TitleJizanpeptins, Cyanobacterial Protease Inhibitors from a Symploca sp. Cyanobacterium Collected in the Red Sea.
Publication TypeJournal Article
Year of Publication2018
AuthorsGallegos DA, Saurí J, Cohen RD, Wan X, Videau P, Vallota-Eastman AO, Shaala LA, Youssef DTA, R Williamson T, Martin GE, Philmus B, Sikora AE, Ishmael JE, McPhail KL
JournalJ Nat Prod
Date Published2018 May 29
ISSN1520-6025
Abstract

Jizanpeptins A-E (1-5) are micropeptin depsipeptides isolated from a Red Sea specimen of a Symploca sp. cyanobacterium. The planar structures of the jizanpeptins were established using NMR spectroscopy and mass spectrometry and contain 3-amino-6-hydroxy-2-piperidone (Ahp) as one of eight residues in a typical micropeptin motif, as well as a side chain terminal glyceric acid sulfate moiety. The absolute configurations of the jizanpeptins were assigned using a combination of Marfey's methodology and chiral-phase HPLC analysis of hydrolysis products compared to commercial and synthesized standards. Jizanpeptins A-E showed specific inhibition of the serine protease trypsin (IC = 72 nM to 1 μM) compared to chymotrypsin (IC = 1.4 to >10 μM) in vitro and were not overtly cytotoxic to HeLa cervical or NCI-H460 lung cancer cell lines at micromolar concentrations.

DOI10.1021/acs.jnatprod.8b00117
Alternate JournalJ. Nat. Prod.
PubMed ID29808677