Fabclavine diversity in Xenorhabdus bacteria

• Sebastian L. Wenski,
• Harun Cimen,
• Natalie Berghaus,
• Sebastian W. Fuchs,
• Selcuk Hazir and
• Helge B. Bode

Beilstein J. Org. Chem. 2020, 16, 956–965, doi:10.3762/bjoc.16.84

• unknown derivatives were identified and confirmed by MALDI–MS and MALDI–MS2 experiments in combination with an optimized sample preparation. This led to a total number of 22 novel fabclavine derivatives in eight strains, increasing the overall number of fabclavines to 32. Together with the identification

• of fabclavines as major antibiotics in several entomopathogenic strains, our work lays the foundation for the rapid fabclavine identification and dereplication as the basis for future work of this widespread and bioactive SM class. Keywords: antibiotic; fabclavine; NRPS-PKS hybrid; secondary

• modification step (Figure S1, Supporting Information File 1) [25]. Identification of new fabclavine derivatives To analyze the identified fcl BGCs, mutant strains were generated with a chemically inducible promoter in front of fclC or corresponding homologues (Figure 2). The inducible promoter was integrated

Six-fold C–H borylation of hexa-peri-hexabenzocoronene

• Mai Nagase,
• Kenta Kato,
• Akiko Yagi,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

• –Ishiyama borylation step is possibly increased by further conditions screening. The thus-obtained 1 was identical to the product from the C–H borylation of HBC according to 1H NMR spectroscopy, and the 13C NMR and HRMS by MALDI–TOF MS results also supported the identification. The hexaborylated HBC 1 was

Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211

• Ken-ichi Nakashima,
• Junko Tomida,
• Takao Hirai,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28

• leaves of Selaginella tamariscana (Selaginellaceae) were cultivated in Tajimi City, Gifu, Japan. The methods of isolation and identification of endophytic fungi were performed in a similar manner as described previously [8]. Based on the DNA sequencing of ITS of rDNA and the D1/D2 domain of 26S rDNA

Synthesis, liquid crystalline behaviour and structure–property relationships of 1,3-bis(5-substituted-1,3,4-oxadiazol-2-yl)benzenes

• Afef Mabrouki,
• Malek Fouzai,
• Armand Soldera,
• Abdelkader Kriaa and
• Ahmed Hedhli

Beilstein J. Org. Chem. 2020, 16, 149–158, doi:10.3762/bjoc.16.17

• realized in cooling and heating cycles for compounds 2b, 4a and 4b (Figure 2). POM technique has illustrated smectic phases for all compounds. Identification of the phase textures was accomplished by comparing with those reported in literature [24]. The texture of 2b (Figure 2a) seems to be a variant of

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

• Soleiman E. Helaly,
• Wilawan Kuephadungphan,
• Patima Phainuphong,
• Mahmoud A. A. Ibrahim,
• Kanoksri Tasanathai,
• Suchada Mongkolsamrit,
• Janet Jennifer Luangsa-ard,
• Souwalak Phongpaichit,
• Vatcharin Rukachaisirikul and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

• results for bioassays, as well as species identification of the pigmentosin and glycoasperfuran producers. Acknowledgements This work was supported by the TRF through the Royal Golden Jubilee Ph.D. program (grant no. PHD/0163/2556 to WK); Alexander von Humboldt Foundation (Georg-Forster Grant to SEH

Two new aromatic polyketides from a sponge-derived Fusarium

• Mada Triandala Sibero,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Ocky K. Karna Radjasa,
• Agus Sabdono,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289

• summary, our chemical analysis of a sponge-derived fungus of the genus Fusarium led to the identification of two new and three known aromatic polyketides (1 and 2, and 3–5, respectively) and two sesquiterpenes (6 and 7). Although secondary metabolites of Fusarium were extensively studied in the past [26

Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

• Alonso Pardo-Vargas,
• Priya Bharate,
• Martina Delbianco and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2019, 15, 2936–2940, doi:10.3762/bjoc.15.288

