Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives

Nudicaulins are yellow flower pigments accounting for the color of the petals of Papaver nudicaule (Papaveraceae). These glucosidic compounds belong to the small group of indole/flavonoid hybrid alkaloids. Here we describe in vivo and in vitro experiments which substantiate the strongly pH-dependent...

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Autores principales: Dudek, Bettina, Schnurrer, Florian, Dahse, Hans-Martin, Paetz, Christian, Warskulat, Anne-Christin, Weigel, Christiane, Voigt, Kerstin, Schneider, Bernd
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320756/
https://www.ncbi.nlm.nih.gov/pubmed/30567384
http://dx.doi.org/10.3390/molecules23123357
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author Dudek, Bettina
Schnurrer, Florian
Dahse, Hans-Martin
Paetz, Christian
Warskulat, Anne-Christin
Weigel, Christiane
Voigt, Kerstin
Schneider, Bernd
author_facet Dudek, Bettina
Schnurrer, Florian
Dahse, Hans-Martin
Paetz, Christian
Warskulat, Anne-Christin
Weigel, Christiane
Voigt, Kerstin
Schneider, Bernd
author_sort Dudek, Bettina
collection PubMed
description Nudicaulins are yellow flower pigments accounting for the color of the petals of Papaver nudicaule (Papaveraceae). These glucosidic compounds belong to the small group of indole/flavonoid hybrid alkaloids. Here we describe in vivo and in vitro experiments which substantiate the strongly pH-dependent conversion of pelargonidin glucosides to nudicaulins as the final biosynthetic step of these alkaloids. Furthermore, we report the first synthesis of nudicaulin aglycon derivatives, starting with quercetin and ending up at the biomimetic fusion of a permethylated anthocyanidin with indole. A small library of nudicaulin derivatives with differently substituted indole units was prepared, and the antimicrobial, antiproliferative and cell toxicity data of the new compounds were determined. The synthetic procedure is considered suitable for preparing nudicaulin derivatives which are structurally modified in the indole and/or the polyphenolic part of the molecule and may have optimized pharmacological activities.
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spelling pubmed-63207562019-01-14 Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives Dudek, Bettina Schnurrer, Florian Dahse, Hans-Martin Paetz, Christian Warskulat, Anne-Christin Weigel, Christiane Voigt, Kerstin Schneider, Bernd Molecules Article Nudicaulins are yellow flower pigments accounting for the color of the petals of Papaver nudicaule (Papaveraceae). These glucosidic compounds belong to the small group of indole/flavonoid hybrid alkaloids. Here we describe in vivo and in vitro experiments which substantiate the strongly pH-dependent conversion of pelargonidin glucosides to nudicaulins as the final biosynthetic step of these alkaloids. Furthermore, we report the first synthesis of nudicaulin aglycon derivatives, starting with quercetin and ending up at the biomimetic fusion of a permethylated anthocyanidin with indole. A small library of nudicaulin derivatives with differently substituted indole units was prepared, and the antimicrobial, antiproliferative and cell toxicity data of the new compounds were determined. The synthetic procedure is considered suitable for preparing nudicaulin derivatives which are structurally modified in the indole and/or the polyphenolic part of the molecule and may have optimized pharmacological activities. MDPI 2018-12-18 /pmc/articles/PMC6320756/ /pubmed/30567384 http://dx.doi.org/10.3390/molecules23123357 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Dudek, Bettina
Schnurrer, Florian
Dahse, Hans-Martin
Paetz, Christian
Warskulat, Anne-Christin
Weigel, Christiane
Voigt, Kerstin
Schneider, Bernd
Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives
title Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives
title_full Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives
title_fullStr Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives
title_full_unstemmed Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives
title_short Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives
title_sort formation of nudicaulins in vivo and in vitro and the biomimetic synthesis and bioactivity of o-methylated nudicaulin derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320756/
https://www.ncbi.nlm.nih.gov/pubmed/30567384
http://dx.doi.org/10.3390/molecules23123357
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