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研究生:吳建璋
研究生(外文):Chien-Chang Wu
論文名稱:福木及雙花金絲桃之活性成分研究
論文名稱(外文):Studies on the Bioactive Principles ofGarcinia subelliptica and Hypericum geminiflorum
指導教授:林忠男林忠男引用關係
指導教授(外文):Chun-Nan Lin
學位類別:博士
校院名稱:高雄醫學大學
系所名稱:藥學研究所
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2009
畢業學年度:97
語文別:中文
論文頁數:277
中文關鍵詞:福木雙花金絲桃抗氧化
外文關鍵詞:Garcinia subellipticaHypericum geminiflorumphloroglucinol
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摘 要
本研究乃將福木(Garcinia subelliptica Merr.)與雙花金絲桃(Hypericum geminiflorum Hemsl.)分別進行成分分離及生物活性探討。
由福木果皮的CHCl3萃取液中分離得到1個新的tautomeric pair,garcinielliptone FC (5/5a)以及6個已知化合物??-amyrin (1),canophyllol (2),canophyllic acid (3),putraflavone (4),cycloart-23-
ene-3??,25-diol (6)以及cycloart-23,25-diene-3??-ol (7)。而garcinielliptone FC (5/5a)以supercoiled plasmid pBR322 DNA測試DNA-cleavage活性時,我們發現當Cu(II)存在時garcinielliptone FC (5/5a)會使得pBR322 DNA 斷裂。而斷裂的原因則和H2O2, OH˙及O2˙-有關。因此,在Cu(II)的存在下,garcinielliptone FC (5/5a)會與Cu(II)螯和,而產生上面所列之reactive oxygen species (ROS)進而造成DNA斷裂。
由雙花金絲桃心材的CHCl3萃取液中分離得到1個新的xanthone,1,5,7-trihydroxy-6-methoxyxanthone (9),3個具新骨格tautomeric pairs,hyperielliptone HA (17/17a),hyperielliptone HB (18/18a),hyperielliptone HE (29/29a),及3個新的xanthonolignoids,hyperielliptone HC (19),hyperielliptone HD (20),hyperielliptone HF (30)。以及16個已知化合物??-sitosterol (8),1,3,8-trihydroxy-2-
methoxyxanthone (10),1,7-dihydroxyxanthone (11),2,3-methylene-
dioxyxanthone(12),1,5-dihydroxy-6-methoxyxanthone (13),2-hydroxy-xanthone (14),2,3-dimethoxyxanthone (15),2,6-dimethoxy-
[1,4]-benzoquinone (16),cadensin D (21),1,8-dihydroxy-3-methoxy-
xanthone (22),Stigmast-4-en-6??-ol-3-one (23),??-sitosteryl-3??-gluco-
pyranoside-6′-O-palmitate (24),2,6,2′,6′-tetramethoxy-4,4′-bis(2,3-
epoxy-1-hydroxypropyl)biphenyl (25),4-hydroxy-3,5-dimethoxy-
benzenemethanol (26),deprenylated rheediaxanthone (27),hexadecanamide (28)。而hyperielliptone HB (18/18a)以supercoiled plasmid pBR322 DNA測試oxidative DNA damage活性時,發現其對xanthine oxidase有顯著的抑制活性。18/18a在3 ?嵱濃度下會增強cisplatin對NTUB1 cells之毒性,但在較高濃度下卻有保護細胞的作用,18/18a在NTUB1 cells內會增加活性氧化物(reactive oxygen species, ROS)而導致癌細胞死亡。
由雙花金絲桃分離得到之hyperielliptone HA (17/17a)和HB (18/18a)具有antioxidant activity。其中compound 18/18a活性較強。在一連串測試中可知其作用機轉與抑制xanthine oxidase比較有關。未來可進一步探討其詳細的作用機轉。
Abstract
