Fungus Aspergillus Versicolor Research Articles

Two new types of structures from soft coral-associated epiphytic fungus Aspergillus versicolor CGF9-1-2

Global Natural Products Social (GNPS) molecular networking platform was applied to discovery the undescribed compounds from the common marine fungi Aspergillus versicolor CGF9-1-2, ultimately resulting in isolation of four new polyketides, decumbenone E (1), decumbenone F (2), 2′-epi-8-O-methylnidurufin (6), (−)-phomoindene A (7), one new nucleoside, 3-methyl-9-(2-methylbutene)-xanthine (8), and five known analogues. Their structures were elucidated based on 1D/2D NMR spectroscopic and HRESIMS data analyses, meanwhile, the absolute configurations of new compounds were established based on the X-ray crystallographic experiments, as well as the electronic circular dichroism (ECD) analysis. All compounds were predicted pharmaceutical chemistry with ten commonly disease-related proteins by molecular docking. In addition, all compounds against TDP1 were performed in vitro, which was consistent with the docking result, and compound 6 shown a weak inhibitory activity.

Isolation, identification and screening of Polyurethane polymer degrading microbe isolated from contaminated site

The objective of this research was to isolate soil-based bacteria that may destroy polyurethane (PU). PU plays a crucial role in many parts of our daily life. Polyurethanes are a significant and adaptable group of synthetic polymers utilized in a wide range of industrial, automotive and medical sectors. Due of its widespread use and challenges in recycling or reusing, PU primarily becomes garbage. PU has been observed to be degraded by a variety of bacteria and fungi. The objective of this study was to isolate polyurethane degrading microbes from the soil sample. Two bacteria Bacillus subtilis and Pseudomonas aeruginosa and three fungi Aspergillus versicolor, Aspergillus fumigatus and Aspergillus Niger, were isolated and identified from the soil sample based on morphological and biochemical characteristics. In this study, the fungus Aspergillus versicolor shows the high degradation percentage on polyurethane film. Scanning electron microscopy and ATR-FTIR were used in this study to evaluate the surface and chemical alterations of PU.

Citriquinolinones A and B: Rare Isoquinolinone-Embedded Citrinin Analogues and Related Metabolites from the Deep-Sea-Derived Aspergillus versicolor 170217.

A systematic chemical investigation of the deep-sea-derived fungus Aspergillus versicolor 170217 resulted in the isolation of six new (1-6) and 45 known (7-51) compounds. The structures of the new compounds were established on the basis of exhaustive analysis of their spectroscopic data and theoretical-statistical approaches including GIAO-NMR, TDDFT-ECD/ORD calculations, DP4+ probability analysis, and biogenetic consideration. Citriquinolinones A (1) and B (2) feature a unique isoquinolinone-embedded citrinin scaffold, representing the first exemplars of a citrinin-isoquinolinone hybrid. Dicitrinones K-L (3-4) are two new dimeric citrinin analogues with a rare CH-CH3 bridge. Biologically, frangula-emodin (32) and diorcinol (17) displayed remarkable anti-food allergic activity with IC50 values of 7.9 ± 3.0 μM and 13.4 ± 1.2 μM, respectively, while diorcinol (17) and penicitrinol A (20) exhibited weak inhibitory activity against Vibrio parahemolyticus, with MIC values ranging from 128 to 256 μM.

New Indole Diketopiperazine Alkaloids from Soft Coral-Associated Epiphytic Fungus Aspergillus versicolor CGF 9-1-2.

Two new indole diketopiperazine alkaloids (IDAs), (+)19-epi-sclerotiamide (1) and (-)19-epi-sclerotiamide (2), along with 13 known analogs (3-15), were isolated from a soft coral-associated epiphytic fungus Aspergillus versicolor CGF 9-1-2. The structures of two new compounds were established based on the combination of HR-ESI-MS, 1D and 2D NMR spectroscopy, optical rotation measurements and quantum chemical 13 C-NMR, the absolute configurations were determined by experimental and electronic circular dichroism (ECD) calculations. The results of molecular docking showed that all the compounds had a good binding with TDP1, TDP2, TOP1, TOP2, Ache, NLRP3, EGFR, EGFR L858R, EGFR T790M and EGFR T790/L858. Biological evaluation of compounds 3, 6, 8, 11 showed that 3 exerted a strong inhibitory effect on TDP2 with a rate of 81.72 %.

Chromones from the Tobacco Derived Fungus Aspergillus versicolor and Their Antiviral Activity

Chromones from the Tobacco Derived Fungus Aspergillus versicolor and Their Antiviral Activity

Bioactive Metabolite from Endophytic Aspergillus versicolor SB5 with Anti-Acetylcholinesterase, Anti-Inflammatory and Antioxidant Activities: In Vitro and In Silico Studies.

