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BACKGROUND: Evaluation of herbicidal activity and identification of active compounds are important bases for the development of new botanical herbicides. RESULTS: This study confirmed that Symphoricarpos orbiculatus has high herbicidal activities against mono‐dicotyledonous weeds, including Echinochloa crusgalli, Digitaria sanguinalis, Amaranthus retroflexus and Portulaca oleracea. By bioassay‐guided isolation, 12 compounds were isolated and identified from S. orbiculatus for the first time, including iridoids: naucledal (K1), loganin (K2), loganigenin (K3), loganin acid (K4), glucologanin (K5) and vogeloside (K6), as well as flavonoids: quercetine (K7), luteolin (K8), nobiletin (K9), astragalin (K10), isorhamnetin 3‐d‐glucoside (K11) and rutin (K12). Biological assays showed that iridoids are the main active ingredients of S. orbiculatus. The compounds of K5 and K6 could inhibit both the root (IC50 = 37.54 and 38.91 μg mL−1, respectively) and shoot (IC50 = 42.78 and 45.72 μg mL−1, respectively) of Portulaca oleracea, which have a weeding toxicity similar to that of the commercialized plant‐based herbicide pelargonic acid. In addition, the results of pot culture assay showed that S. orbiculatus ethanol extracts had high fresh weight control effect against Digitaria sanguinalis and P. oleracea at the concentration of 40 g L−1. After 7 days, both the soil treatment and the stem and leaf spray method resulted in severe leaf necrosis and significant leaf etiolation. CONCLUSION: Symphoricarpos orbiculatus and its herbicidal active compounds have the potential to develop into botanical herbicides, and are first reported in the present study. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Introduction: Genistin, as a kind of natural isoflavone glycoside, has good biological activity, and its weak absorption makes it closely related to intestinal flora. However, the roleof theintestinal flora is still unclear andwhether themetabolites produced by the intestinal flora are absorbed systemically is also variable. Methods: Genistin was fermented for 24 h based on fecal bacteria fermentation technology. The components were qualitatively and quantitatively analyzed by HPLC and UHPLC-Q-Exactive Orbitrap Mass spectrometry. The composition of intestinal flora in fermentation samples from fecal bacteria was detected by 16S rRNA sequencing. Five representative probiotics were cultured in vitro and fermented with genistin to determine similarities and differences in genistin metabolites by different bacteria at different times. Finally, the absorption results of metabolites by fermentation were verified by a Caco-2 cell monolayer. Results: The HPLC results of fecal fermentation showed that genistein levels increased from 0.0139 ± 0.0057 mg/mL to 0.0426 ± 0.0251 mg/mL and two new metabolites were produced. A total of 46 metabolites following fecal fermentation were identified, resulting from various biotransformation reaction products, such as decarbonylation, hydroxylation, and methylation. Simultaneously, the 16S rRNA results showed that the intestinal flora changed significantly before and after fermentation and that the intestinal microorganisms in the control (Con) group and the fermentation (Fer) group showed a significant separation trend. Five genera, Lactobacillus, Bifidobacterium, Parabacteroides, Sutterella, and Dorea, were considered the dominant flora for genistin fermentation. The qualitative results of fermentation of genistin by five probiotics at different times showed that there were significant differences in small molecule metabolites by fermentation of different bacteria. Meanwhile, most metabolites could be identified following fecal bacteria fermentation, which verified the importance of the dominant bacteria in the feces for the biotransformation of components. Finally, the absorption results of the metabolites based on the Caco-2 cell monolayer showed that 14 metabolites could be absorbed into the circulation in vivo through the mesentery. Discussion: The small molecule metabolites of genistin by fermentation of fecal bacteria can be well absorbed systemically by the body. These studies provide a reference value for explaining the transformation and absorption of flavonoid glycosides in the intestine. [ABSTRACT FROM AUTHOR]

Camellia flavida var. flavida, commonly known as "Jinhua Tea", has its flowers and leaves traditionally utilized as tea and functional food sources. However, there is limited knowledge about its bioactive components and their biological activities. This study isolated ten previously unidentified glycoside compounds from the flowers of Camellia flavida, including three oleanane-type triterpenoid saponins (compounds 1–3) and seven flavonoid glycosides (compounds 4–10), collectively named flavidosides A–J. This study assessed the cytotoxicity of these compounds against a panel of human cancer cell lines and their α-glucosidase inhibitory activities. Notably, flavidoside C showed significant cytotoxicity against BEL-7402 and MCF-7 cell lines, with IC50 values of 4.94 ± 0.41 and 1.65 ± 0.39 μM, respectively. Flavidoside H exhibited potent α-glucosidase inhibitory activity, with an IC50 value of 1.17 ± 0.30 mM. These findings underscore the potential of Camellia flavida in the development of functional foods. [ABSTRACT FROM AUTHOR]

Ocimum species have a great interest in different traditional medicinal systems. This study examined the chemical composition, antioxidant properties, enzyme inhibitory effects, and antibacterial and antifungal activities of the aerial parts of Ocimum gratissimum, Ocimum americanum, and Ocimum basilicum from the Comoros Islands. The extracts were analyzed using high‐performance liquid chromatography‐mass spectrometry (HPLC‐MS) to determine their chemical composition. Antioxidant activity was assessed using 2,2‐Diphenyl‐1‐picrylhydrazyl (DPPH), 2,2′‐Azino‐bis(3‐ethylbenzothiazoline‐6‐sulfonic acid) diammonium salt (ABTS), cupric reducing antioxidant capacity (CUPRAC), ferric reducing antioxidant power (FRAP), chelating ability, and phosphomolybdenum radical scavenging assays. Enzyme inhibitory activities against acetylcholinesterase (AChE), butrylcholinesterase (BChE), tyrosinase, amylase, and glucosidase were evaluated using spectrophotometric methods. Antibacterial and antifungal activities were tested using the broth microdilution method against selected pathogenic microorganisms. The selected enzymes and proteins were evaluated using in silico methods with biomolecules from these plants. In addition, 111 different metabolites were identified in the tested extracts using advanced HPLC/MS techniques. The most significant number of detected compounds were derivatives of hydroxycinnamic acids, followed by flavonoid glycosides and aglycones and derivatives of hydroxybenzoic acids. All three Ocimum species exhibited significant antioxidant activities, O. gratissimum exhibited the best‐reducing abilities in CUPRAC and FRAP assays. In addition, enzyme inhibitory assays revealed that O. americanum had the most potent inhibitory effect on tyrosinase (48.01 ± 3.89 mg kojic acid equivalent [KAE]/g), and amylase (1.08 ± 0.02 mmol acarbose equivalent [ACAE]/g). Antibacterial and antifungal tests demonstrated that the extracts possess broad‐spectrum activity. Molecular docking results showed that compounds exhibited remarkable binding energies with target enzymes and proteins. The molecular dynamics simulations identified chicoric acid with MurE of Staphylococcus aureus complex as the most promising drug candidate. These findings support their traditional medical and nutraceutical uses and suggest possibilities for natural functional applications. Summary: The study suggests that chicoric acid and MurE possessed an excellent interaction for Staphylococcus aureus, and chicoric acid may be a valuable candidate against S. aureus. [ABSTRACT FROM AUTHOR]

Insecticidal potential of extracts of Citrus aurantifolia, family Rutaceae, was evaluated to control whiteflies, Bemisia tabaci. Biocidal activity directed chromatographic separation of chloroform and butanol fractions, with spectral identification (1D-NMR, 2D-NMR, ESIMS) of the active fractions have been resulted in separation and structural elucidation of for previously described coumarins (bergapten 1, limettin 2, isopimpinellin 3, oxypeucedanin hydrate 4) in addition to a new dimeric coumarin (12R, 12'R)-aurantifolin 5, two known limonoids; 21,23-dihydro-23-methoxy-21-oxolimonin 6, 21,23-dihydro-23-methoxy-21-oxonomilin 7, and two known flavonoid glycosides; scoparin 8, and narcissin 9. Amongst these compounds, narcissin 9 was the most effective after 24 h. of treatment while, (12R, 12'R)-aurantifolin 5 was the most potent against B. tabaci, 3rd instar nymphs after 72 h. of treatment and under laboratory conditions, with LC50 values of 33.31and 15.92 ppm, respectively comparing with the positive control azadirachtin. [ABSTRACT FROM AUTHOR]

