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Keywords = Penicillium purpurogenum

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15 pages, 3658 KB  
Article
The Effect of Particles from Rotten Spruce Logs and Recycled Wooden Composites on Changes in the Bio-Resistance of Three-Layer Particleboards Against the Decaying Fungus Coniophora puteana and Mixture of Moulds
by Zuzana Vidholdová, Viktória Satinová and Ladislav Reinprecht
Forests 2024, 15(11), 2043; https://doi.org/10.3390/f15112043 - 19 Nov 2024
Viewed by 1419
Abstract
Wood-based particleboards (PBs) are widely used in construction and interior applications, yet their durability, particularly against biological degradation, remains a challenge. Recycling wood and incorporating degraded particles from rotted wood can potentially enhance PB sustainability and align with circular bioeconomy principles. This study [...] Read more.
Wood-based particleboards (PBs) are widely used in construction and interior applications, yet their durability, particularly against biological degradation, remains a challenge. Recycling wood and incorporating degraded particles from rotted wood can potentially enhance PB sustainability and align with circular bioeconomy principles. This study investigates the biological resistance of the three-layer, laboratory-prepared PBs with varied amounts of particles, from sound spruce wood to particles, and from spruce logs attacked by brown- or white rot, respectively, to particles from recycled wooden composites of laminated particleboards (LPBs) or blockboards (BBs), i.e., 100:0, 80:20, 50:50, and 0:100. The bio-resistance of PBs was evaluated against the brown-rot fungus Coniophora puteana, as well as against a mixture of moulds’ “microscopic fungi”, such as Aspergillus versicolor BAM 8, Aspergillus niger BAM 122, Penicillium purpurogenum BAM 24, Stachybotrys chartarum BAM 32, and Rhodotorula mucilaginosa BAM 571. PBs containing particles from brown-rotten wood or from recycled wood composites, particularly LPBs, had a partly enhanced decay resistance, but their mass loss was nevertheless more than 30%. On the other hand, the mould resistance of all variants of PBs, evaluated in the 21st day, was very poor, with the highest mould growth activity (MGA = 4). These findings suggested that some types of rotten and recycled wood particles can improve the biological resistance of PBs; however, their effectiveness is influenced by the type of wood degradation and the source of recycled materials. Further, the results highlight the need for improved biocidal, chemical, or thermal modifications of wood particles to enhance the overall biological durability of PBs for specific uses. Full article
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13 pages, 2204 KB  
Article
Purification, Characterization and Antifungal Activity of the Aspergillus niveus Chitinase Produced Using Shrimp Shells
by Pedro Henrique Ornela and Luis Henrique Souza Guimarães
Appl. Biosci. 2024, 3(2), 220-232; https://doi.org/10.3390/applbiosci3020015 - 11 May 2024
Cited by 5 | Viewed by 3628
Abstract
Chitinases are biotechnologically relevant enzymes that can be applied in such different sectors as pharmaceutical, food, environmental management, the biocontrol of pests and in the paper and cellulose industry. Microorganisms as filamentous fungi are the most important source of these biomolecules. The fungus [...] Read more.
