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Search for "Penicillium" in Full Text gives 39 result(s) in Beilstein Journal of Organic Chemistry.
Chemical structure metagenomics of microbial natural products: surveying nonribosomal peptides and beyond
Beilstein J. Org. Chem. 2024, 20, 3050–3060, doi:10.3762/bjoc.20.253
- invention of the bioactivity-guided fractionation (BGF) workflow by Selman Waksman to search systematically for new bioactive small molecules (Figure 1) [11]. He believed that the fungus Penicillium rubens produces penicillin to suppress the growth of other microorganisms, especially those it competes with
Natural resorcylic lactones derived from alternariol
Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187
- unambiguously confirmed by total syntheses [139][140][141]. β-ᴅ-Galactopyranoside 10 was isolated from Penicillium sp. [142], where it turned out to be cytotoxic against A559 cells (IC50: 6.8 μg/mL) but not against further tested cell lines. Alternariol-derived glucopyranoside 6 was identified together with
- Penicillium chermesinum [184] and later additionally from Rhizopycnis vagu [171] and Hyalodendriella sp. [172]. It had already previously been obtained as intermediate in a TMC-264 total synthesis [185]. Penicilliumolide D showed some antibacterial activity, was cytotoxic against A549 and HTC116 cell lines
- block (Figure 12). The verrulactones were isolated from Penicillium verruculosum [187][193][221] and verrulactone A and B were further isolated from Alternaria alternata [159][160]. Constitution and relative configuration of these compounds was determined by NMR-spectroscopic methods, where the
Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations
Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151
- brassicicenes 27–29. In situ generation of highly reactive intermediates: trichodimerol and the bisorbicillinoid family The bisorbicillinoid family, isolated from fungi such as Penicillium chrysogenum, has dimeric intricate scaffolds, as exemplified by trichodimerol (2) (Scheme 4) [28][29]. The biosynthetic
- phase catalyzed by BscA. (B) Oxidation phase and scaffold rearrangements by modification enzymes. Chemo-enzymatic total synthesis of cotylenol (1) and brassicicenes. (A) Chemical cyclization phase. (B) Chemical and enzymatic oxidation phase. (A) Biosynthetic pathway for trichodimerol (2) in Penicillium
A Diels–Alder probe for discovery of natural products containing furan moieties
Beilstein J. Org. Chem. 2024, 20, 1001–1010, doi:10.3762/bjoc.20.88
- isolated from a sea sponge, Plakortis simplex [3][4]. Wortmannin, which also has a furan, was isolated from Penicillium wortmannin and shows anticancer activity via potent inhibition of phosphoinositide 3-kinase [5]. These are just a handful of the bioactive natural products containing furans that exist
Confirmation of the stereochemistry of spiroviolene
Beilstein J. Org. Chem. 2024, 20, 852–858, doi:10.3762/bjoc.20.77
- ancestors of SvS generated by ancestral sequence reconstruction [8][9]. Related natural products with the same 5-5-5-5 tetracyclic ring system, including spirograterpene A (2) from Penicillium granulatum MCCC 3A00475 [10], and GJ1012A (3) from an engineered E. coli strain harboring FgGS (FgJ07623) cloned
Chemical and biosynthetic potential of Penicillium shentong XL-F41
Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52
- Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai, 201203, China 10.3762/bjoc.20.52 Abstract Penicillium strains are renowned for producing diverse secondary metabolites with unique structures and promising bioactivities. Our chemical
- investigations, accompanied by fermentation media optimization, of a newly isolated fungus, Penicillium shentong XL-F41, led to the isolation of twelve compounds. Among these are two novel indole terpene alkaloids, shentonins A and B (1 and 2), and a new fatty acid 3. Shentonin A (1) is distinguished by an
- activity against Candia albicans. Moreover, genome sequencing of Penicillium shentong XL-F41 uncovered abundant silent biosynthetic gene clusters, indicating the need for future efforts to activate these clusters and unlock the full chemical potential of the fungus. Keywords: genome analysis; indole
Recent developments in the engineered biosynthesis of fungal meroterpenoids
Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50
- Aspergillus nidulans, within the same phylogenetic clade. Expression of this enzyme in place of Trt1 resulted in the formation of the 6-6-6-6-membered ring protoaustinoid A (8) (Figure 2) [9]. In addition, the expression of the cyclase AdrI (38% identity with Trt1) from Penicillium chrysogenum produced the 6
A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001
Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44
- ), fungi (e.g., Aspergillus sojae and Penicillium roquefortii), and bacteria (e.g., Acinetobacter calcoaceticus, Brucella abortus, and Bacillus sp.) [15]. It is also known to be a component of some natural products, such as enterobactin, showing strong radical scavenging activity or antioxidant activity
Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793
Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42
- gloeosporioides, Coniothyrium diplodiella, Curvularia spicifera, Fusarium proliferatum, and Penicillium digitatum) (Table 2). In the antibacterial screening, none of the compounds displayed potent activity against the tested strains (MIC ≥ 32 μg/mL). The antifungal assays showed that compounds 1–3 exhibited
- , Alternaria brassicae QDAU-11, Penicillium digitatum QDAU-14, Coniothyrium diplodiella QDAU-15, Curvularia spicifera QDAU-18, and Fusarium proliferatum QDAU-19) were determined by a serial dilution technique using 96-well microtiter plates [21] with minor modifications as our previously report [22]. Briefly
Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108
- cereus, Bacillus subtilis, Staphylococcus epidermidis, Corynebacterium pseudodiphtheriticum), four Gram-negative bacteria (Escherichia coli, Proteus mirabilis, Enterobacter aerogenes, Enterobacter cloacae), and three fungi (Saccharomyces cerevisiae, Candida albicans, Penicillium chrysogenum). The goal of
Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs
Beilstein J. Org. Chem. 2023, 19, 1452–1459, doi:10.3762/bjoc.19.104
- higher concentrations (10 μg L−1) [15]. The compound has received considerable attention because of its potential to cause odour episodes in water supply systems [16][17]. The production of 1 by Penicillium can add to the flavour of cheese [18], while its occurrence in fish and coffee leads to an
Functional characterisation of twelve terpene synthases from actinobacteria
Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100
- ), hundreds of plant terpene synthases have been identified [3][4], including terpene synthases of microbial type [5]. Also many fungal terpene synthases are known that can either be monofunctional as in case of the aristolochene (3) synthases from Aspergillus terreus [6] and Penicillium roqueforti [7], or
A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1H-pyrrole-2,3-diones with diazooxindoles
Beilstein J. Org. Chem. 2022, 18, 1532–1538, doi:10.3762/bjoc.18.162
- and J [16] were also isolated from the fungus Penicillium commune and contain a furan fragment spiro-annulated by 2-oxindole. These compounds exhibit anticancer [13] and antimicrobial [17] activities. One of the expeditious methods for obtaining dihydrofurans is the cycloaddition reaction of diazo
The stereochemical course of 2-methylisoborneol biosynthesis
Beilstein J. Org. Chem. 2022, 18, 818–824, doi:10.3762/bjoc.18.82
- contaminations in water supply systems [10][11]. In addition, the liverwort Lophocolea heterophylla [12] and various strains of Penicillium [13] have been reported as a source of compound 1. As a consequence of cheese fermentation with Penicillium, compound 1 can add to the flavor of Camembert and Brie [14], but
Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus
Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124
- molecules like non-ribosomal peptides (NRP), polyketides (PK), terpenes or indole alkaloids [10][11]. The vast majority of fungal BGCs is found in the genomes of members of the Basidiomycota and Ascomycota including the genus Penicillium in which the first BGC was identified in 1990 [12][13][14
- ]. Penicillium species belong to the Pezizomycotina, a subdivision within the Ascomycotina including several species that are closely associated with humans at many different levels. Aside from being a source of many medically relevant compounds including antibiotics like penicillin they offer food sources in
