Search Results (115)

NMR spectroscopy enables the study of complex mixtures, including plant extracts. The interpretation of specific ranges of ¹H NMR spectra allows for the determination of polyphenolic compound, sugar, amino acid, and fatty acid profiles. The main goal of ¹H NMR analyses of plant extracts is to identify the unique “fingerprint” of the material being studied. The aim of this study was to determine the metabolomic profile and antioxidant activity of various Lavandula angustifolia (Betty’s Blue, Elizabeth, Hidcote, and Blue Mountain White) and Lavandula × intermedia cultivars (Alba, Grosso, and Gros Bleu) grown in Poland. Modern green chemistry extraction methods (supercritical fluid extraction (SFE) and ultrasound-assisted extraction (UAE)) were used to prepare the lipophilic and hydrophilic extracts, respectively. The secondary metabolite profiles were determined using the diagnostic signals from ¹H NMR and HPLC-DAD analyses. These metabolomic profiles were used to illustrate the differences between the different lavender and lavandin cultivars. The HPLC-DAD analysis revealed that both lavender species have similar polyphenolic profiles but different levels of individual compounds. The extracts from L. angustifolia were characterized by higher phenolic acid and flavonoid contents, while the extracts from L. × intermedia had a higher coumarin content. Diagnostic ¹H NMR signals can be used to verify the authenticity and origin of plant extracts, and identify directions for further research, providing a basis for applications such as in cosmetics. Full article

This study aimed to develop a sustainable approach for isolating bioactive lipophilic components from Taraxacum officinale flowers using supercritical carbon dioxide extraction (SFE-CO₂) and to assess the effect of adding 5% ethanol (EtOH) as a co-solvent on extraction yield, in vitro antioxidant capacity in CUPRAC and ABTS assays (TEAC_CUPRAC and TEAC_ABTS), total phenolic (TPC) and flavonoid (TFC) content, β-carotene concentration, and photoprotective potential, expressed as the sun protection factor (SPF). SFE-CO₂ at 35 MPa and 40 °C resulted in 50% of the total yield within 15 min, with equilibrium reached after 120 min (final yield of 4.6 g/100 g flowers). Co-solvent addition increased yield by ~50% and shortened extraction time. The EtOH-modified extract exhibited markedly higher antioxidant activity, with a 2-fold increase in TEAC_CUPRAC (167 mg TE/g E), an 11-fold increase in TEAC_ABTS (194 mg TE/g E), and a 3-fold increase in TPC (91 mg GAE/g E), along with improved recovery of flavonoids and β-carotene. Volatile profiling revealed monoterpenoids, aldehydes, and esters as dominant groups, with carvone (14.0–16.5%) and dill ether (4.2–5.8%) as major contributors to aroma. The SFE-CO₂ + 5% EtOH extract achieved the highest SPF value (49.5 at 1 mg/mL; SPF > 6 at >0.1 mg/mL), indicating strong photoprotective potential and potential suitability for natural antioxidant and cosmetic applications. Full article

Isabella grape pomace (IGP) the primary by-product of Colombia’s winemaking industry, represents a promising source of nutraceuticals with potential uses in the food industry. This study developed a sequential green extraction process to recover nutraceutical from IGP. The approach integrated supercritical fluid extraction with CO₂ (SFE-CO₂) to obtain lipophilic compounds, followed by SFE with ethanol/water as co-solvent (SFE-CO₂/EtOH:H₂O) for medium-polarity phenolics, and pressurized liquid extraction (PLE) with EtOH:H₂O to recover the polar phenolic-rich fraction. The extraction parameters were optimized using response surface methodology, and optimal conditions were identified: SFE-CO₂ at 31.7 MPa/58.9 °C yielded 6.95% extract rich in linoleic acid (65.5%) and α-tocopherol (107.2 mg/kg); SFE-CO₂/EtOH:H₂O with 15% of co-solvent produced extracts with high phenolic content (105.35 mg GAE/g) and antioxidant activity (0.18 mmol TE/g); while PLE at 58.91% of EtOH/107.98 °C achieved notable recovery of flavonoids (757.18 mg QE/g), anthocyanins(1508 μg MAE/g) and condensed tannins (258.39 mg ECE/g), with potent antioxidant capacity (130.40 mmol TE/g). The sequential process demonstrated synergistic effects, with a total cumulative yield of 41.08% and phenolic recovery of 349.89 mg GAE/g extract. This approach offers a sustainable biorefinery approach for transforming IGP into high-value nutraceutical ingredients. Full article

