臺灣博碩士論文加值系統

番荔枝科植物Uvaria flexuosa僅分佈於柬埔寨和越南等地，針對其甲醇萃取物所進行的研究共得到7個新化合物(UF-1–UF-7)以及4個已知黃酮類化合物(UF-8–UF-11)。在新化合物當中，包含1個3-methyl-4,5-dihydro-oxepine [flexuvaroxepine A (UF-1)]、4個polyoxygenated seco-cyclohexene [flexuvarins A–D (UF-2–UF-5)]和2個polyoxygenated cyclohexene [flexuvarols A and B (UF-6 and UF-7)]等骨架之衍生物。所有化合物的結構都是經由許多不同的光譜資料分析而決定。本研究也有針對這些新化合物可能的生合成途徑進行探討。
　　本研究的另一個題目為台灣產黑潮花裙海葵Zoanthus kuroshio。黑潮花裙海葵是ㄧ種色彩豐富的海葵，具有螢光粉紅色口腔盤以及棕色觸手，在本次研究中，從Z. kuroshio的乙醇萃取物中共分離得到6個新zoanthamine-type alkaloids [5α-iodozoanthenamine (ZK-1), 11β-chloro-11-deoxykuroshine A (ZK-2), 18-epi-kuroshine A (ZK-3), 7α-hydroxykuroshine E (ZK-4), 5α-methoxykuroshine E (ZK-5) and 18-epi-kuroshine E (ZK-6)]以及6個已知zoanthamine-type alkaloids (ZK-7–ZK-12)。其中ZK-1和ZK-2是此類生物鹼中首次發現的鹵化衍生物，而ZK-3與ZK-6則是首次發現A/B環結構為cis-junction的zoanthamine-type alkaloids立體異構物。
　　所有化合物的抗發炎活性則是藉由superoxide anion generation和elastase release試驗來進行評估。在所有從U. flexuosa分離的到的化合物中，UF-7和UF-9對於superoxide anion generation和elastase release皆具有顯著的抑制活性，IC50值落在2.25－5.55 µM之間，而UF-8僅對於superoxide anion generation具有選擇性的抑制活性，其IC50值為1.19 ± 0.34 µM。至於所有zoanthamines類化合物，在10 µM濃度下僅有ZK-1對於superoxide anion generation和elastase release具有顯著的抑制活性，其抑制百分率分別為24 ± 6%和43 ± 2%。

The phytochemical investigation of the methanolic extract of Uvaria flexuosa (Annonaceae) have led to the isolation of seven new compounds, including one 3-methyl-4,5-dihydro-oxepine [flexuvaroxepine A (UF-1)], four polyoxygenated seco-cyclohexene [flexuvarins A–D (UF-2–UF-5)], two polyoxygenated cyclohexene [flexuvarols A and B (UF-6 and UF-7)] derivatives, together with four known flavones (UF-8–UF-11). The structures of the isolated compounds were elucidated using different spectroscopic techniques. A plausible biogenetic route of the new compounds was discussed.
Zoanthus kuroshio is a colorful zoanthid with a fluorescent pink oral disc and brown tentacles. Six new zoanthamines [5α-iodozoanthenamine (ZK-1), 11β-chloro-11-deoxykuroshine A (ZK-2), 18-epi-kuroshine A (ZK-3), 7α-hydroxykuroshine E (ZK-4), 5α-methoxykuroshine E (ZK-5) and 18-epi-kuroshine E (ZK-6)] and six known compounds (ZK-7–ZK-12) were isolated from the ethanolic extract. Among those zoanthamines, ZK-1 and ZK-2 are the first examples of halogenated zoanthamine-type alkaloids isolated from nature. ZK-3 and ZK-6 are the first zoanthamine stereoisomers with a cis-junction of the A/B rings.
The anti-inflammatory activity of all isolates was evaluated by superoxide anion generation and elastase release assays in human neutrophils. Among those from U. flexuosa, UF-7 and UF-9 showed potent anti-inflammatory effect by inhibiting superoxide anion generation and elastase release with IC50 2.25－5.55 µM. UF-11 showed selective inhibitory activity on superoxide anion generation with an IC50 of 1.19 ± 0.34 µM. As for those zoanthamines, only ZK-1 showed potent inhibitory activity on both superoxide anion generation (24 ± 6%) and elastase release (43 ± 2%) at 10 µM.

