Flavonoid Glycosides Rutin Research Articles

Hydrolyzed Flavonoids from Cyrtosperma johnstonii with Superior Antioxidant, Antiproliferative, and Anti-Inflammatory Potential for Cancer Prevention.

Cyrtosperma johnstonii is one of the most interesting traditional medicines for cancer treatment. This study aimed to compare and combine the biological activities related to cancer prevention of the flavonoid glycosides rutin (RT) and isorhamnetin-3-o-rutinoside (IRR) and their hydrolysis products quercetin (QT) and isorhamnetin (IR) from C. johnstonii extract. ABTS and MTT assays were used to determine antioxidant activity and cytotoxicity against various cancer cells, as well as normal cells. Anti-inflammatory activities were measured by ELISA. The results showed that the antioxidant activities of the compounds decreased in the order of QT > IR > RT > IRR, while most leukemia cell lines were sensitive to QT and IR with low toxicity towards PBMCs. The reduction of IL-6 and IL-10 secretion by QT and IR was higher than that induced by RT and IRR. The combination of hydrolysis products (QT and IR) possessed a strong synergism in antioxidant, antiproliferative and anti-inflammatory effects, whereas the combination of flavonoid glycosides and their hydrolysis products revealed antagonism. These results suggest that the potential of the combination of hydrolyzed flavonoids from C. johnstonii can be considered as natural compounds for the prevention of cancer.

New molecular complex of ammonium glycyrrhizate with rutin

A new 1:1 molecular complex of triterpene glycoside ammonium glycyrrhizate (GC) with flavonoid glycoside rutin (Rut) was obtained in aqueous ethanol. The stability constant (9.7±0.2)×104 (mol/L)–1 was calculated for the complex via isomolar curves. The complexation was studied by UV- and ATR IR-Fourier spectroscopy and a method of isomolar series. The hydrogen bonds and hydrophobic interactions are formed in the molecular complex. A preliminary antioxidant activity assessment of the complex was made.

Target Discovery of Novel α-L-Rhamnosidases from Human Fecal Metagenome and Application for Biotransformation of Natural Flavonoid Glycosides.

As a green and powerful tool, biocatalysis has emerged as a perfect alternative to traditional chemistry. The bottleneck during process development is discovery of novel enzymes with desired properties and independent intellectual property. Herein, we have successfully bioprospected three novel bacterial α-L-rhamnosidases from human fecal metagenome using a combinatorial strategy by high-throughput de novo sequencing combined with in silico searching for catalytic key motifs. All three novel α-L-rhamnosidases shared low sequence identities with reported (< 35%) and putative ones (< 57%) from public database. All three novel α-L-rhamnosidases were over-expressed as soluble form in Escherichia coli with high-level production. Furthermore, all three novel α-L-rhamnosidases hydrolyzed the synthetic substrate p-nitrophenyl α-L-rhamnopyranoside and natural flavonoid glycosides rutin and naringin with some excellent properties, such as high activity in acidic pH, high activity at low or high temperature, and good tolerance for alcohols and DMSO. Our findings would provide a convenient route for target discovery of the promising biocatalysts from the metagenomes for biotransformation and biosynthesis.

QUANTITATIVE ESTIMATION OF RUTIN IN RUE (RUTA GRAVEOLENS L.) CULTIVATED IN IRAQ WITH THE EVALUATION OF ITS ANTIOXIDANT ACTIVITY

Objective: This study was designed to estimate the quantity of the flavonoid glycoside (rutin) as an important active compound in rue plant grown inIraq with the evaluation of its antioxidant activity.Methods: The cultivated rue plant at the garden of medicinal plant in the pharmacognosy and medicinal plants department was collected and dried at room temperature. Total flavonoids content was determined using aluminum chloride method, and a standard calibration curve is used for estimation of rutin glycoside. Antioxidant activity of the ethanolic extract was measured using the (1,1-diphenyl-2-picrylhydrazyl radical).Results: The results were showed that 100 g of the plant produced 7 g powdered extract, and each gram of the extract contains 133 mg rutin. The extract showed a positive antioxidant activity as compared with standard quercetin.Conclusion: Ruta graveolens plant contains the flavonoid glycoside rutin which showed antioxidant activity; therefore, further studies are required to identify other constituents in this plant.Keywords: Rue, Rutin, Flavonoids and antioxidant.

