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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]

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]

[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]

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]

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]

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]

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]

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]

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]

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]

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]

Tilianin (Til), a flavonoid glycoside, is well-known for its therapeutic promise in treating inflammatory disorders. Its poor water solubility and permeability limit its clinical applicability. In order to overcome these restrictions, an antisolvent precipitation and ultrasonication technique was used to prepare amorphous tilianin nanocrystals (Til NCs). We have adjusted the organic solvents, oil-to-water ratio, stabilizer composition, and ultrasonic power and time by combining single-factor and central composite design (CCD) methodologies. The features of Til NCs were characterized using powder X-ray diffraction (PXRD), scanning calorimetry (DSC), and transmission electron microscopy (TEM). Specifically, the optimized Til NCs were needle-like with a particle size ranging from 90 to 130 nm. PVA (0.3%, w/v) and TPGS (0.08%, w/v) stabilized them well. For at least two months, these Til NCs stayed amorphous and showed an impressive stability at 4 °C and 25 °C. Remarkably, Til NCs dissolved almost 20 times faster in simulated intestinal fluid (SIF) than they did in crude Til. In RAW264.7 cells, Til NCs also showed a better cellular absorption as well as safety and protective qualities. Til NCs were shown to drastically lower reactive oxygen species (ROS), TNF-α, IL-1β, and IL-6 in anti-inflammatory experiments, while increasing IL-10 levels and encouraging M1 macrophages to adopt the anti-inflammatory M2 phenotype. Our results highlight the potential of amorphous Til NCs as a viable approach to improve Til's anti-inflammatory effectiveness, solubility, and dissolving rate. [ABSTRACT FROM AUTHOR]

【Objective】Xihuangcao is a traditional Chinese herbal medicine commonly used in Chinese folk culture. As a medicinal commodity, “Xihuangcao” has about 3-4 plant species as its source. The existing identification and researches suggest that Isodon lophanthoides is one of the authentic products of “Xihuangcao”. The widely cultivated Isodon lophanthoides plants are mostly of the purple flower type. The project team used metabolomics technology to conduct comparative studies on the metabolites of newly obtained white flower type germplasm and conventional purple flower type germplasm, which could provide a basis for the creation of authentic I. lophanthoides germplasm and the breeding of new varieties. 【Method】With white flower germplasm as the research object and widely cultivated purple flower germplasm as the control, UPLC-MS/MS technology was used to compare the differential metabolites between the two germplasms and conduct differential metabolite enrichment pathway analysis.【Result】A total of 125 differential metabolites were screened from 868 metabolites detected in two germplasm samples, of which 67 were significantly upregulated and 58 were downregulated in the white flower germplasm. The differential metabolites between the two germplasms mainly included flavonoids, organic acids, amino acids and their derivatives, phenolic acids, alkaloids, free fatty acids, and etc. Among them, flavonoids accounted for the highest proportion, reaching 45.6%. Among the three differential metabolites of flavonoids, flavonoid glycosides and isoflavones, their upregulated quantity of white flower germplasm were higher than that of purple flower germplasm; flavonoids were the category with the most differential metabolites between the two germplasms, and most of them were significantly upregulated in purple flower germplasm. Further pathway enrichment analysis revealed that 125 differential metabolites were annotated into 47 metabolic pathways. Among them, significantly enriched pathways included flavonoid, isoflavone, anthocyanin, flavone, flavanol, stilbenoid, diarylheptanoid and gingerol biosynthesis and purine metabolism, etc.【Conclusion】The contents of flavonoids and flavonols in white flower I. lophanthoides germplasm are significantly higner than those in the purple flower germplasm. This will provide good materials for the exploration, creation and new variety selection of I. lophanthoides germplasm resources in the later stage. [ABSTRACT FROM AUTHOR]

