Dissertations / Theses on the topic 'Antitumoral properties'
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Panosa, Roqueta Clara. "Antitumoral properties of epidermal growth factor derivatives." Doctoral thesis, Universitat de Girona, 2015. http://hdl.handle.net/10803/369050.
Full textEls receptors i lligands de la família del factor de creixement epidèrmic (EGF)/ErbB són dianes molt importants en el desenvolupament de teràpies contra el càncer. No obstant, l’eficàcia terapèutica dels fàrmacs dirigits a atacar aquesta via i que són utilitzats actualment en clínica és limitada. Per aquest motiu la recerca de noves molècules que inactivin els receptors d’aquesta família mitjançant noves estratègies és avui dia una de les vies més explorades. En aquesta tesi s’ha desenvolupat un pèptid idèntic al factor de creixement epidèrmic EGF que li manca la seva part C-terminal (EGFt) com a nou inhibidor de EGFR. El disseny d’aquest pèptid truncat s’ha basat en la superposició tridimensional de l’estructura de l’EGF i de l’inhibidor de la carboxipeptidasa de patata (PCI), un bloquejador de la via de l’EGFR descrit prèviament pel nostre grup. El pèptid ha estat produït en E.coli i s’ha aconseguit obtenir un alt rendiment de la proteïna i amb la seva conformació estructural correcta. Hem observat que l’EGFt in vitro té una capacitat molt menor per induir dímers del receptor i també la seva fosforilació si la comparem amb l’activitat que té l’hEGF natiu. Per altra banda, l’EGFt promou la internalització del receptor i la seva translocació al nucli cel·lular tal i com ho fa l’hEGF, tot i que no estimula el creixement cel·lular. A més, l’EGFt competeix amb els lligands natius de la família i inhibeix la proliferació cel·lular. La manca d’activitat estimuladora del creixement cel·lular d’aquest pèptid quan s’uneix a l’EGFR ens va portar a provar la utilització de l’EGFt com a vehicle de toxines dirigit a cèl·lules tumorals que sobreexpresessin EGFR. Concretament, es va produir un radioconjugat de EGFt amb l’isòtop radioactiu emissor d’electrons Auger Indi-111. Les propietats d’aquest radioconjugat es van analitzar i es van comparar amb el radioconjugat produït amb hEGF natiu. En primer lloc es va determinar que 111In-DTPA-EGFt té una alta especificitat i afinitat per EGFR. No obstant, la captació cel·lular de 111In-DTPA-EGFt va resultar ser menor que la de 111In-DTPA-hEGF. Un cop internalitzat, 111In-DTPA-EGFt va mostrar una alta eficiència per acumular-se en el nucli de la cèl·lula, on la radioactivitat emesa per 111In danya l'ADN. 111In-DTPA-EGFt va mostrar ser citotòxic in vitro contra cèl·lules de càncer de mama, encara que la seva citotoxicitat va ser menor en comparació amb 111In-DTPA-hEGF. Els estudis in vivo van revelar una vida mitjana més llarga en sang per 111In-DTPA-EGFt que per 111In-DTPA-hEGF, una major captació en el ronyó i una menor acumulació en altres teixits normals. 111In-DTPA-EGFt es va detectar en els tumors de cèl·lules MDA-MB-468 on el radiocompost es va acumular preferentment en el nucli de la cèl·lula. Les dades recollides en aquest treball indiquen que l’EGFt pot tenir un gran potencial com a bloquejador en teràpia pel càncer i a més pot ser un bon lligand per utilitzar com a vehicle d’agents citotòxics dirigits al nucli de cèl·lules tumorals positives en EGFR.
Tonello, Andrea <1988>. "Synthesis and Engineering of PLGA-based Nanoparticles with antitumoral Properties." Master's Degree Thesis, Università Ca' Foscari Venezia, 2014. http://hdl.handle.net/10579/5394.
Full textZou, Yu. "Dendrimères et dendrons phosphorés : synthèse, propriétés et applications en nanomédecine." Electronic Thesis or Diss., Université de Toulouse (2023-....), 2024. http://www.theses.fr/2024TLSES093.
