Molecules

12 pages, 2191 KiB

Open AccessArticle

Phenolic and Iridoid Glycosides from Leonurus cardiaca L. and Their Effects on the α, δ, and γ Subtypes of the PPAR System—Including the Discovery of the Novel Phenylethanoid Cardiaphenyloside A and the Most Active 7-Chloro-6-desoxy-harpagide

by Kenny Kuchta, Nobuyasu Matsuura, Tung Huu Nguyen, Christian Rusch, Munekazu Iinuma, Yukihiro Shoyama and Hans Wilhelm Rauwald

Molecules 2025, 30(2), 419; https://doi.org/10.3390/molecules30020419 (registering DOI) - 20 Jan 2025

Abstract

Leonurus cardiaca L. is known in Europe for its cardioactivity—also in interrelation with known risk factors of the metabolic syndrome—just as L. japonicus Houtt. in East Asia; however, up to now, no active constituents could be identified. The three sub-types of PPARs (α, [...] Read more.

Leonurus cardiaca L. is known in Europe for its cardioactivity—also in interrelation with known risk factors of the metabolic syndrome—just as L. japonicus Houtt. in East Asia; however, up to now, no active constituents could be identified. The three sub-types of PPARs (α, δ, and γ), are involved in controlling the lipid metabolism in the liver and skeletal muscles. Although PPARδ especially is a potential therapeutic target for the metabolic syndrome, insulin resistance, and obesity, no PPARδ agonists with clinical potential have presently been developed. Therefore, nineteen dominant isolated constituents of both species were screened for activity on the metabolic syndrome related PPAR α, δ, and γ in a newly developed luciferase reporter gene assay. Eight phenylethanoid glycosides not previously detected in L. cardiaca, including the novel cardiaphenyloside A, as well as the iridoids ajugol and harpagide were found via bioassay-guided isolation and structural elucidation of spectroscopic and chemical evidence. For the PPARδ experiment, all nineteen isolated constituents and GW0742 (positive control) were added to the medium of transfected COS-1 cells and further processed according to a standardized luciferase assay protocol. Only the major iridoid 7-chloro-6-desoxy-harpagide displayed significant activity in the PPARδ assay at 50 μg/mL, while the result for 100 μg/mL was higher than for the GW0742 positive control. Rutin, chicoric acid, and cardiaphenyloside A at 100 μg/mL showed PPARα agonistic activity. For PPARγ, no significant effects were observed. This activity of Leonurus extracts and especially of their active constituent 7-chloro-6-desoxy-harpagide on the δ subtype of the PPAR system strongly indicates their potential for anti-obesity therapy. Full article

(This article belongs to the Special Issue Bioactivity of Natural Compounds: From Plants to Humans)

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17 pages, 7586 KiB

Open AccessArticle

Corrosion of Low-Alloy Steel in Ethanolamine Steam Generator Chemistry—The Effect of Temperature and Flow Rate

by Iva Betova, Martin Bojinov and Vasil Karastoyanov

Molecules 2025, 30(2), 418; https://doi.org/10.3390/molecules30020418 (registering DOI) - 20 Jan 2025

Abstract

The corrosion of low-alloy steel in ethanolamine solution, simulating steam generator chemistry, is studied by in situ chronopotentiometry and electrochemical impedance spectroscopy combined with ex situ analysis of the obtained oxide films and model calculations. Hydrodynamic calculations of the proposed setup to study [...] Read more.

The corrosion of low-alloy steel in ethanolamine solution, simulating steam generator chemistry, is studied by in situ chronopotentiometry and electrochemical impedance spectroscopy combined with ex situ analysis of the obtained oxide films and model calculations. Hydrodynamic calculations of the proposed setup to study flow-assisted corrosion demonstrate that turbulent conditions are achieved. Quantum chemical calculations indicate the adsorption orientation of ethanolamine on the oxide surface. Interpretation of impedance spectra with a kinetic approach based on the mixed-conduction model enabled estimating the rate constants of oxidation at the alloy–oxide interface, as well as charge transfer and ionic transport resistances of the corrosion process. In turbulent conditions, the dissolution of Fe oxide and ejection of Fe cations are enhanced, leading to Cr enrichment in the oxide and alteration of its electronic and electrochemical properties that influence the corrosion rate. Full article

(This article belongs to the Section Electrochemistry)

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28 pages, 4327 KiB

Open AccessFeature PaperReview

Recent Advances in Paper Conservation Using Nanocellulose and Its Composites

by Mei Jiang, Jingjing Yao, Qiang Guo, Yueer Yan, Yi Tang and Yuliang Yang

Molecules 2025, 30(2), 417; https://doi.org/10.3390/molecules30020417 (registering DOI) - 19 Jan 2025

Abstract

Paper-based cultural relics experience aging and deterioration during their long-term preservation, which poses a serious threat to their lifetime. The development of conservation materials with high compatibility and low intervention has been expected to extend the lifetime of paper artifacts. As a new [...] Read more.

