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

• including Acinetobacter baumannii (DSM 30008), Escherichia coli (DSM 1116), Chromobacterium violaceum (DSM 30191), and Pseudomonas aeruginosa (PA14) were included in the assessment. Gentamicin and nystatin served as positive controls against most bacteria and all fungi, respectively. For specific

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• , Don Young Road, Brisbane, 4111, Australia 10.3762/bjoc.20.266 Abstract The marine sponge Suberea ianthelliformis was investigated for new chemistry after the recent discovery that polyamines ianthelliformisamines A–C (1–3) – originally sourced from this Australian sponge – act as Pseudomonas

• ; Pseudomonas; Suberea; total synthesis; Introduction The marine environment covers over two thirds of the earth’s surface and it encompasses a wide range of complex ecosystems that are highly variable in their physical attributes including pressure, salinity, temperature, and light availability. Both flora

• activity against both Pseudomonas aeruginosa and Staphylococcus aureus, has contributed to a surge in the interest of polyamines as new antibacterial leads [6]. To date the total synthesis of ianthelliformisamines A–C (1–3) has been described [7] and numerous synthetically related analogues have been

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

• unambiguously confirmed by independent synthesis [130]. It showed inhibitory activity against Pseudomonas syringae pv. actinidae with an MIC value of 25 μg/mL [127]. O-Glucosides, O-acetates, and O-sulfates of alternariol: As for all natural products bearing hydroxy groups, especially of phenolic hydroxy groups

• turned out to be antibacterially active, inter alia, against Pseudomonas syringae pv. lachrymans, Staphylococcus haemolyticus, and Xanthomonas vesicatoria (IC50 values of 7.3, 10.8, and 10.1 µM, respectively) [163], X. oryzae pv. oryzae, X. o. pv. oryzicola, and Ralstonia solanacearum (MIC: 13.8, 1.7

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

Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

• Moisés Alejandro Alejo Hernandez,
• Katia Pamela Villavicencio Sánchez,
• Rosendo Sánchez Morales,
• Karla Georgina Hernández-Magro Gil,
• David Silverio Moreno-Gutiérrez,
• Eddie Guillermo Sanchez-Rueda,
• Yanet Teresa-Cruz,
• Brian Choi,
• Armando Hernández Garcia,
• Alba Romero-Rodríguez,
• Oscar Juárez,
• Siseth Martínez-Caballero,
• Mario Figueroa and
• Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

• Pseudomonas aeruginosa PA14. This is the first report of lanthipeptides from the Clostridium genus produced with its native biosynthetic machinery, as well as chemically and biologically characterized. This study showcases the immense potential of genome mining in identifying new RiPP synthetases and

Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

• Yu Fan,
• Ahmed El Rhaz,
• Stéphane Maisonneuve,
• Emilie Gillon,
• Maha Fatthalla,
• Franck Le Bideau,
• Guillaume Laurent,
• Samir Messaoudi,
• Anne Imberty and
• Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

• formation is one of main causes of bacterial antimicrobial resistance infections. It is known that the soluble lectins LecA and LecB, produced by Pseudomonas aeruginosa, play a key role in biofilm formation and lung infection. Bacterial lectins are therefore attractive targets for the development of new

• bacterial infections occur by adhesion to host tissues through receptor–ligand interaction between bacterial carbohydrate-binding proteins (lectins) and oligosaccharides at the host cell surface. Pseudomonas aeruginosa (PA), a Gram-negative, opportunistic and ubiquitous environmental bacterium, is known as

• agreement with a stronger enthalpy of interaction, while the entropy barrier could arise from a limitation of flexibility and/or blocking of water molecules at the new interface. Conclusion We have designed and synthesized in three to five steps O- and S-galactosyl azobenzenes targeting the Pseudomonas

Enhancing structural diversity of terpenoids by multisubstrate terpene synthases

• Min Li and
• Hui Tao

Beilstein J. Org. Chem. 2024, 20, 959–972, doi:10.3762/bjoc.20.86

• selectivity with the noncanonical prenyl substrates. To enable the biotechnological synthesis of irregular terpenes, the product selectivity of 2-methylenebornane synthase from Pseudomonas fluorescenes was altered using a semi-rational engineering approach [56]. In contrast to GPP methylation, modification of

Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria

• Kara A. Strickland,
• Brenda Martinez Rodriguez,
• Ashley A. Holland,
• Shelby Wagner,
• Michelle Luna-Alva,
• David E. Graham and
• Jonathan D. Caranto

Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75

• assignment of NnlA as a heme-binding PAS domain protein. As previously reported for a structural homology model of Vs NnlA, the heme position was estimated by overlaying the AlphaFold model with the structure of Pseudomonas aeruginosa Aer2 (Figure 5B). By this method, the His73 is located near the heme