NADESs represent a modern class of extraction media that align with the principles of green chemistry. They are considered non-toxic and biodegradable, but relatively little is known about their biological activity. This study investigated the antioxidant, antibacterial, and antifungal properties of 40 NADESs. The systems were developed from primary (PRIM) based on choline chloride (ChCl), and specialized (HEVO) plant-derived metabolites, particularly based on thymol and menthol. Their antioxidant activity was evaluated using spectrophotometric tests. The antimicrobial activity was evaluated by the disk diffusion method. The data obtained were analyzed using principal component analysis (PCA) and partial least squares discriminant analysis (PLS-DA). NADESs based on PRIM exhibited negligible antioxidant activity and relatively low antimicrobial activity. By contrast, NADESs containing HEVO, particularly thymol-based systems, indicated significant antioxidant activity, with stronger activity observed at higher molar proportions of thymol. In the 1,8-cineole:thymol system, ABTS activity ranged from 167.37 ± 24.17 to 861.25 ± 33.03 mg Trolox equivalents/mL NADES (molar ratios 9:1 and 1:9, respectively). The 1,8-cineole:thymol system (1:9) also showed strong antimicrobial activity, with a maximum inhibition zone of 39.33 ± 2.52 mm against Staphylococcus aureus. In summary, NADESs based on HEVO exhibit significantly stronger biological activity than those containing only PRIM. Full article

This study systematically investigated lipophilic and polar metabolites of Atraphaxis virgata (Polygonaceae) and assessed its immunomodulatory activity in vivo. Supercritical CO₂ extraction of the aerial parts yielded a lipophilic fraction analyzed by means of gas chromatography–mass spectrometry (GC–MS), which identified 42 compounds, including fatty acid esters, sterols, hydrocarbons, and terpenoids. The residual plant meal was subjected to ultrasound-assisted extraction with 70% aqueous ethanol at 30–35 °C, using a solid-to-solvent ratio of 1:8 for 120 min. This polar extract was evaluated for amino acids, proteins, and carbohydrates, while solvent–solvent partitioning with chloroform, ethyl acetate, and water enabled isolation of phenolic- and flavonoid-enriched fractions. Six phenolic constituents, including four flavonol glycosides and two phenolic acids, were structurally confirmed. The extracts were rich in unsaturated fatty acids and water-soluble antioxidants, supporting their nutritional and pharmacological relevance. In vivo evaluation using a cyclophosphamide-induced myelosuppression model in Wistar rats demonstrated stimulation of erythropoiesis and leukopoiesis, confirming immunomodulatory potential. Collectively, this work provides the first comprehensive chemical and biological characterization of A. virgata and establishes a foundation for mechanistic studies and pharmacological validation. Full article

Valorization of Phoenix dactylifera L. (date) seeds, an abundant agro-industrial byproduct, offer a sustainable approach to developing multifunctional ingredients for dermocosmetic photoprotection. Rich in polyphenols, flavonoids, and lipophilic antioxidants, date seed extracts and oils demonstrate promising UV-absorbing, anti-inflammatory, and free-radical-scavenging properties. Recent in vitro, ex vivo, and preclinical studies underscore their potential as bioactive agents in sunscreen formulations, supporting both skin barrier integrity and oxidative stress mitigation, although clinical validation is still required. This review consolidates current knowledge on the phytochemical profile and biological efficacy of date seed derivatives, with emphasis on their integration into advanced delivery systems such as nanocarriers, Pickering emulsions, and cyclodextrin complexes to enhance photostability, skin permeability, and esthetic acceptability. Safety aspects, including allergenicity, phototoxicity, and regulatory gaps, are critically examined alongside environmental and ethical advantages, including biodegradability and vegan suitability. The findings advocate for the inclusion of Phoenix dactylifera L. seed actives in next-generation dermocosmetic sunscreens that align with circular bioeconomy principles, consumer demand for “reef-safe” products, and evolving international regulations. Further clinical validation is encouraged to fully translate these botanically derived agents into effective and ethically sound sun care innovations. Full article

