oxepins and depsidone

Three new depsidones ( 1, 3, and 4), a new diaryl ether ( 5), and a new natural pyrone ( 9) (synthetically known), together with three known depsidones, nidulin ( 6), nornidulin ( 7), and 2-chlorounguinol ( 8), were isolated from the marine-derived fungus ASPERGILLUS UNGUIS CRI282-03. Aspergillusidone C ( 4) showed the most potent aromatase inhibitory activity with the IC (50) value of 0.74 µM, while depsidones 1, 3, 6- 8 inhibited aromatase with IC (50) values of 1.2-11.2 µM. It was found that the structural feature of depsidones, not their corresponding diaryl ether derivatives (e.g. 5), was important for aromatase inhibitory activity. Aspergillusidones A ( 1) and B ( 3) showed radical scavenging activity in the XXO assay with IC (50) values of 16.0 and < 15.6 µM, respectively. Compounds 1 and 3- 7 were mostly inactive or showed only weak cytotoxic activity against HuCCA-1, HepG2, A549, and MOLT-3 cancer cell lines.

Topics: Animals; Aromatase Inhibitors; Aspergillus; Base Sequence; Cell Line, Tumor; Cell Survival; Depsides; DNA, Fungal; DNA, Ribosomal; Drug Screening Assays, Antitumor; Free Radical Scavengers; Humans; Inhibitory Concentration 50; Lactones; Magnetic Resonance Spectroscopy; Molecular Sequence Data; Molecular Structure; Oxepins; Porifera; Sequence Analysis, DNA

Two new depsidones, livistones A (1) and B (2), and a new benzofurane, livistone C (3), together with the 11 known compounds including three stilbenes (4-6), four steroids, three flavan-3-ols, and an alkaloid were isolated from the fruits of Livistona chinensis. The structures of the new compounds were determined by spectroscopic methods. Compounds 1, 4-6 exhibited remarkable cell protective activities against H(2)O(2)-induced SH-SY5Y cell damage.

Topics: Alkaloids; Arecaceae; Benzofurans; Depsides; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal; Fruit; Humans; Hydrogen Peroxide; Lactones; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oxepins; Phenols; Phytosterols; Stereoisomerism; Stilbenes

Two new beta-orcinol depsidones, 1 and 2, together with 13 known compounds were isolated from the lichen Usnea articulata. The structures of 1 and 2 were elucidated by spectroscopic analyses and those of known compounds by comparison of their spectroscopic data with literature values or by direct comparison with authentic standards. Compounds 1, 2, and 5 exhibited moderate antiradical activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The depsidones 4 and 5 showed better superoxide anion scavenging activity (IC50 = 566 and 580 microM, respectively) than quercetin (IC50 = 754 microM).

Topics: Antioxidants; Biphenyl Compounds; Depsides; Free Radical Scavengers; Heterocyclic Compounds, 4 or More Rings; Indonesia; Inhibitory Concentration 50; Lactones; Molecular Structure; Oxepins; Picrates; Quercetin; Superoxides; Usnea