The compositions of volatile components in the aerial parts of six Astragalus species, namely A. campylotrichus (Aca), A. chiwensis (Ach), A. lehmannianus (Ale), A. macronyx (Ama), A. mucidus (Amu) and A. sieversianus (Asi), were investigated using gas chromatograph-mass spectrometry (GC-MS) analysis. Ninety-seven metabolites were identified, accounting for 73.28, 87.03, 74.38, 87.93, 85.83, and 91.39% of Aca, Ach, Ale, Ama, Amu and Asi whole oils, respectively. Sylvestrene was the most predominant component in Asi, Amu and Ama, with highest concentration in Asi (64.64%). In addition, (E)-2-hexenal was present in a high percentage in both Ale and Ach (9.97 and 10.1%, respectively). GC-MS based metabolites were subjected to principal component analysis (PCA) and hierarchal cluster analysis (HCA) to explore the correlations between the six species. The PCA score plot displayed clear differentiation of all Astragalus species and a high correlation between the Amu and Ama species. The antioxidant activity was evaluated in vitro using various assays, phosphomolybdenum (PM), 2,2 diphenyl-1-picryl-hydrazyl-hydrate (DPPH), 2,2-azino bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), cupric reducing antioxidant capacity (CUPRAC), ferric reducing power (FRAP) and ferrous ion chelation (FIC) assays. In addition, the potential for the volatile samples to inhibit both acetyl/butyrylcholinesterases (AChE, BChE), α- amylase, α-glucosidase and tyrosinase was assessed. Most of the species showed considerable antioxidant potential in the performed assays. In the DPPH assay, Ama exhibited the maximum activity (24.12 ± 2.24 mg TE/g sample), and the volatiles from Amu exhibited the highest activity (91.54 mgTE/g oil) in the ABTS radical scavenging assay. The effect was more evident in both CUPRAC and FRAP assays, where both Ale and Ama showed the strongest activity in comparison with the other tested species (84.06, 80.28 mgTE/g oil for CUPRAC and 49.47, 49.02 mgTE/g oil for FRAP, respectively). Asi demonstrated the strongest AChE (4.55 mg GALAE/g oil) and BChE (3.61 mg GALAE/g oil) inhibitory effect. Furthermore, the best tyrosinase inhibitory potential was observed for Ale (138.42 mg KAE/g). Accordingly, Astragalus species can be utilized as promising natural sources for many medicinally important components that could be tested as drug candidates for treating illnesses such as Alzheimer's disease, diabetes mellitus and oxidative stress-related diseases.

Asteraceae species Tanacetum balsamita L. (costmary) is renowned for its traditional usage as an aromatic, carminative and tonic plant. This work aimed at in-depth study of the phytochemical and in vitro biological profilings of methanol−aqueous extracts from the costmary leaves, flower heads and roots. An UHPLC-HRMS analysis revealed more than 100 secondary metabolites including 24 acylquinic acids, 43 flavonoid glycosides, aglycones and methoxylated derivatives together with 15 phenolic acids glycosides. For the first time, 91 compounds are reported in the costmary. The flower heads extract possessing the highest content of total phenolics and flavonoids, actively scavenged DPPH (84.54 ± 3.35 mgTE/g) and ABTS radicals (96.35 ± 2.22 mgTE/g), and showed the highest reducing potential (151.20 and 93.22 mg TE/g for CUPRAC and FRAP, respectively). The leaves extract exhibited the highest inhibition towards acetyl- and butyrylcholinesterase (2.11 and 2.43 mg GALAE/g, respectively) and tyrosinase (54.65 mg KAE/g). The root extract inhibited α-glucosidase (0.71 ± 0.07 mmol ACAE/g), α-amylase (0.43 ± 0.02 mmol ACAE/g) and lipase (8.15 ± 1.00 mg OE/g). At a concentration >2 µg/mL, a significant dose dependent reduction of cell viability towards THP-1 monocyte leukemic cells was observed. Costmary could be recommended for raw material production with antioxidant and enzyme inhibitory properties.