Ficus lindsayana is recognized for its medicinal properties, with previous studies highlighting the antioxidant and anti-inflammatory effects of its latex (FLtA) and root (FRE) extracts. Harvesting these plant parts, however, raises ecological concerns. This study evaluates the phytochemical profiles, safety, and biological activities of F. lindsayana leaf (FL) extracts as more sustainable alternatives. Leaves were extracted using hot water (FLA) and 80% ethanol (FLE), yielding 32.9% and 11.4%, respectively. Metabolomic and targeted HPLC-MS/MS analyses revealed distinct phytochemical compositions. FLE was enriched in flavonoid aglycones and lipophilic compounds, while FLA contained higher levels of polar phenolics. FLA showed greater total phenolic and flavonoid contents and stronger antioxidant activity, with an SC₅₀ of 159 μg/mL for the DPPH assay. In contrast, FLE demonstrated more pronounced anti-inflammatory activity. In LPS-stimulated RAW 264.7 macrophages, FLE significantly reduced nitric oxide production and iNOS expression at both the protein and mRNA levels. FLE also reduced IL-6 secretion in a dose-dependent manner without affecting TNF-α, suggesting selective cytokine modulation. Both extracts exhibited low cytotoxicity (IC₂₀ > 800 µg/mL in most cell types), non-hemolytic properties, and no mutagenic activity in the Drosophila wing spot assay. Compared to root and latex extracts, FLE ranked second in anti-inflammatory potency (FRE > FLE > FLA = FLtA). FLE, therefore represents a promising candidate, combining potent bioactivity with environmental responsibility and supporting the further development of F. lindsayana leaf-derived products for use in functional foods or botanical therapeutics. Full article

The inflammatory response is a defence mechanism triggered by tissue damage, aiming to eliminate harmful agents and initiate healing. Conventional anti-inflammatory drugs, such as NSAIDs and corticosteroids, are widely used but often cause severe side effects. Flavonoids, particularly flavanones, have shown significant anti-inflammatory activity with fewer adverse effects. In this study, eight analogues (1a–1d) and (2a–2d) were obtained from natural flavanones (1) and (2) using a pharmacomodulation strategy. NMR, FTIR, structurally confirmed all compounds and MS. Theoretical physicochemical analyses, including molecular orbital energies, dipole moments, and Log P, suggested favourable drug-like properties for these analogues. The anti-inflammatory activity was evaluated in vivo using a TPA-induced mouse ear edema model. Analogue (2c) exhibited the highest inhibition (98.62 ± 1.92%), followed by (2d) (76.12 ± 1.74%) and (1c) (71.64 ± 1.86%). Notably, structural modifications such as cyclization, methoxylation, and prenylation were associated with increased lipophilicity and biological activity, suggesting that tuning physicochemical properties may enhance pharmacological efficacy while preserving drug-likeness. Overall, these findings highlight semi-synthetic derivatization of flavanones as a valuable approach for developing potent and selective anti-inflammatory agents, positioning analogue (2c) as a promising lead for further pharmacological development. Full article

This study aims to provide a comprehensive evaluation of the bioactive compounds present in honeysuckle flower (Lonicera japonica Thunb.) extract (HSF) and their remarkable antioxidant activity. A docking simulation was performed to clarify the binding affinities of the identified phytochemicals to enzymes associated with anti-aging and anti-inflammatory activities. In addition, the low-energy nanoemulsions based on optimally formulated polyglycerol fatty acid esters (PGFEs), developed through D-optimality, were designed for the incorporation of HSF extract. The result revealed that HSF is a rich source of diverse phenolic and flavonoid compounds that contribute to its remarkable antioxidant capacity. Molecular docking analysis indicates that its compounds exhibit anti-aging and anti-inflammatory activities, particularly through collagenase, hyaluronidase, and TNF-α inhibition. Furthermore, D-optimality revealed that HSF-loaded nanoemulsions can be fabricated by a surfactant to oil ratio (SOR) of 2:1 with a ratio of low hydrophilic-lipophilic balance (HLB) surfactant to high HLB surfactant (LHR) of 1:2. Polyglyceryl-6 laurate as a high HLB surfactant produced the optimal nanoemulsion with small particle size and possessed an encapsulation efficiency (EE) of 74.32 ± 0.19%. This is the first report to combine D-optimal design-based nanoemulsion development with a multi-level analysis of HSF, including phytochemical profiling, antioxidant evaluation, and in silico molecular docking. These findings highlight that HSF-loaded polyglycerol fatty acid ester-based nanoemulsions could be a skin health-promoting ingredient and effective alternative for a variety of skincare applications. Full article

