ABSTRACT
A new glyoxylate-containing benzene derivative, methyl 2-(4-hydroxy-3-(3'-methyl-2'-butenyl)phenyl)-2-oxoacetate (1), together with ten known compounds (2-11), were isolated from the marine algicolous fungus, Aspergillus sp. SCSIO 41304. Their planar structures and absolute configurations were elucidated by detailed NMR, MS spectroscopic analysis and comparing with literature data. Compound 1 was isolated as a new fungal secondary metabolite, possessing a methyl glyoxylate moiety R-CO-CO-OCH3, which is rare in natural sources. All the isolated compounds (1-11) were tested for their antibacterial and enzyme inhibitory activities against acetylcholinesterase (AChE) and pancreatic lipase (PL). Among these compounds, aspulvinone H (4) showed moderate inhibition against AChE and PL with IC50 values of 25.95 and 47.06 µM, respectively. Further molecular docking simulation exhibited that compound 4 could well bind to the catalytic pockets of the AChE and PL.
Subject(s)
Acetylcholinesterase , Aspergillus , Acetylcholinesterase/metabolism , Molecular Docking Simulation , Molecular Structure , Aspergillus/chemistry , Glyoxylates/metabolismABSTRACT
Six undescribed 4-quinolone alkaloids, including four racemic mixtures, (±)-oxypenicinolines A-D, and two related ones, penicinolines F and G, together with seven known analogues, were isolated from the mangrove-derived fungus Penicillium steckii SCSIO 41025 (Trichocomaceae). The racemates were separated by HPLC using chiral columns. Their structures including absolute configurations were elucidated by extensive spectroscopic analysis, electronic circular dichroism (ECD) experiments, and single-crystal X-ray diffraction analysis. Structurally, (±)-oxypenicinolines A-D shared with an unusual 6/6/5/5 tetracyclic system incorporating a rare tetrahydro-pyrrolyl moiety. A plausible biosynthetic pathway for pyrrolyl 4-quinolone alkaloids is proposed. (±)-oxypenicinoline A and quinolactacide displayed α-glucosidase inhibitory activity with the IC50 values of 317.8 and 365.9 µΜ, respectively, which were more potent than that of acarbose (461.0 µM). Additionally, penicinoline and penicinoline E showed weak inhibitions toward acetylcholinesterase (AChE).
Subject(s)
Alkaloids , Penicillium , 4-Quinolones , Fungi , Molecular StructureABSTRACT
Twelve indole alkaloids, including α-cyclopiazonic acid (CPA) (1), nine 2-oxo indole CPA derivatives (2-10), and two open-ring indole CPA derivatives (11 and 12), were isolated from the fermentation broth of a deep-sea derived fungus Aspergillus sp. SCSIO 41024. Their structures and absolute configurations were elucidated mainly by using extensive NMR spectroscopic, mass spectrometric and single crystal X-ray diffraction analysis. To the best of our knowledge, the crystallographic data of 3 and 7 were firstly reported, and the absolute configuration of 3 was confirmed for the first time by the single crystal X-ray diffraction analysis. Most isolated compounds were tested for their antimicrobial, antitumor and radical scavenging activities. In addition, compounds 1, 2 and 11 showed moderate antioxidative activity against DPPH with IC50 values of 190.1, 31.9, 228.4 µg/mL, respectively.
Subject(s)
Antioxidants , Indole Alkaloids , Aspergillus , Fungi , IndolesABSTRACT
One new sesquiterpenoid, 1-methoxypestabacillin B (1), along with one known sesquiterpenoid (2) and six known chrodrimanin-type meroterpenoids (3â8) were obtained from the solid cultures of a mangrove endophytic fungus Diaporthe sp. SCSIO 41011. Their structures including the absolute configuration at C-6 of compound 1, were determined by extensive spectroscopic analyses and ECD calculations. Meanwhile, the X-ray crystal structures and absolute configurations of two previously reported chrodrimanins E (3) and H (6), are described for the first time. All the compounds were examined for HIV latency-reversal and anti-influenza A virus activities.