[Display omitted] • Rutin (Ru), an antioxidant flavonoid, is prevalent in plant-based human diets. • Ru/MnO 2 was synthesized using a straightforward, rapid one-step process. • Ru/MnO 2 exhibits significantly higher T 1 relaxivity than previously reported MnO 2. • Ru/MnO 2 can target glucose transporters (GLUTs) overexpressed in various tumors. • Ru/MnO 2 shows promise in MRI and photothermal therapy of malignant tumors. Manganese oxide nanoparticles (MONs)-based contrast agents have attracted increasing attention for magnetic resonance imaging (MRI), attributed to their good biocompatibility and advantageous paramagnetism. However, conventional MONs have poor imaging performance due to low T 1 relaxivity. Additionally, their lack of tumor-targeting theranostics capabilities and complex synthesis pathways have impeded clinical applications. Rutin (Ru) is an ideal tumor-targeted ligand that targets glucose transporters (GLUTs) overexpressed in various malignant tumors, and exhibits photothermal effects upon chelation with metal ions. Herein, a series of Ru-coated MONs (Ru/MnO 2) were synthesized using a straightforward, rapid one-step process. Specifically, Ru/MnO 2 -5, with the smallest crystal size of approximately 4 nm, exhibits the highest T 1 relaxivity (33.3 mM-1s−1 at 1.5 T, surpassing prior MONs) along with notable stability, photothermal efficacy, and tumor-targeting ability. Furthermore, Ru/MnO 2 -5 shows promise in MRI and photothermal therapy of H22 tumors owing to its superior GLUTs-mediated tumor-targeting capability. [ABSTRACT FROM AUTHOR]

Copyright of Science & Technology of Food Industry is the property of Science & Technology of Food Industry Editorial Office and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Our previous study found that the aerial parts of Chinese liquorice (Glycyrrhiza uralensis Fisch.) had pharmacological effects against chronic non-bacterial prostatitis in rats, however the pharmacologically active compounds remain unclear. Here, a method based on UPLC-Q-Exactive Orbitrap-MS was established to qualitatively analyse the flavonoid glycosides rich fraction extracted from the aerial part of G. uralensis Fisch., after pretreatment with n-butanol and enrichment using AB-8 macroporous resin. Using both positive and negative ion modes, 52 compounds were identified or tentatively characterised by comparison with standards and the literature: 40 flavonoids, 8 organic acids, 2 chromones, 1 coumarin, and 1 phenylethanoid glycoside. This study provides not only an approach to enrich flavonoid glycosides but also a methodology for quickly determining the relevant bioactive components in the aerial parts of G. uralensis Fisch. [ABSTRACT FROM AUTHOR]

The World Health Organization reports that 30% of adults worldwide suffer from insomnia, while 10% of people worldwide suffer with various forms of anxiety. The significant negative effects of conventional medications used to treat anxiety and insomnia, such as abuse, addiction, amnesia, and cognitive and sexual dysfunction, have led to an increased preference for naturally derived substances with fewer side effects. Accordingly, in this study, the sedative and anxiolytic effects of n-hexane, ethyl acetate (EtOAc), methanol (MeOH) and water extracts of the aerial parts of Capparis sicula Duhamel., which is used for sedative purposes in folk medicine, were evaluated. To evaluate the sedative and anxiolytic effects of each extract, bioassay systems were used including traction and hole-board tests. The MeOH extract of C. sicula was the most active extract on in vivo traction and hole-board tests compared to Diazepam. From the MeOH extract, major components were isolated, and their structures were identified as three flavonoid glycosides [rutin (1), quercetin-3-O-glucoside (2), and quercetin 3-O-rhamnoside (3)] using spectral techniques. The most abundant component was determined to be rutin, comprising 8mg/100mg dry extract in MeOH extract and 76.7 mg/100 mg dry fraction in fraction C using HPLC. The molecular docking studies evaluated the interaction of isolated flavonoid glycosides with the interaction energies and protein-ligand interaction details of the anxiety-related receptors GABAA and GABAB. For the GABAA receptor, quercetin-3-O-glucoside demonstrated the highest docking score. Quercetin-3-O-rhamnoside and rutin also show promising interactions, particularly with the GABAB receptor, highlighting their potential as modulators of these receptors. In conclusion, the use of C. sicula for sedative purposes in folk medicine has been confirmed for the first time by in vivo studies, and its possible active compounds and sedative-anxiolytic mechanism have been determined through phytochemical and in silico studies. [ABSTRACT FROM AUTHOR]

High-density olive groves, despite their interesting production potential, have several limitations, including their high fruit load and irrigation requirements. This study aimed to evaluate the effects of fruit load and deficit irrigation on oil yield, fruit quality, and olive chemical composition in a high-density olive grove (cv Sikitita). Our main hypothesis was that primary metabolism, as influenced by crop load and stress, could modify the accumulation of different phenolic classes. Different fruit loads were generated through flower thinning (66%, 50%, 33%, 0%), and two deficit irrigation treatments (−60%, −75%) were compared to the well-watered control (920 m3/ha). Thinning treatments had a limited effect on oil yield; on the other hand, deficit irrigation caused considerably less oil accumulation in the fruit on all sampling dates. Thinning 66% and deficit irrigation 75% were considered with the control for untargeted metabolomic analysis, including three sampling dates. A total of 233 distinct phenolic compounds were annotated. Multivariate HCA results indicated that harvest time had an impact on the phenolic profile of olive fruits, obtaining two separated clusters that grouped t1 and t2 together and apart from t3, which clustered independently. Regarding agronomic techniques, they played a differential role in the phenolic profile (supervised OPLS-DA). Fruit load mostly affected flavonoid glycosides. In contrast, the phenolic response to deficit irrigation was more heterogeneous, with phenolic acids (35%), flavonoids (25%), LMW, and other phenols (25%). [ABSTRACT FROM AUTHOR]

Free radicals are highly reactive compounds that lead to the onset of a variety of serious health conditions, known as "oxidative stress". Antioxidants, on the other hand, act as defense mechanisms to fight the accumulation of free radicals and maintain cell homeostasis. Urtica dioica L. is a medicinal plant with unique antioxidant properties, mainly attributable to the presence of polar phenolic compounds. This study aimed to optimize the combination of determinant factors toward the maximum extraction of antioxidants from U. dioica L. Furthermore, it investigated the protective role of the extract on red blood cells that were exposed to oxidative stress. The extraction optimization was performed using Response Surface Methodology and the in vitro antioxidant activity of the extract was determined with Folin–Ciocalteu, FRAP, and DPPH assays. Based on the results, the highest value of antioxidant activity and polar phenolic compounds was recorded using 34% (v/v) ethanol as a solvent in an ultrasonic process carried out at 42 °C for 87 min. In addition, UV–Vis spectrum of the extract revealed the presence of chlorophylls, carotenoids, and flavonoid glycosides. This study also provided insight into the in vitro protective effect of the plant extract on red blood cells morphology under oxidative stress conditions. The findings highlighted the good predictability of the extraction model and the potential role of the extract as an antioxidant product. [ABSTRACT FROM AUTHOR]

Summary: In order to investigate the hypoglycaemic mechanism and potential applications of four hypoglycaemic flavonoid glycosides, namely myricitrin, Cyanidin‐3‐O‐glucoside (C3G), hyperoside and quercitrin in Myrica rubra pomace, the stability of these four flavonoid glycosides and their binding mechanisms were studied using molecular docking. The results demonstrated that pH value affects on the stability of these four components in M. rubra pomace. C3G exhibited the most significant inhibitory effect on α‐glucosidase at pH 5, with myricitrin, hyperoside and quercitrin showing the highest inhibitory effect at pH 7. Moreover, an increase in temperature and storage time reduced the inhibitory effect of these four glycosidic components on α‐glucosidase. Molecular docking analysis revealed that myricitrin formed hydrogen bonds with the active site residues of α‐glucosidase, namely Phe550, Ile552, Asp555, Ser574 and Arg576, and also engaged in hydrophobic interactions with Lys551. Hyperoside formed hydrogen bonds with α‐glucosidase, formed hydrophobic interactions with Lys50 and exhibited π‐cation interaction with Lys53. Quercitrin formed hydrogen bonds with α‐glucosidase, formed hydrophobic interactions with Lys500 and established salt bridges with Lys50. C3G formed hydrogen bonds and hydrophobic interactions with α‐glucosidase and showed π‐π interactions with Phe301. These findings will provide valuable insights for the application of these four chemicals. [ABSTRACT FROM AUTHOR]