【Objective】Drynaria fortunei is a perennial traditional Chinese medicinal herb. Currently, most medicinal materials of this herb are obtained through wild collection, with few reports on artificial cultivation. Due to excessive collection, the wild resources of D. fortune have been severely damaged, leading to a significant decline in medicinal resources. As a result, artificial cultivation has become an inevitable trend. On the basis of exploring the greenhouse cultivation technology of D. fortune, a targeted metabolomics comparative study was conducted between greenhouse-cultivated rhizomes and wild rhizomes by using metabolomics technology. The study aimed to explore the differences in the main metabolites between cultivated and wild rhizomes to provide a basis for the promotion of artificial cultivation technology of D. fortune.【Method】Taking the original plant of Rhizoma Drynariae, D. fortune as research object, and UPLC-MS/MS analysis technology was utilized to compare and analyze the differential metabolites between three-year greenhouse-cultivated rhizomes and three-year wild rhizomes. Subsequently, enrichment pathway analysis of differential metabolites was conducted by the KEGG pathway database. 【Result】Among 749 metabolites detected from two D. fortune samples, 100 differential metabolites were screened. Compared with wild samples, there were 58 upregulated metabolites and 42 downregulated metabolites in greenhouse-cultivated samples. These differential metabolites mainly included flavonoids, organic acids, amino acids and their derivatives, phenolic acids, alkaloids, free fatty acids and other metabolites. In greenhouse-cultivated samples, flavonols, flavonoid glycosides, sugars and carbohydrate metabolites were all upregulated. Conversely, in wild samples, amino acids and their derivatives, phenolic acids, lysophosphatidylcholine and anthocyanin metabolites were upregulated to a greater extent. Further pathway enrichment analysis revealed that 100 differential metabolites were annotated into 47 metabolic pathways. Significantly enriched pathways included vitamin B6 metabolism, astragalus compound biosynthesis, diarylheptanoids biosynthesis, gingerol biosynthesis, flavonoid and flavonol biosynthesis, cysteine and methionine metabolism, anthocyanin biosynthesis and aminoacyl tRNA biosynthesis. 【Conclusion】The contents of flavonols, flavonoid glycosides, sugars and carbohydrate metabolites in D. fortune cultivated in greenhouse are significantly higher than those in wild-collected D. fortune. Considering that the total flavonoids of D. fortune are recognized as the main active ingredients, greenhouse-cultivated D. fortune has the advantage of containing higher levels of active ingredients compared to wild-collected D. fortune. This finding can serve as a scientific basis for large-scale cultivation or artificial cultivation of D. fortune [ABSTRACT FROM AUTHOR]

Fructus Aurantii (FA) is an edible and medicinal functional food used worldwide that enhances digestion. Since raw FA (RFA) possesses certain side effects for some patients, processed FA (PFA) is commonly used in clinical practice. This study aimed to establish an objective and comprehensive quality evaluation of the PFA that employed the technique of steaming and fermentation. Combined with the volatile and non‐volatile components, as well as the regulation of gut microbiota, the differentiation between RFA and PFA was analyzed. The results showed that the PFA considerably reduced the contents of flavonoid glycosides while increasing hesperidin‐7‐O‐glucoside and flavonoid aglycones. The electronic nose and GC‐MS (Gas chromatography/mass spectrometry) effectively detected the variation in flavor between RFA and PFA. Correlation analysis revealed that eight volatile components (relative odor activity value [ROAV] ≥ 0.1) played a key role in inducing odor modifications. The original floral and woody notes were subdued due to decreased levels of linalool, sabinene, α‐terpineol, and terpinen‐4‐ol. After processing, more delightful flavors such as lemon and fruity aromas were acquired. Furthermore, gut microbiota analysis indicated a significant increase in beneficial microbial taxa. Particularly, Lactobacillus, Akkermansia, and Blautia exhibited higher abundance following PFA treatment. Conversely, a lower presence of pathogenic bacteria, including Proteobacteria, Flexispira, and Clostridium. This strategy contributes to a comprehensive analysis technique for the quality assessment of FA, providing scientific justifications for processing FA into high‐value products with enhanced health benefits. Practical Application: This study provided an efficient approach to Fructus Aurantii quality evaluation. The methods of fermentation and steaming showed improved quality and safety. [ABSTRACT FROM AUTHOR]

