Molecules

15 pages, 3488 KiB

Open AccessFeature PaperArticle

Preparation and Compatibilization of PBS/Whey Protein Isolate Based Blends

by Maria-Beatrice Coltelli, Laura Aliotta, Vito Gigante, Maria Bellusci, Patrizia Cinelli, Elodie Bugnicourt, Markus Schmid, Andreas Staebler and Andrea Lazzeri

Molecules 2020, 25(14), 3313; https://doi.org/10.3390/molecules25143313 - 21 Jul 2020

Cited by 12 | Viewed by 4260

Abstract

In this paper the production of biopolymeric blends of poly(butylene succinate) PBS and plasticized whey protein (PWP), obtained from a natural by-product from cheese manufacturing, has been investigated for the production of films and/or sheets. In order to add the highest possible whey [...] Read more.

In this paper the production of biopolymeric blends of poly(butylene succinate) PBS and plasticized whey protein (PWP), obtained from a natural by-product from cheese manufacturing, has been investigated for the production of films and/or sheets. In order to add the highest possible whey protein content, different formulations (from 30 to 50 wt.%) were studied. It was found that by increasing the amount of PWP added to PBS, the mechanical properties were worsened accordingly. This trend was attributed to the low compatibility between PWP and PBS. Consequently, the effect of the addition of soy lecithin and glycerol monostearate (GMS) as compatibilizers was investigated and compared to the use of whey protein modified with oleate and laurate groups obtained by Schotten-Baumann reaction. Soy lecithin and the Schotten-Baumann modified whey were effective in compatibilizing the PWP/PBS blend. In fact, a significant increase in elastic modulus, tensile strength and elongation at break with respect to the not compatibilized blend was observed and the length of aliphatic chains as well as the degree of modification of the Schotten–Baumann proteins affected the results. Moreover, thanks to DSC investigations, these compatibilizers were also found effective in increasing the PBS crystallinity. Full article

(This article belongs to the Special Issue Biobased Biodegradable Polymers)

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20 pages, 3278 KiB

Open AccessArticle

Artificial Intelligence Methods for Constructing Wine Barrels with a Controlled Oxygen Transmission Rate

by Víctor Martínez-Martínez, Ignacio Nevares and Maria del Alamo-Sanza

Molecules 2020, 25(14), 3312; https://doi.org/10.3390/molecules25143312 - 21 Jul 2020

Cited by 2 | Viewed by 2731

Abstract

Oxygen is an important factor in the wine aging process, and the oxygen transmission rate (OTR) is the parameter of the wood that reflects its oxygen permeation. OTR has not been considered in the cooperage industry yet; however, recent studies proposed a nondestructive [...] Read more.

Oxygen is an important factor in the wine aging process, and the oxygen transmission rate (OTR) is the parameter of the wood that reflects its oxygen permeation. OTR has not been considered in the cooperage industry yet; however, recent studies proposed a nondestructive method for estimating the OTR of barrel staves, but an efficient method to combine these staves to build barrels with a desired OTR is needed to implement it in the industry. This article proposes artificial intelligence methods for selecting staves for the construction of barrel heads or bodies with a desired target OTR. Genetic algorithms were used to implement these methods in consideration of the known OTR of the staves and the geometry of the wine barrels. The proposed methods were evaluated in several scenarios: homogenizing the OTR of the actual constructed barrels, constructing low-OTR and high-OTR barrels based on a preclassification of the staves and implementing the proposed method in real cooperage conditions. The results of these experiments suggest the suitability of the proposed methods for their implementation in a cooperage in order to build controlled OTR barrels. Full article

(This article belongs to the Special Issue Alcoholic Beverages Aging Technologies)

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31 pages, 9109 KiB

Open AccessReview

Small Molecules, Non-Covalent Interactions, and Confinement

by Gerd Buntkowsky and Michael Vogel

Molecules 2020, 25(14), 3311; https://doi.org/10.3390/molecules25143311 - 21 Jul 2020

Cited by 31 | Viewed by 4371

Abstract

This review gives an overview of current trends in the investigation of small guest molecules, confined in neat and functionalized mesoporous silica materials by a combination of solid-state NMR and relaxometry with other physico-chemical techniques. The reported guest molecules are water, small alcohols, [...] Read more.

This review gives an overview of current trends in the investigation of small guest molecules, confined in neat and functionalized mesoporous silica materials by a combination of solid-state NMR and relaxometry with other physico-chemical techniques. The reported guest molecules are water, small alcohols, and carbonic acids, small aromatic and heteroaromatic molecules, ionic liquids, and surfactants. They are taken as characteristic role-models, which are representatives for the typical classes of organic molecules. It is shown that this combination delivers unique insights into the structure, arrangement, dynamics, guest-host interactions, and the binding sites in these confined systems, and is probably the most powerful analytical technique to probe these systems. Full article

(This article belongs to the Special Issue Gulliver in the Country of Lilliput: An Interplay of Noncovalent Interactions)

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14 pages, 2399 KiB

Open AccessArticle

Advanced Extraction of Lipids with DHA from Isochrysis galbana with Enzymatic Pre-Treatment Combined with Pressurized Liquids and Ultrasound Assisted Extractions

by María Señoráns, Natalia Castejón and Francisco Javier Señoráns

Molecules 2020, 25(14), 3310; https://doi.org/10.3390/molecules25143310 - 21 Jul 2020

Cited by 26 | Viewed by 3999

Abstract

Microalgal biomass is a sustainable and valuable source of lipids with omega-3 fatty acids. The efficient extraction of lipids from microalgae requires fast and alternative extraction methods, frequently combined with biomass pre-treatment by different procedures. In this work, Pressurized liquid extraction (PLE) was [...] Read more.

Microalgal biomass is a sustainable and valuable source of lipids with omega-3 fatty acids. The efficient extraction of lipids from microalgae requires fast and alternative extraction methods, frequently combined with biomass pre-treatment by different procedures. In this work, Pressurized liquid extraction (PLE) was optimized and compared with traditional lipid extraction methods, Folch and Bligh and Dyer, and with a new Ultrasound Assisted Extraction (UAE) method for lipids from microalgae Isochrysis galbana. To further optimize PLE and UAE, enzymatic pre-treatment of microalga Isochrysis galbana was studied with commercial enzymes Viscozyme and Celluclast. No significant differences were found for lipid yields among different extraction techniques used. However, advanced extraction techniques with or without pre-treatment are a green, fast, and toxic solvent free alternative to traditional techniques. Lipid composition of Isochrysis was determined by HPLC-ELSD and included neutral and polar lipids, showing that each fraction comprised different contents in omega-3 polyunsaturated fatty acids (PUFA). The highest polar lipids content was achieved with UAE (50 °C and 15 min) and PLE (100 °C) techniques. Moreover, the highest omega-3 PUFA (33.2%), eicosapentaenoic acid (EPA) (3.3%) and docosahexaenoic acid (DHA) (12.0%) contents were achieved with the advanced technique UAE, showing the optimized method as a practical alternative to produce valuable lipids for food and nutraceutical applications. Full article

(This article belongs to the Special Issue Microalgae for Production of Bioproducts and Biofuels)

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12 pages, 1024 KiB

Open AccessArticle

Design of Healthy Snack Based on Kiwifruit

by Urszula Tylewicz, Malgorzata Nowacka, Katarzyna Rybak, Kinga Drozdzal, Marco Dalla Rosa and Massimo Mozzon

Molecules 2020, 25(14), 3309; https://doi.org/10.3390/molecules25143309 - 21 Jul 2020

Cited by 34 | Viewed by 5348

Abstract

Kiwifruit is an excellent source of vitamin C and other bioactive compounds, which contribute to its high antioxidant activity. However, the fruits with small size and low weight are considered waste and are unprofitable; therefore, the production of healthy kiwifruit-based dried snacks, which [...] Read more.