Chitinases are biotechnologically relevant enzymes that can be applied in such different sectors as pharmaceutical, food, environmental management, the biocontrol of pests and in the paper and cellulose industry. Microorganisms as filamentous fungi are the most important source of these biomolecules. The fungus Aspergillus niveus produces extracellular chitinase when cultured under submerged fermentation using shrimp shells, a residue generated by the fish industry, as a carbon source, for 96 h at 30 °C and 100 rpm. The particle size and concentration of the shrimp shells affected enzyme production. The chitinase was purified until electrophoretic homogeneity through the use of a Sephadex G-100 chromatographic column. It is a monomeric glycoprotein with a molecular mass of 47 kDa estimated using SDS-PAGE and 49.3 kDa determined using gel filtration. The carbohydrate content was 22.8%. The best temperature and pH for enzyme activity were 65 °C and 6.0, respectively. Approximately 80% of the enzymatic activity was preserved at pH 4.0 and 5.0 for 48 h, and the half-life (t50) was maintained for 48 h at 40 °C. Salts, EDTA and β-mercaptoethanol did not affect chitinase activity significantly, but organic solvents reduced it. The kinetic parameters determined using p-NPGlycNac were Km of 2.67 mmol L−1, Vmax of 12.58 U mg of protein−1, Kcat of 2.47 s−1 and K cat/Km of 0.93 s−1 mmol L−1. The A. niveus chitinase inhibited the growth of all fungal strains used, especially Trichoderma harzianum (MIC = 22.4 μg mL−1) and Penicillium purpurogenum (MIC = 11.2 μg mL−1). The chitinase produced by A. niveus presented interesting characteristics that indicate its potential of application in different areas. Full article
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14 pages, 4237 KB  
Article
Chemical Profiling, Bioactivity Evaluation and the Discovery of a Novel Biopigment Produced by Penicillium purpurogenum CBS 113139
by Antonis D. Tsiailanis, Chrysanthi Pateraki, Mary Kyriazou, Christos M. Chatzigiannis, Maria Chatziathanasiadou, Nikolaos Parisis, Ioanna Mandala, Andreas G. Tzakos and Apostolis Koutinas
Molecules 2022, 27(1), 69; https://doi.org/10.3390/molecules27010069 - 23 Dec 2021
Cited by 6 | Viewed by 4046
Abstract
Biobased pigments are environmentally friendly alternatives to synthetic variants with an increased market demand. Production of pigments via fermentation is a promising process, yet optimization of the production yield and rate is crucial. Herein, we evaluated the potential of Penicillium purpurogenum to produce [...] Read more.
Biobased pigments are environmentally friendly alternatives to synthetic variants with an increased market demand. Production of pigments via fermentation is a promising process, yet optimization of the production yield and rate is crucial. Herein, we evaluated the potential of Penicillium purpurogenum to produce biobased pigments. Optimum sugar concentration was 30 g/L and optimum C:N ratio was 36:1 resulting in the production of 4.1–4.5 AU (namely Pigment Complex A). Supplementation with ammonium nitrate resulted in the production of 4.1–4.9 AU (namely Pigment Complex B). Pigments showed excellent pH stability. The major biopigments in Pigment Complex A were N-threonyl-rubropunctamin or the acid form of PP-R (red pigment), N-GABA-PP-V (violet pigment), PP-O (orange pigment) and monascorubrin. In Pigment Complex B, a novel biopigment annotated as N-GLA-PP-V was identified. Its basic structure contains a polyketide azaphilone with the same carboxyl-monascorubramine base structure as PP-V (violet pigment) and γ-carboxyglutamic acid (GLA). The pigments were not cytotoxic up to 250 μg/mL. Full article
(This article belongs to the Special Issue Microbial Bioconversions and Valuable Compounds Production)
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14 pages, 1317 KB  
Article
New Antifungal Microbial Pigment Applied to Improve Safety and Quality of Processed Meat-Products
by Hatem Ali Salama, Ahmed Noah Badr, Manal F. Elkhadragy, Ahmed Mohamed Said Hussein, Ibrahim Abdel-Salam Shaban and Hany M. Yehia
Microorganisms 2021, 9(5), 989; https://doi.org/10.3390/microorganisms9050989 - 4 May 2021
Cited by 12 | Viewed by 4548
Abstract
Minced meat is involved within numerous products, where their color attributes are affected by consumer preferences. This study was aimed to ameliorate processed meat color, using a microbial red pigment. Antibacterial, antifungal, citrinin-free, and toxicity of pigment were determined. Meatballs and burgers were [...] Read more.
