title: New prenylated aeruginosin, microphycin, anabaenopeptin and micropeptin analogues from a Microcystis bloom material collected in Kibbutz Kfar Blum, Israel.
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 5-11 inhibited trypsin with sub-μM IC50s, while Compounds 11-13 inhibited chymotrypsin with sub-μM IC50s. The structures and biological activities of the new natural products and our procedures of dereplication are described.
authors.affiliation: Raymond and Beverly Sackler Faculty of Exact Sciences, Raymond and Beverly Sackler School of Chemistry, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel. shirapeer@gmail.com.
authors.forename: Shira
authors.initials: S
authors.lastname: Elkobi-Peer
authors.affiliation: Raymond and Beverly Sackler Faculty of Exact Sciences, Raymond and Beverly Sackler School of Chemistry, Tel Aviv University, Ramat Aviv, Tel Aviv 69978, Israel. carmeli@post.tau.ac.il.
authors.forename: Shmuel
authors.initials: S
authors.lastname: Carmeli
mesh_terms: D017756:Aquaculture; D001430:Bacteriocins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D002918:Chymotrypsin / Q000037:antagonists & inhibitors / Q000378:metabolism; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004151:Dipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006146:Guanidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D057097:Harmful Algal Bloom; D007557:Israel; D008387:Marine Toxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D046931:Microcystis / Q000737:chemistry* / Q000254:growth & development / Q000302:isolation & purification; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D061005:Ponds / Q000382:microbiology; D017368:Protein Prenylation; D015842:Serine Proteinase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry; D014361:Trypsin Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D001430:Bacteriocins; D047630:Depsipeptides; D004151:Dipeptides; D006146:Guanidines; D008387:Marine Toxins; D009842:Oligopeptides; D010456:Peptides, Cyclic; D015842:Serine Proteinase Inhibitors; D014361:Trypsin Inhibitors; D014508:Urea; D002918:Chymotrypsin