Full textThe objective of this thesis work was to prepare new phosphorous dendrimers or phosphorous dendrons, either neutral, cationic or anionic, with the aim of broadening the range of applications in the field of nanomedicine as molecules active by per se. or in combination with certain medications. In Chapter 1, the synthesis of a new polycationic phosphorus dendrimer comprising 5 pyrrolidinium groups on the surface and a protonated amine was successfully completed. This dendrimer associated with microRNA-30d makes it possible to obtain polyplexes which are transferred into cancer cells in an optimal N/P ratio of 10. These polyplexes are cytocompatible and transfer miR-30d to suppress glycolysis associated with SLC2A1. The inhibition of the migration and invasion of murine cancer cells in vitro and in vivo were thus demonstrated. This dendrimer can be considered as an important component for therapy based on the use of miR-30d. In Chapter 2, we develop a drug delivery system capable of penetrating BBB (blood brain barrier) to provide treatment for degenerative disorders. For this, the formation of a nanocomplex was developed consisting of a phosphorus dendrimer carrying hydroxyl groups on the surface, combined with fibronectin, which regulates proliferation and differentiation and cell motility. In a mouse model of Parkinson's disease, effective penetration at the level of the BBB of the phosphorous dendrimer assembly AK-123 and fibronectin was demonstrated, exerting an anti-inflammatory and antioxidant activity allowing to decrease effectively the symptoms observed and demonstrating the great potential for clinical treatment of Parkinson's disease but also hold great promise to be used to tackle other neurodegenerative disorders. In Chapter 3, the results obtained in the field of Parkinson's disease during the combined action of a generation 2 phosphorous dendrimer comprising 48 hydroxyl groups on the surface and fibronectin have encouraged us to diversify the nature and structure of these dendrimers in order to have first indications of their activity in general and to possibly approach a SAR (structure activity relationship) study. According to these, we prepared a whole set of new neutral phosphorus dendrimers of generations 1 and 2, characterized by internal structures different from those of the dendrimers used in the previous chapter, incorporating long chains on the surface and also comprising hydroxyl groups. These dendrimers have the advantage of having protonated amine groups allowing solubility in an aqueous medium. We were also able to prepare neutral and charged phosphorous dendrons. Preliminary results concerning their properties have been demonstrated. In Chapter 4, the aim of this study was focused on the synthesis of original anionic phosphorus dendrimers and the application of these dendrimers, and particularly of the dendrimer AK 137 which presents optimal anti-inflammatory activity and great efficiency for the delivery of proteins. We demonstrate that the AK-137@FN NCs association blocks the activation of certain signalling pathways (NF-kB and P13K/Akt), induces the polarization of macrophages towards M2 phenotypes, inhibits the secretion of pro-cytokines. (TNF-alpha, IL-1beta and IL6) and increases the antioxidant properties of FN in vitro. The therapeutic effects of the AK-137@FN combination have been demonstrated in ALI (acute lung injury) and AGA (acute gout arthritis) mouse models without observation of systemic toxicity
Salvador, Cátia Sofia Clemente. "Caracterização de cogumelos silvestres da espécie Amanita ponderosa: produção de metabolitos com atividade biológica." Doctoral thesis, Universidade de Évora, 2014. http://hdl.handle.net/10174/13391.
Full textBrink, Susanna. "Structure-activity relationships of titanocene complexes with antitumor properties." Pretoria : [s.n.], 2003. http://upetd.up.ac.za/thesis/available/etd-09052005-101713/.
Full textChen, Chujian 1966. "Antitumor properties of kefir : possible bioactive component(s) and mechanism(s)." Thesis, McGill University, 2005. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=85139.
Full textSun, Wai-yin Raymond, and 辛偉賢. "The antitumor and antiviral properties of gold (III) porphyrins and their related complexes." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2004. http://hub.hku.hk/bib/B31245973.
Full textZhang, Zhouen. "Tumor-targeting antitumor prodrugs and noninvasive molecular imaging probes : designs, syntheses and properties." 京都大学 (Kyoto University), 2005. http://hdl.handle.net/2433/144557.
Full text0048
新制・課程博士
博士(工学)
甲第11886号
工博第2579号
新制||工||1361(附属図書館)
23666
UT51-2005-N720
京都大学大学院工学研究科物質エネルギー化学専攻
(主査)教授 西本 清一, 教授 中條 善樹, 教授 木村 俊作
学位規則第4条第1項該当
BUSA', Rosalia. "Evaluation of antitumor and immunomodulatory properties of Indicaxanthin from Opuntia Ficus Indica (L. Mill) fruit." Doctoral thesis, Università degli Studi di Palermo, 2020. http://hdl.handle.net/10447/395264.
Full textMedvetz, Douglas Allen. "The Synthesis, Characterization, and Antitumor Properties of Ag(I), Cu(II), and Rh(III) Metal Complexes." University of Akron / OhioLINK, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=akron1216840371.
Full textKnapp, Amanda R. "Antimicrobial and Antitumor Properties of Free and Poly(Ethylene Glycol)-Poly(Lactic Acid) Encapsulated Silver N-Heterocyclic Carbene Complexes." University of Akron / OhioLINK, 2011. http://rave.ohiolink.edu/etdc/view?acc_num=akron1309211795.
Full textGoubau, Delphine. "Distinct roles of interferon regulatory factor (IRF)-3 and IRF-7 in the activation of the antitumor properties of human macrophages." Thesis, McGill University, 2008. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=18752.
Full textLes facteurs régulateurs d'interferons (IRF) sont les médiateurs transcriptionnels de la réponse immunitaire innées. Deux de ces facteurs, IRF-3 et IRF-7, induisent l'expression des interferons de type I (IFN-alpha et -beta) importants pour la réponse antivirale et antitumorale. Les IFNs ont également des effets antiprolifératifs et antiangiogénics et sont couramment utilisés comme adjuvants en thérapie contre le cancer. Après activation, les macrophages presentment des activités antitumorales ce qui en font une alternative prometteuse au thérapie standard. À cet effet, la tolérance et l'activité des macrophages autologues humains activés à l'IFN-gamma (cellules MAK) ont été évaluées dans des essais pilotes chez des patients souffrants du cancer. Afin d'étudier le role d'IRF-3 et IRF-7 dans la regulation des fonctions antitumorales des macrophages, des vecteurs adénoviraux ont été produits pour livrer les formes constitutivement actives d'IRF-3 (Ad-F3) ou d'IRF-7 (Ad-F7) dans les macrophages humains. L' expression des gènes dans les macrophages transduits avec Ad-F3 ou Ad-F7 a été mesurée par microarray. IRF-3 induit fortement l'expression du gène pro-apoptotic Noxa. En revanche, IRF-7 induit faiblement Noxa mais induit Mcl-1 - un inhibiteur de l'apoptose qui interagit avec et inhibe Noxa. La transduction avec Ad-F3 induit l'activation rapide de la voie apoptotique mitochondriale dans les macrophages. La forme active d'IRF-7 induit l'expression des molecules tumoricidales (TRAIL et IFN-alpha et -beta) de chemokines et de genes impliqués dans la presentation d'antigènes. De plus, les macrophages transduits avec Ad-F7 exercent une activité cytostatique sur différentes lignées cancéreuses et une capacité de presentation-croisée accrue. En conclusion, Ad-F3 ou Ad-F7 semblent réguler l'apoptose et les propriétés anti-tumorales des macrophages de manière différente, l'expression d'IRF-7 menant à l'acquisition de fonctions e
Strioga, Marius. "Expression of biomarkers, representing immunosuppressive, cytotoxic or immunomodulating properties of CD8h T lymphocytes in the peripheral blood of patients with immunogenic cancer forms." Doctoral thesis, Lithuanian Academic Libraries Network (LABT), 2010. http://vddb.laba.lt/obj/LT-eLABa-0001:E.02~2010~D_20100702_105111-42651.