Kiwifruit is an excellent source of vitamin C and other bioactive compounds, which contribute to its high antioxidant activity. However, the fruits with small size and low weight are considered waste and are unprofitable; therefore, the production of healthy kiwifruit-based dried snacks, which contain a lot of health-beneficial ingredients, could be a viable alternative for their use. The aim of this study was to develop formulations and methods to produce attractive and nutritionally valuable dried snacks based on yellow kiwifruit. Three different puree formulations (kiwifruit; fennel; and strawberry, lemon, or spinach) with or without addition of sugar were subjected to two drying methods: freeze-drying (fruit bars) and conventional hot air drying (fruit leathers). The obtained products were analysed for their content of total polyphenols (TPs), flavonoids, and vitamin C, as well as their antioxidant activity. The results showed that snacks prepared by freeze-drying (fruit bars) presented higher TP, vitamin C, and flavonoids content than those prepared by convective drying; however, the antioxidant activity did not always follow this trend. The amount of bioactive compounds depended on the formulation used for the preparation of snacks. The effect of the sugar addition seems to be strictly related to the mix used and specific bioactive compound investigated. Full article

(This article belongs to the Special Issue Bioactive Compounds of Fruits, Vegetables and Mushrooms)

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27 pages, 3368 KiB

Open AccessArticle

Synthesis, Characterization, and Biologic Activity of New Acyl Hydrazides and 1,3,4-Oxadiazole Derivatives

by Irina Zarafu, Lilia Matei, Coralia Bleotu, Petre Ionita, Arnaud Tatibouët, Anca Păun, Ioana Nicolau, Anamaria Hanganu, Carmen Limban, Diana Camelia Nuta, Roxana Maria Nemeș, Carmen Cristina Diaconu and Cristiana Radulescu

Molecules 2020, 25(14), 3308; https://doi.org/10.3390/molecules25143308 - 21 Jul 2020

Cited by 16 | Viewed by 4370

Abstract

Starting from isoniazid and carboxylic acids as precursors, thirteen new hydrazides and 1,3,4-oxadiazoles of 2-(4-substituted-phenoxymethyl)-benzoic acids were synthesized and characterized by appropriate means. Their biological properties were evaluated in terms of apoptosis, cell cycle blocking, and drug metabolism gene expression on HCT-8 and [...] Read more.

Starting from isoniazid and carboxylic acids as precursors, thirteen new hydrazides and 1,3,4-oxadiazoles of 2-(4-substituted-phenoxymethyl)-benzoic acids were synthesized and characterized by appropriate means. Their biological properties were evaluated in terms of apoptosis, cell cycle blocking, and drug metabolism gene expression on HCT-8 and HT-29 cell lines. In vitro antimicrobial tests were performed by the microplate Alamar Blue assay for the anti-mycobacterial activities and an adapted agar disk diffusion technique for other non-tubercular bacterial strains. The best antibacterial activity (anti-Mycobacterium tuberculosis effects) was proved by 9. Compounds 7, 8, and 9 determined blocking of G1 phase. Compound 7 proved to be toxic, inducing apoptosis in 54% of cells after 72 h, an effect that can be predicted by the increased expression of mRNA caspases 3 and 7 after 24 h. The influence of compounds on gene expression of enzymes implicated in drug metabolism indicates that synthesized compounds could be metabolized via other pathways than NAT2, spanning adverse effects of isoniazid. Compound 9 had the best antibacterial activity, being used as a disinfectant agent. Compounds 7, 8, and 9, seemed to have antitumor potential. Further studies on the action mechanism of these compounds on the cell cycle may bring new information regarding their biological activity. Full article

(This article belongs to the Section Organic Chemistry)

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17 pages, 4616 KiB

Open AccessFeature PaperArticle

Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation

by Ádám Tajti, Nóra Tóth, Bettina Rávai, István Csontos, Pál Tamás Szabó and Erika Bálint

Molecules 2020, 25(14), 3307; https://doi.org/10.3390/molecules25143307 - 21 Jul 2020

Cited by 14 | Viewed by 3303

Abstract

A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, [...] Read more.

A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, the reaction time and the molar ratio of the starting materials. To evaluate the potential of MW irradiation, comparative thermal experiments were also carried out. In order to obtain “real time” information about the condensation, the special Kabachnik–Fields reaction of 2-formylbenzoic acid, butylamine and diethyl phosphite was monitored by in situ FT-IR spectroscopy. The novel title compounds could be prepared in high yields at low temperature under a short reaction time. A suitable method could also be developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor. Full article

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

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13 pages, 8966 KiB

Open AccessArticle

Structure and Properties of Polylactic Acid Biocomposite Films Reinforced with Cellulose Nanofibrils

by Qianqian Wang, Chencheng Ji, Jianzhong Sun, Qianqian Zhu and Jun Liu

Molecules 2020, 25(14), 3306; https://doi.org/10.3390/molecules25143306 - 21 Jul 2020

Cited by 51 | Viewed by 5082

Abstract

Polylactic acid (PLA) is one of the most promising biodegradable and recyclable thermoplastic biopolymer derived from renewable feedstock. Nanocellulose reinforced PLA biocomposites have received increasing attention in academic and industrial communities. In the present study, cellulose nanofibrils (CNFs) was liberated by combined enzymatic [...] Read more.

Polylactic acid (PLA) is one of the most promising biodegradable and recyclable thermoplastic biopolymer derived from renewable feedstock. Nanocellulose reinforced PLA biocomposites have received increasing attention in academic and industrial communities. In the present study, cellulose nanofibrils (CNFs) was liberated by combined enzymatic pretreatment and high-pressure homogenization, and then subsequently incorporated into the PLA matrix to synthesize PLA/CNF biocomposite films via solution casting and melt compression. The prepared PLA/CNF biocomposite films were characterized in terms of transparency (UV-Vis spectroscopy), chemical structure (attenuated total reflectance-Fourier transform infrared, ATR-FTIR; X-ray powder diffraction, XRD), thermal (thermogravimetric analyzer, TGA; differential scanning calorimetry, DSC), and tensile properties. With 1.0–5.0 wt % additions of CNF to the PLA matrix, noticeable improvements in thermal and physical properties were observed for the resulting PLA/CNF biocomposites. The 2.5 wt % addition of CNF increased the tensile strength by 8.8%. The T_onset (initial degradation temperature) and T_max (maximum degradation temperature) after adding 5.0 wt % CNF was increased by 20 °C, and 10 °C, respectively in the nitrogen atmosphere. These improvements were attributed to the good dispersibility and improved interfacial interaction of CNF in the PLA matrix. Full article

(This article belongs to the Special Issue Cellulose Nanomaterials: Production and Applications)

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19 pages, 685 KiB

Open AccessReview

High Homogenization Pressures to Improve Food Quality, Functionality and Sustainability

by José Mesa, Leidy Indira Hinestroza-Córdoba, Cristina Barrera, Lucía Seguí, Ester Betoret and Noelia Betoret

Molecules 2020, 25(14), 3305; https://doi.org/10.3390/molecules25143305 - 21 Jul 2020

Cited by 48 | Viewed by 5220

Abstract

Interest in high homogenization pressure technology has grown over the years. It is a green technology with low energy consumption that does not generate high CO₂ emissions or polluting effluents. Its main food applications derive from its effect on particle size, causing [...] Read more.

