Next Article in Journal
Photochemical Reactions in Dialdehyde Starch
Previous Article in Journal
Resveratrol-Induced White Adipose Tissue Browning in Obese Mice by Remodeling Fecal Microbiota
Open AccessArticle

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

1
Max Planck Institute for Chemical Ecology, Hans-Knöll-Str. 8, D-07745 Jena, Germany
2
Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI), Adolf-Reichwein-Straße 23, D-07745 Jena, Germany
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2018, 23(12), 3357; https://doi.org/10.3390/molecules23123357
Received: 9 November 2018 / Revised: 3 December 2018 / Accepted: 15 December 2018 / Published: 18 December 2018
(This article belongs to the Section Natural Products Chemistry)
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. View Full-Text
Keywords: nudicaulins; flower pigments; indole alkaloids; biomimetic synthesis; bioassays nudicaulins; flower pigments; indole alkaloids; biomimetic synthesis; bioassays
Show Figures

Graphical abstract

MDPI and ACS Style

Dudek, B.; Schnurrer, F.; Dahse, H.-M.; Paetz, C.; Warskulat, A.-C.; Weigel, C.; Voigt, K.; Schneider, B. Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives. Molecules 2018, 23, 3357.

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.

Article Access Map by Country/Region

1
Back to TopTop