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Special Issue "Structure-Activity Relationship of Natural Products 2018"

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

Deadline for manuscript submissions: 30 May 2018

Special Issue Editor

Guest Editor
Prof. Dr. Antonio Evidente

Department of Chemical Sciences, University of Naples “Federico II”, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy
Website | E-Mail
Interests: organic chemistry; bioactive natural substances; natural product isolation and characterization; spectroscopy; structure–activity relationship studies

Special Issue Information

Dear Colleagues,

Microbial, plant and terrestrial and marine organisms hold a great deal of promise in biosynthesizing secondary metabolites. These metabolites belong to all the different classes of natural compounds, such as terpenes, phenylpropanoids, polyketides, alkaloids, etc. Thus, these organisms represent a very good source of natural substances, frequently possessing very interesting biological activities with potential applications in different fields. Their practical applications sometimes require an increase in their stability, selectivity, solubility in water, or the best suitable formulation. Studies carried out on the relationship between the chemical structure of a natural compound and its biological activities is an important starting point to obtain information on structural features that are essential for biological activity. Furthermore, the same studies give the necessary information to reach the aims mentioned above for their practical application. All researchers working in the field, are cordially invited to contribute original research papers or reviews to this Special Issue of Molecules, which reports on the structure–activity relationship studies of natural products with different biological activities.

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 papers will be 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. Molecules 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 1800 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

  • natural products
  • source and chemical characterization
  • biological activities
  • chemical modification
  • structure activity relationships (SAR)

Published Papers (5 papers)

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Research

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Open AccessArticle Evaluating Molecular Properties Involved in Transport of Small Molecules in Stratum Corneum: A Quantitative Structure-Activity Relationship for Skin Permeability
Molecules 2018, 23(4), 911; doi:10.3390/molecules23040911
Received: 17 March 2018 / Revised: 11 April 2018 / Accepted: 12 April 2018 / Published: 15 April 2018
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Abstract
The skin permeability (Kp) defines the rate of a chemical penetrating across the stratum corneum. This value is widely used to quantitatively describe the transport of molecules in the outermost layer of epidermal skin and indicate the significance of skin absorption.
[...] Read more.
The skin permeability (Kp) defines the rate of a chemical penetrating across the stratum corneum. This value is widely used to quantitatively describe the transport of molecules in the outermost layer of epidermal skin and indicate the significance of skin absorption. This study defined a Kp quantitative structure-activity relationship (QSAR) based on 106 chemical substances of Kp measured using human skin and interpreted the molecular interactions underlying transport behavior of small molecules in the stratum corneum. The Kp QSAR developed in this study identified four molecular descriptors that described the molecular cyclicity in the molecule reflecting local geometrical environments, topological distances between pairs of oxygen and chlorine atoms, lipophilicity, and similarity to antineoplastics in molecular properties. This Kp QSAR considered the octanol-water partition coefficient to be a direct influence on transdermal movement of molecules. Moreover, the Kp QSAR identified a sub-domain of molecular properties initially defined to describe the antineoplastic resemblance of a compound as a significant factor in affecting transdermal permeation of solutes. This finding suggests that the influence of molecular size on the chemical’s skin-permeating capability should be interpreted with other relevant physicochemical properties rather than being represented by molecular weight alone. Full article
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products 2018)
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Open AccessArticle Identification of Bichalcones as Sirtuin Inhibitors by Virtual Screening and In Vitro Testing
Molecules 2018, 23(2), 416; doi:10.3390/molecules23020416
Received: 23 January 2018 / Revised: 9 February 2018 / Accepted: 10 February 2018 / Published: 14 February 2018
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Abstract
Sirtuins are nicotinamide adenine dinucleotide (NAD+)-dependent class III histone deacetylases, which have been linked to the pathogenesis of numerous diseases, including HIV, metabolic disorders, neurodegeneration and cancer. Docking of the virtual pan-African natural products library (p-ANAPL), followed by in vitro testing,
[...] Read more.
Sirtuins are nicotinamide adenine dinucleotide (NAD+)-dependent class III histone deacetylases, which have been linked to the pathogenesis of numerous diseases, including HIV, metabolic disorders, neurodegeneration and cancer. Docking of the virtual pan-African natural products library (p-ANAPL), followed by in vitro testing, resulted in the identification of two inhibitors of sirtuin 1, 2 and 3 (sirt1–3). Two bichalcones, known as rhuschalcone IV (8) and an analogue of rhuschalcone I (9), previously isolated from the medicinal plant Rhus pyroides, were shown to be active in the in vitro assay. The rhuschalcone I analogue (9) showed the best activity against sirt1, with an IC50 value of 40.8 µM. Based on the docking experiments, suggestions for improving the biological activities of the newly identified hit compounds have been provided. Full article
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products 2018)
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Open AccessCommunication Novel Topologically Complex Scaffold Derived from Alkaloid Haemanthamine
Molecules 2018, 23(2), 255; doi:10.3390/molecules23020255
Received: 8 January 2018 / Revised: 24 January 2018 / Accepted: 25 January 2018 / Published: 28 January 2018
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Abstract
The generation of natural product-like compound collections has become an important area of research due to low hit rates found with synthetic high-throughput libraries. One method of generating compounds occupying the areas of chemical space not accessible to synthetic planar heterocyclic structures is
[...] Read more.
The generation of natural product-like compound collections has become an important area of research due to low hit rates found with synthetic high-throughput libraries. One method of generating compounds occupying the areas of chemical space not accessible to synthetic planar heterocyclic structures is the utilization of natural products as starting materials. In the current work, using a ring-closing iodoalkoxylation reaction, alkaloid haemanthamine was transformed into a unique structural framework possessing an intricate ring system and a large number of stereocenters. The structure of the new compound was confirmed with an X-ray analysis. A small number of derivatives of this new compound were synthesized as a demonstration of the possibility of generating a large natural product-like compound collection based on the new structural framework. Full article
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products 2018)
Figures

