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

• respiratory chain. They were shown to block the electron flow at complex I of mitochondria (NADH:ubiquinone oxidoreductase) in a competitive manner, but do not act on bacterial complex I [71][72]. This explains why the myxalamids are mainly active against fungi [71]. The myxovirescins comprise a family of

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• -pyrones Dibenzo-α-pyrones (16) harbor the α-pyrone moiety in the middle part and consist of three ring structures (Figure 2). Aromatic rings are fused to edge c and e of the central 2-pyrone, yielding the basic structure of 16. Many dibenzo-α-pyrone-producing fungi have been described. However, it seems

• that they are mainly distributed in the Alternaria species and mycobionts. Especially endophytic fungi can be regarded as source organisms. Alternariol (17), altenuene (18), and alternariol 9-methyl ether (19) have been described from Alternaria sp. [17], botrallin (20) from Hyalodendriella sp. [18

• ], and graphislactone A (21) from Cephalosporium acremonium IFB-E007 (Figure 3) [19]. These compounds show toxic effects in plants and animals. In addition, Alternaria spp. have been involved in the contamination of food, even in refrigerated stocks, since the fungi is able to grow also at low

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• against entomopathogenic fungi [58], and the defensive character of Spiroplasma species (Tenericutes phylum) associated with Drosophila species [59][60]. Defensive bacterial symbionts of fungus-growing insects Insects, such as ants [61][62], termites [63], beetles [64], and even some bees [65] engage in

• fungi culture [66]. Fungus-growing insects create fungal gardens underground or in wooden galleys in which they grow an obligate food fungus that they supply with organic matter (Figure 4). The nutrient-rich fungus gardens are prone to exploitation by parasitic microorganisms, nematodes and other

• resembles iterative enzymes normally only found in fungi. Subsequently, genomes of phylogenetically diverse bacteria from various environments were screened for the biosynthetic pathways of frontalamide-like compounds using a degenerate primer-based PCR screen. The respective gene clusters were broadly

Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol

• Miriana Kfoury,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2016, 12, 29–42, doi:10.3762/bjoc.12.5

• increasing the shelf-life of food products [7][8]. This is due to their potent activity against a broad range of natural spoilage bacteria, fungi and foodborne pathogens [9][10] as well as their pronounced antioxidant effect [11][12]. Consequently, they could be employed as alternatives to synthetic

Recent highlights in biosynthesis research using stable isotopes

• Jan Rinkel and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2015, 11, 2493–2508, doi:10.3762/bjoc.11.271

• . on the anthraquinone crysophanol, for which different folding modes in fungi (F type folding) and in bacteria (S type, “Streptomyces” type) were found by isotopic labeling experiments for one and the same compound [30]. As an additional concluding remark of this chapter, the role of isotopic labeling

Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

• Qun Göthel,
• Thanchanok Sirirak and
• Matthias Köck

Beilstein J. Org. Chem. 2015, 11, 2334–2342, doi:10.3762/bjoc.11.254

• comparison with 21, compound 3 showed one extra aliphatic carbon and was named aplysinin B. The new compounds 14-debromo-11-deoxyfistularin-3 (1) and aplysinin A (2) were tested for their antimicrobial activity against different Gram-positive and Gram-negative bacteria, fungi, and for their antiproliferative

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) – precursors for dyes and drugs

• Enas M. Malik,
• Younis Baqi and
• Christa E. Müller

Beilstein J. Org. Chem. 2015, 11, 2326–2333, doi:10.3762/bjoc.11.253

• ; Introduction Anthraquinones (AQs, anthracene-9,10-diones) represent an important class of organic compounds. They may be produced synthetically, but many derivatives can also be found in nature, e.g., in medicinal plants, as well as in bacteria, fungi and some insects [1][2][3][4][5][6]. Both, natural and

The marine sponge Agelas citrina as a source of the new pyrrole–imidazole alkaloids citrinamines A–D and N-methylagelongine

• Christine Cychon,
• Ellen Lichte and
• Matthias Köck

Beilstein J. Org. Chem. 2015, 11, 2029–2037, doi:10.3762/bjoc.11.220

• pyrrole–pyridinium alkaloid N-methylagelongine (5) was also isolated from Agelas citrina. Compound 5 is the N-methylated pyrrole derivative of agelongine (12). The debromo compound is known as daminin (21). The citrinamines A–D (1–4) were tested against several pathogenic bacteria, fungi, and cultures of

• liquid agar medium to a final OD of 0.01 (bacteria) or 0.1 (yeasts). Spores of fungi were collected from well-grown Petri dishes, which were rinsed with 10 mL of sterile H2O. One mL of the spore suspension was added to 100 mL of molten agar medium. Plates were incubated at 30 °C, and the diameters of

SmI₂-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B

• Nils Marsch,
• Peter G. Jones and
• Thomas Lindel

Beilstein J. Org. Chem. 2015, 11, 1700–1706, doi:10.3762/bjoc.11.184

• plants [1][2][3] and also in fungi [4] and myxobacteria [5][6]. One example is raputindole A (1), isolated in 2010 from the Rutaceous tree Raputia simulans Kallunki [1], which exhibits a unique tetrahydrocyclopenta[f]indole partial structure (Figure 1) probably formed by dimerization of (E)-6-(3

