Micropeptins from Microcystis sp. collected in Kabul Reservoir, Israel

Bladt, Tanja Thorskov; Kalifa-Aviv, Sivan; Larsen, Thomas Ostenfeld; Carmeli, Shmuel

doi:10.1016/j.tet.2013.12.009

Cited by 12 publications

(5 citation statements)

References 22 publications

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“…The activity of micropeptin TR1058 ( 1 ) is in line with the structure-activity relationship of the Ahp-containing cyclic micropeptins [ 9 ]. Structurally related micropeptin KR1030 inhibits chymotrypsin and elastase with IC 50 values of 13.9 and 28.0 μM, respectively [ 28 ]. Interestingly, the acid-catalyzed hydrolysis of the glutamine residue of 1 in the acidic conditions of the HPLC mobile-phase (0.1% TFA/MeCN) produced glutamic acid and methoxyglutamate, and neither inhibited chymotrypsin catalytic activity.…”

Section: Resultsmentioning

confidence: 99%

Inhibitors of Serine Proteases from a Microcystis sp. Bloom Material Collected from Timurim Reservoir, Israel

Hasan-Amer

Carmeli

2017

Marine Drugs

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Two new natural products, micropeptin TR1058 (1) and aeruginosin TR642 (2), were isolated from the hydrophilic extract of bloom material of Microcystis sp. collected from the Timurim water reservoir in Israel. The structures of compounds 1 and 2 were determined using 1D and 2D NMR spectroscopy and HR ESI MS and MS/MS techniques. Micropeptin TR1058 (1) was extremely unstable under the isolation conditions, and several degradation products were identified. NMR analysis of aeruginosin TR642 (2) revealed a mixture of eight isomers, and elucidation of its structure was challenging. Aeruginosin TR642 contains a 4,5-didehydroaraginal subunit that has not been described before. Micropeptin TR1058 (1) inhibited chymotrypsin with an IC50 of 6.78 µM, and aeruginosin TR642 (2) inhibited trypsin and thrombin with inhibition concentration (IC50) values of 3.80 and 0.85 µM, respectively. The structures and biological activities of the new compounds are discussed.

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Section: Resultsmentioning

confidence: 99%

Inhibitors of Serine Proteases from a Microcystis sp. Bloom Material Collected from Timurim Reservoir, Israel

Hasan-Amer

Carmeli

2017

Marine Drugs

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“…Different structures belonging to micropeptins, such as KB928, KB956, KB970A, KB970B, KB984, KB970C, KB1048, KB992, KB1046, TR1058, KR1030, KR1002, KR998, MZ845, MZ859, MZ939A, MZ925, MZ939B, MZ1019, MZ771, LH920, LH1021, LH1048, LH1062, LH911A, LH911B, LH911C, and LH925 were isolated from a Microcystis collected in diverse water reservoirs (fishpond, secondary water pond, etc.,) (Zafrir and Carmeli, 2010; Bladt et al, 2014; Elkobi-Peer and Carmeli, 2015; Hasan-Amer and Carmeli, 2017).…”

Section: Chemical Analysis and Biological Activities Of Several Impormentioning

confidence: 98%

“…For other compounds, MeOH/H 2 O extract was separated by reversed phase (ODS) open column followed by separation on Sephadex LH-20. Further they were separated by preparative HPLC to yield different variants of KR and LH (Vegman and Carmeli, 2013; Bladt et al, 2014).…”

Section: Chemical Analysis and Biological Activities Of Several Impormentioning

confidence: 99%

“…The 19-membered core structure contains a unique 3-amino-6-hydroxypiperidinone (Ahp) moiety and an α-amino- β-hydroxy acid (L-threonine or β-hydroxy-γ-methylproline). The structure of micropeptin KR1002 contain the sequences of acid residues as Val, N- MeTyr, N, N -disubstituted-Phe, Ahp, HcAla, Thr, Gln, and BA (Bladt et al, 2014). Structure of several micropeptin analogs are depicted in Figure 3A.…”

Section: Chemical Analysis and Biological Activities Of Several Impormentioning

confidence: 99%

“…Bladt et al (2014) evaluated the enzyme inhibitory activity of micropeptin KR1030, KR1002, and KR998 against serine proteases like chymotrypsin, elastase, and trypsin. It was concluded that IC 50 of variants KR1030, KR1002, and KR998 against chymotrypsin was 13.9, 18.8 and 5.9 μM.…”

Section: Chemical Analysis and Biological Activities Of Several Impormentioning

confidence: 99%

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Recent Advances in Exploration and Biotechnological Production of Bioactive Compounds in Three Cyanobacterial Genera: Nostoc, Lyngbya, and Microcystis

Thuần

Shrestha

et al. 2019

Front. Chem.

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Cyanobacteria, are only Gram-negative bacteria with the capacity of oxygenic photosynthesis, so termed as “Cyanophyta” or “blue-green algae.” Their habitat is ubiquitous, which includes the diverse environments, such as soil, water, rock and other organisms (symbiosis, commensalism, or parasitism, etc.,). They are characterized as prominent producers of numerous types of important compounds with anti-microbial, anti-viral, anti-inflammatory and anti-tumor properties. Among the various cyanobacterial genera, members belonging to genera Nostoc, Lyngbya, and Microcystis possess greater attention. The major reason for that is the strains belonging to these genera produce the compounds with diverse activities/structures, including compounds in preclinical and/or clinical trials (cryptophycin and curacin), or the compounds retaining unique activities such as protease inhibitor (micropeptins and aeruginosins). Most of these compounds were tested for their efficacy and mechanism of action(MOA) through in vitro and/or in vivo studies. Recently, the advances in culture techniques of these cyanobacteria, and isolation, purification, and chromatographic analysis of their compounds have revealed insurmountable novel bioactive compounds from these cyanobacteria. This review provides comprehensive update on the origin, isolation and purification methods, chemical structures and biological activities of the major compounds from Nostoc, Lyngbya, and Microcystis. In addition, multi-omics approaches and biotechnological production of compounds from selected cyanobacterial genera have been discussed.

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