Pub Date : 2024-10-31DOI: 10.3390/molecules29215154
Anna Spagnoletta, Daniela Valeria Miniero, Nicola Gambacorta, Francesca Oppedisano, Anna De Grassi, Orazio Nicolotti, Ciro Leonardo Pierri, Annalisa De Palma
The 2-oxoglutarate carrier (OGC), pivotal in cellular metabolism, facilitates the exchange of key metabolites between mitochondria and cytosol. This study explores the influence of NADPH on OGC transport activity using proteoliposomes. Experimental data revealed the ability of NADPH to modulate the OGC activity, with a significant increase of 60% at 0.010 mM. Kinetic analysis showed increased Vmax and a reduction in Km for 2-oxoglutarate, suggesting a direct regulatory role. Molecular docking pointed to a specific interaction between NADPH and cytosolic loops of OGC, involving key residues such as K206 and K122. This modulation was unique in mammalian OGC, as no similar effect was observed in a plant OGC structurally/functionally related mitochondrial carrier. These findings propose OGC as a responsive sensor for the mitochondrial redox state, coordinating with the malate/aspartate and isocitrate/oxoglutarate shuttles to maintain redox balance. The results underscore the potential role of OGC in redox homeostasis and its broader implications in cellular metabolism and oxidative stress responses.
{"title":"Modulatory Effect of Nicotinamide Adenine Dinucleotide Phosphate (NADPH) on the 2-Oxoglutarate Mitochondrial Carrier.","authors":"Anna Spagnoletta, Daniela Valeria Miniero, Nicola Gambacorta, Francesca Oppedisano, Anna De Grassi, Orazio Nicolotti, Ciro Leonardo Pierri, Annalisa De Palma","doi":"10.3390/molecules29215154","DOIUrl":"10.3390/molecules29215154","url":null,"abstract":"<p><p>The 2-oxoglutarate carrier (OGC), pivotal in cellular metabolism, facilitates the exchange of key metabolites between mitochondria and cytosol. This study explores the influence of NADPH on OGC transport activity using proteoliposomes. Experimental data revealed the ability of NADPH to modulate the OGC activity, with a significant increase of 60% at 0.010 mM. Kinetic analysis showed increased Vmax and a reduction in Km for 2-oxoglutarate, suggesting a direct regulatory role. Molecular docking pointed to a specific interaction between NADPH and cytosolic loops of OGC, involving key residues such as K206 and K122. This modulation was unique in mammalian OGC, as no similar effect was observed in a plant OGC structurally/functionally related mitochondrial carrier. These findings propose OGC as a responsive sensor for the mitochondrial redox state, coordinating with the malate/aspartate and isocitrate/oxoglutarate shuttles to maintain redox balance. The results underscore the potential role of OGC in redox homeostasis and its broader implications in cellular metabolism and oxidative stress responses.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547764/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-31DOI: 10.3390/molecules29215175
Alcina M M B Morais, Decha Kumla, Valter F R Martins, Ana Alves, Luis Gales, Artur M S Silva, Paulo M Costa, Sharad Mistry, Anake Kijjoa, Rui M S C Morais
Two monoterpenoid lactones, loliolide (1) and epi-loliolide (2), were isolated from the crude dichloromethane extract of a microalga, Thalassiosira sp.). The structures of loliolide (1) and epi-loliolide (2) were elucidated by 1D and 2D NMR analysis, as well as a comparison of their 1H or/and 13C NMR data with those reported in the literature. In the case of loliolide (1), the absolute configurations of its stereogenic carbons were confirmed by X-ray analysis, whereas those of epi-loliolide (2) were determined by NOESY correlations. Loliolide (1) and epi-loliolide (2) were tested for their growth inhibitory activity against two Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) bacteria, as well as one clinical isolate (E. coli SA/2, an extended-spectrum β-lactamase producer-ESBL) and two environmental isolates, S. aureus 74/24, a methicillin-resistant (MRSA), and E. faecalis B3/101, a vancomycin-resistant (VRE) isolates. The results showed that none of the tested compounds exhibited antibacterial activity at the highest concentrations tested (325 μM), and both revealed low antioxidant activity, with ORAC values of 2.786 ± 0.070 and 2.520 ± 0.319 µmol TE/100 mg for loliolide (1) and epi-loliolide (2), respectively.
