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

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 14329

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Special Issue Editors

Dr. Ewa Maria Musiol-Kroll

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Guest Editor

Department of Microbiology/Biotechnology, Interfaculty Institute of Microbiology and Infection Medicine Tuebingen (IMIT), University Tuebingen, Auf der Morgenstelle 28, 72076 Tuebingen, Germany
Interests: actinomycetes; streptomycetes; bioactive natural products; antibiotics; polyketides; aminoglycosides; polyketide biosynthesis; polyketide acyltransferase; engineering; tools

Prof. Dr. Yvonne Mast

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Guest Editor

Department Bioresources for Bioeconomy and Health Research Inhoffenstraße 7B, DSMZ-German Collection of Microorganisms and Cell Cultures GmbH, Leibniz Institute, 38124 Braunschweig, Germany
Interests: antibiotics; Streptomycetes; biosynthesis; silent gene cluster; genome mining; genetic engineering; synthetic biology; regulation; overproduction; streptogramins
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Special Issue Information

Dear Colleague,

Natural products (NPs) are chemical compounds of biological origin, which show diverse bioactivities and therefore serve as important sources for novel drugs. NPs and NP-derived compounds are used in medicine, agriculture, the food industry, and other fields. The chemical structures of NPs can be very diverse, ranging from simple to very complex molecules (e.g., primary metabolites versus secondary metabolites). Many bioactive NPs are secondary metabolites that have been derived from microorganisms. For example, two thirds of all clinically used antibiotics were originally obtained from actinomycetes, particularly from the genus Streptomyces. In this Special Issue on “Biosynthesis and Biological Activities of Natural Products”, we intend to focus on microbial NPs (e.g., polyketides (PKs), nonribosomal peptides (NRPs), ribosomally synthesized and post-translationally modified peptides (RiPPs), aminoglycosides, terpenes). The structural diversity of microbial NPs results from the variety of biosynthetic pathways encoded in the genome of the producer strains. The biosynthetic processes involve multiple steps, including provision of precursors and co-factors, supply of the required enzymes of the pathway, assembly (condensation of the precursors), modification of the synthesized compound, as well as export mechanisms. Many of these steps are subject to regulation by complex regulatory networks, which makes the biosynthetic process a highly coordinated fine-tuned system. Recent advances in molecular biology techniques, bioinformatics, and chemistry have accelerated research in the field. New bioactive NPs have been identified, and NP pathways characterized and engineered to produce derivatives with improved pharmacokinetic properties or to increase product yields.

This Special Issue will focus on recent studies in the field of microbial NP research. More specifically, we endorse the publication of original research articles, communications, and reviews that cover the following topics:

Identification and characterization of NP biosynthetic pathways;
New bioactive NPs;
New bioactivities of known NPs;
Engineering of NP biosynthesis;
Optimization of NP biosynthesis;
Production and impact of NPs in complex systems (e.g., microbial communities);
New tools and approaches for investigation and engineering of NP biosynthesis and/or their bioactivity.

Dr. Ewa Maria Musiol-Kroll
Prof. Dr. Yvonne Mast
Guest Editors

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. Molecules is an international peer-reviewed open access semimonthly 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

natural products
bioactivity
drugs
producers
biosynthetic genes
biosynthesis
engineering
tools

Published Papers (5 papers)

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Research

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11 pages, 2579 KiB

Open AccessArticle

Investigation on Metabolites in Structure and Biosynthesis from the Deep-Sea Sediment-Derived Actinomycete Janibacter sp. SCSIO 52865

by Wenping Ding, Yanqun Li, Xinpeng Tian, Zhihui Xiao, Ru Li, Si Zhang and Hao Yin

Molecules 2023, 28(5), 2133; https://doi.org/10.3390/molecules28052133 - 24 Feb 2023