BACKGROUND: Obesity is recognized as a lifestyle‐related disease and the main risk factor for a series of pathological conditions, including cardiovascular diseases, hypertension and type 2 diabetes. Citrus limon is an important medicinal plant, and its fruits are rich in flavonoids investigated for their potential in managing obesity. In the present work, a green extraction applied to lemon squeezing waste (LSW) was optimized to recover pancreatic lipase (PL) inhibitors. RESULTS: The microwave‐assisted procedure yielded an extract with higher lipase inhibitory activity than those obtained by maceration and ultrasound. The main compounds present in the extract were identified by high‐performance liquid chromatographic–mass spectrometric analysis, and hesperidin, eriocitrin and 4′‐methyllucenin II were isolated. The three compounds were evaluated for in vitro PL inhibitory activity, and 4′‐methyllucenin II resulted in the most promising inhibitor (IC50 = 12.1 μmol L−1; Ki = 62.2 μmol L−1). Multispectroscopic approaches suggested the three flavonoids act as competitive inhibitors and the binding studies indicated a greater interaction between PL and 4′‐methyllucenin II. Docking analysis indicated the significant interactions of the three flavonoids with the PL catalytic site. CONCLUSION: The present work highlights flavonoid glycosides as promising PL inhibitors and proposes LSW as a safe ingredient for the preparation of food supplements for managing obesity. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Copyright of Science & Technology of Food Industry is the property of Science & Technology of Food Industry Editorial Office and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Abstract Insecticidal potential of extracts of Citrus aurantifolia, family Rutaceae, was evaluated to control whiteflies, Bemisia tabaci. Biocidal activity directed chromatographic separation of chloroform and butanol fractions, with spectral identification (1D-NMR, 2D-NMR, ESIMS) of the active fractions have been resulted in separation and structural elucidation of for previously described coumarins (bergapten 1, limettin 2, isopimpinellin 3, oxypeucedanin hydrate 4) in addition to a new dimeric coumarin (12R, 12’R)-aurantifolin 5, two known limonoids; 21,23-dihydro-23-methoxy-21-oxolimonin 6, 21,23-dihydro-23-methoxy-21-oxonomilin 7, and two known flavonoid glycosides; scoparin 8, and narcissin 9. Amongst these compounds, narcissin 9 was the most effective after 24 h. of treatment while, (12R, 12’R)-aurantifolin 5 was the most potent against B. tabaci, 3rd instar nymphs after 72 h. of treatment and under laboratory conditions, with LC50 values of 33.31and 15.92 ppm, respectively comparing with the positive control azadirachtin.

Copyright of Shipin Kexue/ Food Science is the property of Food Science Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Strychnos peckii (Loganiaceae) is an important active ingredient in curare poisons in the Amazon rainforest. Although previous studies have identified this species as a promising source of monoterpene indole alkaloids (MIAs), knowledge about other natural products is still scarce. Thus, to detect and guide the isolation of unprecedented bioactive compounds from the leaves of S. peckii, an untargeted high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS) analysis was performed with the leaf aqueous extract. The HPLCMS analysis allowed the detection of eleven compounds, including the alkaloids harman-3-carboxylic acid (5) and N,ß-glucopyranosyl vincosamide (6), and the flavonoids quercetin 3-O-rhamnopyranoside (9) and kaempferol 3-Orhamnopyranoside (10), all not previously reported in the Loganiaceae family. These compounds, along with strictosidine (3), 5-carboxystrictosidine (7), and desoxycordifoline (8) were isolated through modern chromatographic techniques and determined by using NMR spectroscopy in combination with MS. Overall, the untargeted HPLC-MS analysis proved to be a simple and effective approach to guide the isolation of substances not yet identified from S. peckii. [ABSTRACT FROM AUTHOR]

Background: Grewia flava infusions are consumed to assist with kidney problems and stomach ailments. However, there are no scientific data on the phytochemical profile or biological properties to validate its folklore use. Thus, the study aimed to assess the phytochemical profile, antioxidant, and antimicrobial activities of Grewia flava twig extracts. Methodology: The antioxidant activities of the extracts were assayed using 1,1-diphenyl-2-picrylhydrazyl radical scavenging, reducing power, metal chelation, and total phenolic and flavonoid content assays. The agar well diffusion and microdilution methods were used for crude extracts and fractions (from 80% methanol extract) for antimicrobial screening against P. aeruginosa, S. aureus, E. coli, B. subtilis, A. niger, and R. oryzae. Results: The 80% methanol twig extract (250.00 ± 2 GAE/g) exhibited a high concentration of phenolic content, followed by the distilled water extract (192.00 ± 2 mg GAE/g) and the hexane extract (43.10 ± 0.2 mg GAE/g). Fraction 14 of the methanol twig extract exhibited MIC values of 0.21–0.31 mg/mL against all test microorganisms. The root and twig extracts exhibited significant antioxidant and antimicrobial activities, which were attributed to the extracts of bioactive phytochemical compounds such as alkaloids, flavonoids, saponins, steroids, glycosides, anthraquinones, and tannins that were detected in the extracts. Also, the root and twig non-polar extracts were subjected to gas chromatography–mass spectrometry analysis, which identified several bioactive compounds like betulin, β-amyrin, palmitic acid, lupenone, and phytol, highlighting the potential of the plant species as a botanical drug. Conclusions: The study supports the traditional use of plant roots and twigs for treating various ailments, indicating their medicinal value. The twigs can be used in place of the roots to guarantee Grewia flava harvesting that is sustainable. However, a comparison of the quantities of the active compound in the twigs and roots using LC–MS is crucial. [ABSTRACT FROM AUTHOR]

Flavonoids are usually present in forms of glucosides in plants, which could be catabolized by β‐glucosidase (BGLU) to form their corresponding flavonoid aglycones. In this study, we isolated three abiotic‐responsive BGLU genes (MtBGLU17, MtBGLU21 and MtBGLU22) from Medicago truncatula, and found only the recombinant MtBGLU17 protein could catalyse the hydrolysis of flavonoid glycosides. The recombinant MtBGLU17 protein is active towards a variety of flavonoid glucosides, including glucosides of flavones (apigenin and luteolin), flavonols (kaempferol and quercetin), isoflavones (genistein and daidzein) and flavanone (naringenin). In particular, the recombinant MtBGLU17 protein preferentially hydrolyses flavonoid‐7‐O‐glucosides over their corresponding 3‐O‐glucosides. The content of luteoin‐7‐O‐glucoside was reduced in the MtBGLU17 overexpression plants but increased in the Tnt‐1 insertional mutant lines, whereas luteoin content was increased in the MtBGLU17 overexpression plants but reduced in the Tnt‐1 insertional mutant lines. Under drought and salt (NaCl) treatment, the MtBGLU17 overexpression lines showed relatively higher DPPH content, and higher CAT and SOD activity than the wild type control. These results indicated that overexpression lines of MtBGLU17 possess higher antioxidant activity and thus confer drought and salt tolerance, implying MtBGLU17 could be potentially used as a candidate gene to improve plant abiotic stress tolerance. Summary statement: MtBGLU17 gene from Medicago truncatula encodes a β‐glucosidase that is able to hydrolyse a variety of flavonoid glucosides. Both gain‐of‐function and loss‐of‐function studies in M. truncatula demonstrated that MtBGLU17 is involved in drought and salt tolerance by balancing the accumulation of flavonoid aglycones with ROS scavenging activity. [ABSTRACT FROM AUTHOR]

A number of studies have indicated the potential role of secondary metabolites, referred to as 'resistance factors', in plant defence against insect pests. Nevertheless, it remains unclear which metabolites serve as predictors of resistance in chrysanthemum cultivars against thrips. In the present study, the phenolic compounds of chrysanthemum leaves at different ontogenetic stages were analysed using high-performance liquid chromatography (HPLC). Furthermore, the relative epidermal flavonol contents in the leaves were quantified using the Dualex® Scientific 4 sensor, and the suitability of this non-destructive method for the rapid discrimination of resistance levels was evaluated. The results demonstrated that the most notable discrepancies in phenolic metabolite profiles were observed in the older leaves and the vegetative state of the chrysanthemum plants. Multiple discriminant analysis was conducted using HPLC-analysed metabolites to predict the importance of metabolites in resistant, susceptible, or highly susceptible plants in the vegetative stage. The results demonstrated that multiple metabolites, rather than a single metabolite, are responsible for thrips resistance in chrysanthemum. However, the relative flavonol content did not reflect the HPLC-analysed flavonoid glycosides or hydroxycinnamic acid derivatives, indicating that the Dualex® sensor is not a suitable device for determining resistance levels in chrysanthemums. Testing is required to extend and analyse the results in greater depth. [ABSTRACT FROM AUTHOR]

Objective: In our study, we researched the chemical composition of Linaria corifolia Desf. We also tested in vitro antioxidant, and anticholinesterase activities of different extracts, and compounds from L. corifolia. Methods: We isolated from ethyl acetate and n-butanol extracts of L. corifolia aerial parts. We used various spectroscopic methods. We also compared the results with data in the literature. This allowed us to determine the structure of the compounds. We used different spectroscopic methods and comparisons with literature data to determine the structure of the compounds. We evaluated the antioxidant activities of 20% aqueous methanol, ethyl acetate, and n-butanol extracts using DPPH, ABTS Radical Scavenging Effect, and CUPRAC Assay, and also examined total phenol and flavonoid contents. We used Ellman's method to find the cholinesterase inhibitor activities of the extracts, and isolated compounds. Results: We isolated 6 compounds in ethyl acetate and n-butanol extracts. These compounds have terpenoid (iridoid glycosides), and phenolics (flavonoid, and phenylpropanoid structures). We isolated linariin and acteoside (verbascoside) from ethyl acetate. We isolated antirrhinoside, 6-ß-Hydroxyantirrhide, catalpol, and aucubin from n-butanol extract. The ethyl acetate extract was most active in all antioxidant methods due to its high phenolic content. In contrast to phenolic content, n-butanol extract had more flavonoids. The ethyl acetate extract had higher acetylcholinesterase inhibitory activity at 200 and 400 μg/ml. Linariin had the highest acetylcholinesterase inhibitory effect among the pure compounds. The extracts and pure compounds inhibited butyrylcholinesterase less than acetylcholinesterase. Conclusion: The isolated compounds are new compounds for the L. corifolia plant. The plant's cholinesterase inhibitor activity was investigated for the first time. We found low anti-acetylcholinesterase and butyrylcholinesterase activities. [ABSTRACT FROM AUTHOR]