Echinophora tenuifolia L. inflorescences: phytochemistry and in vitro antioxidant and anti-inflammatory properties in LPS-stimulated RAW 264.7 macrophages

During the last decades, different natural compounds have been demonstrated to modulate inflammatory pathways. In this study, methanolic extract of Echinophora tenuifolia L. inflorescences was investigated for its chemical composition and in vitro antioxidant and anti-inflammatory properties. Phytochemical profile was investigated by means of high-performance thin layer chromatography (HPTLC) and gas chromatography–mass spectrometry analyses. Myristic acid and palmitic acid were found to be the major constituents. Six terpenes were identified: α-phellandrene, o-cymene, dihydroactinidiolide, neophytadiene, phytol and β-amyrin, and two phenolic compounds: carvacrol and ferulic acid. HPTLC analysis of the ethyl acetate fraction highlighted the presence of the flavonoid glycosides rutin and quercitrin. This sample showed the best diphenylpicrylhydrazyl scavenging capacity, with an IC50 value equal to 40.39 μg/ml, and the strongest capacity to protect linoleic acid from peroxidation, as assessed by the β-carotene bleaching test (IC50 = 16.31 μg/ml). All samples inhibited nitric oxide production in cell supernatants in a dose-dependent manner, being the two apolar fractions (n-hexane and dichloromethane) even more active than the positive control indomethacin. A relevant biological activity was observed for dichloromethane fraction (IC50 value equal to 39.97 μg/ml). Obtained results indicate that this sample could be an excellent candidate for further investigations aimed at the development of new antioxidant and anti-inflammatory drugs.

Photoinduced oxidation reactions of the pendent macrocyclic complexes: Al(III) phthalocyanine and Ni(II) annulene mechanistic considerations

The goal of the work was to expand the understanding of the photoinduced redox reactions of the Al(III) sulfonated phthalocyanine, HOAlIIItspc, and Ni(II) tertramethyldibenzotetraazaannnulene, [NiII(tmdbTAA)], as components of polymeric structures in which poly(ethyleneimino) and poly(isobutyl-alt-maleate) are the respective backbones of poly(HOAlIIItspc) and poly([NiII(tmdbTAA)]). Saccharide and flavonoid glycosides form adducts that quench the photo-generated oxidizing radicals in the case of poly(HOAlIIItspc) with rate constants≈1×104s−1, largely independent of reductant structure. The charge-separated intermediate, CS, in the case of poly([NiII(tmdbTAA)]) shows greater reactivity with the saccharides and flavonoid glycosides, particularly with the flavonoid glycoside rutin where the rate constant is 2.7×106s−1. While phthalocyanine-centered radicals in poly(HOAlIIItspc) were reduced by dAMP (adenosine-5-monophosphate) and CT-DNA, energy transfer with these reagents competed with the formation of the CS intermediate in poly([NiII(tmdbTAA)]). A study of the intensity of the upper conversion luminescence (λem<500nm), modulated by the concentration of dAMP suggests that this is attributed to the formation of adducts of poly([NiII(tmdbTAA)]) with dAMP that affect the deactivation of the electronically excited Ni(II) tetraazaannnulene pendants before the formation of the CS intermediate.