Three new phloroglucinols, garcinielliptone FC (5/5a), hyperielliptones HA (17/17a) and HE (29/29a), and a new spirophloroglucinol possessing an unprecedented skeleton, hyperielliptone HB (18/18a), were isolated from the pericarp of Garcinia subelliptica and the heartwood of Hypericum geminiflorum. A new xanthone, 1,5,7-trihydroxy-6-methoxyxanthone (9), and three new xanthonolignoids, hyperielliptones HC (19), HD (20) and HF (30) were also isolated from these plants. The structures and relative configurations of these compounds were elucidated by spectroscopic methods. In biological testing, compound 5/5a caused significant breakage of supercoiled plasmid pBR322 DNA in the presence of Cu(II). The involvement of H2O2, OH˙, and O2˙- in 5/5a-mediated scission was established by inhibition or no protection of DNA breakage by various oxygen radical scavengers. Thus, in the presence Cu(II) 5/5a may show a prooxidant effect on DNA and induce cell death. Compound 18/18a revealed significant inhibition of oxidative DNA damage and an inhibitory effect on xanthine oxidase. NTUB1 cells treated with 18/18a induced the generation of ROS and caused the death of cancer cells. 18/18a increased the cisplatin-induced death of NTUB1 cells at 3 ?嵱, but it inhibited the cisplatin-induced death of NTUB1 cells at higher concentration. Thus, the antioxidant activity of 18/18a should be not inhibited the generation of ROS. It should be inhibited the xanthine oxidase.
目錄
中文摘要………………………………………………………… 1
英文摘要………………………………………………………… 3
第一章 研究動機與目的………………………………………… 5
第二章 福木化學成分研究……………………………………… 7
第一節 研究回顧……………………………………………… 7
第二節 植物形態……………………………………………… 31
第三節 抽取與分離…………………………………………… 33
第四節 化學成分之結構證明………………………………… 37
第一項 β-Amyrin (1)的結構證明…... ………………… 37
第二項 Canophyllol (2)的結構證明………………….… 40
第三項 Canophyllic acid (3)的結構證明……………… 43
第四項 Putraflavone (4)的結構證明………………….. 46
第五項 Garcinielliptone FC (5/5a)的結構證明…………50
第六項 Cycloart-23-ene-3β,25-diol (6)的結構證明……58
第七項 Cycloart-23,25-diene-3β-ol (7)的結構證明……62
第三章 雙花金絲桃化學成分研究………………………………66
第一節 研究回顧……………………………………………… 66
第二節 植物形態…………………………………………..….81
第三節 抽取與分離……………………………………..…… 83
第四節 化學成分之結構證明………………………………… 90
第一項 β-Sitosterol (8)的結構證明…………………….90
第二項 1,5,7-Trihydroxy-6-methoxyxanthone (9)的結構
證明………………….…………………………. 93
第三項 1,3,8-Trihydroxy-2-methoxyxanthone (10)的結
構證明……………..…………………………… 98
第四項 1,7-Dihydroxyxanthone (11)的結構證明………101
第五項 2,3-Methylenedioxyxanthone (12)的結構證明…104
第六項 1,5-Dihydroxy-6-methoxyxanthone (13)的結構
證明…………………………………………….....107
第七項 2-Hydroxyxanthone (14)的結構證明…………… 110
第八項 2,3-Dimethoxyxanthone (15)的結構證明……….113
第九項 2,6-Dimethoxy-[1,4]benzoquinone (16)的結構證
