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State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of...
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State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021

A special issue of Biomolecules (ISSN 2218-273X).

Deadline for manuscript submissions: closed (15 December 2021) | Viewed by 62506

Special Issue Editor

Prof. Dr. Antonio Evidente

E-Mail Website
Guest Editor
Institute of Sciences of Food Production, National Research Council, Via Amendola 122/O, 70125 Bari, Italy
Interests: chemistry of natural substance; spectroscopy; biosynthesis; structure activity relationships
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue aims to provide a comprehensive overview of the Isolation, Chemical and Biological Characterization, Synthesis, and Formulation of Natural Products. We invite the submission of research papers that will consolidate our understanding in this area. This Special Issue will publish original research articles and systematic reviews. Potential topics include, but are not limited to:

  • isolation and chemical and biological characterization of natural products;
  • determination of the relative and absolute configuration of natural products;
  • total and partial synthesis of natural products and analogues and derivatives;
  • structure–activity relationships and the mode of action of natural products;
  • bioformulation of natural products for potential practical application in different fields (e.g., agriculture, food packaging, medicine, and cosmetics).

Prof. Dr. Antonio Evidente
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Biomolecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • isolation and chemical and biological characterization of natural products
  • determination of the relative and absolute configuration of natural products
  • total and partial synthesis of natural products and analogues and derivatives
  • structure–activity relationships and the mode of action of natural products
  • bioformulation of natural products for potential practical application in different fields (e.g., agriculture, food packaging, medicine, and cosmetics).

Published Papers (22 papers)

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Research

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11 pages, 1882 KiB  
Article
Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-p-menthane as a Case Study
by Giulia Marsico, Umberto Calice, Patrizia Scafato, Sandra Belviso, Antonio Evidente and Stefano Superchi
Biomolecules 2022, 12(3), 421; https://0-doi-org.brum.beds.ac.uk/10.3390/biom12030421 - 09 Mar 2022
Cited by 1 | Viewed by 1860
Abstract
In this study, the computational analysis of electronic circular dichroism (ECD) spectra and the employment of biphenyl chiroptical probes were compared in the absolute configuration assignment of (-)-1α,2α,3β-trihydroxy-p-menthane (1), taken as a representative example of a UV-transparent chiral natural [...] Read more.
In this study, the computational analysis of electronic circular dichroism (ECD) spectra and the employment of biphenyl chiroptical probes were compared in the absolute configuration assignment of (-)-1α,2α,3β-trihydroxy-p-menthane (1), taken as a representative example of a UV-transparent chiral natural product. The usefulness of chiroptical probes in the configurational assignments of natural products and their complementarity to the computational protocols is herein highlighted. The biphenyl probe approach proves to be straightforward, reliable, and suitable for conformationally mobile and ECD silent compounds, not treatable by computational analysis of chiroptical data. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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11 pages, 1640 KiB  
Article
Inuloxin A Inhibits Seedling Growth and Affects Redox System of Lycopersicon esculentum Mill. and Lepidium sativum L.
by Alessandra Villani, Maria Chiara Zonno, Silvana de Leonardis, Maurizio Vurro and Costantino Paciolla
Biomolecules 2022, 12(2), 302; https://0-doi-org.brum.beds.ac.uk/10.3390/biom12020302 - 12 Feb 2022
Cited by 1 | Viewed by 1850
Abstract
Allelochemicals are considered an environment-friendly and promising alternative for weed management, although much effort is still needed for understanding their mode of action and then promoting their use in plant allelopathy management practices. Here, we report that Inuloxin A (InA), an allelochemical isolated [...] Read more.
Allelochemicals are considered an environment-friendly and promising alternative for weed management, although much effort is still needed for understanding their mode of action and then promoting their use in plant allelopathy management practices. Here, we report that Inuloxin A (InA), an allelochemical isolated from Dittrichia viscosa, inhibited root elongation and growth of seedlings of Lycopersicon esculentum and Lepidium sativum at the highest concentrations tested. InA-induced antioxidant responses in the seedlings were investigated by analysing the contents of glutathione (GSH) and ascorbate (ASC), and their oxidized forms, dehydroascorbate (DHA), and glutathione disulphide (GSSG), as well as the redox state of thiol-containing proteins. An increase in ASC, DHA, and GSH levels at high concentrations of InA, after 3 and 6 days, were observed. Moreover, the ASC/DHA + ASC and GSH/GSSG + GSH ratios showed a shift towards the oxidized form. Our study provides the first insight into how the cell redox system responds and adapts to InA phytotoxicity, providing a framework for further molecular studies. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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13 pages, 1961 KiB  
Article
Identification of the Marine Alkaloid Lepadin A as Potential Inducer of Immunogenic Cell Death
by Genoveffa Nuzzo, Carmela Gallo, Fabio Crocetta, Lucia Romano, Giusi Barra, Giuseppina Senese, Mario dell’Isola, Dalila Carbone, Valentina Tanduo, Federica Albiani, Guido Villani, Giuliana d’Ippolito, Emiliano Manzo and Angelo Fontana
Biomolecules 2022, 12(2), 246; https://0-doi-org.brum.beds.ac.uk/10.3390/biom12020246 - 02 Feb 2022
Cited by 8 | Viewed by 2265
Abstract
Natural products and their synthetic analogs and derivatives are a traditional source of bioactive molecules with potential development as drug candidates. In this context, Marine Natural Products (MNPs) represent a rich reservoir of diverse molecular skeletons with potential pharmacological activity that, so far, [...] Read more.
