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1
Schmeisser, Michael. "Anthocyanins in selected Proteaceae." Thesis, Stellenbosch : Stellenbosch University, 2002. http://hdl.handle.net/10019.1/52685.
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Thesis (MScAgric)--University of Stellenbosch, 2002.ENGLISH ABSTRACT: Trials were conducted to follow colour development during the growth season of the commercial Leucadendron cultivar 'Siivan' Red', as well as the Protea cultivars 'Ivy', 'Carnival' and 'Sylvia'. HPLC analysis showed that pigments responsible for red colour in Leucadendron and Protea cultivars are anthocyanins. Initial extraction of anthocyan ins from freeze-dried and finely ground Leucadendron leaves, using 5% formic acid in methanol, resulted in the precipitation of gel-like compounds, making the extracts impossible to filter for HPLC. Trials were conducted to determine the optimum extraction solvent and extraction time for anthocyanin quantification in Leucadendron, using 'Safari Sunset' (Leucadendron sa/ignurn x L. /aureo/urn) as reference material. Acetone, 80% acetone, 5% formic acid in water and 5% formic acid in methanol were added to freeze dried leaf samples and allowed to extract for one hour. Extracts were analysed by reverse-phase HPLC. Extractions with methanol and water yielded extracts with a high content of pectin-like compounds, making them difficult to purify for HPLC. 80% acetone proved to be the most efficient extraction solvent, yielding the highest anthocyanin concentration, and showing the least amount of insoluble compounds. Optimal extraction time was determined for 80% acetone by testing 1, 6 and 24-hour extractions respectively. Although 6 hour extraction showed a slightly higher yield, a 1-hour extraction should suffice for quantification of anthocyanin changes over time, as trends will clearly be evident. 'Siivan Red' shoots meeting export quality can generally be harvested from mid February to mid April (late summer to autumn). The harvesting period ends as the colour of the distal leaves forming the flower head change from red to green. Anthocyanin, chlorophyll and carotenoid fluctuations were investigated in 'Siivan Red' during the 2000 growth season. The observed red colour loss is the result of the net degradation of anthocyanins and appeared to be correlated to the phenological development of the shoot. Although a positive correlation was noted between anthocyanin content and average daily temperature and mean daily sunlight hours, it appears unlikely that they are the causal factors for the observed colour change. Anthocyanin degradation started during conditions of long exposure to high light intensities and continued during a period of low temperature (autumn), both which are known to favour anthocyanin synthesis rather than its degradation. Therefore it appears that colour development in 'Silvan Red' is developmentally regulated. The Leucadendron cultivar 'Safari Sunset' with the same parentage as 'Siivan Red', is noted for its more intense red-purple colouration, which it does not lose during its development. The more intense colouration of 'Safari Sunset' has been ascribed to the higher total anthocyanin concentration, which was almost double that encountered in 'Siivan Red'. 'Safari Sunset' was shown to contain the same major types of anthocyanins, and hence the purple colouration (not seen in 'Siivan Red') can not be explained in terms of different types of anthocyanins being present. However, the ratio between the two major anthocyanins present in both 'Safari Sunset' and 'Siivan Red' were significantly different in that 'Safari Sunset' showed a considerably higher concentration of peak 1, which is most likely responsible for the observed purple colouration. High anthocyanin concentrations have been noted to buffer against visual changes in colour, which is the most probable reason that a colour loss is not observed in 'Safari Sunset'. Colour development of the innermost involucral bracts of three Protea cultivars was followed from an initially selected inflorescence size to commercial harvest (when flowers have opened slightly). 'Ivy', 'Carnival' and 'Sylvia' show a light pink, dark pink and red colouration respectively, which has been ascribed to differences in total anthocyanin concentration. Colour development in 'Carnival' showed a quadratic trend with time, with the highest rate of anthocyanin synthesis occurring a week prior to harvest. Colour development in 'Ivy' and 'Sylvia' were shown to be linear with time. As inflorescences are closed during their development and anthocyanin synthesis in the innermost involucral bracts occurred in darkness, light does not appear to have a major influence on colour development. Temperature did not appear to have a significant effect on flower colour, as flowers developing later in the season, when ambient temperatures were lower, showed no significant differences in anthocyanin concentration to those harvested earlier. Hence, it appears that colour development in all three cultivars is developmentally regulated.
AFRIKAANSE OPSOMMING: Hierdie studie is onderneem om kleurontwikkeling van die Leucadendron kultivar 'Silvan Red' en die Protea kultivars 'Ivy', 'Carnival' en 'Sylvia' te ondersoek. Die rooi kleur van distale 'Siivan Red' blare en Protea omwindselblare is te wyte aan antosianiene. Eerstens is gepoog om die ektraksie van antosianiene vir kwantifisering deur hoë druk vloeistof chromatografie (HPLC) te verfyn. Aanvanklik is 5% mieresuur in metanol gebruik om antosianien vanuit gefriesdroogde en fyngemaalde Leucadendron blare te ekstraheer. 'n Gelagtige neerslag het dit egter onmoontlik gemaak om die ekstrak te filtreer. Vervolgens is eksperimente uitgevoer om die geskiktheid van asetoon, 80% asetoon, 5% mieresuur in water en 5% mieresuur in metanol as alternatiewe vir 5% mieresuur in metanol te bepaal. Antosianiene is deur middel van HPLC gekwantifiseer na 'n uurlange ekstraksie vanuit 'Safari Sunset' (Leucadendron sa/ignurn x L. /aureo/urn) blaarmonsters. 'n Onoplosbare neerslag van onsuiwerhede na ekstraksie met metanol en water het filtrasie bemoeilik. 80% asetoon was die doeltreffendste ekstraheermiddel deurdat dit beide die hoogste opbrengs van antosianiene en die minste onsuiwerhede gelewer het. Vervolgens is die optimale duur van antosianienekstraksie met 80% asetoon bepaal deur vir een, ses en 24 uur te ekstraheer. Resultate het getoon dat, alhoewel ses uur ekstraksie 'n effense hoër antosianienkonsentrasie lewer, 'n uur voldoende behoort te wees vir kwantifisering van antosianien. Uitvoergehalte 'Siivan Red' lote word gewoonlik vanaf middel Februarie tot middel April (Iaat somer tot herfs) geoes. Die oestyd eindig met 'n verandering in die kleur van distale blare van rooi na groen wat die bemarkbaarheid van lote verlaag. Ten einde hierdie kleurverandering te kwantifiseer is veranderinge in die konsentrasies van antosianien, chlorofiel en karotenoide in distale 'Siivan Red' blare gedurende die 2000 groeiseisoen gemeet en in verband gebring met omgewingstoestande en ontwikkelingstadiums. Rooi kleurverlies van distale 'Silvan Red' blare hou klaarblyklik verband met 'n geleidelike afname in hul antosianienkonsentrasies vanweë netto degradasie. Veranderinge in die kleur en antosianienkonsentrasie van blare het saamgeval met spesifieke ontwikkelingsperiodes. Kleurveranderinge in 'Siivan Red' kon nie met omgewingstoestande verbind word nie. Kleuronwikkeling word klaarblyklik intern gereguleer om saam te val met spesifieke ontwikkelingstadia. Die Leucadendron kultivars 'Safari Sunset' en 'Siivan Red' het dieselfde ouers. Eersgenoemde kultivar het egter In intenser rooi-pers kleur wat ook stabiel blyoor die hele groeiseisoen. Die intenser kleur kan toegeskryf word aan die bykans twee keer hoër antosianienkonsentrasies wat 'Safari Sunset' blare oor die groeisoen handhaaf. Hierdie hoër antosianienkonsentrasie is moontlik ook die rede vir die oëskynlik groter kleurstabiliteit van 'Safari Sunset' aangesien hoë pigmentvlakke kleur buffer teen veranderinge in pigmentkonsentrasie. 'Safari Sunset' se pers skynsel is moontlik te wyte aan die relatief groter bydrae van piek 1 op die chromatogram tot die totale antosianienkonsentrasie. Andersins het die twee kultivars 'n soortgelyke antosianienprofiel. Ten einde die regulering van kleurontwikkeling in Protea te ondersoek, is antosianienkonsentrasies in die binneste bloeiwyse-omwindelsblare van die Protea kultivars 'Ivy', 'Carnival' en 'Sylvia' gemeet vanaf 'n pre-geselekteerde blomgrootte tot en met kommersiële oestyd wanneer die blomme begin oopgaan. Die drie kultivars wisselonderskeidelik in kleur van lig pienk en donker pienk tot rooi. Hierdie kleurverskille was te wyte aan verskille in antosianienkonsentrasie. Antosianienkonsentrasies in 'Ivy' en 'Sylvia' het lineêr toegeneem oor tyd, terwyl in die geval van 'Carnival', maksimum antosianienvlakke reeds 'n week voor oes bereik is. Blomme wat by laer temperature later in die seisoen of vroeër by hoër temperature ontwikkel het, het nie betekenisvol verskil in antosianienkonsentrasie nie. Gevolglik is lig en temperatuur klaarblyklik van mindere belang vir Protea kleurontwikkeling. Soos met Leucadendron die geval was, word kleurontwikkeling in Protea dus ook intern gereguleer.
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Matsumoto, Hitoshi. "Physiological Effects of Blackcurrant Anthocyanins." Kyoto University, 2003. http://hdl.handle.net/2433/149024.
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Sindi, Hebah Abbas. "Bioactivity of anthocyanins from Hibiscus sabdariffa." Thesis, University of Leeds, 2013. http://etheses.whiterose.ac.uk/5910/.
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A systematic study on extraction of Hibiscus sabdariffa was carried out for the first time using different solvents (water, methanol, ethyl acetate and hexane) in the presence and absence of formic acid, using different extraction times and temperatures. The extracts were analysed for total phenol content, antioxidant capacity using DPPH, FRAP and TEAC assays, and total monomeric anthocyanin content. In addition, specific anthocyanins were determined using HPLC and LC-MS. The results showed the highest antioxidant capacities were obtained by extracting using water, with or without formic acid, for 10 min at 100 °C. These extracts provided the highest concentrations of cyanidin 3-sambubioside and delphinidin 3-sambubioside. Commercially available herbal teas containing H. sabdariffa were analysed. The study found that contents of total phenols, anthocyanins and antioxidant capacity were higher when using the optimal extraction procedure, suggesting that putative health benefits could be increased by altering processing methods. The partition coefficients (log p) of anthocyanins found in H. sabdariffa, were measured showed that aglycone and glucoside forms of hibiscus anthocyanins behave differently when in the presence of cell wall material. Such behaviour could, in vivo, affect the absorption and bioactivity of these anthocyanins, and therefore, their efficacy. A human crossover study investigated the effect of daily consumption for 8 weeks of a H. sabdariffa juice for 8 weeks on the blood pressure of healthy subjects (n= 29). Cranberry juice was used as the control. A significant reduction was found in systolic blood pressure (but not diastolic) compared to the baseline. No significant effect on blood pressure was seen with cranberry juice. The study suggests that regular consumption of extracts of H. sabdariffa may reduce the risk of cardiovascular disease, on the other hand people with low blood pressure should consumed it very carefully due to hypotensive effect of the extract.
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Neill, Samuel Oliver. "The functional role of anthocyanins in leaves." Thesis, University of Auckland, 2002. http://hdl.handle.net/2292/497.
