Marine-derived Fungus Aspergillus Versicolor Research Articles

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.

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.

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.

(±)-Brevianamides Z and Z1, New Diketopiperazine alkaloids from the marine-derived fungus Aspergillus versicolor

(±)-brevianamide Z [(±)-1] and (±)-brevianamide Z1 [(±)-2], two new pairs of diketopiperazine alkaloids, along with nine known analogues [(±)-3, (±)-4, (±)-5, 6, 7, and 8], were isolated from the marine-derived fungus Aspergillus versicolor. The structures of 1–8 including their absolute configurations were assigned based on extensive spectroscopic analysis, and calculated NMR, ECD, ORD and DP4+ methods. All the obtained compounds were evaluated for their cytotoxic, antibacterial, and antifungal activities. Among them, 7 exhibited potent cytotoxic activity against the HGC-27 cell line with an IC50 value of 4.54 µM, stronger than that of cisplatin (IC50, 8.63 µM).

Two new nucleoside derivatives isolated from the marine-derived Aspergillus versicolor and their intramolecular transesterification

Two new nucleoside derivatives, kipukasins M (1a) and N (1b), along with one known analogue, kipukasin J (2), were obtained from the marine-derived fungus Aspergillus versicolor, which was isolated from the mud collected in the South China Sea. The structures of compounds 1a and 1b were elucidated by extensive spectroscopic analysis, mainly including 1D & 2D NMR and HRESIMS data, and the absolute configuration of 1a was further confirmed by single-crystal X-ray diffraction analysis. Interestingly, intramolecular transesterification occurs in compounds 1a and 1b, which exist as a pair of inseparable regioisomers. All isolated compounds were tested for the cytotoxic and antimicrobial activities.

Alkaloids and Sesquiterpenoids from the Marine-Derived Fungus Aspergillus versicolor

Alkaloids and Sesquiterpenoids from the Marine-Derived Fungus Aspergillus versicolor

Alkaloids and Polyketides from the Marine-Derived Fungus Aspergillus versicolor

Alkaloids and Polyketides from the Marine-Derived Fungus Aspergillus versicolor

Aromatic Compounds from the Marine-Derived Fungus Aspergillus versicolor

Aromatic Compounds from the Marine-Derived Fungus Aspergillus versicolor

Epigenetic Agents Trigger the Production of Bioactive Nucleoside Derivatives and Bisabolane Sesquiterpenes From the Marine-Derived Fungus Aspergillus versicolor.

Epigenetic agents, histone deacetylase inhibitor (SAHA) and DNA methyltransferase inhibitor (5-Aza), were added to Czapek-Dox medium to trigger the chemical diversity of marine-derived fungus Aspergillus versicolor XS-20090066. By HPLC and 1H NMR analysis, the diversity of fungal secondary metabolites was significantly increased compared with the control. With the aid of MS/MS-based molecular networking, two new nucleoside derivatives, kipukasins K (1) and L (2) were obtained. Meanwhile, the yields of four known nucleoside derivatives were significantly enhanced. In addition, one new bisabolane sesquiterpene, aspergillusene E (7), along with ten known derivatives were also isolated. The structures were elucidated by comprehensive spectroscopic methods of NMR and HRESIMS analysis. Compounds 1 and 7 displayed antibacterial activities against Staphylococcus epidermidis and Staphylococcus aureus with the MIC values of 8–16 μg/mL. Our study revealed that the fungus A. versicolor XS-20090066 has been effectively induced by chemical epigenetic manipulation with a combination of SAHA and 5-Aza to produce new metabolites.

