Regioselective chemoenzymatic syntheses of ferulate conjugates as chromogenic substrates for feruloyl esterases

• Olga Gherbovet,
• Fernando Ferreira,
• Apolline Clément,
• Mélanie Ragon,
• Julien Durand,
• Sophie Bozonnet,
• Michael J. O'Donohue and
• Régis Fauré

Beilstein J. Org. Chem. 2021, 17, 325–333, doi:10.3762/bjoc.17.30

• regioselective functionalization of 4-nitrocatechol and enzymatic transferuloylation. The use of this strategy to characterize type A feruloyl esterase from Aspergillus niger reveals the advantages of this substrate for the characterizations of feruloyl esterases. Keywords: esterase; feruloylated conjugates

• from Aspergillus niger (AnFaeA, Figure 1C). Coloration is the result of successive reactions: (i) release of the free 5-bromo-4-chloro-indoxyl-3-ol by an enzyme cascade, wherein TxAbf-catalyzed cleavage of the glycosidic bond was made possible by the prior release by AnFaeA of the ferulate moiety [21

Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

• Ken-ichi Nakashima,
• Junko Tomida,
• Tomoe Tsuboi,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177

• classes Eutiomycetes (e.g., Monascus, Penicillium, and Aspergillus spp.) and Sordariomycetes (e.g., Chaetomium, Hypoxylon, and Diaporthe spp.) [5]. In addition, some of the azaphilones have been also found in the Dothideomycetes class such as Pithomyces [6], Cochliobolus [7][8], and Leptosphaeria spp. [9

Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)

• Cora Hertzer,
• Stefan Kehraus,
• Nils Böhringer,
• Fontje Kaligis,
• Robert Bara,
• Dirk Erpenbeck,
• Gert Wörheide,
• Till F. Schäberle,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132

• for a wide chemodiversity of terpenoid natural products [14][81]. Besides, the marine fungi Penicillium spp. and Aspergillus spp. are often associated with sponge hosts and were found to produce various terpenoids as well [15][82][83]. Hence, if sponges are not the origin of these metabolites, it is

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• , Australia School of Molecular Sciences, The University of Western Australia, WA 6009, Australia Department of Molecular Sciences, Macquarie University, NSW 2109, Australia 10.3762/bjoc.15.256 Abstract Chemical investigation of an undescribed Australian fungus, Aspergillus nanangensis, led to the

• : Aspergillus; biosynthesis; drimane; secondary metabolites; sesquiterpenoid; terpenes; Introduction The fungal genus Aspergillus is well recognised as a source of structurally diverse terpenoids comprising monoterpenoids [1], sesquiterpenoids [2][3][4][5], diterpenoids [6], sesterterpenoids [7][8][9

• [21], A. ochraceus [22], A. pseudodeflectus [17], A. carneus [23] and Aspergillus sp. strain IBWF002-96 [4][5] are biosynthetic sources of the drimane sesquiterpenoids. Drimane sesquiterpenoids, which are derived from a parent C15 pentamethyl-trans-decalin skeleton, are known to occur in plants

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• from Phalaris coerulescens (Figure 3). Likewise, maremycins [13] and spirotryprostatin B [14] have been isolated from marine Streptomyces and from the fermentation broth of Aspergillus fumigatus. Among benzo-fused γ-lactam chemical entities, natural and synthetic isoindolinones are a prominent class of

Influence of per-O-sulfation upon the conformational behaviour of common furanosides

• Alexey G. Gerbst,
• Vadim B. Krylov,
• Dmitry A. Argunov,
• Maksim I. Petruk,
• Arsenii S. Solovev,
• Andrey S. Dmitrenok and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2019, 15, 685–694, doi:10.3762/bjoc.15.63

• , including fragments of a galactomannan from Aspergillus fumigatus [17][18][19], diheteroglycan from Enterococcus faecalis [20], galactan I from Klebsiella pneumoniae [21] and fucoidan from brown seaweed Chordaria flagelliformis [22]. In this communication the conformational analysis of three common per-O

Volatiles from three genome sequenced fungi from the genus Aspergillus

• Jeroen S. Dickschat,
• Ersin Celik and
• Nelson L. Brock

Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77

• Abstract The volatiles emitted by agar plate cultures of three genome sequenced fungal strains from the genus Aspergillus were analysed by GC–MS. All three strains produced terpenes for which a biosynthetic relationship is discussed. The obtained data were also correlated to genetic information about the

• from cantaloupe a structural revision to the Z stereoisomer is proposed. Ethyl (Z)-hept-4-enoate also occurs in Aspergillus clavatus and was identified by synthesis of an authentic standard. Keywords: Aspergillus; GC–MS; genomics; terpenes; volatiles; Introduction Ascomycete fungi are a highly

• productive and biosynthetically exceptionally creative source of secondary metabolites from all classes of natural products. Many prominent compounds such as lovastatin from Aspergillus terreus [1] or the penicillin antibiotics from Penicillium [2] are used for human wellfare, whilst others including

Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines

• Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 416–429, doi:10.3762/bjoc.14.30

• with pectinase from Aspergillus aculeatus, which has both mannosidase and galactosidase activity, at 50 °C for 48 h in a 50 mM acetate buffer (pH 5.0) resulted in the production of a mixture of compounds, from which the Manβ(1–4)Man disaccharide was readily purified by acetylation (typically in ≈30

Selective enzymatic esterification of lignin model compounds in the ball mill

• Ulla Weißbach,
• Saumya Dabral,
• Laure Konnert,
• Carsten Bolm and
• José G. Hernández

Beilstein J. Org. Chem. 2017, 13, 1788–1795, doi:10.3762/bjoc.13.173

• (Scheme 1a) [8]. Similarly, immobilized lipases (triglycerol acylhydrolases EC 3.1.1.3) such as Amano lipase PS-IM from Burkholderia cepacia immobilized on diatomaceous earth and lipase B from Candida antarctica (expressed in Aspergillus niger) adsorbed on polymethacrylate beads (ca. 400 μm–600 μm in

• Immobead), immobilized lipase from Burkholderia cepacia (PS-IM) and lipase A from Aspergillus niger were tested. Firstly, hoping to find differences between the two hydrolases derived from Candida antarctica, an experiment using CALA was conducted. Despite CALB and CALA being produced by the same yeast

Mechanochemical enzymatic resolution of N-benzylated-β³-amino esters

• Mario Pérez-Venegas,
• Gloria Reyes-Rangel,
• Adrián Neri,
• Jaime Escalante and
• Eusebio Juaristi

Beilstein J. Org. Chem. 2017, 13, 1728–1734, doi:10.3762/bjoc.13.167

• , 480 mg weight) using water (3.6 μL, 0.5 equiv), 0.2 mL of 2-methyl-2-butanol (2M2B) as a LAG additive (η = 1.63) and 40 mg of CALB (Novozym 435, Novozymes, recombinant, expressed in Aspergillus niger, immobilized in acrylic resin, >10000 U/g) at 25 Hz during 30 min. Gratifyingly, 55% conversion to the

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• Galf, a five-membered form of galactose found in nonmammalian pathogenic species, i.e., the fungus Aspergillus, is able to modulate the innate immune response via dendritic cells, suggesting Galf-GNPs as versatile tools in functional studies to address the role of Galf in host-pathogen interaction. DC

First total synthesis of kipukasin A

• Chuang Li,
• Haixin Ding,
• Zhizhong Ruan,
• Yirong Zhou and
• Qiang Xiao

Beilstein J. Org. Chem. 2017, 13, 855–862, doi:10.3762/bjoc.13.86

• , antiparasitic and antitumor properties. Kipukasins A–G were firstly isolated from solid-substrate fermentation cultures of Hawaiian Aspergillus Versicolor in 2007 (Figure 1) [11]. Later on, kipukasins H, I [12] and J [13] were also isolated from the fungus Aspergillus flavus, which was collected at the South

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil

• Joyce Azzi,
• Pierre-Edouard Danjou,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2017, 13, 835–844, doi:10.3762/bjoc.13.84

• cabreuva essential oil (EO) (Myrocarpus fastigiatus) [3]. Due to its antimicrobial effects against a wide range of microorganisms such as Staphylococcus aureus, Salmonella enterica and Aspergillus niger [4], Ner can be employed as natural alternative to traditional synthetic food preservatives. To achieve

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• antibacterial activity against Escherichia coli and Bacillus subtilis, and antifungal activity against Aspergillus niger and Penicillium notatum. Among the synthesized series of 1-indanone derivatives 64, the highest antibacterial activity was exhibited by derivatives 64k and 64l, whereas the most potent

Adsorption of RNA on mineral surfaces and mineral precipitates

• Elisa Biondi,
• Yoshihiro Furukawa,
• Jun Kawai and
• Steven A. Benner

Beilstein J. Org. Chem. 2017, 13, 393–404, doi:10.3762/bjoc.13.42

• nucleate the formation of an aragonite precipitate over a calcite precipitate. Initial results were auspicious. Feigl’s stain suggested that CaCO3 precipitated preferentially as aragonite in the presence of RNA, here isolated from Aspergillus. This was first observed when a solution of Na2CO3 (1 M) was

O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside

• Roman Sommer,
• Dirk Hauck,
• Annabelle Varrot,
• Anne Imberty,
• Markus Künzler and
• Alexander Titz

Beilstein J. Org. Chem. 2016, 12, 2828–2833, doi:10.3762/bjoc.12.282

• determination [21][22]. This method has now successfully been applied to solve the structure of the bacterial lectins RSL from Ralstonia solanacearum [23], BC2L-C from Burkholderia cenocepacia [24], and the fungal lectin AFL from Aspergillus fumigatus [25] using methyl α-L-selenofucoside (1, Figure 1) as heavy