Natural products and their synthetic analogs and derivatives are a traditional source of bioactive molecules with potential development as drug candidates. In this context, Marine Natural Products (MNPs) represent a rich reservoir of diverse molecular skeletons with potential pharmacological activity that, so far, has been mostly explored in cancer and infectious diseases. Starting from the development of a novel bioassay-guided screening platform for immunomodulatory compounds from an in-house MNPs library, we report the identification of the alkaloid lepadin A as a new model compound for immune-based anticancer activity with characteristics that suggest a possible mechanism as Immunogenic Cell Death inducer. The work describes the molecular-based bioprospecting in the Gulf of Naples together with the bioassay-guided fractionation, the chemical characterization of the alkaloid, and the biological activity in mouse dendritic cells (D1). Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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26 pages, 9681 KiB  
Article
In Silico, In Vitro, and In Vivo Analysis of Tanshinone IIA and Cryptotanshinone from Salvia miltiorrhiza as Modulators of Cyclooxygenase-2/mPGES-1/Endothelial Prostaglandin EP3 Pathway
by Anella Saviano, Simona De Vita, Maria Giovanna Chini, Noemi Marigliano, Gianluigi Lauro, Gian Marco Casillo, Federica Raucci, Maria Iorizzi, Robert Klaus Hofstetter, Katrin Fischer, Andreas Koeberle, Oliver Werz, Francesco Maione and Giuseppe Bifulco
Biomolecules 2022, 12(1), 99; https://0-doi-org.brum.beds.ac.uk/10.3390/biom12010099 - 07 Jan 2022
Cited by 2 | Viewed by 2097
Abstract
Tanshinone IIA (TIIA) and cryptotanshinone (CRY) from Salvia miltiorrhiza Bunge were investigated for their inhibitory activity against the cyclooxygenase-2 (COX-2)/microsomal prostaglandin E synthase-1 (mPGES-1)/endothelial prostaglandin 3 (EP3) pathway using in silico, in vitro, in vivo, and ex vivo assays. From the analysis of [...] Read more.
Tanshinone IIA (TIIA) and cryptotanshinone (CRY) from Salvia miltiorrhiza Bunge were investigated for their inhibitory activity against the cyclooxygenase-2 (COX-2)/microsomal prostaglandin E synthase-1 (mPGES-1)/endothelial prostaglandin 3 (EP3) pathway using in silico, in vitro, in vivo, and ex vivo assays. From the analysis of the docking poses, both diterpenoids were able to interact significantly with COX-2, 5-lipoxygenase (5-LO), platelet-activating factor receptor (PAFR), and mPGES-1. This evidence was further corroborated by data obtained from a cell-free assay, where CRY displayed a significant inhibitory potency against mPGES-1 (IC50 = 1.9 ± 0.4 µM) and 5-LO (IC50 = 7.1 µM), while TIIA showed no relevant inhibition of these targets. This was consistent with their activity to increase mice bleeding time (CRY: 2.44 ± 0.13 min, p ≤ 0.001; TIIA: 2.07 ± 0.17 min p ≤ 0.01) and with the capability to modulate mouse clot retraction (CRY: 0.048 ± 0.011 g, p ≤ 0.01; TIIA: 0.068 ± 0.009 g, p ≤ 0.05). For the first time, our results show that TIIA and, in particular, CRY are able to interact significantly with the key proteins involved not only in the onset of inflammation but also in platelet activity (and hyper-reactivity). Future preclinical and clinical investigations, together with this evidence, could provide the scientific basis to consider these compounds as an alternative therapeutic approach for thrombotic- and thromboembolic-based diseases. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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14 pages, 3478 KiB  
Article
Polysaccharide Based Polymers Produced by Scabby Cankered Cactus Pear (Opuntia ficus-indica L.) Infected by Neofusicoccum batangarum: Composition, Structure, and Chemico-Physical Properties
by Gabriella Santagata, Alessio Cimmino, Giovanni Dal Poggetto, Domenico Zannini, Marco Masi, Alessandro Emendato, Giuseppe Surico and Antonio Evidente
Biomolecules 2022, 12(1), 89; https://0-doi-org.brum.beds.ac.uk/10.3390/biom12010089 - 06 Jan 2022
Cited by 5 | Viewed by 1750
Abstract
Neofusiccocum batangarum is the causal agent of scabby canker of cactus pear (Opuntia ficus-indica L.). The symptoms of this disease are characterized by crusty, perennial cankers, with a leathery, brown halo. Characteristically, a viscous polysaccharide exudate, caking on contact with air, leaks [...] Read more.
