Separation and Purification of Rosmarinic Acid and Rutin from Glechoma hederacea L. using High-Speed Counter-Current Chromatography

Rosmarinic acid and rutin were successfully separated from Glechoma hederaceaL. using high-speed counter-current chromatography for the first time. Eleven milligrams of rosmarinic acid (chromatographic purity 97.2 %) and 10 mg of rutin (chromatographic purity 98.1 %) were obtained from 100 mg ethyl acetate extract and 100 mg n -butanol extract of Glechoma hederacea L., respectively, with the separation procedure less than 2 h. Their structures were characterized by UV, MS, and NMR. The established methods were simple, fast, and convenient, which can be applied to the preparation of reference substances of rosmarinic acid and rutin.     

Electro-oxidation of rutin in the presence of <Emphasis Type="Italic">p</Emphasis>-toluenesulfinic acid

We report the electrochemical oxidation of rutin in acetonitrile-sodium phosphate (4:1 (v/v); pH 2.0) in the presence of p-toluenesulfinic acid. Cyclic voltammetry and controlled potential electrolysis were used to study rutin electro-oxidation and to prepare the sulfone derivatives. Chromatographic methods were employed to separate the products and IR, ¹H NMR, ¹³C NMR, MS and microanalysis to their characterization. Data from cyclic voltammetry allow the identification of three rutin oxidation processes in the presence of p-toluenesulfinic acid (E _p^I = 0.56 V, E _p^II = 0.81 V and E _p^III = 1.32 V). Only the electrode process around peak I was exhaustively studied. The first oxidation step leads to the formation of the corresponding o-quinone, which participates in a Michael addition reaction with the p-toluenesulfinic acid, forming the 6′(4-methylphenylsulfonyl)rutin and 6′(4-methylphenylsulfonyl)quercetin as majority products.     

Rutin-Chitosan Nanoparticles: Fabrication,Characterization and Application in Dental Disorders

In the present investigation, we report the preparation and evaluation of antimicrobial potential of rutin-loaded chitosan nanoparticles (CRNPs). Developed CRNPs were characterized for particle size and zeta potential. Antibacterial potential of CRNPs was evaluated against dental caries pathogen, in vitro. Results revealed that chitosan enhances the anticariogenic potential of rutin. A stability study of pure rutin and CRNPs was performed in simulated saliva fluid. Results revealed that the antibacterial potential of rutin was significantly enhanced by developing it as CRNPs. The MIC and MBC against Bacillus pumilus and Enterococcus faecalis for CRNPs differed significantly compared with bare rutin or chitosan.     

Plant secondary compounds as oviposition deterrents for cabbage butterfly,Pieris rapae (Lepidoptera: Pieridae)

Oviposition byPieris rapae butterflies was deterred by spraying the plant secondary compounds coumarin and rutin on cabbage plants in greenhouse choice tests. In no-choice tests ranging from 5 min to 24 hr, acceptance of rutin-treated plants for oviposition increased with trial duration. Both coumarin and rutin deterred oviposition primarily by affecting prealighting rather than postalighting behavior, indicating that deterrence was mediated by noncontact cues.     

One Step Large-Scale Separation and Purification of Rutin from Boenninghausenia sessilicarpa by Countercurrent Chromatography

In this study, a preparative countercurrent chromatography (CCC) method for isolation and purification of the bioactive component rutin directly from the ethanol extract of Boenninghausenia sessilicarpa was successfully established by using n-butanol-ethyl acetate-water as the two-phase solvent system. The upper phase of n-butanol-ethyl acetate-water (4:1:5, v/v) was used as the stationary phase of CCC. Under the optimum conditions, 112 mg of rutin at 98.6% purity was obtained from 2.0 g of the crude extract in a single CCC separation. The peak fraction of CCC was identified by negative ESI, ¹H NMR, and ¹³C NMR.     

