紫杉醇為1960年代所發現的一種能穩固微管進而抑制癌細胞分裂及增生的有效抗癌藥物，紅豆杉雙萜類化合物因品種、採收季節與生長環境不同而結構多樣化，故引起各方學者的研究熱潮。為了找尋新穎和更具抗癌活性的紅豆杉雙萜類，本研究遂以高雄縣六龜鄉林區所採集的七年生及十年生南洋紅豆杉(Taxus sumatrana)枝葉為材料，進行成分分析。
實驗中將所採集之南洋紅豆杉以丙酮三次萃取，合併粗萃物後，由色層分析方法分離純化，接著以核磁共振磁譜技術，包括1H-NMR、13C-NMR、DEPT、COSY、HMQC、HMBC和NOESY等分析方法，以及其他物理方法如質譜(EIMS)、紅外線光譜(IR)、紫外線光譜(UV)與旋光度之測量，加上相關文獻之比對進行紅豆杉雙萜類成分的化學結構分析。
本研究經確認得到三十七個紫杉烷類化合物，分別是sumataxin A (1)、sumataxin B (2)、sumataxin C (3)、sumataxin D (4)、taxuyunnanine C (5)、5a,7B,9a,10B,13a-petaacetoxy-4(20),11-taxadiene (6)、2a,5a,9a,10B,14B-pentaacetoxytaxa-4(20),11-taxadiene (7)、14B-hydroxytaxusin (8)、2a-deacetoxytaxinine J (9)、taxa-4-(20),11-diene-2a,5a,7B,9a,10B,13a-hexaol hexaacetate (10)、1-dehydroxy baccatin VI (11)、7B,9a,10B,13a,20-pentaacetoxy-2a-benzoyloxy-4a,5a-dihydroxytax-11-ene (12)、taxacin (13)、baccatin VI (14)、taxuspinanane J (15)、2-deacetoxy-5-decinnamoyltaxinine J (16)、N-Methyl taxol C (17)、10-deacetyl yunnanaxane (18)、taxumairol B (19)、taxinine M (20)、baccatin III (21)、taxuspinanane I (22)、taxumairol K (23)、wallifoliol (24)、13-oxo-baccatin III (25)、taxol (26)、7-epi-10-deacetyl taxol (27)、10-deacetyl-13-oxo-baccatin III (28)、19-hydroxybaccatin III (29)、10-deacetyl taxol (30)、10-deacetyl-baccatin III (31)、13-acetyl-13-decinamoyltaxachinin B (32)、5-deacetyltaxachitriene B (33)、5-epicanadensene (34)、taxezopidine F (35)、13a,7B-diacetoxy-2a,5a,10B-trihydroxy-9-keto-2(3→20)abeotaxane (36)、2-deacetyl taxine B (37)。其中化合物1、2、3、4為在天然界首次發現的新化合物，化合物2a-deacetoxytaxinine J (9)、taxuspinanane J (15)具有免疫細胞促進增生活性，而sumataxin A、D (1、4)對於第一型疱疹病毒有輕微的抑制效果。

Taxol is a complex polyoxygenated diterpene isolated from Pacific yew (Taxus brevifolia). The structures of Taxoids are diversified with species, season and growth environment and the clinical effectiveness of Taxol as a microtubule-stabilizing therapeutic agent for treatment of several malignancies has motivated many scientists to isolate new taxoids and investigate their anti-tumor activities.
In this continuing search for new and bioactive natural taxoids, reinvestigation of the acetone extract of the twigs, needles and branches of Taxus sumatrana (Taxaceae) afforded thirty-seven taxane diterpenes esters, including sumataxins sumataxin A (1)、sumataxin B (2)、sumataxin C (3)、sumataxin D (4)、taxuyunnanine C (5)、5a,7B,9a,10B,13a-petaacetoxy-4(20),11-taxadiene (6)、2a,5a,9a,10B,14B-pentaacetoxytaxa-4(20),11-taxadiene (7)、14B-hydroxytaxusin (8)、2a-deacetoxytaxinine J (9)、taxa-4-(20),11-diene-2a,5a,7B,9a,10B,13a-hexaol hexaacetate (10)、1-dehydroxy baccatin VI (11)、7B,9a,10B,13a,20-pentaacetoxy-2a-benzoyloxy-4a,5a-dihydroxytax-11-ene (12)、taxacin (13)、baccatin VI (14)、taxuspinanane J (15)、2-deacetoxy-5-decinnamoyltaxinine J (16)、N-Methyl taxol C (17)、10-deacetyl yunnanaxane (18)、taxumairol B (19)、taxinine M (20)、baccatin III (21)、taxuspinanane I (22)、taxumairol K (23)、wallifoliol (24)、13-oxo-baccatin III (25)、taxol (26)、7-epi-10-deacetyl taxol (27)、10-deacetyl-13-oxo-baccatin III (28)、19-hydroxybaccatin III (29)、10-deacetyl taxol (30)、10-deacetyl-baccatin III (31)、13-acetyl-13-decinamoyltaxachinin B (32)、5-deacetyltaxachitriene B (33)、5-epicanadensene (34)、taxezopidine F (35)、13a,7B-diacetoxy-2a,5a,10B-trihydroxy-9-keto-2(3→20)abeotaxane (36)、2-deacetyl taxine B (37). The structures of new compounds were established on the basis of their spectroscopic analyses. Among them, compounds 1, 2, 3 and 4 are new compounds from natural source, 2a-deacetoxytaxinine J (9)、taxuspinanane J (15) had effects on PBMC (Peripheral Blood Mononuclear Cells) proliferation, and sumataxin A、D (1、4) had light exhibitedactivity of HSV-1.