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The anthocyanins, a relatively small group of pigments in the diverse flavonoid family, are largely responsible for the red-blue colouration in a large number plant species worldwide. Their occurrence in fruits and flowers seems to offer clear benefits in attracting pollinators and aiding seed dispersal, however their presence in the vacuoles of leaves remains obscure. The accumulation of anthocyanin pigments in leaves can be induced by a host of disparate environmental and anthropogenic stressors, such as UV-exposure, wounding, pathogen infection, high light, chilling, pollution, osmotic stress, and nutrient deficiency. Anthocyanins are in some species expressed throughout leaf development; in others the pigments are found exclusively in the young, rapidly expanding leaves, or at later stages of leaf senescence. Many researchers have explored the possible functional role(s) of anthocyanins within leaves, although none of the hypotheses provides a unified explanation for the diverse range of environmental triggers, or for the variability in the pigment’s location and expression at particular stages of development. Differences in the cellular location of cyanic pigments had little effect on the optical properties of leaves from several native New Zealand species. Instead, the absorptance of green-yellow light was strongly proportional to the concentration of anthocyanin. Red leaves absorbed up to 17 % more PAR (400-700 nm) than green leaves of same species. The reflectance of red light was independent of leaf anthocyanin content. In Lactuca sativa, the absorption of light by anthocyanic cell vacuoles in the upper epidermis led to a reduction in the light incident on subjacent chlorenchyma. Under high irradiances, the dissipation of excess energy through non-photochemical processes (qNP) was lower in the red regions of the leaves than in the green regions. Red L. sativa, maintained higher photochemical efficiencies (0PSII), and had greater rates of photochemical quenching (qP) than the green tissues. Moreover, the cyanic areas were photoinhibited significantly less (7 %), as measured by levels of maximum PSII efficiency (Fv/Fm), than green areas during a high light treatment of 1300 mmol m-2 s-1. Chloroplast suspensions from shade adapted L. sativa generated less superoxide (O2 -) through the Mehler reaction and had reduced rates of chlorophyll bleaching, when irradiated with 300 mmol m-2 s-1 of red light rather than white light. These data demonstrated the impact of the light-filtering effects of anthocyanins on the photophysiology of the leaves. Complementary to their light-shielding functions, anthocyanins also demonstrated potent antioxidant capabilities at pH values typical of both the cytoplasm and the vacuole. The addition of cyanidin-3-malonylglucoside, which was colourless at the cytoplasmic pH, to a chloroplast suspension receiving high irradiance resulted in the significant scavenging of O2 -. The red, flavylium form of anthocyanin was also oxidised by O2 -. After 15 minutes, this oxidation equated to a 40 % reduction in antioxidant potential of the anthocyanin, as measured by cyclic voltammetry. The data suggested that anthocyanins could provide widespread cellular protection to cellular membranes, organelles, and DNA. Analysis of the overall antioxidant defence in red and green leaves of Elatostema rugosum, a shade-adapted herb native to New Zealand, and Quintinia serrata, a native tree found on exposed ridges, provided evidence for a photoprotective role of anthocyanins. Red leaves of E. rugosum were on average five-times more effective at scavenging DPPH radicals than were green leaves. The anthocyanins constituted the most active phenolic component, providing a greater relative contribution to the antioxidant pool than the flavones, flavonols, and hydroxycinnamic acids. In contrast, red and green leaves of Q. serrata exhibited comparable ranges in antioxidant activities. The data suggest that for some species, anthocyanins can supplement the pool of low molecular weight antioxidants but are not a prerequisite for protection from oxidative stress. It is likely that the localised accumulation of anthocyanins in the leaves of Q. serrata serves to shield photosynthetic tissues that are the more susceptible to photodamage. In conclusion, the accumulation of anthocyanins represents a multifunctional mechanism to; i) directly reduce ROS through scavenging and possibly metal chelation, acting in conjunction with other antioxidants, and ii) to shield photosynthetic processes experiencing excessive irradiances, thereby reducing the extent of photooxidation, photoinhibition, and wasteful dissipatory systems. Such protection may be vital for leaves experiencing stressful environments.
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Cahyana, Yana. "Factors affecting the biovailability of dietary anthocyanins." Thesis, University of Reading, 2014. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.630468.
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Beneficial health effects of anthocyanin-rich fruits and vegetables have been well documented. Subsequently extensive research on anthocyanins has been carried out to better understand the behaviour of anthocyanins. Bioavailability is one aspect which has been frequently investigated but the studies have not studied factors affecting anthocyanin bioavailability. Knowledge of the mechanism of anthocyanin absorption is also lacking. A bioavailability study was conducted with human volunteers whose urine was analysed following consumption of strawberry and red grape juice. Since anthocyanins are absorbed and present in biological fluids, their interactions with human serum albumin (HSA) were further examined. The study was then completed with an in-vitro test using Caco-2 cells to assess the uptake of anthocyanins by intestinal cells, and factors affecting uptake and the absorption mechanism through the apical cellular membrane.
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Katsuno, Yoshitaka. "Effect of extrusion cooking on strawberry anthocyanins /." free to MU campus, to others for purchase, 2004. http://wwwlib.umi.com/cr/mo/fullcit?p1421146.
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Buchweitz, Maria [Verfasser]. "Stabilisation of anthocyanins and anthocyanin-metal chelates with hydrocolloids for their application as red and blue food colourants / Maria Buchweitz." Aachen : Shaker, 2013. http://d-nb.info/1050343255/34.
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Jing, Pu. "Purple corn anthocyanins chemical structure, chemoprotective activity and structure/function relationships /." Columbus, Ohio : Ohio State University, 2006. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=osu1155738398.
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Dee, Stacy. "Identification and stability of anthocyanins in Plantago lanceolata." Greensboro, N.C. : University of North Carolina at Greensboro, 2007. http://libres.uncg.edu/edocs/etd/1419/umi-uncg-1419.pdf.
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Thesis (M.S.)--University of North Carolina at Greensboro, 2007.Title from PDF t.p. (viewed Oct. 22, 2007). Directed by Nadja B. Cech; submitted to the Dept. of Chemistry and Biochemistry. Includes bibliographical references (p. 76-79).
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Willemse, Chandre Monique. "Comprehensive two-dimensional liquid chromatographic analysis of anthocyanins." Thesis, Stellenbosch : Stellenbosch University, 2015. http://hdl.handle.net/10019.1/96675.
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Thesis (PhD)--Stellenbosch University, 2015.ENGLISH ABSTRACT: Anthocyanins are naturally occurring pigments responsible for the colour of many natural products, including grapes and wine. These pigments are important to the food industry and have been recognised for their nutritional value since they play an important role in the reduced risk of various chronic diseases in humans. Anthocyanins also play an important role in the aesthetic perception and quality of red wine. However, due to the large structural diversity of grape-derived anthocyanins and the many derivatives formed from these during wine ageing, the accurate analysis of wine pigments is extremely challenging. Reversed-phase liquid chromatography (RP-LC) is mostly used for anthocyanin analysis, although the technique often provides insufficient resolving power for complex mixtures of anthocyanins. In addition, the lack of commercially available standards and identical mass spectral characteristics hampers identification of these compounds. The coupling of multiple orthogonal separation systems in comprehensive 2-dimensional liquid chromatography (LC×LC) offers a more powerful approach for the separation of complex mixtures. The current work therefore focussed on exploring the potential of LC×LC for the improved analysis of anthocyanins and derived pigments in natural products and wine. The first part of this work focussed on developing a hydrophilic interaction chromatography (HILIC) method as an alternative to RP-LC for the anthocyanin analysis. Following extensive optimisation, the method proved suitable for the analysis of a diverse range of anthocyanins in natural products. Significantly, it also showed alternative selectivity compared to RP-LC. The optimised HILIC method was then used in combination with RP-LC to develop an off-line LC×LC approach for anthocyanins. For this purpose, half-minute fractions of the HILIC effluent were collected and reinjected onto a RP-LC column. The off-line HILIC×RP-LC method demonstrated exceptionally high resolving power, as measured in terms of the practical peak capacity, with many compounds separated in two dimensions that co-eluted in 1-dimensional HPLC. Interestingly, group-type separation was also observed based on the degree and/or nature of glycosylation and acylation of anthocyanins. In the final part of the work, a systematic approach was used for the development and optimisation of and on-line HILIC×RP-LC method by using a 10-port switching valve to automatically transfer fractions between the two columns. This method was then coupled to high resolution mass spectrometry (MS) to allow the detailed investigation of anthocyanins and derived products in wine. Ninety four pigments were identified in one- and six-year old Pinotage wines based on HILIC×RPLC separation in combination with accurate mass MS data and fragmentation information. Significant differences in especially the content of derived pigments were observed between the wines. In summary, the methods developed in this work provide the means to improve anthocyanin analysis, and therefore also show promise for the detailed investigation of these important compounds and their alteration in natural products and their derived commodities.
AFRIKAANSE OPSOMMING: Antosianiene is natuurlike pigmente wat verantwoordelik is vir die kleur van baie natuurlike produkte, insluitende dié van druiwe en wyn. Hierdie pigmente is belangrik vir die voedsel industrie en word gereken vir hul voedingswaarde aangesien hulle 'n belangrike rol speel in die verlaagde risiko van verskeie chroniese siektes onder die mens. Antosianiene speel ook 'n belangrike rol in die estetiese persepsie en kwaliteit van rooiwyn. Desnieteenstaande, as gevolg van die groot strukturele diversiteit van druifgeproduseerde antosianiene en die vele chemiese afgeleides wat uit hulle gevorm kan word tydens wyn bereiding en veroudering, is die akkurate analise van natuurlike wyn-pigmente uiters uitdagend. Omgekeerde-fase vloeistofchromatografie (RP-LC) word meestal gebruik vir die analise van antosianiene. Dié tegniek bied egter dikwels onvoldoende skeidingsvermoë vir komplekse mengsels van antosianiene en verwante molekules. Verder belemmer die onbeskikbaarheid van kommersiële standaarde en identiese massa spektrale eienskappe die identifikasie van hierdie verbindings. Die kombinasie van verskillende ortogonale skeidings meganismes in omvattende 2- dimensionele vloeistofchromatografie (LC×LC) bied egter 'n baie kragtiger benadering vir die skeiding van komplekse mengsels. Die huidige werk fokus dus op die ontginning van die potensiaal van LC×LC vir die verbeterde ontleding van antosianiene en verwante afgeleide pigmente in natuurlike produkte en wyn. Die eerste deel van hierdie werk het gefokus op die ontwikkeling van 'n hidrofiliese interaksie chromatografiese (HILIC) metode as ʼn alternatief vir RP-LC analise van antosianiene. Na uitgebreide optimisering, is gevind dat die metode geskik is vir die ontleding van 'n verskeidenheid van antosianiene in natuurlike produkte. Van groot belang is dat dit ook alternatiewe selektiwiteit in vergelyking met RP-LC demonstreer. Hierdie geoptimiseerde HILIC metode word dan voorts gebruik in kombinasie met RP-LC vir die ontwikkeling van ʼn af-lyn LC×LC benadering vir die analise van antosianiene. Hiervoor is half-minuut fraksies van die HILIC uitvloei opgevang en her-ingespuit op 'n RP-LC kolom. Dié af-lyn HILIC×RP-LC metode toon buitengewoon hoë skeidingsvermoë, gemeet in terme van die bereikbare praktiese piek kapasiteit, met baie verbindings wat geskei is in die twee dimensies wat saam elueer in 1-dimensionele HPLC. Interessant genoeg is groep-tipe skeiding ook waargeneem gebaseer op die graad en / of aard van glukosilasie en asilering van die antosianiene. In die laaste deel van die werk, is 'n sistematiese benadering gevolg vir die ontwikkeling en optimisering van ʼn aan-lyn HILIC×RP-LC deur gebruik te maak van 'n 10-poort oorskakelingsklep wat fraksies outomaties oordra tussen die twee kolomme. Die bogenoemde metode is ook verder gekoppel aan hoë resolusie massaspektrometrie (HR-MS) om ʼn gedetailleerde ondersoek van antosianiene en hulle afgeleide verbindings in wyn moontlik te maak. Vier en negentig pigmente is in een- en ses jaar oue Pinotage wyne geïdentifiseer gebaseer op HILIC×RP-LC skeiding in kombinasie met akkurate massa MS data en fragmentasie inligting. Beduidende verskille in veral die inhoud van antosianien-afgeleide pigmente is tussen die wyne waargeneem. Ter samevatting, die metodes ontwikkel in hierdie werk baan die weg om antosianien ontleding te verbeter en stel gevolglik die moontlikheid van selfs meer gedetailleerde studies van hierdie belangrike verbindings in natuurlike produkte in die vooruitsig.
