Dissertations / Theses on the topic 'Flavonoids – Synthesis'
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Schicker, Susanna Heidi. "Synthesis of intermediates for chalcone and 6-MSA biosynthesis." Thesis, University of Bristol, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.336910.
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Baugaard, Carlo. "The synthesis and electrochemical studies of chalcones and flavanones: an investigation of their antioxidant activity." Thesis, University of Western Cape, 2013. http://hdl.handle.net/11394/3312.
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>Magister Scientiae - MScFlavonoids, one of the biggest classes of secondary metabolites, are found abundantly in nature in a broad range of fruits, vegetables and beverages such as tea, coffee, beer, wine and fruit drinks. Flavonoids have been reported to exert multiple biological functions as well as tremendous pharmacological activity, including anticancer activity, protection, antioxidant activity, cardiovascular protection, antibacterial, antifungal and antiviral activity. The antioxidant activity of flavones is reported to be associated with those bearing hydroxyl functions. In the present study, several reaction steps have been carried out to synthesize three sub classes of flavonoids namely; chalcones, dihydrochalcones and flavanones with various substituents attached. The first step involved protection of hydroxyl groups of acetophenone and benaldehyde as starting materials. Thereafter the Clasien Schmidt condensation reaction, under basic conditions, was performed to afford chalcone intermediates. Treatment of these chalcones with sodium acetate, under reflux, afforded flavanones as a single product in high yields. Thereafter all protecting groups where removed to yield the final products. All products and intermediates where purified by column chromatography and were characterized by Nuclear Magnetic Resonance Spectroscopy (NMR) (1H NMR and 13C NMR). An electrochemical analysis on all flavonoid compounds was performed by Cyclic Voltammetry (CV) and Square Wave Voltammetry (SWV) to give information on the accessible redox couples identified by their oxidation potentials. Oxidation potentials, which gave valuable information about reducing ability and hence the antioxidant activity, where used to compare all compounds. The antioxidant activity was observed to increase with the addition of hydroxyl groups on the B-ring. Compounds with a combination of hydroxyl groups on the A-ring and methoxy groups on the B-ring showed increased antioxidant activity when compared to those with only hydroxyl groups on the base structure. 2, 5, 4’-trihydroxy dihydrochalcone showed moderate antioxidant ability. However the 2, 5, 4’-trihydroxychalcone, containing the α, β unsaturated double bond, proved to have the greatest antioxidant ability.
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Chalumeau, Céline. "Développement d’outils chimiques pour l’élucidation de la biosynthèse des flavonoïdes du raisin : anthocyanes versus proanthocyanidines." Thesis, Bordeaux 1, 2010. http://www.theses.fr/2010BOR14188/document.
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Ces dernières années, des progrès remarquables ont été accomplis afin d’élucider la biosynthèse des flavonoïdes. Cependant les dernières étapes menant à la formation des proanthocyanidines ou tannins condensés issus de la vigne, restent à ce jour inconnues. Dans le but de déterminer si une ou plusieurs enzyme(s) spécifique(s) sont impliquées dans cette voie de biosynthèse, nous avons développé une approche de protéomique chimique, impliquant des matrices d’affinité constituées de substrats de type flavanols greffés sur un support solide. La validation de ces outils à l’aide de LDOX, une enzyme issue de Vitis vinifera a pu être menée à bien dans le cadre de ces travaux de thèseRemarkable progress toward the complete elucidation of the biosynthesis of flavonoids has been accomplished during the last decade, but the final step leading to proanthocyanidins still remain to be elucidated, in particular, the exact nature of starter and extension units as well as the enzymatic or non enzymatic condensation process. In order to answer whether some specific enzymes are involved in the biosynthesis of grapevine proanthocyanidins, we have developped a chemical proteomics approach, with an affinity chromatography-based tool in which a flavanol type substrate is loaded on an appropriate solid support. The validation of these tools with the LDOX enzyme from Vitis vinifera was developped and performed in this Ph.D work
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Schmid, Matthias [Verfasser], and Thomas [Akademischer Betreuer] Magauer. "Biomimetic synthesis of complex flavonoids from East Indian Dragon's blood & total synthesis of salimabromide / Matthias Schmid ; Betreuer: Thomas Magauer." München : Universitätsbibliothek der Ludwig-Maximilians-Universität, 2019. http://d-nb.info/1191691993/34.
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Bauer, Anne-Katrin [Verfasser], Ludger A. [Akademischer Betreuer] Wessjohann, and Wolf-Dieter [Akademischer Betreuer] Fessner. "Biocatalytic synthesis of taste-modifying flavonoids / Anne-Katrin Bauer ; Ludger A. Wessjohann, Wolf-Dieter Fessner." Halle, 2016. http://d-nb.info/1120409942/34.
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Shih, Chun-hat, and 施振翮. "Molecular characterization and metabolic engineering of flavonoid biosynthesis in higher plants." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2009. http://hub.hku.hk/bib/B41633829.
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Castell, Auví Anna. "The effects of grape seed procyanidin extract on insulin synthesis and secretion." Doctoral thesis, Universitat Rovira i Virgili, 2012. http://hdl.handle.net/10803/79133.
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Las procianidinas son compuestos bioactivos presentes en frutas y vegetales. Aunque se conocen los efectos beneficiosos de estos compuestos en la homeostasis de la glucosa, su acción en la funcionalidad de la célula β no es clara. La presente tesis doctoral se ha centrado en describir los efectos de las procianidinas en la síntesis y secreción de insulina. Nuestros resultados muestran la capacidad de las procianidinas de modificar la funcionalidad de la célula β aumentando la relación insulina plasmática/mRNA, aunque la efectividad del tratamiento depende de la situación fisiológica. En situaciones no patológicas, las procianidinas afectan la insulinemia modificando la síntesis, secreción y/o degradación de la insulina. En situaciones de resistencia a la insulina, el tratamiento crónico con procianidinas disminuye la síntesis y secreción de insulina gracias a su acción limitando el acúmulo de lípidos. En cambio, en un modelo más dañado (obesidad genética), las procianidinas ejercen efectos similares pero no son capaces de mejorar la hipersinulinemia. En conclusión, las procianidinas, en las dosis ensayadas, pueden utilizarse únicamente como compuestos bioactivos limitando la disfuncionalidad de la célula β en sus estados iniciales.Les procianidines són compostos bioactius presents en fruites i vegetals. Tot i que es coneixen els efectes beneficiosos d’aquests compostos en l’homeòstasi de la glucosa, la seva acció en la funcionalitat de la cèl•lulaβ no és clara. La present tesi doctoral s’ha centrat en descriureels efectes de les procianidines en la síntesi i secreció d’insulina. Els nostres resultats mostren la capacitat de les procianidines de modificar la funcionalitat de la cèl•lula β augmentant la relació insulina plasmàtica/mRNA, tot i que l’efectivitat del tractamentdepèn de la situaciófisiològica. En situacions no patològiques, les procianidines afecten la insulinèmia modificant la síntesi, secreciói/o degradació d’insulina. En situacions de resistència a la insulina, el tractamentcrònicamb procianidines disminueix la síntesi i secreció d’insulina gràcies a la seva acció limitant l’acumulació de lípids. En canvi, en un model més danyat (obesitat genètica), les procianidines exerceixen efectes similars però no son capaces de millorar la hiperinsulinèmia. En conclusió, les procianidines, en les dosis assajades, podenutilitzar-seúnicament coma compostos bioactiuslimitant la disfuncionalitat de la cèl•lula β en els seus estats inicials.
Procyanidins are bioactive compounds found in fruits and vegetables widely consumed. It has been reported that procyanidins show some beneficial effects on glucose homeostasis, although their effects on β-cell functionality remain unresolved. This doctoral thesis is focus on describing the effects of procyanidins on insulin synthesis and secretion. Our results showed that procyanidins modify β-cell functionality through increasing the plasma insulin/mRNA ratio, although the effectiveness of the treatment depends on the physiological situation. Under non-pathological situation, procyanidins affected insulinaemia by modifying insulin synthesis, secretion and/or degradation activity. Under insulin-resistance situation, chronic procyanidins administration decreased insulin synthesis and secretion, thanks to its lipid-lowering effect. Otherwise in a more damaged model, Zucker fatty rat, procyanidins treatment is not able to reduce insulin plasma levels although they repress insulin expression. In conclusion, procyanidins could be used as bioactive compound to limit β-cell dysfunctions under high-palatable diets, but at the assayed doses, it is not enough to counteract a strong metabolic disruption.
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GONZALEZ, EMMANUEL. "Contribution a l'etude des flavonoides. Synthese et activite anti-radicalaire de flavonols isolement, identification et syntheses d'anthocyanes." Université Louis Pasteur (Strasbourg) (1971-2008), 2000. http://www.theses.fr/2000STR13077.
