ABSTRACT
Six new isocoumarin derivative talaromarins A-F (1-6), along with 17 known analogues (7-23), were isolated from the mangrove-derived fungus Talaromyces flavus (Eurotiales: Trichocomaceae) TGGP35. Their structures were identified by detailed IR, UV, 1D/2D NMR and HR-ESI-MS spectra. The absolute configurations of new compounds were determined by the modified Mosher's method and a comparison of their CD spectra with dihydroisocoumarins described in the literature. The antioxidant, antibacterial, anti-phytopathogenic and inhibitory activity against α-glucosidase of all the isolated compounds were tested. Compounds 6-11, 17-19 and 21-22 showed similar or better antioxidant activity than the IC50 values ranging from 0.009 to 0.27 mM, compared with the positive control trolox (IC50 = 0.29 mM). Compounds 10, 18, 21 and 23 exhibited strong inhibitory activities against α-glucosidase with IC50 values ranging from 0.10 to 0.62 mM, while the positive control acarbose had an IC50 value of 0.5 mM. All compounds showed no antibacterial or anti-phytopathogenic activity at the concentrations of 50 µg/mL and 1 mg/mL, respectively. These results indicated that isocoumarins will be useful to developing antioxidants and as diabetes control agents.
Subject(s)
Talaromyces , alpha-Glucosidases , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Isocoumarins/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Talaromyces/chemistry , alpha-Glucosidases/metabolismABSTRACT
A new isocoumarin, penicimarin N (1), along with five known compounds (2-6), were isolated from the mangrove-derived fungus Penicillium sp. TGM112. The structure of 1 was elucidated on the basis of extensive spectroscopic data analysis, and the absolute configuration of 1 was determined by comparison of their circular dichroism (CD) spectra with the literature. The structures of known compounds were determined by comparison with the literature data. All the isolated compounds were examined for their antioxidant and α-glucosidase activities. Compound 1 showed strong antioxidant activity with the IC50 value of 1.0 mM, and 1 also exhibited moderate inhibitory activity against α-glucosidase with the IC50 value of 620 µM.
Subject(s)
Isocoumarins , Penicillium , Fungi/metabolism , Molecular Structure , Penicillium/chemistry , alpha-Glucosidases/metabolismABSTRACT
Two new isocoumarins penicimarins L-M (1-2), along with seven known analogues (3-9) were isolated from the mangrove-derived fungus Penicillium sp. MGP11. Compounds 1-2 were established by spectroscopic methods and comparison of their circular dichroism (CD) spectra with the literature. All isolated compounds were evaluated for antioxidant and α-glucosidase inhibitory activities. Compound 8 had better antioxidant activity (IC50 = 4.6 µM) than positive control trolox (IC50 = 12.9 µM). Compounds 5, 8 and 9 exhibited α-glucosidase inhibitory activity with the IC50 values of 776.5, 683.7 and 868.7 µM, respectively.[Formula: see text].
Subject(s)
Penicillium , Fungi , Isocoumarins/chemistry , Molecular Structure , Penicillium/chemistryABSTRACT
A new phenol derivative, 3-chloro-5-hydroxy-4-methoxyphenylacetic acid methyl ester (1), along with five known compounds methyl 4-hydroxyphenylacetate (2), cytosporone B (3), (R)-striatisporolide A (4), (R)-butanedioic acid (5) and ergosterol (6) were isolated from the mangrove-derived fungus Eupenicillium sp. HJ002. Their structures were established by spectroscopic methods, GIAO based 13C NMR chemical shift calculations and comparison with the data of literature. Compounds 1-5 were isolated from Xylocarpus granatum Koening-derived fungus for the first time.
Subject(s)
Eupenicillium , Meliaceae , Fungi , Molecular Structure , PhenolABSTRACT
A new α,ß-unsaturated 7-ketone sterol, 5ß,6ß-epoxy-3ß, 15α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-7-one (1), along with five known sterone derivatives, 5ß,6ß-epoxy-3ß,7α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (2), 5ß,6ß-epoxy-3ß,7α,9α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (3), 3ß,9α,15α-trihydroxy-(22E,24R)-10(5â4)-abeo-ergosta-6,8(14),22-trien-5-one (4), 3,15-dihydroxyl-(22E,24R)-ergosta-5,8(14),22-trien-7-one (5) and (22E,24R)-ergosta-4,6,8(14),22-tetraen-3,15-dione (6) were isolated from the mangrove-derived fungus Phomopsis sp. MGF222. Their structures were established on the basis of extensive spectroscopic data and comparison with the data of literature. Compound 2 showed weak antibacterial activity against Micrococcus tenuis with the MIC value of 28.2 (±0.52) µM. Compound 5 exhibited moderate antibacterial activity against Staphylococcus aureus with the MIC value of 14.6 (±0.47) µM.