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Simmons, Steven Tyler. "Commercial Applicability of an Innovative Anthocyanin Purification Technique, Utilizing Mixed-Mode Solid-Phase Extraction." The Ohio State University, 2012. http://rave.ohiolink.edu/etdc/view?acc_num=osu1332267706.
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Small, Pamela Beth. "Development of a Soy-blueberry Burger and the Changes in Anthocyanins and Phenolics During Storage and Broiling." Fogler Library, University of Maine, 2007. http://www.library.umaine.edu/theses/pdf/SmallPB2007.pdf.
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Compton, Benjamin Jason, and n/a. "Synthesis towards a carbon labelled Anthocyanin." University of Otago. Department of Chemistry, 2008. http://adt.otago.ac.nz./public/adt-NZDU20081208.141123.
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The total synthesis of cyanindin-3-glucoside (C3G) appropriate for ��C enrichment at C-1` and C-6` has been achieved for metabolic studies.
Construction of the phenolic ring-B was achieved by a Diels-Alder reaction employing a novel diene, (2R,3R)-2,3-dimethyoxy-2,3-dimethyl-5,6-dimethylene-1,4-dioxane, which incorporates a butane diacetal protecting motif. Reaction with a (labelled) dienophile affords the protected catechol.
Formation of the flavone skeleton was achieved by condensation of the benzamide (ring-B) with an acetophenone (ring-A).
Esterification of the flavone skeleton in ring-A was found to be essential for oxidation at C-3 with dimethyldioxirane affording the flavonol. Glycosylation using a glucosyl bromide gave the β-adduct exclusively which was reduced to the target compound, C3G.
The overall synthetic design permits the synthesis of the labelled anthocyanin in nine steps (23%) from the dienophile.
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Lewis, Christine Elaine. "Anthocyanins and related compounds in potatoes (Solanum tuberosum L.)." Thesis, University of Canterbury. Plant and Microbial Sciences, 1996. http://hdl.handle.net/10092/6549.
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Coloured potatoes may have economic value as natural food colourants and as food products such as novelty potato crisps and coloured potato salads. This thesis investigated the biochemistry and physiology of anthocyanins and related compounds in Solanum tuberosum L., and the relationship to tuber colour. These factors were discussed in terms of consumer requirements.
Phenolic acids, flavonoids and anthocyanins were surveyed and quantified in the tubers (skin and flesh), flowers and leaves of twenty nine cultivars of S. tuberosum and eight other Solanum species (S. acaule, S. berthaultii, S. gourlayi, S. oplocense, S. sanctaerosae, S. spars/pilum, S. speggazzinii, S. stenotomum). The main anthocyanin found in red tubers was pelargonidin-3-(p-coumaroyl-rutinoside)-5-glucoside (200-2000μg/gFW) with lower amounts of peonidin-3-(p-coumaroyl-rutinoside)-5-glucoside (20-400μg/gFW), Light to medium pmple coloured tubers contained mostly petunidin-3- (p-coumaroyl-rutinoside)-5-glucoside (400-2000μg/gFW) pills low concentrations of malvidin-3-(p-coumaroyl- rutinoside)-5-glucoside (20-200μg/gFW), whilst dark purple black coloured tubers contained a similar concentration of petunidin-3-(p-coumaroyl-rutinoside)-5-glucoside (1000-2000μg/gFW) to the light to medium purple tubers, but with high concentrations of malvidin-3-(p-coumaroyl-rutinoside)-5-glucoside (2000- 5000μg/gFW). Red and purple tubers also contained a number of minor anthocyanins, with the same aglycones as above, but mostly as the 3-rutinosides. Tubers contained high concentrations of phenolic acids (2000-5000μg/gFW), with chlorogenic acid making up 60-90%. Apart from the anthocyanins, there were low concentrations of other flavonoids (200-300μg/gFW). The major anthocyanin present in the flowers was petunidin-3-(p-coumaroyl-rutinoside)-5-glucoside. Flowers and leaves contained higher concentrations of flavonoids (1000-3000μg/gFW), the major flavonoids being quercetinglycosides. The flavonoid patterns of flowers and leaves fell into two different categories with some cultivars containing high concentrations of quercetin-glycosides, whilst others contained low concentrations.
Tubers of the other available Solanum species did not show the range of colours shown by S. tuberosum cultivars, and were mostly white or light purple, with petunidin-3-(pcoumaroyl-rutinoside)-5-glucoside being the major anthocyanin (when present) in the skin of tubers of the other Solanum species. The major anthocyanin in flowers of the other Solanum species was petunidin-3-(p-coumaroyl-rutinoside)-5-glucoside, with levels similar to those found in S. tuberosum flowers. Low levels of anthocyanin were found in the leaves of the other Solanum species whereas in S. tuberosum no anthocyanins were found in the leaves. There was considerable variation among plants and species in both phenolic acid and flavonoid concentrations, but generally a similar pattern was found in the other Solanum species as in S. tuberosum cultivars, except that S. tuberosum flowers contained lower concentrations of total phenolic acids and flavonoids on average, and tubers and leaves contained high concentrations of flavonoids.
The expression of different pathways appeared to depend on the species, plant tissue and environmental factors. Diseased tubers contained higher concentrations of phenolic acids, flavanones and flavonols than healthy tubers, and some flavonols which were not present in healthy tubers were produced in diseased tubers. There was differential expression of anthocyanins, flavonoids and phenolic acids in the different parts of the plant (tubers, flowers and leaves). These compounds also responded differently to light, with anthocyanins showing a large increase, flavonoids a smaller increase, and phenolic acids no change in concentration, in minitubers after indirect exposure to light.
The biosynthesis of anthocyanins in tubers was investigated throughout tuber development and during storage. Newly initiated tubers contained no anthocyanin, and subsequent production of colour occurred firstly at the stem end of the developing tuber, and then proceeded to the bud end. Anthocyanin concentrations increased throughout the development of the tuber, reaching a maximum at a tuber size which was dependent on the cultivar (about 150-200g for Desiree). Concentrations were higher at the stem end of the tuber than the bud end for most of tuber development although, as the maximum anthocyanin concentration was reached, the distribution of anthocyanin over the tuber became more uniform. This suggested that the transport of some compound (carbohydrate or "trigger”) was responsible for the initiation of anthocyanin biosynthesis. Concentration of other flavonoids also increased and followed a similar pattern to that of the anthocyanins, with maximum concentrations occurring in Desiree tubers about 150-200g. Phenolic acid concentrations also increased during tuber development, although these reached a maximum concentration in slightly smaller tubers (about 70-100g).
Microscopical studies of anthocyanin-containing cells showed that the difference in colour intensities of the different cultivars was because of differences in the amount of anthocyanin produced in individual cortex cells, in the proportion of cortical cells within a layer producing anthocyanin, and the number of layers of coloured cells. Totally white tubers did not contain any anthocyanin coloured cells, whilst more highly coloured tubers contained a greater number of more highly coloured cells in these layers. Additionally, the strongly coloured tubers had increased amounts of anthocyanin present in the phellem cells and intense1y coloured deposits of anthocyanin around the cell walls of these cells.
Cold storage (4°C) of tubers caused an increased concentration of anthocyanins, especially at the bud end of the tuber, so that the distribution pattern of anthocyanins was reversed from that found in developing tubers. Storage at higher temperatures (10°C and above) caused a decrease in anthocyanin concentration. These changes in anthocyanin concentration were thought to be related to sprouting and also the sugar concentration within the tuber. Cooking (boiling, steaming or crisping) of tubers (until they were ready to eat) did not result in any significant loss in anthocyanin colour, although after two to three times the normal cooking time some loss of anthocyanin colour occurred.
Anthocyanin colour may have been affected by the high concentration of starch or sugars found in tubers. Addition of amylose, amylopectin, α-cyclodextrin and β-cyclodextrin to anthocyanin solutions caused a decrease in anthocyanin colour, whilst the addition of sugars (glucose, sucrose and maltose) resulted in increased anthocyanin colour.
Tissue-cultured minitubers were used to investigate the effects of light on anthocyanin biosynthesis. Although anthocyanins were produced in the dark in field grown tubers, the presence of light on the plant leaves was necessary for anthocyanin production in some cultivars. Anthocyanin concentration increased with increased light intensities in all cultivars studied (to a maximum of about 3.2ng/cm² of surface area in Desirée minitubers), and the activities of enzymes (phenylalanine ammonia-lyase, cinnamic acid 4-hydroxylase, chalcone isomerase, flavanone 3-hydroxylase, flavonoid 3'-hydroxylase, dihydroflavonol reductase and glycosyltransferase) showed related increases. Biosynthesis of anthocyanins was a high irradianceresponse and required at least eight hours of exposure to light for a significant increase in anthocyanin concentration to occur, after which anthocyanin concentration (to a similar maximum concentration) increased linearly with increasing time of exposure. Both phytochrome and cryptochrome light receptors were thought to be involved because light of blue, red and purple wavelengths enhanced anthocyanin production, compared with white light of similar intensity.
The regulation of anthocyanin biosynthesis in potato tubers is different from most other plants and tissues because direct light exposure of the tuber is not necessary for anthocyanin production. However, for maximum anthocyanin synthesis the exposure of the plant leaves to light is required. It is proposed that this synthesis of anthocyanins intubers in the dark requires genetic capability of the tubers, a supply of carbohydrates, and is mediated by a "trigger" compound produced after the exposure of the leaves to light and transported to the tubers.
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Willig, Jennifer A. "Analysis of Antiviral and Chemoprotective Effects of Strawberry Anthocyanins." UKnowledge, 2013. http://uknowledge.uky.edu/animalsci_etds/28.
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This study investigated the antiviral, chemoprotective and proliferative effects of strawberry anthocyanins on herpes simplex virus type-1, cancerous cell lines HT-29 and AGS, and normal cell lines Hs 738.St/Int and CCD-18Co. Antiviral properties were measured by infecting vero cells from adult grivet (Cercopithecus aethiops) with herpes simplex virus type-1 (HSV-1) and treating with a concentration of 1.25-20 µg/mL of strawberry anthocyanins. Infectivity and replication were quantified for herpes simplex virus type-1 using the direct plaque assay and reporting PFU/mL. Strawberry anthocyanins (>20 µg/mL) inhibited the herpes simplex virus infectivity in vero cells by 100% (p<0.05). Strawberry anthocyanins at concentrations of 5, 10 and 20 μg/mL were reduced to 75.36, 57.98, and 31.46 percent of the control (100%) (p<0.05).
Chemoprotective and proliferative effects of strawberry anthocyanins were analyzed for the human cell lines AGS, Hs 738.St/Int, HT-29, and CCD-18Co at a concentration of 25-200 µg/mL and quantified using the sulforhodamine-B assay. Growth inhibition occurred at a level of ≥87% for treatment concentrations 100 and 200 µg/mL for the cancerous AGS and HT-29 cell lines (p<0.0001). Proliferation rates for the normal Hs 738.St/Int and CCD-18Co cell lines increased at all treatment concentrations of 25-200 μg/mL (p<0.0001); suggestingthat the observed proliferative activity may be associated with anthocyanin treatment.Strawberry anthocyanin treatment concentration worked in a dose dependent manner for the HSV-1 and the cancerous AGS and HT-29 cells. The caspase-3 assay was performed to demonstrate potential mechanism of action and confirmed thatanthocyanin treatments play a role in apoptosisby the up regulation of caspase-3.Significantdifferences were seen between the growth characteristics of cancerous cell linescompared to their equivalent normal cell lines (p<0.0001).
In summary, the antiviral findings suggest that strawberry anthocyanin extracts could be an effective topical treatment and/or prophylactic agent for oral herpetic infections (HSV-1). Also, the in vitro chemoprotective effect of strawberry anthocyanins found may be relevant to in vivo work in the future because when anthocyanins are consumed in the diet they come in direct contact with the gastrointestinal tract and may provide chemoprotection upon contact with the stomach and gastrointestinal tract’s epithelial cell layer.
