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Molecules, Volume 25, Issue 19 (October-1 2020) – 239 articles

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Cover Story (view full-size image) This work focuses on the synthesis of a novel Bi(III)-Cu(II) aminohydroximate complex (derived from [...] Read more.
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Open AccessArticle
Magnolol Enhances the Therapeutic Effects of TRAIL through DR5 Upregulation and Downregulation of c-FLIP and Mcl-1 Proteins in Cancer Cells
Molecules 2020, 25(19), 4591; https://doi.org/10.3390/molecules25194591 - 08 Oct 2020
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Abstract
Magnolol is a biologically active compound, isolated from the Chinese herb Magnolia, that regulates antiproliferative, anticancer, antiangiogenic and antimetastatic activities. We found that magnolol sensitizes TRAIL-induced apoptotic cell death via upregulation of DR5 and downregulation of cellular FLICE-inhibitory protein (c-FLIP) and Mcl-1 [...] Read more.
Magnolol is a biologically active compound, isolated from the Chinese herb Magnolia, that regulates antiproliferative, anticancer, antiangiogenic and antimetastatic activities. We found that magnolol sensitizes TRAIL-induced apoptotic cell death via upregulation of DR5 and downregulation of cellular FLICE-inhibitory protein (c-FLIP) and Mcl-1 in cancer cells, but not in normal cells. Mechanistically, magnolol increased ATF4-dependent DR5 expression at the transcription level, and knockdown of ATF4 markedly inhibited magnolol-induced DR5 upregulation. Silencing DR5 with siRNA prevented combined treatment with magnolol and TRAIL-induced apoptosis and PARP cleavage. Magnolol induced proteasome-mediated Mcl-1 downregulation, while magnolol-induced c-FLIP downregulation was regulated, at least in part, by lysosomal degradation. Our results revealed that magnolol enhanced TRAIL-induced apoptosis via ATF4-dependent DR5 upregulation and downregulation of c-FLIP and Mcl-1 proteins. Full article
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Open AccessArticle
Aromadendrin Inhibits T Cell Activation via Regulation of Calcium Influx and NFAT Activity
Molecules 2020, 25(19), 4590; https://doi.org/10.3390/molecules25194590 - 08 Oct 2020
Viewed by 310
Abstract
The objective of this study was to assess the inhibitory effect of the flavonoid aromadendrin on T cell activity to identify a non-cytotoxic immunosuppressive reagent. Conventional and qualitative PCR, MTT assays, flow cytometry and Western blotting were used to evaluate the effect of [...] Read more.
The objective of this study was to assess the inhibitory effect of the flavonoid aromadendrin on T cell activity to identify a non-cytotoxic immunosuppressive reagent. Conventional and qualitative PCR, MTT assays, flow cytometry and Western blotting were used to evaluate the effect of aromadendrin on the activity, cell viability and confluency, and proximal signal transduction of activated T cells. Aromadendrin effectively regulated IL-2 and IFNγ production in vitro from activated Jurkat T cells without cytotoxicity. Pre-treatment with aromadendrin also suppressed the expression levels of surface molecules CD69, CD25, and CD40L. Reduced calcium (Ca2+) influx in activated T cells pre-treated with aromadendrin was observed. Western blotting revealed that aromadendrin blocked the dephosphorylation of nuclear factor of activated T (NFAT) cells and its nuclear translocation. Involvement of the NFκB and MAPK pathways in the inhibitory effect of aromadendrin was also demonstrated. Results obtained demonstrated the suppressive effect of aromadendrin on T cell activation by Ca2+ influx regulation through NFAT activity suppression of the activated T cells. Full article
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Open AccessArticle
In Vitro Interaction of AB-FUBINACA with Human Cytochrome P450, UDP-Glucuronosyltransferase Enzymes and Drug Transporters
Molecules 2020, 25(19), 4589; https://doi.org/10.3390/molecules25194589 - 08 Oct 2020
Viewed by 299
Abstract
AB-FUBINACA, a synthetic indazole carboxamide cannabinoid, has been used worldwide as a new psychoactive substance. Because drug abusers take various drugs concomitantly, it is necessary to explore potential AB-FUBINACA-induced drug–drug interactions caused by modulation of drug-metabolizing enzymes and transporters. In this study, the [...] Read more.
AB-FUBINACA, a synthetic indazole carboxamide cannabinoid, has been used worldwide as a new psychoactive substance. Because drug abusers take various drugs concomitantly, it is necessary to explore potential AB-FUBINACA-induced drug–drug interactions caused by modulation of drug-metabolizing enzymes and transporters. In this study, the inhibitory effects of AB-FUBINACA on eight major human cytochrome P450s (CYPs) and six uridine 5′-diphospho-glucuronosyltransferases (UGTs) of human liver microsomes, and on eight clinically important transport activities including organic cation transporters (OCT)1 and OCT2, organic anion transporters (OAT)1 and OAT3, organic anion transporting polypeptide transporters (OATP)1B1 and OATP1B3, P-glycoprotein, and breast cancer resistance protein (BCRP) in transporter-overexpressing cells were investigated. AB-FUBINACA inhibited CYP2B6-mediated bupropion hydroxylation via mixed inhibition with Ki value of 15.0 µM and competitively inhibited CYP2C8-catalyzed amodiaquine N-de-ethylation, CYP2C9-catalyzed diclofenac 4′-hydroxylation, CYP2C19-catalyzed [S]-mephenytoin 4′-hydroxylation, and CYP2D6-catalyzed bufuralol 1′-hydroxylation with Ki values of 19.9, 13.1, 6.3, and 20.8 µM, respectively. AB-FUBINACA inhibited OCT2-mediated MPP+ uptake via mixed inhibition (Ki, 54.2 µM) and competitively inhibited OATP1B1-mediated estrone-3-sulfate uptake (Ki, 94.4 µM). However, AB-FUBINACA did not significantly inhibit CYP1A2, CYP2A6, CYP3A4, UGT1A1, UGT1A3, UGT1A4, UGT1A6, or UGT2B7 enzyme activities at concentrations up to 100 µM. AB-FUBINACA did not significantly inhibit the transport activities of OCT1, OAT1/3, OATP1B3, P-glycoprotein, or BCRP at concentrations up to 250 μM. As the pharmacokinetics of AB-FUBINACA in humans and animals remain unknown, it is necessary to clinically evaluate potential in vivo pharmacokinetic drug–drug interactions induced by AB-FUBINACA-mediated inhibition of CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, OCT2, and OATP1B1 activities. Full article
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Open AccessArticle
Qualitative and Quantitative Analysis of Ukrainian Iris Species: A Fresh Look on Their Antioxidant Content and Biological Activities
Molecules 2020, 25(19), 4588; https://doi.org/10.3390/molecules25194588 - 08 Oct 2020
Viewed by 390
Abstract
The major groups of antioxidant compounds (isoflavonoids, xanthones, hydroxycinnamic acids) in the rhizome methanol extracts of four Ukrainian Iris sp. (Iris pallida, Iris hungarica, Iris sibirica, and Iris variegata) were qualitatively and quantitatively analyzed using HPLC-DAD and UPLC-MS/MS. [...] Read more.