Interest in high homogenization pressure technology has grown over the years. It is a green technology with low energy consumption that does not generate high CO₂ emissions or polluting effluents. Its main food applications derive from its effect on particle size, causing a more homogeneous distribution of fluid elements (particles, globules, droplets, aggregates, etc.) and favoring the release of intracellular components, and from its effect on the structure and configuration of chemical components such as polyphenols and macromolecules such as carbohydrates (fibers) and proteins (also microorganisms and enzymes). The challenges of the 21st century are leading the processed food industry towards the creation of food of high nutritional quality and the use of waste to obtain ingredients with specific properties. For this purpose, soft and nonthermal technologies such as high pressure homogenization have huge potential. The objective of this work is to review how the need to combine safety, functionality and sustainability in the food industry has conditioned the application of high-pressure homogenization technology in the last decade. Full article

(This article belongs to the Special Issue Opportunities and Challenges in High Pressure Processing of Foods)

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9 pages, 2027 KiB

Open AccessArticle

Cassaine Diterpenoid Amide from Stem Bark of Erythrophleum fordii Suppresses Cytotoxic and Induces Apoptosis of Human Leukemia Cells

by Tu Thanh Thi Nguyen, Dao Cuong To, Phuong Hien Thi Vo, Thanh Hoa Tran, Phi Hung Nguyen, Hien Minh Nguyen and Manh Hung Tran

Molecules 2020, 25(14), 3304; https://doi.org/10.3390/molecules25143304 - 21 Jul 2020

Cited by 4 | Viewed by 3040

Abstract

Cassaine diterpenoids amides from the stem bark of Vietnamese Erythrophleum fordii Oliver were screened for their cytotoxic activity against human cancer cells. The cell proliferation assay results showed that, among the active compounds, 3β-acetyl-nor-erythrophlamide (3AEP) exhibited the most potential cytotoxicity against human leukemia [...] Read more.

Cassaine diterpenoids amides from the stem bark of Vietnamese Erythrophleum fordii Oliver were screened for their cytotoxic activity against human cancer cells. The cell proliferation assay results showed that, among the active compounds, 3β-acetyl-nor-erythrophlamide (3AEP) exhibited the most potential cytotoxicity against human leukemia HL-60 and KG cells with IC₅₀ values of 12.0 ± 1.2 and 18.1 ± 2.7 µM, respectively. Treatment of 3AEP resulted in the apoptosis of HL-60 cells via the activation of caspase 3, and poly (ADP-ribose) polymerase (PARP). Molecular docking in silico results showed that the 3AEP can bind to both the procaspase-3 allosteric site and the PARP-1 active site, with binding energies of −7.51 and −9.63 kcal/mol respectively. These results indicated that the stem bark of Vietnamese E. fordii and its cassaine diterpenoid amides may be useful in the apoptosis induction of human leukemia cancer cells. Full article

(This article belongs to the Section Natural Products Chemistry)

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16 pages, 446 KiB

Open AccessReview

One Hundred Faces of Geraniol

by Wanda Mączka, Katarzyna Wińska and Małgorzata Grabarczyk

Molecules 2020, 25(14), 3303; https://doi.org/10.3390/molecules25143303 - 21 Jul 2020

Cited by 102 | Viewed by 9215

Abstract

Geraniol is a monoterpenic alcohol with a pleasant rose-like aroma, known as an important ingredient in many essential oils, and is used commercially as a fragrance compound in cosmetic and household products. However, geraniol has a number of biological activities, such as antioxidant [...] Read more.

Geraniol is a monoterpenic alcohol with a pleasant rose-like aroma, known as an important ingredient in many essential oils, and is used commercially as a fragrance compound in cosmetic and household products. However, geraniol has a number of biological activities, such as antioxidant and anti-inflammatory properties. In addition, numerous in vitro and in vivo studies have shown the activity of geraniol against prostate, bowel, liver, kidney and skin cancer. It can induce apoptosis and increase the expression of proapoptotic proteins. The synergy of this with other drugs may further increase the range of chemotherapeutic agents. The antibacterial activity of this compound was also observed on respiratory pathogens, skin and food-derived strains. This review discusses some of the most important uses of geraniol. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products)

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14 pages, 3312 KiB

Open AccessArticle

Silage Fermentation: A Potential Biological Approach for the Long-Term Preservation and Recycling of Polyphenols and Terpenes in Globe Artichoke (Cynara scolymus L.) By-Products

by Zhuoyan Fan, Kai Chen, Lingyin Ban, Yu Mao, Caiyun Hou and Jingming Li

Molecules 2020, 25(14), 3302; https://doi.org/10.3390/molecules25143302 - 21 Jul 2020

Cited by 11 | Viewed by 3524

Abstract

An economic and effective method for storage is necessary to make full use of the nature of active components in artichoke by-products and ease environmental pressure. In this paper, the potential of silage fermentation for the preservation and recycling of polyphenols and terpenes [...] Read more.

An economic and effective method for storage is necessary to make full use of the nature of active components in artichoke by-products and ease environmental pressure. In this paper, the potential of silage fermentation for the preservation and recycling of polyphenols and terpenes in artichoke by-products is evaluated. The silage of artichoke by-products is characterized by lactic acid bacteria fermentation. Silage distinctly increases the abundance of lactic acid bacteria in artichoke by-products, such as Lactobacillus, Lactococcus, Serratia, and Weissella, and greatly increases the abundance of Firmicutes. The improvement of the microorgan structure and composition is of great significance for the quality of artichoke by-products. Polyphenols in the stems and leaves of artichokes are preserved well in silage. Among the 18 polyphenol compounds detected by high performance liquid chromatography coupled with triple quadrupole tandem mass spectrometry (HPLC-QqQ-MS/MS), the contents of 11 phenolic acids and four flavonoids increased significantly. For terpenes detected by gas chromatography-mass spectrometry (GC-MS), the contents of four pentacyclic triterpenoids increased significantly, while two sterols were kept stable in the silage process. Silage is a potential biotechnology for the long-term preservation of bioactive components, such as polyphenols and terpenes in artichoke by-products, and the results provide a scientific basis for the efficient utilization of by-products. Full article

(This article belongs to the Special Issue Secondary Metabolites in Plant Foods)

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12 pages, 1777 KiB

Open AccessArticle

Properties of Polyhexamethylene Guanidine (PHMG) Associated with Fatal Lung Injury in Korea

by Dong-Uk Park, Jihoon Park, Kee Won Yang, Ju-Hyun Park, Jung-Hwan Kwon and Han Bin Oh

Molecules 2020, 25(14), 3301; https://doi.org/10.3390/molecules25143301 - 21 Jul 2020

Cited by 27 | Viewed by 5258

Abstract

The use of humidifier disinfectant (HD) has been determined to be associated with lung injuries (HDLI) in Korea. Although HD brands containing polyhexamethylene guanidine (PHMG) oligomers have been found to cause more HDLI compared to brands containing other disinfectants, the physicochemical properties of [...] Read more.

