Kaempferol Derivatives Research Articles

Antibacterial and Antioxidant Activities of Flavonoids, Phenolic and Flavonoid Glycosides from Gouania longispicata Leaves

The leaves of Gouania longispicata Engl. (GLE) have been traditionally used to treat more than forty ailments in Uganda, including stomachache, lung and skin cancers, syphilis, toothache, and allergies. In this study, pure compounds were isolated from the methanolic extract of GLE leaves and their structures elucidated using ultraviolet visible spectroscopy, liquid chromatography–tandem mass spectrometry, high performance liquid chromatography, and 1D and 2D NMR techniques. The antibacterial and antioxidant activities of the compounds were assessed using the broth dilution and DPPH assays, respectively. Two known flavonoid glycosides (kaempferol-3-O-α-rhamnopyranoside and rutin), a phenolic glycoside (4,6-dihydroxy-3-methylacetophenone-2-O-β-D-glucopyranoside), and flavonoids (kaempferol and quercetin) were characterized. This is the first time that the kaempferol derivative, the acetophenone as well as free forms of quercetin, kaempferol, and rutin, are being reported in GLE and the Gouania genus. The compounds exhibited antibacterial activity against Streptococcus pneumoniae and Escherichia coli with minimum inhibitory concentrations between 16 µg/mL and 125 µg/mL. The radical scavenging activities recorded half-minimum inhibitory concentrations (IC50) ranging from 18.6 ± 1.30 µg/mL to 28.1 ± 0.09 µg/mL. The IC50 of kaempferol and quercetin were not significantly different from that of ascorbic acid (p > 0.05), highlighting their potential as natural antioxidant agents. These results lend credence to the use of GLE leaves in herbal treatment of microbial infections and oxidative stress-mediated ailments.

Mexican calea (Calea zacatechichi Schltdl.) interferes with cholinergic and dopaminergic pathways and causes neuroglial toxicity

Ethnopharmacological relevanceThe use of “Mexican calea” (Calea zacatechichi Schltdl.) in ritualistic ceremonies, due to its dream-inducing effects, was until recently limited to indigenous communities in Mexico. However, the plant has recently gained popularity in Western societies being commonly used in recreational settings. Despite the traditional and recreational uses, mechanisms underlying its reported oneirogenic effects remain unknown, with no data available on its neurotoxic profile. Aim of the studyThe scarcity of toxicological data and the unknown role of major neurotransmitter systems in the dream-inducing properties of the plant prompted us to investigate which neurotransmitters might be affected upon its consumption, as well as the potential cytotoxic effects on neurons and microglial cells. Furthermore, we aimed to explore a relationship between the recorded effects and specific constituents. Materials and methodsEffects on cholinergic and monoaminergic pathways were investigated using enzymatic assays, with the latter also being conducted in neuronal SH-SY5Y cells along with the impact on glutamate-induced excitotoxicity. Investigation of the neurotoxic profile was approached in neuronal SH-SY5Y and microglial BV-2 cells, evaluating effects on metabolic performance and membrane integrity using MTT and LDH leakage assays, respectively. Potential interference with oxidative stress was monitored by assessing free radical's levels, as well as 5-lipoxygenase mediated lipid peroxidation. Phenolic constituents were identified through HPLC-DAD-ESI(Ion Trap)MSn analysis. ResultsBased on the significant inhibition upon acetylcholinesterase (p < 0.05) and tyrosinase (IC50 = 60.87 ± 7.3 μg/mL; p < 0.05), the aqueous extract obtained from the aerial parts of C. zacatechichi interferes with the cholinergic and dopaminergic systems, but has no impact against monoamine oxidase A. Additionally, a notable cytotoxic effect was observed in SH-SY5Y and BV-2 cells at concentrations as low as 125 and 500 μg/mL (p < 0.05), respectively, LDH leakage suggesting apoptosis may occur at these concentrations, with necroptosis observed at higher ones. Despite the neurocytotoxic profile, these effects appear to be independent of radical stress, as the C. zacatechichi extract scavenged nitric oxide and superoxide radicals at concentrations as low as 62.5 μg/mL, significantly inhibiting also 5-lipoxygenase (IC50 = 72.60 ± 7.3 μg/mL; p < 0.05). Qualitative and quantitative analysis using HPLC-DAD-ESI(Ion Trap)MSn enabled the identification of 28 constituents, with 24 of them being previously unreported in this species. These include a series of dicaffeoylquinic, caffeoylpentoside, and feruloylquinic acids, along with 8 flavonols not previously known to occur in the species, mainly 3-O-monoglycosylated derivatives of quercetin, kaempferol, and isorhamnetin. ConclusionsOur findings regarding the neuroglial toxicity elicited by C. zacatechichi emphasize the necessity for a thorough elucidation of the plant's toxicity profile. Additionally, evidence is provided that the aerial parts of the plant inhibit both acetylcholinesterase and tyrosinase, potentially linking its psychopharmacological effects to the cholinergic and dopaminergic systems, with an apparent contribution from specific phenolic constituents previously unknown to occur in the species. Collectively, our results lay the groundwork for a regulatory framework on the consumption of C. zacatechichi in recreational settings and contribute to elucidating previous contradictory findings regarding the mechanisms underlying the dream-inducing effects of the plant.