{"title":"Monoterpene Hydroxy Lactones Isolated from <i>Thalassiosira</i> sp. Microalga and Their Antibacterial and Antioxidant Activities.","authors":"Alcina M M B Morais, Decha Kumla, Valter F R Martins, Ana Alves, Luis Gales, Artur M S Silva, Paulo M Costa, Sharad Mistry, Anake Kijjoa, Rui M S C Morais","doi":"10.3390/molecules29215175","DOIUrl":"10.3390/molecules29215175","url":null,"abstract":"<p><p>Two monoterpenoid lactones, loliolide (<b>1</b>) and <i>epi</i>-loliolide (<b>2</b>), were isolated from the crude dichloromethane extract of a microalga, <i>Thalassiosira</i> sp.). The structures of loliolide (<b>1</b>) and <i>epi</i>-loliolide (<b>2</b>) were elucidated by 1D and 2D NMR analysis, as well as a comparison of their <sup>1</sup>H or/and <sup>13</sup>C NMR data with those reported in the literature. In the case of loliolide (<b>1</b>), the absolute configurations of its stereogenic carbons were confirmed by X-ray analysis, whereas those of <i>epi</i>-loliolide (<b>2</b>) were determined by NOESY correlations. Loliolide (<b>1</b>) and <i>epi</i>-loliolide (<b>2</b>) were tested for their growth inhibitory activity against two Gram-positive (<i>Staphylococcus aureus</i> ATCC 29213, <i>Enterococcus faecalis</i> ATCC 29212) and two Gram-negative (<i>Escherichia coli</i> ATCC 25922, <i>Pseudomonas aeruginosa</i> ATCC 27853) bacteria, as well as one clinical isolate (<i>E. coli</i> SA/2, an extended-spectrum β-lactamase producer-ESBL) and two environmental isolates, <i>S. aureus</i> 74/24, a methicillin-resistant (MRSA), and <i>E. faecalis</i> B3/101, a vancomycin-resistant (VRE) isolates. The results showed that none of the tested compounds exhibited antibacterial activity at the highest concentrations tested (325 μM), and both revealed low antioxidant activity, with ORAC values of 2.786 ± 0.070 and 2.520 ± 0.319 µmol TE/100 mg for loliolide (<b>1</b>) and <i>epi</i>-loliolide (<b>2</b>), respectively.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547300/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624496","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-31DOI: 10.3390/molecules29215159
Nguyen Thi Kim Tuyen, Dong Min Kim, Jung-Woo Lee, Jaehan Jung
3D printing has garnered significant attention across academia and industry due to its capability to design and fabricate complex architectures. Applications such as those requiring intricate geometries or custom designs, including footwear, healthcare, energy storage, and electronics applications, greatly benefit from exploiting 3D printing processes. Despite the recent advancement of structural 3D printing, its use in functional devices remains limited, requiring the need for the development of functional materials suitable for 3D printing in device fabrication. In this review, we briefly introduce various 3D printing techniques, including material extrusion and vat polymerization, and highlight the recent advances in 3D printing for energy and biomedical devices. A summary of future perspectives in this area is also presented. By highlighting recent developments and addressing key challenges, this review aims to inspire future directions in the development of functional devices.
