Molecules

85 pages, 448309 KiB

Open AccessReview

Evaluation of Substituted Pyrazole-Based Kinase Inhibitors in One Decade (2011–2020): Current Status and Future Prospects

by Mohammed I. El-Gamal, Seyed-Omar Zaraei, Moustafa M. Madkour and Hanan S. Anbar

Molecules 2022, 27(1), 330; https://doi.org/10.3390/molecules27010330 - 05 Jan 2022

Cited by 23 | Viewed by 5749

Abstract

Pyrazole has been recognized as a pharmacologically important privileged scaffold whose derivatives produce almost all types of pharmacological activities and have attracted much attention in the last decades. Of the various pyrazole derivatives reported as potential therapeutic agents, this article focuses on pyrazole-based [...] Read more.

Pyrazole has been recognized as a pharmacologically important privileged scaffold whose derivatives produce almost all types of pharmacological activities and have attracted much attention in the last decades. Of the various pyrazole derivatives reported as potential therapeutic agents, this article focuses on pyrazole-based kinase inhibitors. Pyrazole-possessing kinase inhibitors play a crucial role in various disease areas, especially in many cancer types such as lymphoma, breast cancer, melanoma, cervical cancer, and others in addition to inflammation and neurodegenerative disorders. In this article, we reviewed the structural and biological characteristics of the pyrazole derivatives recently reported as kinase inhibitors and classified them according to their target kinases in a chronological order. We reviewed the reports including pyrazole derivatives as kinase inhibitors published during the past decade (2011–2020). Full article

(This article belongs to the Special Issue Designing Next-Generation Drug-Like Molecules for Medicinal Applications)

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12 pages, 2167 KiB

Open AccessArticle

Laser-Induced Interdigital Structured Graphene Electrodes Based Flexible Micro-Supercapacitor for Efficient Peak Energy Storage

by Apurba Ray, Jenny Roth and Bilge Saruhan

Molecules 2022, 27(1), 329; https://doi.org/10.3390/molecules27010329 - 05 Jan 2022

Cited by 23 | Viewed by 4361

Abstract

The rapidly developing demand for lightweight portable electronics has accelerated advanced research on self-powered microsystems (SPMs) for peak power energy storage (ESs). In recent years, there has been, in this regard, a huge research interest in micro-supercapacitors for microelectronics application over micro-batteries due [...] Read more.

The rapidly developing demand for lightweight portable electronics has accelerated advanced research on self-powered microsystems (SPMs) for peak power energy storage (ESs). In recent years, there has been, in this regard, a huge research interest in micro-supercapacitors for microelectronics application over micro-batteries due to their advantages of fast charge–discharge rate, high power density and long cycle-life. In this work, the optimization and fabrication of micro-supercapacitors (MSCs) by means of laser-induced interdigital structured graphene electrodes (LIG) has been reported. The flexible and scalable MSCs are fabricated by CO₂-laser structuring of polyimide-based Kapton ^® HN foils at ambient temperature yielding interdigital LIG-electrodes and using polymer gel electrolyte (PGE) produced by polypropylene carbonate (PPC) embedded ionic liquid of 1-ethyl-3-methyl-imidazolium-trifluoromethansulphonate [EMIM][OTf]. This MSC exhibits a wide stable potential window up to 2.0 V, offering an areal capacitance of 1.75 mF/cm² at a scan rate of 5.0 mV/s resulting in an energy density (E_a) of 0.256 µWh/cm² @ 0.03 mA/cm² and power density (P_a) of 0.11 mW/cm² @0.1 mA/cm². Overall electrochemical performance of this LIG/PGE-MSC is rounded with a good cyclic stability up to 10,000 cycles demonstrating its potential in terms of peak energy storage ability compared to the current thin film micro-supercapacitors. Full article

(This article belongs to the Special Issue The Chemistry of Sustainable Energy Conversion and Storage)

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10 pages, 1176 KiB

Open AccessArticle

Nanosheets with High-Performance Electrochemical Oxygen Reduction Reaction Revived from Green Walnut Peel

by Yifei Zhou, Lei Yan and Junhua Hou

Molecules 2022, 27(1), 328; https://doi.org/10.3390/molecules27010328 - 05 Jan 2022

Cited by 6 | Viewed by 2320

Abstract

The synthesis of metal-free carbon-based electrocatalysts for oxygen reduction reactions (ORR) to replace conventional Pt-based catalysts has become a hot spot in current research. This work proposes an activation-assisted carbonization strategy, to manufacture N-doped ultra-thin carbon nanosheets (GWS180M800) with high catalytic activity, namely, [...] Read more.

The synthesis of metal-free carbon-based electrocatalysts for oxygen reduction reactions (ORR) to replace conventional Pt-based catalysts has become a hot spot in current research. This work proposes an activation-assisted carbonization strategy, to manufacture N-doped ultra-thin carbon nanosheets (GWS180M800) with high catalytic activity, namely, melamine is used as an accelerator/nitrogen source, and walnut green peels biological waste as a carbon source. The melamine acts as a nitrogen donor in the hydrothermal process, effectively enhancing the nitrogen doping rate. The content of pyridine nitrogen groups accounts for up to 48.5% of the total nitrogen content. Electrochemical tests show that the GWS180M800 has excellent ORR electrocatalytic activity and stability, and makes a quasi-four-electron ORR pathway clear in the alkaline electrolyte. The initial potential and half slope potential are as high as 1.01 and 0.82 V vs. RHE, respectively. The GWS180M800 catalyst has a better ability to avoid methanol cross poisoning than Pt/C has. Compared with 20 wt% Pt/C, GWS180M800 has improved methanol tolerance and stability. It is a metal-free biochar ORR catalyst with great development potential and application prospects. This result provides a new space for the preparation of valuable porous nano-carbon materials based on carbonaceous solid waste and provides new ideas for catalyzing a wide range of electrochemical reactions in the future. Full article

(This article belongs to the Special Issue Carbon-Based Materials for Sustainable Chemistry)

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12 pages, 1930 KiB

Open AccessArticle

Unpredicted Concentration-Dependent Sensory Properties of Pyrene-Containing NBN-Doped Polycyclic Aromatic Hydrocarbons

by Hang Xiao, Tao Li, Xiao-Li Sun, Wen-Ming Wan, Hongli Bao, Qingrong Qian and Qinghua Chen

Molecules 2022, 27(1), 327; https://doi.org/10.3390/molecules27010327 - 05 Jan 2022

Cited by 3 | Viewed by 2709

Abstract

Pyrene molecules containing NBN-doped polycyclic aromatic hydrocarbons (PAHs) have been synthesized by a simple and efficient intermolecular dehydration reaction between 1-pyrenylboronic acid and aromatic diamine. Pyrene-B (o-phenylenediamine) with a five-membered NBN ring and pyrene-B (1,8-diaminonaphthalene) with a six-membered NBN ring show differing luminescence. [...] Read more.

Pyrene molecules containing NBN-doped polycyclic aromatic hydrocarbons (PAHs) have been synthesized by a simple and efficient intermolecular dehydration reaction between 1-pyrenylboronic acid and aromatic diamine. Pyrene-B (o-phenylenediamine) with a five-membered NBN ring and pyrene-B (1,8-diaminonaphthalene) with a six-membered NBN ring show differing luminescence. Pyrene-B (o-phenylenediamine) shows concentration-dependent luminescence and enhanced emission after grinding at solid state. Pyrene-B (1,8-diaminonaphthalene) exhibits a turn-on type luminescence upon fluoride ion addition at lower concentration, as well as concentration-dependent stability. Further potential applications of Pyrene-B (o-phenylenediamine) on artificial light-harvesting film were demonstrated by using commercial NiR dye as acceptor. Full article

(This article belongs to the Special Issue Selected Papers from the 3rd Chinese Chemical Society Conference on Boron Sciences)

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14 pages, 2962 KiB

Open AccessArticle

Comparison of a Rapid Light-Induced and Forced Test to Study the Oxidative Stability of White Wines

by Emilio Celotti, Georgios Lazaridis, Jakob Figelj, Yuri Scutaru and Andrea Natolino

Molecules 2022, 27(1), 326; https://doi.org/10.3390/molecules27010326 - 05 Jan 2022

Cited by 4 | Viewed by 2136

Abstract

The oxidation processes of white wines can occur during storage and commercialization due to several factors, and these can negatively affect the color, aroma, and quality of the wine. Wineries should have faster and simpler methods that provide valuable information on oxidation stability [...] Read more.

