Kaempferol Derivatives Research Articles

Flavonoid rich extract of Trigonella foenum-graecum leaves ameliorate liver fibrosis

Liver fibrosis is a leading cause of mortality and morbidity globally. For decades, plant secondary metabolites such as flavonoids and saponins have attained much consideration due to their safer therapeutic potential against chronic liver diseases. Trigonella foenum-graecum (Common name “Fenugreek”) is an annual herb used as a spice to increase the taste and aroma of food. Its fresh leaves are used as food and are rich in flavonoids. In the current study antifibrotic potential of Trigonella foenum-graecum flavonoid-rich leaf extract (TF) was evaluated in CCl4-induced hepatic fibrosis in mice. The ALT, AST, MDA, CAT, and GSH analysis illustrated that the treatment group significantly reverses CCl4-induced liver damage. The TF extract was found to be rich in quercetin and kaempferol derivatives analyzed through ESI-MS/MS. After four weeks of the TF treatment, hepatocyte architecture improved and collagen deposition in mice liver tissues reduced considerably. The expression of fibrotic markers, including COL-IA, α-SMA, PDGF, and TIMP1, was downregulated, and MMP3 was upregulated significantly at mRNA and protein levels. Interestingly, TF significantly downregulated NF-κB expression and TGF-β/Smad signaling pathway and upregulated miR-146a and miR-29b. Taking together, these results demonstrated that Trigonella foenum-graecum flavonoid-rich leaf extract ameliorated liver inflammatory and fibrogenic responses through miR-146a/miR-29b/TGF-β/Smad axis.

Biochemical and Ultrastructural Studies for Toxicity of Kaempferol Derivative Recovered from the Plant Lysimachia Ramosa

Leaves of Lysimachia ramosa are used by various tribes of Meghalaya to cure intestinal helminth infections. Preliminary investigations disclosed impressive anthelmintic effects of the kaempferol derivative, an active component of the plant, however, toxic effects on its consumers, if any, are not known. Therefore, the present study has been undertaken to investigate the acute and sub-acute toxic effects of kaempferol derivative, of the plant, taking Wistar rats as a model. Following OECD 407, 250 mg, 500 mg, and 1000 mg/kg body weight doses of the active component have been selected to treat the animals for 28 days. On the 29th day, the animals have been sacrificed to assess different toxicological effects on animals. The LD50 value of the anthelmintic component was found to be more than 5000 mg/kg body weight of rats. Histological, ultrastructural, haematological, biochemical, andorgano-somatic (HSI and RSI) studies demonstrate changes in surface characteristics of various cellular organelles of different vital organs such as the liver, kidney, and intestine. Alterations were also recorded in different vital enzymes such as AST, ALT, and ALP in the phytochemical exposed rats at higher doses. The results revealed that treatment with the active component at a higher concentration may lead to toxicological effects if treatment persists for a longer period.

Sb(V) Kaempferol and Quercetin Derivative Complexes: Synthesis, Characterization and Antileishmanial Activities.

Recent studies on Leishmaniasis treatment have confirmed the antiparasitic effects of flavonols and organic antimony pentavalent [(Sb(V)] complexes. This study aimed to identify new Sb(V) complexes by combining the benefits of antimonials and flavonols as well as by optimizing their properties. Kaempferol and quercetin peracetate were prepared using acetic anhydride in pyridine. By performing regioselective synthesis, 7-O-paramethylbenzyl as an electron-donating group and 7-O-paranitrobenzyl as an electron-withdrawing group were added to quercetin, and, then, the synthesis of Sb(V) kaempferol and quercetin derivative complexes were performed using SbCl5 solution in glacial acetic acid. The structures were confirmed by UV, ESI mass, IR, 1H-, and 13C-NMR spectral data, and the Stoichiometry of the ligand-metal complex by the mole ratio method. Computational molecular modeling was conducted using the Gaussian program. The structures were confirmed based on the results from UV, nuclear magnetic resonance (NMR), and electrospray ionization (ESI) mass analyses (3-12). Among the produced compounds, 11 and 12 as newly described, and other compounds as pre-defined compounds were identified. According to the results from biological test, kaempferol triacetate with more lipophilicity showed the highest anti-promastigote activity with an IC50 value of 14.93 ± 2.21 µM. As for anti-amastigote activity, despite the differences, all antimony complexes showed anti-amastigote effects in vitro with IC50 values of 0.52 to 14.50 µM. All flavonol Sb(V) complexes showed higher activity compared to meglumine antimonate in anti-amastigote effect. Inside the host macrophages, by breaking down the complex into antimony and quercetin or kaempferol analogs, the observed antiparasitic effects may have been related to both Sb(V)/Sb(III) conversion and flavonoid antileishmanial activities.