Minced meat is involved within numerous products, where their color attributes are affected by consumer preferences. This study was aimed to ameliorate processed meat color, using a microbial red pigment. Antibacterial, antifungal, citrinin-free, and toxicity of pigment were determined. Meatballs and burgers were manufactured using pigment at 3 mg/g of meat. Texture, color, shelf life extension, and organoleptic properties were estimated for treated meats. Results were expressed by a real antimicrobial for pigment, even via several extracting systems. The MIC and MFC of pigment were 320 µg/g and 2.75 mg/g media, respectively. Bioactive components of pigment were detected using the GC–MS and the FTIR apparatus. The bioactive carbohydrates include oligo and polysaccharides were manifested with real curves. Secretion of ochratoxin A and aflatoxins in fungal media receives pigment was decreased by up to 54% and 45%, respectively. The presence of bioactive carbohydrates may trap mycotoxin out of the recovered amounts. The manufactured products were enhanced for their color and taste with fine texture changes. The shelf life of colored-frying meat was recorded by an extension compared to the control. In conclusion, the results were recommended microbial red-pigment implementation in meats manufacturing for ameliorating recorded of color, as antimycotoxigenic, and shelf life extension. Full article
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16 pages, 3744 KB  
Article
The Impact of a CO2 Laser on the Adhesion and Mold Resistance of a Synthetic Polymer Layer on a Wood Surface
by Ladislav Reinprecht and Zuzana Vidholdová
Forests 2021, 12(2), 242; https://doi.org/10.3390/f12020242 - 20 Feb 2021
Cited by 12 | Viewed by 3037
Abstract
In the wood industry, laser technologies are commonly applied for the sawing, engraving, or perforation of solid wood and wood composites, but less knowledge exists about their effect on the joining and painting of wood materials with synthetic polymer adhesives and coatings. In [...] Read more.
In the wood industry, laser technologies are commonly applied for the sawing, engraving, or perforation of solid wood and wood composites, but less knowledge exists about their effect on the joining and painting of wood materials with synthetic polymer adhesives and coatings. In this work, a CO2 laser with irradiation doses from 2.1 to 18.8 J·cm−2 was used for the modification of European beech (Fagus sylvatica L.) and Norway spruce (Picea abies /L./ Karst) wood surfaces—either in the native state or after covering them with a layer of polyvinyl acetate (PVAc) or polyurethane (PUR) polymer. The adhesion strength of the phase interface “synthetic polymer—wood”, evaluated by the standard EN ISO 4624, decreased significantly and proportionately in all the laser modification modes, with higher irradiation doses leading to a more apparent degradation and carbonization of the wood adherent or the synthetic polymer layer. The mold resistance of the polymers, evaluated by the standard EN 15457, increased significantly for the less mold-resistant PVAc polymer after its irradiation on the wood adherent. However, the more mold-resistant PUR polymer was able to better resist the microscopic fungi Aspergillus niger Tiegh. and Penicillium purpurogenum Stoll. when irradiation doses of higher intensity acted firstly on the wood adherent. Full article
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17 pages, 13825 KB  
Article
Quality of Oil- and Wax-Based Surface Finishes on Thermally Modified Oak Wood
by Zuzana Vidholdová, Gabriela Slabejová and Mária Šmidriaková
Coatings 2021, 11(2), 143; https://doi.org/10.3390/coatings11020143 - 28 Jan 2021
Cited by 22 | Viewed by 6488
Abstract
In this study, natural linseed oil, hard wax oil, and hard wax, commonly used as finishes for wooden furniture and parquet, were used for surface finishes on Turkey oak wood (Quercus cerris L.), thermally modified at temperatures of 175 °C and 195 [...] Read more.
