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Metabolomics-Guided Discovery of Microginin Peptides from Cultures of the Cyanobacterium Microcystis aeruginosa

Author:
Stewart, Allison K., Ravindra, Rudravajhala, Van Wagoner, Ryan M., Wright, Jeffrey L. C.
Source:
Journal of natural products 2018 v.81 no.2 pp. 349-355
ISSN:
1520-6025
Subject:
Microcystis aeruginosa, derivatization, inhibitory concentration 50, metabolomics, methionine, peptides, peptidyl-dipeptidase A, spectral analysis
Abstract:
We report a mass-spectrometry-based metabolomics study of a laboratory-cultured strain of Microcystis aeruginosa (UTEX LB2385), which has led to the discovery of five peptides (1–5) belonging to the microginin class of linear cyanopeptides. The structures and configurations of these peptides were determined by spectroscopic analyses and chemical derivitization. The microginin peptides described herein are the first reported derivatives containing N-methyl methionine (1, 5) and N-methyl methionine sulfoxide (2–4). The two tripeptide microginin analogues (4, 5) identified represent the smallest members of this peptide family. Their angiotensin-converting enzyme (ACE) inhibitory activity was also investigated. Microginin 527 (4) was the most potent of the group, with an IC₅₀ of 31 μM.
Agid:
6043063