目錄
目錄 ----I
圖目錄 ----III
表目錄 -----IX
第一章 緒論----1
第一節 前言----1
第二節 曲葉紫玉盤Uvaria flexuosa之型態及分佈----4
第三節 紫玉盤屬Uvaria之文獻回顧----7
第四節 黑潮花裙海葵Zoanthus kuroshio之型態及分佈----64
第五節 花裙海葵屬Zoanthus文獻回顧----66
第六節 研究動機----84
第二章 研究材料與方法----85
第一節 曲葉紫玉盤Uvaria flexuosa之研究材料與方法----85
第二節 黑潮花裙海葵Zoanthus kuroshio之研究材料與方法----89
第三章 Uvaria flexuosa化合物結構解析與生合成探討----95
第一節 Flexuvaroxepine A (UF-1)之結構解析----95
第二節 Flexuvarin A (UF-2)之結構解析----106
第三節 Flexuvarin B (UF-3)之結構解析----117
第四節 Flexuvarin C (UF-4)之結構解析----128
第五節 Flexuvarin D (UF-5)之結構解析----138
第六節 Flexuvarol A (UF-6)之結構解析----148
第七節 Flexuvarol B (UF-7)之結構解析----159
第八節 UF系列化合物生合成探討----170
第四章 Zoanthus kuroshio之Zoanthamine-type alkaloids結構解析----174
第一節 5α-Iodozoanthenamine (ZK-1)之結構解析----181
第二節 11β-Chloro-11-deoxykuroshine A (ZK-2)之結構解析----195
第三節 18-epi-Kuroshine A (ZK-3)之結構解析-----208
第四節 7α-Hydroxykuroshine E (ZK-4)之結構解析----219
第五節 5α-Methoxykuroshine E (ZK-5)之結構解析----231
第六節 18-epi-Kuroshine E (ZK-6)之結構解析----243
第五章 抗發炎活性試驗------254
第一節 UF系列化合物抗發炎活性試驗結果----254
第二節 ZK系列化合物抗發炎活性試驗結果----256
第六章 結論----258
第七章 相關實驗部分----267
第一節 儀器與材料-----267
第二節 曲葉紫玉盤Uvaria flexuosa分離純化流程----270
第三節 黑潮花裙海葵Zoanthus kuroshio分離純化流程----277
第四節 化合物之物理與光譜數據總整理----283
第五節 抗發炎活性試驗----306
第八章 參考文獻----309
第九章 著作發表與相關產出----321
第一節 期刊論文發表----321
第二節 研討會論文發表----324
第三節 發明專利----332
第四節 新型專利----333
第五節 專書著作----334

圖目錄
圖2-1-1 U. flexuosa分配萃取與分離流程圖----86
圖2-2-1 黑潮花裙海葵實景圖----89
圖2-2-1 Z. kuroshio分配萃取與分離流程圖----90
圖3-1-1 化合物UF-1之UV圖譜----101
圖3-1-2 化合物UF-1之IR圖譜----101
圖3-1-3 化合物UF-1之HRESIMS圖譜----102
圖3-1-4 化合物UF-1之13C NMR圖譜(150 MHz, CDCl3)----102
圖3-1-5 化合物UF-1之DEPT圖譜----103
圖3-1-6 化合物UF-1之1H NMR圖譜(600 MHz, CDCl3)----103
圖3-1-7 化合物UF-1之HSQC圖譜----104
圖3-1-8 化合物UF-1之COSY圖譜----104
圖3-1-9 化合物UF-1之HMBC圖譜----105
圖3-1-10 化合物UF-1之NOESY圖譜----105
圖3-2-1 化合物UF-2之UV圖譜----112
圖3-2-2 化合物UF-2之IR圖譜----112
圖3-2-3 化合物UF-2之HRESIMS圖譜----113
圖3-2-4 化合物UF-2之13C NMR圖譜(150 MHz, CDCl3) ----113
圖3-2-5 化合物UF-2之DEPT圖譜----114
圖3-2-6 化合物UF-2之1H NMR圖譜(600 MHz, CDCl3) ----114
圖3-2-7 化合物UF-2之HSQC圖譜----115
圖3-2-8 化合物UF-2之COSY圖譜----115
圖3-2-9 化合物UF-2之HMBC圖譜----116