In this study, natural linseed oil, hard wax oil, and hard wax, commonly used as finishes for wooden furniture and parquet, were used for surface finishes on Turkey oak wood (Quercus cerris L.), thermally modified at temperatures of 175 °C and 195 °C for 4 h. Several resistance surface properties were investigated. The mechanical resistance properties of all surface finishes were very much allied to interactions between the finish and the type of substrate. The adhesion strength and impact resistance decreased if higher temperature was used for thermal modification of the substrate. The surface hardness and the resistance to abrasion were high and increased slightly with increasing temperature during thermal modification of wood. It was also found that surface adhesion, hardness and resistance to impact were very much related to interactions between the coating film and the substrate. The resistance properties of finishes, such as resistance to cold liquids and mold, were mainly influenced by the type of the surface finish. The resistance to cold liquids increased in the order: surface finish with hard wax < linseed oil < finish system of linseed oil + hard wax oil. The lowest resistance to cold liquids showed up in condensed milk and sanitizer. Resistance to Aspergillus niger and Penicillium purpurogenum was relatively weak, however apparently improved during the first 7 days of the fungal test; the surfaces were covered with a lower distribution density of fungal mycelium after 21 days of the fungal test. Individual surface performances of oil and wax-based surface finishes on native wood were different from thermally modified wood. Full article
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19 pages, 3732 KB  
Article
Marine-Derived Penicillium purpurogenum Reduces Tumor Size and Ameliorates Inflammation in an Erlich Mice Model
by Amanda Mara Teles, Leticia Prince Pereira Pontes, Sulayne Janayna Araújo Guimarães, Ana Luiza Butarelli, Gabriel Xavier Silva, Flavia Raquel Fernandes do Nascimento, Geusa Felipa de Barros Bezerra, Carla Junqueira Moragas-Tellis, Rui Miguel Gil da Costa, Marcos Antonio Custódio Neto da Silva, Fernando Almeida-Souza, Kátia da Silva Calabrese, Ana Paula Silva Azevedo-Santos and Maria do Desterro Soares Brandão Nascimento
Mar. Drugs 2020, 18(11), 541; https://doi.org/10.3390/md18110541 - 29 Oct 2020
Cited by 9 | Viewed by 3852
Abstract
Background: This study addresses the antitumoral properties of Penicillium purpurogenum isolated from a polluted lagoon in Northeastern Brazil. Methods: Ethyl Acetate Extracellular Extract (EAE) was used. The metabolites were studied using direct infusion mass spectrometry. The solid Ehrlich tumor model was used for [...] Read more.
Background: This study addresses the antitumoral properties of Penicillium purpurogenum isolated from a polluted lagoon in Northeastern Brazil. Methods: Ethyl Acetate Extracellular Extract (EAE) was used. The metabolites were studied using direct infusion mass spectrometry. The solid Ehrlich tumor model was used for antitumor activity. Female Swiss mice were divided into groups (n = 10/group) as follows: The negative control (CTL−), treated with a phosphate buffered solution; the positive control (CTL+), treated with cyclophosphamide (25 mg/kg); extract treatments at doses of 4, 20, and 100 mg/kg; animals without tumors or treatments (Sham); and animals without tumors treated with an intermediate dose (EAE20). All treatments were performed intraperitoneally, daily, for 15 days. Subsequently, the animals were euthanized, and the tumor, lymphoid organs, and serum were used for immunological, histological, and biochemical parameter evaluations. Results: The extract was rich in meroterpenoids. All doses significantly reduced tumor size, and the 20 and 100 mg/kg doses reduced tumor-associated inflammation and tumor necrosis. The extract also reduced the cellular infiltration of lymphoid organs and circulating TNF-α levels. The extract did not induce weight loss or renal and hepatic toxic changes. Conclusions: These results indicate that P. purpurogenum exhibits immunomodulatory and antitumor properties in vivo. Thus, fungal fermentation is a valid biotechnological approach to the production of antitumor agents. Full article
(This article belongs to the Special Issue Marine Natural Products as Anticancer Agents)
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21 pages, 7653 KB  
Article
Production and New Extraction Method of Polyketide Red Pigments Produced by Ascomycetous Fungi from Terrestrial and Marine Habitats
by Juliana Lebeau, Mekala Venkatachalam, Mireille Fouillaud, Thomas Petit, Francesco Vinale, Laurent Dufossé and Yanis Caro
J. Fungi 2017, 3(3), 34; https://doi.org/10.3390/jof3030034 - 28 Jun 2017
Cited by 82 | Viewed by 11191
Abstract
The use of ascomycetous fungi as pigment producers opens the way to an alternative to synthetic dyes, especially in the red-dye industries, which have very few natural pigment alternatives. The present paper aimed to bio-prospect and screen out 15 selected ascomycetous fungal strains, [...] Read more.