Paper-based cultural relics experience aging and deterioration during their long-term preservation, which poses a serious threat to their lifetime. The development of conservation materials with high compatibility and low intervention has been expected to extend the lifetime of paper artifacts. As a new type of biological macromolecule, nanocellulose has been extensively utilized in paper conservation, attributed to its excellent paper compatibility, high optical transparency, outstanding mechanical strength, and large specific surface area with abundant hydroxyl groups. This review systematically summarizes the latest development of three kinds of nanocellulose (cellulose nanofibril, cellulose nanocrystal, and bacterial nanocellulose) and their composites used for the multifunctional conservation of paper relics. Owing to the strong hydrogen bond interactions between hydroxyls of nanocellulose and paper fibers, nanocellulose can effectively consolidate paper without adding adhesives. The composite of nanocellulose with other functional materials greatly expands its application scope, and the superior performance has been emphasized in paper deacidification, consolidation, antimicrobial effect, antioxidation, UV resistance, self-cleaning, promotion of printing property, reduction in air permeability, and flame retardancy. The application characteristics and future prospects of nanocellulose composites are highlighted in the conservation of paper-based cultural relics. Full article

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21 pages, 462 KiB

Open AccessArticle

Crude Drugs for Clearing Heat Contain Compounds Exhibiting Anti-Inflammatory Effects in Interleukin-1β-Treated Rat Hepatocytes

by Airi Fujii, Saki Onishi, Nodoka Watanabe, Mizuki Kajimura, Kentaro Ito, Keita Minamisaka, Yuto Nishidono, Saki Shirako, Yukinobu Ikeya and Mikio Nishizawa

Molecules 2025, 30(2), 416; https://doi.org/10.3390/molecules30020416 (registering DOI) - 19 Jan 2025

Abstract

Traditional Japanese medicines, i.e., Kampo medicines, consist of crude drugs (mostly plants) that have empirical pharmacological functions (‘Yakuno’ in Japanese), such as clearing heat. Crude drugs with cold properties, such as Phellodendron bark, have the empirical function of clearing heat as [...] Read more.

Traditional Japanese medicines, i.e., Kampo medicines, consist of crude drugs (mostly plants) that have empirical pharmacological functions (‘Yakuno’ in Japanese), such as clearing heat. Crude drugs with cold properties, such as Phellodendron bark, have the empirical function of clearing heat as they cool the body. Because we found that anti-inflammatory compounds were present in several crude drugs for clearing heat, it is speculated that the empirical function of clearing heat may be linked to anti-inflammatory activities. When 10 typical crude drugs were selected from 22 herbal crude drugs for clearing heat, we identified anti-inflammatory compounds in five crude drugs, including Phellodendron bark. In this study, the other crude drugs were extracted and partitioned with ethyl acetate (EtOAc) and n-butanol to obtain three crude fractions. All the EtOAc-soluble fractions, except that from Forsythia fruits, inhibited interleukin (IL)-1β-induced nitric oxide (NO) production in primary-cultured rat hepatocytes. Anti-inflammatory compounds were identified from these EtOAc-soluble fractions: baicalein from Scutellaria roots, (−)-nyasol from Anemarrhena rhizomes, and loniflavone from Lonicera leaves and stems. (+)-Phillygenin was purified from Forsythia fruits by removing cytotoxic oleanolic and betulinic acids. These compounds suppressed the production of NO and cytokines in hepatocytes. Anti-inflammatory compounds were not purified from the EtOAc-soluble fraction of Rehmannia roots because of their low abundance. Collectively, these findings indicate that anti-inflammatory compounds are present in all 10 crude drugs for clearing heat, confirming that these anti-inflammatory compounds in crude drugs provide the empirical functions for clearing heat. Other empirical functions of Kampo medicine can also be explained by modern pharmacological activities. Full article

(This article belongs to the Special Issue Natural Bioactive Compounds from Traditional Asian Plants)

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14 pages, 1435 KiB

Open AccessArticle

Concise Synthesis of Naphthalene-Based 14-Aza-12-Oxasteroids

by Smriti Srivastava, Jun Luo, Daniel Whalen, Katherine N. Robertson and Amitabh Jha

Molecules 2025, 30(2), 415; https://doi.org/10.3390/molecules30020415 (registering DOI) - 19 Jan 2025

Abstract

A concise, transition metal-free four-step synthetic pathway has been developed for the synthesis of tetracyclic heterosteroidal compounds, 14-aza-12-oxasteroids, starting from readily available 2-naphthol analogues. After conversion of 2-naphthols to 2-naphthylamines by the Bucherer reaction, subsequent selective C-acetylation was achieved via the Sugasawa reaction [...] Read more.