The major groups of antioxidant compounds (isoflavonoids, xanthones, hydroxycinnamic acids) in the rhizome methanol extracts of four Ukrainian Iris sp. (Iris pallida, Iris hungarica, Iris sibirica, and Iris variegata) were qualitatively and quantitatively analyzed using HPLC-DAD and UPLC-MS/MS. Gallic acid, caffeic acid, mangiferin, tectoridin, irigenin, iristectorigenin B, irisolidone, 5,6-dihydroxy-7,8,3′,5′-tetramethoxyisoflavone, irisolidone-7-O-β-d-glucopyranoside, germanaism B, and nigricin were recognized by comparing their UV/MS spectra, chromatographic retention time (tR) with those of standard reference compounds. I. hungarica and I. variegata showed the highest total amount of phenolic compounds. Germanaism B was the most abundant component in the rhizomes of I. variegata (7.089 ± 0.032 mg/g) and I. hungarica (6.285 ± 0.030 mg/g). The compound analyses showed good calibration curve linearity (r2 > 0.999) and low detection and quantifications limit. These results validated the method for its use in the simultaneous quantitative evaluation of phenolic compounds in the studied Iris sp. I. hungarica and I. variegata rhizomes exhibited antioxidant activity, as demonstrated by the HPLC-ABTS system and NRF2 expression assay and anti-inflammatory activity on respiratory burst in human neutrophils. Moreover, the extracts showed anti-allergic and cytotoxic effects against cancer cells. Anti-coronavirus 229E and lipid formation activities were also evaluated. In summary, potent antioxidant marker compounds were identified in the examined Iris sp. Full article
(This article belongs to the Special Issue Phytotherapy: Medicinal Plants and Natural Products in Healthcare)
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Open AccessArticle
Chemical Composition of 21 Cultivars of Sour Cherry (Prunus cerasus) Fruit Cultivated in Poland
Molecules 2020, 25(19), 4587; https://doi.org/10.3390/molecules25194587 - 08 Oct 2020
Viewed by 302
Abstract
Sour cherry (Prunus cerasus L.) is a very important fruit crop for producers as well as consumers. To obtain information on sour cherry fruit, we determined the sugar and organic acid composition and phenolic compound contents of twenty-one cultivars and genotypes of [...] Read more.
Sour cherry (Prunus cerasus L.) is a very important fruit crop for producers as well as consumers. To obtain information on sour cherry fruit, we determined the sugar and organic acid composition and phenolic compound contents of twenty-one cultivars and genotypes of Prunus cerasus L. by HPLC quantification. Antioxidant capacity was determined by DPPH radical scavenging, reducing power (FRAP) and determination of substances reacting with Folin–Ciocalteu reagent (FCRS). The main organic acids in sour cherries were malic and malonic acids, and the main sugars were glucose and fructose. The highest sugar content was found in the “Lucyna” cultivar and the highest organic acids in “Paraszt Meggy” and “Suda Hardy”. The richest in phenolic compounds were “Wieluń 17”, “Sokówka Nowotomyska”, “Grosenkirch” “Sokówka Nowotomyska” “Grosenkirch” (anthocyanins, flavanols and total phenolics), and “Meteor” (phenolic acids). Flavan 3-ols were not quantified in every cultivar. “Dradem, “Turgieniewka”, “Wróble”, and “Nana” contained the smallest amounts of phenolic compounds. Antioxidant capacity was highly correlated with phenolic compound composition. According to principal component analysis (PCA), it was concluded that cultivars whose harvest maturity was medium to late contained more flavonols and anthocyanins and were characterized by higher antioxidant capacity than those whose harvest maturity was classified as early or early to medium. Full article
(This article belongs to the Special Issue Antioxidant Activity of Natural Compounds)
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Open AccessArticle
Antiproliferative and Antimigration Activities of Beauvericin Isolated from Isaria sp. on Pancreatic Cancer Cells
Molecules 2020, 25(19), 4586; https://doi.org/10.3390/molecules25194586 - 08 Oct 2020
Viewed by 322
Abstract
This study describes the antiproliferative and antimigration effects of beauvericin from a culture broth of Isaria sp. in human pancreatic cancer cells (PANC-1). Activity-guided fractionation of the EtOAc extract of cultured broth of Isaria sp. RD055140 afforded beauvericin (1), a new [...] Read more.
This study describes the antiproliferative and antimigration effects of beauvericin from a culture broth of Isaria sp. in human pancreatic cancer cells (PANC-1). Activity-guided fractionation of the EtOAc extract of cultured broth of Isaria sp. RD055140 afforded beauvericin (1), a new isariotin derivative, 7-O-methylisariotin C (2), together with the known isariotin analogs, TK-57-164A (3) and B (4). As a result of the measurement of the cell viability, 1 inhibited cell growth (IC50 = 4.8 µM) of PANC-1 cells. Furthermore, 1 was found to inhibit the migration activity of PANC-1 cells by upregulating the expression of the E-cadherin gene and reducing N-cadherin and Snail genes in a dose-dependent manner (0.1–1 µM). These activities of 1 had lower concentrations than the cytotoxic activity. These findings suggest that 1 can be used as an anticancer agent against human pancreatic carcinoma. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle
Initial In Vitro and In Vivo Evaluation of a Novel CCK2R Targeting Peptide Analog Labeled with Lutetium-177
Molecules 2020, 25(19), 4585; https://doi.org/10.3390/molecules25194585 - 08 Oct 2020
Viewed by 316
Abstract
Targeting of cholecystokinin-2 receptor (CCK2R) expressing tumors using radiolabeled minigastrin (MG) analogs is hampered by rapid digestion of the linear peptide in vivo. In this study, a new MG analog stabilized against enzymatic degradation was investigated in preclinical studies to characterize the metabolites [...] Read more.
Targeting of cholecystokinin-2 receptor (CCK2R) expressing tumors using radiolabeled minigastrin (MG) analogs is hampered by rapid digestion of the linear peptide in vivo. In this study, a new MG analog stabilized against enzymatic degradation was investigated in preclinical studies to characterize the metabolites formed in vivo. The new MG analog DOTA-DGlu-Pro-Tyr-Gly-Trp-(N-Me)Nle-Asp-1Nal-NH2 comprising site-specific amino acid substitutions in position 2, 6 and 8 and different possible metabolites thereof were synthesized. The receptor interaction of the peptide and selected metabolites was evaluated in a CCK2R-expressing cell line. The enzymatic stability of the 177Lu-labeled peptide analog was evaluated in vitro in different media as well as in BALB/c mice up to 1 h after injection and the metabolites were identified based on radio-HPLC analysis. The new radiopeptide showed a highly increased stability in vivo with >56% intact radiopeptide in the blood of BALB/c mice 1 h after injection. High CCK2R affinity and cell uptake was confirmed only for the intact peptide, whereas enzymatic cleavage within the receptor specific C-terminal amino acid sequence resulted in complete loss of affinity and cell uptake. A favorable biodistribution profile was observed in BALB/c mice with low background activity, preferential renal excretion and prolonged uptake in CCK2R-expressing tissues. The novel stabilized MG analog shows high potential for diagnostic and therapeutic use. The radiometabolites characterized give new insights into the enzymatic degradation in vivo. Full article
(This article belongs to the Special Issue Radiolabeled Compounds for Diagnosis and Treatment of Cancer)
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Open AccessArticle
Synthesis, Biological Evaluation and Stability Studies of Some Novel Aza-Acridine Aminoderivatives
Molecules 2020, 25(19), 4584; https://doi.org/10.3390/molecules25194584 - 08 Oct 2020
Viewed by 367
Abstract
Several new amino-substituted aza-acridine derivatives bearing a basic side chain have been designed and synthesized. The antiproliferative activity of the target compounds has been evaluated against three cancer cell lines—namely HCT-116 (colorectal), the uterine sarcoma MES-SA, and its doxorubicin-resistant variant MES-SA/Dx5. A limited [...] Read more.