Open AccessArticle Antioxidant and Cytoprotective Effects of the Di-O-Caffeoylquinic Acid Family: The Mechanism, Structure–Activity Relationship, and Conformational Effect
Molecules 2018, 23(1), 222; doi:10.3390/molecules23010222
Received: 8 December 2017 / Revised: 6 January 2018 / Accepted: 18 January 2018 / Published: 20 January 2018
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Abstract
In this study, a series of di-O-caffeoylquinic acids (di-COQs) were systematically investigated for their antioxidant and cytoprotective effects towards •OH-damaged bone marrow-derived mesenchymal stem cells (bmMSCs). Five di-COQs were measured using a set of antioxidant assays. The results show
[...] Read more.
In this study, a series of di-O-caffeoylquinic acids (di-COQs) were systematically investigated for their antioxidant and cytoprotective effects towards •OH-damaged bone marrow-derived mesenchymal stem cells (bmMSCs). Five di-COQs were measured using a set of antioxidant assays. The results show that adjacent 4,5-Di-O-caffeoylquinic acid (4,5-COQ) and 3,4-di-O-caffeoylquinic acid (3,4-COQ) always gave lower IC50 values than did non-adjacent di-COQs. In the Fe2+-chelating assay, 4,5-COQ and 3,4-COQ presented greater UV-Vis spectra and darker colors than did non-adjacent di-COQs. In the UPLC-ESI-MS/MS analysis, no corresponding radical adduct formation (RAF) peak was found in the reaction products of di-COQs with PTIO•. In the MTT assay, all di-COQs (especially 1,5-COQ, 1,3-COQ, and 4,5-COQ) dose-dependently increased the cellular viabilities of •OH-damaged bmMSCs. Based on this evidence, we conclude that the five antioxidant di-COQs can protect bmMSCs from •OH-induced damage. Their antioxidant mechanisms may include electron-transfer (ET), H+-transfer, and Fe2+-chelating, except for RAF. Two adjacent di-COQs (4,5-COQ and 3,4-COQ) always possessed a higher antioxidant ability than the non-adjacent di-COQs (1,3-COQ, 1,5-COQ, and 3,5-COQ) in chemical models. However, non-adjacent 1,3-COQ and 1,5-COQ exhibited a higher cytoprotective effect than did adjacent di-COQs. These differences can be attributed to the relative positions of two caffeoyl moieties and, ultimately, to the conformational effect from the cyclohexane skeleton. Full article
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products 2018)
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Review

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Open AccessReview Fungal Metabolites Antagonists towards Plant Pests and Human Pathogens: Structure-Activity Relationship Studies
Molecules 2018, 23(4), 834; doi:10.3390/molecules23040834
Received: 5 March 2018 / Revised: 29 March 2018 / Accepted: 2 April 2018 / Published: 5 April 2018
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Abstract
Fungi are able to produce many bioactive secondary metabolites that belong to different classes of natural compounds. Some of these compounds have been selected for their antagonism against pests and human pathogens and structure–activity relationship (SAR) studies have been performed to better understand
[...] Read more.
Fungi are able to produce many bioactive secondary metabolites that belong to different classes of natural compounds. Some of these compounds have been selected for their antagonism against pests and human pathogens and structure–activity relationship (SAR) studies have been performed to better understand which structural features are essential for the biological activity. In some cases, these studies allowed for the obtaining of hemisynthetic derivatives with increased selectivity and stability in respect to the natural products as well as reduced toxicity in view of their potential practical applications. This review deals with the SAR studies performed on fungal metabolites with potential fungicidal, bactericidal, insecticidal, and herbicidal activities from 1990 to the present (beginning of 2018). Full article
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products 2018)
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