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

• District, Shenzhen, 518102, China Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education of China, School of Pharmaceutical Sciences, Wuhan University, Wuhan, 430071, China 10.3762/bjoc.12.196 Abstract The chemical investigation of the mangrove endophytic fungus Aspergillus

• , respectively. In addition, compounds 1 and 3 exhibited weak radical scavenging activity with EC50 values of 125 and 138 μM, respectively. Keywords: α-glucosidase; Aspergillus; DPPH·; furoisocoumarin; isocoumarin; Introduction Isocoumarins are an important group of natural products with diverse structural

• derived from the South China Sea [10][11][12][13][14][15]. In a previous study, a chemical investigation of the endophytic fungal strain Aspergillus sp. 085242 allowed us to identify two novel sesquiterpenoids, asperterpenols A and B with an unusual 5/8/6/6 tetracyclic ring skeleton [15]. The unique

Enantioconvergent catalysis

• Justin T. Mohr,
• Jared T. Moore and
• Brian M. Stoltz

Beilstein J. Org. Chem. 2016, 12, 2038–2045, doi:10.3762/bjoc.12.192

• (Aspergillus niger and Beauveria sulfurescens) were capable of resolving racemic styrene oxide (31, Scheme 7) by hydrolytic kinetic resolution [35]. It was recognized that these two biocatalysts exhibited opposite enantiomer preference in the kinetic resolution event. Moreover, the major hydrolysis byproduct

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

• chain, attached to the C3 of an oxidised isobenzofuran (Scheme 15). The respective biosynthetic cluster contains seven genes and has been identified by Wang and co-workers through a genome mining approach in Aspergillus nidulans [76]. Later on, the same group annotated a highly homologous gene cluster

• in Aspergillus terreus and elucidated the timing and mechanism of asperfuranone biosynthesis by step-wise heterologous expression of the individual genes in A. nidulans [77]. Thus, genes involved in asperfuranone biosynthesis have been renamed from “afo” to “ateafo”. This bipartite azaphilone

• the formation of a five-membered ring hemiacetal in 91. Spontaneous dehydration installs the furan moiety and after keto reduction by an endogenous reductase, asperfuranone (93) is obtained. Aflatoxins. Aflatoxins 94–99 are highly toxic carcinogens produced in several Aspergillus species (Figure 3

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

• during the purification process. Interestingly, the authors found a NaCl-dependent production of haliangicin [51]. The optimal production range is at 2–3% NaCl (w/v) in the medium, which is the same range as for optimal growth. Haliangicin showed activity against some fungal organisms, e.g., Aspergillus

Biosynthesis of α-pyrones

• Till F. Schäberle

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

• are applied for defense against competitors and predators. The biological activities these compounds exhibit is immense, including antimicrobial [2], antitumor [3][4], and cytotoxic activities [5]. Aflatoxins, produced by several Aspergillus species, are known to cause food poisoning due to their

• kill their prey [45][46]. Fusapyrone (32) and the derivative deoxyfusapyrone (33) had been isolated from Fusarium semitectum [39]. These compounds show considerable antifungal activity, e.g., a minimum inhibitory concentration against Botrytis cinerea, Aspergillus parasiticus, and Penicillium brevi

• molecules, e.g., photopyrones (8–15) from Photorhabdus luminescens are synthesized by such a head-to-head condensation of two acyl moieties [60]. Also the csypyrones (79–81, Figure 21), first reported from Aspergillus oryzae, are composed of two independent chains which are interconnected thereafter [85

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

• , Scheme 5), a toxin from Aspergillus oryzae, provides an interesting example. Its importance arises from the use of the producing organism in Asian food industry [46]. The biosynthesis of 20 can be hypothesized from phenylalanine and glycine. To investigate this, (ring-2H5)Phe and (2-13C)Gly were fed 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

• cytotoxic activity. Classical agar diffusion assays were performed using the fungus Aspergillus niger, the yeast Saccharomyces cerevisiae as well as the Gram-negative bacterium Escherichia coli, and the Gram-positive bacterium Micrococcus luteus and Mycobacterium phlei as test organisms. In agar diffusion

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

• Mohamed Ramadan El Sayed Aly,
• Hosam Ali Saad and
• Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

• antifungal activities against the filamentous fungal strain Aspergillus flavus (Link) and the yeast forming fungal strain Candida albicans (ATCC 7102) were moderate compared with amphotericin B in vitro. In the cytotoxicity study, this derivative was the most cytotoxic one against the prostate cancer PC3

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

• , 10, and 12 (MIC 2 μg/mL for each compound mentioned). Evidently, short dialkyl derivatives (8, 10, 12) are more effective against the tested fungi than analogous monoalkyl derivatives (9, 11), longer monoalkyl (15) and dialkyl derivatives (13, 14, 17). Among the tested strains of fungi, Aspergillus

• -dibutyl derivative (13) with MIC of 16 μg/mL inhibits the growth of Aspergillus niger at lower concentrations in comparison to that of 7·HCl. Conclusion Different pathways leading to diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside and several N-alkyl derivatives are reported. Investigations of their