Identification of Secondary Metabolites from Marine Microorganisms
해양미생물의 이차대사산물 규명

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dc.description학위논문 (박사)-- 서울대학교 대학원 자연과학대학 지구환경과학부, 2017. 8. 강헌중.-
dc.description.abstractThe marine environment has become a rich source of secondary metabolites which are structurally unique and biologically active. Marine microorganisms living in the diverse environment have been considered as new sources of pharmaceutical leads and actual producers of bioactive natural products.
In our search for new bioactive compounds from marine actinobacteria, we obtained novel compounds, anmindenols A-B, marinopyrones A-D and 11A020-3A from the actinomycetes. Their structures were elucidated by the interpretation of 1D, 2D NMR and MS spectroscopic data. Anmindenols A-B and marinopyrone D were examined for their inhibition of nitric oxide production in LPS-stimulated RAW 264.7 macrophage cells and exhibited weak inhibitory activity on nitric oxide production with the IC50 value of 23 μM, 19 μM and 13 μM, respectively. 11A020-3A showed antibacterial activity with IC50 value of 0.1 μM, 64 μM, 8 μM and 64 μM against Bacillus subtilis, Kocuria rhizophila, Staphylococcus aureus and Escherichia coli, respectively.
In the course of our research for the chemical investigation of secondary metabolites from marine fungi, F8015-2B-2B, 2C, 2E and 2I were obtained from the fungus Mycosphaerella nawae. The structures of the compounds were determined by comparison of NMR and MS data.
dc.description.abstract해양환경은 구조적으로 특이한 생리활성을 가진 2차 대사산물을 발견할 수 있는 다양한 자원을 가지고 있다. 특히 해양미생물은 약제학적 선도물질이 될 수 있는 생리활성을 가진 천연물의 실제적인 생산자이다.
해양미생물 중에서 현재까지 가장 많은 생리활성물질이 보고된 해양방선균의 새로운 2차 대사산물을 탐색하는 과정에서 신규물질 안민디놀 A와 B, 마리노파이론 A-D 그리고 11A020-3A를 발견할 수 있었다. 이 물질의 구조는 1D, 2D NMR 스펙트럼 데이터 분석과 질량분석을 통해 규명하였다. 안민디놀 A와 B, 마리노파이론 D는 항염증성 정도를 측정하는 생리활성 테스트인 LPS-stimulated RAW 264.7 대식세포 상에서 일산화질소의 생성을 억제하는 실험을 수행한 결과 각각 23 μM, 19 μM, 13 μM의 활성을 보였으며, 11A020-3A는 항균실험 결과 Bacillus subtilis, Kocuria rhizophila, Staphylococcus aureus 그리고 Escherichia coli에 대해 각각 0.1 μM, 64 μM, 8 μM, 64 μM 활성을 보였다.
해양곰팡이의 2차대사산물을 탐색화는 과정에서는 곰팡이 Mycosphaerella nawae 종에서 F8015-2B-2B, 2C, 2E, 2I 이렇게 총 4개의 새로운 우스닉산 유도체를 발견하였다. 이 물질 역시 NMR 스펙트럼 데이터와 질량분석 데이터를 통해 구조를 규명하였다.
dc.description.tableofcontentsChapter 1. Introduction of Marine Natural Products
1.1 Marine Natural Products
1.1.1 Marine Natural Products in General 1
1.1.2 Drug Development from Marine Natural Products 9
1.2 Marine Microorganisms as a Source for Natural Products
1.2.1 Marine Microorganisms 12
1.2.2 Bioactive Metabolites from Marine Bacteria 14
1.2.3 Bioactive Metabolites from Marine Fungi 18

Chapter 2. Marinopyrones A-D, -Pyrones from Marine-Derived Actinomycetes of the Family Nocardiopsaceae
2.1 Introduction 26
2.2 Results and Discussion
2.2.1 Structural Elucidation of Marinopyrones Marinopyrone A (1) 29 Marinopyrone B (2) 33 Marinopyrone C (3) 35 Marinopyrone D (4) 38
2.2.2 Biological Activities Antibacterial Activity 41 Cytotoxicity 41 Anti-Inflammatory Activity 41
2.3 Experimental Section
2.3.1 Instruments and Data Collection 44
2.3.2 Bacterial Material 45
2.3.3 Cultivation, Extraction and Isolation 46
2.3.4 Determination of the Absolute Configuration for compound 4 47
2.3.5 Bioassays MIC Assay 48 MTT Assay 49 Nitric Oxide Assay 49

Chapter 3. Anmindenols A and B, sesquiterpenoids from a Marine-derived Streptomyces sp.
3.1 Introduction 51
3.2 Results and Discussion
3.2.1 Structural Elucidation of Anmindenols Anmindenol A (5) 57 Anmindenol B (6) 60
3.2.2 Biological Activities Antibacterial Activity 63 Cytotoxicity 63 Anti-Inflammatory Activity 63
3.3 Experimental Section
3.3.1 Instruments and Data Collection 66
3.3.2 Bacterial Material 67
3.3.3 Cultivation, Extraction and Isolation 67
3.3.4 Electronic Circular Dichroism of a Dimolybdenum Complex 68
3.3.5 Bioassays MIC Assay 69 MTT Assay 69 Nitric Oxide Assay 69

Chapter 4. 11A020-3A from mudflat derived Actinoalloteichus Hymeniacidonis sp.
4.1 Introduction 70
4.2 Results and Discussion
4.2.1 Structural Elucidation of 11A020-3A 11A020-3A (7) 73
4.2.2 Biological Activities Antibacterial Activity 77
4.3 Experimental Section
4.3.1 Instruments and Data Collection 78
4.3.2 Bacterial Material 78
4.3.3 Cultivation, Extraction and Isolation 79
4.3.4 Bioassays MIC assays 80
Chapter 5. Usnic Acid Derivatives from Mycosphaerella nawae
5.1 Introduction 81
5.2 Results and Discussion
5.2.1 Structural Elucidation of Usnic Acid Derivatives F8015-2B-2E (8) 83 F8015-2B-2I (9) 86 F8015-2B-2B (10) 88 F8015-2B-2C (11) 90
5.3 Experimental Section
5.3.1 Instruments and Data Collection 92
5.3.2 Fungal Material 92
5.3.3 Cultivation, Extraction and Isolation 93

Appendix A 95
Appendix B 120
Appendix C 135
Appendix D 142
한글초록 161
dc.format.extent7135827 bytes-
dc.publisher서울대학교 대학원-
dc.subjectMarine natural products-
dc.subjectMarine microorganisms-
dc.subjectSecondary metabolites-
dc.titleIdentification of Secondary Metabolites from Marine Microorganisms-
dc.title.alternative해양미생물의 이차대사산물 규명-
dc.contributor.AlternativeAuthorJihye Lee-
dc.contributor.affiliation자연과학대학 지구환경과학부-
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College of Natural Sciences (자연과학대학)Dept. of Earth and Environmental Sciences (지구환경과학부)Theses (Ph.D. / Sc.D._지구환경과학부)
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