Transcriptome analysis reveals biosynthesis and regulation of flavonoid in common bean seeds during grain filling

The Andean domesticated common beans (Phaseolus vulgaris) are significant sources of phenolic compounds associated with health benefits. However, the regulation of biosynthesis of these compounds during bean seed development remains unclear. To elucidate the gene expression patterns involved in the regulation of the flavonoid pathway, we conducted a transcriptome analysis of two contrasting Chilean varieties, Negro Argel (black bean) and Coscorron (white bean), at three developmental stages associated with seed color change, as well as different flavonoid compound accumulations. Our study reveals that phenolic compound synthesis initiates during seed filling, although it exhibits desynchronization between both varieties. We identified 10,153 Differentially Expressed Genes (DEGs) across all comparisons. The KEGG pathway ‘Flavonoid biosynthesis’ showed enrichment of induced DEGs in Negro Argel (PV172), consistent with the accumulation of delphinidin, petunidin, and malvidin hexosides in their seeds, while catechin glucoside, procyanidin and kaempferol derivatives were predominantly detected in Coscorrón (PV24). Furthermore, while the flavonoid pathway was active in both varieties, our results suggest that enzymes involved in the final steps, such as ANS and UGT, were crucial, inducing anthocyanin formation in Negro Argel. Additionally, during active anthocyanin biosynthesis, the accumulation of reserve proteins or those related to seed protection and germination was induced. These findings provide valuable insights and serve as a guide for plant breeding aimed at enhancing the health and nutritional properties of common beans.

Exploring the potential mechanisms of the ethyl acetate fraction of Hippophae rhamnoides L. seeds as a natural healing agent for wound repair

Ethnopharmacological relevanceSea buckthorn (Hippophae rhamnoides L.) has been designated a "medicine food homology" fruit by the National Health Commission of China due to its nutritional value. In traditional Chinese ethnomedicine, Hippophae rhamnoides L. is commonly used to treat nonhealing wounds such as burns, sores, and gastric ulcers. The aim of this study was to explore the healing effects of the ethyl acetate extract of sea buckthorn seeds (SBS-EF) on burn wounds. Aim of the studyThe primary objectives of this research were to determine the most effective medicinal site of action for treating burns with sea buckthorn seeds (SBS) and to investigate the underlying material basis and mechanisms of their therapeutic effects. Materials and methodsThe effects of different components of SBS-EF on the proliferation and migration of human skin fibroblasts (HSFs) were evaluated via MTT assays, scratch assays, transwell assays, and hydroxyproline secretion analysis. SBS-EF displayed the greatest activity amongst the extracts. Subsequent analyses included network pharmacology methodology, molecular docking studies, ultraperformance liquid chromatography UPLC-Orbitrap-Exploris-120-MS and a severe second-degree burn rat model to investigate the chemical constituents and potential therapeutic mechanisms of the SBS-EF. ResultsIn vitro studies demonstrated the efficacy of SBS-EF in promoting HSF growth and migration. UPLC-Orbitrap-Exploris-120-MS analysis revealed that SBS-EF had ten major constituents, with flavonoids being the predominant compounds, especially catechin, quercetin, and kaempferol derivatives. Network pharmacology and molecular docking analyses indicated that SBS-EF may exert its healing effects by modulating the Wnt/β-catenin signalling pathway. Subsequent in vivo experiments demonstrated that SBS-EF accelerated burn wound healing in rats, increased hydroxyproline expression in skin tissue, facilitated skin structure repair, and enhanced collagen production and organisation over a 21 d period. Additionally, exposure to SBS-EF upregulated WNT3a and β-catenin while downregulating GSK-3β levels in rat skin tissue. ConclusionsThe wound healing properties of SBS-EF were attributed to its ability to enhance HSF growth and migration, increase hydroxyproline levels in the skin, promote collagen accumulation, reduce scarring, and decrease the skin water content. SBS-EF may also provide therapeutic benefits for burns by modulating the Wnt/β-catenin signalling pathway, as evidenced by its effective site and likely mechanism of action in the treatment of burned rats.