{"title":"Innovative Hybrid Nanocomposites in 3D Printing for Functional Applications: A Review.","authors":"Nguyen Thi Kim Tuyen, Dong Min Kim, Jung-Woo Lee, Jaehan Jung","doi":"10.3390/molecules29215159","DOIUrl":"10.3390/molecules29215159","url":null,"abstract":"<p><p>3D printing has garnered significant attention across academia and industry due to its capability to design and fabricate complex architectures. Applications such as those requiring intricate geometries or custom designs, including footwear, healthcare, energy storage, and electronics applications, greatly benefit from exploiting 3D printing processes. Despite the recent advancement of structural 3D printing, its use in functional devices remains limited, requiring the need for the development of functional materials suitable for 3D printing in device fabrication. In this review, we briefly introduce various 3D printing techniques, including material extrusion and vat polymerization, and highlight the recent advances in 3D printing for energy and biomedical devices. A summary of future perspectives in this area is also presented. By highlighting recent developments and addressing key challenges, this review aims to inspire future directions in the development of functional devices.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547392/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624384","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-31DOI: 10.3390/molecules29215149
Katarzyna Żurawska, Anna Byczek-Wyrostek, Anna Kasprzycka, Krzysztof Walczak
3,4-Dichloro-5-hydroxy-2(5H)-furanone and its dibromo analog are highly reactive molecules. Both are members of the 2(5H)-furanone family, which are important as pharmacophores present in drugs and natural products. Compounds possessing the 2(5H)-furanone skeleton isolated from plants and marine organisms exhibit bioactivity against various microorganisms and viruses and can also be used in other medical treatments. The structures of these 3,4-dihalo-2(5H)-furanones cause their high reactivity due to the presence of a carbonyl group on the C2 carbon conjugated with a double bond and a hydroxyl group on the C5 carbon. Two labile halogen atoms on carbons 3 and 4 offer additional possibilities for the introduction of other substituents. These structural features make 3,4-dihalo-5-hydroxy-2(5H)-furanones versatile reactants in chemical synthesis. In this review, we present methods of 3,4-dihalo-5-hydroxy-2(5H)-furanone synthesis, their applications as substrates in various chemical transformations, and examples of their biologically active derivatives.
{"title":"3,4-Dihalo-5-hydroxy-2(5<i>H</i>)-furanones: Highly Reactive Small Molecules.","authors":"Katarzyna Żurawska, Anna Byczek-Wyrostek, Anna Kasprzycka, Krzysztof Walczak","doi":"10.3390/molecules29215149","DOIUrl":"10.3390/molecules29215149","url":null,"abstract":"<p><p>3,4-Dichloro-5-hydroxy-2(5<i>H</i>)-furanone and its dibromo analog are highly reactive molecules. Both are members of the 2(5<i>H</i>)-furanone family, which are important as pharmacophores present in drugs and natural products. Compounds possessing the 2(5<i>H</i>)-furanone skeleton isolated from plants and marine organisms exhibit bioactivity against various microorganisms and viruses and can also be used in other medical treatments. The structures of these 3,4-dihalo-2(5<i>H</i>)-furanones cause their high reactivity due to the presence of a carbonyl group on the C2 carbon conjugated with a double bond and a hydroxyl group on the C5 carbon. Two labile halogen atoms on carbons 3 and 4 offer additional possibilities for the introduction of other substituents. These structural features make 3,4-dihalo-5-hydroxy-2(5<i>H</i>)-furanones versatile reactants in chemical synthesis. In this review, we present methods of 3,4-dihalo-5-hydroxy-2(5<i>H</i>)-furanone synthesis, their applications as substrates in various chemical transformations, and examples of their biologically active derivatives.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547709/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624396","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Sol-gel spin coating method was employed for depositing TiO2 and Ag-doped TiO2 films. The effects of Ag doping and the annealing temperatures (300-600 °C) were studied with respect to their structural, morphological, vibrational, and optical properties. Field Emission Scanning Electron microscopy (FESEM) investigation exhibited the grained, compact structures of TiO2-based films. Ag incorporation resulted in a rougher film surface. X-ray diffraction (XRD) results confirmed the formation of Ag nanoparticles and AgO phase, along with anatase and rutile TiO2, strongly depending on Ag concentration and technological conditions. AgO fraction diminished after high temperature annealing above 500 °C. The vibrational properties were characterized by Fourier Transform Infrared (FTIR) spectroscopy. It was found that silver presence induced changes in IR bands of TiO2 films. UV-VIS spectroscopy revealed that the embedment of Ag NPs in titania matrix resulted in higher absorbance across the visible spectral range due to local surface plasmon resonance (LSPR). Ag doping reduced the optical band gap of sol-gel TiO2 films. The optical and plasmonic modifications of TiO2:Ag thin films by the number of layers and different technological conditions (thermal and UV treatment) are discussed.
