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

• antimicrobial activity against fungi and yeast of 26 was simultaneously reported with its isolation [16]. Moreover, with IC50 values in the low nanomolar range (1–20 nM), staurosporine (26) is one of the most potent protein kinase inhibitors to date [18]. It took nine years to identify the crucial protein

• instance compounds 156, 157 and 159–161, can be extracted from Stachybotrys fungi (Figure 8) [130][131][132][133][134][135]. Memnobotrin A (158) is found in the closely related Memnoniella echinata fungus [136], and hericenone B (162) and erinacerin A (163) were isolated from the mushroom Hericium

• 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

ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans

• Willmen Youngsaye,
• Cathy L. Hartland,
• Barbara J. Morgan,
• Amal Ting,
• Partha P. Nag,
• Benjamin Vincent,
• Carrie A. Mosher,
• Joshua A. Bittker,
• Sivaraman Dandapani,
• Michelle Palmer,
• Luke Whitesell,
• Susan Lindquist,
• Stuart L. Schreiber and
• Benito Munoz

Beilstein J. Org. Chem. 2013, 9, 1501–1507, doi:10.3762/bjoc.9.171

• ability to chemosensitize the C. albicans test strains CaCi-2 and CaCi-8 towards fluconazole. As described above, the fungi were simultaneously incubated with test compounds and fluconazole (8 µg/mL) for 48 hours to determine if any combinations could fully inhibit fungal growth. The DMSO/fluconazole

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

• Paweł Borowiecki,
• Małgorzata Milner-Krawczyk and
• Jan Plenkiewicz

Beilstein J. Org. Chem. 2013, 9, 516–525, doi:10.3762/bjoc.9.56

• bacteria and fungi. Results and Discussion Synthesis and enzymatic resolution of the N-2-hydroxypropylazoles In this paper we report the synthesis of racemic 1-(1H-imidazol-1-yl)propan-2-ol and 1-(1H-1,2,4-triazol-1-yl)propan-2-ol and the procedure for lipase-catalyzed kinetic separation of their

• liquids Antibacterial and antifungal activities of the synthesized racemic CILs were evaluated against a wide range of microorganisms. The studies were conducted on three strains of gram-negative bacteria, two strains of gram-positive bacteria, and eight strains of fungi. For the preliminary screening of

• , the filamentous fungi displayed high tolerance towards the tested CILs. Nevertheless, the relation between the alkyl chain substituent and the antifungal activity of the tested compounds could still be observed, with the strongest toxicity demonstrated by CILs with an alkyl chain substituent of 12

Polymerization of novel methacrylated anthraquinone dyes

• Christian Dollendorf,
• Susanne Katharina Kreth,
• Soo Whan Choi and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 453–459, doi:10.3762/bjoc.9.48

• the use of azo dyes, especially in the case of bright blue shades. Anthraquinone dyes can be obtained synthetically and by isolation from fungi such as Dermocybe sanguinea or other fungal species [5][10][11][12][13], to give them a higher compatibility with the environment and an improved availability

Caryolene-forming carbocation rearrangements

• Quynh Nhu N. Nguyen and
• Dean J. Tantillo

Beilstein J. Org. Chem. 2013, 9, 323–331, doi:10.3762/bjoc.9.37

• intermediates; terpene; Introduction The cytotoxic sesquiterpenol caryol-1(11)-en-10-ol (1, Figure 1) was isolated by Barrow et al. in 1988 during an investigation of antiviral/antitumor compounds from New Zealand marine invertebrates [2]. Similar sesquiterpenoids were also found in Campanella fungi

The multicomponent approach to N-methyl peptides: total synthesis of antibacterial (–)-viridic acid and analogues

• Ricardo A. W. Neves Filho,
• Sebastian Stark,
• Bernhard Westermann and
• Ludger A. Wessjohann