Full textDarbo tikslas buvo įvertinti imunosupresines (FOXP3, NKG2A), citotoksines (perforin) bei citotoksines / imunomoduliuojančias (IFNγ) savybes atspindinčių žymenų raiškos skirtumus išplitusiu inkstų vėžiu ar didelės rizikos odos melanoma sergančių pacientų periferinio kraujo CD8h T limfocitų populiacijoje, lyginant su kontroline grupe. Skirtingas T limfocitų savybes atspindinčių žymenų raiška buvo tiriama tėkmės citometrijos būdu. Nustatyta, kad inkstų vėžiu ar odos melanoma sergančių pacientų periferiniame kraujyje Įvairių subpopuliacijų (ypač imunosupresinės) nuošimčio nustatymas CD8hCD57+ T limfocitų populiacijoje ateityje gali būti naudingas klinikinėje praktikoje, individualizuojant priešnavikinę imunoterapiją ir selektyviai parenkant tik tuos pacientus, kuriems imuninės sistemos aktyvinimas sukeltų navikinių ląstelių naikinimą, o ne dar labiau gilintų imunosupresiją.
Saha, Chaitrali. "Unravelling the therapeutic intervention of inflammation and cancer by Viscum album : understanding its anti-inflammatory and immunostimulatory properties." Thesis, Compiègne, 2015. http://www.theses.fr/2015COMP2210/document.
Full textViscum album (VA) preparations, commonly known as European mistletoe, are frequentlyused as complementary therapy in cancer, mainly to improve quality of life of the patients andto reduce the tumor growth. They are known to exert anti-tumoral effects. There is increasing evidence of the convoluted connection of cancer and inflammation. As cyclooxygenase-2(COX-2)-induced prostaglandin E2 (PGE2) plays a key role in the inflammation, I explored the regulation of COX-2-PGE2 axis by VA and underlying mechanisms. I found that VA exerts anti-inflammatory effects by selectively inhibiting COX-2 expression and ensuing PGE2 production. Inhibition of COX-2 expression implicates COX-2 mRNA destabilisation. In addition to their cytotoxic properties, they have also been shown to have immunostimulatory properties. Each VA preparations are highly heterogeneous because oftheir chemical composition which varies depending on the time of harvest, species of host treeand manufacturing methods, together which might influence clinical efficacy of VA.Therefore I performed a comparative study involving five different preparations of VA concerning maturation and activation of dendritic cells (DCs) which in turn may manifestanti-tumoral immune response. Results showed that among all five preparations, VA Qu Spez significantly induces DC activation, secretion of pro-inflammatory cytokines such as IL-6, Il-8 and TNF-α, enhancing IFN-γ production hence promoting Th1 immune response. The orchestration of myelomonocytic cell function is a key element that links inflammation and cancer and provides a paradigm for macrophage plasticity and function. My study reveals the effect of VA Qu Spez in switching the M2 macrophages which are known to participate inpolarizing Th2 responses, help with parasite clearance, dampen inflammation, promote tissue remodelling and tumor progression and have immunoregulatory functions, towards classicallyactivated M1 macrophages which are part of a polarized Th1 response and mediate resistance13to intracellular pathogens and tumors and elicit tissue-disruptive reactions. These results together should assist in understanding the anti-inflammatory and immunostimulatory properties of VA preparations and further research is warranted to improve the therapeutic strategies of use of VA and their role as complimentary therapy in cancer
Glorani, Giulia. "Structural studies of a Tremella fuciformis mushroom lectin: a novel protein with antitumoral properties." Doctoral thesis, 2019. http://hdl.handle.net/11562/994597.
Full textBrink, Susanna. "Structure-activity relationship of titanocene complexes with antitumor properties." Thesis, 2003. http://hdl.handle.net/2263/27746.
Full textOyun-Enkh and 歐優娜˙龐扎克. "The induction of apoptosis and antitumor properties of Mongolian plants." Thesis, 2011. http://ndltd.ncl.edu.tw/handle/75391887780018879682.
Full text中山醫學大學
牙醫學系碩士班
99
Euphorbia Fisheriana Steudal (EF) and Saussurea Involucrata (SI) are rare plants which were used in ancient Eastern medicine. In this study, the antitumor properties of EF and SI were assessed by MTT assay, Western immunobloting, DNA fragmentation and nuclei staining methods. We have found that both of the plant extracts promote the apoptotic death of tumor cells by activation of proapoptotic regulators of Bcl-2 family and MAPK pathway, especially SAPK/JNK2. In case when EF was employed, the initiation of apoptosis was linked to the activation of intrinsic pathway and p38. No visible changes were detected in relation to ERK and JNK1. P38 inhibition and gene silencing by siJNK2 caused an inhibition of Bax and p53, at the same time procaspase-9 was distinctly up-regulated in contrast to caspase-9. Different outcome was observed after induction with SI. Apoptosis was triggered via activation of caspase-8 and caspase-9; no changes were detected in relation to p38 and ERK. The specific aspect of SI treatment was in inhibition of JNK1. Gene silencing by siJNK2 down-regulated Bax and p53; and up-regulated procaspase-9. These results suggest that EF and SI are potent inhibitors in the growth of cancer cells, and the apoptotic mechanism might be related to the activation of JNK2, rather than p38. Additionally, SI is an effective inhibitor of JNK1. Euphorbia Fisheriana Steudal and Saussurea Involucrata would be novel natural drugs nowadays, less toxic and with a higher cost benefit in comparison to chemical drugs in cancer treatment.