圖3-2-10 化合物UF-2之NOESY圖譜----116
圖3-3-1 化合物UF-3之UV圖譜----123
圖3-3-2 化合物UF-3之IR圖譜----123
圖3-3-3 化合物UF-3之HRESIMS圖譜----124
圖3-3-4 化合物UF-3之13C NMR圖譜(100 MHz, CDCl3)----124
圖3-3-5 化合物UF-3之DEPT圖譜----125
圖3-3-6 化合物UF-3之1H NMR圖譜(400 MHz, CDCl3)----125
圖3-3-7 化合物UF-3之HSQC圖譜----126
圖3-3-8 化合物UF-3之COSY圖譜----126
圖3-3-9 化合物UF-3之HMBC圖譜----127
圖3-3-10 化合物UF-3之NOESY圖譜----127
圖3-4-1 化合物UF-4之UV圖譜----133
圖3-4-2 化合物UF-4之IR圖譜----133
圖3-4-3 化合物UF-4之HREIMS圖譜----134
圖3-4-4 化合物UF-4之13C NMR圖譜(100 MHz, CDCl3)----134
圖3-4-5 化合物UF-4之DEPT圖譜----135
圖3-4-6 化合物UF-4之1H NMR圖譜(400 MHz, CDCl3) ----135
圖3-4-7 化合物UF-4之HSQC圖譜----136
圖3-4-8 化合物UF-4之COSY圖譜----136
圖3-4-9 化合物UF-4之HMBC圖譜----137
圖3-4-10 化合物UF-4之NOESY圖譜----137
圖3-5-1 化合物UF-5之UV圖譜----143
圖3-5-2 化合物UF-5之IR圖譜----143
圖3-5-3 化合物UF-5之HRESIMS圖譜----144
圖3-5-4 化合物UF-5之13C NMR圖譜(150 MHz, CDCl3) ----144
圖3-5-5 化合物UF-5之DEPT圖譜----145
圖3-5-6 化合物UF-5之1H NMR圖譜(600 MHz, CDCl3) ----145
圖3-5-7 化合物UF-5之HSQC圖譜-----146
圖3-5-8 化合物UF-5之COSY圖譜----146
圖3-5-9 化合物UF-5之HMBC圖譜----147
圖3-5-10 化合物UF-5之NOESY圖譜----147
圖3-6-1 化合物UF-6之UV圖譜----154
圖3-6-2 化合物UF-6之IR圖譜----154
圖3-6-3 化合物UF-6之HREIMS圖譜----155
圖3-6-4 化合物UF-6之13C NMR圖譜(150 MHz, CDCl3)----155
圖3-6-5 化合物UF-6之DEPT圖譜----156
圖3-6-6 化合物UF-6之1H NMR圖譜(600 MHz, CDCl3)----156
圖3-6-7 化合物UF-6之HSQC圖譜----157
圖3-6-8 化合物UF-6之COSY圖譜----157
圖3-6-9 化合物UF-6之HMBC圖譜----158
圖3-6-10 化合物UF-6之NOESY圖譜----158
圖3-7-1 化合物UF-7之UV圖譜----165
圖3-7-2 化合物UF-7之IR圖譜----165
圖3-7-3 化合物UF-7之HREIMS圖譜----166
圖3-7-4 化合物UF-7之13C NMR圖譜(150 MHz, CDCl3) ----166
圖3-7-5 化合物UF-7之DEPT圖譜----167
圖3-7-6 化合物UF-7之1H NMR圖譜(600 MHz, CDCl3) ----167
圖3-7-7 化合物UF-7之HSQC圖譜----168
圖3-7-8 化合物UF-7之COSY圖譜----168
圖3-7-9 化合物UF-7之HMBC圖譜----169
圖3-7-10 化合物UF-7之NOESY圖譜----169
圖3-8-1 Flexuvaroxepine A (UF-1)生合成路徑圖----171
圖3-8-2 Flexuvarin D (UF-3 - UF-5)生合成路徑圖----171
圖3-8-3 Flexuvarin A (UF-2)生合成路徑圖----172
圖3-8-3 Flexuvarol A (UF-6)與Flexuvarol B (UF-7)生合成路徑圖----173
圖4-1-1 化合物ZK-1之UV圖譜----189
圖4-1-2 化合物ZK-1之IR圖譜----189
圖4-1-3 化合物ZK-1之ESI-MS圖譜----190
圖4-1-4 化合物ZK-1之HRESIMS圖譜----190
圖4-1-5 化合物ZK-1之13C NMR圖譜(150 MHz, C5D5N) ----191
圖4-1-6 化合物ZK-1之DEPT圖譜----191