Haemaphysalis longicornis is a common Ixodida tick species found in temperate areas of Asian countries. An anti-tick assay was conducted on adult female H. longicornis ticks. Plant extract solutions were prepared at concentrations of 50, 25, and 10 mg/mL. Tick survival and mortality were assessed by counting the number of dead and live ticks at 24 h, 48 h, 72 h, and 96 h posttreatment. Out of 11 plant extracts screened, Artemisia judaica extract exhibited the highest potency with 100% mortality (5/5) at 48 h when applied at high and moderate concentrations (50 and 25 mg/mL). Similar results were observed at 96 h for the 10 mg/mL group compared to the untreated ticks. Cleome droserifolia extract demonstrated partial activity with 60% (3/5) and 20% (1/5) mortality at 96 h posttreatment at concentrations of 50 and 25 mg/mL, respectively. Forsskaolea tenacissima extract showed a weak effect with 100% tick mortality (5/5) only at the highest treatment concentration after 96 h. To confirm the activity of A. judaica, trial 2 was conducted. A. judaica demonstrated potency within 48 h in high dose and 72 h in moderate dose, with 100% mortality (15/15) at 96 h posttreatment compared to untreated ticks. The median lethal time 50 (LT50) values were 30.37 h for the high and 55.08 h for the moderate doses. Liquid chromatography‒mass spectrometry was performed on the most potent candidate (A. judaica) to identify its phytochemical components. The results revealed the presence of 9 compounds identified through manual annotation and 74 compounds from the Global Natural Products Social library. These compounds included terpenoids, steroids, phenylpropanoids, flavonoid glycosides, flavonoids, and benzenoids. Camphor was identified as the major component via both approaches. These findings suggest the potential use of A. judaica extract in the future development of acaricidal therapeutics. [ABSTRACT FROM AUTHOR]

Tragopogon coelesyriacus is a pharmacotherapeutic herbaceous plant belonging to the Asteraceae family and consumed as a vegetable. Here, the methanolic and water extracts of T. coelesyriacus were obtained from its aboveground parts (stem, leaves, and flowers), and the phytochemical potentials were investigated by LC‐HRMS (liquid chromatography–high resolution mass spectrometry) analysis for the first time. The antibacterial, antifungal, and anticarcinogenic activities of T. coelesyriacus extracts were investigated using experimental and in silico methods. T. coelesyriacus methanol extract revealed remarkable inhibitory activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Klebsiella pneumonia (MICs = 0.83, 1.67, and 1.67 mg/mL, respectively) compared to Escherichia coli and Enterobacter aerogenes (MIC = 53.3 mg/mL). Inhibitory effects of T. coelesyriacus methanolic extracts were also observed in all Candida species tested, with the highest inhibition on Candida krusei (MIC = 0.83 mg/mL), whereas no inhibitory effect was identified from the water extract. Additionally, both T. coelesyriacus methanolic (IC50 = 86 μg/mL) and water (IC50 = 92 μg/mL) extracts revealed significant selective anticarcinogenic effects on AR42J pancreatic cancer cells. HeLa and MDA‐MB‐231 cells were, however, more resilient to methanol and water extract, respectively. In silico analyses further elucidated the noteworthy antibacterial potential of keracyanin chloride on S. aureus MurB enzyme and the remarkable inhibitory potential of naringin on FYN kinase specific for pancreatic cancer (AR42J) development. In conclusion, T. coelesyriacus phytochemicals with antibacterial, antifungal, and anticancer properties were revealed for the first time, and molecular docking studies on potential targets confirmed good agreement with experimental findings. Therefore, the current studies on T. coelesyriacus provide the basis for investigating new pharmaceutical potentials of other Tragopogon members. [ABSTRACT FROM AUTHOR]

Olive leaves (OLLs) are an exceptional bioresource of natural polyphenols with proven antioxidant activity, yet the applicability of OLL extracts is constrained by the relatively high polarity of the major polyphenols, which occur as glycosides. To overcome this limitation, OLLs were subjected to both hydrothermal and ethanol organosolv treatments, fostered by acid catalysis to solicit in parallel increased polyphenol recovery and polyphenol modification into simpler, lower-polarity substances. After an initial screening of natural organic acids, oxalic acid (OxAc) was found to be the highest-performing catalyst. The extraction behavior using OxAc-catalyzed hydrothermal and ethanol organosolv treatments was appraised using kinetics, while treatment optimization was accomplished by deploying response-surface methodology. The comparative assessment of the composition extracts produced under optimal conditions of residence time and temperature was performed with liquid chromatography–tandem mass spectrometry and revealed that OLLs treated with 50% ethanol/1.5% HCl suffered extensive oleuropein and flavone glycoside hydrolysis, affording almost 23.4 mg hydroxytyrosol and 2 mg luteolin per g dry weight. On the other hand, hydrothermal treatment with 5% OxAc provided 20.2 and 0.12 mg of hydroxytyrosol and luteolin, respectively. Apigenin was in all cases a minor extract constituent. The study presented herein demonstrated for the first time the usefulness of using a natural, food-grade organic acid to perform such a task, yet further investigation is needed to maximize the desired effect. [ABSTRACT FROM AUTHOR]

Introduction: As a new discipline, network pharmacology has been widely used to disclose the material basis and mechanism of Traditional Chinese Medicine in recent years. However, numerous researches indicated that the material basis of TCMs identified based on network pharmacology was the mixtures of beneficial and harmful substances rather than the real material basis. In this work, taking the anti-NAFLD (non-alcoholic fatty liver disease) effect of Bai Shao (BS) as a case, we attempted to propose a novel bioinformatics strategy to uncover the material basis and mechanism of TCMs in a precise manner. Methods: In our previous studies, we have done a lot work to explore TCMinduced hepatoprotection. Here, by integrating our previous studies, we developed a novel computational pharmacology method to identify hepatoprotective ingredients from TCMs. Then the developed method was used to discover the material basis and mechanism of Bai Shao against Nonalcoholic fatty liver disease by combining with the techniques of molecular network, microarray data analysis, molecular docking, and molecular dynamics simulation. Finally, literature verification method was utilized to validate the findings. Results: A total of 12 ingredients were found to be associated with the anti-NAFLD effect of BS, including monoterpene glucosides, flavonoids, triterpenes, and phenolic acids. Further analysis found that IL1-ß, IL6, and JUN would be the key targets. Interestingly, molecular docking and molecular dynamics simulation analysis showed that there indeed existed strong and stable binding affinity between the active ingredients and the key targets. In addition, a total of 23 NAFLD-related KEGG pathways were enriched. The major biological processes involved by these pathways including inflammation, apoptosis, lipid metabolism, and glucose metabolism. Of note, there was a great deal of evidence available in the literature to support the findings mentioned above, indicating that our method was reliable. Discussion: In summary, the contributions of this work can be summarized as two aspects as follows. Firstly, we systematically elucidated the material basis and mechanism of BS against NAFLD from multiple perspectives. These findings further enhanced the theoretical foundation of BS on NAFLD. Secondly, a novel computational pharmacology research strategy was proposed, which would assist network pharmacology to uncover the scientific connotation TCMs in a more precise manner. [ABSTRACT FROM AUTHOR]

