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Isolation and Structure Determination of Bioactive Natural Products (2nd Edition)

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: 31 January 2025 | Viewed by 5784

Special Issue Editors


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Guest Editor
Department of Environmental Chemistry and Ecoanalytics, Faculty of Chemistry, Nicolaus Copernicus University, Gagarin 7, PL-87 100 Torun, Poland
Interests: chromatographic techniques (GC/MS, LC/MS, TLC-MS); sample preparation methods (SPME, SPE, LLE); analysis of plant materials; food and water; determination of VOCs; biomedical chemistry; trace analysis
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Guest Editor
Faculty of Chemistry, Nicolaus Copernitus University in Toruń, Toruń, Poland
Interests: antioxidant capacity; new synthetic antioxidants; oilseeds; vegetable oils; emulsions; confectionery; biodegradable smart packaging; new analytical methods; spectroscopic techniques; chemometric tools

Special Issue Information

Dear Colleagues,

Due to the presence of biologically active compounds, many extracts obtained from natural products have various antioxidant, anti-inflammatory, antifungal, and other properties. These components are widely spread in herbs, fruits, and natural products. Their isolation, separation, and analysis are of great interest in several fields, such as the pharmaceutical and food industries, biochemistry, medical cell biology, nutrition, and biotechnology research. In recent years, the most frequently used approaches, including the selective isolation, preconcentration, and separation of primary and secondary plant metabolites, especially sugars (including cyclitols), polyphenols, terpenes, carotenoids, nitrogen-containing alkaloids, and saponins, present in a range of complex matrices, have been subject to discussion. Various conventional and nonconventional sample preparation methods have been used for the extraction of the abovementioned compounds. Moreover, chromatographic techniques, which are characterized by high sensitivity, selectivity, and versatility, are widely applied for the determination of these compounds.

This Special Issue is dedicated to featuring the latest research that is ongoing in the field of bioactive natural products. It is expected that most submissions will focus on the methodology of the isolation and determination of biologically active compounds, but structural analyses will also be considered. Original research (communications, full papers, and reviews) that discusses innovative methodologies for the research of bioactive natural products with potential applications in various industries is therefore welcome.

Dr. Magdalena Ligor
Prof. Dr. Aleksandra Szydłowska-Czerniak
Guest Editors

Manuscript Submission Information

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Keywords

  • primary and secondary plant metabolites
  • sample preparation methods
  • hyphenated analytical methods
  • natural product research
  • measuring biological activity
  • structure-activity relationships

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Related Special Issue

Published Papers (4 papers)