Several new amino-substituted aza-acridine derivatives bearing a basic side chain have been designed and synthesized. The antiproliferative activity of the target compounds has been evaluated against three cancer cell lines—namely HCT-116 (colorectal), the uterine sarcoma MES-SA, and its doxorubicin-resistant variant MES-SA/Dx5. A limited number of the new acridines showed marginal cytotoxicity against the tested cell lines; nevertheless, these analogues possessed a similar substitution pattern. The moderate biological activity of these derivatives was attributed to their instability in aqueous media, which has been studied by mass spectrometry and computational chemistry experiments at the density functional level of theory (DFT). Full article
(This article belongs to the Section Bioorganic Chemistry)
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Open AccessArticle
Inhibition of Staphylococcus aureus LC 554891 by Moringa oleifera Seed Extract either Singly or in Combination with Antibiotics
Molecules 2020, 25(19), 4583; https://doi.org/10.3390/molecules25194583 - 07 Oct 2020
Viewed by 444
Abstract
Bacterial outbreaks caused by Staphylococcus aureus (S. aureus) are interesting due to the existence of multidrug resistant (MDR) isolates. Therefore, there is a need to develop novel ways to control such MDR S. aureus. In this study, some natural agents [...] Read more.
Bacterial outbreaks caused by Staphylococcus aureus (S. aureus) are interesting due to the existence of multidrug resistant (MDR) isolates. Therefore, there is a need to develop novel ways to control such MDR S. aureus. In this study, some natural agents such as honey bee (HB), extracts of either Moringa oleifera seeds (MSE), or leaves (MLE) and essential oils of garlic, clove, and moringa were studied for their inhibitory activity against this S. aureus pathogen. About 100 food samples including beef luncheon (n = 25), potato chips (n = 50), and corn flakes (n = 25) were investigated for possible pollution with the S. aureus bacteria. The isolated bacteria suspected to belong S. aureus that grew well onto Baird–Parker agar (Oxoid) and shiny halo zones and positive coagulase reaction were selected and identified by API-Kits; all of them that were approved belong to S. aureus (18 strains). The sensitivity of the obtained 18 S. aureus bacterial strains to 12 antibiotics were evaluated; all of them were resistant to ofloxacin; however, other antibiotics tested showed variable results. Interestingly, the S. aureus No. B3 isolated from beef luncheon was resistant to 10 antibiotics out of 12 ones tested. Multiple antibiotic resistance index (MAR) of this S. aureus strain was about 83.3%. Therefore, its identification was confirmed by sequencing of a 16S rRNA gene which approved a successful biochemical identification carried out by API Kits and such strain was designated S. aureus LC 554891. The genome of such strain appeared to contain mecA gene encoding methicillin resistance; it was found to contain hla, hlb, tsst-1, and finbA that encode α-blood hemolysis, β-blood hemolysis, toxic shock syndrome gene, and fibrinogen-binding protein gene, respectively. In addition, the virulence factors viz. sea; seb; sec encoding enterotoxins were detected in the DNA extracted from S. aureus B3 strain. Aqueous extract of Moringa oleifera seeds (MSE) showed inhibitory activity against S. aureus LC 554891 better than that obtained by tetracycline, essential oils or HB. Minimum inhibitory concentration (MIC) of MSE was 20µg/mL. Instrumental analysis of MSE showed 14 bioactive chemical compounds. Combinations of both MSE and tetracycline showed distinctive inhibitory activity against S. aureus LC 554891 than that obtained by either tetracycline or MSE singly. Full article
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Open AccessReview
Natural Compound-Derived Cytochrome bc1 Complex Inhibitors as Antifungal Agents
Molecules 2020, 25(19), 4582; https://doi.org/10.3390/molecules25194582 - 07 Oct 2020
Viewed by 402
Abstract
The high incidence of fungal pathogens has become a global issue for crop protection. A promising strategy to control fungal plant infections is based on the use of nature-inspired compounds. The cytochrome bc1 complex is an essential component of the cellular respiratory chain [...] Read more.
The high incidence of fungal pathogens has become a global issue for crop protection. A promising strategy to control fungal plant infections is based on the use of nature-inspired compounds. The cytochrome bc1 complex is an essential component of the cellular respiratory chain and is one of the most important fungicidal targets. Natural products have played a crucial role in the discovery of cytochrome bc1 inhibitors, as proven by the development of strobilurins, one of the most important classes of crop-protection agents, over the past two decades. In this review, we summarize advances in the exploration of natural product scaffolds for the design and development of new bc1 complex inhibitors. Particular emphasis is given to molecular modeling-based approaches and structure–activity relationship (SAR) studies performed to improve the stability and increase the potency of natural precursors. The collected results highlight the versatility of natural compounds and provide an insight into the potential development of nature-inspired derivatives as antifungal agents. Full article
(This article belongs to the Special Issue Design of Natural Products Lead Molecules Using Organic Synthesis)
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Open AccessArticle
Chemotaxonomic Monitoring of Genetically Authenticated Amomi Fructus Using High-Performance Liquid Chromatography–Diode Array Detector with Chemometric Analysis
Molecules 2020, 25(19), 4581; https://doi.org/10.3390/molecules25194581 - 07 Oct 2020
Viewed by 318
Abstract
Amomi Fructus is widely used to treat digestive disorders, and Amomum villosum, A. villosum var. xanthioides, and A. longiligulare are permitted medicinally in national pharmacopeias. However, there are a variety of adulterants present in herbal markets owing to their morphological similarities [...] Read more.
