Rindera graeca is a Greek endemic plant of the Boraginaceae family which has never been studied before. Consequently, this study attempted to phytochemically examine the aerial parts of this species. Nine phenolic secondary metabolites were identified, consisting of seven caffeic acid derivatives and two flavonol glucosides, namely rutin and quercetin-3-rutinoside-7-rhamnoside. These flavonoids, together with rosmarinic acid, were isolated via column chromatography and structurally determined through spectral analysis. Quercetin-3-rutinoside-7-rhamnoside is an unusual triglycoside, which is identified for the first time in Rindera genus and among Boraginaceae plants. This metabolite was further examined with thermal analysis and its 3D structure was simulated, revealing some intriguing information on its interaction with biological membrane models, which might have potential applications in microcirculation-related conditions. R. graeca was also analyzed for its pyrrolizidine alkaloids content, and it was found to contain echinatine together with echinatine N-oxide and rinderine N-oxide. Additionally, the total phenolic and flavonoid contents of R. graeca methanol extract were determined, along with free radical inhibition assays. High total phenolic content and almost complete inhibition at experimental doses at the free radical assays indicate a potent antioxidant profile for this plant. Overall, through phytochemical analysis and biological activity assays, insight was gained on an endemic Greek species of the little-studied Rindera genus, while its potential for further applications has been assessed.
This study focuses on the phytochemical analysis of the aerial parts of three Alkanna species: A. orientalis (L.) Boiss., A. tinctoria Tausch. and A. kotschyana A. DC. (Boraginaceae) growing wild in the Mediterranean basin, as mostly the roots of the genus have been widely researched. Their methanol extracts were subjected to qualitative LC-MS analyses, resulting in the annotation of 28 different secondary metabolites, with 27 originating from A. orientalis, 25 from A. tinctoria and 23 from A. kotschyana. The detected metabolites are categorized into three chemical types: organic acids (2), flavonoids and their glycosides (17), and caffeic acid derivatives (9). Furthermore, the chemical profiles of the three species are discussed chemotaxonomically. Caffeic acid and its derivatives, along with glucosides of quercetin and kaempferol, were identified in all three studied species. Additionally, their total phenolic and flavonoid contents were determined. The antioxidant capacity was evaluated through various chemical assays, as well as their in vitro enzyme inhibitory properties towards cholinesterases (AChE and BChE), α-amylase and α-glucosidase. The results showed that A. tinctoria exhibited the strongest antioxidant activity (211 mgTE/g extract in DPPH and 366 mgTE/g extract in ABTS), probably due to its high total phenolic (53.3 mgGAE/g extract) and flavonoid (20.8 mgRE/g extract) content, followed by A. kotschyana. These chemical and biological findings provide valuable insights for potential promising applications of the aerial parts of the species outside of the well-known uses of their roots.
The aim of the present study was the phytochemical analysis of the aerial parts of Heliotropium procumbens Mill., a herb from Boraginaceae plant family not previously studied. The methanol (ME) and aqueous extracts (WE) of the aerial parts were assayed for their total phenolic and flavonoid content and antioxidant properties, using free radical scavenging (DPPH, ABTS), reducing power (FRAP, CUPRAC), phosphomolybdenum and metal chelating assays. The extracts displayed considerable free radical scavenging activity against DPPH and ABTS radicals, with potential values of 46.88 and 68.31 mg TE/g extract for ME, and 93.43 and 131.48 mg TE/g extract for WE, respectively. Key clinical enzymes involved in neurodegenerative diseases AChE and BChE, diabetes (α-amylase and α-glucosidase) and skin whitening (tyrosinase) were also assayed. The phytochemical profile of the studied species was determined through UHPLC–HRMS, whereby 26 secondary metabolites were identified, three of which (luteolin-7-glucoside, lithospermic and rosmarinic acids) were isolated and structurally determined by NMR spectral means. H. procubens was found to harbor bioactive metabolites and could, hence, serve as a source of biological activities which could be further explored and exploited for potential applications.