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De, Ferrars Rachel. "The metabolic fate and bioactivity of anthocyanins in humans." Thesis, University of East Anglia, 2014. https://ueaeprints.uea.ac.uk/49475/.
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Anthocyanins, the class of flavonoid responsible for giving a red hue to many berries, have been associated with a decreased risk of cardiovascular disease. However, numerous intervention studies feeding anthocyanin-rich foods report limited (<1%) bioavailability of the parent anthocyanins in vivo. Due to the instability of anthocyanins at neutral pH, it is postulated that degradation products and metabolites of anthocyanins may be responsible for the perceived bioactive effects. The aims of the present thesis were: (1) To model and establish analytical methods for the extraction and quantification of putative anthocyanin metabolites in urine, serum and faecal samples. (2) To identify and explore the pharmacokinetics of anthocyanin metabolites via the analysis of urine, serum and faecal samples from two human interventions, feeding either (a) 500 mg of isotopically (13C5) labelled anthocyanin or (b) 500 mg elderberry anthocyanins for 12 wks. (3) To explore the impact of acute (500 mg) versus chronic (500 mg/day for 12 wks) anthocyanin consumption on their metabolism and (4) To investigate the anti-inflammatory activity of six anthocyanin metabolites at physiologically relevant concentrations (0.01 μM to 10 μM) using human umbilical vein endothelial cells (HUVECs). Following the consumption of 500 mg elderberry anthocyanins, 28 anthocyanin metabolites were identified in urine and 21 in plasma, with the phenolic metabolites within plasma identified at 45 fold higher levels than their parent compounds. Similar results were observed within the 13C-labelled anthocyanin intervention, where 17 13C-labelled compounds were identified in serum and 31 in urine. However, chronic consumption of anthocyanins had no impact on the formation of the metabolites. The cardiovascular bioactivity of anthocyanins may be linked to the antiinflammatory activity of their metabolites. IL-6 and VCAM-1 are cytokines and adhesion molecules integral to the initiation and progression of inflammation. In vitro, anthocyanin metabolites reduced CD40L and TNF-α stimulated expression of the inflammatory markers, sVCAM-1 and IL-6, indicating that the anti-inflammatory effects of anthocyanins are likely attributed to their metabolites. In conclusion, the present thesis provides a new understanding into the metabolism and bioactivity of anthocyanins, which should provide an informative insight into how the consumption of higher intakes of anthocyanins may contribute to optimising human health.
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He, Jian. "Absorption, excretion, and transformation of individual anthocyanins in rats." College Park, Md. : University of Maryland, 2004. http://hdl.handle.net/1903/1765.
Full textAbstract:
Thesis (M.S.) -- University of Maryland, College Park, 2004.Thesis research directed by: Dept. of Nutrition and Food Science. Title from t.p. of PDF. Includes bibliographical references. Published by UMI Dissertation Services, Ann Arbor, Mich. Also available in paper.
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Rosales, Soto Maria U. "Phenolics, anthocyanins and antioxidant activity in red raspberry muffins." Pullman, Wash. : Washington State University, 2008. http://www.dissertations.wsu.edu/Thesis/Fall2008/M_Rosales_082708.pdf.
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Thesis (M.S. in food science)--Washington State University, December 2008.Title from PDF title page (viewed on Dec. 31, 2008). "School of Food Science and Human Nutrition." Includes bibliographical references.
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Su, Xiaoyu. "Identification and quantification of anthocyanins in the transgenic tomato." Thesis, Kansas State University, 2014. http://hdl.handle.net/2097/17719.
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Master of ScienceFood Science Institute
Weiqun Wang
Anthocyanins, a sub-class of flavonoids, are natural pigments derived from phenylpropanoid pathway. Most tomato cultivars found in nature have very low content of anthocyanins, but dark purple tomatoes by ectopic co-expression of two transcription factors Delila (Del) and Rosea1 (Ros1) from snapdragon and chalcone isomerase (CHI) from onion accumulated high levels of anthocyanins. This study is to identify and quantitate anthocyanins in these transgenic tomato lines. Seven anthocyanins including two new anthocyanins [malvidin-3-(p-coumaroyl)-rutinoside-5-glucoside and malvidin-3- (feruloyl) -rutinoside-5-glucoside] have been identified in transgenic lines by HPLC-MS. The top two anthocyanins are petunidin 3-(trans-coumaroyl)-rutinoside- 5-glucoside and delphinidin 3-(trans-coumaroyl)-rutinoside-5-glucoside that contribute for 85% of total anthocyanins in whole fruit. Comparing with undetectable anthocyanins in the wild type, Del/Ros1-expressing tomatoes contain total anthocyanins at 4.95±0.42 g/kg dry matter in whole fruit, 5.09±0.62 g/kg dry matter in peel, and 5.56±0.29 g/kg dry matter in flesh, while CHI×Del/Ros1-coexpressing tomatoes have 9.61±0.71 g/kg dry matter in whole fruit, 29.9±1.64 g/kg dry matter in peel, and 8.65±0.39 g/kg dry matter in flesh. No anthocyanins are detectable in the seeds of each line tested. Enrichment of tomato fruit with new and high anthocyanins may provide potential health-promoting benefits.
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Amini, Anna Maria. "Effects of anthocyanins on the immune and cardiovascular system." Thesis, University of Reading, 2017. http://centaur.reading.ac.uk/78064/.
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Anthocyanins are increasingly being recognized for their potential health benefits, including effects on the immune and cardiovascular system. This PhD research project addressed some key research gaps by evaluating the effects of anthocyanins and an anthocyanin-rich blackcurrant beverage on markers of immunity and cardiovascular disease (CVD) risk. Cellular screening models examined the anti-inflammatory effects of pelargonidin-3-Oglucoside and three of its plasma metabolites in THP-1 monocytes, THP-1 macrophages and whole blood cultures. There were modest effects on the production of interleukin (IL)-6 and IL-10, while no effects were observed on IL-1β, IL-8 and tumor necrosis factor-α. The effects were dependent on the experimental model employed and the data suggest differential antiinflammatory potencies of the tested phenolic compounds and only modest effect sizes. The whole blood culture model also examined, for the first time, the effects of pelargonidin-3- O-glucoside and three of its plasma metabolites on phagocytosis and oxidative burst activity, but there were no significant effects. Subsequent studies should explore other immunomodulatory effects of dietary anthocyanins. An acute RCT investigated, for the first time, the effects of an anthocyanin-rich blackcurrant beverage in response to a high-fat meal on selected markers of CVD risk in healthy middleaged men and women. The anthocyanin-rich blackcurrant beverage significantly improved flow-mediated dilation, platelet function, systolic blood pressure and IL-8 concentrations. The effects were observed with 711 mg anthocyanins, which corresponds to 120 mg fresh blackcurrants, an amount that is high but achievable through the diet. There were no significant effects of the beverage on diastolic blood pressure, arterial stiffness, plasma concentrations of nitrite, nitrate, or numbers of endothelial or platelet microparticles. In conclusion, the data suggest that anthocyanins can attenuate deleterious effects of a dietary fat challenge and could represent an effective tool for CVD prevention.
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Boss, Paul K. "The molecular biology of anthocyanin biosynthesis in grape berry skins." Title page, contents and abstract only, 1998. http://web4.library.adelaide.edu.au/theses/09PH/09phb745.pdf.
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Sigurdson, Gregory T. "Evaluating the Effects of Anthocyanin Structure and the Role of Metal Ions on the Blue Color Evolution of Anthocyanins in Varied pH Environments." The Ohio State University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=osu1461253897.
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Munshi, Abdullah Ahmad. "Genetics and chromatography of anthocyanins in flowers of zonal pelargoniums." Thesis, Swansea University, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.507973.
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Kallam, Kalyani. "Side chain decoration of anthocyanins : mechanisms and effects on functionality." Thesis, University of East Anglia, 2012. https://ueaeprints.uea.ac.uk/42384/.
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Anthocyanins are plant pigments offering a range of colours to fruits and flowers. Many properties of anthocyanins are influenced by the degree and type of side chain modifications. Though much is known about the biosynthesis of anthocyanins and the enzymes involved in side-chain decoration, there is limited understanding of the structural features of anthocyanin acyltransferases that determine their substrate preference. Anthocyanin acyltransferases belong to the BAHD family of enzymes and are involved in acylation. Through mutagenesis I showed that an arginine positioned close to motif-1 in aliphatic anthocyanin acyltransferase determines the enzyme’s specificity for malonyl transfer. Modification of arginine to phenylalanine in Ch3MAT, led to gain of acetylation property. This study thus suggests that CoA interacting residues are conserved in aliphatic acyltansferases. A phenylalanine in a similar position, close to motif 1 in aromatic anthocyanin acyltransferases is crucial for the specificity for aromatic-CoA of aromatic acyltransferases. To understand the influence of different side-chain modifications on the formation of anthocyanic vacuolar inclusions (AVIs), I showed that coumaroylation of anthocyanins leads to AVI formation when high levels of anthocyanins are accumulating. Malonylation does not lead to the formation of AVIs, suggesting that the ability of aromatic moieties to form intra-molecular stacks can cause formation of AVIs. Neither the presence of flavonols nor light or high amounts of anthocyanins can lead to the formation of AVIs. Therefore, the type of decoration mainly aromatic acylation of anthocyanins is responsible for AVI formation. From understanding the molecular mechanisms of acyltransferases for side chain decoration to their activity, anthocyanins can be engineered by anthocyanin acyltransferases in plants for novel functionalities. I showed that coumaroylation of anthocyanins promotes copigmentation more effectively than 5-glucosylation. 5- glucosylation, together with coumaroylation, offered stability to anthocyanins, both invitro and in-vivo. I also showed that flavonols copigment better than phenolics with anthocyanins, a property which could be useful for developing natural food colours. Thus, my study provided an in-depth investigation from molecular mechanisms to final applications of side chain decoration of anthocyanins.
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Cooke, Darren. "Pre-clinical development of anthocyanins as colorectal cancer chemopreventive agents." Thesis, University of Leicester, 2008. http://hdl.handle.net/2381/29865.
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The hypothesis was tested that dietary Mirtoselect, a standardised mixture of 15 anthocyanins, or the isolated anthocyanin cyanidin-3-glucoside (C3G) affect adenoma development in the ApcMIN mouse, a genetic model of colorectal cancer. Anthocyanins were added to the diet at 0.03, 0.1 or 0.3% (w/w) for the animals' life time. Adenoma number and size were measured at the end of the experiment (week 16). Both interventions reduced adenoma number/burden in a dose-dependent fashion. A potential mechanism by which anthocyanins are thought to exert cancer chemoprevention is anti-oxidation. Anti-oxidant effects of the interventions were investigated in DNA from ApcMIN murine adenoma tissue by analysis of the pyrimidopurinone adduct of deoxyguanosine M1dG, a product of the reaction of DNA with malondialdehyde. At the dietary dose of 0.3% C3G and Mirtoselect significantly reduced levels of M1dG, suggesting that antioxidation may contribute to anthocyanin-mediated interference with adenoma development. C57BL mice, the ApcMIN background strain, received C3G po or I.V. at 500 or 1 mg/kg, respectively. Levels of anthocyanins in plasma and tissue were measured using a newly developed HPLC method. C3G bioavailability was 3.28%, consistent with literature values after ingestion of berries/fruits. Anthocyanin species were detected in the plasma, urine, mucosa, liver, kidneys, heart, lung, gall bladder and brain. Absorption, distribution and excretion in the urine were rapid. The mean time of peak levels for all tissues studied was ∼26 min. The work described here defines further the potential role of anthocyanins in colorectal cancer chemoprevention. It also describes pharmacokinetic and pharmacodynamic features which may help optimise future clinical chemoprevention trials.
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Xu, Jianteng. "Identification and stability of acylated anthocyanins in purplefleshed sweetpotato p40." Thesis, Kansas State University, 2013. http://hdl.handle.net/2097/16910.