明……………………………………………….. 116
第十項 Hyperielliptone HA (17/17a)的結構證明………119
第十一項 Hyperielliptone HB (18/18a)的結構證明……127
第十二項 Hyperielliptone HC (19)的結構證明…………135
第十三項 Hyperielliptone HD (20)的結構證明…………142
第十四項 Cadensin D (21)的結構證明…………………. 149
第十五項 1,8-Dihydroxy-3-methoxyxanthone (22)的結
構證明………………………………………... 153
第十六項 Stigmast-4-en-6β-ol-3-one (23)的結構證明…154
第十七項 β-Sitosteryl-3β-glucopyranoside-6′-Opalmitate
(24)的結構證明…..……………….. 159
第十八項 2,6,2′,6′-Tetramethoxy-4,4′-bis(2,3-epoxy-1-
hydroxypropyl)biphenyl (25)的結構證明…… 163
第十九項 4-Hydroxy-3,5-dimethoxybenzenemethanol
(26)的結構證明……………………………… 166
第二十項 Deprenylated rheediaxanthone (27)的結構證
明… 169
第二十一項 Hexadecanamide (28)的結構證明…………. 172
第二十二項 Hyperielliptone HE (29/29a)的結構證
明…………………………………………... 175
第二十三項 Hyperielliptone HF (30)的結構證明……….183
第四章 生物活性試驗…………………………………………….190
第一節 DNA strand scission assay………………………… 190
第二節Flow cytometry……………………………………….. 191
第三節Antioxidant Activity………………………………….192
第五章 結論……………………………………………………….199
第六章 實驗部分………………………………………………… 201
第一節 儀器與材料………………………………………….. 201
第二節 生物活性試驗篩選方法……………………………. 204
第七章 化合物之物理化學性質………………………………….213
參考文獻……………………………………………………………247
論文著作……………………………………………………………264
圖表目錄
Figure 1-1. β-Amyrin (1)之IR 光譜……..………………… 38
Figure 1-2. β-Amyrin (1)之1H NMR 光譜…...………………38
Figure 1-3. β-Amyrin (1)之13C NMR 光譜……………………39
Figure 1-4. β-Amyrin (1)之EIMS 光譜………….……………39
Figure 2-1. Canophyllol (2)之IR 光譜………………………41
Figure 2-2. Canophyllol (2)之1H NMR 光譜…….………… 41
Figure 2-3. Canophyllol (2)之DEPT 光譜……….………… 42
Figure 2-4. Canophyllol (2)之EIMS 光譜……………………42
Figure 3-1. Canophyllic acid (3)之IR 光譜……………… 44
Figure 3-2. Canophyllic acid (3)之1H-NMR 光譜………… 44
Figure 3-3. Canophyllic acid (3)之DEPT 光譜…………… 45
Figure 3-4. Canophyllic acid (3)之EIMS 光譜…………… 45
Figure 4-1. Putraflavone (4)之IR 光譜…………………… 47
Figure 4-2. Putraflavone (4)之ESIMS 光譜……………… 48
Figure 4-3. Putraflavone (4)之1H-NMR 光譜……………… 48
Figure 4-4. Putraflavone (4)之13C NMR 光譜………………49
Figure 5-1. garcinielliptone FC (5/5a)之1H-1H COSY 和
HMBC 關係圖.............................. 52
Figure 5-2. Garcinielliptone FC (5/5a)之IR 光譜……… 53
Figure 5-3. Garcinielliptone FC (5/5a)之HRESIMS 光譜…53
Figure 5-4. Garcinielliptone FC (5/5a)之1H NMR 光譜… 54
Figure 5-5. Garcinielliptone FC (5/5a)之DEPT 光譜…… 54
Figure 5-6. Garcinielliptone FC (5/5a)之COSY 光譜…… 55
Figure 5-7. Garcinielliptone FC (5/5a)之NOSEY 光譜……55
Figure 5-8. Garcinielliptone FC (5/5a)之HMQC 光譜…… 56
Figure 5-9. Garcinielliptone FC (5/5a)之HMBC 光譜…… 56