采用溶胶-凝胶旋涂法沉积二氧化钛和掺杂银的二氧化钛薄膜。研究了 Ag 掺杂和退火温度(300-600 °C)对其结构、形态、振动和光学特性的影响。场发射扫描电子显微镜(FESEM)研究表明,基于二氧化钛的薄膜具有颗粒状的紧凑结构。银的加入使薄膜表面更加粗糙。X 射线衍射 (XRD) 结果证实,Ag 纳米颗粒和 AgO 相的形成,以及锐钛型和金红石型 TiO2 的形成,在很大程度上取决于 Ag 浓度和技术条件。在 500 ℃ 以上高温退火后,AgO 部分减少。傅立叶变换红外光谱(FTIR)对振动特性进行了表征。结果发现,银的存在引起了二氧化钛薄膜红外波段的变化。紫外-可见光谱显示,由于局部表面等离子体共振(LSPR)的作用,银纳米粒子嵌入二氧化钛基体后,在可见光谱范围内的吸光度更高。银掺杂降低了溶胶凝胶二氧化钛薄膜的光带隙。讨论了层数和不同技术条件(热处理和紫外线处理)对 TiO2:Ag 薄膜的光学和等离子修饰。
{"title":"Crystallization and Optical Behaviour of Nanocomposite Sol-Gel TiO<sub>2</sub>:Ag Films.","authors":"Tatyana Ivanova, Antoaneta Harizanova, Tatyana Koutzarova, Raphael Closset","doi":"10.3390/molecules29215156","DOIUrl":"10.3390/molecules29215156","url":null,"abstract":"<p><p>Sol-gel spin coating method was employed for depositing TiO<sub>2</sub> and Ag-doped TiO<sub>2</sub> films. The effects of Ag doping and the annealing temperatures (300-600 °C) were studied with respect to their structural, morphological, vibrational, and optical properties. Field Emission Scanning Electron microscopy (FESEM) investigation exhibited the grained, compact structures of TiO<sub>2</sub>-based films. Ag incorporation resulted in a rougher film surface. X-ray diffraction (XRD) results confirmed the formation of Ag nanoparticles and AgO phase, along with anatase and rutile TiO<sub>2</sub>, strongly depending on Ag concentration and technological conditions. AgO fraction diminished after high temperature annealing above 500 °C. The vibrational properties were characterized by Fourier Transform Infrared (FTIR) spectroscopy. It was found that silver presence induced changes in IR bands of TiO<sub>2</sub> films. UV-VIS spectroscopy revealed that the embedment of Ag NPs in titania matrix resulted in higher absorbance across the visible spectral range due to local surface plasmon resonance (LSPR). Ag doping reduced the optical band gap of sol-gel TiO<sub>2</sub> films. The optical and plasmonic modifications of TiO<sub>2</sub>:Ag thin films by the number of layers and different technological conditions (thermal and UV treatment) are discussed.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547583/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142622490","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-31DOI: 10.3390/molecules29215163
Abdelrahman Y Sherif, Ehab M Elzayat, Mohammad A Altamimi
Thermoresponsive self-nanoemulsifying drug delivery systems (T-SNEDDS) offer a promising solution to the limitations of conventional SNEDDS formulations. Liquid SNEDDS are expected to enhance drug solubility; however, they are susceptible to leakage during storage. Even though solid SNEDDS offers a solution to this storage instability, they introduce new challenges, namely increased total dosage and potential for drug trapping within the formulation. The invented T-SNEDDS was used to overcome these limitations and improve the dissolution of glibenclamide (GBC). Solubility and transmittance studies were performed to select a suitable oil and surfactant. Design of Experiments (DoE) software was used to study the impact of propylene glycol and Poloxamer 188 concentrations on measured responses (liquefying temperature, liquefying time, and GBC solubility). The optimized formulation was subjected to an in vitro dissolution study. The optimized T-SNEDDS consisted of Kolliphor EL and Imwitor 308 as surfactants and oil. The optimized propylene glycol and Poloxamer 188 concentrations were 13.7 and 7.9% w/w, respectively. It exhibited a liquefying temperature of 35.0 °C, a liquefying time of 119 s, and a GBC solubility of 5.51 mg/g. In vitro dissolution study showed that optimized T-SNEDDS exhibited 98.8% dissolution efficiency compared with 2.5% for raw drugs. This study presents a promising approach to enhance pharmaceutical applicability by resolving the limitations of traditional SNEDDS.
