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Two new natural products, micropeptin TR1058 ( 1 ) and aeruginosin TR642 ( 2 ), were isolated from the hydrophilic extract of bloom material of Microcystis sp. collected from the Timurim water reservoir in Israel. The structures of compounds 1 and 2 were determined using 1D and 2D NMR spectroscopy and HR ESI MS and MS/MS techniques. Micropeptin TR1058 ( 1 ) was extremely unstable under the isolation conditions, and several degradation products were identified. NMR analysis of aeruginosin TR642 ( 2 ) revealed a mixture of eight isomers, and elucidation of its structure was challenging. Aeruginosin TR642 contains a 4,5-didehydroaraginal subunit that has not been described before. Micropeptin TR1058 ( 1 ) inhibited chymotrypsin with an IC 50 of 6.78 µM, and aeruginosin TR642 ( 2 ) inhibited trypsin and thrombin with inhibition concentration (IC 50 ) values of 3.80 and 0.85 µM, respectively. The structures and biological activities of the new compounds are discussed.

Inhibitors of Serine Proteases from a Microcystis sp. Bloom Material Collected from Timurim Reservoir, Israel