Release of β-galactosidase from poloxamine/α-cyclodextrin hydrogels

• César A. Estévez,
• José Ramón Isasi,
• Eneko Larrañeta and
• Itziar Vélaz

Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330

• expressed in lactase units per milliliter of solution (ALU/mL). The official monograph USP 37 assay, used to determine lactase activity of preparations derived from Aspergillus oryzae, is based on hydrolysis of the substrate o-nitrophenyl β-D-galactopyranoside (ONPG) at 37 °C and pH 4.5 (buffer prepared

A carbohydrate approach for the formal total synthesis of (−)-aspergillide C

• Pabbaraja Srihari,
• Namballa Hari Krishna,
• Ydhyam Sridhar and
• Ahmed Kamal

Beilstein J. Org. Chem. 2014, 10, 3122–3126, doi:10.3762/bjoc.10.329

• rings) are unexpected, novel, secondary metabolites, isolated from the marine-derived fungus Aspergillus ostianus strain 01F313 in bromine-modified 1/2PD culture medium [1][2][3][4]. Interestingly, these compounds show cytotoxicity against mouse lymphocytic leukemia cells (L1210) with LD50 values of 2.1

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

• Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People’s Republic of China 10.3762/bjoc.10.282 Abstract An unusual C18 norditerpenoid, aspergiloid I (1), was isolated from the culture broth of Aspergillus sp. YXf3, an endophytic fungus

• , 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

• previous chemical investigation of the bioactive secondary metabolites produced by the endophytic Aspergillus sp. YXf3 associated with Ginkgo biloba led to the isolation of new p-terphenyls and novel types of diterpenoids including pimarane-type diterpenoids (sphaeropsidins A and B, aspergiloids D and E

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

• , Malaekeh-Nikouei et al. studied the interaction between benzalkonium chloride with HP-γ-CD and SBE-β-CD with or without ethylenediaminetetraacetic acid (EDTA, preservative potentiator) and fluorometholone [72]. Their biocidal activity against E. coli, P. aeruginosa, S. aureus, C. albicans and Aspergillus

• 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

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

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• of cycloadducts 108 and 109 in molar ratios varied from 1:1 to 12:1. Compounds 108 were inactive against Aspergillus fumigatus or Candida albicans at concentration of 125 µg/mL. Nucleoside analogs 110 with the 3,4-dihydroquinazoline-derived nucleobase were obtained by Siddiqui et al. under microwave

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

• the cytotoxic sesquiterpenoid quadrone (55) from Aspergillus terreus [52][53] started from tricyclic ketone 52 [54], which was converted into tricycle 53 in 12 steps. Trans-divinylcyclopropane 53 underwent the desired DVCPR after trans-cis-isomerization of the vinyl moiety at 175 °C, forming bridged

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

• Tatyana L. Pavlovskaya,
• Fedor G. Yaremenko,
• Victoria V. Lipson,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Vladimir I. Musatov and
• Alexander S. Karpenko

Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

• commutatа [4], mitraphylline from Uncaria tomentosa [5] and spirotryprostatines A and B from the secondary metabolites of Aspergillus fumigatus [6][7][8]. In particular, oxindole derivatives are well known as powerful anti-tumor agents due to their kinase inhibitory properties, especially as tyrosine kinase

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

• production of inhibitors of survivin promoter activity, a new drimane sesquiterpene lactone, SF002-96-1, was isolated from fermentations of an Aspergillus species. The compound inhibited survivin promoter activity in transiently transfected Colo 320 cells in a dose dependent manner with IC50 values of 3.42

• attractive target for new anticancer therapeutics [13]. In a search for new inhibitors of survivin expression from natural sources, we found that cultures of Aspergillus sp. strain IBWF002-96 produced a new drimane sesquiterpene lactone, SF002-96-1, with inhibitory activity on survivin promoter activity in

• optical rotation was measured on a Perkin-Elmer 241 polarimeter at 578 nm and 546 nm and extrapolated to 589 nm using Drude’s equation [34]. Producing organism, fermentation and isolation of compound SF002-96-1 Aspergillus sp. strain IBWF002-96 was obtained from the culture collection of the Institute of