The use of ascomycetous fungi as pigment producers opens the way to an alternative to synthetic dyes, especially in the red-dye industries, which have very few natural pigment alternatives. The present paper aimed to bio-prospect and screen out 15 selected ascomycetous fungal strains, originating from terrestrial and marine habitats belonging to seven different genera (Penicillium, Talaromyces, Fusarium, Aspergillus, Trichoderma, Dreschlera, and Paecilomyces). We identified four strains, Penicillium purpurogenum rubisclerotium, Fusarium oxysporum, marine strains identified as Talaromyces spp., and Trichoderma atroviride, as potential red pigment producers. The extraction of the pigments is a crucial step, whereby the qualitative and quantitative compositions of each fungal extract need to be respected for reliable identification, as well as preserving bioactivity. Furthermore, there is a growing demand for more sustainable and cost-effective extraction methods. Therefore, a pressurized liquid extraction technique was carried out in this study, allowing a greener and faster extraction step of the pigments, while preserving their chemical structures and bioactivities in comparison to conventional extraction processes. The protocol was illustrated with the production of pigment extracts from P. purpurogenum rubisclerotium and Talaromyces spp. Extracts were analyzed by high-performance liquid-chromatography combined with photodiode array-detection (HPLC-DAD) and high-resolution mass spectrometry (UHPLC-HRMS). The more promising strain was the isolate Talaromyces spp. of marine origin. The main polyketide pigment produced by this strain has been characterized as N-threoninerubropunctamine, a non-toxic red Monascus-like azaphilone pigment. Full article
(This article belongs to the Special Issue Fungal Pigments)
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18 pages, 484 KB  
Article
Rare Chromones from a Fungal Mutant of the Marine-Derived Penicillium purpurogenum G59
by Ming-Wen Xia, Cheng-Bin Cui, Chang-Wei Li, Chang-Jing Wu, Ji-Xing Peng and De-Hai Li
Mar. Drugs 2015, 13(8), 5219-5236; https://doi.org/10.3390/md13085219 - 18 Aug 2015
Cited by 35 | Viewed by 6201
Abstract
Three new and rare chromones, named epiremisporine B (2), epiremisporine B1 (3) and isoconiochaetone C (4), along with three known remisporine B (1), coniochaetone A (5) and methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (6 [...] Read more.
Three new and rare chromones, named epiremisporine B (2), epiremisporine B1 (3) and isoconiochaetone C (4), along with three known remisporine B (1), coniochaetone A (5) and methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (6) were isolated from a mutant from the diethyl sulfate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. The structures of 24 including the absolute configurations were determined by spectroscopic methods, especially by NMR analysis and electronic circular dichroism (ECD) experiments in conjunction with calculations. The absolute configuration of the known remisporine B (1) was determined for the first time. Compounds 2 and 3 have a rare feature that has only been reported in one example so far. The compounds 16 were evaluated for their cytotoxicity against several human cancer cell lines. The present work explored the great potential of our previous DES mutagenesis strategy for activating silent fungal pathways, which has accelerated the discovery of new bioactive compounds. Full article
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23 pages, 1261 KB  
Article
Activation of the Silent Secondary Metabolite Production by Introducing Neomycin-Resistance in a Marine-Derived Penicillium purpurogenum G59
by Chang-Jing Wu, Le Yi, Cheng-Bin Cui, Chang-Wei Li, Nan Wang and Xiao Han
Mar. Drugs 2015, 13(4), 2465-2487; https://doi.org/10.3390/md13042465 - 22 Apr 2015
Cited by 32 | Viewed by 8410
Abstract
Introduction of neomycin-resistance into a marine-derived, wild-type Penicillium purpurogenum G59 resulted in activation of silent biosynthetic pathways for the secondary metabolite production. Upon treatment of G59 spores with neomycin and dimethyl sulfoxide (DMSO), a total of 56 mutants were obtained by single colony [...] Read more.