• ]. Identification of novel anti-TB agents that specifically target AMs with high sensitivity are required. Pure AM oligosaccharides may help to identify new lead compounds for the development of diagnostics. Since the isolation of pure oligosaccharides from MTB strains in sufficient quantities is challenging, the

Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum

• Xinlu Chen,
• Tobias G. Köllner,
• Wangdan Xiong,
• Guo Wei and
• Feng Chen

Beilstein J. Org. Chem. 2019, 15, 2872–2880, doi:10.3762/bjoc.15.281

• and gene expression patterns, the products of most DdTPSs were released as volatiles from D. discoideum at the multicellular developmental stage [14][15]. TPS genes previously were known to exist only in bacteria, fungi, and plants [13][17][18]. The identification of TPS genes in dictyostelid social

• . At the 18th day after the transfer, essentially the same profile of volatiles was detected (Figure 1A). Four terpene synthase genes were identified in P. polycephalum With the identification of terpenes from the headspace of P. polycephalum (Figure 1), the next question was how they are synthesized

• for one hour, the SPME fiber was withdrawn and then inserted into the injector port of a Shimadzu 17A gas chromatograph coupled to a Shimadzu QP5050A quadrupole mass selective detector for volatile identification and identification. Separation was performed on a Restek Rxi-5Sil MS column (30 m × 0.25

An improved, scalable synthesis of Notum inhibitor LP-922056 using 1-chloro-1,2-benziodoxol-3-one as a superior electrophilic chlorinating agent

• Nicky J. Willis,
• Elliott D. Bayle,
• George Papageorgiou,
• David Steadman,
• Benjamin N. Atkinson,
• William Mahy and
• Paul V. Fish

Beilstein J. Org. Chem. 2019, 15, 2790–2797, doi:10.3762/bjoc.15.271

• penetration is an essential requirement of the compound but would be an ideal peripherally restricted control. These data will contribute to the understanding of drug levels of 1 to overlay with appropriate in vivo efficacy endpoints, i.e., the PK-PD relationship. The identification of a suitable analogue of

• tool by capping off the acid as an amide. Although significant Notum inhibition activity could be achieved, none of these amides demonstrated the required combination of metabolic stability along with cell permeability without evidence of P-gp mediated efflux. The identification of a suitable analogue

A photochemical determination of luminescence efficiency of upconverting nanoparticles

• Baptiste Amouroux,
• Clément Roux,
• Jean-Claude Micheau,
• Fabienne Gauffre and
• Christophe Coudret

Beilstein J. Org. Chem. 2019, 15, 2671–2677, doi:10.3762/bjoc.15.260

• after identification by TEM. Yet, this type of work has remained isolated. Moreover, in these conditions, the nanoparticles do not work in conditions close to their foreseen applications. As we became interested in the design of such nanoparticles [21], we envisioned a “chemical approach” of this

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• identification of the nanangenines – a family of seven new and three previously reported drimane sesquiterpenoids. The structures of the nanangenines were elucidated by detailed spectroscopic analysis supported by single crystal X-ray diffraction studies. The compounds were assayed for in vitro activity against

• bacteria, fungi, mammalian cells and plants. Bioinformatics analysis, including comparative analysis with other acyl drimenol-producing Aspergilli, led to the identification of a putative nanangenine biosynthetic gene cluster that corresponds to the proposed biosynthetic pathway for nanangenines. Keywords

• production of terpenoids as the dominant biosynthetic class of secondary metabolites. Results and Discussion Purification and identification The metabolite profile of A. nanangensis was examined on a limited range of solid and liquid media suitable for fungal metabolite production. The metabolite profile

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

• Shital K. Chattopadhyay,
• Subhankar Ghosh,
• Sarita Sarkar and
• Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

