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Hop (Humulus lupulus L.) essential oils and xanthohumol derived from extraction process using solvents of different polarity
Katja Bizaj, Mojca Škerget, Iztok Jože Košir, Željko Knez, 2022, original scientific article

Abstract: This study evaluates the content of essential oils (EOs) and prenylated flavonoid Xanthohumol (XN) in extracts of Slovenian hops, cultivar Aurora, obtained by using fluids of different polarity. It is a continuation of our previous work, investigating the extraction of bitter acids from hops. Extraction was conducted semi-continuously, using sub- and supercritical fluids of different polarity, i.e., carbon dioxide (CO2) and propane as non-polar and dimethyl ether (DME) as the polar solvent. The experiments explored a temperature range between 20 °C and 80 °C and pressures ranging from 50 bar to 150 bar. The content of XN in extracts was analysed using high-performance liquid chromatography and experiments demonstrated the largest concentration of XN was obtained using DME. In order to analyse the EO components in extracts, connected with a distinct odour, the steam distillation of extracts was performed and GC analysis was employed. Hop oil derived from CO2 extracts at specific conditions, had the highest relative concentration of linalool, β-caryophyllene and α-humulene, and oil derived from propane extracts had the highest content of all other five selected components (myrcene, geraniol, farnesene, α-selinene and δ-cadinene). The relative content of the investigated EO components in DME extracts was similar to that in propane extracts.
Keywords: hop extract, hop essential oils, flavonoids, carbon dioxide, propane, dimethyl ether
Published in DKUM: 17.08.2023; Views: 219; Downloads: 29
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Development of polymeric materials with rutin and polyrutin for healing of chronic leg ulcers
Tanja Pivec, 2018, doctoral dissertation

Abstract: In this work, the development of cellulose wound dressing materials with rutin (RU) and polyrutin (PR) for the healing of chronic leg ulcers is presented as a new approach of local treatment of this wound type. The flavonoid rutin is a known antioxidant substance of plant origin with wound healing promoting properties. Despite the proven beneficial properties of rutin, its potential application in wound healing is limited due to its low water solubility. This limitation can be overcome by polymerization of rutin into polyrutin. In this work an enzymatic polymerization of rutin in water without addition of organic solvents was performed to obtain a water-soluble polymer polyrutin. The chemical structure of rutin and polyrutin were investigated using UV-Vis spectroscopy, nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, size-exclusion chromatography and potentiometric titrations. Biological activity related to a desired positive influence on chronic leg ulcers was investigated through the determination of the antioxidant activity, iron-chelation ability, cell viability, determination of cell proliferation and through use of the so called “scratch assay” to measure in vitro wound healing performance. Results indicate that rutin and polyrutin have a positive influence on the healing of chronic wounds. Rutin and polyrutin water dispersions at different pH and ionic strength were further characterised by means of dynamic light scattering in order to determine the size of particles and their pH dependent ζ-potential. The knowledge gained from these measurements aided the systematic interaction studies of rutin and polyrutin dispersions with cellulose-based surfaces via model and real wound healing systems. The model cellulose surfaces were thin films prepared by dissolution of trimethylsilyl cellulose in tetrahydrofuran, spin-coating of this solution on sensors of a quartz crystal microbalance (QCM-D) and subsequent regeneration of trimethylsilyl cellulose to cellulose with acid vapors. The influence of pH, salt concentration, and rutin/polyrutin concentration on the interaction with cellulose thin films was evaluated by means of a quartz crystal microbalance with dissipation. This knowledge was transferred to the application of the coatings on real wound healing systems i.e. cellulose non-wovens. The surface morphology was further characterised on model and real wound healing systems. The antioxidant activity and release kinetics were investigated for a real wound healing system, similar to the clinically used, cellulose based wound dressing materials. The main results showed that a higher solubility of polyrutin at low ionic strength contributes to the formation of continuous layers of polyrutin on cellulose surface, while the low solubility of rutin and reduced solubility of polyrutin at higher ionic strengths contribute to deposition of particles of rutin and polyrutin on the cellulose surface. The presence of particles on the surface of non-woven cellulose fibres led to a faster initial release of rutin and polyrutin. On the contrary, a continuous layer of the well soluble polyrutin contributes to a prolonged release. Namely, adsorption of the water soluble polyrutin at pH 2 without the addition of salt results in higher masses of attached polyrutin that release slower and over longer time periods. Since wound dressing materials for chronic leg ulcers often require a lower frequency of dressing change, the latter could provide an efficient therapeutic approach to their treatment.
Keywords: Chronic wounds, Wound dressings, Cellulose, Polymerization of flavonoids, Rutin, Polyrutin
Published in DKUM: 11.06.2018; Views: 1609; Downloads: 235
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Potential of phenolic antioxidants
Iva Ružić, Mojca Škerget, Željko Knez, 2010, review article

