Abstract
Perezone, a sesquiterpene quinone, is a very important molecule due to its pharmacological activities in addition to the fact that it is considered to be the first secondary metabolite isolated in the new world (America–Mexico, 1852). This study aims to offer a green comparative study about the extraction of the target molecule from the roots of the vegetable specimen Acourtia platyphilla (A. Grey). The study was performed comparing five different modes of extraction: supercritical CO2, electromagnetic infrared and microwave irradiations, mechanical-wave ultrasound versus typical mantle heating procedure. An exhaustive comparative-discussion of the obtained results is provided. It is worth noting that the corresponding quantifications were established using 1H NMR, correlating appropriately the integrals of the vinylic proton H-6 of perezone with the aromatic singlet of p-dinitrobenzene employed as an internal reference. It is also important to highlight that the four presented procedures are novel modes to extract perezone. Finally, a complementary study about the solubility of the target sesquiterpene quinone related to the use of supercritical CO2 is also reported.
Highlights
Many quinones are interesting secondary metabolites which are mainly isolated from plants [1], in particular, for this study perezone or pipitzaoic acid, a sesquiterpene quinone (Figure 1), is recognized as the first secondary metabolite isolated on the American continent (New World) by Leopoldo Río de la Loza [2] from the roots of Perezia ( Acourtia) specimens
This important molecule has been the target of many chemical, structural, 46 and biological studies, e.g., its reactivity into pipitzols [3,4,5], its transformation into isoperezone [6], structural
Silica gel on thin-layer chromatography (TLC) Al foils, 1,4-dinitrobencene and CDCl3 were acquired from Sigma-Aldrich
Summary
Many quinones are interesting secondary metabolites which are mainly isolated from plants [1], in particular, for this study perezone or pipitzaoic acid, a sesquiterpene quinone (Figure 1), is recognized as the first secondary metabolite isolated on the American continent (New World) by Leopoldo Río de la Loza [2] from the roots of Perezia ( Acourtia) specimens. In 1856, Dr de la Loza received a gold medal for his chemical discoveries from the Society for the Protection of Industrial Arts in London. This important molecule has been the target of many chemical, structural, and biological studies, e.g., its reactivity into pipitzols [3,4,5], its transformation into isoperezone [6], several green contributions [7,8], Molecules 2019, 24, 3035; doi:10.3390/molecules24173035 www.mdpi.com/journal/molecules. This important molecule has been the target of many chemical, structural, 46 and biological studies, e.g., its reactivity into pipitzols [3,4,5], its transformation into isoperezone [6], structural (NMR studies) [9,10,11].
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