Mentha spicata is one of the most popular species in the genus, and it is of great interest as a gastrointestinal and sedative agent in the folk medicine system. In this study, different M. spicata extracts, obtained by the use of four solvents (hexane, chloroform, acetone and acetone/water) were chemically characterized using HPLC-ESI-MS n, which allowed for identification of 27 phenolic compounds. The extracts' antioxidant and enzyme inhibitory properties were investigated. In addition, neuroprotective effects were evaluated in hypothalamic HypoE22 cells, and the ability of the extracts to prevent the hydrogen peroxide-induced degradation of dopamine and serotonin was observed. The best antioxidant effect was achieved for all the extraction methods using acetone/water as a solvent. These extracts were the richest in acacetin, eriodictyol, hesperidin, sagerinic acid, naringenin, luteolin, chlorogenic acid, chrysoeriol and apigenin. The intrinsic antioxidant and enzyme inhibition properties of the acetone/water extract could also explain, albeit partially, its efficacy in preventing prostaglandin E2 overproduction and dopamine depletion (82.9% turnover reduction) in HypoE22 cells exposed to hydrogen peroxide. Thus, our observations can provide a scientific confirmation of the neuromodulatory and neuroprotective effects of M. spicata.

The Artemisia L. genus includes over five hundred species with great economic and medicinal properties. Our study aimed to provide a comprehensive metabolite and bioactivity profile of Artemisia campestris subsp. lednicensis (Spreng.) Greuter & Raab-Straube collected from north-eastern Romania. Liquid chromatography with tandem high-resolution mass spectrometry (LC-HRMS/MS) analysis of different polarity extracts obtained from the aerial parts led to the identification of twelve flavonoids, three phenolic acids, two sesquiterpene lactones, two fatty acids, one coumarin, and one lignan. The antioxidant and enzyme inhibitory properties were shown in the DPPH (0.71−213.68 mg TE/g) and ABTS (20.57−356.35 mg TE/g) radical scavenging, CUPRAC (38.56−311.21 mg TE/g), FRAP (121.68−202.34 mg TE/g), chelating (12.88−22.25 mg EDTAE/g), phosphomolybdenum (0.92−2.11 mmol TE/g), anti-acetylcholinesterase (0.15−3.64 mg GALAE/g), anti-butyrylcholinesterase (0−3.18 mg GALAE/g), anti-amylase (0.05−0.38 mmol ACAE/g), anti-glucosidase (0.43−2.21 mmol ACAE/g), and anti-tyrosinase (18.62−48.60 mg KAE/g) assays. At 100 μg/mL, Artemisia extracts downregulated the secretion of tumor necrosis factor (TNF)-α in a lipopolysaccharide (LPS)-stimulated human neutrophil model (29.05−53.08% of LPS+ control). Finally, the Artemisia samples showed moderate to weak activity (minimum inhibitory concentration (MIC) > 625 mg/L) against the seventeen tested microbial strains (bacteria, yeasts, and dermatophytes). Overall, our study shows that A. campestris subsp. lednicensis is a promising source of bioactives with putative use as food, pharmaceutical and cosmetic ingredients.

The quest for sustainable strategies aimed at increasing the bioactive properties of plant-based foods has grown quickly. In this work, we investigated the impact of exogenously applied phenolics, i.e., chlorogenic acid (CGA), hesperidin (HES), and their combinations (HES + CGA), on Lactuca sativa L. grown under normal- and mild-salinity conditions. To this aim, the phenolic profile, antioxidant properties, and enzyme inhibitory activity were determined. The untargeted metabolomics profiling revealed that lettuce treated with CGA under non-stressed conditions exhibited the highest total phenolic content (35.98 mg Eq./g). Lettuce samples grown under salt stress showed lower phenolic contents, except for lettuce treated with HES or HES + CGA, when comparing the same treatment between the two conditions. Furthermore, the antioxidant capacity was investigated through DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,20-azinobis-(3-ethylbenzothiazoline-6-sulfonate)), and FRAP (ferric reducing antioxidant power) assays, coupled with metal-chelating activity and phosphomolybdenum capacity. An exciting increase in radical scavenging capacity was observed in lettuce treated with exogenous phenolics, in both stress and non-stress conditions. The inhibitory activity of the samples was evaluated against target health-related enzymes, namely cholinesterases (acetylcholinesterase; AChE; butyryl cholinesterase; BChE), tyrosinase, α-amylase, and α-glucosidase. Lettuce treated with HES + CGA under non-stress conditions exhibited the strongest inhibition against AChE and BChE, while the same treatment under salinity conditions resulted in the highest inhibition capacity against α-amylase. Additionally, CGA under non-stress conditions exhibited the best inhibitory effect against tyrosinase. All the functional traits investigated were significantly modulated by exogenous phenolics, salinity, and their combination. In more detail, flavonoids, lignans, and stilbenes were the most affected phenolics, whereas glycosidase enzymes and tyrosinase activity were the most affected among enzyme assays. In conclusion, the exogenous application of phenolics to lettuce represents an effective and green strategy to effectively modulate the phenolic profile, antioxidant activity, and enzyme inhibitory effects in lettuce, deserving future application to produce functional plant-based foods in a sustainable way.