Kalanchoe tomentosa: Phytochemical Profiling, and Evaluation of Its Biological Activities In Vitro, In Vivo, and In Silico.

In this work, the leaves of K. tomentosa were macerated with hexane, chloroform, and methanol, respectively. The phytochemical profiles of hexane and chloroform extracts were unveiled using GC/MS, whereas the chemical composition of the methanol extract was analyzed using UPLC/MS/MS. The antibacterial activity of extracts was determined against gram-positive and gram-negative strains through the minimal inhibitory concentration assay, and in silico studies were implemented to analyze the interaction of phytoconstituents with bacterial peptides. The antioxidant property of extracts was assessed by evaluating their capacity to scavenge DPPH, ABTS, and H2O2 radicals. The toxicity of the extracts was recorded against Artemia salina nauplii and Caenorhabditis elegans nematodes. Results demonstrate that the hexane and chloroform extracts contain phytosterols, triterpenes, and fatty acids, whereas the methanol extract possesses glycosidic derivatives of quercetin and kaempferol together with sesquiterpene lactones. The antibacterial performance of extracts against the cultured strains was appraised as weak due to their MIC90 values (>500 μg/mL). As antioxidants, treatment with extracts executed high and moderate antioxidant activities within the range of 50-300 μg/mL. Extracts did not decrease the viability of A. salina, but they exerted a high toxic effect against C. elegans during exposure to treatment. Through in silico modeling, it was recorded that the flavonoids contained in the methanol extract can hamper the interaction of the NAM/NAG peptide, which is of great interest since it determines the formation of the peptide wall of gram-positive bacteria. This study reports for the first time the biological activities and phytochemical content of extracts from K. tomentosa and proposes a possible antibacterial mechanism of glycosidic derivatives of flavonoids against gram-positive bacteria.

Comparative Analysis of Acetylated Flavonoids' Chemopreventive Effects in Different Cancer Cell Lines.

Flavonoids, a class of natural compounds with anticancer activity, exhibit varying biological activities and potencies based on their structural differences. Acylation, including acetylation of flavonoids, generally increases their structural diversity, which is closely related to the diversity of bioactivity within this group of compounds. However, it remains largely unknown how acetylation affects the bioactivity of many flavonoids. Based on our previous findings that O-acetylation enhances quercetin's bioactivity against various cancer cells, we synthesized 12 acetylated flavonoids, including seven novel compounds, to investigate their anticancer activities in the MDA-MB-231, HCT-116, and HepG2 cell lines. Our results showed that acetylation notably enhanced the cell proliferation inhibitory effect of quercetin and kaempferol across all cancer cell lines tested. Interestingly, while the 5,7,4'-O-triacetate apigenin (3Ac-A) did not show an enhanced the effect of inhibition of cell proliferation through acetylation, it exhibited significantly strong anti-migration activity in MDA-MB-231 cells. In contrast, the 7,4'-O-diacetate apigenin (2Ac-Q), which lacks acetylation at the 5-position hydroxy group, showed enhanced cell proliferation inhibitory effect but had weaker anti-migration effects compared to 3Ac-A. These results indicated that acetylated flavonoids, especially quercetin, kaempferol, and apigenin derivatives, are promising for anticancer applications, with 3Ac-A potentially having unique anti-migration pathways independent of apoptosis induction. This study highlights the potential application of flavonoids in novel chemopreventive strategies for their anti-cancer activity.