• °C in deoxygenated 30 mM tricine buffer at pH 7.5. Alpha-fold model of Vs NnlA dimer (cyan) overlayed with Pseudomonas aeruginosa (grey; PDB: 3VOL [35][36]) to estimate the position and orientation of the heme cofactor. Conserved residues in the distal heme pocket are labeled. Conserved basic

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• bacteria (Bacillus cereus NBRC 15305 and Kocuria rhizophila NBRC 12708). In addition, several in-house collections of plant pathogens including Erwinia rhapontici_D020, Pantoea agglomerans_G054_1, Agrobacterium tumefaciens_K021_1, Pseudomonas syringae_E029, Ralstonia basilensis_M004 and Paraburkholderia Sp

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• all isolated compounds against a panel of microorganisms (Table 4), including Escherichia coli (ATCC 25922), Candida albicans (ATCC 76485), Staphylococcus aureus (ATCC 27154), Pseudomonas fulva (CGMCC 1.15147), and Enterobacter hormaechei (CGMCC 1.10608). The results indicated that compounds 3, 5, 6

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• –3 were tested against seven human- and marine-derived aquatic pathogenetic bacteria (Edwardsiella tarda, Escherichia coli, Micrococcus luteus, Pseudomonas aeruginosa, Vibrio anguillarum, Vibrio harveyi, and Vibrio vulnificus), and six plant pathogenic fungi (Alternaria brassicae, Colletotrichum

• pathogenic bacteria (Escherichia coli QDIO-1 and Pseudomonas aeruginosa QDIO-4) and aquatic pathogens (Edwardsiella tarda QDIO-2, Micrococcus luteus QDIO-3, V. anguillarum QDIO-6, Vibrio harveyi QDIO-7, and V. vulnificus QDIO-10), as well as plant pathogenic fungi (Colletotrichum gloeosporioides QDAU-2

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• -quinolones produced by the Gram-negative opportunistic pathogen Pseudomonas aeruginosa and related species feature a saturated long-chain substituent at position 2 and are sometimes referred to as pseudanes [34][35]. Pseudomonas aeruginosa alone produces over 50 different quinolones, among which the most

• conditions, and allows easy installation of long-chain substituents at the C-2 position of the quinolone core. These characteristics of the synthetic method could be particularly attractive in the search of novel mimics of the Pseudomonas quorum-sensing signal molecules. The high activity of compounds 4d and

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

• ]. Natural products that are structurally related to 1–6 were discovered in Pseudomonas aeruginosa. It was shown that these compounds function as signaling molecules involved in quorum sensing and stress response [24] which might be an explanation for their low bioactivity against the tested bacteria. Upon

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

• ), Pseudomonas aeruginosa (strain 1111) (Gram-negative). Compared to the reference substance, nitroxoline, the compounds generally showed lower levels of activity. However, some of the compounds demonstrated weak antimicrobial effects, as evidenced by their ability to inhibit the growth of the test

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

• Sanaz Ahmadipour,
• Alice J. C. Wahart,
• Jonathan P. Dolan,
• Laura Beswick,
• Chris S. Hawes,
• Robert A. Field and
• Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

• pathogen in these cases is mucoid Pseudomonas aeruginosa. Such infections are characterised by overproduction of the exopolysaccharide alginate. We present herein the design and chemoenzymatic synthesis of sugar nucleotide tools to probe a critical enzyme within alginate biosynthesis, GDP-mannose

• evaluation against GMD. Keywords: alginate; chemical probe; enzymatic synthesis; GDP-mannose dehydrogenase; sugar nucleotide; Introduction The opportunistic Gram-negative pathogen, Pseudomonas aeruginosa (PA), becomes the dominant pathogen in patients suffering from cystic fibrosis (CF) and causes a

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• , PPK2) was found in Pseudomonas aeruginosa in 2002 [5]. PPK2 were later subdivided into three classes: PPK2-I, PPK2-II, and PPK2-III phosphorylating nucleotide diphosphates (NDPs), nucleotide monophosphates (NMPs), and both, respectively [6]. Nevertheless, these substrate profiles rather seem to be

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• antimicrobial activities [27], the antimicrobial activity of compounds 1–4 was also evaluated against the bacteria Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa. However, all of them were found to be devoid of inhibitory activity (MIC >250

• against nitric oxide (NO) production in LPS-stimulated RAW 264.7 mouse macrophages. The antibacterial activities of compounds 1–4 against Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa were also tested, however, none of them showed

• concentration in the supernatants with Griess reagent as described previously [28]. Antimicrobial assay Compounds 1–4 were evaluated for their antimicrobial activities against Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa. Antimicrobial