Amomi Fructus is widely used to treat digestive disorders, and Amomum villosum, A. villosum var. xanthioides, and A. longiligulare are permitted medicinally in national pharmacopeias. However, there are a variety of adulterants present in herbal markets owing to their morphological similarities to the genuine Amomum species. Forty-two Amomi Fructus samples from various origins were identified using internal transcribed spacer and chloroplast barcoding analyses, and then their chromatographic profiles were compared using chemometric analysis for chemotaxonomic monitoring. Among the Amomi Fructus samples, A. villosum, A. longiligulare, A. ghaticum, and A. microcarpum were confirmed as single Amomum species, whereas a mixture of either these Amomum species or with another Amomum species was observed in 15 samples. Chemotaxonomic monitoring results demonstrated that two medicinal Amomum samples, A. villosum and A. longiligulare, were not clearly distinguished from each other, but were apparently separated from other non-medicinal Amomum adulterants. A. ghaticum and A. microcarpum samples were also chemically different from other samples and formed their own species groups. Amomum species mixtures showed diverse variations of chemical correlations according to constituent Amomum species. Genetic authentication-based chemotaxonomic monitoring methods are helpful in classifying Amomi Fructus samples by their original species and to distinguish genuine Amomum species from the adulterants. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle
Hemocyanin Modification of Chitosan Scaffolds with Calcium Phosphate Phases Increase the Osteoblast/Osteoclast Activity Ratio—A Co-Culture Study
Molecules 2020, 25(19), 4580; https://doi.org/10.3390/molecules25194580 - 07 Oct 2020
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Abstract
The ongoing research on biomaterials that support bone regeneration led to the quest for materials or material modifications that can actively influence the activity or balance of bone tissue cells. The bone biocompatibility of porous chitosan scaffolds was modified in the present study [...] Read more.
The ongoing research on biomaterials that support bone regeneration led to the quest for materials or material modifications that can actively influence the activity or balance of bone tissue cells. The bone biocompatibility of porous chitosan scaffolds was modified in the present study by the addition of calcium phosphates or hemocyanin. The first strategy comprised the incorporation of calcium phosphates into chitosan to create a biomimetic chitosan—mineral phase composite. The second strategy comprised dip-coating of chitosan scaffolds with hemocyanin extracted from crayfish hemolymph. The cytocompatibility was assessed in a mono-culture of human bone marrow stromal cells (hBMSCs) and their differentiation to osteoblasts; in a mono-culture of human monocytes (hMs) and their maturation to osteoclasts; and in a co-culture of hBMSC/osteoblasts—hM/osteoclasts. Mineral incorporation caused an increase in scaffold bioactivity, as shown by reduced calcium concentration in the cell culture medium, delayed differentiation of hBMSCs, and reduced osteoclastic maturation of hMs in mono-culture. Dip-coating with hemocyanin led to increased proliferation of hBMSCs and equivalent osteoclast maturation in mono-culture, while in co-culture, both an inhibitory effect of mineral incorporation on osteoblastogenesis and stimulatory effects of hemocyanin were observed. It was concluded that highly bioactive scaffolds (containing mineral phases) restrain osteoblast and osteoclast development, while hemocyanin coating significantly supports osteoblastogenesis. These influences on the osteoblasts/osteoclasts activity ratio may support scaffold-driven bone healing in the future. Full article
(This article belongs to the Special Issue Chitin and Chitosan: Derivatives and Applications)
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Open AccessArticle
Verbascoside-Rich Abeliophyllum distichum Nakai Leaf Extracts Prevent LPS-Induced Preterm Birth Through Inhibiting the Expression of Proinflammatory Cytokines from Macrophages and the Cell Death of Trophoblasts Induced by TNF-α
Molecules 2020, 25(19), 4579; https://doi.org/10.3390/molecules25194579 - 07 Oct 2020
Viewed by 379
Abstract
Background: Preterm birth is a known leading cause of neonatal mortality and morbidity. The underlying causes of pregnancy-associated complications are numerous, but infection and inflammation are the essential high-risk factors. However, there are no safe and effective preventive drugs that can be [...] Read more.
Background: Preterm birth is a known leading cause of neonatal mortality and morbidity. The underlying causes of pregnancy-associated complications are numerous, but infection and inflammation are the essential high-risk factors. However, there are no safe and effective preventive drugs that can be applied to pregnant women. Objective: The objectives of the study were to investigate a natural product, Abeliophyllum distichum leaf (ADL) extract, to examine the possibility of preventing preterm birth caused by inflammation. Methods: We used a mouse preterm birth model by intraperitoneally injecting lipopolysaccharides (LPS). ELISA, Western blot, real-time PCR and immunofluorescence staining analyses were performed to confirm the anti-inflammatory efficacy and related mechanisms of the ADL extracts. Cytotoxicity and cell death were measured using Cell Counting Kit-8 (CCK-8) analysis and flow cytometer. Results: A daily administration of ADL extract significantly reduced preterm birth, fetal loss, and fetal growth restriction after an intraperitoneal injection of LPS in mice. The ADL extract prevented the LPS-induced expression of TNF-α in maternal serum and amniotic fluid and attenuated the LPS-induced upregulation of placental proinflammatory genes, including IL-1β, IL-6, IL-12p40, and TNF-α and the chemokine gene CXCL-1, CCL-2, CCL3, and CCL-4. LPS-treated THP-1 cell-conditioned medium accelerated trophoblast cell death, and TNF-α played an essential role in this effect. The ADL extract reduced LPS-treated THP-1 cell-conditioned medium-induced trophoblast cell death by inhibiting MAPKs and the NF-κB pathway in macrophages. ADL extract prevented exogenous TNF-α-induced increased trophoblast cell death and decreased cell viability. Conclusions: We have demonstrated that the inhibition of LPS-induced inflammation by ADL extract can prevent preterm birth, fetal loss, and fetal growth restriction. Full article
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Open AccessArticle
Maillard Reaction Intermediates and Related Phytochemicals in Black Garlic Determined by EPR and HPLC Analyses
Molecules 2020, 25(19), 4578; https://doi.org/10.3390/molecules25194578 - 07 Oct 2020
Viewed by 337
Abstract
The Maillard reaction intermediates and related phytochemicals in garlic (Allium sativum L.), which was heated for various lengths of time, using X-band (9 GHz) electron paramagnetic resonance (EPR) and high performance liquid chromatography (HPLC) were investigated. Non-spin-trap and non-destructive EPR detected the [...] Read more.
The Maillard reaction intermediates and related phytochemicals in garlic (Allium sativum L.), which was heated for various lengths of time, using X-band (9 GHz) electron paramagnetic resonance (EPR) and high performance liquid chromatography (HPLC) were investigated. Non-spin-trap and non-destructive EPR detected the total reaction intermediates (radicals). The g-value of the signal was 2.004. The signal with a peak-to-peak linewidth (ΔHpp) was approximately 0.67 milli Tesla (mT). The values of the intermediates are suggestive of organic compounds. The garlic darkened in color with the increasing number of heating days. Melanoidin, responsible for darkening of the garlic, was detected at an absorbance of 400 nm. Analysis of the correlation between the EPR intensity and melanoidin absorbance showed a good correlation coefficient (0.98). In addition, 5-hydroxymethyl furfural (5-HMF) and total phenolic compounds increased with the increasing number of heating days. Moreover, trace amount of Fe3+ was observed in the black garlic by EPR. Non-destructive EPR is a useful method for evaluating not only Maillard reaction intermediates, but also the pigment associated with the reaction processes. Full article
(This article belongs to the Special Issue Measurement of Antioxidant Activity: Advances and Perspectives)
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Open AccessArticle
Topical Application of Aronia melanocarpa Extract Rich in Chlorogenic Acid and Rutin Reduces UVB-Induced Skin Damage via Attenuating Collagen Disruption in Mice
Molecules 2020, 25(19), 4577; https://doi.org/10.3390/molecules25194577 - 07 Oct 2020
Viewed by 197
Abstract
Aronia melanocarpa, a black chokeberry, contains high levels of phenolic acids and polyphenolic flavonoids and displays antioxidative and anti-inflammatory effects. Through high-performance liquid chromatography for extracts from Aronia melanocarpa, we discovered that the extract contained chlorogenic acid and rutin as major [...] Read more.