Song, Tuzz-Ying, and 宋祖瑩. "Studies on Antioxidant and Antitumor Properties of Antrodia camphorata in Submerged Culture." Thesis, 2003. http://ndltd.ncl.edu.tw/handle/23404381735808384640.
Full text國立中興大學
食品科學系
91
This study evaluated antioxidant and Anti-tumor properties of extracts from Antrodia camphorata in submerged culture (ACSC). Chapter 2 focuses on the studies of biologically active compounds and the antioxidant activity as well as free radical scavenging effects of dry matter of cultural medium (DMCM), filtrate (DMF) and different solvent extracts of mycelia from Antrodia camphorata in submerged culture (ACSC). DMF showed the strongest inhibition of lipid peroxidation as a function of its concentration, and was comparable to the antioxidant activity of BHA at the same concentration of 0.2 mg/ml. The hexane extract of mycelia had the weakest antioxidant ability, whereas other mycelial extracts exhibited a modest inhibition of lipid peroxidation. DMF and water extract of mycelia (WEM) showed marked activity in free radical scavenging. The antioxidant activities of filtrate and mycelial extracts were correlated to the presence of total polyphenols, the crude triterpenoid and the protein/polysaccharide ratio of the crude polysaccharide. It was found that DMCM had lower antioxidant ability than DMF in different model systems; indicating that the major antioxidant components in DMF must be derived from the secondary metabolites of mycelia. The results presented herein indicated that DMF could possibly act as a chemopreventing agent with respect to free radical-related diseases. Chapter 3 focuses on studies of the protective effects of DMF from Antrodia camphorata in ACSC on H2O2-induced cytotoxicity in HepG2 and carbon tetrachloride (CCl4)-induced hepatotoxicity in SD rats, and the possible mechanisms involved in this protection were also investigated. The preliminary study showed that the inhibitory effect of DMF and its crude triterpenoids on lipid peroxidation was in a dose-response manner in AAPH/linoleic acid system. HepG2 cells were pretreated with DMF at the concentration of 0.10 mg/ml for 4 h, significantly (p<0.05) decreased the lipid peroxidation which was measured by the formation of malondialdehyde induced by 1 h treatment of H2O2 (100 M). The oral pretreatment with DMF (0.25 and 0.50 mg/kg b.w.) for 5 consecutive days prior to the administration of a single dose of 40 % CCl4 (0.10 ml/100g b.w., ip) significantly prevented the increase in serum levels of hepatic enzyme markers (alanine and aspartate aminotransferase) and liver lipid peroxidation (p<0.05). The histopathological evaluation of the rat liver revealed that DMF reduced the incidence of liver lesions including neutrophil infiltration, hydropic swelling and necrosis induced by CCl4 in rats. Moreover, GSH-dependent enzymes (Glutathione peroxidase, Glutathione reductaser and Glutathione S-transferase) and the GSH/GSSG ratio were significantly improved in the oral pretreatment DMF of rats (p<0.01). Based on the above results, we speculate that DMF may play a role in preventing oxidative damage in living systems by up-regulating hepatic GSH-dependent enzymes to preserve the normal GSH/GSSH ratio and directly scavenging free radicals formed during CCl4 metabolism. Chapter 4 focuses on the studies of the effect of methanolic extracts of mycelial (MEM) inhibited cell viability and the mechanism of MEM-induced cytotoxic in hepatoma cells. The IC50 of MEM on the proliferation of HepG2 (wild type p53) and Hep3B (delete p53) was 49.5 and 62.7 g/ml, respectively, on day 2. The effect of MEM on inhibiting cell viability was about 0.2-fold of that methanolic extracts of Antrodia camphorata fruiting bodies (MEAF). There is no observable cytotoxicity of MEM in Chang liver cells and rat primary hepatocytes at the concentration of 100 g/ml. MEM-mediated HepG2 and Hep3B cells death by apoptosis were determined by cell morphological changes, DNA fragmentation and cell cycle analysis. Cell cycle analysis revealed that MEM induced apoptosis on HepG2 via G0/G1 cell cycle arrest. HepG2 and Hep3B treated with MEM (100 g/ml) for 72 h, the apoptotic cells were 98.3 and 39.5%, respectively. It was speculated that MEM-induced cells apoptosis in HepG2 was mediated by p53-dependent that was why HepG2 was more susceptible than Hep3B. The results suggest that MEM induced HepG2 apoptosis through inhibition cell growth and up-regulation of Fas/FasL to activate the pathway of caspase-3 and -8 cascade. Chapter 5 focuses on the studies of purification and identification of antitumor components of methanol extracts of mycelia (MEM) from ACSC. The fractions separated by HPLC from MEM were examined to evaluate the antitumor effect of inhibition cell viability on Hep3B. Then, the antitumor fraction in MEM, which was high in amount and possessed potent antitumor activity, was selected to precede purification and identification. There were six fractions (A-F) in MEM separated by analytical column of HPLC. Based on the integration of peak area, fraction C was the most abundant fraction (40%), fractions B (16%) and C (13%) was the next, and the other fraction were about 4-8% in quantity. Hep3B was treated with fraction B, C, D, and E for 24 h, and the IC50 on Hep3B was about 26-45 g/ml. However, fractions A and F showed no inhibition effect on cell viability in Hep3B. Fraction C was further separated and purified by the preparative HPLC and TLC, respectively. The molecular formula and weight of compound C were C16H22O3 and 262.2, respectively and was identified by UV, MS, IR and 1H-, and 13C-NMR. Keywords: Antrodia camphorata in submerged culture; antioxidant; anti-tumor; apoptosis; hepatoma cells
Grau, L., M. Romero, C. Privat-Contreras, Daniela Presa, M. Viñas, J. Morral, Klaus Pors, J. Rubio-Martinez, and M. D. Pujol. "Multigram scale synthesis of polycyclic lactones and evaluation of antitumor and other biological properties." 2019. http://hdl.handle.net/10454/17526.