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Research

20 pages, 5382 KiB  
Article
Selectivity Screening and Structure–Cytotoxic Activity Observations of Selected Oleanolic Acid (OA)-Type Saponins from the Amaranthaceae Family on a Wide Panel of Human Cancer Cell Lines
by Karolina Grabowska, Agnieszka Galanty, Łukasz Pecio, Anna Stojakowska, Janusz Malarz, Paweł Żmudzki, Paweł Zagrodzki and Irma Podolak
Molecules 2024, 29(16), 3794; https://doi.org/10.3390/molecules29163794 - 10 Aug 2024
Viewed by 1138
Abstract
Plants from the Amaranthaceae family are a source of oleanolic acid (OA)-type saponins with cytotoxic activity. Two known OA-type saponins, calenduloside E and chikusetsusaponin IVa, were isolated from the roots of Chenopodium strictum Roth. Their structures were confirmed using MS and NMR techniques. [...] Read more.
Plants from the Amaranthaceae family are a source of oleanolic acid (OA)-type saponins with cytotoxic activity. Two known OA-type saponins, calenduloside E and chikusetsusaponin IVa, were isolated from the roots of Chenopodium strictum Roth. Their structures were confirmed using MS and NMR techniques. This constitutes the inaugural report of the saponins in Ch. strictum. Both the isolated saponins and structurally similar compounds, momordin Ic and OA, were compared for their cytotoxicity against various cancer and normal cell lines (including skin, breast, thyroid, gastrointestinal, and prostate panels). Their effects were dose- and time-dependent, varying with the specific cell line and compound structure. A chemometric approach demonstrated the effects of the compounds on the cell lines. The study discusses the structure–activity observations. The key structural elements for potent cytotoxic activity included the free carboxyl group 28COOH in the sapogenin structure (OA) and the presence of a sugar moiety. The monodesmosides with glucuronic acid (GlcA) at the C3 position of OA were generally more cytotoxic than bidesmosides or OA alone. The addition of xylose in the sugar chain modified the activity towards the cancer cells depending on the specific cell line. OA-type saponins with GlcA (particularly calenduloside E and momordin Ic) represent a promising avenue for further investigation as potential anticancer agents. Full article
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12 pages, 5325 KiB  
Article
The Peculiar H-Bonding Network of 4-Methylcatechol: A Coupled Diffraction and In Silico Study
by Mattia Lopresti, Luca Palin, Giovanni Calegari and Marco Milanesio
Molecules 2024, 29(10), 2173; https://doi.org/10.3390/molecules29102173 - 7 May 2024
Cited by 1 | Viewed by 919
Abstract
The crystal structure of 4-methylcatechol (4MEC) has, to date, never been solved, despite its very simple chemical formula C7O2H8 and the many possible applications envisaged for this molecule. In this work, this gap is filled and the structure [...] Read more.
The crystal structure of 4-methylcatechol (4MEC) has, to date, never been solved, despite its very simple chemical formula C7O2H8 and the many possible applications envisaged for this molecule. In this work, this gap is filled and the structure of 4MEC is obtained by combining X-ray powder diffraction and first principle calculations to carefully locate hydrogen atoms. Two molecules are present in the asymmetric unit. Hirshfeld analysis confirmed the reliability of the solved structure, since the two molecules show rather different environments and H-bond interactions of different directionality and strength. The packing is characterised by a peculiar hydrogen bond network with hydroxyl nests formed by two adjacent octagonal frameworks. It is noteworthy that the observed short contacts suggest strong inter-molecular interactions, further confirmed by strong inter-crystalline aggregation observed by microscopic images, indicating the growth, in many crystallization attempts, of single aggregates taller than half a centimetre and, often, with spherical shapes. These peculiarities are induced by the presence of methyl group in 4MEC, since the parent compound catechol, despite its chemical similarity, shows a standard layered packing alternating hydrophobic and polar layers. Finally, the complexity and peculiarity of the packing and crystal growth features explain why a single crystal could not be obtained for a standard structural analysis. Full article
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25 pages, 3061 KiB  
Article
Comparative Studies of Extracts Obtained from Brassica oleracea L. Plants at Different Stages of Growth by Isolation and Determination of Isothiocyanates: An Assessment of Chemopreventive Properties of Broccoli
by Magdalena Ligor, Małgorzata Szultka-Młyńska, Katarzyna Rafińska and Agata Cwudzińska
Molecules 2024, 29(2), 519; https://doi.org/10.3390/molecules29020519 - 20 Jan 2024
Cited by 1 | Viewed by 1540
Abstract
The main goal of this work was to develop analytical procedures for the isolation and determination of selected isothiocyanates. As an example, particularly sulforaphane from plants of the Brassicaceae Burnett or Cruciferae Juss family. The applied methodology was mainly based on classical extraction [...] Read more.
The main goal of this work was to develop analytical procedures for the isolation and determination of selected isothiocyanates. As an example, particularly sulforaphane from plants of the Brassicaceae Burnett or Cruciferae Juss family. The applied methodology was mainly based on classical extraction methods and high-performance liquid chromatography coupled with tandem mass spectrometry. Moreover, the effect of temperature on the release of isothiocyanates from plant cells was considered. The cytotoxic activity of the obtained plant extracts against a selected cancer cell line has also been included. The results allow evaluating the usefulness of obtained plant extracts and raw sprouts regarding their content of isothiocyanates—bioactive compounds with chemopreventive properties. Full article
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11 pages, 984 KiB  
Article
Anticholinesterase and Antityrosinase Secondary Metabolites from the Fungus Xylobolus subpileatus
by Kristóf Felegyi, Zsófia Garádi, Elżbieta Studzińska-Sroka, Viktor Papp, Imre Boldizsár, András Dancsó, Szabolcs Béni, Przemysław Zalewski and Attila Ványolós
Molecules 2024, 29(1), 213; https://doi.org/10.3390/molecules29010213 - 30 Dec 2023
Cited by 1 | Viewed by 1634
Abstract
Xylobolus subpileatus is a widely distributed crust fungus reported from all continents except Antarctica, although considered a rare species in several European countries. Profound mycochemical analysis of the methanol extract of X. subpileatus resulted in the isolation of seven compounds (1 [...] Read more.
Xylobolus subpileatus is a widely distributed crust fungus reported from all continents except Antarctica, although considered a rare species in several European countries. Profound mycochemical analysis of the methanol extract of X. subpileatus resulted in the isolation of seven compounds (17). Among them, (3β,22E)-3-methoxy-ergosta-4,6,814,22-tetraene (1) is a new natural product, while the NMR assignment of its already known epimer (2) has been revised. In addition to a benzohydrofuran derivative fomannoxin (3), four ergostane-type triterpenes 47 were identified. The structure elucidation of the isolated metabolites was performed by one- and two-dimensional NMR and MS analysis. Compounds 27 as well as the chloroform, n-hexane, and methanol extracts of X. subpileatus were evaluated for their tyrosinase, acetylcholinesterase, and butyrylcholinesterase inhibitory properties. Among the examined compounds, only fomannoxin (3) displayed the antityrosinase property with 51% of inhibition, and the fungal steroids proved to be inactive. Regarding the potential acetylcholinesterase (AChE) inhibitory activity of the fungal extracts and metabolites, it was demonstrated that the chloroform extract and compounds 34 exerted noteworthy inhibitory activity, with 83.86 and 32.99%, respectively. The butyrylcholinesterase (BChE) inhibitory assay revealed that methanol and chloroform extracts, as well as compounds 3 and 4, exerted notable activity, while the rest of the compounds proved to be only weak enzyme inhibitors. Our study represents the first report on the chemical profile of basidiome of the wild-growing X. subpileatus, offering a thorough study on the isolation and structure determination of the most characteristic biologically active constituents of this species. Full article
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