{"title":"Optimization of Glibenclamide Loaded Thermoresponsive SNEDDS Using Design of Experiment Approach: Paving the Way to Enhance Pharmaceutical Applicability.","authors":"Abdelrahman Y Sherif, Ehab M Elzayat, Mohammad A Altamimi","doi":"10.3390/molecules29215163","DOIUrl":"10.3390/molecules29215163","url":null,"abstract":"<p><p>Thermoresponsive self-nanoemulsifying drug delivery systems (T-SNEDDS) offer a promising solution to the limitations of conventional SNEDDS formulations. Liquid SNEDDS are expected to enhance drug solubility; however, they are susceptible to leakage during storage. Even though solid SNEDDS offers a solution to this storage instability, they introduce new challenges, namely increased total dosage and potential for drug trapping within the formulation. The invented T-SNEDDS was used to overcome these limitations and improve the dissolution of glibenclamide (GBC). Solubility and transmittance studies were performed to select a suitable oil and surfactant. Design of Experiments (DoE) software was used to study the impact of propylene glycol and Poloxamer 188 concentrations on measured responses (liquefying temperature, liquefying time, and GBC solubility). The optimized formulation was subjected to an in vitro dissolution study. The optimized T-SNEDDS consisted of Kolliphor EL and Imwitor 308 as surfactants and oil. The optimized propylene glycol and Poloxamer 188 concentrations were 13.7 and 7.9% <i>w</i>/<i>w</i>, respectively. It exhibited a liquefying temperature of 35.0 °C, a liquefying time of 119 s, and a GBC solubility of 5.51 mg/g. In vitro dissolution study showed that optimized T-SNEDDS exhibited 98.8% dissolution efficiency compared with 2.5% for raw drugs. This study presents a promising approach to enhance pharmaceutical applicability by resolving the limitations of traditional SNEDDS.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547575/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624544","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-31DOI: 10.3390/molecules29215161
Sharmin Sultana, Md Lokman Hossain, Tom Sostaric, Lee Yong Lim, Kevin J Foster, Cornelia Locher
This is the first study to report on high performance thin layer chromatography (HPTLC) generated spectrophotometric data to systematically capture flavonoid compounds using optimized derivatization with either AlCl3 or NaNO2-AlCl3-NaOH as visualisation reagents. While the traditional AlCl3 colorimetric method using UV-Vis analysis provides valuable insights into the presence of flavonoids and allows derivation of the total flavonoid content (TFC) of a sample, HPTLC fingerprints obtained after spraying with AlCl3 or NaNO2-AlCl3-NaOH enable the visualization of the various flavonoids present in a sample based on their respective absorption shifts, thus complementing the traditional TFC assay. In this study, 40 different flavonoids representing different classes (flavonols, flavanolols, flavan-3-ol, flavones, flavanones, and isoflavonoids) were analysed. Upon derivatization with AlCl3 most of the investigated flavonoids recorded bathochromic shifts, yielding characteristic λmax values between 370 and 420 nm, while spraying with NaNO2-AlCl3-NaOH triggered hyperchromic shifts, and thus an increase in absorbance intensity in flavonoids with particular substitution patterns. A few non-flavonoid components with structural similarities to flavonoids (e.g., rosmarinic acid, gallic acid, aspirin, salicylic acid) served as the negative control in this study to determine whether the derivatization reagents allowed exclusive detection of flavonoids. The method was then applied to the analysis of flavonoid containing supplements as well as red clover honey to demonstrate the method's application in the analysis of natural products.