The concomitant utilization of flavonoids and α-tocopherol has the potential to establish a comprehensive antioxidant system that operates in both hydrophilic and lipophilic environments. The objective of this study was to examine the antioxidant interactions between dihydroquercetin, a flavonoid that has shown promise in various studies, as well as structurally related flavonoids, and α-tocopherol in various ratios. The antioxidant capacity was assessed using two ABTS^•+ radical-cation inhibition assays: a decolorization assay and a lag-time assay. The results of this study indicated that formulations of dihydroquercetin, quercetin, rutin, or morin with α-tocopherol exhibited additive or mildly subadditive interactions, independent of their ratios. A two-phase pattern was exhibited by the lag-time data, which, in comparison with individual components, allowed us to suggest that α-tocopherol appeared to dominate the initial phase of radical scavenging, while flavonoids became active in the later phase. This finding indicates that α-tocopherol may play a role in protecting flavonoids from premature oxidation in alcoholic media. The findings could prove valuable for the rational design of antioxidant formulations in the nutraceutical, cosmeceutical, and pharmaceutical industries. Additionally, the two-stage antioxidant behavior offers prospects for the formulation of straightforward, cost-effective analytical approaches to measure components in binary antioxidant formulations. Full article

Flavonoids and chalcones, widely recognised for their diverse biological activities, have garnered attention due to their potential therapeutic applications. This review discusses fluorinated flavonoids and chalcones, focusing on their prospective anti-inflammatory, antidiabetic, anticancer, antiosteoporotic, cardioprotective, neuroprotective, hepatoprotective, antimicrobial, and antiparasitic applications. The enhanced biological activities of fluorinated derivatives, particularly the antibacterial, antiviral, and anticancer properties, are attributed to the introduction of fluorine groups, which increase lipophilicity and metabolic stability. Key findings indicate that fluorinated flavonoids and chalcones exhibit synergistic effects with antibiotics, inhibit bacterial efflux pumps, and reveal potent antiviral and anticancer properties. However, challenges such as cytotoxicity and structural optimisation have to be addressed. The synthesis of fluorinated flavonoids and chalcones is discussed, with emphasis on various synthetic methods such as condensation and cyclisation reactions starting from fluorinated precursors, as well as fluorination strategies, including the use of molecular fluorine or fluorinating agents. Fluorinated flavonoids and chalcones represent candidates for therapeutic development and have the potential to overcome drug resistance. However, further studies are necessary to adjust their pharmacological profiles. Full article

This investigation aimed at studying the effect of enrichment of corn oil, which was used as a model lipid, using waste orange peel (WOP), polyphenolic antioxidants, to provide effective shielding against oxidation. An initial comparison of two modes, a stirred-tank and an ultrasound-assisted one, evidenced that the latter was more efficacious in enriching corn oil with total polyphenols. However, detailed examination of the polyphenolic composition revealed that the oil enriched with the stirred-tank mode may have almost two times higher polyphenolic content, which totaled 109 mg per kg of oil. The major polyphenolic constituents identified were polymethylated flavones, but also ferulic acid and naringenin. Oil stability trials, including the monitoring of peroxide value and p-anisidin value, demonstrated that the oil enriched with WOP polyphenols using the stirred-tank mode exhibited significantly higher oxidative resilience compared to control (neat oil), but also compared to the oil enriched using ultrasonication. Furthermore, it was observed that when neat oil was ultrasonicated, it also displayed exceptional stability against oxidation. Based on the outcome of this study, it is recommended that WOP, owed to its richness in lipophilic flavonoids, might be an ideal candidate for edible oil fortification, which could provide the oil with natural powerful antioxidants. Such a process could lend oils high oxidative resilience, but also functional ingredients. Full article

This research aimed to assess how irrigation can affect the sustainability and quality of two Italian tomato cultivars: the “Riccio di Parma Casertano,” which is grown without irrigation, and the “Piennolo del Vesuvio DOP,” which requires irrigation. Life cycle assessment and water footprint analysis were used for sustainability assessment, while, for quality assessment, the content of bioactive compounds was analyzed by UV-Vis spectrophotometric assays. The results indicate that ‘Riccio di Parma Casertano’ is a more sustainable cultivar than ‘Piennolo del Vesuvio DOP’, with lower environmental impacts in all 18 impact categories, showing reductions ranging from 54.55% to 99.90%. This higher sustainability performance of “Riccio di Parma Casertano” is also characterized by increases of +32% in total polyphenol content and +43% in total flavonoid content as an adaptive response to water stress compared with “Piennolo del Vesuvio DOP”. However, “Piennolo del Vesuvio DOP” has a higher yield and better overall nutritional and functional quality, with higher concentrations of hydrophilic and lipophilic compounds, such as lycopene and β-carotene, due to irrigation. The results, therefore, show how the choice between the two cultivars might depend on a trade-off between sustainability and quality. In particular, ’Riccio di Parma Casertano’ could excel in contexts with low water availability while maintaining a good nutritional profile due to the synthesis of bioactive compounds; on the other hand, “Piennolo del Vesuvio DOP” could offer higher yield and nutritional qualities, although it needs improved agricultural practices to reduce overall environmental impacts. Full article