Abstract: In vitro studies have shown a link between the consumption of food rich in (poly)phenols, especially flavonoids, and reduced risk of coronary heart diseases. Several flavonoids have been reported to prevent low density lipoprotein cholesterol oxidation in vitro. The aim of our work was to determine antioxidant and radical scavenging activity of flavonoids myricetin,quercetin, rutin, luteolin, apigenin, kaempferol, catechin, epicatechin and epigallocatechin gallate and to study the influence of chemical structure and flavonoid interactions on the ability to inhibit oxidation and scavenge free radicals. Two in vitro methods, i.e. oxidation of â-carotene in an emulsion system and DPPH (1,1-Diphenyl-2-picrylhydrazyl) radical scavenging assay, were applied. In addition, a review of in vivo studies that investigate the effectiveness of food flavonoids in reducing oxidative damage in human body was done and their results were analyzed and compared to in vitro results obtained in our laboratory. Although all tested flavonoids except apigenin showed strong antioxidant and antiradical properties in vitro, these findings can not be completely confirmed from the reviewed in vivo human studies since those results are sometimes contradictoryand inconsistent.
Keywords: phenolics, flavonoids, antioxidant activity, antiradical activity
Published in DKUM: 10.07.2015; Views: 1342; Downloads: 76
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Laccase-mediated functionalization of chitosan with phenolic acids and flavonoid quercetin
Mojca Božič, Selestina Gorgieva, Janez Štrancar, Vanja Kokol, 2012, published scientific conference contribution abstract

Keywords: functionalization, phenolic acid, flavonoids
Published in DKUM: 10.07.2015; Views: 1186; Downloads: 34
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Isolation and Characterisation of Flavonoids From Citrus Peels
Katja Makovšek, 2013, doctoral dissertation

Abstract: Citrus flavonoids are very interesting for food and pharmaceutical industry since they possess many antioxidant properties and biological activities. Mandarin peels represent an important source of hesperidin and polymethoxy flavones nobiletin and tangeretin. Pommelo peels represent an important source of naringin that can be used as precursor for naringin dihdydro-2,3-chalcone artificial sweetener. Since pommelo peels possess good antioxidant and antimicrobial properties, their extracts are very interesting products for food industry. Therefore isolation of flavonoid from mandarin and pommelo peels is an important topic of investigations. The investigation of the doctoral dissertation is divided in four parts. The first part is focused on the determination of the optimal conditions for the isolation of hesperidin and naringin from mandarin and pommelo peels by conventional extraction. The optimal conditions and the influence of extraction parameters are determined by Taguchi methodology. Very good isolation efficiency of hesperidin, 61.3 mg HES from 1 g of mandarin peels, was obtained by 70 % acetone solution and extraction conditions: 60 °C, 90 min, material to solvent ratio 1/50 g/mL and 3 stages of extraction. The highest amount of naringin, 32.8 mg NAR were isolated from 1 g of material at conditions: conventional extraction, 120 min, albedo, 60 % ethanol, material to solvent ratio 1/50 g/mL and 60 °C. The simple procedure of conventional extraction shows results comparable to more sophisticated methods such as extraction with microwave and ultrasound. Taguchi experimental design was proved to be an efficient methodology to determine the optimal conditions and the parameters that significantly influence product properties. The second part of the investigation focuses on the characterization of mandarin and pommelo peel extracts and their antioxidant properties. Radical scavenging activity against DPPH and antioxidant capacity of lipid soluble and water soluble compounds were determined for mandarin and pommelo extracts. Taguchi experimental design was applied for determination of the influence of extraction parameters on antioxidant properties. The optimal conditions to prepare extracts with high antioxidant properties were also determined. In the third part the investigation focuses on the concentration and separation of citrus flavonoids by extraction with supercritical fluids. Supercritical CO2 was applied for the separation of polymethoxylated flavones (PMF) and flavanone glycoside from mandarin peels. The optimal conditions and the parameter influence on the separation were determined by using Taguchi experimental design. The influence of supercritical fluid extraction parameters on material pre-treatment and isolation of flavonoids was studied. These investigations show that supercritical CO2 is a potential solvent for isolation and separation of PMF from mandarin peels. The fourth and last part of the investigation focuses on the concentration of flavonoids in extract solutions. Since membrane separation processes are very interesting concentration methods in industry, microfiltration, ultrafiltration, nanofiltration and revese osmosis were used for concentration of mandarin and pommelo peel extract solutions. Microfiltration and ultrafiltration could be used in the separation steps after extraction, since they did not influence the amount of dry material and valuable compounds in tested solutions. Reverse osmosis and nanofiltration were shown as useful methods for separation of solvent from extract solutions.
Keywords: Flavonoids, hesperidin, naringin, citrus peels, mandarin (Citrus reticulata), pommelo (Citrus maxima), conventional extraction, supercritical fluid extraction, membrane separation processes, Taguchi experimental design
Published in DKUM: 22.04.2013; Views: 3731; Downloads: 463
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