• ,ß-dehydro-SAHA derivatives relied on the identification that a successful cross metathesis between anilide 7a (Scheme 1) containing a terminal double bond and N-benzyloxyacrylamide (8) may provide access to α,ß-dehydro-SAHA derivative 10a, which may serve as precursor of both SAHA and its dehydro

Indium-mediated C-allylation of melibiose

• Christian Denner,
• Manuel Gintner,
• Hanspeter Kählig and
• Walther Schmid

Beilstein J. Org. Chem. 2019, 15, 2458–2464, doi:10.3762/bjoc.15.238

• unprotected elongated disaccharides in the equilibrium of the pyranoid as well as furanoid isomers in both anomeric forms, respectively. Per-O-acetylation has been performed to facilitate separation of the isomeric mixture for structural identification. The main product revealed to adopt a β-pyranoid form of

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• nitrogen-containing heterocycles with potential biological activity" (0119U100716) and the Ministry of Education and Science of Ukraine for financial support in the frame of project “Molecular docking for express identification of new potential drugs” (0119U002550).

Current understanding and biotechnological application of the bacterial diterpene synthase CotB2

• Ronja Driller,
• Daniel Garbe,
• Norbert Mehlmer,
• Monika Fuchs,
• Keren Raz,
• Dan Thomas Major,
• Thomas Brück and
• Bernhard Loll

Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228

• sequences of other bacterial TPSs for the presence of the RY pair, also called “basic pair” [61][62] and their flanking regions, led to the identification of a conserved tryptophan six amino acids upstream of the RY pair (Figure 6) [37]. In CotB2, residues of the motif are located at the end of the C

• diterpene synthases. Hence, the discovery of this novel motif might help in the identification and functional assignment of novel TPSs. The importance of the tryptophan residue in the WXXXXXRY motif of CotB2 was proven by mutation to glycine (W288G), where the product was changed to 3,7,18-dolabellatriene

Perspective isomorphs – a new classification of molecular structures based on artistic and chemical concepts

• Jannis Neumann,
• Ansgar Schnurr and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2019, 15, 2319–2326, doi:10.3762/bjoc.15.224

• substances by transforming their structural information into an explicit character sequence for identification. The information is given in terms of layers around the atoms and their bond connectivity, tautomeric information, isotope information, stereochemistry, and electronic charge information. In

Isolation of fungi using the diffusion chamber device FIND technology

• Benjamin Libor,
• Henrik Harms,
• Stefan Kehraus,
• Ekaterina Egereva,
• Max Crüsemann and
• Gabriele M. König

Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216

• . Unfortunately, sequences for only 33 Chrysosporium species are available as reference sequences, and thus no identification on the species level could be achieved. Interestingly, the sequence of our isolated Leucothecium species is 100% identical to the reference sequence of an uncultured fungus isolated from

• attached carbon atoms with an HSQC experiment, analysis of the 1H,1H-COSY data led to the identification of two major 1H–1H spin systems, one corresponding to the H-2–H-1b–H-6 moiety (spin system A) and the second to the H2-8–H3-13 subunit (spin system B; Figure 2). Spin system B was extended by a

• be cultivated for further purposes like taxonomic identification or natural product isolation. Isolation methods like baiting may lead to bait-specific fungi only. A strain of A. umbrinum was isolated by Deshmukh et al. using a hair baiting technique. The majority of those isolates showed

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• -derived tris(crown ether) host (eTC) via a dynamic covalent chemistry approach involving triple threading and a Grubbs-catalyzed ring-closing metathesis [68]. 1H NMR titration experiments have been used for the identification of co-conformations of the four related stable states of 19. The authors have

Characterization of two new degradation products of atorvastatin calcium formed upon treatment with strong acids

• Jürgen Krauß,
• Monika Klimt,
• Markus Luber,
• Peter Mayer and
• Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2085–2091, doi:10.3762/bjoc.15.206

• structures of the degradation products. Here we report the identification of two novel degradation products of atorvastatin, which are formed only under drastic acidic conditions. While treatment with conc. sulfuric acid led to a loss of the carboxanilide residue (accompanied by an expectable lactonization