Cited by 6 | Viewed by 1427

Abstract

For exploring structurally diverse metabolites and uniquely metabolic mechanisms, we systematically investigated the chemical constituents and putative biosynthesis of Janibacter sp. SCSIO 52865 derived from the deep-sea sediment based on the OSMAC strategy, molecular networking tool, in combination with bioinformatic analysis. As a result, one new diketopiperazine (1), along with seven known cyclodipeptides (2–8), trans-cinnamic acid (9), N-phenethylacetamide (10) and five fatty acids (11–15), was isolated from the ethyl acetate extract of SCSIO 52865. Their structures were elucidated by a combination of comprehensive spectroscopic analyses, Marfey’s method and GC-MS analysis. Furthermore, the analysis of molecular networking revealed the presence of cyclodipeptides, and compound 1 was produced only under mBHI fermentation condition. Moreover, bioinformatic analysis suggested that compound 1 was closely related to four genes, namely jatA–D, encoding core non-ribosomal peptide synthetase and acetyltransferase. Full article

(This article belongs to the Special Issue Biosynthesis and Biological Activities of Natural Products)

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15 pages, 2217 KiB

Open AccessArticle

Fluorinated Analogues of Lepidilines A and C: Synthesis and Screening of Their Anticancer and Antiviral Activity

by Grzegorz Mlostoń, Mateusz Kowalczyk, Małgorzata Celeda, Marcin Jasiński, Marta Denel-Bobrowska and Agnieszka B. Olejniczak

Molecules 2022, 27(11), 3524; https://doi.org/10.3390/molecules27113524 - 30 May 2022

Cited by 5 | Viewed by 1698

Abstract

Starting with fluorinated benzylamines, a series of 2-unsubstituted imidazole N-oxides was prepared and subsequently deoxygenated in order to prepare the corresponding imidazoles. The latter were treated with benzyl halides yielding imidazolium salts, which are considered fluorinated analogues of naturally occurring imidazolium alkaloids known as lepidilines A and C. A second series of oxa-lepidiline analogues was obtained by O-benzylation of the initially synthetized imidazole N-oxides. Both series of imidazolium salts were tested as anticancer and antiviral agents. The obtained results demonstrated that the introduction of a fluorine atom, fluoroalkyl or fluoroalkoxy substituents (F, CF₃ or OCF₃) amplifies cytotoxic properties, whereas the cytotoxicity of some fluorinated lepidilines is promising in the context of drug discovery. All studied compounds revealed a lack of antiviral activity against the investigated viruses in the nontoxic concentrations. Full article

(This article belongs to the Special Issue Biosynthesis and Biological Activities of Natural Products)

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14 pages, 2557 KiB

Open AccessArticle

Understanding the Mechanism of Action of NAI-112, a Lanthipeptide with Potent Antinociceptive Activity

by Arianna Tocchetti, Marianna Iorio, Zeeshan Hamid, Andrea Armirotti, Angelo Reggiani and Stefano Donadio

Molecules 2021, 26(22), 6764; https://doi.org/10.3390/molecules26226764 - 9 Nov 2021

Cited by 6 | Viewed by 1924

Abstract

NAI-112, a glycosylated, labionine-containing lanthipeptide with weak antibacterial activity, has demonstrated analgesic activity in relevant mouse models of nociceptive and neuropathic pain. However, the mechanism(s) through which NAI-112 exerts its analgesic and antibacterial activities is not known. In this study, we analyzed changes in the spinal cord lipidome resulting from treatment with NAI-112 of naive and in-pain mice. Notably, NAI-112 led to an increase in phosphatidic acid levels in both no-pain and pain models and to a decrease in lysophosphatidic acid levels in the pain model only. We also showed that NAI-112 can form complexes with dipalmitoyl-phosphatidic acid and that Staphylococcus aureus can become resistant to NAI-112 through serial passages at sub-inhibitory concentrations of the compound. The resulting resistant mutants were phenotypically and genotypically related to vancomycin-insensitive S. aureus strains, suggesting that NAI-112 binds to the peptidoglycan intermediate lipid II. Altogether, our results suggest that NAI-112 binds to phosphate-containing lipids and blocks pain sensation by decreasing levels of lysophosphatidic acid in the TRPV1 pathway. Full article

