Umbelliferone instability during an analysis involving its extraction process

Abstract

Umbelliferone (7-hydroxycoumarin) is one of the most popular compounds of the coumarins family. This compound receives the attention of scientists due to its diverse bioactivities in a number of applications in various therapeutic fields. An interesting aspect of umbelliferone is its structural lability. The enzymatic degradation process of umbelliferone to its hydroxylated (esculetin), glucosylated (skimmin), and methylated (herniarin) derivatives is already known from the literature. In this paper, we describe the possibility of umbelliferone transformation to other derivatives. We found that eight compounds were formed from umbelliferone during its simulated extraction under reflux performed in different conditions (different heating times and solvents used). Six of them (4,7-dihydroxy-3,4-dihydro-2H-chromen-2-one, 3,7-dihydroxy-3,4-dihydro-2H-chromen-2-one, methyl (2E)-3-(2,4-dihydroxyphenyl)prop-2-enoate, ethyl (2E)-3-(2,4-dihydroxyphenyl)prop-2-enoate, (2E)-3-[2-(acetyloxy)-4-hydroxyphenyl]prop-2-enoic acid, (2E)-3-(2-amino-4-hydroxyphenyl)prop-2-enoic acid) have not been reported yet. Some of these compounds were also identified in extracts of plant materials containing umbelliferone—chamomile flower and cinnamon bark. Compound separation was carried out using the HPLC apparatus. All compounds were identified based on their MS fragmentation paths. The presented results are useful for food producers and consumers, as umbelliferone transformation products can be formed during food product storage, their preparation or processing.Graphical abstract Electronic supplementary materialThe online version of this article (10.1007/s00706-018-2188-9) contains supplementary material, which is available to authorized users.

Exploring the Potential of Supercritical Fluid Extraction of Matricaria chamomilla White Ray Florets as a Source of Bioactive (Cosmetic) Ingredients

“…Plant coumarins, often called phytoalexins, are believed to be compounds that help plants defend themselves when living and nonliving things cause stress [74]. The literature previously described the enzymatic breakdown of umbelliferone (COU2) to its glucosylated (skimmin (COU1)) and methylated (herniarin (COU3)) derivatives [75]. Our results support what other studies have found: higher concentrations of herniarin than umbelliferone can be extracted from chamomile flower heads [40,76].…”

Emission Color Tuning and White Light Generation from a Trimolecular Cocktail in Cationic Micellar System with Promising Applicability in the Anticounterfeiting Technology

“…The pH-dependent spectral properties of FLU have been already elaborated in the literature , and have been attributed to the existence of different protolytic forms of the dye and the occurrence of protolytic reactions in the excited state (Scheme S1). Even though some researchers have elucidated the pH-dependent spectral properties of UMB , , there is a lack of literature studies explaining the relation between its fluorescence behavior and the corresponding structural changes vis-a-vis pH variation.…”

Extraction of bioactive coumarins from lime peel as sample pretreatment before chromatographic analysis

“…Organic solvents are mostly used in extraction of coumarins from different matrices; however, extraction methods operating at higher temperatures, pressures, or with energy field assistance offer some advantages such as lower organic solvent consumption and shorter extraction time (Rodríguez-García and Raghavan, 2022) 1). However, such high temperatures may cause the decomposition of thermolabile components and extraction of undesirable impurities (e.g., umbelliferone is chemically and thermally unstable, which may result in many compounds formed during its reflux extraction by methanol, ethanol, buffers, and buffered or non-buffered alcohol/water mixtures (Dawidowicz et al, 2018)). Extraction efficiency depends also on the extraction time and mostly increases with the increased extraction time in a certain time interval.…”