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In this study, an ethanolic extract from Portuguese propolis was prepared, fractionated by high-performance liquid chromatography, and the identification of the phenolic compounds was done by electrospray mass spectrometry in the negative mode. This technical approach allowed the identification of 37 phenolic compounds, which included not only the typical phenolic acids and flavonoids found in propolis from temperate zones but also several compounds in which its occurrence have never been referred to in the literature. Four of the novel phenolic compounds were methylated and/or esterified or hydroxylated derivatives of common poplar flavonoids, although six peculiar derivatives of pinocembrin/pinobanksin, containing a phenylpropanoic acid derivative moiety in their structure, were also identified. Furthermore, the Portuguese propolis sample was shown to contain a p-coumaric ester derivative dimer. [ABSTRACT FROM AUTHOR]

In the present study, aqueous extracts of Salvia africana, Salvia officinalis 'Icterina' and Savia mexicana origin were screened for their phenolic composition and for antibacterial, antioxidant, anti-inflammatory and cytotoxic properties. The three aqueous extracts contained distinct phenolic compounds, with S. africana presenting the highest total levels (231.6 ± 7.5 μg/mg). Rosmarinic acid was the dominant phenolic compound in all extracts, yet that of S. africana origin was characterized by the present of yunnaneic acid isomers, which overall accounted for about 40% of total phenolics. In turn, S. officinalis 'Icterina' extract presented glycosidic forms of apigenin, luteolin and scuttelarein, and the one obtained from S. mexicana contained several simple caffeic acid derivatives. S. africana aqueous extract exhibited high antioxidant potential in four methods, namely the DPPH• (2,2-diphenyl-1-picrylhydrazyl) scavenging ability, iron-reducing power, inhibition of β-carotene bleaching and of thiobarbituric acid reactive substances (TBARS), for which EC50 values were equal or only 1.3–3.1 higher than those of the standard compounds. Moreover, this extract was able to lower the levels of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages (EC50 = 47.8 ± 2.1 μg/mL). In addition, the three sage aqueous extracts showed promising cytotoxic effect towards hepatocellular HepG2, cervical HeLa, and breast carcinoma cells MCF-7. Overall this study highlights the potential of three little-exploited Salvia species, with commercial value for applications in food or pharmaceutical industries. [ABSTRACT FROM AUTHOR]

To explore whether and how glucuronidation affects pyrogallol-type phytophenols, scutellarein and scutellarin (scutellarein-7-O-glucuronide) were comparatively investigated using a set of antioxidant analyses, including spectrophotometric analysis, UV-vis spectra analysis, and ultra-performance liquid chromatography coupled with electrospray ionization-quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) analysis. In spectrophotometric analyses of the scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH•), 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+•), and 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radicals (PTIO•) and the reduction of Cu2+ ions, scutellarein showed lower IC50 values than scutellarin. However, in •O2−-scavenging spectrophotometric analysis, scutellarein showed higher IC50 value than scutellarin. The analysis of UV-Vis spectra obtained after the Fe2+-chelating reaction of scutellarin showed a typical UV-Vis peak (λmax = 611 nm), while scutellarein showed no typical peak. In UPLC-ESI-Q-TOF-MS/MS analysis, mixing of scutellarein with DPPH• yielded MS peaks (m/z 678, 632, 615, 450, 420, 381, 329, 300, 288, 227, 196, 182, 161, and 117) corresponding to the scutellarein-DPPH adduct and an MS peak (m/z 570) corresponding to the scutellarein-scutellarein dimer. Scutellarin, however, generated no MS peak. On the basis of these findings, it can be concluded that glucuronidation of pyrogallol-type phytophenol antioxidants has a dual effect. On the one hand, glucuronidation can decrease the antioxidant potentials (except for •O2− scavenging) and further lower the possibility of radical adduct formation (RAF), while on the other hand, it can enhance the •O2−-scavenging and Fe2+-chelating potentials. [ABSTRACT FROM AUTHOR]

Thymus x citriodorus is a Lamiaceae plant extensively cultivated in the Mediterranean region and used for centuries in culinary and in traditional medicine. The present work describes the detailed phenolic composition of T. x citriodorus for the first time, by means of HPLC–DAD, ESI–MS and MSn and nuclear magnetic resonance (NMR) analyses. The ethanolic extract of T. x citriodorus was analyzed by reversed phase HPLC. The method of analysis was also validated concerning its linearity, instrumental and method precision (for repeatability, immediate precision and intermediate precision) and accuracy (absolute recovery study). The technique was combined with electrospray mass spectrometry in order to identify the phenolic compounds and the structure of the main phenolics was also confirmed by NMR analysis. The in-house validated HPLC–DAD method showed good linearity for the tested reference compounds as well as satisfactory repeatability and immediate precision values, for both instrument and method. Furthermore, the satisfactory results of intermediate precision analysis and recovery assays indicated that the chromatographic method could be used to quantify the main phenolic compounds of T. x citriodorus with adequate precision and accuracy. The extract was rich in rosmarinic acid (10.4±0.6mg/g extract) that is a widespread phenolic acid in Thymus plants, but also in luteolin-7-O-α-glucuronide (12±2mg/g extract), that was herein reported in Thymus for the first time. Other novel compounds comprised one eriodictyol dihexoside with O-glycosidic linkages, two eriodictyol-O-monohexosides, one quercetagetin dimethyl ether-O-hexoside, one naringenin-O-hexoside and chrysoeriol-7-β-O-glucoside. Having in mind the health-promoting properties reported in literature for some of the main polyphenols found in T. x citriodorus, we suggest that this plant has a high potential for being used as a functional food. [ABSTRACT FROM AUTHOR]

Abstract: The phenolic composition of the ethanolic extract obtained from the flowers of the medicinal plant Cytisus multiflorus has been elucidated by high performance liquid chromatography, electrospray mass spectrometry and nuclear magnetic resonance analysis. The extract was mainly composed of flavones, including the common chrysin, orientin, luteolin-5-O-glucoside, luteolin-7-O-glucoside, apigenin and apigenin-7-O-glucoside, which appeared as minor components. The major flavone in the extract was chrysin-7-O-β-d-glucopyranoside, and it also contained moderate amounts of a dihydroxyflavone isomer of chrysin, as well as of 2″-O-pentosyl-6-C-hexosyl-luteolin, 2″-O-pentosyl-8-C-hexosyl-luteolin and 6″-O-(3-hydroxy-3-methylglutaroyl)-2″-O-pentosyl-C-hexosyl-apigenin, which are not commonly found in the Fabaceae family. Other novel phenolic compounds found in the ethanolic extract of C. multiflorus comprised the flavones 2″-O-pentosyl-6-C-hexosyl-apigenin, 2″-O-pentosyl-8-C-hexosyl-apigenin and 6″-O-(3-hydroxy-3-methylglutaroyl)-2″-O-pentosyl-C-hexosyl-luteolin. The assessment of the biological activities of the main compounds of this extract are now keen, in order to determine their relevance in the beneficial properties of the plant. [Copyright &y& Elsevier]