Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities

• Rémy B. Teponno,
• Sara R. Noumeur and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48

• [14]. Massarilactones A and B were earlier shown to exhibit antimicrobial activity against Bacillus subtilis (ATCC 6051) and Staphylococcus aureus (ATCC 29213), affording zones of inhibition varying from 12 to 19 mm at 200 μg/disk [8], while massarilactone H displayed moderate cytotoxicity against

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• potential cytotoxic molecules that might require further mechanistic investigation. In the antimicrobial activity assay (Table 2), farinosone B (3), beauvericins A (4) and B (5) were the most potent metabolites, especially against S. aureus and Bacillus subtilis with MIC values between 4.2 and 16.6 µg/mL

• 2656), Schizosaccharomyces pombe (DSM 70572), Rhodotorula glutinis (DSM 10134), and Wickerhamomyces anomalus (DSM 6766). Additionally, various Gram-positive bacteria such as Staphylococcus aureus (DSM 346), Bacillus subtilis (DSM 10), Mycobacterium smegmatis (ATCC 700084), and Gram-negative bacteria

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

• contamination with the strongly mutagenic altertoxins [82][83]. When administered to rats, AME induced gene mutations, chromosome breakage, and DNA damage [114]. AME turned out to be active against bacteria (Bacillus subtilis, Staphylococcus haemolyticus, Agrobacterium tumefaciens, Pseudomonas lachrymans

• sp. [172][180] and Rhizopycnis vagum [171]. Palmariol A and B showed weak antifungal activity against Mucor racemosus (8 mm inhibition zone at 20 μM/disc) and palmariol A was furthermore active against Bacillus subtilis (9 mm) [178]. Palmariol B was found to show a higher antimicrobial activity than

• 9-O-methylalternariol, obviously due to the additional chlorine substituent. It was active against Agrobacterium tumefaciens, Bacillus subtilis, Pseudomonas lachrymans, Ralstonia solanacearum, and Xanthomonas vesicatoria (IC50 values from 16.7 to 18.1 μg/mL) and disclosed antinematodal activity

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

• -terminally methylated nisin retains its antibiotic activity, with MIC (minimal inhibitory concentration) values of 1 µM and 4 µM against Lactococcus lactis and Bacillus subtilis, respectively. Haloduracin is a two-component lanthibiotic that is methylated at both cyclised N-termini by CypM. These experiments

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

• Weimao Zhong and
• Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

• enzyme RagaA7 was produced in a Bacillus subtilis host and characterized to be a neoagarotetraose-producing GH-16 family endo-type β-agarase with a pH and temperature optima being 7.0 and 50 °C, respectively. Another thermostable neoagarotetraose-producing GH-16 endo-type β-agarase rAgaA was identified

Substrate specificity of a ketosynthase domain involved in bacillaene biosynthesis

• Zhiyong Yin and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2024, 20, 734–740, doi:10.3762/bjoc.20.67

• understanding of polyketide biosynthesis has been reached, including a detailed knowledge of the extender unit selection and the stereochemical implications that are predictable from amino acid sequences [5][6]. The polyene antibiotic bacillaene was first isolated from Bacillus subtilis [7]. This soil-dwelling

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• Bacillus subtilis, BsIDH, has an optimal pH between 9.5–10 [12][13]. We also compared product formation between reactions with Hyg17 or BsIDH and myo-inositol using thin-layer chromatography (Supporting Information File 1, Figure S3). We found that both enzymes generated a ketone product with identical

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• -positive bacteria, Kocuria rhizophila ATCC 9341 and Bacillus subtilis ATCC 6633; two strains of Gram-negative bacteria, Escherichia coli Europe NIHJ and Xanthomona campestis pv. oryzae KB 88; and two strains of fungi, Candida albicans ATCC 64548 and Mucor racemosus IFO 4581. All strains were tested by

Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells

• Fumihiro Ishikawa,
• Sho Konno,
• Hideaki Kakeya and
• Genzoh Tanabe

Beilstein J. Org. Chem. 2024, 20, 445–451, doi:10.3762/bjoc.20.39

• ]. Moreover, the intracellular concentrations of a series of AMS derivatives in Escherichia coli, Bacillus subtilis, and Mycobacterium smegmatis have been investigated by Tan et al., demonstrating non-obvious correlations between the chemical structure and permeability among various bacteria, owing to the

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• cereus, Bacillus subtilis, Staphylococcus epidermidis, Corynebacterium pseudodiphtheriticum), four Gram-negative bacteria (Escherichia coli, Proteus mirabilis, Enterobacter aerogenes, Enterobacter cloacae), and three fungi (Saccharomyces cerevisiae, Candida albicans, Penicillium chrysogenum). The goal of

