Search Results (14)

Jatobá (Hymenaea courbaril) is a native tree abundant in Brazil. The fruit coat is an industrial by-product of jatobá flour processing, typically discarded. Presently, within the circular bioeconomy concept, there are efforts underway that aim at finding economically viable applications for the bio-residues of jatobá. Within this context, the present work attempts to find possible applications for the jatobá coat in glycemic control through inhibition of α-amylase activity. Aqueous and hydroethanolic extracts were used. In vitro experiments included detailed kinetic studies with an α-amylase catalyzed reaction. Starch absorption in vivo was assessed by means of a starch tolerance test in mice. Both extracts inhibited α-amylase. The IC₅₀ values for the aqueous and hydroalcoholic extracts were 81.98 ± 3.53 µg/mL and 51.06 ± 0.42 µg/mL, respectively. The inhibition was of the non-competitive type. Both extracts reduced hyperglycemia caused by starch administration in mice, the aqueous extract being effective over a larger dose range. This action can be attributed to the α-amylase inhibition. In silico studies suggested that procyanidin dimers, taxifolin 7-O-rhamnoside, and quercetin 7-rhamnoside contribute, but several other not-yet-identified substances may be involved. The findings suggest that aqueous and hydroalcoholic extracts from jatobá coat warrant further investigations as potential modulators of glycemia following starch ingestion. Full article

Plants in the genus Juniperus have been reported to produce a variety of chemical components, such as coumarins, flavonoids, lignans, sterols, and terpenoids. Here, ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS) and ultra-high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) were applied to qualitatively and quantitatively analyze the major bioactive components in an ethanolic crude extract from the leaves of Juniperus chinensis L., which grows naturally in Korea. In addition, the antibacterial activity of the crude extract against pathogenic bacteria was investigated. Using LC-QTOF-MS analysis, we identified ten compounds, of which six were confirmed to be flavonoid and lignan-based components as the major bioactive components, i.e., isoquercetin, quercetin-3-O-α-l-rhamnoside, hinokiflavone, amentoflavone, podocarpusflavone A, and matairesinoside. Among them, a quantitative analysis performed using LC-MS/MS revealed that the levels of quercetin-3-O-α-l-rhamnoside and amentoflavone in the crude extract were 203.78 and 69.84 mg/g, respectively. Furthermore, the crude extract exhibited potential antibacterial activity against 10 pathogenic bacteria, with the highest antibacterial activity detected against Bordetella pertussis. Thus, further studies of the leaf extract of J. chinensis L. must be carried out to correlate the compounds present in the extract with the antibacterial activity and elucidate the mechanisms of action of this extract against bacteria. Full article

A magnetically functionalized Fe₃O₄@ZIF−67 metal–organic framework (MOF) was prepared by electrostatic self-assembly using magnetic Fe₃O₄ nanoparticles as the core and ZIF−67 as the shell. The composite was characterized by electron microscopy, X-ray diffraction, Fourier- transform infrared spectroscopy, and Brunauer–Emmett–Teller measurements. Magnetic solid-phase extraction (MSPE) was performed on five flavonoids from Dicranopteris pedata using Fe₃O₄@ZIF−67 as an adsorbent. The developed MSPE method was combined with high-performance liquid chromatography–ultraviolet detection to preconcentrate and separate five flavonoids (rutin, quercitrin, kaempferol-3-O-α-L-rhamnoside, quercetin, and kaempferol) from Dicranopteris pedata. The factors affecting the extraction, such as the amount of Fe₃O₄@ZIF−67 adsorbent, salt ion concentration in the sample solution, vortex time, type and amount of desorbing solvent, concentration of formic acid to acidify the desorbing solvent, and acetonitrile ratio, were optimized. The developed method showed good linearity over the concentration range of 1.09–70.0 μg∙mL⁻¹ for the five flavonoids, with R² values between 0.9901 and 0.9945. The limits of detection and average recoveries for the five flavonoids were in the ranges of 39.5–56.2 ng∙mL⁻¹ and 92.2–100.7%, respectively. The method presented herein is simple, efficient, and sensitive; it can be used for enrichment analysis of the five flavonoids in Dicranopteris pedata. Full article