The oxidation processes of white wines can occur during storage and commercialization due to several factors, and these can negatively affect the color, aroma, and quality of the wine. Wineries should have faster and simpler methods that provide valuable information on oxidation stability of wines and allow fast decision-making procedures, able to trigger suitable technological interventions. Using a portable prototype instrument for light irradiations at different wavelengths and times was considered and evaluated on sensorial, spectrophotometric, and colorimetric parameters of white wines. The sensorial analysis revealed that white and light blue were the most significant, after only 1 h of irradiation. The experimental results showed that hydrogen peroxide could enhance the effect of light treatment, allowing a contemporary evaluation of the oxidation stability of wine against light and chemical stresses. As expected, a good correlation (R² > 0.89) between optical density at 420 nm and b* parameter was highlighted. The synergic effect of light and H₂O₂ was also studied on the hydrolyzable and condensed tannins’ additions to white wine. The proposed methodology could be used to evaluate the oxidative stability of white wines, but also to evaluate the effect of some oenological adjuvants on wine stability. Full article

(This article belongs to the Special Issue Wine Sensory Faults: Origin, Prevention and Removal)

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18 pages, 5884 KiB

Open AccessArticle

Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

by Lesly Dasilva Wandji Djouonkep, Arnaud Kamdem Tamo, Ingo Doench, Naomie Beolle Songwe Selabi, Emmanuel Monga Ilunga, Arnaud Regis Kamgue Lenwoue, Mario Gauthier, Zhengzai Cheng and Anayancy Osorio-Madrazo

Molecules 2022, 27(1), 325; https://doi.org/10.3390/molecules27010325 - 05 Jan 2022

Cited by 15 | Viewed by 2944

Abstract

In this work, the feasibility of replacing petroleum-based poly(ethylene terephthalate) (PET) with fully bio-based copolyesters derived from dimethyl 2,5-thiophenedicarboxylate (DMTD), dimethyl 2,5-dimethoxyterephthalate (DMDMT), and polysaccharide-derived 1,6-hexanediol (HDO) was investigated. A systematic study of structure-property relationship revealed that the properties of these poly(thiophene–aromatic) copolyesters [...] Read more.

In this work, the feasibility of replacing petroleum-based poly(ethylene terephthalate) (PET) with fully bio-based copolyesters derived from dimethyl 2,5-thiophenedicarboxylate (DMTD), dimethyl 2,5-dimethoxyterephthalate (DMDMT), and polysaccharide-derived 1,6-hexanediol (HDO) was investigated. A systematic study of structure-property relationship revealed that the properties of these poly(thiophene–aromatic) copolyesters (PHS(20–90)) can be tailored by varying the ratio of diester monomers in the reaction, whereby an increase in DMTD content noticeably shortened the reaction time in the transesterification step due to its higher reactivity as compared with DMDMT. The copolyesters had weight-average molar masses (Mw) between 27,500 and 38,800 g/mol, and dispersity Đ of 2.0–2.5. The different polarity and stability of heterocyclic DMTD provided an efficient mean to tailor the crystallization ability of the copolyesters, which in turn affected the thermal and mechanical performance. The glass transition temperature (T_g) could be tuned from 70–100 °C, while the tensile strength was in a range of 23–80 MPa. The obtained results confirmed that the co-monomers were successfully inserted into the copolyester chains. As compared with commercial poly(ethylene terephthalate), the copolyesters displayed not only enhanced susceptibility to hydrolysis, but also appreciable biodegradability by lipases, with weight losses of up to 16% by weight after 28 weeks of incubation. Full article

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

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13 pages, 720 KiB

Open AccessReview

Glutathione in Brain Disorders and Aging

by Igor Y. Iskusnykh, Anastasia A. Zakharova and Dhruba Pathak

Molecules 2022, 27(1), 324; https://doi.org/10.3390/molecules27010324 - 05 Jan 2022

Cited by 70 | Viewed by 15172

Abstract

Glutathione is a remarkably functional molecule with diverse features, which include being an antioxidant, a regulator of DNA synthesis and repair, a protector of thiol groups in proteins, a stabilizer of cell membranes, and a detoxifier of xenobiotics. Glutathione exists in two states—oxidized [...] Read more.

Glutathione is a remarkably functional molecule with diverse features, which include being an antioxidant, a regulator of DNA synthesis and repair, a protector of thiol groups in proteins, a stabilizer of cell membranes, and a detoxifier of xenobiotics. Glutathione exists in two states—oxidized and reduced. Under normal physiological conditions of cellular homeostasis, glutathione remains primarily in its reduced form. However, many metabolic pathways involve oxidization of glutathione, resulting in an imbalance in cellular homeostasis. Impairment of glutathione function in the brain is linked to loss of neurons during the aging process or as the result of neurological diseases such as Huntington’s disease, Parkinson’s disease, stroke, and Alzheimer’s disease. The exact mechanisms through which glutathione regulates brain metabolism are not well understood. In this review, we will highlight the common signaling cascades that regulate glutathione in neurons and glia, its functions as a neuronal regulator in homeostasis and metabolism, and finally a mechanistic recapitulation of glutathione signaling. Together, these will put glutathione’s role in normal aging and neurological disorders development into perspective. Full article

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5 pages, 206 KiB

Open AccessEditorial

Tribute to Professor Raphael Mechoulam, The Founder of Cannabinoid and Endocannabinoid Research

by Mauro Maccarrone

Molecules 2022, 27(1), 323; https://doi.org/10.3390/molecules27010323 - 05 Jan 2022

Viewed by 2719

Abstract

During the last 60 years the relevance for human health and disease of cannabis (Cannabis sativa or Cannabis indica) ingredients, like the psychoactive compound Δ⁹-tetrahydrocannabinol (THC), cannabidiol, 120+ cannabinoids and 440+ non-cannabinoid compounds, has become apparent [...] Full article

(This article belongs to the Special Issue A Themed Issue in Honor of Professor Raphael Mechoulam: The Father of Cannabinoid and Endocannabinoid Research)

21 pages, 2701 KiB

Open AccessArticle

Antibacterial Activity of Pharmaceutical-Grade Rose Bengal: An Application of a Synthetic Dye in Antibacterial Therapies

by Michio Kurosu, Katsuhiko Mitachi, Junshu Yang, Edward V. Pershing, Bruce D. Horowitz, Eric A. Wachter, John W. Lacey III, Yinduo Ji and Dominic J. Rodrigues

Molecules 2022, 27(1), 322; https://doi.org/10.3390/molecules27010322 - 05 Jan 2022

Cited by 14 | Viewed by 4829

Abstract

Rose bengal has been used in the diagnosis of ophthalmic disorders and liver function, and has been studied for the treatment of solid tumor cancers. To date, the antibacterial activity of rose bengal has been sporadically reported; however, these data have been generated [...] Read more.