A chemical analysis of the Pelargonium species: P. odoratissimum, P. graveolens, and P. zonale identifies secondary metabolites with activity against gram-positive bacteria with multidrug-resistance.

The Pelargonium genus encompasses around 280 species, most of which are used for medicinal purposes. While P. graveolens, P. odoratissimum, and P. zonale are known to exhibit antimicrobial activity, there is an evident absence of studies evaluating all three species to understand their chemical differences and biological effects. Through the analysis of the hydroalcoholic extracts of P. graveolens, P. odoratissimum, and P. zonale, using HPLC-DAD-MS/MS, quercetin and kaempferol derivatives were identified in these three species. Conversely, gallotannins and anthocyanins were uniquely detected in P. zonale. P. graveolens stood out due to the various types of myricetin derivatives that were not detected in P. odoratissimum and P. zonale extracts. Evaluation of their biological activities revealed that P. zonale displayed superior antibacterial and antibiofilm activities in comparison to the other two species. The antibacterial efficacy of P. zonale was observed towards the clinically relevant strains of Staphylococcus aureus ATCC 25923, Methicillin-resistant Staphylococcus aureus (MRSA) 333, Enterococcus faecalis ATCC 29212, and the Vancomycin-resistant E. faecalis INSPI 032. Fractionation analysis of P. zonale suggested that the antibacterial activity attributed to this plant is due to the presence of quercetin derivatives and kaempferol and its derivatives, alongside their synergistic interaction with gallotannins and anthocyanins. Lastly, the three Pelargonium species exhibited notable antioxidant activity, which may be attributed to their high content of total phenolic compounds.

Characterization of key genes in anthocyanin and flavonoid biosynthesis during floral development in Rosa canina L.

This study investigates the transition of Rosa canina L. petals from pink to white, driven by genetic and biochemical factors. It characterizes the expression of ten key genes involved in anthocyanin and flavonoid biosynthesis across five developmental stages, correlating gene expression with flavonoid and anthocyanin concentrations and colorimetric changes. Initially, the petals exhibit a rich flavonoid profile, dominated by Rutin and Kaempferol derivatives. The peak anthocyanin concentration, corresponding to the deepest color saturation, occurs in the subsequent stage. Advanced chromatographic analyses identify key flavonoids persisting into the final white petal stage. Notably, the ANS gene shows a dramatic 137.82-fold increase in expression at the final stage, indicating its crucial role in petal color maturation despite the absence of visible pigmentation. The study provides a comprehensive characterization of the genetic and biochemical mechanisms underlying petal pigmentation, suggesting that reduced anthocyanin synthesis and increased flavonol concentration led to white petals. It also highlights the roles of other genes such as PAL, CCD1, FLS, CHI, CHS, UFGT, F3H, DFR, and RhMYB1, indicating that post-translational modifications and other regulatory mechanisms may influence anthocyanin stability and degradation.

Identification and quantification of flavonoids in edible dock based on UPLC-qTOF MS/MS and molecular networking

Edible dock, also known as Rumex patientia L.×Rumex tianschanicus A. LOS., exhibiting the characteristics of high yield, high protein and high nutrition, is widely used in the functional food industry and Chinese herbal medicine while short of secondary metabolites research. This study used UPLC-qTOF MS with two ion polarity in conjunction with Molecular Networking from Global Natural Products Social (GNPS) platform. Then, these 16 flavonoid substances including quercetin derivatives and kaempferol derivatives, firstly were identified from leaves in edible dock and were systematically investigated by UPLC-qTOF MS/MS. MS/MS experiments found that quercetin derivatives have five common characteristic ions, including m/z 300, m/z 271, m/z 255, m/z 243, and m/z 151. In addition, kaempferol derivatives have three common characteristic ions, including m/z 284, m/z 255, and m/z 227. Subsequently, 7 representative constituents were quantified via UPLC-QQQ MS with chemometrics, and the total content of 7 major flavonoids in its dry leaves is 6.988 mg/g in the 21st day samples. The work provided abundant metabolites information of flavonoids in edible dock, and the common characteristic ions will facilitate the building blocks-based molecular network (BBMN) to predict novel framework compounds from quercetin derivatives and kaempferol derivatives, laying the basis for exploitation of edible dock in the fields of pharmaceuticals, health food, and livestock feed.