Simple Summary: The presence of secondary metabolites like flavonoids, alkaloids, and phenolic compounds in white mulberry (Morus alba) make it an ornamental tree mainly in the Asian subcontinent. These secondary metabolites are synthesized through various biosynthetic pathways. Flavonoids like rutin, quercetin, and kaempferol are produced via the phenylpropanoid and flavonoid biosynthetic pathways. The key enzymes responsible for this pathway include phenylalanine ammonia-lyase, chalcone synthase, and flavonoid hydroxylases. Phenolic compounds like resveratrol and oxyresveratrol are produced via the phenylpropanoid pathway using phenylalanine as a precursor. Presences of these secondary metabolites, like in the case of flavonoids (rutin and quercetin), in the mulberry tree have potential biological activities like antioxidant, anti-inflammatory and neuroprotective effects. Also, they have been found to have great medicinal importance, for example in treating diabetes, obesity and neurodegenerative diseases. Also, phenolic compounds like reservertrol exhibit cardio-protective, anticancer, and anti-aging properties. Traditional natural products have been the focus of research to explore their medicinal properties. One such medicinally important plant is the white mulberry, Morus alba, widely distributed in the Asian subcontinent. It is one of the most cultivated species of mulberry tree and has attracted more focus from researchers because of its abundance in phytochemicals as well as multipurpose uses. The leaves, fruits and other parts of the white mulberry plant act as a source of valuable bioactive compounds like flavonoids, phenolic acids, terpenoids and alkaloids. These secondary metabolites have manifold healthy uses as they possess antioxidant, anti-inflammatory, antidiabetic, neutrotrophic, and anticancer properties. Despite the increasing scientific interest in this plant, there are very few reviews that highlight the phytochemistry and biological potential of white mulberry for biomedical research. To this end, this review elaborates the phytochemistry, biosynthetic pathways and pharmacological activities of the glycoside flavonoids of Morus alba. A comprehensive analysis of the available literature indicates that Morus alba could emerge as a promising natural agent to combat diverse conditions including diabetes, cancer, inflammation and infectious diseases. To achieve such important objectives, it is crucial to elucidate the biosynthesis and regulation mechanisms of the bioactive compounds in white mulberry as well as the multifaceted pharmacological effects attributed to this plant resource. The present review paper is intended to present a summary of existing scientific data and a guide for further research in the phytochemistry and pharmacology of white mulberry. Further, a biosynthetic pathway analysis of the glycoside flavonoid in mulberry is also given. Lastly, we discuss the pros and cons of the current research to ensure the prudent and effective therapeutic value of mulberry for promoting human and animal health. [ABSTRACT FROM AUTHOR]

Summary: The poor water solubility of flavonoids has always been a bottleneck restricting industrial production and application. The key problem of water‐solubility of flavonoids was solved by establishing an alkali substrate‐feeding engineering conversion platform using recombinant rhamnosidase. The results showed that the recombinant enzyme had α‐L‐rhamnosidase activity. Using this enzyme, four kinds of flavonoids such as hesperidin (HSD) were successfully hydrolyzed to products such as hesperetin 7‐O‐glucoside (HMG). Four key enzyme reaction conditions such as temperature, pH, feed rate and substrate specificity were investigated, and the optimum process parameters of the conversion platform were obtained. That was, under the conditions of temperature 50 °C, pH 6 and feeding speed 0.5 mL min−1, HSD conversion efficiency can reach 8.65 mg min−1. In addition, the changes in enzyme protein structure during basic feeding were elucidated by circular binary chromatography (CD) and fluorescence spectrum. The platform has the advantages of low cost, simple process, green environmental protection, high conversion rate and product purity. This method laid a solid foundation for the resource utilisation of flavonoid glycosides and industrial production. [ABSTRACT FROM AUTHOR]

SUMMARY: 4‐Coumarate‐CoA Ligase (4CL) is an important enzyme in the phenylpropanoid biosynthesis pathway. Multiple 4CLs are identified in Ocimum species; however, their in planta functions remain enigmatic. In this study, we independently overexpressed three Ok4CL isoforms from Ocimum kilimandscharicum (Ok4CL7, ‐11, and ‐15) in Nicotiana benthamiana. Interestingly, Ok4CL11 overexpression (OE) caused a rootless or reduced root growth phenotype, whereas overexpression of Ok4CL15 produced normal adventitious root (AR) growth. Ok4CL11 overexpression in N. benthamiana resulted in upregulation of genes involved in flavonoid biosynthesis and associated glycosyltransferases accompanied by accumulation of specific flavonoid‐glycosides (kaempferol‐3‐rhamnoside, kaempferol‐3,7‐O‐bis‐alpha‐l‐rhamnoside [K3,7R], and quercetin‐3‐O‐rutinoside) that possibly reduced auxin levels in plants, and such effects were not seen for Ok4CL7 and ‐15. Docking analysis suggested that auxin transporters (PINs/LAXs) have higher binding affinity to these specific flavonoid‐glycosides, and thus could disrupt auxin transport/signaling, which cumulatively resulted in a rootless phenotype. Reduced auxin levels, increased K3,7R in the middle and basal stem sections, and grafting experiments (intra and inter‐species) indicated a disruption of auxin transport by K3,7R and its negative effect on AR development. Supplementation of flavonoids and the specific glycosides accumulated by Ok4CL11‐OE to the wild‐type N. benthamiana explants delayed the AR emergence and also inhibited AR growth. While overexpression of all three Ok4CLs increased lignin accumulation, flavonoids, and their specific glycosides were accumulated only in Ok4CL11‐OE lines. In summary, our study reveals unique indirect function of Ok4CL11 to increase specific flavonoids and their glycosides, which are negative regulators of root growth, likely involved in inhibition of auxin transport and signaling. [ABSTRACT FROM AUTHOR]

Diabetes mellitus is a metabolic disorder commonly associated with atherosclerosis. Plants with therapeutic potential, such as Lippia origanoides Kunth, emerge as effective alternatives for treating these diseases. Therefore, this work aims to analyze the antihyperglycemic and antidyslipidemic potential of the hydroalcoholic extract of Lippia origanoides Kunth (ELo) in alloxan‐diabetic rats. Animals were treated orally: normal control, hyperglycemic control, positive control glibenclamide (5 mg/kg), and groups treated with ELo (75, 150, and 250 mg/kg). Preclinical evaluation of ELo showed hypoglycemic, hypolipidemic, hepatic, and renal protective effects. At all doses, ELo significantly reduced hyperglycemia, triglycerides, total cholesterol, low‐density lipoprotein, atherogenic index, atherogenic coefficient, and cardiovascular risk index (p <.05). Elo at different doses promoted an increase in insulin release compared to untreated animals (p <.05) and showed α‐glucosidase inhibitory activity (p <.05). Also, ELo (250 mg/kg group) showed maximum reduction of hyperglycemia, alanine transaminase, aspartate aminotransferase, malonaldehyde, and urea compared to the hyperglycemic and glibenclamide groups, and creatinine only compared to the hyperglycemic groups (p <.05). The promising action of ELo in the context of diabetes may be related to the synergistic action of flavonoid compounds identified in liquid chromatography, whose pharmacological capabilities have already been documented in previous studies. The mechanisms may be the stimulation of insulin release; the inhibitory activity of α‐glucosidase; improving general clinical conditions; and the antioxidant effects of the extract. These findings pave the way for the future development of an herbal presentation of L. origanoides Kunth as a hypoglycemic and cardiovascular protector with a lipid‐lowering effect. [ABSTRACT FROM AUTHOR]

Type 2 diabetes (T2D) is the most common metabolic disorder. The undesirable effects of synthetic drugs demand a search for safe antidiabetic agents. This study aimed to assess the antidiabetic activity of different fractions of Atriplex halimus (petroleum ether 60–80, methylene chloride, ethyl acetate, and n‐butanol) using Drosophila melanogaster larvae. Titers of total glucose and trehalose, as well as larval weight, were measured and compared with those of control and diabetic larvae. The expression of Drosophila insulin‐like peptides (DILP2 and DILP3) and adipokinetic hormone (AKH) was evaluated. The results revealed a significant increase in total glucose, trehalose, and a decrease in body weight in the larvae fed a high‐sugar diet compared with those in the control. When larvae fed diets containing the tested fractions, the total glucose and trehalose decreased to the control level, and the body weight increased. DILP2, DILP3, and AKH exhibited significant decreases upon treatment with A. halimus ethyl acetate. Metabolomic profiling of the ethyl acetate fraction of A. halimus revealed the presence of flavonoids and flavonoid glycosides. After docking screening to predict the most powerful moiety, we discovered that flavonoid glycosides (especially eriodictyol‐7‐O‐neohesperidoside) have a greater affinity for the pocket than the other moieties. The results indicated the therapeutic activity of the A. halimus ethyl acetate fraction against induced T2D in Drosophila larvae. The antidiabetic activity may be attributed to flavonoids, which are the main components of the A. halimus ethyl acetate fraction. Research Highlights: Atriplex halimus L. ethyl acetate fraction showed the best antidiabetic activity in Drosophila larvae.It contains flavonoids and flavonoid glycosides, which may contribute tothis activity. Docking revealed eriodictyol‐7‐O‐neohesperidoside has the greatest affinity for the pocket. [ABSTRACT FROM AUTHOR]

Antimicrobial resistance poses a global health threat, with Staphylococcus aureus emerging as a notorious pathogen capable of forming stubborn biofilms and regulating virulence through quorum sensing (QS). In the quest for novel therapeutic strategies, this groundbreaking study unveils the therapeutic potential of Paederia foetida Linn., an Asian medicinal plant containing various bioactive compounds, contributing to its antimicrobial activities, in the battle against S. aureus. Through a comprehensive approach, we investigated the effect of ethanolic P. foetida leaf extract on S. aureus biofilms, QS, and antimicrobial activity. The extract exhibited promising inhibitory effects against S. aureus including the biofilm-forming strain and MRSA. Real-time PCR analysis revealed significant downregulation of key virulence and biofilm genes, suggesting interference with QS. Biofilm assays quantified the extract's ability to disrupt and prevent biofilm formation. LC-MS/MS analysis identified quercetin and kaempferol glycosides as potential bioactive constituents, while molecular docking studies explored their binding to the QS transcriptional regulator SarA. Computational ADMET predictions highlighted favorable intestinal absorption but potential P-glycoprotein interactions limiting oral bioavailability. While promising anti-virulence effects were demonstrated, the high molecular weights and excessive hydrogen bond donors/acceptors of the flavonoid glycosides raise concerns regarding drug-likeness and permeability. This integrated study offers valuable insights for developing novel anti-virulence strategies to combat antimicrobial resistance. [ABSTRACT FROM AUTHOR]