We carried out a qualitative and quantitative analysis of the phytochemical composition of the fruits of large cranberry cultivars ‘Ben Lear’, ‘Bergman’, ‘Kalnciema agra’, ‘Lemunyon’, ‘Pilgrim’, ‘Stevens’, and ‘Tina’ grown in Latvian climatic conditions. The following predominant compounds were found in cranberry fruit samples: peonidin-3-O-galactoside, peonidin-3-O-arabinoside, cyanidin-3-O-galactoside, cyanidin-3-O-arabinoside, myricetin-3-galactoside, quercetin-3-galactoside, quercetin-3-α-L-arabinofuranoside, quercetin 3-rhamnoside, ursolic acid, and oleanolic acid. During the berry ripening period (from 16 August until 15 September), a trend of decreasing amounts of compounds was found in the fruit samples of the studied cranberry cultivars: the total amount of proanthocyanidins decreased by 1.3 times, the total amount of the identified flavonols decreased by 1.3 times, the total amount of triterpenoids decreased by 1.2 times, and the total amount of chlorogenic acid decreased by 1.7 times. During the period from 16 August until 15 September, the total amount of anthocyanins in the cranberry fruit samples increased by 2.6 to 17 times. The highest total amount of anthocyanins (5305.80 ± 27 µg/g) was detected in fruit samples of the cranberry cultivar ‘Kalnciema agra’ collected on 15 September. The amount of biologically active compounds in cranberry fruit samples varies during berry ripening. Thus, the choice of the picking time is one of the factors that determines the phytochemical composition of raw cranberry material. Full article

Raspberry (Rubus idaeus L.), known as one of the famous healthy fruits an d are consumed fresh or processed products all over the world. The antioxidation activity of raspberry fruits as well as leaves have been widely investigated. To better understand the metabolite accumulation mechanisms and to develop different functional cultivars, we performed a non-targeted metabolomics analysis using LC-MS/MS to investigate the contents of existing components from three raspberry cultivars, Autumn Britten, Autumn Bliss, and Red Autumn leaves, respectively. The results show multiple differentially accumulated metabolites among three cultivars, especially for the lipids (α-linolenic acid and eicosatetraenoic acid), amino acids and their derivatives (L-cysteine, Phenylalanine), flavonoids (Kaempferol 3-O-rhamnoside-7-O-glucoside, Quercetin 3-glucoside), and vitamins (Biotin, Thiamine, Vitamin K2), etc. The in vitro cellular antioxidant activities of three raspberry cultivars leaves ethanol extracts (RLEE) were also characterized. Through comparison the superoxide dismutase (SOD), glutathione (GSH), catalase (CAT), and reactive oxygen species (ROS) levels before or after RLEE protection of L929 fibroblast cells upon excessive UVB exposure, we evaluated the antioxidation potentials for all three cultivar RLEEs. It turns out the raspberry Autumn Britten leaf extract holds the greatest potential for protecting the L929 fibroblast cells from UVB induced damage. Our study provides theoretical support for screening of active metabolites from three raspberry cultivars leaves, spanning metabolites’ accumulation to cell damage protection, which could be used to refine bioactivity assessment for different raspberry cultivars suitable for antioxidant products extraction. Full article