Rose bengal has been used in the diagnosis of ophthalmic disorders and liver function, and has been studied for the treatment of solid tumor cancers. To date, the antibacterial activity of rose bengal has been sporadically reported; however, these data have been generated with a commercial grade of rose bengal, which contains major uncontrolled impurities generated by the manufacturing process (80–95% dye content). A high-purity form of rose bengal formulation (HP-RBf, >99.5% dye content) kills a battery of Gram-positive bacteria, including drug-resistant strains at low concentrations (0.01–3.13 μg/mL) under fluorescent, LED, and natural light in a few minutes. Significantly, HP-RBf effectively eradicates Gram-positive bacterial biofilms. The frequency that Gram-positive bacteria spontaneously developed resistance to HP-RB is extremely low (less than 1 × 10⁻¹³). Toxicity data obtained through our research programs indicate that HP-RB is feasible as an anti-infective drug for the treatment of skin and soft tissue infections (SSTIs) involving multidrug-resistant (MDR) microbial invasion of the skin, and for eradicating biofilms. This article summarizes the antibacterial activity of pharmaceutical-grade rose bengal, HP-RB, against Gram-positive bacteria, its cytotoxicity against skin cells under illumination conditions, and mechanistic insights into rose bengal’s bactericidal activity under dark conditions. Full article

(This article belongs to the Special Issue Antibacterial Agents 2021)

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21 pages, 4291 KiB

Open AccessArticle

Design, Synthesis, and Biological Evaluation of 5,6,7,8-Tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines as Microtubule Targeting Agents

by Farhana Islam, Arpit Doshi, Andrew J. Robles, Tasdique M. Quadery, Xin Zhang, Xilin Zhou, Ernest Hamel, Susan L. Mooberry and Aleem Gangjee

Molecules 2022, 27(1), 321; https://doi.org/10.3390/molecules27010321 - 05 Jan 2022

Cited by 4 | Viewed by 3077

Abstract

A series of eleven 4-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines were designed and synthesized and their biological activities were evaluated. Synthesis involved the Gewald reaction to synthesize ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate ring, and S_NAr reactions. Compound 4 was 1.6- and ~7-fold more potent than the [...] Read more.

A series of eleven 4-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines were designed and synthesized and their biological activities were evaluated. Synthesis involved the Gewald reaction to synthesize ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate ring, and S_NAr reactions. Compound 4 was 1.6- and ~7-fold more potent than the lead compound 1 in cell proliferation and microtubule depolymerization assays, respectively. Compounds 4, 5 and 7 showed the most potent antiproliferative effects (IC₅₀ values < 40 nM), while compounds 6, 8, 10, 12 and 13 had lower antiproliferative potencies (IC₅₀ values of 53–125 nM). Additionally, compounds 4–8, 10 and 12–13 circumvented Pgp and βIII-tubulin mediated drug resistance, mechanisms that diminish the clinical efficacy of paclitaxel (PTX). In the NCI-60 cell line panel, compound 4 exhibited an average GI₅₀ of ~10 nM in the 40 most sensitive cell lines. Compound 4 demonstrated statistically significant antitumor effects in a murine MDA-MB-435 xenograft model. Full article

(This article belongs to the Special Issue Design, Synthesis and Applications of New Anti-cancer Agents II)

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12 pages, 2125 KiB

Open AccessArticle

Cool Temperature Enhances Growth, Ferulic Acid and Flavonoid Biosynthesis While Inhibiting Polysaccharide Biosynthesis in Angelica sinensis

by Han Dong, Meiling Li, Ling Jin, Xiaorong Xie, Mengfei Li and Jianhe Wei

Molecules 2022, 27(1), 320; https://doi.org/10.3390/molecules27010320 - 05 Jan 2022

Cited by 15 | Viewed by 2609

Abstract

Angelica sinensis, a perennial herb that produces ferulic acid and phthalides for the treatment of cardio-cerebrovascular diseases, prefers growing at an altitude of 1800–3000 m. Geographical models have predicted that high altitude, cool temperature and sunshade play determining roles in geo-authentic formation. [...] Read more.

Angelica sinensis, a perennial herb that produces ferulic acid and phthalides for the treatment of cardio-cerebrovascular diseases, prefers growing at an altitude of 1800–3000 m. Geographical models have predicted that high altitude, cool temperature and sunshade play determining roles in geo-authentic formation. Although the roles of altitude and light in yield and quality have been investigated, the role of temperature in regulating growth, metabolites biosynthesis and gene expression is still unclear. In this study, growth characteristics, metabolites contents and related genes expression were investigated by exposing A. sinensis to cooler (15 °C) and normal temperatures (22 °C). The results showed that plant biomass, the contents of ferulic acid and flavonoids and the expression levels of genes related to the biosynthesis of ferulic acid (PAL1, 4CLL4, 4CLL9, C3H, HCT, CCOAMT and CCR) and flavonoids (CHS and CHI) were enhanced at 15 °C compared to 22 °C. The contents of ligustilide and volatile oils exhibited slight increases, while polysaccharide contents decreased in response to cooler temperature. Based on gene expression levels, ferulic acid biosynthesis probably depends on the CCOAMT pathway and not the COMT pathway. It can be concluded that cool temperature enhances plant growth, ferulic acid and flavonoid accumulation but inhibits polysaccharide biosynthesis in A. sinensis. These findings authenticate that cool temperature plays a determining role in the formation of geo-authentic and also provide a strong foundation for regulating metabolites production of A. sinensis. Full article

(This article belongs to the Special Issue Plant Secondary Metabolites with Health Effects: Discovery and Engineering)

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35 pages, 22752 KiB

Open AccessReview

Recent Progress in the Development of Indole-Based Compounds Active against Malaria, Trypanosomiasis and Leishmaniasis

by Paulo A. F. Pacheco and Maria M. M. Santos

Molecules 2022, 27(1), 319; https://doi.org/10.3390/molecules27010319 - 05 Jan 2022

Cited by 18 | Viewed by 3487

Abstract

Human protozoan diseases represent a serious health problem worldwide, affecting mainly people in social and economic vulnerability. These diseases have attracted little investment in drug discovery, which is reflected in the limited available therapeutic arsenal. Authorized drugs present problems such as low efficacy [...] Read more.

Human protozoan diseases represent a serious health problem worldwide, affecting mainly people in social and economic vulnerability. These diseases have attracted little investment in drug discovery, which is reflected in the limited available therapeutic arsenal. Authorized drugs present problems such as low efficacy in some stages of the disease or toxicity, which result in undesirable side effects and treatment abandonment. Moreover, the emergence of drug-resistant parasite strains makes necessary an even greater effort to develop safe and effective antiparasitic agents. Among the chemotypes investigated for parasitic diseases, the indole nucleus has emerged as a privileged molecular scaffold for the generation of new drug candidates. In this review, the authors provide an overview of the indole-based compounds developed against important parasitic diseases, namely malaria, trypanosomiasis and leishmaniasis, by focusing on the design, optimization and synthesis of the most relevant synthetic indole scaffolds recently reported. Full article

(This article belongs to the Special Issue Molecules Medicinal Chemistry Reviews)

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13 pages, 565 KiB

Open AccessArticle

Effect of Ultrasound and Enzymatic Mash Treatment on Bioactive Compounds and Antioxidant Capacity of Black, Red and White Currant Juices

by Marcin Kidoń and Guruprasath Narasimhan

Molecules 2022, 27(1), 318; https://doi.org/10.3390/molecules27010318 - 05 Jan 2022

Cited by 11 | Viewed by 2093

Abstract

Ultrasound treatment is recognized as a potential technique for improvement in the nutritional values of fruit juices. This study was initiated with the objective of evaluating bioactive compounds and some important quality parameters of black (BC), red (RC) and white (WC) currant juices [...] Read more.

