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Natural Product Reports

Yuan Liu, Shuangyang Ding, Jianzhong Shen, Kui Zhu
Covering: 2000 to 2018, particularly from 2010 to early 2018The increase in the incidence of antibiotic resistant infections is threatening to overwhelm healthcare practices worldwide. Most antibiotics in clinical use are becoming ineffective, so therefore it is imperative to develop new antibiotics and novel therapeutic strategies. Traditionally, the chemical and mechanistic diversity of nonribosomal antibacterial peptides (NRAPs) as lead compounds have meant that their structures are ideal for antibiotic discovery...
October 16, 2018: Natural Product Reports
Akimasa Miyanaga
Covering: up to July 2018Polyketides constitute a large family of natural products exhibiting various biological activities. Polyketide biosynthetic systems employ several strategies for the production of structurally diverse polyketides. Among the polyketide biosynthetic enzymes, a growing number of enzymes that catalyze a Michael-type addition have been identified. These enzymes are responsible for constructing unique polyketide backbone structures, forming heterocycles, and incorporating heteroatoms into the polyketide backbone, all of which contribute to the diversification of the polyketide structure...
October 12, 2018: Natural Product Reports
Cooper S Jamieson, Masao Ohashi, Fang Liu, Yi Tang, K N Houk
Covering: 2000 to 2018Pericyclic reactions are a distinct class of reactions that have wide synthetic utility. Before the recent discoveries described in this review, enzyme-catalyzed pericyclic reactions were not widely known to be involved in biosynthesis. This situation is changing rapidly. We define the scope of pericyclic reactions, give a historical account of their discoveries as biosynthetic reactions, and provide evidence that there are many enzymes in nature that catalyze pericyclic reactions. These enzymes, the "pericyclases," are the subject of this review...
October 12, 2018: Natural Product Reports
Melany P Puglisi, Jennifer M Sneed, Raphael Ritson-Williams, Ryan Young
Covering: Most of 2013 up to the end of 2015This review highlights the 2013-2015 marine chemical ecology literature for benthic bacteria and cyanobacteria, macroalgae, sponges, cnidarians, molluscs, other benthic invertebrates, and fish.
September 28, 2018: Natural Product Reports
Marialuisa Menna, Concetta Imperatore, Alfonso Mangoni, Gerardo Della Sala, Orazio Taglialatela-Scafati
Covering: up to 2018Even today, when planar structures of natural products can be determined with microgram samples, the configurational assignment continues to be a challenge. The relative and absolute configurations of natural products can be assigned by devising original approaches, relying on carefully acquired data on a case-by-case basis. In this review, the most widely available methods and techniques for the absolute configuration determination of novel natural products are concisely discussed. Selected illustrative examples (case studies) are presented, where original approaches integrating different chemical, spectroscopic, and/or computational methods have been devised to solve intriguing stereochemistry issues of natural small molecules...
September 24, 2018: Natural Product Reports
Alessandro Palmieri, Marino Petrini
Covering: up to 2018Tryptophol (indole-3-ethanol) is a metabolite produced by plants, bacteria, fungi and sponges. This review reports on the natural occurrence, bioactivity and various synthetic approaches to the preparation of tryptophol and its derivatives. Syntheses of various naturally occurring tryptophol derivatives known for their enhanced pharmacological profile are also presented.
September 19, 2018: Natural Product Reports
Yuye Chen, Jing Zhao, Shaoping Li, Jing Xu
Covering: January 2012 to January 2018Sesterterpenoids are a small family of terpenes that often possess intriguing biological profiles and complicated chemical structures. Their total syntheses are usually remarkably challenging, requiring methodological and strategic innovation. In this review, we summarize and discuss the total syntheses of sesterterpenoids published during the coverage period, and the key chemical transformations are highlighted.
September 14, 2018: Natural Product Reports
Serina L Robinson, James K Christenson, Lawrence P Wackett
Covering: up to 2018β-Lactones are strained rings that are useful organic synthons and pharmaceutical warheads. Over 30 core scaffolds of β-lactone natural products have been described to date, many with potent bioactivity against bacteria, fungi, or human cancer cell lines. β-Lactone natural products are chemically diverse and have high clinical potential, but production of derivatized drug leads has been largely restricted to chemical synthesis partly due to gaps in biochemical knowledge about β-lactone biosynthesis...
September 7, 2018: Natural Product Reports
Yi-Ling Du, Katherine S Ryan
Covering: up to mid-2018Pyridoxal 5'-phosphate (PLP) is a versatile organic cofactor used to catalyze diverse reactions on amino acid, oxoacid, and amine substrates. Here we review the reactions catalyzed by PLP-dependent enzymes, highlighting enzymes reported in the natural product biosynthetic literature. We describe enzymes that catalyze transaminations, Claisen-like condensations, and β- and γ-eliminations and substitutions, along with epimerizations, decarboxylations, and transaldolations. Finally, we describe a newly reported group of O2-, PLP-dependent enzymes...
September 5, 2018: Natural Product Reports
David F Ackerley, Gregory L Challis, Max J Cryle
No abstract text is available yet for this article.
November 14, 2018: Natural Product Reports
Camilla Knudsen, Nethaji Janeshawari Gallage, Cecilie Cetti Hansen, Birger Lindberg Møller, Tomas Laursen
Covering: up to 2018 Plants are sessile organisms. To compensate for not being able to escape when challenged by unfavorable growth conditions, pests or herbivores, plants have perfected their metabolic plasticity by having developed the capacity for on demand synthesis of a plethora of phytochemicals to specifically respond to the challenges arising during plant ontogeny. Key steps in the biosynthesis of phytochemicals are catalyzed by membrane-bound cytochrome P450 enzymes which in plants constitute a superfamily...