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Le travail decrit dans cette these porte sur la famille des flavonoides et en particulier sur les flavonols et les anthocyanes. Dans la premiere partie, nous presentons une nouvelle methode de synthese de flavonols basee sur le rearrangement de baker-venkataraman, a partir de reactifs communs peu couteux, et donnant de bons rendements globaux. Les reactions utilisees ne mettent pas en uvre des oxydants puissants prejudiciables a des substituants sensibles ou au flavonol synthetise lui-meme. Nous avons ainsi prepare une serie homologue de flavonols dont nous avons mesure et compare l'efficacite reductrice vis-a-vis du radical stable colore 1, 1-diphenyl-2-picryl-hydrazyle (dpph) en solution modele. Une echelle relative du pouvoir antioxydant incluant l'acide ascorbique, un antioxydant bien connu, a ete construite. La comparaison de l'efficacite anti-radicalaire des flavonols a permis de degager des relations reliant leur structure a leur reactivite. Dans la deuxieme partie, nous exposons la synthese d'anthocyanes substituee en position 4 par des chaines alkyles, montrant une relative stabilite de leur couleur dans des conditions inhabituelles. En modifiant la longueur et la nature de la chaine alkyle, on modifie egalement la coloration resultante qui va du jaune au bleu. Nous avons etudie les anthocyanes responsables de la couleur des fleurs rouges et de la couleur des fleurs violettes du cultivar festival de petunia hybrida. Nous avons cherche, isole et identifie par diverses techniques spectroscopiques les anthocyanes du milieu vacuolaire afin d'en determiner le ph. Nous y avons decouvert deux nouvelles anthocyanes de structures complexes jamais decrites dans la litterature.
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Keßberg, Anton. "Enantioselektive Synthese bioaktiver Flavane und Isoflavane." Doctoral thesis, Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden, 2018. http://nbn-resolving.de/urn:nbn:de:bsz:14-qucosa-236526.
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Im Rahmen dieser Arbeit wird eine neuartige Deoxygenierungskaskade von Flavanonen bzw. Isoflavanonen via asymmetrischer Transferhydrierung (ATH) beschrieben. Diese Methodik ermöglicht einen einstufigen Zugang zu enantiomerenreinen Flavanen bzw. Isoflavanen aus entsprechenden racemischen Ketonen. Unter Verwendung der ATH-Deoxygenierungskaskade werden hoch enantioselektive Naturstoffsynthesen elaboriert. So erfolgt eine effiziente Darstellung der Flavane Brosimin A, Brosimin B, Brosimacutin L, Kazinol U und 7,3‘-Dihydroxy-4‘-methoxyflavan. Darüber hinaus wird mittels dynamischer kinetischer Racematspaltung die Totalsynthese der Isoflavane Equol, Manuifolin K und Eryzerin D beschrieben.
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Caldwell, Stuart Thomas. "The synthesis of isotopically labelled flavonoid glucosides." Thesis, University of Glasgow, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.250932.
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Arnaudinaud, Valérie. "Hémisynthèse et synthèse totale de flavonoi͏̈des marqués." Bordeaux 2, 2000. http://www.theses.fr/2000BOR28764.
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Perruchon, Sophie. "Synthese und Struktur-Aktivitäts-Beziehungen von Flavonoiden." [S.l. : s.n.], 2004. http://elib.tu-darmstadt.de/diss/000409.
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Gelebe, Aifheli Carlson. "Synthetic and spectrometric studies of benzodioxepinone derivatives." Thesis, Rhodes University, 1995. http://hdl.handle.net/10962/d1005047.
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An extensive range of oxygen and sulphur substituted benzodiazepine analogues has been synthesised via Baeyer-Villiger and Schmidt reactions of specially prepared flavanone and N-acetyl-4-quinolone precursors. Alternative, cyclisation routes have also been used to prepare some of these compounds. Ring-opening reactions of 1,5-benzodioxepinones have been investigated and a detailed kinetic-mechanistic study of the Baeyer-Villiger reaction of flavanones has been carried out using 1 H NMR spectroscopy to explain the observed regiochemistry of oxygen insertion. The electron-impact mass spectrometric fragmentation patterns of series of 4-aryl-l ,5-benzoxathiepinones, 3-aryl-4, I-benzoxathiepinones and 3-aryl-4,1-benzoxathiepines have been studied using a combination of low-resolution, highresolution and metastable-peak analyses. The 170 NMR spectroscopic properties of various oxygenated analogues have also been studied. The binding affinities of selected benzodiazepine analogues for rat brain benzodiazepine receptors have been evaluated using a radioreceptor assay technique; at certain concentrations, some of test compounds exhibited remarkable potentiation of diazepam binding, others the ability to displace diazepam from benzodiazepine receptors. A conformational analysis of the 7-membered ring systems has been undertaken, using lH NMR spectroscopic, computer modelling and x-ray crystallographic techniques, and certain conformational preferences have been identified.
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Adiji, Olubu Adeoye. "Identification, Characterization and Engineering of UDP-Glucuronosyltransferases for Synthesis of Flavonoid Glucuronides." Thesis, University of North Texas, 2020. https://digital.library.unt.edu/ark:/67531/metadc1752363/.
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Flavonoids are polyphenolics compounds that constitute a major group of plant specialized metabolites, biosynthesized via the phenylpropanoid/polymalonate pathways. The resulting specialized metabolites can be due to decoration of flavonoid compounds with sugars, usually glucose, by the action of regiospecific UDP-glycosyltransferase (UGT) enzymes. In some cases, glycosylation can involve enzymatic attachment of other sugar moieties, such as glucuronic acid, galactose, rhamnose or arabinose. These modifications facilitate or impact the bioactivity, stability, solubility, bioavailability and taste of the resulting flavonoid metabolites. The present work shows the limitations of utilizing mammalian UDP-glucuronosyltransferases (UGATs) for flavonoid glucuronidation, and then proceeds to investigate plant UG(A)T candidates from the model legume Medicago truncatula for glucuronidating brain-targeted flavonoid metabolites that have shown potential in neurological protection. We identified and characterized several UG(A)T candidates from M. truncatula which efficiently glycosylate various flavonoids compounds with different/multiple regiospecificities. Biochemical characterization identified one enzyme, UGT84F9, that efficiently glucuronidates a range of flavonoid compounds in vitro. In addition, examination of the ugt84f9 gene knock-out mutation in M. truncatula indicates that UGT84F9 is the major UG(A)T enzyme that is necessary and sufficient for attaching glucuronic acid to flavonoid aglycones, particularly flavones, in this species. Finally, the identified UG(A)T candidates were analyzed via homology modeling and site-directed mutagenesis towards increasing the repertoire of UG(A)Ts applicable for synthesis of flavonoid glucuronides with potential human health benefits in neurological protection.
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Hernández, Blanco Inés Angeles. "Synthese und Untersuchung der antioxidativen Eigenschaften von vinylog verlängerten Flavonoiden antioxidative Eigenschaften von natürlichen Carotinoiden /." [S.l. : s.n.], 2003. http://deposit.ddb.de/cgi-bin/dokserv?idn=969925425.
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Hoffmann, Thomas. "Modifizierte Flavonoide als neuartige UVA-Schutzmittel Synthese, Untersuchungen zur Photostabilität und zum Singulett-Sauerstoff-Quenchverhalten /." [S.l.] : [s.n.], 2004. http://deposit.ddb.de/cgi-bin/dokserv?idn=971538832.
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Nay, Bastien. "Intérêts, statégies et approches expérimentales en synthèse chimique totale de flavanoi͏̈des et tanins condensés." Bordeaux 2, 1998. http://www.theses.fr/1998BOR2P100.
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Pouget, Christelle. "Pharmacomodulation de flavonoi͏̈des : conception et synthese de nouveaux inhibiteurs de l'aromatase." Limoges, 2001. http://www.theses.fr/2001LIMO308H.
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BUFFNOIR, STEPHANE. "Synthese et marquage de flavonoides mettant en jeu la chimie organometallique - synthese de la prenylcatechine et acces aux dimeres de flavonoides - activation du couplage de stille par l'ion fluorure - marquages de la catechine et de l'epicatechine." Paris 6, 1998. http://www.theses.fr/1998PA066050.
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Nous avons developpe une nouvelle voie d'acces selectif aux dimeres de flavonoides, par synthese convergente, a partir de la (+)-catechine. L'utilisation d'une activation par l'ion fluorure de la reaction de couplage de stille permet d'acceder aux dimeres de type catechine(4-8)catechine. Par ailleurs, nous avons utilise cette activation dans la synthese de la prenylcatechine naturelle qui n'avait jamais ete realisee. Nous avons mis en evidence l'activation de la reaction de couplage de stille, en conditions douces dans le tetrahydrofurane, par l'ion fluorure. Les difluorotriorganostannates presentent une activation par rapport aux derives tetraorganostannanes correspondant. Nous avons fait, in situ, des derives monofluorotetraorganostannates par reaction de tetraorganostannanes avec une source d'ion fluorure. Ces composes presentent, dans les conditions douces du couplage de stille, une incroyable activation par rapport aux reactifs tetracoordines habituellement utilises. Nous avons fait plusieurs etudes sur le catalyseur, le solvant, la temperature et le nombre d'equivalent d'ion fluorure. Cette activation a ete etendu en version carbonylante ainsi qu'aux elements proches dans la classification periodique. Nous avons mis en evidence le meme type d'activation pour les derives du silicium, du germanium, du plomb et du bismuth. Enfin, nous avons developpe un marquage selectif de l'heterocycle des flavan-3-ols par oxydation et reduction successives de la fonction alcool en position 3. Nous obtenons la catechine et l'epicatechine deuteree et tritiee sur la position 3 avec de bons rendements, de bons exces diastereomeriques et une activite specifique forte. L'ensemble des stereochimies des molecules synthetises a ete verifiee par la methode des esters de mosher couplee a la rmn du proton et du fluor.
