Search Results (107)

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

Scutellaria baicalensis Georgi is a valuable medicinal plant of the Lamiaceae family. Its roots have been used in Traditional Chinese Medicine (under the name Huang-qin) since antiquity and are nowadays included in Chinese and European Pharmacopoeias. It is abundant in bioactive compounds which constitute up to 20% of dried root mass. These substances are lipophilic flavones with unsubstituted B-ring, baicalein, and wogonin and their respective glucuronides–baicalin and wogonoside being the most abundant. The content of these compounds is variable and the environmental factors causing this remain partially unknown. The role of these compounds in stress response is still being investigated and in our efforts to measure the effect of NaCl treatment on S. baicalensis growth and metabolic profile, we hope to contribute to this research. Short-term exposure to salt stress (50, 100, and 150 mM NaCl) resulted in a marked increase of baicalein from 1.55 mg to 2.55 mg/g DM (1.6-fold), baicalin from 8.2 mg to 14.7 mg (1.8-fold), wogonin from 4.9 to 6.8 (1.4-fold), and wogonoside from 3.3 to 6.8 mg/g DM (2-fold) in the roots. Conversely, in the aerial parts, the content of individual major flavonoids: carthamidine-7-O-glucuronide and scutellarein-7-O-glucuronide decreased the most by 10–50% from 18.6 mg to 11.3 mg/g (1.6-fold less) and from 6.5 mg to 3.4 mg/g DM (0.52-fold less), respectively. The amino acid profile was also altered with an increase in root concentrations of the following amino acids: arginine from 0.19 to 0.33 mg/g (1.7-fold), glutamate from 0.09 to 0.16 mg/g DM (1.6-fold), alanine from 0.009 to 0.06 mg/g (6.8-fold), proline from 0.011 to 0.029 (2.4-fold) and lysine from 0.016 to 0.063 mg/g (3.9-fold). Aspartate concentration decreased from 0.01 to 0.002 mg/g (4.8-fold less) at 150 mM NaCl. In the aerial parts, the concentration and variation in levels of specific amino acids differed among groups. For instance, the glutamate content exhibited a significant increase exclusively in the treatment group, rising from 0.031 to 0.034 mg/g, representing a 1.2-fold increase. Proline concentration showed a marked increase across all treated groups with the highest from 0.011 to 0.11 mg/g (10-fold). In conclusion, moderate salt stress was shown to increase S. baicalensis root biomass and flavonoid content which is rarely observed in a glycophyte species and provides a foundation for further studies on the mechanisms of osmotic stress adaptation on the specialized metabolism level. Full article

Quercetin, a well-known flavonoid with significant medicinal potential, was derivatized at the C8 position with a tetrahydroisoquinoline (THIQ) moiety, and physicochemical and pharmacological properties, inhibition potential, antioxidant activity, and cytotoxicity of new compounds were evaluated. Physicochemical and pharmacological properties, including lipophilicity, membrane permeability, and P-glycoprotein substrate affinity, were assessed theoretically using the SwissADME software. The metal-chelating ability of the new compounds was evaluated on metal ions Fe²⁺, Zn²⁺, and Cu²⁺, whose homeostasis disruption is linked to the development of Alzheimer’s disease. Inhibition potential was tested on the cholinergic enzymes acetylcholinesterase and butyrylcholinesterase, as well as Na⁺, K⁺-ATPase, an enzyme commonly overexpressed in tumours. Antioxidant potential was assessed using the DPPH assay. Cytotoxicity studies were conducted on healthy MRC-5 cells and three cancer cell lines: HeLa, MDA-231, and MDA-468. The results indicated that derivatization of quercetin with THIQ yielded compounds with lower toxicity, preserved chelating ability, improved antioxidant potential, increased selectivity toward the cholinergic enzyme butyrylcholinesterase, and enhanced inhibition potential toward Na⁺, K⁺-ATPase and butyrylcholinesterase compared to quercetin alone. Therefore, the synthesized derivatives represent compounds with an improved profile and could be promising candidates for further optimization in developing drugs for neurodegenerative and cancer diseases. Full article