An effective separation and purification of rutin and scoparone from Herba Artemisiae Scopariae by solid-phase extraction cartridges packed with an ionic liquid-based silica

Five types of ionic liquid-based silica were synthesized as solid-phase extraction (SPE) sorbents for separation and purification of bioactive compounds, that is, rutin and scoparone extracted from Herba Artemisiae Scopariae. The SilprBImCl material with the highest adsorption capacity was selected as the sorbent for SPE packing. Ethyl acetate and water were found to be suitable washing and eluting solvents, respectively. SilprBImCl was then applied to multi-phase extraction, and its superiority as a sorbent over the commercial cartridge was proven with high rutin and scoparone recoveries of 90.5% and 83.9%, respectively. This highlights the potential of ionic liquid-based silica materials applied to SPE and MPE.     

Fabrication of electrospun antioxidant nanofibers by rutin‐pluronic solid dispersions for enhanced solubility

In this study, solid dispersions (SDs) and electrospinning combined methods were used to increase the bioavailability and solubility of a water insoluble drug. Pullulan (PUL) nanofibers containing rutin‐Pluronic SDs (PUL&RU@PF) were fabricated by electrospinning. Rutin was efficiently loaded with Pluronic SDs using a facile mixing method and the prepared SDs indicated that 4% w/v Pluronic concentration provided the optimal drug loading efficiency. Scanning electron microscopy (SEM) verified that the morphology of the complex nanofibers had a uniformly smooth surface with a porous structure. The amorphous state of rutin was examined by XRD and DSC. Moreover, rutin in the electrospun PUL‐rutin‐Pluronic complex structure displayed a fast release profile and equivalent antioxidant ability compared to that of raw rutin. In conclusion, PUL&RU@PF may be a promising alternative for enhanced solubility and UV stability with remaining rutin's inherent antioxidant ability. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134, 44859.     

Are Chemical Compounds Important for Soybean Resistance to <Emphasis Type="Italic">Anticarsia gemmatalis</Emphasis>?

The identification and quantification of flavonoids (rutin and genistin) present in extracts of soybean genotypes, and their effects on the biology and physiology of Anticarsia gemmatalis Hübner (Lep.: Noctuidae) were studied. Analysis of covariance and bicoordinate utilization plots were used to remove the effect of feeding time from pupal weight and consumption as well as to separate pre- and postingestive effects of treatment on A. gemmatalis growth. Genotypes PI 274454, PI 227687, and “IAC-100” extracts in general, caused higher mortality, negatively influenced initial larval and pupal weight, and elongated larval cycle. Larvae fed on the “IAC-100” extract diet ingested larger amounts of food per unit of time, but were less efficient in its conversion to biomass. Leaf extracts of PI 227687 had the largest concentration of rutin (quercitin 3-O-rhamnosylglucoside), followed by PI 274454, and “IAC-100”; PI 74454 also had the highest genistin (genistein 7-O-glucoside) content. The susceptible cultivar “BR-16” showed only a kaempferol-based flavonoid in its chemical profile, indicating that after successive crosses, secondary compounds responsible for plant defenses were eliminated. Genotypes PI 274454, PI 227687, and “IAC-100” showed accentuated resistance characteristics and were considered inadequate sources for the development of A. gemmatalis. Considering rutin and genistin concentration in these genotypes, it is suggested that flavonoids are important factors conferring resistance to A. gemmatalis.     

Interaction of nuclear polyhedrosis virus with catechols: Potential incompatibility for host-plant resistance against noctuid larvae

