Micropeptins from Microcystis aeruginosa collected in Dalton reservoir, Israel

Simi Adiv; Regina Aharonv-Nadborny; Shmuel Carmeli

doi:10.1016/j.tet.2010.06.071

Micropeptins from Microcystis aeruginosa collected in Dalton reservoir, Israel

Simi Adiv, Regina Aharonv-Nadborny, Shmuel Carmeli^*

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

Three new micropeptins, micropeptin DR1056, DR1060 and DR1006 and three known metabolites, micropeptin SF909, aeruginosins 298A and B were isolated from the extracts of a Microcystis aeruginosa bloom material collected in Dalton reservoir, Israel. The planar structure of the compounds was determined by homonuclear and inverse-heteronuclear 2D NMR techniques as well as high-resolution mass spectrometry. The absolute configuration of the asymmetric centers of the amino acids was studied using Marfey's method for HPLC. The inhibitory activity of the compounds was determined for the serine proteases: trypsin, chymotrypsin, and elastase and for amino peptidase N.

Original language	English
Pages (from-to)	7429-7436
Number of pages	8
Journal	Tetrahedron
Volume	66
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2010.06.071
State	Published - 11 Sep 2010

Funding

Funders	Funder number
Israel Science Foundation	776/06, 037/02

Keywords

Cyanobacteria
Microcystis aeruginosa
Micropeptins
Natural products
Protease inhibitors

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10.1016/j.tet.2010.06.071

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title = "Micropeptins from Microcystis aeruginosa collected in Dalton reservoir, Israel",

abstract = "Three new micropeptins, micropeptin DR1056, DR1060 and DR1006 and three known metabolites, micropeptin SF909, aeruginosins 298A and B were isolated from the extracts of a Microcystis aeruginosa bloom material collected in Dalton reservoir, Israel. The planar structure of the compounds was determined by homonuclear and inverse-heteronuclear 2D NMR techniques as well as high-resolution mass spectrometry. The absolute configuration of the asymmetric centers of the amino acids was studied using Marfey's method for HPLC. The inhibitory activity of the compounds was determined for the serine proteases: trypsin, chymotrypsin, and elastase and for amino peptidase N.",

keywords = "Cyanobacteria, Microcystis aeruginosa, Micropeptins, Natural products, Protease inhibitors",

author = "Simi Adiv and Regina Aharonv-Nadborny and Shmuel Carmeli",

note = "Funding Information: We thank Noam Tal, The Mass Spectrometry Laboratory of The School of Chemistry, Tel Aviv University, for the ESI mass spectra measurements. This research was supported by the Israel Science Foundation grants 037/02 and 776/06 . ",

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doi = "10.1016/j.tet.2010.06.071",

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AU - Adiv, Simi

AU - Aharonv-Nadborny, Regina

AU - Carmeli, Shmuel

N1 - Funding Information: We thank Noam Tal, The Mass Spectrometry Laboratory of The School of Chemistry, Tel Aviv University, for the ESI mass spectra measurements. This research was supported by the Israel Science Foundation grants 037/02 and 776/06 .

PY - 2010/9/11

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AB - Three new micropeptins, micropeptin DR1056, DR1060 and DR1006 and three known metabolites, micropeptin SF909, aeruginosins 298A and B were isolated from the extracts of a Microcystis aeruginosa bloom material collected in Dalton reservoir, Israel. The planar structure of the compounds was determined by homonuclear and inverse-heteronuclear 2D NMR techniques as well as high-resolution mass spectrometry. The absolute configuration of the asymmetric centers of the amino acids was studied using Marfey's method for HPLC. The inhibitory activity of the compounds was determined for the serine proteases: trypsin, chymotrypsin, and elastase and for amino peptidase N.

KW - Cyanobacteria

KW - Microcystis aeruginosa

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KW - Natural products

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Micropeptins from Microcystis aeruginosa collected in Dalton reservoir, Israel

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