Molecular networking-assisted flavonoid profile of Gypsophila glomerata extract in relation to its protective effects on carbon tetrachloride-induced hepatorenal damage in rats

The aim of the study was to provide an in-depth characterization of the methanol-aqueous extract from the aerial parts of Gypsophila glomerata Pall. Ex Adams (Caryophyllaceae) (EGG) and to assess its protective potential on carbon tetrachloride (CCl4)-induced liver and kidney damage in male Wistar rats. Twenty-two flavonoid C-, O- and C,O-glycosides in EGG were annotated by mass spectrometry-based molecular networking; nine of them are reported in this species for the first time. Fourteen-day oral administration of EGG at a dose 200 mg kg–1 bm prevented significantly CCl4-induced liver injury, discerned by an amelioration of the markers of oxidative stress (GSH and MDA) and transaminase activity. EGG decreased the serum level of urea and creatinine as well. The observed improvement of biochemical parameters was supported by histopathological observations. The protective hepatorenal effects of EGG, rich in 2"-О-pentosyl-6-С-hexosyl-apigenin/luteolin/methylluteolin and their acetyl- and methoxycinnamoyl-derivatives, were comparable with the effects of the positive control silymarin

LC-MS analysis of phenolic compounds and oleraceins in aerial parts of Portulaca oleracea L.

Portulaca oleracea L. (purslane) is a well-known edible and ethnomedicinal plant and it has been called “vegetable for long life” in the Chinese herbal medicine. The plant is recognized for the high content of polyphenols, including flavonoids and phenolic acids.In this study, hydromethanolic purslane extracts from Bulgarian and Greek locations were screened for polyphenolic content. Based on polyphenols, saponins and DPPH antioxidant activity, an orthogonaldesign L9(34) was performed in order to improve the ultrasound assisted extraction procedure of dry and fresh plant material. An UHPLC-Orbitrap-MS method in parallel-reaction monitoring mode was developed for the simultaneous identification and quantification of 14 compounds comprising hydroxybenzoic, hydroxycinnamic and caffeoylquinic acids, as well as 2 flavonol glycosides. The quantitative analysis was validated for curve fit, range, instrumental detection limit (IDL), instrumental quantification limit (IQL), LOD, LOQ, precision, recovery and accuracy. The UHPLC-MS quantification method revealed good linearity (r2 > 0.9950), LOD < 925.85 ng/g dw and LOQ < 3055.31 ng/g dw. Moreover, 11 cylco-dopa amides (Oleraceins A-D, N-Q, S, U and W) were tentatively identified through UHPLC-MS and their MS2 mass fragmentation was described

Innovative Biochemometric Approach to the Metabolite and Biological Profiling of the Balkan Thistle (Cirsium appendiculatum Griseb.), Asteraceae

The widespread genus Cirsium Mill. (Asteraceae) is renowned in traditional medicine. In the present study, an innovative biochemometric-assisted metabolite profiling of the flower heads, aerial parts and roots of Cirsium appendiculatum Griseb. (Balkan thistle) in relation to their antioxidant and enzyme inhibitory potential was developed. The workflow combines ultra-high-performance liquid chromatography–high-resolution mass spectrometry (UHPLC–HRMS) with partial least-square analysis to discriminate the herbal extracts and identify the most prominent biological activities. The annotation and dereplication of 61 secondary metabolites were evidenced, including 15 carboxylic (including hydroxybenzoic and hydroxycinnamic) acids and their glycosides, 11 acylquinic acids, 26 flavonoids and 9 fatty acids. All compounds were reported for the first time in the studied species. The root extract revealed the highest cupric and ferric reducing power (618.36 ± 5.17 mg TE/g and 269.89 ± 8.50 mg TE/g, respectively) and antioxidant potential in phosphomolybdenum (3.36 ± 0.15 mmol TE/g) as well as the most prominent enzyme inhibitory potential on α-glucosidase (0.72 ± 0.07 mmol ACAE/g), acetylcholinesterase (4.93 ± 0.25 mg GALAE/g) and butyrylcholinesterase (3.80 ± 0.26 mg GALAE/g). Nevertheless, the flower heads were differentiated by their higher metal chelating activity (32.53 ± 3.51 mg EDTAE/g) and total flavonoid content (46.59 ± 0.89 mgRE/g). The partial least-square discriminant and heat-map analysis highlighted the root extract as the most active and a promising source of bioactive compounds for the therapeutic industry

The genus Rubus L.: An insight into phytochemicals and pharmacological studies of leaves from the most promising species