圖4-1-7 化合物ZK-1之1H NMR圖譜(600 MHz, C5D5N) ----192
圖4-1-8 化合物ZK-1之HSQC圖譜----192
圖4-1-9 化合物ZK-1之COSY圖譜----193
圖4-1-10 化合物ZK-1之HMBC圖譜----193
圖4-1-11 化合物ZK-1之NOESY圖譜----194
圖4-2-1 化合物ZK-2之UV圖譜----202
圖4-2-2 化合物ZK-2之IR圖譜----202
圖4-2-3 化合物ZK-2之ESI-MS圖譜----203
圖4-2-4 化合物ZK-2之HRESIMS圖譜----203
圖4-2-5 化合物ZK-2之13C NMR圖譜(100 MHz, C5D5N)----204
圖4-2-6 化合物ZK-2之DEPT圖譜----204
圖4-2-7 化合物ZK-2之1H NMR圖譜(400 MHz, C5D5N) ----205
圖4-2-8 化合物ZK-2之HSQC圖譜----205
圖4-2-9 化合物ZK-2之COSY圖譜----206
圖4-2-10 化合物ZK-2之HMBC圖譜----206
圖4-2-11 化合物ZK-2之NOESY圖譜----207
圖4-3-1 化合物ZK-3之UV圖譜----214
圖4-3-2 化合物ZK-3之IR圖譜----214
圖4-3-3 化合物ZK-3之HRESIMS圖譜----215
圖4-3-4 化合物ZK-3之13C NMR圖譜(100 MHz, C5D5N) ----215
圖4-3-5 化合物ZK-3之DEPT圖譜----216
圖4-3-6 化合物ZK-3之1H NMR圖譜(400 MHz, C5D5N) ----216
圖4-3-7 化合物ZK-3之HSQC圖譜----217
圖4-3-8 化合物ZK-3之COSY圖譜----217
圖4-3-9 化合物ZK-3之HMBC圖譜----218
圖4-3-10 化合物ZK-3之NOESY圖譜----218
圖4-4-1 化合物ZK-4之UV圖譜----226
圖4-4-2 化合物ZK-4之IR圖譜----226
圖4-4-3 化合物ZK-4之HRESIMS圖譜----227
圖4-4-4 化合物ZK-4之13C NMR圖譜(150 MHz, C5D5N)----227
圖4-4-5 化合物ZK-4之DEPT圖譜----228
圖4-4-6 化合物ZK-4之1H NMR圖譜(600 MHz, C5D5N) ----228
圖4-4-7 化合物ZK-4之HSQC圖譜----229
圖4-4-8 化合物ZK-4之COSY圖譜----229
圖4-4-9 化合物UF-4之HMBC圖譜----230
圖4-4-10 化合物UF-4之NOESY圖譜----230
圖4-5-1 化合物ZK-5之UV圖譜----238
圖4-5-2 化合物ZK-5之IR圖譜----238
圖4-5-3 化合物ZK-5之HRESIMS圖譜----239
圖4-5-4 化合物ZK-5之13C NMR圖譜(150 MHz, C5D5N) ----239
圖4-5-5 化合物ZK-5之DEPT圖譜----240
圖4-5-6 化合物ZK-5之1H NMR圖譜(600 MHz, C5D5N) ----240
圖4-5-7 化合物ZK-5之HSQC圖譜----241
圖4-5-8 化合物ZK-5之COSY圖譜----241
圖4-5-9 化合物ZK-5之HMBC圖譜----242
圖4-5-10 化合物ZK-5之NOESY圖譜----242
圖4-6-1 化合物ZK-6之UV圖譜----249
圖4-6-2 化合物ZK-6之IR圖譜----249
圖4-6-3 化合物ZK-6之HRESIMS圖譜----250
圖4-6-4 化合物ZK-6之13C NMR圖譜(150 MHz, C5D5N)----250
圖4-6-5 化合物ZK-6之DEPT圖譜----251
圖4-6-6 化合物ZK-6之1H NMR圖譜(600 MHz, C5D5N)----251
圖4-6-7 化合物ZK-6之HSQC圖譜----252
圖4-6-8 化合物ZK-6之COSY圖譜----252
圖4-6-9 化合物ZK-6之HMBC圖譜----253
圖4-6-10 化合物ZK-6之NOESY圖譜----253
圖5-1-1 所有UF系列化合物結構----254
圖5-2-1 所有ZK系列化合物結構----256
圖7-2-1 U. flexuosa之萃取以及分配萃取流程----270
圖7-2-2 U. flexuosa之水摻甲醇層(UFM)分離流程----271
圖7-2-3 U. flexuosa之劃分層UFM-6分離流程----272
圖7-2-4 U. flexuosa之劃分層UFM-7分離流程----273
圖7-2-5 U. flexuosa之劃分層UFM-8+UFM-9+UFM-10分離流程----274