This study aimed to assess the impact of genotype, location, and type of cultivation (organic) on the nutrient and anti-nutrient components of seven large-seeded bean (Phaseolus vulgaris L.) populations. All genotypes were cultivated during 2014 and 2015 in randomized complete block (RCB) experimental designs in three areas of the Prespa region (Pili, Patoulidio, Agios Germanos) in Greece. Particularly, total protein (18.79–23.93%), fiber (7.77–12%), starch (40.14–55.26%), and fat (1.84–2.58%) contents were analyzed and showed significant differences. In order to assess mineral content, firstly, the total ash percentage (4.31% to 5.20%) and secondly, trace elements and heavy metals were determined. The concentrations of identified inorganic metals showed large variations. The total phenolic content of the samples varied from 0.18 to 0.29 mg/g gallic acid equivalent (GAE). A major limitation of increasing the use of grain legumes as feed is the presence of diverse compounds in their grain, commonly referred to as antinutritional factors, and these are mainly trypsin inhibitors. Trypsin inhibitor levels were evaluated, with results varying from 21.8 to 138.5 TIU/g. Pili 2014 and 2015 were differently associated regarding the year of cultivation. Pili 2015 location was also very closely associated with the Patoulidio region, whereas Agios Germanos and Pili 2014 were the most different in terms of nutritional and antinutritional content.
As part of our ongoing research on phytoconstituents that can act as promising antimicrobial agents, the essential oils of nine selected Apiaceae plants, cultivated in Poland, were studied. The volatiles of the aerial parts with fruits (herba cum fructi) of Silaum silaus, Seseli devenyense, Seseli libanotis,Ferula assa-foetida, Glehnia littoralis and Heracleum dulce, in addition to the fruits (fructi) of Torilis japonica and Orlaya grandiflora as well as of the aerial parts (herba) of Peucedanum luxurians were investigated through Gas Chromatography–Mass Spectrometry to identify more than 60 different metabolites. The essential oils from S. devenyense, H. dulce, T. japonica and P. luxurians are reported for the first time. All examined species were also assayed for their antimicrobial activities against several human pathogenic Gram-positive and -negative bacteria and fungi. The species H. dulce, S. devenyense and S. libanotis exerted the strongest antimicrobial activity, mostly against Gram-positive bacteria strains (MIC values 0.90–1.20 mg/mL). To the best of our knowledge, this is the first attempt to determine the antimicrobial activity of the above Apiaceae species.
The volatiles of different aerial parts of three kumquat species (Fortunella margarita Swingle–Nagami, Fortunella japonica Swingle–Marumi, and Fortunella crassifolia Swingle–Meiwa) growing in Greece were analyzed via GC-MS and evaluated for their antimicrobial properties against nine human pathogenic microorganisms. A total number of 23 compounds were identified in the peel, 38 in the leaves, and 30 in the flowers of the examined species. Limonene was the dominant metabolite in the peels of all three species, germacrene-D was present in the leaves of Nagami and Marumi kumquats, while limonene was the most abundant in the flower of Marumi and Meiwa kumquat but with significant differences in the composition of the total fracture of the essential oil, since compounds with high antimicrobial activity were only present in the flower of Meiwa kumquat. The essential oils from the leaf and peel of the three kumquat species were either inactive or showed weak antimicrobial activity, respectively, against Gram-positive and Gram-negative bacterial strains and pathogenic fungi. Only the essential oil from the flower of F. crassifolia Swingle (Meiwa) showed a stronger effect (MIC values 3.5–7.48 mg/mL) against all the assayed microorganisms. Furthermore, through multivariate statistical analysis, we studied the relationships between the samples regarding their origin (species and plant part), as well as between the chemical composition of the corresponding essential oils and their antimicrobial activity. Considering its chemical profile and antimicrobial activity, the Greek Meiwa flowers’ essential oil seemed a promising essential oil for further exploitation in the food and/or medicinal industry.