Figure 5-10. Garcinielliptone FC (5/5a)之3D 立體圖……57
Figure 6-1. Cycloart-23-ene-3β,25-diol (6)之IR 光譜….59
Figure 6-2. Cycloart-23-ene-3β,25-diol (6)之1H NMR 光
譜…… 60
Figure 6-3. Cycloart-23-ene-3β,25-diol (6)之13C NMR 光
譜…… 60
Figure 6-4. Cycloart-23-ene-3β,25-diol (6)之EIMS 光譜 61
Figure 7-1. Cycloart-23,25-diene-3β-ol (7)之IR 光譜… 63
Figure 7-2. Cycloart-23,25-diene-3β-ol (7)之1H NMR 光
譜…… 64
Figure 7-3. Cycloart-23,25-diene-3β-ol (7)之13C NMR 光
譜…… 64
Figure 7-4. Cycloart-23,25-diene-3β-ol (7) 之EIMS 光
譜……… 65
Figure 8-1. β-Sitosterol (8) 之IR 光譜……………………91
Figure 8-2. β-Sitosterol (8) 之EIMS 光譜…………………91
Figure 8-3. β-Sitosterol (8) 之1H NMR 光譜………………92
Figure 8-4. β-Sitosterol (8) 之13C NMR 光譜…………… 92
Figure 9-1. 1,5,7-trihydroxy-6-methoxyxanthone (9)之
HMBC 關係圖……………………………………… 94
Figure 9-2. 1,5,7-Trihydroxy-6-methoxyxanthone (9)之
IR 光譜... 94
Figure 9-3. 1,5,7-Trihydroxy-6-methoxyxanthone (9)之
HRESIMS 光譜………………………………………95
Figure 9-4. 1,5,7-Trihydroxy-6-methoxyxanthone (9)之
1H-NMR 光譜………………………………… 95
Figure 9-5. 1,5,7-Trihydroxy-6-methoxyxanthone (9)之
13C NMR 光譜………………………………………96
Figure 9-6. 1,5,7-Trihydroxy-6-methoxyxanthone (9)之
HMQC光譜..................................96
Figure 9-7. 1,5,7-Trihydroxy-6-methoxyxanthone (9)之
HMBC 光譜.................................97
Figure 10-1. 1,3,8-Trihydroxy-2-methoxyxanthone (10)之
IR 光譜…................................99
Figure 10-2. 1,3,8-Trihydroxy-2-methoxyxanthone (10)之
EIMS 光譜…………………………………………99
Figure 10-3. 1,3,8-Trihydroxy-2-methoxyxanthone (10)之
1H-NMR 光譜………………………..………… 100
Figure 10-4. 1,3,8-Trihydroxy-2-methoxyxanthone (10)之
13C NMR 光譜……………………………………100
Figure 11-1. 1,7-Dihydroxyxanthone (11)之IR 光譜…… 102
Figure 11-2. 1,7-Dihydroxyxanthone (11)之EIMS 光譜….102
Figure 11-3. 1,7-Dihydroxyxanthone (11)之1H NMR 光譜 103
Figure 11-4. 1,7-Dihydroxyxanthone (11)之13C NMR 光譜103
Figure 12-1. 2,3-Methylenedioxyxanthone (12)之IR 光譜105
Figure 12-2. 2,3-Methylenedioxyxanthone (12)之EIMS 光
譜….. 105
Figure 12-3. 2,3-Methylenedioxyxanthone (12)之1H NMR
光譜.. 106
Figure 12-4. 2,3-Methylenedioxyxanthone (12)之13C NMR
光譜. 106
Figure 13-1. 1,5-Dihydroxy-6-methoxyxanthone (13)之
IR 光譜.. 108
Figure 13-2. 1,5-Dihydroxy-6-methoxyxanthone (13)之
EIMS 光譜……………………………………… 108
Figure 13-3. 1,5-Dihydroxy-6-methoxyxanthone (13)之
1H NMR 光譜…………………………………… 109
Figure 13-4. 1,5-Dihydroxy-6-methoxyxanthone (13)之
13C NMR 光譜………………………… 109
Figure 14-1. 2-Hydroxyxanthone (14)之IR 光譜………… 111
Figure 14-2. 2-Hydroxyxanthone (14)之EIMS 光譜……… 111