Chronic disease inflammation requires safe complementary treatments. The pericarp of Passiflora tripartita var. mollissima (PTM) contains potential anti-inflammatory metabolites. This study aimed to evaluate the bioactive components, antioxidant capacity, and anti-inflammatory effects of PTM extracts at two ripening stages. The bioactive compounds in the hydrophilic and lipophilic extracts of mature and green pericarps were identified by GC-MS and UV–VIS, while the antioxidant capacity was measured by free radical reduction. Anti-inflammatory effects were tested using a rat paw edema model with carrageenan-induced edema, indomethacin, or PTM extracts (100, 250, and 500 mg/kg). The effect of mature hydrophilic extract was further evaluated in an air pouch model, where rats received the placebo, carrageenan, indomethacin, or the extract (500 and 1000 mg/kg). Leukocytes, cytokines, and markers of oxidative stress were evaluated. The results showed the presence of organic compounds, total phenols, and flavonoids. The mature hydrophilic extract exhibited the highest antioxidant activity. At 500 mg/kg, it reduced edema, leukocyte migration, and levels of IL-1β, IL-6, and TNF-α while managing oxidative stress and preventing histological damage. In conclusion, PTM contains bioactive compounds with potential pharmacological properties. The hydrophilic extract of the mature pericarp, at a dose of 500 mg/kg, exhibits an enhanced antioxidant and anti-inflammatory effect. Full article

Cannabis sativa is known for producing over 120 distinct phytocannabinoids, with Δ⁹-tetrahydrocannabinol (Δ⁹-THC) and cannabidiol (CBD) being the most prominent, primarily in their acidic forms. Beyond Δ⁹-THC and CBD, a wide array of lesser-known phytocannabinoids, along with terpenes, flavonoids, and alkaloids, demonstrate diverse pharmacological activities, interacting with the endocannabinoid system (eCB) and other biological pathways. These compounds, characterized by phenolic structures and hydroxyl groups, possess lipophilic properties, allowing them to cross the blood–brain barrier (BBB) effectively. Notably, their antioxidant, anti-inflammatory, and neuro-modulatory effects position them as promising agents in treating neurodegenerative disorders. While research has extensively examined the neuropsychiatric and neuroprotective effects of Δ⁹-THC, other minor phytocannabinoids remain underexplored. Due to the well-established neuroprotective potential of CBD, there is growing interest in the therapeutic benefits of non-psychotropic minor phytocannabinoids (NMPs) in brain disorders. This review highlights the emerging research on these lesser-known compounds and their neuroprotective potential. It offers insights into their therapeutic applications across various major neurological conditions. Full article

Xanthohumol (1) is a major prenylated flavonoid in hops (Humulus lupulus L.) which exhibits a broad spectrum of health-promoting and therapeutic activities, including anti-inflammatory, antioxidant, antimicrobial, and anticancer effects. However, due to its lipophilic nature, it is poorly soluble in water and barely absorbed from the gastrointestinal tract, which greatly limits its therapeutic potential. One method of increasing the solubility of active compounds is their conjugation to polar molecules, such as sugars. Sugar moiety introduced into the flavonoid molecule significantly increases polarity, which results in better water solubility and often leads to greater bioavailability. Entomopathogenic fungi are well known for their ability to catalyze O-glycosylation reactions. Therefore, we investigated the ability of selected entomopathogenic filamentous fungi to biotransform xanthohumol (1). As a result of the experiments, one aglycone (2) and five glycosides (3–7) were obtained. The obtained (2″E)-4″-hydroxyxanthohumol 4′-O-β-D-(4‴-O-methyl)-glucopyranoside (5) has never been described in the literature so far. Interestingly, in addition to the expected glycosylation reactions, the tested fungi also catalyzed chalcone–flavanone cyclization reactions, which demonstrates chalcone isomerase-like activity, an enzyme typically found in plants. All these findings undoubtedly indicate that entomopathogenic filamentous fungi are still an underexploited pool of novel enzymes. Full article