{"title":"Investigating Flavonoids by HPTLC Analysis Using Aluminium Chloride as Derivatization Reagent.","authors":"Sharmin Sultana, Md Lokman Hossain, Tom Sostaric, Lee Yong Lim, Kevin J Foster, Cornelia Locher","doi":"10.3390/molecules29215161","DOIUrl":"10.3390/molecules29215161","url":null,"abstract":"<p><p>This is the first study to report on high performance thin layer chromatography (HPTLC) generated spectrophotometric data to systematically capture flavonoid compounds using optimized derivatization with either AlCl<sub>3</sub> or NaNO<sub>2</sub>-AlCl<sub>3</sub>-NaOH as visualisation reagents. While the traditional AlCl<sub>3</sub> colorimetric method using UV-Vis analysis provides valuable insights into the presence of flavonoids and allows derivation of the total flavonoid content (TFC) of a sample, HPTLC fingerprints obtained after spraying with AlCl<sub>3</sub> or NaNO<sub>2</sub>-AlCl<sub>3</sub>-NaOH enable the visualization of the various flavonoids present in a sample based on their respective absorption shifts, thus complementing the traditional TFC assay. In this study, 40 different flavonoids representing different classes (flavonols, flavanolols, flavan-3-ol, flavones, flavanones, and isoflavonoids) were analysed. Upon derivatization with AlCl<sub>3</sub> most of the investigated flavonoids recorded bathochromic shifts, yielding characteristic λ<sub>max</sub> values between 370 and 420 nm, while spraying with NaNO<sub>2</sub>-AlCl<sub>3</sub>-NaOH triggered hyperchromic shifts, and thus an increase in absorbance intensity in flavonoids with particular substitution patterns. A few non-flavonoid components with structural similarities to flavonoids (e.g., rosmarinic acid, gallic acid, aspirin, salicylic acid) served as the negative control in this study to determine whether the derivatization reagents allowed exclusive detection of flavonoids. The method was then applied to the analysis of flavonoid containing supplements as well as red clover honey to demonstrate the method's application in the analysis of natural products.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547264/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624443","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Melanoma is a malignant neoplasm of melanocytes in the skin, and its occurrence is increasing annually. Plant-based products contain active compounds with low toxicity and are accessible alternatives for melanoma cancer treatment. The biotechnology approach for obtaining plant-based products provides continuity and allows the high-yield production of phytochemically uniform biomass. The callus biomass of Eryngium planum L. and Lychnis flos-cuculi L. was induced on Murashige and Skoog (MS) medium supplemented with growth regulators. A combination of 3.0 mg/L of 3,6-dichloro-2-methoxybenzoic acid (dicamba) and 0.3 mg/L of 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea-(thidiazuron) was used to obtain E. planum callus. Meanwhile, the callus of L. flos-cuculi was cultivated on MS medium with 2.0 mg/L of 2,4-dichlorophenoxyacetic acid (2,4-D). Methanolic extracts (EpME and LFcME), including 40% MeOH fractions (Ep40MF and LFc40MF) and 80% MeOH fractions (Ep80MF and LFc80MF), of E. planum and L. flos-cuculi cell biomass were prepared. Their cytotoxicity activity was assessed in human fibroblast cells (MRC-5) and human melanoma cells (MeWo) by direct cell counting and 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) assay. Qualitative analyses using thin-layer chromatography and UPLC-HRMS/MS chromatograms showed the presence of phenolic acids and saponins within the extracts and fractions of both cell biomasses. LFc80MF and Ep80MF showed the strongest toxicity against the MeWo cell line, with IC50 values of 47 ± 0.5 and 52 ± 4 μg/mL after 72 h of treatment. EpME and LFcME had IC50 values of 103 ± 4 and 147 ± 4 µg/mL, respectively. On the other hand, Ep40MF and LFc40MF were less toxic against the MeWo cell line compared to the extracts and 80% MeOH fractions, with IC50 values of 145 ± 10 and 172 ± 7 µg/mL. This study suggests that the obtained extracts and fractions of E. planum and L. flos-cuculi cell biomass potentially possess significant cytotoxic activity against MeWo cells, which work in a time and dose-dependent manner. Although the extracts and 80% MeOH fractions were more potent, the 40% MeOH was shown to be more selective against the MeWo than the control MRC-5 cells.
