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

• compounds 1–6, various assays were carried out. The antimicrobial activity of the isolated compounds against Bacillus subtilis DSM10, Escherichia coli DSM498, Candida tenuis MUCL29892, and Mucor plumbeus MUCL49355 was determined as described by Kuephadungphan and co-workers [8]. The nematicidal activity

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• antimicrobial, cytotoxic, and nematicidal activities, as described in the Experimental section. However, compounds 1–5 were devoid of activity in these assays, whereas tyromycin A (6) and skeletocutin A–L had been reported before to be active against several Gram-positive bacteria [4], namely Bacillus subtilis

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

• avoided. A hint in this direction could be that in an in vitro experiment with Spodoptera frugiperda insect cells, a high resilience could be detected with an IC50 of 68 µM. Furthermore, Gram-positive bacteria are significantly growth inhibited through thunbergol (18) exposure with an IC50 for Bacillus

• subtilis of 9 µM and 10 µM for Micrococcus luteus, respectively [25]. For the sustainable, high yield production of bioactive diterpenoids various aspects have to be considered. One key issue in yielding high recombinant terpene production titers, are metabolic bottlenecks in the precursor supply, which

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

• Amit Raj Sharma,
• Enjuro Harunari,
• Tao Zhou,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

• luteus ATCC9341, Bacillus subtilis ATCC6633, Escherichia coli NIHJ JC-2, Ralstonia solanacearum SUPP1541, Rhizobium radiobacter NBRC14554, and Candida albicans NBRC0197 (MIC > 100 μg/mL) but weakly active against Saccharomyces cerevisiae S100 (MIC 100 μg/mL). Conclusion In summary, chemical investigation

• microtiter plates against six bacteria, Bacillus subtilis ATCC6633, Micrococcus luteus ATCC9341, Staphylococcus aureus FDA209P JC-1, Ralstonia solanacearum SUPP1541, Rhizobium radiobacter NBRC14554, Escherichia coli NIHJ JC-2, and two yeasts Candida albicans NBRC0197 and Saccharomyces cerevisiae S100 as

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

• Maryna V. Murlykina,
• Oleksandr V. Kolomiets,
• Maryna M. Kornet,
• Yana I. Sakhno,
• Sergey M. Desenko,
• Victoriya V. Dyakonenko,
• Svetlana V. Shishkina,
• Oleksandr A. Brazhko,
• Vladimir I. Musatov,
• Alexander V. Tsygankov,
• Erik V. Van der Eycken and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

• experiments. Particularly, the evaluation of the antibacterial activity of the small library of new compounds 11 and 12 was carried out. We next screened some selected compounds for their antibacterial activity (Table 2, Supporting Information File 1) against the reference bacterial strains Bacillus subtilis

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

• Hilke Bruns,
• Lisa Ziesche,
• Nargis Khakin Taniwal,
• Laura Wolter,
• Thorsten Brinkhoff,
• Jennifer Herrmann,
• Rolf Müller and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276

• program for their antimicrobial activity (Table 3). While the valine derivative 9 was virtually inactive, the other compounds showed some activity. Glycine compound 11 showed good activity against the Gram-positive bacteria Bacillus subtilis, Staphylococcus aureus, and Micrococcus luteus, and against the

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

• Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

• ], Helicobacter pylori [41], Pseudomonas aeruginosa [42], Campylobacter jejuni [43], Treponema pallidum [44], the cyanobacterium Synechocystis spp. [45], Mesorhizobium loti [46] and Mycoplasma pneumoniae [47]. Furthermore, partial PINs for Bacillus subtilis [48] and Streptococcus pneumoniae [49] have been

• and Gram-negative pathogens, namely Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Acinetobacter baylyi with MICs ranging from 39 to 78 μM [62]. A year later, further SAR investigations from the same research group led to the identification of another tetrahydrocarbazole derivative 12

• paratuberculosis and Mycobacterium bovis, and Gram-negative pathogens Escherichia coli (wt and imp4213), Bacillus subtilis, Neisseria gonorrhoeae, Neisseria meningitidis and Neisseria lactamica [76]. As a result, the compounds were able to successfully inhibit the growth of some of the bacteria tested. The authors