Extraction optimization for the antioxidants from Nigella sativa seeds using response surface methodology

Although many studies have explored the bioactive compound content of Nigella sativa (black seed – BS) essential oil, data on the phenolic compound content in the extracts of Nigella sativa seeds gives inconclusive results [1–3]. In this study, response surface methodology (RSM) with a central composite plan (CCP) was used for the experimental design and identification of the optimal conditions for maximizing the phenolic content and the antioxidant activity of BS extract. The independent variables were as followed: temperature (22.9–67.1ºC), time (31.7–208.2 min), and methanol concentration in water (5.9–94.1% v/v). Different response variables (total polyphenols – TPC, total flavonoids – TFC and the antioxidant activity – DPPH and TEAC) required different optimal conditions to maximize them. The multi-response optimization was performed to determine the extraction conditions, which would simultaneously ensure the highest phenolic content and the antioxidant activity. The optimal conditions derived from the multi-response desirability function were as followed: 120 min, 56 °C and 50% methanol, giving the TPC = 7.05 mg/g, TFC = 3.05 mg/g, DPPH = 9.04 µmol/g and TEAC = 33.24 µmol/g (with desirability function coefficient = 0.83). Solvent concentration was established as a crucial parameter for the extraction of antioxidants from BS. A quercetin derivative and two derivatives of kaempferol were determined by HPLC (high performance liquid chromatography) analysis of the BS extract at the optimal conditions. The accuracy of the models for all response variables was confirmed by a high correlation coefficient (r = 0.99) between the experimental values and those predicted under optimal conditions.

Spray-drying Microencapsulation of an Extract from Tilia tomentosa Moench Flowers: Physicochemical Characterization and in Vitro Intestinal Activity

Silver linden (Tilia tomentosa Moench, TtM) flowers possess several health-promoting properties, especially at the neurological level, such as intestinal relaxation activity associated with specific flavonols, particularly quercetin and kaempferol derivatives. However, such molecules are susceptible to degradation upon different triggers like heat, light and extreme pH values. To overcome the scarce stability of TtM flowers bioactive molecules and make them suitable for developing functional food and supplements, we applied microencapsulation. Spray-drying microencapsulation of TtM flowers extract was performed using three starch-derived wall materials: maltodextrin 12 DE (MD12) and 19 DE (MD19), and OSA-modified starch (OSA-S). The stability of total phenols, flavanols, and antioxidant capacity was monitored for 70 days under accelerated stress conditions (40 °C/70% RH) by HPLC and spectrophotometric methods, and the intestinal contractile activity was tested in a murine model. In comparison to MD12 and MD19, OSA-S stood out for the higher encapsulation efficiency of quercetin and kaempferol glycosides (+ 36–47% compared to MD12 and + 18–24% compared to MD19) and stability thereof (half-life on average + 30% compared to MD12 and + 51% compared to MD19). The intestinal contractile activity of OAS-S powders resulted comparable to the original extract, indicating that flavonols were biologically active and accessible. Our results underly the potential advantages of OSA-S encapsulated formulation as a functional ingredient for the development of nutraceutical products.

Phenolic Compounds' Occurrence in Opuntia Species and Their Role in the Inflammatory Process: A Review.

