 4-hydroxypyridines; [...] Read more.

The ability to degrade aromatic hydrocarbons, including (i) benzene, toluene, o-xylene, naphthalene, anthracene, phenanthrene, benzo[a]anthracene, and benzo[a]pyrene; (ii) polar substituted derivatives of benzene, including phenol and aniline; (iii) N-heterocyclic compounds, including pyridine; 2-, 3-, and 4-picolines; 2- and 6-lutidine; 2- and 4-hydroxypyridines; (iv) derivatives of aromatic acids, including coumarin, of 133 Rhodococcus strains from the Regional Specialized Collection of Alkanotrophic Microorganisms was demonstrated. The minimal inhibitory concentrations of these aromatic compounds for Rhodococcus varied in a wide range from 0.2 up to 50.0 mM. o-Xylene and polycyclic aromatic hydrocarbons (PAHs) were the less-toxic and preferred aromatic growth substrates. Rhodococcus bacteria introduced into the PAH-contaminated model soil resulted in a 43% removal of PAHs at an initial concentration 1 g/kg within 213 days, which was three times higher than that in the control soil. As a result of the analysis of biodegradation genes, metabolic pathways for aromatic hydrocarbons, phenol, and nitrogen-containing aromatic compounds in Rhodococcus, proceeding through the formation of catechol as a key metabolite with its following ortho-cleavage or via the hydrogenation of aromatic rings, were verified. Full article

(This article belongs to the Special Issue Biologically Active Arene Derivatives in the Environment—Risks and Solutions)

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13 pages, 3542 KiB

Open AccessArticle

One-Step Synthesis of a Non-Precious-Metal Tris (Fe/N/F)-Doped Carbon Catalyst for Oxygen Reduction Reactions

by Huitian Yang, Hao Wu, Lei Yao, Siyan Liu, Lu Yang, Jieling Lu, Hongliang Peng, Xiangcheng Lin, Ping Cai, Huanzhi Zhang, Fen Xu, Kexiang Zhang and Lixian Sun

Molecules 2023, 28(5), 2392; https://doi.org/10.3390/molecules28052392 - 05 Mar 2023

Cited by 1 | Viewed by 1383

Abstract

Advancements in inexpensive, efficient, and durable oxygen reduction catalysts is important for maintaining the sustainable development of fuel cells. Although doping carbon materials with transition metals or heteroatomic doping is inexpensive and enhances the electrocatalytic performance of the catalyst, because the charge distribution [...] Read more.

Advancements in inexpensive, efficient, and durable oxygen reduction catalysts is important for maintaining the sustainable development of fuel cells. Although doping carbon materials with transition metals or heteroatomic doping is inexpensive and enhances the electrocatalytic performance of the catalyst, because the charge distribution on its surface is adjusted, the development of a simple method for the synthesis of doped carbon materials remains challenging. Here, a non-precious-metal tris (Fe/N/F)-doped particulate porous carbon material (2₁P₂-Fe₁-850) was synthesized by employing a one-step process, using 2-methylimidazole, polytetrafluoroethylene, and FeCl₃ as raw materials. The synthesized catalyst exhibited a good oxygen reduction reaction performance with a half-wave potential of 0.85 V in an alkaline medium (compared with 0.84 V of commercial Pt/C). Moreover, it had better stability and methanol resistance than Pt/C. This was mainly attributed to the effect of the tris (Fe/N/F)-doped carbon material on the morphology and chemical composition of the catalyst, thereby enhancing the catalyst’s oxygen reduction reaction properties. This work provides a versatile method for the gentle and rapid synthesis of highly electronegative heteroatoms and transition metal co-doped carbon materials. Full article

(This article belongs to the Special Issue Energy-Relevant Advanced Materials)

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14 pages, 2705 KiB

Open AccessArticle

Experiments and Numerical Simulation of N-decane/Ethanol Bi-Component Droplet Evaporation

by Zhenzhong Zhang, Xuefeng Huang and Jiangrong Xu

Molecules 2023, 28(5), 2391; https://doi.org/10.3390/molecules28052391 - 05 Mar 2023

Cited by 2 | Viewed by 1374

Abstract

The evaporation characteristics of n-decane-based bi-component or multi-component droplets have been veiled for application in advanced combustion. This paper proposes to experimentally investigate the evaporation of n-decane/ethanol bi-component droplets settled in the convective hot air, and numerically simulate the key parameters affecting the [...] Read more.

The evaporation characteristics of n-decane-based bi-component or multi-component droplets have been veiled for application in advanced combustion. This paper proposes to experimentally investigate the evaporation of n-decane/ethanol bi-component droplets settled in the convective hot air, and numerically simulate the key parameters affecting the evaporation charactersitics. It was found that the evaporation behavior was interactively affected by the mass fraction of ethanol and the ambient temperature. For mono-component n-decane droplets, the evaporation process included the transient heating (non-isothermal) and steady evaporation (isothermal) stages. In the isothermal stage, the evaporation rate followed d²-law. The evaporation rate constant linearly increased as the ambient temperature enhanced (573~873 K). For n-decane/ethanol bi-component droplets, at low mass fractions (≤0.2), the isothermal evaporation processes were steady due to the good miscibility between n-decane and ethanol, like mono-component n-decane, whereas at high mass fractions (≥0.4), the evaporation process experienced ultrashort heating and fluctuating evaporation stages. During the fluctuating evaporation, the bubbles formed inside the bi-component droplets and expanded, resulting in the occurrence of the microspray (secondary atomization) and the microexplosion. The evaporation rate constant of bi-component droplets increased as the ambient temperature enhanced, and showed a “V-shaped” trend with the increase of the mass fraction, and the evaporation rate constant was the smallest at 0.4. The evaporation rate constants based on the numerical simulation by using the multiphase flow model and Lee model showed reasonable agreement with the experimental ones, suggesting a potential of application in practical engineering. Full article