New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y₂) isolated from the South China Sea

• Senhua Chen,
• Zhaoming Liu,
• Yayue Liu,
• Yongjun Lu,
• Lei He and
• Zhigang She

Beilstein J. Org. Chem. 2015, 11, 1187–1193, doi:10.3762/bjoc.11.133

• ; Meyerozyma guilliermondii; Introduction Depsidones are characterized by the presence of cyclic diaryl ethers with an ester link joining the two aromatic rings [1][2]. They have been isolated mainly from various lichens [3][4][5] and other fungi [6][7][8][9][10][11]. These metabolites displayed a wide range

• of bioactivities including antibacterial [10], antifungal [6], antiviral [12], antioxidant [5], and cytotoxic [9]. In the last decade, our research group has been focused on isolating novel compounds from endophytic fungi growing on mangroves in the South China Sea and investigating their bioactivity

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity

• Agata Walczewska,
• Daria Grzywacz,
• Dorota Bednarczyk,
• Małgorzata Dawgul,
• Andrzej Nowacki,
• Wojciech Kamysz,
• Beata Liberek and
• Henryk Myszka

Beilstein J. Org. Chem. 2015, 11, 869–874, doi:10.3762/bjoc.11.97

• glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have no inhibitory activity against Gram-negative bacteria, whereas many of the tested N-alkyl saponins were found to inhibit the growth of Gram-positive bacteria and human pathogenic fungi

• vitro activity against 5 strains of Gram-negative bacteria, 5 strains of Gram-positive bacteria, and 3 strains of human pathogenic fungi. Respective minimum inhibitory concentration (MIC) values determined by a serial dilution microplate method according to the guidelines of the Clinical and Laboratory

• probably due to the lower solubility of the compounds with longer N-alkyl groups or to the micelle formation. Studies on the activity of the synthesized N-alkyl derivatives of diosgenyl 2-deoxy-2-amino-β-D-glucopyranoside (8–15 and 17) against 3 strains of the human pathogenic fungi (Table 3) indicate that

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• , antimicrobial, anti-oxidant and enzyme inhibitory activities of 1 were evaluated. Keywords: Aspergillus; endophytic fungus; Ginkgo biloba; natural product; norditerpenoid; Trichocomaceae; Introduction Plant-derived fungi, which have drawn considerable attention from natural product chemists, have been proved

• avenae subsp. Citrulli, Erwinia amylovora, Pseudomonas syringae pv. Lachrymans, Clavibacter michiganense subsp. Sepedonicus, and Pectobacterium carotovorum subsp. carotovorum) and fungi (Rhizoctonia solani Kühn, Rhizotonia cerealis van der Hoeven, Phytophthora capsici Leonian, Fusarium moniliforme Sheld

• , Clavibacter michiganense subsp. Sepedonicus, and Pectobacterium carotovorum subsp. carotovorum) and fungi (Rhizoctonia solani Kühn, Rhizotonia cerealis van der Hoeven, Phytophthora capsici Leonian, Fusarium moniliforme Sheld, Alternaria solani Jones et Grout, Sclerotinia sclerotiorum de Bary, Fusarium

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• solubility. Carbendazim is a widely used systemic fungicide against different fungi affecting plants [38][39]. Its mechanism is linked to its antimitotic properties that inhibit the bacterial growth [40]. Due to its poor water-solubility, its application becomes a major constraining factor. In 1996, Schmidt

• , allowing thus the fungi to grow in the presence of relatively high pentachlorophenol concentrations [57]. Unfortunately, the mineralization was inhibited by this CD because of the formation of a too stable complex. Indeed, the complexed pentachlorophenol was not accessible to the degradative system of

• nanoparticles were efficient in vitro against P. aeruginosa, S. aureus, Serratia marcescens, E. coli and Klebsiella pneumoniae. In 2011, the same group extended the scope of microorganisms to human opportunistic pathogenic fungi such as Aspergillus fumigatus, Mucor ramosissimus and Chrysosporium species [86

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• of fumonisin mycotoxins produced by fungi of the genus Fusarium, a common grain mold. It is a close structural analogue of fumonisin B1, the most prevalent member of the family of fumonisins [79][80]. Fumonisin B1, B2 and other fumonisins frequently contaminate maize and other crops [81][82][83

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

Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

• Vincent Fagan,
• Istvan Toth and
• Pavla Simerska

Beilstein J. Org. Chem. 2014, 10, 1741–1748, doi:10.3762/bjoc.10.181

• type of PRR (e.g., Toll Like Receptor (TLR)), an appropriate immune response can be induced for each type of pathogen [7]. The TLR2 is a receptor present on cells of the innate and adaptive immune system. It recognizes lipidic structural components of bacteria, fungi and viruses, and plays a key role

Concise total synthesis of two marine natural nucleosides: trachycladines A and B