Neofusiccocum batangarum is the causal agent of scabby canker of cactus pear (Opuntia ficus-indica L.). The symptoms of this disease are characterized by crusty, perennial cankers, with a leathery, brown halo. Characteristically, a viscous polysaccharide exudate, caking on contact with air, leaks from cankers and forms strips or cerebriform masses on the surface of cactus pear cladodes. When this polysaccharide mass was partial purified, surprisingly, generated a gel. The TLC analysis and the HPLC profile of methyl 2-(polyhydroxyalkyl)-3-(o-tolylthiocarbomoyl)-thiazolidine-4R-carboxylates obtained from the mixture of monosaccharides produced by acid hydrolysis of the three EPSs examined in this research work [the polysaccharide component of the exudate (EPSC) and the EPSs extracted from asymptomatic (EPSH) and symptomatic (EPSD) cladodes] showed the presence of d-galactose, l-rhamnose, and d-glucose in a 1:1:0.5 ratio in EPSC while d-galactose, l-rhamnose, d-glucose, and d-xylose at the same ratio were observed in EPSH and EPSD. The presence of uronic acid residues in EPSC was also showed by solid state NMR and IR investigation. Furthermore, this manuscript reports the chemical-physical characterization of the gel produced by the infected cactus pear. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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12 pages, 2741 KiB  
Article
The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of Chiliadenus lopadusanus Metabolites
by Giuseppe Mazzeo, Alessio Cimmino, Giovanna Longhi, Marco Masi, Antonio Evidente and Sergio Abbate
Biomolecules 2021, 11(12), 1902; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11121902 - 18 Dec 2021
Cited by 2 | Viewed by 2232
Abstract
9-Hydroxynerolidol, 9-oxonerolidol, and chiliadenol B are three farnesane-type sesquiterpenoids isolated from Chiliadenus lopadusanus that have shown an interesting activity against human pathogens as Gram+ and Gram− bacteria resistant to antibiotics. However, the absolute configuration (AC) of these interesting sesquiterpenes has not been assigned [...] Read more.
9-Hydroxynerolidol, 9-oxonerolidol, and chiliadenol B are three farnesane-type sesquiterpenoids isolated from Chiliadenus lopadusanus that have shown an interesting activity against human pathogens as Gram+ and Gram− bacteria resistant to antibiotics. However, the absolute configuration (AC) of these interesting sesquiterpenes has not been assigned so far. Vibrational and electronic circular dichroism spectra have been recorded and correlations are pointed out for the three compounds. Density functional theory (DFT) calculations are used in conjunction with Mosher’s method of investigation to assign AC. Statistical analysis is considered to quantitatively define the choice of AC from VCD spectra. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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13 pages, 2687 KiB  
Article
Pseudomonas fluorescens Showing Antifungal Activity against Macrophomina phaseolina, a Severe Pathogenic Fungus of Soybean, Produces Phenazine as the Main Active Metabolite
by Stefany Castaldi, Marco Masi, Francisco Sautua, Alessio Cimmino, Rachele Isticato, Marcelo Carmona, Angela Tuzi and Antonio Evidente
Biomolecules 2021, 11(11), 1728; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11111728 - 19 Nov 2021
Cited by 13 | Viewed by 2597
Abstract
Pseudomonas fluorescens 9 and Bacillus subtilis 54, proposed as biofungicides to control Macrophomina phaseolina, a dangerous pathogen of soybean and other crops, were grown in vitro to evaluate their ability to produce metabolites with antifungal activity. The aim of the manuscript was [...] Read more.
Pseudomonas fluorescens 9 and Bacillus subtilis 54, proposed as biofungicides to control Macrophomina phaseolina, a dangerous pathogen of soybean and other crops, were grown in vitro to evaluate their ability to produce metabolites with antifungal activity. The aim of the manuscript was to identify the natural compounds responsible for their antifungal activity. Only the culture filtrates of P. fluorescens 9 showed strong antifungal activity against M. phaseolina. Its organic extract contained phenazine and mesaconic acid (1 and 2), whose antifungal activity was tested against M. phaseolina, as well as Cercospora nicotianae and Colletotrichum truncatum, other pathogens of soybean; however, only compound 1 exhibited activity. The antifungal activity of compound 1 was compared to phenazine-1-carboxylic acid (PCA, 3), 2-hydroxyphenazine (2-OH P, 4), and various semisynthetic phenazine nitro derivatives in order to perform a structure–activity relationship (SAR) study. PCA and phenazine exhibited the same percentage of growth inhibition in M. phaseolina and C. truncatum, whereas PCA (3) showed lower activity against C. nicotianae than phenazine. 2-Hydroxyphenazine (4) showed no antifungal activity against M. phaseolina. The results of the SAR study showed that electron attractor (COOH and NO2) or repulsor (OH) groups significantly affect the antifungal growth, as well as their α- or β-location on the phenazine ring. Both PCA and phenazine could be proposed as biopesticides to control the soybean pathogens M. phaseolina, C. nicotianae, and C. truncatum, and these results should prompt an investigation of their large-scale production and their suitable formulation for greenhouse and field applications. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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17 pages, 1865 KiB  
Article
Extraction and Chemical Characterization of Functional Phenols and Proteins from Coffee (Coffea arabica) By-Products
by Barbara Prandi, Maura Ferri, Stefania Monari, Chiara Zurlini, Ilaria Cigognini, Stefanie Verstringe, Dennis Schaller, Martha Walter, Luciano Navarini, Annalisa Tassoni, Stefano Sforza and Tullia Tedeschi
Biomolecules 2021, 11(11), 1571; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11111571 - 22 Oct 2021
Cited by 16 | Viewed by 4437
Abstract
Not all the coffee produced goes to the roasting stage, because non-compliant green coffee beans are usually discarded by roasters and the silverskin of the coffee is usually removed and discarded. In the present work, non-compliant green coffee beans and coffee silverskins were [...] Read more.