Background: Geographical factors affect the nutritional, therapeutic and commercial values of fruits. Dragon fruit (Hylocereus spp) is a popular fruit in Asia and a potential functional food with diverse pharmacological attributes. Although it is produced in various localities, the information related to the altitudinal variation of dragon fruit nutrients and active compounds is scarce. Hence, this study aimed to investigate the variations in metabolite profiles of H. polyrhizus (variety Jindu1) fruit pulps from three different altitudes of China, including Wangmo (WM, 650 m), Luodian (LD, 420 m), and Zhenning (ZN, 356 m). Jindu1 is the main cultivated pitaya variety in Guizhou province, China. Results: The LC-MS (liquid chromatography-mass spectroscopy)-based widely targeted metabolic profiling identified 645 metabolites, of which flavonoids (22.64%), lipids (13.80%), phenolic acids (12.40%), amino acids and derivatives (10.39%), alkaloids (8.84%), and organic acids (8.37%) were dominant. Multivariate analyses unveiled that the metabolite profiles of the fruit differed regarding the altitude. Fruits from WM (highest altitude) were prime in quality, with higher levels of flavonoids, alkaloids, nucleotides and derivatives, amino acids and derivatives, and vitamins. Fruits from LD and ZN had the highest relative content of phenolic acids and terpenoids, respectively. We identified 69 significantly differentially accumulated metabolites across the pulps of the fruits from the three locations. KEGG analysis revealed that flavone and flavonol biosynthesis and isoflavonoid biosynthesis were the most differentially regulated. It was noteworthy that most active flavonoid compounds exhibited an increasing accumulation pattern along with the increase in altitude. Vitexin and isovitexin were the major differentially accumulated flavonoids. Furthermore, we identified two potential metabolic biomarkers (vitexin and kaempferol 3-O-[2-O-β-D-galactose-6-O-a-L-rhamnose]-β-D-glucoside) to discriminate between dragon fruits from different geographical origins. Conclusion: Our findings provide insights into metabolic changes in dragon fruits grown at different altitudes. Furthermore, they show that growing pitaya at high altitudes can produce fruit with higher levels of bioactive compounds, particularly flavonoids. [ABSTRACT FROM AUTHOR]

Exploring phytochemicals from ethnomedicinal plants for pharmacological applications is a promising research area. By studying ethnomedicine, researchers can identify plants used for centuries to treat ailments and investigate their phytochemicals. Consequently, phytochemicals can be isolated, characterized, and tested for pharmacological activities, leading to new drug development. This research also helps preserve traditional knowledge and biodiversity. Lithospermum officinale L., found in Eurasia, Argentina (South), Colombia, and the United States, is valued for its medicinal properties, including anti-inflammatory, antioxidant, and antimicrobial effects. The current review emphasizes L. officinale L. as a significant reservoir of bioactive phytochemicals, with alkaloids, quinones, glucosides, phenolics, flavonoids, and lipids identified as the principal metabolites. It also unveils the unexplored potential of this plant for future research endeavors. Continued research on L. officinale L. can unlock its full potential, providing insights into its medicinal uses and contributing to biodiversity preservation. [ABSTRACT FROM AUTHOR]

Piper aduncum L. is widely distributed in tropical regions and the ethnobotanical uses of this species encompass medicinal applications for the treatment of respiratory, antimicrobial, and gynecological diseases. Chemical studies reveal a diverse array of secondary metabolites, including terpenes, flavonoids, and prenylated compounds. Extracts from P. aduncum have shown antibacterial, antifungal, and larvicidal activities. Our study explores the activity of extracts and partitions against Mycobacterium tuberculosis H37Rv, as well as the chemical diversity of the bioactive partition. This marks the first investigation of the bioactive partition of P. aduncum from agroecological cultivation. The ethyl acetate partition from the ethanolic leaf extract (PAEPL) was found to be the most active. PAEPL was subjected to column chromatography using Sephadex LH-20 and the obtained fractions were analyzed using UHPLC-HRMS/MS. The MS/MS data from the fractions were submitted to the online GNPS platform for the generation of the molecular network, which displayed 1714 nodes and 167 clusters. Compounds were identified via manual inspection and different libraries, allowing the annotation of 83 compounds, including flavonoids, benzoic acid derivatives, glycosides, free fatty acids, and glycerol-esterified fatty acids. This study provides the first chemical fingerprint of an antimycobacterial sample from P. aduncum cultivated in an agroecological system. [ABSTRACT FROM AUTHOR]