Figure 14-3. 2-Hydroxyxanthone (14)之1H NMR 光譜…… 112
Figure 14-4. 2-Hydroxyxanthone (14)之13C NMR 光譜……112
Figure 15-1. 2,3-Dimethoxyxanthone (15)之IR 光譜…… 114
Figure 15-2. 2,3-Dimethoxyxanthone (15)之EIMS 光譜… 114
Figure 15-3. 2,3-Dimethoxyxanthone (15)之1H NMR 光譜.115
Figure 15-4. 2,3-Dimethoxyxanthone (15)之13C NMR 光譜 115
Figure 16-1. 2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione
(16)之IR 光譜…………………..…………… 117
Figure 16-2. 2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione
(16)之EIMS 光譜……………… 117
Figure 16-3. 2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione
(16)之1H-NMR 光譜………………..……………118
Figure 16-4. 2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione
(16)之13C NMR 光譜……………..…………… 118
Figure 17-1. Hyperielliptone HA (17/17a)之IR 光譜…… 122
Figure 17-2. Hyperielliptone HA (17/17a)之HRESIMS 光譜 122
Figure 17-3. Hyperielliptone HA (17/17a)之1H-NMR 光譜…123
Figure 17-4. Hyperielliptone HA (17/17a)之DEPT 光譜……123
Figure 17-5. Hyperielliptone HA (17/17a)之COSY 光譜……124
Figure 17-6. Hyperielliptone HA (17/17a)之NOSEY 光譜… 124
Figure 17-7. Hyperielliptone HA (17/17a)之HMQC 光譜… 125
Figure 17-8. Hyperielliptone HA (17/17a)之HMBC 光譜……125
Figure 17-9. Hyperielliptone HA (17)之3D 立體圖……… 126
Figure 17-10. Hyperielliptone HA (17)之1H-1H COSY 和
HMBC 關係圖..............................126
Figure 18-1. Hyperielliptone HB (18/18a)之IR 光譜………129
Figure 18-2. Hyperielliptone HB (18/18a)之HRESIMS 光譜 130
Figure 18-3. Hyperielliptone HB (18/18a)之1H-NMR 光譜…130
Figure 18-4. Hyperielliptone HB (18/18a)之DEPT 光譜……131
Figure 18-5. Hyperielliptone HB (18/18a)之COSY 光譜……131
Figure 18-6. Hyperielliptone HB (18/18a)之NOSEY 光譜… 132
Figure 18-7. Hyperielliptone HB (18/18a)之HMQC 光譜……132
Figure 18-8. Hyperielliptone HB (18/18a)之HMBC 光譜……133
Figure 18-9. Hyperielliptone HB (18)之3D 立體圖…………133
Figure 18-10. Hyperielliptone HB (18)之1H-1H COSY 和
HMBC 關係圖..............................134
Figure 19-1. Hyperielliptone HC (19)之IR 光譜……………137
Figure 19-2. Hyperielliptone HC (19)之HRESIMS 光譜…… 138
Figure 19-3. Hyperielliptone HC (19)之1H-NMR 光譜………138
Figure 19-4. Hyperielliptone HC (19)之DEPT 光譜…………139
Figure 19-5. Hyperielliptone HC (19)之COSY 光譜…………139
Figure 19-6. Hyperielliptone HC (19)之NOSEY 光譜……… 140
Figure 19-7. Hyperielliptone HC (19)之HMQC 光譜…………140
Figure 19-8. Hyperielliptone HC (19)之HMBC 光譜…………141
Figure 19-9. Hyperielliptone HC (19)之1H-1H COSY 和
HMBC 關係圖……………………………………… 141
Figure 20-1. Hyperielliptone HD (20)之IR 光譜……………144