Not all the coffee produced goes to the roasting stage, because non-compliant green coffee beans are usually discarded by roasters and the silverskin of the coffee is usually removed and discarded. In the present work, non-compliant green coffee beans and coffee silverskins were fully characterized from a chemical point of view. In addition, enzyme-assisted extraction was applied to recover a fraction rich in proteins and polyphenols, tested for antimicrobial, antityrosinase, and antioxidant activities. Non-compliant green coffee beans showed higher amounts of polyphenols, flavanols, flavonoids, and caffeine than coffee silverskins (which were richer in tannins). The enzymatic extraction of non-compliant coffee green beans produced extracts with a good protein content and with a consistent quantity of polyphenols. The extract showed antioxidant, antityrosinase, and antimicrobial activity, thus representing a promising strategy to recover defective green coffee beans. The antioxidant and antimicrobial activity of coffee silver skins is lower than that of non-compliant coffee green beans extracts, while the antityrosinase activity is comparable. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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18 pages, 9321 KiB  
Article
Biological Profile of Two Gentiana lutea L. Metabolites Using Computational Approaches and In Vitro Tests
by Simona De Vita, Maria Giovanna Chini, Gabriella Saviano, Claudia Finamore, Carmen Festa, Gianluigi Lauro, Simona De Marino, Roberto Russo, Carmen Avagliano, Agostino Casapullo, Antonio Calignano, Giuseppe Bifulco and Maria Iorizzi
Biomolecules 2021, 11(10), 1490; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11101490 - 09 Oct 2021
Cited by 4 | Viewed by 2266
Abstract
Natural products have been the main source of bioactive molecules for centuries. We tested the biological profile of two metabolites extracted from Gentiana lutea L. by means of computational techniques and in vitro assays. The two molecules (loganic acid and gentiopicroside) were tested [...] Read more.
Natural products have been the main source of bioactive molecules for centuries. We tested the biological profile of two metabolites extracted from Gentiana lutea L. by means of computational techniques and in vitro assays. The two molecules (loganic acid and gentiopicroside) were tested in silico using an innovative technique, named Inverse Virtual Screening (IVS), to highlight putative partners among a panel of proteins involved in inflammation and cancer events. A positive binding with cyclooxygenase-2 (COX-2), alpha-1-antichymotrypsin, and alpha-1-acid glycoprotein emerged from the computational experiments and the outcomes from the promising interaction with COX-2 were confirmed by Western blot, highlighting the reliability of IVS in the field of the natural products. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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21 pages, 5746 KiB  
Article
Isolation and Biological Characterization of Homoisoflavanoids and the Alkylamide N-p-Coumaroyltyramine from Crinum biflorum Rottb., an Amaryllidaceae Species Collected in Senegal
by Marco Masi, Manoj Koirala, Antonella Delicato, Roberta Di Lecce, Natacha Merindol, Seydou Ka, Matar Seck, Angela Tuzi, Isabel Desgagne-Penix, Viola Calabrò and Antonio Evidente
Biomolecules 2021, 11(9), 1298; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11091298 - 31 Aug 2021
Cited by 11 | Viewed by 3706
Abstract
Crinum biflorum Rottb. (syn. Crinum distichum) is an Amaryllidaceae plant used in African traditional medicine but very few studies have been performed on this species from a chemical and applicative point of view. Bulbs of C. biflorum, collected in Senegal, were [...] Read more.
Crinum biflorum Rottb. (syn. Crinum distichum) is an Amaryllidaceae plant used in African traditional medicine but very few studies have been performed on this species from a chemical and applicative point of view. Bulbs of C. biflorum, collected in Senegal, were extracted with ethanol by Soxhlet and the corresponding organic extract was purified using chromatographic methods. The pure compounds were chemically characterized by spectroscopic techniques (1D and 2D 1H and 13C NMR, HR MS and ECD) and X-ray analysis. Four homoisoflavonoids (1–4) and one alkylamide (5) were isolated and characterized as 5,6,7-trimethoxy-3-(4-hydroxybenzyl)chroman-4-one (1), as 3-hydroxy-5,6,7-trimethoxy-3-(4-hydroxybenzyl)chroman-4-one (2), as 3-hydroxy-5,6,7-trimethoxy-3-(4-methoxybenzyl)chroman-4-one (3) and as 5,6,7-trimethoxy-3-(4-methoxybenzyl)chroman-4-one (4), and the alkylamide as (E)-N-(4-hydroxyphenethyl)-3-(4-hydroxyphenyl)acrylamide (5), commonly named N-p-coumaroyltyramine. The relative configuration of compound 1 was verified thanks to the X-ray analysis which also allowed us to confirm its racemic nature. The absolute configurations of compounds 2 and 3 were assigned by comparing their ECD spectra with those previously reported for urgineanins A and B. Flavanoids 1, 3 and 4 showed promising anticancer properties being cytotoxic at low micromolar concentrations towards HeLa and A431 human cancer cell lines. The N-p-coumaroyltyramine (5) was selectively toxic to A431 and HeLa cancer cells while it protected immortalized HaCaT cells against oxidative stress induced by hydrogen peroxide. Compounds 1–4 also inhibited acetylcholinesterase activity with compound 3 being the most potent. The anti-amylase and the strong anti-glucosidase activity of compound 5 were confirmed. Our results show that C. biflorum produces compounds of therapeutic interest with anti-diabetic, anti-tumoral and anti-acetylcholinesterase properties. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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10 pages, 857 KiB  
Article
Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian Centaurea omphalotricha
by Sara Kebbi, Maria Letizia Ciavatta, Ali Mokhtar Mahmoud, Marianna Carbone, Alessia Ligresti, Ramdane Seghiri and Margherita Gavagnin
Biomolecules 2021, 11(7), 1053; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11071053 - 18 Jul 2021
Cited by 7 | Viewed by 2364
Abstract
In continuing our investigation on the chemical diversity of Algerian plants, we examined Centaurea omphalotricha, whose chemical composition has been poorly studied. The present work was aimed at characterizing the secondary metabolite pattern of the CHCl3 extract of the aerial parts [...] Read more.