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• against Staphylococcus aureus and Bacillus subtilis at MIC values comparable to gentamycin and oxytetracycline (positive controls), respectively. Keywords: antimicrobial activity; Fomitopsis carnea; lanostane glycosides; Polyporales; Introduction Great success was realized on antibiotic discovery

• compound 1 was moderately active against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus at MIC values of 8.3 µg/mL and 16.6 µg/mL, respectively. The antagonism of 1 against B. subtilis and S. aureus was compared to the positive controls oxytetracycline and gentamycin, with MICs

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

• Till Steinmetz,
• Blaise Kimbadi Lombe and
• Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

• signal at δH 7.62 ppm characteristic for an amide. In vitro tests were conducted for all compounds to assess their antibacterial activities against three Gram-negative bacteria (Escherichia coli, Agrobacterium tumefaciens and Pseudomonas fluorescens) and one Gram-positive bacterium (Bacillus subtilis

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• 8b is rather low in Ugi reactions. Antibacterial activity In the following experiment, we tested a specific group of compounds for their ability to act as antibacterial agents against Bacillus subtilis (strain 1211), Staphylococcus aureus (strain 2231) (Gram-positive), Escherichia coli (strain 1257

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• ) against the bacteria Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, Escherichia coli, Klebsiella pneumoniae, and the fungi Aspergillus niger, Aspergillus terreus, and Aspergillus flavus. Unfortunately, all compounds were found to be inactive [14]. The use of compounds capable to delay

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• established by comparison of optical rotation values with synthetically prepared authentics. Compound 1 inhibited the growth of Bacillus subtilis and Staphylococcus aureus at MIC of 50 μg/mL and 100 μg/mL, respectively. Keywords: antibacterial; cyanobacterium; edible; monoacylglycerol; Nostochopsis lobatus

• ethanolic extract of this alga and found that a mid-polar fraction inhibited the growth of two Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus. Activity-guided fractionation led to the discovery of a new monoacylglycerol, nostochopcerol (1, Figure 1). Part of this study have been

• -hexane. The resulting three layers were tested against four Gram-positive bacteria, five Gram-negative bacteria, six fungi, and two yeasts, which detected antibacterial activity against two Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, from the 90% aqueous MeOH layer. The

Solid-phase total synthesis and structural confirmation of antimicrobial longicatenamide A

• Takumi Matsumoto,
• Takefumi Kuranaga,
• Yuto Taniguchi,
• Weicheng Wang and
• Hideaki Kakeya

Beilstein J. Org. Chem. 2022, 18, 1560–1566, doi:10.3762/bjoc.18.166

• developed [4]. Among the isolated longicatenamides, compound 1 exhibits weak but preferential antimicrobial activity against Bacillus subtilis. Because peptides 1–4 are not detected in the monoculture broth of Streptomyces sp. KUSC_F05, they are key tools for understanding chemical communication in the

• (MIC) = 50 μM) exhibited moderate but selective antimicrobial activity against Bacillus subtilis similar to natural 1 (MIC = 100 μM). Conclusion We accomplished solid-phase total synthesis of longicatenamide A (1). Initially, commercially unavailable building blocks 7 and 10 were chemically synthesized

Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

• Houchao Xu,
• Anne Wochele,
• Minghe Luo,
• Gregor Schnakenburg,
• Yuhui Sun,
• Heike Brötz-Oesterhelt and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165, doi:10.3762/bjoc.18.120

• against Bacillus subtilis [1]. Together with a structural revision from 29Z to 29E configuration and further biological evaluation of its hepatoprotective properties, its biosynthetic gene cluster was recently identified [2]. The biosynthetic machinery is composed of a hybrid trans-acyltransferase (trans

• growth retardation of the Gram-positive species Bacillus subtilis 168 and Acinetobacter baumannii 09987 (Figure 3A and B). However, growth inhibition was not strong enough to yield a clear MIC value, as the determination of a MIC requires complete inhibition of visible bacterial growth and residual

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

• /mL, while compound 4p was the most active one against Bacillus subtilis with a MIC value of 70 µg/mL. Interestingly, compounds 4a and 4u exerted selective activity against Gram-positive bacteria. The synthesized compounds showed good activity against A. fumigatus and C. albicans and compound 4v

• biological activities such as anti-COVID-19 [5], anticancer [6][7][8], antibacterial activity against Staphylococcus aureus and Bacillus subtilis [9][10], antifungal agents against Candida albicans and phytopathogenic fungi [11][12], and antiproliferative against different cell lines (e.g., PC3, HCT-116, and

• for their in vitro antibacterial potential against Staphylococcus aureus and Bacillus subtilis as examples of Gram-positive bacteria as well as against Escherichia coli and Proteus vulgaris as examples of Gram-negative bacteria [35]. They were also evaluated for their in vitro antifungal activity

