An improved method for the isolation of amarogentin, the bitter principle of yellow gentian roots

Fiorito, Serena; Epifano, Francesco; Marchetti, Lorenzo; Palumbo, Lucia; Mascioli, Fabrizio; Bastianini, Maria; Cardellini, Fabio; Spogli, Roberto; Genovese, Salvatore

doi:10.1016/j.foodchem.2021.130383

Cited by 12 publications

(8 citation statements)

References 21 publications

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“…The same general procedure as reported previously was followed for the extraction of plant material, solid-phase adsorption, and HPLC analyses. 3 Analytical conditions and parameters are detailed in the Supporting Information.…”

Section: ■ Associated Contentmentioning

confidence: 99%

“…The values of their respective bitterness indexes, 58 × 10 6 for amarogentin (2) and 12 × 10 3 for gentiopicroside (1), reveal why these two secondary metabolites can be regarded as the most widely used naturally occurring bitter-tasting substances. 3 Thus, amarogentin (2) and gentiopicroside (1) are the main determinants of the typical bitter taste of alcoholic beverages obtained traditionally from gentian roots. These are used widely by local populations mostly in the form of homemade liqueurs.…”

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confidence: 99%

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Leaves of Yellow Gentian (Gentiana lutea) as an Alternative Source of Bitter Secoiridoid Glycosides

et al. 2022

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In a search for methods of manufacturing bitter principles from Gentiana lutea, mainly represented by gentiopicroside (1) and amarogentin (2), as an alternative to extraction from the roots of this plant, in this short communication it is shown that the leaves of this plant can be regarded as an additional source of such phytochemicals. Extraction of G. lutea leaves was coupled to solid-phase adsorption by differently structured solids as a separation technology step, providing a selective isolation of both these secondary metabolites in good to excellent yields. Thus, the extraction of bitter secoiridoids can be achieved in an equivalent or improved way rather than processing the roots of G. lutea while preserving the biodiversity of the species.

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Section: ■ Associated Contentmentioning

confidence: 99%

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confidence: 99%

Leaves of Yellow Gentian (Gentiana lutea) as an Alternative Source of Bitter Secoiridoid Glycosides

et al. 2022

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“…The same apparatus as already described was used to accomplish HPLC/DAD analyses [18]. Each chromatographic run was done in triplicate.…”

Section: Nmr and Hrms Analysesmentioning

confidence: 99%

“…All the precision measurements were expressed as relative standard deviations (RSDs) and ranged from 0.18 to 1.23. Precision was calculated at 3 concentration levels, namely quality control QC Low = 0.50 µg/ mL, QC Medium = 5.0 µg/mL, and QC High = 100.0 µg/mL, and assessed following the criteria already reported [18]. Accuracy was determined by spiking the samples obtained after the extraction process with 3 concentrations of the chemical standards (low, medium, and high spikes).…”

Section: Nmr and Hrms Analysesmentioning

confidence: 99%

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Modulation of the biosynthesis of oxyprenylated coumarins in calli from Ferulago campestris elicited by ferulic acid

Fiorito

Palumbo

Epifano

et al. 2022

Biomass Conv. Bioref.

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Previous and recent literature acquisitions suggested that cultured calli are an efficient and meaningful model to investigate the extent and fate of prenylation of phenylpropanoid cores in plants belonging to the Rutaceae and Apiaceae families upon administration of putative biosynthetic precursors. To this concern, in the present manuscript, we investigated the effect of supplementation of ferulic acid and umbelliferone on the biosynthesis of their oxyprenylated counterparts in Ferulago campestris (Besser) Grecescu (Fam. Apiaceae) cultured calli. Dried plant biomass material has been extracted by an ultrasound-assisted extraction with EtOH. O-prenyl secondary metabolites, namely 3,3-dimethylallyloxy, geranyloxy, and farnesyloxy derivatives of both ferulic acid and umbelliferone, were identified and quantified by HPLC/DAD analyses. Supplementation with ferulic acid was the only treatment providing appreciable results. Quite surprisingly, its addition to cultured calli did not affect the formation of its oxyprenylated phytochemicals but boosted the biosynthesis of umbelliferone and its farnesyloxy-derivative umbrelliprenin. The findings reported herein enforce and underline the role of ferulic acid as an elicitor of selected classes of secondary metabolites in apiaceous species, as recently observed. In addition to these results, a novel hitherto unknown metabolite from F. campestris, namely 7-[[(2E)-7-hydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-2H-1-benzopyran-2-one, was characterized by NMR and LC–MS analyses.

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Solid‐phase adsorption methodologies of naturally occurring anthraquinones: A review

Palumbo

Fiorito

Epifano

et al. 2023

Phytochemical Analysis

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Introduction: Solid-phase extraction applied to plant matrices is nowadays a wellvalidated technique allowing to concentrate and purify different secondary metabolites. Several classes of phytochemicals have been selectively extracted by this methodology. During the last decade attention has been focused on biologically active anthraquinones from numerous sources like edible, healthy, and medicinal plants. Objectives: The aim of this review is to provide a detailed literature survey of the solid-phase adsorption methodologies for the extraction of natural anthraquinones reported so far and to discuss and propose future directions in this field of research. Materials and Methods: Substructure search was performed in the SciFinder Scholar, PubMed, Medline, and Scopus databases. Results: The first report about application of solid-phase adsorption for the purification of anthraquinones appeared in the literature in 2002. From this date, and in particular during recent years, the most notable examples included the use of chitin-and chitosan-based polymers, of molecularly imprinted polymers, of coated magnetic nanoparticles, of miniaturized matrix solid-phase dispersion, of functionalized resins, of differently structured lamellar solids, and finally of vortex-synchronized matrix solid-phase dispersion. Conclusions:The herein detailed solid-phase adsorption methodologies are powerful tools to selectively extract natural anthraquinones and/or provide anthraquinoneenriched phytopreparations. Nevertheless, many other important methods have been applied to synthetic anthraquinones (e.g., azo dyes). These could be conveniently employed also for natural anthranoids. Studies in this field are discussed in this review article.

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An improved method for the isolation of amarogentin, the bitter principle of yellow gentian roots

Cited by 12 publications

References 21 publications

Leaves of Yellow Gentian (Gentiana lutea) as an Alternative Source of Bitter Secoiridoid Glycosides

Leaves of Yellow Gentian (Gentiana lutea) as an Alternative Source of Bitter Secoiridoid Glycosides

Modulation of the biosynthesis of oxyprenylated coumarins in calli from Ferulago campestris elicited by ferulic acid

Solid‐phase adsorption methodologies of naturally occurring anthraquinones: A review

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