The study aimed at the metabolite profiling and evaluation of antioxidant and enzyme inhibitory properties of methanol extracts from flowers, leaves, and tubers of unexplored Eminium intortum (Banks & Sol.) Kuntze and E. spiculatum (Blume) Schott (Araceae). A total of 83 metabolites, including 19 phenolic acids, 46 flavonoids, 11 amino, and 7 fatty acids were identified by UHPLC-HRMS in the studied extracts for the first time. E. intortum flower and leaf extracts had the highest total phenolic and flavonoid contents (50.82 ± 0.71 mg GAE/g and 65.08 ± 0.38 RE/g, respectively). Significant radical scavenging activity (32.20 ± 1.26 and 54.34 ± 0.53 mg TE/g for DPPH and ABTS) and reducing power (88.27 ± 1.49 and 33.13 ± 0.68 mg TE/g for CUPRAC and FRAP) were observed in leaf extracts. E. intortum flowers showed the maximum anticholinesterase activity (2.72 ± 0.03 mg GALAE/g). E. spiculatum leaves and tubers exhibited the highest inhibition towards α-glucosidase (0.99 ± 0.02 ACAE/g) and tirosinase (50.73 ± 2.29 mg KAE/g), respectively. A multivariate analysis revealed that O-hydroxycinnamoylglycosyl-C-flavonoid glycosides mostly accounted for the discrimination of both species. Thus, E. intortum and E. spiculatum can be considered as potential candidates for designing functional ingredients in the pharmaceutical and nutraceutical industries.

This work searched for the phyto-therapeutic potential and nutritional value of seeds from the halophyte Cladium mariscus L. (Pohl.), aiming at its use as a source of bioactive ingredients for the food industry. Hence, the nutritional profile, including minerals, of seeds biomass was determined; food-grade samples were prepared, and their phytochemical fingerprinting assessed. Extracts were evaluated for in vitro antioxidant potential, inhibitory capacity towards enzymes related to neuroprotection, diabetes, and hyperpigmentation, and anti-inflammatory properties, along with a toxicological assessment. Sawgrass seeds can be considered a proper nutritional source with a good supply of minerals. All extracts had a high level of total phenolics (65.3−394.4 mg GAE/g DW) and showed a chemically rich and diverse profile of metabolites that have several biological properties described (e.g., antioxidant, anti-inflammatory). Extracts had no significant toxicity (cell viabilities > 80%) and were overall strong antioxidants (particularly at radical scavenging and reducing iron), effective tyrosinase inhibitors (55−71 mg KAE/g DW), showed anti-inflammatory properties (30−60% NO decrease), and had moderate capacity to inhibit enzymes related to neuroprotection (AChE 3.7−4.2, BChE 4.3−6.0 mg GALE/g DW) and diabetes (α-glucosidase 1.0−1.1, α-amylase 0.8−1.1 mmol ACAE/g). Altogether, results suggest that sawgrass seeds have the potential to be exploited as a new food product and are a reservoir of bioactive molecules with prospective applications as ingredients for value-added, functional, and/or preservative food products.