{"title":"Evaluation of Cytotoxic Activity of Cell Biomass from <i>Eryngium planum</i> and <i>Lychnis flos-cuculi</i> on Melanoma Cancer Cell.","authors":"Anastasia Aliesa Hermosaningtyas, Ewa Totoń, Natalia Lisiak, Dariusz Kruszka, Anna Budzianowska, Małgorzata Kikowska","doi":"10.3390/molecules29215158","DOIUrl":"10.3390/molecules29215158","url":null,"abstract":"<p><p>Melanoma is a malignant neoplasm of melanocytes in the skin, and its occurrence is increasing annually. Plant-based products contain active compounds with low toxicity and are accessible alternatives for melanoma cancer treatment. The biotechnology approach for obtaining plant-based products provides continuity and allows the high-yield production of phytochemically uniform biomass. The callus biomass of <i>Eryngium planum</i> L. and <i>Lychnis flos-cuculi</i> L. was induced on Murashige and Skoog (MS) medium supplemented with growth regulators. A combination of 3.0 mg/L of 3,6-dichloro-2-methoxybenzoic acid (dicamba) and 0.3 mg/L of 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea-(thidiazuron) was used to obtain <i>E. planum</i> callus. Meanwhile, the callus of <i>L. flos-cuculi</i> was cultivated on MS medium with 2.0 mg/L of 2,4-dichlorophenoxyacetic acid (2,4-D). Methanolic extracts (EpME and LFcME), including 40% MeOH fractions (Ep40MF and LFc40MF) and 80% MeOH fractions (Ep80MF and LFc80MF), of <i>E. planum</i> and <i>L. flos-cuculi</i> cell biomass were prepared. Their cytotoxicity activity was assessed in human fibroblast cells (MRC-5) and human melanoma cells (MeWo) by direct cell counting and 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) assay. Qualitative analyses using thin-layer chromatography and UPLC-HRMS/MS chromatograms showed the presence of phenolic acids and saponins within the extracts and fractions of both cell biomasses. LFc80MF and Ep80MF showed the strongest toxicity against the MeWo cell line, with IC<sub>50</sub> values of 47 ± 0.5 and 52 ± 4 μg/mL after 72 h of treatment. EpME and LFcME had IC<sub>50</sub> values of 103 ± 4 and 147 ± 4 µg/mL, respectively. On the other hand, Ep40MF and LFc40MF were less toxic against the MeWo cell line compared to the extracts and 80% MeOH fractions, with IC<sub>50</sub> values of 145 ± 10 and 172 ± 7 µg/mL. This study suggests that the obtained extracts and fractions of <i>E. planum</i> and <i>L. flos-cuculi</i> cell biomass potentially possess significant cytotoxic activity against MeWo cells, which work in a time and dose-dependent manner. Although the extracts and 80% MeOH fractions were more potent, the 40% MeOH was shown to be more selective against the MeWo than the control MRC-5 cells.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547748/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624414","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-31DOI: 10.3390/molecules29215177
Shannon Bober, Dmitry Kurouski
Colored textiles are valuable physical evidence often found at crime scenes. Analysis of the chemical structure of textiles could be used to establish a connection between fabric found at a crime scene and suspect cloths. High-performance liquid chromatography (HPLC) and mass spectroscopy coupled HPLC are traditionally used for the identification of dyes in fabric. However, these techniques are invasive and destructive. A growing body of evidence indicates that near-infrared excitation (λ = 830 nm) Raman spectroscopy (NIeRS) could be used to probe the chemical signature of such colorants. At the same time, it remains unclear whether environmental factors, such as solar light could lower the accuracy of NIeRS-based identification of dyes in textiles. In this study, we exposed cotton fabric colored with six different dyes to light and investigated the extent to which colorants fade during seven weeks using NIeRS. We found a decrease in the intensities of all vibrational bands in the acquired spectra as the time of the exposition of fabric to light increased. Nevertheless, utilization of partial least-squared discriminant analysis (PLS-DA) enabled identification of the colorants at all eight weeks. These results indicate that the effect of light exposure should be strongly considered by forensic experts upon the NIeRS-based analysis of colored fabric.
{"title":"Elucidation of the Effect of Solar Light on the Near-Infrared Excitation Raman Spectroscopy-Based Analysis of Fabric Dyes.","authors":"Shannon Bober, Dmitry Kurouski","doi":"10.3390/molecules29215177","DOIUrl":"10.3390/molecules29215177","url":null,"abstract":"<p><p>Colored textiles are valuable physical evidence often found at crime scenes. Analysis of the chemical structure of textiles could be used to establish a connection between fabric found at a crime scene and suspect cloths. High-performance liquid chromatography (HPLC) and mass spectroscopy coupled HPLC are traditionally used for the identification of dyes in fabric. However, these techniques are invasive and destructive. A growing body of evidence indicates that near-infrared excitation (λ = 830 nm) Raman spectroscopy (NIeRS) could be used to probe the chemical signature of such colorants. At the same time, it remains unclear whether environmental factors, such as solar light could lower the accuracy of NIeRS-based identification of dyes in textiles. In this study, we exposed cotton fabric colored with six different dyes to light and investigated the extent to which colorants fade during seven weeks using NIeRS. We found a decrease in the intensities of all vibrational bands in the acquired spectra as the time of the exposition of fabric to light increased. Nevertheless, utilization of partial least-squared discriminant analysis (PLS-DA) enabled identification of the colorants at all eight weeks. These results indicate that the effect of light exposure should be strongly considered by forensic experts upon the NIeRS-based analysis of colored fabric.