Within the Cactaceae family, Opuntia comprises the most widespread species, with a recognized importance in human life, including feeding, domestic use as home natural barriers, and as a traditional remedy for diverse diseases and conditions such asthma, edema, and burns. Indeed, scientific reports have stated that these health benefits may be due to various active compounds, particularly polyphenols, which are ubiquitously found in plants and have proven their pharmacological efficiency by displaying antimicrobial, anti-cancer, and anti-inflammatory activities, among others. Opuntia species contain different classes of phenolic compounds that are recognized for their anti-inflammatory potential. Among them, quercetin, isorhamnetin, and kaempferol derivates were reported to greatly contribute to modulate cells’ infiltration and secretion of soluble inflammatory mediators, with key implications in the inflammatory process. In this review, we make a summary of the different classes of phenolic compounds reported in Opuntia species so far and explore their implications in the inflammatory process, reported by in vitro and in vivo bioassays, supporting the use of cactus in folk medicine and valorizing them from the socio-economic point of view.

Phytochemical Profile and Biological Activity of the Ethanolic Extract from the Aerial Part of Crocus alatavicus Regel & Semen Growing Wildly in Southern Kazakhstan.

The composition of the ethanolic extract from the aerial parts of Crocus alatavicus Regel & Semen from southern Kazakhstan spontaneous flora was analyzed together with the determination of its antibacterial, antifungal, antiviral and anticancer activity. The phytochemical profile analysis by high-performance liquid chromatography-electrospray ionization-quadrupole-time of flight-mass spectrometry (HPLC/ESI-QTOF-MS) revealed the presence of multiple kaempferol derivatives. High-performance reverse-phase liquid chromatography combined with a photodiode-array detection (RP-HPLC/PDA) found that kaempferol 3-O-dihexoside and kaempferol 3-O-acyltetrahexoside accounted for 70.5% of the kaempferol derivatives. The minimum inhibitory concentration (MIC) values of the extract for all the tested reference microorganisms were high, reaching 10 mg/mL for yeasts and 20 mg/mL for bacteria. In contrast, antiviral activity was observed at 2 mg/mL, resulting in the inhibition of the HSV-1-induced cytopathic effect and the reduction in virus infectious titer by 1.96 log, as well as the viral load by 0.85 log. Among the tested prostate cancer cell lines, significant cytotoxic activity of the extract was noted only on the LNCaP cell line, with an IC50 value of 1.95 mg/mL. The LNCaP cell line treated with 2 mg/mL of the extract showed a noticeably reduced number of spindle-shaped cells with longer cellular projections, a significant increase in the peak corresponding to the population of apoptotic cells in the sub-G1 phase and a decreased intracellular glutathione (GSH) level, suggesting the prooxidative properties of the extract. The obtained data provide novel information about the flavonoids present in the aerial part of C. alatavicus and suggest its potential application as a source of the compounds active against HSV-1 and metastatic, androgen-sensitive prostate cancer.

An Integrated Metabolome and Transcriptome Analysis Reveal the Regulation Mechanisms of Flavonoid Biosynthesis in a Purple Tea Plant Cultivar.

Purple tea plant cultivars, enrich with flavonoids and anthocyanins, are valuable materials for manufacturing tea with unique color and flavor. Researchers found that ‘Zijuan’ leaves changed from purple to green mainly caused by the decreased flavonoids and anthocyanins concentrations. The mechanism of flavonoids and anthocyanin biosynthesis has been studied in many purple tea plant cultivars and the key genes which regulated the biosynthesis of flavonoid and anthocyanins in different purple tea plant cultivars were quite different. Also, the molecular regulation mechanism underlying the flavonoids and anthocyanins biosynthesis during leaves development and color changes is less-thoroughly understood. In this study, an integrative analysis of transcriptome and metabolome was performed on the purple leaves and green leaves of ‘Zijuan’ tea plant to reveal the regulatory networks correlated to flavonoid biosynthesis and to identify key regulatory genes. Our results indicated that the ‘Zijuan’ new shoots leaves were purple might be due to the copigmentation of quercetin and kaempferol derivatives. In ‘Zijuan’ tea plant cultivar, flavonoids metabolites concentrations in purple leaves and green leaves were significantly influenced by the genes involved in flavonoid biosynthesis, transcriptional regulation, transport, and hormone response. Transcription factors including NAC008, MYB23, and bHLH96 and transporters such as ABC transporter I might be responsible for the flavonoid and anthocyanins accumulation in purple leaves. This study provides a new insight into the metabolism and molecular mechanisms underlying flavonoid and anthocyanin biosynthesis in tea plant.