This study aimed to establish a rapid in vitro plant regeneration method from rhizome buds of Kaempferia parviflora to obtain the valuable secondary metabolites with antioxidant and enzyme inhibition properties. The disinfection effect of silver oxide nanoparticles (AgO NPs) on rhizome and effects of plant growth regulators on shoot multiplication and subsequent rooting were investigated. Surface sterilization of rhizome buds with sodium hypochlorite was insufficient to control contamination. However, immersing rhizome buds in 100 mg L-1 AgO NPs for 60 min eliminated contamination without affecting the survival of explants. The number of shoots (12.2) produced per rhizome bud was higher in Murashige and Skoog (MS) medium containing 8 µM of 6-Benzyladenine (6-BA) and 0.5 µM of Thidiazuron (TDZ) than other treatments. The highest number of roots (24), with a mean root length of 7.8 cm and the maximum shoot length (9.8 cm), were obtained on medium MS with 2 µM of Indole-3-butyric acid (IBA). A survival rate of 98% was attained when plantlets of K. parviflora were acclimatized in a growth room. Liquid chromatography with tandem mass spectrometry (LC-MS/MS) was used to determine the chemical profile of K. parviflora leaf extracts. Results showed that several biologically active flavonoids reported in rhizomes were also present in leaf tissues of both in vitro cultured and ex vitro (greenhouse-grown) plantlets of K. parviflora. We found 40 and 36 compounds in in vitro cultured and ex vitro grown leaf samples, respectively. Greenhouse leaves exhibited more potent antioxidant activities than leaves from in vitro cultures. A higher acetylcholinesterase inhibitory ability was obtained for greenhouse leaves (1.07 mg/mL). However, leaves from in vitro cultures exhibited stronger butyrylcholinesterase inhibitory abilities. These results suggest that leaves of K. parviflora, as major byproducts of black ginger cultivation, could be used as valuable alternative sources for extracting bioactive compounds.

Leonurus cardiaca L. (Lamiaceae) is a perennial herb distributed in Asia and Southeastern Europe and has been used in traditional medicine since antiquity for its role against cardiac and gynecological disorders. The polar extracts obtained from L. cardiaca aerial parts contain several compounds among which alkaloids, iridoids, labdane diterpenes, and phenylethanoid glycosides play a major role in conferring protection against the aforementioned diseases. On the other hand, the antioxidant activities and the enzyme inhibitory properties of these extracts have not yet been deeply studied. On the above, in the present study, crude and purified extracts were prepared from the aerial parts of L. cardiaca and have been chemically characterized by spectrophotometric assays and HPLC-DAD-MS analyses. Notably, the content of twelve secondary metabolites, namely phenolic acids (chlorogenic, caffeic, caffeoylmalic and trans-ferulic acids), flavonoids (rutin and quercetin), phenylethanoid glycosides (verbascoside and lavandulifolioside), guanidine pseudoalkaloids (leonurine), iridoids (harpagide), diterpenes (forskolin), and triterpenes (ursolic acid), has been determined. Furthermore, the extracts were tested for their antioxidant capabilities (phosphomolybdenum, DPPH, ABTS, FRAP, CUPRAC, and ferrous chelating assays) and enzyme inhibitory properties against cholinesterase, tyrosinase, amylase, and glucosidase. The purified extracts contained higher phytochemical content than the crude ones, with caffeoylmalic acid and verbascoside as the most abundant compounds. A linear correlation between total phenolics, radical scavenging activity, and reducing power of extracts has been found. Notably, quercetin, caffeic acid, lavandulifolioside, verbascoside, chlorogenic acid, rutin, and ursolic acid influenced the main variations in the bioactivities found in L. cardiaca extracts. Our findings provide further insights into the chemico-biological traits of L. cardiaca and a scientific basis for the development of nutraceuticals and food supplements.

