A new member of the fusaricidin family – structure elucidation and synthesis of fusaricidin E

• Marcel Reimann,
• Louis P. Sandjo,
• Luis Antelo,
• Eckhard Thines,
• Isabella Siepe and
• Till Opatz

Beilstein J. Org. Chem. 2017, 13, 1430–1438, doi:10.3762/bjoc.13.140

• family which were isolated from several strains of Paenibacillus polymyxa [3][4]. Fusaricidins exhibit antimicrobial activity against Gram-positive bacteria and a wide range of fungi including Leptosphaeria maculans, a plant pathogenic fungus responsible for the blackleg disease on Brassica crops [5][6

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• to about 1,500. Interestingly, about 60% of them were obtained ligated to carbohydrates, which range from monosaccharides to 10 residue-long oligosaccharides. Lectins occur in plants, animals, algae, bacteria, fungi and yeasts, and viruses. Their involvement in key biologically-important recognition

Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides

• Li Yang,
• Ping Wu,
• Jinghua Xue,
• Huitong Tan,
• Zheng Zhang and
• Xiaoyi Wei

Beilstein J. Org. Chem. 2017, 13, 1039–1049, doi:10.3762/bjoc.13.103

• Blue assay (MABA) [19]. For the filamentous fungi, C. gloeosporioides and P. infestans, the strains were grown on PDA cultures for 7 days. The spore suspensions were harvested by flooding the colony with PDB medium, rubbing the surface with a sterile scraper, and filtering with four layers of gauze

• S. cerevisiae were the same as mentioned above for the two filamentous fungi. Evaluation of tumor cell toxicity The evaluation was conducted as previously described [23]. Photoinduced interconversion between 2 and 3 The mixture of 2 and 3 (7:3) was separated by a SPOLAR C18 column (4.6 × 250 mm, 5

Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

• Yuta Isoda,
• Norihiko Sasaki,
• Kei Kitamura,
• Shuji Takahashi,
• Sujit Manmode,
• Naoko Takeda-Okuda,
• Jun-ichi Tamura,
• Toshiki Nokami and
• Toshiyuki Itoh

Beilstein J. Org. Chem. 2017, 13, 919–924, doi:10.3762/bjoc.13.93

• synthesis was completed by Yu [8][9]. Although the activity of TMG-chitotriomycin (1) was moderate, it selectively inhibits glucosaminidases derived from insects and fungi. Therefore, TMG-chitotriomycin (1) has a potential as a lead compound for safe insecticides and pesticides. Recently, the total

Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems

• Katarina Kemper,
• Max Hirte,
• Markus Reinbold,
• Monika Fuchs and
• Thomas Brück

Beilstein J. Org. Chem. 2017, 13, 845–854, doi:10.3762/bjoc.13.85

• largest and most structurally diverse group of natural products. They are ubiquitous in bacteria, plants, animals and fungi, conducting several biological functions such as cell wall components or defense mechanisms. Industrial applications entail among others pharmaceuticals, food additives, vitamins

• the diverse biosynthesis of the structurally highly diverse family of isoprenoids. Both pathways use intermediate products of the central sugar metabolism as carbon sources [25]. In most eukaryotes (all mammals, yeast, fungi, archaea and plants (more precisely in the cytosol and mitochondria)) the

• ) derive almost exclusively from plants; terpene synthases and other enzymes that are involved in precursor formation (indicated with green knot) can be obtained from various organisms (indicated through symbolic bacteria, leaf (representing plants in general) and fungi). 2: Eukaryotic enzymes have to be

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• wall of yeast and fungi [57]. Chitin is also the precursor of chitosan, which is formed by N-deacetylation to partially free amino groups, and is notoriously insoluble in water. Despite this fact, Shchipunov et al. demonstrated in 2015, the first hydrothermal synthesis of CDs derived from chitin in a

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

• Enjuro Harunari,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

• recently, isolation of butyrolactols C and D was presented but the details are not available in public domains [10]. 1 has a broad antimicrobial activity against fungi ranging from Candida albicans to Trichophyton mentagrophytes with comparative activity to nystatin [9]. Despite the uniqueness of the

Solid-phase enrichment and analysis of electrophilic natural products

• Frank Wesche,
• Yue He and
• Helge B. Bode

Beilstein J. Org. Chem. 2017, 13, 405–409, doi:10.3762/bjoc.13.43

• producing microbes. Much more compounds have been identified than originally thought, but often these are produced only at a very low level. This is also reflected by the genome sequences of bacteria and fungi that often encode numerous biosynthesis gene clusters (BGC) with most of the corresponding natural

• also be applied to extracts of other bacteria, fungi and plants and can give at least hints on new electrophilic natural products, where their reactivity against azide might also reflect their biological activity. (A) HPLC–MS base peak chromatograms of a crude XAD extract of P. luminescens TT01 and

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

• Darcy J. Atkinson,
• Briar J. Naysmith,
• Daniel P. Furkert and
• Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