Subject(s)
Phomopsis , Rhodophyta , Fungi , Ketones , Molecular Structure , Sterols/pharmacologyABSTRACT
Two new polyketides, 8-O-methylnodulisporin F (1) and nodulisporin H (2), two new naphthoquinones, 5-hydroxy-2-methoxy-6,7-dimethyl-1,4-naphthoquinone (3) and 5-hydroxy-2-methoxynaphtho[9-c]furan-1,4-dione (4), and a new naphthofuran 1,3,8-trimethoxynaphtho[9-c]furan (5), along with five known compounds 4-O-methyl eleutherol (6), 2-acetyl-7-methoxybenzofuran (7), (-)-orthosporin (8), diaporthin (9), and 6-hydroxymellein (10), were obtained from the EtOAc extract of the mangrove-derived fungus Daldinia eschscholtzii HJ004. The structures of the isolated compounds were elucidated by extensive NMR and MS analyses, while the absolute configurations of the stereogenic carbons were established based on experimental and calculated electronic circular dichroism spectra. Compounds 4 and 7 displayed a potent inhibitory activity against α-glucosidase with the IC50 values of 5.7 and 1.1 µg/mL, respectively. Compounds 1 and 2 showed a moderate antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus (MRSA) and Bacillus cereus, with minimum inhibitory concentration (MIC) values ranging from 6.25 to 12.5 µg/mL. Compound 3 exhibited antibacterial activity against B. cereus with the MIC value of 12.5 µg/mL.
Subject(s)
Fungi/metabolism , Heterocyclic Compounds/chemistry , Rhizophoraceae/microbiology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Fungi/chemistry , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Heterocyclic Compounds/metabolism , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular StructureABSTRACT
Five new tetralones, daldiniones A-E (1-5), three new chromones, 7-hydroxy-5-methoxy-2,3-dimethylchromone (9), 5-methoxy-2-propylchromone (10), and 7-ethyl-8-hydroxy-6-methoxy-2,3-dimethylchromone (11), and two new lactones, helicascolides D and E (16 and 17), together with nine known metabolites (6-8, 12-15, and 18-19) were isolated from the mangrove-derived fungus Daldinia eschscholtzii HJ004. The structures and absolute configurations of the new compounds were determined by analyzing MS and NMR data and utilizing GIAO based 13C NMR chemical shift calculations and quantum chemical electronic circular dichroism (ECD) calculations. Compounds 9, 13, and 18 showed inhibitory activities against α-glucosidase with IC50 values of 13, 15, and 16 µM, respectively.
Subject(s)
Avicennia/chemistry , Polyketides/isolation & purification , Xylariales/chemistry , Avicennia/microbiology , Molecular Structure , Polyketides/chemistry , Spectrum Analysis/methods , Xylariales/isolation & purificationABSTRACT
Three new lactones penicilactones A-C (1-3) were obtained from the mangrove-derived fungus Penicillium sp. TGM112. Their structures and absolute configurations were determined by detailed NMR, MS spectroscopic data, Mo2(OAc)4-induced electronic circular dichroism (ECD), and circular dichroism (CD) spectroscopy. Compound 1 showed antibacterial activity against Staphylococcus aureus with an MIC value of 6.25 µg/mL. Compound 2 showed insecticidal activity against newly hatched larvae of Culex quinquefasciatus with the LC50 value of 78.5 (±0.58) µg/mL.