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Master of ScienceDepartment of Food Science
Weiqun Wang
We previously selected a purple-fleshed sweetpotato p40 clone that has been shown to protect against colorectal cancer in a murine model. This study is to identify anthocyanins by using HPLC/MS-MS and assess the stability during various coking conditions. P40 possesses a high content of anthocyanins up to 13 mg/g dry matter. Total 12 acylated anthocyanins with caffeic, ferulic, and p-hydrobenzoic acid have been identified on either cyanidin or peonidin bases. The top three major anthocyanins are cyanidin 3-caffeoyl-p-hydroxybenzoyl sophoroside-5-glucoside, peonidin 3-caffeoyl sophoroside-5-glucoside, and cyanidin 3-(6'' -caffeoyl-6''-feruloylsophoroside)-5-glucoside, which account for an half of the total anthocyanin contents. Seven non-, mono-, or di-acylated cyanidin species and five mono- or di-acylated peonidin species contribute for 69% and 31% of total anthocyanins, respectively. Over 80% of total anthocyanins measured by acid hydrolysis were cyanidin derivatives. Therefore, as a cyanidin-predominated variety, p40 is unique when compared with other reported purple-fleshed sweetpotatoes that usually contain more peonidin than cyanidin. While baking does not impact overall contents of anthocyanins, steaming, high pressure cooking, microwaving, and frying significantly reduce 20% of total anthocyanin contents. Mono-acylated anthocyanins show a higher resistance against heat than di- and non-acylated. Among of which, cyaniding 3-p-hydroxybenzoylsophoroside-5-glucoside exhibits the best thermal stability. Better understanding of dietary anthocyanins and their stabilities may lead to the development of a functional anthocyanin-enriched sweetpotato product for health benefits.
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Mishra, Dharmendra Kumar. "Kinetic parameter estimation for degradation of anthocyanins in grape pomace." Diss., Connect to online resource - MSU authorized users, 2008.
Find full textAbstract:
Thesis (M.S.)--Michigan State University. Dept. of Biosystems and Agricultural Engineering, 2008.Title from PDF t.p. (viewed on Aug. 3, 2009) Includes bibliographical references. Also issued in print.
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Tucakovic, Lada. "Role of anthocyanins in attenuating obesity and obesity-induced inflammation." Thesis, Griffith University, 2018. http://hdl.handle.net/10072/381005.
Full textAbstract:
The incidence of obesity and its related metabolic diseases, such as diabetes,
cardiovascular disease and hypertension, has escalated dramatically over the past decades
worldwide, so much so that it has reached epidemic proportions. It has become a
significant public health issue and a massive burden to the health-care system in
developed and developing countries. Obesity is the fifth leading risk for human mortality
around the globe, resulting in 2.8 million adult deaths each year. Another alarming fact is
that childhood obesity has increased dramatically since 1990. Childhood obesity is one
of the serious public health challenges of the 21st century, with there expected to be about
60 million obese children by 2020 globally.
Obesity is connected with chronic low-grade inflammation manifested by increased
circulatory levels of several cytokines and acute phase proteins associated with
inflammation. While many are secreted by adipocytes, it is believed that increased
adipose tissue mass is either directly or indirectly associated with the increased
production of inflammation-related factors.
Several therapeutic options have been used for short-term treatment of obesity, however
many of these cause unpleasant side-effects, including dizziness, headache, anxiety,
elevated heart rate and gastro-intestinal issues. There is strong evidence supporting the
therapeutic use of polyphenols such as stilbenes, flavonoids and curcuminoids, given that
they show potential in the prevention and/or treatment of obesity and its metabolic
complications. They are widely accepted in health promotion due to their antioxidant,
anti-inflammatory, anti-carcinogenic, anti-obesity, anti-diabetic, and anti-ageing
properties. The actions of their effect are thought to be through the suppression of
adipocyte differentiation and proliferation, inhibition of fat absorption from the gut, inhibition of lipogenesis, stimulation of β-oxidation, inhibition of production of proinflammatory
adipokines, and the stimulation of adiponectin secretion.
Polyphenols, specifically anthocyanins, present in a novel plum variety, Queen-Garnet
plums (QGP), have been studied in the first clinical trial. It was hypothesised that
anthocyanin-rich QGP juice could be effective in reducing body weight and production
of adipose tissue hormones (Chapter 4). It was observed that QGPJ significantly reduced
body weight in humans after 4 weeks of supplementation. Furthermore, anthocyanins had
significant effects on secretion of adiponectin as well as effects on the production of
leptin.
Anti-inflammatory actions of anthocyanins extracted from bilberries (Vaccinium
myrtillus) and blackcurrant (Ribes nigrum) and their effect on pro-inflammatory markers
were studied in the second clinical trial. It was hypothesised that high-dose anthocynin
supplementation, in the form of MEDOX® capsules, would downregulate inflammatory
adipocytokines in overweight and obese individuals (Chapter 5). Results illustrated the
significant effect of anthocynins on secretion of MCP1/CCL2 and IL-6 in overweight and
obese populations, as well as an effect on TNF-α production in obese individuals.
The anti-obesity effect of anthocynin supplementation on body weight and production of
adipose tissue hormones was also evaluated in the second clinical trial. It was
hypothesised that high-dose anthocyanins would regulate the secretion of hormones as
well as decrease the body weight in overweight and obese populations after 4 weeks of
supplementation (Chapter 6). It was demonstrated that supplementation with
anthocyanins resulted in significant increases in adiponectin secretion as well as
significant decreases in leptin production in overweight and obese individuals.
Due to the showed beneficial effects of polyphenols on anti and pro inflammatory
adipocytokine secretion, the influence of anthocyanins present in QGPJ and MEDOX® supplements on the gene expression of these markers was investigated (Chapters 4, 5 and
6). Interestingly, it was observed that polyphenols did not have a significant effect on the
modulation of anti and pro-inflammatory markers’ gene expression.
From the observed effects of polyphenols, specifically anthocyanins, on secretion and
production of anti and pro-inflammatory markers as well as hormones, further studies
with a larger number of volunteers and for a longer time are needed. Investigation of other
anti and pro-inflammatory markers, as well as comparison of anthocyanins supplements
to current anti-inflammatory and anti-obesity therapies and treatments, could also be
beneficial.Thesis (PhD Doctorate)
Doctor of Philosophy (PhD)
School of Medical Science
Griffith Health
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VALENZA, ALICE MARIA. "Anthocyanins rescue Macrophage infiltration in a Drosophila model of obesity." Doctoral thesis, Università degli Studi di Milano, 2019. http://hdl.handle.net/2434/644637.
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For years, scientific research has availed itself of the opportunity of using animal models to understand the cellular and molecular mechanisms that regulate several human diseases. In this thesis, I showed the great importance to employ Drosophila melanogaster as model organism for the study of chronic diseases. Drosophila is considered an excellent and innovative model thanks to its peculiar characteristics such as low cost, small genome size, short generation time.
About 75% of human disease-causing genes have functional homologs in Drosophila; furthermore, the fruit fly shows extreme genetic flexibility and a number of genetic systems has been developed to answer specific biological questions, such as the UAS-GAL4 binary system that allows the expression of target genes in a tissue-specific manner.
For all these reasons, Drosophila can be used for the study of different metabolic diseases among which obesity. In particular, in our laboratory we created a new Drosophila model of obesity that shows similar characteristics as those present in obese people, promoting an Adipose Tissue Macrophages infiltration (ATM) phenotype.
Using this new model of obesity, I tried to understand the role of important compounds like Flavonoids and Anthocyanins, both considered anti-inflammatory and antioxidant agents, which regular consumption reduces the risk to develop metabolic disorders.
Anthocyanins represent the major red, purple, and blu pigment in many plants and fruits. I have discovered that Anthocyanins are able to rescue the ATM phenotype by reducing the Drosophila hemocytes (similar to human macrophages) migration in the larval fat body, which carries out human adipose tissue and liver functions.
Anthocyanins also show potential health benefits by reducing ROS levels, thus acting as antioxidant agents. This antioxidant activity may be due to the capacity to modulate the expression of some redox regulators like Glutathione-S-Transferase (GST) and the Nuclear factor erythroid 2-Related Factor 2 (NRF2).
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Fenger, Julie-Anne. "Les anthocyanes acylées en tant que colorants naturels : réactivité en solution aqueuse, complexation métallique et stabilisation pour des applications alimentaires The chemical reactivity of anthocyanins and its consequences in food science and nutrition The influence of acylation and metal binding on the thermal stability of red cabbage anthocyanins The fate of acylated anthocyanins in neutral solution." Thesis, Avignon, 2020. http://www.theses.fr/2020AVIG0278.
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Les anthocyanes sont des pigments d’origine végétale exprimant des couleurs vives allant du rouge au bleu. Ce sont donc de bons candidats pour remplacer les colorants alimentaires artificiels. Cependant, leur faible stabilité est un frein à ces applications, tout particulièrement en milieu neutre requis pour l’expression de la couleur bleue. Une perspective prometteuse est le recours aux anthocyanes acylées par les acides phydroxycinnamiques, car ces pigments développent des mécanismes protecteurs de la couleur (copigmentation intramoléculaire, auto-association) basés sur de fortes interactions d’empilement entre le chromophore et les résidus acyl. Ce travail étudie donc les transformations structurales d’anthocyanes acylées (transferts de proton, addition d’eau), leur affinité pour les ions métalliques et leur stabilité au cours d’un traitement thermique. Dans ce but, des études cinétiques et thermodynamiques par spectroscopie UV-visible sont combinées à l’identification de produits de dégradation par UPLC-DAD/MS. L’impact des groupements acyl (nombre, position, type) a été étudié grâce à une gamme de pigments isolés du chou rouge et de la patate douce pourpre. Pour les premiers, les groupements acyl sur le sucre externe du groupement sophorose confèrent a) une protection optimale contre les attaques par H2O, H2O2 and SO32-, b) une plus grande affinité pour les ions métalliques, c) une plus grande stabilité thermique (pour les pigments et leurs complexes). En revanche, l’acide caféique, qu’il soit libre ou bien sous forme de résidu acyl (cas des anthocyanes de la patate douce violette), accélère la dégradation des anthocyanes, bien qu’il stabilise la couleur. Un traitement thermique modéré à pH 7 a converti les anthocyanes du chou rouge en acylsophoroses, phloroglucinaldéhyde-2-O-glucoside, acide protocatéchuique, dérivés de la 3,5,7-trihydroxycoumarine et de l’acide 2,4,6-trihydroxyphenylacétique. Un phénomène de migration intramoléculaire de résidus acyl a également été mis en évidence. La base anionique, une forme colorée majeure à pH 7, apparaît comme la plus vulnérable à l’autoxydation. Le peroxyde d’hydrogène ainsi formé est également impliqué dans la dégradation des anthocyanes. Globalement, nos résultats montrent que la forte association des anthocyanes acylées avec les ions du fer et de l’aluminium, voire l’ajout d’antioxydants naturels (par ex., la Nacétylcystéine), constituent des voies d’avenir pour le développement de colorants bleus naturels stablesAnthocyanins are ubiquitous plant pigments that exhibit bright colors from red to blue. Thus, they are good candidates to replace the synthetic food colors. However, the low stability of anthocyanin colors is a real hurdle to their industrial applications, especially under near neutral conditions required to express the blue color. A promising perspective is to resort to anthocyanins acylated by p-hydroxycinnamic acids, as these pigments develop colorstabilizing mechanisms (intramolecular copigmentation, self-association) based on strong stacking interactions between the anthocyanidin chromophore and the acyl residues. Therefore, this work investigates the structural transformations of acylated anthocyanins (proton transfer, water addition), their affinity to metal ions and their resistance to thermal degradation in the presence or absence of added metal ions. To that purpose, kinetic and thermodynamic studies by UV-visible spectroscopy are combined with the identification of degradation products by UPLC-DAD/MS. The impact of the acyl residues (number, location, type) was deciphered from a series of isolated pigments from red cabbage and purple sweet potato. With the former, the acyl residue bound to the external glucose of the sophorose moiety provides a) optimal protection against attacks by H2O, H2O2 and sulfite, b) improved affinity for metal ions, c) enhanced resistance against thermal degradation (for anthocyanins and their metal complexes). By contrast, caffeic acid, whether free or as an acyl residue (in purple sweet potato), accelerates the degradation of anthocyanins in spite of stabilizing the color. Under moderate heating at pH 7, red cabbage anthocyanins were degraded into acylsophoroses, phloroglucinaldehyde-2-O-glucoside, protocatechuic acid, 3,5,7trihydroxycoumarin derivatives, and 2,4,6-trihydroxyphenylacetic acid derivatives. Intramolecular acyl migration was also evidenced. The anionic base, a major colored form at pH 7, appears most vulnerable to autoxidation. The hydrogen peroxide thus produced is further involved in anthocyanin degradation. Overall, the tight binding of acylated anthocyanins to iron and aluminum ions and possibly the addition of natural antioxidants (e.g., N-acetylcysteine) are promising perspectives for the development of stable natural blue colors
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Yuste, Silvia. "Red-fleshed apple as novel anthocyanin-biofortified food: Effect of food processing on the (poly)phenolic composition, bioavailability assessment and cardiometabolic effects of anthocyanins." Doctoral thesis, Universitat de Lleida, 2021. http://hdl.handle.net/10803/671437.
