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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
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.
September 13, 2018: Natural Product Reports
Thierry Izoré, Max J Cryle
Covering: up to July 2018Non-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...
September 12, 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
Greg J Dodge, Finn P Maloney, Janet L Smith
Covering: up to the end of 2018Polyketides 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...
September 6, 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
Dominik A Herbst, Craig A Townsend, Timm Maier
Covering: up to mid of 2018Type 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...
August 23, 2018: Natural Product Reports
Diana I S P Resende, Papichaya Boonpothong, Emília Sousa, Anake Kijjoa, Madalena M M Pinto
Covering: this review covers the literature from 1992 to 2018To date, approximately 80 naturally-occurring secondary metabolites which are structurally-related to fumiquinazolines have been isolated, mainly from marine sources. These alkaloids can be classified into twelve different groups and exhibit different structure motifs depending on the amino acids from which they are derived. This review is focused on isolation, structure elucidation, biological activities, biosynthetic pathways, and synthetic studies of these natural products...
August 9, 2018: Natural Product Reports
Didier F Vargas, Enrique L Larghi, Teodoro S Kaufman
Covering: 2006 to 2018The application of the 6π-azaelectrocyclization of azatrienes as a key strategy for the synthesis of natural products, their analogs and related bioactive or biomedically-relevant compounds (from 2006 to date) is comprehensively reviewed. Details about reaction optimization studies, relevant reaction mechanisms and conditions are also discussed.
August 9, 2018: Natural Product Reports
Carmien Tolmie, Martha S Smit, Diederik J Opperman
Covering: up to end of June 2018Baeyer-Villiger monooxygenases (BVMOs) are flavin-dependent enzymes that catalyse the oxidation of ketones and cyclic ketones to esters and lactones, respectively, by using molecular oxygen and NAD(P)H. BVMOs also catalyse sulfoxidations and N-oxidations. BVMOs are widely studied as attractive biocatalysts, but also catalyse key reactions in metabolic pathways of the organisms from which they are sourced. BVMOs are involved in the primary metabolism of atypical carbon sources, thereby conferring an evolutionary advantage to the host organism...
August 3, 2018: Natural Product Reports
Akimasa Miyanaga, Fumitaka Kudo, Tadashi Eguchi
Covering: up to early 2018Polyketides 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...
August 3, 2018: Natural Product Reports
Alistair S Brown, Mark J Calcott, Jeremy G Owen, David F Ackerley
Covering: up to May 2018Non-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...
August 2, 2018: Natural Product Reports
Florian Baldeweg, Dirk Hoffmeister, Markus Nett
Covering: up to February 2018In recent years, genome sequencing revealed the full biosynthetic potential of bacteria causing plant diseases. Bioinformatics and advanced analytical techniques paved the way to clarify the structures of long-sought natural products with a role in virulence. Furthermore, several compounds without disease-associated function were discovered. The exploration of these molecules disclosed persistence strategies of plant pathogenic bacteria outside their hosts and provided access to new bioactive compounds with therapeutic potential...
July 31, 2018: Natural Product Reports
Immacolata Castellano, Florian P Seebeck
Covering: up to 2018Ovothiols are sulfur-containing natural products biosynthesized by marine invertebrates, microalgae, and bacteria. These compounds are characterized by unique chemical properties suggestive of numerous cellular functions. For example, ovothiols may be cytoprotectants against oxidative stress, serve as building blocks of more complex structures and may act as molecular messengers for inter- and intracellular signaling. Detailed understanding of ovothiol physiological role in marine organisms may unearth novel concepts in cellular redox biochemistry and highlight the therapeutic potential of this antioxidant...
July 27, 2018: Natural Product Reports
Andrew M Gulick, Courtney C Aldrich
Covering: up to early 2018The 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...
July 26, 2018: Natural Product Reports
Aochiu Chen, Rebecca N Re, Michael D Burkart
Covering: up to April 5, 2018Metabolites 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...
July 26, 2018: Natural Product Reports
James M Wood, Daniel P Furkert, Margaret A Brimble
Covering: up to April 20182-Formylpyrroles are ubiquitous in nature, arising from the non-enzymatic Maillard reactions of amines and sugars. Often confused for secondary metabolites, these Maillard products display interesting biological activities including hepatoprotective, immunostimulatory, antiproliferative and antioxidant effects. This review presents all 2-formylpyrrole natural products reported to date and identifies structural sub-classes for their categorisation. The origin, biological activity and chemical syntheses of these natural products are discussed herein...
July 24, 2018: Natural Product Reports
Ashley C Lindsay, Se Hun Kim, Jonathan Sperry
Covering: 1969 to 2018Azepinoindole natural products can be broadly classified as being of monoterpenoid or non-monoterpenoid origin. The non-monoterpenoid azepinoindoles have not received as much attention in the literature as their more revered monoterpenoid counterparts. In this review, an overview of all non-monoterpenoid azepinoindoles is provided. Various biological and chemical aspects are discussed, including their isolation, biosynthesis and the elegant total synthesis studies that have been inspired by these alkaloids...
July 19, 2018: Natural Product Reports
Maude Cloutier, Kevin Muru, Gokulakrishnan Ravicoularamin, Charles Gauthier
Covering: up to 2018Burkholderia species are a vast group of human pathogenic, phytopathogenic, and plant- or environment-associated bacteria. B. pseudomallei, B. mallei, and B. cepacia complex are the causative agents of melioidosis, glanders, and cystic fibrosis-related infections, respectively, which are fatal diseases in humans and animals. Due to their high resistance to antibiotics, high mortality rates, and increased infectivity via the respiratory tract, B. pseudomallei and B. mallei have been listed as potential bioterrorism agents by the Centers for Disease Control and Prevention...
July 19, 2018: Natural Product Reports
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