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547680/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624362","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Macroporous resin is an efficient separation technology that plays a crucial role in the separation and purification of traditional Chinese medicine (TCM). However, the application of macroporous resins in TCM pharmaceuticals is hindered by serious fouling caused by the complex materials used in TCM. This study examines the impact of ultrafiltration (UF) membrane technology on the macroporous resin adsorption behavior of TCM extracts. In this paper, Bupleurum chinense DC. (B. chinense) water extracts were included as an example to study the effect of UF pretreatment on the macroporous resin adsorption of total saponins. The study results indicated that the adsorption of total saponins constituents from the water extracts of B. chinense on the macroporous resin followed the pseudo-second-order kinetic model and the Langmuir model. The thermodynamic parameters of adsorption, including enthalpy changes and Gibbs free energies, were negative, while entropy changes were positive. These results demonstrated that the total saponin components form a monolayer adsorption layer by spontaneous thermal adsorption on the macroporous resin, and that the adsorption rate is not determined by the rate of intraparticle diffusion. Following treatment with a UF membrane with an average molecular weight cut-off of 50 kDa, the protein, starch, pectin, tannin, and other impurities in the water extracts of B. chinense were reduced, while the total saponin content was retained at 82.32%. The adsorption kinetic model of the saponin constituents on the macroporous resin remained unchanged and was consistent with both the second-order kinetic model and the Langmuir model; the adsorption rate of the second-order kinetic model increased by 1.3 times and in the Langmuir model at 25 °C, the adsorption performance improved by 1.16 times compared to the original extracts. This study revealed that UF technology as a pretreatment method can reduce the fouling of macroporous resin by TCM extracts and improve the adsorption performance of macroporous resin.
{"title":"Effect of the Total Saponins of <i>Bupleurum chinense</i> DC. Water Extracts Following Ultrafiltration Pretreatment on Macroporous Resin Adsorption.","authors":"Ruihong Wang, Hongbo Liu, Zhishu Tang, Huaxu Zhu, Huan Liu, Ran Guo, Zhongxing Song, Hongbo Xu, Bo Li, Guolong Li, Yue Zhang","doi":"10.3390/molecules29215153","DOIUrl":"10.3390/molecules29215153","url":null,"abstract":"<p><p>Macroporous resin is an efficient separation technology that plays a crucial role in the separation and purification of traditional Chinese medicine (TCM). However, the application of macroporous resins in TCM pharmaceuticals is hindered by serious fouling caused by the complex materials used in TCM. This study examines the impact of ultrafiltration (UF) membrane technology on the macroporous resin adsorption behavior of TCM extracts. In this paper, <i>Bupleurum chinense</i> DC. (<i>B. chinense</i>) water extracts were included as an example to study the effect of UF pretreatment on the macroporous resin adsorption of total saponins. The study results indicated that the adsorption of total saponins constituents from the water extracts of <i>B. chinense</i> on the macroporous resin followed the pseudo-second-order kinetic model and the Langmuir model. The thermodynamic parameters of adsorption, including enthalpy changes and Gibbs free energies, were negative, while entropy changes were positive. These results demonstrated that the total saponin components form a monolayer adsorption layer by spontaneous thermal adsorption on the macroporous resin, and that the adsorption rate is not determined by the rate of intraparticle diffusion. Following treatment with a UF membrane with an average molecular weight cut-off of 50 kDa, the protein, starch, pectin, tannin, and other impurities in the water extracts of <i>B. chinense</i> were reduced, while the total saponin content was retained at 82.32%. The adsorption kinetic model of the saponin constituents on the macroporous resin remained unchanged and was consistent with both the second-order kinetic model and the Langmuir model; the adsorption rate of the second-order kinetic model increased by 1.3 times and in the Langmuir model at 25 °C, the adsorption performance improved by 1.16 times compared to the original extracts. This study revealed that UF technology as a pretreatment method can reduce the fouling of macroporous resin by TCM extracts and improve the adsorption performance of macroporous resin.</p>","PeriodicalId":19041,"journal":{"name":"Molecules","volume":"29 21","pages":""},"PeriodicalIF":4.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11547492/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142624226","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}