A concise, transition metal-free four-step synthetic pathway has been developed for the synthesis of tetracyclic heterosteroidal compounds, 14-aza-12-oxasteroids, starting from readily available 2-naphthol analogues. After conversion of 2-naphthols to 2-naphthylamines by the Bucherer reaction, subsequent selective C-acetylation was achieved via the Sugasawa reaction and reduction of the acetyl group using borohydride, which resulted into the corresponding amino-alcohols. The naphthalene-based amino-alcohols underwent double dehydrations and double intramolecular cyclization with oxo-acids leading to one-pot formation of a C-N bond, a C-O bond and an amide bond in tandem, to generate two additional rings completing the steroidal framework. A series of 14-aza-12-oxasteroids were synthesized using our developed synthetic strategy in moderate yields, and the structure of one of the final products, 12a-Methyl-11-phenyl-11,12a-dihydro-1H-naphtho[2,1-d]pyrrolo[2,1-b][1,3]oxazin-3(2H)-one, was further confirmed by single crystal X-ray crystallography. Full article

(This article belongs to the Special Issue Advances in the Synthesis of Heterocyclic Compounds and Their Applications)

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12 pages, 1455 KiB

Open AccessFeature PaperArticle

Enzymatic β-Mannosylation of Phenylethanoid Alcohols

by Lucia Černáková, Peter Haluz, Vladimír Mastihuba, Zuzana Košťálová, Elena Karnišová Potocká and Mária Mastihubová

Molecules 2025, 30(2), 414; https://doi.org/10.3390/molecules30020414 (registering DOI) - 19 Jan 2025

Abstract

Phenylethanoid glycosides (PhGs) are widely occurring secondary metabolites of medicinal plants with interesting biological activities such as antioxidant, anti-inflammatory, neuroprotective, antiviral, hepatoprotective, immunomodulatory, etc. They are characterized by a structural core formed by a phenethyl alcohol, usually tyrosol or hydroxytyrosol, attached to β-D-glucopyranose [...] Read more.

Phenylethanoid glycosides (PhGs) are widely occurring secondary metabolites of medicinal plants with interesting biological activities such as antioxidant, anti-inflammatory, neuroprotective, antiviral, hepatoprotective, immunomodulatory, etc. They are characterized by a structural core formed by a phenethyl alcohol, usually tyrosol or hydroxytyrosol, attached to β-D-glucopyranose via a glycosidic bond. This core is usually further decorated by attached phenolic acids or another saccharide. Several studies suggest an important role of the saccharidic fragment in the biological activities of PhGs, provoking demand for new glycovariants of natural PhGs. This study presents the preparation of β-mannosylated analogs of tyrosol β-D-glucopyranoside (salidroside) and hydroxytyrosol β-D-glucopyranoside (hydroxysalidroside). While the chemical synthesis of β-D-mannopyranosides is rather challenging, they can be prepared by enzymatic catalysis. We found that Novozym 188, an industrial β-glucosidase, also contains β-mannosidase and used this enzyme in the preparation of tyrosol β-D-mannopyranoside and hydroxytyrosol β-D-mannopyranoside in 12 and 16% chemical yields, respectively, by transglycosylation from β-D-mannopyranosyl-(1→4)-D-mannose. The mannosylation was chemoselective and occurred exclusively on the primary hydroxyls of tyrosol and hydroxytyrosol, and the glycosylation of phenolic moieties of the aglycons was observed. Full article

(This article belongs to the Section Natural Products Chemistry)

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12 pages, 592 KiB

Open AccessArticle

An Electrochemical Dopamine Assay with Cobalt Oxide Palatinose Carbon Dots

by Ram Chandra Nepal, Elif S. Seven, Roger M. Leblanc and Charles C. Chusuei

Molecules 2025, 30(2), 413; https://doi.org/10.3390/molecules30020413 (registering DOI) - 19 Jan 2025

Abstract

Elevated dopamine (DA) levels in urine denote neuroblastoma, a pediatric cancer. Saccharide-derived carbon dots (CDs) were applied to assay DA detection in simulated urine (SU) while delineating the effects of graphene defect density on electrocatalytic activity. CDs were hydrothermally synthesized to vary graphene [...] Read more.

Elevated dopamine (DA) levels in urine denote neuroblastoma, a pediatric cancer. Saccharide-derived carbon dots (CDs) were applied to assay DA detection in simulated urine (SU) while delineating the effects of graphene defect density on electrocatalytic activity. CDs were hydrothermally synthesized to vary graphene defect densities using sucrose, raffinose, and palatinose, depositing them onto glassy carbon electrodes (GCEs). Co₃O₄ nanoparticles (NPs) were encapsulated by the CDs. Cyclic (CV) and linear sweep (LSV) voltammetry measurements were obtained, drop-casting the CDs onto GCEs and measuring DA in a phosphate-buffer solution (pH = 7). DA had an oxidation peak at +0.2 V with SucCDs, with the highest current correlating with the highest defect density. PalCD-Co₃O₄ exhibited the largest signal for DA detection in simulated urine (SU) using the oxidation peak at +0.5 V; the composite had a lower defect density compared to SucCD-Co₃O₄. The Co₃O₄-PalCDs had a DA detection range of 1 to 90 µM with an LOD of 0.88 μM in SU. SEM-EDX analysis of the electrode surface revealed semi-spherical structures with an average particle diameter of 80 ± 19 nm (n = 347) with PalCDs decorating the Co₃O₄ NPs. XRD characterization showed the incorporation of PalCD and Co₃O₄ within the composite. XPS showed electron density donation from the PalCD to Co₃O₄. Full article

(This article belongs to the Section Electrochemistry)

19 pages, 4186 KiB

Open AccessArticle

Thiamine and Thiamine Pyrophosphate as Non-Competitive Inhibitors of Acetylcholinesterase—Experimental and Theoretical Investigations

by Łukasz Szeleszczuk, Dariusz Maciej Pisklak and Błażej Grodner

Molecules 2025, 30(2), 412; https://doi.org/10.3390/molecules30020412 (registering DOI) - 19 Jan 2025

Abstract

Vitamin B₁ (thiamine) plays an important role in human metabolism. It is essential for the proper growth and development of the body and has a positive effect on the functioning of the digestive, cardiovascular, and nervous systems. Additionally, it stimulates the brain [...] Read more.

