Coumaroyl Flavonol Glycosides and More in Marketed Green Teas: An Intrinsic Value beyond Much-Lauded Catechins

Candela, Lorenzo; Formato, Marialuisa; Crescente, Giuseppina; Piccolella, Simona; Pacifico, Severina

doi:10.3390/molecules25081765

Cited by 14 publications

(11 citation statements)

References 61 publications

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“…In fact, the [M−H] − ion at m/z 577.1355 dissociated losing the A-ring of the flavanolic unit (−126 Da) through the heterocyclic ring fission (HRF) mechanism, producing the fragment ion at m/z 451.1030. The fragment ion at m/z 425.0863 was due to retro-Diels Alder (RDA) mechanism, and the monomeric unit at m/z 289.0710 was generated through the quinone methide fission [37]. Moreover, the deprotonated molecular ion at m/z 289.0708 for compound 15 was in accordance with the molecular formula C 15 H 14 O 6 and (epi)catechin compound.…”

Section: Flavonoidsmentioning

confidence: 92%

UHPLC-HRMS Analysis of Fagus sylvatica (Fagaceae) Leaves: A Renewable Source of Antioxidant Polyphenols

et al. 2021

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European beech (Fagus sylvatica L.) is a deciduous tree, widely distributed in Europe and largely appreciated for its wood and nutritive nuts. Beech leaf also enjoys food use as salad, but an understanding of its nutraceutical value is still far from being achieved. Indeed, and also taking into account beech leaf as a consistent biomass residue available beechwood production and use, it needs to be explored as a valuable renewable specialized source of bioactive molecules. In this context, an untargeted ultra-high-performance liquid chromatography hyphenated with high resolution mass spectrometry (UHPLC-HRMS) approach was favorably applied to a beech leaf alcoholic extract, which also was evaluated for its antiradical capability (by means of assays based on 2,2-diphenyl-1-picrylhydrazyl (DPPH) and [2,2’-azinobis-(3-ethylbenzothiazolin-6-sulfonic acid)] (ABTS) radical cation) and its ferric ion reducing power. Redox mitochondrial activity towards Caco-2 cells paved the way to explore the extract’s capability to inhibit intracellular Reactive Oxygen Species (ROS) using 2’,7’dichlorofluorescin diacetate (DCFH-DA) assay. Hydroxycinnamoyl derivatives, mainly belonging to the chlorogenic acid class, and flavonoids were the main constituents. Uncommon flavanone C-glycosides were also found, together with a plentiful flavonol diversity. Cell-free and cell-based assays highlight its dose-dependent antioxidant efficacy, providing a foundation for further investigation of beech leaf constituents and its valorization and use as a reservoir of bioactive natural products with potential nutraceutical applications.

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Section: Flavonoidsmentioning

confidence: 92%

UHPLC-HRMS Analysis of Fagus sylvatica (Fagaceae) Leaves: A Renewable Source of Antioxidant Polyphenols

et al. 2021

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“…TOF-MS/MS spectra clearly displayed typical catechins’ neutral losses attributable to decarboxylation and A-ring cleavage, as well as the characteristic HRF ion at m / z 125.0247 and 125.0252. In the MS 2 spectrum of compound 9 , the base peak at m / z 109.0308 could be due to deprotonated catechol moiety (B ring), whereas the ion at m / z 123.0461 was from the benzofurane-forming fission reaction [ 27 ].…”

Section: Resultsmentioning

confidence: 99%

Theobromacacao Criollo var. Beans: Biological Properties and Chemical Profile

Lavorgna

Pacifico

Nugnes

et al. 2021

Foods

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Theobroma cacao provides precious products such as polyphenol-rich beans that are useful for nutraceutical purposes. The geographical area may influence the chemical composition of raw cocoa beans in terms of the polyphenols and biological qualities of the products. This work aimed to investigate the biological properties and the chemical composition of two different samples of Criollo var. cocoa raw beans coming from two areas (Indonesia; Peru). Beans underwent biphasic extraction obtaining lipophilic and hydroalcoholic extracts. The extracts were tested for antiradical, antimutagenic, and antigenotoxic effects. Cell viability inhibition toward breast, gastric/esophageal colorectal adenocarcinoma, and hepatoblastoma human cell lines was evaluated. Extracts were chemically investigated through UV-Vis spectroscopy and ultra-high-pressure liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry (UHPLC-ESI-QqTOF MS/MS). Results showed that the Indonesian bean hydroalcoholic extracts were able to scavenge 2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) cation radical better than the Peruvian hydroalcoholic extracts (ECs50: 72.63 vs. 322.20 μg/mL). Extracts showed antimutagenic and antigenotoxic activity. The viability inhibitory effect on breast and hepatic cancer cells was reached only for the Indonesian hydroalcoholic extracts at hundreds of μg/mL. Phenylpropenoyl-L-amino acids, hydroxycinnamoyl aminoacids conjugates, and procyanidin compounds were found mainly in the hydroalcoholic extracts, whereas fatty acids and lyso-phospholipids were found mainly in lipophilic fractions. Fatty acid and (epi)catechins appeared to be affected by different environmental conditions of the geographical areas.

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“…Briefly, the peroxyl radical reacts with fluorescein (FL, marker ) to form a non-fluorescent product, which can be easily quantified by spectrofluorimetric measurements. The antioxidant capacity was determined by the decreasing rate and the loss of fluorescence, due to the oxidation of the marker over time [ 34 ]. ΔAUC values (AUC = Area Under Curve) could be calculated as the difference of areas below the decay curve of fluorescein in the tested sample and the blank ( Figure 4 ).…”

Section: Resultsmentioning

confidence: 99%

Chemical Fractionation Joint to In-Mixture NMR Analysis for Avoiding the Hepatotoxicity of Teucrium chamaedrys L. subsp. chamaedrys

et al. 2021

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Dietary supplements based on Teucrium chamaedrys L. subsp. chamaedrys aerial parts were banned, due to the hepatotoxicity of furan-containing neo-clerodane constituents. Indeed, the plant leaf content in phenolic compounds could be further exploited for their antioxidant capability. Accordingly, bio-guided fractionation strategies have been applied, obtaining seven partially purified extracts. These latter were chemically investigated through 1D and 2D NMR techniques and tested for their antiradical, reducing and cytotoxic capability. Data acquired highlighted that, through a simple phytochemical approach, a progressive neo-clerodane depletion occurred, while maximizing phenylethanoid glycosides in alcoholic fractions. Thus, although the plant cannot be used as a botanical remedy as such, it is suggested as a source of healthy compounds, pure or in mixture, to be handled in pharmaceutical, nutraceutical and/or cosmeceutical sectors.

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Coumaroyl Flavonol Glycosides and More in Marketed Green Teas: An Intrinsic Value beyond Much-Lauded Catechins

Cited by 14 publications

References 61 publications

UHPLC-HRMS Analysis of Fagus sylvatica (Fagaceae) Leaves: A Renewable Source of Antioxidant Polyphenols

UHPLC-HRMS Analysis of Fagus sylvatica (Fagaceae) Leaves: A Renewable Source of Antioxidant Polyphenols

Theobromacacao Criollo var. Beans: Biological Properties and Chemical Profile

Chemical Fractionation Joint to In-Mixture NMR Analysis for Avoiding the Hepatotoxicity of Teucrium chamaedrys L. subsp. chamaedrys

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