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Szent István University Faculty of Horticultural Science Department of Genetics and Plant Breeding 10.14751/SZIE.2016.071 SZENT ISTVÁN UNIVERSITY FACULTY OF HORTICULTURAL SCIENCE DEPARTMENT OF GENETICS AND PLANT BREEDING ANALYSIS OF THE GLYCOSIDE BIOSYNTHESIS IN RHODIOLA ROSEA L. DOCTORAL (Ph.D.) DISSERTATION SEYED IMAN MIRMAZLOUM SUPERVISOR: BENYÓNÉ DR. GYÖRGY ZSUZSANNA BUDAPEST 2016 1 10.14751/SZIE.2016.071 Ph.D School Name: Doctoral School of Horticultural Science Field: Crop Sciences and Horticulture Head of the Ph.D school: Prof. Dr. Zámboriné Németh Éva, Doctor of the Hungarian Academy of Science Head of Department of Medicinal and Aromatic SZENT ISTVÁN UNIVERSITY, Faculty of Horticultural Science Supervisor: Benyóné Dr. György Zsuzsanna Department of Genetics and Plant Breeding SZENT ISTVÁN UNIVERSITY, Faculty of Horticultural Sciences The applicant met the requirement of the Ph.D regulations of the SZENT ISTVÁN UNIVERSITY and the thesis is accepted for the defense process. .................................. ................................ Head of Ph.D. School Supervisor 2 10.14751/SZIE.2016.071 JURY MEMBERS: Chairman: Dr. Jenő Bernáth DSc Scientific committee: Dr. István Papp DSc Dr. György Bisztray PhD Dr. Éva Szőke DSc Dr. Alexandra Soltész PhD Opponents: Dr. Tamás Deák PhD Dr. Ágnes Dalmadi PhD 3 10.14751/SZIE.2016.071 CONTENT LIST OF ABBREVIATIONS…………………………………………………………………….....6 1. INTRODUCTION AND OBJECTIVES ....................................................................................... 7 2. LITERATURE REVIEW ......................................................................................................... 9 2.1. Rhodiola rosea L. botany ............................................................................................ 9 2.2. Conservation ............................................................................................................. 10 2.3. R. rosea, as a traditional medicine and as a modern adaptogen .................................. 11 2.4. Active constituents and secondary metabolites .......................................................... 14 2.5. Mechanism of action ................................................................................................. 16 2.6. Biosynthetic pathways for Rhodiola phytopharmaceuticals.........................................18 2.6.1. Cinnamyl alcohol glycosides (CAGs) biosynthesis pathway ................................... 20 2.6.2. Salidroside biosynthesis pathway ........................................................................... 22 2.7. The enhancement of roseroot secondary metabolites in in vitro cultures .................... 26 2.7.1. In vitro culture of R. rosea ..................................................................................... 26 2.7.2. Explants for in vitro culture .................................................................................... 27 2.7.3. Callus induction and tissue culture ....................................................................... 27 3. MATERIALS AND METHODS .............................................................................................. 29 3.1. Plant materials .......................................................................................................... 29 3.2. In vitro experiments of roseroot ................................................................................ 29 3.2.1. In vitro cultures ...................................................................................................... 30 3.2.2. Transgenic callus culture establishment .................................................................. 30 3.2.2.1. Transformation of the callus .............................................................................. 30 3.2.2.2. DNA extraction and polymerase chain reaction (PCR) ........................................ 31 3.2.2.3. Histochemical GUS assay ................................................................................... 32 3.2.3. Hormonal effects of antibiotics on callus culture .................................................... 32 3.2.4. Precursor feeding and biotransformation ................................................................ 32 3.3. Phytochemical analysis ............................................................................................. 33 3.3.1. Extraction and HPLC ............................................................................................. 33 3.3.2. Statistical analysis ....... ..............................................................................................34 3.3.3. Definition and comparison of the values of dissimilarity index ............................... 34 3.3.4. The characteristic code of accumulation process .................................................... 34 3.4. Molecular biology experiments ................................................................................. 35 3.4.1. Genomic DNA extraction ....................................................................................... 36 3.4.2. RNA extraction ...................................................................................................... 36 3.4.3. Reverse transcription (cDNA synthesis) ................................................................. 37 3.4.4. Rapid amplification of cDNAs end (RACE) ........................................................... 37 3.4.4.1. 3′ cDNA end amplification .................................................................................. 37 3.4.4.2. 5′ cDNA end amplification .................................................................................. 38 3.4.5. Data mining and degenerate primer design ............................................................. 39 3.4.6. R. rosea specific UDPG and AAD primer design .................................................. 40 3.4.7. Isolation of full length UDPG and AAD open reading frame................................... 40 3.4.8. Genomic sequence of UDPG and AAD................................................................... 41 3.4.9. Phylogenetic trees .................................................................................................. 42 3.4.10. Heterologous expression of UDPG ....................................................................... 42 3.4.10.1. Plasmid vector and restriction sites .................................................................... 42 3.4.10.2. Primer design and PCR amplification ................................................................ 43 3.4.10.3. Preparation of the expression vector for ligation ................................................ 44 4 10.14751/SZIE.2016.071 3.4.10.4. Ligation cloning of UDPG into pET-24 vector.................................................. 44 3.4.10.5. Cloning of UDPG in BL21 (DE3) pLysS E. coli ............................................... 45 3.4.10.6. Expression induction and SDS-PAGE ............................................................... 45 3.4.10.7. Affinity chromatography................................................................................... 46 3.4.10.8. Western blotting ............................................................................................... 47 3.4.10.9. UDPG and AAD gene expression analysis......................................................... 47 3.4.11. Gene expression analysis in rosavins biosynthesis pathway ................................. 49 3.4.11.1. Primer design and qPCR ................................................................................... 49 3.4.11.2. Analysis of the gene expression data ................................................................. 50 4. RESULTS ........................................................................................................................... 52 4.1. In vitro experiments of roseroot ................................................................................ 52 4.1.1. In vitro culture ........................................................................................................ 52 4.1.2. Transgenic roseroot callus culture establishment .................................................... 54 4.1.3. Hormonal effects of antibiotics on R. rosea callus culture ....................................... 56 4.1.4. Precursor feeding and biotransformation ................................................................. 58 4.1.4.1. Precursor feeding in salidroside pathway ............................................................. 59 4.1.4.2. Precursor feeding in cinnamyl alcohol glycosides (CAGs) pathway ..................... 61 4.2. Roseroot phytochemical analysis during the vegetation period .................................. 67 4.3. Molecular biology experiments............................................... ....................................71 4.3.1. Isolation of R. rosea UDP- glycosyltransferase gene ............................................... 71 4.3.2. Phylogenetic tree for R. rosea UDPG gene ............................................................. 74 4.3.3. Isolation of R. rosea Aryl Alcohol Dehydrogenase (AAD) gene .............................. 74 4.3.4. Phylogenetic tree for R. rosea AAD gene ................................................................ 76 4.3.5. Heterologous expression of R. rosea UDPG gene ................................................... 79 4.3.6. UDPG and AAD gene expression analysis in vitro .................................................. 82 4.3.7. Gene expression analysis in vivo ............................................................................. 90 5. DISCUSSION
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