Vitamin B₁ (thiamine) plays an important role in human metabolism. It is essential for the proper growth and development of the body and has a positive effect on the functioning of the digestive, cardiovascular, and nervous systems. Additionally, it stimulates the brain and improves the psycho-emotional state. In vivo, vitamin B₁ occurs in free form as thiamine or as its ester with phosphate residue(s), i.e., as mono-, di-, or triphosphate. It has been proven that supportive therapy with vitamin B₁ can not only provide neuroprotection but also has a positive effect on advanced neurodegenerative diseases, such as Parkinson’s disease, Alzheimer’s disease, Wernicke–Korsakoff syndrome, or Huntington’s disease. This paper presents studies on the effect of free thiamine (T) and thiamine pyrophosphate (TPP) on the activity of acetylcholinesterase (AChE), which is an enzyme considered to play an important role in the therapies for neurodegenerative diseases, especially Alzheimer’s disease. The mechanisms of action of these compounds as potential inhibitors of AChE were evaluated using both experimental (enzymatic activity) as well as computational (molecular docking, molecular dynamics simulations, and MM-GBSA calculations) methods. The results of the current study indicate a non-competitive type of enzyme inhibition, in contrast to the previously published works suggesting a competitive one. Full article

(This article belongs to the Special Issue Enzyme Inhibitors: Design, Synthesis and Biological Evaluation, 2nd Edition)

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22 pages, 3257 KiB

Open AccessReview

Compounds Involved in the Invasive Characteristics of Lantana camara

by Hisashi Kato-Noguchi and Midori Kato

Molecules 2025, 30(2), 411; https://doi.org/10.3390/molecules30020411 (registering DOI) - 19 Jan 2025

Abstract

Lantana camara L. is native to tropical America and has naturalized in many other tropical, subtropical, and temperate regions in Asia, Africa, Oceania, North and South America, and Europe. L. camara infests diverse habitats with a wide range of climatic factors, and its [...] Read more.

Lantana camara L. is native to tropical America and has naturalized in many other tropical, subtropical, and temperate regions in Asia, Africa, Oceania, North and South America, and Europe. L. camara infests diverse habitats with a wide range of climatic factors, and its population increases aggressively as one of the world’s 100 worst invasive alien species. Its infestation reduces species diversity and abundance in the natural ecosystems and reduces agricultural production. The life history characteristics of L. camara, such as its high reproductive ability and high adaptive ability to various environmental conditions, may contribute to its ability to infest and increase its population. Possible evidence of the compounds involved in the defense functions of L. camara against natural enemies, such as herbivore mammals and insects, parasitic nematodes, pathogenic fungi and bacteria, and the allelochemicals involved in its allelopathy against neighboring competitive plant species, have accumulated in the literature over three decades. Lantadenes A and B, oleanonic acid, and icterogenin are highly toxic to herbivore mammals, and β-humulene, isoledene, α-copaene thymol, and hexadecanoic acid have high insecticidal activity. β-Caryophyllene and cis-3-hexen-1-ol may function as herbivore-induced plant volatiles which are involved in sending warning signals to undamaged tissues and the next plants of the same species. Farnesol and farnesal may interrupt insect juvenile hormone biosynthesis and cause abnormal metamorphosis of insects. Several triterpenes, such as lantanolic acid, lantoic acid, pomolic acid, camarin, lantacin, camarinin, ursolic acid, and oleanonic acid, have demonstrated nematocidal activity. Lantadene A, β-caryophyllene, germacrene-D, β-curcumene, eicosapentaenoic acid, and loliolide may possess antimicrobial activity. Allelochemicals, such as caffeic acid, ferulic acid, salicylic acid, α-resorcylic acid, p-hydroxybenzoic acid, vanillic acid, unbelliferone, and quercetin, including lantadenes A and B and β-caryophyllene, suppress the germination and growth of neighboring plant species. These compounds may be involved in the defense functions and allelopathy and may contribute to L. camara’s ability to infest and to expand its population as an invasive plant species in new habitats. This is the first review to focus on how compounds enhance the invasive characteristics of L. camara. Full article

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17 pages, 2379 KiB

Open AccessFeature PaperArticle

New Insights on Quality, Safety, Nutritional, and Nutraceutical Properties of Honeydew Honeys from Italy

by Andrea Mara, Federica Mainente, Vasiliki Sorsou, Yolanda Picó, Iratxe Perales, Asma Ghorab, Gavino Sanna, Isabel Borrás-Linares, Gianni Zoccatelli and Marco Ciulu

Molecules 2025, 30(2), 410; https://doi.org/10.3390/molecules30020410 (registering DOI) - 19 Jan 2025

Abstract

Honeydew honey is less studied than nectar honey, although it is characterized by peculiar nutritional properties. This is mainly due to its challenging production, which leads to easy counterfeiting and difficult valorization. This contribution aims to provide a comprehensive characterization of the physico-chemical, [...] Read more.