Plant extracts are considered as a large source of active biomolecules, especially in phytosanitary and pharmacological fields. Anthyllis henoniana is a woody Saharan plant located in the big desert of North Africa. Our previous research paper proved the richness of the methanol extract obtained from the stems in flavonoids and phenolic compounds as well as its remarkable antioxidant activity. In this research, we started by investigating the phytochemical composition of the methanol extract using high performance liquid chromatography coupled with electrospray ionization mass spectrometry (LC–MS/MS). Among the 41 compounds identified, we isolated and characterized (structurally and functionally) the most abundant product, a flavonoid triglycoside (AA770) not previously described in this species. This compound, which presents no cytotoxic activity, exhibits an interesting cellular antioxidant effect by reducing reactive oxygen species (ROS) generation, and an antiproliferative action on breast cancer cells. This study provides a preliminary investigation into the pharmacological potential of the natural compound AA770, isolated and identified from Anthyllis henoniana for the first time. [ABSTRACT FROM AUTHOR]

Background: Achyranthes bidentata (AR) is a traditional Chinese herb used for the treatment of hypertension and cerebral ischemia, but its pharmacological effects are not known. Aim of study: We aimed to detect and accurately identify the components and metabolites of AR in the plasma and brain tissue of Sprague Dawley rats. Methods: We employed ultrahigh performance liquid chromatography–high-resolution mass spectrometry (UHPLC–HR-MS) to detect AR components in the plasma and brain tissue of rats. The absorption and metabolites in the plasma and brain tissue of normal control rats and rats that underwent middle cerebral artery occlusion (MCAO) were characterized and compared. Results: A total of 281 compounds, including alkaloids, flavonoids, terpenoids, phenylpropanes, sugars and glycosides, steroids, triterpenes, amino acids, and peptides, was identified in samples of Achyranthes bidentata (TCM-AR). Four types of absorbable prototype components and 48 kinds of metabolites were identified in rats in the normal control plasma group which were given AR (AR plasma group), and five kinds of metabolites were identified in rats of the normal control brain tissue group which were given AR (AR brain group). Three absorbed prototype components and 13 metabolites were identified in the plasma of rats which underwent MCAO and were given AR (MCAO + AR plasma group). Six absorbed prototype components and two metabolites were identified in the brain tissue of rats who underwent MCAO and were administered AR (MCAO + AR brain group). These results showed that, after the oral administration of AR, the number of identified components in plasma was more than that in brain tissue. The number of prototype components in the AR plasma group was higher than that in the MCAO + AR plasma group, which may indicate that metabolite absorption in rats undergoing MCAO was worse. The number of prototype components in the MCAO + AR brain group was higher than that in the AR brain group, indicating that the blood–brain barrier was destroyed after MCAO, resulting in more compounds entering brain tissue. Conclusions: UHPLC–HR-MS was used to rapidly analyze the components and metabolites of AR in the blood and brain of rats under normal and pathologic conditions, and to comprehensively characterize the components of TCM-AR. We also analyzed and compared the absorbable components and metabolites of normal rats under cerebral ischemia-reperfusion injury to explore the potential mechanism of action. This method could be applied to various Chinese herbs and disease models, which could promote TCM modernization. [ABSTRACT FROM AUTHOR]

The flavonoids in citrus fruits are crucial physiological regulators and natural bioactive products of high pharmaceutical value. Melatonin is a pleiotropic hormone that can regulate plant morphogenesis and stress resistance and alter the accumulation of flavonoids in these processes. However, the direct effect of melatonin on citrus flavonoids remains unclear. In this study, nontargeted metabolomics and transcriptomics were utilized to reveal how exogenous melatonin affects flavonoid biosynthesis in "Bingtangcheng" citrus fruits. The melatonin treatment at 0.1 mmol L−1 significantly increased the contents of seven polymethoxylated flavones (PMFs) and up-regulated a series of flavonoid pathway genes, including 4CL (4-coumaroyl CoA ligase), FNS (flavone synthase), and FHs (flavonoid hydroxylases). Meanwhile, CHS (chalcone synthase) was down-regulated, causing a decrease in the content of most flavonoid glycosides. Pearson correlation analysis obtained 21 transcription factors co-expressed with differentially accumulated flavonoids, among which the AP2/EREBP members were the most numerous. Additionally, circadian rhythm and photosynthesis pathways were enriched in the DEG (differentially expressed gene) analysis, suggesting that melatonin might also mediate changes in the flavonoid biosynthesis pathway by affecting the fruit's circadian rhythm. These results provide valuable information for further exploration of the molecular mechanisms through which melatonin regulates citrus fruit metabolism. [ABSTRACT FROM AUTHOR]

Leaf extracts are known to be rich in phytoconstituent biomolecules, making them a valuable source of medicinal compounds. They also serve as both capping and reducing agents in nanoparticle fabrication. A reaction between CuSO4.5H2O aqueous solution and the Indigofera tinctoria leaf extract results in the formation of stable copper nanoparticles. Phytochemical screening of the Indigofera tinctoria leaf extract revealed the presence of various compounds including carbohydrates, terpenoids, phenol, tannins, flavonoids, saponins, and glycosides in the sample. The biosynthesized copper nanoparticles (CuNPs) were subsequently subjected to various forms of analysis. Techniques used included UV-visible (UV-vis) spectroscopy, Fourier transform infrared spectroscopy (FTIR), and scanning electron microscopy. An observable change in the color of solutions from pale to thick brown indicated the formation of CuNPs. Further confirmation came from UV-vis spectroscopy, which established the production of CuNPs at 500 nm. FTIR analysis revealed that the CuNPs were covered by organic residues. The particles ranged from 210 nm to 260 nm as indicated from the SEM analysis. [ABSTRACT FROM AUTHOR]

Daucus capillifolius Gilli is a rare annual wild herb grown in Libya. It belongs to the Apiaceae family, which is one of the largest flowering plant families. Plants of this family are outstanding sources of various secondary metabolites with various biological activities. A UPLC-ESI-MS/MS analysis of different extracts of in vivo and in vitro tissues of Daucus capillifolius together with the fruit extract of the cultivated plant in both ionization modes was carried out for the first time in the current study. Our results reveal the tentative identification of eighty-seven compounds in the tested extracts, including thirty-two phenolic acids and their derivatives; thirty-seven flavonoid glycosides and aglycones of apigenin, luteolin, diosmetin, myricetin and quercetin, containing glucose, rhamnose, pentose and/or glucuronic acid molecules; seven anthocyanins; six tannins; three acetylenic compounds; and three nitrogenous compounds. The tentative identification of the above compounds was based on the comparison of their retention times and ESI-MS/MS fragmentation patterns with those previously reported in the literature. For this Apiaceae plant, our results confirm the presence of a wide array of secondary metabolites with reported biological activities. This study is among the first ones to shed light on the phytoconstituents of this rare plant. [ABSTRACT FROM AUTHOR]

Perilla frutescens var. acuta (Lamiaceae) is widely used not only as an oil or a spice, but also as a traditional medicine to treat colds, coughs, fever, and indigestion. As an ongoing effort, luteolin-7-O-diglucuronide (1), apigenin-7-O-diglucuronide (2), and rosmarinic acid (3) isolated from P. frutescens var. acuta were investigated for their anti-adipogenic and thermogenic activities in 3T3-L1 cells. Compound 1 exhibited a strong inhibition against adipocyte differentiation by suppressing the expression of Pparg and Cebpa over 52.0% and 45.0%, respectively. Moreover, 2 inhibited the expression of those genes in a dose-dependent manner [Pparg: 41.7% (5 µM), 62.0% (10 µM), and 81.6% (50 µM); Cebpa: 13.8% (5 µM), 18.4% (10 µM), and 37.2% (50 µM)]. On the other hand, the P. frutescens var. acuta water extract showed moderate thermogenic activities. Compounds 1 and 3 also induced thermogenesis in a dose-dependent manner by stimulating the mRNA expressions of Ucp1, Pgc1a, and Prdm16. Moreover, an LC-MS/MS chromatogram of the extract was acquired using UHPLC-MS2 and it was analyzed by feature-based molecular networking (FBMN) and the Progenesis QI software (version 3.0). The chemical profiling of the extract demonstrated that flavonoids and their glycoside derivatives, including those isolated earlier as well as rosmarinic acid, are present in P. frutescens var. acuta. [ABSTRACT FROM AUTHOR]