Subject(s)
Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Insecticides/chemistry , Insecticides/pharmacology , Lactones/chemistry , Lactones/pharmacology , Penicillium/chemistry , Animals , Circular Dichroism/methods , Culex/drug effects , Magnetic Resonance Spectroscopy/methods , Microbial Sensitivity Tests/methods , Staphylococcus aureus/drug effectsABSTRACT
Two new meroterpenoids, penicianstinoids A and B (1 and 2), and eight new isocoumarins, peniciisocoumarins A-H (3-10), together with 10 known analogues (11-20) were obtained from the mangrove-derived fungus Penicillium sp. TGM112. The structures and absolute configurations of 1-10 were determined by interpretation of detailed NMR, MS spectroscopic data, X-ray diffraction analyses, modified Mosher's method, and calculated electronic circular dichroism data. Compounds 1-4, 7, 8, 10, 12, 13, and 16 showed growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner with IC50 values ranging from 50 to 200 µg/mL, respectively. Compounds 1, 2, and 11-15 displayed activity against Caenorhabditis elegans with EC50 values ranging from 9.4 (± 1.0) to 38.2 (± 0.6) µg/mL, respectively. Compound 1 represents an austinoid-like meroterpenoid that is reported here for the second time, in which a carbon-carbon double bond was oxidized to a carbonyl group at C-1'-C-2'.
Subject(s)
Isocoumarins/isolation & purification , Penicillium/chemistry , Rhizophoraceae/microbiology , Terpenes/isolation & purification , Cell Line, Tumor , Humans , Isocoumarins/chemistry , Isocoumarins/pharmacology , Magnetic Resonance Spectroscopy , Terpenes/chemistry , Terpenes/pharmacologyABSTRACT
Three new cytosporone derivatives dothiorelones K-M (1, 2 and 7), together with six known ones (3-6, 8 and 9) were isolated from the mangrove-derived fungus Dothiorella sp. ML002. Their structures were determined by comprehensive 1D, 2D NMR spectroscopic and HR-ESI-MS spectroscopic data. Compounds 1, 2 and 5 displayed inhibitory activities against α-glucosidase with the IC50 values of 22.0, 77.9 and 5.4⯵g/mL, respectively. Additionally, compounds 1, 2, and 5 also exhibited antibacterial activities against Staphylococcus aureus (ATCC 6538) with the same MIC values of 50⯵g/mL, respectively. The results indicated that cytosporone derivatives will be useful to as diabetes control agents.
Subject(s)
Ascomycota/chemistry , Benzopyrans/pharmacology , Resorcinols/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/toxicity , Benzopyrans/isolation & purification , Benzopyrans/toxicity , Cell Line, Tumor , Glycoside Hydrolase Inhibitors/isolation & purification , Glycoside Hydrolase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/toxicity , Humans , Microbial Sensitivity Tests , Resorcinols/isolation & purification , Resorcinols/toxicity , Staphylococcus aureus/drug effectsABSTRACT
Two new compounds penibenzophenones A-B (1-2), and the synthetic α,ß-unsaturated amide alkaloid (E)-tert-butyl(3-cinnamamidopropyl)carbamate (4), newly identified as a natural product, alone with three known ones (3, 5-6) were isolated from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Compound 1 was a chlorinated benzophenone. The structures of 1-6 were elucidated by extensive NMR spectral interpretation, MS data and X-ray analysis. The new compound 2 displayed cytotoxic activity against human A549 cell lines with an IC50 value of 15.7 µg/mL, and 1 showed antibacterial activity against Staphylococcus aureus with a MIC value of 20 µg/mL.
Subject(s)
Alkaloids/pharmacology , Anti-Bacterial Agents/pharmacology , Benzophenones/pharmacology , Penicillium/chemistry , A549 Cells , Alkaloids/chemistry , Alkaloids/isolation & purification , Amides/chemistry , Anti-Bacterial Agents/isolation & purification , Benzophenones/isolation & purification , Crystallography, X-Ray , Drug Evaluation, Preclinical/methods , Endophytes/chemistry , Humans , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Rhizophoraceae/microbiology , Staphylococcus aureus/drug effects , WetlandsABSTRACT
Three new indole diterpenes, penicilindoles A-C (1-3), were isolated from the mangrove-derived fungus Eupenicillium sp. HJ002. Their planar structures and absolute configurations were determined by interpretation of NMR spectroscopic data, HR-ESIMS, and X-ray diffraction analysis using Cu Kα radiation. The cytotoxic and antibacterial activities were evaluated in vitro; penicilindole A (1) showed cytotoxic activity against human A549 and HepG2 cell lines with IC50 values of 5.5 and 1.5 µM, respectively.