- fungi also produce compounds with antibacterial, antifungal and insecticidal properties to ward of both competitors and predators. The mycotoxins aflatoxin B1 (1) from Aspergillus flavus and patulin (2), produced by Aspergillus and Penicillium species, exhibit insecticidal activity against Drosophila
Total synthesis of decarboxyaltenusin
Beilstein J. Org. Chem. 2021, 17, 224–228, doi:10.3762/bjoc.17.22
- -methyl-[1,1’-biphenyl]-3,3’,4-triol (1, Scheme 1) has been first mentioned 1974 as a reduction and decarboxylation product of dehydroaltenusin [1]. As the compound has later been isolated from Ulocladium sp. [2], Nigrospora sphaerica, Phialophora sp. [3], Penicillium pinophilum SD-272 [4], Alternaria sp
Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale
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)
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
Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211
Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28
- esters [3], and globosuxanthone B [4], among others. Diversonolic esters were firstly reported by Holker from cultures of Talaromyces diversus, anamorph Penicillium diversum [3]; however, the originally proposed structures of the diversonolic esters were revised after 25 years, following their total
Isolation of fungi using the diffusion chamber device FIND technology
Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216
- axenic. From experiment 1, 39 isolates were microscopically identified as belonging to genera common in soil, e.g., Fusarium, Penicillium or Trichoderma and thus were not further processed. The addition of antibiotics prevented bacterial contamination in all marine samples. However, a few antibiotic
Volatiles from the hypoxylaceous fungi Hypoxylon griseobrunneum and Hypoxylon macrocarpum
Beilstein J. Org. Chem. 2018, 14, 2974–2990, doi:10.3762/bjoc.14.277
- producing and non-producing Penicillium roqueforti isolates [6]. On the other hand, fungal volatiles are interesting, because they contribute with their aroma to the flavour of many edible mushrooms. One of the first identified and certainly most widespread compounds is matsutake alcohol, (R)-oct-1-en-3-ol
Synthesis of spirocyclic scaffolds using hypervalent iodine reagents
Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152
- drugs for the treatment of several health problems [9][10]. Annosqualine (1) is an isoquinoline-cored alkaloid and it was isolated in 2004 from the stem of Annona squamosa [11] (Figure 1). Griseofulvin (2) is a spirobenzofuranone-based naturally occurring compound which was isolated from Penicillium
Volatiles from three genome sequenced fungi from the genus Aspergillus
Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77
- 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
Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone
Beilstein J. Org. Chem. 2018, 14, 547–552, doi:10.3762/bjoc.14.41
- -(pent-1-enyl)-α-pyrone and trans-6-(pent-1,4-dienyl)-α-pyrone, which are naturally occurring metabolites isolated from Trichoderma viride and Penicillium, in high chemical yield and with excellent stereo selectivity. Keywords: Corey–Winter reaction; electrosynthesis; 6-pentyl-2H-pyran-2-ones; reduction
- 1–3 was reported by our research group [7]. These molecules proved to be enantiomers of metabolites isolated from Trichoderma spp and Penicillium isolates. Unfortunately, our efforts for obtaining the natural metabolite trans-6-(pent-1-enyl)-α-pyrone (5) (isolable from Trichoderma viride [8]) via a
- , N2 bubbling 5 min, WE = vitreous carbon, CE = Pt wire, RE = Ag/AgCl in MeO/H2O (80:20) in AcOH/AcONa buffer 0.5 M media. The Corey–Winter reaction in general. Proposed route for the synthesis of metabolites isolated from Trichoderma and Penicillium species from 7,3-LXF. Preparation of thiocarbonate
Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)
Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9
- biocontrol agents [6]. On the contrary, fungi can also produce mycotoxins, which must be excluded for their safe usage in agricultural biocontrol. Some volatiles, especially terpenes, point to the production of certain toxins in fungi, e.g., aristolochene (3) is the precursor of PR toxin in Penicillium
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