The instability of ester bonds, low water solubility, and increased cytotoxicity of flavonoid glycoside esters significantly limit their application in the food industry. Therefore, the present study attempted to resolve these issues through liposome encapsulation. The results showed that baicalin butyl ester (BEC4) and octyl ester (BEC8) have higher encapsulation and loading efficiencies and lower leakage rate from liposomes than baicalin. FTIR results revealed the location of BEC4 and BEC8 in the hydrophobic layer of liposomes, which was different from baicalin. Additionally, liposome encapsulation improved the water solubility and stability of BEC4 and BEC8 in the digestive system and PBS but significantly reduced their cytotoxicity. Furthermore, the release rate of BEC4 and BEC8 from liposomes was lower than that of baicalin during gastrointestinal digestion. These results indicate that liposome encapsulation alleviated the negative effects of fatty chain introduction into flavonoid glycosides. [ABSTRACT FROM AUTHOR]

Zika virus (ZIKV) is involved in the etiology of serious nervous system pathologies. Currently, there are no specific and effective vaccines or antiviral drugs to prevent the diseases caused by ZIKV. This study aimed to assess the activity of flavonoids present in crude hydroethanolic extract (CHE) and fractions obtained from B. holophylla leaves against ZIKV. O-glycosylated flavonoids were characterized by high-performance liquid chromatography coupled with high-resolution mass spectrometry (LC-HRMS/MS). The cytotoxic concentration and the effective concentration for 50% of the cells (CC50 and EC50, respectively) were determined, and the selectivity index (SI) was calculated. Molecular networks were constructed based on the chemical composition of the samples and global antiviral activity data using the Global Natural Products Social Molecular Networking (GNPS) platform. Protein–ligand docking was performed in the NS2B-NS3 protease, NS3 helicase, and NS5 methyltransferase of the ZIKV. CHE showed greater antiviral activity at a multiplicity of infection (MOI) of 1.0, with an EC50 of 11.93 µg/mL, SI = 13.38, and reduced cytopathic effects. Molecular networks indicated that O-glycosylated flavonoids are responsible for the activity against ZIKV, being quercetin-O-deoxyhexoside more selective and effective. Molecular docking confirmed the inhibitory activity of quercetin-O-deoxyhexoside, which showed an affinity for the tested targets, especially for NS2B-NS3 protease. The results showed that B. holophylla has flavonoids with potential for future therapeutic applications against ZIKV. [ABSTRACT FROM AUTHOR]

Background: Atherosclerotic cardiovascular disease (ASCVD) continues to be a significant contributor to global mortality, impacting over 523 million individuals worldwide. Dyslipidemia stands as one of the foremost risk factors for ASCVD. Thus, prioritizing the reduction of low-density lipoprotein cholesterol (LDL-C) levels is essential in mitigating cardiovascular complications. Objective: This study aimed to evaluate the lipid-lowering activity of a dietary supplement containing monoglucosyl rutin (MR) in individuals with low to mild hypercholesterolemia. Methods: This was a randomized, placebo-controlled, double-blind, parallel-group study conducted from April 20 to December 24, 2022. The study population included 56 healthy Japanese adult participants with LDL-C levels between 120-139 mg/dL who were randomly allocated to either the MR or placebo groups (n = 28/group) using a computerized random number generator. 200 mg of MR or placebo divided into 3 tablets was given daily; participants were instructed to take 1 tablet with water after each meal for 12 weeks. The main focus was on measuring the serum LDL-C level as the primary outcome, with additional attention given to secondary outcomes such as serum high-density lipoprotein cholesterol (HDL-C), total cholesterol, and non-HDL-C levels. The study also evaluated the percentage of participants achieving serum LDL-C levels below 120 mg/dL after the 12-week intervention. Assessments were conducted after 4, 8, and 12 weeks of intervention. Results: There were 54 (27 in each group) participants in the per-protocol set (PPS) and 53 (placebo group, 26; MR group, 27) participants in the modified PPS (mPPS). A statistically significant group difference in serum LDL-C levels was observed (P < 0.05), with a 5.0% decrease from preintervention to after 12 weeks. The reduction in LDL-C levels coincided with statistically significant decreases in total cholesterol levels, non-HDL-C levels, and the LDL-C/HDL-C ratio. During the study period, there was no adverse event or concern about the safety of MR. Conclusions: MR has potential as a preventive or therapeutic tool for improving improve long-term health and reducing cardiovascular morbidity. [ABSTRACT FROM AUTHOR]

Despite being recognized as a specialty food in four Chinese provinces with established safety standards, Dendrobium officinale Kimura et Migo (Orchidaceae) leaf physicochemical indices overlook vital flavonoid glycoside components. Given the inconsistency in flavonoid quality under current standards, we devised a quantitative analysis targeting vicenin 2, vicenin 3, rutin, and isoviolanthin. Our analysis revealed significant seasonal variations, with harvests yielding the highest total content of these four flavonoid glycosides in February (1.6378 mg/g) and July (2.0642 mg/g). This finding provides a scientific basis for optimal collection timing, enhancing quality control and utilization. Furthermore, we optimized the extraction conditions (59.63 °C, 22.44 min, 1:37.91 g/mL solid-to-liquid ratio, 43.24 % ethanol) to maximize the flavonoid glycoside content. This study lays a foundation for refining D. officinale leaf quality standards and advancing related product development in China.

This article explores the use of multistage mass spectrometry (MSn) for structural annotation of compounds in complex matrices. It discusses the challenges in constructing accurate mass spectral trees and proposes a smart pipeline for MSn measurements. The article also discusses the use of in-source collision-induced dissociation (CID) to produce pseudo-MS3 spectra, which can aid in identifying aglycones. The authors conducted experiments using quercetin and its glycosides to evaluate the consistency of pseudo-MS3 spectra and their potential for aglycone identification. They propose a strategy for identifying substructures by matching pseudo-MS3 spectra with known compound spectra. The study demonstrates the viability of this strategy and investigates the impact of the DP value on glycosidic bond dissociation. Overall, this strategy offers a versatile way to improve confidence in structural identification. [Extracted from the article]

Sweet cherry pomace waste (CPW) obtained after juice production still contains high amounts of dietary fiber and added value compounds such as polyphenols. For this reason, it can be employed as renewable feedstock to produce novel commodities, bioactive compounds and bio-functional materials. In this study, a sustainable biorefinery approach has been developed combining the use of natural deep eutectic solvents (NADESs) for the recovery of polyphenolic compounds and bio-based ionic liquids (bio-ILs) for the treatment and conversion of the remaining lignocellulosic residue into an ionogel. The extraction efficiency and selectivity of different classes of (NA)DESs were evaluated varying both the hydrogen bond acceptor, HBA (choline chloride (ChCl), betaine (Bet) and L -proline (Pro)) and the hydrogen bond donor, HBD (carboxylic acids and polyols). The extracted phenolic compounds were qualitatively and quantitatively analyzed by UHPLC-HR-ESI-MS leading to the identification of more than 25 compounds, classifiable into four main subclasses (phenolic acids, flavonoid glycosides, flavonoid aglycones, and anthocyanins). The majority of ChCl-based DESs improved the total phenol extraction compared to classical solvents (up to twice). ChCl : ethylene glycol 1 : 2 was identified as the best performing system in terms of total phenolic content (total phenol 759 ± 85 μg g−1 of dried CPW) and was employed as the extraction medium for further optimization of the operative conditions and recycling study. The solvent was quantitatively recovered for three cycles with retention of the extraction efficiency towards all the identified subclasses of phenols. Finally, cholinium arginate (ChArg) allowed for obtaining cellulose enriched material (35 wt% of dried biomass) that was subsequently dissolved at 2 wt% in cholinium levulinate (ChLev) to prepare a weak physical ionogel, a functional biomaterial potentially useful in medical and pharmaceutical sectors. [ABSTRACT FROM AUTHOR]

The Stachys L. genus has been widely used in traditional medicine in many countries throughout the world. The study aimed to investigate the chemical composition and bioactivity of the hydroethanolic extract (50% v/v) obtained by ultrasonication from the aerial flowering parts of Stachys sylvatica L. (SSE) collected in Almaty region (Southern Kazakhstan). According to RP-HPLC/PDA analysis the leading metabolites of the SSE belonged to polyphenols: chlorogenic acid and its isomers (2.34 mg/g dry extract) and luteolin derivatives (1.49 mg/g dry extract), while HPLC-ESI-QTOF-MS/MS-based qualitative fingerprinting revealed the presence of 17 metabolites, mainly chlorogenic acid and its isomers, flavonoid glycosides, and verbascoside with its derivatives. GC-MS analysis of the volatile metabolites showed mainly the presence of diterpenoids and fatty acid esters. A reduction in the viability of nematodes Rhabditis sp. was obtained for the SSE concentration of 3.3 mg/mL, while 11.1 mg/mL showed activity comparable to albendazole. The SSE exhibited higher activity against Gram-positive (MIC = 0.5-2 mg/mL) than Gram-negative bacteria and yeast (MIC = 8 mg/mL), exerting bactericidal and fungicidal effects but with no sporicidal activity. The SSE showed some antiviral activity against HCoV-229E replicating in MRC-5 and good protection against the cytopathic effect induced by HHV-1 in VERO. The SSE was moderately cytotoxic towards human cervical adenocarcinoma (H1HeLa) cells (CC50 of 0.127 mg/mL after 72 h). This study provides novel information on the SSE extract composition and its biological activity, especially in the context of the SSE as a promising candidate for further antiparasitic studies. [ABSTRACT FROM AUTHOR]