Modulation of class III peroxidase pathways and phenylpropanoids in Arundo donax under salt and phosphorus stress

Arundo donax L. is an invasive species that has been recently employed for biomass production due to its well-known ability to colonize harsh environment. Based on previous observations, the present study investigated the potential role of phenylpropanoids and class III peroxidases to confer adaptation through biochemical and transcriptomic analysis in A. donax after Na+ and P excess supply, both in single stress and in combination, and after growth at low P level.The levels of hydrogen peroxide, flavonoids (i.e., quercetin, apigenin and kaempferol derivatives) and the activity of class III peroxidases, as well as the expression of several genes encoding for their enzymes involved in their biosynthesis, increased when Na+ was supplied in combination with P. These results suggest that those biomolecules are involved in the response of A. donax, to the presence of +Na and P in the soil. Moreover, even though at the sampling time no significant accumulation of lignin has been determined, the trend of accumulation of such metabolite and most of all the increase of several transcripts involved in its synthesis was found. This work for the first time indicates the need for further investigation devoted to elucidating whether the strengthening of cell walls via lignin synthesis is one of the mechanisms used by A. donax to adapt to harsh environments.

Identification and Quantification of Glucosinolates and Phenolics in a Large Panel of Brassica napus Highlight Valuable Genetic Resources for Chemical Ecology and Breeding.

Glucosinolate (GLS) and phenolic contents in Brassicaceae contribute to biotic and abiotic stress responses. Breeding crop accessions harboring agroecologically relevant metabolic profiles require a characterization of the chemical diversity in Brassica germplasm. This work investigates the diversity of specialized metabolites in 281 accessions of B. napus. First, an LC-HRMS2-based approach allowed the annotation of 32 phenolics and 36 GLSs, revealing 13 branched and linear alkyl-GLSs and 4 isomers of hydroxyphenylalkyl-GLSs, many of which have been rarely reported in Brassica. Then, quantitative UPLC-UV-MS-based profiling was performed in leaves and roots for the whole panel. This revealed striking variations in the content of 1-methylpropyl-GLS (glucocochlearin) and a large variation of tetra- and penta-glucosyl kaempferol derivatives among accessions. It also highlighted two main chemotypes related to sinapoyl-O-hexoside and kaempferol-O-trihexoside contents. By offering an unprecedented overview of the phytochemical diversity in B. napus, this work provides a useful resource for chemical ecology and breeding.

Phytochemical and antidiabetic analysis of Curatella americana L. aqueous extract on the rat pregnancy

Ethnopharmacological relevanceCuratella americana L. is employed in popular medicine for treating diabetes. However, the understanding around its outcomes during pregnancy is unclear. Aim of the studyTo evaluate the phytochemical and hypoglycemic analysis of the C. americana extract and its maternal-fetal effect on diabetic rats. Materials and methodDiabetes was chemically induced 24 h after birth in Wistar female newborn rats. At adulthood, after diabetes status confirmation, the rats were mated and randomized into four experimental groups: Nondiabetic (Control): given water; Treated: given C. americana extract; Diabetic, and Treated Diabetic rats. The aqueous extract of C. americana leaves (300 mg/kg) was administered daily through oral route during pregnancy. Maternal toxicity and biochemical profile, reproductive outcomes, fetal development, and phenolic composition and biogenic amines in aqueous extract were analyzed. Results and conclusionPhytochemical analysis revealed that the main phenolic components are 3-hydroxytyrosol, kaempferol, and quercetin, while tryptophan and putrescine derivatives were identified as the dominant amines. C. americana extract treatment improved the lipid profile, although no effect on hyperglycemic control in diabetic rats was observed. Maternal diabetes or C. americana extract caused embryo losses confirmed by the lower number of pre-embryos in early pregnancy and higher percentage of abnormal morphologically pre-embryos. C. americana extract previously caused premature pre-embryo fixation before implantation window in nondiabetic and diabetic mothers and intrauterine growth restriction in the fetuses of treated nondiabetic dams, complicating the embryo fetal development. These findings reinforce the caution of indiscriminate use of medicinal plants, especially during pregnancy.