A new antimicrobial indoloditerpene from a marine-sourced fungus aspergillus versicolor ZZ761

A new indoloditerpene (1) and fifteen known compounds (2–16) were isolated from a marine-derived fungus Aspergillus versicolor ZZ761. Structure of the new compound was elucidated as (3 R,9S,12R,13S,17S,18S)-2-carbonyl-3-hydroxylemeniveol based on its HRESIMS data, NMR spectroscopic analyses, the Mosher′s method, and ECD calculation. This new indoloditerpene (1) showed antimicrobial activities with MIC values of 20.6 μM against Escherichia coli and 22.8 μM against Candida albicans. Diorcinol (2) and versicolorin B (6) had activities in inhibiting the proliferation of human glioma U87MG and U251 cells with IC50 values of 4.4 and 6.2 μM and 11.3 and 30.5 μM, respectively.

One new xanthenone from the marine-derived fungus Aspergillus versicolor MF160003

A new xanthenone derivative, 3-hydroxy pinselin (1), together with five known analogues (2–6) were isolated from the marine-derived fungus Aspergillus versicolor MF160003. Their structures were identified by extensive 1D- and 2D-NMR, and high-resolution mass spectrometry data. Compounds 5 and 6 showed moderate bioactivities against BCG with MIC values of 40 and 20 μg/mL, respectively.

Induction of Secondary Metabolites from the Marine-Derived Fungus Aspergillus versicolor through Co-cultivation with Bacillus subtilis.

A new cyclic pentapeptide, cotteslosin C (1: ), a new aflaquinolone, 22-epi-aflaquinolone B (3: ), and two new anthraquinones (9: and 10: ), along with thirty known compounds (2, 4: - 8, 11: - 34: ) were isolated from a co-culture of the sponge-associated fungus Aspergillus versicolor with Bacillus subtilis. The new metabolites were only detected in the co-culture extract, but not when the fungus was grown under axenic conditions. Furthermore, the co-culture extract exhibited an enhanced accumulation of the known constituents versicolorin B (14: ), averufin (16: ), and sterigmatocyctin (19: ) by factors of 1.5, 2.0, and 4.7, respectively, compared to the axenic fungal culture. The structures of the isolated compounds were elucidated on the basis of 1D and 2D NMR spectra and mass spectrometry as well as by comparison with literature data. The absolute configuration of compounds 3, 9: , and 10: was determined by ECD (electronic circular dichroism) analysis aided by TDDFT-ECD (time-dependent density functional theory electronic circular dichroism) calculations. Compounds 15, 18: - 21: , and 26: exhibited strong to moderate cytotoxic activity against the mouse lymphoma cell line L5178Y, with IC50 values ranging from 2.0 to 21.2 µM, while compounds 14, 16, 31, 32: , and 33: displayed moderate inhibitory activities against several gram-positive bacteria, with MIC values ranging from 12.5 to 50 µM.

Antibacterial anthraquinone dimers from marine derived fungus Aspergillus sp

As a continue investigation of the bioactive secondary metabolites from marine derived fungi, two new anthraquinone dimers (1, 2), along with three known anthraquinones (3–5) and two known xanthones (6, 7) were isolated from the marine-derived fungus Aspergillus versicolor. Their structures, including the absolute configurations, were elucidated by NMR, HRMS, and comparison with reported ones. Among them, compounds 1 and 2 were identified as anthraquinone dimers which dimerized by a rare C-O-C ether linkage, and both of them showed selective antibacterial activity against Gram-positive Staphylococcus aureus; whilst compound 6 exhibited moderate cytotoxicity against human cancer cell lines.

Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor.

Asperversiamides A-H (1-8), eight linearly fused prenylated indole alkaloids featuring an unusual pyrano[3,2- f]indole unit, were isolated from the marine-derived fungus Aspergillus versicolor. The structures and absolute configurations of these compounds were elucidated by extensive spectroscopic analyses, single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations, and optical rotation (OR) calculations. The relative configuration of C-21 of iso-notoamide B was herein revised, and a new methodology for preliminarily determining if the relative configuration of the bicyclo[2.2.2]diazaoctane moiety of a spiro-bicyclo[2.2.2]diazaoctane-type indole alkaloid is syn or anti was developed. The anti-inflammatory activities of the isolated compounds were all tested, and of these compounds, 7 exhibited a potent inhibitory effect against iNOS with an IC50 value of 5.39 μM.

