Synthesis and characterization of bio-based quaternary ammonium salts with gibberellate or l -tryptophanate anion
- PDF / 1,490,419 Bytes
- 9 Pages / 595.276 x 790.866 pts Page_size
- 41 Downloads / 171 Views
ORIGINAL PAPER
Synthesis and characterization of bio‑based quaternary ammonium salts with gibberellate or l‑tryptophanate anion Daria Szymaniak1 · Juliusz Pernak1 · Tomasz Rzemieniecki1 · Damian Krystian Kaczmarek1 · Roman Andrzejak2 · Tomasz Kosiada2 · Beata Janowska2 Received: 30 May 2020 / Accepted: 10 August 2020 © The Author(s) 2020
Abstract Numerous biologically active acids can be transformed into an ionic form in a facile way and combined with appropriate quaternary ammonium cation to improve their application properties or biological activity. This study describes the synthesis of new quaternary ammonium salts with anions of gibberellic acid, a common plant growth regulator from the gibberellin group, or l-tryptophan, an important precursor of auxin biosynthesis. The surface-active tetrapentylammonium ion and natural substances such as acetylcholine, choline, and quinine were the sources of cations. Novel salts of gibberellic acid and l-tryptophan were obtained with high yields exceeding 97% as a result of the metathesis reaction or the neutralization of quaternary ammonium hydroxides. Phase transition temperatures, thermal and chemical stability, and solubility in solvents with different polarities were determined for all obtained salts. On the basis of studies regarding the influence of synthesized salts on the post-harvest longevity and quality of leaves of Convallaria majalis, it was established that the biological activity of the natural plant regulators in most cases was maintained. Therefore, it can be concluded that the conversion of the active substance into the form of a quaternary ammonium salt results in obtaining novel forms of plant growth regulators with favourable physicochemical properties while maintaining the efficacy of the biological active ingredients. Graphic abstract
Keywords Bioorganic chemistry · Ionic liquids · Natural compounds · Phytochemistry · Plant growth regulators
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-020-02672-9) contains supplementary material, which is available to authorized users. * Juliusz Pernak [email protected] 1
Faculty of Chemical Technology, Poznan University of Technology, ul. Berdychowo 4, 60‑965 Poznan, Poland
Faculty of Horticulture and Landscape Architecture, Poznan University of Life Sciences, ul. Dąbrowskiego 159, 60‑594 Poznan, Poland
2
The ageing process of plant organs is the final phase of ontogenesis, during which irreversible changes that result in cell degradation and plant death are initiated [1]. Postharvest longevity is a species-specific trait, even at a varietal level; hence, the ageing of cut flowers occurs at different rates and is the main limitation for the marketing of many species [2]. The situation is similar for species grown as florist’s greens. The longevity of the leaves of many species is unsatisfactory; hence, it is necessary to carry out additional
13
Vol.:(0123456789)
post-harvest treatments, which are desig
Data Loading...