The effect of thermal pretreatment processing on the distribution of free and bound phenolics in virgin Camellia oleifera seed oil

The effect of thermal pretreatments on the distribution of free (FP) and bound phenolic (BP) in virgin C. oleifera seed oil, via mixed materials by hot air at 90–150 °C for 0–120 min before pressing, was investigated, using ultra-performance-liquid-chromatography tandem quadrupole time-of-flight mass-spectrometry (UPLC Q-TOF MS). In total, 162 components were tentatively identified, consisting of 76 phenolic acids, 33 flavonols, 22 flavones, 12 flavan-3-ols, 11 flavanones, 5 stilbenes and 3 others. The contents of total phenolic profiles ranged from 84.8 to 154.5 mg/kg, occupied 43.7–57.8%, 16.5–36.7% and 16.0–26.4% in FP, base-bound (BP–B) and acid-bound phenolic (BP-A), respectively. Gallic acid derivatives of phenolic acids, kaempferol derivatives of flavonols, and dimer of flavan-3-ols were the chief phenolic profiles, but presented dissimilarly in phenolic forms. The PCA suggested in comparison with the control, the distribution of BP-B had a remarkable variation as soon as the heating, and different behaviours occurred at 90 °C after 60 min and 150 °C after 60 min in BP-A and FP, respectively. Similarly, prominent differences were discovered for the main contributors among phenolic forms. This novel perspective could be of significance to explore the proper pretreatment processing of virgin C. oleifera seed before oil production.

Hypericum lanceolatum Lam. Medicinal Plant: Potential Toxicity and Therapeutic Effects Based on a Zebrafish Model.

Hypericum lanceolatum Lam. (H. lanceolatum) is a traditional medicinal plant from Reunion Island used for its pleiotropic effects mainly related to its antioxidant activity. The present work aimed to 1) determine the potential toxicity of the plant aqueous extract in vivo and 2) investigate its putative biological properties using several zebrafish models of oxidative stress, regeneration, estrogenicity, neurogenesis and metabolic disorders. First, we characterized the polyphenolic composition by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and identified chlorogenic acid isomers, quercetin and kaempferol derivatives as the major compounds. We then evaluated for the first time the toxicity of an aqueous extract of H. lanceolatum and determined a maximum non-toxic concentration (MNTC) in zebrafish eleutheroembryos from 0 to 96 hpf following OECD (Organization for Economic Cooperation and Development) guidelines. This MNTC test was also determined on hatched eleutheroembryos after 2 days of treatment (from 3 to 5 dpf). In our study, the anti-estrogenic effects of H. lanceolatum are supported by the data from the EASZY assay. In a tail amputation model, we showed that H. lanceolatum at its MNTC displays antioxidant properties, favors immune cell recruitment and tissue regeneration. Our results also highlighted its beneficial effects in metabolic disorders. Indeed, H. lanceolatum efficiently reduces lipid accumulation and body mass index in overfed larva- and adult-models, respectively. In addition, we show that H. lanceolatum did not improve fasting blood glucose levels in a hyperglycemic zebrafish model but surprisingly inhibited neurogenesis impairment observed in diabetic conditions. In conclusion, our study highlights the antioxidant, pro-regenerative, anti-lipid accumulation and pro-neurogenic effects of H. lanceolatum in vivo and supports the use of this traditional medicinal plant as a potential alternative in the prevention and/or treatment of metabolic disorders.

Characterization, Large-Scale HSCCC Separation and Neuroprotective Effects of Polyphenols from Moringa oleifera Leaves

