UHPLC-UV/Vis Quantitative Analysis of Hydroxylated and O-prenylated Coumarins in Pomegranate Seed Extracts

Abstract

A simple and rapid analytical UHPLC methodology with spectrophotometric (UV/Vis) detection, coupled with different extraction procedures, has been perfected to investigate the presence of biologically active O-prenylated umbelliferone derivatives, such as auraptene and umbelliprenin, in pomegranate (Punica granatum L.) seed extracts. Absolute ethanol was the most efficient extraction solvent in terms of yields, after a short ultrasound-assisted. The highest concentration values recorded under these experimental conditions were 1.99 μg/g of dry extract and 6.53 μg/g for auraptene and umbelliprenin, respectively. The parent metabolite umbelliferone was also detected (0.67 μg/g). The extraction and UHPLC analytical methodology set up in the present study proved to be an efficient, powerful, and versatile technique for the simultaneous qualitative analysis and quantification of oxyprenylated coumarins in pomegranate seed extracts. The characterization of such secondary metabolites in the mentioned phytopreparation represents, to the best of our knowledge, the first example in the literature.

Promising New Inhibitors of Tyrosyl-DNA Phosphodiesterase I (Tdp 1) Combining 4-Arylcoumarin and Monoterpenoid Moieties as Components of Complex Antitumor Therapy

“…In particular, a large number of coumarin derivatives with high antitumor activity have been found in recent years [7][8][9][10][11][12][13][14][15][16][17][18]. Natural derivatives of 7-hydroxycoumarin containing terpene fragments have also attracted the attention of the medicinal chemistry community [19][20][21]. The best-known compound of this structural type is auraptene (Figure 1), for which a variety of biological activities are known, including antitumor properties [22].…”

Rhaphiolepis indica Fruit Extracts for Control Fusarium solani and Rhizoctonia solani, the Causal Agents of Bean Root Rot

“…The identification of the polyphenolic components present in the Rhaphiolepis fruits extract (acetone and hexane) was carried out using an HPLC analysis with an Agilent 1260 series. The extraction process was conducted as previously described [30] and Fiorito et al [31]. The chromatographic separation was conducted utilizing an Eclipse C18 column with dimensions of 4.6 mm inner diameter, 250 mm length, and a particle size of 5 µm.…”

Auraptene and umbelliprenin: a review on their latest literature acquisitions

“…Auraptene 2is the most abundant geranyloxycoumarin found in nature and its natural sources have been reviewed in 2011 for the first time (Genovese and Epifano 2011). In more recent years its presence has been also documented in the following plants: grapefruit (Citrus x paradisi Macfad) peels (Genovese et al 2020), Ferula assa-fetida L. rhizome dried latex (Eidi et al 2020), and pomegranate (Punica granatum L.) seeds (Fiorito et al 2019b), and Eremurus persicus (Joub & Spach) Boiss crude extract of the whole plant (Mottaghipisheh et al 2020). Although few, papers on the analysis of auraptene from novel plant sources appeared across the end of 2019 and the mid of 2020 have all substantial elements of novelty.…”

“…Amaranthaceae) (Fiorito et al 2017), Anethum greaveolens L., Pimpinella anisum L., Angelica archangelica L. (Apiaceae) (Taddeo et al 2017), Melaleuca alternifolia (Maiden & Betche) Cheel (Fam. Myrtaceae) (Scotti et al 2018), Punica granatum L. (Fiorito et al 2019b), Spinacia oleracea L. (Fam. Amaranthaceae), Lycium barbarum L. (Fam.…”