Inflammation is a pivotal factor in the development and advancement of conditions like NAFLD and asthma. Diet can affect several phases of inflammation and significantly influence multiple inflammatory disorders. Siraitia grosvenorii, a traditional Chinese edible and medicinal plant, is considered beneficial to health. Flavonoids can suppress inflammatory cytokines, which play a crucial role in regulating inflammation. In the present experiments, kaempferol 3-O-α-L-rhamnoside-7-O-β-D-xylosyl(1→2)-O-α-L-rhamnoside (SGPF) is a flavonoid glycoside that was first isolated from S. grosvenorii. A series of experimental investigations were carried out to investigate whether the flavonoid component has anti-inflammatory and hepatoprotective effects in this plant. The researchers showed that SGPF has a stronger modulation of protein expression in LPS-induced macrophages (MH-S) and OA-induced HepG2 cells. The drug was dose-dependent on cells, and in the TLR4/NF-κB/MyD88 pathway and Nrf2/HO-1 pathway, SGPF regulated all protein expression. SGPF has a clear anti-inflammatory and hepatoprotective function in inflammatory conditions. [ABSTRACT FROM AUTHOR]

Honeysuckle, as an important medicinal and edible plant, contains a variety of chemical active components, mainly including volatile oils, flavonoids, organic acids and iridoid glycosides, etc., which have antibacterial, antiinflammatory, antiviral, antioxidant, antipyretic, and immunomodulatory effects. Honeysuckle and its extract can improve the digestion, absorption and utilization rate of feed, promote the growth and development of livestock and poultry and meat quality, regulate the metabolism of energy, protein, lipids and sugar of livestock and poultry, and improve the immune function and antioxidant capacity of livestock and poultry. In the paper, the main active components, physiological functions, and application status of honeysuckle and its extracts in livestock and poultry production were summarized, in order to provide a reference for honeysuckle and its extracts to improve the production efficiency and product quality of livestock and poultry, and to replace antibiotics in livestock and poultry production. [ABSTRACT FROM AUTHOR]

The present study focused on the mushroom Ganoderma, which has been used in Eastern countries for centuries as a food and medicinal source. Specifically, the fruiting bodies of Ganoderma applanatum from the Kerala Forest Research Institute in Thirussur, Kerala, India, were analyzed for their nutritional and medicinal properties. The methanolic extracts of G. applanatum were used to examine secondary metabolites and proximate profiles, revealing the presence of various phytochemicals such as terpenoids, phenolics, glycosides, alkaloids, flavonoids, and saponins. Further analysis revealed the presence of significant amounts of calcium, sodium, phosphorus, and manganese. The compounds were characterized using chromatographic analysis, FTIR, and GC-MS, which revealed potential therapeutic compounds with C-H and C-O bonds in the amide group, β-glycosides, and C-C/C-O vibrations of phenolic substances. Mushroom extract at a concentration of 100 µg mL−1 exhibited potent antimicrobial activity against various pathogens. This study suggests that G. applanatum has a rich biochemical composition and pharmacological potential, making it a promising candidate for drug development and traditional medicine, and contributes valuable insights into its diverse therapeutic applications. [ABSTRACT FROM AUTHOR]