Endophytic fungi are a highly unpredictable group of microorganisms that can create a diverse range of secondary metabolites with biological activity. These metabolites enhance the host's ability to tolerate stress caused by various factors, such as disease, insects, pathogens, and herbivores. The secondary metabolites produced by endophytic fungi may have potential applications in agriculture, pharmacy, and medicine. The purpose of this study was to examine the anti-acetylcholinesterase activity of secondary metabolites extracted from endophytic fungi. Aspergillus versicolor SB5 was one of the many endophytic fungi isolated from Juncus rigidus and identified genetically with accession number ON872302. Our study utilized fermentation and microbial cultivation techniques to obtain secondary metabolites. During the course of our investigation, we isolated a compound called Physcion (C1) from the endophytic fungus Aspergillus versicolor SB5. We subsequently identified that C1 possesses inhibitory activity against COX-2 and LOX-1, with IC50 values of 43.10 and 17.54 µg/mL, respectively, making it an effective anti-inflammatory agent. Moreover, we found that C1 also exhibited potent anticholinesterase activity (86.9 ± 1.21%). In addition to these promising therapeutic properties, our experiments demonstrated that C1 possesses strong antioxidant capacity, as evidenced by its ability to scavenge DPPH, ABTS, O2 radicals, and NO and inhibit lipid peroxidation. To further investigate the molecular mechanisms underlying C1 pharmacological properties, we employed SwissADME web tools to predict the compound's ADME-related physicochemical properties and used Molecular Operating Environment and PyMOL for molecular docking studies.

Secondary metabolites from the Cordyceps-colonizing fungus Aspergillus versicolor ZJUTE2

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 IC50 values of 54.73 ± 2.69 and 56.59 ± 1.77 μM, respectively.

Structure Revisions of Phenolic Bisabolane Sesquiterpenes and a Ferroptosis Inhibitor from the Marine-Derived Fungus Aspergillus versicolor YPH93.

Seven new phenolic bisabolane sesquiterpenoids (1-7), along with 10 biogenetically related analogues (8-17), were obtained from the deep-sea-derived fungus Aspergillus versicolor YPH93. The structures were elucidated based on extensive analyses of the spectroscopic data. Compounds 1-3 are the first examples of phenolic bisabolanes that contain two hydroxy groups attached to the pyran ring. The structures of sydowic acid derivatives (1-6 and 8-10) were carefully studied, leading to the structure revisions of six known analogues, including a revision of the absolute configuration for sydowic acid (10). All metabolites were evaluated for their effects on ferroptosis. Compound 7 exerted inhibition on erastin/RSL3-induced ferroptosis with EC50 values ranging from 2 to 4 μM, while it exhibited no effects on TNFα-induced necroptosis or H2O2-induced cell necrosis.

Kojicone C, new anti-inflammatory polyketide from insect-associated fungus Aspergillus versicolor

The chemical study of EtOAc extracts of the insect-associated fungus Aspergillus versicolor led to the isolation of a new polyketide kojicone C ( 1 ) and its precursor (2 R ,4 R )−4-hydroxy-5-methoxy-2,4-dimethyl-2-[(2 R )−2-methylbutyryloxy]−5-cyclohexen-1,3-dione ( 2 ). Kojicone C belongs to the rare tricycle cyclohexen-1,3-dione adduct class. The structures of 1 and 2 were determined by HRESIMS (high resolution electrospray ionization mass spectroscopy) data, 1D and 2 D NMR (nuclear magnetic resonance) spectroscopic analysis, ECD (electronic circular dichroism) calculations, and CD exciton chirality method. Compound 1 exhibited moderate anti-inflammatory activities that reduced LPS-induced NO production of RAW 264.7 cells (IC 50 = 35.8 μ Μ). It could also significantly inhibit LPS-induced mRNA expression of TNF- α , IL-1 β , and IL-6 of this cell line at a concentration of 20 μ Μ. • One new polyketide was isolated from Aspergillus versicolor . • The new compound is a rare tricycle cyclohexen-1,3-dione adduct. • The new compound exhibited potent anti-inflammatory activities.

Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog, asperpyrroindotide A, using LC–MS/MS-based molecular networking

Further insights on the secondary metabolites of a soft coral-derived fungus Aspergillus versicolor under the guidance of MS/MS-based molecular networking led to the isolation of seven known cycloheptapeptides, namely, asperversiamides A–C (1–3) and asperheptatides A–D (4–7) and an unusual pyrroloindoline-containing new cycloheptapeptide, asperpyrroindotide A (8). The structure of 8 was elucidated by comprehensive spectroscopic data analysis, and its absolute configuration was determined by advanced Marfey’s method. The semisynthetic transformation of 1 into 8 was successfully achieved and the reaction conditions were optimized. Additionally, a series of new derivatives (10−19) of asperversiamide A (1) was semi-synthesized and their anti-tubercular activities were evaluated against Mycobacterium tuberculosis H37Ra. The preliminary structure−activity relationships revealed that the serine hydroxy groups and the tryptophan residue are important to the activity.