The use of humidifier disinfectant (HD) has been determined to be associated with lung injuries (HDLI) in Korea. Although HD brands containing polyhexamethylene guanidine (PHMG) oligomers have been found to cause more HDLI compared to brands containing other disinfectants, the physicochemical properties of PHMG have been poorly defined. We aimed to quantify the PHMG dissolved in HD brands, characterize the number-average (M_n) and weight-average (M_w) molecular masses, and identify the polymerization degree of PHMG. Analysis of the PHMG oligomers was performed using a matrix-assisted laser desorption/ionization time-of-flight mass spectrometer (MALDI-TOF MS) operated in positive-ion reflectron mode. Eight brands of HD containing PHMG were identified. The PHMG concentrations in these brands ranged from 160 to 37,200 ppm (mean = 3100.9 ppm). Concentration was a significant variable among and within HD brands. The degree of PHMG oligomerization fell within the range of two to four. The averages of M_n and M_w were 517.2 g/mol (range: 422–613 g/mol) and 537.3 g/mol (range: 441.0–678.0 g/mol), respectively. Based on the average molecular weight and the degree of polymerization, the PHMG examined here could be regarded as oligomers, which may be associated with the highest proportion of HDLI being caused by PHMG. Full article

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9 pages, 1231 KiB

Open AccessArticle

Alkylated Sesamol Derivatives as Potent Antioxidants

by Ivanete C. Palheta, Lanalice R. Ferreira, Joyce K. L. Vale, Osmarina P. P. Silva, Anderson M. Herculano, Karen R. H. M. Oliveira, Antonio M. J. Chaves Neto, Joaquín M. Campos, Cleydson B. R. Santos and Rosivaldo S. Borges

Molecules 2020, 25(14), 3300; https://doi.org/10.3390/molecules25143300 - 21 Jul 2020

Cited by 8 | Viewed by 2962

Abstract

Sesamol is a phenolic derivative. Its antioxidant activity is low than that of Trolox and depends on benzodioxole moiety. Thus, a molecular modification strategy through alkylation, inspired by natural and synthetic antioxidants, was studied by molecular modeling at the DFT/B3LYP level of theory [...] Read more.

Sesamol is a phenolic derivative. Its antioxidant activity is low than that of Trolox and depends on benzodioxole moiety. Thus, a molecular modification strategy through alkylation, inspired by natural and synthetic antioxidants, was studied by molecular modeling at the DFT/B3LYP level of theory by comparing the 6-31+G(d,p) and 6-311++G(2d,2p) basis sets. All proposed derivatives were compared to classical related antioxidants such as Trolox, t-butylated hydroxytoluene (BHT) and t-butylated hydroxyanisole (BHA). According to our results, molecular orbitals, single electron or hydrogen-atom transfers, spin density distributions, and alkyl substitutions at the ortho positions related to phenol moiety were found to be more effective than any other positions. The trimethylated derivative was more potent than Trolox. t-Butylated derivatives were stronger than all other alkylated derivatives and may be new alternative forms of modified antioxidants from natural products with applications in the chemical, pharmaceutical, and food industries. Full article

(This article belongs to the Special Issue Computational Methods in Drug Design and Food Chemistry)

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26 pages, 3455 KiB

Open AccessArticle

Impact of Grapevine Red Blotch Disease on Cabernet Sauvignon and Merlot Wine Composition and Sensory Attributes

by Raul Cauduro Girardello, Monica L. Cooper, Larry A. Lerno, Charles Brenneman, Sean Eridon, Martina Sokolowsky, Hildegarde Heymann and Anita Oberholster

Molecules 2020, 25(14), 3299; https://doi.org/10.3390/molecules25143299 - 21 Jul 2020

Cited by 21 | Viewed by 4573

Abstract

Grapevine red blotch disease (GRBD) is a recently identified viral disease that affects grapevines. GRBD has been shown to impact grapevine physiology and grape composition by altering specific ripening events. However, no studies have been reported on the impact of GRBD on wine [...] Read more.

Grapevine red blotch disease (GRBD) is a recently identified viral disease that affects grapevines. GRBD has been shown to impact grapevine physiology and grape composition by altering specific ripening events. However, no studies have been reported on the impact of GRBD on wine composition and its sensory attributes. This study evaluated the impact of GRBD on wine primary and secondary metabolites, in addition to its sensory properties, when making wines from Cabernet Sauvignon and Merlot grapes during two seasons. Wines made with GRBD-impacted fruit were lower in ethanol content when compared to wines made with grapes from healthy grapevines. This was attributed to the lower total soluble sugar (TSS) levels of diseased grapes due to delayed ripening at harvest. GRBD impacted wine phenolic composition by decreasing anthocyanin concentrations and increasing flavonol concentrations in some instances. Additionally, proanthocyanidin concentrations were also consistently higher in GRBD wines compared to wines made from healthy fruit. Descriptive analysis demonstrated that GRBD can impact wine style by altering aroma, flavor, and mouthfeel attributes. However, the extent of GRBD impact on wine composition and sensory properties were site and season dependent. Full article

(This article belongs to the Section Natural Products Chemistry)

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14 pages, 9087 KiB

Open AccessArticle

Flavanone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics for Mitochondria-Imaging and Zebrafish-Imaging

by Na Li, Liyan Liu, Huiqing Luo, Huaqiao Wang, Depo Yang and Feng He

Molecules 2020, 25(14), 3298; https://doi.org/10.3390/molecules25143298 - 21 Jul 2020

Cited by 13 | Viewed by 3162

Abstract

Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds [...] Read more.

Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds were readily prepared by the thermal dehydration of chalcone that was obtained by the reaction of o-hydroxyacetophenone and benzaldehyde. Two of these compounds showed significant AIEE characteristics by fluorescence performance experiments, including optical spectra, fluorescence spectra, fluorescence quantum yield (φ_F), fluorescence lifetime, and scanning electron microscopy (SEM). Compared with traditional organic fluorescent dyes, these compounds have high fluorescence emission and high fluorescence quantum yield in solid or aggregated state, which overcomes the shortcoming of aggregation-caused quenching (ACQ). More importantly, the two compounds exhibited low cytotoxicity and good cytocompatibility in A549 lung cells at the experimental concentration range and they specifically targeted mitochondria, which make it of great potential use in mitochondria labeling. In addition, they were embryonic membrane permeable and had different affinities for different tissues and organs of zebrafish, but mainly distributed in the digestive system, providing a basis for the application of such compounds in bioimaging. These AIEE compounds with superior properties could be of great potential use in mitochondria imaging and other in vivo studies. Full article

(This article belongs to the Section Chemical Biology)

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15 pages, 1619 KiB

Open AccessArticle

Microencapsulated Pomegranate Modifies the Composition and Function of High-Density Lipoproteins (HDL) in New Zealand Rabbits

by Alan Dorantes-Morales, Diego Estrada-Luna, Rocío Bautista-Pérez, Gabriel Betanzos-Cabrera, María Luna-Luna, Cristóbal Flores-Castillo, Gilberto Vargas-Alarcón, José Manuel Fragoso, Óscar Pérez-Méndez and Elizabeth Carreón-Torres

Molecules 2020, 25(14), 3297; https://doi.org/10.3390/molecules25143297 - 21 Jul 2020

Cited by 6 | Viewed by 3000

Abstract

Previous studies demonstrated that pomegranate, which is a source of several bioactive molecules, induces modifications of high-density lipoproteins (HDL) lipid composition and functionality. However, it remains unclear whether the beneficial effects of pomegranate are related to improvement in the lipid components of HDL. [...] Read more.

Previous studies demonstrated that pomegranate, which is a source of several bioactive molecules, induces modifications of high-density lipoproteins (HDL) lipid composition and functionality. However, it remains unclear whether the beneficial effects of pomegranate are related to improvement in the lipid components of HDL. Therefore, in this placebo-controlled study, we characterized the size and lipid composition of HDL subclasses and assessed the functionality of these lipoproteins after 30 days of supplementation with a pomegranate microencapsulated (MiPo) in New Zealand white rabbits. We observed a significant decrease in plasma cholesterol, triglycerides, and non−HDL sphingomyelin, as well as increases in HDL cholesterol and HDL phospholipids after supplementation with MiPo. Concomitantly, the triglycerides of the five HDL subclasses isolated by electrophoresis significantly decreased, whereas phospholipids, cholesterol, and sphingomyelin of HDL subclasses, as well as the HDL size distribution remained unchanged. Of particular interest, the triglycerides content of HDL, estimated by the triglycerides-to-phospholipids ratio, decreased significantly after MiPo supplementation. The modification on the lipid content after the supplementation was associated with an increased resistance of HDL to oxidation as determined by the conjugated dienes formation catalyzed by Cu²⁺. Accordingly, paraoxonase-1 (PON1) activity determined with phenylacetate as substrate increased after MiPo. The effect of HDL on endothelial function was analyzed by the response to increasing doses of acetylcholine of aorta rings co-incubated with the lipoproteins in an isolated organ bath. The HDL from rabbits that received placebo partially inhibited the endothelium-dependent vasodilation. In contrast, the negative effect of HDL on endothelial function was reverted by MiPo supplementation. These results show that the beneficial effects of pomegranate are mediated at least in part by improving the functionality of HDL, probably via the reduction of the content of triglycerides in these lipoproteins. Full article

(This article belongs to the Special Issue Bioactives and Functional Ingredients in Foods and Beverages)

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10 pages, 274 KiB

Open AccessArticle

Antimicrobial Potential of Essential Oils from Cerrado Plants against Multidrug−Resistant Foodborne Microorganisms

by Genilson Silva de Jesus, Ana Camila Micheletti, Rafael Gonçalves Padilha, Jessica de Souza de Paula, Flavio Macedo Alves, Cassia Rejane Brito Leal, Fernanda Rodrigues Garcez, Walmir Silva Garcez and Nidia Cristiane Yoshida

Molecules 2020, 25(14), 3296; https://doi.org/10.3390/molecules25143296 - 21 Jul 2020

Cited by 20 | Viewed by 4197

Abstract

Foodborne pathogens are a real public health concern in an escalating antimicrobial resistance scenario. Natural products represent a promising source of bioactive molecules, and essential oils have attracted much attention due to their myriad of biological properties, including antibacterial activities. In this context, [...] Read more.

Foodborne pathogens are a real public health concern in an escalating antimicrobial resistance scenario. Natural products represent a promising source of bioactive molecules, and essential oils have attracted much attention due to their myriad of biological properties, including antibacterial activities. In this context, essential oils obtained from the leaves of Chromolaena squalida, Campomanesia sessiliflora, Myrsine guianensis, Matayba guianensis, Siparuna guianensis, Ocotea minarum and Endlicheria paniculata—species from the Cerrado biome of Midwest Brazil—were extracted and evaluated for their antibacterial activity against a panel of four standard and three clinical multidrug−resistant bacterial strains. All tested oils showed moderate to good activity against at least four bacterial strains, including Salmonella Typhi and oxacillin−resistant Staphylococcus. The essential oils from C. squalida, C. sessiliflora, My. guianensis and Ma. guianensis showed strong inhibition of clinical Staphylococcus strains, which cause bovine mastitis and are related to milk−borne diseases. Their chemical profiles were investigated by gas chromatography coupled to mass spectrometry (GC/MS), which revealed a predominance of mono− and sesquiterpene hydrocarbons, some of which with well−known antimicrobial properties. The essential oil from Cerrado plants proved active against resistant Gram−positive and Gram−negative bacteria, revealing their potentialities for the development of new alternative agents to prevent the spreading of resistant bacterial contamination. Full article

(This article belongs to the Special Issue Essential Oils in Weed Control and Food Preservation)

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14 pages, 17971 KiB

Open AccessArticle

The Spectroscopic Similarity between Breast Cancer Tissues and Lymph Nodes Obtained from Patients with and without Recurrence: A Preliminary Study

by Joanna Depciuch, Agata Stanek-Widera, Nadia Khinevich, Hanna V. Bandarenka, Michal Kandler, Vadim Bayev, Julia Fedotova, Dariusz Lange, Jadwiga Stanek-Tarkowska and Jozef Cebulski

Molecules 2020, 25(14), 3295; https://doi.org/10.3390/molecules25143295 - 21 Jul 2020

Cited by 5 | Viewed by 3068

Abstract

Lymph nodes (LNs) play a very important role in the spread of cancer cells. Moreover, it was noticed that the morphology and chemical composition of the LNs change in the course of cancer development. Therefore, finding and monitoring similarities between these characteristics of [...] Read more.