Yinhua Pinggan Granule (YPG) is an approved compounded traditional Chinese medicine (TCM) prescription for the treatment of cold, cough, viral pneumonia, and related diseases. Due to its complicated chemical composition, the material basis of YPG has not been systematically investigated. In this study, an analytical method based on high-performance liquid chromatography (HPLC) coupled with Q-Exactive mass spectrometry was established. Together with the help of a self-built compound database and Compound Discoverer software 3.1, the chemical components in YPG were tentatively identified. Subsequently, six main components in YPG were quantitatively characterized with a high-performance liquid chromatography–diode array detector (HPLC-DAD) method. As a result, 380 components were annotated, including 19 alkaloids, 8 organic acids, 36 phenolic acids, 27 other phenols, 114 flavonoids, 75 flavonoid glycoside, 72 terpenes, 11 anthraquinones, and 18 other compounds. Six main components, namely, chlorogenic acid, puerarin, 3′-methoxypuerarin, polydatin, glycyrrhizic acid, and emodin, were quantified simultaneously. The calibration curves of all six analytes showed good linearity (R2 > 0.9990) within the test ranges. The precision, repeatability, stability, and recovery values were all in acceptable ranges. In addition, the total phenol content and DPPH scavenging activity of YPG were also determined. The systematic elucidation of the chemical components in YPG in this study may provide clear chemical information for the quality control and pharmacological research of YPG and related TCM compounded prescriptions. [ABSTRACT FROM AUTHOR]

Glycosylation is catalyzed by UDP-glycosyltransferase (UGT) and plays an important role in enriching the diversity of flavonoids. Rubus plants contain a lot of natural flavonoid glycosides, which are important plants with a homology of medicine and food. However, information about the Rubus UGT gene family is very limited. In this study, we carried out genome-wide analysis and identified the 172, 121, 130, 121 UGT genes in R. chingii, R. corchorifolius, R. idaeus, and R. occidentalis, respectively, and divided them into 18 groups. The analysis of the protein motif and gene structure showed that there were structural and functional conservations in the same group, but there were differences among different groups. Gene replication analysis showed that raspberry and dicotyledons had a higher homology. The expansion of the UGTs gene family was mainly driven by tandem replication events, and experienced purified selection during the long evolution of the raspberry. Cis-acting element analysis showed that they were related to plant growth and development, hormone regulation, and stress response. In addition, according to a comprehensive analysis of the co-expression network constructed by transcriptome data and phylogenetic homology, RchUGT169 was identified as a flavonoid glucosyltransferase. Through the transient expression in tobacco, it was verified that RchUGT169 could catalyze the conversion of kaempferol and quercetin to the corresponding flavonoid glycosides. In conclusion, this research enriched the understanding of the diversity of UGTs in Rubus and determined that RcUGT169 can catalyze flavonoids. [ABSTRACT FROM AUTHOR]

Medicinal plant tissue cultures are potential sources of bioactive compounds. In this study, we report the chemical characterization of the callus cultures of three medicinal Tilia spp. (Tilia cordata, Tilia vulgaris and Tilia tomentosa), along with the comparison to bracts and flowers of the same species. Our aim was to show that calli of Tilia spp. are good alternatives to the calli of T. americana for the production of polyphenols and are better sources of a subset of polyphenolic metabolites, compared to the original organs. Calli were initiated from young bracts and grown on woody plant medium containing 1 mg L−1 2,4-D and 0.1 mg L−1 BAP. For chemical characterization, a quality-controlled untargeted metabolomics approach and the quantification of several bioactive compounds was performed with the use of LC-ESI-MS/MS. While bracts and flowers contained flavonoid glycosides (astragalin, isoquercitrin) as major polyphenols, calli of all species contained catechins, coumarins (fraxin, esculin and scopoletin) and flavane aglyca. T. tomentosa calli contained 5397 µg g DW−1 catechin, 201 µg g DW−1 esculin, 218 µg g DW−1 taxifolin and 273 µg g DW−1 eriodictyol, while calli from other species contained lower amounts. T. cordata and T. tomentosa flowers were rich in isoquercitrin, containing 8134 and 6385 µg g DW−1, respectively. The currently tested species contained many of the bioactive metabolites described from T. americana. The production of catechin was shown to be comparable to the most efficient tissue cultures reported. Flowers and bracts contained flavonoid glycosides, including tiliroside, resembling bioactive fractions of T. americana. In addition, untargeted metabolomics has shown fingerprint-like differences among species, highlighting possible chemotaxonomic and quality control applications, especially for bracts. [ABSTRACT FROM AUTHOR]

Leontopodium leontopodioides (Willd.) Beauv. (L. leontopodioides.) has been used to treat lung diseases in traditional Chinese medicine (TCM). However, a systematic analysis of its chemical components has not been reported so far. In this study, UPLC-Q-Orbitrap MS and GC-MS were applied to investigate the chemical composition of the water extracts and essential oils of L. leontopodioides. UPLC-Q-Orbitrap MS adopts a heating electrospray ionization source, collecting primary and secondary mass spectrometry data in positive and negative ions, respectively, and uses Compound Discoverer 3.2 software to analyze the collected raw data. As a result, a total of 39 compounds were identified from their high-resolution mass spectra in both positive and negative ionization modes, including 13 flavonoids and their glycosides, 15 phenolic acids, 4 oligosaccharides and glycosides, 4 pentacyclic triterpenoids, and 3 other compounds. Among them, 18 chemical components have not been reported in L. leontopodioides. In the GC-MS section, two common organic solvents (n-hexane and diethyl ether) were used to extract essential oils, and the mass spectra were recorded at 70 eV (electron impact) and scanned in the range of 35∼450 m/z. Compounds were identified using NIST (version 2017), and the peak area normalization method was used to calculate their relative amounts. Finally, 17 components were identified in the volatile oil extracted with n-hexane, accounting for 80.38% of the total volatile oil, including monoterpenoids, phenylpropene, fatty acids, and aliphatic hydrocarbons. In the volatile oil extracted with diethyl ether, 16 components were identified, accounting for 73.50% of the total volatile oil, including phenylpropene, aliphatic hydrocarbons, monoterpenoids, fatty acids, and esters. This study was the first to conduct a comprehensive analysis of the chemical composition of the L. leontopodioides water extract and its essential oil, and a comprehensive chemical composition spectrum was constructed, to lay a foundation for its further pharmacodynamic material basis and quality evaluation. [ABSTRACT FROM AUTHOR]

This article discusses a new method for synthesizing chromone C-glycosides using a Pd-catalyzed reaction. The researchers successfully applied this method to different glycals with various protecting groups, resulting in the production of glycosides with moderate to high yields. They also explored the potential of this approach for modifying natural products and pharmaceutical compounds linked to glycals, leading to the synthesis of their respective glycosides. The researchers further demonstrated the scalability of their method and its applicability in producing valuable products, including 2-deoxy-chromone C-glycosides. Overall, this research introduces a unique collection of chromone glycosides that could be beneficial for drug discovery efforts. [Extracted from the article]

Summary: Biosynthesis of flavonoid aglycones and glycosides is well established. However, key genes involved in their catabolism are poorly understood, even though the products of hydrolysis and oxidation play important roles in plant resistance to biotic stress.Here, we report on catabolism of dihydrochalcones (DHCs), the most abundant flavonoids in domesticated apple and wild Malus. Two key genes, BGLU13.1 and PPO05, were identified by activity‐directed protein purification. BGLU13.1‐A hydrolyzed phlorizin, (the most abundant DHC in domesticated apple) to produce phloretin which was then oxidized by PPO05. The process differed in some wild Malus, where trilobatin (a positional isomer of phlorizin) was mainly oxidized by PPO05.The effects of DHC catabolism on apple resistance to biotic stresses was investigated using transgenic plants. Either directly or indirectly, phlorizin hydrolysis affected resistance to the phytophagous pest two‐spotted spider mite, while oxidation of trilobatin was involved in resistance to the biotrophic fungus Podosphaera leucotricha. DHC catabolism did not affect apple resistance to necrotrophic pathogens Valsa mali and Erwinia amylovara.These results suggest that different DHC catabolism pathways play different roles in apple resistance to biotic stresses. The role of DHC catabolism on apple resistance appeared closely related to the mode of invasion/damage used by pathogen/pest. [ABSTRACT FROM AUTHOR]