Introduction of neomycin-resistance into a marine-derived, wild-type Penicillium purpurogenum G59 resulted in activation of silent biosynthetic pathways for the secondary metabolite production. Upon treatment of G59 spores with neomycin and dimethyl sulfoxide (DMSO), a total of 56 mutants were obtained by single colony isolation. The acquired resistance of mutants to neomycin was testified by the resistance test. In contrast to the G59 strain, the EtOAc extracts of 28 mutants inhibited the human cancer K562 cells, indicating that the 28 mutants have acquired the capability to produce bioactive metabolites. HPLC-photodiode array detector (PDAD)-UV and HPLC-electron spray ionization (ESI)-MS analyses further indicated that diverse secondary metabolites have been newly produced in the bioactive mutant extracts. Followed isolation and characterization demonstrated that five bioactive secondary metabolites, curvularin (1), citrinin (2), penicitrinone A (3), erythro-23-O-methylneocyclocitrinol (4) and 22E-7α-methoxy-5α, 6α-epoxyergosta-8(14),22-dien-3β-ol (5), were newly produced by a mutant, 4-30, compared to the G59 strain. All 15 were also not yet found in the secondary metabolites of other wild type P. purpurogenum strains. Compounds 15 inhibited human cancer K562, HL-60, HeLa and BGC-823 cells to varying extents. Both present bioassays and chemical investigations demonstrated that the introduction of neomycin-resistance into the marine-derived fungal G59 strain could activate silent secondary metabolite production. The present work not only extended the previous DMSO-mediated method for introducing drug-resistance in fungi both in DMSO concentrations and antibiotics, but also additionally exemplified effectiveness of this method for activating silent fungal secondary metabolites. This method could be applied to other fungal isolates to elicit their metabolic potentials to investigate secondary metabolites from silent biosynthetic pathways. Full article
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24 pages, 1192 KB  
Article
Seven New and Two Known Lipopeptides as well as Five Known Polyketides: The Activated Production of Silent Metabolites in a Marine-Derived Fungus by Chemical Mutagenesis Strategy Using Diethyl Sulphate
by Chang-Jing Wu, Chang-Wei Li and Cheng-Bin Cui
Mar. Drugs 2014, 12(4), 1815-1838; https://doi.org/10.3390/md12041815 - 28 Mar 2014
Cited by 60 | Viewed by 7459
Abstract
AD-2-1 is an antitumor fungal mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59. The G59 strain originally did not produce any metabolites with antitumor activities in MTT assays using K562 cells. Tracing newly produced metabolites under guidance of MTT [...] Read more.
AD-2-1 is an antitumor fungal mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59. The G59 strain originally did not produce any metabolites with antitumor activities in MTT assays using K562 cells. Tracing newly produced metabolites under guidance of MTT assay and TLC analysis by direct comparison with control G59 extract, seven new (17) and two known (89) lipopeptides were isolated together with five known polyketides 1014 from the extract of mutant AD-2-1. Structures of the seven new compounds including their absolute configurations were determined by spectroscopic and chemical evidences and named as penicimutalides A–G (17). Seven known compounds were identified as fellutamide B (8), fellutamide C (9), 1′-O-methylaverantin (10), averantin (11), averufin (12), nidurufin (13), and sterigmatocystin (14). In the MTT assay, 114 inhibited several human cancer cell lines to varying extents. All the bioassays and HPLC-photodiode array detector (PDAD)-UV and HPLC-electron spray ionization (ESI)-MS analyses demonstrated that the production of 114 in the mutant AD-2-1 was caused by the activated production of silent metabolites in the original G59 fungal strain. Present results provided additional examples for effectiveness of the chemical mutagenesis strategy using diethyl sulphate mutagenesis to discover new compounds by activating silent metabolites in fungal isolates. Full article
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27 pages, 1162 KB  
Article
A Practical Strategy to Discover New Antitumor Compounds by Activating Silent Metabolite Production in Fungi by Diethyl Sulphate Mutagenesis
by Shi-Ming Fang, Chang-Jing Wu, Chang-Wei Li and Cheng-Bin Cui
Mar. Drugs 2014, 12(4), 1788-1814; https://doi.org/10.3390/md12041788 - 27 Mar 2014
Cited by 44 | Viewed by 7815
Abstract
Many fungal biosynthetic pathways are silent in standard culture conditions, and activation of the silent pathways may enable access to new metabolites with antitumor activities. The aim of the present study was to develop a practical strategy for microbial chemists to access silent [...] Read more.