Aronia melanocarpa, a black chokeberry, contains high levels of phenolic acids and polyphenolic flavonoids and displays antioxidative and anti-inflammatory effects. Through high-performance liquid chromatography for extracts from Aronia melanocarpa, we discovered that the extract contained chlorogenic acid and rutin as major ingredients. In this study, we examined the protective effects of the extract against ultraviolet B- (UVB)-induced photodamage in the dorsal skin of institute of cancer research (ICR) mice. Their dorsal skin was exposed to UVB, thereafter; the extract was topically applied once a day for seven days. Photoprotective properties of the extract in the dorsal skin were investigated by clinical skin severity score for skin injury, hematoxylin and eosin staining for histopathology, Masson’s trichrome staining for collagens. In addition, we examined change in collagen type I and III, and matrix metalloproteinase (MMP)-1 and MMP-3 by immunohistochemistry. In the UVB-exposed mice treated with the extract, UVB-induced epidermal damage was significantly ameliorated, showing that epidermal thickness was moderated. In these mice, immunoreactivities of collagen type I and III were significantly increased, whereas immunoreactivities of MMP-1 and 3 were significantly decreased compared with those in the UVB-exposed mice. These results indicate that treatment with Aronia melanocarpa extract attenuates UV-induced photodamage by attenuating UVB-induced collagen disruption: these findings might be a result of the chlorogenic acid and rutin contained in the extract. Based on the current results, we suggest that Aronia melanocarpa can be a useful material for developing photoprotective adjuvant. Full article
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Open AccessArticle
Essential Oil Compositions of Three Invasive Conyza Species Collected in Vietnam and Their Larvicidal Activities against Aedes aegypti, Aedes albopictus, and Culex quinquefasciatus
Molecules 2020, 25(19), 4576; https://doi.org/10.3390/molecules25194576 - 07 Oct 2020
Viewed by 216
Abstract
Mosquito-borne infectious diseases are a persistent problem in tropical regions of the world, including Southeast Asia. Vector control has relied principally on synthetic insecticides, but these have detrimental environmental effects and there is an increasing demand for plant-based agents to control insect pests. [...] Read more.
Mosquito-borne infectious diseases are a persistent problem in tropical regions of the world, including Southeast Asia. Vector control has relied principally on synthetic insecticides, but these have detrimental environmental effects and there is an increasing demand for plant-based agents to control insect pests. Invasive weedy plant species may be able to serve as readily available sources of essential oils, some of which may be useful as larvicidal agents for control of mosquito populations. We hypothesize that members of the genus Conyza (Asteraceae) may produce essential oils that may have mosquito larvicidal properties. The essential oils from the aerial parts of Conyza bonariensis, C. canadensis, and C. sumatrensis were obtained by hydrodistillation, analyzed by gas chromatography–mass spectrometry, and screened for mosquito larvicidal activity against Aedes aegypti, Ae. albopictus and Culex quinquefasciatus. The essential oils of C. canadensis and C. sumatrensis, both rich in limonene (41.5% and 25.5%, respectively), showed notable larvicidal activities against Ae. aegypti (24-h LC50 = 9.80 and 21.7 μg/mL, respectively) and Ae. albopictus (24-h LC50 = 18.0 and 19.1 μg/mL, respectively). These two Conyza species may, therefore, serve as sources for alternative, environmentally-benign larvicidal control agents. Full article
(This article belongs to the Special Issue Insecticide, Acaricide, Repellent and Antimicrobial Development)
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Open AccessArticle
Electrografting of 4-Carboxybenzenediazonium on Glassy Carbon Electrode: The Effect of Concentration on the Formation of Mono and Multilayers
Molecules 2020, 25(19), 4575; https://doi.org/10.3390/molecules25194575 - 07 Oct 2020
Viewed by 237
Abstract
Grafting of electrodes with diazonium salts using cyclic voltammetry (CV) is a well-established procedure for surface modification. However, little is known about the effect of the concentration of the diazonium salt on the number of layers grafted on the electrode surface. In this [...] Read more.
Grafting of electrodes with diazonium salts using cyclic voltammetry (CV) is a well-established procedure for surface modification. However, little is known about the effect of the concentration of the diazonium salt on the number of layers grafted on the electrode surface. In this work, the impact of concentration on the grafting of 4-carboxybenzenediazonium (4-CBD) onto a glassy carbon electrode (GCE) is elucidated. The number of layers grafted on the GCE was linearly dependent on the concentration of 4-CBD and varied between 0.9 and 4.3 when the concentration was varied between 0.050 and 0.30 mmol/L at 0.10 V.s−1. Characterization of modified glassy carbon surface with X-ray photoelectron spectroscopy (XPS) confirmed the grafting of carboxyphenyl layer on the surface. Grafting with 0.15 mmol/L 4-CBD (1 CV cycle) did not form a detectable amount of carboxyphenyl (CP) moieties at the surface, while a single scan with higher concentration (2.5 mmol/L) or multiple scans (22 cycles) gave detectable signals, indicating formation of multilayers. We also demonstrate the possibility of removing the thin layer grafted on a glassy carbon electrode by applying high oxidation potential +1.40 V. Full article
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Open AccessArticle
A Bibenzyl Component Moscatilin Mitigates Glycation-Mediated Damages in an SH-SY5Y Cell Model of Neurodegenerative Diseases through AMPK Activation and RAGE/NF-κB Pathway Suppression
Molecules 2020, 25(19), 4574; https://doi.org/10.3390/molecules25194574 - 07 Oct 2020
Viewed by 198
Abstract
Moscatilin can protect rat pheochromocytoma cells against methylglyoxal-induced damage. Elimination of the effect of advanced glycation end-products (AGEs) but activation of AMP-activated protein kinase (AMPK) are the potential therapeutic targets for the neurodegenerative diseases. Our study aimed to clarify AMPK signaling’s role in [...] Read more.