Luteolin-7-O-β-d-glucuronide (LGU) is a major active flavonoid glycoside compound that is extracted from Ixeris sonchifolia (Bge.) Hance, and it is a Chinese medicinal herb mainly used for the treatment of coronary heart disease, angina pectoris, cerebral infarction, etc. In the present study, the neuroprotective effect of LGU was investigated in an oxygen glucose deprivation (OGD) model and a middle cerebral artery occlusion (MCAO) rat model. In vitro, LGU was found to effectively improve the OGD-induced decrease in neuronal viability and increase in neuronal death by a 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and a lactate dehydrogenase (LDH) leakage rate assay, respectively. LGU was also found to inhibit OGD-induced intracellular Ca2+ overload, adenosine triphosphate (ATP) depletion, and mitochondrial membrane potential (MMP) decrease. By Western blotting analysis, LGU significantly inhibited the OGD-induced increase in expressions of receptor-interacting serine/threonine-protein kinase 3 (RIP3) and mixed lineage kinase domain-like protein (MLKL). Moreover, molecular docking analysis showed that LGU might bind to RIP3 more stably and firmly than the RIP3 inhibitor GSK872. Immunofluorescence combined with confocal laser analyses disclosed that LGU inhibited the aggregation of MLKL to the nucleus. Our results suggest that LGU ameliorates OGD-induced rat primary cortical neuronal injury via the regulation of the RIP3/MLKL signaling pathway in vitro. In vivo, LGU was proven, for the first time, to protect the cerebral ischemia in a rat middle cerebral artery occlusion (MCAO) model, as shown by improved neurological deficit scores, infarction volume rate, and brain water content rate. The present study provides new insights into the therapeutic potential of LGU in cerebral ischemia. [ABSTRACT FROM AUTHOR]

Plants' bioactive chemicals have been utilized throughout human history as supplements and medicines to support the body's natural physiological processes. When their function is discovered, many substances are added for medical uses. Herbs are known to contain a variety of organic substances. These crucial herbs are the main ingredients in many pharmaceutical and healthcare products. Traditional folk medical practices offer essential information for the extraction and creation of numerous medications and activities as well. The production of a few highly active pharmaceuticals is justified by the extraction and characterization of a variety of bioactive chemicals from green factories. This study uses quantitative analysis of ethyl acetate, ethanol, n-hexane, chloroform and aqueous extract along with established methodologies to assess the phytochemicals. Alkaloids, flavonoids, reducing sugars, proteins, amino acids, saponins, tannins, terpenoids and glycosides were discovered in the quantification and phytochemical screening results. Due to the presence of several phytochemical substances, the entire plant of Psychotria octosulcataW. A. Talbotdemonstrated a diversity of medicinal potential. The cytotoxicity activity of the plant extracts was predicted using brine shrimp lethality assay (BSLA). The results showed that the shrimp in the ethanolic extract of Psychotria octosulcata W. A. Talbotare extremely hazardous in higher concentrations. Only 10 shrimps are discovered to be lethal at lowest concentrations even after 24 h. This can be due to the presence of bioactive substances. [ABSTRACT FROM AUTHOR]

Flavonoids are a group of polyphenolic compounds known to possess good radical scavenging activity. It was also shown that their anti/prooxidant properties are strongly structure‐dependent and can be modified by metal ion binding. The structural parameters also appear to be key factors during their DNA‐binding abilities. This work deals with spectroscopic and theoretical studies of two flavonoids, baicalein and scutellarein, alone, and in the presence of redox‐active metal ion Cu(II). Cu(II) is the catalytic active ion in Fenton‐like reactions and can enhance the production of reactive oxygen species or, when bound to the flavonoid, influence its antioxidant potential. UV–Vis spectroscopy showed that the electronic properties of the parent flavonoids are changed following the CuCl2 addition. Job's plot method revealed the 1:1 binding mode of interaction in DMSO and DMSO/PBS solvent. The ABTS•+ assay showed only a negligible effect of Cu(II) presence on the antioxidant properties of baicalein and scutellarein. The mix of the natural reductant, glutathione, with flavonoids showed a synergistic effect in ABTS•+ inhibition; however, this effect was suppressed by the presence of Cu(II). Absorption titration and molecular docking studies showed an effective DNA binding of both flavonoids that is further enhanced by the presence of Cu(II). DFT calculations were carried out to identify the most energetically stable Cu(II)–flavonoid structures as well as to determine the ability of their hydroxyl groups to undergo homolytic or heterolytic cleavage. [ABSTRACT FROM AUTHOR]