Many fungal biosynthetic pathways are silent in standard culture conditions, and activation of the silent pathways may enable access to new metabolites with antitumor activities. The aim of the present study was to develop a practical strategy for microbial chemists to access silent metabolites in fungi. We demonstrated this strategy using a marine-derived fungus Penicillium purpurogenum G59 and a modified diethyl sulphate mutagenesis procedure. Using this strategy, we discovered four new antitumor compounds named penicimutanolone (1), penicimutanin A (2), penicimutanin B (3), and penicimutatin (4). Structures of the new compounds were elucidated by spectroscopic methods, especially extensive 2D NMR analysis. Antitumor activities were assayed by the MTT method using human cancer cell lines. Bioassays and HPLC-photodiode array detector (PDAD)-UV and HPLC-electron spray ionization (ESI)-MS analyses were used to estimate the activated secondary metabolite production. Compounds 2 and 3 had novel structures, and 1 was a new compound belonging to a class of very rare natural products from which only four members are so far known. Compounds 13 inhibited several human cancer cell lines with IC50 values lower than 20 μM, and 4 inhibited the cell lines to some extent. These results demonstrated the effectiveness of this strategy to discover new compounds by activating silent fungal metabolic pathways. These discoveries provide rationale for the increased use of chemical mutagenesis strategies in silent fungal metabolite studies. Full article
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24 pages, 1239 KB  
Article
Three New and Eleven Known Unusual C25 Steroids: Activated Production of Silent Metabolites in a Marine-Derived Fungus by Chemical Mutagenesis Strategy using Diethyl Sulphate
by Ming-Wen Xia, Cheng-Bin Cui, Chang-Wei Li and Chang-Jing Wu
Mar. Drugs 2014, 12(3), 1545-1568; https://doi.org/10.3390/md12031545 - 13 Mar 2014
Cited by 53 | Viewed by 8209
Abstract
Three new (13) and 11 known (414) C25 steroids with an unusual bicyclo[4.4.1]A/B ring system were isolated by tracing newly produced metabolites in the EtOAc extract of an antitumor mutant AD-1-2 obtained by the diethyl [...] Read more.
Three new (13) and 11 known (414) C25 steroids with an unusual bicyclo[4.4.1]A/B ring system were isolated by tracing newly produced metabolites in the EtOAc extract of an antitumor mutant AD-1-2 obtained by the diethyl sulphate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. HPLC-PDAD-UV and HPLC-ESI-MS analyses indicated that the G59 strain did not produce these metabolites and the production of 114 in the mutant AD-1-2 extract was caused by the activation of silent metabolites in the original G59 strain by DES mutagenesis. The structures of the new compounds, named antineocyclocitrinols A (1) and B (2) and 23-O-methylantineocyclocitrinol (3), including their absolute configurations were determined by various spectroscopic methods, especially the NMR and Mo2-induced CD analyses. Compounds 13 provide the first examples of the C25 bicyclo[4.4.1]A/B ring steroids with the Z-configuration of 20,22-double bond. All of 114 weakly inhibited several human cancer cell lines to varying extents. These results provided additional examples for the successful application of the chemical mutagenesis strategy using DES to discover new compounds by activating silent metabolites in fungal isolates and supported also the effectiveness and usefulness of this new strategy. Full article
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22 pages, 962 KB  
Article
Purpurogemutantin and Purpurogemutantidin, New Drimenyl Cyclohexenone Derivatives Produced by a Mutant Obtained by Diethyl Sulfate Mutagenesis of a Marine-Derived Penicillium purpurogenum G59
by Shi-Ming Fang, Cheng-Bin Cui, Chang-Wei Li, Chang-Jing Wu, Zhi-Jun Zhang, Li Li, Xiao-Jun Huang and Wen-Cai Ye
Mar. Drugs 2012, 10(6), 1266-1287; https://doi.org/10.3390/md10061266 - 4 Jun 2012
Cited by 65 | Viewed by 9839
Abstract
Two new drimenyl cyclohexenone derivatives, named purpurogemutantin (1) and purpurogemutantidin (2), and the known macrophorin A (3) were isolated from a bioactive mutant BD-1-6 obtained by random diethyl sulfate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. [...] Read more.