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Petrella, Dominic Paul. "The Induction and Photoregulation of Flavonoid Synthesis in Poa trivialis L. and its Impact on Salt Stress Sensitivity." The Ohio State University, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=osu1490679768554881.
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McDonald, Lucas J. "Synthesis and Characterization of Novel Flavonoid-Based Fluorescent Sensors and other Sensors with Excited State Intramolecular Proton Transfer for Biological Applications." University of Akron / OhioLINK, 2018. http://rave.ohiolink.edu/etdc/view?acc_num=akron1524658238472646.
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BEUDOT, CECILE. "Evaluation de la mutagenicite et de l'antimutagenicite de flavonols et de flavones d'origine naturelle et de synthese par le test d'ames." Aix-Marseille 2, 1998. http://www.theses.fr/1998AIX22117.
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De nombreuses proprietes physiologiques et pharmacologiques caracterisent les flavonoides, principales molecules d'origine vegetale presentes dans notre alimentation. Parmi celles-ci, des activites mutagenes et antimutagenes ont ete mises en evidence dans des tests a court terme de mutagenese. Notre travail a consiste a rechercher la mutagenicite et l'antimutagenicite de 49 4-oxo-flavonoides d'origine naturelle et de synthese par le test d'ames. Les resultats montrent que la quercetine est le flavonol le plus mutagene parmi les molecules naturelles, c'est aussi la plus polaire (cinq groupements hydroxyles). La plupart des 3-nitroflavones et des 3-aminoflavones de synthese se revele mutagene ; leur mutagenicite s'exerce selon deux mecanismes : soit par une activite intrinseque des molecules soit par la reduction des groupements nitro et amino portes par les cycles aromatiques. Les proprietes antimutagenes des molecules ont ete recherchees vis-a-vis de 11 mutagenes de reference : le tnf, le bpde, l'icr191, le 2af, le 2aa, le bap, le 4-nqo, l'ems, le mms, le mnng et la mitc. Nous avons obtenu une efficacite d'inhibition maximale avec l'isorhamnetine et avec la 3-chloroflavone. A faibles doses, une dualite d'action en mutagenese et en antimutagenese a pu etre detectee pour la quercetine, la rhamnetine, la tamarixetine et le kaempferide. Ce phenomene a fait l'objet d'une etude plus approfondie avec la quercetine en presence d'icr191. Nos resultats montrent que le flavonol agit en realite comme un inhibiteur competitif vis-a-vis de l'icr191. Des etudes de chromatographie liquide haute pression ont enfin permis de suivre la stabilite des flavonols mutagenes d'origine naturelle et de la 3-nitroflavone. Les flavonols se revelent instables a partir d'un ph de 7,4 ; la quercetine est fortement degradee dans les conditions du test d'ames et la 3-nitroflavone se transforme en un compose plus polaire depourvu d'activite mutagene a ph 7,4.
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Medu, Erere Ohwofasa. "Examination of the antibacterial activities of some semi-synthetic chalcone-derivatives alone and in combination with polymyxin B." Thesis, Robert Gordon University, 2013. http://hdl.handle.net/10059/832.
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In view of the increasing global challenge of bacterial resistance, there exists an urgent need for the rationale development of antibacterial compounds with either novel or multiple mechanisms of action. Two chalcone-derivatives, F1 and F23, demonstrated MICs within the range of 16 to >512 μg/ml against two plant pathogens (P. caratovoram and C. michiganensis subsp. michiganensis) as well as important clinical bacterial species. Both compounds displayed an MIC of 32 μg/ml against quinolone-resistant S. aureus. Whilst possessing weak activities individually, each semi-synthetic agent displayed notable synergistic action with polymyxin B against S. aureus, C. violaceum, E. coli and Ps. aeruginosa, thereby recording FICs within the range of <0.093 to 2 that indicated the existence of synergism in some instance. These chalcone compounds applied with polymyxin B displayed a notable FICindex of <0.093 against the Neisseriaceae C. violaceum, and a potential noteworthy capacity to extend the spectrum of activity of the latter antibiotic to include Gram-positive S. aureus species. F1 inhibited staphylococcal replication in broth and the combination of either of both chalcone-derivatives with polymyxin B instituted a metabolic blockage in S. aureus and other bacterial species as determined through a modified MTT reduction assay. The combined agents inflicted major disruptions to the S. aureus cytoplasmic membrane bilayer as evidenced by the release of intracellular potassium as well as the influx of Sytox Green fluorescent stain. Notable levels of cell membrane potential dissipation, leakage of intracellular potassium ions and blockage of reducing enzymes activities occurred within the first 30 minutes, well in advance of significant loss in cell viability that was recorded usually after 4 – 8 hours, suggesting these activities were prerequisites to cell death. In erythrocyte lysis assay, the synergistic combinations of 128 μg/ml of either of both chalcone derivatives with 128 μg/ml polymyxin B displayed the lowest degree of haemolysis, followed by that occurring with 32 μg/ml of the chalcone-derivatives combined with 256 μg/ml of the polypeptide antibiotic. In conclusion, further structure activity modifications aimed at improving the aqueous solubility of these chalcone-derivatives as well as the antibacterial activity recorded for certain combination concentrations of polymyxin B with either of these semi-synthetic agents may be required before considerations are made for the possibility for potential external formulations. Such preparations may include antiseptic creams, lotions, ointments, as well as aerosols that can be applied with nebulizers in targeted delivery for such cases like cystic fibrosis.
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Mende, Steffen [Verfasser], Thomas [Akademischer Betreuer] Lindel, and Stefan [Akademischer Betreuer] Schulz. "Naturstoffe mit oxidierter Chroman-Teilstruktur : Totalsynthese des Flavonols Morin aus dem Färbermaulbeerbaum Maclura tinctoria und Untersuchungen zur Synthese von Dankastatin C aus dem Pilz Gymnascella dankaliensis / Steffen Mende ; Thomas Lindel, Stefan Schulz." Braunschweig : Technische Universität Braunschweig, 2020. http://d-nb.info/121529364X/34.
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Huang, Wei-Hao, and 黃瑋豪. "Synthesis the Derivatives of Flavonoids." Thesis, 2012. http://ndltd.ncl.edu.tw/handle/72646072169434842872.
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碩士國立東華大學
化學系
100
Flavonoids such as wogonin and oroxylin A performed potent anti-free radical activity, anti-inflammation, anti-lipid peroxidation, and inhibition of tumor cell growth. Wogonin was isolated from Scutellaria baicalensis Georgi, and found can induce cell apoptosis. In addition, oroxylin A effectively induces the vasodilatation to prevent or alleviate the hypertention. One of the flavonoids, PD98059 selectively blocks the activity of MAP kinase kinase (MAPKK), therefore inhibits the activation of MAP kinase (MAPK) and cell growth. Furthermore, another study found that PD98059 remarkably attenuates low-density lipoprotein (LDL) and decreases the cardiovascular diseases caused by atherosclerosis. In this work, the synthesis of flavonoids analogues conjugated the structures of wogonin, oroxylin A, and PD98059. We got two kinds of methods to synthesize these derivatives of flavonoid compound. We expect these compounds with good biological activity.
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Hsieh, Cheng-Kuo, and 謝正國. "Synthesis and Bioactivities of Flavonoids." Thesis, 2004. http://ndltd.ncl.edu.tw/handle/68089234110768365729.
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碩士國防醫學院
藥學研究所
92
Flavonoids, exerting antioxidant, anti-inflammatory, antiallergic, antibacterial, antiviral, antineoplastic, anti-thrombotic, hepatoprotective and hormone regulatory activity, are the natural polyphenol compounds. Four series of flavonoid analogs, flavones (6a-e), 3-phenylcoumarins (11-12), 4-hydroxy-3-phenylcoumarins (14a-d) and coumestans (15a-b), were synthesized and evaluated in vitro bioactivities of inhibition of NO production, free radical scavenging, antineoplastic and anti-HBV activities. The preliminary screenings showed that 6a, 6b, 6c, 6d , 12 and 15b have potent inhibitory activity of NO production, 12, 14c and 14d exerting good activity of free radical scavenging, 6c, 6d and 15b exhibiting antineoplastic activity at 20µg/ml and 6a, 6d, 15a and intermediate 13b bearing good anti-HBV activity at 25-100 µM. The results demonstrated that compounds bearing 2,2-dimethyltetrahydropyran moiety enhance the cell cytotoxicity and anti-HBV activity, whereas compounds flanking more hydroxyl groups increase the inhibitory activity of NO production and free radical scavenging activity.
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CHU, HAN-WEI, and 朱漢威. "Total Synthesis of Flavonoids and Related Precursor of Theaflavin." Thesis, 2004. http://ndltd.ncl.edu.tw/handle/37392034921862430988.
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碩士國立彰化師範大學
化學系
92
Abstract This thesis describes the total synthesis of a series of natural occurring flavonoids including quercetin 1-4, flavone 5-6, and polymethoxylated flavones such as isosinensetin 7, sinensetin 8, 5-hydroxylsinensetin 9, 5-hydroxylimocitrin 10, hexa- methoxylimocitrin 11, nobiletin 12, natsudaidain 13 and 3,3’,4’,5,6,7,8-heptamethoxy- flavone 14. All of the target molecules were completed from the key intermediate 1-(2-hydroxy-4,6-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)-propenone (16) via the subsequent processes: (1) regioselective methylation and demethylation reaction, (2) I2/pyridine oxidative cyclization reaction and, above all, (3) regioselective hydroxylation by DMD. Furthermore, the relative result was utilized in synthesizing the precursor of theaflavin.