In continuing our investigation on the chemical diversity of Algerian plants, we examined Centaurea omphalotricha, whose chemical composition has been poorly studied. The present work was aimed at characterizing the secondary metabolite pattern of the CHCl3 extract of the aerial parts of this plant that displayed antiproliferative properties in a preliminary screening on HeLa cell line. The chemical analysis led us to characterize the bioactive oxygenated terpenoid fraction which includes, within major known metabolites, two new minor sesquiterpene lactones, centaurolide-A (1) and centaurolide-B (2). The structures of two compounds exhibiting the 12,8-guaianolide skeleton were determined by spectroscopic methods as well as by chemical correlation with inuviscolide (3), a well-known bioactive guaianolide isolated from Dittrichia (=Inula) viscosa. Centaurolides A and B represent the first report of 8,12-guaianolide skeleton in Centaurea genus. The effect of new compounds 1 and 2 and inuviscolide (3) on HeLa cell has also been evaluated. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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14 pages, 1583 KiB  
Article
Chemical Fractionation Joint to In-Mixture NMR Analysis for Avoiding the Hepatotoxicity of Teucrium chamaedrys L. subsp. chamaedrys
by Simona Piccolella, Monica Scognamiglio, Brigida D’Abrosca, Assunta Esposito, Antonio Fiorentino and Severina Pacifico
Biomolecules 2021, 11(5), 690; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11050690 - 05 May 2021
Cited by 5 | Viewed by 1993
Abstract
Dietary supplements based on Teucrium chamaedrys L. subsp. chamaedrys aerial parts were banned, due to the hepatotoxicity of furan-containing neo-clerodane constituents. Indeed, the plant leaf content in phenolic compounds could be further exploited for their antioxidant capability. Accordingly, bio-guided fractionation strategies have [...] Read more.
Dietary supplements based on Teucrium chamaedrys L. subsp. chamaedrys aerial parts were banned, due to the hepatotoxicity of furan-containing neo-clerodane constituents. Indeed, the plant leaf content in phenolic compounds could be further exploited for their antioxidant capability. Accordingly, bio-guided fractionation strategies have been applied, obtaining seven partially purified extracts. These latter were chemically investigated through 1D and 2D NMR techniques and tested for their antiradical, reducing and cytotoxic capability. Data acquired highlighted that, through a simple phytochemical approach, a progressive neo-clerodane depletion occurred, while maximizing phenylethanoid glycosides in alcoholic fractions. Thus, although the plant cannot be used as a botanical remedy as such, it is suggested as a source of healthy compounds, pure or in mixture, to be handled in pharmaceutical, nutraceutical and/or cosmeceutical sectors. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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13 pages, 1953 KiB  
Article
Combined Analytical Approaches to Standardize and Characterize Biomaterials Formulations: Application to Chitosan-Gelatin Cross-Linked Hydrogels
by Sofia Magli, Lorenzo Rossi, Cesare Consentino, Sabrina Bertini, Francesco Nicotra and Laura Russo
Biomolecules 2021, 11(5), 683; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11050683 - 01 May 2021
Cited by 11 | Viewed by 3107
Abstract
A protocol based on the combination of different analytical methodologies is proposed to standardize the experimental conditions for reproducible formulations of hybrid hydrogels. The final hybrid material, based on the combination of gelatin and chitosan functionalized with methylfuran and cross-linked with 4-arm-PEG-maleimide, is [...] Read more.
A protocol based on the combination of different analytical methodologies is proposed to standardize the experimental conditions for reproducible formulations of hybrid hydrogels. The final hybrid material, based on the combination of gelatin and chitosan functionalized with methylfuran and cross-linked with 4-arm-PEG-maleimide, is able to mimic role, dynamism, and structural complexity of the extracellular matrix. Physical–chemical properties of starting polymers and finals constructs were characterized exploiting the combination of HP-SEC-TDA, UV, FT-IR, NMR, and TGA. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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9 pages, 2082 KiB  
Article
Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages
by Giuseppina Chianese, Francesca Masi, Donatella Cicia, Daniele Ciceri, Sabrina Arpini, Mario Falzoni, Ester Pagano and Orazio Taglialatela-Scafati
Biomolecules 2021, 11(4), 494; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11040494 - 25 Mar 2021
Cited by 8 | Viewed by 2456
Abstract
A madecassoside-rich fraction obtained from the industrial purification of Centella asiatica leaves afforded a new triterpene glycoside, named isomadecassoside (4), characterized by an ursane-type skeleton and migration of the double bond at Δ20(21) in ring E. The structure of isomadecassoside [...] Read more.