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La millora d'aliments tradicionals mitjançant la biofortificación amb compostos saludables ha aparegut com una possible estratègia per prevenir malalties cardiovasculars. En aquesta Tesi s'ha estudiat el potencial d'una nova varietat de poma de polpa vermella biofortificada amb antocians i obtinguda per mètodes de creuament tradicionals. Primerament es va avaluar l'impacte de diferents tecnologies de processament tèrmic i no tèrmic en el contingut de (poli)fenols i en la seva biodisponibilitat, per al desenvolupament d’un snack de poma, resultant l'snack liofilitzat el producte òptim. Un estudi postprandial realitzat amb humans va mostrar que els (poli)fenols de la poma es metabolitzen extensament, i de tots els metabòlits detectats, la floretina glucurònid, la cianidina-3-O-galactòsid i la peonidina-3-O-galactòsid, es van definir com a biomarcadors de consum. En un estudi preliminar amb rates Wistar hipercolesterolèmiques, es van observar efectes cardiometabòlics a través de la reducció del gruix aòrtic i una millora de la funció renal després de la ingesta de poma vermella. Aquests efectes van ser diferents entre mascles i femelles, el que podria estar relacionat amb diferències en la biodisponibilitat dels (poli)fenols de la poma depenent del sexe.La mejora de alimentos tradicionales mediante la biofortificación con compuestos saludables ha aparecido como una estrategia potencial para prevenir enfermedades cardiovasculares. En esta Tesis se ha explorado el potencial de una nueva variedad de manzana de pulpa roja biofortificada con antocianos y obtenida por métodos de cruzamiento tradicionales. Para el desarrollo de un snack de esta manzana, se evaluó el impacto de diferentes tecnologías de procesamiento térmico y no térmico en el contenido de (poli)fenoles y en su biodisponibilidad, resultando el snack liofilizado el óptimo. El estudio postprandial realizado con humanos mostró que los (poli)fenoles de la manzana se metabolizaron extensamente, de todos los metabolitos detectados, la floretina glucurónido, la cianidina-3-O-galactósido y la peonidina-3-O-galactósido se definieron como los biomarcadores de consumo específicos. Los primeros efectos cardiometabólicos de la manzana de pulpa roja se observaron en ratas Wistar hipercolesterolémicas en las que se observó una reducción del grosor aórtico y una mejora de la función renal. Estos efectos fueron diferentes entre machos y hembras, lo que podría estar relacionado con diferencias en la biodisponibilidad de los (poli)fenoles de la manzana relacionadas con el sexo.
Enhancing traditional foods through biofortification with healthy compounds has appeared as a potential strategy to prevent cardiovascular diseases. In this Thesis the potential of a new apple variety with red flesh biofortified in anthocyanins obtained by traditional breeding methods has been explored. The impact of different thermal and non-thermal processing technologies on the (poly)phenolic content and its bioavailability was evaluated for the development of an apple snack product, resulting in the freeze-dried snack as the optimal one. A human postprandial study was performed and apple (poly)phenols appeared to be extensively metabolized, out of all the metabolites detected, phloretin glucuronide, cyanidin-3-O-galactoside and peonidin-3-O-galactoside were defined as specific consumption biomarkers. First insights into the cardiometabolic effects of red-fleshed apple showed a reduction of the aorta thickness and improvement of the renal function in hipercholesterolemic Wistar rats. These effects were different between males and females and could be related to sex-related differences in apple (poly)phenol bioavailability.
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Carey, Charles Champney. "Three regulators of the maize anthocyanin pathway /." view abstract or download file of text, 2002. http://wwwlib.umi.com/cr/uoregon/fullcit?p3061938.
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Thesis (Ph. D.)--University of Oregon, 2002.Typescript. Includes vita and abstract. Includes bibliographical references (leaves 210-219). Also available for download via the World Wide Web; free to University of Oregon users.
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Sampaio, Patricia Gisela. "Otimização da extração, esterilização e identificação de antocianinas obtidas a partir de frutas." [s.n.], 2008. http://repositorio.unicamp.br/jspui/handle/REPOSIP/250115.
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Orientador: Adriana Vitorino RossiDissertação (mestrado) - Universidade Estadual de Campinas, Instituto de Quimica
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Resumo: Antocianinas (ACYS) são pigmentos naturais de origem vegetal classificados quimicamente como flavonóides. O uso industrial de ACYS é restrito em função de algumas limitações, como seu alto custo e sua relativa baixa estabilidade. Neste contexto, o objetivo deste trabalho foi utilizar frutas do Brasil como fontes para extração de ACYS, testando-se estratégias para estabilização dos extratos e identificação das ACYS. Foram obtidos extratos de ACYS, a partir de frutos de jabuticaba (Myrciaria cauliflora), amora (Morus nigra), amora preta (Rubus sp) e jambolão (Eugenia jambolana Lam), otimizando- se condições de extração com a variação de solventes, temperatura de extração, uso de agitação e de trituração mecânica. Foram utilizadas cascas, frutas inteiras e descaroçadas na proporção 1:3 fonte de ACYS:solvente (m/v). Os extratos com maior quantidade de ACYS foram obtidos a partir de extração com etanol 94% v/v, a 55ºC por 30 minutos e, em alguns casos, com uso de trituração mecânica. Para aumentar a estabilidade dos extratos de ACYS, investigaram-se processos de esterilização como a tindalização dos extratos e o branqueamento das frutas. Este último mostrou-se mais favorável, pois além de aumentar a estabilidade dos extratos, que podem durar 360 dias sem aparecimento de fungos, elevou a quantidade de ACYS extraída. Para identificação de ACYS foram avaliados 3 métodos, aplicando-se como técnica de separação a cromatografia líquida de alta eficiência (HPLC). Testaram-se métodos envolvendo padrões de ACYS; comparação relativa de tempos de retenção e espectrometria de massas com ionização por eletrospray e analisador quadrupolo-tempo de vôo (ESI-Q-TOF-MS). A antocianina majoritária identificada foi a cianidina-3-glicosídeo nos extratos de jabuticaba, amora e amora preta. O método por comparação relativa de tR é uma boa opção para a identificação de ACYS, pois envolve procedimento simples e não requer o uso de padrões, mas tem limitações que foram superadas com a viabilização ou confirmação da identificação de ACYS por HPLC-ESI-Q-TOF-MS
Abstract: Anthocyanins (ACYS) are natural pigments of plant origin, chemically classified as flavonoids. The industrial use of ACYS is restricted according to some limitations, such as its high cost and relative low stability. In this context, the objective of this study was to use jaboticaba (Myrciaria cauliflora), mulberry (Morus nigra), blackberry (Rubus spp) and jambolão (Eugenia jambolana Lam), whose are common Brazilians fruits, as sources of ACYS to test extraction conditions, extracts stabilization strategies and ACYS identification strategies. The extraction conditions were optimized varying solvents, temperature, and using or not the stirrer and the mechanic grinding. Peels, whole fruits and fruits without pits were used in the proportion of 1:3 ACYS source: solvent (m/v). The extracts with the greatest amount of ACYS were obtained from extraction with ethanol 94% v/v, 55 ºC for 30 minutes and, in some cases, using mechanical grinding. To increase the stability of the ACYS extracts, sterilization processes such as tyndalization of the extracts and blanching of fruit were investigated. The blanching was more favorable because it increased the stability of the extracts, which can last for 360 days without appearance of fungi, and increased the amount of ACYS extracted. Using the high performance liquid chromatography (HPLC) for separation, three methods were evaluated in order to identify ACYS: the method with ACYS patterns; the relative comparison of retention time (tR); and mass spectrometry using electrospray ionization and quadrupole-time-of-flight mass analysis (ESI-Q-TOF-MS). The majority anthocyanin identified in extracts of jaboticaba, mulberry and blackberry was cyanidin-3- glycoside. The method with comparison of tR was a good option for the ACYS identification because it is a simple procedure and does not require the use of standards, but it has limitations that could be overcome making possible or confirming the ACYS identification using HPLC-ESI-Q-TOF-MS
Mestrado
Quimica Analitica
Mestre em Química
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Paissoni, Maria Alessandra. "Characterization of anthocyanins and condensed tannins from grapes and their qualitative incidence on astringency and bitterness sensory properties." Thesis, Bordeaux, 2018. http://www.theses.fr/2018BORD0383/document.
