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Systematic, large-scale, studies at the genomic, metabolomic, and functional level have transformed the natural product sciences. Improvements in technology and reduction in cost for obtaining spectroscopic, chromatographic, and genomic data coupled with the creation of readily accessible curated and functionally annotated data sets have altered the practices of virtually all natural product research laboratories. Gone are the days when the natural products researchers were expected to devote themselves exclusively to the isolation, purification, and structure elucidation of small molecules. We now also engage with big data in taxonomic, genomic, proteomic, and/or metabolomic collections, and use these data to generate and test hypotheses. While the oft stated aim for the use of large-scale -omics data in the natural products sciences is to achieve a rapid increase in the rate of discovery of new drugs, this has not yet come to pass. At the same time, new technologies have provided unexpected opportunities for natural products chemists to ask and answer new and different questions. With this viewpoint, we discuss the evolution of big data as a part of natural products research and provide a few examples of how discoveries have been enabled by access to big data. We also draw attention to some of the limitations in our existing engagement with large datasets and consider what would be necessary to overcome them., Big data is changing how we do natural products research and creating exciting new possibilities. Continued attention to enhancing data quality, increasing access, and preserving foundational skills is needed.

Bromide and chloride analogs of the commonly used zinc iodide-based metal organic framework for the crystalline sponge method were synthesized and evaluated. Inclusion of (1R)-(–)-menthyl acetate into these MOFs was analysed using third-generation synchrotron radiation, and the effects and potential benefits of varying the MOF terminal ligand are discussed.

This Viewpoint article provides a brief and selective summary of research on the chemical ecology underlying symbioses between bacteria and animals. Animals engage in multiple highly specialized interactions with bacteria that reflect their long coevolutionary history. The article focuses on a few illustrative but hardly exhaustive examples in which bacterially produced small molecules initiate a developmental step with important implications for the evolution of animals, provide signals for the maturation of mammalian immune systems, and furnish chemical defenses against microbial pathogens.

We report a preliminary functional and complete structural characterization of a highly unusual geldanamycin analog, natalamycin A, that was isolated from Streptomyces strain M56 recovered from a South African nest of Macrotermes natalensis termites. Bioassay-guided fractionation based on antifungal activity led to the isolation of natalamycin A, and a combination of NMR spectroscopy and X-ray crystallographic analysis, including highly-accurate quantum-chemical NMR calculations on the largest and most conformationally-flexible system to date, revealed natalamycin A’s three-dimensional solid- and solution-state structure. This structure along with the structures of related compounds isolated from the same source suggest a geldanamycin-like biosynthetic pathway with unusual post-PKS modifications.

Dieser Beitrag ist mit Zustimmung des Rechteinhabers aufgrund einer (DFG geförderten) Allianz- bzw. Nationallizenz frei zugänglich. This publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively. Covering: 1988 to 2012 This review presents recommended nomenclature for the biosynthesis of ribosomally synthesized and post-translationally modified peptides (RiPPs), a rapidly growing class of natural products. The current knowledge regarding the biosynthesis of the >20 distinct compound classes is also reviewed, and commonalities are discussed.

The study of bacterial symbionts of eukaryotic hosts has become a powerful discovery engine for chemistry. This highlight looks at four case studies that exemplify the range of chemistry and biology involved in these symbioses: a bacterial symbiont of a fungus and a marine invertebrate that produce compounds with significant anticancer activity, and bacterial symbionts of insects and nematodes that produce compounds that regulate multilateral symbioses.

Treatment of chalcone-epoxide 1 with lithium tetramethylpiperidide gives two anions: enolate 3 and the remote anion 4 which upon formation, 4 adds to unreacted starting material 1 to yield the diastereoisomeric products 5 and 6.

The structures of a new type of cyclopentane icosanoids from the marine diatom, Nitzschia pungens f. multiseries, have been confirmed by X-ray crystallography, and their absolute configurations determined.

The crystal and molecular structures of (±)- and meso-bivalvane have been determined by single-crystal three-dimensional X-ray diffraction methods. The (±)-hydrocarbon (2) crystallizes in the monoclinic space group P21/c with lattice parameters a= 9.779(1), b= 17.219(2), c= 9.635(1)A, and β= 99.89(1)°. The structure was refined to R 0.049 for 1 853 observed reflections. The meso-hydrocarbon (4) is also monoclinic, space group P21/n, with Z= 2 in a cell of dimensions a= 6.377(1), b= 6.306(1), c= 19.553(2)A, and β= 90.87(1)°. The molecule spans a crystallographic inversion centre. Refinement converged at R 0.039 for 928 observed reflections. Both bivalvanes adopt strain-free extended conformations, the triquanane-part structures of which appear to be regular in their geometry.

A new tricarbocyclic diterpene, chromophycadiol monoacetate (2), possessing a novel carbon skeleton, was isolated from a brown alga Dictyota sp. and its structure together with stereochemical features were determined by X-ray crystallography.

The structure of two closely related helogenated sesquiterpenes: rhodolaureol (1) and rhodolauradiol (5), isolated from a marine alga of the genus Laurencia, have been determined by X-ray diffraction analysis.

An X-ray crystallographic investigation of the complex dimer, [(MeO)3P]2Pd2(Cl)2(CSNMe)2, revealed two bridging C(S)NMe2 ligands which link the two Pd atoms by co-ordinating through the C and S atoms; this is the first example of a metal complex containing thiocarbamoyl bridging ligands.

Two new antibacterial metabolites, phlebiakauranol (1) and phlebianorkauranol (3) have been isolated from Phlebia strigosozonata and shown to have highly oxygenated kaurane structures.

The absolute configuration of the dinoflagellate toxins, brevetoxins, has been unequivocally determined by X-ray crystallography of a chiral dioxolane derivative.

A highly stereospecific oxidation of 2-phospholene 1-oxides gives the first successful preparation of phospho sugars, having phosphorus as the sugar ring hetero atom, the relative configuration being confirmed by X-ray crystallography.

Diphenylacetylene and 1,1-dimethyl-2,5-diphenyl-1-silacyclopentadiene crystallize from solution as a 1:1 crystal complex, not as the Diels-Alder adduct; the structure of this complex was determined by X-ray diffraction.

The structure of the triterpenoid oxide from Rhododendron macrophyllum has been determined by single crystal X-ray analysis.

Bromination of semibullvalene proceeds with stereoselective cis,exo-1,4-addition in contrast to bullvalene where kinetically controlled trans-1,4-addition occurs.

The molecular structure of the title compound (3) has been elucidated by single crystal X-ray diffraction analysis.