Structural characterization and immunomodulatory activity of an exopolysaccharide from marine-derived Aspergillus versicolor SCAU141

Until now, relatively little is known about marine-derived fungal polysaccharides and their activities. Exopolysaccharide AVP141-A was isolated from the broth of marine-derived fungus Aspergillus versicolor SCAU141 and purified by Diethylaminoethyl-Sepharose Fast Flow and Sephadex G-100. The structural characteristics of AVP141-A was studied by chemical analysis together with high-performance gel permeation chromatography, ion chromatography, Fourier-transform infrared spectroscopy, gas chromatography–mass spectrometry and nuclear magnetic resonance spectroscopy. The results showed that AVP141-A with the molecular weight of 5.10 kDa was mainly composed of →4)-α-D-Glcp-(1→, branched by α-D-Glcp-(1→ and →6)-α-D-Glcp-(1→ at C-6 positions of the glucan backbone. In particular, sulfate ester (approximately 3.62 %) was found in AVP141-A, which was frequently considered to occur in marine-derived microbial polysaccharides rather than other microbial polysaccharides. Furthermore, AVP141-A significantly enhanced the activity of the inflammatory factors NO, COX-2 and TNF-α in RAW264.7 macrophages by activating the MAPK/p38 and NF-κB/p65 pathways. In addition, metabolomic analysis revealed that most of the pathways with significant changes in RAW264.7 macrophages treated with AVP141-A were amino acid-related pathways, and arginine was the characteristic metabolite. In conclusion, this study identified AVP141-A as a marine fungus-derived sulfated exopolysaccharide with potential for development as an immune activator.

The anti-TMV potency of the tobacco-derived fungus Aspergillus versicolor and its active alkaloids, as anti-TMV activity inhibitors

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 IC50 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.

Two New Anthraquinones from the Cigar Tobacco-Derived Fungus Aspergillus versicolor and Their Bioactivities

Two New Anthraquinones from the Cigar Tobacco-Derived Fungus Aspergillus versicolor and Their Bioactivities

Two New CPA-Type Indole Alkaloids from the Tobacco-Derived Fungus Aspergillus versicolor and the Anti-TMV Activity

Two New CPA-Type Indole Alkaloids from the Tobacco-Derived Fungus Aspergillus versicolor and the Anti-TMV Activity

Discovery of a novel jellyfish venom metalloproteinase inhibitor from secondary metabolites isolated from jellyfish-derived fungus Aspergillus versicolor SmT07

The major jellyfish stings that occur in China are caused by scyphozoan Nemopilema nomurai, whose venom exhibits significant metalloproteinase activity that contributes to the toxic effects of jellyfish envenomation. Researching effective inhibitors suppressing the metalloproteinase activity of jellyfish venom represents a new attempt to cure jellyfish envenomations. In the present study, secondary metabolites produced by the jellyfish-associated fungus Aspergillus versicolor SmT07 were isolated and evaluated for their anti-proteolytic activities. Two xanthones, sterigmatocystin (JC-01) and oxisterigmatocystin C (JC-06), and four alkaloids, cottoquinazoline A (JC-02), phenazine-1-carboxylic acid (JC-03), viridicatin (JC-04) and viridicatol (JC-05), were isolated and identified. Only phenazine-1-carboxylic acid (PCA) showed significant anti-proteolytic activity of jellyfish venom assayed on azocasein, and the IC50 value was 2.16 mM. PCA also significantly inhibited fibrinogenolytic activity, protecting the Bβ chain of fibrinogen from degradation when preincubated with jellyfish venom at a ratio of >1:0.6 (PCA:venom, w/w). Molecular docking with several well-characterized snake venom metalloproteinases suggested the venom metalloproteinases inhibitory property of PCA by forming complex interactions with the active site via hydrogen bonds, π-π stacking and salt bridges, which was distinct from the binding mode of batimastat. The present study represents the first study identifying natural jellyfish venom metalloproteinase inhibitors from marine natural products, which may provide an alternative to develop therapeutic agents for treating jellyfish envenomations.