Moscatilin can protect rat pheochromocytoma cells against methylglyoxal-induced damage. Elimination of the effect of advanced glycation end-products (AGEs) but activation of AMP-activated protein kinase (AMPK) are the potential therapeutic targets for the neurodegenerative diseases. Our study aimed to clarify AMPK signaling’s role in the beneficial effects of moscatilin on the diabetic/hyperglycemia-associated neurodegenerative disorders. AGEs-induced injury in SH-SY5Y cells was used as an in vitro neurodegenerative model. AGEs stimulation resulted in cellular viability loss and reactive oxygen species production, and mitochondrial membrane potential collapse. It was observed that the cleaved forms of caspase-9, caspase-3, and poly (ADP-ribose) polymerase increased in SH-SY5Y cells following AGEs exposure. AGEs decreased Bcl-2 but increased Bax and p53 expression and nuclear factor kappa-B activation in SH-SY5Y cells. AGEs also attenuated the phosphorylation level of AMPK. These AGEs-induced detrimental effects were ameliorated by moscatilin, which was similar to the actions of metformin. Compound C, an inhibitor of AMPK, abolished the beneficial effects of moscatilin on the regulation of SH-SY5Y cells’ function, indicating the involvement of AMPK. In conclusion, moscatilin offers a promising therapeutic strategy to reduce the neurotoxicity or AMPK dysfunction of AGEs. It provides a potential beneficial effect with AGEs-related neurodegenerative diseases. Full article
(This article belongs to the Special Issue Biological Activities of Natural Products)
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Open AccessArticle
Flavonoid Profiles of Two New Approved Romanian Ocimum Hybrids
Molecules 2020, 25(19), 4573; https://doi.org/10.3390/molecules25194573 - 07 Oct 2020
Viewed by 244
Abstract
Basil (Ocimum spp.) is a traditional herbal medicine abundant in antioxidants such as phenolic compounds. As part of a diet, this herb is proved to have some roles in decreasing the risk of cancer, and in the treatment of inflammation and neurodegenerative [...] Read more.
Basil (Ocimum spp.) is a traditional herbal medicine abundant in antioxidants such as phenolic compounds. As part of a diet, this herb is proved to have some roles in decreasing the risk of cancer, and in the treatment of inflammation and neurodegenerative diseases. This study aims to explore the total phenolic and flavonoid content of two new basil hybrids growing in Romania, namely “Aromat de Buzau” (AB) and “Macedon” (MB). The antioxidant capacity of those two species was also analyzed by DPPH and cyclic voltammetry. Six different flavonoids, such as catechin (+), rutin, hyperoside, naringin, naringenin, and genistein, were separated, identified, and quantified by HPLC–DAD chromatography, for the first time, from romanian basil hybrids. The main flavonoid of the extracts was found to be naringin which is present in the highest amount (26.18 mg/kg) in “Aromat de Buzau” (O. basilicum) methanolic extract. These results suggest that dietary intake of these new hybrids can be a source of antioxidant compounds. Full article
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Open AccessFeature PaperReview
ATP-Binding and Hydrolysis in Inflammasome Activation
Molecules 2020, 25(19), 4572; https://doi.org/10.3390/molecules25194572 - 07 Oct 2020
Viewed by 305
Abstract
The prototypical model for NOD-like receptor (NLR) inflammasome assembly includes nucleotide-dependent activation of the NLR downstream of pathogen- or danger-associated molecular pattern (PAMP or DAMP) recognition, followed by nucleation of hetero-oligomeric platforms that lie upstream of inflammatory responses associated with innate immunity. As [...] Read more.
The prototypical model for NOD-like receptor (NLR) inflammasome assembly includes nucleotide-dependent activation of the NLR downstream of pathogen- or danger-associated molecular pattern (PAMP or DAMP) recognition, followed by nucleation of hetero-oligomeric platforms that lie upstream of inflammatory responses associated with innate immunity. As members of the STAND ATPases, the NLRs are generally thought to share a similar model of ATP-dependent activation and effect. However, recent observations have challenged this paradigm to reveal novel and complex biochemical processes to discern NLRs from other STAND proteins. In this review, we highlight past findings that identify the regulatory importance of conserved ATP-binding and hydrolysis motifs within the nucleotide-binding NACHT domain of NLRs and explore recent breakthroughs that generate connections between NLR protein structure and function. Indeed, newly deposited NLR structures for NLRC4 and NLRP3 have provided unique perspectives on the ATP-dependency of inflammasome activation. Novel molecular dynamic simulations of NLRP3 examined the active site of ADP- and ATP-bound models. The findings support distinctions in nucleotide-binding domain topology with occupancy of ATP or ADP that are in turn disseminated on to the global protein structure. Ultimately, studies continue to reveal how the ATP-binding and hydrolysis properties of NACHT domains in different NLRs integrate with signaling modules and binding partners to control innate immune responses at the molecular level. Full article
(This article belongs to the Special Issue Inflammasome Inhibitors)
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Open AccessArticle
Photoluminescence as a Valuable Tool in the Optical Characterization of Acetaminophen and the Monitoring of Its Photodegradation Reactions
Molecules 2020, 25(19), 4571; https://doi.org/10.3390/molecules25194571 - 07 Oct 2020
Viewed by 190
Abstract
In this work, new evidence for the photodegradation reactions of acetaminophen (AC) is reported by photoluminescence (PL), Raman scattering and FTIR spectroscopy. Under excitation wavelength of 320 nm, AC shows a PL band in the spectral range of 340–550 nm, whose intensity decreases [...] Read more.
In this work, new evidence for the photodegradation reactions of acetaminophen (AC) is reported by photoluminescence (PL), Raman scattering and FTIR spectroscopy. Under excitation wavelength of 320 nm, AC shows a PL band in the spectral range of 340–550 nm, whose intensity decreases by exposure to UV light. The chemical interaction of AC with the NaOH solutions, having the concentration ranging between 0.001 and 0.3 M, induces a gradual enhancement of the photoluminescence excitation (PLE) and PL spectra, when the exposure time of samples at the UV light increases until 140 min, as a result of the formation of p-aminophenol and sodium acetate. This behavior is not influenced by the excipients or other active compounds in pharmaceutical products as demonstrated by PLE and PL studies. Experimental arguments for the obtaining of p-aminophenol and sodium acetate, when AC has interacted with NaOH, are shown by Raman scattering and FTIR spectroscopy. Full article
(This article belongs to the Special Issue Drugs in the Environment—Risks and Solutions)
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Open AccessArticle
Protein-Water and Water-Water Long-Time Relaxations in Protein Hydration Water upon Cooling—A Close Look through Density Correlation Functions
Molecules 2020, 25(19), 4570; https://doi.org/10.3390/molecules25194570 - 07 Oct 2020
Viewed by 152
Abstract
We report results on the translational dynamics of the hydration water of the lysozyme protein upon cooling obtained by means of molecular dynamics simulations. The self van Hove functions and the mean square displacements of hydration water show two different temperature activated relaxation [...] Read more.
We report results on the translational dynamics of the hydration water of the lysozyme protein upon cooling obtained by means of molecular dynamics simulations. The self van Hove functions and the mean square displacements of hydration water show two different temperature activated relaxation mechanisms, determining two dynamic regimes where transient trapping of the molecules is followed by hopping phenomena to allow to the structural relaxations. The two caging and hopping regimes are different in their nature. The low-temperature hopping regime has a time scale of tenths of nanoseconds and a length scale on the order of 2–3 water shells. This is connected to the nearest-neighbours cage effect and restricted to the supercooling, it is absent at high temperature and it is the mechanism to escape from the cage also present in bulk water. The second hopping regime is active at high temperatures, on the nanoseconds time scale and over distances of nanometers. This regime is connected to water displacements driven by the protein motion and it is observed very clearly at high temperatures and for temperatures higher than the protein dynamical transition. Below this temperature, the suppression of protein fluctuations largely increases the time-scale of the protein-related hopping phenomena at least over 100 ns. These protein-related hopping phenomena permit the detection of translational motions of hydration water molecules longly persistent in the hydration shell of the protein. Full article
(This article belongs to the Special Issue Physical Chemistry of Aqueous Solutions and Glass Forming Systems)
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Open AccessArticle
High Reserve in δ-Tocopherol of Peganum harmala Seeds Oil and Antifungal Activity of Oil against Ten Plant Pathogenic Fungi
Molecules 2020, 25(19), 4569; https://doi.org/10.3390/molecules25194569 - 06 Oct 2020
Viewed by 309
Abstract
This investigation included the chemical analysis of Peganum harmala (P. harmala) seed oil and its antifungal properties against 10 fungal species. Seed oils of six populations were analyzed using high performance liquid chromatography (HPLC) and gas chromatograph/mass spectrometry (GC-MS). The HPLC [...] Read more.