Optimization of rutin isolation from Amaranthus paniculatus leaves by high pressure extraction and fractionation techniques

A procedure based on the application of pressurized liquid extraction (PLE) was employed to recover the major Amaranthus spp. flavonoid glycoside rutin from dried ground plant leaves. A central composite design (CCD) was used to optimize rutin extraction; three factors were considered: extraction solvent (water/ethanol ratio, from 0/100 to 100/0), extraction time (from 5 to 20min) and extraction temperature (from 50 to 200°C). Optimization of the three extraction parameters revealed that water/ethanol ratio in the solvent mixture was the most-significant factor influencing rutin yield, followed by extraction temperature. The total rutin recovery varied from 6.95 to 14.03g/kg dry matter (DM) depending on the experimental conditions tested. The optimum extraction conditions for the highest rutin content were 70/30 (v/v) water/ethanol ratio, at 188°C and 20min as static extraction time. In this case rutin recovery from the leaves (14.30g/kg DM) was 4-times higher compared to that attainable using conventional ultrasound assisted extraction (3.62g/kg DM) with methanol:ethanol mixture (90:10) as solvent. Rutin recovery from defatted and non-defatted seeds of amaranth under optimum PLE conditions was 35.3 and 41.1mg/kg DM, respectively, whereas using ultrasound assisted extraction 19.7 and 34.6mg/kg DM were obtained, respectively.Extracts obtained under optimum conditions were further fractionated by using supercritical antisolvent fractionation (SAF). Extracts of amaranth leaves containing 70% water were mixed with supercritical CO2 and separated into two fractions according to the molecular mass and solubility of the contained compounds. A central composite experimental design was applied for the determination of the best fractionation conditions to maximize rutin enrichment. Maximum rutin concentration in raffinate (22.57g/kg) was recovered at 15MPa using a feed mixture flow rate of 0.3mL/min.

Evaluation of reduction kinetics of 2,2-diphenyl-1-picrylhydrazyl radical by flavonoid glycoside Rutin in mixed solvent based micellar media

The work evaluates the reduction kinetics of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical by Rutin in different mixed solvent based micellar media comprising of various cationic, anionic, zwitterionic, nonionic and their binary mixtures using spectrophotometric, fluorimetric and tensiometric methods. The analysis of kinetic measurements in micellar systems was done using models proposed by Goupy et al. and Sendra et al. applicable to initial and overall DPPH reduction kinetics respectively. The rate constants observed in the methanol–water media containing micelles (except in cationic micellar medium) were significantly faster than those without micelles suggesting the use of such media as efficient systems for evaluation of DPPH activity in comparison with the pure organic solvents having environmental concern. Rate of DPPH reduction was dependent on nature as well as concentration of amphiphile used. The results were explained on the basis of compartmentalization and mode of interaction of Rutin with micellar nanostructures.

Modes of complexation of rutin with the flavonoid reagent diphenylborinic acid 2-aminoethyl ester

The interaction of the model flavonoid glycoside rutin with the flavonoid reagent diphenylborinic acid 2-aminoethyl ester (DPBA) was investigated using a combination of HPLC–DAD–ESI–MS analysis, UV–visible spectroscopy, and semiempirical calculations. Mass spectra and spectroscopic data made it possible to describe the complexation pathway as addition of diphenylboron groups to the two available 3′,4′-o-diphenolic and the 5-hydroxy-4-keto coordinating sites of rutin. Semiempirical calculations were carried out to obtain the conformation of the most stable DPBA/rutin adducts. The results showed that a number of complexation dynamics can occur as a function of the characteristics of the medium (type and pH of the solvent) and of the amount of DPBA. This work suggests the possibility of substantially improving existing procedures for recognition of flavonoid compounds by choice of suitable experimental conditions.

Rate and forms of Mineral Nutrition CAN Influence Dry Matter Accumulation and Saponin Content of Puncture Vine (Tribulus Terrestris L.)

ABSTRACTEffect of mineral nutrition (soil or foliar supply of nutrients) on the growth, dry matter and saponin content of the shoot biomass of Bulgarian variety puncture vine (Tribulus terrestris L.) grown on soil as pot experiment in green house were studied. Soil fertilization rate of 100mgN/kg or 90P/kg of dry soil, oppositely to the results obtained from the foliar fed plants (0.3 % solution of liquid fertilizer AgroleafR (Scotts Co, USA) with formulation N12P52K5, increased shoot total N and P without significant change of dry matter. Changes of total reducing sugars, amino acids, phenolics and flavonoids and activity of leaf photosynthetic apparatus (chlorophyll (Chl) a, b and carotenoids content and parameters of chlorophyll a prompt fluorescence) were found to relate to the variation of individual saponin content analysed by HPLC technique. Soil fertilized plants in contrast to the foliar fed plants showed more protodioscin, prototribestan and dioscin than control but contained less of flavonoid glycoside rutin.

