ABSTRACT
Two salicylaldehyde derivatives (1 and 2), a hydroxymethylphenol (3), five dihydroisobenzofuran (4-8) derivatives, and a 5-chloro-3-deoxyisoochracinic acid (9), together with a known 3-deoxyisoochracinic acid (10) were isolated from the marine fungus Zopfiella marina BCC 18240 (or NBRC 30420). The structures of these compounds were elucidated by extensive spectroscopic analysis. Compound 1 showed weak antituberculous activity against Mycobacterium tuberculosis H37Ra, and antibacterial activity against Bacillus cereus with MIC values of 25 and 12.5 µg/mL, respectively.
Subject(s)
Aldehydes/isolation & purification , Anti-Bacterial Agents/isolation & purification , Benzofurans/isolation & purification , Fungi/chemistry , Aldehydes/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacillus cereus/drug effects , Marine Biology , Microbial Sensitivity Tests , Molecular Structure , Mycobacterium tuberculosis/drug effects , Spectrum AnalysisABSTRACT
Five highly oxygenated chromones, rhytidchromones A-E, were isolated from the culture broth of a mangrove-derived endophytic fungus, Rhytidhysteron rufulum, isolated from Thai Bruguiera gymnorrhiza. Their structures were determined by analysis of 1D and 2D NMR spectroscopic data. The structure of rhytidchromone A was further confirmed by single-crystal X-ray diffraction analysis. These compounds were evaluated for cytotoxicity against four cancer cell lines (MCF-7, Hep-G2, Kato-3 and CaSki). All compounds, except for rhytidchromone D, displayed cytotoxicity against Kato-3 cell lines with IC50 values ranging from 16.0 to 23.3µM, while rhytidchromones A and C were active against MCF-7 cells with IC50 values of 19.3 and 17.7µM, respectively.
Subject(s)
Antineoplastic Agents/isolation & purification , Ascomycota/chemistry , Chromones/isolation & purification , Rhizophoraceae/microbiology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Chromones/chemistry , Chromones/pharmacology , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Female , Hep G2 Cells , Humans , MCF-7 Cells , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oxygen , ThailandABSTRACT
As part of our ongoing efforts to investigate natural products with potential for use as cancer treatments, we have recently disclosed the cytotoxicity of unique nor-chamigrane (1) and chamigrane (2, 3) endoperoxides from a Thai mangrove-derived fungus. Reinvestigation of this fungus in a large-scale fermentation led to the isolation of an additional new chamigrane endoperoxide (4) and one known analogue (5). Among these isolated metabolites, compound 3 (merulin C) exhibited potent antiangiogenic activity mainly by suppression of endothelial cell proliferation and migration in a dose-dependent manner, and its effect is mediated by reduction in the phosphorylation of Erk1/2. Merulin C also displayed promising activity in a rat aortic ring sprouting (ex vivo) and a mouse Matrigel (in vivo) assay.
Subject(s)
Angiogenesis Inhibitors/isolation & purification , Angiogenesis Inhibitors/pharmacology , Basidiomycota/chemistry , Peroxides/isolation & purification , Peroxides/pharmacology , Angiogenesis Inhibitors/chemistry , Animals , Aorta/drug effects , Dose-Response Relationship, Drug , Meliaceae/microbiology , Mice , Molecular Structure , Peroxides/chemistry , Plant Leaves/microbiology , Rats , ThailandABSTRACT
A new nor-chamigrane endoperoxide, merulin A (1), and two new chamigrane endoperoxides, merulins B and C (2, 3), were isolated from the culture broth extract of an endophytic fungus of Xylocarpus granatum. Their structures were elucidated on the basis of spectroscopic, mainly NMR and MS, data. X-ray crystallographic analysis confirmed the structure of 1. Compounds 1 and 3 displayed significant cytotoxicity against human breast (BT474) and colon (SW620) cancer cell lines.
Subject(s)
Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Basidiomycota/chemistry , Peroxides/isolation & purification , Peroxides/pharmacology , Antineoplastic Agents/chemistry , Breast Neoplasms/drug therapy , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Female , Humans , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Peroxides/chemistryABSTRACT
A new linear polyester, menisporopsin B, along with the known macrocyclic polyester, menisporopsin A, was isolated from the seed fungus Menisporopsis theobromae BCC 4162. The structure of menisposopsin B was addressed primarily by spectroscopic analyses, and the stereochemistry was established by chemical correlation. Menisporopsin B exhibited antimalarial activity with an IC(50) value of 1.0 microg/ml.