Full textAn efficient four-step synthesis of tetracyclic lactones from 1,4-benzodioxine-2-carboxylic acid was developed. Ellipticine derivatives exhibit antitumor activity however only a few derivatives without carbazole subunit have been studied to date. Herein, several tetracyclic lactones were synthesized and biologically evaluated. Several compounds (2a, 3a, 4a and 5a) were found to be inhibitors of the Kras-Wnt pathway. The lactone 2a also exerted a potent inhibition of Tau protein translation and was shown to have capacity for CYP1A1-bioactivation. The results obtained are further evidence of the therapeutic potential of tetracyclic lactones related to ellipticine. Molecular modeling studies showed that compound 2a is inserted between helix α3 and α4 of the KRas protein making interactions with the hydrophobic residues Phe90, Glu91, Ile9364, Hie94, Leu133 and Tyr137and a hydrogen bond with residue Arg97.
The Spanish Minister (CTQ2011-29285-C02-02) the SGR(2014)-1017 Generalitat de Catalunya and the Laboratories Servier (France)
Liu, Hsiu-Wen, and 劉秀雯. "In vitro and in vivo antitumor properties of Antrodia salmonea against human colon cancer cells." Thesis, 2018. http://ndltd.ncl.edu.tw/handle/83szz8.
Full textCatarino, Marcelo Dias. "Fucus vesiculosus phlorotannins: extraction, structural characterization and effects throughout the gastrointestinal tract." Doctoral thesis, 2021. http://hdl.handle.net/10773/31275.
Full textDesde a antiguidade que as macroalgas marinhas têm sido tradicionalmente usadas pelos povos de extremo oriente, quer para consumo direto, como fonte de nutrientes, como para fins medicinais. Nos últimos anos estes organismos marinhos têm vindo a ganhar uma crescente popularidade entre as populações ocidentais que começam a estar cada vez mais conscientes do potencial que estas possuem como uma possível fonte de compostos bioativos de grande interesse. De entre os seus compostos destacam-se os florotaninos, um grupo de compostos fenólicos derivados do floroglucinol, reivindicados pelos seus benefícios para a saúde, e cuja ocorrência é exclusiva das macroalgas castanhas. Apesar de várias propriedades bioativas terem já sido demonstradas para estes compostos, existe ainda um longo percurso a percorrer até à compreensão dos mecanismos por detrás destas, sendo isto particularmente verdade no que diz respeito às propriedades anti-inflamatórias e antitumorais dos florotaninos provenientes da macroalga Fucus vesiculosus. Além disso, pouco se sabe acerca do destino destes compostos durante a sua passagem pelo trato gastrointestinal. Neste contexto, neste trabalho pretendeu-se otimizar a extração de florotaninos a partir desta macroalga e elucidar a composição destes extratos através da técnica de UHPLC-DAD-ESI-MSn , bem como clarificar as potencialidades bioativas de extrato bruto ou frações do ponto de vista de atuação ao longo to trato gastrointestinal, nomeadamente os efeitos antioxidante, anti-inflamatório, antitumoral e prébiotico. Recorrendo à técnica de superfície-resposta, as condições determinadas para o máximo de recuperação de florotaninos da alga F. vesiculosus foram: acetona a 67% (v/v) numa proporção de 70 mL/g de farinha de alga a 25 ºC. Após um passo de purificação intermédio, a fração rica em florotaninos (EtOAc) revelou um complexo perfil cromatográfico composto por vários fucóis, fucofloretóis, fualóis e outros derivados de florotaninos. Foram ainda detetados três potenciais novos derivados de florotaninos, nomeadamente o fucofurodifloretol, fucofurotrifloretol e o fucofuropentafloretol. Tanto o extrato bruto como a EtOAc revelaram boa atividade antioxidante, em particular contra o radical de óxido nítrico, um importante interveniente na cascata sinalizadora da inflamação. De facto, uma atividade anti-inflamatória pronunciada foi confirmada em células RAW 264.7 estimuladas com lipopolissacarídeo (LPS). A partir da EtOAc foram ainda obtidas 9 sub-frações de florotaninos com diferentes pesos moleculares que, após testadas na mesma linha celular, revelaram algumas diferenças ao nível da atividade anti inflamatória que possivelmente estarão relacionados com a sua complexidade e peso molecular. Um efeito anti-inflamatório bastante marcado foi ainda observado para uma sub-fração em particular, a F2, caracterizada pela presença de um composto derivado de florotaninos com peso molecular de 508 g/mol. Esta fração, a 200 µg/mL, foi capaz de inibir a fosforilação e degradação da proteína IκBα, consequentemente bloqueando a cascata sinalizadora da inflamação ao nível transcricional. A fração EtOAc bem como algumas das posteriores sub-frações, nomeadamente F1 e F5, demostraram ainda propriedades antitumorias promissoras, provocando um efeito citotóxico seletivo apenas contra células tumorais de cancro gástrico (MKN-28) e cancro do colon (Caco-2 e HT-29), não afetando células normais. Das três amostras, a F5, caracterizada pela presença de fucóis, fucofloretóis, um fucofurodifloretol e eckstolonol, foi a que revelou o efeito mais acentuado em todas