This investigation included the chemical analysis of Peganum harmala (P. harmala) seed oil and its antifungal properties against 10 fungal species. Seed oils of six populations were analyzed using high performance liquid chromatography (HPLC) and gas chromatograph/mass spectrometry (GC-MS). The HPLC analysis indicated that P. harmala seed oil exhibited a very high level of tocopherol contents, with values in the range of 2385.66–2722.68 mg/100 g. The most abundant tocopherol isomer was δ-tocopherol (90.39%), followed by γ-tocopherol (8.08%) and α-tocopherol (1.14%). We discovered for the first time the presence of tocotrenols in P. harmala seed oils of the six populations studied. The GC-MS analyses revealed that linoleic acid was the main fatty acid (65.17%), followed by oleic acid (23.12%), palmitic acid (5.36%) and stearic acid (3.08%). We also studied the antifungal activity of seed oil of the Medenine (MD) population on ten fungal pathogens. The antifungal effects differed among pathogens and depended on oil concentrations. Seed oil of the MD population caused a significant decrease in mycelial growth of all fungi tested, with values ranging 31.50–82.11%, except for Alternaria sp., which showed no inhibition. The antifungal activity against the 10 selected fungi can be explained by the richness in tocols of the extracted oil and make P. harmala a promising crop for biological control. Furthermore, the importance of fatty acids and the wide geographic spread in Tunisia of this species make this crop a potential source of renewable energy. Full article
(This article belongs to the collection Herbal Medicine Research)
Open AccessReview
Trypanocidal Essential Oils: A Review
Molecules 2020, 25(19), 4568; https://doi.org/10.3390/molecules25194568 - 06 Oct 2020
Viewed by 324
Abstract
Trypanosomiases are diseases caused by parasitic protozoan trypanosomes of the genus Trypanosoma. In humans, this includes Chagas disease and African trypanosomiasis. There are few therapeutic options, and there is low efficacy to clinical treatment. Therefore, the search for new drugs for the [...] Read more.
Trypanosomiases are diseases caused by parasitic protozoan trypanosomes of the genus Trypanosoma. In humans, this includes Chagas disease and African trypanosomiasis. There are few therapeutic options, and there is low efficacy to clinical treatment. Therefore, the search for new drugs for the trypanosomiasis is urgent. This review describes studies of the trypanocidal properties of essential oils, an important group of natural products widely found in several tropical countries. Seventy-seven plants were selected from literature for the trypanocidal activity of their essential oils. The main chemical constituents and mechanisms of action are also discussed. In vitro and in vivo experimental data show the therapeutic potential of these natural products for the treatment of infections caused by species of Trypanosoma. Full article
(This article belongs to the Special Issue Essential Oils as Antimicrobial and Anti-infectious Agents II)
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Open AccessReview
Recent Techniques in Nutrient Analysis for Food Composition Database
Molecules 2020, 25(19), 4567; https://doi.org/10.3390/molecules25194567 - 06 Oct 2020
Viewed by 330
Abstract
Food composition database (FCD) provides the nutritional composition of foods. Reliable and up-to date FCD is important in many aspects of nutrition, dietetics, health, food science, biodiversity, plant breeding, food industry, trade and food regulation. FCD has been used extensively in nutrition labelling, [...] Read more.
Food composition database (FCD) provides the nutritional composition of foods. Reliable and up-to date FCD is important in many aspects of nutrition, dietetics, health, food science, biodiversity, plant breeding, food industry, trade and food regulation. FCD has been used extensively in nutrition labelling, nutritional analysis, research, regulation, national food and nutrition policy. The choice of method for the analysis of samples for FCD often depends on detection capability, along with ease of use, speed of analysis and low cost. Sample preparation is the most critical stage in analytical method development. Samples can be prepared using numerous techniques; however it should be applicable for a wide range of analytes and sample matrices. There are quite a number of significant improvements on sample preparation techniques in various food matrices for specific analytes highlighted in the literatures. Improvements on the technology used for the analysis of samples by specific instrumentation could provide an alternative to the analyst to choose for their laboratory requirement. This review provides the reader with an overview of recent techniques that can be used for sample preparation and instrumentation for food analysis which can provide wide options to the analysts in providing data to their FCD. Full article
(This article belongs to the Special Issue Recent Advances in Studies of Food and Beverages II)
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Open AccessArticle
Synthesis of Novel Chalcone-Based Phenothiazine Derivatives as Antioxidant and Anticancer Agents
Molecules 2020, 25(19), 4566; https://doi.org/10.3390/molecules25194566 - 06 Oct 2020
Viewed by 384
Abstract
Based on reported results for the potential medicinal impact of phenothiazine core, as well as the chalcone skeleton that is widely present in many natural products, together with their reported bioactivities, the present work was aimed at combining both moieties in one molecular [...] Read more.
Based on reported results for the potential medicinal impact of phenothiazine core, as well as the chalcone skeleton that is widely present in many natural products, together with their reported bioactivities, the present work was aimed at combining both moieties in one molecular skeleton and to synthesize and characterize a novel series of chalone-based phenothiazine derivatives. For this purpose, 2-acetylphenothiazine was N-alkylated, followed by the Claisen-Schmidt reaction to produce the chalcones with good yield. Antioxidant activity, as evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging, was assessed to determine if their antioxidant potential was comparable with ascorbic acid, and attributable to the phenothiazine core. Screening anticancer activities of the synthesized chalone-based phenothiazine derivatives against human breast cancer cell line MCF-7 cells, and human hepatocellular carcinoma HepG-2 cells, compared with standard drugs cisplatin and doxorubicin, was evaluated. The results revealed that compounds 4a, 4b, 4d, 4h, 4j, 4k, 4m, 4o, and 4p were good against human hepatocellular carcinoma HepG-2 cells, and among these compounds 4b and 4k were the most effective compounds, with IC50 values of 7.14 μg/mL and 7.6 1 μg/mL, respectively. On the other hand, compounds 4a, 4b, 4k, and 4m were good against human breast cancer cell line MCF-7 cells and, among these compounds, 4k and 4b were the most effective compounds, with IC50 values of 12 μg/mL and 13. 8 μg/mL, respectively. The overall results suggest that these compounds could, potentially, be further modified for the formation of more potent antioxidant and anticancer agents. Full article
(This article belongs to the Special Issue Recent Advances in Anticancer Drugs II)
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Open AccessArticle
Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)
Molecules 2020, 25(19), 4565; https://doi.org/10.3390/molecules25194565 - 06 Oct 2020
Viewed by 276
Abstract
A novel series of some hydrazones bearing thiazole moiety were generated via solvent-drop grinding of thiazole carbohydrazide 2 with various carbonyl compounds. Also, dehydrative-cyclocondensation of 2 with active methylene compounds or anhydrides gave the respective pyarzole or pyrazine derivatives. The structures of the [...] Read more.
