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Title Page

ABSTRACT

Contents

I. Introduction 16

1. Seaweeds 17

2. Properties of the brown alga, E. bicyclis 18

3. Antioxidant activity 19

4. Anti-obesity activity 21

5. Anti-inflammatory activity 23

6. Purpose of the study 25

II. Materials and Methods 26

1. Materials 27

2. Analysis of nutritional component of E. bicylcis 27

2.1. Analysis of proximate composition, dietary fiber and mineral 27

2.2. Analysis of monosaccharide compositions 28

2.3. Extraction of E. bicyclis 29

2.4. Determination of total polyphenol content (TPC) 30

2.5. Determination of total sugar 30

2.6. Determination of reducing sugar 31

3. Evaluation of biological activities from E. bicyclis 32

3.1. Antioxidant activity of E. bicyclis extract 32

3.2. Anti-obesity activity of seaweeds extract (in vitro) 33

3.3. Anti-obesity activity of E. bicyclis extract on 3T3-L1 adipocyte differentiation 34

3.4. Anti-obesity activity of E. bicyclis extract (in vivo) 36

4. Isolation of active compounds from E. bicyclis 38

4.1. Isolation and extraction of E. bicyclis 38

4.2. Analysis of structure from active compound 40

4.3. Contents of five compounds E. bicyclis ethanol and water extracts 40

5. Antioxidant activity of active compounds isolated from E. bicyclis 41

5.1. Materials and chemicals 41

5.2. Total polyphenol content(TPC) of solvent-partitioned fraction from E.bicyclis 41

5.3. DPPH radical scavenging activity 42

5.4. ABTS radical scavenging activity 42

5.5. Reducing power ability 43

5.6. Activity of singlet oxygen quenching 43

5.7. Statistical analysis 44

6. Anti-obesity activity of five pure compounds isolated from E. bicyclis and its mechanism 45

6.1. Materials and chemicals 45

6.2. Cell culture and adipocyte differentiation 46

6.3. MTT assay for measurement of cell viability 46

6.4. Oil red O staining 47

6.5. Western blot analysis 47

6.6. RT-PCR 48

6.7. Statistical analysis 50

7. Anti-inflammatory activity of five pure compounds isolated from E. bicyclis and its mechanism 51

7.1. Materials and chemicals 51

7.2. Cell culture 52

7.3. Nitrite assay and measurenent of cee viability 52

7.4. Western blot analysis 53

7.5. RT-PCR 54

III. Results and Discussion 55

Part 1. Nutritional component of E. bicyclis 56

1.1. Proximate composition and mineral content 56

1.2. Monosaccharide compositions 58

1.3. Total polyphenol, total sugar, and reducing sugar contents 59

Part 2. Biological activities from E. bicyclis 61

2.1. Antioxidant activity (DPPH radical scavenging activity) 61

2.2. Anti-obesity activity of E. bicyclis extract (in vitro) 63

2.3. Anti-obesity activity of E, bicyclis (in vivo) 69

Part 3. Isolation of active compounds from E. bicyclis and its biological activity 73

3.1. Isolation of active compounds from E. bicyclis 73

3.2. Antioxidant activity of active compounds isolated from Eisenia bicyclis 88

3.3. Anti-obesity activity of five compounds isolated from E. bicyclis and their mechanism 100

3.4. Anti-inflammatory activity of five pure compounds isolated from E. bicyclis and their mechanism 118

IV. Conclusion 127

V. REFERENCES 129

초록 139

List of Tables

Table 1. The conditions for analysis of monosaccharide content 28

Table 2. Composition of experimental diets 37

Table 3. Proximate compositions of E. bicyclis (dry basis) 57

Table 4. Mineral contents of E. bicyclis (dry basis) 57

Table 5. Monosaccharide compositions from E. bicyclis (dry basis) 58

Table 6. Contents of total ployphenol, total sugar and reducing sugar from E. bicyclis extracts 60

Table 7. DPPH radical scavenging activities of E. bicyclis ethanol and water extracts 62

Table 8. Lipase inhibitory activities of E. bicyclis ethanol and water extracts 64

Table 9. α-Amylase inhibitory activities of E. bicyclis ethanol and water extracts 66

Table 10. Effect of E. bicyclis on body weight 69

Table 11. Effect of E. bicyclis on lipid profiles, insulin and leptin in the serum 71

Table 12. Total phenolic contents and radical scavenging activity of solvent partitioned fractions from E. bicyclis 91

Table 13. DPPH radical scavenging activities of five compounds isolated from E. bicyclis 95

Table 14. ABTS radical scavenging activities of five compounds isolated from E. bicyclis 96