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Martins, Beatriz Torgal. "Synthetic analogues of marine natural flavonoids as antifouling agents: synthesis and biological evaluation." Dissertação, 2017. https://hdl.handle.net/10216/107436.
Full text
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Martins, Beatriz Torgal. "Synthetic analogues of marine natural flavonoids as antifouling agents: synthesis and biological evaluation." Master's thesis, 2017. https://hdl.handle.net/10216/107436.
Full text
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Lee, Jian-Ming, and 李健銘. "Synthesis of Neoflavonoids and Flavonoids catalysed by Montmorillonite K-10." Thesis, 2002. http://ndltd.ncl.edu.tw/handle/14542992854533278642.
Full textAbstract:
碩士國立彰化師範大學
化學系
90
Synthesis of Neoflavonoids and Flavonoids Catalysed by Montmorillonite K-10 Large number of natural products and medicinal compounds have the skeleton of flavone which are known as potential antitumor agents and humanimmounodeficiency virus (HIV) type 1 integrase inhibitors. As part of a recent search to prepare new biologically active substance, we were attracted to the coumarin and flavonoide family whose members are widely distributed in biologically important natural products and pharmaceutical agents. Because of the biological activity, we undertook to search an useful method on synthesis both of them. Here in, we report a new approach to synthesis of neoflavonoids and flavones based on Montmorillonite K-10. And the stereo-selectivity of flavonoids will be discussed.
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Deodhar, Mandar Chemistry Faculty of Science UNSW. "Synthesis of heterocyclic dimers derived from isoflavones and flavones." 2007. http://handle.unsw.edu.au/1959.4/40832.
Full textAbstract:
The primary aim of this project was to synthesize new heterocyclic dimers of isoflavones and flavones, and investigate various methodologies for their synthesis. The secondary aim of the project was to synthesize some flavonoid natural products. Dimeric systems were synthesized using various methodologies including acid catalyzed arylation of isoflavanols and flavanols, acid catalyzed dimerization of flavenes, oxidative dimerization, Sonogashira coupling, Ullmann coupling and Suzuki-Miyaura coupling reactions. The acid catalyzed arylation of isoflavanols was found to proceed in a very stereoselective fashion to give trans-4-arylisoflavans in good yield in a single step. However, related flavanols under similar conditions gave mixtures of cis and trans isomers of 4-arylflavans. Interestingly, it was found that appropriately substituted flavenes, upon treatment with acid undergo stereoselective rearrangement and dimerization to give benzopyranobenzopyrans in high yields. A rationale for the rearrangement is proposed and this dimerization was used for the stereoselective synthesis of the natural product dependensin. As part of the project, some polycyclic natural products such as octandrenolone, flemiculosin, 3-deoxy-MS-II and laxichalcone were also synthesized. Oxidative dimerization of activated isoflavones was found to be very regioselective, and novel isoflavone dimeric systems were synthesized. Related flavones however, failed to undergo dimerization under similar conditions. A probable explanation for high regioselectivity in the case of isoflavones and unreactivity of flavones has been presented. Phenol oxidative coupling was used for the one-step synthesis of another natural product kudzuisoflavone-A from daidzein. Sonogashira coupling was utilized for the synthesis of dimeric systems linked via an acetylic linker. A variety of soflavone isoflavone, flavone-flavone and isoflavone-flavone dimers were synthesized in "one-pot" by this methodology and in excellent yields. Although Ullmann coupling was found not to be suitable for the synthesis of isoflavone or flavone dimers, one-pot Suzuki-Miyaura methodology gave flavone dimers and various other heterocyclic dimers in good yields.
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Swinny, Ewald Eugene. "The structure and synthesis of metabolites from virgilia oroboides and chlorophora excelsa (Iroko)." Thesis, 1989. http://hdl.handle.net/10413/9967.
Full textAbstract:
In the present study the acetone extract of the heartwood of two trees, Virgilia oroboides and Chlorophora excelsa, were investigated. The heartwood of Virgilia oroboides afforded a variety of known flavonoids, as well as a new pterocarpene and a new α-hydroxydihydrochalcone, viz.;
3-hydroxy-8, 9-methylenedioxy-6a,11a-dihydropterocarpan
(αS), 2' ,4'-trihydroxy-4-methoxydihydrochalcone. A series comprising substituted hydroxygeranylstilbenes, substituted benzenoid compounds and quercitin-type flavones were isolated from the acetone extract of the heartwood of Chlorophora excelsa. The new compounds isolated from this tree are: 3,5-dihydroxy-4-geranylbenzaldehyde; 3' ,4,5'-trihydroxy-4'-geranylstilbene; 2'-methoxy-3, 4',7-tri-O-methylquercitin.
A combination of solvent extraction, Craig countercurrent,
column (LH 20 and silica gel) and thin layer chromatography
procedures were used to isolate and purify the compounds
mentioned. Structures were elucidated by high resolution (300 MHz) ¹HNMR spectroscopy (including NOE and spin-spin decoupling experiments) and mass spectrometry.
The proposed structural assignments of the following compounds were confirmed by synthesis:
3, 5-dihydroxy-4-geranylbenzaldehyde; 3' ,4 ,5'-trihydroxy-4' -geranylstilbene; 2 ,3' ,4 ,5'-tetrahydroxy-4' -geranylstilbene (chlorophorin).
The modified Wittig reation was used to synthesize 3' ,4 ,5' trihydroxystilbene.
U.V. irradiation experiments were performed on chlorophorin in an attempt to synthesize the cis-isomer and a phenanthrene-type compound. Biosynthetic pathways showing the structural relationships of the identified compounds in Virgilia oroboides and Chlorophora excelsa were proposed. An attempt to synthesize (+)-catechin lignoid involved the coupling of (+)-catechin to sinapyl alcohol, with the latter synthesized from 2 ,6-dimethoxyphenol via vinyl quinone methide. Further investigations on lignoid currently in progress.Thesis (M.Sc.)-University of Durban-Westville, 1989.
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Selepe, Mamoalosi Alix-Maria. "Synthesis and analysis of Eriosema isoflavonoids and derivatives thereof." Thesis, 2011. http://hdl.handle.net/10413/6409.
Full textAbstract:
Kraussianone 1 and kraussianone 2 were previously isolated as active compounds from the roots of Eriosema kraussianum Meisn., a plant used for the treatment of male impotence and urinary complaints in KwaZulu-Natal. The objectives of this study were firstly, to develop a method for the analysis of metabolites from E. kraussianum and other Eriosema plants that are used for erectile dysfunction and secondly, to develop synthetic methods for
kraussianone 1 and structurally related compounds.
A reversed-phase HPLC-PDA method was developed for the analysis of the extracts of plants from different sources, two of which were authentic E. kraussianum collected from the Drakensberg and Pietermaritzburg. The roots of other Eriosema species called ubangalala and uqonsi in Isizulu were also analysed. These plants were bought from the local herbal traders. The extracts of the two E. kraussianum plants and one uqonsi sample
showed a similar chemical profile, even though there were variations in the relative concentrations of the metabolites within each plant. In these three plants, kraussianone 1, the most active metabolite of E. kraussianum, occurred in relatively low quantities, whereas kraussianone 2 was one of the major constituents. The other commercial plants that were analysed contained different compounds from those found in E. kraussianum.
The HPLC method developed herein facilitates rapid identification and relative quantification of metabolites from E. kraussianum.
Strategies based on semi-synthesis and total synthesis were employed for the preparation of kraussianone 1. The semi-synthetic route was based on the transformation of the prenyl side chain of kraussianone 2 into a linear dimethylpyran scaffold fused to the A-ring. Two routes were investigated for the semi-synthesis of kraussianone 1 from kraussianone 2. In
the first route, the dimethylchromene ring was to be prepared by the acid-catalysed cyclisation of the prenyl group of kraussianone 2, followed by dehydrogenation of the resulting dimethylchroman chromophore. This route was abandoned due to poor regioselectivity of the cyclisation reaction and the difficulty of oxidising the dimethylchroman scaffold on the phloroglucinol moiety into a dimethylchromene. The second strategy involved selective protection of the OH-2', followed by DDQ-mediated oxidative cyclisation of the prenyl group to OH-7. This was the most viable route and
kraussianone 1 was prepared in an overall yield of 54% from kraussianone 2.
The total synthesis of kraussianone 1, on the other hand, employed the Suzuki-Miyaura reaction for the construction of the isoflavone nucleus and the regioselective introduction of the dimethylpyran scaffolds to the A- and B-rings. The key precursors in this synthesis were 3-iodo-5,7-dimethoxymethoxychromone and a boronic acid coupling partner, 7-
benzyloxy-2,2-dimethylchromene-6-boronic acid, already bearing the prerequisite chromene scaffold attached to the B-ring. The isoflavones genistein, 2-hydroxygenistein, eriosemaone D and a geranyl analogue of kraussianone 1 were prepared via the route developed for the total synthesis of kraussianone 1 by structural modifications of rings A and B. Furthermore, this synthetic approach was expanded to the synthesis of the
coumarochromones lupinalbin A and lupinalbin H. The development of the feasible semi-synthetic and total synthetic routes described herein
for kraussianone 1 is of importance for the production of material for an in depth study of the pharmacological activities and the structure-activity relationship studies of kraussianone 1 and related compounds.Thesis (Ph.D.)-University of KwaZulu-Natal, 2011.