Figure 20-2. Hyperielliptone HD (20)之HRESIMS 光譜…… 145
Figure 20-3. Hyperielliptone HD (20)之1H NMR 光譜………145
Figure 20-4. Hyperielliptone HD (20)之DEPT 光譜…………146
Figure 20-5. Hyperielliptone HD (20)之COSY 光譜…………146
Figure 20-6. Hyperielliptone HD (20)之NOSEY 光譜……… 147
Figure 20-7. Hyperielliptone HD (20)之HMQC 光譜…………147
Figure 20-8. Hyperielliptone HD (20)之HMBC 光譜…………148
Figure 20-9. Hyperielliptone HD (20)之1H-1H COSY 和
HMBC 關係圖...............................148
Figure 21-1. Cadensin D (21)之IR 光譜………………………150
Figure 21-2. Cadensin D (21)之FABMS 光譜………………… 151
Figure 21-3. Cadensin D (21)之1H NMR 光譜…………………151
Figure 21-4. Cadensin D (21)之13C NMR 光譜……………… 152
Figure 22-1. 1,8-Dihydroxy-3-methoxyxanthone (22)之IR 光
譜.. 154
Figure 22-2. 1,8-Dihydroxy-3-methoxyxanthone (22)之
EIMS 光譜………………………………………… 154
Figure 22-3. 1,8-Dihydroxy-3-methoxyxanthone (22)之
1H-NMR 光譜…………………..………………… 155
Figure 22-4. 1,8-Dihydroxy-3-methoxyxanthone (22)之
13C NMR 光譜…………………………..…………155
Figure 23-1. Stigmast-4-en-6β-ol-3-one (23)之IR 光譜… 157
Figure 23-2. Stigmast-4-en-6β-ol-3-one (23)之EIMS 光譜 157
Figure 23-3. Stigmast-4-en-6β-ol-3-one (23)之1H NMR 光
譜….. 158
Figure 23-4. Stigmast-4-en-6β-ol-3-one (23)之13C NMR 光
譜…. 158
Figure 24-1. β-Sitosteryl-3β-glucopyranoside-6′-O-
palmitate (24)之IR 光譜…… 160
Figure 24-2. β-Sitosteryl-3β-glucopyranoside-6′-O-
palmitate (24)之FABMS 光譜 161
Figure 24-3. β-Sitosteryl-3β-glucopyranoside-6′-O-
palmitate (24)之1H NMR 光譜………………… 161
Figure 24-4. β-Sitosteryl-3β-glucopyranoside-6′-O-
palmitate (24)之13C NMR 光譜…………………162
Figure 25-1. 2,6,2′,6′-Tetramethoxy-4,4′-bis(2,3-epoxy-
1-hydroxypropyl)biphenyl (25)之IR 光譜……164
Figure 25-2. 2,6,2′,6′-Tetramethoxy-4,4′-bis(2,3-epoxy-
1-hydroxypropyl)biphenyl (25)之EIMS 光譜…164
Figure 25-3. 2,6,2′,6′-Tetramethoxy-4,4′-bis(2,3-epoxy-
1-hydroxypropyl)biphenyl (25)之1H NMR 光譜 165
Figure 25-4. 2,6,2′,6′-Tetramethoxy-4,4′-bis(2,3-epoxy-
1-hydroxypropyl)biphenyl (25)之13C NMR 光譜165
Figure 26-1. 4-Hydroxy-3,5-dimethoxybenzenemethanol (26)
之IR 光譜………………………………………… 167
Figure 26-2. 4-Hydroxy-3,5-dimethoxybenzenemethanol (26)
之EIMS 光譜…………………………………… 167
Figure 26-3. 4-Hydroxy-3,5-dimethoxybenzenemethanol (26)
之1H NMR 光譜………………………………… 168
Figure 26-4. 4-Hydroxy-3,5-dimethoxybenzenemethanol (26)
之13C NMR 光譜…………………… 168
Figure 27-1. Deprenylated rheediaxanthone (27)之IR 光譜 170
Figure 27-2. Deprenylated rheediaxanthone (27)之
ESIMS 光譜.. 170
Figure 27-3. Deprenylated rheediaxanthone (27)之
1H NMR 光譜 171
Figure 27-4. Deprenylated rheediaxanthone (27)之
