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

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

• different fungal species [1]. Zearalenone (ZEN, 1) is a well-known RAL type mycotoxin for which maximum tolerated levels in food and feed were enacted and recommended, respectively, in Europe [2][3]. ZEN is produced by several plant pathogenic Fusarium species, including Fusarium graminearum and Fusarium

• first chemical synthesis of the ZEN-derivative 14-O-acetylzearalenone (14-AcZEN, produced by some Fusarium strains) [28] is reported. Results and Discussion The general strategy for regiocontrolled conjugation at position 2’ of resorcylic acid esters and lactones is shown in Scheme 1. Regioselective

• Austrian Science Fund (FWF) special research project SFB Fusarium (F3706 and F3708).

Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids

• Angélica de Fátima S. Barreto,
• Otilie E. Vercillo,
• Ludger A. Wessjohann and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2014, 10, 1017–1022, doi:10.3762/bjoc.10.101

• cyclic depsipeptide is sansalvamide A (San A, Figure 1) [20][21][22][23][24][25][26][27][28][29], which was isolated from a marine fungus (Fusarium spp.) [20] and exhibits antitumor activity against multiple cancer cell lines. It is cytotoxic against colon (HCT-116) [20][23][25][26], pancreatic (S2-013

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

• grown on LB agar. The fungus Fusarium verticillioides strain S68 and Rhizoctonia solani strain GXE4 were grown on potato dextrose agar. Test compounds were absorbed onto individual paper disks (6 mm diameter) at 30 μg/disc and placed on the surface of the agar. The assay plates were incubated at 28 °C

The myxocoumarins A and B from Stigmatella aurantiaca strain MYX-030

• Tobias A. M. Gulder,
• Snežana Neff,
• Traugott Schüz,
• Tammo Winkler,
• René Gees and
• Bettina Böhlendorf

Beilstein J. Org. Chem. 2013, 9, 2579–2585, doi:10.3762/bjoc.9.293

• fungicides, although on a somewhat lower activity level. To further substantiate these results, liquid culture assays against a set of fungal pathogens were performed, showing strong intrinsic antifungal activities against M. grisea (100% inhibition at 0.7 mg/L) as well as B. cinerea, Fusarium culmorum, and

• (Pythium ultimum Trow; Rhizoctonia solani Kühn) or conidia of the fungus from cryogenic storage (B. cinerea; P. nodorum; P. grisea; Fusarium culmorum (Wm. G. Sm.) Sacc.) were directly mixed into PDB potato dextrose broth. 10 µL test solution in DMSO (2%) of different concentration of 7 was placed into

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• completed the synthesis of stachybotrylactam I (157). Chlorinated isoindolinone alkaloids: Pestalachloride A (193) was isolated from the plant endophytic fungus Pestalotiopsis adusta as a racemate and displays potent antifungal activities against Fusarium culmorum (IC50 = 0.89 µM) [147]. Pestalone (192), a

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

• (Candida albicans) nor on molds (Mucor hiemalis, Fusarium oxysporum, Alternaria alternata). The natural compound 4 was one of the most active compounds, but also shorter chain analogues 9 and 10 inhibited, for instance, the growth of Staphylococcus aureus at concentrations in the low µg/mL range, whereas

Phytoalexins of the Pyrinae: Biphenyls and dibenzofurans

• Cornelia Chizzali and
• Ludger Beerhues

Beilstein J. Org. Chem. 2012, 8, 613–620, doi:10.3762/bjoc.8.68

• inhibited by the phytoalexins at concentrations that are supposed to be present at local infection sites [10]. For example, the effective dose 50% (ED50) for inhibition of Fusarium culmorum ranged from 12 to 84 μg/mL [4][13][15][21]. When the dibenzofuran eriobofuran (17) and its O-glucoside malusfuran (20

Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10

• Teresa Weise,
• Marco Kai,
• Anja Gummesson,
• Armin Troeger,
• Stephan von Reuß,
• Silvia Piepenborn,
• Francine Kosterka,
• Martin Sklorz,
• Ralf Zimmermann,
• Wittko Francke and
• Birgit Piechulla

Beilstein J. Org. Chem. 2012, 8, 579–596, doi:10.3762/bjoc.8.65

• bacteria were different for growth on media (nutrient broth) with or without glucose. Keywords: Aspergillus nidulans; Fusarium solani; growth inhibition and promotion; methylketones; 10-methylundecan-2-one; Rhizoctonia solani; volatile organic compound (VOC); Xanthomonas campestris pv. vesicatoria

• other organisms, three fungi, Aspergillus nidulans, Fusarium solani and Rhizoctonia solani, were cocultivated with X. c. pv. vesicatoria 85-10 in compartmentalized Petri dishes (Figure 1). This ensures that only volatiles can diffuse between the compartments to act on the fungal test organisms. Since it

• . Interestingly, Fusarium solani was only weakly influenced by the volatiles of X. c. pv. vesicatoria 85-10, indicating species-specific reactions. Similar results were obtained when ten different rhizobacteria were tested with various fungi [27]. Most of the tested fungi, including R. solani, Verticillium

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• lipolytica and Fusarium oxysporum. (4R)-N-((1-((2S,3R)-2-(4-chlorophenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)-1H-1,2,3-triazole-4-yl)methyl)-4-((3R,5R,10R,12S,13R)-hexadecahydro-3,12-dihydroxy-5,10,13-trimethyl-1H-cyclopenta[a]phenanthren-17-yl)pentanamide (3, Figure 2) had the most potent activity [20

• , phenoxyacetic acid derivatives and carbon disulfide, respectively. Their antifungal activity was investigated against Aspergillus niger and Fusarium oxysporum. Among the series of synthesized compounds, 7-(3-chlorophenyl)-6,7-dihydro-5H-imidazo[2,1-c][1,2,4]triazole-3-thiol (8, Figure 6) showed the most

• pathogens such as Zygomycetes, Fusarium spp. or Scedosporium spp. have become increasingly important pathogens. Their susceptibility to currently available antifungals may be limited and resulting mortality rate is ≥70% in patients with haematological malignancies [40]. For many years, the only available

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

• Wentao Gao,
• Jia Liu,
• Yun Jiang and
• Yang Li

Beilstein J. Org. Chem. 2011, 7, 210–217, doi:10.3762/bjoc.7.28

• a major factor in the defense system against Fusarium wilt [12][13]. On the other hand, the methylenedioxy unit, present in many natural products such as safrole [14], Leucettamine B [15], and Steganacin [16], exhibits a wide variety of biological activities [17][18][19][20]. The methylenedioxy unit

A facile synthesis and fungicidal activities of 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin- 4(3H)-ones

• Yang-Gen Hu,
• Ai-Hua Zheng,
• Xu-Zhi Ruan and
• Ming-Wu Ding

Beilstein J. Org. Chem. 2008, 4, No. 49, doi:10.3762/bjoc.4.49

• listed in Table 1. Fungicidal activity The fungicidal activities of compounds 6 and 8 were screened against six kinds of fungi, Fusarium oxysporum, Rhizoctonia solani, Botrytis cinerea, Gibberella zeae, Dothiorella gregaria, Colletotrichum gossypii at a concentration of 50 mg/L according to the reported