as linhas celulares tumorais, demonstrando valores de IC50 de 56.3 ± 14.7, 97.4 ± 11.6 e 118.8 ± 19.7 µg/mL para MKN-28, Caco-2 e HT-29, respetivamente. Curiosamente, enquanto a EtOAc exerceu este efeito através do bloqueio do ciclo celular e ativação de mecanismos de morte celular, a sub-fração F1 apenas promoveu o bloqueio do ciclo celular enquanto a sub-fração F5 apenas ativou a morte celular via ativação de mecanismos de apoptose/necrose. Por fim, verificou-se uma boa capacidade inibidora das enzimas digestivas por parte destes compostos, em particular da enzima α-glucosidase cujo IC50 foi 45 a 250 vezes inferior ao da acarbose, revelando potencial terapêutico contra a diabetes do tipo-II. No entanto, à semelhança dos polifenóis das plantas, os florotaninos revelaram-se suscetíveis a degradação e perda de atividade antioxidante durante a sua passagem ao pelo trato gastrointestinal, com menos de 15% dos florotaninos totais da amostra inicial ficando bioacessíveis e disponíveis para absorção. Em contrapartida, apesar de a fração não bioacessível das amostras de F. vesiculosus terem apenas contribuído com um efeito modestamente positivo na modulação da microbiota humana, estas demonstraram uma capacidade interessante de estimular a produção de propionato e butirato, dois ácidos gordos de cadeia curta com propriedades benéficas para a saúde do hospedeiro bem estabelecidas. Em conclusão, este estudo não só permitiu compreender melhor a composição dos florotaninos presentes na alga F. vesiculosus, como também demonstrou que os seus extratos e/ou frações purificadas podem ter um impacto relevante na manutenção de uma boa saúde gastrointestinal atuando em diferentes níveis. Em última instância, este trabalho contribui para a valorização da espécie F. vesiculosus como uma possível fonte de compostos naturais com grande potencial biológico e de aplicabilidade.
Programa Doutoral em Química Sustentável
Heleno, Sandrina Alves. "Important human metabolites of phenolic acids from diet with wild mushrooms: chemical synthesis and studies of their antioxidant, antitumor and antimicrobial properties." Doctoral thesis, 2014. http://hdl.handle.net/1822/35721.
Full textIn this study, seven wild mushroom species (Ganoderma lucidum, Coprinopsis atramentaria, Rhodotus palmatus, Lactarius bertillonii, Lactarius vellereus, Xerocomus chrysenteron and Morchella esculenta), were characterized for their nutritional value (macronutrients and energy) and chemical composition (fatty acids, tocopherols, sugars and organic acids). A special focus was given to the analysis of phenolic acids and related compounds in mushroom fruiting bodies, spores and in vitro produced mycelia, by using chromatographic and mass spectrometry techniques. After mushrooms ingestion, the mentioned compounds suffer conjugation reactions, such as methylation and glucuronidation, and their structure can vary, modifying or not, their bioactive properties. With that aim, circulating metabolites of phenolic acids found in humans, such as methyl and glucuronide derivatives, were prepared by chemical synthesis and further characterized by the usual methods (melting point, 1H and 13C-nuclear magnetic resonance, and high resolution mass spectrometry). The bioactive properties of the synthesized compounds were evaluated and compared with the parent phenolic acid, and also with the mushroom phenolic extract. The bioactivities assessed were: i) antioxidant activity, measured by free radicals scavenging activity, reducing power and lipid peroxidation inhibition in vitro assays; ii) antimicrobial activity, including antibacterial and antifungal properties with evaluation of demelanizing capacity, determined by disc diffusion and microdilution methods; and iii) inhibitory growth activity against different human tumor cell lines, and also against non-tumor porcine liver primary cells culture to evaluate toxicity, using sulforhodamine B assay. The studied edible mushroom species are a good choice to include in our daily diet due to their richness in nutrients such as carbohydrates and proteins, and bioactive molecules, being also low caloric foods due to the low fat and energy contents. Furthermore, mushroom phenolic extracts showed antioxidant and antimicrobial properties, and also the capacity to inhibit the growth of human tumor cell lines. The synthesized methylated and acetyl glucuronated methyl esters derivatives revealed, in general, higher inhibitory growth activity against human tumor cell lines and antimicrobial activity than their parent compounds being, in the latter case, even higher than the one showed by standard antibiotics. Moreover, all the tested compounds revealed no toxicity against non-tumor cells. This means that the inclusion of methyl and acetyl glucuronic methyl ester groups in the molecule can, in some cases, increase the phenolic acids bioactivity. Nevertheless, future studies are needed in order to understand and clarify the specific mechanistic pathways of these important metabolites or metabolite derivatives.