Diabetes is a major health problem that is associated with high risk of various complications. Medicinal plants hold great promise against diabetes. The traditional use of Cleome droserifolia as an antidiabetic agent was correlated to its flavonol glycosides content. In the current study, five major flavonol glycosides appeared on the RP-HPLC chromatogram of the aqueous extract namely; quercetin-3-O-β-d-glucosyl-7-O-α-rhamnoside (1), isorhamnetin-7-O-β-neohesperidoside (2), isorhamnetin-3-O-β-d-glucoside (3) kaempferol-4′-methoxy-3,7-O-α-dirhamnoside (4), and isorhamnetin-3-O-α-(4″-acetylrhamnoside)-7-O-α-rhamnoside (5). The inhibitory activities of these compounds were tested in vitro against several enzymes involved in diabetes management. Only the relatively less polar methoxylated flavonol glycosides (4, 5) showed mild to moderate α-amylase and α-glucosidase inhibitory activities. Compounds 1–4 displayed remarkable inhibition of dipeptidyl peptidase IV (DPPIV) enzyme (IC₅₀ 0.194 ± 0.06, 0.573 ± 0.03, 0.345 ± 0.02 and 0.281 ± 0.05 µg/mL, respectively) comparable to vildagliptin (IC₅₀ 0.154 ± 0.02 µg/mL). Moreover, these compounds showed high potential in preventing diabetes complications through inhibiting aldose reductase enzyme and combating oxidative stress. Both isorhamnetin glycoside derivatives (2, 3) exhibited the highest activities in aldose reductase inhibition and compound 2 (IC₅₀ 5.45 ± 0.26 µg/mL) was even more potent than standard quercetin (IC₅₀ 7.77 ± 0.43 µg/mL). Additionally, these flavonols exerted excellent antioxidant capacities through 2, 2-diphenyl-1-picrylhydrazil (DPPH) and ferric reducing antioxidant (FRAP) assays. Full article

Crataegus almaatensis, an endemic ornamental plant in Kazakhstan is used in popular medicine due to its cardiotonic properties. The most studied species of the same genus are commonly found in Europe, which shows the importance of having the Kazakh species validated via its chemical and pharmacological studies. High-speed countercurrent chromatography (HSCCC) operated under optimized conditions enabled an isolation of the three main compounds from the aqueous phase of the leaves ethanol extract, further identified by nuclear magnetic resonance (NMR), as quercetin 3-O-rhamnoside (quercitrin) (4.02% of the crude extract-CECa); quercetin 3-O-β-galactoside (hyperoside) (1.82% of CECa); kaempferol 3-O-α-L-rhamnoside (afzelin) (0.94% of CECa). The CECa, the aqueous phase of the crude extract (APCa) together with the isolates were evaluated for their vascular (vascular reactivity in human internal mammary artery-HIMA), anti-nociceptive (formalin-induced liking response and hot plate) and anti-inflammatory (subcutaneous air-pouch model-SAP) activities. CECa at the concentrations of 0.014 and 0.14 mg/mL significantly increased the maximum contractility response of HIMA to noradrenaline. The APCa CR curve (0.007–0.7 mg/mL) showed an intrinsic relaxation effect of the HIMA. APCa at the dose of 100 mg/kg i.p. significantly decreased the total leukocyte count and the IL-1β release in the SAP wash. Full article

Deep eutectic solvents (DESs) are commonly employed as environmentally-friendly solvents in numerous chemical applications owing to their unique physicochemical properties. In this study, a novel and environmentally-friendly extraction method based on ultrasound assisted-deep eutectic solvent extraction (UAE-DES) was investigated for the extraction of flavonoids from Cyclocarya paliurus (Batal.) Iljinskaja (C. paliurus) leaves, and the antioxidant activities of these flavonoids were evaluated. Nine different DES systems based on either two or three components were tested, and the choline chloride/1,4–butanediol system (1:5 molar ratio) was selected as the optimal system for maximizing the flavonoid extraction yields. Other extraction conditions required to achieve the maximum flavonoid extraction yields from the leaves of C. paliurus were as follows: DES water content (v/v), 30%; extraction time, 30 min; temperature, 60 °C; and solid-liquid ratio, 20 mg/mL. Liquid chromatography-mass spectrometry allowed the detection of five flavonoids in the extract, namely kaempferol-7-O-α-l-rhamnoside, kaempferol, quercetin, quercetin-3-O-β-d-glucuronide, and kaempferol-3-O-β-d-glucuronide. In vitro antioxidant tests revealed that the flavonoid-containing extract exhibited strong DPPH and ABTS radical-scavenging abilities. Results indicate that UAE-DES is a suitable approach for the selective extraction of flavonoids from C. paliurus leaves, and DESs can be employed as sustainable extraction media for other bioactive compounds. Full article