Kefir-based fermentation products exhibit antioxidant and anti-inflammatory effects against oxidative stress, inflammation, platelet activation and aggregation, and other related manifestations, thereby preventing the onset and development of several chronic diseases. Specifically, water kefir, a symbiotic culture of various microorganisms used for the production of several bio-functional fermented products, has been proposed for its health-promoting properties. Thus, water kefir grains and its apple pomace-based fermentation beverage were studied for bioactive amphiphilic and lipophilic lipid compounds with antioxidant, antithrombotic, and anti-inflammatory properties. Total lipids (TL) were extracted and further separated into their total amphiphilic (TAC) and total lipophilic content (TLC), in which the total phenolic and carotenoid contents (TPC and TCC, respectively) and the fatty acid content of the polar lipids (PL) were quantified, while the antioxidant activity of both TAC and TLC were assessed in vitro, by the ABTS, DPPH, and FRAP bioassays, along with the anti-inflammatory and antithrombotic activity of TAC against human platelet aggregation induced by the thrombo-inflammatory mediator, platelet-activating factor (PAF) or standard platelet agonists like ADP.ATR-FTIR spectra facilitated the detection of specific structural, functional groups of phenolic, flavonoid, and carotenoid antioxidants, while LC−MS analysis revealed the presence of specific anti-inflammatory and antithrombotic PL bioactives bearing unsaturated fatty acids in their structures, with favorable omega-6 (n-6)/omega-3 (n-3)polyunsaturated fatty acids (PUFA), which further support the findings that the most potent antioxidant, anti-inflammatory and antithrombotic bioactivities were observed in the TAC extracts, in both water kefir grains and beverage cases. The detection of such bioactive components in both the uncultured water kefir grains and in the cultured beverage further supports the contribution of water kefir microorganisms to the bioactivity and the bio-functionality of the final fermented product. Nevertheless, the extracts of the beverage showed much stronger antioxidant, anti-inflammatory, and antithrombotic activities, which further suggests that during the culture process for producing this beverage, not only was the presence of bioactive compounds produced by kefir microflora present, but biochemical alterations during fermentation of bioactive components derived from apple pomace also seemed to have taken place, contributing to the higher bio-functionality observed in the apple pomace—water kefir-based beverage, even when compared to the unfermented apple pomace. The overall findings support further studies on the use of water kefir and/or apple pomace as viable sources of antioxidant, anti-inflammatory, and antithrombotic amphiphilic bioactive compounds for the production of novel health-promoting bio-functional fermented products. Full article

2-phenylchromen-4-one, commonly known as flavone, plays multifaceted roles in biological response that can be abundantly present in natural sources. The methoxy group in naturally occurring flavones promotes cytotoxic activity in various cancer cell lines by targeting protein markers, in facilitating ligand–protein binding mechanisms and activating cascading downstream signaling pathways leading to cell death. However, the lipophilic nature of these analogs is a key concern as it impacts drug membrane transfer. While lipophilicity is crucial for drug efficacy, the excessive lipophilic effects in flavonoids can reduce water solubility and hinder drug transport to target sites. Recent in vitro studies suggest that the incorporation of polar hydroxyl groups which can form hydrogen bonds and stabilize free radicals may help overcome the challenges associated with methoxy groups while maintaining their essential lipophilic properties. Naturally coexisting with methoxyflavones, this review explores the synergistic role of hydroxy and methoxy moieties through hydrogen bonding capacity in maximizing cytotoxicity against cancer cell lines. The physicochemical analysis revealed the potential intramolecular interaction and favorable electron delocalization region between both moieties to improve cytotoxicity levels. Together, the analysis provides a useful strategy for the structure–activity relationship (SAR) of flavonoid analogs in distinct protein markers, suggesting optimal functional group positioning to achieve balanced lipophilicity, effective hydrogen bonding, and simultaneously minimized steric hindrance in targeting specific cancer cell types. Full article