A madecassoside-rich fraction obtained from the industrial purification of Centella asiatica leaves afforded a new triterpene glycoside, named isomadecassoside (4), characterized by an ursane-type skeleton and migration of the double bond at Δ20(21) in ring E. The structure of isomadecassoside was established by means of HR-ESIMS and detailed analysis of 1D and 2D NMR spectra, which allowed a complete NMR assignment. Studies on isolated J774A.1 macrophages stimulated by LPS revealed that isomadecassoside (4) inhibited nitrite production at non-cytotoxic concentrations, thus indicating an anti-inflammatory effect similar to that of madecassoside. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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17 pages, 1926 KiB  
Article
Phytochemical Analysis and Biological Activities of the Ethanolic Extract of Daphne sericea Vahl Flowering Aerial Parts Collected in Central Italy
by Claudio Frezza, Alessandro Venditti, Daniela De Vita, Fabio Sciubba, Pierpaolo Tomai, Marco Franceschin, Mirella Di Cecco, Giampiero Ciaschetti, Antonella Di Sotto, Annarita Stringaro, Marisa Colone, Alessandra Gentili, Mauro Serafini and Armandodoriano Bianco
Biomolecules 2021, 11(3), 379; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11030379 - 03 Mar 2021
Cited by 5 | Viewed by 2716
Abstract
In this paper, the first phytochemical analysis of the ethanolic extract of Daphne sericea Vahl flowering aerial parts collected in Italy and its biological activities were reported. Eleven compounds were identified i.e., α-linolenic acid (1), tri-linoleoyl-sn-glycerol (2), [...] Read more.
In this paper, the first phytochemical analysis of the ethanolic extract of Daphne sericea Vahl flowering aerial parts collected in Italy and its biological activities were reported. Eleven compounds were identified i.e., α-linolenic acid (1), tri-linoleoyl-sn-glycerol (2), pheophorbide a ethyl ester (3), pilloin (4), sinensetin (5), yuanhuanin (6), rutamontine (7), syringin (8), p-coumaric acid (9), p-anisic acid (10) and caffeic acid (11). To the best of our knowledge, compounds (1-4, 7-8 and 10) were isolated from D. sericea for the first time during this work, whereas sinensetin (5) represents a newly identified component of the entire Thymelaeaceae family. The extract was found to possess radical scavenging against both DPPH• and 2,2′-azino-bis(3-thylbenzothiazoline-6-sulfonic acid (ABTS•+) radicals, with at least a 40-fold higher potency against the latter. Moreover, chelating abilities against both ferrous and ferric ions have been highlighted, thus suggesting a possible indirect antioxidant power of the extract. Although the precise bioactive compounds remain to be discovered, the polyphenolic constituents, including phenolic acids, tannins and flavonoids, seem to contribute to the antioxidant power of the phytocomplex. In addition, the extract produced cytotoxic effects in MDA-MB-231 and U87-MG cancer cell lines, especially at the concentration of 625 μg/mL and after 48–72 h. Further studies are required to clarify the contribution of the identified compounds in the bioactivities of the extract and to support possible future applications. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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13 pages, 2872 KiB  
Article
Fungal Metabolites with Antagonistic Activity against Fungi of Lithic Substrata
by Marco Masi, Mariagioia Petraretti, Antonino De Natale, Antonino Pollio and Antonio Evidente
Biomolecules 2021, 11(2), 295; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11020295 - 16 Feb 2021
Cited by 6 | Viewed by 1880
Abstract
Fungi are among the biotic agents that can cause deterioration of building stones and cultural heritage. The most common methods used to control fungal spread and growth are based on chemical pesticides. However, the massive use of these synthetic chemicals produces heavy environmental [...] Read more.
Fungi are among the biotic agents that can cause deterioration of building stones and cultural heritage. The most common methods used to control fungal spread and growth are based on chemical pesticides. However, the massive use of these synthetic chemicals produces heavy environmental pollution and risk to human and animal health. Furthermore, their use is time dependent and relies on the repetition of treatments, which increases the possibility of altering building stones and culture heritage through environmental contamination. One alternative is the use of natural products with high antifungal activity, which can result in reduced toxicity and deterioration of archeological remains. Recently, three fungal strains, namely Aspergillus niger, Alternaria alternata and Fusarium oxysporum, were isolated as damaging agents from the external tuff wall of the Roman remains “Villa of Poppea” in Oplontis, Naples, Italy. In this manuscript, three selected fungal metabolites, namely cyclopaldic acid, cavoxin and epi-epoformin, produced by fungi pathogenic for forest plants, were evaluated as potential antifungal compounds against the above fungi. Cavoxin and epi-epoformin showed antifungal activity against Asperigillus niger and Fusarium oxysporum, while cyclopaldic acid showed no activity when tested on the three fungi. The same antifungal activity was observed in vitro experiments on infected stones of the Neapolitan yellow tuff (NYT), a volcanic lithotype widely diffused in the archeological sites of Campania, Italy. This study represents a first step in the use of these two fungal metabolites to allow better preservation of artworks and to guarantee the conditions suitable for their conservation. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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23 pages, 2994 KiB  
Article
Arabidopsis Defense against the Pathogenic Fungus Drechslera gigantea Is Dependent on the Integrity of the Unfolded Protein Response
by Simone Samperna, Angela Boari, Maurizio Vurro, Anna Maria Salzano, Pierluigi Reveglia, Antonio Evidente, Angelo Gismondi, Antonella Canini, Andrea Scaloni and Mauro Marra
Biomolecules 2021, 11(2), 240; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11020240 - 08 Feb 2021
Cited by 5 | Viewed by 2985
Abstract
Drechslera gigantea Heald & Wolf is a worldwide-spread necrotrophic fungus closely related to the Bipolaris genus, well-known because many member species provoke severe diseases in cereal crops and studied because they produce sesterpenoid phytoxins named ophiobolins which possess interesting biological properties. The unfolded [...] Read more.