第ㄧ部份 緒論
第一章 前言---------------------------------------------------------------------- 1
第二章 紅豆杉植物的簡介---------------------------------------------------- 3
第三章 Taxus屬紅豆杉最近研究之相關文獻回顧¬¬¬---------------------- 6
第一節 歐洲紅豆杉 (Taxus baccata)-------------------------------- 6
第二節 加拿大紅豆杉 (Taxus canadensis)------------------------ 7
第三節 中國紅豆杉 (Taxus chinensis)----------------------------- 11
第四節 日本紅豆杉 (Taxus cuspidata)---------------------------- 12
第五節 南方紅豆杉 (Taxus mairei)--------------------------------- 17
第六節 南洋紅豆杉 (Taxus sumatrana)--------------------------- 20
第四章 研究目的與展望----------------------------------------------------- 22
第二部份 材料與方法
第一章 結構之鑑定----------------------------------------------------------- 24
第一節 儀器-------------------------------------------------------------- 24
第二節 矽膠與溶劑----------------------------------------------------- 25
第二章 樣品的採集----------------------------------------------------------- 25
第三章 分離與純化----------------------------------------------------------- 26
第三部份 結果與討論
第一章 台灣產南洋紅豆杉(Taxus sumatrana)成分化合物結構鑑定
第一節 化合物1的結構解析------------------------------------------ 40
第二節 化合物2的結構解析------------------------------------------ 44
第三節 化合物3的結構解析----------------------------------------- 48
第四節 化合物4的結構解析----------------------------------------- 52
第五節 化合物5的結構解析----------------------------------------- 56
第六節 化合物6的結構解析----------------------------------------- 56
第七節 化合物7的結構解析----------------------------------------- 57
第八節 化合物8的結構解析----------------------------------------- 57
第九節 化合物9的結構解析----------------------------------------- 58
第十節 化合物10的結構解析---------------------------------------- 58
第十一節 化合物11的結構解析------------------------------------- 59
第十二節 化合物12的結構解析------------------------------------- 59
第十三節 化合物13的結構解析------------------------------------- 60
第十四節 化合物14的結構解析------------------------------------- 60
第十五節 化合物15的結構解析------------------------------------- 61
第十六節 化合物16的結構解析------------------------------------- 61
第十七節 化合物17的結構解析------------------------------------- 62
第十八節 化合物18的結構解析------------------------------------- 62
第十九節 化合物19的結構解析------------------------------------- 63
第二十節 化合物20的結構解析------------------------------------- 63
第二十一節 化合物21的結構解析---------------------------------- 64
第二十二節 化合物22的結構解析---------------------------------- 64
第二十三節 化合物23的結構解析---------------------------------- 65
第二十四節 化合物24的結構解析---------------------------------- 65
第二十五節 化合物25的結構解析---------------------------------- 66
第二十六節 化合物26的結構解析---------------------------------- 66
第二十七節 化合物27的結構解析---------------------------------- 67
第二十八節 化合物28的結構解析---------------------------------- 67
第二十九節 化合物29的結構解析---------------------------------- 68
第三十節 化合物30的結構解析------------------------------------- 68
第三十一節 化合物31的結構解析---------------------------------- 69
第三十二節 化合物32的結構解析---------------------------------- 69
第三十三節 化合物33的結構解析---------------------------------- 70
第三十四節 化合物34的結構解析---------------------------------- 70
第三十五節 化合物35的結構解析---------------------------------- 71
第三十六節 化合物36的結構解析---------------------------------- 71
第三十七節 化合物37的結構解析---------------------------------- 72
第二章 活性測試結果-------------------------------------------------------- 73
第四部份 結論----------------------------------------------------------------- 76
第五部份 參考文獻----------------------------------------------------------- 78
第六部份 附錄
第一章 sumataxin A (1)之物理資料及NMR光譜資料---------------- 83
第二章 sumataxin B (2)之物理資料及NMR光譜資料---------------- 88
第三章 sumataxin C (3)之物理資料及NMR光譜資料--------------- 93
第四章 sumataxin D (4)之物理資料及NMR光譜資料--------------- 98
第五章 已知化合物5-37之1H-NMR光譜資料------------------------ 103

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