Neste trabalho, caracterizaram-se sete espécies de cogumelos silvestres (Ganoderma lucidum, Coprinopsis atramentaria, Rhodotus palmatos, Lactarius bertillonii, Lactarius vellereus, Xerocomus chrysenteron, e Morchella esculenta) quanto ao seu valor nutricional (macronutrientes e energia) e composição química (ácidos gordos, tocoferóis, açúcares e ácidos orgânicos). Deu-se uma maior relevância aos ácidos fenólicos e compostos relacionados que foram analisados utilizando técnicas de cromatografia e de espetrometria de massa no corpo frutífero, esporos e ainda no micélio produzido in vitro. Após a ingestão de cogumelos, os compostos mencionados sofrem reações de conjugação, tais como metilação e glucuronidação, o que pode alterar a sua estrutura e, consequentemente, as suas propriedades bioativas. Assim, sintetizaram-se possíveis metabolitos ou derivados de metabolitos de ácidos fenólicos que circulam no organismo humano, nomeadamente compostos metilados e ésteres metílicos do ácido glucurónico acetilado. Estes compostos foram completamente caracterizados utilizando técnicas de ponto de fusão, ressonância magnética nuclear 1H e 13C, e ainda espetrometria de massa de alta resolução. As propriedades bioativas dos compostos sintetizados foram avaliadas e comparadas com as dos ácidos fenólicos parentais, assim como com as dos extratos fenólicos de cogumelos. As bioatividades analisadas foram: i) atividade antioxidante, em ensaios in vitro de avaliação da atividade captadora de radicais livres, poder redutor e inibição da peroxidação lipídica; ii) atividade antimicrobiana incluindo propriedades antibacterianas e antifúngicas com determinação da capacidade desmelanizante, avaliadas por métodos de difusão em disco e de microdiluição; e iii) actividade inibitória do crescimento em diferentes linhas celulares tumorais humanas, e em células não tumorais de fígado de porco, usando uma cultura primária para avaliar a sua toxicidade, usando o método da sulforrodamina B. As espécies de cogumelos comestíveis estudadas mostraram ser uma boa opção para inclusão na nossa dieta diária dada a sua riqueza em nutrientes como glúcidos e proteínas, baixos teores calóricos e energéticos, e também por serem ricos em moléculas bioativas. Para além disso, os extratos fenólicos de cogumelos revelaram atividade antioxidante, antimicrobiana e também mostraram inibir o crescimento em linhas celulares tumorais humanas. Em geral, os derivados metilados e ésteres metílicos do ácido glucurónico acetilado mostraram maior actividade inibitória do crescimento (em linhas celulares tumorais humanas) e atividade antimicrobiana do que os respetivos ácidos fenólicos. De salientar que a atividade antimicrobiana destes possíveis metabolitos foi superior à dos antibióticos utilizados como padrões. Os resultados obtidos permitiram concluir que a inserção de grupos metilo e ésteres metílicos do ácido glucurónico acetilado nos ácidos fenólicos aumentam a sua bioatividade. No entanto, são ainda necessários mais estudos que permitam elucidar completamente os mecanismos de ação envolvidos na bioatividade destes importantes metabolitos e derivados.
Fundação para a Ciência e Tecnologia (FCT)-Portugal for financial support to the Portuguese NMR network and to FCT and FEDER-COMPETE/QREN/EU for the financial support through the research project (PTDC/AGR-ALI/110062/2009) and for my PhD grant (SFRH/BD/70304/2010) that gave me the opportunity to perform this work.
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 textAccording 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.
柯宏儒. "Modification of Roussin’s Red Esters by Incorporation of α-Lipoic Acid Conjugated with Poly(ethylene glycol) for the Study of Photochemical Properties and Antitumor Activity." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/25825472118679886221.
Full text國立嘉義大學
應用化學系研究所
101
Abstract Here, we synthesize two new Roussin’s Red Esters (RREs) : RRE(ALA-TEG) (1) and RRE(ALA-PEG400) (2). These complexes have used IR, EA and TEM to prove their comformation and micelle form. We have also used NO analyer to demonstrate complexes (1) and (2) that can released NO by UV. In addition, we demonstrated that NO can cleavage DNA in direct proportion to its concentration.
Mouffok, Kheira Moufida. "Quality evaluation and biological properties of Algerian commercial honeys labeled as Rosemary, Tamarisk, Thistle and multiflora." Master's thesis, 2020. http://hdl.handle.net/10198/24074.
