ABSTRACT
A new isopimarane-type diterpene clinacanoid A (1) together with seven known terpenoids (2-8) were obtained from the Clinacanthus nutans. Their structures were elucidated based on extensive spectroscopic analysis (NMR, HR-ESI-MS), and the absolute configuration of 1 was established based on single crystal X-ray diffraction. The inhibitory activity of all the compounds on NO production in lipopolysaccharide-induced (LPS) mouse leukemic monocyte macrophage RAW264.7 cells was evaluated. Among them, compounds 1 and 3 showed potential anti-inflammatory activities, with IC50 values of 13.3 ± 0.3 and 12.4 ± 0.4 µM, respectively.
ABSTRACT
A new isoflavone (Z)-5,7,4'-trihydroxy-3'-[3-hydroxy-3-methyl-1-butenyl] isoflavone (1) together with seven known isoflavones (2-8) were isolated from the fruits of the Ficus auriculata. Their structures were established on the basis of 1 D, 2 D-NMR spectroscopic data and HR-ESI-MS analysis. All compounds were evaluated for their antibacterial activities against five pathogenic bacteria in vitro. Compounds 3 and 4 exhibited significant antibacterial activities against five pathogenic bacteria with the MIC values ranging from 1.25 to 20 µg/mL.[Formula: see text].
Subject(s)
Ficus , Isoflavones , Anti-Bacterial Agents/chemistry , Ficus/chemistry , Fruit/chemistry , Isoflavones/chemistry , Molecular Structure , Plant Extracts/chemistryABSTRACT
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
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
One new furofuran lignan 2-methoxy-9ß-hydroxydiasesamin (1), and four analogues (2-5), together with eight alkaloids (6-13), were isolated from the ethanol extract of the aerial part of Clinacanthus nutans. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. All the compounds were isolated from the genus of Clinacanthus for the first time. In addition, lignans isolated from C. nutans was reported for the first time. Compound 1 exhibited modest activity against three human tumor cell lines Hela, MCF-7, and A549, with IC50 values of 68.55, 60.00, and 59.17 µM, respectively.
Subject(s)
Acanthaceae/chemistry , Alkaloids/chemistry , Alkaloids/pharmacology , Lignans/chemistry , Lignans/pharmacology , A549 Cells , Alkaloids/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Lignans/isolation & purification , MCF-7 Cells , Magnetic Resonance Spectroscopy , Molecular Structure , Plants, Medicinal/chemistryABSTRACT
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
A new lactone ficusine D (1), together with six known compounds (2-7) were isolated from the stems of the Ficus auriculata. The new compound 1 was a rare 12-membered lactone containing a quinone ring skeleton. The structure of the 1 was elucidated by comprehensive spectroscopic data. The relative and absolute configurations of 1 were elucidated by the ROESY analysis and biogenesis pathway. All compounds were evaluated for their antibacterial activities against six pathogenic bacteria in vitro. Compounds 6 and 7 exhibited potent antibacterial activities against Bacillus cereus with the MIC values of 2.5 and 5 µM, respectively.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Ficus/chemistry , Lactones/isolation & purification , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacillus cereus/drug effects , Benzoquinones , Lactones/chemistry , Microbial Sensitivity Tests , Molecular Structure , Plant Stems/chemistry , Spectrum AnalysisABSTRACT
Bioassay-guided fractionation of the petroleum ether, chloroform and EtOAc extracts of the stems of Ficus auriculata led to the isolation of five new 12-membered lactones (3R,4R)-4-hydroxy-de-O-methyllasiodiplodin (1), 6-oxolasiodiplodin (2) and ficusines A-C (3-5), together with three known related analogues (6-8). The structures of the new compounds were elucidated by comprehensive spectroscopic data. The absolute configurations of 3 and 8 were established by single crystal X-ray diffraction analysis. Compounds 3-5 represent the first 12-membered lactones with a quinone ring unit. Compounds 6 and 7 exhibited significant proliferation function of primary osteoblasts (OBs) in vitro. Especially, the promotion rate of 6 reached 151.55±1.34% (P<0.001) at the concentration of 100 µM.