Structure Determination of Secondary Metabolites from Marine-Derived Microorganisms, a Streptomyces sp. and Two Bacillus spp. with Their Biological Activities

목차 (Table of Contents)

• 1. Introduction 1
• 1.1 History of Natural Products 1
• 1.2 Marine Natural Products 5
• 1.3 Dereplication 9
• II. Discovery of Secondary Metabolites of Marine-Derived Streptomyces sp. 13G036 13
• 1. Isolation of Bacterial strain and Preparation of Extracts 13
• 1.1 Isolation and Identification of Bacteria Strain 13
• 1.2 Cultivation of Bacterial Strain 15
• 1.3 Preparation of Culture Media Extract of Streptomyces sp. 13G036 16
• 1.4 Molecular Networking Analysis of 13G036 17
• 2. Discovery of Novel Cyclic Octapeptides of Streptomyces sp. 13G036 20
• 2.1 Experimental Section 20
• 2.1.1 General Experiment Procedures 20
• 2.1.2 Isolation of Compounds 1-4 21
• 2.1.3 C3 Marfey's Method 22
• 2.1.4 2D C3 Marfey′s Method 24
• 2.2 Results and Discussion 27
• 2.2.1 Elucidation of Planar Structure of 1-4 27
• 2.2.2 Determination of Absolute Configurations of Compounds 1-4 with C3 and 2D C3 Marfey′s Methods 57
• 3. Discovery of Butenolide from Streptomyces sp. 13G036 71
• 3.1 Experimental Section 71
• 3.1.1 General Experiment Procedures 71
• 3.1.2 Extraction and Isolation of Compounds 5-12 72
• 3.2 Results and Discussion 73
• 3.2.1 Elucidation of Planar Structure of 5-12 73
• 3.2.2 Absolute Configuration Analysis of Compounds 5-12 99
• III. Discovery of Macrolactins from Bacillus sp. HC001 103
• 1. Experimental Section 103
• 1.1 General Experiment Procedures 103
• 1.2 Isolation and Identification of Bacteria Strain 104
• 1.3 Cultivation of Bacterial Strain 105
• 1.4 Preparation of Culture Media Extract of Bacillus sp. HC001 106
• 1.5 Isolation of Compounds 13-15 107
• 1.6 Determination of Absolute Configuration of C-7, C-13, and C-15 in Compound 15 by Mosher′s Esterification 108
• 2. Results and Discussion 109
• 2.1 Structure Elucidation of Compounds 13-15 109
• IV. Structure Identification of 2,4-Di-tert-butylphenol-Containing Compound from Marine-Derived Bacillus sp. 13F045 127
• 1. Experimental Section 127
• 1.1 General Experiment Procedures 127
• 1.2 Isolation and Identification of Bacteria strain 128
• 1.3 Cultivation of Bacterial Strain 129
• 1.4 Preparation of Culture Media Extract of Bacillus sp. 13F045 130
• 1.5 Extraction and Isolation of Compound 16 131
• 1.6 Acid Hydrolysis of Compound 16 132
• 2. Results and Discussion 133
• 2.1 Elucidation of Planar Structure of Compound 16 133
• 2.2 Absolute Configuration Analysis of Glucose unit in 16 139
• V. Biological Activity Investigation of Compounds 1-15 141
• 1. Introduction 141
• 2. Experimental Section 144
• 2.1 Anti-inflammatory and Anti-cancer Assay 144
• 2.2 Antimicrobial Assay 145
• 2.3 Cytoprotective and Anti-inflammatory Assay 146
• 2.4 Effect of Compound 14 on Osteoclastogenesis and Osteoblastogenesis 147
• 3. Results and Discussion 148
• 3.1 Anti-inflammatory, Anti-cancer, and Antimicrobial Activities of Compounds 1-3, 5-8, 10 and 12 148
• 3.2 Cytoprotective and Anti-inflammatory Activities of Compounds 13-15 150
• 3.3 Effect of Compound 14 on Osteoclastogenesis and Osteoblastogenesis 154
• VI. Conclusion 158
• References 161
• Appendix 168