Herpetopanone, a diterpene from Herpetosiphon aurantiacus discovered by isotope labeling

• Xinli Pan,
• Nicole Domin,
• Sebastian Schieferdecker,
• Hirokazu Kage,
• Martin Roth and
• Markus Nett

Beilstein J. Org. Chem. 2017, 13, 2458–2465, doi:10.3762/bjoc.13.242

• performed as previously described [27]. The test organisms included Bacillus subtilis ATCC 6633, Staphylococcus aureus SG 511, Mycobacterium vaccae IMET 10670, Escherichia coli SG 458, Pseudomonas aeruginosa K 799/61, Sporobolomyces salmonicolor SBUG 549, Candida albicans ATCC 14053 and Penicillium notatum

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

• Jihen Ati,
• Pierre Lafite and
• Richard Daniellou

Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180

• ]. More recently, BcGT1 from Bacillus subtilis was shown to efficiently catalyse the glucosylation of thiol-containing acceptors [32]. C-Glycosyltransferases For more than 50 years, C-glycosides have been identified in plants [33][34] as secondary metabolites. At least 5 families of aromatic aglycones

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• not been studied yet, were examined as an amine component in Ugi-4CR and GBB-3CR. The generated compounds were screened for their biological activity towards Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Results and Discussion Since aminoazoles contain an

• compound 9e (Figure 5). Antibacterial activity The antibacterial activity of compounds 4, 6 and 9 (Table 7) was studied (see Experimental part in Supporting Information File 1 for details) against reference bacterial cultures: Bacillus subtilis (strain 1211), Staphylococcus aureus (strain 2231) (Gram

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• antibacterial activity against Escherichia coli and Bacillus subtilis, and antifungal activity against Aspergillus niger and Penicillium notatum. Among the synthesized series of 1-indanone derivatives 64, the highest antibacterial activity was exhibited by derivatives 64k and 64l, whereas the most potent

Posttranslational isoprenylation of tryptophan in bacteria

• Masahiro Okada,
• Tomotoshi Sugita and
• Ikuro Abe

Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37

• same scaffold as that of the ComX pheromones, but with the opposite stereochemistry. This review highlights the biosynthetic pathways and posttranslational isoprenylation of tryptophan. In particular, recent studies on peptide modifying enzymes are discussed. Keywords: Bacillus subtilis

• tryptophan residue of the quorum sensing pheromone from Bacillus subtilis, the ComX pheromone [13]. Quorum sensing is a specific gene expression system dependent on the cell density [14]. In terms of a competition for survival, the cell population density is one of the largest factors for microorganisms

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• the whole E. coli cells and the β-D-2'-deoxyribosides of aforementioned bases have been synthesized in 55–65% yields [1][37][69]. Recently, the comparative effectiveness of immobilized pyrimidine nucleoside phosphorylase from Bacillus subtilis (BsPyNP) and E. coli TP in (i) the phosphorolysis of

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• epidermidis, Escherichia coli, Klebsiella pneumoniae, and Bacillus subtilis. None of the compounds was active at a concentration of 50 μg/mL. In the free radical scavenging assay using 2,2-diphenyl-1-picrylhydrazyl (DPPH), only compounds 1 and 3 exhibited weak activity with EC50 values of 125 and 130 μM

Antibiotics from predatory bacteria

• Juliane Korp,
• María S. Vela Gurovic and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

• consumed the prey bacterium Bacillus subtilis, but not Escherichia coli. Further tests revealed that P. fallax HKI 727 exhibits a prey range that is restricted to Gram-positive bacteria. Culture extracts of strain HKI 727 showed a consistent antimicrobial profile, i.e., they were highly active against Gram

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

• Louis P. Sandjo,
• Victor Kuete and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

• of Trichophyton mentagrophytes (MIC 6.2 µg/mL) and Epidermophyton floccosum (MIC 1.6 µg/mL) [87]. Though no activity was observed against the gram negative bacteria Escherichia coli and Pseudomonas aeruginosa, meridine (56) significantly inhibited the growth of the gram positive bacteria Bacillus