Beilstein J. Org. Chem. 2012, 8, 2085–2090, doi:10.3762/bjoc.8.234

• ; toxin; Ugi reaction; Introduction Viridic acid (1) is a tetrapeptide produced by several fungi of the genus Penicillium, including P. viridicatum, P. nordicum, and P. aurantiogriseum among others [1][2][3][4]. It was first isolated from the basic fraction of the chloroform/methanol extract of P

Synthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance

• Torsten Dittrich,
• Nils Hanekop,
• Nacera Infed,
• Lutz Schmitt and
• Manfred Braun

Beilstein J. Org. Chem. 2012, 8, 1700–1704, doi:10.3762/bjoc.8.193

• tumor cells, ABC-type efflux pumps are also involved in multidrug resistance of pathogenic Gram-positive bacteria and fungi for which inhibitors have only rarely been studied. Therefore, we were interested in developing inhibitors of efflux pumps from bacterial and fungal organisms, namely LmrCD from

Synthetic studies towards bottromycin

• Stefanie Ackermann,
• Hans-Georg Lerchen,
• Dieter Häbich,
• Angelika Ullrich and
• Uli Kazmaier

Beilstein J. Org. Chem. 2012, 8, 1652–1656, doi:10.3762/bjoc.8.189

• fungi, developed efficient defense strategies against their bacterial competitors [1][2][3]. Not surprising, a wide range of common antibiotics such as penicillin or vancomycin are natural products or derivatives thereof. In 1957 Waiswisz et al. reported a new antibiotic peptide isolated from the

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

• Ramona Riclea,
• Julia Gleitzmann,
• Hilke Bruns,
• Corina Junker,
• Barbara Schulz and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2012, 8, 941–950, doi:10.3762/bjoc.8.106

• investigate their activity against several bacteria, fungi, and algae. A specific algicidal activity was observed that may be important in the interaction between the bacteria and their algal hosts in fading algal blooms. Keywords: bacteria-algae symbiosis; lactones; Roseobacter; synthesis; volatiles

• 7/8 and 9/10, respectively, these compounds were also tested as diastereomeric mixtures as obtained in the isomerisation procedures with 7 and 9. Tests were performed with bacteria, including the Gram-negative Escherichia coli and the Gram-positive Bacillus megaterium, fungi, represented by the

• specifically showed partial inhibition of the alga C. fusca, but no activity against the bacteria and fungi. Conclusion More and more data are accumulated demonstrating that bacteria of the marine Roseobacter clade produce bioactive secondary metabolites. In the present work, we have identified five lactones

Synthesis and antifungal properties of papulacandin derivatives

• Marjolein van der Kaaden,
• Eefjan Breukink and
• Roland J. Pieters

Beilstein J. Org. Chem. 2012, 8, 732–737, doi:10.3762/bjoc.8.82

• -glucan synthase [9][10][11][12]. The β-(1,3)-D-glucan is an integral and essential component of the fungal cell wall [13] and the dominant glucan in the cell wall of most medically important fungi, and therefore it is a target that is being actively pursued [14]. The papulacandins have demonstrated a

• very high specific activity against several yeasts, but they are largely inactive against filamentous fungi, bacteria and protozoa [3]. Recently, in a direct comparison, papulacandin B was shown to be superior in some aspects compared to the drug caspofungin and a few drug candidates [15]. Its

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

• organisms such as invertebrates, plants and fungi. As a first step to study volatile-based bacterial–plant interactions, the emission profile of Xanthomonas c. pv. vesicatoria 85-10 was determined by using GC/MS and PTR–MS techniques. More than 50 compounds were emitted by this species, the majority

• ; Introduction Plant surfaces are inhabited by diverse and complex communities of microorganisms, although these habitats may be hostile environments, e.g. [1][2][3][4][5][6]. Bacteria are the most dominant inhabitants, e.g., more than 107 cells per cm2 of leaf surface are present, but also filamentous fungi and