Drechslera gigantea Heald & Wolf is a worldwide-spread necrotrophic fungus closely related to the Bipolaris genus, well-known because many member species provoke severe diseases in cereal crops and studied because they produce sesterpenoid phytoxins named ophiobolins which possess interesting biological properties. The unfolded protein response (UPR) is a conserved mechanism protecting eukaryotic cells from the accumulation of unfolded/misfolded proteins in the endoplasmic reticulum (ER). In plants, consolidated evidence supports the role of UPR in the tolerance to abiotic stress, whereas much less information is available concerning the induction of ER stress by pathogen infection and consequent UPR elicitation as part of the defense response. In this study, the infection process of D. gigantea in Arabidopsis thaliana wild type and UPR-defective bzip28 bzip60 double mutant plants was comparatively investigated, with the aim to address the role of UPR in the expression of resistance to the fungal pathogen. The results of confocal microscopy, as well as of qRT-PCR transcript level analysis of UPR genes, proteomics, microRNAs expression profile and HPLC-based hormone analyses demonstrated that ophiobolin produced by the fungus during infection compromised ER integrity and that impairment of the IRE1/bZIP60 pathway of UPR hampered the full expression of resistance, thereby enhancing plant susceptibility to the pathogen. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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Review

Jump to: Research

24 pages, 5959 KiB  
Review
Role of Sulphur and Heavier Chalcogens on the Antioxidant Power and Bioactivity of Natural Phenolic Compounds
by Maria Laura Alfieri, Lucia Panzella, Riccardo Amorati, Alice Cariola, Luca Valgimigli and Alessandra Napolitano
Biomolecules 2022, 12(1), 90; https://0-doi-org.brum.beds.ac.uk/10.3390/biom12010090 - 06 Jan 2022
Cited by 15 | Viewed by 3014
Abstract
The activity of natural phenols is primarily associated to their antioxidant potential, but is ultimately expressed in a variety of biological effects. Molecular scaffold manipulation of this large variety of compounds is a currently pursued approach to boost or modulate their properties. Insertion [...] Read more.
The activity of natural phenols is primarily associated to their antioxidant potential, but is ultimately expressed in a variety of biological effects. Molecular scaffold manipulation of this large variety of compounds is a currently pursued approach to boost or modulate their properties. Insertion of S/Se/Te containing substituents on phenols may increase/decrease their H-donor/acceptor ability by electronic and stereo-electronic effects related to the site of substitution and geometrical constrains. Oxygen to sulphur/selenium isosteric replacement in resveratrol or ferulic acid leads to an increase in the radical scavenging activity with respect to the parent phenol. Several chalcogen-substituted phenols inspired by Vitamin E and flavonoids have been prepared, which in some cases prove to be chain-breaking antioxidants, far better than the natural counterparts. Conjugation of catechols with biological thiols (cysteine, glutathione, dihydrolipoic acid) is easily achieved by addition to the corresponding ortho-quinones. Noticeable examples of compounds with potentiated antioxidant activities are the human metabolite 5-S-cysteinyldopa, with high iron-induced lipid peroxidation inhibitory activity, due to strong iron (III) binding, 5-S-glutathionylpiceatannol a most effective inhibitor of nitrosation processes, and 5-S-lipoylhydroxytyrosol, and its polysulfides that proved valuable oxidative-stress protective agents in various cellular models. Different methodologies have been used for evaluation of the antioxidant power of these compounds against the parent compounds. These include kinetics of inhibition of lipid peroxidation alkylperoxyl radicals, common chemical assays of radical scavenging, inhibition of the OH• mediated hydroxylation/oxidation of model systems, ferric- or copper-reducing power, scavenging of nitrosating species. In addition, computational methods allowed researchers to determine the Bond Dissociation Enthalpy values of the OH groups of chalcogen modified phenolics and predict the best performing derivative. Finally, the activity of Se and Te containing compounds as mimic of glutathione peroxidase has been evaluated, together with other biological activities including anticancer action and (neuro)protective effects in various cellular models. These and other achievements are discussed and rationalized to guide future development in the field. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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43 pages, 3640 KiB  
Review
Natural Bioactive Cinnamoyltyramine Alkylamides and Co-Metabolites
by Antonio Evidente and Marco Masi
Biomolecules 2021, 11(12), 1765; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11121765 - 25 Nov 2021
Cited by 7 | Viewed by 3138
Abstract
Natural products are a vital source for agriculture, medicine, cosmetic and other fields. Among them alkylamides are a broad and expanding group found in at least 33 plant families. Frequently, they possess a simple carbon skeleton architecture but show broad structural variability and [...] Read more.