Cicerbita alpina (L.) Wallr. is a perennial herbaceous plant in the tribe Cichorieae (Lactuceae), Asteraceae family, distributed in the mountainous regions in Europe. In this study, we focused on the metabolite profiling and the bioactivity of C. alpina leaves and flowering heads methanol-aqueous extracts. The antioxidant activity of extracts, as well as inhibitory potential towards selected enzymes, involving in several human diseases, including metabolic syndrome (α-glucosidase, α-amylase, and lipase), Alzheimer's disease, (cholinesterases: AChE, BchE), hyperpigmentation (tyrosinase), and cytotoxicity were assessed. The workflow comprised ultra-high-performance liquid chromatography-high-resolution mass spectrometry (UHPLC-HRMS). UHPLC-HRMS analysis revealed more than 100 secondary metabolites, including acylquinic, acyltartaric acids, flavonoids, bitter sesquiterpene lactones (STLs), such as lactucin, dihydrolactucin, their derivatives, and coumarins. Leaves showed a stronger antioxidant activity compared to flowering heads, as well as lipase (4.75 ± 0.21 mg OE/g), AchE (1.98 ± 0.02 mg GALAE/g), BchE (0.74 ± 0.06 mg GALAE/g), and tyrosinase (49.87 ± 3.19 mg KAE/g) inhibitory potential. Flowering heads showed the highest activity against α-glucosidase (1.05 ± 0.17 mmol ACAE/g) and α-amylase (0.47 ± 0.03). The obtained results highlighted C. alpina as a rich source of acylquinic, acyltartaric acids, flavonoids, and STLs with significant bioactivity, and therefore the taxon could be considered as a potential candidate for the development of health-promoting applications.

Cakile maritima Scop. (sea rocket) is an edible halophyte plant with several ethnomedicinal uses. This work reports the chemical profile and bioactivities of food grade extracts from sea rocket organs. Toxicity was determined on mammalian cells, and phenolic profiling and the quantitation of the main metabolites were made by high-performance liquid chromatography coupled to mass spectrometry (HPLC-MS). Enzymatic inhibition was determined towards acetyl- and butyrylcholinesterase (AChE, BuChE), α-glucosidase, α-amylase, and tyrosinase. Docking studies were performed to tyrosinase, on the major metabolites, and samples were tested for antioxidant properties. Extracts were not toxic, were constituted mainly by flavonoids, and some compounds (roseoside and oleuropein) are here described for the first time in the species. The aerial organs' ethanol extract had relevant activity towards 2,2-diphenyl-1-picrylhydrazyl [DPPH, half maximal inhibitory concentration (IC50) = 0.59 mg/mL], and ferric-reducing activity power (FRAP, IC50 = 0.99 mg/mL). All samples were more active towards AChE than on BuChE. The ethanol fruits' extract inhibited α-glucosidase [2.19 mmol of equivalent of acarbose (ACAE)/g]. Samples were active against tyrosinase, especially the aerial organs' ethanol extracts [25.9 mg of equivalent of kojic acid (KAE)/g]. Quercetin and kaempferol glycosides fit well into the enzymatic pocket of tyrosinase. Our results suggest sea rocket as a candidate to be further explored as a source of bioactive products.

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.

Pelargonium quercetorum is a medicinal plant traditionally used for treating intestinal worms. In the present study, the chemical composition and bio-pharmacological properties of P. quercetorum extracts were investigated. Enzyme inhibition and scavenging/reducing properties of water, methanol, and ethyl acetate extracts were assayed. The extracts were also studied in an ex vivo experimental model of colon inflammation, and in this context the gene expression of cyclooxygenase-2 (COX-2) and tumor necrosis factor α (TNFα) were assayed. Additionally, in colon cancer HCT116 cells, the gene expression of transient receptor potential cation channel subfamily M (melastatin) member 8 (TRPM8), possibly involved in colon carcinogenesis, was conducted as well. The extracts showed a different qualitative and quantitative content of phytochemicals, with water and methanol extracts being richer in total phenols and flavonoids, among which are flavonol glycosides and hydroxycinnamic acids. This could explain, at least in part, the higher antioxidant effects shown by methanol and water extracts, compared with ethyl acetate extract. By contrast, the ethyl acetate was more effective as cytotoxic agent against colon cancer cells, and this could be related, albeit partially, to the content of thymol and to its putative ability to downregulate TRPM8 gene expression. Additionally, the ethyl acetate extract was effective in inhibiting the gene expression of COX-2 and TNFα in isolated colon tissue exposed to LPS. Overall, the present results support future studies for investigating protective effects against gut inflammatory diseases.

