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Fitoterapia Jun 2023Two new polyketides versicolorones A-B (1-2), one new diketopiperazine derivative aspergiamide B methyl ester (3), along with twenty known compounds 4-23, were obtained...
Two new polyketides versicolorones A-B (1-2), one new diketopiperazine derivative aspergiamide B methyl ester (3), along with twenty known compounds 4-23, were obtained from the EtOAc extract of the Cordyceps-colonizing fungus Aspergillus versicolor ZJUTE2. The structures of 1-3 were established by detailed interpretation of the spectroscopic data and their absolute configurations were established by comparative analyses of the calculated and experimental ECD spectra. In the in-vitro bioassay, compounds 8 and 21 exhibited significant inhibitory activity against the Escherichia coli β-glucuronidase (EcGUS) with IC values of 54.73 ± 2.69 and 56.59 ± 1.77 μM, respectively.
Topics: Cordyceps; Molecular Structure; Aspergillus; Spectrum Analysis
PubMed: 37028494
DOI: 10.1016/j.fitote.2023.105501 -
Environmental Monitoring and Assessment Mar 2021There is a close relationship between human health and the quality of the ration used by domestic animals. Also, molds, like genus of Aspergillus, infect animal and...
There is a close relationship between human health and the quality of the ration used by domestic animals. Also, molds, like genus of Aspergillus, infect animal and human food products with dangerous toxic substances, i.e., aflatoxins that are causing primary and secondary mycotoxicosis in animals and human. The aim of this study was to compare fungal species that contaminated and produced aflatoxin in livestock and poultry feed in Gonabad that is a semi-arid city in northeast of Iran. Sampling was randomly performed three times from two livestock feed mills and two poultry feed mills during summer and autumn. Samples were cultured in two forms of solid and suspension in Sabouraud dextrose agar with chloramphenicol medium (SC) for 5 days in 28 °C. Microscopic diagnostic test and also molecular diagnostic test were used to determine fungal species in culture based on β-tubulin gene sequencing. A total of 27.25% and 31.7% of two livestock feed and two poultry feed samples were contaminated with Aspergillus, respectively. Aspergillus flavus (n = 4), Aspergillus Fumigatus (n = 2), Aspergillus versicolor (n = 2), Aspergillus niger (n = 2), Aspergillus parasiticus (n = 1), Aspergillus ochraceus (n = 1), and Aspergillus terreus (n = 1) were detected by molecular PCR test. The rate of contamination to genus of Aspergillus in autumn was higher than summer (P value = 0.008). Poultry feed sample showed more contamination to Aspergillus species compared with livestock feed.
Topics: Aflatoxins; Animal Feed; Animals; Aspergillus; Aspergillus flavus; Diagnostic Tests, Routine; Environmental Monitoring; Fungi; Humans; Iran
PubMed: 33759035
DOI: 10.1007/s10661-021-08990-7 -
Fitoterapia Oct 2021Two novel kojic acid derivatives, kojicones A and B (1 and 2), along with the precursors kojic acid (3) and (2R,4R)-4-hydroxy-5-methoxy-2,4-dimethyl-2-...
Two novel kojic acid derivatives, kojicones A and B (1 and 2), along with the precursors kojic acid (3) and (2R,4R)-4-hydroxy-5-methoxy-2,4-dimethyl-2- [(2R)-2-methylbutyryloxy]-5-cyclohexen-1,3-dione (4), were isolated from a fungal strain Aspergillus versicolor. Their structures and absolute configurations were accurately confirmed by HRESIMS data, NMR analysis, and electronic circular dichroism (ECD) calculations. Kojicones A and B were the first examples of kojic acid adducts with cyclohexen-1,3-dione possessing unprecedented tricycle skeletons. Compounds 1-3 were found to have inhibition on the NO production of murine RAW 264.7 cells. They can also reduce the mRNA expression of four cytokines (IL-6, IL-1β, TNF-α, and iNOS) and promote the expression of IL-4 at 20 μM. Moreover, kojic acid (3) could treat the DSS (dextran sulfate sodium)-induced colitis on mice with the effectiveness similar to that of the positive control. The results suggested that kojic acid and its derivatives could be a promising anti-inflammatory source for the medicinal and cosmetic industry.
Topics: Animals; Anti-Inflammatory Agents; Aspergillus; China; Colitis; Cytokines; Heteroptera; Mice; Molecular Structure; Nitric Oxide; Pyrones; RAW 264.7 Cells
PubMed: 34492330
DOI: 10.1016/j.fitote.2021.105027 -
Phytochemistry Jan 2023Nicotiana tabacum (tobacco) has attracted interest as one of the most economically important industrial crops widely cultivated in China, whose dried leaves are...