Subject(s)
Cytotoxins/pharmacology , Diterpenes/pharmacology , Eupenicillium/chemistry , Rhizophoraceae/microbiology , A549 Cells , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Cell Line, Tumor , Crystallography, X-Ray , Cytotoxins/chemistry , Diterpenes/chemistry , Fungi , HeLa Cells , Hep G2 Cells , Humans , Indoles/chemistry , Indoles/pharmacology , Magnetic Resonance Spectroscopy/methods , Penicillium/chemistryABSTRACT
One new cytochalasin metabolite [11]-cytochalasa-5(6),13-diene-1,21-dione-7,18-dihydroxy-16,18-dimethyl-10-phenyl-(7S*,13E,16S*,18R*) (1), together with three known compounds (2-4) were obtained from the EtOAc extract of the endophytic fungus Daldinia eschscholtzii HJ001 isolated from the mangrove Brguiera sexangula var. rhynchopetala collected in the South China Sea. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compounds 1 and 2 were evaluated for their antibacterial and cytotoxic activities.
Subject(s)
Cytochalasins/chemistry , Xylariales/metabolism , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Cytochalasins/metabolism , Cytochalasins/pharmacology , Endophytes/chemistry , Endophytes/metabolism , Hep G2 Cells , Humans , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Wetlands , Xylariales/chemistryABSTRACT
Two new chlorinated metabolites 4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one (1) and 2'-acetoxy-7-chlorocitreorosein (2), together with three known compounds (3-5), were obtained from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. All compounds were evaluated for their antibacterial and topoisomerase I inhibitory activities. Compound 2 exhibited antibacterial activity against Vibrio parahaemolyticus with an MIC value of 10 µm.
Subject(s)
Anthraquinones/isolation & purification , Penicillium/metabolism , Rhizophoraceae/microbiology , Xanthones/isolation & purification , Anthraquinones/chemistry , Anthraquinones/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Microbial Sensitivity Tests , Penicillium/isolation & purification , Spectrum Analysis , Topoisomerase I Inhibitors/chemistry , Topoisomerase I Inhibitors/isolation & purification , Topoisomerase I Inhibitors/pharmacology , Vibrio parahaemolyticus/drug effects , Xanthones/chemistry , Xanthones/pharmacologyABSTRACT
Three new dihydroisocoumarin penicimarins G-I (1-3), together with one known dihydroisocoumarin (4) and three known meroterpenoids (5-7), were obtained from a fungus Penicillium citrinum isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Their structures were elucidated by the detailed analysis of spectroscopic data. The absolute configuration of 1 was determined by the X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of 2 and 3 were determined by comparison of their circular dichroism (CD) spectra with the literature. All compounds were evaluated for their antibacterial activities and cytotoxic activities.
Subject(s)
Coumarins/chemistry , Penicillium/chemistry , Rhizophoraceae/microbiology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antibiotics, Antineoplastic/chemistry , Antibiotics, Antineoplastic/pharmacology , Bacteria/drug effects , Cell Line, Tumor , Circular Dichroism , Coumarins/pharmacology , Humans , Microbial Sensitivity Tests , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Spectrometry, Mass, Electrospray Ionization , X-Ray DiffractionABSTRACT
One new benzopyran derivative (2R(*),4R(*))-3,4-dihydro-5-methoxy-2-methyl-2H-1-benzopyran-4-ol (1), together with five known compounds (2-6), were obtained from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Brguiera sexangula var. rhynchopetala collected in the South China Sea. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. All compounds were evaluated for their antibacterial activities. Compound 6 exhibited potent inhibitory activity against Bacillus subtilis, Bacillus cereus and Micrococcus tetragenus with the same MIC values of 6.94 µM.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Benzopyrans/isolation & purification , Penicillium/chemistry , Rhizophoraceae/microbiology , Anti-Bacterial Agents/chemistry , Benzopyrans/chemistry , China , Molecular Structure , Spectrum AnalysisABSTRACT
By using the hydrothermal method, carbon microspheres (CMS) were fabricated and used for electrode modification. The characteristics of CMS were investigated using various techniques. The biocompatible sensing platform was built by immobilizing hemoglobin (Hb) on the micrometer-sized CMS-modified electrode with a layer of chitosan membrane. On the cyclic voltammogram, a couple of quasi-reversible cathodic and anodic peaks appeared, showing that direct electrochemistry of Hb with the working electrode was achieved. The catalytic reduction peak currents of the bioelectrode to trichloroacetic acid was established in the linear range of 2.0~70.0 mmol·L(-1) accompanied by a detection limit of 0.30 mmol·L(-1) (3σ). The modified electrode displayed favorable sensitivity, good reproducibility and stability, which suggests that CMS is promising for fabricating third-generation bioelectrochemical sensors.