Background: Metabolic syndrome is a global health concern, affecting a significant portion of the population worldwide. According to the World Health Organization (WHO), the prevalence of metabolic syndrome is increasing globally due to the rising of obesity and physical inactivity. Objectives: In the present study, we evaluated Lupinus angustifolius seeds for their potential in alleviating metabolic abnormalities associated with metabolic syndrome induced by High Fructose Diet. Materials and Methods: Hexane and ethyl acetate seeds extracts of L. angustifolius (HELA and EAELA) were screened for phytochemical constituents. Normoglycemic male albino Wistar rats were distributed into 6 groups with 6 in each. Fructose solution (10% w/v) administered p.o. for 8 weeks caused induction of Metabolic Disorder. The metabolic parameters were assessed and recorded before and after the administration of 200 mg/kg of extracts over 8 weeks. Results: Preliminary screening demonstrated the presence of flavonoids, alkaloids, glycosides among others from both extracts. HELA and EAELA showed a significant (p<0.001) decrease in obesity. They also led to significantly (p<0.001) decreased expression of inflammatory mediators like IL-6, TGFβ, and TNF-α. Hematological parameters exhibited improvement whereas HbA1C expressed a significant (p<0.001) increase in plasma insulin and HOMA IR revealed a significant (p<0.001) decrease in insulin resistance when compared to disease control. Metabolic hormone levels also showed a positive change after administration where leptin and adiponectin levels are decreased (p<0.001 and p<0.1 respectively) and gherlin levels were increased non-significantly (p<0.05). Antihyperlipidemic, antioxidant potential of the extracts was more proficient. Conclusion: The EAELA at 200 mg/kg displayed significant capacity in inhibiting the Metabolic Syndrome induced by High fructose diet when compared to that of HELA at 200 mg/kg which was effective in comparison with Standard. [ABSTRACT FROM AUTHOR]

Aim: Multi-drug-resistant bacteria is a growing concern worldwide. Plants have emerged as a promising avenue due to their bioactive compounds. Newbouldia laevis and Stereospermum acuminatissimum are two plants with a long history of use in traditional medicine. This study aimed at exploring the antimicrobial activity of their extracts against multi-drug-resistant bacteria. Material and Methods: Extracts were prepared by maceration of pulverized leaves or stem barks (250 g) in 2L dichloromethane/methanol (30/70) filtered and the filtrate was dried using a rotary evaporator. The crude extracts were then tested against five pathogenic multi-resistant bacterial strains and Minimum Inhibition Concentration (MIC) was determined using the broth dilution method. The combinations of extracts and reference drug ceftriaxone was carried out following the checkerboard technique. Results: The overall results showed that Newbouldia laevis and Stereospermum acuminatissimum crude extracts contain various phytochemicals such as alkaloids, flavonoids, terpenoids, and polyphenols, which were found to be associated with strong anti-bacterial effects against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumonia, exhibiting MICs values ranging from 100 μg/ mL to 400 μg/mL. The combinatorial analysis showed a combination and strains dependent-out, including synergism, additivity, and antagonism. Conclusion: These findings suggest that Newbouldia laevis and Stereospermum acuminatissimum could be used as alternative sources of antimicrobial agents for treating bacterial infections [ABSTRACT FROM AUTHOR]