November 14, 2018: Natural Product Reports
Thierry Izoré, Max J Cryle
Covering: up to July 2018 Non-ribosomal peptide synthetase (NRPS) machineries are complex, multi-domain proteins that are responsible for the biosynthesis of many important, peptide-derived compounds. By decoupling peptide synthesis from the ribosome, NRPS assembly lines are able to access a significant pool of amino acid monomers for peptide synthesis. This is combined with a modular protein architecture that allows for great variation in stereochemistry, peptide length, cyclisation state and further modifications...
November 14, 2018: Natural Product Reports
Akimasa Miyanaga, Fumitaka Kudo, Tadashi Eguchi
Covering: up to early 2018 Polyketides and nonribosomal peptides are two major families of natural product with a broad range of biological activities. Polyketide synthases (PKSs) assemble small acetic acid-type acyl building blocks into polyketides through C-C bonds, and nonribosomal peptide synthetases (NRPSs) assemble amino acids into peptides through amide bonds. PKS-NRPS hybrid assembly lines build structurally complex polyketide-amino acid/peptide hybrid molecules that incorporate both acyl and aminoacyl building blocks into their products...
November 14, 2018: Natural Product Reports
Alistair S Brown, Mark J Calcott, Jeremy G Owen, David F Ackerley
Covering: up to May 2018 Non-ribosomal peptide synthetases (NRPSs) are mega-enzymes that form modular templates to assemble specific peptide products, independent of the ribosome. The autonomous nature of the modules in the template offers prospects for re-engineering NRPS enzymes to generate modified peptide products. Although this has clearly been a primary mechanism of natural product diversification throughout evolution, equivalent strategies have proven challenging to implement in the laboratory. In this review we examine key examples of successful and less-successful re-engineering of NRPS templates to generate novel peptides, with the aim of extracting practical guidelines to inform future efforts...
November 14, 2018: Natural Product Reports
Andrew M Gulick, Courtney C Aldrich
Covering: up to early 2018 The Nonribosomal Peptide Synthetases (NRPSs) and Polyketide Synthases (PKSs) are families of modular enzymes that produce a tremendous diversity of natural products, with antibacterial, antifungal, immunosuppressive, and anticancer activities. Both enzymes utilize a fascinating modular architecture in which the synthetic intermediates are covalently attached to a peptidyl- or acyl-carrier protein that is delivered to catalytic domains for natural product elongation, modification, and termination...
November 14, 2018: Natural Product Reports
Simone Kosol, Matthew Jenner, Józef R Lewandowski, Gregory L Challis
Covering: up to 2018 The construction of polyketide natural products by type I modular polyketide synthases (PKSs) requires the coordinated action of several protein subunits to ensure biosynthetic fidelity. This is particularly the case for trans-AT PKSs, which in contrast to most cis-AT PKSs, contain split modules and employ several trans-acting catalytic domains. This article summarises recent advances in understanding the protein-protein interactions underpinning subunit assembly and intra-subunit communication in such systems and highlights potential avenues and approaches for future research...
October 17, 2018: Natural Product Reports
Robert A Hill, Andrew Sutherland
A personal selection of 32 recent papers is presented covering various aspects of current developments in bioorganic chemistry and novel natural products such as huperphlegmine A from Huperzia phlegmaria.
October 17, 2018: Natural Product Reports
Greg J Dodge, Finn P Maloney, Janet L Smith
Covering: up to the end of 2018 Polyketides are a valuable source of bioactive and clinically important molecules. The biosynthesis of these chemically complex molecules has led to the discovery of equally complex polyketide synthase (PKS) pathways. Crystallography has yielded snapshots of individual catalytic domains, di-domains, and multi-domains from a variety of PKS megasynthases, and cryo-EM studies have provided initial views of a PKS module in a series of defined biochemical states. Here, we review the structural and biochemical results that shed light on the protein-protein interactions critical to catalysis by PKS systems with an embedded acyltransferase...
October 17, 2018: Natural Product Reports
Dominik A Herbst, Craig A Townsend, Timm Maier
Covering: up to mid of 2018 Type I fatty acid synthases (FASs) are giant multienzymes catalyzing all steps of the biosynthesis of fatty acids from acetyl- and malonyl-CoA by iterative precursor extension. Two strikingly different architectures of FAS evolved in yeast (as well as in other fungi and some bacteria) and metazoans. Yeast-type FAS (yFAS) assembles into a barrel-shaped structure of more than 2 MDa molecular weight. Catalytic domains of yFAS are embedded in an extensive scaffolding matrix and arranged around two enclosed reaction chambers...
October 17, 2018: Natural Product Reports
Aochiu Chen, Rebecca N Re, Michael D Burkart
Covering: up to April 5, 2018 Metabolites from type II fatty acid synthase (FAS) and polyketide synthase (PKS) pathways differ broadly in their identities and functional roles. The former are considered primary metabolites that are linear hydrocarbon acids, while the latter are complex aromatic or polyunsaturated secondary metabolites. Though the study of bacterial FAS has benefitted from decades of biochemical and structural investigations, type II PKSs have remained less understood. Here we review the recent approaches to understanding the protein-protein and protein-substrate interactions in these pathways, with an emphasis on recent chemical biology and structural applications...
October 17, 2018: Natural Product Reports
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