Natural products are a vital source for agriculture, medicine, cosmetic and other fields. Among them alkylamides are a broad and expanding group found in at least 33 plant families. Frequently, they possess a simple carbon skeleton architecture but show broad structural variability and important properties such as immunomodulatory, antimicrobial, antiviral, larvicidal, insecticidal and antioxidant properties, amongst others. Despite to these several and promising biological activities, up to today, only two reviews have been published on natural alkylamides. One focuses on their potential pharmacology application and their distribution in the plant kingdom and the other one on the bioactive alkylamides specifically found in Annona spp. The present review is focused on the plant bioactive cinnamoyltyramine alkylamides, which are subject of several works reported in the literature. Furthermore, the co-metabolites isolated from the same natural sources and their biological activities are also reported. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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29 pages, 8078 KiB  
Review
The Surprising Story of Fusicoccin: A Wilt-Inducing Phytotoxin, a Tool in Plant Physiology and a 14-3-3-Targeted Drug
by Mauro Marra, Lorenzo Camoni, Sabina Visconti, Anna Fiorillo and Antonio Evidente
Biomolecules 2021, 11(9), 1393; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11091393 - 21 Sep 2021
Cited by 21 | Viewed by 2945
Abstract
Fusicoccin is the α glucoside of a carbotricyclic diterpene, produced by the fungus Phomopsis amygdali (previously classified as Fusicoccum amygdali), the causal agent of almond and peach canker disease. A great interest in this molecule started when it was discovered that it [...] Read more.
Fusicoccin is the α glucoside of a carbotricyclic diterpene, produced by the fungus Phomopsis amygdali (previously classified as Fusicoccum amygdali), the causal agent of almond and peach canker disease. A great interest in this molecule started when it was discovered that it brought about an irreversible stomata opening of higher plants, thereby inducing the wilting of their leaves. Since then, several studies were carried out to elucidate its biological activity, biosynthesis, structure, structure-activity relationships and mode of action. After sixty years of research and more than 1800 published articles, FC is still the most studied phytotoxin and one of the few whose mechanism of action has been elucidated in detail. The ability of FC to stimulate several fundamental plant processes depends on its ability to activate the plasma membrane H+-ATPase, induced by eliciting the association of 14-3-3 proteins, a class of regulatory molecules widespread in eukaryotes. This discovery renewed interest in FC and prompted more recent studies aimed to ascertain the ability of the toxin to influence the interaction between 14-3-3 proteins and their numerous client proteins in animals, involved in the regulation of basic cellular processes and in the etiology of different diseases, including cancer. This review covers the different aspects of FC research partially treated in different previous reviews, starting from its discovery in 1964, with the aim to outline the extraordinary pathway which led this very uncommon diterpenoid to evolve from a phytotoxin into a tool in plant physiology and eventually into a 14-3-3-targeted drug. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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61 pages, 22057 KiB  
Review
Tailored Functionalization of Natural Phenols to Improve Biological Activity
by Barbara Floris, Pierluca Galloni, Valeria Conte and Federica Sabuzi
Biomolecules 2021, 11(9), 1325; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11091325 - 07 Sep 2021
Cited by 16 | Viewed by 5773
Abstract
Phenols are widespread in nature, being the major components of several plants and essential oils. Natural phenols’ anti-microbial, anti-bacterial, anti-oxidant, pharmacological and nutritional properties are, nowadays, well established. Hence, given their peculiar biological role, numerous studies are currently ongoing to overcome their limitations, [...] Read more.
Phenols are widespread in nature, being the major components of several plants and essential oils. Natural phenols’ anti-microbial, anti-bacterial, anti-oxidant, pharmacological and nutritional properties are, nowadays, well established. Hence, given their peculiar biological role, numerous studies are currently ongoing to overcome their limitations, as well as to enhance their activity. In this review, the functionalization of selected natural phenols is critically examined, mainly highlighting their improved bioactivity after the proper chemical transformations. In particular, functionalization of the most abundant naturally occurring monophenols, diphenols, lipidic phenols, phenolic acids, polyphenols and curcumin derivatives is explored. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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15 pages, 2770 KiB  
Review
Cannabinoquinones: Synthesis and Biological Profile
by Diego Caprioglio, Daiana Mattoteia, Orazio Taglialatela-Scafati, Eduardo Muñoz and Giovanni Appendino
Biomolecules 2021, 11(7), 991; https://0-doi-org.brum.beds.ac.uk/10.3390/biom11070991 - 05 Jul 2021
Cited by 5 | Viewed by 3057
Abstract
Neutral cannabinoids are oxidatively unstable and are converted into quinone derivatives by atmospheric- and/or chemical oxidative dearomatization. The study of cannabinoquinones has long been plagued by their lability toward additional oxidative degradation, but full substitution of the quinone ring, as well as the [...] Read more.
Neutral cannabinoids are oxidatively unstable and are converted into quinone derivatives by atmospheric- and/or chemical oxidative dearomatization. The study of cannabinoquinones has long been plagued by their lability toward additional oxidative degradation, but full substitution of the quinone ring, as well as the introduction of steric hindrance on the alkyl substituent, have provided sufficient stability for a systematic investigation of their bioactivity and for further clinical development. These studies culminated in the discovery of the aminocannabinoquinone VCE-004.8 (5), a compound under phase 2 clinical development with orphan drug status by EMA and FDA for the management of scleroderma. The synthesis and rich chemistry of these compounds will be described, summarizing their biological profile and clinical potential. Full article
(This article belongs to the Special Issue State-of-the-Art Isolation, Chemical and Biological Characterization, Synthesis and Formulation of Natural Products in Italy 2020–2021)
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