Ultrasound treatment is recognized as a potential technique for improvement in the nutritional values of fruit juices. This study was initiated with the objective of evaluating bioactive compounds and some important quality parameters of black (BC), red (RC) and white (WC) currant juices obtained from fruit mash preliminarily treated by enzymes combined with ultrasound. Individual and total phenolic content (TPC), anthocyanins, color parameters, ascorbic acid, antioxidant capacity (TEAC), juice yield, pH, titratable acidity, and soluble solids were investigated. Significant increases in the levels of TPC and antioxidant capacity of sonicated samples were observed. However, ultrasound treatment had no effect on individual phenolic compounds of juices. Sonication of mash before juice pressing did not cause any noticeable changes in ascorbic acid content. Only in the case of WC was an increase in content of vitamin C noticed. The color of juices obtained after treatment was similar to the control sample. It was demonstrated that enzymatic combined with ultrasound treatment of mash for different colored currant fruit did not have any dismissive effect and could even improve some parameters of the juice obtained. Full article

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15 pages, 1692 KiB

Open AccessArticle

Different Fruit-Specific Promoters Drive AtMYB12 Expression to Improve Phenylpropanoid Accumulation in Tomato

by Xiangyu Ding, Ziyi Yin, Shaoli Wang, Haoqi Liu, Xiaomeng Chu, Jiazong Liu, Haipeng Zhao, Xinyu Wang, Yang Li and Xinhua Ding

Molecules 2022, 27(1), 317; https://doi.org/10.3390/molecules27010317 - 05 Jan 2022

Cited by 6 | Viewed by 2345

Abstract

Tomato is an economically crucial vegetable/fruit crop globally. Tomato is rich in nutrition and plays an essential role in a healthy human diet. Phenylpropanoid, a critical compound in tomatoes, reduces common degenerative and chronic diseases risk caused by oxidative stress. As an MYB [...] Read more.

Tomato is an economically crucial vegetable/fruit crop globally. Tomato is rich in nutrition and plays an essential role in a healthy human diet. Phenylpropanoid, a critical compound in tomatoes, reduces common degenerative and chronic diseases risk caused by oxidative stress. As an MYB transcription factor, ATMYB12 can increase phenylpropanoid content by activating phenylpropanoid synthesis related genes, such as PAL, C4H, 4CL, CHS. However, the heterologous expression of AtMYB12 in tomatoes can be altered through transgenic technologies, such as unstable expression vectors and promoters with different efficiency. In the current study, the efficiency of other fruit-specific promoters, namely E8S, 2A12, E4, and PG, were compared and screened, and we determined that the expression efficiency of AtMYB12 was driven by the E8S promoter was the highest. As a result, the expression of phenylpropanoid synthesis related genes was regulated by AtMYB12, and the phenylpropanoid accumulation in transgenic tomato fruits increased 16 times. Additionally, the total antioxidant capacity of fruits was measured through Trolox equivalent antioxidant capacity (TEAC) assay, which was increased by 2.4 times in E8S transgenic lines. TEAC was positively correlated with phenylpropanoid content. Since phenylpropanoid plays a crucial role in the human diet, expressing AtMYB12 with stable and effective fruit-specific promoter E8S could improve tomato’s phenylpropanoid and nutrition content and quality. Our results can provide genetic resources for the subsequent improvement of tomato varieties and quality, which is significant for human health. Full article

(This article belongs to the Special Issue Phenolic Composition, Antioxidant Potential and Bioactive Potential of Natural Products)

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17 pages, 4680 KiB

Open AccessArticle

Chemical Composition and Thermogravimetric Behaviors of Glanded and Glandless Cottonseed Kernels

by Zhongqi He, Sunghyun Nam, Hailin Zhang and Ocen Modesto Olanya

Molecules 2022, 27(1), 316; https://doi.org/10.3390/molecules27010316 - 05 Jan 2022

Cited by 16 | Viewed by 2308

Abstract

Common “glanded” (Gd) cottonseeds contain the toxic compound gossypol that restricts human consumption of the derived products. The “glandless” (Gl) cottonseeds of a new cotton variety, in contrast, show a trace gossypol content, indicating the great potential of cottonseed for agro-food applications. This [...] Read more.

Common “glanded” (Gd) cottonseeds contain the toxic compound gossypol that restricts human consumption of the derived products. The “glandless” (Gl) cottonseeds of a new cotton variety, in contrast, show a trace gossypol content, indicating the great potential of cottonseed for agro-food applications. This work comparatively evaluated the chemical composition and thermogravimetric behaviors of the two types of cottonseed kernels. In contrast to the high gossypol content (3.75 g kg⁻¹) observed in Gd kernels, the gossypol level detected in Gl kernels was only 0.06 g kg⁻¹, meeting the FDA’s criteria as human food. While the gossypol gland dots in Gd kernels were visually observed, scanning electron microcopy was not able to distinguish the microstructural difference between ground Gd and Gl samples. Chemical analysis and Fourier transform infrared (FTIR) spectroscopy showed that Gl kernels and Gd kernels had similar chemical components and mineral contents, but the former was slightly higher in protein, starch, and phosphorus contents. Thermogravimetric (TG) processes of both kernels and their residues after hexane and ethanol extraction were based on three stages of drying, de-volatilization, and char formation. TG-FTIR analysis revealed apparent spectral differences between Gd and Gl samples, as well as between raw and extracted cottonseed kernel samples, indicating that some components in Gd kernels were more susceptible to thermal decomposition than Gl kernels. The TG and TG-FTIR observations suggested that the Gl kernels could be heat treated (e.g., frying and roasting) at an optimal temperature of 140–150 °C for food applications. On the other hand, optimal pyrolysis temperatures would be much higher (350–500 °C) for Gd cottonseed and its defatted residues for non-food bio-oil and biochar production. The findings from this research enhance the potential utilization of Gd and Gl cottonseed kernels for food applications. Full article

(This article belongs to the Special Issue Feature Papers in Food Chemistry)

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14 pages, 2389 KiB

Open AccessArticle

Simultaneous Detoxification of Aflatoxin B1, Zearalenone and Deoxynivalenol by Modified Montmorillonites

by Jiaqi Mao, Ying Zhou, Guanglie Lv and Renxian Zhou

Molecules 2022, 27(1), 315; https://doi.org/10.3390/molecules27010315 - 05 Jan 2022

Cited by 9 | Viewed by 2195

Abstract

Raw Ca-based montmorillonite (MMT) was treated by H₂SO₄, calcination and organic compounds (hexadecyltrimethyl ammonium bromide (HTAB), cetylpyridinium chloride (CPC) and chitosan (CTS)), respectively. The modified montmorillonites were characterized by different methods and their adsorption performances for three mycotoxins (Aflatoxin [...] Read more.

Raw Ca-based montmorillonite (MMT) was treated by H₂SO₄, calcination and organic compounds (hexadecyltrimethyl ammonium bromide (HTAB), cetylpyridinium chloride (CPC) and chitosan (CTS)), respectively. The modified montmorillonites were characterized by different methods and their adsorption performances for three mycotoxins (Aflatoxin B1 (AFB1), zearalenone (ZEA) and deoxynivalenol (DON)) were evaluated at pH = 2.8 and 8.0, respectively. The results indicate that surfactants (CPC and HTAB) intercalation is the most efficient modification, which obviously improves the adsorption performance of montmorillonite for mycotoxins, with adsorption efficiency of above 90% for AFB1 and ZEA whether under acid or alkaline conditions, due to the increase in basal spacing and the improvement of hydrophobicity. Moreover, the adsorption efficiencies of AFB1 and ZEA over CPC-modified montmorillonite (CPC-AMMT-3) coexisting with vitamin B6 or lysine are still at a high level (all above 94%). All modified montmorillonites, however, have low adsorption efficiency for DON, with somewhat spherical molecular geometry. Full article

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12 pages, 605 KiB

Open AccessArticle

Tunisian Native Mentha pulegium L. Extracts: Phytochemical Composition and Biological Activities

by Jed Jebali, Hanene Ghazghazi, Chedia Aouadhi, Ines ELBini-Dhouib, Ridha Ben Salem, Najet Srairi-Abid, Naziha Marrakchi and Ghayth Rigane

Molecules 2022, 27(1), 314; https://doi.org/10.3390/molecules27010314 - 05 Jan 2022

Cited by 9 | Viewed by 2735

Abstract

Mint species (Lamiaceae family) have been used as traditional remedies for the treatment of several diseases. In this work, we aimed to characterize the biological activities of the total phenolic and flavonoid contents of Mentha pulegium L. extracts collected from two different [...] Read more.