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"Structural and synthetic studies of sesquiterpenoids and flavonoids isolated from Helichrysum species." Thesis, 2008. http://hdl.handle.net/10413/164.
Full textAbstract:
The genus Helichrysum (Asteraceae) consists of approximately 500 species worldwide,
with 245 indigenous to South Africa. As a result of the large number of species, the
chemistry and biological activity of several species have not yet been investigated. The aim
of this project was to investigate the phytochemistry of three species and propose a
synthetic route to one of the antibacterial compounds isolated.
An extensive literature review regarding the widespread traditional uses, biological activity
and phytochemistry of the South African Helichrysum species is provided.
From Helichrysum splendidum, a plant used traditionally to treat rheumatism, two
monomeric guaianolides and a dimeric guaianolide, helisplendidilactone, were isolated.
The stereochemistry of these known compounds was confirmed and the NMR assignments
for certain peaks of helisplendidilactone were corrected. An X-ray structure for
helisplendidilactone was obtained for the first time.
The phytochemistry of Helichrysum montanum was investigated for the first time and new
diastereoisomers of known guaianolides were isolated. The phytochemistry of H.
splendidum and H. montanum is remarkably similar and supports their morphological
classification in the same taxonomic group. The chloroform:methanol extract of H.
montanum yielded a new dimeric guaianolide, 13’-epihelisplendidilactone, which is related
to helisplendidilactone, as well as three monomeric guaianolides (of which one is a new
diastereomer of a known compound). The extract also yielded spathulenol (a
sesquiterpene), umbelliferone (a coumarin) and 4’,5,7-trihydroxy-3,3’,8-trimethoxyflavone
(a flavonoid).
Thirty-five Helichrysum species were screened for antimicrobial activity against six microorganisms
and a preliminary cytotoxic assay, which included the use of “normal” and
cancer cell lines, was performed. H. excisum was selected for further study based on the
fact that it exhibited promising antimicrobial activity and relative low toxicity.
Furthermore, with the exception of the essential oil, the phytochemistry of this species has
not been investigated. From the aerial parts of H. excisum, five flavonoids, identified as pinocembrin, gnaphaliin,
lepidissipyrone, 5-hydroxy-7,8-dimethoxyflavone and isoscutellarein 7-O-b-glucoside
were isolated. Four of these flavonoids have an unsubstituted B-ring, a phenomenon often
observed in flavonoids isolated from Helichrysum species. The active antimicrobial
component of H. excisum has been identified as lepidissipyrone.
Owing to the interesting biological activities reported for phloroglucinol a-pyrones and the
synthetic challenges associated with these molecules, lepidissipyrone was selected for a
synthetic study. Both the flavanone and pyrone moieties present in lepidissipyrone have
been successfully synthesised. A successful strategy towards the CH2 linker between the
two units has been illustrated. The strategy could be used to synthesise similar
phloroglucinol-derived pyrones.Thesis (Ph.D.) - University of KwaZulu-Natal, Pietermaritzburg, 2008.
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Ahmed, Ishtiaq [Verfasser]. "Study of enantioselective epoxidation, asymmetric reduction and synthesis of bioactive oligomeric flavonoids / von Ishtiaq Ahmed." 2007. http://d-nb.info/989595676/34.
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Ndoile, Monica Mbaraka. "Structure, synthesis and biological activities of biflavonoids isolated from Ochna serrulata (Hochst.) Walp." Thesis, 2012. http://hdl.handle.net/10413/8586.
Full textAbstract:
The phytochemistry of Ochna serrulata (Hochst.) Walp. was investigated for the first
time; two new dimeric chalcones (5-deoxyurundeuvine C and serrulone A) and two
new biflavonoid derivatives (4,4’,7-tri-O-methylisocampylospermone A and 4”’-de-Omethylafzelone
A) were isolated. These compounds were isolated along with the
known compounds lophirone A, afzelone B, campylospermone A,
isocampylospermone A, ochnaflavone, 2”,3”-dihydroochnaflavone, lophirone C,
psilosin, 3’-O-methylpsilosin, a cyanoglucoside, epicatechin, (2’,4’-
dihydroxyphenyl)acetic acid, methyl (2’,4’-dihydroxyphenyl)acetate, irisolone 4’-
methyl ether, iriskumaonin 3’-methyl ether, 3',4'-dimethoxy-6,7-methylenedioxyisoflavone, lophirone L, syringaresinol and 16α,17-dihydroxy-entkauran-19-oic acid.
The growth inhibitory effect of these compounds was evaluated against three cancer
cell line panel of TK 10 (renal), UACC62 (melanoma) and MCF7 (breast) using a
sulforhodamine B (SRB) assay. Ochnaflavone and 3’-methoxypsilosin demonstrated
selectivity and only inhibited the growth of melanoma cancer cells. However,
ochnaflavone showed higher activity by totally inhibiting the growth of melanoma
cancer cells at 12.91 μM, whereas, 3’-O-methylpsilosin has this effect at a
concentration of 14.11 μM. Lophirone C, a dimeric chalcone, demonstrated the
highest cytotoxic activity amongst all isolated compounds against renal, melanoma
and breast cancer cells with TGI at 35.63 μM, 11.67 μM and 30.35 μM, respectively.
Lophirone A, a rearranged biflavonoid, showed TGI against these cancer cells at
58.96 μM, 26.23 μM and 40.01 μM, respectively. The rest of the compounds showed
no significant cytotoxicity against the three cancer cells.
The new biflavonoid, 4,4’,7-tri-O-methylisocampylospermone A demonstrated the
highest antimalarial activity against chloroquine-resistant strains of Plasmodium
falciparum (FCR-3) with IC50 of 11.46 μM, followed by ochnaflavone (17.25 μM).
iv
Serrulone A (26.52 μM), lophirone A (29.78 μM), 5-deoxyurundeuvine C (31.07 μM),
lophirone C (35.31 μM), 4”’-de-O-methylafzelone A (38.43 μM), afzelone B (39.54
μM), irisolone 4’-methyl ether (40.72 μM) and syringaresinol (42.66 μM) were
moderately active. The following compounds exhibited the lowest antimalarial activity,
2”,3”-dihydroochnaflavone (61.86 μM), iriskumaonin 3’-O-methyl ether (93.69 μM),3’-
O-methylpsilosin (106.35 μM) and16α,17-dihydroxy-ent-kauran-19-oic acid (106.48
μM).
Owing to the observed and reported biological/pharmacological activity, ochnaflavone
(an ether-linked biflavone consisting of apigenin and luteolin moieties) was selected
for synthetic studies. An older method, nucleophilic aromatic substitution (SNAr) was
successfully applied in the construction of the diary ether. Oxidative ring cyclization of
the ether-linked dimeric chalcone was achieved by using heated pyridine and iodine.
The two methods can be extended further in the synthesis of other novel biflavones
with ether linkage.Thesis (Ph.D.)-University of KwaZulu-Natal, Pietermaritzburg, 2012.
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Cheng, Zhi-Jiao, and 鄭智交. "Studies on the antioxidant activities of plant flavonoids and the inhibitory action mechanisms of Broussochalcone A on nitric oxide synthesis in macrophages." Thesis, 2000. http://ndltd.ncl.edu.tw/handle/89403819237261758267.