• these cell-to-cell-based interactions, additional modes of action of X. campestris may influence growth of the plant directly or indirectly. Although antagonistic features of Xanthomonas spp. against fungi have been only sparsely studied, it is known that Xanthomonas competes with fungi [3]. The

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

• elucidated yet (trehalose is absent in blood), in the intestine it hydrolyses ingested trehalose [8]. However, trehalose hydrolysis is fundamental for insect flight [9], growth resumption of resting cells, and spore germination in fungi. Trehalase is an inverting glycosidase [10], belonging to the GH37

Aldol elaboration of 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridin-4-ones, masked precursors to acylpyridones

• Raymond C. F. Jones,
• Abdul K. Choudhury,
• James N. Iley,
• Mark E. Light,
• Georgia Loizou and
• Terence A. Pillainayagam

Beilstein J. Org. Chem. 2012, 8, 308–312, doi:10.3762/bjoc.8.33

• elfamycin antibiotics [5]. Interest has also been stimulated in these metabolites by the use of the entomopathogenic fungi such as Cordyceps sp., many of which contain pyridone metabolites, in traditional Chinese medicine to strengthen the immune system and improve cognitive function. Farinosone A (2d) from

Derivatives of phenyl tribromomethyl sulfone as novel compounds with potential pesticidal activity

• Krzysztof M. Borys,
• Maciej D. Korzyński and
• Zbigniew Ochal

Beilstein J. Org. Chem. 2012, 8, 259–265, doi:10.3762/bjoc.8.27

• -halogenthiophenol. The development of an effective method for the preparation of the title compounds allowed an evaluation of their biological activity against certain fungi to be carried out. Results and Discussion Our initial synthetic efforts were aimed at the preparation of the starting compound 4-halogenphenyl

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

• Jeroen S. Dickschat,
• Hilke Bruns and
• Ramona Riclea

Beilstein J. Org. Chem. 2011, 7, 1697–1712, doi:10.3762/bjoc.7.200

• of bacterial cell membranes can be tuned, e.g., by the introduction of methyl branches or olefinic double bonds [1]. The biosynthesis of FAs is a repetitive chain elongation process catalysed in animals and fungi by multifunctional megasynthases, and in plants or bacteria by a set of discrete enzymes

• methylmalonyl-CoA was determined by feeding experiments [14]. During our ongoing analysis of the volatiles released by different bacteria and fungi with high potential for secondary metabolism, the actinomycete Micromonospora aurantiaca ATCC 27029 came to our attention. This gram-positive, sporulating bacterial

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

• activity against the tested organisms. Compounds 9–11 exhibited comparable activity to ampicillin against the tested bacteria and moderate to weak antifungal activity against the tested organisms. Furthermore, compounds 1–8 showed moderate to weak activities against all the tested bacteria and fungi

• 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

• microorganisms were obtained from the Regional Center for Mycology & Biotechnology (RCMP), Al-Azhar University. The activities of these compounds were tested by using the disc-diffusion method [23] for bacteria and the paper-disk-diffusion method [24] for fungi. The area of zone inhibition was measured with

Tertiary alcohol preferred: Hydroxylation of trans-3-methyl-L-proline with proline hydroxylases

• Christian Klein and
• Wolfgang Hüttel

Beilstein J. Org. Chem. 2011, 7, 1643–1647, doi:10.3762/bjoc.7.193

• , proline hydroxylases exclusively hydroxylate the free L-amino acid and are limited to some bacteria and filamentous fungi. As far as it is known, they are involved in secondary metabolism, for example, in the biosynthesis of the non-ribosomal peptide antibiotics etamycin, telomycin and pneumocandin [22

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

• B (2) showed selective antagonistic activity towards the serotonin receptor 5-HT2B with a Ki value of 7.7 µM. Keywords: marine fungi; natural products; phthalides; polyketides; Introduction Phthalides are a class of structurally very diverse secondary metabolites with more than 180 naturally