Mint species (Lamiaceae family) have been used as traditional remedies for the treatment of several diseases. In this work, we aimed to characterize the biological activities of the total phenolic and flavonoid contents of Mentha pulegium L. extracts collected from two different regions of Tunisia. The highest amounts of total phenols (74.45 ± 0.01 mg GAE/g DW), flavonoids (28.87 ± 0.02 mg RE/g DW), and condensed tannins (4.35 ± 0.02 mg CE/g DW) were found in the Bizerte locality. Methanolic leaf extracts were subjected to HPLC-UV analysis in order to identify and quantify the phenolic composition. This technique allowed us to identify seven phenolic compounds: two phenolic acids and five flavonoid compounds, such as eriocitrin, hesperidin, narirutin, luteolin, and isorhoifolin, which were found in both extracts with significant differences between samples collected from the different regions (p < 0.05). Furthermore, our results showed that the methanolic extract from leaves collected from Bizerte had the highest antioxidant activities (DPPH IC₅₀ value of 16.31 μg/mL and 570.08 μmol Fe²⁺/g, respectively). Both extracts showed high radical-scavenging activity as well as significant antimicrobial activity against eight tested bacteria. The highest antimicrobial activities were observed against Gram-positive bacteria with inhibition zone diameters and MIC values ranging between 19 and 32 mm and 40 and 160 µg/mL, respectively. Interestingly, at 10 μg/mL, the extract had a significant effect on cell proliferation of U87 human glioblastoma cells. These findings open perspectives for the use of Mentha pulegium L. extract in green pharmacy, alternative/complementary medicine, and natural preventive therapies for the development of effective antioxidant, antibacterial, and/or antitumoral drugs. Full article

(This article belongs to the Special Issue Biological Activity of Plant Compounds and Extracts)

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31 pages, 3682 KiB

Open AccessReview

Plant Secondary Metabolites Produced in Response to Abiotic Stresses Has Potential Application in Pharmaceutical Product Development

by Karma Yeshi, Darren Crayn, Edita Ritmejerytė and Phurpa Wangchuk

Molecules 2022, 27(1), 313; https://doi.org/10.3390/molecules27010313 - 05 Jan 2022

Cited by 124 | Viewed by 10731

Abstract

Plant secondary metabolites (PSMs) are vital for human health and constitute the skeletal framework of many pharmaceutical drugs. Indeed, more than 25% of the existing drugs belong to PSMs. One of the continuing challenges for drug discovery and pharmaceutical industries is gaining access [...] Read more.

Plant secondary metabolites (PSMs) are vital for human health and constitute the skeletal framework of many pharmaceutical drugs. Indeed, more than 25% of the existing drugs belong to PSMs. One of the continuing challenges for drug discovery and pharmaceutical industries is gaining access to natural products, including medicinal plants. This bottleneck is heightened for endangered species prohibited for large sample collection, even if they show biological hits. While cultivating the pharmaceutically interesting plant species may be a solution, it is not always possible to grow the organism outside its natural habitat. Plants affected by abiotic stress present a potential alternative source for drug discovery. In order to overcome abiotic environmental stressors, plants may mount a defense response by producing a diversity of PSMs to avoid cells and tissue damage. Plants either synthesize new chemicals or increase the concentration (in most instances) of existing chemicals, including the prominent bioactive lead compounds morphine, camptothecin, catharanthine, epicatechin-3-gallate (EGCG), quercetin, resveratrol, and kaempferol. Most PSMs produced under various abiotic stress conditions are plant defense chemicals and are functionally anti-inflammatory and antioxidative. The major PSM groups are terpenoids, followed by alkaloids and phenolic compounds. We have searched the literature on plants affected by abiotic stress (primarily studied in the simulated growth conditions) and their PSMs (including pharmacological activities) from PubMed, Scopus, MEDLINE Ovid, Google Scholar, Databases, and journal websites. We used search keywords: “stress-affected plants,” “plant secondary metabolites, “abiotic stress,” “climatic influence,” “pharmacological activities,” “bioactive compounds,” “drug discovery,” and “medicinal plants” and retrieved published literature between 1973 to 2021. This review provides an overview of variation in bioactive phytochemical production in plants under various abiotic stress and their potential in the biodiscovery of therapeutic drugs. We excluded studies on the effects of biotic stress on PSMs. Full article

(This article belongs to the Special Issue Bioactive Molecules and Drug Lead Compounds)

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9 pages, 1189 KiB

Open AccessCommunication

The Caenorhabditis elegans DEG-3/DES-2 Channel Is a Betaine-Gated Receptor Insensitive to Monepantel

by Tina V. A. Hansen, Heinz Sager, Céline E. Toutain, Elise Courtot, Cédric Neveu and Claude L. Charvet

Molecules 2022, 27(1), 312; https://doi.org/10.3390/molecules27010312 - 05 Jan 2022

Cited by 5 | Viewed by 2085

Abstract

Natural plant compounds, such as betaine, are described to have nematocidal properties. Betaine also acts as a neurotransmitter in the free-living model nematode Caenorhabditis elegans, where it is required for normal motility. Worm motility is mediated by nicotinic acetylcholine receptors (nAChRs), including [...] Read more.

Natural plant compounds, such as betaine, are described to have nematocidal properties. Betaine also acts as a neurotransmitter in the free-living model nematode Caenorhabditis elegans, where it is required for normal motility. Worm motility is mediated by nicotinic acetylcholine receptors (nAChRs), including subunits from the nematode-specific DEG-3 group. Not all types of nAChRs in this group are associated with motility, and one of these is the DEG-3/DES-2 channel from C. elegans, which is involved in nociception and possibly chemotaxis. Interestingly, the activity of DEG-3/DES-2 channel from the parasitic nematode of ruminants, Haemonchus contortus, is modulated by monepantel and its sulfone metabolite, which belong to the amino-acetonitrile derivative anthelmintic drug class. Here, our aim was to advance the pharmacological knowledge of the DEG-3/DES-2 channel from C. elegans by functionally expressing the DEG-3/DES-2 channel in Xenopus laevis oocytes and using two-electrode voltage-clamp electrophysiology. We found that the DEG-3/DES-2 channel was more sensitive to betaine than ACh and choline, but insensitive to monepantel and monepantel sulfone when used as direct agonists and as allosteric modulators in co-application with betaine. These findings provide important insight into the pharmacology of DEG-3/DES-2 from C. elegans and highlight the pharmacological differences between non-parasitic and parasitic nematode species. Full article

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

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18 pages, 1116 KiB

Open AccessReview

The Role of Neuropeptide-Stimulated cAMP-EPACs Signalling in Cancer Cells

by Zhengyin Gao, Weng I Lei and Leo Tsz On Lee

Molecules 2022, 27(1), 311; https://doi.org/10.3390/molecules27010311 - 05 Jan 2022

Cited by 7 | Viewed by 2723

Abstract

Neuropeptides are autocrine and paracrine signalling factors and mainly bind to G protein-coupled receptors (GPCRs) to trigger intracellular secondary messenger release including adenosine 3′, 5′-cyclic monophosphate (cAMP), thus modulating cancer progress in different kind of tumours. As one of the downstream effectors of [...] Read more.

Neuropeptides are autocrine and paracrine signalling factors and mainly bind to G protein-coupled receptors (GPCRs) to trigger intracellular secondary messenger release including adenosine 3′, 5′-cyclic monophosphate (cAMP), thus modulating cancer progress in different kind of tumours. As one of the downstream effectors of cAMP, exchange proteins directly activated by cAMP (EPACs) play dual roles in cancer proliferation and metastasis. More evidence about the relationship between neuropeptides and EPAC pathways have been proposed for their potential role in cancer development; hence, this review focuses on the role of neuropeptide/GPCR system modulation of cAMP/EPACs pathways in cancers. The correlated downstream pathways between neuropeptides and EPACs in cancer cell proliferation, migration, and metastasis is discussed to glimmer the direction of future research. Full article

(This article belongs to the Special Issue Neuropeptides: From Physiology to Therapeutic Applications)

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15 pages, 3775 KiB

Open AccessArticle

Co-Ingestion of Natal Plums (Carissa macrocarpa) and Marula Nuts (Sclerocarya birrea) in a Snack Bar and Its Effect on Phenolic Compounds and Bioactivities

by Vimbainashe E. Manhivi, Retha M. Slabbert and Dharini Sivakumar

Molecules 2022, 27(1), 310; https://doi.org/10.3390/molecules27010310 - 04 Jan 2022

Cited by 7 | Viewed by 2059

Abstract

This study investigated the effect of co-ingesting Natal plums (Carissa macrocarpa) and Marula nuts (Sclerocarya birrea) on the bioaccessibility and uptake of anthocyanins, antioxidant capacity, and the ability to inhibit α-glucosidase. A Natal plum–Marula nut bar was made by [...] Read more.