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

• architecture and was first isolated from the fungus Aspergillus awamori in 2002 [74]. The highly functionalized pentacyclic skeleton comprises a unique 12-oxatricyclo[6.3.1.02,7]dodecane ring system and ten stereogenic centers. Its carbon framework is closely related to other members of the aspochalasin

• erinaceum [137][138]. Another member of this family, aspernidine A (164), was recently isolated form the fungus Aspergillus nidulans by Hertweck [139]. A comprehensive review about meroterpenoids produced by fungi was published by Simpson in 2009 [140]. The isolated molecules display a broad spectrum of

Activation of cryptic metabolite production through gene disruption: Dimethyl furan-2,4-dicarboxylate produced by Streptomyces sahachiroi

• Dinesh Simkhada,
• Huitu Zhang,
• Shogo Mori,
• Howard Williams and
• Coran M. H. Watanabe

Beilstein J. Org. Chem. 2013, 9, 1768–1773, doi:10.3762/bjoc.9.205

• kb) [6][7]. Direct manipulation, “induced” biosynthetic activation, of a sequenced cluster has also met with some success. The Aspergillus nidulans genome was mined for cryptic orphan gene clusters from which a single, unexpressed PKS-NRPS hybrid was identified. The expression of the gene cluster was

The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure

• Francesco Airaghi,
• Andrea Fiorati,
• Giordano Lesma,
• Manuele Musolino,
• Alessandro Sacchetti and
• Alessandra Silvani

Beilstein J. Org. Chem. 2013, 9, 147–154, doi:10.3762/bjoc.9.17

• has led to new classes of biologically active tetracyclic compounds, both naturally occurring and synthetically made [18]. Highly complex natural products displaying the fused, tetracyclic THBC-DKP ring system were recently isolated from the fungus Aspergillus fumigatus [19] and have been shown to

A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues

• James R. Cochrane,
• Dong Hee Yoon,
• Christopher S. P. McErlean and
• Katrina A. Jolliffe

Beilstein J. Org. Chem. 2012, 8, 1344–1351, doi:10.3762/bjoc.8.154

• . The antifungal activity of 1 and 20–23 was evaluated by using a standardised serial dilution sensitivity assay [28] against reference strains of Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus (Table 3). Synthetic LI-F04a was found to exhibit good activity against both C. albicans

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

• inhibited the growth of Rhizoctonia solani and Aspergillus nidulans and to a certain extent that of Fusarium solani. The inhibition was stronger when X. c. pv. vesicatoria 85-10 was grown on NB as compared to NBG. Both methods, GC/MS and PTR–MS, indicated the emission of a multitude of volatile compounds

Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors

• Davide Bini,
• Francesca Cardona,
• Matilde Forcella,
• Camilla Parmeggiani,
• Paolo Parenti,
• Francesco Nicotra and
• Laura Cipolla

Beilstein J. Org. Chem. 2012, 8, 514–521, doi:10.3762/bjoc.8.58

• 19th century in Aspergillus niger [4] and S. cerevisiae [5], and has since then been reported in several other organisms, including mammals, where it is found both in the kidney brush border membranes [6] and in the intestinal villae membranes [7]. While the role of trehalase in the kidney has not been

Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

• Hany M. Mohamed,
• Ashraf H. F. Abd EL-Wahab,
• Ahmed M. EL-Agrody,
• Ahmed H. Bedair,
• Fathy A. Eid,
• Mostafa M. Khafagy and
• Kamal A. Abd-EL-Rehem

Beilstein J. Org. Chem. 2011, 7, 1688–1696, doi:10.3762/bjoc.7.199

• bacteria, namely Staphylococcus aureus (NCTC-7447), Bacillus cereus (ATCC-14579), and two Gram-negative bacteria, namely Escherichia coli (NCTC-10410), Serratia marcescens (IMRU-70); and against two species of fungi, namely Aspergillus fumigatus (MTCC-3008) and Candida albicans (MTCC-227). The tested

Marilones A–C, phthalides from the sponge-derived fungus Stachylidium sp.