Full textAbstract:
博士國立臺灣大學
藥理學研究所
88
The antioxidant activities of some plant flavonoids were investigated in this study. Besides, we studied the inhibitory action mechanism of broussochalcone A (BCA), one of the plant flavonoids, on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophages. The antioxidant properties of prenylflavones, isolated from Artocarpus heterophyllus Lam., were evaluated in this sutdy. Among them, artocarpine, artocarpetin, artocarpetin A and cycloheterophyllin diacetate and peracetate had no effect on iron-induced lipid peroxidation in rat brain homogenate. They also did not scavenge the stable free raidcal 1,1-diphenyl-2-picrylhydrazyl (DPPH). In contrast, artonin A, artonin B and cycloheterophyllin inhibited iron-induced lipid peroxidation in rat brain homogenate (IC50： 0.47±0.24, 0.71±0.13 and 0.96±0.21 mM) and scavenged DPPH radical (IC0.20： 8.4±0.3, 12.2±0.6 and 9.6±0.7 mM). They also scavenged peroxyl radical and hydroxyl radical that were generated by 2,2''-azobis(2-amidinopropane) dihydrochloride (AAPH) and Fe3+-ascorbate-EDTA-H2O2 system, respectively. However, they did not scavenge superoxide radical derived from xanthine/xanthine oxidase system, hydrogen peroxide, carbon-centered radical or peroxyl radical derived from 2,2''-azobis(2,4-dimethylvaleronitrile) (AMVN) in hexane. Moreover, artonin A, artonin B and cycloheterophyllin inhibited copper-catalyzed oxidation of human low-density lipoprotein (LDL), as measured by fluorescence intensity, thiobarbituric acid-reactive substance (TBARS) formation and LDL electrophoretic mobility. It is concluded that artonin A, artonin B and cycloheterophyllin serve as powerful antioxidants against lipid peroxidation when biomembranes are exposed to oxygen radicals. Butein, isolated from Dalbergia odorifera T. Chen, inhibited iron-induced lipid peroxidation in rat brain homogenate in a concentration-dependent manner with an IC50, 3.3±0.4 mM. It also scavenged the stable free radical DPPH with an IC0.20 , 9.2±1.8 mM, and inhibited the activity of xanthine oxidase with an IC50 , 5.9±0.3 mM. Besides, butein scavenged the peroxyl radical derived from AAPH in aqueous phase, but not that from AMVN in hexane. Furthermore, butein inhibited copper-catalyzed oxidation of human LDL, as measured by conjugated-dienes and TBARS formations and LDL electrophoretic mobility in a concentration-dependent manner. Spectral analysis revealed that butein was a metal chelator of ferrous and copper ions. It is proposed that butein serves as a powerful antioxidant against lipid and LDL peroxidation by its versatile free radical scavenging actions and metal ions chelation. The antioxidant properties of BCA and its effects on NO production in LPS-activated macrophages were investigated in this study. BCA, isolated from Broussonetia papyrifera Vent., inhibited iron-induced lipid peroxidation in rat brain homogenate in a concentration-dependent manner with an IC50 , 0.63 ± 0.03 mM. In DPPH assay system, the radical-scavenging activity of BCA seemed as potent as a-tocopherol and their IC0.20 were 7.6 ± 0.8 mM and 10.8 ± 0.8 mM, respectively. BCA could directly scavenge superoxide and hydroxyl radicals. These results indicate that BCA is a powerful antioxidant with versatile free radicals scavenging activity. On the other hand, we found that BCA suppressed NO production concentration-dependently in LPS-activated macrophages with IC50 , 11.3±0.8 mM. This effect was not the consequence of a direct inhibitory action on the enzyme activity of iNOS. Our results indicated that BCA exerts potent inhibitory effects on NO production, apparently by its suppression on IkBa phosphorylation, IkBa degradation, NF-kB activation and iNOS expression. Therefore, we conclude that the antioxidant activities of BCA and its inhibition on IkBa degradation and iNOS protein expression may have therapeutically potential, because the excessive free radicals and NO production are associated with various inflammatory diseases.
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Guimarães, Cristina Rafaela dos Santos Albuquerque. "Towards antioxidant and antitumor properties of wild medicinal plants traditionally used in Portugal: extracts, isolated flavonoids, and their human metabolites obtained by chemical synthesis." Doctoral thesis, 2016. http://hdl.handle.net/1822/41853.
Full textAbstract:
Tese de Doutoramento em Ciências (Especialidade em Química)According their empirical relevance in traditional medicine and diets, six wild species from the Portuguese medicinal flora were selected as important sources of phenolic compounds, namely flavonoids. The present study aimed to characterize the phenolic composition and evaluate bioactive properties (antioxidant, antitumor and antiangiogenic) of methanolic extracts, infusions and decoctions prepared from Chamaemelum nobile and Matricaria recutita, and Prunus spinosa, Arbutus unedo, Rosa micrantha and Rosa canina fruits; and to synthesize derivatives/metabolites of some flavonoids present in the studied samples. The main phenolic compounds in C. nobile extract, decoction and infusion were flavonols, flavones, phenolic acids and derivatives. The extract gave the highest antioxidant activity in the β-carotene bleaching and TBARS formation inhibition assays. The highest radical scavenging activity and reducing power were observed in the infusion. The extract showed the highest antitumor (in different human tumor cell lines) and antiangiogenic (phosphorylation inhibition of VEGFR-2) activities. M. recutita infusion and decoction showed better results than the extract in the radical scavenging activity and β-carotene bleaching inhibition assays. The antitumor activity of the extract and infusion showed to be selective for HCT-15 and HeLa cell lines. Luteolin-O-acylhexoside was the most abundant flavonoid in the three preparations. 3- O-Caffeoylquinic acid was the most abundant phenolic compound in P. spinosa, quercetin 3-O-glucoside in A. unedo, and taxifolin in R. micrantha and R. canina. P. spinosa revealed to be the most rich in anthocyanins. Two different enriched phenolic extracts were prepared, in order to compare their bioactivity: non-anthocyanin phenolic compounds enriched extract (PE) and anthocyanins enriched extract (AE). A. unedo (PE) and R. canina (AE) presented the highest antioxidant activity in all the assays, and the highest antitumor activity was observed in A. unedo (PE and AE). The synthesis of derivatives/metabolites of flavonoids was performed using quercetin or quercetin 3-Orutinoside (rutin) (identified in the studied samples) affording O-tri and different O-tetra protected (benzyl or methyl) quercetins that were submitted to glucuronidation attempts using acetobromo-α-ᴅ-glucuronic acid methyl ester in order to obtain possible precursors of human metabolites. As complex mixtures were obtained, further studies are needed to allow the formation of higher amounts of the required glucuronide derivatives to enable their isolation in a pure form.
De acordo com a sua relevância empírica na medicina tradicional e utilização em dietas, foram selecionadas seis espécies silvestres da flora medicinal Portuguesa, como fontes importantes de compostos fenólicos, nomeadamente flavonoides. O presente estudo teve como objetivo caracterizar a composição fenólica e avaliar as propriedades bioativas (antioxidante, antitumoral e antiangiogénica) de extratos, infusões e decocções preparadas a partir de Chamaemelum nobile e Matricaria recutita, e frutos de Prunus spinosa, Arbutus unedo, Rosa micrantha e Rosa canina; e sintetizar derivados/ metabolitos de alguns flavonoides presentes nas espécies estudadas. Os compostos fenólicos mais abundantes no extrato, decocção e infusão de C. nobile foram flavonóis, flavonas, ácidos fenólicos e derivados. O extrato mostrou a maior atividade antioxidante nos ensaios de inibição da descoloração do β-caroteno e da formação de TBARS. A maior atividade captadora de radicais livres e o maior poder redutor foram observados na infusão. O extrato mostrou maior atividade antitumoral (nas diferentes linhas celulares tumorais) e antiangiogénica (inibição da fosforilação do VEGFR-2). A infusão e a decocção de M. recutita mostraram maior atividade captadora de radicais livres e inibição da descoloração do β-caroteno do que o extrato. Os efeitos antitumorais do extrato e da infusão mostraram ser seletivos para as linhas celulares HeLa e HCT-15. A luteolina-Oacil- hexósido foi o flavonoide mais abundante nas três preparações. O ácido 3-Ocafeoilquínico foi o composto fenólico mais abundante em P. spinosa, enquanto que a quercetina 3-O-glucósido foi o maioritário em A. unedo, e a taxifolina foi o mais abundante em R. canina e R. micrantha. P. spinosa revelou o maior teor em antocianinas. Prepararam-se dois extratos fenólicos diferentes de forma a comparar a sua bioatividade: um extrato enriquecido em compostos fenólicos sem antocianinas (PE) e um extrato enriquecido em antocianinas (AE). A. unedo (PE) e R. canina (AE) apresentaram a maior atividade antioxidante em todos os ensaios, e a maior atividade antitumoral foi observada em A. unedo (PE e AE). A síntese de derivados/metabolitos dos flavonoides foram realizados usando a quercetina e rutina (quercetina 3-O-rutinósido) (identificados nas amostras estudadas) obtendo-se O-tri e diferentes O-tetra (benzil ou metil) quercetinas protegidas, que foram submetidas a tentativas de glucuronidação usando o éster metílico do ácido acetobromo-α-ᴅ-glucurónico a fim de obter possíveis precursores de metabolitos humanos. Tendo-se obtido misturas complexas, são necessários mais estudos para permitir a formação de quantidades mais elevadas dos glucuronidos requeridos, que possibilitem o isolamento dos compostos numa forma pura.
Fundação para a Ciência e Tecnologia (FCT) - Portugal for the financial support through to the Portuguese NMR network and through PEst-C/QUI/UI0686/2011- 2012 and 2013-2014, PEst-OE/AGR/UI0690/2011-2012, 2013 and 2014, supporting the research centres (CQUM and CIMO, respectively) and through my PhD grant (SFRH/BD/ 8307/2011) also supported by POPH-QREN and FSE.
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Ramonetha, Thata Golden. "Synthetic and spectroscopic studies of 6-substituted chromone derivatives." Diss., 2015. http://hdl.handle.net/11602/772.
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Lu, Wei-chieh, and 呂葳婕. "Synthetic Studies and Pharmacy Testing of Flavonoids." Thesis, 2007. http://ndltd.ncl.edu.tw/handle/20657533127812370001.
Full textAbstract:
碩士嘉南藥理科技大學
藥物科技研究所
95
In this report, 5,6,7-trimethoxy flavonoids derivatives were synthesized starting from 3,4,5-trimethoxyphenol. The synthesized flavonoids were also experiment for their antioxidant activities, evaluated using assays of 1,1-diphenyl-2-picrylhydrazyl (DPPH), trolox equivalent antioxidant capacity (TEAC), and inhibit liposome peroxidation methods. And they were also evaluated using assays of inhibit tyrosinase for skin-lightening. In the other, thery were experiments using the MTT assay to measure the effects of flavonoisd on cell cytotoxicity. In 1,1-diphenyl-2-picryl-Hydrazyl (DPPH) radical scavenging activity and inhibit liposome peroxidation methods, which free radical scavenging activity were very weak. In TEAC assay, compound 24、28 present more then 75% scavenging activity when the sample concentration were at 0.20 mg/mL and 0.40 mg/mL. In inhibit tyrosinase test, the inhibition activity of compound 25、27 and 28 were between 35% to 40% when the sample concentration were 0.20 mg/ml. In MTT assay demonstrated that the toxicity of three carbon more then two carbon substitute for B-ring of C’4 position on the flavonoids derivatives.
