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Mar. Drugs 2015, 13(4), 2347-2375; doi:10.3390/md13042347

New Prenylated Aeruginosin, Microphycin, Anabaenopeptin and Micropeptin Analogues from a Microcystis Bloom Material Collected in Kibbutz Kfar Blum, Israel

Raymond and Beverly Sackler Faculty of Exact Sciences, Raymond and Beverly Sackler School of Chemistry, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel
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Academic Editor: Sylvia Urban
Received: 23 November 2014 / Revised: 16 March 2015 / Accepted: 18 March 2015 / Published: 15 April 2015
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Abstract

Thirteen new and eighteen known natural products were isolated from a bloom material of an assembly of various Microcystis spp. collected in November, 2008, from a commercial fishpond near Kibbutz Kfar Blum, the Jordan Valley, Israel. The new natural products included the prenylated aeruginosin KB676 (1), microphycin KB921 (2), anabaenopeptins KB906 (3) and KB899 (4) and micropeptins KB928 (5), KB956 (6), KB970A (7), KB970B (8), KB984 (9), KB970C (10), KB1048 (11), KB992 (12) and KB1046 (13). Their structures were elucidated primarily by interpretation of their 1D and 2D nuclear magnetic resonance spectra and high-resolution mass spectrometry. Marfey’s and chiral-phase high performance liquid chromatography methods were used to determine the absolute configurations of their chiral centers. Aeruginosin KB676 (1) contains the rare (2S,3aS,6S,7aS)-Choi and is the first prenylated aeruginosin derivative described in the literature. Compounds 1 and 511 inhibited trypsin with sub-μM IC50s, while Compounds 1113 inhibited chymotrypsin with sub-μM IC50s. The structures and biological activities of the new natural products and our procedures of dereplication are described. View Full-Text
Keywords: Microcystis; aeruginosin; anabaenopeptin; micropeptin; microphycin; cyclic peptide; protease inhibitor; nuclear magnetic resonance; mass spectrometry Microcystis; aeruginosin; anabaenopeptin; micropeptin; microphycin; cyclic peptide; protease inhibitor; nuclear magnetic resonance; mass spectrometry
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Elkobi-Peer, S.; Carmeli, S. New Prenylated Aeruginosin, Microphycin, Anabaenopeptin and Micropeptin Analogues from a Microcystis Bloom Material Collected in Kibbutz Kfar Blum, Israel. Mar. Drugs 2015, 13, 2347-2375.

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