Green “one-pot” fluorescent bis-indolizine synthesis with whole-cell plant biocatalysis

Abstract

An efficient one-pot route leading to bis-indolizine symmetric compounds has been developed via a new approach from the dipyridinium heterocyclic compound, reactive halogenated derivative, and activated alkyne through biocatalysis. A set of local plants was evaluated for its catalytic potential in “one-pot” biocatalysis of these valuable fluorescent compound synthesis reactions. Most of these biocatalysts containing enzymes from the oxidoreductase class (peroxidase: 0.56–1.08 mmol purpurogallin‧g−1 fresh weight‧min−1, polyphenol oxidase (PPO) : 27.19–48.95 PPO units‧mg tissue−1, CAT: 3.27–21.71 µmol O2‧g−1 fresh weight‧min−1), were used as green catalysts in the multi-component cycloaddition reaction, in an aqueous buffer solution, for the production of bis-indolizine compounds in moderate to excellent yields (45–85%). The horseradish root (Armoracia rusticana) has been selected as the most promising biocatalyst source among the evaluated plants, and the obtained yields were greater than in the conventional synthesis method. The structures of indolizine derivatives were confirmed by nuclear magnetic resonance spectra, elemental analyses, as well as Fourier transform-infrared spectra. The cytotoxicity of the latter obtained indolizine compounds on the growth of the model microorganism, Saccharomyces cerevisiae MIUG 3.6 yeast strain, was also evaluated. Various parameters (number of generations, growth rate, generation time, dry matter yield, the degree of the budding yeast cells, and the degree of yeast autolysis, fermentation intensity), which describe the yeast growth, suggest that the nutrient broth supplemented with different concentrations of bis-indolizine compounds (10 and 1 µM) had no toxic effect on the yeast strain growth, under submerged cultivation conditions.