title: Stigonemapeptin, an Ahp-containing depsipeptide with elastase inhibitory activity from the bloom-forming freshwater cyanobacterium Stigonema sp.
abstract: Stigonemapeptin (1), a depsipeptide containing an Ahp (3-amino-6-hydroxy-2-piperidone) residue, was isolated from a bloom sample of the freshwater cyanobacterium Stigonema sp. collected from North Nokomis Lake in the Highland Lake District of northern Wisconsin. The planar structure was determined by 1D and 2D NMR experiments as well as HRESIMS analysis. The absolute configurations of the amino acids were determined using the advanced Marfey's method after acid hydrolysis. Stigonemapeptin (1), characterized by the presence of the Ahp residue, also contained the modified amino acids Abu (2-amino-2-butenoic acid) and N-formylated Pro. Stigonemapeptin (1) showed in vitro elastase and chymotrypsin inhibitory activity, with IC(50) values of 0.26 and 2.93 μM, respectively.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612, USA.
authors.forename: Hahk-Soo
authors.initials: HS
authors.lastname: Kang
authors.forename: Aleksej
authors.initials: A
authors.lastname: Krunic
authors.forename: Jimmy
authors.initials: J
authors.lastname: Orjala
mesh_terms: D000596:Amino Acids / Q000032:analysis; D000818:Animals; D002417:Cattle; D002918:Chymotrypsin / Q000037:antagonists & inhibitors; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005618:Fresh Water / Q000382:microbiology; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010179:Pancreas / Q000201:enzymology; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors*; D010881:Piperidones / Q000737:chemistry; D013552:Swine; D014922:Wisconsin
chemical_list: C555955:3-amino-6-hydroxy-2-piperidone; D000596:Amino Acids; D047630:Depsipeptides; D010881:Piperidones; C573615:stigonemapeptin; D002918:Chymotrypsin; D010196:Pancreatic Elastase