Lymph nodes (LNs) play a very important role in the spread of cancer cells. Moreover, it was noticed that the morphology and chemical composition of the LNs change in the course of cancer development. Therefore, finding and monitoring similarities between these characteristics of the LNs and tumor tissues are essential to improve diagnostics and therapy of this dreadful disease. In the present study, we used Raman and Fourier transform infrared (FTIR) spectroscopies to compare the chemical composition of the breast cancer tissues and LNs collected from women without (I group-4 patients) and with (II group-4 patients) recurrence. It was shown that the similarity of the chemical composition of the breast tissues and LNs is typical for the II group of the patients. The average Raman spectrum of the breast cancer tissues from the I group was not characterized by vibrations in the 800–1000 cm⁻¹ region originating from collagen and carbohydrates, which are typical for tumor-affected breast tissues. At the same time, this spectrum contains peaks at 1029 cm⁻¹, corresponding to PO²⁻ from DNA, RNA and phospholipids, and 1520 cm⁻¹, which have been observed in normal breast tissues before. It was shown that Raman bands of the average LN spectrum of the II group associated with proteins and carbohydrates are more intensive than those of the breast tissues spectrum. The intensity of the Raman spectra collected from the samples of the II group is almost three times higher compared to the I group. The vibrations of carbohydrates and amide III are much more intensive in the II group’s case. The Raman spectra of the breast cancer tissues and LNs of the II group’s samples do not contain bands (e.g., 1520 cm⁻¹) found in the Raman spectra of the normal breast tissues elsewhere. FTIR spectra of the LNs of the I group’s women showed a lower level of vibrations corresponding to functional group building nucleic acid, collagen, carbohydrates, and proteins in comparison with the breast cancer tissues. Pearson’s correlation test showed positive and more significant interplay between the nature of the breast tissues and LN spectra obtained for the II group of patients than that in the I group’s spectra. Moreover, principal component analysis (PCA) showed that it is possible to distinguish Raman and FTIR spectra of the breast cancer tissues and LNs collected from women without recurrence of the disease. Full article

(This article belongs to the Special Issue A New Diagnosis Tool of Cancer by Spectroscopic Analysis)

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17 pages, 2197 KiB

Open AccessFeature PaperArticle

Molecular Hydrogen as a Lewis Base in Hydrogen Bonds and Other Interactions

by Sławomir J. Grabowski

Molecules 2020, 25(14), 3294; https://doi.org/10.3390/molecules25143294 - 20 Jul 2020

Cited by 10 | Viewed by 3221

Abstract

The second-order Møller–Plesset perturbation theory calculations with the aug-cc-pVTZ basis set were performed for complexes of molecular hydrogen. These complexes are connected by various types of interactions, the hydrogen bonds and halogen bonds are most often represented in the sample of species analysed; [...] Read more.

The second-order Møller–Plesset perturbation theory calculations with the aug-cc-pVTZ basis set were performed for complexes of molecular hydrogen. These complexes are connected by various types of interactions, the hydrogen bonds and halogen bonds are most often represented in the sample of species analysed; most interactions can be classified as σ-hole and π-hole bonds. Different theoretical approaches were applied to describe these interactions: Quantum Theory of ‘Atoms in Molecules’, Natural Bond Orbital method, or the decomposition of the energy of interaction. The energetic, geometrical, and topological parameters are analysed and spectroscopic properties are discussed. The stretching frequency of the H-H bond of molecular hydrogen involved in intermolecular interactions is considered as a parameter expressing the strength of interaction. Full article

(This article belongs to the Special Issue Spectroscopic Aspects of Noncovalent Interactions)

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10 pages, 2550 KiB

Open AccessArticle

Potential Health Benefits of Ropy Exopolysaccharides Produced by Lactobacillus plantarum

by Tülin Yılmaz and Ömer Şimşek

Molecules 2020, 25(14), 3293; https://doi.org/10.3390/molecules25143293 - 20 Jul 2020

Cited by 34 | Viewed by 4020

Abstract

The ability of Lactobacillus plantarum to produce exopolysaccharides (EPS) of various structures and properties is effective in showing both starter and probiotic culture qualification. In this study, the potential health promoting functions of the ropy EPS produced by Lactobacillus plantarum strains isolated from [...] Read more.

The ability of Lactobacillus plantarum to produce exopolysaccharides (EPS) of various structures and properties is effective in showing both starter and probiotic culture qualification. In this study, the potential health promoting functions of the ropy EPS produced by Lactobacillus plantarum strains isolated from tarhana were tested. A stimulation of the pro-inflammatory IL-12 and TNF-α cytokines was observed in the presence of the ropy EPS suggesting an in vitro immune modulation. Similarly, the tested EPS demonstrated promoted the growth of the probiotic strains in fermentation medium. A medium level of radical scavenging activities of ropy EPS was observed whereas the superoxide and hydroxyl scavenging activities were more effective. The ropy EPS also showed α-glucosidase inhibition and cholesterol removal characteristics depending on their concentration. These findings revealed the potential health-promoting functions of ropy EPS from L. plantarum strains and EPS from L. plantarum PFC311 and PFC310 strains demonstrated multiple health-improving effects that can be further evaluated in food and other industries. Full article

(This article belongs to the Special Issue Bioproducts for Health)

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15 pages, 6969 KiB

Open AccessArticle

Caution: Chemical Instability of Natural Biomolecules During Routine Analysis

by Anaïs Pannequin, Erik Laurini, Laurent Giordano, Alain Muselli, Sabrina Pricl and Aura Tintaru

Molecules 2020, 25(14), 3292; https://doi.org/10.3390/molecules25143292 - 20 Jul 2020

Viewed by 3227

Abstract

Natural products (NPs) constitute a significant source of active biomolecules widely used in medicine, pharmacology and cosmetics. However, NPs structural characterization has the drawback of their chemical instability during the extraction steps and their likely transformation during the analytical protocol. In particular, tamariscol [...] Read more.

Natural products (NPs) constitute a significant source of active biomolecules widely used in medicine, pharmacology and cosmetics. However, NPs structural characterization has the drawback of their chemical instability during the extraction steps and their likely transformation during the analytical protocol. In particular, tamariscol and conocephalenol are two compounds largely used in the cosmetic industry for their odorant properties. Thus, in the present study, we focused on the evolution of these two metabolites (extracted from Frullania tamarisci and Conocephalum conicum, respectively), as followed by NMR. Interestingly, we found that, once dissolved in deuterated chloroform, these two tertiary alcohols are both subjected to transformation processes, leading to degradation compounds with altered structures. Accordingly, these detected degradation compounds have been fully characterized by NMR and the experimental findings were supported by computational chemistry data. Full article

(This article belongs to the Special Issue The Applications of Quantitative NMR in Food and Natural Products Science)

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22 pages, 1817 KiB

Open AccessReview

Royal Jelly—A Traditional and Natural Remedy for Postmenopausal Symptoms and Aging-Related Pathologies

by Andreea Bălan, Marius Alexandru Moga, Lorena Dima, Sebastian Toma, Andrea Elena Neculau and Costin Vlad Anastasiu

Molecules 2020, 25(14), 3291; https://doi.org/10.3390/molecules25143291 - 20 Jul 2020

Cited by 33 | Viewed by 10004

Abstract

Women’s life stages are based on their reproductive cycle. This cycle begins with menstruation and ends with menopause. Aging is a natural phenomenon that affects all humans, and it is associated with a decrease in the overall function of the organism. In women, [...] Read more.