Moringa oleifera leaves have been widely used for the treatment of inflammation, diabetes, high blood pressure, and other diseases, due to being rich in polyphenols. The main objective of this work was to largely separate the main polyphenols from Moringa oleifera leaves using the technique of high-speed counter-current chromatography (HSCCC). The phenolic composition in Moringa oleifera leaves was first analyzed qualitatively and quantitatively by UPLC-Q-Exactive Orbitrap/MS and UPLC-QqQ/MS, respectively, indicating that quercetin and kaempferol derivatives, phenolic acid and apigenin are the main polyphenols in Moringa oleifera leaves, with quercetin and kaempferol derivatives predominating. Furthermore, the conditions of HSCCC for large-scale separation of polyphenols from Moringa oleifera leaves were optimized, which included the selection of the solvent system, flow rate and the sample load. Only by one-step HSCCC separation (within 120 min) under the optimized conditions, six quercetin and kaempferol derivatives, a phenolic acid and an apigenin could be individually isolated at a large scale (yield from 10% to 98%), each of which possessed high purity. Finally, the isolated polyphenols and phenolic extract from Moringa oleifera leaves (MLPE) were verified to have strong neuroprotective activities against H2O2-induced oxidative stress in PC-12 cells, suggesting that these compounds would contribute to the main beneficial effects of Moringa oleifera leaves.

Effect of Kaempferol and Its Glycoside Derivatives on Antioxidant Status of HL-60 Cells Treated with Etoposide.

Kaempferol is a well-known antioxidant found in many plants and plant-based foods. In plants, kaempferol is present mainly in the form of glycoside derivatives. In this work, we focused on determining the effect of kaempferol and its glycoside derivatives on the expression level of genes related to the reduction of oxidative stress—NFE2L2, NQO1, SOD1, SOD2, and HO-1; the enzymatic activity of superoxide dismutases; and the level of glutathione. We used HL-60 acute promyelocytic leukemia cells, which were incubated with the anticancer drug etoposide and kaempferol or one of its three glycoside derivatives isolated from the aerial parts of Lens culinaris Medik.—kaempferol 3-O-[(6-O-E-caffeoyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P2), kaempferol 3-O-[(6-O-E-p-coumaroyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P5), and kaempferol 3-O-[(6-O-E-feruloyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P7). We showed that none of the tested compounds affected NFE2L2 gene expression. Co-incubation with etoposide (1 µM) and kaempferol (10 and 50 µg/mL) leads to an increase in the expression of the HO-1 (9.49 and 9.33-fold at 10 µg/mL and 50 µg/mL, respectively), SOD1 (1.68-fold at 10 µg/mL), SOD2 (1.72-fold at 10–50 µg/mL), and NQO1 (1.84-fold at 50 µg/mL) genes in comparison to cells treated only with etoposide. The effect of kaempferol derivatives on gene expression differs depending on the derivative. All tested polyphenols increased the SOD activity in cells co-incubated with etoposide. We observed that the co-incubation of HL-60 cells with etoposide and kaempferol or derivative P7 increases the level of total glutathione in these cells. Taken together, our observations suggest that the antioxidant activity of kaempferol is related to the activation of antioxidant genes and proteins. Moreover, we observed that glycoside derivatives can have a different effect on the antioxidant cellular systems than kaempferol.

Effect of Sanguisorba minor on scopolamine-induced memory loss in rat: involvement of oxidative stress and acetylcholinesterase.

Sanguisorba minor (S. minor) has neuroprotective and antioxidant activities. However, its potential benefits in ameliorating learning and memory functions have been explored in no studies up to now. So, in the current study, rats were treated with S. minor hydro-ethanolic extract (50, 100, and 200mg/kg, intraperitoneal (i.p.)) as well as rivastigmine (0.5mg/kg, i.p.) for 21 consecutive days. Thereafter, their behavioral performance was assessed using Morris water maze (MWM) and passive avoidance (PA) tasks. Notably, 30min before conducting the tasks, scopolamine was injected. Finally, the biochemical assessments were done using the brain tissue. The extract characterization was performed by liquid chromatography-mass spectrometry, which confirmed the presence of quercetin, myricetin, kaempferol, catechin, ellagic acid, and gallic acid derivatives. In the MWM test, the extract reduced both escape latency and the travelled distance, compared to the scopolamine group. Moreover, in the PA test, the latency to enter the dark chamber significantly increased by the extract, compared to the scopolamine group (p < 0.05-p < 0.001). Notably, the beneficial effects of S. minor on cognitive performance of the scopolamine-treated rats appeared to be similar or even better than rivastigmine in behavior performance. Similar to rivastigmine, it was observed that the extract attenuated both AChE activity and oxidative injury in the brain as evidenced by the increased antioxidant enzymes and total thiol content; however, it decreased malondialdehyde level (p < 0.05-p < 0.001). In conclusion, the results suggested the effectiveness of S. minor in preventing cognitive dysfunction induced by scopolamine. Accordingly, these protective effects might be produced by the regulation of cholinergic activity and oxidative stress. S. minor could be considered as a potential alternative therapy in cognition disorders.

