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Evaluation of Neuroprotective Potential of Polyphenols Derived from Portuguese Native Plants: Juniperus Sp

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Evaluation of Neuroprotective Potential of Polyphenols Derived from Portuguese Native Plants: Juniperus Sp Evaluation of neuroprotective potential of polyphenols derived from Portuguese native plants: Juniperus sp. and Rubus sp. Lucélia Rodrigues Tavares Dissertation presented to obtain the Ph.D degree in Biochemistry Instituto de Tecnologia Química e Biológica | Universidade Nova de Lisboa Oeiras, November, 2012 Evaluation of neuroprotective potential of polyphenols derived from Portuguese native plants: Juniperus sp. and Rubus sp. Lucélia Rodrigues Tavares Dissertation presented to obtain the Ph.D degree in Biochemistry Instituto de Tecnologia Química e Biologica | Universidade Nova de Lisboa Oeiras, November, 2012 INSTITUTO DE TECNOLOGIA QUIMICA E BI0L0GICA / UNL Knowledge Creation The work presented in this thesis was developed at: Disease and Stress Biology Laboratory Instituto de Tecnologia Química e Biológica Universidade Nova de Lisboa Av. da República, Apartado 127 2781-901 Oeiras, Portugal Supervised by: Doctor Ricardo Boavida Ferreira Doctor Maria Cláudia Nunes dos Santos Funded by FCT and FSE in the scope of QCA, grant SFRH/BD/37382/2007 ii Table of contents Acknowledgements…………………..……………………………………………….iv Abreviation list………………………..……………………………………..….….….v Abstract………………………………..……………………………………..............ix Resumo………………………………………………….…………………………..….xi Thesis outline…………………………..………………………………………….…xiii Chapter 1: General introduction………………..………..………………………...1 Juniperus sp. .…………………………………………………………......…………59 Chapter 2: The neuroprotective potential of phenolic-enriched fractions from four Juniperus species found in Portugal …………………………...….61 Chapter 3: Elucidating phytochemical production in Juniperus sp.: seasonality and response to stress situations ……………………..…………87 Rubus sp. ……………………………………………………………..……………..113 Chapter 4 : Neuroprotective effect of blackberry (Rubus sp.) polyphenols is potentiated after simulated gastrointestinal digestion……………..…..115 Chapter 5: Neuroprotective effects of digested polyphenols from wild blackberry species……………………………………………………………..…..141 Chapter 6: Differential expression of genes involved in neuroprotection conferred by blackberry polyphenols after simulated gastrointestinal digestion………………………………………………………………..…….…..…169 Chapter 7: General discussion……………………………………….…..…..…221 Appendix: Comparison of different methods for DNA-free RNA isolation from SK-N-MC neuroblastoma …………………………………………………...A.1 iii Acknowledgements I dedicate this thesis to my all family, specially to my parents, my sister and my grandfather “Zé” that always believe on me and supported me. I also would like to acknowledge to my supervisors for all knowledge, advices and support. A special thank to Cláudia for being in the last years my “mom”, my “sister” and specially my friend. To my all lab colleagues. Many thanks for the time we shared together, on the lab and besides it. They enriched my life in many diverse aspects. A special thanks to all that help me in “flow cytometry marathon” and in thesis revision and to Rui for the amazing plant pictures. To my all friends not included above, that always support me and make me laugh, thanks. To Doctors Helena Vieira, Derek Stewart and Gordon McDougall I would like to acknowledge all the help and the involvement into the work. Last but not least, I thank to ITQB for hosting me and all people that make this work possible providing or helping in the search of plants, namely Doctors Carlos Aguiar, Pedro Oliveira, Dalila Espírito-Santo and Fátima Rodrigues. iv Abbreviation list Abbreviation Term m Mitochondrial transmembrane potential 4CL 4-coumarate:CoA ligase 6-OHDA 6-hydroxydopamine 8-OHdG 8-hydroxydeoxyguanosine A -amyloid ABC ATP-binding cassette AC Antioxidant capacity ACC Acetyl-CoA carboxylase ACh Acetylcholine AChE Acetylcholinesterase ACT Actin AD Alzheimer’s disease Aha1 ATPase homolog 1 Akt Protein kinase B ALP Autophagy-lysosome pathway ALS Amyotrophic lateral sclerosis ANR Anthocyanidin reductase ANS Anthocyanidin synthase AP-1 Activating protein-1 APC/CDC20 Anaphase-promoting complex/cell division cycle 20 homolog APP Amyloid precursor protein Arc Activity-regulated cytoskeleton-associated protein ARE Antioxidant response element Bcl-2 B-cell lymphoma 2 BDNF Brain-derived neurotrophic factor bp Base pair Brca Breast and ovarian cancer susceptibility protein BuChE Butyrulcholinesterase C3H p-coumarate 3 hydroxylase C4H Cinnamate 4-hydroxylase cAMP Cyclic adenosine monophosphate CAT Catalase CBF Cerebral blood flow CE Catechin equivalents CFTR Cystic fibrosis transmembrane conductance regulator CHI Chalcone isomerise CHS Chalcone synthase CNS Central nervous system COP Coat protein complex COX Cyclooxigenase CREB cAMP response element