New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species
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| Sprache: | English |
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2018
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| 100 | 1 | |a Mudalungu, Cynthia Muhavi |e Verfasser |0 (DE-588)1165269198 |4 aut | |
| 245 | 1 | 0 | |a New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species |c vorgelegt von M.Sc. Cynthia Muhavi Mudalungu, aus Kakamega, Kenia |
| 264 | 1 | |a Berlin |c 2018 | |
| 300 | |a vi, 134 Seiten |b Diagramme |c 21 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |b Dissertation |c Technische Universität Berlin |d 2018 | ||
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
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| 856 | 4 | |u http://verlag.tu-berlin.de/abstracts/diss/mudalungu_cynthia_abstract.pdf |3 Abstract | |
| 856 | 4 | |u http://verlag.tu-berlin.de/abstracts/diss/mudalungu_cynthia_inhalt.pdf |3 Inhaltsverzeichnis | |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030535590&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-030535590 | |
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| _version_ | 1819756067017457664 |
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| adam_text | TABLE OF CONTENTS
ABBREVIATIONS.........................................................................................................................................I
LIST OF
FIGURES........................................................................................................................................III
LIST OF
TABLES.........................................................................................................................................VI
1
INTRODUCTION...............................................................................................................................
1
1.1 NATURAL PRODUCTS AND THEIR PHARMACOLOGICAL RELEVANCE
..............................................
1
1.1.1 SOME NOVEL METABOLITES FROM UNDEREXPLORED SOURCES
........................................
2
1.1.2 SELECTED CLASSES OF PATHWAY-SPECIFIC SECONDARY METABOLITES
..........................
3
1.1.2.1
PEPTIDES.........................................................................................................3
1.1.2.2
POLYKETIDES....................................................................................................
6
1.1.2.3
TERPENES.......................................................................................................
7
1.2 RECENT ADVANCES TOWARDS DISCOVERY OF NOVEL BIOACTIVE METABOLITES
.........................
8
1.2.1 UNCULTURED ORGANISMS AND NEW ECOLOGICAL NICHES
...............................................
9
1.2.2
BIOINFORMATICS.....................................................................................................10
1.3 THE PHYLUM
BASIDIOMYCOTA.........................................................................................10
1.3.1 CYATHANE DITERPENOID METABOLITES
....................................................................
11
1.4 THE GENUS
STREPTOMYCES AND SOME OF ITS IMPORTANT
METABOLITES...............................12
1.5 ESSENTIAL TOOLS SUPPORTING THE DISCOVERY OF NOVEL METABOLITES
................................
13
1.5.1 MASS SPECTROMETRY
(MS).....................................................................................13
1.5.2 GENOME
MINING...................................................................................................13
1.5.3 NUCLEAR MAGNETIC RESONANCE (NMR) SPECTROSCOPY
..........................................
14
2 AIM OF THE
STUDY....................................................................................................................
15
2.1 OBJECTIVES 15
3
MATERIALS...................................................................................................................................16
3.1 EQUIPMENT AND
SOFTWARE.............................................................................................16
3.1.1
EQUIPMENT............................................................................................................16
3.1.2
SOFTWARE...............................................................................................................18
3.2
CHEMICALS.....................................................................................................................
18
3.3
MICROORGANISMS...........................................................................................................19
3.4 CULTURE MEDIA
TYPES.....................................................................................................21
3.5 BUFFERS AND
SOLUTIONS...................................................................................................22
4
METHODS....................................................................................................................................23
4.1 ISOLATION AND CHARACTERIZATION OF LAXITEXTINE COMPOUNDS FROM
LAXITEXTUM
INCRUSTATUM
(BASIDIOMYCOTA)................................................................................................23
4.1.1 STRAIN COLLECTION AND CHARACTERIZATION
................................................................
23
4.1.2 FERMENTATION OF LAXITEXTUM INCRUSTATUM (STMA 14285)
...................................