Canolol and its derivatives: A novel bioactive with antioxidant and anticancer properties.

The health and safety concerns associated with synthetic antioxidants has resulted in an urgent search for natural sources of antioxidants. Such antioxidants are not only convenient but may also have important therapeutic properties. Oilseed crops, for example, are rich in phenolic compounds some of which exhibit powerful antioxidant properties that have broad applications in both the food and feed industry. Often, the concentration of these phenolic compounds is affected by many processing conditions including temperature, pressure, pH, and extracting solvents. Hence it is important to optimize processing conditions to obtain maximum levels of those antioxidants with superior antioxidant activity. Oilseeds, such as canola and mustard, are rich sources of sinapates and kaempferol derivatives. When subjected to different processing conditions, including pressurized temperature, sinapates are converted to vinyl phenol derivatives, of which the major one is canolol. This chapter will focus on the nature of canolol and its applications in food and medicine.

Synthesis, biological and computational studies of flavonoid acetamide derivatives.

This study reports the synthesis and characterization of a novel class of flavonoid acetamide derivatives (FA) of quercetin, apigenin, fisetin, kaempferol, and luteolin. Flavonoids display numerous biological properties but are limited by aqueous insolubility, enzymatic degradation, instability, and low bioavailability. FAs were synthesized, with 80–82% yields, through the sequential modification of the flavonoid hydroxyl groups into the acetamide moieties. Bioavailability, antioxidant, and ADMET are structure–activity-dependent properties that vary across different classes of flavonoids and dictate the prevalent biological applications of the flavonoids. Thus, the FAs were evaluated for their bioavailability, antioxidant, and ADMET toxicity properties versus the unmodified flavonoids (UFs). In vitro bioavailability analysis shows that the UFs have bio-availabilities in the range of 10.78–19.29% against that of the FAs in the range of 20.70–34.87%. The antioxidant capacity was measured using the 2,2-diphenyl-1-picrylhydrazyl (DPPH·) assay with recorded IC50 values of 2.19–13.03 μM for the UFs. Conversely, the FAs had high DPPH IC50 values ranging from 33.83 to 67.10 μM and corresponding to lower antioxidant activity. The FAs showed favorable ADMET properties. The modification of flavonoids into FAs significantly improves the bioavailability and the ADMET toxicity properties, albeit with decreased antioxidant activity. This work highlights the effect of the global modification of the flavonoids with the acetamide groups on the bioavailability, antioxidant, and ADMET toxicity properties which are critical determinants in the biological applications of the flavonoids.

Phenolic Compounds from Leaves of Cariniana estrellensis (Raddi) Kuntze (Lecythidaceae): A Brazilian Atlantic Forest Tree

Cariniana estrellensis (Raddi) Kuntze seedlings have been used in forest restoration programs in the Atlantic Forest biome. However, despite the economic and ecological relevance of this species, to date no general method for rapid identification of primary and secondary metabolites of C. estrellensis leaves has been reported. In this work, we explore the feasibility of using rapid analysis by nuclear magnetic resonance techniques and liquid chromatography coupled to diode array, charged aerosol, and mass detection. The main secondary metabolites identified were hydrolysable tannins, quinic acid, hydroxycinnamic acids (trans-p-coumaric acid, cis-p-coumaric acid, and trans-ferulic acid), and flavonoids (kaempferol and quercetin derivatives). These compounds are particularly useful as chemotaxonomic markers for the genus Cariniana and for the family Lecythidaceae, and may also be important for pharmacological uses and for the survival of the seedlings in reforestation programs.

Reproductive Toxicity in Male Wistar Rats Caused by Kaempferol Derivative Isolated from Lysimachia ramosa

Reproductive Toxicity in Male Wistar Rats Caused by Kaempferol Derivative Isolated from Lysimachia ramosa