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12 pages, 3021 KiB

Open AccessArticle

Infrared Spectroscopy as a Potential Diagnostic Tool for Medulloblastoma

by Kornelia Łach, Aneta Kowal, Marta Perek-Polnik, Paweł Jakubczyk, Christopher J. Arthur, Wioletta Bal, Monika Drogosiewicz, Bożenna Dembowska-Bagińska, Wiesława Grajkowska, Józef Cebulski and Radosław Chaber

Molecules 2023, 28(5), 2390; https://doi.org/10.3390/molecules28052390 - 05 Mar 2023

Cited by 3 | Viewed by 2033

Abstract

Introduction: Medulloblastoma (MB) is the most common malignant tumor of the central nervous system in childhood. FTIR spectroscopy provides a holistic view of the chemical composition of biological samples, including the detection of molecules such as nucleic acids, proteins, and lipids. This study [...] Read more.

Introduction: Medulloblastoma (MB) is the most common malignant tumor of the central nervous system in childhood. FTIR spectroscopy provides a holistic view of the chemical composition of biological samples, including the detection of molecules such as nucleic acids, proteins, and lipids. This study evaluated the applicability of FTIR spectroscopy as a potential diagnostic tool for MB. Materials and methods: FTIR spectra of MB samples from 40 children (boys/girls: 31/9; age: median 7.8 years, range 1.5–21.5 years) treated in the Oncology Department of the Children’s Memorial Health Institute in Warsaw between 2010 and 2019 were analyzed. The control group consisted of normal brain tissue taken from four children diagnosed with causes other than cancer. Formalin-fixed and paraffin-embedded tissues were sectioned and used for FTIR spectroscopic analysis. The sections were examined in the mid-infrared range (800–3500 cm⁻¹) by ATR-FTIR. Spectra were analysed using a combination of principal component analysis, hierarchical cluster analysis, and absorbance dynamics. Results: FTIR spectra in MB were significantly different from those of normal brain tissue. The most significant differences related to the range of nucleic acids and proteins in the region 800–1800 cm⁻¹. Some major differences were also revealed in the quantification of protein conformations (α-helices, β-sheets, and others) in the amide I band, as well as in the absorbance dynamics in the 1714–1716 cm⁻¹ range (nucleic acids). It was not, however, possible to clearly distinguish between the various histological subtypes of MB using FTIR spectroscopy. Conclusions: MB and normal brain tissue can be distinguished from one another to some extent using FTIR spectroscopy. As a result, it may be used as a further tool to hasten and enhance histological diagnosis. Full article

(This article belongs to the Special Issue IR Spectroscopy: An Emerging Analytical Tool)

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13 pages, 3001 KiB

Open AccessArticle

Rectangular Transition Metal-rTCNQ Organic Frameworks Enabling Polysulfide Anchoring and Fast Electrocatalytic Activity in Li-Sulfur Batteries: A Density Functional Theory Perspective

by Jie-Zhen Xia, Lu-Chao Zhao, Man-Hua Liao and Qi Wu

Molecules 2023, 28(5), 2389; https://doi.org/10.3390/molecules28052389 - 05 Mar 2023

Cited by 1 | Viewed by 1554

Abstract

Two-dimensional metal-organic frameworks (MOFs) have shown great development po-tential in the field of lithium-sulfur (Li-S) batteries. In this theoretical research work, we propose a novel 3d transition metals (TM)-embedded rectangular tetracyanoquinodimethane (TM-rTCNQ) as a potential high-performance sulfur host. The calculated results show [...] Read more.

Two-dimensional metal-organic frameworks (MOFs) have shown great development po-tential in the field of lithium-sulfur (Li-S) batteries. In this theoretical research work, we propose a novel 3d transition metals (TM)-embedded rectangular tetracyanoquinodimethane (TM-rTCNQ) as a potential high-performance sulfur host. The calculated results show that all TM-rTCNQ structures have excellent structural stability and metallic properties. Through exploring different adsorption patterns, we discovered that TM-rTCNQ (TM = V, Cr, Mn, Fe and Co) monolayers possess moderate adsorption strength for all polysulfide species, which is mainly due to the existence of the TM-N₄ active center in these frame systems. Especially for the non-synthesized V-rCTNQ, the theoretical calculation fully predicts that the material has the most suitable adsorption strength for polysul-fides, excellent charging-discharging reaction and Li-ion diffusion performance. Additionally, Mn-rTCNQ, which has been synthesized experimentally, is also suitable for further experimental con-firmation. These findings not only provide novel MOFs for promoting the commercialization of Li-S batteries, but also provide unique insights for fully understanding their catalytic reaction mecha-nism. Full article

(This article belongs to the Special Issue Research Progress on Lithium–Sulfur Batteries)

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Molecules, Volume 28, Issue 5 (March-1 2023) – 418 articles

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