Subject(s)
Ascomycota/chemistry , Avicennia/chemistry , Terpenes/chemistry , Crystallography, X-Ray , Fungi , Molecular Structure , Proton Magnetic Resonance Spectroscopy , Sesquiterpenes/chemistry , Spectrometry, Mass, Electrospray IonizationABSTRACT
Penicildiones A-D (1-4), four new steroids derivatives together with three known compounds including 16α-methylpregna-17α,19-dihydroxy-(9,11)-epoxy-4-ene-3,18-dione-20-acetoxy (5), stachybotrylactone B (6) and stachybotrin (7) were isolated from the soft coral-derived fungus Penicillium sp. SCSIO41201, cultured in the 1% NaCl PDB substrate. Their structures were determined through spectroscopic methods and X-ray crystallography. Biological evaluation results revealed that 6 exhibited significant cytotoxic activity against HL-60, K562, MOLT-4, ACHN, 786-O, and OS-RC-2 cell lines with IC50 values of 5.23, 4.12, 4.31, 23.55, 7.65 and 10.81 µmol·L-1, respectively, while other compounds showed weak or no cytotoxicity at 50 µmol·L-1.
Subject(s)
Penicillium/chemistry , Steroids/chemistry , Steroids/isolation & purification , Aquatic Organisms , Cell Line, Tumor , Humans , Molecular StructureABSTRACT
Two new compounds, 5-[2-hydroxypropane-1-yl]-2,6-dimethlbenzene-1,3-diol (1) and coniochaetone L (2), together with 19 known compounds (3-21), were isolated from a deep-sea fungus, Penicillium sp. SCSIO 06720. Their structures and absolute configurations were elucidated by detailed NMR, MS spectroscopic analyses, chiral-phase HPLC analysis, and electronic circular dichroism spectra. All the isolated compounds (1-21) were tested for their antibacterial and HIV latency-reversal activities. Among these compounds, compound 16 showed moderate antibacterial activities against Staphylococcus aureus ATCC 29213 and Methicillin-Resistant Staphylococcus Aureus-shh-1 with MIC values of 10.4 ± 3.7 µg/mL and 46.9 ± 29.7 µg/mL, respectively, which were comparable to that of the positive control ampicillin with MIC values of 0.5 ± 0.4 µg/mL and 2.7 ± 0.9 µg/mL, respectively.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Anti-HIV Agents/isolation & purification , Penicillium/chemistry , Polyketides/isolation & purification , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Anti-HIV Agents/chemistry , Anti-HIV Agents/pharmacology , Methicillin-Resistant Staphylococcus aureus/drug effects , Microbial Sensitivity Tests , Molecular Structure , Polyketides/chemistry , Polyketides/pharmacology , Staphylococcus aureus/drug effectsABSTRACT
A new C11-norisoprenoid derivative, sargassumone (1), has been isolated from Sargassum naozhouense together with six known norisoprenoids and a highly oxygenated cyclopentene: (2R,6S,8S,9S)-hexahydro-2,9-dihydroxy-4,4,8-trimethyl-6-acetyloxy-3(2H)-benzofuranone (2), (6S,8S,9R)-hexahydro-6,9-dihydroxy-4,4,8-trimethyl-2(2H)-benzofuranone (3), (6S,8S,9R)-hexahydro-6,9-dihydroxy-4,4,8-trimethyl-2(2H)-benzofuranone (4), loliolide (5), (+)-epiloliolide (6), spheciospongones A (7), and (+)-kjellmanianone (8). Compound 1 was identified on the basis of nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis, and the absolute stereochemistry was defined by NOESY spectroscopy, minimizing energy calculation, and circular dichroism (CD) spectra. The known compounds 2-8, isolated from S. naozhouense for the first time, were identified by comparison of their physical and spectroscopic data with those reported in the literature. Compound 6 was tested for its inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), antioxidant activity with 1,1-diphyl-2-picrylhydrazyl (DPPH) free radicals, and antimicrobial activity against resistant clinical isolates of Candida albicans, methicillin-resistant Staphylococcus aureus (MRSA), and Escherichia coli.
Subject(s)
Norisoprenoids/chemistry , Norisoprenoids/pharmacology , Sargassum/chemistry , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Circular Dichroism , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Magnetic Resonance Spectroscopy , Molecular Structure , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitorsABSTRACT
Seven new compounds, including four new chlorinated diphenyl ethers, namely chrysines A-D (1-4), one new dichlorinated xanthone, chrysoxanthone (5), dichloroorcinol (6), and one new benzeneacetic acid derivative, 3-isopentyl-4-hydroxy phenylacetic acid methyl ester (7), along with fourteen known compounds (8-21), were isolated from a deep-sea-derived fungus Penicillium chrysogenum SCSIO 41001. Their structures were determined by extensive spectroscopic methods and X-ray single-crystal diffraction analysis. All of the isolated compounds (1-21) were evaluated for their α-glucosidase inhibitory activity using PNPG method. Among them, nine compounds (2, 3, 5, 6, 8, 9, 13, 17, and 18) exhibited inhibitory activity against α-glucosidase with IC50 values of 0.35, 0.20, 0.04, 0.16, 0.15, 0.09, 0.14, 0.14, and 0.12mM, respectively (IC50 0.28mM for the positive control acarbose).