Full textHoney is considered a natural sweet substance produced by honeybees, from the nectars of plant flowers and honeydews. Honey has always been regarded as a food that is beneficial for human health with several therapeutic qualities described. The quality of honey is still a top concern for experts as no good method has been defined so far for the simultaneous detection of different types of honey. Consequently, the development of easy, quick, precise analytical tools that may give data for assessing honey authenticity, is important. Because of that, it is essential to inform consumers of the mislabeling of honey with lower quality. This study aimed to evaluate the physicochemical characteristics and to assess the quality of Algerian honey from different botanical and geographical origins. For that, ten samples of honey with different marked botanical origins were analyzed, including three samples from rosemary honey, three from tamarisk honey, three from milk thistle honey and one multiflora honey. The quality of the samples was determined through different parameters. Melissopalynological and physicochemical analyses (color, moisture, pH, acidity, electrical conductivity, diastase index, proline, 5-hydroxymethylfurfural, mineral content, proteins, carbohydrates, energy, and ash) were performed, as well as the profile evaluation of sugar and phenolic compounds. Antioxidant activity (reducing power and DPPH free radical scavenging activity) antitumor and anti-inflammation activity were also evaluated. Finally, the presence of antibiotics, recurrent residues in honey, such as tetracyclines and sulphonamides were screened using the multi-analyte receptor assay system Charm II. The melissopalinological analysis showed the presence of 10 major types of pollen grains, with Rosmarinus officinalis, Cytisus stratitus and Centaurea sp. pollens as the most abundant. Furthermore, since no honeydew elements were detected, all the samples were classified as nectar honeys. Samples R1, R2, and R3 were classified as rosemary monofloral honey; samples T1, T2 and MF were classified as Cytisus striatus honey; CH1-CH3 were classified as Centaurea sp. and T3 as multifloral, which not always agreed with the labeled botanical origin. Generally, honey samples presented values of moisture, free acidity, 5-HMF, proline content, and diastase index within the limits of the legal requirements, suggesting that the honey was extracted at a correct ripeness stage. The results showed that almost all honey samples have light amber color, except the rosemary honeys which presented an extra white amber color. Although exhibiting a normal diastase index, the R2 and R3 samples presented a 5-HMF value higher than the admitted in the legislation, suggesting that less adequate heat treatments and/or conservation methods might have been employed. The most common minerals were potassium, sodium, calcium, manganese, while copper and Manganese were present in some samples in minor quantities and the heavy metals (cadmium and lead) are absent from all samples. The sugar profile, analyzed by high pressure liquid chromatography with refractive index detection (HPLC-RI), showed that fructose and glucose were the most abundant compounds, representing more than 60% of total sugars. Other sugars, such as turanose, maltulose and maltose were also detected in a lower proportion. Regarding the phenolic profile, nineteen compounds (eight phenolic acids and seven flavonoids), two isoprenoid compounds (trans, trans- and cis, trans- abscisic acid), one spermidine and one phenolic diterpene were identified. T2 sample showed a higher amount of phenolic acids than flavonoids. However, the most abundant compounds were the benzoic acid derivative which was detected in all samples. Concerning the evaluation of the antitumor activity and anti-inflammatory activity the samples showed a significant potential. Finally, concerning the antibiotics screening, not all the samples showed negative results.
O mel é considerado uma substância doce natural produzida pelas abelhas, a partir dos néctares das flores das plantas e de meladas. O mel sempre foi considerado um alimento benéfico para a saúde, com várias qualidades terapêuticas descritas. A sua qualidade ainda é uma das principais preocupações para os especialistas, pois não há um método ideal para a classificação simultânea de diferentes tipos de mel. Consequentemente, é importante o desenvolvimento de ferramentas analíticas simples, rápidas e precisas que possam fornecer dados que permitam avaliar a autenticidade do mel. Por esse motivo, é essencial informar os consumidores da incorreta rotulagem de méis com baixa qualidade. O objetivo deste estudo foi avaliar as características físico-químicas e desse modo aferir a qualidade de méis argelinos com diferentes origens botânicas e geográficas. Para isso, foram recolhidas dez amostras de méis rotulados com diferentes origens botânicas, nomeadamente: três de mel de alecrim, três de mel de tamarino, três de mel de cardo e um de mel multifloral. A qualidade dos méis foi aferida através de diferentes parâmetros. Foram realizadas análises melissopalinológicas e físico-químicas (cor, humidade, pH, acidez, condutividade elétrica, índice diastático, prolina, 5-hidroximetilfurfural, conteúdo em minerais, proteínas, hidratos de carbono, energia e cinzas), bem como a avaliação do perfil em açúcares e compostos fenólicos. Também foi avaliada a atividade antioxidante (poder redutor e poder bloqueador de radicais livres) e atividade antitumoral e antiinflamatório. Finalmente, a presença de antibióticos, resíduos recorrentes no mel, como tetraciclinas e sulfonamidas, foram investigados através do sistema de despistagem Charm II. A análise melissopalinológica mostrou a presença de 10 tipos de grãos de pólen maioritários, sendo os pólenes de Rosmarinus officinalis, Cytisus stratitus e Centaurea sp. os mais abundantes. Além disso, e como não foram detetados elementos de melada, as amostras analisadas foram classificadas como méis de néctar: as amostras R1, R2 e R3 foram classificadas como mel monofloral de alecrim; as amostras T1, T2 e MF foram classificadas como mel de Cytisus striatus; CH1-CH3 foram classificados como de Centaurea sp. e T3 como multifloral, nem sempre coincidindo com a classificação utilizada no rótulo. De uma forma geral, as amostras de mel apresentaram valores de humidade, acidez livre, 5-HMF, teor de prolina e índice de diástase dentro dos limites requeridos legalmente, sugerindo que os méis foram extraídos no nível de maturação correto. Os resultados mostram que quase todas as amostras de mel apresentaram uma color âmbar clara, exceto o mel de alecrim que apresentou uma color âmbar extra clara. Apesar de apresentarem um índice de diástase normal, as amostras R2 e R3 apresentaram um valor de 5-HMF superior ao admitido na legislação, sugerindo a utilização de tratamentos térmicos e/ou métodos de conservação menos adequados. Os minerais mais comuns identificados foram o potássio, sódio, cálcio, enquanto cobre e manganês estiveram presentes em algumas amostras em quantidades menores e os metais pesados (cádmio e chumbo) estão ausentes em todas as amostras. O perfil dos açúcares, analisado por cromatografia líquida de alta pressão com deteção de índice de refração (HPLC-RI), mostrou que a frutose e a glucose foram os compostos mais abundantes, representando mais de 60% dos açúcares totais. Outros açúcares, como a turanose, a maltulose e a maltose, também foram detetados em menor proporção. Em relação ao perfil fenólico, foram identificados dezanove compostos (oito ácidos fenólicos e sete flavonóides), dois compostos isoprenóides (ácido trans, trans- e cis, trans-abscísico), uma espermidina e um diterpeno fenólico. No que diz respeito à avaliação da atividade antitumoral e atividade anti-inflamatória, as amostras apresentam potencial significativo. Finalmente, após o estudo de deteção de antibióticos verificou-se que nem todas as amostras estão isentas de resíduos.