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Burke, Anthony. "Studies in the Synthesis and Chemistry of Flavonoid epoxides." Doctoral thesis, 1992. http://hdl.handle.net/10174/24673.
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Huang, Min-Huei, and 黃敏惠. "Synthesis of Acylated Flavonoide Glycosides Analogue in Old Oolong Tea." Thesis, 2011. http://ndltd.ncl.edu.tw/handle/k7wjwe.
Full textAbstract:
碩士國立中興大學
化學系所
99
We successfully synthesized two acylated monoglycosides by coupling D-glucose with cinnamic acid and coumaric acid, separately. Then these two acylated monoglycosides underwent glycosidation to produce acylated diglycosides. The developed synthetic method allows the preparation of acylated flavonoide glycosides derivatives for further explorations toward the origins of their biological activities.
43
Alves, Joana Filipa Catarino. "Chemo-enzymatic synthesis of new flavonoid derivatives with anti-inflammatory activity." Master's thesis, 2018. http://hdl.handle.net/10316/84606.
Full textAbstract:
Dissertação de Mestrado em Química Farmacêutica Industrial apresentada à Faculdade de FarmáciaNos últimos anos, vários estudos epidemiológicos apontaram o consumo prolongado de alimentos ricos em flavonoides como um benefício para a saúde, no qual se inclui a prevenção de várias doenças, como o cancro e a diabetes, além das doenças cardiovasculares e neurodegenerativas. Alguns dos seus efeitos protetores têm sido associados à sua atividade anti-inflamatória. A inflamação crónica é, de facto, uma das principais causas de mortalidade no mundo ocidental, uma vez que desencadeia várias patologias humanas, incluindo a diabetes, aterosclerose, cancro e Alzheimer. Visto que os fármacos anti-inflamatórios atuais apresentam diversas limitações e que a produção anormal de mediadores pro-inflamatórios aumenta e sustenta a inflamação, compostos direcionados para a expressão destes últimos são bons candidatos para a atenuação de doenças inflamatórias, como por exemplo, substâncias químicas direcionadas à expressão da isoforma indutível da sintase do óxido nítrico (iNOS) e à produção de óxido nítrico (NO). A baixa estabilidade e solubilidade em meio lipofílico limitam a aplicação prática de flavonoides. Assim sendo, a síntese enzimática de derivados acilados de flavonoides glicosilados surge como uma estratégia eficaz para superar este problema. O uso de processos químicos requer muitas etapas de proteção/desproteção para obter acilação seletiva e, portanto, a via biocatalítica, que é regio e estereosseletiva, é escolhida como um método eficaz para a realização de tais reações e assim melhorar a sua lipofilicidade. Tendo em conta estas premissas, o presente trabalho visa sintetizar e caracterizar novos derivados acilados dos flavonoides rutina e naringina, utilizando a Novozym 435 como catalisador, com vários ésteres vinílicos (acetato de vinilo, propionato de vinilo, butirato de vinilo e cinamato de vinilo) como doadores de grupo acilo e também mostrar os potenciais efeitos anti-inflamatórios dos derivados de naringina, utilizando o modelo de inflamação in vitro de macrófagos RAW 264.7 estimulados com lipopolisacárido (LPS). Os resultados obtidos sugerem que a natureza do doador do grupo acilo pode ser um fator determinante para a regiosseletividade da lipase e para o rendimento da reação. Além disto, os resultados mostram que a acilação da naringina aumentou a sua atividade no que diz respeito à inibição do NO. Particularmente, a naringina 6''-butanoato (C4) foi o composto mais potente no que diz respeito à inibição da expressão de iNOS, seguido por naringina 6''-propanoato (C3), levando a supor que compostos diacilados ou compostos acilados com doadores de cadeia longa podem interagir melhor com a membrana celular devido ao aumento do seu carácter lipofílico, aumentando a internalização da naringina pelas células e melhorando assim o seu efeito anti-inflamatório.
In the last years, epidemiological studies suggested that long term consumption of food rich in flavonoids is related to health benefits, such as prevention of diverse diseases including cancer and diabetes, along with cardiovascular and neurodegenerative diseases. Some of their protective effects have been associated to their anti-inflammatory activity. As a matter of fact, chronic inflammation is one of the leading causes of mortality in western world since it triggers multiple human pathologies, including diabetes, atherosclerosis, cancer and Alzheimer. Since the current anti-inflammatory drugs have several limitations and the abnormal production of pro-inflammatory mediators increases and sustains inflammation, compounds targeting their expression are good candidates for attenuating inflammatory diseases, for example chemicals targeting inducible nitric oxide synthase (iNOS) expression and nitric oxide (NO) production. The low stability and solubility in lipophilic medium limit the practical application of flavonoids. Therefore, enzymatic synthesis of acylated derivatives of glycosylated flavonoids arises as an effective strategy to overcome this problem. Moreover, the use of chemical processes requires many protection/deprotection steps to obtain selective acylation, and the biocatalytic route, which is region- and stereoselective, is chosen as an effective method to perform such reactions and to improve their lipophilicity. Taking into account these assumptions, the present work aims to synthesize and characterize new acylated derivatives of the flavonoids rutin and naringin, catalysed by Novozym 435, with various vinyl esters (vinyl acetate, vinyl propionate, vinyl butyrate and vinyl cinnamate) as acyl donors and to disclose the potential anti-inflammatory effects of naringin derivatives using the in vitro model of inflammation lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. The results obtained suggest that the nature of the acyl donor can be a determining factor for the regioselectivity of the lipase and for the reaction yields. Moreover, the results show that the acylation of naringin enhanced its activity towards NO inhibition. Particularly, naringin 6''-butanoate (C4) was the most potent compound in inhibiting iNOS expression, followed by naringin 6''-propanoate (C3), leading to hypothesize that diacylated compounds or acylated compounds with long chain acyl donors can better interact with the cell membrane due to its increased lipophilicity, providing a mean of enhancing the internalization of naringin by cells, thus improving its anti-inflammatory effect.
44
劉諺至. "Antioxidation and Antitumor Effects of the Synthetic Flavonoid Derivatives." Thesis, 2004. http://ndltd.ncl.edu.tw/handle/60186784581720154129.
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45
Perruchon, Sophie. "Synthese und Struktur-Aktivitäts-Beziehungen von Flavonoiden." Phd thesis, 2004. https://tuprints.ulb.tu-darmstadt.de/409/1/Thesis_Perruchon_2004_D_AllTeil.pdf.
Full textAbstract:
Flavonoide sind polyphenolische Verbindungen, die in zahlreichen Pflanzen weit verbreitet sind. Viele von ihnen besitzen biologische Eigenschaften (als Radikalfänger, Entzündungshemmer...), die möglicherweise auf kosmetischem Gebiet möglicherweise nutzbar sind. Flavonoide absorbieren beispielsweise im UV-Bereich, was ihnen gute UV-Filtereigenschaften verleiht. In unserem Labor wurden Flavonoide und polyphenolische Derivate untersucht um zu verstehen, welcher Teil des Moleküls für die obengenannten Eigenschaften verantwortlich ist. Ausgehend von mono- oder polyhydroxylierten Aromaten wurden einfache Synthesen von bekannten und neuen, mono- und polyphenolischen Verbindungen entwickelt, die in einer Substanzbibliothek zusammengefasst wurden. Durch Veränderung der Hydroxylierungsposition an den Benzolringen, war es möglich Moleküle mit sehr interessanten Eigenschaften zu erhalten. Unter diesen absorbiert das 7-Hydroxy-4?-methoxyflavon sowohl im UVB-, als auch im UVA- Bereich mit sehr hohen Extinktionskoeffizienten. Einige der synthetisierten Moleküle besitzen beste Voraussetzungen, um als Abfänger für freie Radikale zu wirken. Es könnte gezeigt werden, dass diese in vitro auf molarer Basis wirksamere Antioxidanzien sind als Vitamin E. Diese Ergebnisse wurden sowohl durch Variation des Substitutionsmusters um den Kern der Flavonoide als auch des Oxydationsgrads der Verbindungen erreicht (z.B. Bacalein). Die biologische Wirkung von 7-O-Glucosyl-4?-methoxyflavon wurde daruberhinaus mit cDNA-Matrizen geprüft, welche eine Gruppe von mehr als 400 mit der Haut assoziierte Gene enthalten. Ausgesuchte Verbindungen der Musterbibliothek wurden außerdem darauf hin untersucht, inwieweit sie in der Lage sind Tyrosine-Kinasen zu hemmen.
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Tomé, Sara Mirassol. "Synthesis of flavonoid-type compounds and sugar-substituted phenolics of pharmacological importance." Doctoral thesis, 2021. http://hdl.handle.net/10773/31390.
Full textAbstract:
Flavonoids are a large class of secondary metabolites widespread in the Plant
Kingdom. These natural organic compounds possess a prominent interest as
therapeutic agents. Among the vast range of biological properties of both natural
and synthetic derivatives are their antioxidant and anti-inflammatory activities.