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Dans le vin rouge, les composés phénoliques sont souvent associés à la qualité du produit. Parmi eux, les anthocyanes sont responsables de la couleur du vin rouge et chaque cépage possède un génome spécifique déterminant le profil anthocyanique de chacun. Les pratiques culturales peuvent influencer l’accumulation de ces molécules dans la baie de raisin, tandis que les différentes techniques fermentaires peuvent modifier leur extraction. Les flavanols monomères, oligomères et polymères des pépins et des pellicules contribuent à l’amertume et l’astringence des vins. Pendant la vinification et l’élevage, ceux-ci réagissent avec les anthocyanes modifiant les propriétés du vin. De nombreuses publications concernant les caractéristiques sensorielles des flavanols ont été réalisées, alors que la contribution sensorielle des anthocyanes est encore mal connue. Cette thèse se décompose en deux parties. La première partie s’intéresse à l’étude de l’utilisation d’ozone gazeux comme technique pré-fermentaire sur les cépages rouges Nebbiolo et Barbera après récolte et pendant le passerillage. L’ozone est une technique innovante pour la réduction des contaminations microbiennes et la réduction du dioxyde de soufre. L’influence de cette technique sur les parois cellulaire des pellicules, sur l’extraction, la concentration en flavanols et en anthocyanes pendant la macération a été évaluée. L’étude montre que l’ozone possède un impact sur la macération des raisins, induisant une extraction plus importante des anthocyanes dans le Nebbiolo. En revanche, l’ozone n’influence ni les anthocyanes moléculaires, ni le profil variétal de chaque cépage. Pendant le passerillage, l’inverse a été étudié. L’extraction des anthocyanes dans le Nebbiolo est diminuée. A l’inverse, bien que moins d’anthocyanes soient retrouvées dans le raisin de Barbera, le traitement ne possède aucun impact sur l’extraction de celles-ci. Concernant les flavanols, l’extraction est moins influencée par le traitement à l’ozone. Des différences ont été retrouvées dans le cépage Nebbiolo. Les flavonols sont plus concentrés après le traitement avec l’ozone sur les raisins post-récolte, alors qu’ils diminuent pendant le passerillage. La modification causée sur la paroi cellulaire par l’ozone ainsi que la dureté des pellicules pourraient prédire l’extraction des anthocyanes et des flavanols, grâce à des analyses multi-variées. En conséquence, le traitement avec l’ozone doit être adapté en fonction du cépage et du produit final désiré. Dans la deuxième partie, les anthocyanes des raisins ont été extraites à partir des raisins et ces extraits ont été fractionnés en trois fractions, glucoside, acetyl-glucoside et cinnamoyl-glucoside, par Chromatographie de Partage Centrifuge (CPC) et CLHP (Chromatographie Liquide Haute Performance) préparative. L’évaluation de l’astringence a été réalisée par des analyses de précipitation protéique avec une protéine modèle BSA (Bovine Serum Albumin) et des protéines salivaires, les anthocyanes réagissant avec ces dernières. Les analyses sensorielles et l’évaluation de l’astringence ont été combinées. La concentration en anthocyane diminue après le traitement avec les protéines salivaires, dans l’extrait total et dans les fractions, en particulier les cinnamoyl-glucosides apparaissent comme les plus réactives avec les protéines salivaires. Les seuils de perception gustatifs ont été calculés avec la méthode “Best estimate threshold” dans le vin modèle. Les fractions acétyl-glucosides et cinnamoyl-glucosides, suivies de la fraction glucoside, possèdent des seuils de perception plus bas aux concentrations retrouvées dans les vins. Les descripteurs associés à ces fractions sont l’amertume et l’astringence. Ces résultats démontreraient que les anthocyanes apportent une contribution sensorielle dans la perception du vin en bouche, corrélée à l’acétylation des moléculesIn red wine, phenolic compounds are generally associated with the quality of products. Among them, anthocyanins extracted from skins are responsible for wine colour. The grapevine genomes determine the anthocyanins profiles, but several factors in the vineyard can influence their accumulation, as well as post-harvest techniques can modify their extraction during winemaking. Monomeric, oligomeric and polymeric flavanols from skins and seeds contribute to astringency and bitterness of wine and during winemaking and ageing complexes formation with anthocyanins modifies wine characteristics. Several publications are available to understand flavanols sensory characteristics, whereas anthocyanins role has not consensus in scientific literature. This PhD thesis is composed by two parts. The first part deal with the evaluation of the use of gaseous ozone as post-harvest technique in red wine grapes Nebbiolo and Barbera used on both fresh grape and during withering. Ozone treatment is an innovative technology proved to avoid mycobiota spoilage and preserving from the use of sulphur dioxide. Its influence on flavanol and anthocyanin contents and extractabilities during maceration was evaluated, considering skin cell wall modification. In fresh grape, ozone influenced skin maceration for both the varieties, leading to a higher anthocyanin extraction in Nebbiolo grapes and lower in Barbera. Ozone did not influence the final individual anthocyanin extractability, respecting the varietal anthocyanin fingerprint. During dehydration, opposite trend was found: in Nebbiolo reported no change in the content of total anthocyanins just after ozone-assisted dehydration, but their extraction yield was lower. On the contrary, although lower contents of anthocyanins were found in Barbera grapes no differences in final extractability was found. Regarding oligomeric and polymeric flavanols, their extractability was less affected by the ozone treatment. Only in Nebbiolo, both oligomeric and polymeric flavanol extraction was increased in fresh grape, whereas it is slightly decrease during dehydration. The ozone-induced modification of skin cell wall composition together with skin hardness parameters fitted well in multivariate models to predict anthocyanins, oligomeric flavanols and polymeric flavanols extraction. Therefore, the ozone treatment should be adapted depending on the variety and on the target wine. In the second part, grape anthocyanins were isolated depending on the acylation patterns, i.e. glucoside, acetyl-glucoside, and cinnamoyl-glucoside by a combination of centrifugal partition chromatography (CPC) and preparative-HPLC. Protein precipitation analyses to assess astringency and sensorial analysis were carried out. Anthocyanins reacted with both bovine serum albumine and salivary proteins, in different extent, since higher interaction between anthocyanins and salivary proteins was found with a significative reduction of total extract and fractions glucoside, acetyl-glucoside, and cinnamoyl-glucoside. The latter in particular is the more reactive to salivary proteins. Sensorial analysis was carried out as detection threshold test. Best estimated threshold (BET) of anthocyanins were resulted in wine-range scale, in particular acetyl-glucoside and cinnamoyl-glucoside BET are lower of glucoside threshold, and descriptors reported were astringency and bitterness. These results show that anthocyanins can be detected as in-mouth properties contributors, and the magnitude of their involvement is related to anthocyanins acylation
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Della, Vedova Chris. "RNA silencing of an endogenous gene in maize /." free to MU campus, to others for purchase, 2004. http://wwwlib.umi.com/cr/mo/fullcit?p3144411.
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Sandoval, Ramírez Berner Andrée. "The tissue bioavailability, biomarkers, and effects of anthocyanins on human health. Studied through systematic reviews on anthocyanin-rich foods and a nutritional pre-clinical study with anthocyanin-rich red fleshed-apples. The AppleCOR Project." Doctoral thesis, Universitat Rovira i Virgili, 2021. http://hdl.handle.net/10803/672575.
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ompleix els criteris per ser considerat un biomarcador d'ingesta de baies en el plasma i l'orina humans. 3) consumir 100-150 g / dia d'illes senceres millora múltiples factors de risc de malaltia cardiovascular (MCV), i mortalitat per MCV. 4) a partir de la intervenció animal, les pomes riques en ACN tenen un efecte antiinflamatori, mentre que les pomes de polpa blanca redueixen les proteïnes relacionades amb el sistema de l'complement a cors i aortes de rates hipercolesterolémicas, el que suggereix un efecte de matriu de poma beneficiós, independentment del seu contingut d'ACN. 5) la ingesta oral d'ACN, independentment del seu origen, s'associa amb un risc reduït de DM2 i hipertensió en humans. A més, els ACN orals també milloren el perfil de lípids plasmàtics, el metabolisme de la glucosa i la funció endotelial, el que explica raonablement la reducció de el risc de DM2 associat amb la ingesta dietètica d'ACN. 6), L'administració oral de PC en animals millora la integritat i funció de la barrera intestinal a partir de tres mecanismes principals: a) la reducció de molècules proinflamadando respuesta a diversas preguntas como la biodisponibilidad tisular del ACN, el biomarcador de consumo y los efectos de su ingesta en la salud humana. Métodos: Se realizó 1 experimento animal en ratas hipercolesterolémicas y 6 revisiones sistemáticas de la literatura científica siguiendo los procedimientos metodológicos más adecuados entre febrero de 2018 y febrero de 2021. Resultados: De varias revisiones sistemáticas: 1) las ACN se pueden detectar en múltiples tejidos diana con relevancia médica sugiriendo efectos sobre la salud. 2) C3G es el único ACN que cumple los criterios para ser considerado un biomarcador de ingesta de bayas en el plasma y la orina humanos. 3) consumir 100-150 g/día de manzanas enteras mejora múltiples factores de riesgo de enfermedad cardiovascular (ECV), y mortalidad por ECV. 4) a partir de la intervención animal, las manzanas ricas en ACN tienen un efecto antiinflamatorio, mie
periment on hypercholesterolemic rats and 6 systematic reviews from the scientific literature were conducted following the most adequate methodological proceedings between February 2018 and February 2021. Results: From various systematic reviews: 1st, ACNs can be detected in multiple target tissues with medical relevance, suggesting some health effects. 2nd, C3G is the only ACN fulfilling the criteria to be considered an adequate food-intake biomarker for berry consumption in human plasma and urine. 3rd, consuming 100-150 g/day of whole-apples improves multiple CVD risk factors and reduces the risk of CVD and CVD mortality. 4th, from the animal intervention, ACN-rich apples have an anti-inflammatory
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Zeng, Hainian. "FOLIAR ANTHOCYANINS AND PROANTHOCYANIDINS IN SIX ORNAMENTAL VARIETIES OF ACER PALMATUM." NCSU, 2009. http://www.lib.ncsu.edu/theses/available/etd-11062009-103243/.
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Anthocyanins are one of the richest pigments, which belong to flavonoid compounds in plant kingdom. They have many biological and ecological functions. Over the past many years, numerous efforts have been made to determine the biosynthetic pathway of anthocyanins and also to identify several regulatory proteins mainly in flowers and fruits of model plants and crop plants. However, many questions concerning the metabolism of anthocyanins in foliage remains unsolved. One example is âHow can developmental processes impact on accumulation patterns of anthocyanins in leavesâ. In this study, we choose several cultivars from one of the most popular ornamental plants Acer palmatum Thunb. to understand the mechanism of developmental changes of pigmentation in leaf. Several other maple species were also analyzed. We propose that the metabolism of anthocyanins play an essential role in such changes. We use an integrated approach of phytochemistry and metabolic profiling to determine the biosynthesis and metabolism of anthocyanins and their impacts on foliage color. Proanthocyanidin analysis was carried out as well to determine their relationship to both anthocyanin production and foliar coloration. We have found that even for green leaves with no/trace amount of detectable anthocyanins, the biosynthetic pathway of anthocyanidin/proanthocyanidin is still activated. Our results indicate that metabolic channeling directing the anthocyanin pathway to the proanthocyanidin biosynthesis plays a very important role in pigmentation pattern change along developmental processes.
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Jing, Pu. "Purple corn anthocyanins: chemical structure, chemoprotective sctivity and structure/function relationships." The Ohio State University, 2006. http://rave.ohiolink.edu/etdc/view?acc_num=osu1155738398.
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Kamonpatana, Kom. "Metabolism and Anti-inflammatory Activity of Anthocyanins in Human Oral Cavity." The Ohio State University, 2012. http://rave.ohiolink.edu/etdc/view?acc_num=osu1354655642.
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Zikri, Nancy N. "A study of the chemopreventive effects of black raspberry components in rat esophageal epithelial cells." Columbus, Ohio : Ohio State University, 2008. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=osu1198691632.
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Henderson, Amy Elizabeth. "Can the Consumption of Fruits Containing Anthocyanins Reduce the Risk of Developing Type 2 Diabetes?" Fogler Library, University of Maine, 2007. http://www.library.umaine.edu/theses/pdf/HendersonAE2007.pdf.
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Petersson, Erik V. "Analysis of Acrylamide and Anthocyanins in Foods : Extraction Optimization for Challenging Analytes." Doctoral thesis, Uppsala universitet, Analytisk kemi, 2009. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-109752.
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In this thesis, the main concern has been to improve the reliability of different parts of the analytical workflow (Paper I, II, IV &V). Additionally, one of the resulting optimized methods was used in a real application (Paper III). Paper I-II concerned the extraction of acrylamide (AA) from foods. In Paper I different parameters such as sample particle size, extraction solvent, extraction time and extraction temperature were optimized, leading to a method that showed good agreement with the assigned AA levels of several proficiency test samples. Later, after the publication of the paper, the method showed good performance in a collaborative trial validation, in terms of trueness, repeatability and reproducibility figures. It was labeled “undoubtedly fit for the purpose”. In Paper II, it was shown that the ‘extra’ amounts of AA obtained during extraction of foods with an alkaline aqueous solution was not due to improved extractability of AA from the food matrix. Strongly alkaline conditions seemed to rather induce net formation of AA from water-soluble precursors formed during thermolysis. This phenomenon should therefore be regarded as an extraction artifact. Paper III was an application of the optimized method from Paper I, where it was used to study the reduction of AA in potato chips (crisps) by using pre-treatments and frying at reduced pressure. There were significant reductions in AA, down to below the limit of quantification (5 µg/kg) for the method. Paper IV-V concerned analysis of anthocyanins (AC) in red onion. In Paper IV, a new separation method using capillary electrophoresis was developed, and its rapidness combined with an acidic background electrolyte helped in preventing AC degradation. Furthermore, its alternative separation mechanism is a complement to that of the more commonly used liquid chromatography technique. In Paper V, simultaneous extraction and degradation of anthocyanins from red onion was studied in a static batch reactor at 110ºC. The extraction and degradation kinetics were successfully separated, and an ideal theoretical extraction curve was constructed by compensating mathematically for degradation effects, showing that more anthocyanins, 21 to 36% depending on different species, could be extracted if no degradation occurred. The results give important information about the different kinetics competing during an extraction procedure, and also show that quantitative extraction is not to recommend in the batch system used in the study.