List of Figures

Fig. 1. Flow chart of extraction of seaweed. 29

Fig. 2. Procedure of the purification and extraction from E. bicyclis. 39

Fig. 3. Effect of E. bicyclis water and ethanol extracts on adipocyte differentiation (x100). 68

Fig. 4. Images of H&E staining of epididymal adipose tissues. (x200) 72

Fig. 5. HPLC chromatogram of five compounds isolated from E. bicyclis. 75

Fig. 6. ¹H NMR (A), FAB-mass spectrum (B) and ¹³C NMR (C) of 6,6'-bieckol isolated from E. bicyclis. 77

Fig. 7. ¹H NMR (A), FAB-mass spectrum (B) and ¹³C NMR (C) of 6,8'-bieckol isolated from E. bicyclis. 79

Fig. 8. ¹H NMR (A), FAB-mass spectrum (B) and ¹³C NMR (C) of 8,8'-bieckol isolated from E. bicyclis. 81

Fig. 9. ¹H NMR (A), FAB-mass spectrum (B) and ¹³C NMR (C) of dieckol isolated from E. bicyclis. 83

Fig. 10. ¹H NMR (A), FAB-mass spectrum (B) and ¹³C NMR (C) of phlorofiicofuroeckol-A isolated from E. bicyclis. 85

Fig. 11. Chemical structures of five compounds isolated from E. bicyclis. 86

Fig. 12. Contents of five compounds of E. bicyclis ethanol and water extracts. 87

Fig. 13. Reducing power ability of solvent partitioned fractions from E. bicyclis. 92

Fig. 14. Reducing power ability of five compounds isolated from E. bicyclis. 97

Fig. 15. Kinetics of singlet oxygen quenching of pure compounds isolated from E. bicyclis. 99

Fig. 16. Cell viability in 3T3-L1 adipocytes of five compounds isolated from edible brown alga, E. bicyclis. 101

Fig. 17. Effect of five compounds isolated from edible brown alga, E. bicyclis on lipid accumulation in 3T3-L1 adipocytes. The lipid accumulation in 3T3-L1 adipocytes were measured using Oil-Red O staining. 103

Fig. 18. Protein expression effects of 6,6'-bieckol on adipocyte differentiation in 3T3-L1 cells. 106

Fig. 19. Protein expression effects of 6,8'-bieckol on adipocyte differentiation in 3T3-L1 cells. 107

Fig. 20. Protein expression effects of 8,8'-bieckol on adipocyte differentiation in 3T3-L1 cells. 108

Fig. 21. Protein expression effects of dieckol on adipocyte differentiation in 3T3-L1 cells. 109

Fig. 22. Protein expression effects of phlorofiicofuroekcol-A on adipocyte differentiation in 3T3-L1 cells. 110

Fig. 23. Gene expression effects of 6,6'-bieckol on adipocyte differentiation in 3T3-L1 cells confirmed by RT-PCR. 113

Fig. 24. Gene expression effects of 6,8'-bieckol on adipocyte differentiation in 3T3-L1 cells confirmed by RT-PCR. 114

Fig. 25. Gene expression effects of 8,8'-bieckol on adipocyte differentiation in 3T3-L1 cells confirmed by RT-PCR. 115

Fig. 26. Gene expression effects of dieckol on adipocyte differentiation in 3T3-L1 cells confirmed by RT-PCR. 116

Fig. 27. Gene expression effects of phlorofucofuroeckol-A on adipocyte differentiation in 3T3-L1 cells confirmed by RT-PCR. 117

Fig. 28. Dieckol inhibited NO production in the range of concentrations used. 119

Fig. 29. Dieckol attenuated mRNA expressions of proinflammatory mediators. Cells were pre-treated with dieckol (12.5- 50 μM) for 30 min and then simulated with LPS for 18 h.... 122

Fig. 30. The effect of dieckol on iNOS and COX-2 protein expressions. Cells were pretreated with dieckol (12.5-50 μM) and then simulated with LPS (0.1 ㎍/ml) for 24 h to determine iNOS and COX-2 protein expressions. 123

Fig. 31. The effect of dieckol on p-IKK-α/β, and IκB-α. Cells were pretreated with dieckol (12.5-50 μM) and then simulated with LPS (0.1 ㎍/ml) for 24 h to determine the protein expressions. 125

Fig. 32. The effect of dieckol on PI3K/Akt and MAPK, p38,ERK, and JNK. Cells were pretreated with dieckol (12.5-50 μM) and then simulated with LPS (0.1 ㎍/ml) for 24 h to determine the protein expressions. 126

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