This study investigated the effect of co-ingesting Natal plums (Carissa macrocarpa) and Marula nuts (Sclerocarya birrea) on the bioaccessibility and uptake of anthocyanins, antioxidant capacity, and the ability to inhibit α-glucosidase. A Natal plum–Marula nut bar was made by mixing the raw nuts and the fruit pulp in a ratio 1:1 (v/v). The cyanidin-3-O-sambubioside (Cy-3-Sa) and cyanidin-3-O-glucoside content (Cy-3-G) were quantified using the ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UHPLC/Q-TOF-MS). Inclusion of Natal plum in the Marula nut bar increased the Cy-3-Sa, Cy-3-G content, antioxidants capacity and α-glucosidase inhibition compared to ingesting Marula nut separately at the internal phase. Adding Natal plum to the Marula nut bar increased bioaccessibility of Cy-3-Sa, Cy-3-G, quercetin, coumaric acid, syringic acid and ferulic acid to 80.2% and 71.9%, 98.7%, 95.2%, 51.9% and 89.3%, respectively, compared to ingesting the Natal plum fruit or nut separately. Full article

(This article belongs to the Special Issue Characterisation of Phenolics in Foods and Beverages and Their Role as Functional Constituents)

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18 pages, 9761 KiB

Open AccessArticle

Green Synthesis of Oxoquinoline-1(2H)-Carboxamide as Antiproliferative and Antioxidant Agents: An Experimental and In-Silico Approach to High Altitude Related Disorders

by Amena Ali, Abuzer Ali, Musarrat Husain Warsi, Mohammad Akhlaquer Rahman, Mohamed Jawed Ahsan and Faizul Azam

Molecules 2022, 27(1), 309; https://doi.org/10.3390/molecules27010309 - 04 Jan 2022

Cited by 1 | Viewed by 2038

Abstract

At high altitudes, drops in oxygen concentration result in the creation of reactive oxygen and nitrogen species (RONS), which cause a variety of health concerns. We addressed these health concerns and reported the synthesis, characterization, and biological activities of a series of 10 [...] Read more.

At high altitudes, drops in oxygen concentration result in the creation of reactive oxygen and nitrogen species (RONS), which cause a variety of health concerns. We addressed these health concerns and reported the synthesis, characterization, and biological activities of a series of 10 oxoquinolines. N-Aryl-7-hydroxy-4-methyl-2-oxoquinoline-1(2H)carboxamides (5a–j) were accessed in two steps under ultrasonicated irradiation, as per the reported method. The anticancer activity was tested at 10 µM against a total of 5 dozen cancer cell lines obtained from nine distinct panels, as per the National Cancer Institute (NCI US) protocol. The compounds 5a (TK-10 (renal cancer); %GI = 82.90) and 5j (CCRF-CEM (Leukemia); %GI = 58.61) showed the most promising anticancer activity. Compound 5a also demonstrated promising DPPH free radical scavenging activity with an IC₅₀ value of 14.16 ± 0.42 µM. The epidermal growth factor receptor (EGFR) and carbonic anhydrase (CA), two prospective cancer inhibitor targets, were used in the molecular docking studies. Molecular docking studies of ligand 5a (docking score = −8.839) against the active site of EGFR revealed two H-bond interactions with the residues Asp855 and Thr854, whereas ligand 5a (docking = −5.337) interacted with three H-bond with the residues Gln92, Gln67, and Thr200 against the active site CA. The reported compounds exhibited significant anticancer and antioxidant activities, as well as displayed significant inhibition against cancer targets, EGFR and CA, in the molecular docking studies. The current discovery may aid in the development of novel compounds for the treatment of cancer and oxidative stress, and other high altitude-related disorders. Full article

(This article belongs to the Special Issue Sustainable Chemistry in the Organic Synthesis of Bioactive Compounds)

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18 pages, 2949 KiB

Open AccessArticle

Characterization of the Volatile Compounds in Camellia oleifera Seed Oil from Different Geographic Origins

by Jing Wang, Xuxiao Tang, Qiulu Chu, Mengyu Zhang, Yingzhong Zhang and Baohua Xu

Molecules 2022, 27(1), 308; https://doi.org/10.3390/molecules27010308 - 04 Jan 2022

Cited by 10 | Viewed by 2490

Abstract

Volatile flavor of edible oils is an important quality index and factor affecting consumer choice. The purpose of this investigation was to characterize virgin Camellia oleifera seed oil (VCO) samples from different locations in southern China in terms of their volatile compounds to [...] Read more.

Volatile flavor of edible oils is an important quality index and factor affecting consumer choice. The purpose of this investigation was to characterize virgin Camellia oleifera seed oil (VCO) samples from different locations in southern China in terms of their volatile compounds to show the classification of VCO with respect to geography. Different samples from 20 producing VCO regions were collected in 2020 growing season, at almost the same maturity stage, and processed under the same conditions. Headspace solid-phase microextraction (HS-SPME) with a gas chromatography–mass spectrometer system (GC–MS) was used to analyze volatile compounds. A total of 348 volatiles were characterized, including aldehydes, ketones, alcohols, acids, esters, alkenes, alkanes, furans, phenols, and benzene; the relative contents ranged from 7.80–58.68%, 1.73–12.52%, 2.91–37.07%, 2.73–46.50%, 0.99–12.01%, 0.40–14.95%, 0.00–27.23%, 0.00–3.75%, 0.00–7.34%, and 0.00–1.55%, respectively. The VCO geographical origins with the largest number of volatile compounds was Xixiangtang of Guangxi (L17), and the least was Beireng of Hainan (L19). A total of 23 common and 98 unique volatile compounds were detected that reflected the basic and characteristic flavor of VCO, respectively. After PCA, heatmap and PLS-DA analysis, Longchuan of Guangdong (L8), Qingshanhu of Jiangxi (L16), and Panlong of Yunnan (L20) were in one group where the annual average temperatures are relatively low, where annual rainfalls are also low. Guangning of Guangdong (L6), Yunan of Guangdong (L7), Xingning of Guangdong (L9), Tianhe of Guangdong (L10), Xuwen of Guangdong (L11), and Xiuying of Hainan (L18) were in another group where the annual average temperatures are relatively high, and the altitudes are low. Hence, volatile compound distributions confirmed the differences among the VCO samples from these geographical areas, and the provenance difference evaluation can be carried out by flavor. Full article

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13 pages, 2439 KiB

Open AccessArticle

Computational Studies of Coinage Metal Anion M⁻ + CH₃X (X = F, Cl, Br, I) Reactions in Gas Phase

by Fan Wang, Xiaoyan Ji, Fei Ying, Jiatao Zhang, Chongyang Zhao and Jing Xie

Molecules 2022, 27(1), 307; https://doi.org/10.3390/molecules27010307 - 04 Jan 2022

Cited by 3 | Viewed by 1958

Abstract

We characterized the stationary points along the nucleophilic substitution (S_N2), oxidative insertion (OI), halogen abstraction (XA), and proton transfer (PT) product channels of M⁻ + CH₃X (M = Cu, Ag, Au; X = F, Cl, Br, I) reactions [...] Read more.