DEPT 光譜… 171
Figure 28-1. Hexadecanamide (28)之IR 光譜………………… 173
Figure 28-2. Hexadecanamide (28)之ESIMS 光譜………………173
Figure 28-3. Hexadecanamide (28)之1H NMR 光譜…………….174
Figure 28-4. Hexadecanamide (28)之13C NMR 光譜……………174
Figure 29-1. Hyperielliptone HE (29/29a)之IR 光譜……… 177
Figure 29-2. Hyperielliptone HE (29/29a)之HRESIMS 光譜…178
Figure 29-3. Hyperielliptone HE (29/29a)之1H-NMR 光譜… 178
Figure 29-4. Hyperielliptone HE (29/29a)之DEPT 光譜…… 179
Figure 29-5. Hyperielliptone HE (29/29a)之COSY 光譜…… 179
Figure 29-6. Hyperielliptone HE (29/29a)之NOSEY 光譜……180
Figure 29-7. Hyperielliptone HE (29/29a)之HMQC 光譜…… 180
Figure 29-8. Hyperielliptone HE (29/29a)之HMBC 光譜…….181
Figure 29-9. Hyperielliptone HE (29)之3D 立體圖………… 181
Figure 29-10. Hyperielliptone HE (29)之1H-1H COSY 和
HMBC 關係圖…………………………………… 182
Figure 30-1. Hyperielliptone HF (30)之IR 光譜…………… 185
Figure 30-2. Hyperielliptone HF (30)之HRESIMS 光譜………186
Figure 30-3. Hyperielliptone HF (30)之1H-NMR 光譜……… 186
Figure 30-4. Hyperielliptone HF (30)之DEPT 光譜………… 187
Figure 30-5. Hyperielliptone HF (30)之COSY 光譜………… 187
Figure 30-6. Hyperielliptone HF (30)之NOSEY 光譜…………188
Figure 30-7. Hyperielliptone HF (30)之HMQC 光譜………… 188
Figure 30-8. Hyperielliptone HF (30)之HMBC 光譜………… 189
Figure 30-9. Hyperielliptone HF (30)之1H-1H COSY 和
HMBC 關係圖……………………………………… 189
Figure 31. Agarose gel electrophoretic patterns of
plasmid DNA treated with 5/5a in the presence
of Cu(II) ion….. 193
Figure 32. Effect of neocuproine (600 μM) on
5/5a (300 μM)-Cu(II) (300 μM)-induced
breakage of pBR322 DNA… 193
Figure 33. Effect of active oxygen scavengers on 5/5a-
Cu(II)-mediated DNA breakage…………………… 193
Figure 34. Flow cytometry analysis of 5/5a treated
MCF-7 cells… 194
Figure 35. Fluorescence microscopy observation of
chromatin condensation in MCF-7 cells
induced by 5/5a……….... 194
Figure 36. Flow cytometry analysis of 5/5a (with and
without copper) treated MCF-7 cells……………195
Figure 37. Inhibition of DNA strand breaks induced by
O2—․(generated by xanthine/xanthine oxidase)
in the presence of SOD, quercetin, 17/17a, and
18/18a…….... 195
Figure 38. Dose-dependent inhibition of xanthine oxidase
by 18/18a and allopurinol……………………… 196
Figure 39. Inhibition of the cisplatin-induced NTUB cells
death in the presence of 18/18a…………………196
Figure 40. Cisplatin and 18/18a induces ROS production…197
Figure 41. Cisplatin with 18/18a induces ROS production 198
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