圖7-2-6 U. flexuosa之劃分層UFM-15與UFM-15-L3分離流程----275
圖7-2-7 U. flexuosa之劃分層UFM-15-L4分離流程----276
圖7-3-1 Z. kuroshio之萃取以及分配萃取流程----277
圖7-3-2 Z. kuroshio之劃分層ZO1-M與ZO1-M-S2分離流程----278
圖7-3-3 Z. kuroshio之劃分層ZO1-M-S2-1分離流程----279
圖7-3-4 Z. kuroshio之劃分層ZO1-M-S2-2分離流程----280
圖7-3-5 Z. kuroshio之劃分層ZO1-M-S2-3分離流程----281
圖7-3-6 Z. kuroshio之劃分層ZO1-M-S2-4分離流程----282

表目錄
表1-3-1 紫玉盤屬植物之黃酮類化合物文獻回顧整理----8
表1-3-2 紫玉盤屬植物之多氧取代環己烯類化合物文獻回顧整理----17
表1-3-3 紫玉盤屬植物之番荔枝乙醯生合成物文獻回顧整理----29
表1-3-4 紫玉盤屬植物之苯類化合物文獻回顧整理----36
表1-3-5 紫玉盤屬植物之生物鹼類化合物文獻回顧整理----42
表1-3-6 紫玉盤屬植物之三萜類化合物文獻回顧整理----48
表1-3-7 紫玉盤屬植物之固醇類化合物文獻回顧整理----51
表1-3-8 紫玉盤屬植物之長鏈類化合物文獻回顧整理----52
表1-3-9 紫玉盤屬植物之倍半萜類化合物文獻回顧整理----52
表1-3-10 紫玉盤屬植物之dihydrooxepine類化合物文獻回顧整理----53
表1-3-11 紫玉盤屬植物之木酚素類化合物文獻回顧整理----54
表1-3-12 紫玉盤屬植物之單萜類化合物文獻回顧整理----55
表1-3-13 紫玉盤屬植物之香豆素類化合物文獻回顧整理----56
表1-3-14 紫玉盤屬植物之其他類化合物文獻回顧整理----56
表1-5-1 花群海葵屬之zoanthamine-type生物鹼類文獻回顧整理----67
表1-5-2 花裙海葵屬之固醇類化合物文獻回顧整理----74
表1-5-3 花裙海葵屬之長鏈化合物與脂肪酸文獻回顧整理----78
表1-5-4 花裙海葵屬之sulfated sphingolipid類化合物文獻回顧整理----80
表2-1-1 紫玉盤屬植物U. flexuosa分離成分分類----87
表2-2-1 黑潮花裙海葵Z.kuroshio分離成分結構----91
表3-1-1 1H and 13C NMR Spectroscopic Data of UF-1----100
表3-2-1 1H and 13C NMR Spectroscopic Data of UF-2----111
表3-3-1 1H and 13C NMR Spectroscopic Data of UF-3 and Grandiuvarin C----122
表3-4-1 1H and 13C NMR Spectroscopic Data of UF-4 and Flexuvarin B----132
表3-5-1 1H and 13C NMR Spectroscopic Data of UF-5 and Flexuvarin C----142
表3-6-1 1H and 13C NMR Spectroscopic Data of UF-6 and Uvamalol C----153
表3-7-1 1H and 13C NMR Spectroscopic Data of UF-7 and Flexuvarol A----164
表4-1-1 1H and 13C NMR Spectroscopic Data of ZK-1 and Zoanthenamine----188
表4-2-1 1H and 13C NMR Spectroscopic Data of ZK-2 and Kuroshine A----201
表4-3-1 1H and 13C NMR Spectroscopic Data of ZK-3 and Kuroshine A----213
表4-4-1 1H and 13C NMR Spectroscopic Data of ZK-4 and Kuroshine E----225
表4-5-1 1H and 13C NMR Spectroscopic Data of ZK-5 and Kuroshine E----237
表4-6-1 1H and 13C NMR Spectroscopic Data of ZK-6 and Kuroshine E----248

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