Nicotiana tabacum (tobacco) has attracted interest as one of the most economically important industrial crops widely cultivated in China, whose dried leaves are popularly consumed medicinally and recreationally by human societies. In this study, five undescribed alkaloids derivatives, isoaspergillines A-E, together with eight known alkaloids, notoamide D, (1R,4S)-4-benzyl-1-isopropyl-2,4-dihydro-1H-pyrazino-[2,1-b]quinazoline-3,6-dione, protuboxepin K, notoamide C, notoamide M, deoxybrevianamide E, cyclo (D-Pro-L-Trp), and versicolamide B, were obtained from the culture of the Nicotiana tabacum-derived fungus Aspergillus versicolor. Their structures were mainly elucidated through comprehensive analyses of spectroscopic data. Bioactivity evaluation of all isolated compounds revealed that isoaspergilline A and notoamide M exhibited anti-TMV activities with IC values of 20.0 and 22.8 μM, respectively. Molecular docking suggested that isoaspergilline A and notoamide M were well located into the active site of anti-TMV by interacting with SER138, SER143, and ASN73 residues. This study enlightens the therapeutic potential of the endophytic fungus A. versicolor and it is helpful to find undescribed anti-TMV activity inhibitors, as well as searching for new anti-TMV candidates from natural sources.
Topics: Humans; Nicotiana; Molecular Docking Simulation; China
PubMed: 36334789
DOI: 10.1016/j.phytochem.2022.113485 -
Fitoterapia Jan 2018A pair of 3-arylisoindolinone enantiomers: (+)-asperglactam A (1), (-)-asperglactam A (1) and a pair of nor-bisabolane enantiomers: (+)-1-hydroxyboivinianic acid (2),...
A pair of 3-arylisoindolinone enantiomers: (+)-asperglactam A (1), (-)-asperglactam A (1) and a pair of nor-bisabolane enantiomers: (+)-1-hydroxyboivinianic acid (2), (-)-1-hydroxyboivinianic acid (2), along with seven known compounds (3-8) were obtained from the mangrove endophytic fungus Aspergillus versicolor SYSU-SKS025. Their structures were determined on the basis of HRESIMS and NMR spectroscopic data, and X-ray diffraction. (+)-Asperglactam A (1) and (-)-asperglactam A (1) are the first optically pure examples in the 3-arylisoindolinone family, which are rarely found in natural sources. All isolated compounds were evaluated for α-glucosidase inhibitory activity. The enantiomers of 1-3 showed moderate inhibitory activity against α-glucosidase with IC values ranging from 50 to 190μM. Compound 7 exhibited significant inhibitory activity against α-glucosidase with IC value of 7.5μM. In addition, compound 7 was found to inhibit nitric oxide production in RAW 264.7 macrophages with IC value of 12.5μM.
Topics: Animals; Aspergillus; Endophytes; Euphorbiaceae; Glycoside Hydrolase Inhibitors; Mice; Molecular Structure; Phthalimides; RAW 264.7 Cells; Sesquiterpenes; Stereoisomerism; alpha-Glucosidases
PubMed: 29126957
DOI: 10.1016/j.fitote.2017.11.006 -
Genes Sep 2022Three strains of the complex were isolated from a salty marsh at a former uranium mining site in Thuringia, Germany. The strains from a metal-rich environment were not...
Three strains of the complex were isolated from a salty marsh at a former uranium mining site in Thuringia, Germany. The strains from a metal-rich environment were not only highly salt tolerant (up to 20% NaCl), but at the same time could sustain elevated Cs and Sr (both up to 100 mM) concentrations as well as other (heavy) metals present in the environment. During growth experiments when screening for differential cell morphology, the occurrence of guttation droplets was observed, specifically when elevated Sr concentrations of 25 mM were present in the media. To analyze the potential of metal tolerance being promoted by these excretions, proteomics and metabolomics of guttation droplets were performed. Indeed, proteins involved in up-regulated metabolic activities as well as in stress responses were identified. The metabolome verified the presence of amino sugars, glucose homeostasis-regulating substances, abscisic acid and bioactive alkaloids, flavones and quinones.
Topics: Abscisic Acid; Amino Sugars; Aspergillus; Flavones; Glucose; Quinones; Sodium Chloride; Uranium
PubMed: 36140799
DOI: 10.3390/genes13091631 -
Marine Drugs Jan 2023Despite low temperatures, poor nutrient levels and high pressure, microorganisms thrive in deep-sea environments of polar regions. The adaptability to such extreme...
Despite low temperatures, poor nutrient levels and high pressure, microorganisms thrive in deep-sea environments of polar regions. The adaptability to such extreme environments renders deep-sea microorganisms an encouraging source of novel, bioactive secondary metabolites. In this study, we isolated 77 microorganisms collected by a remotely operated vehicle from the seafloor in the Fram Strait, Arctic Ocean (depth of 2454 m). Thirty-two bacteria and six fungal strains that represented the phylogenetic diversity of the isolates were cultured using an One-Strain-Many-Compounds (OSMAC) approach. The crude EtOAc extracts were tested for antimicrobial and anticancer activities. While antibacterial activity against methicillin-resistant (MRSA) and was common for many isolates, only two bacteria displayed anticancer activity, and two fungi inhibited the pathogenic yeast . Due to bioactivity against and rich chemical diversity based on molecular network-based untargeted metabolomics, PS108-62 was selected for an in-depth chemical investigation. A chemical work-up of the SPE-fractions of its dichloromethane subextract led to the isolation of a new PKS-NRPS hybrid macrolactone, versicolide A (), a new quinazoline (-)-isoversicomide A (), as well as three known compounds, burnettramic acid A (), cyclopenol () and cyclopenin (). Their structures were elucidated by a combination of HRMS, NMR, [α], FT-IR spectroscopy and computational approaches. Due to the low amounts obtained, only compounds and could be tested for bioactivity, with inhibiting the growth of (IC 7.2 µg/mL). These findings highlight, on the one hand, the vast potential of the genus to produce novel chemistry, particularly from underexplored ecological niches such as the Arctic deep sea, and on the other, the importance of untargeted metabolomics for selection of marine extracts for downstream chemical investigations.