Subject(s)
Glycoside Hydrolase Inhibitors/isolation & purification , Halogenated Diphenyl Ethers/isolation & purification , Penicillium chrysogenum/chemistry , Xanthones/isolation & purification , Molecular Structure , Seawater/microbiology , alpha-GlucosidasesABSTRACT
Three new polyketides, chaetochromones A - C (1 - 3), together with a chromone (4), were isolated from the ethyl acetate extract of mangrove-derived fungus Phomopsis sp. SCSIO 41006. Their structures were elucidated by means of spectroscopic techniques (UV, IR, MS, 1D- and 2D-NMR). The absolute configurations of the new compounds were established by CD data.
Subject(s)
Fungi/metabolism , Polyketides/chemistry , Rhizophoraceae/microbiology , A549 Cells , Anti-Infective Agents/chemistry , Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Cell Line, Tumor , Cell Survival/drug effects , Chromones/chemistry , Chromones/isolation & purification , Chromones/pharmacology , Circular Dichroism , Fungi/classification , Fungi/isolation & purification , Humans , K562 Cells , Magnetic Resonance Spectroscopy , Molecular Conformation , Phylogeny , Polyketides/isolation & purification , Polyketides/pharmacology , Polyketides/toxicity , Salmonella typhi/drug effects , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Ultraviolet , Staphylococcus aureus/drug effectsABSTRACT
Ten new salicyloid derivatives, namely vaccinols J-S (1-10), along with five known compounds (11-15) were isolated from Pestalotiopsis vaccinii (cgmcc3.9199) endogenous with the mangrove plant Kandelia candel (L.) Druce (Rhizophoraceae). Their structures including absolute configurations were established on the basis of spectroscopic analysis, optical rotation, CD spectra, quantum ECD calculations. To the best of our knowledge, vaccinol J (1) is the first example of salicyloid derivatives containing 2-methylfuran moiety. All of the new compounds were tested for their anti-enterovirus 7l (EV71) and cytotoxic activities. Among them, vaccinol J (1) exhibited in vitro anti-EV71 with IC50 value of 30.7µM (IC50 177.0µM for the positive control ribavirin).
Subject(s)
Rhizophoraceae/microbiology , Salicylates/pharmacology , Xylariales/chemistry , Antiviral Agents/isolation & purification , Antiviral Agents/pharmacology , Cell Line, Tumor , Enterovirus A, Human/drug effects , Humans , Molecular Structure , Salicylates/isolation & purificationABSTRACT
Background: Non-alcoholic fatty liver disease (NAFLD) is one of the most common liver diseases in China. It is usually asymptomatic and transabdominal ultrasound (USS) is the usual means for diagnosis, but it may not be feasible to have USS screening of the whole population. Objective: To develop a risk scoring model for predicting the presence of NAFLD using parameters that can be easily obtain in clinical settings. Methods: A retrospective study on the data of 672 adults who had general health check including a transabdominal ultrasound. Fractional polynomial and multivariable logistic regressions of sociodemographic and biochemical variables on NAFLD were used to identify the predictors. A risk score was assigned to each predictor using the scaled standardized ß-coefficient to create a risk prediction algorithm. The accuracy for NAFLD detection by each cut-off score in the risk algorithm was evaluated. Results: The prevalence of NAFLD in our study population was 33.0% (222/672). Six significant factors were selected in the final prediction model. The areas under the curve (AUC) was 0.82 (95% CI: 0.78-0.85). The optimal cut-off score, based on the ROC was 35, with a sensitivity of 76.58% (95% CI: 70.44-81.98%) and specificity of 74.89% (95% CI: 70.62-78.83%). Conclusion: A NAFLD risk scoring model can be used to identify asymptomatic Chinese people who are at risk of NAFLD for further USS investigation.