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• H-13 (Figure 6). Thus, an S-configuration, corresponding to an ʟ-chirality for tryptophan, was assigned. Compounds 1–6 were not cytotoxic against P388 murine leukemia cells (IC50 > 100 μM), nor antimicrobial against five bacteria, Bacillus subtilis, Staphylococcus aureus, Ralstonia solanacearum

Biological properties and conformational studies of amphiphilic Pd(II) and Ni(II) complexes bearing functionalized aroylaminocarbo-N-thioylpyrrolinate units

• Samet Poyraz,
• Samet Belveren,
• Sabriye Aydınoğlu,
• Mahmut Ulger,
• Abel de Cózar,
• Maria de Gracia Retamosa,
• Jose M. Sansano and
• H. Ali Döndaş

Beilstein J. Org. Chem. 2021, 17, 2812–2821, doi:10.3762/bjoc.17.192

• organometallic compounds were screened for their antibacterial activity against a range of Gram-positive (Staphylococcus aureus, Bacillus subtilis) and Gram-negative (Aeromonas hydrophila, Escherichia coli, Acinetobacter baumannii) bacteria and antimycobacterial activity against M. tuberculosis H37Rv strains

• range of 15.62–250 μg/mL when compared to reference drugs. The L3-Ni complex possessing the indole ring is the most active compound among the other complexes against Bacillus subtilis with a value of 15.62 μg/mL. The activities of the samples were compared with the results obtained with ampicillin (0.9

• [ATCC 25925], Bacillus subtilis [ATCC 6633], Aeromonas hydrophila [ATCC 95080], Escherichia coli [ATCC 25923], and Acinetobacter baumannii [ATCC 02026]) was determined with a resazurin microtitre assay (REMA). These standard strains were obtained from Refik Saydam Hıfzıssıhha Institute (Ankara, Turkey

Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

• Zhiwei Zhang,
• Tao Zhou,
• Taehui Yang,
• Keisuke Fukaya,
• Enjuro Harunari,
• Shun Saito,
• Katsuhisa Yamada,
• Chiaki Imada,
• Daisuke Urabe and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2194–2202, doi:10.3762/bjoc.17.141

• absolute configuration was determined by combination of NOESY/ROESY and ECD analyses. Nomimicins B, C, and D showed antimicrobial activity against Gram-positive bacteria, Kocuria rhizophila and Bacillus subtilis, with MIC values in the range of 6.5 to 12.5 μg/mL. Nomimicins B and C also displayed

• antimicrobial activity against Kocuria rhizopila with a MIC value of 6.5 μg/mL and 1 and 2 were also active against Bacillus subtilis with a MIC value of 12.5 μg/mL. Compounds 1–3 were inactive against Staphylococcus aureus, Ralstonia solanacearum, Rhizobium radiobacter, and Candida albicans. In addition, 1 and

Molecular basis for protein–protein interactions

• Brandon Charles Seychell and
• Tobias Beck

Beilstein J. Org. Chem. 2021, 17, 1–10, doi:10.3762/bjoc.17.1

• a lower resolution of protein structures and size requirements of the proteins under investigation. Nonetheless, resolution and size barriers are continuously being broken, with resolutions of up to 1.15 Å (human apoferritin, EMD-11668, PDB: 7a6a [17]) and structures as small as 25 kDa (Bacillus

• subtilis 50S subunit-nascent chain-tRNA complex, EMD-4799, no available PDB [18]) were solved. Protein crystals can also be used in conjunction with cryo-EM, employing a technique known as microcrystal electron diffraction (MicroED). With this method, thin 3D crystal slices are used to obtain the protein

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• , Kgs. Lyngby, Denmark 10.3762/bjoc.16.248 Abstract Secondary metabolites provide Bacillus subtilis with increased competitiveness towards other microorganisms. In particular, nonribosomal peptides (NRPs) have an enormous antimicrobial potential by causing cell lysis, perforation of fungal membranes

• to understand their ecological role. Keywords: Bacillus subtilis; bacterial community; chemical ecology; Lysinibacillus fusiformis; nonribosomal peptides; surfactin; Introduction In nature, bacteria live in complex communities where they interact with various other microorganisms. Most microbial

• neighbouring organisms induce and increase the SM production in the tested strains. Bacillus subtilis is a well-studied soil bacterium and is used as a model organism for biofilm formation and sporulation [30]. It has been shown that several members of the B. subtilis species complex have exceptional plant

Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

• Jan Geldsetzer and
• Markus Kalesse

Beilstein J. Org. Chem. 2020, 16, 670–673, doi:10.3762/bjoc.16.64

• (Cmc5) by the groups of Höfle and Reichenbach in 2003 [12]. This PKS/NRPS-derived natural product shows only weak antibiotic effects in agar diffusion tests against Micrococcus luteus, Schizosaccharomyces pombe, Bacillus subtilis and Staphylococcus aureus [12]. The relative and absolute stereochemistry