A novel series of some hydrazones bearing thiazole moiety were generated via solvent-drop grinding of thiazole carbohydrazide 2 with various carbonyl compounds. Also, dehydrative-cyclocondensation of 2 with active methylene compounds or anhydrides gave the respective pyarzole or pyrazine derivatives. The structures of the newly synthesized compounds were established based on spectroscopic evidences and their alternative syntheses. Additionally, the anti-viral activity of all the products was tested against SARS-CoV-2 main protease (Mpro) using molecular docking combined with molecular dynamics simulation (MDS). The average binding affinities of the compounds 3a, 3b, and 3c (−8.1 ± 0.33 kcal/mol, −8.0 ± 0.35 kcal/mol, and −8.2 ± 0.21 kcal/mol, respectively) are better than that of the positive control Nelfinavir (−6.9 ± 0.51 kcal/mol). This shows the possibility of these three compounds to effectively bind to SARS-CoV-2 Mpro and hence, contradict the virus lifecycle. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle
Development of Ultra-Performance Liquid Chromatography–Mass Spectrometry Method for Simultaneous Determination of Three Cationic Dyes in Environmental Samples
Molecules 2020, 25(19), 4564; https://doi.org/10.3390/molecules25194564 - 06 Oct 2020
Viewed by 315
Abstract
Lower dye concentrations and the presence of several dyes along with other matrices in environmental samples restrict their determination. Herein, a highly sensitive and rapid ultra-performance tandem mass spectrometric method was developed for simultaneous determination of cationic dyes, namely methylene blue (MB), rhodamine [...] Read more.
Lower dye concentrations and the presence of several dyes along with other matrices in environmental samples restrict their determination. Herein, a highly sensitive and rapid ultra-performance tandem mass spectrometric method was developed for simultaneous determination of cationic dyes, namely methylene blue (MB), rhodamine B (RB) and crystal violet (CV), in environmental samples. To preconcentrate environmental samples, solid-phase extraction cartridges were developed by using hydrogen peroxide modified pistachio shell biomass (MPSB). The surface morphological and chemical functionalities of MPSB were well characterized. The developed method was validated considering different validation parameters. In terms of accuracy and precision, the %RSD for all three dyes at all four concentration points was found to be between 1.26 and 2.76, while the accuracy reported in terms of the recovery was found to be 98.02%-101.70%. The recovery was found to be in the range of 98.11% to 99.55%. The real sample analysis shows that MB, RB, and CV were found in the ranges of 0.39–5.56, 0.32–1.92 and 0.27–4.36 μg/mL, respectively. Full article
(This article belongs to the Special Issue Recent Advances in Dyes Removal Technologies)
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Open AccessArticle
(+)-Erythro8′-7S,8R-dihydroxy-3,3′,5′-trimethoxy-8-O-4′-neolignan, an Anti-Acne Component in Degreasing Myristica fragrans Houtt
Molecules 2020, 25(19), 4563; https://doi.org/10.3390/molecules25194563 - 06 Oct 2020
Viewed by 266
Abstract
Acne is a common skin condition observed in adolescents. Nutmeg (Myristica fragrans Houtt) (MF) is a well-known traditional Chinese medicine; its major toxic components, safrole and myristicin, are rich in essential oils. Essential oils of MF (MFO) were extracted by hydrodistillation; the [...] Read more.
Acne is a common skin condition observed in adolescents. Nutmeg (Myristica fragrans Houtt) (MF) is a well-known traditional Chinese medicine; its major toxic components, safrole and myristicin, are rich in essential oils. Essential oils of MF (MFO) were extracted by hydrodistillation; the residue was extracted using 50% methanol (MFE-M). The minimum inhibitory concentration (MIC) of MFE-M against Cutibacterium acnes and Staphylococcus aureus was 0.64 mg. Four compounds were obtained from MFE-M: myristicin (1), (+)-erythro8′-7S,8R- dihydroxy-3,3,5′-trimethoxy-8-O-4′-neolignan (2), (+)-erythro-Δ8’-7-hydroxy-3,4,3’,5’-tetramethoxy 8-O-4-neolignan (3), and erythro8′-7-acetoxy-3,4,3′,5′-tetramethoxy-8-O-4′-neolignan (4). Compound 2 exerted the strongest antimicrobial activity, with MICs of 6.25 and 3.12 μg/mL against C. acnes and S. aureus, respectively. Moreover, 2 inhibited NO, PGE2, iNOS, and COX-2 levels in RAW 264.7 cells induced by LPS or heat-killed C. acnes; NO production at 50% inhibitory concentrations (IC50) was 11.07 and 11.53 μg/mL, respectively. Myristicin and safrole content was higher in MFO than in MFE-M. MFO and MFE-M caused no skin irritation after a single topical application in Wistar rats. MFE-M, with low safrole and myristicin content, did not cause skin irritation and exhibited an anti-acne effect; moreover, 2 was identified as the active substance. Therefore, MFE-M could be employed to develop anti-acne compounds for use in cosmetics. Full article
(This article belongs to the Special Issue Food and Drug Analysis Ⅱ)
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Open AccessReview
An Insight into the Solid-State Miscibility of Triacylglycerol Crystals
Molecules 2020, 25(19), 4562; https://doi.org/10.3390/molecules25194562 - 06 Oct 2020
Viewed by 248
Abstract
The crystallization properties of triacylglycerols (TAGs) strongly determine the functional properties of natural lipids. The polymorphic and mixing phase behavior of TAG molecules have long been, and still are, a hot topic of research with special relevance for the cosmetic, pharmaceutical, and food [...] Read more.
The crystallization properties of triacylglycerols (TAGs) strongly determine the functional properties of natural lipids. The polymorphic and mixing phase behavior of TAG molecules have long been, and still are, a hot topic of research with special relevance for the cosmetic, pharmaceutical, and food industry. To avoid the difficulties arising from the study of whole real fats, studies at the molecular level on mixtures of a limited number of TAGs has become an indispensable tool to identify the underlying causes of the physical properties in lipid systems. In particular, phase diagrams of binary mixtures of TAGs exhibiting a different degree of heterogeneity (monoacid or mixed fatty acids; molecular symmetry; the presence of cis or trans double bonds) have resulted in a significant breakthrough in our knowledge about structure–interaction–function relationships. The present work aims to provide an overview of the main reports regarding binary and ternary TAG systems, from the early studies to the most recent developments. Full article
(This article belongs to the Special Issue Crystallization of Lipids: From Fundamentals to Applications)
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