Subject(s)
Body Mass Index , Non-alcoholic Fatty Liver Disease/diagnosis , Non-alcoholic Fatty Liver Disease/epidemiology , Surveys and Questionnaires , China/epidemiology , Female , Humans , Male , Middle Aged , Non-alcoholic Fatty Liver Disease/diagnostic imaging , Obesity/diagnosis , Retrospective Studies , Risk Factors , Ultrasonography/methods , Waist CircumferenceABSTRACT
Two new polyketides, aspergchromones A (1) and B (2), together with five known compounds, secalonic acid D (3), noreugenin (4), (3S)-5-hydroxymellein (5), (4S)-6-hydroxyisosclerone (6), and (-)-regiolone (7), were isolated from the ethyl acetate extract of marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. Their structures were elucidated by means of spectroscopic techniques (1D and 2D NMR, MS, UV, and IR). The absolute configurations of the new compounds were established by ECD calculations. Compound 3 showed moderate antimicrobial activity.
Subject(s)
Aspergillus/chemistry , Polyketides/isolation & purification , Porifera/microbiology , Xanthones/isolation & purification , Animals , Marine Biology , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Polyketides/chemistry , Xanthones/chemistryABSTRACT
Fifteen compounds, including six quinone/hydroquinone meroterpenoids, purpurogemutantin (1), macrophorin A (2), 4'-oxomacrophorin (3), 7-deacetoxyyanuthone A (4), 2,3-hydro-deacetoxyyanuthone A (5), 22-deacetylyanuthone A (6), anicequol (7), three roquefortine derivatives, roquefortine C (8), (16S)-hydroxyroquefortine C (9), (16R)-hydroxyroquefortine C (10), dihydroresorcylide (11), nectriapyrone (12), together with three fatty acid derivatives, methyl linoleate (13), phospholipase A2 (14), methyl elaidate (15), were isolated from the sponge-derived fungus Gliomastix sp. ZSDS1-F7 isolated from the sponge Phakellia fusca Thiele collected in the Yongxing island of Xisha. Their structures were elucidated mainly by extensive NMR spectroscopic and mass spectrometric analyses. Among these compounds, compounds 1-3 and 5-7 showed significant in vitro cytotoxicities against the K562, MCF-7, Hela, DU145, U937, H1975, SGC-7901, A549, MOLT-4 and HL60 cell lines, with IC50 values ranging from 0.19 to 35.4 µM. And compounds 2-4 exhibited antitubercular activity with IC50 values of 22.1, 2.44 and 17.5 µM, respectively. Furthermore, compound 7 had anti-enterovirus 71 activity with MIC value of 17.8 µM. To the best of our knowledge, this is the first report to product two quinone/hydroquinone meroterpenoids skeletons (linear skeleton and drimane skeleton) from the same fungal strain.
Subject(s)
Antibiotics, Antineoplastic/pharmacology , Antitubercular Agents/pharmacology , Hydroquinones/pharmacology , Mitosporic Fungi/metabolism , Porifera/microbiology , Quinones/pharmacology , Animals , Cell Line, Tumor , HumansABSTRACT
Cellular delivery is an important concern for the efficiency of medicines and sensors for disease diagnoses and therapy. However, this task is quite challenging. Self-assembly virus capsid proteins might be developed as building blocks for multifunctional cellular delivery vehicles. In this work, we found that SV40 VP1 (Simian virus 40 major capsid protein) could function as a new cell-penetrating protein. The VP1 protein could carry foreign proteins into cells in a pentameric structure. A double color structure, with red QDs (Quantum dots) encapsulated by viral capsids fused with EGFP, was created for imaging cargo delivery and release from viral capsids. The viral capsids encapsulating QDs were further used for cellular delivery of micron-sized iron oxide particles (MPIOs). MPIOs were efficiently delivered into live cells and controlled by a magnetic field. Therefore, our study built virus-based cellular delivery systems for different sizes of cargos: protein molecules, nanoparticles, and micron-sized particles. FROM THE CLINICAL EDITOR: Much research is being done to investigate methods for efficient and specific cellular delivery of drugs, proteins or genetic material. In this article, the authors describe their approach in using self-assembly virus capsid proteins SV40 VP1 (Simian virus 40 major capsid protein). The cell-penetrating behavior provided excellent cellular delivery and should give a new method for biomedical applications.