We characterized the stationary points along the nucleophilic substitution (S_N2), oxidative insertion (OI), halogen abstraction (XA), and proton transfer (PT) product channels of M⁻ + CH₃X (M = Cu, Ag, Au; X = F, Cl, Br, I) reactions using the CCSD(T)/aug-cc-pVTZ level of theory. In general, the reaction energies follow the order of PT > XA > S_N2 > OI. The OI channel that results in oxidative insertion complex [CH₃–M–X]⁻ is most exothermic, and can be formed through a front-side attack of M on the C-X bond via a high transition state OxTS or through a S_N2-mediated halogen rearrangement path via a much lower transition state invTS. The order of OxTS > invTS is inverted when changing M⁻ to Pd, a d¹⁰ metal, because the symmetry of their HOMO orbital is different. The back-side attack S_N2 pathway proceeds via typical Walden-inversion transition state that connects to pre- and post-reaction complexes. For X = Cl/Br/I, the invS_N2-TS’s are, in general, submerged. The shape of this M⁻ + CH₃X S_N2 PES is flatter as compared to that of a main-group base like F⁻ + CH₃X, whose PES has a double-well shape. When X = Br/I, a linear halogen-bonded complex [CH₃−X∙··M]⁻ can be formed as an intermediate upon the front-side attachment of M on the halogen atom X, and it either dissociates to CH₃ + MX⁻ through halogen abstraction or bends the C-X-M angle to continue the back-side S_N2 path. Natural bond orbital analysis shows a polar covalent M−X bond is formed within oxidative insertion complex [CH₃–M–X]⁻, whereas a noncovalent M–X halogen-bond interaction exists for the [CH₃–X∙··M]⁻ complex. This work explores competing channels of the M⁻ + CH₃X reaction in the gas phase and the potential energy surface is useful in understanding the dynamic behavior of the title and analogous reactions. Full article

(This article belongs to the Special Issue Chemical Bonding and Valency: A Special Issue Celebrating the 80th Birthday of Prof. Frank Weinhold)

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18 pages, 19616 KiB

Open AccessArticle

Integrated Metabolomic and Transcriptomic Analysis Reveals Differential Mechanism of Flavonoid Biosynthesis in Two Cultivars of Angelica sinensis

by Tiantian Zhu, Minghui Zhang, Hongyan Su, Meiling Li, Yuanyuan Wang, Ling Jin and Mengfei Li

Molecules 2022, 27(1), 306; https://doi.org/10.3390/molecules27010306 - 04 Jan 2022

Cited by 14 | Viewed by 2664

Abstract

Angelica sinensis is a traditional Chinese medicinal plant that has been primarily used as a blood tonic. It largely relies on its bioactive metabolites, which include ferulic acid, volatile oils, polysaccharides and flavonoids. In order to improve the yield and quality of A. [...] Read more.

Angelica sinensis is a traditional Chinese medicinal plant that has been primarily used as a blood tonic. It largely relies on its bioactive metabolites, which include ferulic acid, volatile oils, polysaccharides and flavonoids. In order to improve the yield and quality of A. sinensis, the two cultivars Mingui 1 (M1), with a purple stem, and Mingui 2 (M2), with a green stem, have been selected in the field. Although a higher root yield and ferulic acid content in M1 than M2 has been observed, the differences of flavonoid biosynthesis and stem-color formation are still limited. In this study, the contents of flavonoids and anthocyanins were determined by spectrophotometer, the differences of flavonoids and transcripts in M1 and M2 were conducted by metabolomic and transcriptomic analysis, and the expression level of candidate genes was validated by qRT-PCR. The results showed that the contents of flavonoids and anthocyanins were 1.5- and 2.6-fold greater in M1 than M2, respectively. A total of 26 differentially accumulated flavonoids (DAFs) with 19 up-regulated (UR) and seven down-regulated (DR) were obtained from the 131 identified flavonoids (e.g., flavonols, flavonoid, isoflavones, and anthocyanins) in M1 vs. M2. A total 2210 differentially expressed genes (DEGs) were obtained from the 34,528 full-length isoforms in M1 vs. M2, and 29 DEGs with 24 UR and 5 DR were identified to be involved in flavonoid biosynthesis, with 25 genes (e.g., CHS1, CHI3, F3H, DFR, ANS, CYPs and UGTs) mapped on the flavonoid biosynthetic pathway and four genes (e.g., RL1, RL6, MYB90 and MYB114) belonging to transcription factors. The differential accumulation level of flavonoids is coherent with the expression level of candidate genes. Finally, the network of DAFs regulated by DEGs was proposed. These findings will provide references for flavonoid production and cultivars selection of A. sinensis. Full article

(This article belongs to the Special Issue Plant Secondary Metabolites with Health Effects: Discovery and Engineering)

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17 pages, 2528 KiB

Open AccessArticle

Quinolizidine-Based Variations and Antifungal Activity of Eight Lupinus Species Grown under Greenhouse Conditions

by Willy Cely-Veloza, Diego Quiroga and Ericsson Coy-Barrera

Molecules 2022, 27(1), 305; https://doi.org/10.3390/molecules27010305 - 04 Jan 2022

Cited by 10 | Viewed by 2232

Abstract

Fusarium oxysporum is an aggressive phytopathogen that affects various plant species, resulting in extensive local and global economic losses. Therefore, the search for competent alternatives is a constant pursuit. Quinolizidine alkaloids (QA) are naturally occurring compounds with diverse biological activities. The structural diversity [...] Read more.

Fusarium oxysporum is an aggressive phytopathogen that affects various plant species, resulting in extensive local and global economic losses. Therefore, the search for competent alternatives is a constant pursuit. Quinolizidine alkaloids (QA) are naturally occurring compounds with diverse biological activities. The structural diversity of quinolizidines is mainly contributed by species of the family Fabaceae, particularly the genus Lupinus. This quinolizidine-based chemo diversity can be explored to find antifungals and even mixtures to address concomitant effects on F. oxysporum. Thus, the antifungal activity of quinolizidine-rich extracts (QREs) from the leaves of eight greenhouse-propagated Lupinus species was evaluated to outline promising QA mixtures against F. oxysporum. Thirteen main compounds were identified and quantified using an external standard. Quantitative analysis revealed different contents per quinolizidine depending on the Lupinus plant, ranging from 0.003 to 32.8 mg/g fresh leaves. Bioautography showed that all extracts were active at the maximum concentration (5 µg/µL). They also exhibited >50% mycelium growth inhibition. All QREs were fungistatic except for the fungicidal QRE of L. polyphyllus Lindl. Angustifoline, matrine, 13α-hydroxylupanine, and 17-oxolupanine were ranked to act jointly against the phytopathogen. Our findings constitute reference information to better understand the antifungal activity of naturally afforded QA mixtures from these globally important plants. Full article

(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)

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17 pages, 10990 KiB

Open AccessArticle

Acid-Catalyzed Liquefaction of Biomasses from Poplar Clones for Short Rotation Coppice Cultivations

by Ivo Paulo, Luis Costa, Abel Rodrigues, Sofia Orišková, Sandro Matos, Diogo Gonçalves, Ana Raquel Gonçalves, Luciana Silva, Salomé Vieira, João Carlos Bordado and Rui Galhano dos Santos

Molecules 2022, 27(1), 304; https://doi.org/10.3390/molecules27010304 - 04 Jan 2022

Cited by 6 | Viewed by 1974

Abstract

Liquefaction of biomass delivers a liquid bio-oil with relevant chemical and energetic applications. In this study we coupled it with short rotation coppice (SRC) intensively managed poplar cultivations aimed at biomass production while safeguarding environmental principles of soil quality and biodiversity. We carried [...] Read more.