Honeydew honey is less studied than nectar honey, although it is characterized by peculiar nutritional properties. This is mainly due to its challenging production, which leads to easy counterfeiting and difficult valorization. This contribution aims to provide a comprehensive characterization of the physico-chemical, palynological, functional, and food safety properties of a large sampling of honeydew honeys collected throughout Italy. The honeydew elements, conductivity, color, antioxidant properties, total polyphenol content, hydroxymethylfurfural, major and trace elements, toxic and rare earth elements, and pesticide residues were measured in 59 samples of honeydew honey from forest, eucalyptus, fir, oak, and citrus sources. Physico-chemical and antioxidant properties were unable to differentiate the botanical origin of Italian honeydew honeys. Similarly, the mineral composition did not vary significantly, whereas rare earth elements appeared to be promising markers for classifying their origin. Multivariate analysis allowed discriminating fir honeydews from the other varieties. Concerning safety aspects, pesticide residues were detected in 90% of the samples, with fir honeydews exhibiting the lowest contamination levels, probably due to its production in less industrialized areas. Acetamiprid and imidacloprid were the most prevalent pesticide residues, but their concentrations were below the limit indicated by the EFSA. These findings suggest the need for a continuous monitoring program for contaminants to ensure safety and to assess risk. Full article

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13 pages, 1492 KiB

Open AccessFeature PaperArticle

Screening of Solvent Systems for Countercurrent Chromatography Separation of Polar Constituents from Ginkgo biloba L. Seeds

by Ruxi Hu, Zhuo Liu, Yi Zhou, Peng Tian, Luqi Li, Zhi Yang and Yatuan Ma

Molecules 2025, 30(2), 409; https://doi.org/10.3390/molecules30020409 (registering DOI) - 19 Jan 2025

Abstract

The separation of large polar constituents presents a substantial challenge in natural product research when employing column chromatography techniques, as the process is both complex and time-consuming. In this study, an acetonitrile/tetrahydrofuran/di-(2-ethylhexyl) phosphoric acid/aqueous saturated sodium chloride solvent system was developed and utilized [...] Read more.

The separation of large polar constituents presents a substantial challenge in natural product research when employing column chromatography techniques, as the process is both complex and time-consuming. In this study, an acetonitrile/tetrahydrofuran/di-(2-ethylhexyl) phosphoric acid/aqueous saturated sodium chloride solvent system was developed and utilized for the countercurrent chromatography of polar constituents from Ginkgo biloba L. seeds. Five polar constituents were effectively isolated using an acetonitrile/tetrahydrofuran/di-(2-ethylhexyl) phosphoric acid/aqueous saturated sodium chloride (2:2:0.8:3, v/v) solvent system using a two-step countercurrent chromatography method. In the initial countercurrent chromatography process, three constituents were successfully purified from the methanol extract: compound 1, compound 4, and compound 5. Compounds 2 and 3, co-eluted from the column, were further subjected to three inner-recycling chromatographic procedures. At last, five constituents were purified and identified, including 4′-O-methylpyridoxine (1); two indole alkaloid N-glucosides, ginkgoside B (2) and ginkgoside A (3); 2-(4-hydroxybenzyl) malic acid (4); and coniferyl alcohol (5). The results demonstrated that the acetonitrile/tetrahydrofuran/di-(2-ethylhexyl) phosphoric acid/aqueous saturated sodium chloride solvent system serves as a feasible system for the efficient countercurrent chromatography separation of polar components. Full article

(This article belongs to the Topic Counter-Current Chromatography in Natural Products Isolation)

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11 pages, 221 KiB

Open AccessArticle

Evaluation of the Proximate Composition of Amsonia tabernaemontana Walt. Seeds and Glyceride Oil

by Olga Teneva, Zhana Petkova, Ana Dobreva, Anatoli Dzhurmanski and Ginka Antova

Molecules 2025, 30(2), 408; https://doi.org/10.3390/molecules30020408 (registering DOI) - 19 Jan 2025

Abstract

The genus Amsonia, a member of the Apocynaceae family, comprises plants with notable medicinal benefits. In 2022 and 2023, Amsonia tabernaemontana Walt. seeds introduced to Bulgaria were collected and analyzed. Given the limited information available on the chemical composition of A. tabernaemontana, [...] Read more.