Extraction of kaempferol derivatives from Zygophyllum paulayanum and its diverse biological activities

Zygophyllum paulayanum (Zygophyllaceae), is a plant commonly found in the desert region, well-known for its antioxidant, anticancer, wound healing, anti-inflammatory and antibacterial, properties. In this present work, we have studied the extraction of kaempferol derivatives from Z. paulayanum which showed excellent biological activities. The whole plant (root, leaves and stem) was extracted using ethanol, hydrolysed with HCl, and studied for the identification of active molecules. Different techniques like TLC, HPLC, and LCMS have been used to identify and confirm the kaempferol aglycone flavonoid. A mass spectrometric method based on electrospray ionisation has confirmed the presence of kaempferol flavonoid. Apart from the hydrolysed extract, the unhydrolyzed extract was also tested for LCMS which confirms the presence of glycosides such as kaempferol 3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside, kaempferol 3-O-β –rutinoside and kaempferol-3-o-rhamnoside. Both extracts of Z. paulayanum exhibited superior antioxidant, anti-inflammatory, antimicrobial, phytoestrogenic and cytotoxic properties which might be due to the presence of kaempferol derivatives.

Kaempferol Derivatives from Hippophae rhamnoides Linn. Ameliorate H2O2-Induced Oxidative Stress in SH-SY5Y Cells by Upregulating Nrf2.

As a medicinal and edible resource, Hippophae rhamnoides Linn. subsp. sinensis Rousi is rich in bioactive secondary metabolites, including flavonoids and their derivatives, which offer protective effects against oxidative damage. This study reported the isolation of three new kaempferol derivatives from the seed residue of H. rhamnoides - Hippophandine A, B, and C (compounds 1-3). Their structures were elucidated by high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), nuclear magnetic resonance (NMR), and chemical analyses. The compounds were evaluated for their ability to mitigate hydrogen peroxide (H2O2)-induced cell death in SH-SY5Y cells. The results elucidated that Hippophandine A-C at concentrations of 1, 5, and 10 μM reduced the levels of malondialdehyde (MDA) and increased the activity of antioxidative enzymes, such as superoxide dismutase (SOD), glutathione (GSH), and catalase (CAT). Furthermore, they significantly altered the protein expression of nuclear factor erythroid 2-related factor 2 (Nrf2) and its downstream heme oxygenase-1 (HO-1), which is an indicator of redox detection in H2O2-induced SH-SY5Y.

Network pharmacology and in silico approaches to uncover multitargeted mechanism of action of Zingiber zerumbet rhizomes for the treatment of idiopathic pulmonary fibrosis

Background Idiopathic pulmonary fibrosis (IPF) is a disease with high mortality, and there are only two specific drugs available for therapeutic management with limitations. The study aims to identify comprehensive therapeutic mechanisms of Zingiber zerumbet rhizomes (ZZR) to treat IPF by using network pharmacology followed battery of in silico studies. Methods The protein-protein interaction network was developed using Cytoscape to obtain core disease targets involved in IPF and their interactive molecules of ZZR. Based on the pharmacophore properties of phytomolecules from ZZR, the drug targets in IPF were explored. Protein-protein interaction network was built in Cytoscape to screen potential targets and components of ZZR. Molecular docking and dynamics were conducted as an empirical study to investigate the mechanism explored through network pharmacology in relation to the hub targets. Results The network analysis conferred kaempferol derivatives that had demonstrated a promising therapeutic effect on the perturbed, robust network hubs of TGF-β1, EGFR, TNF-α, MMP2 &amp; MMP9 reported to alter the biological process of mesenchymal transition, myofibroblast proliferation, and cellular matrix deposition in pulmonary fibrosis. The phytomolecules of ZZR act on two major significant pathways, namely the TGF-β-signaling pathway and the FOXO-signaling pathway, to inhibit IPF. Confirmational molecular docking and dynamics simulation studies possessed good stability and interactions of the protein-ligand complexes by RMSD, RMSF, rGyr, SASA, and principal component analysis (PCA). Validated molecular docking and dynamics simulations provided new insight into exploring the mechanism and multi-target effect of ZZR to treat pulmonary fibrosis by restoring the alveolar phenotype through cellular networking. Conclusions Network pharmacology and in silico studies confirm the multitargeted activity of ZZR in the treatment of IPF. Further in vitro and in vivo studies are to be conducted to validate these findings.