Two new drimenyl cyclohexenone derivatives, named purpurogemutantin (1) and purpurogemutantidin (2), and the known macrophorin A (3) were isolated from a bioactive mutant BD-1-6 obtained by random diethyl sulfate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. Structures and absolute configurations of 1 and 2 were determined by extensive spectroscopic methods, especially 2D NMR and electronic circular dichroism (ECD) analysis. Possible biosynthetic pathways for 13 were also proposed and discussed. Compounds 1 and 2 significantly inhibited human cancer K562, HL-60, HeLa, BGC-823 and MCF-7 cells, and compound 3 also inhibited the K562 and HL-60 cells. Both bioassay and chemical analysis (HPLC, LC-ESIMS) demonstrated that the parent strain G59 did not produce 13, and that DES-induced mutation(s) in the mutant BD-1-6 activated some silent biosynthetic pathways in the parent strain G59, including one set for 13 production. Full article
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24 pages, 1162 KB  
Article
Activation of the Dormant Secondary Metabolite Production by Introducing Gentamicin-Resistance in a Marine-Derived Penicillium purpurogenum G59
by Yun-Jing Chai, Cheng-Bin Cui, Chang-Wei Li, Chang-Jing Wu, Cong-Kui Tian and Wei Hua
Mar. Drugs 2012, 10(3), 559-582; https://doi.org/10.3390/md10030559 - 2 Mar 2012
Cited by 76 | Viewed by 11612
Abstract
A new approach to activate silent gene clusters for dormant secondary metabolite production has been developed by introducing gentamicin-resistance to an originally inactive, marine-derived fungal strain Penicillium purpurogenum G59. Upon treatment of the G59 spores with a high concentration of gentamicin in aqueous [...] Read more.
A new approach to activate silent gene clusters for dormant secondary metabolite production has been developed by introducing gentamicin-resistance to an originally inactive, marine-derived fungal strain Penicillium purpurogenum G59. Upon treatment of the G59 spores with a high concentration of gentamicin in aqueous DMSO, a total of 181 mutants were obtained by single colony isolation. In contrast to the strain G59, the EtOAc extracts of nine mutant cultures showed inhibitory effects on K562 cells, indicating that the nine mutants had acquired capability to produce antitumor metabolites. This was evidenced by TLC and HPLC analysis of EtOAc extracts of G59 and the nine mutants. Further isolation and characterization demonstrated that four antitumor secondary metabolites, janthinone (1), fructigenine A (2), aspterric acid methyl ester (3) and citrinin (4), were newly produced by mutant 5-1-4 compared to the parent strain G59, and which were also not found in the secondary metabolites of other Penicillium purpurogenum strains. However, Compounds 14 inhibited the proliferation of K562 cells with inhibition rates of 34.6% (1), 60.8% (2), 31.7% (3) and 67.1% (4) at 100 μg/mL, respectively. The present study demonstrated the effectiveness of a simple, yet practical approach to activate the production of dormant fungal secondary metabolites by introducing acquired resistance to aminoglycoside antibiotics, which could be applied to the studies for eliciting dormant metabolic potential of fungi to obtain cryptic secondary metabolites. Full article
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