The genus Amsonia, a member of the Apocynaceae family, comprises plants with notable medicinal benefits. In 2022 and 2023, Amsonia tabernaemontana Walt. seeds introduced to Bulgaria were collected and analyzed. Given the limited information available on the chemical composition of A. tabernaemontana, this study aimed to evaluate the phytochemical profile of the plant seeds collected over two consecutive years. Although members of the genus Amsonia are not conventional oilseed crops, the glyceride oil content was 7.8% and 11.1% in the respective samples. The chemical composition was meticulously analyzed, revealing carbohydrates in the largest amounts (60.4% and 61.3%), with crude fibers at 18.3% and 24.8%, and protein content at 19.5% and 13.0%. The amounts of ash and moisture content were also quantified. Additionally, the fatty acids, sterols, tocopherols, and phospholipids of the seed oil were examined. β-Sitosterol emerged as the main component in both harvests. The total tocopherol content was relatively low (52.7 mg/kg vs. 20.0 mg/kg), with α-tocopherol being predominant. Phosphatidylcholine, phosphatidylinositol, and phosphatidylethanolamine were identified as the principal components of the phospholipid fraction. The fatty acid composition primarily included linoleic (61.0 and 61.2%) and oleic acids (28.7 and 28.6%). Full article

(This article belongs to the Special Issue Analysis and Biological Evaluation of Bioactive Compounds from Natural Sources)

16 pages, 2571 KiB

Open AccessArticle

Removal of Malachite Green Dye from Aqueous Solution by a Novel Activated Carbon Prepared from Baobab Seeds Using Chemical Activation Method

by Samah Daffalla

Molecules 2025, 30(2), 407; https://doi.org/10.3390/molecules30020407 (registering DOI) - 19 Jan 2025

Abstract

Two activated carbons were synthesized from baobab seeds (BSs) using two activators, sulfuric acid (BS-AAC) and sodium hydroxide (BS-BAC), for dye removal from aqueous solutions. Malachite green (MG) was used as a model dye. SEM, FTIR, TGA, and surface area were used to [...] Read more.

Two activated carbons were synthesized from baobab seeds (BSs) using two activators, sulfuric acid (BS-AAC) and sodium hydroxide (BS-BAC), for dye removal from aqueous solutions. Malachite green (MG) was used as a model dye. SEM, FTIR, TGA, and surface area were used to characterize the feedstock and synthesis activated carbons. According to the SEM results, the surface morphology differed significantly from that of the raw material due to the many pores created by activating agents during carbonization. Various surface groups existed on the activated carbon surface as shown by FTIR analysis. An oxidation process utilizing hydrogen peroxide (H₂O₂) was investigated for MG. Various reaction parameters such as pH value, H₂O₂ concentration, and activated carbon dosage were investigated for the oxidative degradation of MG. By using BS-AAC and BS-BAC, 97.9% and 78% dye degradation efficiency in aqueous solutions, respectively, was achieved under optimal conditions. This study reveals that MG dye degradation increases with solution pH, making BS-AAC and BS-BAC ineffective at low pH values. However, degradation declines above pH 6. Based on the BS-AAC data, MG removal kinetics were fitted with a first-order kinetic model, while BS-BAC data were fitted with a second-order kinetic model. It was demonstrated that activating baobab with sulfuric acid can form a novel activated carbon that can quickly remove MG from aqueous solutions. The results showed that the removal of malachite green was over 89% for AC-AAC and 77% for AC-BAC, even after four regeneration cycles. Full article

(This article belongs to the Special Issue Porous and Nanoporous Materials in Heterogeneous Catalysis)

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13 pages, 6133 KiB

Open AccessFeature PaperArticle

Specialized Metabolite Profiling-Based Variations of Watercress Leaves (Nasturtium officinale R.Br.) from Hydroponic and Aquaponic Systems

by Ivon Buitrago-Villanueva, Ricardo Barbosa-Cornelio and Ericsson Coy-Barrera

Molecules 2025, 30(2), 406; https://doi.org/10.3390/molecules30020406 (registering DOI) - 19 Jan 2025

Abstract

Watercress (Nasturtium officinale), a freshwater aquatic plant in the Brassicaceae family, is characterized by its high content of specialized metabolites, including flavonoids, glucosinolates, and isothiocyanates. Traditionally, commercial cultivation is conducted in submerged beds using river or spring water, often on soil [...] Read more.

Watercress (Nasturtium officinale), a freshwater aquatic plant in the Brassicaceae family, is characterized by its high content of specialized metabolites, including flavonoids, glucosinolates, and isothiocyanates. Traditionally, commercial cultivation is conducted in submerged beds using river or spring water, often on soil or gravel substrates. However, these methods have significant environmental impacts, such as promoting eutrophication due to excessive fertilizer use and contaminating water sources with pesticides. This study aimed to explore two emerging cultivation strategies, i.e., hydroponics and aquaponics, to grow watercress and evaluate its specialized metabolite content using an untargeted metabolomic approach. The goal was to characterize metabolic profiles, identify component variations, and assess changes in metabolite accumulation at two harvest times. Two culture systems (hydroponic and aquaponic) and two harvest stages (‘baby leaf’ and traditional harvest) were examined. The results revealed 23 key metabolites, predominantly glucosinolates and flavonoids, that significantly influenced the metabolic profile discrimination, with the aquaponic system yielding the highest diversity and relative abundance of metabolites (variable importance in the projection (VIP) > 1). Important condition-related compounds were identified via cross-validation (area under the curve (AUC) > 0.7), including isorhamnetin sophoroside–glucoside and gluconasturtiin at the traditional harvest in the hydroponic system and glucoarabin at the ‘baby leaf’ stage in the aquaponic system. These findings highlight the potential of aquaponic and hydroponic systems as sustainable alternatives for watercress cultivation, offering environmental benefits and enhanced metabolite quality. Full article