Asperfurandiones A and B, two antifungal furandione analogs from a marine-derived fungus Aspergillus versicolor

Two new furandione derivatives, designated as asperfurandiones A (1) and B (2), were isolated from the solid culture of the marine-derived fungus Aspergillus versicolor. Their structures were elucidated using a combination of mass spectrometry and NMR spectroscopy. Additionally, asperfurandiones A and B both showed moderate antifungal activity against Gaeumannomyces graminis, Cryptococcus neoformans, and Candida albicans with MIC values of 64 μg/mL.

Asperversins A and B, Two Novel Meroterpenoids with an Unusual 5/6/6/6 Ring from the Marine-Derived Fungus Aspergillus versicolor.

Asperversins A (1) and B (2), two novel meroterpenoids featuring an uncommon 5/6/6/6 ring system, along with five new analogues (3–7) and a known compound asperdemin (8), were obtained from the marine-derived fungus Aspergillus versicolor. Their structures and absolute configurations were confirmed by extensive spectroscopic analyses, single-crystal X-ray diffraction studies, and electronic circular dichroism (ECD) calculation. All new compounds were tested for their acetylcholinesterase enzyme (AChE) inhibitory activities and cytotoxic activities, of which compound 7 displayed moderate inhibitory activity against the AChE with an IC50 value of 13.6 μM.

Discovery of a new biphenyl derivative by epigenetic manipulation of marine-derived fungus Aspergillus versicolor

Cultivation of the marine-derived Aspergillus versicolor MCCC 3A00080 with the addition of a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), significantly enhanced the diversity of secondary metabolites. From the culture treated, a new biphenyl derivative, named versiperol A (1), along with two known compounds, 2,4-dimethoxyphenol (2) and diorcinol (3) were isolated. The structures of 1–3 were established based on spectroscopic analysis and comparison with literature data. Among the isolates, versiperol A (1) exhibited modest inhibition of Staphylococcus aureus growth with MIC value of 8 μg/mL.

Antimicrobial activity and molecular docking studies of a novel anthraquinone from a marine-derived fungus Aspergillus versicolor

A novel anthraquinone, 2-(dimethoxymethyl)-1-hydroxyanthracene-9,10-dione (1), together with nine known compounds (2–10), were isolated from the fermentation of Aspergillus versicolor derived from deep sea sediment. Their structures were established through spectroscopic methods. Compound 1 exhibited strong inhibitory activities against MRSA ATCC 43300 and MRSA CGMCC 1.12409 (with MIC values of 3.9 and 7.8 μg/mL respectively) and moderate activities against tested strains of Vibrio (with MIC values ranging from 15.6 to 62.5 μg/mL). Compound 1 was subjected to molecular docking studies for inhibition of topoisomerase IV and AmpC β-lactamase enzymes indicating its usefulness as antimicrobial agent.

Antioxidative phenolic compounds from a marine-derived fungus Aspergillus versicolor

Bioassay-guided fractionation and chromatographic separation of a deep-sea fungus Aspergillus versicolor resulted in the isolation of 22 phenolic compounds, of which six were new natural products namely aspergilols A–F (1–6). The structures of the new compounds were determined through extensive spectroscopic analysis, including the ECD data and chemical conversion for the configurational assignment. Aspergilols A and B presented as a new scaffold with a C–C fusion of an anthraquinone and orcinol unit. The trolox equivalent antioxidant capacity (TEAC) assay indicated most of the phenolic compounds possessing antioxidant activities, while four compounds (12, 14, 21, and 22) exerted strong free-radical scavenging effects with the TEAC values around five folds more than trolox. In addition, an Nrf2-dependent luciferase reporter gene assay revealed that compounds 12–14 and 17–18 potentially activated the expression of Nrf2-regulated gene. The primary structure–activity relationship was discussed. These findings provided the evidence that the deep-sea derived microorganisms are the promising and new source for the discovery of antioxidant agents.