In this study, a high-speed counter-current chromatography (HSCCC) separation method target guided by centrifugal ultrafiltration with high-performance liquid chromatography-mass spectrometry (CU-LC-MS) was proposed. This method was used to analyze α-amylase inhibitors from Kadsura longipedunculata extract. According to previous screening with CU-LC-MS, two screened potential α-amylase inhibitors was successfully isolated from Kadsura longipedunculata extract using HSCCC under the optimized experimental conditions. The isolated two target compounds (with purities of 92.3% and 94.6%) were, respectively, identified as quercetin-3-O-rhamnoside (1) and protocatechuic acid (2) based on the MS, UV, and ¹H-NMR spectrometry data. To verify the inhibition of screened compounds, the inhibitory activities of quercetin-3-O-rhamnoside (1) and protocatechuic acid (2) on α-amylase were tested, and it demonstrated that the experimental IC₅₀ values of quercetin-3-O-rhamnoside (1) and protocatechuic acid (2) were 28.8 and 12.5 μmol/L. These results proved that the hyphenated technique using CU-LC-MS and HSCCC was a rapid, competent, and reproductive method to screen and separate potential active compounds, like enzyme inhibitors from the extract of herbal medicines. Full article

Chinese bayberry (Morella rubra Sieb. et Zucc.) fruit have a diverse flavonoid composition responsible for the various medicinal activities, including anti-diabetes. In the present study, efficient simultaneous purification of four flavonoid glycosides, i.e., cyanidin-3-O-glucoside (1), myricetin-3-O-rhamnoside (2), quercetin-3-O-galactoside (3), quercetin-3-O-rhamnoside (4), from Chinese bayberry pulp was established by the combination of solid phase extract (SPE) by C18 Sep-Pak^® cartridge column chromatography and semi-preparative HPLC (Prep-HPLC), which was followed by HPLC and LC-MS identification. The purified flavonoid glycosides, as well as different fractions of fruit extracts of six bayberry cultivars, were investigated for α-glucosidase inhibitory activities. The flavonol extracts (50% methanol elution fraction) of six cultivars showed strong α-glucosidase inhibitory activities (IC₅₀ = 15.4–69.5 μg/mL), which were higher than that of positive control acarbose (IC₅₀ = 383.2 μg/mL). Four purified compounds 1–4 exerted α-glucosidase inhibitory activities, with IC₅₀ values of 1444.3 μg/mL, 418.8 μg/mL, 556.4 μg/mL, and 491.8 μg/mL, respectively. Such results may provide important evidence for the potential anti-diabetic activity of different cultivars of Chinese bayberry fruit and the possible bioactive compounds involved. Full article

Phytochemical investigations of ethyl acetate-soluble part of the aerial part of Hypericum scabrum L. delivered eight pure phenolic compounds 1–8. The pure compounds were identified through physico-chemical, NMR (1D, 2D) and mass spectrometric studies as: 3-8′′-bisapigenin (1), quercetin (2), quercetin-3-O-α-l-arabinofuranoside (3), quercetin-3-O-α-l-rhamnoside (4), quercetin-3-O-β-d-glucopyranoside (5), quercetin-3-O-β-d-galactopyranoside (6), (−)-epicatechin (7), (+)-catechin (8). Total polyphenolic compounds and total flavonoids contents were determined in the extract as 0.107 mg∙mg⁻¹ and 0.023 mg∙mg⁻¹ of the dried extract, respectively. Antioxidant activity using DPPH free radical scavenging assay delivered very strong activity for compounds 2 and 5, 6 and crude extract 10. Protein tyrosine phosphatase 1B (PTP-1B) inhibition experiment of isolated compounds and crude extracts resulted in significant inhibition activity for samples 2, 7a, 8a, 11 and 12 with IC₅₀ values ranging from 1.57 to 2.91 µM. Antimicrobial activity of the pure compounds and extracts produced average results against Staphylococcus aureus, Escherichia coli and Candida albicans strains. From our literature survey, it appears that all pure compounds except 2 were isolated and reported for the first time in H. scabrum. Full article