(This article belongs to the Special Issue Phytochemical Profiling, Bioactivity, Biotechnology Studies and Practical Applications of Medicinal and Cosmetic Plants)

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13 pages, 4758 KiB

Open AccessArticle

Evaluation of Mechanochemically Prepared CePO₄∙H₂O Nanoparticles as UV Filter for Photoprotective Formulations

by Stanislav Kurajica, Filip Brleković, Sabina Keser, Goran Dražić, Katarina Mužina and Vanesa Mihajlović

Molecules 2025, 30(2), 405; https://doi.org/10.3390/molecules30020405 (registering DOI) - 18 Jan 2025

Abstract

Rhabdophane, CePO₄∙H₂O, nanoparticles were prepared by mechanochemical synthesis with different durations and thoroughly characterized by various characterization techniques. X-ray diffraction analysis showed that the optimal synthesis duration was 15 min, since, in this case, pure rhabdophane is obtained, without [...] Read more.

Rhabdophane, CePO₄∙H₂O, nanoparticles were prepared by mechanochemical synthesis with different durations and thoroughly characterized by various characterization techniques. X-ray diffraction analysis showed that the optimal synthesis duration was 15 min, since, in this case, pure rhabdophane is obtained, without traces of contamination by the vessel material. The size of the obtained nanoparticles, as determined from high-resolution transmission electron microscopy images, was around 5 nm. According to UV-Vis diffuse reflectance spectroscopy results, rhabdophane nanoparticles show transparency to visible light and high absorption in the UV region, with a direct bandgap of 3.1 eV. The photocatalytic activity in the Castor oil degradation process and the cytotoxicity for human skin cells were determined and compared to commercial TiO₂ nanoparticles, with rhabdophane nanoparticles exhibiting superior properties. Small particle size, purity, absorption in the UV range, transparency to visible light, low photocatalytic activity, and low cytotoxicity indicated the possibility of prepared rhabdophane application as an inorganic UV filter in photoprotective formulations. Full article

(This article belongs to the Section Materials Chemistry)

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12 pages, 3229 KiB

Open AccessArticle

Anion-Directed Assembly of a Bimetallic Pd/Ag Nanocluster: Synthesis, Characterization, and HER Activity

by Yu-Rong Ni, Rugma Thekke Pangal, Michael N. Pillay, Tzu-Hao Chiu, Samia Kahlal, Jean-Yves Saillard and C. W. Liu

Molecules 2025, 30(2), 404; https://doi.org/10.3390/molecules30020404 (registering DOI) - 18 Jan 2025

Abstract

Palladium-doped silver nanoclusters (NCs) have been highlighted for their unique physicochemical properties and potential applications in catalysis, optics, and electronics. Anion-directed synthesis offers a powerful route to control the morphology and properties of these NCs. Herein, we report a novel Pd-doped Ag NC, [...] Read more.

Palladium-doped silver nanoclusters (NCs) have been highlighted for their unique physicochemical properties and potential applications in catalysis, optics, and electronics. Anion-directed synthesis offers a powerful route to control the morphology and properties of these NCs. Herein, we report a novel Pd-doped Ag NC, [Pd(H)Ag₁₃(S){S₂P(OⁱPr)₂}₁₀] (PdHAg₁₃S), synthesized through the inclusion of sulfide and hydride anions. This NC features a unique linear S-Pd-H axis enclosed in a 4-5-4 stacked arrangement of silver atoms. The distinctive hydride environment was characterized by NMR spectroscopy, and the total structure was determined by single-crystal X-ray diffraction (SCXRD) and supported by computational studies. Mass spectrometry and X-ray photoelectron spectroscopy (XPS) further confirmed the assigned composition. This unique construct exhibits promising hydrogen evolution reaction (HER) activity. Our findings highlight the potential of anion-directed synthesis for creating novel bimetallic NCs with tailored structures and catalytic properties. Full article

(This article belongs to the Special Issue Exclusive Feature Papers in Inorganic Chemistry, 2nd Edition)

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12 pages, 2122 KiB

Open AccessArticle

Label-Free Surface-Enhanced Raman Scattering for Genomic DNA Cytosine Methylation Reading

by Kazi Morshed Alom, Anastasiia Tukova, Nana Lyu, Alison Rodger and Yuling Wang

Molecules 2025, 30(2), 403; https://doi.org/10.3390/molecules30020403 (registering DOI) - 18 Jan 2025

Abstract

DNA methylation has been widely studied with the goal of correlating the genome profiles of various diseases with epigenetic mechanisms. Multiple approaches have been developed that employ extensive steps, such as bisulfite treatments, polymerase chain reactions (PCR), restriction digestion, sequencing, mass analysis, etc., [...] Read more.

