Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity

ChemBioChem
2020.0

Abstract

<jats:title>Abstract</jats:title><jats:p>A new cyclic lipopeptide, phototemtide A (<jats:bold>1</jats:bold>), was isolated from <jats:italic>Escherichia coli</jats:italic> expressing the biosynthetic gene cluster <jats:italic>pttABC</jats:italic> from <jats:italic>Photorhabdus temperata</jats:italic> Meg1. The structure of <jats:bold>1</jats:bold> was elucidated by HR‐ESI‐MS and NMR experiments. The absolute configurations of amino acids and 3‐hydroxyoctanoic acid in <jats:bold>1</jats:bold> were determined by using the advanced Marfey's method and comparison after total synthesis of <jats:bold>1</jats:bold>, respectively. Additionally, three new minor derivatives, phototemtides B–D (<jats:bold>2</jats:bold>–<jats:bold>4</jats:bold>), were identified by detailed HPLC–MS analysis. Phototemtide A (<jats:bold>1</jats:bold>) showed weak antiprotozoal activity against <jats:italic>Plasmodium falciparum</jats:italic>, with an IC<jats:sub>50</jats:sub> value of 9.8 μ<jats:sc>m</jats:sc>. The biosynthesis of phototemtides A–D (<jats:bold>1</jats:bold>–<jats:bold>4</jats:bold>) was also proposed.

Knowledge Graph

Similar Paper

Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from <i>Photorhabdus temperata</i> Meg1, Shows Selective Antiprotozoal Activity
ChemBioChem 2020.0
Structure, Biosynthesis, and Bioactivity of Photoditritide from <i>Photorhabdus temperata</i> Meg1
Journal of Natural Products 2019.0
Hoshinoamides A and B, Acyclic Lipopeptides from the Marine Cyanobacterium <i>Caldora penicillata</i>
Journal of Natural Products 2018.0
Novel Cyclic Hexapeptides from Marine-Derived Fungus, Aspergillus sclerotiorum PT06-1
Organic Letters 2009.0
Bioactive Cyclic Peptides from the Psychrotolerant Fungus Penicillium algidum
The Journal of Antibiotics 2005.0
Luminmycins A–C, Cryptic Natural Products from <i>Photorhabdus luminescens</i> Identified by Heterologous Expression in <i>Escherichia coli</i>
Journal of Natural Products 2012.0
Isolation of D-erythro-neopterin 2′:3′-cyclic phosphate from Photobacterium phosphoreum
Biochimica et Biophysica Acta (BBA) - General Subjects 1973.0
Luminmycins A–C, Cryptic Natural Products from <i>Photorhabdus luminescens</i> Identified by Heterologous Expression in <i>Escherichia coli</i>
Journal of Natural Products 2012.0
Hoshinoamides A and B, Acyclic Lipopeptides from the Marine Cyanobacterium <i>Caldora penicillata</i>
Journal of Natural Products 2018.0
Methionine-Containing Rhabdopeptide/Xenortide-like Peptides from Heterologous Expression of the Biosynthetic Gene Cluster <i>kj12ABC</i> in <i>Escherichia coli</i>
Journal of Natural Products 2018.0