47492-60-4Relevant academic research and scientific papers
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
, (2018)
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.
Synthesis of 8-aryl-3,5,7,3′,4′-penta-O-methylcyanidins from the corresponding quercetin derivatives by reduction with LiAlH4
Kimura, Yuki,Oyama, Kin-ichi,Kondo, Tadao,Yoshida, Kumi
supporting information, p. 919 - 922 (2017/02/18)
Synthesis of 8-aryl-3,5,7,3′,4′-penta-O-methylcyanidins from the corresponding quercetin derivatives by reduction with LiAlH4is reported. Regioselective iodination at the 8-position of penta-O-methylquercetin followed by a Suzuki-Miyaura reaction gave the 8-arylated quercetin derivatives. By the reduction of 8-arylated quercetins using 4 equiv. of LiAlH4at room temperature for 30 min, the corresponding anthocyanidins were obtained with a good yield.