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Wang, Xiaoxi. "Isolation and Purification of Anthocyanins from Black Bean Wastewater Using Macroporous Resins." DigitalCommons@USU, 2012. http://digitalcommons.usu.edu/etd/1523.
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Isolation and purification of anthocyanins from black bean canning wastewater by column chromatography with macroporous resins were investigated in this study. Different adsorption materials and adsorption conditions were compared and the most effective material and adsorption conditions were selected to purify anthocyanins. Purified anthocyanins then were identified by high performance liquid chromatography electrospray tandem mass spectrometry. The most effective macroporous resin was selected by comparing the adsorption performance of five different types of macroporous resins (Diaion Hp20, Sepabeads Sp70, Sepabeads Sp207, Sepabeads Sp700, and Sepabeads Sp710). Equilibrium adsorption isotherms of five resins with wastewater were measured and analyzed using Langmuir and Freundlich isotherm models. Both Langmuir and Freundlich models could describe the adsorption process. The adsorption and desorption behaviors of anthocyanins were studied using a dynamic method on the five types of resins, and Sp700 presented the highest adsorption capacity as well as desorption capacity, indicating that Sp700 is a good candidate for purification of anthocyanins from black bean canning wastewater. The most effective adsorption conditions were tested using Sp700. Dynamic adsorption and desorption were performed in glass columns packed with Sepabead Sp700 to optimize the purification process. Temperature during adsorption and desorption (25°C and 35°C) did not significantly affect the adsorption and desorption ratio. Adsorption ratio was significantly reduced when the flow rate increased from 1.5 mL/min to 2.5 mL/min. However, desorption ratio was not affected by flow rate (from 1.5mL/min to 0.3mL/min). Ethanol concentration (from 30% to 60%) did not affect desorption ratio. Four kinds of anthocyanins were identified in black bean canning wastewater. The major anthocyanins were delphinidin 3-glucoside, petunidin 3-glucoside, and maldvidin 3-glucoside, with a small amount of petunidin 3, 5-diglucoside also in the final product.
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Hosseini-Beheshti, Elham. "Characterization of antioxidant activities from fruits rich in delphinidin or malvidin anthocyanins." Thesis, University of British Columbia, 2008. http://hdl.handle.net/2429/912.
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Anthocyanins have been shown to possess specific antioxidant capacities, which
may provide an underlying protective effect against many chronic diseases . Although the
antioxidant capacity of anthocyanins has been well established, less is known about the
extent to which specific anthocyanin composition affects total antioxidant capacity . The
aim of the present study was to compare the antioxidant capacity of two different soft
fruits, blackcurrant and grape, which have distinctly different anthocyanin profiles.
The anthocyanin profiles of grape and blackcurrant were characterized by
HPLC/MS coupled with a diode array detector. Results showed that blackcurrant
contained four predominant anthocyanins, cyanidin 3-glucoside, delphinidin 3-glucoside,
cyanidin 3-rutinoside, and delphinidin 3-rutinoside . In contrast, malvidin 3-glucoside,
delphinidin 3-glucoside, cyanidin 3-glucoside, petunidin 3-glucoside, and peonidin 3-
glucoside were the major anthocyanins found in grape . The concentration of individual
anthocyanins in all berries was quantified with HPLC/UV using cyanidin 3-glucoside as
an external standard . Finally, results showed a greater (p<0.05) antioxidant capacity of
blackcurrant compared to grape. The total antioxidant capacity of crude extracts from
each was measured by Oxygen Radical Absorbance Capacity (ORAC) and ABTS assays.
Anthocyanin antioxidant capacity index (AACI), derived from the product of
antioxidant (ORAC) activity for each of major anthocyanin present in blackcurrant and
grape, was also used to determine whether the antioxidant capacity of crude anthocyanin
fractions represents either the sum total anthocyanin content or, alternatively, a synergy
between different anthocyanins components . Our results indicated that a plausible
potential synergy between anthocyanin components in regards to ORAC antioxidant
capacity existed in blackcurrant and grape semi-purified anthocyanin extracts.
Furthermore, it could be concluded that both total anthocyanin content as well as
the composition of individual anthocyanins in soft fruits is important to assess total
antioxidant capacity of different berry sources .
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Linsey, C. J. "A study on the analysis and the stability of anthocyanins from blackberries." Thesis, London South Bank University, 1985. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.353590.
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Polit, Maria Fernanda. "Characterization and quantification of anthocyanins and other phenolics in native Andean potatoes." Columbus, Ohio : Ohio State University, 2009. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=osu1243955949.
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Lago, C. "STUDY OF MAIZE GENOTYPES RICH IN ANTHOCYANINS FOR HUMAN AND ANIMAL NUTRITION." Doctoral thesis, Università degli Studi di Milano, 2014. http://hdl.handle.net/2434/230010.
Full textAbstract:
Anthocyanins are very important nutraceuticals not only because they protect plants against biotic and abiotic stresses (Winkel-Shirley, 2002) and they seem to be involved in plant yield (Frascaroli and Landi, 1998), but also because they exert antioxidant abilities able to protect human and animal health (Virgili and Marino, 2008). Maize is able to accumulate anthocyanin in different tissues (Escribano-Bailon et al., 2004; de Pascual-Teresa et al., 2002), so that it can be considered a functional food. On this basis the general aim of this PhD project was to develop maize genotypes with the usual commercial and nutritional value and at the same time able to accumulate anthocyanins in kernels, so to confer the new colored varieties a surplus value compared to the uncolored traditional ones.
In maize different allele combinations of the anthocyanin regulatory genes are able to color different tissues, in different extent. From the evaluation of these different genotypes some interesting results came to light: while the r1 gene seemed to be involved in maize yield, the B/Pl genotypes were able to reach the highest anthocyanin amounts in kernels. Therefore they were used to generate the lines characterized in this PhD thesis (popcorn, polenta and sweet corn). To develop uniform individuals, the parameters affecting the anthocyanin final amount in kernels had been studied: the seed weight, the pericarp thickness, the environment and the expression level of the regulatory genes. Among all, a primary role of the epigenetic phenomena emerged; this fact can complicate the breeding work because it force to select the most colored individuals generation by generation, so surely this aspect must be examined more in depth.
In the meanwhile a recurrent breeding scheme was used to develop pop corn, polenta and sugary corn colored with anthocyanin: a commercial yellow line was crossed with the colored variety carrying the B/Pl alleles for the anthocyanin biosynthesis. using the Marker Assisted Selection (M.A.S) to help the selection. The anthocyanin final amount in the kernels of the new developed colored lines has been considered as competitive compared to the usual anthocyanin sources, even if the cooking processing affected – but not wiped off- the pigment content and the antioxidant ability.
However the anthocyanin presence seemed not to affect the appreciability degree tested on a blinded group of subjects, so that the new color products could be ready for the market.
This kind of work and analyses are very interesting in regard the fact that two Near Isogenic Lines (NIL), differing for the synthesis of only one class of metabolites, are under comparison. This fact can simplify the study of the advantage given by the presence of the anthocyanins in foods; moreover these isogenic foods can also be used to analyze the relationship between the presence of the pigments in foods and the human and animal health and consequently to confer a property to a specific single class of molecules, simplifying the analyses and the reading of results.
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Watrelot, Aude. "Interactions non-covalentes entre les polyphénols et les pectines : Etude sur un substrat modèle : la pomme." Thesis, Avignon, 2013. http://www.theses.fr/2013AVIG0656/document.
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Les paramètres thermodynamiques et les cinétiques d’interactions entre des polyphénols (des procyanidines et des anthocyanes) et des fractions pectiques ont été déterminés par des méthodes physico-chimiques en solution et sur support solide. Les expériences ont été réalisées avec les anthocyanes majoritaires de cassis ou des procyanidines de type B (extraites de pomme) avec différents degrés de polymérisation et des fractions pectiques issues de pectines de pomme présentant divers degrés de méthylation et différentes chaines latérales d’oses neutres.Les interactions entre les anthocyanes et les pectines sont influencées par les substituants osidiques et le nombre de groupements hydoxyles du noyau B des anthocyanes ainsi que par la composition des fractions pectiques. Les constantes d’affinité entre les pectines et les procyanidines en solution sont les plus élevées quand le degré de polymérisation des procyanidines et le degré de méthylation des pectines sont les plus élevés. De plus, le niveau de ramification des pectines limite leur association avec les procyanidines. Ces interactions impliquent à la fois des liaisons hydrogènes et des interactions hydrophobes. Après les modifications chimiques et l’immobilisation des procyanidines sur une surface, les unités de résonance obtenues par résonance plasmonique de surface entre la (-)-épicatéchine ou le dimère DP2 et les pectines de pomme sont similaires à celles obtenues avec la protéine riche en proline IB5, mais plus faible qu’avec la sérum albumine bovineThermodynamical parameters and kinetics of interactions between polyphenols (procyanidins and anthocyanins) and pectic fractions were defined by physico-chemical methods in solution and with a solid support. Experiments confronted major anthocyanins presents in blackcurrant or B-type procyanidins from apple with various degrees of polymerization to pectic fractions from apple pectins presenting different degree of methylation and different neutral sugar side chains.Interactions between anthocyanins and pectins are influenced by the glycosyl substituent and the number of hydroxyl groups in the B-ring of anthocyanins, and by the composition of pectins. The affinity constant of procyanidins – pectins interaction in solution are the highest when both the procyanidins degree of polymerization and the pectins degree of methylation are the highest. Moreover, the ramification state of pectins limits their association with procyanidins. Those interactions are due to hydrogen bonds and hydrophobic interactions.After chemical modifications of procyanidins and immobilization on a solid support, the resonance units obtained by surface plasmon resonance between (-)-epicatechin or dimer B2 and apple pectins are similar to those obtained with the prolin-rich protein IB5 and lower than with bovine serum albumin
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Donner, Horst. "The anthocyanins of red onions, Allium cepa L, extraction, characterization, complexation and stabilization." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1998. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp05/mq23285.pdf.
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Georgilas, Athanasios-Panagiotis. "Animal proteins used as fining agents and their influence on the anthocyanins' profile." Master's thesis, ISA/UL, 2012. http://hdl.handle.net/10400.5/8610.
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Mestrado Vinifera EuroMaster - Instituto Superior de AgronomiaThe treatment of wine with fining agents is a common practice in the wine industry which aims to achieve wine’s clarity and improves its stability along the time. The objective of this work was to examine the influence of various animal proteins used as fining agents on the anthocyanins’ profile. For this experiment, two Portuguese varieties, Touriga Nacional and Trincadeira have been used in which two different concentrations have been applied for each fining product. The fining agents are commercial fining products widely used in the wine industry such as Egg Albumin, Isinglass, PVPP, Gelatin, Casesol. These proteins were added in the wines in order to perceive the effect of the adding protein and other fining agents on the wine’s anthocyanidins final composition, since that these monomeric anthocyanins have an important function on the sensory characteristics of wines, such as colour. The clarification process lasted 7 days for each fining product. At the end of each clarification period, monomeric anthocyanin analysis was carried out by HPLC. By the analysis in the HPLC, we perceived that in general the biggest impact from all the fining agents is displayed to the acylated and coumarylated derivatives of the monomeric anthocyanins rather than the 3-glucoside antocyanidins. Having this as a fact and learning through the initial analysis that Touriga Nacional is richer in these two groups rather than in glucoside derivatives we are able to explain why Touriga Nacional was more affected in all the fining treatments compared to Trincadeira that is poorer in acylated derivatives and in general it was less influenced by the fining agents. Moreover, further analysis have been carried out in order to examine the influence of the fining agents on the concentration of pigments, the quantity of condensed tannins as well as on the chromatic characteristics of the wine after fining. For the quantity of condensed tannins after fining, the results have shown that all the fining agents promoted a reduction on the final quantity of tannins after the treatments whereas for the pigments and colour intensity the impact was notably lower compared with the tannins. Regarding the impact on the colour anthocyanins, Casesol promoted the greatest influence on their quantity. In addition, the general tendency indicates that the fining products in high concentrations provoke a bigger decrease on the amount of total anthocyanins compared with the small concentrations