Protective effect and antioxidative efficacy of Moringa stenopetala leaf extract in BV-2 microglial cell

Moringa stenopetala is often consumed as food and used in folkloric medicine for the management of several diseases including neurodegenerative diseases. This study investigated the protective effect and antioxidant efficacy of aqueous extract of Moringa stenopetala in BV-2 microglial cells. Aqueous extracts of M. stenopetala were prepared, lyophilized and reconstituted in 0.5% dimethylsulphoxide (DMSO). Cells were treated with M. stenopetala extracts (0.1–100 µg/ml) for cell viability assay and nitric oxide (NO) production tests. However, M. stenopetala extract (50 µg/ml) was used in the treatment of cells for the determination of protein carbonyl content and reactive oxygen species (ROS) level. Incubation of BV-2 microglia cell with M. stenopetala extract maintained cell viability, diminished NO and ROS levels, and reduced protein carbonyl contents. Chlorogenic acid, rutin, kaempferol and quercetin derivatives were the main phenolic compounds identified in M. stenopetala leaf extract. In conclusion, this study suggests that M. stenopetala extract is rich in antioxidant and contains bioactive neuroprotective agents.

Evidences of in vivo cytotoxic and apoptotic potential of anthelmintic phytochemical kaempferol derivative isolated from Lysimachia ramosa (Wall. ex Duby) in Wistar rats

BackgroundLysimachia ramosa (Wall. ex Duby) is a traditionally used medicinal plant in Meghalaya, a northeastern state of India. The people use the leaves of the plant to cure gastrointestinal worm infection. Kaempferol derivative, isolated from the leaves of the plant L. ramosa, was found to be the active anthelmintic compound in previous studies. The phytochemical present in the leaves causes alterations in the ultrastructure of the tegument of cestode, its glycogen content and tegumental enzymes. However, it has been found in the review of the literature that phytoproduct should be consumed in a limited dose during longtime treatment period to avoid any potential ill effects on the health of the consumers as many plant-based products are found to be toxic beyond a safe dose limit. Thereby, it becomes necessary to check the potential toxic effects of the active compound taking an animal model. Hence, the present study had been carried out to evaluate the toxicity of the active component on Wistar rats to find out the safe dose of the test compound for oral consumption through observations, if any, on chromosomal abnormalities, ultrastructural changes in bone marrow cells and apoptosis in liver and kidney.ResultsThe result shows kaempferol derivative causes a significant rise in chromosomal abnormalities (2.83 ± 0.19%, 3.83 ± 0.11%) and a significant decline in mitotic indices (3.17 ± 0.02%, 3.10 ± 0.01%) upon treatment with 500 mg and 1000 mg/kg b.w. dosages. At this level, the number of micronucleated erythrocytes increases significantly in the animals (2.33 ± 0.33%, 3.15 ± 0.24%). Intercellular integrity and eosinophil in the bone marrow are observed to be deformed and damaged on treatment with 1000 mg compound/kg b.w. of animals. Apoptotic indices are seen to be increased significantly (3.12 ± 0.18%, 6.17 ± 0.17%) and (2.43 ± 0.13%, 4.17 ± 0.17%) for the liver and kidney, respectively, in the animals of higher-dose treatment groups.ConclusionsThe compound, kaempferol derivative in the present study, has been found to have cytotoxic and pro-apoptotic effects on the test animals beyond a certain dose, if consumed for longer period of time. Therefore, it can be concluded that kaempferol derivative extracted from Lysimachia ramosa should be tested for future trials on animals/humans at dose below 250 mg/kg body weight.