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

• intermediate 37 was resolved using a lipase in t-BuOMe, resulting in a high enantiomeric excess. They used an enzymatic resolution of an acetoxy sulfide with a Pseudomonas fluorescens lipase to obtain compound 38. Reaction of chiral acetoxy sulfide 38 with HCl in dry ethanol induced acetate removal by

• isolated oxathiolane precursor 41, as discussed earlier, by enzymatic resolution of an acetoxy sulfide by a Pseudomonas fluorescens lipase. Using this pure precursor 41, the synthesis of 3TC (1) was accomplished by N-glycosylation with silylated base using trimethylsilyl trifluoromethanesulfonate (TMSOTf

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• Infectious Diseases Research in Africa, University of Cape Town, Rondebosch, 7701, South Africa 10.3762/bjoc.17.156 Abstract Five new phenolic siderophores 1–5 were isolated from the organic extract of a culture broth in a modified SGG medium of Pseudomonas sp. UIAU-6B, obtained from sediments collected

• ; pseudomonine; Pseudomonas sp.; vancomycin-sensitive Enterococcus faecium; Introduction The introduction of antimicrobial drugs in the mid-20th century has had an unprecedented positive impact on human health, but the current threat of multiple drug resistance may well roll back all these past achievements [1

• ]. One way out of this is an extensive search for novel bioactive natural products from microbial sources [2][3]. There is focus on the genus Pseudomonas for scientific research due to its widespread distribution in water, soil, and extreme habitats, including the exceptional ability to colonize the

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• . Observations revealed that the conventional refluxing method produced only 10% of the desired product and brought microwave assistance to light. The synthesized molecules showed good antimicrobial activity against Escherichia coli, Candida tropicalis, Staphylococcus aureus and Pseudomonas aeruginosa (Scheme 12

β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes

• Zafar Iqbal,
• Lijuan Zhai,
• Yuanyu Gao,
• Dong Tang,
• Xueqin Ma,
• Jinbo Ji,
• Jian Sun,
• Jingwen Ji,
• Yuanbai Liu,
• Rui Jiang,
• Yangxiu Mu,
• Lili He,
• Haikang Yang and
• Zhixiang Yang

Beilstein J. Org. Chem. 2021, 17, 711–718, doi:10.3762/bjoc.17.60

• in clinical practice in combination with ceftazidime [6]. Followed by avibactam, a relebactam/imipenem/cilastatin [6] combination has been approved by the FDA for the treatment of clinical indications against carbapenemases, ESBLs, and MDR Enterobacteriaceae as well as Pseudomonas aeruginosa [19][20

Identification of volatiles from six marine Celeribacter strains

• Anuj Kumar Chhalodia,
• Jan Rinkel,
• Dorota Konvalinkova,
• Jörn Petersen and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

• from the roseobacter group is the production of the sulfur-containing antibiotic tropodithietic acid (TDA) in Phaeobacter piscinae DSM 103509T [28], a compound that is in equilibrium with its tautomer thiotropocin [29] that was first described from Pseudomonas sp. CB-104 [30]. Its biosynthesis depends

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

• %), and Gaiella (3–4%). The communities of the 12 h precultivated soil suspension consisted primarily of the two genera Bacillus (56–65%) and Acinetobacter (29–34%). Additional genera with an abundance higher than 1% were Lysinibacillus (1.2–3.2%), Pseudomonas (1.0–2.2%), and Viridibacillus (0.6–1.5

• Acinetobacter correlated best with the communities supplemented with the NRP-producing B. subtilis strains, hinting a higher frequency of these in NRP-treated communities. Additionally, three ASVs, identified as Pseudomonas, Citrobacter, and Sphingobacterium, correlated with two communities treated with the

• communities, compared to the precultivated soil suspensions and contained 11–18 genera (Figure 3). The most abundant genera, having a proportion greater than 0.19% in at least one B. subtilis-treated or untreated mock community were Acinetobacter, Lysinibacillus, Pseudomonas, Chryseobacterium, Bacillus

Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

• David Liese,
• Hans Henning Wenk,
• Xin Lu,
• Jochen Kleinen and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2020, 16, 2820–2830, doi:10.3762/bjoc.16.232

• Pseudomonas aeruginosa, a Gram-negative rod-shaped bacterium [5][6][7][8]. RL are built up by one or two rhamnose sugar units as well as one to three β-hydroxy fatty acids, which can also be unsaturated. These highly functional biomolecules exhibit interesting biological and antibacterial properties, as

Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol

• Ekaterina E. Stepanova,
• Maksim V. Dmitriev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2020, 16, 2322–2331, doi:10.3762/bjoc.16.193

• (detailed data on biological assays is given in Supporting Information File 1). Unfortunately, we found that tested BTAs 3 did not show any significant antimicrobial activity (against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, Candida