Subject(s)
Capsid Proteins/metabolism , Delayed-Action Preparations/metabolism , Ferric Compounds/administration & dosage , Fluorescent Dyes/administration & dosage , Green Fluorescent Proteins/administration & dosage , Quantum Dots/administration & dosage , Simian virus 40/metabolism , Animals , Chlorocebus aethiops , Drug Delivery Systems/methods , Ferric Compounds/analysis , Fluorescent Dyes/analysis , Green Fluorescent Proteins/analysis , Magnetic Fields , Microscopy, Fluorescence , Optical Imaging , Particle Size , Quantum Dots/analysis , Vero CellsABSTRACT
Two new phenyl derivatives (1 and 3), along with two new natural products (4 and 5), and three known compounds (2, 6 and 7), were isolated from an endophytic fungus Botryosphaeria sp. SCSIO KcF6. The structures of these compounds 1-7 were elucidated by the extensive 1D and 2D-NMR and HRESIMS Data analysis, and compared with those of reported data. The absolute configuration of the compounds 1 and 3 were assigned by optical rotation and CD data. The isolated compounds were evaluated for their cytotoxic, anti-inflammatory (COX-2) and antimicrobial activities. Compound 3 exhibited a specific COX-2 inhibitory activity with the IC50 value of 1.12 µM.
Subject(s)
Ascomycota/chemistry , Biological Products/chemistry , Biological Products/pharmacology , Drug Evaluation, Preclinical/methods , Rhizophoraceae/microbiology , Sesquiterpenes/chemistry , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Ascomycota/physiology , Biological Products/isolation & purification , Cell Line, Tumor/drug effects , Cyclooxygenase 2 Inhibitors/chemistry , Cyclooxygenase 2 Inhibitors/pharmacology , Endophytes/chemistry , Fermentation , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , Sesquiterpenes/pharmacology , WetlandsABSTRACT
Two new asteltoxins named asteltoxin E (2) and F (3), and a new chromone (4), together with four known compounds were isolated from a marine sponge-derived fungus, Aspergillus sp. SCSIO XWS02F40. The structures of the compounds (1-7) were determined by the extensive 1D- and 2D-NMR spectra, and HRESIMS spectrometry. All the compounds were tested for their antiviral (H1N1 and H3N2) activity. Compounds 2 and 3 showed significant activity against H3N2 with the prominent IC50 values of 6.2 ± 0.08 and 8.9 ± 0.3 µM, respectively. In addition, compound 2 also exhibited inhibitory activity against H1N1 with an IC50 value of 3.5 ± 1.3 µM.
Subject(s)
Antiviral Agents/pharmacology , Aspergillus/metabolism , Porifera/microbiology , Pyrones/pharmacology , Animals , Antiviral Agents/chemistry , Antiviral Agents/isolation & purification , Influenza A Virus, H1N1 Subtype/drug effects , Influenza A Virus, H3N2 Subtype/drug effects , Microbial Sensitivity Tests , Molecular Structure , Pyrones/chemistry , Pyrones/isolation & purificationABSTRACT
A new citromycetin analogue, ascomycotin A (1), together with eight known compounds, wortmannilactone E (2), orcinol (3), orsellinic acid (4), isosclerone (5), (3R,4S)-( - )-4-hydroxymellein (6), diorcinol (7), chaetocyclinone B (8) and 2,5-dimethoxy-3,6-di(p-methoxypheny1)-1,4-benzoquinone (9), was isolated from the fungal strain Ascomycota sp. Ind19F07, which was isolated from the deep sea sediment of the Indian Ocean. The structures of the compounds were established by spectroscopic data including 1D and 2D NMR and HR-ESI-MS. Compounds (1-9) were evaluated for antibacterial activity.
Subject(s)
Anti-Bacterial Agents/chemistry , Ascomycota/chemistry , Heterocyclic Compounds, 3-Ring/chemistry , Pyrones/chemistry , Anti-Bacterial Agents/isolation & purification , Geologic Sediments/microbiology , Heterocyclic Compounds, 3-Ring/isolation & purification , Indian Ocean , Molecular Structure , Pyrones/isolation & purificationSubject(s)
Anti-Bacterial Agents/pharmacology , Antiviral Agents/pharmacology , Aspergillus/metabolism , Porifera/microbiology , Sesquiterpenes/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Antiviral Agents/chemistry , Aspergillus/chemistry , Bacteria/drug effects , Influenza A Virus, H3N2 Subtype/drug effects , Microbial Sensitivity Tests , Molecular Structure , Sesquiterpenes/chemistryABSTRACT
Axinelline A, a new cyclooxygenase-2 (COX-2) inhibitor, was isolated from Streptomyces axinellae SCSIO02208. The structures of compounds 1-9 were determined by analysing the NMR and MS data. The absolute configuration of 1 was determined by using optical rotation and comparing with the reported data. Compound 1 exhibited COX-2 inhibitory activity, the IC50 value being 2.8 µM.