23
4.1.3 EXTRACTION AND
ISOLATION........................................................................................24
4.1.4 THE ANALYTICAL TECHNIQUES USED IN STRUCTURE
ELUCIDATION.....................................24
4.1.5 ANTIBACTERIAL
ASSAYS..............................................................................................25
4.1.6 CYTOTOXICITY
ASSAYS...............................................................................................25
4.2 ISOLATION AND CHARACTERIZATION OF THE STREPTOMYCES-DERIVED
METABOLITES
.................
25
4.2.1 ISOLATION OF THE ANGUCYCLINONE AND ANTHRACYCLINE
COMPOUNDS..........................25
4.2.1.1 CULTIVATION, EXTRACTION AND
FRACTIONATION....................................................25
4.2.1.2 PURIFICATION OF THE
ANGUCYCLINONE................................................................
26
4.2.1.3 PURIFICATION OF THE ANTHRACYCLINES
................................................................
26
4.2.2 ISOLATION OF THE NOURSAMYCIN
COMPOUNDS........................................................... 27
4.2.2.2 PURIFICATION OF THE
NOURSAMYCINS...............................................................27
4.2.3 ISOLATION OF THE LINARIDIN PEPTIDES
.....................................................................
28
4.2.3.1 CULTIVATION, EXTRACTION AND FRACTIONATION
...................................................
28
4.2.3.2 PURIFICATION OF THE LINARIDINS
.......................................................................
28
4.2.4 HPLC-MS
ANALYSES..............................................................................................29
4.2.5 MALDI-TOF/TOF-MS ANALYSIS
.............................................................................
30
4.2.6 MS/MS ANALYSIS AND SPECTRAL NETWORKING
..........................................................
30
4.2.7 AMINO ACID
ANALYSIS.............................................................................................30
4.2.8 NMR SPECTROSCOPIC ANALYSIS
...............................................................................
31
4.2.9 GENOMIC DNA EXTRACTION AND SEQUENCING
........................................................
31
4.2.10 BIOACTIVITY TESTS
...............................................................................................
31
4.2.10.1 AGAR-DIFFUSION ASSAYS
..................................................................................
31
4.2.10.2 MICRO-DILUTION ASSAY FOR THE DETERMINATION OF MIC VALUES
.......................
32
4.2.10.3 CYTOTOXICITY
.................................................................................................
32
5 RESULTS AND
DISCUSSION..........................................................................................................33
5.1 CYATHANE XYLOSIDES FROM LAXITEXTUM INCRUSTATUM
....................................................
33
5.1.1 BIOACTIVITY GUIDED ISOLATION
................................................................................
33
5.1.2 STRUCTURE ELUCIDATION AND CHARACTERIZATION
.......................................................
34
5.1.2.1 HPLC-ESI-MASS SPECTROMETRY OF THE LAXITEXTINE COMPOUNDS
.....................
34
5.1.2.2 NMR SPECTROSCOPIC ANALYSIS OF COMPOUND 1 (LAXITEXTINE A)
.....................
35
5.1.2.3 NMR ANALYSIS OF COMPOUND 2 (LAXITEXTINE B)
............................................
41
5.1.2.4 PHYSICO-CHEMICAL PROPERTIES OF LAXITEXTINES A AND B
.................................
47
5.1.3 BIOSYNTHESIS OF LAXITEXTINE A AND B (CYATHANE DERIVATIVES)
..............................
47
5.1.4 ANTIBACTERIAL
ACTIVITY...........................................................................................
49
5.1.5
CYTOTOXICITY...........................................................................................................50
5.2 ANGUCYCLINONE AND ANTHRACYCLINES FROM STREPTOMYCES
RK57...................................51
5.2.1 ANGUCYCLINONE: ISOLATION AND CHEMICAL
CHARACTERIZATION....................................51
5.2.1.1 HPLC-ESI-MASS SPECTROMETRY OF ANGUCYCLINONE
.........................................
51
5.2.1.2 NMR ANALYSIS OF
ANGUCYCLINONE...................................................................52
5.2.2 ANTHRACYCLINES: ISOLATION AND CHEMICAL
CHARACTERIZATION....................................58
5.2.2.1 HPLC-ESI-MASS SPECTROMETRY OF ANTHRACYCLINE RK57A AND RK57B
.............
