Three new bisindole alkaloids of the hamacanthin class (1-3) and one new bisindole alkaloid of the topsentin class (6) were isolated along with known bisindole alkaloids (4, 5, 7-11) from the MeOH extract of a marine sponge Spongosorites sp. by bioactivity-guided fractionation. The planar structures were established on the basis of NMR, MS, and IR spectroscopic analyses. Configurations of compounds 1-4 were derived from 1H NMR data and optical rotation. Compounds 1, 4, 5, and 11 showed moderate to significant cytotoxicity against five human tumor cell lines, and compounds 1-5 showed weak antibacterial activity against clinically isolated methicillin-resistant strains.
Seven new (1 and 3-8) and seven known (2 and 9-14) bisindole alkaloids of the topsentin and hamacanthin classes were isolated from the MeOH extract of a marine sponge Spongosorites sp. by bioactivity-guided fractionation. The structure of compound 7 is a revision from our previous report. The planar structures were established on the basis of NMR and MS spectroscopic analyses. Configurations of these compounds were defined by NMR spectroscopy and optical rotation. It is noteworthy that both R and S isomers were isolated for the hamacanthins (1-4, 9, 10, 15, and 16), while a single stereoisomer was isolated for dihydrohamacanthins (5, 11-14, 17, and 18). Compounds 1-4, 6, and 8-14 showed marginal cytotoxicity against five human solid tumor cell lines, and compound 2 showed weak antibacterial activity against clinically isolated methicillin-resistant strains.
This report reviews biologically active secondary metabolites from marine-derived members of the fungal genus Aspergillus. Pharmacological activities and biological roles of the secondary metabolites from marine-derived Aspergillus spp. were addressed in respect of pharmaceutical potential.
In the course of our search for bioactive metabolites from a sponge-derived fungus Acremonium sp., new sesquiterpenoids (1-4) were isolated along with known derivatives by bioactivity-guided fractionation. The unique cyclic skeleton of compounds 2 and 3 is unprecedented. The absolute configurations were determined by modified Mosher's method and CD spectroscopy, along with comparison of (1)H and (13)C NMR spectroscopic data and specific optical rotation values with those reported. The anti-inflammatory activity of the isolated compounds (1, 5, 7-13) was evaluated by measuring their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in RAW 264.7 murine macrophage cells. Among the compounds tested, compounds 7 and 9 significantly inhibited the production of NO and TNF-alpha at the concentration of 100 microM, while compounds 11 and 12 showed selective inhibition of NO production at the same concentration.
Seven (1–7) monoindole derivatives were isolated from the MeOH extract of a marine sponge Spongosorites sp. by bioactivity-guided fractionation. The planar structures were established on the basis of NMR and MS spectroscopic analyses. Compounds 1–5 are unique indole pyruvic acid derivatives. Compounds 1–2 and 4–6 are isolated for the first time from a natural source although they were previously reported as synthetic intermediates. Compound 3 was defined as a new compound. Co-occurring bisindoles such as hamacanthins and topsentins might be biosynthesized by condensation of two units of these compounds. The compounds were tested for cytotoxicity against a panel of five human solid tumor cell lines, and compound 7 displayed weak activity.
A bacterial strain with good antibacterial activities against Staphylococus aureus and Escherichia coli was isolated from a marine sponge Stelleta sp., and it was identified as a Psychrobacter sp. by comparative 16S rDNA sequence analysis. In our search for bioactive secondary metabolites from this psychrophillic and halotolerent bacterium, sixteen cyclic dipeptides (1-16) were isolated and their structures were identified on the basis of NMR analysis. In the test of the compounds for the protective effect against Vibrio vulnificusinduced cytotoxicity in human intestinal epithelial cells, cyclo-(L-Pro-L-Phe) (5) exhibited significant protective effect. Compounds 2, 6, and 11, which contain D-amino acid, were first isolated from bacteria.
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