Liquefaction of biomass delivers a liquid bio-oil with relevant chemical and energetic applications. In this study we coupled it with short rotation coppice (SRC) intensively managed poplar cultivations aimed at biomass production while safeguarding environmental principles of soil quality and biodiversity. We carried out acid-catalyzed liquefaction, at 160 °C and atmospheric pressure, with eight poplar clones from SRC cultivations. The bio-oil yields were high, ranging between 70.7 and 81.5%. Average gains of bio-oil, by comparison of raw biomasses, in elementary carbon and hydrogen and high heating, were 25.6, 67, and 74%, respectively. Loss of oxygen and O/C ratios averaged 38 and 51%, respectively. Amounts of elementary carbon, oxygen, and hydrogen in bio-oil were 65, 26, and 8.7%, and HHV averaged 30.5 MJkg⁻¹. Correlation analysis showed the interrelation between elementary carbon with HHV in bio-oil or with oxygen loss. Overall, from 55 correlations, 21 significant and high correlations among a set of 11 variables were found. Among the most relevant ones, the percentage of elementary carbon presented five significant correlations with the percentage of O (−0.980), percentage of C gain (0.902), percentage of O loss (0.973), HHV gain (0.917), and O/C loss (0.943). The amount of carbon is directly correlated with the amount of oxygen, conversely, the decrease in oxygen content increases the elementary carbon and hydrogen concentration, which leads to an improvement in HHV. HHV gain showed a strong positive dependence on the percentage of C (0.917) and percentage of C gain (0.943), while the elementary oxygen (−0.885) and its percentage of O loss (0.978) adversely affect the HHV gain. Consequently, the O/C loss (0.970) increases the HHV positively. van Krevelen’s analysis indicated that bio-oils are chemically compatible with liquid fossil fuels. FTIR-ATR evidenced the presence of derivatives of depolymerization of lignin and cellulose in raw biomasses in bio-oil. TGA/DTG confirmed the bio-oil burning aptitude by the high average 53% mass loss of volatiles associated with lowered peaking decomposition temperatures by 100 °C than raw biomasses. Overall, this research shows the potential of bio-oil from liquefaction of SRC biomasses for the contribution of renewable energy and chemical deliverables, and thereby, to a greener global economy. Full article

(This article belongs to the Special Issue Sustainable Development and Application of Renewable Chemicals from Biomass and Waste)

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10 pages, 2238 KiB

Open AccessArticle

Spray Deposition Synthesis of Locally Ordered Mesoporous Polycrystalline Titania Films at Low Temperature

by Gunnar Símonarson, Antiope Lotsari and Anders E. C. Palmqvist

Molecules 2022, 27(1), 303; https://doi.org/10.3390/molecules27010303 - 04 Jan 2022

Cited by 1 | Viewed by 1425

Abstract

A low-temperature spray deposition synthesis was developed to prepare locally hexagonally ordered mesoporous titania films with polycrystalline anatase pore walls in an evaporation-induced self-assembly process. The titania film preparation procedure is conducted completely at temperatures below 50 °C. The effects of spray time, [...] Read more.

A low-temperature spray deposition synthesis was developed to prepare locally hexagonally ordered mesoporous titania films with polycrystalline anatase pore walls in an evaporation-induced self-assembly process. The titania film preparation procedure is conducted completely at temperatures below 50 °C. The effects of spray time, film thickness, synthesis time prior to spray deposition, and aging time at high relative humidity after deposition on the atomic arrangement and the mesoorder of the mesoporous titania were studied. We find the crystallite size to depend on both the synthesis time and aging time of the films, where longer times result in larger crystallites. Using the photocatalytic activity of titania, the structure-directing agent is removed with UV radiation at 43–46 °C. The capability of the prepared films to remove the polymer template increased with longer synthesis and aging times due to the increased crystallinity, which increases the photocatalytic efficiency of the titania films. However, with increasingly longer times, the crystallites grow too large for the mesoorder of the pores to be maintained. This work shows that a scalable spray coating method can be used to prepare locally ordered mesoporous polycrystalline titania films by judiciously tuning the synthesis parameters. Full article

(This article belongs to the Special Issue Ordered Mesoporous Materials: New Developments in Synthesis, Characterization and Applications)

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14 pages, 667 KiB

Open AccessArticle

Ab Initio Study of Fine and Hyperfine Interactions in Triplet POH

by Luca Bizzocchi, Silvia Alessandrini, Mattia Melosso, Víctor M. Rivilla and Cristina Puzzarini

Molecules 2022, 27(1), 302; https://doi.org/10.3390/molecules27010302 - 04 Jan 2022

Cited by 1 | Viewed by 1853

Abstract

Phosphorous-containing molecules have a great relevance in prebiotic chemistry in view of the fact that phosphorous is a fundamental constituent of biomolecules, such as RNA, DNA, and ATP. Its biogenic importance has led astrochemists to investigate the possibility that P-bearing species could have [...] Read more.

Phosphorous-containing molecules have a great relevance in prebiotic chemistry in view of the fact that phosphorous is a fundamental constituent of biomolecules, such as RNA, DNA, and ATP. Its biogenic importance has led astrochemists to investigate the possibility that P-bearing species could have formed in the interstellar medium (ISM) and subsequently been delivered to early Earth by rocky bodies. However, only two P-bearing molecules have been detected so far in the ISM, with the chemistry of interstellar phosphorous remaining poorly understood. Here, in order to shed further light on P-carriers in space, we report a theoretical spectroscopic characterisation of the rotational spectrum of POH in its

^{3}

A

^{″}

ground electronic state. State-of-the-art coupled-cluster schemes have been employed to derive rotational constants, centrifugal distortion terms, and most of the fine and hyperfine interaction parameters, while the electron spin–spin dipolar coupling has been investigated using the multi-configuration self-consistent-field method. The computed spectroscopic parameters have been used to simulate the appearance of triplet POH rotational and ro-vibrational spectra in different conditions, from cold to warm environments, either in gas-phase experiments or in molecular clouds. Finally, we point out that the predicted hyperfine structures represent a key pattern for the recognition of POH in laboratory and interstellar spectra. Full article

(This article belongs to the Special Issue Reactivity and Properties of Radicals and Radical Ions)

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18 pages, 6092 KiB

Open AccessArticle

Schemes for Single Electron Transistor Based on Double Quantum Dot Islands Utilizing a Graphene Nanoscroll, Carbon Nanotube and Fullerene

by Vahideh Khademhosseini, Daryoosh Dideban, Mohammad Taghi Ahmadi and Hadi Heidari

Molecules 2022, 27(1), 301; https://doi.org/10.3390/molecules27010301 - 04 Jan 2022

Cited by 4 | Viewed by 2404

Abstract

The single electron transistor (SET) is a nanoscale switching device with a simple equivalent circuit. It can work very fast as it is based on the tunneling of single electrons. Its nanostructure contains a quantum dot island whose material impacts on the device [...] Read more.

The single electron transistor (SET) is a nanoscale switching device with a simple equivalent circuit. It can work very fast as it is based on the tunneling of single electrons. Its nanostructure contains a quantum dot island whose material impacts on the device operation. Carbon allotropes such as fullerene (C₆₀), carbon nanotubes (CNTs) and graphene nanoscrolls (GNSs) can be utilized as the quantum dot island in SETs. In this study, multiple quantum dot islands such as GNS-CNT and GNS-C₆₀ are utilized in SET devices. The currents of two counterpart devices are modeled and analyzed. The impacts of important parameters such as temperature and applied gate voltage on the current of two SETs are investigated using proposed mathematical models. Moreover, the impacts of CNT length, fullerene diameter, GNS length, and GNS spiral length and number of turns on the SET’s current are explored. Additionally, the Coulomb blockade ranges (CB) of the two SETs are compared. The results reveal that the GNS-CNT SET has a lower Coulomb blockade range and a higher current than the GNS-C₆₀ SET. Their charge stability diagrams indicate that the GNS-CNT SET has smaller Coulomb diamond areas, zero-current regions, and zero-conductance regions than the GNS-C₆₀ SET. Full article

(This article belongs to the Special Issue Fullerenes, Graphenes and Carbon Nanotubes Nanocomposites)

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Molecules, Volume 27, Issue 1 (January-1 2022) – 330 articles

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