Two major orthodihydroxy phenolics ofLycopersicon esculentum, rutin and chlorogenic acid, have previously been identified as potential sources of host-plant resistance against the tomato fruitwormHeliothis zea. We report here the possible incompatibility of these chemically based resistance factors with viral control ofH, zea. We have found that both rutin and chlorogenic acid significantly inhibited the infectivity of nuclear polyhedrosis viruses. Chlorogenic acid, when added to tissue culture medium containing TN-368 ovarian cells, inhibited the infectivity of a multiply embedded virus (AcMNPV) by over 86%. Rutin or chlorogenic acid, when fed toH. zea, inhibited the infectivity of a singly embedded nuclear polyhedrosis virus (HzSNPV), with the greatest degree of inhibition occurring at low doses of viral inoculum. Additionally, the ingestion of these phytochemicals significantly prolonged the survival time of virally infectedH. zea larvae. These results suggest that the effectiveness of nuclear polyhedrosis viruses in controllingH. zea populations may be adversely affected by varieties ofL. esculentum with significant levels (eg. 3.5 mol/g wet weight) of rutin or chlorogenic acid.     

Stability and Bioaccessibility of β-Carotene in Oil in Water Emulsions: Impact of Antioxidant Type and Emulsifier

The objective of this study is to explore the influence of proteins type and antioxidants on the physicochemical properties, in vitro digestion, and bioaccessibility of β-carotene laden emulsions. The combination of rutin and whey protein isolate provides optimal bioaccessibility while also stabilizing the emulsion system and effectively preventing β-carotene degradation. This is due to the amphiphilic rutin adsorbed into the interface of the emulsion stabilized by whey protein, resulting in partially replacing and further improving the physical and oxidative stability of the β-carotene emulsion. Meanwhile, the rutin emulsions remain stable and carotene content is still higher (22.38–32.07%) than others even after digestion. Hence, these emulsions show great potential to be applied for delivering β-carotene based on oil-in-water emulsions. This study provides valuable information to build up stable excipient emulsions for functional foods and nutraceuticals. Practical applications: β-carotene is being exploited for a range of biomedical applications. Concentrate on the blend of antioxidants and proteins displaying various properties in β-carotene O/W emulsions that can more likely convey β-carotene to the body and better keep up with natural movement.     

Sensitive detection of rutin based on β-cyclodextrin@chemically reduced graphene/Nafion composite film

An electrochemical sensor based on chemically reduced graphene (CRG) was developed for the sensitive detection of rutin. To construct the base of the sensor, a novel composite was initially fabricated and used as the substrate material by combining CRG and β-cyclodextrin (β-CD) via a simple sonication-induced assembly. Due to the high rutin-loading capacity on the electrode surface and the upstanding electric conductivity of graphene, the electrochemical response of the fabricated sensor was greatly enhanced and displayed excellent analytical performance for rutin detection from 6.0 × 10⁻⁹ to 1.0 × 10⁻⁵ mol L⁻¹ with a low detection limit of 2.0 × 10⁻⁹ mol L⁻¹ at 3σ. Moreover, the proposed electrochemical sensor also exhibited good selectivity and acceptable reproducibility and could be used for the detection of rutin in real samples. Therefore, the present work offers a new way to broaden the analytical applications of graphene in pharmaceutical analysis.     

The composition,active components and bacteriostatic activity of propolis in dietetics

The composition and bacteriostatic activities of fifteen propolis samples from various botanic and geographic origins were determined. Twenty-six phenolic components were identified by high-performance liquid chromatography with array photodiode detector. Acacetin and apigenin were most abundant. Pinocembrin, quercetin, rutin and vanillin were present in lesser quantities. Variance analysis shows significant differences (P≤0.05) in the contents of phenols, flavonoids and active components. The minimum inhibitory concentration of propolis is about 53 times higher than that reported for tetracycline againstBacillus subtilis andStaphylococcus aureus, and about 400 times higher againstEscherichia coli.     