Chamomile is one of the most consumed medicinal plants worldwide. Various chamomile preparations are widely used in various branches of both traditional and modern pharmacy. However, in order to obtain an extract with a high content of the desired components, it is necessary to optimize key extraction parameters. In the present study, optimization of process parameters was performed using the artificial neural networks (ANN) model using a solid-to-solvent ratio, microwave power and time as inputs, while the outputs were the yield of the total phenolic compounds (TPC). Optimized extraction conditions were as follows: a solid-to-solvent ratio of 1:80, microwave power of 400 W, extraction time of 30 min. ANN predicted the content of the total phenolic compounds, which was later experimentally confirmed. The extract obtained under optimal conditions was characterized by rich composition and high biological activity. Additionally, chamomile extract showed promising properties as growth media for probiotics. The study could make a valuable scientific contribution to the application of modern statistical designs and modelling to improve extraction techniques.

Nepeta baytopii is a poorly studied, endemic Nepeta species (Lamiaceae) of Turkey. For the first time, the biological activities (antioxidant, enzyme inhibition, and cytotoxicity properties) of the hexane, ethyl acetate, methanol, water/methanol, and water extracts and essential oil prepared from N. baytopii aerial parts were assessed. Hydro-methanol (41.25 mg gallic acid equivalent (GAE)/g) and water extracts (50.30 mg GAE/g), respectively showed the highest radical scavenging (94.40 and 129.22 mg Trolox equivalent (TE)/g, for 2,2-diphenyl-1-picrylhydrazyl radical and 2,2-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid radical scavenging assays) and reducing (229.37 and 129.55 mg TE/g, for ferric-reducing antioxidant power and cupric-reducing antioxidant capacity assays) capacities in vitro. An interestingly high inhibition was observed for ethyl acetate extract against butyrylcholinesterase (10.85 mg galantamine equivalent/g). The methanol extract showed high cytotoxicity (31.7%) against HepG2 cells. Caryophyllene oxide was identified in high concentrations in the essential oil (39.3%). Luteolin and apigenin and their derivatives were identified from the methanol and water extracts. The results obtained from this study highlighted that the abundance of highly bioactive compounds from Nepeta baytopii ensures the multiple biological activities of the tested extracts, and this suggests a potential use in the pharmaceutical and nutraceutical fields, and therefore should be investigated further.

The members of the genus Hypericum have great potential to develop functional uses in nutraceutical and pharmaceutical applications. With this in mind, we aimed to determine the chemical profiling and biological properties of different extracts (ethyl acetate, methanol and water) from two Hypericum species (H. montbretii and H. origanifolium). We combined two approaches (LC-DAD-MS and LC-NMR) to identify and quantify chemical compounds of the extracts. Antioxidant properties (free radical quenching, reducing power and metal chelating) and enzyme inhibitory effects (cholinesterase, tyrosinase, amylase and glucosidase) were determined as biological properties. The tested extracts were rich in caffeic acid derivatives and flavonoids, and among them, 3-caffeoyl quinic acid and myricetin-3-O-rhamnoside were found to be the main compounds. The total phenolic and flavonoid levels were determined to be 50.97-134.99 mg GAE/g and 9.87-82.63 mg RE/g, respectively. With the exception of metal chelating, the methanol and water extracts showed stronger antioxidant properties than the ethyl acetate extracts. However, different results were obtained for each enzyme inhibition assay, and in general, the ethyl acetate extracts present more enzyme-inhibiting properties than the water or methanol extracts. Results from chemical and biological analyses were combined using multivariate analysis, which allowed establishing relationships between composition and observed effects of the Hypericum extracts based on the extraction solvents. To gain more insights between chemical compounds and enzyme-inhibiting effects, we performed molecular docking analysis. We observed favorable interactions between certain compounds and the tested enzymes during our analysis, confirming the data obtained from the multivariate approach. In conclusion, the obtained results may shed light on the road from natural sources to functional applications, and the tested Hypericum species may be considered potential raw materials, with promising chemical constituents and biological activities.