Among the naturally occurring oxygen containing heterocyclic compounds,
flavones (2-arylchromones) assume pronounced importance due to both their
spread and diverse abundance as well as their well-known wide range of
pharmacological properties. Halogenated derivatives of this privileged structure
already proved to display enhanced biological activities and are also valuable
frameworks as intermediates in the synthesis of more elaborated compounds,
namely through metal cross-coupling reactions. Although several methods have
already been developed towards the synthesis of haloflavones, there is still much
room for improvement regarding the regioselectivity control of the halogenation
process. The chemistry of this scarce group of natural compounds remains,
therefore, an interesting challenge to organic chemists.
Part of the work described in this thesis was focused on the synthesis of
flavonoid-type compounds. Regarding the synthesis of flavones, synthetic
pathways towards different substituted patterns of methoxy-, hydroxy- and
chloroflavones were studied. The newly synthesised compounds were evaluated
for their antioxidant, anti-inflammatory and antidiabetic properties and several of
them exhibited remarkable activities including a great potential towards the
treatment of type 2 diabetes mellitus. The structure–activity relationship study
(SAR) of the prepared compounds was performed. Moreover, it were achieved
the stereoselective synthesis of the novel (E,E)-aminoaurone-type compounds,
as well as the preparation of different new analogues of
iodophenyloxybenzaldeydes and iodoxanthones.
Natural occurring phenolic compounds are frequently attached to carbohydrate
moieties. The recognized prominent interest on C-glycosyl-substituted phenolic
compounds in medicinal chemistry lies on the combination of the distinguishing
hydrolytic stability of their C-glycosidic bond and the high hydrophilic character
of the carbohydrate unit together with the well-known biological activities of
phenolic compounds. Accordingly, the development of general approaches for
the synthesis of C-glycosyl phenolic compounds is of great importance. In this thesis the study on the synthesis of C–C sugar-substituted phenolics is
also described. The used synthetic strategy was based on the Heck cross coupling of vinylfuranose or vinylpyranose sugar scaffolds with different
halophenolic frameworks. This straightforward wide in scope methodology lead
to different types of phenolic-sugar hybrid molecules: phenoxybenzaldehyde–,
xanthone–, chromone–, (E)-2-styrylchromone–, and (E,E)-aminoaurone-type–
sugar hybrids.
The unequivocal structural elucidation of all synthesised compounds was
performed by 1D and 2D nuclear magnetic resonance experiments and
supported by mass spectrometry and by either elemental analysis or high
resolution mass spectrometry.Os flavonoides são uma ampla família de metabolitos secundários ubíquos no Reino Vegetal. Estes compostos orgânicos de ocorrência natural têm sido alvo de grande interesse de estudo devido ao seu reconhecido potencial farmacológico. Entre as suas múltiplas propriedades biológicas destacam-se as atividades antioxidante e anti-inflamatória tanto de derivados naturais como de derivados sintéticos. No universo dos compostos heterocíclicos de oxigénio, as flavonas (2- arilcromonas) assumem especial importância devido à sua abundância, diversidade e amplo leque de propriedades farmacológicas às quais estão associadas. Alguns derivados halogenados desta estrutura molecular tão privilegiada provaram possuir atividades biológicas aprimoradas, sendo ainda valiosos intermediários na síntese de outros compostos orgânicos, nomeadamente mediante reações de acoplamento cruzado. Apesar de existirem vários métodos de síntese de haloflavonas, muito permanece ainda por desvendar relativamente ao controlo da regiosseletividade na halogenação. Parte do trabalho descrito nesta tese centrou-se na síntese de compostos do tipo flavonoide. Foram desenvolvidas novas rotas de síntese para a obtenção de novas flavonas com diferentes padrões de substituição: flavonas metoxiladas, hidroxiladas e cloradas em várias posições do seu esqueleto carbonado. Foi efetuada a avaliação biológica destes compostos assim como o estudo da relação estrutura–atividade (SAR), tendo alguns derivados exibido atividades antioxidante e anti-inflamatória muito satisfatórias e comprovado potencial no tratamento da diabetes mellitus tipo 2. Foram ainda estudadas a síntese estereoesseletiva de novos derivados do tipo (E,E)-aminoaurona e a preparação de novos análogos de iodofeniloxibenzaldeídos e iodoxantonas. Na natureza os compostos fenólicos encontram-se frequentemente associados a unidades de hidratos de carbono. No âmbito da química medicinal, o reconhecido e crescente interesse nos compostos fenólicos C-glicosilados advém da combinação de várias caraterísticas vantajosas a estes inerentes: a distinta estabilidade hidrolítica da ligação C-glicosídica, o elevado caráter hidrofílico proporcionado pelas unidades de açúcar e ainda tudo isto associado à reconhecida importância biológica dos compostos fenólicos. Nesta dissertação é também descrito o estudo efetuado no âmbito da síntese de novos compostos fenólicos substituídos por unidades de açúcar mediante ligações C–C. Para tal, foram preparados derivados vinilados de açúcar (do tipo furanose e piranose) e também derivados halofenólicos do tipo fenoxibenzaldeído, xantona, cromona, (E)-2-estirilcromona e (E,E)- aminoaurona. Tendo como estratégia-chave a reação de acoplamento cruzado de Heck, foi possível a síntese de vários novos derivados fenólicos contendo unidades de açúcar. A elucidação estrutural inequívoca de todos os compostos sintetizados foi efetuada através da espetroscopia de ressonância magnética nuclear 1D e 2D e sustentada pela análise de espetrometria de massa, análise elementar ou espetrometria de massa de alta resolução.
Programa Doutoral em Química
47
Chen, Chih-An, and 陳志安. "Synthesis of Flavonoid C-Glycosides as Antioxidants for Protection of Retinal Pigment Epithelial Cells." Thesis, 2008. http://ndltd.ncl.edu.tw/handle/49190313271853512744.
Full textAbstract:
碩士國立臺灣大學
化學研究所
96
A variety of C-glycosylflavonoids are found widely distributed in the plant kingdom. Dendrobium huoshanense is a well-known traditional Chinese medicine. Apigenin 6,8-di-C-glycosides have been suggested to exist in D. huoshanense to exhibit an activity for eye protection. Because the structure of the chemical constituent and the biological mechanism were unclear, we aim to synthesize a series of apigenin 6,8-di-C-glycosides and analogues for the structure–activity relationship study. A key reaction was carried out by using Sc(OTf)3 as the promoter to furnish the C-glycosylation on phloroacetophenone with unprotected saccharides. The key compound was further converted to mono- and di-C-glycosides of apigenin. In order to increase the diversity, different sugars (D-glucose, L-arabinose, D-xylose etc.), and phenols were used to synthesize the analogues.
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Perruchon, Sophie [Verfasser]. "Synthese und Struktur-Aktivitäts-Beziehungen von Flavonoiden / vorgelegt von Sophie Perruchon." 2004. http://d-nb.info/97036184X/34.
Full text
49
Mohammed, Hamdoon [Verfasser]. "Natural and synthetic flavonoid derivatives with potential antioxidant and anticancer activities / von Hamdoon Mohammed." 2009. http://d-nb.info/999319167/34.
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50
Chuang, Da-Wei, and 莊大緯. "The improvement in manufacturing of protoapigenone and the synthetic design of its flavonoid derivatives." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/25210645079947513380.
Full textAbstract:
博士高雄醫學大學
天然藥物研究所
101
Protoapigenone, a novel flavonoid isolated from the endemic fern of Taiwan (Thelypteris torresiana, Thelypteridaceae), possesses unique anti-tumor activity against several cancer cell lines that is even comparable to effect of the clinical drug doxorubicin. With the help of the National Science and Technology Program for Biotechnology and Pharmaceuticals (NSTPBP), several pre-clinical studies related to protoapigenone had begun, and some of them are completed recently. However, in order to support the need of every pre-clinical test, there must be a way to provide stable and large-scale sources of compounds. Although the original total synthetic study of protoapigenone has been accomplished, there are a lot of problems remain to be solved when it comes to a large-scale preparation. This study is aiming to modify the original synthetic method and provide a more efficient way to the scale-up condition. By using the commercial available naringenin as the starting material and iodine as the oxidizing agent, apigenin can be obtained with high yield without purification. After aids of microwave and hypervalent iodine reagents, protoapigenone is obtained with an improved yield in only two steps compared to the previous six-step reaction. This modification not only affords a higher total yield for the whole scheme but also greatly saves the time for the production of protoapigenone. Besides the modification of original synthetic scheme, this study also focuses on the research of flavone precursor synthesis and a useful crown-ether mediated cyclization strategy is developed. By combining the microwave-assisted oxidation, different protoapigenone derivatives will be synthesized efficiently. Finally, from the viewpoint of structure-activity relationship (SAR), the study of quinolones and β-naphthoflavone derivatives are also investigated. Among all the compounds synthesized, 59l exhibited the best in vitro activity and currently this compound is selected as one of the new lead candidates in the project of National Research Program for Biopharmaceuticals (NRPB). Now a series of pharmacology and animal studies about 59l have proceeded. We hope that through the cooperation of different scholars from different academic fields a new anti-cancer drug could be developed from 59l derivatives and make great contributions to the health of human beings.