binding CyDAGlc Cyanidin-3-O-dioxayl-glucoside CyGlc Cyanidin-3-O-glucoside CyHMGG Cyanidin-3-O-hydroxymethyl-glutaroyl glucoside CyMalG Cyanidin-3-O-malonylglucoside CyXyl Cyanidin-3-O-xyloside CyXyl Cyanidin-3-O-xyloside DAPI 4',6-diamidino-2-phenylindole DAVID Database for Annotation, Visualization and Integrated Discovery DCF 2’,7’-dichlorofluorescein DFR Dihydroflavonol reductase DG Dentate gyrus DiOC (3) 3,3’-dihexyloxacarbocyanine iodide 6 DSB Double strain break DW Dry weight EA Ellagic acid ECAC European Collection of Cell Cultures v EF1A Elongation factor 1α EGCG Epigallocatechin gallate eIF2 Eukaryotic translation initiation factor 2 EMEM Eagle Minimum Essential Medium ENaC Epithelium sodium channel ER Endoplasmic reticulum ERK Extracellular-signal-regulated kinase ET Ellagitannin F3’5’H Flavonoid 3′5′-hydroxylase F3’H Flavonoid 3′-hydroxylase F3GT Flavonoid-3-glucosyltransferase F3H Favanone 3-hydroxylase FA Formic acid FBS Foetal bovine serum FLS Flavonol synthase FS Flavone synthase GA Golgi apparatus GABA Gamma-aminobutyric acid A GAE Gallic acid equivalents GAPDH Glyceraldeide 3-phosphate dehydrogenase GCN2 General control nonrepressed 2 GI Gastrointestinal GITC Guanidine Isothiocyanate GPx Glutathione peroxidase GR Glutathione reductase GRAS Generally Recognized As Safe Grx Glutaredoxin GSH Glutathione (reduced form) GSK 3 Glycogen synthase kinase 3 GSSG Glutathione disulphide H DCFDA 2’,7’-dichlorofluorescein diacetate 2 HD Huntington’s disease HNE 4-hydroxynonenal HO-1 Heme oxygenase HSD Honest Significant Difference HSP Heat shock protein IAPs Inhibitors of apoptosis IL-1 Interleukin-1 iNOS Inducible nitric oxide synthase IVD In vitro digestion JNK c-Jun N-terminal kinase KV Voltage-gated K+ Lamb Lambertianin C LAR Leucoanthocyanidin reductase LC-MS Liquid chromatography-mass spectrometry LPO Lipid peroxidation m/z Mass-to-charge ratio MAPK Mitogen-activated protein kinase MEAD Methyl ellagic acid derivative MeEAGlcA Methyl ellagic acid glucuronide MeEApent Methyl ellagic acid pentose MeJa Methyl jasmonate MEK Mitogen-activated protein kinase kinase MMR Mismatch repair MPP+ 1-methyl-4-phenylpyridinium Chk2 Cell cycle checkpoint kinase 2 MPTP 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine MRE11 Meiotic recombination element 11 MRN MRE11/Rad50/NBS1 complex mTOR Mammalian target of rapamycin vi NBT Nitro blue tetrazolium NDDs Neurodegenerative diseases NER Nucleotide excision repair Nf-B Nuclear factor-B NFT Neutrophin NHEJ Non-homologous end joining NMDA N-Methyl-D-aspartic acid NP Natural product NQO1 NAD(P)H dehydrogenase, quinone 1 Nrf2 Nuclear factor erythroid 2-related factor 2 OMT o-methyltransferase OPA Orthophthalaldehyde ORAC Oxygen radical absorbance capacity OST Oligosaccharyltransferase PAL Phenylalanine ammonia-lyase PBS Phosphate buffer saline PCD Programmed cell death PCNA Proliferating cell nuclear antigen PCR Polymerase chain reaction PD Parkinson’s disease PDA Photo diode array PEF Phenolic-enriched fraction PG Post gastric (digest) PI Propidium iodide PI3K 1. Phosphoinositide 3-kinase PKA cAMP-dependent protein kinase PLA2 Group II phospholipase A2 POLR2A DNA-directed RNA polymerase II subunit A PP Polyphenol PP1-cat Protein phosphatase catalytic subunit PP2A Protein phosphatase 2A catalytic subunit PP2C Protein phosphatase 2C QGlc Quercetin-glucoside QGlcA Quercetin-glucuronide QHMGG Quercetin-HMG-glucoside QHMGGlc Quercetin-HMG-glucoside Qpent Quercetin pentose Qrut Quercetin-rutinoside QXyl Quercetin-xyloside RAN Ras-related nuclear protein RMA Robust Multi-array average RNS Reactive nitrogen species RONS Reactive oxygen and nitrogen species ROS Radical oxygen species RT Retention time RT-PCR Reverse transcription-polymerase chain reaction Sang Sanguiin SD Standard deviation SIRT1 Sirtuin 1 SN Substancia nigra SOD Superoxide dismutase SPE Solid phase extraction STS Stilbene synthase TE Trolox equivalents TFC Total flavonoid content TFIIH Transcription factor II H TOP Topoisomerase TPC Total phenolic content TrkB Tyrosin-related kinase B UFGT UDP glucose-flavonoid 3-glucosyltransferase vii UPS Ubiquitin-proteasome system UPW Ultra pure water XPG Xeroderma pigmentosum complementation group G XRE Xenobiotic responsive element viii Abstract Neurodegenerative diseases have become a challenge to modern societies in industrialized countries due to the high social and economic impacts and therefore demand intensive research. These diseases present diverse common features, in which oxidative stress plays a very important role. As result of oxidative stress, some molecular mechanisms become dysfunctional and ultimately lead to cell death. Amongst the compounds displaying neuroprotective activity, phenolics have been identified amongst the most active substances from natural sources. The purpose of the work presented in this thesis was to address the neuroprotective capacity of phenolic compounds from juniper
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