Next Article in Journal
Collagens of Poriferan Origin
Previous Article in Journal
ATG5 Promotes Death Signaling in Response to the Cyclic Depsipeptides Coibamide A and Apratoxin A
Article Menu
Issue 3 (March) cover image

Export Article

Open AccessArticle
Mar. Drugs 2018, 16(3), 78; https://doi.org/10.3390/md16030078

Microginins from a Microcystis sp. Bloom Material Collected from the Kishon Reservoir, Israel

Raymond and Beverly Sackler School of Chemistry and Faculty of Exact Sciences, Tel Aviv University, Ramat-Aviv, Tel Aviv 69978, Israel
*
Author to whom correspondence should be addressed.
Received: 4 January 2018 / Revised: 25 February 2018 / Accepted: 28 February 2018 / Published: 2 March 2018
Full-Text   |   PDF [739 KB, uploaded 2 March 2018]   |  

Abstract

During blooms, cyanobacteria produce diverse modified peptides. Among these are the microginins, which inhibit zinc-containing metalloproteases. Ten microginins, microginins KR767 (1), KR801(2), KR835 (3), KR785 (4), KR604 (5), KR638 (6), KR781 (7), KR815 (8), FR3 (9), and FR4 (10), were isolated from the extract of a bloom material of Microcystis sp. (IL-405) collected from the Kishon Reservoir, Israel in the fall of 2009. The structures of the pure compounds were elucidated using 1D and 2D NMR techniques and high-resolution mass spectrometry. The absolute configuration of the chiral centers of the amino acids were determined by Marfey’s and advance Marfey’s methods and by comparison of 1H and 13C NMR chemical shifts of the Ahda derivatives with those of known microginins. These microginins differ in sequence and absolute configuration of the chiral centers of the Ahda moieties and by N-methylation of the Ahda amine group and extent of chlorination of the Ahda terminal methyl group. The compounds were evaluated for inhibition of the zinc metalloprotease, aminopeptidase M, and exhibited low- to sub-nanomolar half maximal inhibitory concentration (IC50) values. View Full-Text
Keywords: microginins; cyanobacteria; Microcystis; aminopeptidase M inhibitors microginins; cyanobacteria; Microcystis; aminopeptidase M inhibitors
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Lodin-Friedman, A.; Carmeli, S. Microginins from a Microcystis sp. Bloom Material Collected from the Kishon Reservoir, Israel. Mar. Drugs 2018, 16, 78.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top