BACKGROUND: Fig (Ficus carica L.) fruit is consumed worldwide as a functional food. It contains phytochemicals that have been related to health benefits. However, the characteristic chemicals remain unclear. In this work, phytochemicals were prepared from figus by ultrasound‐assisted extraction under optimized conditions. The chemical composition of fig fruit and leaves was characterized by ultra‐high performance liquid chromatography‐tandem mass spectrometry (UPLC‐MS/MS). RESULTS: One hundred and fifty‐seven compounds were identified, including 58 flavonoids, 29 coumarins, 19 acids, 15 terpenoids, 11 alkaloids, and 25 other compounds. The mass spectrum (MS) fragmentation pathways of representative chemicals were elucidated. Flavonoid glycosides and prenylated flavonoids were mainly present in fig fruit, whereas coumarins were abundant in leaves. Both fig fruit and leaf extracts showed good cellular antioxidant activity. CONCLUSION: The full phytochemical profile of fig was revealed by UPLC‐MS/MS. Prenylated flavonoids and prenylated coumarins were the characteristic phytochemicals. These data provided useful information for the extensive utilization of fig fruit in functional food. © 2023 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Radix Fici Simplicissimae (RFS) is widely studied, and is in demand for its value in medicines and food products, with increased scientific focus on its cultivation and breeding. We used ultra-high-performance liquid chromatography quadrupole-orbitrap mass spectrometry-based metabolomics to elucidate the similarities and differences in phytochemical compositions of wild Radix Fici Simplicissimae (WRFS) and cultivated Radix Fici Simplicissimae (CRFS). Untargeted metabolomic analysis was performed with multivariate statistical analysis and heat maps to identify the differences. Eighty one compounds were identified from WRFS and CRFS samples. Principal component analysis and orthogonal partial least squares discrimination analysis indicated that mass spectrometry could effectively distinguish WRFS from CRFS. Among these, 17 potential biomarkers with high metabolic contents could distinguish between the two varieties, including seven phenylpropanoids, three flavonoids, one flavonol, one alkaloid, one glycoside, and four organic acids. Notably, psoralen, apigenin, and bergapten, essential metabolites that play a substantial pharmacological role in RFS, are upregulated in WRFS. WRFS and CRFS are rich in phytochemicals and are similar in terms of the compounds they contain. These findings highlight the effects of different growth environments and drug varieties on secondary metabolite compositions and provide support for targeted breeding for improved CRFS varieties. [ABSTRACT FROM AUTHOR]

Among C‐glycosides, C‐alkyl glycosides are significant building blocks for natural products and glycopeptides. However, research on efficient construction methods for C‐alkyl glycosides remains relatively limited. Compared with Michael acceptors, non‐activated olefins are more challenging substrates and have rarely been employed in the construction of C‐glycosides. Here, a highly efficient and convenient approach for the synthesis of C‐alkyl glycosides through a nickel‐catalyzed C(sp3)‐C(sp3) coupling reaction is presented. A distinctive feature of this method is its utilization of non‐activated olefins as the anomeric radical acceptors for hydroalkylation, allowing for the direct formation of C‐glycoside bonds in a single step. Furthermore, this method demonstrates excellent compatibility with a broad scope of highly reactive functional groups. Mechanistic investigations suggest that the reaction proceeds via a free radical pathway, leading predominantly to the formation of products with α‐configuration. Overall, this innovative methodology offers a versatile and practical approach for the synthesis of C‐alkyl glycosides, offering new avenues for the production of intricate glycosides with potential applications in drug discovery and chemical biology. [ABSTRACT FROM AUTHOR]

The presence of oropharyngeal human papillomavirus (HPV)-18 E6 and E7 oncoproteins is highly significant in the progression of oropharyngeal cancer. Natural flavonoid compounds have potential as photosensitizers for light-activated antimicrobial therapy against HPV-associated oropharyngeal cancer. This study evaluated five natural flavonoid glycosides including Fisetin, Kaempferol, Morin, Myricetin, and Quercetin as photosensitizers against HPV-18 E6 and E7 oncoproteins using computational methods. After obtaining the amino acid sequences of HPV-18 E6 and E7, various tools were used to predict and verify their properties. The PubChem database was then examined to identify potential natural flavonoid glycosides, followed by predictions of their drug-likeness and ADMET properties. Subsequently, molecular docking was conducted to enhance the screening accuracy and to gain insights into the interactions between the natural compounds and the active sites of HPV-18 E6 and E7 oncoproteins. The protein structures of E6 and E7 were predicted and validated to be reliable. The results of molecular docking demonstrated that Kaempferol exhibited the highest binding affinity to both E6 and E7. All compounds satisfied Lipinski's rules of drug-likeness, except Myricetin. They showed high absorption, distribution volume and similar ADMET profiles with no toxicity. In summary, natural flavonoid glycosides, especially Kaempferol, show potential as photosensitizers for antimicrobial photodynamic therapy against HPV-associated oropharyngeal cancer through inhibition of E6 and E7 oncoproteins. These findings provide insights into the development of novel therapeutic strategies based on antimicrobial photodynamic therapy. [ABSTRACT FROM AUTHOR]