Croton species are used in folk medicine in the management of infections, inflammation and oxidative stress-related diseases. In order to isolate, characterize and evaluate the bioactive constituents of Croton menyharthii Pax leaf extracts, repeated column fractionation of the ethyl acetate fraction from a 20% aqueous methanol crude extract afforded three flavonols identified by NMR (1D and 2D) spectroscopic methods as myricetrin-3-O-rhamnoside (myricetrin, 1), quercetin-3-O-rhamnoside (2) and quercetin (3) along with an indole alkaloid, (E)-N-(4-hydroxycinnamoyl)-5-hydroxytryptamine, [trans-N-(p-coumaroyl) serotonin, 4]. All the compounds are reported from the leaf extract of this plant for the first time. The crude extracts, four solvent fractions (hexane, DCM, ethyl acetate and butanol) and isolated compounds obtained from the leaves were evaluated for their inhibitory effects on selected bacteria, a fungus (Candida albicans), cyclooxygenase (COX-2), α-glucosidase and acetylcholinesterase (AChE). Amongst the compounds, quercetin (3) was the most active against Bacillus subtilis and Candida albicans while myricetrin-3-O-rhamnoside (1) and trans-N-(p-coumaroyl) serotonin (4) were the most active compounds against Escherichia coli, Klebsiella pneumonia and Staphylococcus aureus. The inhibitory activity of myricetrin-3-O-rhamnoside (1) against COX-2 was insignificant while that of the other three compounds 2–4 was low. The AChE inhibitory activity of the alkaloid, trans-N-(p-coumaroyl) serotonin was high, with a percentage inhibitory activity of 72.6% and an IC₅₀ value of 15.0 µg/mL. The rest of the compounds only had moderate activity. Croton menyharthii leaf extracts and isolated compounds inhibit α-glucosidase at very low IC₅₀ values compared to the synthetic drug acarbose. Structure activity relationship of the isolated flavonols 1–3 is briefly outlined. Compounds 1–4 and the leaf extracts exhibited a broad spectrum of activities. This validates the ethnomedicinal use of the plant in folk medicine. Full article

A sensitive and accurate ultra-performance liquid chromatography coupled with triple quadrupole mass (UPLC-MS/MS) method was developed for the determination of quercetin-3-O-β-D-glucopyranoside-(4→1)-α-L-rhamnoside (QGR) in rat plasma using rutin as internal standard. Chromatographic separation was achieved on a Acquity BEH C₁₈ column (100 mm × 2.1 mm, 1.7 μm) with a gradient elution of acetonitrile and 0.10% formic acid (v/v) at a flow rate of 0.4 mL/min. QGR and rutin were detected using electrospray negative ionization mass spectrometry in the multiple reaction monitoring (MRM) mode. The method demonstrated good linearity and did not show any endogenous interference with the QGR and rutin peaks. This method was successfully applied to a pharmacokinetic study of QGR in rats after intravenous (20 mg/kg) and oral (40 mg/kg) administration, and the results showed that the compound was poorly absorbed, with an absolute bioavailability of approximately 3.41%. Full article

An acylated kaempferol glycoside, namely kaempferol-3-O-α-L-(2”,3”-di-E-pcoumaroyl)-rhamnoside (1) was isolated from the flowers of Foeniculum vulgare Mill. and F. dulce DC. It is thus isolated for the first time from family Apiaceae. In addition, the different organs of both plants afforded six flavonoid glycosides - namely afzelin (kaempferol-3-O-α-L-rhamnoside) (2), quercitrin (3), isorhamnetin-3-O-β-D-glucoside (4), isoquercitrin (5), rutin (6), and miquelianin (quercetin-3-O-β-D-glucuronide) (7). Structure elucidation of the above mentioned flavonoids was achieved by UV, ¹H- and ¹³C-NMR, ¹H-¹H COSY, HMQC and EI-MS. Full article