(This article belongs to the Special Issue Biosynthesis and Biological Activities of Natural Products)

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24 pages, 3185 KiB

Open AccessArticle

Activation and Identification of a Griseusin Cluster in Streptomyces sp. CA-256286 by Employing Transcriptional Regulators and Multi-Omics Methods

by Charlotte Beck, Tetiana Gren, Francisco Javier Ortiz-López, Tue Sparholt Jørgensen, Daniel Carretero-Molina, Jesús Martín Serrano, José R. Tormo, Daniel Oves-Costales, Eftychia E. Kontou, Omkar S. Mohite, Erik Mingyar, Evi Stegmann, Olga Genilloud and Tilmann Weber

Molecules 2021, 26(21), 6580; https://doi.org/10.3390/molecules26216580 - 30 Oct 2021

Cited by 8 | Viewed by 3479

Abstract

Streptomyces are well-known producers of a range of different secondary metabolites, including antibiotics and other bioactive compounds. Recently, it has been demonstrated that “silent” biosynthetic gene clusters (BGCs) can be activated by heterologously expressing transcriptional regulators from other BGCs. Here, we have activated a silent BGC in Streptomyces sp. CA-256286 by overexpression of a set of SARP family transcriptional regulators. The structure of the produced compound was elucidated by NMR and found to be an N-acetyl cysteine adduct of the pyranonaphtoquinone polyketide 3′-O-α-d-forosaminyl-(+)-griseusin A. Employing a combination of multi-omics and metabolic engineering techniques, we identified the responsible BGC. These methods include genome mining, proteomics and transcriptomics analyses, in combination with CRISPR induced gene inactivations and expression of the BGC in a heterologous host strain. This work demonstrates an easy-to-implement workflow of how silent BGCs can be activated, followed by the identification and characterization of the produced compound, the responsible BGC, and hints of its biosynthetic pathway. Full article

(This article belongs to the Special Issue Biosynthesis and Biological Activities of Natural Products)

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Review

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29 pages, 4510 KiB

Open AccessReview

Pseudomonas Lipopeptide-Mediated Biocontrol: Chemotaxonomy and Biological Activity

by Feyisara Eyiwumi Oni, Qassim Esmaeel, Joseph Tobias Onyeka, Rasheed Adeleke, Cedric Jacquard, Christophe Clement, Harald Gross, Essaid Ait Barka and Monica Höfte

Molecules 2022, 27(2), 372; https://doi.org/10.3390/molecules27020372 - 7 Jan 2022

Cited by 22 | Viewed by 3469

Abstract

Pseudomonas lipopeptides (Ps-LPs) play crucial roles in bacterial physiology, host–microbe interactions and plant disease control. Beneficial LP producers have mainly been isolated from the rhizosphere, phyllosphere and from bulk soils. Despite their wide geographic distribution and host range, emerging evidence suggests that LP-producing pseudomonads and their corresponding molecules display tight specificity and follow a phylogenetic distribution. About a decade ago, biocontrol LPs were mainly reported from the P. fluorescens group, but this has drastically advanced due to increased LP diversity research. On the one hand, the presence of a close-knit relationship between Pseudomonas taxonomy and the molecule produced may provide a startup toolbox for the delineation of unknown LPs into existing (or novel) LP groups. Furthermore, a taxonomy–molecule match may facilitate decisions regarding antimicrobial activity profiling and subsequent agricultural relevance of such LPs. In this review, we highlight and discuss the production of beneficial Ps-LPs by strains situated within unique taxonomic groups and the lineage-specificity and coevolution of this relationship. We also chronicle the antimicrobial activity demonstrated by these biomolecules in limited plant systems compared with multiple in vitro assays. Our review further stresses the need to systematically elucidate the roles of diverse Ps-LP groups in direct plant–pathogen interactions and in the enhancement of plant innate immunity. Full article

(This article belongs to the Special Issue Biosynthesis and Biological Activities of Natural Products)

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