臺灣博碩士論文加值系統

分別以甲醇萃取番荔枝 (Annona squamosa)與山刺番荔枝 (A. montana)的種子，經由管柱層析與高效能液相層析儀分離純化，共得到三十四個化合物。於番荔枝(A. squamosa)之種子部分，共分離純化得到二十八個化合物，包含：七個cyclopeptides類化合物，squamin A (1)、squamin B (2)、cherimolacyclopeptide B (3)、cyclosquamosin D (4)、cyclosquamosin E (5)、cyclosquamosin A (6)及cyclosquamosin J (7)；十九個Annonaceous acetogenins類化合物，glaucafilin (13)、muricatetrocin B (14)、arianacin (15)、squadiolin C (23)，cis- squadiolin C (24)，squamocin B (12)、squamocin O1 (16)、squamocin O2 (17)、purpurediolin (19)、atemotetrolin (20)、annoglaucin (21)、squamocin P (22)、10-hydroxytrilobacin (26)及10-hydroxyasimicin (27)，bullatanocin (10)、12,15-cis-bullatanocin (11)、squamostatin-A (18)、bullatalicin (25) 及squamocinin (34)；二個amide類化合物，N-trans-caffeoyltyramine (8)及N-p-coumaroyltyramine (9)。另外，從山刺番荔枝(A. montana)之種子共分離純化得到五個cyclopeptides類化合物，annomuricatin C (28)、cyclomontanin A (29)、cyclomontanin B (30)、cyclomontanin C (32)、cycmontanin D (33)與一個alkaloids類化合物，(+)-corytuberine (31)。上列三十四個化合物的結構解析經由光譜資料分析、並配合化學方法加以證明確定。其中化合物7、22、24、29、30、32、33及34均為新化合物。
其中，cyclopeptides類化合物4、29及32於in vitro的J774A.1 macrophages模式中，顯示具有抗發炎的活性。而Annonaceous acetogenins類化合物均顯示中等至強效的細胞毒殺活性。

In present investigation, the seeds of Annona squamosa and A. montana were collected and extracted with methanol. The extracts were further separated by column chromatography and high performance liquid chromatography, and gave thirty-four compounds. Twenty-eight compounds were isolated from the seeds of A. squamosa, including seven cyclopeptides: squamin A (1), squamin B (2), cherimolacyclopeptide B (3), cyclosquamosin D (4), cyclosquamosin E (5), cyclosquamosin A (6) and cyclosquamosin J (7); nineteen Annonaceous acetogenins: glaucafilin (13), muricatetrocin B (14), arianacin (15), squadiolin C (23), cis- squadiolin C (24), squamocin B (12), squamocin O1 (16), squamocin O2 (17), purpurediolin (19), atemotetrolin (20), annoglaucin (21), squamocin P (22), 10-hydroxytrilobacin (26), 10-hydroxyasimicin (27), bullatanocin (10), 12,15-cis-bullatanocin (11), squamostatin-A (18), bullatalicin (25) and squamocinin (34); two amides: N-trans-caffeoyltyramine (8) and N-p-coumaroyltyramine (9). Additionally, five cyclopeptides: annomuricatin C (28), cyclomontanin A (29), cyclomontanin B (30), cyclomontanin C (32), cyclomontanin D (33), and one alkaloid: (+)-corytuberine (31) were obtained from the seeds of A. montana. Structures of isolates were elucidated by spectroscopic and chemical methods. Among them, compounds 7, 22, 24, 29, 30, 32, 33 and 34 are new compounds.
Compounds 4, 29, and 32 which are cyclopeptides showed anti-inflammatory activity by in vitro macrophages model. Most Annonaceous acetogenins showed moderate to strong cytotoxicity against tested cell lines.

致謝.................................................. I
中文摘要.............................................. III
英文摘要.............................................. IV
目錄.................................................. VI
圖表目錄.............................................. VIII
第一章 緒論
第一節 前言..................................... 1
第二節 植物型態分佈及應用....................... 4
第三節 Cyclopeptides相關之研究與文獻整理........ 7
第四節 近年來Annonaceous acetogenins之文獻整理.. 33
第二章 實驗流程與步驟
第一節 植物成分之抽取與分離..................... 42
第二節 化學合成................................. 59
第三章 化合物之結構證明
第一節 Annomuricatin C (28) 之結構證明.......... 64
第二節 Cyclomontanin A (29)*之結構證明.......... 77
第三節 Cyclomontanin B (30)*之結構證明.......... 92
第四節 Cyclomontanin C (32)*之結構證明.......... 106
第五節 Cyclomontanin D (33)*之結構證明.......... 122
第六節 Cyclosquamosin A (6)
與Cyclosquamosin J (7)*之結構證明........ 133
第七節 Cyclosquamosin D (4) 之結構證明.......... 140
第八節 Cyclosquamosin E (5) 之結構證明.......... 147
第九節 Squamocin P (22)*之結構證明.............. 154
第十節 Squamocinin (34)*之結構證明.............. 162
第十一節 Squadiolin C (23)
與cis-Squadiolin C (24)*之結構證明....... 170
第十二節 Squamocin O1 (16)
與Squamocin O2 (17)之結構證明............ 178
第四章 生物活性試驗
第一節 生物活性之試驗方法
一、細胞毒殺試驗.............................. 187
二、抗發炎活性試驗............................ 189
第二節 活性篩選結果
一、細胞毒殺活性.............................. 190
二、抗發炎活性….............................. 191
第五章 結論........................................ 193
第六章 各化合物之物理與光譜數據總整理.............. 195
第七章 參考文獻.................................... 215

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