Topics: Methicillin-Resistant Staphylococcus aureus; Phylogeny; Spectroscopy, Fourier Transform Infrared; Aspergillus; Fungi; Metabolome; Anti-Bacterial Agents; Plant Extracts
PubMed: 36827136
DOI: 10.3390/md21020095 -
Chemistry & Biodiversity Apr 2015A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four...
A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F-H (1-3, resp.) and 3-methoxyviolaceol-II (4), eight new bisabolane sesquiterpenoids, named (-)-(R)-cyclo-hydroxysydonic acid (5), (-)-(7S,8R)-8-hydroxysydowic acid (6), (-)-(7R,10S)-10-hydroxysydowic acid (7), (-)-(7R,10R)-iso-10-hydroxysydowic acid (8), (-)-12-acetoxy-1-deoxysydonic acid (9), (-)-12-acetoxysydonic acid (10), (-)-12-hydroxysydonic acid (11), and (-)-(R)-11-dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15-29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA-MB-231, and HEPG2 were also evaluated.
Topics: Antifungal Agents; Antineoplastic Agents, Phytogenic; Aspergillus; Candida albicans; Cell Line, Tumor; Circular Dichroism; Drug Evaluation, Preclinical; Humans; Lichens; Magnetic Resonance Spectroscopy; Molecular Structure; Phenyl Ethers; Secondary Metabolism; Sesquiterpenes; Structure-Activity Relationship
PubMed: 25879502
DOI: 10.1002/cbdv.201400146 -
Natural Product Research Sep 2021A new indoloditerpene () and fifteen known compounds (-) were isolated from a marine-derived fungus ZZ761. Structure of the new compound was elucidated as...
A new indoloditerpene () and fifteen known compounds (-) were isolated from a marine-derived fungus ZZ761. Structure of the new compound was elucidated as (3 ,9,12,13,17,18)-2-carbonyl-3-hydroxylemeniveol based on its HRESIMS data, NMR spectroscopic analyses, the Mosher's method, and ECD calculation. This new indoloditerpene () showed antimicrobial activities with MIC values of 20.6 μM against and 22.8 μM against . Diorcinol () and versicolorin B () had activities in inhibiting the proliferation of human glioma U87MG and U251 cells with IC values of 4.4 and 6.2 μM and 11.3 and 30.5 μM, respectively.
Topics: Anti-Infective Agents; Aquatic Organisms; Aspergillus; Candida albicans; Cell Line, Tumor; Diterpenes; Humans; Phytochemicals
PubMed: 31686531
DOI: 10.1080/14786419.2019.1684281 -
The Science of the Total Environment Jan 2020Moisture-indicative microbes in buildings are associated with a variety of symptoms, ranging from mild irritation to severe clinical illnesses. These symptoms are caused...
Indoor exposure to Streptomyces albus and Aspergillus versicolor elevates the levels of spore-specific IgG, IgG1 and IgG3 serum antibodies in building users - A new ELISA-based assay for exposure assessment.
Moisture-indicative microbes in buildings are associated with a variety of symptoms, ranging from mild irritation to severe clinical illnesses. These symptoms are caused principally by dried, dormant and dead microbe material like spores, mycelium and microbe metabolites, leading to the activation of the immune system and formation of the antigen-specific immunoglobulins. This activation presumably takes place through the respiratory track and is a normal immune reaction against pathogenic invaders. During continuous exposure, a prolonged state of inflammation will follow, and this forms a considerable health risk for a building's occupant. A new ELISA system utilizing spores from two species Streptomyces albus and Aspergillus versicolor as an antigen was developed to reveal the related immunological processes. In 159 persons, microbial exposure was observed to increase the levels of spore-specific IgG, IgG1 and IgG3 serum antibody levels of individuals residing in microbe-dense buildings compared with the control reference buildings. No differences were detected in the levels of S. albus- and A. versicolor-specific serum IgA or IgM levels.
Topics: Air Microbiology; Air Pollution, Indoor; Aspergillus; Environmental Exposure; Enzyme-Linked Immunosorbent Assay; Humans; Immunoglobulin G; Spores, Fungal; Streptomyces
PubMed: 31518785
DOI: 10.1016/j.scitotenv.2019.134335