58
5.2.2.2 NMR SPECTROSCOPIC ANALYSIS OF THE ANTHRACYCLINE
RK57A............................59
5.2.23 NMR ANALYSIS OF THE ANTHRACYCLINE RK57B
..................................................
62
5.2.3 BIOSYNTHESIS OF THE ANGUCYCLIN(ON)E AND
ANTHRACYCLIN(ON)E...............................65
5.2.3.1 BIOSYNTHESIS OF THE
AGLYCON..........................................................................66
5.23.2 BIOSYNTHESIS OF
DEOXYSUGARS........................................................................
66
5.2.4 BIOLOGICAL
ACTIVITY..................................................................................................67
5.3 NOURSAMYCIN PEPTIDES FROM STREPTOMYCES NOURSEI
NTR-SR4....................................68
5.3.1 HPLC-ESI-MASS SPECTROMETRY OF
NOURSAMYCINS..................................................68
5.3.2 SPECTRAL NETWORKING
ANALYSIS...............................................................................
73
5.3.3 STRUCTURE ELUCIDATION OF THE ISOLATED NOURSAMYCIN PEPTIDES
.............................
74
5.3.4 AMINO ACID ANALYSIS OF PEPTIDES A AND B USING
GC-MS.......................................82
5.3.5 BIOSYNTHESIS OF
NOURSAMYCINS.............................................................................
83
5.3.6 BIOLOGICAL
ACTIVITY.................................................................................................
87
5.4 GRISEMYCIN DERIVATIVES - LINARIDIN PEPTIDES FROM STREPTOMYCES SP.
T002
...............
89
5.4.1 IDENTIFICATION OF NEW METABOLITES
89
5.4.2 HPLC-ESI-MASS SPECTROMETRY OF THE 1768 DA PEPTIDE
......................................
91
5.4.3 STRUCTURE ELUCIDATION OF THE 1768 DA
PEPTIDE..................................................93
5.4.4 AMINO ACID ANALYSIS OF THE 1768 DA PEPTIDE
.....................................................
94
5.4.5 IDENTIFICATION OF THE PUTATIVE BIOSYNTHETIC GENE CLUSTER
....................................
94
5.4.6 BIOLOGICAL
ACTIVITY.................................................................................................95
6 CONCLUSIONS AND FUTURE
PERSPECTIVES...................................................................................96
7
REFERENCES................................................................................................................................
98
8
APPENDIX.................................................................................................................................107
|
| any_adam_object | 1 |
| author | Mudalungu, Cynthia Muhavi |
| author_GND | (DE-588)1165269198 |
| author_facet | Mudalungu, Cynthia Muhavi |
| author_role | aut |
| author_sort | Mudalungu, Cynthia Muhavi |
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| bvnumber | BV045145837 |
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| id | DE-604.BV045145837 |
| illustrated | Not Illustrated |
| indexdate | 2024-12-24T06:50:40Z |
| institution | BVB |
| language | English |
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| physical | vi, 134 Seiten Diagramme 21 cm |
| publishDate | 2018 |
| publishDateSearch | 2018 |
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| spellingShingle | Mudalungu, Cynthia Muhavi New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species |
| subject_GND | (DE-588)4113937-9 |
| title | New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species |
| title_auth | New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species |
| title_exact_search | New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species |
| title_full | New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species vorgelegt von M.Sc. Cynthia Muhavi Mudalungu, aus Kakamega, Kenia |
| title_fullStr | New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species vorgelegt von M.Sc. Cynthia Muhavi Mudalungu, aus Kakamega, Kenia |
| title_full_unstemmed | New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species vorgelegt von M.Sc. Cynthia Muhavi Mudalungu, aus Kakamega, Kenia |
| title_short | New bioactive secondary metabolites from Laxitextum incrustatum (Basidiomycota) and selected Streptomyces species |
| title_sort | new bioactive secondary metabolites from laxitextum incrustatum basidiomycota and selected streptomyces species |
| topic_facet | Hochschulschrift |
| url | http://d-nb.info/1161487891/04 http://verlag.tu-berlin.de/abstracts/diss/mudalungu_cynthia_abstract.pdf http://verlag.tu-berlin.de/abstracts/diss/mudalungu_cynthia_inhalt.pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030535590&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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