DNA methylation has been widely studied with the goal of correlating the genome profiles of various diseases with epigenetic mechanisms. Multiple approaches have been developed that employ extensive steps, such as bisulfite treatments, polymerase chain reactions (PCR), restriction digestion, sequencing, mass analysis, etc., to identify DNA methylation. In this article, we report a facile label-free surface-enhanced Raman scattering (SERS) spectroscopy system that utilizes gold nanoparticles (AuNPs) for signal enhancement of methylated DNA. The key innovation of this work is to use anionic nanoparticles at a high ionic strength to introduce the aggregation of AuNPs with anionic DNA. When target methylated DNA is present, the presence of a methyl group in the cytosine C5 position of CpG sites induces a Raman peak at 1350 cm⁻¹. Our amplification-free system has a limit of detection (LOD) of 5% and a limit of quantification (LOQ) of 16% with good specificity. The method was applied to determine the hypermethylated levels of the germline of colorectal cancer cell lines SW48 and SW480. Our simple label-free method holds the potential to read the disease-associated methylation of genomic DNA. Full article

(This article belongs to the Special Issue Molecular Spectroscopy in Applied Chemistry)

12 pages, 2298 KiB

Open AccessArticle

PTR-ToF-MS VOC Profiling of Raw and Cooked Gilthead Sea Bream Fillet (Sparus aurata): Effect of Rearing System, Season, and Geographical Origin

by Iuliia Khomenko, Valentina Ting, Fabio Brambilla, Mirco Perbellini, Luca Cappellin and Franco Biasioli

Molecules 2025, 30(2), 402; https://doi.org/10.3390/molecules30020402 (registering DOI) - 18 Jan 2025

Abstract

This study explores the impact of geographical origin, harvest time, and cooking on the volatile organic compound (VOC) profiles of wild and reared seabream from the Adriatic and Tyrrhenian Seas. A Proton Transfer Reaction–Time of Flight–Mass Spectrometry (PTR-ToF-MS) allowed for VOC profiling with [...] Read more.

This study explores the impact of geographical origin, harvest time, and cooking on the volatile organic compound (VOC) profiles of wild and reared seabream from the Adriatic and Tyrrhenian Seas. A Proton Transfer Reaction–Time of Flight–Mass Spectrometry (PTR-ToF-MS) allowed for VOC profiling with high sensitivity and high throughput. A total of 227 mass peaks were identified. Principal component analysis (PCA) showed a clear separation between cooked and raw samples, with cooking causing a significant increase in 64% of VOCs, especially hydrogen sulphide, methanethiol, and butanal. A two-way ANOVA revealed significant effects of origin, time, and their interaction on VOC concentration, with 102 mass peaks varying significantly based on all three factors. Seasonal effects were also notable, particularly in reared fish from the Adriatic Sea, where compounds like monoterpenes and aromatics were higher during non-breeding months, likely due to environmental factors unique to that area. Differences between wild and reared fish were influenced by lipid content and seasonal changes, impacting the VOC profile of seabream. These findings provide valuable insights into how cooking, geographical origin, and seasonality interact to define the flavour profile of seabream, with potential applications in improving quality control and product differentiation in seafood production. Full article

(This article belongs to the Special Issue Innovative Analytical Techniques in Food Chemistry)

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16 pages, 3461 KiB

Open AccessArticle

Hierarchically Structured Stimuli-Responsive Liquid Crystalline Terpolymer–Rhodamine Dye Conjugates

by Samiksha Vaidya, Meenakshi Sharma, Christian Brückner and Rajeswari M. Kasi

Molecules 2025, 30(2), 401; https://doi.org/10.3390/molecules30020401 (registering DOI) - 18 Jan 2025

Abstract

Optically responsive materials are applied in sensing, actuators, and optical devices. One such class of material is dye-doped liquid crystal polymers that self-assemble into cholesteric mesophases that reflect visible light. We report here the synthesis and characterization of a family of linear and [...] Read more.

Optically responsive materials are applied in sensing, actuators, and optical devices. One such class of material is dye-doped liquid crystal polymers that self-assemble into cholesteric mesophases that reflect visible light. We report here the synthesis and characterization of a family of linear and mildly crosslinked terpolymers prepared by the ROMP of norbornene-based monomers. The three monomers were composed of (i) rhodamine dye through one or two norbornene end groups utilizing flexible C₁₀-alkane spacers, (ii) a cholesteryl liquid crystal (LC) using C₉-alkane spacers, and (iii) PEG side chains. We investigated how these architectural variations in these terpolymers impacted their hierarchically self-assembled mesophase properties. We probed their composition, morphology, thermal, mechanic, photochromic, and mechanochromic properties using, inter alia, ¹H NMR spectroscopy, DSC, temperature-dependent SAXS, diffuse reflectance UV-vis spectroscopy, and optical polarization microscopy. The new terpolymers exhibited architecture-dependent thermochromic, mechanochromic, and piezochromic properties arising from LC–rhodamine dye interactions. We found that a compromise between the rigidity and flexibility of the terpolymer architectures needed to be stricken to fully express stimuli-responsive properties. These terpolymers also showed distinctly different properties compared to those of a previously reported structurally related liquid crystalline copolymer made from two monomers. These findings help to define the design principles for optimally stimuli-responsive liquid crystalline polymers. Full article

(This article belongs to the Special Issue Polymeric Liquid Crystals and Applications, 2nd Edition)

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