This study aimed to explore the capacity of immobilized lipases on the acetylation of six aglycon flavonoids, namely myricetin, quercetin, luteolin, naringenin, fisetin and morin. For this purpose, lipase B from Candida antarctica (CaLB) and lipase from Thermomyces lanuginosus (TLL) were immobilized onto the surface of ZnOFe nanoparticles derived from an aqueous olive leaf extract. Various factors affecting the conversion of substrates and the formation of monoesterified and diesterified products, such as the amount of biocatalyst and the molar ratio of the substrates and reaction solvents were investigated. Both CaLB and TLL-ZnOFe achieved 100% conversion yield of naringenin to naringenin acetate after 72 h of reaction time, while TLL-ZnOFe achieved higher conversion yields of quercetin, morin and fisetin (73, 85 and 72% respectively). Notably, CaLB-ZnOFe displayed significantly lower conversion yields for morin compared with TLL-ZnOFe. Molecular docking analysis was used to elucidate this discrepancy, and it was revealed that the position of the hydroxyl groups of the B ring on morin introduced hindrances on the active site of CaLB. Finally, selected flavonoid esters showed significantly higher antimicrobial activity compared with the original compound. This work indicated that these lipase-based nanobiocatalysts can be successfully applied to produce lipophilic derivatives of aglycon flavonoids with improved antimicrobial activity. Full article

Daily exposure to solar light is not so harmless as previously thought, since UVA and UVB radiation has a significant effect on human health, by inducing skin-related inflammatory manifestations, such as hyperpigmentation, dermatitis, premature aging, erythema, and sunburn, among the most common skin conditions. At the same time, irreversible diseases such as various types of skin cancers, like basal cell carcinoma, melanoma, and squamous cell carcinoma, have begun to increase at dramatic rates, due to inflammatory and oxidative malignant effects of UV radiation exposure. Within this article, the health promoting effects of sunscreen for skin protection and especially of sunscreen enriched with natural antioxidant, anti-inflammatory, anti-allergic, and anti-cancer bio-functional ingredients are thoroughly reviewed. Emphasis is given to bioactives from grape by-products, such as bio-functional phytochemicals like flavonoids, stilbenes, and phenolic acids, as well as to tomato-derived bioactives like lycopene, which act either solely or synergistically and significantly enhance the antioxidant capacity of the composition product, as well as its photo-protection. The promising outcomes from in vitro studies and those reported from in vivo approaches, as well as the mechanisms of the obtained antioxidant, anti-inflammatory, anti-thrombotic, and antitumor action(s) of sunscreens infused with such natural bioactives, are also outlined. Limitations, such as the difficulties in incorporating lipophilic compounds like lycopene and/or amphiphilic phenolics into sunscreen cosmetic formulations, as well as future perspectives on the overall benefits that these compounds give to sunscreens, helping to improve properties such as smell, color, homogeneity, water resistance, and especially the Sun Protection Factor (SPF), are also discussed. Full article

The fruit juice industry generates a significant amount of waste, with a strong impact on the environment and the economy. Therefore, researchers have been focusing on the characterization of resources considered as food waste. This work provides information about the lipophilic and polar metabolites of pear pomace flours (PPFs) as a tool that can shed more light on the bioactive potential of this residue. Using UPLC-PDA, UPLC-FLR, and GC-MS, the study identified and quantified PPF’s polar and non-polar metabolites. Essential, conditional, and non-essential amino acids were found, with asparagine being the most abundant. Isoprenoids, including lutein, zeaxanthin, and carotene isomers, ranged from 10.8 to 22.9 mg/100 g dw. Total flavonoids and phenolic compounds were 520.5–636.4 mg/100 g dw and 536.9–660.1 mg/100 g dw, respectively. Tocotrienols and tocopherols were identified, with concentrations of 173.1–347.0 mg/100 g dw and 468.7–913.4 mg/100 g dw. Fatty acids were the major non-polar compounds. All fractions significantly reduced matrix metalloproteinase-9 (MMP-9) activity. Although PPF had lower antioxidant potential (3–6 mmol Trolox/100 g dw), it inhibited AChE and BuChE by 23–30% compared to physostigmine salicylate. These findings suggest that pear pomace waste can be repurposed into functional products with valuable bioactive properties by re-introducing it in the food chain. Full article