Effective and Preparative Separation of Bioactive Flavonoids From Gynostemma Pentaphyllum Tea Using Elution-Extrusion Counter-Current Chromatography

Elution-extrusion counter-current chromatography (EECCC) was successfully applied for screen and separation of four flavonoids from Gynostemma pentaphyllum tea, a popular herbal tea extract in China. With the hexane/ethyl acetate/methanol/water 5/6/5/6 (v/v) system, 300 mg of G. pentaphyllum tea extract were fractionated on a 180 mL-capacity preparative hydrodynamic CCC column. Satisfactory separation efficiency was achieved, producing milligram-amounts of quercetin, isorhamnetin, and cirsiliol over 90% pure in one EECCC process. Due to the hydrophilic property, the major flavonoid glycoside, rutin, was co-eluted with the solvent front as a mixture. Therefore, another carefully selected biphasic liquid system composed of ethyl acetate/n-butanol/water (4/1/5, v/v) was employed, yielding 35 mg of rutin with 97.1% purity. Structures of all separated compounds were identified by ESI-MS, ¹H NMR, and ¹³C NMR.     

Isolation of polyphenols from the extracts of olive leaves (Olea europaea L.) by adsorption on silk fibroin

General objective of the present work was to assess the isolation of polyphenols from olive leaves. The effects of extraction conditions on the total phenol content and antioxidant activity of olive leaf extract (OLE) were investigated. An extract with good antioxidant activity (7.52 mmol of Trolox equivalent antioxidant capacity (TEAC)/g olive leaf extract), and a high content of oleuropein (13.4%) and rutin (0.18%) could be obtained using 70% ethanol as extraction solvent. There was a good correlation between the antioxidant activity and the total phenol content. Furthermore, silk fibroin was used as a novel adsorbent to recover the polyphenols from the olive leaf extracts. The adsorbed amounts of rutin and oleuropein were 15 mg rutin/g silk fibroin and 96 mg oleuropein/g silk fibroin. Fraction consisting of mainly oleuropein and fraction rich in rutin, luteolin-7-glucoside, verbascoside, apigenin-7-glucoside were obtained by using silk fibroin filled column. Silk fibroin was found to be a promising adsorbent for the purification of oleuropein and rutin from olive leaf extracts.     

α‐L‐Rhamnosyl‐β‐D‐glucosidase (Rutinosidase) from Aspergillus niger: Characterization and Synthetic Potential of a Novel Diglycosidase

We report the first heterologous production of a fungal rutinosidase (6‐O‐α‐L ‐rhamnopyranosyl‐β‐D ‐glucopyranosidase) in Pichia pastoris. The recombinant rutinosidase was purified from the culture medium to apparent homogeneity and biochemically characterized. The enzyme reacts with rutin and cleaves the glycosidic linkage between the disaccharide rutinose and the aglycone. Furthermore, it exhibits high transglycosylation activity, transferring rutinose from rutin as a glycosyl donor onto various alcohols and phenols. The utility of the recombinant rutinosidase was demonstrated by its use for the synthesis of a broad spectrum of rutinosides of primary (saturated and unsaturated), secondary, acyclic and phenolic alcohols as well as for the preparation of free rutinose. Moreover, the α‐L ‐rhamnosidase‐catalyzed synthesis of a chromogenic substrate for a rutinosidase assay – para‐nitrophenyl β‐rutinoside – is described.

     

Flavonoids released by carrot (Daucus carota) seedlings stimulate hyphal development of vesicular-arbuscular mycorrhizal fungi in the presence of optimal CO2 enrichment

Carbon dioxide has been previously identified as a critical volatile factor that stimulates hyphal growth ofGigaspora margarita, a vesiculararbuscular mycorrhizal fungus, and we determined the optimal concentration at 2.0%. The beneficial effect of CO₂ on fungal development is also visible in the presence of stimulatory (quercetin, myricetin) or inhibitory (naringenin) flavonoids. Sterile root exudates from carrot seedlings stimulate the hyphal development ofG. margarita in the presence of optimal CO₂ enrichment. Three flavonols (quercetin, kaempferol, rutin or quercetin 3-rutinoside) and two flavones (apigenin, luteolin) were identified in carrot root exudates by means of HPLC retention time. Flavonols like quercetin and kaempferol are known to have stimulatory effects on hyphal growth ofG. margarita.     