• 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

Natural product biosyntheses in cyanobacteria: A treasure trove of unique enzymes

• Jan-Christoph Kehr,
• Douglas Gatte Picchi and
• Elke Dittmann

Beilstein J. Org. Chem. 2011, 7, 1622–1635, doi:10.3762/bjoc.7.191

• for the specific C-C bond reaction that is unprecedented in natural systems. Further enzymatic transformations of the scytonemin pathway remain to be elucidated [71]. Mycosporine-like amino acids (MAAs) Mycosporines were initially discovered in fungi and found to trigger light-induced fungal

Biosynthesis and function of secondary metabolites

• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2011, 7, 1620–1621, doi:10.3762/bjoc.7.190

• poses severe clinical problems in the treatment of infectious diseases. This Thematic Series on the biosynthesis and function of secondary metabolites deals with the discovery of new biologically active compounds from all kinds of sources, including plants, bacteria, and fungi, and also with their

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

• of the growing emergence of antimicrobial resistance are major concerns to the public health and scientific communities worldwide, especially in the field of multidrug- resistant bacteria and fungi [1][2]. These trends have emphasized the urgent need for new, more effective, less toxic and safe

• significant activity [34]. Antifungal chemotherapy Fungal infections are caused by microscopic organisms that can invade the epithelial tissue. The fungal kingdom includes yeasts, moulds, rusts and mushrooms. Fungi are heterotrophic, which means they obtain nutrients from the environment, not from endogenous

• strain-dependent fungicidal activity against filamentous fungi with the exception of some strains of Cryptococcus neoformans. It is taken orally in capsule form to treat fungal infections that start in the lungs and spread throughout the body. Itraconazole can also be used to treat fungal infections of

Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

• Silke Dubberke,
• Muhammad Abbas and
• Bernhard Westermann

Beilstein J. Org. Chem. 2011, 7, 421–425, doi:10.3762/bjoc.7.54

• cultures of mucoraceous fungi: Blakeslea trispora, Mucor mucedo and Phycomyces blakesleeanus [16]. They stimulate caratenogenesis and zygophore (sex cell) formation. Interestingly, for the biosynthesis of the trisporic acid, mating species of the opposite sex have to cooperate. It has been suggested, that

Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H

• Ludovic Raffier and
• Olivier Piva

Beilstein J. Org. Chem. 2011, 7, 151–155, doi:10.3762/bjoc.7.21

• application to the asymmetric synthesis of different natural products including (R)-lavandulol (8), (R)-arundic acid (9) and 2-fluoroacids or lactones [7][8][9] (Figure 1). Filamentous fungi are the source of a wide range of secondary metabolites which possess very promising biological activities. Among them

Synthesis of (3R,5R)-harzialactone A and its (3R,5S)-isomer

• Gowravaram Sabitha,
• Rangavajjula Srinivas,
• Sukant K. Das and
• Jhillu S. Yadav

Beilstein J. Org. Chem. 2010, 6, No. 8, doi:10.3762/bjoc.6.8

• . Epoxide opening with thioacetal and diastereoselective reductions are used as key reactions. Keywords: dithiane; harzialactone A; hydroxyl directed reduction; stereoisomer; Introduction Marine microorganisms such as bacteria, fungi, and microalgae have proved to be a rich source of structurally novel

2-Phenyl- tetrahydropyrimidine- 4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β²-amino acids

• Markus Nahrwold,
• Arvydas Stončius,
• Anna Penner,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2009, 5, No. 43, doi:10.3762/bjoc.5.43

• ]. Examples are cryptophycin-1 (a highly cytotoxic depsipeptide produced by cyanobacteria Nostoc sp. GSV224 and ATCC53789) [11][12][13][14] as well as a class of lipopeptides isolated from various fungi, comprising topostatin (a topoisomerase I and II inhibitor) [15], YM-170320 (an inhibitor of ergosterol