Isochromenes from the Nicotiana tabacum-derived endophytic fungus Aspergillus versicolor and their anti-tobacco mosaic virus activities

Three new isochromenes, (5-methoxy-7-prenyl-1H-isochromen-3-yl)methanol (1), 3-(3-(hydroxymethyl)-5-methoxy-1H-isochromen-7-yl)propan-1-ol (2), and (5-methoxy-7-methyl-1H-isochromen-3-yl)methanol (3), along with three known analogues (4–6) were isolated from the fermentation products of a Nicotiana tabacum-derived endophytic fungus Aspergillus versicolor. Their structures were elucidated by spectroscopic methods, including extensive 1 D and 2 D NMR techniques. Compounds 1–3 and 6 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compound 2 exhibited high anti-TMV activity with inhibition rate of 46.4%, and this rate is higher than that of positive control. Compounds 1, 3, and 6 also showed potential anti-TMV activity with inhibition rates of 28.6, 30.5, and 26.2%, respectively. The IC50 of compounds 1–3 and 6 were also tested, and showed IC50 values of 49.3, 22.4, 42.2, and 54.1 µM, respectively.

Cyclopeptides Natural Products as Herbicides and Inhibitors of Cyanobacteria: Synthesis of Versicotides E and F

AbstractThe first total synthesis of cyclopeptides versicotide E and F, natural products produced by marine fungus Aspergillus versicolor LZD‐14‐1, was achieved in good yield by solid phase peptide synthesis (SPPS) of their linear precursors and solution phase cyclization. All the versicotides A−F were evaluated as herbicides and inhibitors of cyanobacterial growth. Versicotides A, B, D, E and F showed a significant inhibition of Rye grass seed's radicle growth at a concentration of 67 μg/mL. Versicotides A, B and D also inhibited seed germination and leaf development. On the other hand, Versicotides D and F caused a relevant reduction on Microcystis aeruginosa population when cultures on exponential growth were incubated with 40 μg/mL solutions of these compounds. Evaluation of the concentration of microcystins after these treatments showed that versicotide D inhibited the production of microcystins in a comparable extent to the positive control, colistine. These results indicate versicotides, with versicotides D and F as top hits, could be considered as lead candidates in the development of bioherbicides able to mitigate the environmental impact that the evolution of agriculture has had on water quality.

Aspergillines K and L, Two New Anti-TMV Indole Alkaloids from Fungus Aspergillus versicolor Derived from Tobacco

Aspergillines K and L, Two New Anti-TMV Indole Alkaloids from Fungus Aspergillus versicolor Derived from Tobacco

A Novel Bi-Functional Fibrinolytic Enzyme with Anticoagulant and Thrombolytic Activities from a Marine-Derived Fungus Aspergillus versicolor ZLH-1.

Fibrinolytic enzymes are important components in the treatment of thrombosis-associated disorders. A new bi-functional fibrinolytic enzyme, versiase, was identified from a marine-derived fungus Aspergillus versicolor ZLH-1. The enzyme was isolated from the fungal culture through precipitation with ammonium sulfate at 90% saturation. Additionally, it was further purified by DEAE-based ion-exchange chromatography, with a recovery of 20.4%. The fibrinolytic enzyme presented as one band on both SDS-PAGE and fibrin-zymogram, with a molecular mass of 37.3 kDa. It was elucidated as a member of metalloprotease in M35 family by proteomic approaches. The homology-modeling analysis revealed that versiase shares significant structural homology wuth the zinc metalloendopeptidase. The enzyme displayed maximum activity at 40 °C and pH 5.0. The activity of versiase was strongly inhibited by the metalloprotease inhibitors EDTA and BGTA. Furthermore, versiase hydrolyzed fibrin directly and indirectly via the activation of plasminogen, and it was able to hydrolyze the three chains (α, β, γ) of fibrin(ogen). Additionally, versiase demonstrated promising thrombolytic and anticoagulant activities, without many side-effects noticed. In conclusion, versiase appears to be a potent fibrinolytic enzyme deserving further investigation.

Homo/Hetero-Dimers of Aromatic Bisabolane Sesquiterpenoids with Neuroprotective Activity from the Fungus Aspergillus versicolor A18 from South China Sea

Chromatographic fractionation of the EtOH extracts of the marine-derived fungus Aspergillus versicolor A18 has led to the isolation of 11 homo/hetero-dimers of aromatic bisabolane sesquiterpenoids including eight diphenyl ether-coupled aromatic bisabolanes (1a/1b and 5–10) and three homodimers (2–4), together with their monomers including three aromatic bisabolanes (11–13) and two diphenyl ethers (14 and 15). Their structures and absolute configurations were elucidated by extensive spectroscopic analysis including HRESIMS, 1D/2D NMR, calculated ECD, and the optical rotatory data. Among the four new compounds, (+/−)-asperbisabol A (1a/1b), asperbisabol B (2), and asperbisabol C (3), the enantiomers 1a and 1b represent an unprecedented skeleton of diphenyl ether-coupled aromatic bisabolane sesquiterpenoids with a spiroketal core moiety. The neuroprotective effects of selected compounds against sodium nitroprusside (SNP)-induced injury were evaluated in PC12 cells by the MTT assay. Five compounds (1a, 6, and 8–10) showed remarkable neuroprotective activities at 10 μM, being more active than the positive control edaravone.