Enhanced skin delivery and characterization of rutin-loaded ethosomes

We formulated rutin-loaded ethosomes and compared their vesicle size, loading efficiency, stability, and elasticity. In addition, an in vitro skin penetration experiment was performed. The results of the study indicated that ethosomes loaded with 0.005–0.03% rutin were stable during the four-week study period. Among them, those loaded with 0.03% rutin showed a vesicle size (190.20±14.57 nm) and loading efficiency (73.77%±0.01%). Therefore, the in vitro skin penetration experiment was performed using 0.03% rutin-loaded ethosome. Compared to an ethanolic solution of rutin (44.16%), rutin-loaded liposome (37.80%), and a distilled water (DW) solution of rutin (18.31%), rutin-loaded ethosome (93.31 μg; 61.30%) was superior in delivering rutin. Therefore, we suggest that ethosome loaded with 0.03% rutin enhance the skin penetration of rutin and may be used as a drug delivery system for natural cosmetic materials such as flavonoids.     

Cyclic voltammograms obtained from the optical signals: Study of the successive electro-oxidations of rutin

This paper describes a novel method of obtaining cyclic voltammograms (CVs) from optical signals. The obtained CVs correspond to the various specific species involved in the electrode process, which give more detailed information on the system under investigation than the common CV. For this purpose cyclic voltabsorptometry was used to investigate the successive oxidation processes of rutin on a graphite-wax electrode by using a long optical-path thin-layer electrochemical cell. The dynamic UV spectra of rutin showed the information on the structures of the oxidation products at different potentials. Cyclic voltabsorptiograms (CVAs) were measured in three potential ranges at the characteristic absorption wavelengths of rutin, 346, 254 and 296 nm, respectively. The CVs of three species in solution (rutin and its two products) were obtained from the derivative cyclic voltabsorptiograms (DCVAs). Based on this the redox mechanisms of rutin in different CV peaks were discussed.     

Developmental inhibition ofSpodoptera litura (Fab.) larvae by a novel caffeoylquinic acid from the wild groundnut,Arachis paraguariensis (Chod et Hassl.)

A novel compound, 1-caffeoyl-4-deoxyquinic acid (1-CdQA) has been identified along with 3-caffeoylquinic acid (3-CQA) and 5-caffeoylquinic acid (5-CQA) (syn. chlorogenic acid) in the foliage ofArachis paraguariensis, a wild species of groundnut that is highly resistant to attack by the larvae ofSpodoptera litura. When neonate larvae were fed on diets treated with 3-CQA or 1-CdQA, their development was severely inhibited compared to larvae on untreated diets, and the effects were similar in nature and magnitude to those observed for larvae feeding on diets treated with 5-CQA, rutin, and quercetin. The effects of all the compounds were dose related, and their optimal concentration was approximately 3 mM, which corresponds to the total foliar concentration of both caffeoylquinic acids and quercetin diglycosides inA. paraguariensis. After 24 h, the development of third stadium larvae feeding on diets treated with 5-CQA, rutin and 1-CdQA was promoted compared to larvae on control diets, but after 96 hr larvae feeding on treated diets had gained significantly less weight than those on the control diets. 1-CdQA, 3-CQA, and quercetin dyglycosides (previously identified in the foliage ofA. paraguariensis) are considered to be valuable components in resistance of groundnuts toS. litura and may provide useful genetic markers in future breeding for resistance to this pest.     

Isolation of colour components from flowers of Tabebuia argentea: kinetic and adsorption studies on silk yarn

The colour components from the flowers of Tabebuia argentea have been isolated and characterised as rutin and epigallocatechin gallate using spectral techniques. Adsorption kinetic and thermodynamic studies of these colour components on silk yarn have been investigated. It is noted that the adsorption is an endothermic process. The dyeing studies have been carried out at pH 4. The mordanting studies revealed that the post‐mordanting technique could only increase the dye performance marginally. The fastness properties of the dyed silk were determined. The adsorption isotherm studies showed that the Langmuir model fitted the experimental data very well with a high regression coefficient.