Rubus L. species (Rosaceae) are traditionally used worldwide for their food and medicinal properties. Although raspberries and blackberries are well-known fruits, the leaves hold significant but often overlooked value. The review is focused on the phytochemicals and pharmacological studies on leaves from the most promising taxa. Through a comprehensive search of the MEDLINE, Scopus, and Web of Science databases, numerous research articles were identified. The studies revealed over 160 diterpenoids, triterpenoid acids, saponins, ellagitannins, phenolic and acylquinic acids, and flavonoids in the discussed Rubus species. These compounds contribute to the leaves’ protective effects, including astringent, hypoglycemic, and wound healing activity. Moreover, Rubus leaves are used for relieving diarrhea as well as in the treatment of ulcerative colitis, owing to their anti-inflammatory and antioxidant properties. This review highlights R. sanctus, R. ibericus, and R. chingii, along with R. idaeus, as prospective raw materials for therapeutic applications

The most promising Southeastern European Tanacetum species: a review of chemical composition and biological studies

Several species of the genus Tanacetum L. (Asteraceae) spread in the Southestern Europe are traditionally used as medicinal and aromatic plants, including T. vulgare, T. parthenium, T. macrophyllum, T. balsamita, T. poteriifolium. The review is focused on the phytochemical and pharmacological studies of these taxa. Major chemical constituents are acylquinic acids, sesquiterpenes, sesquiterpene lactones, methoxylated flavonoids. An in-depth depiction of more than 100 secondary metabolites was achieved in Tanacetum species by liquid chromatography-high resolution mass spectrometry. The ethnopharmacological studies indicate that species possess antioxidant, enzyme inhibitory and cytotoxic activity along with antimicrobial and antiviral effects. Reports revealed anti-inflamatory and neuromodulatory activity involved in the pharmacological approach in counteracting migraine attacks. Multivariate data analysis allowed the identification of the most discriminant metabolites and bioactivities in the herbal drugs. This review emphasizes T. vulgare, T. macrophyllum, T. balsamita and T. parthenium as potential raw material for health-promoting application in pharmaceutical area

Chemophenetic Approach to Selected Senecioneae Species, Combining Morphometric and UHPLC-HRMS Analyses

Herein, a chemophenetic significance, based on the phenolic metabolite profiling of three Senecio (S. hercynicus, S. ovatus, and S. rupestris) and two Jacobaea species (J. pancicii and J. maritima), coupled to morphometric data, is presented. A set of twelve morphometric characters were recorded from each plant species and used as predictor variables in a linear discriminant analysis (LDA) model. From a total 75 observations (15 from each of the five species), the model correctly assumed their species’ membership, except for 2 observations. Among the studied species, S. hercynicus and S. ovatus presented the greatest morphological similarity. A phytochemical profiling of phenolic specialized metabolites by UHPLC-Orbitrap-MS revealed 46 hydroxybenzoic, hydroxycinnamic, and acylquinic acids and their derivatives, 1 coumarin and 21 flavonoids. Hierarchical and PCA clustering applied to the phytochemical data corroborated the similarity of S. hercynicus and S. ovatus, observed in the morphometric analysis. This study contributes to the phylogenetic relationships between the tribe Senecioneae taxa and highlights the chemophenetic similarity/dissimilarity of the studied species belonging to Senecio and Jacobaea genera

Antioxidant and enzyme-inhibiting activity of lyophilized extract from Clinopodium vulgare L. (Lamiaceae)

Clinopodium vulgare L. (Lamiaceae) was used in the traditional Bulgarian medicine for treatment of wounds, diabetes and gastric ulcers. The aim of the present study was to evaluate the antioxidant capacity of the extract (CVE) and fractions from C. vulgare (CV) using DPPH, ABTS and FRAP methods. Enzyme inhibitory activity against acetylcholinesterase, α-glucosidase and α-amylase was also investigated. Rosmarinic acid was used as a positive control. The fraction CV3 demonstrated the highest radical scavenging activity with IC50 values of 0.02 mg/ml (DPPH) and 0.0002 mg/ml (ABTS), as well as the strongest ferric reducing potential (FRAP) of 0.89 mM TE/mg dw. The crude aqueous-methanol extract of C. vulgare also showed high activity with IC50 values of 0.05 mg/ml (DPPH), 0.04 mg/ml (ABTS) and 0.89 mM TE/mg dw (FRAP). Moreover, CV3 demonstrated moderate α-glucosidase and α-amylase inhibitory potential

Isoetin 2′-<i>O</i>-α-<span style="font-variant: small-caps">l</span>-arabinopyranoside-5′-<i>O</i>-β-<span style="font-variant: small-caps">d</span>-glucopyranoside

Isoetin derivatives are a rare class of flavonoids with a rather erratic occurrence across the plant kingdom. The Cichorieae tribe of the Asteraceae family has proven to be a rich source and a centre of chemical diversity of this class of compounds. Here, we describe the chromatographic isolation and mainly NMR-based structure elucidation of a previously undescribed isoetin derivative from Leontodon hispidus L. (Asteraceae, Cichorieae). The chemophenetic relevance is discussed briefly