• -positive bacteria, including resistant strains [2][9][20] and Mycobacterium species [21]. No activity was observed against Gram-negative bacteria (except for Neisseria gonorrhoeae), fungi or yeast [9]. The antibacterial activity arises through inhibition of cell wall synthesis [22] by prevention of

A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus

• Jan Rinkel,
• Patrick Rabe,
• Laura zur Horst and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2016, 12, 2317–2324, doi:10.3762/bjoc.12.225

• complexity is reached within the largest, the terpenoids. An estimated number of 75,000 different compounds are known from all kinds of organisms including plants [1], bacteria [2][3][4][5], fungi [6] and, as recently shown, even social amoebae [7]. These molecules are all made from only a handful of linear

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• features and interesting biological activities. They have been widely isolated from fungi, lichens, bacteria, plants, and insects [1][2]. Furoisocoumarins combining a furan ring and an isocoumarin moiety are divided into two subclasses depending on their fusion type: linear furo[2,3-g]isocoumarins and

• a natural source: Coriandrone A isolated from the aerial parts of Coriandrum sativum [6] and other furo[3,2-h]isocoumarins have been reported as synthetic products [7][8][9]. In the last decade, our research group has been devoted to finding novel bioactive compounds from mangrove endophytic fungi

Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291

• Peng Zhang,
• Xiao-Ming Li,
• Xin-Xin Mao,
• Attila Mándi,
• Tibor Kurtán and
• Bin-Gui Wang

Beilstein J. Org. Chem. 2016, 12, 2012–2018, doi:10.3762/bjoc.12.188

• search for structurally unique and bioactive secondary metabolites from marine fungi, especially from marine alga-derived fungi [6][7][8], we discovered evident DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity and diverse antimicrobial activities in the EtOAc extract from Paecilomyces

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• organisms from different classes. Their origin often goes along with characteristic structural elements. Furylidene tetronates are for example exclusively produced by fungi and spirotetronates by Actinobacteria [139]. The biosynthetic studies that were launched since genetic information on more and more

• -PKS-derived anthraquinone precursors [155]. (+)-Geodin (189) was the first chlorinated compound isolated from fungi [156]. During its biosynthesis in Aspergillus terreus, the furan-3-one ring is closed by action of the multicopper blue protein dihydrogeodin oxidase on dihydrogeodin (186) (Scheme 26a

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

• Barbara Dmochowska,
• Karol Sikora,
• Anna Woziwodzka,
• Jacek Piosik and
• Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

• mutagenicity test; quaternary ammonium salt; Introduction Carbohydrates and alditols occur broadly in nature and possess many biological functions essential to living organisms. Sugars not only contribute as energetic substances, but also serve as building materials for fungi, microbes, plants, and animals

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

• Andrew W. Truman

Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120

• PatG belongs to the S8 family. Another S9a family serine protease-like cyclase features in the biosynthesis of α-amanitin (Figure 8B), an amatoxin produced by the fungus Amanita phalloides and related fungi [110]. Amatoxins are responsible for many of the fatalities caused by mushroom poisoning of

Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate

• Sean P. Bew,
• Glyn D. Hiatt-Gipson,
• Graham P. Mills and
• Claire E. Reeves

Beilstein J. Org. Chem. 2016, 12, 1081–1095, doi:10.3762/bjoc.12.103

• protect them against ’attack’ from bacteria, fungi and parasites. Isoprene also helps to protect against abiotic ’stress’ induced by excessive fluctuations in temperature, by drought, exposure to radiation as well as by contact with herbicides and insecticides [7]. Isoprene reacts readily with O3, HO• and

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

• Antonio Dávila-Céspedes,
• Peter Hufendiek,
• Max Crüsemann,
• Till F. Schäberle and
• Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

• niger (AJ117374, MIC: 12.5 μg mL−1) and Fusarium sp. (AJ177167, MIC: 6.3 μg mL−1). These MIC values were in a similar range as those of known antifungal compounds such as amphotericin B or nystatin against the same fungi (MIC: 3.1 μg mL−1 for both compounds). Recently, the 9.4 Mb genome of H. ochraceum

• testing, revealed that the lactone moiety and the configuration of the methoxyacrylate partial structure are crucial for antifungal activity. The latter structural motif is well known from a range of antifungal compounds produced by fungi and myxobacteria, e.g., the strobilurins and the melithiazols [67

A cross-metathesis approach to novel pantothenamide derivatives

• Jinming Guan,
• Matthew Hachey,
• Lekha Puri,
• Vanessa Howieson,
• Kevin J. Saliba and
• Karine Auclair

Beilstein J. Org. Chem. 2016, 12, 963–968, doi:10.3762/bjoc.12.95

• larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood. Keywords: antibiotic; antiplasmodial; coenzyme A; metathesis; pantothenate; Introduction Bacteria, fungi, and parasites are all rapidly acquiring resistance to

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

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