Women’s life stages are based on their reproductive cycle. This cycle begins with menstruation and ends with menopause. Aging is a natural phenomenon that affects all humans, and it is associated with a decrease in the overall function of the organism. In women, aging is related with and starts with menopause. Also, during menopause and postmenopausal period, the risk of various age-related diseases and complaints is higher. For this reason, researchers were pushed to find effective remedies that could promote healthy aging and extended lifespan. Apitherapy is a type of alternative medicine that uses natural products from honeybees, such as honey, propolis, royal jelly, etc. Royal jelly is a natural yellowish-white substance, secreted by both hypopharyngeal and mandibular glands of nurse bees, usually used to feed the queen bees and young worker larvae. Over the centuries, this natural product was considered a gold mine for traditional and natural medicine, due to its miraculous effects. Royal jelly has been used for a long time in commercial medical products. It has been demonstrated to possess a wide range of functional properties, such as: antibacterial, anti-inflammatory, vasodilatative, hypotensive, anticancer, estrogen-like, antihypercholesterolemic, and antioxidant activities. This product is usually used to supplement various diseases such as cardiovascular disease, Alzheimer’s disease, sexual dysfunctions, diabetes or cancer. The main objective of this study is to highlight the effectiveness of royal jelly supplementation in relieving menopause symptoms and aging-related diseases. We also aimed to review the most recent research advances regarding the composition of royal jelly for a better understanding of the effects on human health promotion. Full article

(This article belongs to the Special Issue Bee Products: Recent Progress in Health Benefits Studies)

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22 pages, 17069 KiB

Open AccessArticle

Efficient Multicomponent Synthesis of Diverse Antibacterial Embelin-Privileged Structure Conjugates

by Pedro Martín-Acosta, Rosalyn Peña, Gabriela Feresin, Alejandro Tapia, Isabel Lorenzo-Castrillejo, Félix Machín, Ángel Amesty and Ana Estévez-Braun

Molecules 2020, 25(14), 3290; https://doi.org/10.3390/molecules25143290 - 20 Jul 2020

Cited by 3 | Viewed by 3253

Abstract

A library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl₃ as catalyst. This multicomponent reaction implies Knoevenagel condensation, [...] Read more.

A library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl₃ as catalyst. This multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was found how the conjugation of diverse privileged substructure with embelin led to adducts having enhanced antibacterial activities. Full article

(This article belongs to the Special Issue Strategies toward Bioactive Natural Product Like-Compounds)

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16 pages, 1361 KiB

Open AccessArticle

EPA/DHA Concentrate by Urea Complexation Decreases Hyperinsulinemia and Increases Plin5 in the Liver of Mice Fed a High-Fat Diet

by Alejandra Espinosa, Andrés Ross, Gretel Dovale-Rosabal, Francisco Pino-de la Fuente, Ernesto Uribe-Oporto, Camila Sacristán, Paulina Ruiz, Rodrigo Valenzuela, Nalda Romero, Santiago P. Aubourg and Alicia Rodríguez

Molecules 2020, 25(14), 3289; https://doi.org/10.3390/molecules25143289 - 20 Jul 2020

Cited by 8 | Viewed by 3488

Abstract

Dietary intake of eicosapentaenoic/docosahexaenoic acid (EPA/DHA) reduces insulin resistance and hepatic manifestations through the regulation of metabolism in the liver. Obese mice present insulin resistance and lipid accumulation in intracellular lipid droplets (LDs). LD-associated proteins perilipin (Plin) have an essential role in both [...] Read more.

Dietary intake of eicosapentaenoic/docosahexaenoic acid (EPA/DHA) reduces insulin resistance and hepatic manifestations through the regulation of metabolism in the liver. Obese mice present insulin resistance and lipid accumulation in intracellular lipid droplets (LDs). LD-associated proteins perilipin (Plin) have an essential role in both adipogenesis and lipolysis; Plin5 regulates lipolysis and thus contributes to fat oxidation. The purpose of this study was to compare the effects of deodorized refined salmon oil (DSO) and its polyunsaturated fatty acids concentrate (CPUFA) containing EPA and DHA, obtained by complexing with urea, on obesity-induced metabolic alteration. CPUFA maximum content was determined using the Box–Behnken experimental design based on Surface Response Methodology. The optimized CPUFA was administered to high-fat diet (HFD)-fed mice (200 mg/kg/day of EPA + DHA) for 8 weeks. No significant differences (p > 0.05) in cholesterol, glycemia, LDs or transaminase content were found. Fasting insulin and hepatic Plin5 protein level increased in the group supplemented with the EPA + DHA optimized product (38.35 g/100 g total fatty acids) compared to obese mice without fish oil supplementation. The results suggest that processing salmon oil by urea concentration can generate an EPA+DHA dose useful to prevent the increase of fasting insulin and the decrease of Plin5 in the liver of insulin-resistant mice. Full article

(This article belongs to the Special Issue Natural Bioactive Compounds in the Prevention and Treatment of Chronic Diseases)

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45 pages, 4861 KiB

Open AccessReview

Covalent Organic Frameworks in Sample Preparation

by Javier González-Sálamo, Gabriel Jiménez-Skrzypek, Cecilia Ortega-Zamora, Miguel Ángel González-Curbelo and Javier Hernández-Borges

Molecules 2020, 25(14), 3288; https://doi.org/10.3390/molecules25143288 - 20 Jul 2020

Cited by 36 | Viewed by 6691

Abstract

Covalent organic frameworks (COFs) can be classified as emerging porous crystalline polymers with extremely high porosity and surface area size, and good thermal stability. These properties have awakened the interests of many areas, opening new horizons of research and applications. In the Analytical [...] Read more.

Covalent organic frameworks (COFs) can be classified as emerging porous crystalline polymers with extremely high porosity and surface area size, and good thermal stability. These properties have awakened the interests of many areas, opening new horizons of research and applications. In the Analytical Chemistry field, COFs have found an important application in sample preparation approaches since their inherent properties clearly match, in a good number of cases, with the ideal characteristics of any extraction or clean-up sorbent. The review article is meant to provide a detailed overview of the different COFs that have been used up to now for sample preparation (i.e., solid-phase extraction in its most relevant operational modes—conventional, dispersive, magnetic/solid-phase microextraction and stir-bar sorptive extraction); the extraction devices/formats in which they have been applied; and their performances and suitability for this task. Full article

(This article belongs to the Special Issue Nanomaterials Applied to Analytical Chemistry)

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29 pages, 1890 KiB

Open AccessFeature PaperReview

Natural Products as Modulators of Sirtuins

by Berin Karaman Mayack, Wolfgang Sippl and Fidele Ntie-Kang

Molecules 2020, 25(14), 3287; https://doi.org/10.3390/molecules25143287 - 20 Jul 2020

Cited by 40 | Viewed by 6426

Abstract

Natural products have been used for the treatment of human diseases since ancient history. Over time, due to the lack of precise tools and techniques for the separation, purification, and structural elucidation of active constituents in natural resources there has been a decline [...] Read more.