Mitogenic effect of Carthamus lanatus extracts, fractions and constituents

Extracts, fractions and constituents of Carthamus lanatus were tested for their mitogenic effect on bone marrow cells in mice. Most of the studied samples inhibited cell proliferation and only the flavonoid glycoside rutin caused increasing of mitotic activity.

A beta-rutinosidase from Penicillium rugulosum IFO 7242 that is a peculiar flavonoid glycosidase.

A beta-rutinosidase, which was specific for releasing the disaccharide rutinose from the flavonoid glycoside rutin, was purified from Penicillium rugulosum IFO 7242. This enzyme had the molecular weight of 245,000, a very low optimum pH of 2.2, and the remarkable specificity that the glycosidase did not hydrolyze any other substrates like 4-nitrophenyl beta-glucoside and cellobiose, but only rutin and isoquercitrin.

Flavonoid Deactivation of Ferrylmyoglobin in Relation to Ease of Oxidation as Determined by Cyclic Voltammetry

Fourteen flavonoid aglycones, and the flavonoid glyco-side rutin, with redox potentials ranging from 0.20 (myricetin) to 0.83 V (chrysin) vs. NHE, as determined by cyclic voltammetry at 23°C in aqueous 50 mM phosphate, ionic strength 0.16 (NaCI) with pH = 7.4 and compared with redox potentials determined for four cinnamic acid derivatives, were all found to reduce ferrylmyoglobin, MbFe(IV)=O, to metmyoglo-bin, MbFe(III). Reaction stoichiometry depends strongly on the number of hydroxyl groups in the flavonoid B-ring. All compounds with 3′,4′-dihydroxy substitution reduce 2 equivalents of MbFe(IV)=O, whereas naringenin, hesperitin and kaempferol, with one hydroxyl group in the B-ring, reduce with a one-to-one stoichiometry. As studied spectrophotometrically under pseudo-first-order conditions with flavonoids in excess, rutin and apigenin react with MbFe(IV)=O with very similar and moderately high activation enthalpies of ΔH‡298 = 69 ± 1kJ mol−1 and ΔH‡298 = 65 ± 3kJ mol-1, respectively, and with positive activation entropies of ΔH‡298 = 23 ± 4Jmol-1 K−1 and ΔS‡298 = 13 ± 9Jmol−1K-1, respectively, in agreement with outer-sphere electron transfer as rate determining. For the fifteen plant polyphenols only qualitative relations exist between redox potential and rate constants rather than a linear free energy relationship (r2 = 0.503), and especially the flavone apigenin was found more efficient as reducing agent. For the flava-nones, a linear relation (r2 = 0.971) indicate that, in the absence of a 2,3 double bond, removal of the 4–carbonyl group or addition of a 3–hydroxy group only has minor effect on reactivity. The flavonols are the most efficient reducing agents, effectively reducing MbFe(IV)=O to MbFe(III) and establishing a steady state distribution between the flavonol and MbFe(III) and oxymyoglobin, MbFe(II)O2. Oxidised flavonols reduces MbFe(III) to MbFe(II)02 very efficiently and much faster than the parent flavonol.

High-performance liquid chromatographic study of casimiroa edulis: I. Determination of imidazole derivatives and rutin in aqueous and organic extracts

The imidazolic derivatives present in the seeds and leaves of Casimiroa edulis (Rutaceae), a antihypertensive popular remedy, were successfully separated and estimated by high-performance liquid chromatography. Dimethylhistamine, methylhistamine and casimiroedine were separated by paired ion chromatography while histamine was derivatized and determined in the reversed-phase mode using fluorimetric detection. In addition, the flavonoid glycoside rutin, an important constituent of the leaves, was determined by reversed-phase high-performance liquid chromatography.