• subtilis, giving a MIC of 3.1 µg/mL [87]. 42 displayed in vitro antiparasitic activity against Plasmodium falciparum (K1, NF54), Leshmania donovani, Trypanosoma cruzi and T. rhodesiense but the effect was much lower than that of standard drugs artemisinin and chloroquine [88]. Ascididemin (42) displayed

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• the alkaline protease from Bacillus subtilis on 7 [25]. The carboxyacetyl (malonyl) derivative of some flavonoid glycosides (i.e., 8b) and of ginsenoside Rg1 (9b) could be obtained with two-step sequences. The preliminary CAL-B catalyzed acylations of 8 with dibenzyl malonate and of 9 with bis(2,2,2

Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

• Martin C. N. Brauer,
• Ricardo A. W. Neves Filho,
• Bernhard Westermann,
• Ramona Heinke and
• Ludger A. Wessjohann

Beilstein J. Org. Chem. 2015, 11, 25–30, doi:10.3762/bjoc.11.4

• -libraries of homo- and heterodimers verified by ESI-MS and HPLC. In a preliminary evaluation, some compounds display moderate activity against the Gram-positive bacterium Bacillus subtilis. Keywords: antibacterial; combinatorial; diynes; homodimerization; multicomponent reactions; peptoids; Ugi reaction

• orders of magnitude of concentration anyhow. Therefore no further attempt to optimize for an equal product distribution was deemed necessary. To gain insight into the antibiotic potential of the products, single compound dimers 8a–j were subjected to a preliminary evaluation against Bacillus subtilis

• inhibitory activity against Bacillus subtilis in a preliminary assay. Apoptosis inducer C2-symmetric 1,3-diyne-linked peptide 1 and its inactive monomer 2. Expanded region of the ESI-MS spectrum (positive mode) and the HPLC chromatogram of the crude mixed library of 1,3-diyne peptoids (8f, 8h, 8j, 9, 10 and

A new approach for the synthesis of bisindoles through AgOTf as catalyst

• Jorge Beltrá,
• M. Concepción Gimeno and
• Raquel P. Herrera

Beilstein J. Org. Chem. 2014, 10, 2206–2214, doi:10.3762/bjoc.10.228

• the synthesis of the interesting compound vibrindole A (Scheme 2), an isolated metabolite of the marine bacteria Vibrio parahaemolyticus, which is active against Bacillus subtilis, Staphylococcus aureus and Staphylococcus albus as has been previously demonstrated [43]. In order to prevent the loss of

Sacrolide A, a new antimicrobial and cytotoxic oxylipin macrolide from the edible cyanobacterium Aphanothece sacrum

• Naoya Oku,
• Miyako Matsumoto,
• Kohsuke Yonejima,
• Keijiroh Tansei and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2014, 10, 1808–1816, doi:10.3762/bjoc.10.190

• . Antimicrobial testing against four Gram-positive bacteria (Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus, and Streptomyces lividans), one Gram-negative bacterium (Escherichia coli), two yeasts (Candida albicans and Saccharomyces cerevisiae), and two fungi (Aspergillus oryzae and Penicillum

• the growth of Gram-positive bacteria (Micrococcus luteus, Streptomyces lividans, Staphylococcus aureus, Bacillus subtilis), a yeast (Saccharomyces cerevisiae) and a fungus (Penicillium chrysogenum) (Table 2). Moreover, 1 was cytotoxic to 3Y1 rat fibroblasts (GI50 4.5 μM). Under microscopic observation

Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

• Jens Schmidt,
• Zeinab Khalil,
• Robert J. Capon and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2014, 10, 1228–1232, doi:10.3762/bjoc.10.121

• activity against the Gram-positive bacteria Staphylococcus aureus ATCC 25923 (IC50 1.8 μM), Staphylococcus epidermidis ATCC 12228 (IC50 0.9 μM) and Bacillus subtilis ATCC 6633 (IC50 1.8 μM), but was inactive (IC50 > 30 μM) against the Gram-negative bacteria Pseudomonas aeruginosa ATCC 10145 and Escherichia