Dereplication Tools for Rhizophora mangle Extracts from Different Mangrove Areas and their Potential Against Staphylococcus aureus.

Rhizophora extracts have several potential biological activities, and their metabolites can be used in the pharmaceutical industry. Extracts of Rhizophora species obtained from mangroves have shown prospective activity against Staphylococcus aureus. This study aimed to investigate the chemical profile of Rhizophora mangle leaves from fringe, basin, and transition mangrove zones and their bactericidal/bacteriostatic potential against S. aureus. R. mangle leaves were collected monthly in 2018 from litterfall in three different zones of the mangrove of Guaratiba State Reserve: fringe, basin, and transition. Extracts were prepared from the material collected in October and December for LC-HRMS/MS analysis, and dereplication was performed using a molecular library search and the classical molecular networking GNPS platform. The minimum inhibitory concentrations (MICs) of the aqueous extract of R. mangle against S. aureus were determined. No S. aureus growth was observed compared to the control for extracts collected from September to December. Different compounds were annotated in each region, yet a marked presence of phenolic compounds was noted, among them glycosylated flavonoid derivatives of quercetin and kaempferol. The results suggest bactericidal/bacteriostatic activity for extracts of R. mangle leaves collected in 2018 from three mangrove forest zones.

Flavonoids as dual-action agents for anticancer and anti-tooth caries: a molecular docking and dynamics simulation on MMP2 inhibition

Objective: Cancer pathogenesis is linked to matrix metalloproteinase-2 (MMP2). Numerous studies have indicated an elevated expression of MMP2 in the tissue microenvironment of different cancers, including breast, oral, prostate, ovarian, colorectal, bladder, lung, and hepatocellular carcinoma. The significant role of MMP2 in the degradation of organic compounds in dentin, causing dental caries, has been indicated by accumulating evidence. This study explored the possibility of using flavonoids as natural compounds capable of inhibiting MMP2 to meet the need for new and potent MMP2 inhibitors. Methods: The AutoDock software evaluated the binding energies between selected flavonoids and the MMP2 catalytic domain and ranked the ligands based on their inhibition constant (Ki) values and Gibbs free binding energy scores. The Discovery Studio Visualizer tool demonstrated how the highest-ranked flavonoids interact with the MMP2. Molecular dynamics was conducted for the most potent MMP2 inhibitor in a 100 ns computer simulation. Results: Kaempferol 3-rutinoside-7-sophoroside demonstrated an inhibitory effect against MMP2 with a Ki value and ΔGbinding score of 209.92 fM and −17.30 kcal/mol, respectively. This flavonoid was able to restrict MMP2 activity within a femtomolar range. This study identified eight flavonoids with Ki values in the picomolar range. According to the study, the docked pose of kaempferol 3-rutinoside-7-sophoroside within the MMP2 catalytic domain reached stability after a simulation of ~60 nanoseconds. Conclusion: Inhibition of MMP2 by flavonoids, notably kaempferol derivatives, might be an effective therapeutic strategy for cancer treatment.

From Ethnobotany to Biotechnology: Wound Healing and Anti-Inflammatory Properties of Sedum telephium L. In Vitro Cultures.

Sedum telephium is a succulent plant used in traditional medicine, particularly in Italy, for its efficacy in treating localized inflammation such as burns, warts, and wounds. Fresh leaves or freshly obtained derivatives are directly applied to the injuries for these purposes. However, challenges such as the lack of microbiologically controlled materials and product standardization prompted the exploration of more controlled biotechnological alternatives, utilizing in vitro plant cell cultures of S. telephium. In the present study, we used HPLC-DAD analysis to reveal a characteristic flavonol profile in juices from in vivo leaves and in vitro materials mainly characterized by several kaempferol and quercetin derivatives. The leaf juice exhibited the highest content in total flavonol and kaempferol derivatives, whereas juice from callus grown in medium with hormones and callus suspensions showed elevated levels of quercetin derivatives. The in vitro anti-inflammatory and wound-healing assays evidenced the great potential of callus and suspension cultures in dampening inflammation and fostering wound closure, suggesting quercetin may have a pivotal role in biological activities.