• Celso Almeida,
• Stefan Kehraus,
• Miguel Prudêncio and
• Gabriele M. König

Beilstein J. Org. Chem. 2011, 7, 1636–1642, doi:10.3762/bjoc.7.192

• occurring compounds described [1]. They are produced by a wide range of organisms, i.e., by marine and terrestrial fungi belonging to genera such as Ascochyta [2], Aspergillus [3][4][5], Alternaria [6], Penicillium [7], Hericium [8] or Talaromyces [9], but also by plants and liverworts [1]. Phthalides

• described from the fungus Aspergillus silvaticus [6]. Nidulol and silvaticol (4) are regioisomeric compounds and differ in terms of the position of the carbonyl group, which is either placed peri to the aromatic hydrogen, as in 3 and 4, or it is positioned peri to the aromatic methoxy moiety, e.g., in 1 and

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

• -benzyl]-4-aryl-1,2,4-triazole-3-thiones were synthesized by Ezabadi et al., and evaluated for in vitro antifungal activity against Aspergillus flavus, Aspergillus versicolor, Aspergillus ochraceus, Aspergillus niger, Trichoderma viride and Penicillium funiculosum. Of the compounds obtained, 5-[2-(N,N

• synthesized by Hussain et al. and evaluated for their antifungal activity against Aspergillus niger by the cup plate method. 4-Amino-2-(4-(4-chlorophenyl)-5-mercapto-4H-1,2,4,-triazol-3-yl)phenol (7, Figure 5) with a chloro group at the para position of the phenyl ring exhibited a minimum inhibitory

• concentration (MIC) of 25 μg/mL against Aspergillus niger [33]. Unsubstituted and 3-substituted-7-aryl-5H-6,7-dihydroimidazo[2,1-c][1,2,4]triazoles were designed by Sztanke et al. and obtained from biologically active 1-aryl-2-hydrazonoimidazolidines by cyclocondensation reactions with triethyl orthoformate

Michael-type addition of azoles of broad-scale acidity to methyl acrylate

• Sławomir Boncel,
• Kinga Saletra,
• Barbara Hefczyc and
• Krzysztof Z. Walczak

Beilstein J. Org. Chem. 2011, 7, 173–178, doi:10.3762/bjoc.7.24

• . Other reaction conditions including enzymatic catalysis (Bacillus subtilis) [13], zinc-active-site acylases from Escherichia coli and Aspergillus oryzae [23] as well as ultrasonic irradiation in the presence of montmorillonite [14] have also been reported. In addition, there has been several recent

Sordarin, an antifungal agent with a unique mode of action

• Huan Liang

Beilstein J. Org. Chem. 2008, 4, No. 31, doi:10.3762/bjoc.4.31

• shown in Figure 3. Of note is their activity against a variety of human pathogens belonging to the Candida, Aspergillus, and Pneumocystis spp. In 2001, the same company released the synthesis of a new series of “GW” analogs named “azasordarins”. Similar to superior activity was observed against the

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• and human placenta, α-D-galactosidases from coffee beans and Escherichia coli, β-D-galactosidases from Escherichia coli, bovine liver, Aspergillus niger and Aspergillus orizae, α-N-acetylgalactosaminidase from chicken liver, β-N-acetylglucosaminidases from Jack bean, bovine epididymis A and bovine

• epididymis B, α-D-mannosidase from almonds, β-D-mannosidase from Helix pomatia, and β-xylosidase from Aspergillus niger. For other enzymes: α-D-glucosidase from Bacillus stearothermophilus, amyloglucosidase from Aspergillus niger and Rhizopus mold, β-D-glucosidase from almonds, α-L-fucosidase from bovine

• correlated with an increase in observed activity. Thus, for example we had previously shown that the corresponding C7-voglibose mimic exhibited interesting activity towards amyloglucosidases from Aspergillus niger and Rhizopus mold (35 and 18 μM respectively, unpublished results). Furthermore, even if data