Hahk-Soo Kang1, Aleksej Krunic, Jimmy Orjala. 1. Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612, USA.
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.
Stigonemapeptin (1), a n class="Chemical">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: Sarath P Gunasekera; Margaret W Miller; Jason C Kwan; Hendrik Luesch; Valerie J Paul Journal: J Nat Prod Date: 2010-03-26 Impact factor: 4.050
Authors: George E Chlipala; Megan Sturdy; Aleksej Krunic; Daniel D Lantvit; Qi Shen; Kyle Porter; Steven M Swanson; Jimmy Orjala Journal: J Nat Prod Date: 2010-09-24 Impact factor: 4.050
Authors: Lena Keller; Kirley Marques Canuto; Chenxi Liu; Brian M Suzuki; Jehad Almaliti; Asfandyar Sikandar; C Benjamin Naman; Evgenia Glukhov; Danmeng Luo; Brendan M Duggan; Hendrik Luesch; Jesko Koehnke; Anthony J O'Donoghue; William H Gerwick Journal: ACS Chem Biol Date: 2020-01-28 Impact factor: 5.100
Authors: Shangwen Luo; Aleksej Krunic; Hahk-Soo Kang; Wei-Lun Chen; John L Woodard; James R Fuchs; Steven M Swanson; Jimmy Orjala Journal: J Nat Prod Date: 2014-08-04 Impact factor: 4.050