Integrated transcriptomic and metabolomic analysis provides insights into cold tolerance in lettuce (Lactuca sativa L.)

The popular leafy vegetable lettuce (Lactuca sativa L.) is susceptible to cold stress during the growing season, which slows growth rate, causes leaf yellowing and necrosis, and reduced yield and quality. In this study, transcriptomic and metabolomic analyses of two cold-resistant lettuce cultivars (GWAS-W42 and F11) and two cold-sensitive lettuce cultivars (S13K079 and S15K058) were performed to identify the mechanisms involved in the cold response of lettuce. Overall, transcriptome analysis identified 605 differentially expressed genes (DEGs), including significant enrichment of genes involved in the flavonoid and flavonol (CHS, CHI, F3H, FLS, CYP75B1, HCT, etc.) biosynthetic pathways related to oxidation–reduction and catalytic activity. Untargeted metabolomic analysis identified fifteen flavonoid metabolites and 28 other metabolites potentially involved in the response to cold stress; genistein, quercitrin, quercetin derivatives, kaempferol derivatives, luteolin derivatives, apigenin and their derivatives accumulate at higher levels in cold-resistant cultivars. Moreover, MYBs, bHLHs, WRKYs and Dofs also play positive role in the low temperature response, which affected the expression of structural genes contributing to the variation of metabolites between the resistant and sensitive. These results provide valuable evidence that the metabolites and genes involved in the flavonoid biosynthetic pathway play important roles in the response of lettuce to cold stress.

Actividad antioxidante y antimicrobiana in vitro e in silico de extractos etanólicos de hojas de Cnidoscolus chayamansa

Actividad antioxidante y antimicrobiana in vitro e in silico de extractos etanólicos de hojas de Cnidoscolus chayamansa

The Impact of Deficit Irrigation on the Agronomic Performance and Chemical Composition of Scolymus hispanicus L.

In the current study, the effects of drought stress on the growth and phytochemical profile of Scolymus hispanicus L. (a.k.a. golden thistle) were evaluated. Plants were treated with three irrigation regimes, e.g., plants that received only rainwater (Control; C), deficit irrigation (I1; 50% of field capacity (FC)), and full irrigation (Ι2; 100% of FC). The fresh weight of the rosette of leaves was not negatively impacted by deficit irrigation, whereas root development was severely restrained compared to control and I2 treatments. Drought stress conditions had a positive effect on the nutritional properties of the golden thistle since the treatments of control and deficit irrigation showed the highest content of macronutrients and energy. Oxalic acid was the richest organic acid, especially under the I1 regime. Similarly, α-tocopherol was the only identified vitamin E isoform, whose content was also doubled in I1 treatment. Raffinose, glucose, and sucrose were the most abundant free sugars in amounts that varied among the irrigation treatments, while the total and distinct free sugar content was the highest for the I1 treatment. The most abundant detected fatty acid compounds were α-linolenic acid, followed by palmitic and linoleic acid, with the highest amount being detected in C, I1, and I2 treatments, respectively. Flavonoids were the only class of polyphenols detected in golden thistle leaves, including mostly kaempferol and quercetin derivatives. The greatest antioxidant potency was shown for the control and I1 treatments (for OxHLIA and TBARS methods, respectively). The evaluated leaf samples recorded a varied antimicrobial effect for the different bacterial strains and fungi, whereas no cytotoxic, hepatotoxic, and anti-inflammatory effects against the tested cell lines were recorded. Finally, the mineral content of leaves was significantly affected by the irrigation regime, with Ca, Mg, Cu, and Zn being the highest for the I1 treatment, while the I2 treatment had the highest content of K, Fe, and Mn and the lowest Na content. In conclusion, deficit irrigation showed promising results since it improved the phytochemical content without compromising the fresh weight of leaves, and thus it could be suggested as a sustainable agronomic practice for producing high-added value products without significant constraints in growth development and yield parameters of golden thistle.