• Haixin Ding,
• Wei Li,
• Zhizhong Ruan,
• Ruchun Yang,
• Zhijie Mao,
• Qiang Xiao and
• Jun Wu

Beilstein J. Org. Chem. 2014, 10, 1681–1685, doi:10.3762/bjoc.10.176

• organisms are a main source for the great diversity of naturally occurring nucleosides [1], which play an important role in medical research and pharmaceutical development, especially for the clinical treatment against malignant proliferation and infections by fungi, bacteria and viruses [2][3][4][5][6][7

Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

• Hannes Mikula,
• Julia Weber,
• Dennis Svatunek,
• Philipp Skrinjar,
• Gerhard Adam,
• Rudolf Krska,
• Christian Hametner and
• Johannes Fröhlich

Beilstein J. Org. Chem. 2014, 10, 1129–1134, doi:10.3762/bjoc.10.112

• culmorum. These species, which are the most frequently occurring toxin-producing fungi of the northern temperate zone, are commonly found in cereals and crops throughout the world [4][5]. Significant levels of ZEN are prevalently found in grains such as maize, wheat, and rice [6]. It is known that ZEN can

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

• (diameters of inhibitory zones 11.5, 12.3 and 14.2 mm, respectively) at 30 μg/disc, and modest activity against fungi such as Fusarium verticillioides strain S68 and Rhizoctonia solani strain GXE4 at 30 μg/disc. Interestingly, cuevaenes D (4) and E (5) showed no inhibitory activity against all tested

New sesquiterpene hydroquinones from the Caribbean sponge Aka coralliphagum

• Qun Göthel and
• Matthias Köck

Beilstein J. Org. Chem. 2014, 10, 613–621, doi:10.3762/bjoc.10.52

• -positive and Gram-negative bacteria, fungi, and for antiproliferative activity. The results given in Table 4 show that siphonodictyal E3 (3) and cyclosiphonodictyol A (5) exhibited mild activity against the Gram-positive bacteria Staphylococcus aureus and Micrococcus luteus, while siphonodictyal E4 (4

Tanzawaic acids I–L: Four new polyketides from Penicillium sp. IBWF104-06

• Louis P. Sandjo,
• Eckhard Thines,
• Till Opatz and
• Anja Schüffler

Beilstein J. Org. Chem. 2014, 10, 251–258, doi:10.3762/bjoc.10.20

• preparative HPLC (Waters SunFire, Prep C18 OBD, 5 µm, 19 × 250 mm, 16 mL/min, isocratic conditions, 2:3 acetonitrile/0.1% formic acid) to yield tanzawaic acid I (1, 7.7 mg, tR 9 min) and tanzawaic acid J (2, 12.6 mg, tR 10.5 min). Bioactivity assays. Antimicrobial activities against bacteria and fungi were

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

• Sebastian Krüger and
• Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

• -divinylcyclopropane rearrangement to build up the diterpenoid cyanthin skeleton [181][182][183] like that of allocyathin B2 (226, see Scheme 26), which was isolated from bird’s nest fungi [184][185][186][187][188][189]. Starting from α,β-unsaturated ketone 219 addition of ethynylmagnesium bromide took place, followed

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

• , which were shown to be highly cytotoxic toward cancer cells and fungi. Diastereomers of plakinic acid A, 162a and 162b were synthesized starting from dioxolane ((R)-3-((2R,3E,6S,7E)-2,6-dimethyl-8-phenylocta-3,7-dienyl)-5-(2-methoxyethoxy)-3,5-dimethyl-1,2-dioxolane) (159) [260]. In the first step

SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression

• Silke Felix,
• Louis P. Sandjo,
• Till Opatz and
• Gerhard Erkel

Beilstein J. Org. Chem. 2013, 9, 2866–2876, doi:10.3762/bjoc.9.323

• of apoptosis, regulation of cell proliferation, metastasis and resistance to therapy. Because of its upregulation in malignancy, survivin has currently attracting considerable interest as a new target for anticancer therapy. In a screening of approximately 200 strains of imperfect fungi for the

• promoter and subsequently triggering apoptosis in Colo 320 cells. Drimane sesquiterpenes are widespread in plants, fungi and marine organisms such as algae, sponges and corals and have attracted some attention for their potent antibacterial, antifungal, cytotoxic, antifeedant, phytotoxic, piscicidal and

Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis

• Tao Wang,
• Patrick Rabe,
• Christian A. Citron and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 2767–2777, doi:10.3762/bjoc.9.311

• dichlorodimethoxybenzene (10b or 10k) can arise by a second chlorination from the monochlorodimethoxybenzene (4b or 4f, respectively), suggesting that in both organisms the sets of chlorinated compounds arise via one and the same biosynthetic pathway. Known structurally related compounds from fungi are drosophilin A (19

• our work on volatiles from various bacteria and fungi we rarely encountered chlorinated volatiles. Brominated and iodinated volatiles are even more rare. Investigations on the volatiles released by the actinomycete Streptomyces chartreusis during growth on 84 GYM medium, also collected by use of a