Genome mining in Trichoderma viride J1-030: discovery and identification of novel sesquiterpene synthase and its products

• Xiang Sun,
• You-Sheng Cai,
• Yujie Yuan,
• Guangkai Bian,
• Ziling Ye,
• Zixin Deng and
• Tiangang Liu

Beilstein J. Org. Chem. 2019, 15, 2052–2058, doi:10.3762/bjoc.15.202

• Trichoderma, such as trichodiene synthase homologous gene isolation and characterisation in T. harzianum [32] and functional identification of terpene synthase vir4 in T. virens [33]. However, owing to the general lack of previous studies of terpene synthases in T. viride, Tvi09626 is the first terpene

Multicomponent reactions III

• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1974–1975, doi:10.3762/bjoc.15.192

• environmental concern, the concept of multicomponent reactions (MCRs) [1] has become a particularly powerful principle of synthetic design, combining synthetic efficiency with conceptual efficacy. The importance of rapid lead finding and identification has demanded novel ways of synthetic approaches, ultimately

Analysis of sesquiterpene hydrocarbons in grape berry exocarp (Vitis vinifera L.) using in vivo-labeling and comprehensive two-dimensional gas chromatography–mass spectrometry (GC×GC–MS)

• Philipp P. Könen and
• Matthias Wüst

Beilstein J. Org. Chem. 2019, 15, 1945–1961, doi:10.3762/bjoc.15.190

• ) coupled to a time-of-flight mass spectrometer (TOF–MS) after headspace-solid phase microextraction (HS-SPME). The identification of structurally complex natural compounds, such as sesquiterpenes from fruits and vegetables, is often reported as “tentative”, as authentic standards are not commercially

• chromatograms, i.e., compounds of common structure classes are grouped. The coupling of comprehensive two-dimensional gas chromatography with mass spectrometry as the “third dimension” also provides important information for substance identification. The combination of these advantages makes the GC×GC one of

• , 25 sesquiterpene hydrocarbons were found in the exocarp of ripe grapes (Vitis vinifera L.) of the red wine variety Lemberger. The unequivocal identification of these structurally complex natural compounds was performed by combining multidimensional gas chromatography with in vivo labeling using the

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• anti-inflammatory activity of compound 1 using rat macrophages. Results and Discussion L. archangelica metabolite isolation and identification For isolation of the major metabolites of L. archangelica, we used 100 g of fine ground seeds (Supporting Information File 1, Figure S2) and the method of

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

• Xiao Xie,
• Michela Zuffo,
• Marie-Paule Teulade-Fichou and
• Anton Granzhan

Beilstein J. Org. Chem. 2019, 15, 1872–1889, doi:10.3762/bjoc.15.183

• values cf. Supporting Information, Table S1). In addition, group-average data, i.e., average fluorescence response of each dye towards 12 G4 (DNA and RNA) analytes vs average response to non-G4 (ct DNA and cl RNA) controls, are presented in Figure 6. This plot facilitates the identification of the most

• a set of G4-DNA and G4-RNA analytes, as well as the respective non-G4 controls. The data were analyzed aiming at the identification of structural motifs or physical properties (such as aggregation in aqueous medium) of dyes which could govern their fluorimetric response towards one or another group

Synthesis and biological evaluation of truncated derivatives of abyssomicin C as antibacterial agents

• Leticia Monjas,
• Peter Fodran,
• Johanna Kollback,
• Carlo Cassani,
• Thomas Olsson,
• Maja Genheden,
• D. G. Joakim Larsson and
• Carl-Johan Wallentin

Beilstein J. Org. Chem. 2019, 15, 1468–1474, doi:10.3762/bjoc.15.147

• develop new antibiotics, but the reevaluation of known natural products (NP) and the identification of new NPs and derivatives thereof is considered an especially important pathway in the search for more robust antibiotics [1][2]. The main reasons are the inherent high selectivity and appropriate