Natural products have been used for the treatment of human diseases since ancient history. Over time, due to the lack of precise tools and techniques for the separation, purification, and structural elucidation of active constituents in natural resources there has been a decline in financial support and efforts in characterization of natural products. Advances in the design of chemical compounds and the understanding of their functions is of pharmacological importance for the biomedical field. However, natural products regained attention as sources of novel drug candidates upon recent developments and progress in technology. Natural compounds were shown to bear an inherent ability to bind to biomacromolecules and cover an unparalleled chemical space in comparison to most libraries used for high-throughput screening. Thus, natural products hold a great potential for the drug discovery of new scaffolds for therapeutic targets such as sirtuins. Sirtuins are Class III histone deacetylases that have been linked to many diseases such as Parkinson`s disease, Alzheimer’s disease, type II diabetes, and cancer linked to aging. In this review, we examine the revitalization of interest in natural products for drug discovery and discuss natural product modulators of sirtuins that could serve as a starting point for the development of isoform selective and highly potent drug-like compounds, as well as the potential application of naturally occurring sirtuin inhibitors in human health and those in clinical trials. Full article

(This article belongs to the Special Issue Structure–Activity Relationships (SAR) of Natural Products)

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14 pages, 18475 KiB

Open AccessArticle

Preparation of Poly(glycidyl methacrylate) (PGMA) and Amine Modified PGMA Adsorbents for Purification of Glucosinolates from Cruciferous Plants

by Li Cheng, Jianpeng Wu, Hao Liang and Qipeng Yuan

Molecules 2020, 25(14), 3286; https://doi.org/10.3390/molecules25143286 - 20 Jul 2020

Cited by 7 | Viewed by 4542

Abstract

Glucosinolates (GLs) are of great interest for their potential as antioxidant and anticancer compounds. In this study, macroporous crosslinked copolymer adsorbents of poly (glycidyl methacrylate) (PGMA) and its amine (ethylenediamine, diethylamine, triethylamine)-modified derivatives were prepared and used to purify the GLS glucoerucin in [...] Read more.

Glucosinolates (GLs) are of great interest for their potential as antioxidant and anticancer compounds. In this study, macroporous crosslinked copolymer adsorbents of poly (glycidyl methacrylate) (PGMA) and its amine (ethylenediamine, diethylamine, triethylamine)-modified derivatives were prepared and used to purify the GLS glucoerucin in a crude extract obtained from a cruciferous plant. These four adsorbents were evaluated by comparing their adsorption/desorption and decolorization performance for the purification of glucoerucin from crude plant extracts. According to the results, the strongly basic triethylamine modified PGMA (PGMA-III) adsorbent showed the best adsorption and desorption capacity of glucoerucin, and its adsorption data was a good fit to the Freundlich isotherm model and pseudo-second-order kinetics; the PGMA adsorbent gave the optimum decolorization performance. Furthermore, dynamic adsorption/desorption experiments were carried out to optimize the purification process. Two glass columns were serially connected and respectively wet-packed with PGMA and PGMA-III adsorbents so that glucoerucin could be decolorized and isolated from crude extracts in one process. Compared with KCl solution, aqueous ammonia was a preferable desorption solvent for the purification of glucoerucin and overcame the challenges of desalination efficiency, residual methanol and high operation costs. The results showed that after desorption with 10% aqueous ammonia, the purity of isolated glucoerucin was 74.39% with a recovery of 80.63%; after decolorization with PGMA adsorbent, the appearance of glucoerucin was improved and the purity increased by 11.30%. The process of using serially connected glass columns, wet-packed with PGMA and PGMA-III, may provide a simple, low-cost, and efficient method for the purification of GLs from cruciferous plants. Full article

(This article belongs to the Collection Porous Materials)

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24 pages, 4528 KiB

Open AccessEditor’s ChoiceReview

Insights into the Properties and Potential Applications of Renewable Carbohydrate-Based Ionic Liquids: A Review

by Bartłomiej Gaida and Alina Brzęczek-Szafran

Molecules 2020, 25(14), 3285; https://doi.org/10.3390/molecules25143285 - 20 Jul 2020

Cited by 38 | Viewed by 5506

Abstract

Carbohydrate-derived ionic liquids have been explored as bio-alternatives to conventional ionic liquids for over a decade. Since their discovery, significant progress has been made regarding synthetic methods, understanding their environmental effect, and developing perspectives on their potential applications. This review discusses the relationships [...] Read more.

Carbohydrate-derived ionic liquids have been explored as bio-alternatives to conventional ionic liquids for over a decade. Since their discovery, significant progress has been made regarding synthetic methods, understanding their environmental effect, and developing perspectives on their potential applications. This review discusses the relationships between the structural properties of carbohydrate ionic liquids and their thermal, toxicological, and biodegradability characteristics in terms of guiding future designs of sugar-rich systems for targeted applications. The synthetic strategies related to carbohydrate-based ionic liquids, the most recent relevant advances, and several perspectives for possible applications spanning catalysis, biomedicine, ecology, biomass, and energy conversion are presented herein. Full article

(This article belongs to the Special Issue Ionic Liquids for Materials and Energy)

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15 pages, 3945 KiB

Open AccessArticle

The Essential Oil of Cymbopogon citratus Stapt and Carvacrol: An Approach of the Antitumor Effect on 7,12-Dimethylbenz-[α]-anthracene (DMBA)-Induced Breast Cancer in Female Rats

by Juan Pedro Rojas-Armas, Jorge Luis Arroyo-Acevedo, Miriam Palomino-Pacheco, Oscar Herrera-Calderón, José Manuel Ortiz-Sánchez, Agustín Rojas-Armas, James Calva, Américo Castro-Luna and Julio Hilario-Vargas

Molecules 2020, 25(14), 3284; https://doi.org/10.3390/molecules25143284 - 20 Jul 2020

Cited by 41 | Viewed by 5606

Abstract

C. citratus essential oil and carvacrol have shown an antitumor effect on breast tumor cell lines; the main objective of this research was to evaluate the antitumor effect of the essential oil of Cymbopogon citratus (EOCc) and carvacrol on 7,12-dimethylbenz [a] anthracene (DMBA)-induced [...] Read more.

C. citratus essential oil and carvacrol have shown an antitumor effect on breast tumor cell lines; the main objective of this research was to evaluate the antitumor effect of the essential oil of Cymbopogon citratus (EOCc) and carvacrol on 7,12-dimethylbenz [a] anthracene (DMBA)-induced breast cancer in female rats. Cancer was induced by a single administration of DMBA at dose of 80 mg/kg body weight (BW). A total of 54 female Holtzman rats were randomly assigned into 9 groups (n = 6). Group I: PS (Physiological saline); Group II: DMBA; Groups III, IV, and V: DMBA + EOCc at doses of 50, 100 and 200 mg/kg/day BW, respectively; Groups VI, VII, and VIII: DMBA + carvacrol at doses of 50, 100 and 200 mg/kg/day BW, respectively; and group IX: DMBA + EOCc + carvacrol at doses of 100 mg/kg/day BW. The treatment lasted 14 weeks. As results, EOCc showed a reduction in tumors as well as necrosis and mitosis. Animals treated with carvacrol did not show necrosis, mitosis, or infiltration. Carvacrol at dose of 100 mg/kg/day BW revealed a significant decrease in the cumulative tumor volume down to 0.11 ± 0.05 cm³ compared to 0.38 ± 0.04 cm³ of the DMBA group (p < 0.01). It is concluded that EOCc and carvacrol had an antitumor effect on DMBA-induced breast cancer in female rats. Full article

(This article belongs to the Special Issue Biological Activities of Natural Products)

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