• near Heron Island, Queensland, Australia (Figure 1) [1]. As first in class examples of natural products featuring a 2-nitropyrrole, further elaborated by a farnesyl side chain, the heronapyrroles exhibited promising antibacterial activity against Staphylococcus aureus (ATCC 2593 and 9144) and Bacillus

• subtilis (ATCC 6051 and 6633). Publication of the heronapyrroles was rapidly followed by an account of the biosynthetically related nitropyrrolins A–E, obtained from a different marine-derived actinomycete strain (CNQ-509) (Figure 1) [2]. Of note, the heronapyrroles and nitropyrrolins both feature the same

Cuevaenes C–E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI

• Jing-Jing Deng,
• Chun-Hua Lu,
• Yao-Yao Li,
• Shan-Ren Li and
• Yue-Mao Shen

Beilstein J. Org. Chem. 2014, 10, 858–862, doi:10.3762/bjoc.10.82

• ., Bacillus subtilis strain ATCC 11060) and modest activity against fungi (e.g., Fusarium verticillioides strain S68 and Rhizoctonia solani strain GXE4). However, cuevaenes D (4) and E (5) showed no inhibitory activity against any of the tested microbes. Keywords: antibacterial activity; cuevaenes

• compounds 4 and 5 due to the rotation around the C-5/C-6 single bond (Figure 2). The antimicrobial activities of cuevaenes A–E (1–5) were investigated by paper disc diffusion assay. Cuevaenes A–C (1–3) displayed moderate activity against Gram-positive bacteria such as Bacillus subtilis strain ATCC 11060

• ; found, 354.4193; IR (KBr) vmax: 3338, 3220, 1660, 1592, and 1461 cm−1. For the NMR data see Table 1. Antibacterial and antifungal bioassays: Antibacterial and antifungal activities of compounds 1–5 were tested by the paper disc diffusion method [11]. The bacterial Bacillus subtilis strain ATCC 11060 was

An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y

• Suresh Babu Meruva,
• Akula Raghunadh,
• Raghavendra Rao Kamaraju,
• U. K. Syam Kumar and
• P. K. Dubey

Beilstein J. Org. Chem. 2014, 10, 471–480, doi:10.3762/bjoc.10.45

• antibacterial activity. Eudistomin Y6 (6f) exhibits moderate antibacterial activity against the Gram-positive bacteria Staphylococcus epidermis and Bacillus subtilis. Results and Discussion There are several approaches known in literature for the synthesis of β-carbolines. Most of the syntheses of eudistomin T

Synthesis and biological activities of the respiratory chain inhibitor aurachin D and new ring versus chain analogues

• Xu-Wen Li,
• Jennifer Herrmann,
• Yi Zang,
• Philippe Grellier,
• Soizic Prado,
• Rolf Müller and
• Bastien Nay

Beilstein J. Org. Chem. 2013, 9, 1551–1558, doi:10.3762/bjoc.9.176

• analogue 9 was approximately twice as active as 10. As the 3-methyl analogue 11, aurachin D analogues with variations of the aromatic cycle (17–19) were essentially inactive. Solely analogues 18 and 19 displayed a significant growth inhibitory effect on Bacillus subtilis. Conclusion During this work, not

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

• H. Bauke Albada,
• Alina-Iulia Chiriac,
• Michaela Wenzel,
• Maya Penkova,
• Julia E. Bandow,
• Hans-Georg Sahl and
• Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

• activity against Gram-negative Escherichia coli much more than against Gram-positive Bacillus subtilis [30][31], and only slightly increased the hemolytic activity [32]. Moreover, the alkylation of tryptophan residues by tert-butyl groups resulted in increased activity and low hemolytic activity of the

• in Table 2) The minimal inhibitory concentrations (MIC) were tested against Escherichia coli DSM 30083, Acinetobacter baumannii DSM 30007, Pseudomonas aeruginosa DSM 50071, Bacillus subtilis DSM 402, Staphylococcus aureus DSM 20231 (type strain), and Staphylococcus aureus ATCC 43300 (MRSA) in a